Centre for Surfactants based on Natural Products SNAP

Transcription

SNAP Centre for Surfactants based on Natural Products - 10 year final report
Centre for Surfactants based on
Natural Products
SNAP
Centrum för Naturproduktbaserade Tensider
10 Year Final report
1996 - 2006
21 December 2006
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Contents
EXECUTIVE SUMMARY ..........................................................................................................................................5
SAMMANFATTNING .................................................................................................................................................6
1 THE SNAP COMPETENCE CENTRE. BASIC FACTS ...................................................................................7
1.1 GOALS AND STRATEGY .........................................................................................................................................7
1.2 PARTICIPATING PARTNERS ...................................................................................................................................8
1.3 ECONOMIC ACCOUNTING ....................................................................................................................................11
2 DEVELOPMENT OF SNAP OVER THE 11 YEAR PERIOD .......................................................................12
2.1 MANAGEMENT STRUCTURES ..............................................................................................................................12
2.2 RESEARCH PROGRAMMES ...................................................................................................................................15
3 KEY VALUES ..........................................................................................................................................................17
4 STANDING OF SNAP IN AN INTERNATIONAL AND NATIONAL CONTEXT....................................18
4.1 ATTRACTIVENESS OF SNAP INTERNATIONAL COLLABORATION .....................................................................18
4.2 VISIBILITY OF SNAP ..........................................................................................................................................20
4.3 THE COMPETENCE CENTRE AS A NATIONAL ASSET. CORE COMPETENCES AND CRITICAL MASSES ................21
4.4 THE ROLE AND IMPACT OF THE CENTRE WITHIN THE UNIVERSITY ...................................................................21
4.5 TECHNICAL AND SCIENTIFIC ACHIEVEMENTS ....................................................................................................22
4.6 “SUCCESS STORIES”............................................................................................................................................32
5 BENEFITS TECHNOLOGY TRANSFER. IMPACT ON THE PARTNERS ..............................................34
5.1 PARTNER INVOLVEMENT AND INTERACTION .....................................................................................................34
5.2 CENTRE MECHANISMS AND WAYS OF WORKING IN ORDER TO FACILITATE INDUSTRIAL IMPLEMENTATION ..34
5.3 COMMERCIALIZATION AND TECHNOLOGY TRANSFER .......................................................................................35
5.4 IMPACT ON THE PARTNERS AND THEIR R&D-PERFORMANCE ..........................................................................36
6 PROSPECTS AND STRATEGIES BEYOND THE TEN-YEAR PERIOD ..................................................40
APPENDIX A EXAMINATION ..............................................................................................................................41
LICENTIATE´ S DEGREES ............................................................................................................................................41
DOCTOR´S DEGREES ..................................................................................................................................................41
COMPLETED MSC THESES - DIPLOMA WORKS ........................................................................................................43
APPENDIX B PUBLICATIONS ..............................................................................................................................45
APPENDIX C RESEARCH STAFF 1995-2006 .....................................................................................................57
APPENDIX D CENTER ORGANISATION DURING STAGE 1-4 ..................................................................60
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Executive summary
The competence centre SNAP (Surfactants Based on Natural Products) was in operation
between the end of 1995 until June 2006. SNAP was created due to the vision that the
industrial use of natural raw materials will and should increase and that surfactants derived
from natural products will become common products, known for their unique properties as
compared to petroleum based surfactants. This vision is valid also today, and we see an
increasing emphasis on “Green Chemistry” from consumers, industries, funding agencies and
the society as a whole.
A total of 13 industrial companies and 6 academic departments have participated within
SNAP. The core competence within SNAP included deep knowledge in organic chemistry,
physical chemistry, surface chemistry as well as biochemistry. Besides this cross-disciplinary
nature of the centre, it was also cross-technological since the industrial partners included raw
material producers, surfactant producers and end-users of surfactants. The combined broad
cross-disciplinary and broad cross-technological character of the centre activities made us
rather unique in the world. This has indeed made SNAP a national asset when it comes to
exploring the properties and applications of the new generation environmentally friendly
surfactants. Also, the fact that the industries hardly competed with each other but rather
benefited by collaborating, led to an open and trustful atmosphere within the centre.
17 PhD- and 2 LicD-students have graduated within SNAP between 1998-2006, and 5 more
PhD students will graduate during 2007/2008. A total of 188 scientific articles and book
contributions have, in December 2006, been published and SNAP-researchers have also been
well represented on international conferences. The scientific achievements of SNAP are
versatile, spanning from synthesis of several isomeric forms of complex sugar-based
surfactants and enzymatic synthesis of non-hemolytic surfactants for pharmaceutical use, to
development of new experimental schemes for understanding removal of particulate soil,
polymer-surfactant interactions, effects of the linker group on biodegradability of surfactants,
synergism, and microemulsion formulation, just to mention a few. It is evident that the
understanding of the properties of the next generation, more environmentally friendly,
surfactants have been increased significantly due to SNAP. However, much research remains
to be done in this area since the need for environmentally friendly surfactants is expected to
increase at an accelerating speed in the future.
The industrial partners have found it valuable to work within the competence centre
framework. Some of the mentioned benefits have been the creation of new knowledge, new
collaborations between industrial partners, new patents, method developments, and research
visits of industrial researchers to academic sites and vice versa. Some of the partners that were
active in SNAP have continued to collaborate after the closing of the centre, for example
within the new VINN-Ex centre Supramolecular biomaterials structure dynamics and
properties, within the EU-project Self-organisation under confinement, or within the new
VINN-ExI centra Controlled Delivery and Release. Several other on-going collaborations are
also results from SNAP activities. Thus, even if SNAP has formally closed, the SNAP spirit
still influences our activities, and we predict that it will continue to do so for a long period of
time.
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Sammanfattning
Kompetenscentrumet SNAP (Naturproduktbaserade tensider) var aktivt från slutet av 1995 till
juni 2006. SNAP skapades som ett resultat av visionen att den industriella användningen av
förnyelsebara naturprodukter skall och bör öka, och att tensider tillverkade av dessa råmaterial
kommer att bli vanligt förekommande i produkter kända för deras unika egenskaper jämfört
med syntetiskt framställda tensider från olja. Denna vision är aktuell även idag och vi märker
ett ökas fokus på ”Grön kemi” från konsumenter, industri, anslagsgivare och samhället som
helhet.
Totalt 13 industrier and 6 akademiska partner har deltagit i SNAP. Kärnkompetensen inom
SNAP inkluderar djupa kunskaper i organisk kemi, fysikalisk kemi, ytkemi och biokemi.
Förutom denna bredd i ämnenskunskaper så ingick också kunskaper inom olika
teknologiområden då de industriella parterna var både råmaterialproducenter,
tensidproducenter och slutanvändare av tensider. Kombinationen av tvärvetenskaplig och
tvärteknologisk kompetens gjorde oss unika i världen, vilket gjorde SNAP till en nationell
tillgång vad gäller karakterisering och framtida användning av nästa generations miljövänliga
tensider. Dessutom, eftersom industrierna inom SNAP inte var direkta konkurrenter utan
snarare tjänade på att samarbeta med varandra var arbetsatmosfären inom centrumet god och
öppen.
17 doktorer och 2 licentiater har examinerats från SNAP mellan 1995-2006, och ytterligare 5
doktorander kommer att utexaminerats under 2007/2008. Totalt 188 vetenskapliga artiklar och
bokkapitel har, vid december 2006, publicerats och forskare inom SNAP har varit väl
representerade på internationella konferenser. De vetenskapliga prestationerna inom SNAP
har varit mångsidiga, allt ifrån syntes av ett flertal isomerer av komplexa sockerbaserade
tensider, enzymatisk syntes av icke-hemolytiska tensider för läkemedelsindustrin, till
utveckling av nya experimentella metoder för att förstå och optimera parikelborttagning från
ytor, polymer-tensid växelverkan, effekten av typen av kemisk bindning på nedbrytbarheten
för tensider, synergieffekter, och formulering av mikroemulsioner, för att nämna några
exempel. Förståelsen av egenskaperna hos nästa generation miljövänliga tensider har ökat
väsentligt tack vare SNAP, men mycket forskning återstår att göras inom detta område
eftersom behovet av miljövänliga tensider förväntas öka i framtiden.
Industrierna som medverkat inom SNAP har funnit det värdefullt att arbeta inom
kompetenscentrumstrukturen. Några av fördelarna som nämnts är genereringen av ny
kunskap, nya samarbeten mellan de medverkande industrierna, nya patent, metodutvecklingar,
och besök hos de akademiska parterna. Många av parterna inom SNAP har fortsatt att
samarbeta efter det att centrumet avslutats, till exempel inom det nya VINN-Ex centrumet
Supramolecular biomaterials structure dynamics and properties, inom EU projektet Selforganisation under confinement, eller inom det nya VINN-ExI centrumet Controlled Delivery
and Release. Många andra pågående forskningsamarbeten är resultat av de kontakter som
knöts inom SNAP. Alltså även om SNAP formellt har avslutats påverkar fortfarande SNAP
andan våra aktiviteter och vi förutspår att den kommer att fortsätta göra det under en lång tid
framöver.
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1 The SNAP competence centre. Basic facts
1.1 Goals and strategy
The Centre for Surfactants Based on Natural Products (SNAP) was created due to the vision
that the industrial use of natural raw materials will and should increase and that surfactants
derived from natural products will become common products, known for their unique
properties as compared to petroleum based surfactants. One of the original ideas was that it
should be possible to “tailor-make” molecules based on carbohydrates, fatty acids or other
natural products to fulfil the performance demands set by different applications. This vision is
valid also today, and we see an increasing emphasis on “Green Chemistry” from consumers,
industries, funding agencies and the society as a whole. The increasing number of scientists
with knowledge of both surfactant synthesis and properties will speed-up the development in
this area. We mean that the research and the research education provided by SNAP indeed
have made a significant contribution forwards these goals and visions.
There are many advantages of using natural based products as raw materials for surfactants
compared to petroleum based raw materials:
– Natural products offer unique opportunities to incorporate special structural elements
in the surfactant molecule, which will lead to new or improved functional properties of
the product. For instance, the properties of alkyl glycosides are generally much less
sensitive to temperature then those of ethylene oxide-based surfactants. Their
adsorption behaviour on different surfaces and the short-range interactions between
surfaces coated with surfactants are also different.
– Chemical products based on natural starting materials can often be made more
biodegradable, less toxic and less allergenic.
– Petroleum oils are non-renewable and will in the long term become more expensive as
the resources are limited.
– Petroleum-based products are often subject to environment-related levies such as
special taxes, while reduced taxation or even subsidies usually favour products from
renewable sources.
These reasons have lead to an increasing interest in surfactants based, entirely or partly, on
natural products. This attention has revealed a need to increase the existing knowledge of
these surfactants and how they interact with other components present in formulations. There
is thus a need to build up expertise in this field.
The main goal of the center was to build, from an industrial need, a long-term knowledge and
experience regarding new environmentally safe surfactants derived, entirely or partly, from
natural products. A key issue was to identify the best ways of utilising the properties of the
surfactants.
The five objectives of the center was summarized as follows:
1. to increase the comprehension of surfactants based on natural products, which will
lead to an increased commercial use and a better environment,
2. to identify properties of these surfactants that are unique as compared to traditional
surfactants,
3. to train scientists in the various fields of science within the frame-work of the center,
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4. through an active co-operation strengthen the expertise of the participating industrial
companies and academic institutions,
5. to develop and intensify international collaborations in the field.
The first objective can be regarded as an industrial goal. In order to be feasible for
commercial use the natural raw material should be easily available within 5 years. The second
objective is of great importance both for industry and academia. The third objective is to
increase the number of skilled scientists, which obviously is of particular interest to the
academic partners, but is also of long-term interest to the industry. It should be stressed that
the center did provide an interdisciplinary education. Within the center PhD-students from
physical chemistry, surface chemistry, organic chemistry and biochemistry have worked
together with the industrial partners. The success of the network activities, as formulated in
the fourth objective, can be estimated from the number of joint projects, publications, patents
and site visits. The fifth objective was included in recognition of the relevant work carried out
by research groups outside the center.
The center has aimed at creating an active and sustainable co-operation between academic and
industrial research, and we believe that we have succeeded in this. The research projects
performed in SNAP have been planned and performed in direct co-operation between
academic and industrial partners. In particular, the active participation of the companies
shaped the course of the research activities. The participation of the industry also ensured a
quick transfer and feedback of results between scientists at universities and industries, thus
creating the best conditions to reach the targeted objectives
1.2 Participating partners
The participating academic departments were the following:
1.
Royal Institute of Technology (KTH):
Department of Chemistry, Organic Chemistry
Department of Chemistry, Surface Chemistry
Department of Biotechnology, Biochemistry and Wood Biotechnology
2.
Institute for Surface Chemistry (YKI):
The Chemical and Engineering Industries Section
The Forest Products Section
3.
Lund University (LU):
Department of Physical Chemistry 1
4.
Chalmers University of Technology (CTH):
Department of Materials and Surface Chemistry
Table 1 lists the industrial partners that have been active in SNAP during the different stages.
They include raw material producers, surfactant producers and end-users of surfactants with
an interest in a wide range of applications.
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Table 1. Participating industrial partners in the different stages over the 11 year period.
Akzo Nobel Surface Chemistry AB, Stenungsund.
Number of employees: 1 900 (world wide)
Areas of interest: Synthesis, properties and application of
surfactants.
Arizona Chemical BV, Technology group, Almere,
Netherlands.
Number of employees: 23
Areas of interest: Development of new use for tall oil fatty
acids, use of surfactants in environmentally-adapted dispersions
of rosin acids. Lubrication applications.
AstraZeneca R&D, Mölndal.
Number of employees: 60000 (worldwide) 2500 (Mölndal)
Areas of interest: Enzymatic synthesis of surfactants,
application of surfactants in pharmaceutical formulations.
AstraZeneca R&D, Lund.
Number of employees: 60000 (worldwide)1200 (Lund).
Areas of interest: Enzymatic synthesis of surfactants,
application of surfactants in pharmaceutical formulations.
Castrol AB.
Number of employees:120
Areas of interest: Surfactants in cutting fluids and degreasing.
Karlshamns AB, Karlshamn.
Number of employees: 754 (611 in Sweden)
Areas of interest: Processing of fatty acids and oil.
Multifunctional surface active components in cosmetics.
Kemira Kemi AB,
Areas of interest: Detergents and washing powders
Snowclean AB, Alingsås.
Areas of interest: Formulations for industrial degreasing and car
shampoos.
Svenska Lantmännen (Lantmännen), Stockholm.
Number of employees: 10 268
Areas of interest: Develop the expertise on using emulsifiers in
food products.
Unilever UK Central Resources, United Kingdom
Number of employees: 247 000 (Unilever total)
Areas of interest: Surfactants for laundry detergency and in oral
care applications.
UPM-Kymmene Corporation, Kaukas Chemical Mill,
Lappeenranta, Finland.
Number of employees: 35 000 (UPM-Kymmene total)
Areas of interest: Sterol-based surfactants.
Scotia LipidTeknik AB, Stockholm.
Number of employees: 44 Areas of interest: Isolation and
characterization of polar lipids.
Rolf Kullgren AB, Number of employees: 10, Areas of interest:
Cleaning formulations
Stage 1
19951997
X
Stage 2
19982000
X
Stage 3
20012003
X
Stage 4
20042006
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
X
The combination of broad cross-disciplinary and broad cross-technological expertise of the
industrial and academic partners that have been active in SNAP, illustrated in Figure 1, made
us rather unique in the world.
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.
Figure 1. The participating partners in SNAP illustrating the cross-disciplinary and crosstechnological expertise in the centre.
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1.3 Economic accounting
Table 2. Contributions in cash (C) and in-kind (K) in kSEK from the partners over the centre
life-time. The total contribution is 34,8 % from the industries, 34,7 % from the Universities
and 30,5 % from VINNOVA.
Stage
1
2
3
4
Total
C
K
C
K
C
K
C
K
C
K
Total
1 710
4 049
2 430
3 631
1 500
5 457
700
3 508
6 340
16 645
22 985
Arizona
80
227
150
200
180
378
200
365
610
1 170
1 780
AstraZeneca
80
300
265
1 749
880
2 607
600
1 193
1 825
5 849
7 674
Castrol
80
150
80
150
230
Karlshamn
80
99
210
1 290
1 558
2 848
Kemira
80
271
50
130
271
401
Partner
Akzo
454
Kullgrens
600
542
400
463
100
100
Scotia
50
1 348
3 050
Snowclean
80
153
150
114
180
53
120
SLR
80
350
165
897
600
962
845
Unilever
UPM
Kymmene
Kaukas
Total partners
2 320
Vinnova (Nutek)
6 000
KTH
2 652
6 948
50
4 398
4 448
34
530
354
884
500
1 201
1 345
3 410
4 755
3 890
1 339
2 303
2 184
6 193
8 377
250
666
300
382
200
163
750
1 211
1 961
3 670
10 761
5 185
14 271
4 059
9 229
15 234
41 208
56 442
13 485
1 855
100
2 046
18 000
7 314
2 141
12 000
12 191
804
49 485
4 752
7 643
49 485
26 112
33 755
Lund University
407
1 284
4 372
3 096
9 160
9 160
YKI
453
1 008
3 178
2 233
6 872
6 872
244
3 805
2 521
6 570
6 570
89 922
162 284
Chalmers
Total
Total
Cash + In kind
10 972
9 663
20 635
19 201
20 611
39 812
25 326
37 817
63 143
16 863
21 831
38 694
72 362
162 284
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2 Development of SNAP over the 11 year period
2.1 Management structures
The basic management structure of the centre has remained the same since the start of the
centre (Figure 2). The board leading the centre had four members from industry and two from
academia. There has been in average three boards meeting per year.
Board
Industrial
group
International
advisory group
Centre Director
Centre Coordinator
Programme/Area
Programme leader
from industry
Programme/Area
Programme leader
from industry
Programme/Area
Programme leader
from industry
Figure 2. SNAP management structure.
The industrial group has met once per year in connection with the annual meeting that took
place in the end of September each year. The group consisted of 1-2 members per company.
The industrial group has given input to the board about its views on the current research in the
centre and future reseach directions. The international advisory group has consisted of two
internationally recognised professors, experts in the field of colloid and interface science and
surfactant synthesis. From 1995-2000 the group consisted of Prof. Hans Lyklema from the
Laboratory of Physical Chemistry and Colloidal Science at Wageningen University and of
Prof. Fred Menger from Department of Chemistry at Emory University, Atlanta. Between
2001-2005 Prof. Menger was replaced by Prof. Jaeger from the Department of Chemistry at
University of Wyoming. The international advisory group participated at the annual meetings
and has given valuable feed-back on the quality of the center research as well as suggestions
on new areas of research. A new feature during the three final annual meetings was separate
talks between PhD-students and the international advisors. This was much appreciated by the
students and the advisors.
There have been two center directors, Prof. Torbjörn Norin, Organic chemistry, KTH (19951998) and Prof. Per Claesson, Surface Chemistry, KTH (1998-2006). The centre coordinator
has been located at YKI. There have been overall four coordinators Martin Svensson (19951998), Johanna Brinck (1998-2002), Mikael Kjellin (2002-2006) and Katrin Boschkova
(stand-in for two periods while Mikael was on paternity leave).
The area/programme leaders have been from industry and have had a central role of in the
organization. All research projects performed in SNAP have been organised into a specific
area/programme. The number of programmes and the specific research performed within each
programme has varied over the centre life-time, see description of the different research
programmes below. An important task for the programme leaders has been to balance
fundamental basic research in the programmes with more industrially relevant research. The
programme leader recommended (or not) any new project before the final decision was taken
by the board. This process has contributed to the industrial relevance of the research projects,
and it has also identified areas in which fundamental knowledge is missing. The programme
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leaders have arranged two programme meetings each year where all projects within a given
programme were reported and discussed. One of these meeting took place in connection with
the annual meeting. The programme meetings were essential for the collaborations within
SNAP and for the development of new projects and ideas. They also stimulated direct
collaborations between participating industries. The programmes have not been closed, but
open for all participants within SNAP. During the final years of SNAP the programme
meetings were held on consecutive days to make it more feasible for SNAP members to
participate in all programme meetings. The city chosen for the meetings have been varied, and
often a member company acted as a host.
In order for the center to work efficiently we clearly defined the tasks of the different
functions represented in the management of the center. They were as follows:
Director
– Responsible for the long term scientific strategy
– Responsible for the long term strategy of industrial contacts and development of
applications
– Responsible for the development of visions and goals of the Competence Center
– Responsible for the contribution of the Competence Center to a favorable outcome of
the training of the PhD students
Coordinator
– Make sure that all participants know goals and visions of programs and projects
– Coordinate external communication
– Make sure that the PhD students are satisfied with meetings, information on literature
as well as contacts with the industries etc
– Make sure that the representatives of the industry experience that meetings, flow of
information and contacts with the universities etc work well
– Make follow-ups of the economy
– Assist program leaders in the accomplishment of the scientific goals of their programs
– Prepare the Board meetings and assist as secretary to the Board
Program leader
– Present for approval by the Board, the goals and frames of the program and the
projects.
– In cooperation with the project leaders manage the program and submit project
proposals to the Board
– Cooperate with the coordinator in such a way that the PhD students within the
program experience that the contacts with industry work well
– Promptly identify cases of projects deviating from the goals and attend to this in
cooperation with the project leaders
Project leader/Supervisor
– Watch progress on the research front in their respective field
– Initiate new projects in cooperation with the program leader
– Be responsible for high quality of research being performed consistently
– Supervise PhD students and other personnel within the project area
– Contribute to the exchange between university and industry, of research results and
experience within the project area
– Be responsible for reporting to program leader and coordinator
– Stimulate close contacts with researchers in industry
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Table 3. Oveview of the persons directly active in the SNAP management.
Function
Chairman
Board
Director
Coordinator
Programme leader
International
group
advisory
Name
Lennart Dahlgren
Agne Svanberg
Eva Österberg
Lennart Dahlgren
Sewerin Ekman
Karl-Erik Falk
Ann Segerborg-Fick
Jan Christer Eriksson
Krister Holmberg
Agne Svanberg
Eva Byröd
Jan-Olof Lidefelt
Kenneth Alness
Martin Malmsten
Peter Somfai
Eva Österberg
Ulf Hansson
Bruce Lyne
Torbjörn Norin
Per Claesson
Martin Svensson
Johanna Brinck
Mikael Kjellin
Katrin Boschkova
Ann Segerborg-Fick
Karin Bergström
Torbjörn Norin
Martin Svensson
Johan Berg
Ingegärd Johansson
Affiliation
Akzo Nobel
Akzo Nobel
Akzo Nobel
Akzo Nobel
Kemira Kemi
Astra Hässle
Svenska Lantmännen
KTH
YKI
Akzo Nobel
AstraZeneca
Karlshamns
Svenska Lantmännen
YKI
KTH
Akzo Nobel
Karlshamns
YKI
KTH
KTH
YKI
YKI
YKI
YKI
Svenska Lantmännen
Akzo Nobel
KTH
YKI
Svenska Lantmännen
Akzo Nobel
Stage
1,2
2,3
3,4
1,2
1
1
1
1,2
1
2,3
2,3,4
2
2,3,4
2,3
3,4
3,4
3,4
3,4
1,2
2,3,4
1,2
2,3
3,4
3,4
1 (Area 1)
1 (Area 2)
1 (Area 3)
1 (Area 4)
2 (Programme A)
2,3,4 (Prog. B and Prog.
I-Industrial Applications)
2,3,4 (Prog. C and Prog.
II-Bio applications)
3,4 (Prog.II - Biological
applications)
Christian von Corswant
AstraZeneca
Martin Svensson
Svenska Lantmännen
Prof. Hans Lyklema
Wageningen University
1,2,3,4
Prof. Fred Menger
Prof. David Jaeger
Emory University
University of Wyoming
1,2,3
3,4
14
2.2 Research programmes
The centre has made two reorganisations during its life-time. The reasons behind the
reorganisations and the change of research focus will be described below. The development is
shown in Figure 3. More detailed schemes of the different organisations can be seen in
Appendix D.
Figure 3. Development of SNAP during the center life-time.
2.2.1 Research programme year 1 and 2 (Stage 1, 1995 - 1997)
The work was organised into four Areas during Stage 1:
Area 1 - Developing the natural raw material
The strategy of the centre was to utilise raw materials from various natural sources. Hence the
participation of a range of producers of suitable raw materials was essential for the subsequent
research activity. Examples of starting materials were lipids (animal and vegetable), sterols,
proteins, sugars and other carbohydrates.
Area 2 - Synthesis and Characterisation
This research area formed the major part of the activity of the centre. The objectives were to
find and explain the properties of surfactants that are based, entirely or partly, on natural
material. The work included characterisation of the unique surface chemical properties of
these surfactants as compared to traditional surfactants. The work was focused on different
types of non-ionic carbohydrate-based surfactants (sugar surfactants). The major objectives
can be summarised as:
•Identify surface chemical properties which make polyhydroxy-surfactants more useful than
ethoxylates in some applications.
•Give a comprehensive explanation of the differences in the behaviour between polyhydroxyl
and ethoxylated nonionic surfactants.
15
Area 3 - Surfactants in pharmaceutical applications
The objectives of this area were to develop and characterise amphilic compounds suitable for
pharmaceutical applications.
Area 4 - Technical & Environmental aspects of surfactants
In this research area the properties of technical importance were studied. These include
properties that are of importance in systems like emulsions, foams, and suspensions, which
are of relevance in many industrial applications.
2.2.2 Research programme year 3 to 6 (1998 - 2001)
During the course of Stage 1 we realised that the division of the work into the four areas was
not optimal and did not promote the cross-disciplinary work that we intended to carry out.
Researchers active in the different areas did not interact as efficiently as was intended. This
was also a comment from the international evaluators after Stage 1. Therefore, the centre was
reorganised before entering stage 2 into three programme areas based on the interests of the
participating companies. A brief description of the programmes is given below:
Programme A - Fatty acid based surfactants
The work within this programme was directed towards identifying and characterising new
fatty acids from natural sources. The organic chemists developed easy synthetic routes to
prepare the surfactants, which were characterised by the physical chemists. Special attention
was made to properties like foaming and emulsification, which are important in many of the
industrial applications.
Programme B - Polyhydroxyl surfactants
The objective of this programme was to find and explain the properties of surfactants where
the hydrophilic group is based on polyhydroxyl-containing compounds, like sugars, rather
than polyethers or charged groups. The objective in this programme was also to determine
interactions between polyhydroxyl based amphiphilic compounds and other surfactants or
polymers.
Programme C - Surfactants for life-sciences
Enzymes were used in this programme as catalysts in the synthesis of surfactants. The
objective was to prepare emulsifiers based on carbohydrates and fatty acids suitable for both
pharmaceutical and cosmetic preparations. Enzymes provided a way to carry out
regioselective synthesis of esters of polyhydroxyl substances.
2.2.3 Research programme year 7 to 11 (2002 - 2006)
The second reorganization occurred during Stage 3 and was inspired by the fact that SNAP
had worked very well. Many of our goals had been achieved so the next phase of our research
could be initiated. We felt that we had reached the level of understanding that allowed us to
emphasize properties of more complex systems such as surfactant mixtures and surfactantpolymer mixtures rather than the single surfactant systems that were the main focus
previously. This also had the advantage that we came one step closer to applications, since in
essentially all applications mixtures of surfactants (and polymers) are formulated together to
obtain optimum performance. It is in fact such formulations that need to be changed and
become more efficient and environmentally friendly in order to promote industrial
development and better products for consumers and the environment. In each programme we
16
had industries that are primarily raw material producers, surfactant manufactures and end
users of surfactants. Each programme also contained academic scientists devoted to surfactant
synthesis and characterisation. The programmes were thus cross-disciplinary in both the
industrial and the scientific dimension.
The two programmes were:
Programme I - industrial “hard” applications
Programme I was directed towards “hard” industrial applications such as hard surface
cleaning and detergency.
Programme II - biological “soft” applications
Programme II was dealing with “soft” applications such as pharmaceutical, cosmetic, and
food & feed related applications.
It should be emphasised that there were never any borders between the programmes and most
industries were active within more than one programme, and many of the research projects
were of interest to more than one programme.
3 Key values
There have been a vast number of publications produced as a result of SNAP activities. A
complete list is included in Appendix B. A total of 188 articles or book contributions has been
published or are in press. 42 of these articles were published during stage 1-2 and the rest
during stage 3 and 4. About 33 articles are co-authored by academic and industrial researchers
within SNAP.
A total of 148 staff members have been engaged in SNAP activities since the start of the
centre (Appendix C). The number increased from 42 from the start, obtained a maximum of
80 between 2001-2003 after which the number of active participants decreased somewhat.
The years 2001-2003 were the most active years in terms of number of participants, PhD
students, publications, examinations and international collaborations. The reason for this was
the examination of the first PhD students engaged from the start of the centre and the start of
new PhD projects.
There has been a total of 17 PhD examination and 3 LicD examinations (3 LicD continued for
a PhD). There are still 5 active PhD projects in the end of Stage 4, which will be completed
during 2007/2008:
- Fatty acid surface chemistry in non-aqueous solvent (Sarah Lundgren)
- Block copolymers as efficient boosters (Markus Nilsson)
- Mixed surfactant systems (Iruthayaraj Joseph)
- Topical formulation (Johanna Bender)
- Softeners (Hans Oskarsson, Akzo Nobel Industry PhD)
17
Table 4. SNAP key numbers
1995
1997
- 1998
2000
- 2001
2003
Participants
Industrial partners
9
9
9
Academic partners
4
4
4
Number of researchers active within the center
42
65
80
Industry employees active in centre activities
26
28
33
Number of PhD students:
6
12
16
Number of LicD-students
1
2
0
Number of diploma works
0
5
5
Number of Post-doc or other researchers on specific 5
2
7
projects
Examinations
Number of PhD-examinations
0
3
7
Number of LicD-examinations
0
2
2
Publications and Patents
Publications (see Appendix B)
8
34
80
Patent applications
0
0
4
Mobility between academia and industry
Number of industry employees that are involved in the 12
11
15
centre management, as project leaders, supervisors
Number of joint articles between industry and academia 3
10
9
Number of industry PhD or LicD
0
2
1
Number of PhD or LicD from SNAP that are employed by industry (Dec 2006)
Number of PhD or LicD from SNAP that are employed by former or current SNAP industries (Dec 2006)
Number of PhD or LicD that are employed by academia (Dec 2006)
International collaboration
Collaborations with foreign research groups*
5
18
17
Visiting scientists to the centre*
1
11
12
Members of the centre visiting foreign research groups* 1
7
7
*The given numbers indicates the number of most important collaborations and visits.
- 2004
2006
- 19952006
8
4
68
30
11
0
6
3
12
4
148
76
22
2
16
18
7
1
17
5
66
0
188
4
12
28
11
1
-
33
3
10
-
2
-
6
7
6
4
24
30
19
4 Standing of SNAP in an international and national context
4.1 Attractiveness of SNAP International collaboration
During the centre lifetime we have expanded our knowledge and collaboration with research
groups outside SNAP. The result of these collaborations included visiting scientists to our
centre, visits abroad by SNAP members, many joint publications, and invitations to
international conferences.
International projects that researchers in SNAP have been active in are:
– Marie Curie Research Training Network SOCON (Self-Organisation under
Confinement). This project contain some elements that build on the SNAP experience.
The network was started January 2004. Akzo Nobel Surface Chemistry R&D, Lund
University, and KTH participate in this network along with other research groups in
nine different European countries (www.mcrtn-socon.org).
18
– IENICA (Interactive European Network for Industrial Crops and their Applications
The coordinator in SNAP have been the Swedish national coordinator in this EU
funded project (www.ienica.net).
– COST-Chemistry program D 7 on "Molecular Recognition Chemistry". The main
contribution of the researches at organic chemistry KTH was in the field of polar
lipids. The work has been carried out in collaboration with the group of Pier Luigi
Luisi and Peter Walde at ETH in Zürich. The structures and surface properties of
liposomes from phosphatidyl nucleosides and peptides have been studied mainly by
NMR techniques in order to create a structural model of the liposome surface.
– Brite Euram project "Multifunctional systems for wood preservation based on solvents
derived from renewable resources resulting in water repellent wood". The use of
surfactants to formulate more environmentally friendly wood preservation systems
was investigated.
– EU-project, "New generation surfactants for the latex polymerization process and high
quality environmentally friendly coatings". Emulsion polymerization using alkyl
polyglucosides with large headgroups was studied.
– The EU-funded “European Network on Gemini Surfactants” 1997-2001.
During the last half of the centre life-time SNAP was becoming increasingly concerned with
more complex systems. Thus, our network in the area of polymer-surfactant interactions was
increased including research groups in Germany, Lithuania, Denmark, USA and Hungary.
This network now includes competence that spans from synthesis via bulk association to
association at interfaces, and these groups now collaborate in the EU-programme SOCON.
Besides of the cooperation within SNAP, the members of the centre also have ongoing
collaborations with scientists in the physics community. The common theme is the interest in
novel surfactant structures, their physical-chemical properties and their function in the various
applications. Examples of these kinds of collaborations are given below but the list is of
course far from complete.
– University of Aalborg, Denmark. Development of enzymes for synthesis of sugarbased surfactants.
– CEA, Service de Chimie Moleculaire, Saclay. Structural determination of surfactant
aggregates using small-angle neutron and X-ray scattering.
– Grenzflächenforschung, Berlin, Germany. Comparison of interfacial properties of
purified and commercial surfactants.
– Dr. Masakatsu Hato, National Institute of Materials and Chemical Research, Tsukuba,
Japan. Interfacial properties of glycolipids and sugar-based surfactants.
– Prof. Ronald Neuman, Auburn University, USA. Surface rheological properties of
sugar based surfactants
– The Biochemistry group at KTH has collaborated with Department of Chemistry,
McGill University, Canada to examine new types of solvents (ionic liquids) for use in
enzymatic synthesis. This collaboration has resulted in two joint publications.
– Surface Chemistry at KTH has characterised an enzymatically synthesised sugar ester
surfactant from Dr. Vulfson in Reading. This work resulted in one joint publication.
19
– In the area of physical-chemical characterization of alkyl glucosides the centre has
extensive collaboration with Prof. Eric Kaler at University of Delaware and Prof.
Reinhard Strey at University of Cologne.
– The PhD-student El Ouafi Alami spent a year (2001-2002) in Dr. Julian Eastoes group
at the University of Bristol, UK resulting in 4 joint publications.
– The PhD-student Maria Stjerndahl went to Akzo Nobel in Arnhem, the Netherlands, to
visit Kees van Ginkel who works with biodegradation tests.
– The PhD student Christy Whiddon visited Clifford A. Bunton at UC Santa Barbara
between January 2002-March 2002.
– Surface Chemistry/KTH had a guest researcher, Imre Varga from the Department of
Colloidal Chemistry, Lorand Eotvos University, Budapest Hungary. During April
2004. He is now in Stockholm for a 2 year post-doc period.
– Sven Sauer, ERASMUS-student från Stuttgart worked on the project "Synthesis of
surfactants based on hexoses and 12-OH-stearic acid" during five months (MaySeptember) 2004. Tessie Borg continued on the same project during two months Dec
2004-Feb 2005.
– Markus Nilsson at Lund University has much collaborations with Dpto.Quimica Fisica
Facultade de Quimicas Universidade de Vigo Lagoas-Marcosende s/n 36200 Vigo,
SPAIN.
– Prof. Ricardas Makuska, PhD-students and undergraduate students from Vilnius
University, Lithuania visited Surface Chemistry, KTH on several occasions and to
perform experiments. As a result Akzo Nobel and Unilever now have direct contacts
with this Lithuanian research group. Further the collaboration between KTH and
Vilnius University remain very active today.
– We have had extensive collaborations with a research group at the Australian National
University in Canberra. For example, the PhD-student Britta Folmer spent three
months with Prof. Stephen Hyde in 1999 investigating the structure of liquid
crystalline phases of sterol-based surfactants.
4.2 Visibility of SNAP
One of the most important channels to inform about the centre is through conference
participation and publications in books and journals. As can be seen from Appendix B, SNAP
personnel have contributed to a large number of articles. Some other measures to promote the
visibility of SNAP are briefly described below.
–
–
–
–
In 1998 SNAP organized a workshop in collaboration with YKI entitled
“Environmental Aspects of Surfactants” in Stockholm. This was a one-day workshop
providing information on the trends in surfactant development created by
environmental demands. There were 68 participants from 10 countries, mostly from
industry.
In August 2001 SNAP organised a PhD course concerned with various aspects of
surfactant chemistry. This course enhanced the visibility of SNAP in academia.
A brochure about the competence centre was made. The brochure has been handed out
to visitors to KTH and YKI and has also been exposed at exhibitions such as the
Competence Centre day on October 22, 2002 (over 360 visitors). During this day there
were three presentations from industrial researchers active in SNAP.
A poster about SNAP activities has been shown on different occasions, such as the
YKI member day 2003 at Norra Latin, Stockholm (60 participants from industry and
41 from YKI).
20
–
–
–
–
–
–
–
SNAP was also exposed in VINNOVAs news magazine “VINNOVA nytt” number 2,
2003. The competence centre was exposed as a good example of industry-academia
collaboration in the area of “green materials”.
A website has been created containing general information about the centre, links to
all partners, contact persons, meetings etc. It has been useful for exposing the centre as
evidenced from the number of PhD- and post-doc applications that the centre has got
from abroad.
The coordinators have presented SNAP at several conferences
Representatives from the Estonian government, including the minister of economy,
visited SNAP in May 2002 to discuss the competence centre idea in general and the
experiences gained within SNAP. We note that both academic and industrial partners
in SNAP attended the discussions.
The director of SNAP participated in a briefing held in April 2003 with
“Näringsutskottet”, a working group in the Swedish parliament, in order to describe
how a competence centre promotes collaboration between industry and academia.
Representatives from the Japanese government and the director for the Japanese
National Institute of Science and Technology Policy (NISTEP) visited SNAP on April
13, 2005 to discuss the centre and the experiences gained during the center life-time.
An article about SNAP has been published in Kemivärlden med Kemisk tidskrift,
number 10, 2005. The article reported some main results but also the significant
advantages for industry to participate in a competence centre such as SNAP.
4.3 The Competence Centre as a national asset. Core competences and critical
masses
As mentioned earlier the core competence within SNAP included deep knowledge in organic
chemistry, physical chemistry, surface chemistry as well as biochemistry. Besides this crossdisciplinary nature of the centre, it was also cross-technological since our industrial partners
included raw material producers, surfactant producers and end-users of surfactants. We
believe that this combination of broad cross-disciplinary and broad cross-technological
characters of the centre activities made us rather unique in the world. Most often, the majority
of work related to the establishment of structure-function relations with an emphasis on
environmental aspects was done by companies. In SNAP the industrial companies were
brought together with world-class academic researchers with the common aim of increasing
the use of naturally based surfactants. The number of publications presented in international
journals indicates that we, despite our limited size, have been able to cover this broad range of
topics without sacrificing the scientific quality of our research. This is possible since the
common theme in all applications is novel surfactants for more environmentally friendly
products and processes.
There are, of course, other research centres and universities with high competence in
surfactant systems and their application but in our opinion hardly any of them covers such a
broad area as SNAP did. This has indeed made SNAP a national asset when it comes to
exploring the properties and applications of the new generation environmentally friendly
surfactants.
4.4 The role and impact of the centre within the university
SNAP was hosted by the chemistry department at the Royal Institute of Technology (KTH). It
is one of nine competence centres at KTH funded by VINNOVA. The chemistry department
21
consists of seven divisions, of which two are involved in SNAP, i.e. organic chemistry and
surface chemistry. The director of SNAP, Prof. Per Claesson, is the head of surface chemistry
as well as the chemistry department. Prof. Peter Somfai, who is one of the heads of organic
chemistry is also the dean of the school of chemistry under which the chemistry department is
organised along with two other departments. The third academic partner from KTH is the
department of biochemistry within the school of biotechnology. Hence, SNAP has been an
integral part of the chemistry field at KTH.
Beside the academic institutions at KTH, SNAP also has partners from Lund University and
Chalmers University of Technology. This makes SNAP different from most other competence
centres. We have seen this as an advantage since we thereby have been able to include all
necessary expertise within the centre. This advantage has also been emphasised by the
industrial partners. However, a disadvantage is naturally that the distance between the
academic partners makes spontaneous meetings between researchers less frequent.
The Institute for Surface Chemistry (YKI), participates in SNAP as an academic partner. YKI
is an industrial research institute within applied surface and colloid chemistry and is located
on KTH campus. Since 2005 YKI is a member of the SP group (Swedish Technical Research
Institute). YKI and the division of surface chemistry are located in close vicinity to each other
and therefore by tradition have close and intimate contacts. However, SNAP has in many
ways deepened this collaboration. Since SNAP was started KTH and YKI have shared the
responsibility for the SNAP management in that the director of SNAP has been employed by
KTH whereas the co-ordinator has been employed by YKI.
The importance of SNAP for KTH was, and still is, large. New collaborations with industry
were started, and some of these continue even after the closing of SNAP. New academic
collaboration was initiated, and they formed the basis for the EU-project SOCON. Further, the
research findings have been incorporated in undergraduate courses and researchers use SNAP
findings in their lectures. For YKI, the involvement in SNAP has been of direct importance
for both marketing purposes but above all as a source for new ideas to solve industrially
related problems. The use of natural based products is of high priority for most companies and
several ideas that YKI use to attract customers can be related to SNAP findings.
4.5 Technical and scientific achievements
In this section we will describe some of the major results that has been obtained during the
centre lifetime.
Alkyl polyglucosides (APG)
The program leader Dr. Ingegärd Johansson at Akzo Nobel has coordinated the research on
alkyl polyglucosides. The main progress in this area lies in the increased general
understanding of the properties of alkyl glucosides as surfactants, and how to balance the
surfactant properties by the structure of the hydrophobic and hydrophilic unit. Thus, we now
have a much better understanding on the properties of alkyl glucoside micellar solutions, on
how to form microemulsions with alkyl glucosides and how to "tune" the surfactant films in
such systems. We also have a much broader knowledge on how sugar surfactants adsorbs on
liquid and solid surfaces, which will be further described below.
The results generated have inspired the search for novel surfactant structures. As a result some
new surfactants based on oligodextran units as the polar group was synthesized due to an
initiative of AstraZeneca. It was expected that the flexibility of the 1,6-bonds between the
22
carbohydrate units should give the surfactant the properties sought after. These surfactants
were tested in applications as well as being characterized from a fundamental point of view. It
was eventually found that the purity of this surfactant was not high enough to make a
thorough scientific investigation meaningful. The organic chemistry team at KTH has over the
years produced some novel surfactants having pH-sensitive groups incorporated in the sugar
units. The yield for the designed synthetic route is vastly better than previous reports in the
literature. These surfactants may have ionic or non-ionic character depending on the solution
pH. This, of course, will affect adsorption, micellar-size and cmc as well as surface forces,
and it opens up new possibilities to tune the interfacial properties with respect to applications.
Behaviour of sugar surfactants in solution
The characterization of phase diagrams and formulation of microemulsions has mainly been
performed by Olle Söderman’s research group in Lund. The first completed thesis in SNAP
(Frederik Nilsson, 1998) was about the physical-chemical characterisation of alkyl glucosides
with different hydrophobic chain lengths. The effect of chain length, stereochemistry of the
glucoside linkage (α or β) and degree of branching was investigated as well as
characterisation of the phases formed by the surfactants in aqueous solution. Major
advantages with sugar surfactant systems are that the phase behaviour is very insensitive to
temperature and to salt concentration. In addition alkyl glucosides are stable at alkaline pH,
which makes them ideal for the use under such conditions. The structure of the phases were
characterised by small angle x-ray scattering (SAXS) and nuclear magnetic resonance
(NMR). The characterisation of the sugar surfactant systems were continued in three PhD
projects (Christy Whiddon, Johan Reimer and Caroline Ericsson).
Christy Whiddons (PhD) thesis is about the phase behaviour and micellar structure in binary
alkyl glucoside/water systems. The phase behaviour can be controlled by varying the ratio
between the two surfactants. In particular she focused on the liquid-liquid phase separation
that occurs for some alkyl glycosides when the temperature is raised, with the goal to find the
underlying reason for the phase separation. By careful studies of micellar structure, using
several different techniques, she was able to show that the micelles in alkyl glucoside/water
systems are branched, forming a network, and she suggested that it is the problem of diluting
such a network that drives the phase separation. Of special interest was her finding that the
phase separation is markedly different in heavy water, as compared to ordinary water,
everything else being equal. She also presented some micellar kinetics work using alkyl
glucoside as surfactant. It has also been shown that a substitution of D2O for H2O causes a
large increase in micelle size. A possible explanation is that the size of the head group is
changed due to the exchange of O-H bonds for the shorter O-D bonds. This exchange may
result in a change of the spontaneous curvature of the surfactant aggregates and, as a
consequence, a change in the micellar size. This effect was also observed by Caroline
Ericsson (see below)
Johan Reimer (PhD) focused on the ability of alkyl glucosides to from microemulsions. Since
the alkyl glucosides are quite hydrophilic, and in contrast to ethylene oxide based non-ionic
surfactants cannot readily be tuned by changing the temperature, a co-surfactant was used to
tune the surfactant film. Reimer used octyl glucosides (C8G1) and octanol (C8E0) as cosurfactant and was able to formulate microemulsions containing equal amounts of water and
octane. The evolution of the microstructure as a function of water/oil ratio in the
microemulsions was investigated with NMR diffusometry. To further unravel the phase
behavior, Reimer determined the isothermal phase diagram of the three component
C8G1/water/octane system and discovered a liquid/liquid phase separation as octane is added
23
to a binary C8G1/water solution. This phase separation is related to the phase separation in the
binary system studied by Whiddon, but its cause is possibly different. Reimer was also able to
formulate three component microemulsions with some polar oils, such as methyl octanoate.
Caroline Ericsson (PhD) reports the effects of temperature, salt, concentration and deuterium
exchange on the self-aggregation of n-nonyl-β-D-glucoside (β-C9G1) and n-tetradecyl-β-Dmaltoside (β-C14G2). The data suggest that the surfactant aggregates grow in one dimension
upon increasing concentration, addition of salting-out salts, changes in temperature and a
substitution of D2O for H2O. However, the temperature effect on the micellar size is
dramatically different for the two alkylglycosides. For β-C9G1, a decrease in size is observed
with increasing temperature whereas the opposite is observed for β-C14G2, i.e. an increase in
micellar size with increasing temperature. The effects can be rationalised as effects on unimer
geometry, rather than on unimer solubility. At higher surfactant concentrations the
alkylmaltosides form entangled rod-like micelles whereas alkylglucosides have a stronger
tendency to form branched aggregates and micellar networks. The thermotropic phase
behaviour and phase structure of crystalline and non-crystalline alkylmaltosides as well as
crystalline n-dodecyl-β-D-glucoside (β-C12G1) was investigated. Two different non-crystalline
structures for the alkylmaltosides were identified, a gel and a glass. The gel was formed for
alkylmaltosides with a hydrocarbon chain longer than 12 carbons whereas short- and mediumchained alkylmaltosides formed a glass. The results highlight the importance of
intermolecular head-group interactions for the phase behaviour of alkylglycosides.
Vitaly Kocherbitov (PostDoc) investigated thermodynamic properties of binary sugar
surfactant/water systems using calorimetric techniques. In particular, he focused on the water
poor region of the alkyl glucoside/water system and the phase diagram of this region was
determined for several alkyl glucoside in great detail. In achieving this he used a novel
calorimetric technique, sorption calorimetry, which allows studies of concentration induced
phase transitions. This area of the phase diagram is relevant in many technical applications,
since water uptake in powders, pills etc. often occurs through humidity in air and such uptake
often influences the properties of the material. Of particular interest in this regard is his
characterization of glass transitions in alkyl maltosides, where he showed that these systems
form glasses that are partly ordered and have the same lamellar structure as the liquid crystals
formed by the two maltosides. In order to reflect the presence of glass transition and the state
of the alkyl chains, the terms “glassy crystals” and “glassy liquid crystals” was used to denote
these states.
The efficiency of sugar-based hydrotropes was also investigated within the framework of
SNAP. We have now a candidate compound that has been shown to be efficient in hardsurface cleaning formulations. The hydrotrope was synthesised in larger amount and
evaluated by Snowclean. It was shown that the hydrotrope was as efficient as the currently
used hydrotrope.
Adsorption of sugar based surfactants
The adsorption behaviour and the interfacial properties of alkyl glucosides at surfaces have
been studied mainly by the group of Per Claesson at KTH, by Krister Holmbergs group at
Chalmers and at YKI. In these studies pure surfactants, commercially available and specially
made by enzymatic synthesis, technical surfactant mixtures, as well as carbohydrate
functionalized alkylthiols attached to gold surfaces have been investigated and compared.
This allowed a determination of the relative importance of hydrogen bonds and van der Waals
forces for the short-range attraction observed between surfaces coated by carbohydrate
24
surfactants. The importance of polydispersity in the head-group region as well as the presence
of ionic impurities in technical mixtures has been demonstrated.
Mikael Kjellin (PhD) focused on adsorption of non-ionic sugar-based surfactants with the aim
of understanding the influence of surfactant structure on the surface properties. The effect of
size and flexibility of the sugar head-group was investigated. The project also clarified some
of the differences in behaviour between polyhydroxyl- and ethylene oxide-based surfactants.
The importance of hydrogen bonds between sugar surfactant head-groups for the interfacial
properties of alkylglucosides and intersurface forces between such layers have been of
concern for a rather long time. This question was analysed within this project and also by a
senior scientist (Eva Blomberg). The answer is that the interlayer adhesive interaction is
dominated by van der Waals forces rather than hydrogen bonds. However, the van der Waals
force is sensitive to the water content of the adsorbed layer, which in turn is determined by the
packing within the layer. One finding is that increased head-group flexibility increases
interlayer adhesion forces and the packing density within the layer. This can only be
rationalized provided intralayer hydrogen bonds are of some importance. Thus, hydrogen
bonds between head-groups do play a role in intersurface forces, but it is a second order
effect. Hence, the design rule for a good non-ionic surfactant dispersant is that the surfactant
head-group region should contain much water, thus reducing the van der Waals force. This
must, however, be achieved without significant decrease in the cohesive energy of the
adsorbed layer. In the same area Marcus Persson (PhD) investigated the effect of size of the
sugar head group on the adsorption on different types of hydrophobic surfaces. The
measurements were compared with commercially available technical mixtures and the
influence on small amounts of impurities was investigated.
Adsorption isotherms of several alkyl polyglucosides on TiO2 have been investigated by
Maria Mattson (PhD) with respect to changes in alkyl chain length and head group
polymerization. The adsorbed amount is mainly determined by the head group polymerization
and is largely independent of the alkyl chain length. The adsorption kinetics depends on the
concentration relative to the cmc. The adsorption behaviour on silica was also investigated.
Alkyl glucosides alone do not adsorb on silica, but addition of small amounts of a cationic
surfactant to the alkyl glucoside solution allows for adsorption on silica. A comparison
between the adsorption and bulk properties has shown that mixed micellization explains most,
but not all, effects of the coadsorption properties. Changing the pH in the mixed systems
reveals that a surfactant with a pH-dependent charge and the ability to adapt its charge to the
environment, e.g. a surface, enhances the adsorbed amount over a wider range of pH values
than a purely cationic surfactant.
Amine based surfactants synthesized from naturally occurring raw materials were
characterised by Hans Oskarsson (PhD). These were compared with amine surfactants based
on e.g. oxyethylene hydrophiles. The goal was to find environmental acceptable amine based
surfactants and find head-group structure activity relationships. The industrial use of amine
based surfactants can be found in a large number of applications such as antistatic agents for
softeners, collectors for mineral flotation, dispersants, rheology modifiers, bactericides and
cleaners. For the cationic surfactants there is a demand for finding compounds with decreased
toxicity and increased biodegradation. New legislations force the industry to show that the
products produced are readily biodegradable and that the aquatic toxicity is acceptable.
Surface plasmon resonance has been the main tool for the studies and adsorption to surfaces
that are well defined with regard to hydrophilicity and surface charge has been monitored.
25
Novel hydrophobic and hydrophilic structures
Within SNAP our efforts in using novel hydrophobes for surfactant synthesis and applications
have been coordinated by the program leaders Johan Berg (SLR), Christian von Corswant
(AstraZeneca) and Martin Svensson (Lantmännen). A large emphasis has been put on using
novel hydrophobic units from natural resources as building blocks for surfactants, and to
develop new efficient synthetic routes. Among the novel hydrophobic structures used are
sterols (from UPM-Kymmene), rosin acids (from Arizona), tall oil fatty acids (from Arizona),
and more exotic fatty acids e.g. crepenynic acid produced by crops grown by SLR. Academic
and industrial partners have used these building blocks to synthesize a range of surfactants
and have characterised these with various techniques. Sometimes these natural based
surfactants can have very beneficial properties. For instance, the large size and stiff structure
of the sterols give surfactants with special properties such as very good solubilizing
properties.
Björn Hedman (LicD) used tall oil dehydroabietic acid and tall oil fatty acid to synthesise
surfactants with poly(ethylene oxide) chains of various lengths. Particularly, the fatty acid
contain double bonds in the chain and can therefore be used to synthesise surfactants with one
polar group and two non-polar chains. The packing of these surfactants is vastly different
from surfactants with one hydrocarbon chain and their fundamental properties and usefulness
in applications was investigated. Sterol ethoxylates have been characterised by Britta Folmer
(PhD) who performed an extensive physico-chemical characterisation of β-sitosterol
ethoxylates with different degree of ethoxylation. A new class of heterogemini surfactants
comprising a non-ionic/non-ionic, non-ionic/anionic or a non-ionic/cationic head group was
synthesised and characterised by El-Ouafi Alami (PhD). These surfactants are based on the
nitrile of an unsaturated fatty acid (tall oil). The surfactants exhibit improved performance
over mixed systems of normal surfactants both in terms of micellisation and packing.
The adsorption of surfactants at interfaces can be affected by double bonds in the single
chained compounds. This was explored in the synthesis and charaterisation of fatty acid
monoethanolamide ethoxylates by Britta Folmer (PhD). The possibility of having double
bonds in the hydrophobic tail and the presence of the amide bond that is known to readily
participate in hydrogen bonding are the two characteristic features of this surfactant class.
Particular emphasis has been put on two items: (i) the effect on packing efficiency of the
location and type (cis or trans) double bonds in the chain; (ii) the role of the amide bond for
micelle formation and for adsorption at surfaces. For these types of surfactants, clear evidence
has been found that the amide bond indeed is beneficial for obtaining a high packing density
of the surfactant at interfaces.
Fredrik Viklund (PhD) within the research group of Karl Hult has developed an enzymatic
method for the production of ascorbyl esters with high yields, not only for saturated fatty
acids but also for unsaturated acids. The products have been characterized in a way that has
not been done earlier. A considerable effort has been put into increasing the yield of the
synthesis, which according to the literature still is a problem. It turned out that the
antioxidative properties of one of the compounds produced were superior compared with
ascorbylpalmitat, which is commonly used today.
The effect of the type of linkage between the hydrophilic and hydrophobic groups have been
investigated in several projects (Folmer, Kjellin, Stjerndahl). The different types are for
example ether, amide, ester, and carbonate linkages. Hydrophilicity increases in the order
carbonate < ether < ester < amide. The critical micelle concentration (cmc) and the area per
26
molecule in the adsorbed layer increases in the same order for similar types of molecular
structures.
Kristina Neimert-Andersson (PhD) at Organic chemistry synthesised (with high yields) a
range of isomeric sugar-based surfactants with the intended use for solubilisation of drugs.
Isomeric effects on interfacial properties at the air-water interface were also investigated. This
work constituted the most advanced synthesis work within SNAP.
Peter Piispanen (PhD) from the same group synthesised and characterised a large number of
new surfactants derived from natural products. Much of the characterisation work was
performed together with Mikael Kjellin (PhD) and Marcus Persson (PhD) at KTH. A number
of surfactants were synthesized from sugars and natural hydrophobic compounds. Different
monosaccharides were used for the hydrophilic moiety of the surfactants. The hydrophobic
moiety consisted of steroids, monoterpenes, rosin acids, fatty acids and long chain alkyl
groups, as well as aromatic compounds. The surfactant properties were compared with those
of common commercial surfactants. The aqueous solubility follows the general trend expected
from the HLB of the surfactant when considerations about the character of the head group and
the connecting unit are added. Some surfactants were able to form stable macroemulsions
between water and different oils. Surfactants with open sugar head groups, in contrast to
closed sugar head groups, were found to be better dispersion agents. Increasing the size of the
tail group, by using twin chain tail groups, increased the dispersion properties further. The
wetting properties of the sugar-based surfactants were generally found to be poor. Foaming
properties were low for surfactants with low aqueous solubility.
Solubilisation of drugs
In a joint project between an industrial partner and a PhD-student (Fredrik Viklund)
surfactants were prepared enzymatically with the aim of finding substances that had a high
solubilizing capacity for hydrophobic drugs, but no haemolytic effect. After several years of
frustration the problem was successfully solved and a patent was aquired. We would like to
emphasise that the long perspective of the competence centre was essential for solving this
problem. Another essential element was the trustful atmosphere between the industrial partner
and the academic partner that allowed non-successful attempts to be made before the
important break-through was made. Two post doc projects during Stage 4 (Per Thorén and
Cathy MacNamee) were devoted to explain why these types of surfactants have such nonhemolytic properties.
The aim of another PhD project (Caroline Ericsson) was to build an understanding of the
phase behaviour and micellisation of different alkylglycosides on a molecular level and to
pinpoint the effects of various hydrophobic solubilisates. The long-term objective was to
identify alkylglycoside systems suitable as solubilisers for industrial applications. Micellar
solubilisation of hydrophobic compounds in pharmaceutical applications is normally achieved
by means of non-ionic surfactants based on polyethyleneglycol (PEG). However, PEG has a
low chemical stability in water, which causes problems in terms of chemical degradation. The
degradation products are often toxic and can enhance degradation of unstable drug molecules.
Due to these drawbacks novel surfactants are highly relevant and alkylglycosides have a
number of characteristics that make them interesting in this respect. The solubilisation of
naphthylalkylates and the stabilisation of polypeptides by alkylglycosides were investigated.
The results reveal that the unimer geometry governs both the solubilising and stabilising
capacity.
27
Polar lipids
The work was carried out mainly by Jan Holmbäck (PhD), the department of organic
chemistry and Scotia LipidTeknik AB. The structures of naturally occurring polar lipids was
characterised by combinations of nuclear magnetic resonance (NMR) and mass spectroscopy
(MS). In particular it was found that the use of advanced NMR methodology, e.g. high field
NMR spectrometers in combination with 2D techniques, was very fruitful. It was found to be
important to take into account the effect of solvent, temperature and lipid concentration on the
chemical shift. The work culminated with the identification of novel lipid structures in oats.
Thoretical calculations and Surfactant-surfactant synergies
The synergistic reduction in the critical micelle concentration between different surfactants
has been investigated theoretically by Magnus Bergström (senior scientist). The predictions of
the theroretical models have been verified by experimental work carried out by both PhD and
diploma students. Thus, we have developed the means to predict synergism, beyond the
regular solution model. A key finding is that the entropy of mixing large and small headgroups contributes significantly to a favourable synergy. Magnus Bergström also derived
theoretical expressions for the spontaneous curvature, mean and gaussian bending constants
of surfactant monolayers and bilayers. Further studies included thermodynamic calculations
of the influence of curvature free energy on the micellar size and shape for anisotropic
surfactant micelles
Pernilla Liljekvist (LicD) compared the synergistic behaviour between non-ionic alkyl
polyglycoside, ethyleneoxide-based surfactants and an anionic surfactant in mixed micelle
systems. Synergistic effects with the anionic surfactant were more pronounced for mixtures
containing the ethyleneoxide-based surfactant than for mixtures containing the glucosidebased surfactant. The interaction between the mixed micelles and a hydrophilic polymer was
also studied.
Surfactants-polymer interactions
The effect of different surfactants on adsorbed mucin layers were investigated in a
collaborative work between an industrial researcher (Andra Dédinaité) and a PhD-student
(Luis Bastardo). A significant part of the work was carried out by the industrial researcher at
the company premises. The industrial researcher also visited the academic partner to use their
facilities during two periods, each of three months duration. The driving force for this project
was the need to find milder surfactants in oral care formulations. It was found that surfactants
could remove mucin from solid surfaces by two mechanisms. The first mechanism involves
simply competitive adsorption. The second mechanism is due to association between the
mucin layer and the surfactant. The mucin-surfactant complex formed has in some cases a
lower affinity for the surface than mucin alone and the complex desorbs. Interestingly, it was
found that sugar-based surfactants left mucin layers adsorbed to hydrophilic surfaces intact,
and thus none of the two displacement mechanisms were operative. One design rule for a
surfactant that should leave the protective mucin layer intact is thus clarified. It should not
associate with the mucin and it should not adsorb to the substrate surface.
Some studies of how the presence of non-ionic polyhydroxy surfactants affect the structures
formed between polyelectrolytes and oppositely charged surfactants have also been carried
out. In the particular case investigated the polyelectrolyte and the anionic surfactant was
found to form aggregates with an internal hexagonal structure composed of cylindrical
micelles bound together by polyelectrolytes. The presence of the non-ionic surfactant was
found to, depending on the structure of the non-ionic surfactant, either increase or decrease
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the size of the repeat unit. One may thus use non-ionic surfactants of the polyol-class to
modify the internal structure of polyelectrolyte-surfactant complexes. This, in turn, will
change their properties, e.g. their solubilising capacity.
Block copolymers as efficiency boosters
The aim of this (still on-going) project at Lund University (Marcus Nilsson, PhD) is to study
the interaction of alkylglucoside based microemulsions and polymers, essentially block copolymers. One of the things that are investigated is how the block copolymers can replace
surfactants in microemulsion and act as a “booster”. The idea is to replace surfactant (in a
microemulsion) by small addition of block copolymers and see if there is an enhancement in
solubiliztion capacity of oil and water. As a model system a balanced bicontinuous
microemulsion based on a system of alkylglucoside surfactant is used. This enables us to see
the swelling effect on both the excess phase of water and oil. Several different sugar
surfactant and oil systems have been characterised. The ultimate goal is to find a polymer that
interacts with the microemulsion and gives an enhanced solubilisation capacity of oil and
water. This is important to the industry because the amount of surfactant can be decreased and
replaced by a smaller amount of polymer. This is beneficial from both an economical and
environmentally point of view since the use of less surfactant will be cheaper and less
damaging to the environment. Current studies that are performed in this area include
interactions between cyclodextrins, cationic single chain, gemini, bolaform and sugar based
surfactants, and also the influence of polydispersity on the temperature induced micellization
process for a poly(oxyethylene)-poly(oxypropylene)-poly(oxyethylene) triblock copolymer.
Cleavable surfactants
Surfactants with built-in weak bonds, so-called cleavable surfactants, are interesting
candidates in the search for more environmentally friendly alternatives to traditional
surfactants. The objective of this PhD-project (Maria Stjerndahl) was to perform a systematic
study in which cleavable surfactants with different hydrolyzable bonds were compared with
regard to physicochemical properties, and chemical and biological stability. Nonionic
surfactants where the head group and the tail are linked by an ester, an amide or a carbonate
bond were prepared and characterized. The stability was investigated by subjecting the
surfactants to base-catalyzed hydrolysis, enzyme-catalyzed hydrolysis and biodegradation.
The effect of steric hindrance near the hydrolyzable bond on the surfactant stability was also
investigated. A series of surfactants with different degree of substitution at the α-carbon of
the hydrophobic chain were prepared and compared. Physicochemical properties, such as
critical micelle concentration (CMC) and cloud point, showed that the carbonate group and
the ester group are more hydrophobic than the amide group. It was found that the ester bond
was more labile than a carbonate with respect to base-catalyzed hydrolysis, while the amide
was virtually stable. The surfactants showed a pronounced difference in stability with respect
to the type of substitution in the vicinity of the hydrolyzable bond. Hydrolysis studies above
the CMC revealed that the ester bond of aggregated surfactant is protected from attack by
hydroxide ions. Biodegradation tests showed that all three types of hydrolyzable bonds give
surfactants that fulfil the main criterion for being classified as readily biodegradable.
Furthermore, mixed surfactant systems containing cleavable surfactants were investigated. It
was shown that it is possible to govern the hydrolysis rate of a hydrolyzable surfactant by the
addition of a second surfactant species.
Biopolymers food emulsifiers
Isabel Mira (PhD) investigated the rheological properties of food and non-food grade
emulsifiers and common biopolymers present in cereal based products. The aim is to find
29
combinations that exhibit a rheological behaviour valuable in the processing of cereal-based
products. The onset of the temperature-induced pasting of starch in aqueous suspensions, as
well as the rheological behaviour of the resulting pastes and gels, are properties of importance
for the processing and the final quality of cereal-based products. Additives like lipids and
emulsifiers have proved to exert an important influence on these properties. Starch is a
mixture of two polysaccharides, amylose (AM) and amylopectin, which occurs naturally in
the form of microscopic granules that are abundantly found in tubers, roots, cereal grains and
fruits. In order to bring out their functional properties as thickeners and texture enhancers,
starch granules are often disrupted by heating in excess water. This process, which is referred
to as gelatinisation, causes the granules to swell and exude a fraction of the starch
polysaccharides, resulting in a dramatic increase in the viscosity of the starch suspension.
Surfactants are known to affect the different aspects of the gelatinisation process and, in
particular, the swelling properties of starch. Surfactants are also known to form helical
inclusion complexes with AM, the formation of which plays an important role in many of the
instances in which starch and surfactants interact. This work was carried out in order to gain
insight into how the surfactant structure (head group and chain length) influences the swelling
properties of starch and the molecular mechanisms behind these effects. The investigations
involved the study of the temperature-induced gelatinisation of starch in the presence of
surfactants as well as studies on the association of surfactants to AM in solution and the
solubility of the resulting AM-surfactant complexes. With the exception of the cationic
surfactants (alkyl trimethyl ammonium bromides), short-chain (C10, C12) surfactants induce an
early swelling (swelling at lower temperatures than the control sample) in normal wheat
starch granules, whereas their longer chain counterparts (C14, C16) have the opposite effect.
Contrary to this finding, the effect of surfactants on the swelling of waxy wheat starch
granules, an AM-free starch variety, is not influenced by the surfactant chain length but by the
head group charge of the surfactant.
Topical formulations
The aim of the project performed at Chalmers (Johanna Bender, PhD) is to get new
knowledge about the importance of the physical state of the lipid-based formulations, how
lipid-based formulations interact with cosmetic (UV-absorbers) or pharmaceutical (anticancer drugs) agents and how the formulations interact with skin and the skin lipids. The
results from this project will hopefully be used for formulators in the cosmetic and
pharmaceutical industry who work with skin formulations based on lipids from vegetable
sources.
For the in vitro diffusion studies, passive diffusion and iontophoresis (electrically driven
transport) over porcine ear skin are used to evaluate how different formulations containing
ALA or m-ALA affect the permeability of the skin. Phase behaviour of the formulations is
studied by visual inspection (polarised light), small angle X-ray scattering/diffraction
(SAXS/SAXD) and NMR diffusometry. By changing the lipophilicity of the active agent and
the formulation in a consequent way and make diffusion series of the samples, it is possible to
receive information about how the lipophilicity of the active agent affects the skin
penetration. Changing the internal structure of the formulation (for example a microemulsion
going from W/O, to bicontinuous, to O/W) gives information about how the internal structure
affects the skin or membrane penetration. It has been found that certain cubic phases offer
increased penetration rates for drugs used in the treatment of skin cancer. This enables the
treatment of deeper lying cancer in the skin. The rheological properties of the formulation also
facilitate the treatment on particularly difficult areas on the body, such as in the face.
Moreover, the lipid system was stable toward degradation caused by acidic drugs. Additional
30
support for this project was applied and granted by VINNOVA and the ideas are now ready to
be patented.
Blending nonpolar and polar liquids
This was the last PhD project (Angelica Hull) initiated within SNAP. The Kyoto Protocol and
the actions of nations concerned to protect the environment have lead to an increasingly
important role for bio-based motor fuels in the world economy. So far we have succeeded in
producing a variety of gasoline and diesel biofuels, which meet all the requirements of
standard fuels in standard engines. By a careful study of the physical chemical properties of
oxygenated biofuels and their effect on performance we have aimed at improving the existing
formulations further. The experimental work has consisted of measurements of the vapour
pressure, chemical activities and phase compositions directly using gas chromatography and
of the phase behaviour using optical density. The experiments are performed on 2, 3, and 4
component mixtures of apolar and polar liquids. A demand for these alternative fuels was that
it should be possible to use them in all existing gasoline and diesel engines respectively.
These objectives have been fulfilled. The new fuels consist of 15% renewable oxygenates and
can be used in conventional engines. By using these fuels the net emission of carbon dioxide
can be reduced by more than 15%. The biodiesel fuel is available on the market through the
company Agrofuel.
Fatty acid surface chemistry in non-aqueous solvent
The aim of this PhD project (Sarah Lundgren) is to explore the use of fatty acids as
lubricating additives in nonaqueous solutions and to improve the basic understanding of the
adsorption of fatty acids. The association and aggregation of fatty acids in nonaqueous
solutions has been examined as well as the interaction of the fatty acids with metal surfaces.
Some parameters that have been studied are the following: i) Type of fatty acid and fatty acid
blends, ii) Influence of the type of nonaqueous solvent, iii) Interaction with other amphiphilic
compounds and iv) Effect of temperature and co-solvents such as water. Model systems for
diesel fuels are used in this project but the results can be of use for other applications where
lubrication of metal surfaces is important. This is an ongoing project scheduled to be finished
in the end of 2007.
Particulate soil removal
In two PhD-projects completed in 2002 (Mikael Kjellin and Marcus Persson), the relation
between adsorption at interfaces and changes in surface interactions, particularly adhesion
forces, was emphasised. The knowledge and understanding obtained was later used for
solving problems with particulate soil removal using surfactant mixtures and mixtures of
surfactants and polymers. The studies were carried out by measuring detachment forces. The
procedure is as follows: First, the surfaces are brought in contact in air, and then a surfactant
solution is allowed to enter around the contact region. Finally, the surfaces are separated and
the liquid is allowed to enter between the surfaces. The force needed to separate the surfaces
is the detachment force. This experimental protocol, which has not been used previously,
mimics the situation when a particulate soil is attached to a surface in air and then it is
attempted to remove it in a liquid cleaning formulation. The detachment force is significantly
larger than the adhesion force between the surfaces in the liquid. The reason for this is that the
adhesion force is measured between pre-wetted surfactant loaded contacts whereas the
detachment force is measured between dry contacts free of surfactants. The detachment force
is significantly smaller than the adhesion force between the surfaces in air, which is due to the
surface pressure of the surfactant film adsorbed outside the contact area. We argue that the
detachment force is the relevant force in relation to removal of particulate soils and we mean
31
that the fundamental studies carried out within SNAP will aid the development of better
cleaning formulations. In fact, some improvements in such formulations have already been
achieved. The work has resulted in one patent.
Addition of polymer to the surfactant systems sometimes generates lower detachment forces,
i.e. improves cleaning efficiency. This effect has been studied in two PhD projects (Luis
Bastardo and Iruthayaraj Joseph) and one post doc project (Evgeni Poptoshev).
4.6 “Success stories”
Some examples of break-throughs that have occurred are highlighted below.
Particle removal: We have developed a novel scheme for carrying out surface force
measurements with the aim of measuring detachment forces, i.e. the force needed to remove
particles adsorbed to a surface from air and removed from the surface in a surfactant solution.
The effect of the nature of the polar head-group and branching of the non-polar part of the
surfactant has been investigated. The data obtained has been validated using industrial tests
and it has been of use for development of new cleaning formulations. The methodological
development is a real break-through since it has been very difficult to find other model test
methods that correlate well with the real industrial situation. The studies have highlighted the
complexity of the cleaning process and the balance between the force required to remove a
particle from a surface and the forces required to prevent particle redeposition. Careful studies
of the relation between the adsorbed amount of surfactant and detachment force have been
performed, which have given us further insight into the detachment process. One patent has
been filed.
Particle dispersability and prevention of particle redeposition: Design rules for good
dispersing agents and anti-redeposition agents have been achieved. The surfactants should,
naturally, adsorb to the particle surface and expose the polar part towards solution. Further,
the cohesive forces within the layers should be large, the intralayer surface pressure should be
large, and the water content in the surfactant head-group region should be large.
Mildness towards mucus coatings. Mucin is the main component of protective mucus layers
on many internal bodily surfaces. Two surfactant-induced mechanisms that disrupt the mucin
coatings have been found. Surfactants that should be mild to the protective coating should not
associate with the mucin and it should not adsorb to the underlying substrate surface.
Non-hemolytic surfactants. Surfactants are commonly used as solubilising agents for nonpolar drugs. In such applications the surfactant should have a high solubilising capacity and
be non-hemolytic. To our knowledge no surfactants that have both these properties have
previously been available. A novel set of surfactants, prepared enzymatically within a SNAP
project, fulfils both these criteria. Much work during stage 4 has been devoted to
understanding the reasons behind this effect. We could not observe any relation between the
physicochemical behaviour with the non-haemolytic/haemolytic effects and the surfactants
behaved much like ordinary surfactants. Specific biological effects may therefore be the cause
for these effects. However, leakage studies of calcein from vesicles after surfactant addition
correlates with the haemolytic effect in that much higher leakage is observed for the more
haemolytic surfactants. The leakage method can therefore be used a an initial stage instead of
real animal trials. Two patents have been filed in this area.
32
Novel hydrotropes: In a collaboration project between Akzo Nobel, Snowclean, YKI and
KTH a new sugar-based hydrotrope has been developed. This hydrotrope has been proven to
have beneficial properties in hard-surface cleaning application. The hydrotrope was
synthesised in larger amount and evaluated by Snowclean. It was shown that the hydrotrope
was as efficient as the currently used hydrotrope.
New products for oilfield applications: Akzo Nobel states that the increased knowledge
about cleaning mechanisms will lead to future increased sales of surfactants in cleaning
formulations. Via a former PhD-student, Frederik Nilsson, Akzo Nobels knowledge of
glucosides has lead to development of a new product, which is now being sold to an oilfield
application.
New methodology for studying hemolytic activity: A method to test the hemolytic activity
of surfactants has been developed within SNAP. This method has been shown to be of great
value also for testing the hemolytic activity of new drug substances.
Enzymatic synthesis: Within SNAP the research group of Karl Hult has developed an
enzymatic method for the production of ascorbyl esters with high yields, not only for
saturated fatty acids but also for unsaturated acids. The products have been characterized in a
way that has not been done earlier. A considerable effort has been put into increasing the
yield of the synthesis, which according to the literature still is a problem. It turned out that the
antioxidative properties of one of the compounds produced were superior compared with
ascorbylpalmitat, which is commonly used today.
Polymers as “boosting” agents: The use of polymers as additives (“boosters”) to
microemulsions in order to be able to use lower amounts of surfactants has been explored.
This is beneficial since the polymers are less aggressive to the environment than surfactants.
The work has given insight into the relation between polymer structure and “boosting” effect.
This knowledge is used in the development work at Akzo Nobel Surface Chemistry.
Environmentally friendly diesel and gasoline: Developing alternative fuels for standard
diesel and gasoline engines is of importance for the society. The basic strategy has been to
introduce oxygenates into the fuel compositions. A demand for these alternative fuels is that it
should be possible to use them in all existing gasoline and diesel engines respectively. These
objectives have been fulfilled. The new fuels consist of 15% renewable oxygenates and can be
used in conventional engines. By using these fuels the net emission of carbon dioxide can be
reduced by more than 15%. The biodiesel fuel is available on the market through the company
Agrofuel (a company within Lantmännen) since September 23rd 2006.
New delivery systems for treatment of skin cancer: Johanna Bender discovered in her PhDwork that certain cubic phases offer increased penetration rates for drugs used in the treatment
of skin cancer. This enables the treatment of deeper lying cancer in the skin. The rheological
properties of the formulation also facilitate the treatment on particularly difficult areas on the
body, such as in the face. Moreover, the lipid system was stable toward degradation caused by
acidic drugs. Further support for this project was applied and granted by VINNOVA and the
ideas are now ready to be patented.
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5 Benefits Technology transfer. Impact on the Partners
5.1 Partner involvement and interaction
There was a substantial industrial involvement in the SNAP activities. This was ensured by
the management structure and the design of the PhD-projects. Given below are some points
that show the width of the industrial involvement.
1) The industrial programme leaders had a central role in the SNAP activities as
described previously. This ensures a high involvement of the industries where the
programme leaders are employed (Akzo Nobel, AstraZeneca and Lantmännen). The
programme meetings have been held at the different industrial sites, and they often
included a site visit.
2) All the industrial partners have taken an active part in the work concerning the
development of SNAP after stage 4, either by giving input to surveys or actively
participating in the work-group assigned by the board. The board of SNAP has
consisted of members from four different companies. The board meetings took place
at the different industrial sites.
3) The in-kind contribution from the industries has been large. This contribution includes
all work with SNAP activities such as participating in meetings, performing in-house
experiments and collaborations within the ongoing projects.
4) 33 joint articles between academia and industry have been published.
5) Every PhD project or other project has been of particular interest to at least one, often
several, member companies. There were numerous informal meetings taking place
between the PhD student, researchers and the particular industries.
6) The programme leaders have made several visits to LU, KTH and Chalmers to discuss
the SNAP projects.
7) PhD students have performed numerous research visits to the industry.
8) There have been several visits by industrial partners to the academic partners. For
example, senior scientists and post docs from Unilever have come to perform
measurements at KTH and YKI. In particular, one person from Unilever has done
research at KTH during two periods of a total 6 months.
9) As part of the in-kind contribution from Akzo Nobel Surface Chemistry, Hans
Oskarsson who is employed by the company was doing his PhD within SNAP (at
Chalmers University of Technology).
10) A PhD-student from Lund University, Caroline Ericsson, did most of her lab work at
AstraZeneca in Lund. The industrial interaction within her project was thus large.
5.2 Centre mechanisms and ways of working in order to facilitate industrial
implementation
The way that the centre works and how this facilitates industrial implementation has been
described earlier in this report. For example the reorganisation of the centre activities into two
programmes during stage 3 and 4 focused on the industrial applications of the surfactants
clearly helps industrial implementation. In the final years of SNAP, the PhD projects as well
as the shorter projects were more targeted towards applications than before. The industry has
taken a more active part during the initial stages of the projects and no new projects were
approved unless there was a clear industrial interest in the project, which means that an
application is targeted. The progress of the projects was continuously presented during
follow-up meetings and also at the annual meeting and the programme meetings. An essential
part for the industrial implementation was to examine how the results and conclusions from
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the fundamental research projects can be applied to "real" industrial situations. Such a
validation process was therefore an important part of most research performed in joint
academia-industry projects within SNAP.
Advantages of performing long-term research, as done in SNAP, can be exemplified by the
PhD project of Fredrik Viklund. The initial goal of the project was to perform enzyme
catalysed synthesis of sugar surfactants. It was early shown that this could not be done as
easily as proposed due to the different natures (immiscibility) of the hydrophobic and
hydrophlic parts of the surfactant and the enzyme. However, after much persistent work
Fredrik succeeded with the synthesis and this resulted in a patent. He also showed that the
enzymatic synthesis could be efficiently done using new types of solvents (ionic liquids). This
is a clear example of how long-term research can solve difficult problems.
5.3 Commercialization and technology transfer
Below follows a brief description of the policy and rules applied in SNAP concerning IPRissues. Before any of the project results is made public knowledge the researchers provides
the industrial partners the opportunity to examine the results for a period of 1 month. The
industrial partners then have the right to delay the publication for another three month if they
find that the results may be worth protecting. If not, the researcher retains the ownership of
the results and all intellectual property. According to the IPR-agreement, only one industrial
partner in SNAP should be the sole owner of a patent. However, all other industrial partners
have the right for an irrevocable and non-exclusive licence to use the patentable invention.
The licence shall be free of charge except when used in the acquirers’ business area. The
industrial partner acquiring the patent, as well as any possible licensee, compensates the
research institute with a maximum of 150 000 SEK, except if the invention is of considerable
commercial success when a higher amount can be negotiated. The institute then compensates
the researcher in accordance to their separate agreements. The acquirer and the licensee
should also share all costs in connection with the patent.
There has been four SNAP related patents or patent applications.
1) One patent is about the use of ethoxylated phytosterols and phytostanols as nonhemolytic solubilisers for drug compounds.
2) The former PhD-student Peter Piispanen synthesised an amine-based sugar surfactant,
which was judged to be an interesting candidate for a patent. The PhD thesis defence
was delayed for a couple of months for this reason. Unfortunately, it was eventually
found out that the surfactant had already been synthesised.
3) The former PhD-student Fredrik Viklund has synthesised a new surfactant through an
enzymatic reaction. This surfactant is an excellent solubiliser and much less hemolytic
than the common surfactants of today.
4) In a collaboration inspired by SNAP, a patent was filed on additives for cleaning
formulations.
We note that the SNAP projects also serve to inspire industrial cooperation outside the SNAP
framework. One example is collaboration between Akzo Nobel and Unilever concerning
hetero-gemini surfactants that started with a SNAP PhD project. Another example is
ethoxylation of sito-sterols, where the industrial process was developed by Akzo Nobel. This
later led to a cooperation between UPM Kymmene and Akzo Nobel.
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5.4 Impact on the partners and their R&D-performance
Below follows new and old comments from the industrial members in SNAP.
Akzo Nobel Surface Chemistry
Our own R&D resources for long term research have decreased and the extended resources
that we have within the centre become more and more important for our long-term
understanding of surfactant systems. The annual meetings, project meetings, discussions, etc
serve as a continuous education. As a specific example taken from a project outside the
centre: We used the QCM equipment at KTH/YKI to confirm and understand certain
adsorption effects. Without the Centre this technique would hardly have been known to us.
The work meant a deeper understanding in that context and also the introduction of QCM to
the customer in question, thus increasing our image as a competent cooperation partner. The
general trend when it comes to development of new products today is to form partnerships
between producer and customer and get the benefit of combined forces. To some extent the
centre is our extended competence source to put into partnerships like this.
For us the most important part of the SNAP research concerned the alkyl glucosides. Akzo
Nobel has developed a set of low-foaming alkyl glucosides that we sell as hydrotropes and
wetting agents in alkaline or high electrolyte applications. One of the big areas there was
supposed to be the agro applications where the role of the glucosides as secondary surfactant
was obvious. However, with all tests and permissions that were needed it has taken far more
time than we expected. But now, when the wind towards more environmentally friendly
product has grown stronger the sales are beginning to take off. Our basic knowledge in this
field was inspired and partly built on the SNAP competence centre work.
We now take part in an EU-programme which is abbreviated SOCON (Self-organization
under Confinement ) where we are the only industry among a huge group of networking
academics all over Europe. Hopefully this will be a fruitful cooperation as well. The reason
for being there was the contacts that were established within SNAP.
It is difficult to estimate all the spin-offs that have emerged during the years, but without the
centre we would certainly not have worked in the same way as we do today. And we think
this way is better in line with what our customers expect from us. Partly resulting from SNAP
involvement there is an increased interest from Akzo’s Feed Additives business on natural
emulsifiers from oat oil.
Akzo Nobel Surface Chemistry has had great help from SNAP in improving the sales of our
sugar based surfactant and formulations based on it by the improved knowledge from SNAP.
We have also strengthened our business relations with some of the other participating
companies within SNAP, which will lead to increased business for the future.
Our sugar based surfactants, the APG’s which were studied very carefully within the SNAP
program, are now showing a great interest in the market place in our applications hard surface
cleaning, agrochemicals and petrochemicals and our sales are steadily growing. We have also
used knowledge developed within SNAP when we have been able to successfully exchange
our best selling degreaser formulation for hard surface cleaning with an equivalently efficient
readily biodegradable degreaser formulation. This development was necessary in order to
comply with the new detergent regulation.
36
SNAP has been a very successful competence centre with excellent management and good
cooperation between academia and industry. The concept of developing surfactants based on
natural products was very much before its time but we see now that 10 years after start, there
is a very much different opinion in the marketplace. The work done within SNAP has, in the
eyes of Akzo Nobel Surfactants, been very important for the understanding and development
of new classes of surfactants.
Arizona Chemical
A few years ago Arizona Chemical in Europe made a change in its strategy towards the way it
ran its long-term projects and fundamental development work. The company’s internal
technical resources are now focused on short-term commercialisation projects designed to
impact the business in the near and medium term. The longer-term development projects and
development of our fundamental technical knowledge, which underpins our ability to be
highly effective in implementation of the short term commercialisation projects are now
handled externally. These projects are handled through several routes including collaborative
projects and direct finding of PhD students at universities. The SNAP programme is ideal to
complement the internal programmes.
We are currently actively involved in a PhD student project (by Sarah Lundgren). The project
is designed to build our fundamental knowledge in terms of the mechanics of film formation
and the factors which control this process. This information will provide a sound scientific
understanding from which the chemist can develop the next generation of various types of
surface-active chemicals. These new surface-active chemicals will be used in applications
such as lubrication additives and corrosion prevention.
AstraZeneca
The activities within SNAP have provided us with a wealth of data on the physicochemical
and biological characteristics of novel surfactants, primarily such based on carbohydrates. The
results have laid a solid foundation on which future developments can be built. In a sense, the
work within SNAP can be described as a very thorough concept test of novel surfactant
technology, and the outcome of the test is positive. We now know that sugar-based surfactants
deliver substantial benefits over conventional technology in selected pharmaceutical
applications, and it is our intention to build on the concept and exploit the advantages (see
below).
In more general terms, the work within SNAP, and the interaction between academics and
representatives for various industries within the centre, have had a direct positive impact on
the R&D process.
• Establishment of lasting links and collaboration with Academia.
• Input of fresh ideas from Industries operating in other business fields. Such input
counteracts “tunnel-vision” and generates new ideas and opportunities in the R&D process. A
pertinent example would be systems designed to minimize the required amount of detergent in
a given application. Development of such systems has mainly been driven by the detergent
industry, but similar systems may be used in pharmaceutics in order to minimize the amount
of surfactant in a formulation (surfactants act as irritants on mucosa and there is therefore a
strong impetus behind efforts to minimize the surfactant concentration). Consequently,
concepts and know-how generated in the detergent industry have proved transferable to
pharmaceutics and the competence centre has acted as an efficient medium in this transfer.
37
• Since they have been studying novel phenomena and systems, the PhD students that have
worked in our labs have help us improve the scope and applicability of our existing
equipment.
• The PhD students have help us identify, evaluate and implement techniques to characterize
surfactant systems. This is particularly true for scattering techniques, such as static and
dynamic light scattering, and small-angle neutron scattering (SANS).
AstraZenecas expectations on the centre have thus been fulfilled and even surpassed. To a
significant extent, this positive outcome is attributable to the efficient management of the
centre. We would therefore like to extend out gratitude to those in charge of the
administration and thank them for their hard work over the years.
The work conducted within SNAP has provided us with a good understanding of the
relationships between surfactant structure and function, particularly those pertaining to
pharmaceutical applications. This understanding is currently fed into a project devoted to
enzymatic synthesis of alkylglycosides tailor-made for pharmaceutics. This project is
conducted within the research programme Greenchem, funded by Mistra.
Karlshamns
The collaboration in SNAP has resulted in an extended network within the field of applied
surface chemistry and has helped us in evaluating several interesting and commercially
important product ideas. Our participation has been focussed on life science applications
(food, cosmetics & pharmaceutical excipients). The work in enzymatic synthesis of
surfactants and excipients, as well as functional ingredients like surface-active antioxidants
and sterol esters, shows promise for the future. A conservative estimate of the potential sales
of products developed by Karlshamns in this context amount to 0,5-3 MEuro annually, if fully
and successfully commercialised.
Svenska Lantmännen
SNAP has been a tool for Lantmännen to develop a long-term relationship with YKI and
KTH. Before 1995 Lantmännen had very little contact with YKI. Since 1998 the group have
recruited 3 senior scientists from YKI.
Lantmännen's interest in SNAP has varied during the period. Initially we studied the
possibilities of using various fatty acids, in particularly candidates for transgenic crop
development, as hydrophobic material in surfactants. SNAP assistance was also essential
when we evaluated the potential use of oat oil extracted emulsifiers. The SNAP results
helped us decide whether or not to pursue a patent applications in this field.
Lately we have changed interest to a better understanding of how the surface active agents
that are used in cereal-based food can further improve our products. The study of emulsifierstarch interactions in a PhD project have enabled the producer of baking products to put more
relevant questions to their suppliers of emulsifier and it will hopefully lead to improved
products. The new understanding on the effect of molecular structure of the emulsifiers on the
pasting behaviour of flour has been reported to the marketing and development managers in
the baking section of Lantmännen.
Besides the engagement in SNAP, Lantmännen and YKI has during the period collaborated in
a EU-funded project on biofuels. This project was completed within SNAP during 20052006.In this project it has been possible to pursue our interest in the blending of renewable
components from biomass into petroleum fuels. Thus, finding practically applicable strategies
to achieve the blending of nonpolar and polar liquids is a key technology for the development
38
of this type of now bio-blend fuels. This has been the main subject of the latest project in
SNAP.
Thanks to SNAP we now feel that we have a strong network in surfactant chemistry both with
academia and industry.
Snowclean
As a formulator it is important to create a good knowledge of different surfactants. We do this
through raw material suppliers and our own knowledge in formulation and testing. SNAP has
contributed to a better understanding of surfactant systems from a more scientific angle.
A project which have had an impact on our formulation of microemulsions is the study of
fatty acid esters, alkylglucosides and some other surfactants compatibility with plexiglass.
Another project which we now are working with is the study of N-cyclohexyl-Dgluconamide, synthesized by Dr. Piispanen, in formulation for hard surface cleaning.
Thanks to SNAP we have got many new contacts and have created a network in surface
chemistry.
Unilever
Unilever has been involved in a number of pieces of work resulting from the SNAP
collaboration, namely a new series of surfactants for laundry detergency and the interaction
between sugar based surfactants and mucin.
A series of six surfactants synthesised within the SNAP collaboration where identified as
being possible aids to detergency in a laundry environment. After initial screening the benefits
did not justify inclusion in a commercial product. However further work is planned with these
types of materials. The research programme carried out within Per Claesson’s group will also
help Unilever better understand the fundamentals of detergency. This understanding should
help in the design of new formulations
In the second area of work it was found that certain sugar based surfactants did not remove
mucin which had been pre adsorbed onto a solid substrate. This work may be of benefit in the
design of new a toothpaste.
Of great benefit to Unilever’s R&D programme has been the opportunity to build up our links
with both academic and industrial groups in Sweden. Being involved in the SNAP centre has
encouraged our creative thinking and has been a positive experience.
UPM Kymmene
The involvement of UPM-Kymmene has clearly decreased during stage 3 (especially during
the year 2003) due to some changes of the personnel and their responsibilities, influencing
available resources deployed. The decision to set the focus of R&D more on the company's
main business- areas (pulp and paper applications) has influenced the situation too.
UPM-Kymmene has been involved and interested (during phase 3) especially in studies of
solubilisation of surfactants for pharmaceutical purposes (Non-hemolytic surfactants, cooperation AstraZeneca-UPM-Kymmene) in Programme II and as raw material producer of
wood-based surfactants for the development of cleaning formulations and cleaning studies
(Mixed surfactant systems) in Programme I.
39
UPM-Kymmene is also very interested in following up the progresses of the studies of both
mixed micelles and lubrication properties of surfactants.
The economic impact of the work is not possible to estimate at the moment, because the
increased knowledge of the behaviour of our own products has not yet influenced the sales
figures.
The cooperation with other partners (both companies and academia) has functioned well and
the atmosphere has been quite open and inspiring.
6 Prospects and strategies beyond the ten-year period
Due to a common strive between the SNAP participants to continue the collaboration after the
closing down of the centre, a substantial effort was made during 2003 and 2004 to look for
other means of funding. A work group with both academic and industrial partners was formed
that met on several occasions to discuss this issue. Eventually the three main possibilities
emerged, namely funding by EU, VINNOVA or MISTRA. After further consideration it was
decided that an application would be sent in for a new competence centre (VINN-Ex centre)
funded by VINNOVA. In fact, due to strategic and organisational reasons the SNAP members
decided to apply for two new centres. One application was called Center for HighPerformance Colloid & Surface Materials (HIPECS) and was coordinated by Lund
University, and the other one was called Supramolecular biomaterials structure dynamics and
properties and was coordinated by Chalmers University of Technology. Eventually only the
application from Chalmers was approved. Also, a MC-RTN network, Self-organisation under
confinement (SOCON), was established and supported by EU. The network consists of three
former SNAP-members. Several of the international collaborators that were identified by
SNAP also participate in the European network. The VINN-ExI centra Controlled Delivery
and Release (CODIRECT) at YKI include three former partners in SNAP.
40
Appendix A Examination
Licentiate´s degrees
1.
Tall Oil Products as Raw Materila for Surfactant Synthesis.
Hedman, B. E. O., Royal Institute of Technology (KTH), Stockholm, 2000
2.
Surface tension studies of nonionic-anionic surfactant mixtures
Liljekvist P, Royal Institute of Technology (KTH) and YKI Ytkemiska Institutet,
Stockholm, 2000
3.
Studies on Degradable Surface Active Esters
Stjerndahl, M., Chalmers University of Technology, Gothenburg, 2003
4.
ALA and m-ALA in Bicontinuous Lipid Formulations: -Characterisation and
Transdermal Delivery
Bender, J., Chalmers University of Technology, Gothenburg (2004)
5.
Fatty amine based surfactants, preparation and studies of adsorption behavior
Oskarsson, H., Chalmers University of Technology, Gothenburg (2006)
Doctor´s degrees
1.
Alkylglucosides - physical-chemical properties
Nilsson F, Lund University, Lund, 1998
2.
Magnetic Moments – NMR Spectroscopy in Lipid Science
Holmbäck J, Royal Institute of Technology, Stockholm, 2000
3.
Physico-Chemical Characterisation of Novel Surfactants
Folmer, B. M., Royal Institute of Technology (KTH), Stockholm, 2000
4.
Structure-Property Relationships of Surfactants at Interfaces and PolyelectrolyteSurfactant Aggregates
Kjellin, M., Royal Institute of Technology (KTH), Stockholm, 2002
5.
Novel Gemini Surfactants Based on Natural Products
Alami, El Ouafi, Chalmers, Gothenburg, 2002
6.
Synthesis and Characterization of Surfactants Based on Natural Products
Piispanen, P., Royal Institute of Technology (KTH), Stockholm, 2002
7.
Surfactants at non-polar surfaces
Persson, M., Royal Institute of Technology (KTH), Stockholm, 2002
8.
Green Colloid Chemistry. Characterisation of Environmentally Friendly Nonionic
Surfactant Systems
Whiddon, C. Lund University, Lund 2003
41
9.
Surfactants Based on Natural Products. Enzymatic Synthesis & Functional
Characterization
Viklund, F. Royal Institute of Technology (KTH), Stockholm, 2003
10. Phase Diagrams, Microstructure and Phase Separation in Alkyl Glucoside Systems
Reimer, J., Lund University, Lund 2003
11. Alkylglycoside Surfactants. Self-Assembly, Solid-State Properties and Interactions
with Hydrophobic Molecules
Ericsson, C., Lund University, Lund, 2005
12. Biodegradable Surfactants Containing Hydrolysable Bonds
Stjerndahl, M., Chalmers University of Technology, Gothenburg, 2005
13. Adsorption of polyhydroxyl based surfactants
Matsson, M. K. Royal Institute of Technology (KTH), Stockholm, 2005
14. Self Assembly of Surfactants and Polyelectrolytes in Solutions and at Interfaces
Bastardo, L. A., Royal Institute of Technology (KTH), Stockholm, 2005
15. Synthesis of Novel Polyhydroxyl Surfactants. Influence of the Relative
Stereochemistry on Surfactant Properties.
Neimert-Andersson, K., Royal Institute of Technology (KTH), Stockholm, 2005
16. Physico-chemical properties of binary and ternary mixtures of oxygen-containing
hydrocarbons, hydrocarbons and water : Implications for the design of alternative
fuels
Hull, A. Karlstad University, Karlstad and YKI, Institute for Surface Chemistry,
Stockholm, 2006
17. Interactions between surfactants and starch: From starch granules to amylose
solutions
Mira, I., Royal Institute of Technology (KTH), Stockholm, 2006
At the end of stage 4 there are still five active SNAP-funded PhD projects, which will be
finished during 2007/2008. These are:
-Fatty acid surface chemistry in non-aqueous solvent (Sarah Lundgren)
-Block copolymers as efficient boosters (Markus Nilsson)
-Mixed surfactant systems (Iruthayaraj Joseph)
-Topical formulation (Johanna Bender)
- Softeners (Hans Oskarsson, Akzo Nobel Industry PhD)
42
Completed MSc theses - Diploma works
1.
Enzymatic synthesis of sugar esters in microemulsions
Bell E, Mälardalens Högskola, carried out to a large extent at Biochemistry, KTH and
Institute for Surface Chemistry, 1998
2.
Lubricating properties of cutting fluids stabilised with alkylpolyglucosides : Finding
a correlation between emulsion droplet size, zeta potential and lubricating
properties
Gahnström J, Luleå University of Technology, Luleå and Institute for Surface Chemistry,
Stockholm, 1998
3.
Interactions between polyelectrolytes and oppositely charged surfactants in bulk
solution and at interfaces
Nygren J, KTH 1999
4.
Ytaktiva egenskaper hos sterolbaserade tensider
Nordgreen T, Institutionen för Kemi, Kungliga Tekniska Högskolan och Ytkemiska
Institutet, Stockholm 1999
5.
Adsorption from soybean phosphatidylcholine/n-dodecyl-β-D-maltoside dispersions
at liquid/solid and liquid/air interfaces
Fagefors J, Lund University, Lund 1999
6.
The Influence of Salt Concentration on Synergistic Effects in Mixed Surfactant
Systems
Petra Jonsson, KTH, 2001.
7.
Hemolytic activity and solubilizing capacity of surface active excipients for
pharmaceutical use.
Lina Karlsson, Chalmers, 2001.
8.
Physical-chemical properties of the deuteriumoxid/n-octyl-β-D-glucoside/1-octanol
System. A phase diagram, Self-diffusion NMR, Deuterium NMR, and SAXS study.
Markus Nilsson, Lund University, 2003.
9.
Synthesis and physico-chemical properties of C12-Y-amine and derivatives
Maud Frankenberg, Chalmers, 2003
10. Adsorption of cationic surfactants using Surface Plasmon Resonance technology
Navid Goharzadeh, Chalmers, 2003
11. Adsorption studies of naphtalene sulphonates on hydrophobic surfaces using
Surface Plasmon Resonance
Anders Paalberg, Chalmers, 2005
12. Study of interactions between surfactants and amylose in aqueous solution
Fredrik Hallberg, YKI, 2005
13. Adsorption of sugar-based surfactants on polystyrene latex
43
Karin Österberg, YKI, 2005
14. Phase studies on dialkyl dimethyl ammonium chloride compared with diester
dimethyl ammonium chloride with and without alkyl dimethyl amine oxide
Jesper Hedin, Chalmers, 2005
15. Phase studies on dialkyl dimethyl ammonium chloride compared with diester
dimethyl ammonium chloride with and without alkyl dimethyl amine oxide
Jackey Nguyen, Chalmers, 2005
16. Synergism of mixtures of naphtalene sulphonates and fatty amine ethoxylates
Ingrid Åslund, Chalmers 2006
44
Appendix B Publications
1996
1.
Nilsson, F.; Söderman, O.; Johansson, I., Physical-Chemical Properties of the n-Octyl
b-D-Glucoside/Water System. A phase Diagram, Self-Diffusion NMR and SAXS
Study. Langmuir 1996, 12, (4), 902-908.
1997
2.
von Corswant, C.; Engström, S.; Söderman, O., Microemulsions based oil soybean
phosphatidylcholine and triglycerides. Phase behavior and microstructure. Langmuir
1997, 13, (19), 5061-5070.
3.
Nilsson, F.; Söderman, O.; Johansson, I., Physical-Chemical Properties of Some
Branched Alkyl Glucosides. Langmuir 1997, 13, 3349-3354.
4.
Kronberg, B., Surfactant mixtures. Curr Opin Colloid Interface Sci 1997, 2, 456-463.
5.
Kjellin, U. R. M.; Claesson, P. M.; Audebert, R., Interactions between Adsorbed
Layers of a Low Charge Density Cationic Polyelectrolyte on Mica in the Absence and
Presence of Anoinic Surfactant. J. Colloid Int. Sci. 1997, 190, 476-484.
6.
Folmer, B. M.; Holmberg, K.; Svensson, M., Interaction of rhizomucor miehei lipase
with an amphoteric surfactant at different pH values. Langmuir 1997, 13, 5864-5869.
7.
Eriksson, L. G. T.; Claesson, P. M.; Ohnishi, S.; Hato, M., Stability of
dimethyldioctadecylammonium bromide Langmuir-Blodgett films on mica in aqueous
salt solutions - Implications for surface force measurements. Thin Solid Films 1997,
300, 240-255.
8.
Claesson, P. M.; Dedinaite, A.; Fielden, M.; Kjellin, M.; Audebert, R.,
Polyelectrolyte-surfactant interactions at interfaces. Progr. Colloid Polym. Sci. 1997,
106, 24-33.
1998
9.
von Corswant, C.; Söderman, O., Effect of adding isopropyl myristate to
microemulsions based on soybean phosphatidylcholine and triglycerides. Langmuir
1998, 14, (13), 3506-3511.
10.
von Corswant, C.; Olsson, C.; Söderman, O., Microemulsions based on soybean
phosphatidylcholine and isopropylmyristate. Effects of addition of hydrophilic
surfactants. Langmuir 1998, 14, (24), 6864-6870.
11.
Svensson, M., Surfactants based on sterols and other alicyclic compounds. In Novel
Surfactants: Preparation, Applications and Biodegradability, Marcel Dekker Inc.:
New York, 1998; Vol. 74, pp 179-200.
12.
Skagerlind, P.; Folmer, B.; Jha, B. K.; Svensson, M.; Holmberg, K., Lipase-Surfactant
interactions. Progr Colloid Polym Sci 1998, 108, 47-57.
13.
Nilsson, F.; Söderman, O.; Reimer, J., Phase separation and aggregate-aggregate
interactions in the C9G1/C10G1 ß-alkylglucosides/water system. A phase diagram and
NMR self-diffusion study. Langmuir 1998, 14, (22), 6396-6402.
14.
Nilsson, F.; Söderman, O.; Johansson, I., Four different C8G1 alkylglucosides.
Anomeric effects and the influence of straight vs. branched hydrocarbon chains. J.
Coll. Int. Sci. 1998, 203, (1), 131.
15.
Nilsson, F.; Söderman, O.; Hansson, P.; Johansson, I., Physical-chemical properties of
C9G1 and C10G1 b-alkylglucosides. Phase diagrams and aggregate size/structure.
45
16.
17.
18.
19.
20.
21.
Langmuir 1998, 14, (15), 4050-4058.
Motshegwe, S. M.; Holmbäck, J.; Yeboah, S. O., General properties and the fatty acid
composition of the oil from the mophane caterpillar, Imbrasia belina. J Am Oil Chem
Soc 1998, 75, 725-728.
Matero, A.; Mattsson, Å.; Svensson, M., Alkyl polyglucosides as hydrotropes. J
Surfactants Deterg 1998, 1, 485-489.
Jönsson, B.; Lindman, B.; Holmberg, K.; Kronberg, B., Surfactants and polymers in
aqueous solution. John Wiley & Sons Ltd: Chichester, Sussex, England, 1998.
Jha, B. K.; Svensson, M.; Holmberg, K., A titration calorimetry study of a technical
grade APG. Prog Colloid Polym Sci 1998, 110, 230-234.
Claesson, P. M., Interactions between surfaces coated with carbohydrates, glycolipids
and glycoproteins. In Biopolymers at Interfaces, Malmsten, M., Ed. Marcel Dekker
Inc.: New York, 1998; Vol. 75, pp 281-320.
Blute, I.; Kronberg, B.; Svensson, M.; Unelius, R., Phase behaviour of alkyl glycerol
ether surfactants. Tenside, Surfactants, Deterg 1998, 35, 207-212.
1999
22.
Sierra, M. L.; Svensson, M., Mixed micelles containing alkylglycosides: Effect of the
chain length and the polar head group. Langmuir 1999, 15, 2301-2306.
23.
Johansson, I.; Strandberg, C.; Karlsson, B.; Karlsson, G.; Hammarstrand, K., Use of
mixtures of alkyl alkoxylates and alkyl glucosides in strong electrolytes and highly
alkaline systems. In Industrial applications of surfactants IV, Karsa, D., Ed. Royal
Society of Chemistry: 1999; pp 88-107.
24.
Folmer, B. M.; Svensson, M.; Holmberg, K.; Wyn Brown, J., The Physicochemical
Behaviour of Phytosterol Ethoxylates. Journal of Colloid Interface Science 1999, 213,
112-120.
25.
Claesson, P. M.; Kjellin, U. R. M., Studies of interactions between interfaces across
surfactant solutions employing various surface force techniques. In Modern
Characterization Methods of Surfactant Systems, Binks, B. P., Ed. Marcel Dekker,
Inc: New York, 1999; Vol. 83, pp 255-333.
2000
26.
Söderman, O.; Johansson, I., Polyhydroxyl-based surfactants and their physicochemical properties and applications. Curr. Opin. in Colloid Interface Sci. 2000, 4,
(6), 391-401.
27.
Persson, C. M.; Claesson, P. M.; Johansson, I., Interfacial Behavior of n-Octyl ß-DGlucopyranoside Compared to That of a Technical Mixture Consisting of Octyl
Glucoside. Langmuir 2000, 16, 10227-10235.
28.
Liljekvist, P.; Kronberg, B., Comparing decyl-b-maltoside and octaethyleneglycol
mono n-decyl ether in mixed micelles with dodecyl benzenesulfonate 2. Interaction of
mixed micelles with polyvinylpyrrolidone. Journal of Colloid Interface Science 2000,
222, 165-169.
29.
Liljekvist, P.; Kronberg, B., Comparing decyl-b-maltoside and octaethyleneglycol
mono n-decyl ether in mixed micelles with dodecyl benzenesulfonate 1. Formation of
mixed micelles. Journal of Colloid Interface Science 2000, 222, 159-164.
30.
Johansson, I.; Strandberg, C.; Karlsson, B.; Karlsson, G.; Hammarstrand, K.,
Environmentally benign non-ionic systems for use in highly alkaline media. Progress
46
31.
32.
33.
34.
35.
36.
37.
38.
39.
40.
41.
42.
in Colloid and Polymer Science 2000, 116, 26-32.
Johansson, I.; Strandberg, C. In Microemulsions with medium chain
alkylpolyglucosides, 5th World Surfactants Congress, CESIO 2000, Florens, Italy,
2000; Florens, Italy, 2000.
Johansson, I.; Karlsson, B. In Synergies between alkyl amine derivatives and nonionics such as alkyl glucosides, 5th World Surfactants Congress, CESIO 2000,
Florens, Italy, 2000; Florens, Italy, 2000.
Holmberg, K.; Nydén, M.; Lee, L.-T.; Skagerlind, P.; Folmer, B. In Interactions
between surfactants and a detergent enzyme, 5th World Surfactants Congress, CESIO
2000, Florens, 2000; Florens, 2000.
Hellberg, P.-E.; Bergström, K.; Holmberg, K., Cleavable surfactants. J. Surf. Det.
2000, 3, 81.
Folmer, B. M.; Kronberg, B., Effect of surfactant-polymer association on the stability
of foams and thin films: sodium dodecyl sulphate and poly (vinyl pyrrolidone).
Langmuir 2000, 16, 5987-5992.
Dedinaite, A.; Claesson, P. M.; Bergström, M., Polyelectrolyte-surfactant layers:
Adsorption of preformed aggregates versus adsorption of surfactant to preadsorbed
polyelectrolyte. Langmuir 2000, 16, (12), 5257-5266.
Claesson, P. M.; Bergström, M.; Dedinaite, A.; Kjellin, M.; Legrand, J.-F.; Grillo, I.,
Mixtures of Cationic Polyelectrolyte and Anionic Surfactant Studied with SmallAngle Neutron Scattering. J. Phys. Chem. B 2000, 104, 11689-11694.
Bergström, M.; Pedersen, J. S., A Small-Angle Neutron Scattering Study of Surfactant
Aggregates Formed in Aqueous Mixtures of Sodium Dodecyl Sulfate and
Didodecyldimethylammonium Bromide. Journal of Physical Chemistry B 2000, 104,
(17), 4155-4163.
Bergström, M.; Eriksson, J. C., A theoretical analysis of synergistic effects in mixed
surfactant systems. Langmuir 2000, 16, (18), 7173-7181.
Bergström, M., Thermodynamics of Anisotropic Surfactant Micelles. II. A Molecular
Interpretation of the Micellar Curvature Free Energy. J. Chem. Phys. 2000, 113, (113),
5569-5579.
Bergström, M., Thermodynamics of anisotropic surfactant micelles. I. The Influence
of the Curvature Free Energy on the Micellar Size and Shape. J Chem Phys 2000, 113,
5559-5568.
Bergqvist, M.; Holmbäck, J., Nuclear magnetic resonance spectroscopy and reversedphase
high-performance
liquid
chromatography
of
peracetylated
digalactosyldiacylglycerols. J Am Oil Chem Soc 2000, 77, (7), 757-761.
2001
43.
Whiddon, C.; Söderman, O., Unusually large deuterium isotope effcts in the phase
diagram of a mixed alkylglucoside surfactant/water system. Langmuir 2001, 17, 18031806.
44.
Wassenius, H.; Nydén, M.; Holmberg, K., Dispersion Stability Evaluated by
Experimental Design. J. Disp. Sci. Technol. 2001, 22, 297.
45.
Stålgren, J.; Claesson, P. M.; Wärnheim, T., Adsorption of liposomes and emulsions
studied with a Quartz Crystal Microbalance. Adv Colloid Interface Sci 2001, 89-90,
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Ericsson, C. A.; Söderman, O.; Garamus, V. M.; Bergström, M.; Ulvenlund, S.,
Effects of Temperature, Salt and Deuterium Oxide on the Self-Aggregation of
Alkylglycosides in Dilute Solutions. 2. n-Tetradecyl-b-D-maltopyranoside. Langmuir
2005, 21, 1507-1515.
Ericsson, C. A.; Ericsson, L. C.; Ulvenlund, S., Solid-State Phase Behaviour of
Dodoecylglycosides. Carbohydr. Res. 2005, 340, 1529-1537.
Ericsson, C. A.; Ericsson, L. C.; Kocherbitov, V.; Söderman, O., Thermotropic Phase
Behaviour of Long-Chain Alkylmaltosides. Phys. Chem. Chem. Phys. 2005, 7, (15),
2970-2977.
Ericsson, C. A. Alkylglycoside surfactants: Self-assembly, solid-state properties and
interactions with hydrophobic molecules. Lunds Universitet, Lund, 2005.
Cabaleiro-Lago, C.; Nilsson, M.; Söderman, O., Self-diffusion NMR studies of the
host-guest interaction between beta-cyclodextrin and alkyltrimethylammonium
bromide surfactants. Langmuir 2005, 21, (25), 11637-11644.
Bergström, L. M.; Bastardo, L. A., A small-angle neutron and static light scattering
study of micelles formed in aqueous mixtures of a nonionic alkylglucoside and an
anionic surfactant. J. Phys Chem. B. 2005, 109, (25), 12387-12393.
Bender, J.; Ericson, M. B.; Merclin, N.; Iani, V.; Rosén, A.; Engström, S.; Moan, J.,
Lipid cubic phases for improved topical drug delivery in photodynamic therapy.
Journal of Controlled Release 2005, 106, (3), 350-360.
Bastardo, L. A.; Meszaros, R.; Varga, I.; Gilanyi, T.; Claesson, P. M., Deuterium
isotope effects on the interaction between hyperbranched polyethylene imine and an
anionic surfactant. J. Phys. Chem. B 2005, 109, (33), 16196-16202.
Bastardo, L. A.; Garamus, V. M.; Bergström, M.; Claesson, P. M., The structures of
complexes between polyethylene imine and sodium dodecyl sulfate in D2O. A
scattering study. J. Phys Chem. B. 2005, 109, 167.
Bastardo, L. A. Self Assembly of Surfactants and Polyelectrolytes in Solutions and at
Interfaces. Royal Institute of Technology, Stockholm, 2005.
Iruthayaraj, J.; Poptoshev, E.; Vareikis, A. V.; Makuska, R.; van der Wal, A.;
Claesson, P. M., Adsorption of low charge density polyelectrolyte containing
poly(ethylene oxide) side chains on silica: effects of ionic strength and pH.
Macromolecules 2005, 38, (14), 6152-6160.
2006
173. Söderlind, E.; Karlsson, L., Haemolytic activity of maltopyranoside surfactants.
European Journal of Pharmaceutics and Biopharmaceutics 2006, 62, 254-259.
174. Oskarsson, H.; Holmberg, K., Adsorption of ethoxylated cationic surfactants on selfassembled mono-layers of alkanethiols on gold using surface plasmon resonance
detection. Journal of Colloid and Interface Science 2006, 301, 360.
175. Nilsson, M.; Söderman, O.; Johansson, I., The Effect of Polymers on the Phase
Behavior of Balanced Microemulsions: Block co-polymer and comb-polymers. Coll.
Polymer Sci. 2006, 284, 1229.
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polyhydroxylated compounds as head groups in surfactant synthesis. European
Journal of Organic Chemistry 2006, 69, (11), 3746-3752.
Neimert-Andersson, K.; Sauer, S.; Panknin, O.; Borg, T.; Söderlind, E., Synthesis of
New Sugar-Based Surfactants and Evaluation of Their Hemolytic Activities. Journal
of Organic Chemistry 2006, 71, (9), 3623-3626.
Lundgren, S. M.; Persson, K.; Kronberg, B.; Claesson, P. M., Adsorption of Fatty
Acids in Alkane Solutions: A Quartz Crystal Microbalance Study. Tribology Letters
2006, 22, (1), 15-20.
Hull, A.; Golubkov, I.; Kronberg, B.; van Stam, J., Alternative fuel for a standard
diesel engine. Int. J. Engine Res 2006, 7, 51-63.
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fuel for spark ignition engines. Int. J. Engine Res. 2006, 7, 203-214.
Cabaleiro-Lago, C.; Nilsson, M.; Valente, A. J. M.; Bonini, M.; Söderman, O., NMR
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and Interface Science 2006, 300, 782.
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Oligo(ethylene glycol)-Terminated Self-Assembled Monolayers: Surface Forces,
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Alkylaminoamide Sugar Surfactants at Tailor-Made Surfaces. Journal of Surfactants
and Detergents In press 2006.
185. Nilsson, M.; Cabaleiro-Lago, C.; Valente, A. J. M.; Söderman, O., Interactions
between Gemini Surfactants, 12-s-12, and –cyclodextrin As Investigated by NMR
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56
Appendix C Research staff 1995-2006
Surname
Alami
Alander
Alness
Andersson
Andersson
Annerling
Astikainen
Baeckström
Baeling
Bajouk
Bastardo
Bender
Bengtsson
Berg
Bergström
Bergström
Blomberg
Blute
Borde
Bos
Boschkova
Brewer
Brinck
Byröd
Claesson
Clarke
Dahgren
de Groot
Dédinaité
Eick
Ekelund
Ekman
Engström
Ericsson
Eriksson
Falk
Farre
Findlay
Fogden
Folmer
Fridén
Fritzon
Georgsson
Gottberg-Klingskog
Gröön
Gustafson
Gytel
Hansson
Hedman
Hellberg
First name
El Ouafi
Jari
Kenneth
Ann Charlott
Ulrika
Annika
Marvi
Peter
Peter
Bassem
Luis
Johanna
Anna
Johan
Karin
Magnus
Eva
Irena
A
Martin
Katrin
Mark
Johanna
Eva
Per
Jim
Lennart
Peter
Andra
Susanne
Katarina
Sewerin
Sven
Caroline
Jan Christer
Karl-Erik
Cecilia
P
Andrew
Britta
Marcus
Anna
Thina
Eva
Ingemar
Ingrid
Ulla
Ulf
Björn
Per-Erik
Employment while in SNAP
Chalmers University of Technology
Karlshamns
Svenska Lantmännen
Karlshamns
Snowclean
UPM-Kymmene Oy
KTH
Svenska Lantmännen
KTH
Lund University
Svenska Lantmännen
KTH
KTH
YKI
AstraZeneca
Unilever
YKI
Arizona Chemical
YKI
AstraZeneca
KTH
Arizona Chemical
Unilever
Unilever
Arizona Chemical
AstraZeneca
Kemira Kemi
Fys. Kemi 1, Lunds Universitet
KTH
Astra Hässle
Unilever
YKI
YKI
AstraZeneca
AstraZeneca
YKI
Svenska Lantmännen
AstraZeneca
Kemira Kemi
Karlshamns
KTH
Position in SNAP
PhD student
Senior scientist
Senior scientist
Scientist
Senior scientist
Senior scientist
Technician
Senior scientist
Senior scientist
Scientist
PhD student
PhD student
PhD student
Senior scientist
Senior scientist
Senior scientist
Senior scientist
Scientist
Scientist
Senior scientist
Senior scientist
Senior scientist
Senior scientist
Senior scientist
Professor/Senior scientist
Senior scientist
Senior scientist
Scientist
Scientist
Senior scientist
Senior scientist
Senior scientist
PhD student
Senior scientist
Scientist
Scientist
Senior scientist
PhD
Scientist
Scientist
Scientist
Senior scientist
Scientist
Senior scientist
Senior scientist
PhD/Senior scientist
Scientist
57
Herslöf
Hillerström
Hinkkanen
Holmberg
Holmbäck
Hotanen
Hull
Hult
Högberg
Ihrig
Jacobsson
Jacobsson
Jansson
Johansson
Jonsson
Joseph
Karlsson
Karlsson
Karlsson
Karsa
KarvoPaakkanen
Kaufmann
Kautto
Kene
Kjellin
Kocherbitov
Kronberg
Kumar Jha
Lidefelt
Liljekvist
Lindgren
Lindström
Lundgren
Lyne
MacNab
MacNamee
Malmsten
Matero
Matsson
Mattsson
McKee
Miikki
Mira
Mårtensson
Neimert-Andersson
Nelson
Nilsson
Nilsson
Nilsson
Norberg
Norin
Nydén
Oldgren
Bengt
Anna
Markuu
Krister
Jan
Ulf
Angelica
Karl
Carl-Johan
Klaus
Roger
Ulla
Mikael
Ingegärd
Anders
Iruthayaraj
Bo
Lina
Stefan
David
Marikka
Peter
Thorbjörn
Vanja
Mikael
Vitaly
Bengt
Baresh
Jan-Olof
Pernilla
Jenny
C
Sarah
Bruce
Donna
Cathy
Martin
Anna
Maria
Åsa
Anthony
Vesa
Isabel
Cecilia
Kristina
Lloyd
Markus
Frederik
Svante
Staffan
Torbjörn
Magnus
Jan
Lipid Technologies Provider AB
YKI
UPM-Kymmene Oy
LipoCore Holding AB
UPM-Kymmene Oy
YKI
KTH
KTH
Karlshamns
KTH
Castrol
Svenska Lantmännen
KTH
AstraZeneca
Karlshamns
Arizona Chemical
LipoCore Holding AB
Arizona Chemical
YKI
KTH and YKI
Lund University
YKI
YKI
Karlshamns
YKI
Kemira Kemi
Karlshamns
YKI
YKI
Unilever
Lund University
YKI
YKI
YKI
Snowclean
Unilever
UPM-Kymmene Oy
YKI
KTH
KTH
Arizona Chemical
Lund University
YKI
Karlshamns
KTH
Snowclean
Scientist
Technician
PhD student
Senior scientist
PhD student
PhD student
Senior scientist
Scientist
Senior scientist
Senior scientist
Senior scientist
Scientist
PhD student
Scientist
Scientist
Senior scientist
Senior scientist
Senior scientist
Senior scientist
Scientist
Senior scientist
Scientist
Scientist
Senior scientist
LicD
Senior scientist
Technician
PhD student
Managing Director
Senior scientist
Post doc
Senior scientist
PhD student
Senior scientist
Senior scientist
Senior scientist
PhD student
PhD student
PhD student
Senior scientist
PhD student
PhD student
Senior scientist
Senior scientist
Senior scientist
Senior scientist
58
Olsson
Oskarsson
Park
Persson
Persson
Pettersson
Piispanen
Poptoshev
Pugh
Reimer
Rutherford
Samuelsson
Sandberg
Sandström
Scherlund
Schipper
Segerborg-Fick
Sierra
Sjödin
Skagerlind
Skoog
Sköld
Somfai
Stjerndahl
Strandberg
Svanberg
Svensson
Syrous
Söderlind
Söderman
Tabor
Tavakoli
Thorén
Ulvenlund
Unelius
Valenticevic Häggquist
Waltermo
van de Berg
van der Wal
Vernet
Whiddon
Viklund
Villwock
Wollbratt
von Corswant
Zhou
Österberg
Sara
Hans
S
Marcus
Karin
O
Peter
Evgeni
Robert
Johan
Keith
Anne-Cathrine
Elina
Leif
Marie
Nicolaas
Ann
Marie-Luisa
Peter
Peter
Annika
Rolf
Peter
Maria
Christine
Agne
Martin
Behrouz
Erik
Olle
J
Siavasti
Per
Stefan
Rickard
Dragica
Åsa
Albert
Albert
E
Christy
Fredrik
Kurt
Maria
Christian
B
Eva
KTH
KTH
YKI
Svenska Lantmännen
KTH
KTH
YKI
Unilever
Karlshamns
AstraZeneca
AstraZeneca
Svenska Lantmännen
YKI
Castrol
Kemira Kemi
Kemira Kemi
KTH
Svenska Lantmännen
AstraZeneca
Karlshamns
AstraZeneca
AstraZeneca
KTH
YKI
KTH
Unilever
KTH
Lund University
KTH
Svenska Lantmännen
AstraZeneca
AstraZeneca
Unilever
Scientist
PhD student
PhD student
PhD student
Senior scientist
Scientist
PhD student
Post doc
PhD-student
Senior scientist
Senior scientist
Scientist
Senior scientist
Senior scientist
Senior scientist
Senior scientist
Scientist
Scientist
Senior scientist
Scientist
Senior scientist
PhD student
Senior scientist
Senior scientist
Senior scientist
Technician
Senior scientist
Scientist
Senior scientist
Post doc
Senior scientist
Senior scientist
Scientist
Senior scientist
Senior scientist
Senior scientist
PhD student
PhD student
PhD student
Senior scientist
Technician
Senior scientist
Scientist
Senior scientist
59
Appendix D Center organisation during Stage 1-4
Organisation 1995-1997 (Stage 1)
Organisation 1998-2001 (Stage 2 and one year of Stage 3)
60
Organisation 2002-2003 (Two years of Stage 3)
Organisation 2004-2006 (Stage 4)
61

Centre for Surfactants based on Natural Products SNAP

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