Applications of Maleic Anhydride Chemistry in Skin Care

JANUARY 2015 • Vol. 21 No. 1
New York Society of Cosmetic Chemists
www.nyscc.org
Applications of Maleic Anhydride Chemistry in Skin
Care, Biomedical Devices, and Transdermal Delivery. Part I.
… by Roger L. McMullen
O
ver the last several decades there have been considerable advances
in the use of maleic anhydride chemistry for applications related to
the skin. First and foremost, it is an excellent bioadhesive agent. This
is important for both the biomedical and personal care industries. It is an
imperative component that helps to bind medical devices to the skin,
including biosensors, and also serves as an aid in wound healing. In skin
care, maleic anhydride polymers are used to remove unwanted debris from
facial pores, especially those surrounding the nasal region, and as an aid to
help reduce aluminum in antiperspirant formulations. Moreover, polymers
based on maleic anhydride are used as transdermal delivery agents in both
traditional systems and more innovative designs, such as microneedles.
Maleated compounds also play important roles as emollients in skin care
formulations and as delivery agents for active ingredients, such as vitamin C.
In addition, polymers based on maleic anhydride are used as topical skin
tightening agents and rheology modifiers in various types cosmetic formulations.
Bioadhesives
The area of adhesives is a very broad field that finds applications in many
different industries. In relation to the skin, adhesives are especially important
in the medical device industry. Maleic anhydride polymers are used as
bioadhesive agents in many applications including pressure sensitive tapes
and tapes designed for surgical purposes, dermatological tape strips designed
to remove keratotic material from skin, and wound healing.
Pressure sensitive adhesives are the most common type of material
utilized for application to skin. They adhere to the surface of skin by simply
applying pressure to the tape while on top of the skin. The tape may contain several components, principally the adhesive resin, a tack agent,
pigment, plasticizer, and antioxidant. Usually, these elements are incorporated on top of a backing material made of paper, plastic, or
cloth. The plasticizer provides flexibility to the adhesive resin while antioxidants prevent accelerated aging of the adhesive due to exposure
to solar radiation, heat, etc.
Early work in bioadhesives for skin demonstrated the utility of maleic anhydride-based polymers in pressure sensitive medical and
surgical tapes.1-3 In general, these materials were based on copolymers of maleic anhydride and vinyl ether. In particular, several advantages
(Continued on page 4)
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Applications of Maleic Anhydride Chemistry
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(Continued from page 1)
exist to using these resins. Notably, there is no need to employ additional tack agents as the maleic
anhydride-vinyl ether resin itself has a considerable degree of stickiness. Further, such resins bind to a greater
degree with substrates than they do to themselves. Throughout the 1970s and 1980s, there was less activity
in the patent arena in relation to the use of maleic anhydride-based polymers in adhesives.4 Regardless,
these materials remained in use with some improvements in their formulation and application.5 Cross-linking
of poly(alkyl vinyl ether-maleic acid) resulting in a cross-linked polymeric ester or amide/imide produces a
hydrogel with desirable rheological behavior while maintaining bioadhesion to skin.6 In addition, maleic
acid-based polymers have found utility in ostomy appliances where they serve as an adhesive holding
together a medical device and the skin at the point of a stoma—an opening or orifice surgically created to
provide a pathway from an internal organ to the surface of the body.
Biosensors
In the 1990s, there was some excitement in the maleic anhydride community about the use of
poly(methylvinyl ether-maleic acid) in biomedical sensor applications.7-9 Ag/AgCl inks are used as biosensors
for biomedical monitoring, medical diagnostics, and iontophoretic drug delivery. Typically, the inks are
printed onto a substrate, which then serves as the biosensor. Bioadhesive polymeric hydrogels provide a
very good flexible means for attaching the biosensor to skin. In addition, the hydrogel can be made
conductive by adding electrolyte. In a typical formulation, one could include the bioadhesive component
(poly(vinylmethyl ether-maleic acid), plasticizer (glycerine), viscosity builder (poly(vinyl pyrrolidone)), and
electrolyte (sodium chloride).9 A key advantage of the maleic anhydride chemistry for this application lies
not only in its bioadhesive properties, but also its activation by water in moist environments. This allows the
adhesive to remain efficacious even during perspiration and in moist or damp environments. It should be
noted that over-wetting the adhesive polymer results in a slimy residue that is difficult to dry.
Wound Healing
In addition to their use as adhesives in medical devices, maleic anhydride-based polymers are also
employed in wound healing applications. Nitric oxide is a known agent that is used topically to promote
healing of chronic wounds, such as diabetic ulcers.10 It functions by regulating collagen formation, cell
proliferation, and wound contraction.11 Unfortunately, the short half-life of nitric oxide and its associated
instability have hampered its success in finished pharmaceutical products. To circumvent this problem, a
group at the University of Toronto designed a supramacromolecular complex capable of controlled delivery
of nitric oxide to wound areas of the skin. The general structure of the complex is provided in Figure 1. As
shown in the illustration, poly(methylvinyl ether-maleic acid) is reacted with S-nitrosoglutathione, which
becomes esterified to one of the acid groups. S-nitrosoglutathione contains the functionality of the
antioxidant, glutathione, and contains nitric oxide embedded in the structure, which is released to the tissue.
Figure 1. Reaction scheme of nitrosoglutathione with poly(methylvinyl
ether-maleic anhydride. The resulting molecule may complex with
poly(vinyl pyrrolidone) by a hydrogen bonding mechanism.
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Also shown in the scheme is the complexation of poly(vinylpyrollidone), which associates with
poly(methylvinyl ether-maleic acid) via hydrogen bonds. Overall, the complexation of the two polymers
and the esterification with S-nitrosoglutathione results in a functional controlled release vehicle for nitric
oxide. The addition of poly(vinylpyrollidone) to the supramolecular complex causes an increase in the
hydrophilicity of the complex, which is accompanied by a decrease in the dissociation rate of nitric oxide
due to its delayed release in aqueous mediums. Therefore, it is not surprising that the controlled release of
nitric oxide depends on the concentration ratio of poly(vinylpyrollidone) to poly(methylvinyl ether-maleic
acid), which is optimal at a one-to-one ratio. The kinetic release profiles also depend on the molecular
weight of both poly(methylvinyl ether-maleic acid) and poly(vinylpyrollidone). Not surprisingly, higher
molecular weight species produce slower nitric oxide release profiles. In this case, higher molecular weight
polymers will yield a more structurally extensive complex that undergoes slower dissolution.12
Another important area in wound healing is disinfection, which is extremely important during surgical
procedures. As a preparatory step, the area of skin where the incision is to be administered, as well as the
surrounding regions, is treated with an antibacterial agent. Unfortunately this preparatory procedure is not
sufficient to completely sterilize site or to immobilize unwanted bacterial from migrating into the incision.
In many instances, an additional step is added to the preparatory procedure that consists of treating the site
with incise drapes, which are large sheets of adhesive film. The incise drapes are applied to the site prior to
surgery and incisions are made directly through the drapes. Skin sealants are also used for this purpose and
essentially are thin film skin protectant. Due to its exceptional bioadhesivity, poly(vinyl ether-maleic
anhydride) is included in skin sealant formulations. Typically, the sealant components consist of a suitable
bioadhesive polymer and antibacterial agent that are soluble in ethanol and form a water insoluble film
designed to immobilize bacteria, and prevent infection to the site of incision.13,14
Keratotic Plug Removal
Over the last decade, increasing attention has been given to the topic of skin pores—also often referred
to as facial pores. In this case, the term “pore” evolved from the lay population to describe an opening in
the skin associated with a pilosebaceous unit, which consists of the sebaceous gland and hair follicle. These
“pores” are clearly evident to the human eye and are especially visible in certain anatomical regions of the
body, such as the face where they often present themselves in areas adjacent to the nasal region. Such pores
are generally associated with excessive sebum production.15 Comedones may be formed when there is an
excess of sebum and keratinocyte cell debris (keratotic plugs). In layman’s terms, comedones refer to black
heads (open pore) or white heads (closed pore). The dark color of the black heads originates from oxidation
of the cell debris and sebum. There has been much effort in the personal care industry to design products
to help remove black heads. Two of the most successful products in this area are Pond’s Clear Pore Strips
(manufactured by Unilever, Inc.) and Bioré’s Pore Perfect Strips (manufactured by Kao, Inc.). Both products
are essentially shaped like a Band-Aid strip and are adhered to the nasal
region of the face (see Figure 2). After a certain period of time, the
tape-strip is removed from the skin and it brings with it all of the
gunky dark material from the pore. Looking at the underside
of the nose strip, one normally observes a range of mountain
peaks corresponding to all of the debris collected from the
pore. Of the two commercial products based on this
technology, the Chesebrough-Pond nasal strips by Unilever
were designed based on a high molecular weight (1,500,000
Da) analog of poly(maleic acid-vinyl ether), which serves as
the bioadhesive in the nose strip. The nose strip is constructed
of a flexible non-occlusive substrate sheet that is impregnated
with the bioadhesive.16-18 Prior to application, the nose strip is
immersed in water and placed in the region of interest. After it
dries, the nose strip is then removed from the skin site bringing
with it unwanted black head debris.
Figure 2. Photograph demonstrating the use of
adhesive strips for keratotic plug removal in skin.
(Continued on page 6)
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Applications of Maleic Anhydride Chemistry
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Antiperspirant Technology
In Homo sapiens the principal mode of thermoregulation is accomplished by evaporative cooling that
takes place when sweat is secreted from eccrine glands and evaporated from the surface of the skin. Overall,
such a process ensures that the body's core temperature does not significantly rise above 37 °C to levels
that can lead to heat exhaustion or hyperthermia. There are about 2 to 5 million eccrine glands distributed
over the surface of the body that carry out this function. In addition, there are approximately 100,000
apocrine glands localized in specific regions of the body, most notably the axillae (underarm region).
Although apocrine glands secrete substances that eventually break down to malodorous compounds,
antiperspirant treatments target eccrine glands that are located in the axillae.
The most common mechanism for sweat prevention occurs due the formation of a plug in the lumen of
the sweat gland duct (see Figure 3). Historically, the most frequently employed antiperspirant salts were
aluminum chloride (AlCl3), aluminum chlorohydrate (ACH), and
aluminum zirconium chlorohydrate complex (AZAP). For this
reason, most of our understanding of plug formation comes from
studies conducted with these materials.
In recent years, considerable attempts have been made minimize the use of
Figure 3.
aluminum in antiperspirant formulas.19-23 Such compositions can be achieved by
Illustration of
an antiperspirant
supplementing the antiperspirant formulation with polymers that act as co-gellants with
forming a plug
the aluminum salts thereby allowing lower levels of the aluminum salt to be employed.
(blue) in the
Initial work in this area focused on maintaining the antiperspirant aluminum
eccrine gland
salt and poly(vinyl ether-maleic acid) in two separate phases in the formulation.19
duct.
Upon application of the antiperspirant to the skin, the formulation mixes
allowing the polymer and aluminum salt to interact, resulting in gelation of the
ingredients. The mixture fills the sweat pores, which eventually clog, preventing
the passage of sweat.
The ability of maleic anhydride in its hydrolyzed form to complex with Lewis acids,
such as aluminum chloride, is well known.24 While not explained very well in the literature with specific
reference to antiperspirant salts, the aluminum/zirconium salts are also believed to complex with the diacid
groups of poly(vinyl ether-maleic acid). More than likely, positive charges from the aluminum or zirconium
ions are attracted to the negative charge of the deprotonated acid groups of poly(vinyl ether-maleic acid).
Another approach to maintaining the antiperspirant salt and the maleic anhydride polymer separate
prior to application would be to utilize a water-in-oil emulsion system in which the antiperspirant salt along
with an emulsifier would be present in the continuous oil phase and the polymer in the dispersed water
phase.21 Other types of suspension systems can also be employed.20
Polyelectrolyte complexes formed between poly(methyl vinyl ether-maleic anhydride) and poly(vinyl
pyrrolidone-methacrylamidopropyl trimethylammonium chloride) exist in the form of microgels and may
be utilized in various antiperspirant vehicles, including sticks, aerosols, and roll-ons.22 A key advantage of
the polyelectrolyte system is its low viscosity allowing it to be used in various product vehicles and its ability
to form clear antiperspirant films, which is more aesthetically pleasing to consumers. It is reported that
concentrations as low as 1% (w/w) of antiperspirant salts can be employed in combination with maleic
anhydride-based polyelectrolyte complexes providing the same efficacy as antiperspirant formulations
containing 10% (w/w) of antiperspirant salts.
Concluding Remarks
Maleic anhydride and its derivatives have many applications related to skin. In this first article of the
series, we attempt to review several polymeric entities based on maleic anhydride chemistry and their
application in the biomedical and personal care industry. Universally, polymers based on maleic anhydride
are well known for their bioadhesive properties and are used in a variety of biomedical applications
including biosensors. Furthermore, similar chemistries are found in applications in wound healing acting
as a delivery and retention agent for nitric oxide. In the personal care industry its uses include, but are not
limited to, adjuvants in antiperspirant formulations, skin-tightening agents, and key components of pore
strips for keratotic plug removal. The next sequence of this article will be published in a future issue of
Cosmetiscope and will discuss the role of maleic anhydride derivatives in transdermal delivery.
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References
1. US 2,866,772. J. Sellers, Method of preparing adhesive composition comprising a maleic anhydride copolymer and product
obtained. 1958.
2. US 3,005,802. J. Sellers, Adhesive salt of an ester of a maleic anhydride copolymer. 1961.
3. US 3,002,955. J. Sellers, Cross-linked maleic anhydride copolymers. 1961.
4. US 3,988,495. J. Lowey and T. Frommherz, Methyl vinyl ether-maleic ester copolymer. 1976.
5. US 5,106,914. G. Russell and J. Pelesko, Pressure sensitive adhesive compositions and elements made therefrom. 1992.
6. US 6,583,225 B1. K. Plochocka and J. Lynn, Polymeric hydrogels. 2003.
7. A. Woolfson, D. McCafferty, C. McCallion, E. McAdams, and J. Anderson, Moisture-activated, electrically conducting
bioadhesive hydrogels as interfaces for bioelectrodes: effect of formulation factors on cutaneous adherence in wet
enviroments. J Appl Polym Sci 1995, 56, 1151-1159.
8. A. Woolfson, D. McCafferty, C. McCallion, E. McAdams, and J. Anderson, Moisture-activated, electrically conducting
bioadhesive hydrogels as interfaces for bioelectrodes: effect of film hydration on cutaneous adherence in wet environments.
J Appl Polym Sci 1995, 58, 1291-1296.
9. A. Woolfson, Moisture-activated, electrically conducting bioadhesive interfaces for biomedical sensor applications. Analyst
1996, 121, 711-714.
10. M. Witte, T. Kiyama, and A. Barbul, Nitric oxide enhances experimental wound healing in diabetes. Br J Surg 2002, 89,
1594-1601.
11. M. Witte and A. Barbul, Role of nitric oxide in wound repair. Am J Surg 2002, 183, 406-412.
12. WO 2009/026680 A1. P. Lee and Y. Li, Supramacromolecular polymer complexes providing controlled nitric oxide release
for healing wounds. 2009.
13. WO 2011077281 A2. P. Schorr, D. Hoffman, I. Weart, and K. Yang, Skin preparation that immobilizes bacteria. 2011.
14. EP 2,515,783 A2. P. Schorr, D. Hoffman, I. Weart, and K. Yang, Skin preparation that immobilizes bacteria. 2012.
15. M. Roh, M. Han, D. Kim, and K. Chung, Sebum output as a factor contributing to the pore size of facial pores. Cutan Biol
2006, 155, 890-894.
16. WO 1998042303 A1. B. Crotty, P. Miner, A. Johnson, A. Znaiden, J. Corey, A. Vargas, A. Meyers, and B. Lange, Cosmetic
product. 1998.
17. US 5,968,537. B. Crotty, P. Miner, A. Johnson, and A. Znaiden, Cosmetic product for removal of keratotic plugs from skin
pores. 1999.
18. US 6,174,536 B1. B. Crotty, P. Miner, A. Johnson, and A. Znaiden, Cosmetic product for removal of keratotic plugs from
skin pores. 2001.
19. US 2002/0119108 A1. H. Rieley and K. Smith, Antiperspirant products. 2002.
20. US 2005/0100521 A1. M. Cropper, Antiperspirant compositions. 2005.
21. US 2006/0051306 A1. N. Brown, H. Rieley, I. Smith, and J. Stockton, Antiperspirant emulsion compositions. 2006.
22. US 2010/0297201 A1. T. Gillece, L. Foltis, D. Koelmel, A. Luschen, and C. Barrett, Use of polyelectrolyte complexes in
antiperspirant technology. 2010.
23. WO 2013052454 A1. H. Fares and D. Prettypaul, Antiperspirant/deodorant compositions. 2013.
24. B. Travedi and B. Culbertson, Maleic Anhydride. Plenum Press: New York, 1982.
Making Personal
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About the author:
R
oger is a Principal Scientist in the Materials Science Department at Ashland
Specialty Ingredients. He received a B.S. in Chemistry from Saint Vincent
College and completed a Ph.D. in Biophysical Chemistry at Seton Hall
University. Roger has over 18 years of experience in the Personal Care industry,
having worked in many facets of product development and claims substantiation
leading to the commercial launch of new technologies. His work and professional
activities reflect his dedication and service to the personal care industry with
specialties in imaging and optical techniques used in conjunction with image
analysis to quantify various properties of hair and skin, spectrofluorescence of hair and skin, mechanical
measurements of personal care substrates, and various aspects related to the use of antioxidants and other
active ingredients in skin care. Roger actively speaks at international conferences and is the primary author
of over 25 peer-reviewed book chapters and journal articles. He is also the author of the book, Antioxidants
and the Skin, published in 2013. For the past eight years, Roger has been the editor of the monthly periodical,
Cosmetiscope, of the New York Chapter of the Society of Cosmetic Chemists. He is also an Adjunct Professor
at Fairleigh Dickinson University, where he teaches Biochemistry to students in the Cosmetic Science
Master's program. Prior to pursuing a career in science, Roger served in the U.S. Navy onboard the vessel,
USS YORKTOWN (CG 48).
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Higher clarity suspending
polymer
Contact: 888-776-7337
[email protected]
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89th ACS Colloid & Surface Science Symposium
Carnegie Mellon University • Pittsburgh, PA
June 15-17, 2015
For more info: http: www.colloids2015.org.
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BOTANICAL
EMOLLIENTS
& SPECIALTY
PARTICLES
24/7 Online
Ingredient
Information:
www.floratech.com
Label
The Natural Solution
®
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In the New York
SCC Region:
DWI Leibniz-Institut für Interaktive Materialien
HairS’15
19th International Hair Science Syposium • Trier, Germany
September 2-4, 2015
Essential Ingredients
Michael Manning
201.576.9382
[email protected]
Call for Papers – End of DECEMBER 2014
Abstract Submission
Proposals for oral/poster presentation (1 page max.)
should be sent to [email protected] by March 27, 2015.
Symposium Fee
Early bird fees for registration and payment by August 1, 2015 are:
• 770€ for participants
• 590€ for DWI member companies
• 330€ for speakers (one presenting author per oral presentation,
no reduction for poster authors)
The Soul & Science
of Beauty.
www.evonik.com/personal-care
Fee includes meals, coffee breaks, excursion, conference dinner, book of abstracts, and conference proceedings.
For more info: www.dwi.rwth-aachen.de.
Inspire
Imagine
Innovate
The US Society of Cosmetic Chemists hosts the 29th IFSCC Congress
O
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WF
RONTIERS
Nature’s Science.
Walt Disney World Dolphin Resort
Lake Buena Vista, Florida
BEY
™
OND DREAM
SI
NT
October 23-26, 2016
29TH CONGRESS
O R L A N D O, F L 2 016
INS PIRE IMAGINE INNOVATE
Our Technology.
Your Beauty.
Beyond Dreams into New Frontiers: Inspire, Imagine, Innovate
www.ajiaminobeauty.com
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Helena Rubinstein:
Beauty Is Power
Friday, March 13, 2015
H
The Jewish Museum
elena Rubinstein was a legendary cosmetics entrepreneur whose
ideas challenged and changed the myth of feminine beauty. This
exhibit is devoted to her life and art collection, and presents a
strong female perspective on 20th century visual culture. She introduced
new and different standards of beauty, and exhorted women to control
their own image though makeup and grooming.
Today, the term “beauty salon” is limited to a hair dresser or day spa. However, Rubinstein’s salon was
designed as a place where women could learn not only how to improve their looks, but also how to
reconceive their standards of taste, and to understand design, color, and art to express their own personalities.
Location: The Jewish Museum, 1109 5th Ave. (at 92nd Street), NY, NY
Time: Guided tours at 1:00 pm and 2:00 pm. Each group limited to 20 persons.
Cost/Registration: • NYSCC Pre-registered Member $85.00
• Pre-registered Non Member $105.00
• Emeritus / Students Pre-registered $40.00
• Emeritus at the door $75.00
• At The Door $120.00
Register online by visiting the NYSCC website at www.nyscc.org.
• Limited to the first 40 people.
• Price includes: Guided Tours of “Beauty is Power.”
• General Admission to the museum.
• Discount coupons for the museum store.
• Bus Transportation from New Jersey.
• Validated parking for cars parked at private garage.
• Late lunch or early dinner.
For more information: https://nyscc.org/event-calendar/
Employment Opportunities
For complete ads please go to the NYSCC website: https://nyscc.org/employment/employment-listings/
n Director of Personal Care – Business Development
Gattefossé USA, Paramus, NJ
n Director R&D
Presperse Corporation, Somerset, NJ
n Formulation Chemist – Temporary Position
Hayward Laboratories, Inc., East Stroudsburg, PA
n Sales
Sajmil Corporation, Inc., New York, NY
n Principal Formulation Chemist
Spartan Brands, Inc., New York, NY
n Northeast Account Manager
Presperse Corporation
Home office and New Jersey office.
n Scientist, Clinical Research
BASF, The Chemical Company, Tarrytown, NY
n Marketing Manager – Hair Care
BASF, The Chemical Company, Florham Park, NJ
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n Product Development Chemist
Melaleuca, Inc., Idaho Falls, ID
n Chemist, Technical Services
Kobo Products, Inc., South Plainfield, NJ
n Green Chef Director
Method Products PBC, San Francisco, CA
n Technical Marketing – Lab Services
Verla International, Ltd., United States
n Senior Scientist, Cleansing Platform
Johnson & Johnson, Skillman, NJ
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GORDON RESEARCH CONFERENCE
Barrier Function of Mammalian Skin
Defining, Investigating and
Surmounting the Barrier
August 16-21, 2015
Waterville Valley Resort
Waterville Valley, New Hampshire
Gran Via
Barcelona
April 14-16, 2015
More info: www.in-cosmetics.com.
Make note of it…
Send news of interest, guest editorials, and comments to
Roger McMullen, Editor • E-mail: [email protected]
Call for Papers
T
he Cosmetiscope editorial committee invites all interested parties to submit feature
technical articles for publication in the NYSCC monthly newsletter. Authors of
feature articles are eligible to win the prestigous NYSCC Literature Award
($1,000) for the best front-page article published during the calendar year. Also,
authors receive $200 reimbursement to attend a theatrical performance of their choice.
Writing an article for your peers is a very rewarding experience, both personally and
professionally, and would reserve your place in NYSCC history. You may choose whatever
topic you feel would be interesting to fellow colleagues in our industry. We also
welcome any other types of commentaries or articles that may be published in the
Career Corner, Technical Tidbit section, or as a Letter to the Editor.
Please send correspondence to: [email protected].
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