anti drakkar noir perspirant

SCS Summer School
Fragrance
Marianne Martin
www.earthscentred.co.uk
1
Aims
• To inspire your interest in fragrance
• To encourage an understanding of
the chemistry of perfumery
• To help prepare you for the SCS
distance learning diploma
examination
2
Learner Outcomes
by the end of the session learners will be able to:
• Describe at least one extraction
techniques for fragrance
ingredients of natural origin
• Build a perfume molecule
• Describe the use of at least one
synthetic and one natural
ingredient in modern perfumery
• Use a smelling blotter
3
What are these botanicals?
4
Finding out about:
each other and our sense of smell
In groups of 3 to 5 people find out:
1.
2.
3.
4.
Each other’s name/s
Any professional work with fragrance
Any strong memories related to scent
Can you identify all the botanicals on
the plate between you?
5. If not describe their odour
6. They all contain essential oils in tiny
sacs. You can only see the oil sacs
with the naked eye in one of the
botanicals. Can you see which one?
5
Finding out about:
each other and our sense of smell
In groups of 3 to 5 people find out:
6. They all contain essential oils in tiny
sacs. You can only see the oil sacs
with the naked eye in one of the
botanicals. Can you see which one?
7. Choose a spokes person to tell the
best anecdote or reaction to the
botanicals to the whole group
6
Lemon
Citrus Medica Limonum
• Citrus fruit
• Grown in Sicily
• Essential oil sacs
0.4-0.6mm
diameter
• Cold extraction
techniques
7
Cold pressed or expressed oil production
8
Lemon
Citrus Medica Limonum
• The odour of the fresh
essential oil is mouth
wateringly close to the
original
• Citrus oils are prone to
oxidation and
deteriorate quickly
• How would you store a
citrus oil to improve its
shelf life?
9
What are these botanicals?
10
Rosemary
Rosmarinus Officinalis
• Herb
• Reputed to aid memory
• In ancient Greece students
would rub rosemary on their
foreheads before exams to
help them remember
11
Rosemary
Rosmarinus Officinalis
• Alpha and beta wave patterns
in the brain are affected by
rosemary
• Most people feel more alert
but calm when smelling
rosemary
12
Rosemary
Rosmarinus Officinalis
• Rosemary oil contains camphor
• Camphor is found in medicated products
such as Vick’s vapour rub
• In perfumery we use the term
camphoraceous meaning smells
camphor like
camphor
13
Lavender
Lavandula Aungstifolia
• Relaxing for many people
• Helpful for insomnia
• In perfumery used both for
its floral aspect and its
herbaceous aspect
• Plays a part in the eau de
cologne accord and in
many male fine fragrances
• In studies lavender
treatment decreased beta
waves which indicates
drowsiness
14
Some academic studies confirming the
effects of rosemary oil and lavender
EEG activity, alertness, and mood were assessed in 40 adults given 3 minutes of
aromatherapy using two aromas, lavender (considered a relaxing odor) or
rosemary (considered a stimulating odor). Participants were also given simple
math computations before and after the therapy. The lavender group showed
increased beta power, suggesting increased drowsiness, they had less depressed
mood (POMS) and reported feeling more relaxed and performed the math
computations faster and more accurately following aromatherapy. The rosemary
group, on the other hand, showed decreased frontal alpha and beta power,
suggesting increased alertness. They also had lower state anxiety scores,
reported feeling more relaxed and alert and they were only faster, not more
accurate, at completing the math computations after the aromatherapy session.
(Diego et al, 1998)
A study with 140 participants looked at the effects on memory of lavender oil,
rosemary oil and no odour (the control group). The rosemary group showed
overall improved quality of memory but with an impairment of speed compared
to the control.
(Moss et al, 2003)
Rosemary oil said to have a positive effect on mood, concentration and memory
for 10 subjects.
(Svoboda et al, 2002)
15
Clove Buds
Eugenia Caryophyllus
• Spice
• Contains 75-80% eugenol
• What problems might occur in
personal care products containing
clove oil?
eugenol
Photographs by Tony Burfield
16
Clove Buds
Eugenia Caryophyllus
• Spice
• Contains 75-80% eugenol
• Eugenol is one of the commonly
reported EU allergens
• How could the addition of clove oil
affect the INCI label of a personal
care product?
eugenol
Photographs by Tony Burfield
17
Fragrances including
Clove oil
Old Spice, Shulton, 1938
Opium, Yves St Laurent, 1977
18
Frankincense or Olibanum resin
Boswellia Carterii
• Frankincense oozes from the
stems of a bush and hardens in
the sun
• The bushes grow in arid
regions of Yemen and Southern
Arabia
• In ancient times there was an
incense trade route
• Wars were fought over the
control of frankincense trade
Censer 3rd century BC
Shabwa, Yemen
19
British museum collection
Photo by Muhammad Al Shanfari
20
Frankincense or Olibanum resin
Boswellia Carterii
• Olibanum is processed by steam
distillation to make the essential oil
• Olibanum is also extracted using
hydrocarbon solvents to make the
resinoid
• In which products can the sticky
resinoids cause problems?
21
Fragrances containing
Frankincense or Olibanum resin
Boswellia Carterii
2MAN
Comme des Garçons
2004
22
Benzoin
INCI name
Botanical name
Styrax Benzoin
Styrax Tonkinensis
Geographic Origins
Thailand, Indonesia, Philippines
Botanical part
Exudate from tree trunk
Extract
Resinoid
Odour family
Balsamic
23
Benzoin
Balsamic Family
•
•
•
Balsams are odorous resinous exudates from shrubs found in
the desert
They are sweet smelling and warm so vanilla is included in the
balsamic odour family although it is from a dried bean
Balsams and balsamic notes include:
Benzoin
Myrrh
Frankincense or Olibanum in the perfumery trade
Opoponax
Peru Balsam
Tolu Balsam
Cistus
Labdanum
Vanilla
Olibanum
Myrrh
24
Vanilla
Pink Pepper
Shinus Molle
•
•
Relatively new perfumery
material (1990s onwards)
Extraction method uses
•
liquid CO2
•
under high pressure
•
in costly equipment
•
made of 20mm thick
stainless steel
25
CO2 Extraction
Extraction
columns
charged with
botanical
Condenser – Evaporator
Containing heat exchangers
Liquid CO2
storage tank
Sump collecting crude
extraction product
26
Fragrances including
Pink Pepper
Pleasures, Estée Lauder, 1995
27
Fragrances including Pink Pepper
Prada, Prada, 2004
Tokyo, Kenzo, 2007
Gucci Guilty, Guicci, 2012
28
Fragrances including Pink Pepper
Eau des Merveilles, Hermes, 2004
29
Tonka bean
Dipteryx odorata
The tree that yields tonka
beans is from central
America especially
Venezuala
30
Tonka bean
Dipteryx odorata
Tonka beans contain
coumarin
31
The first synthetic used in perfumery
Coumarin
IUPAC name
Chromen-2-one
Functional group
Lactone
Occurrence
Found in nature
e.g. Tonka beans
Odour note
Powdery
Perfumery uses
Part of the bottom note accord
Blends well with moss, balsamic
notes and other lactones
Fougère Royale, Houbigant,
1882 contained about 50%
of the recently synthesised
chemical coumarin
32
The First “Modern” Perfume
•
Fougère Royale, Houbigant, 1882
contained about 50% of the recently
synthesised chemical coumarin
•
•
•
Fougère means fern in French
Ferns have little or no odour
Houbigant said in his marketing:
“If God had created an odour for fern it
would be Fougere Royale”
33
THE FOUGÈRE ACCORD
Fougère
Houbigant
1882
Paco Rabanne
pour homme
Paco Rabanne
1964
Brut
Shulton
1973
Drakkar Noir
Guy Laroche
1982
1988
Coolwater
Davidoff
Hugo
Hugo Boss
1995
2013
Le Beau Male
Jean Paul Gaultier
34
Variation in Odour Perception
Student Odour Recognition Journal entries for Calone
a) Watermelon; fresh, sweet; reminds me of
a summer picnic with watermelon to eat
b) Smells like watermelons and cucumbers;
fresh, watery, aquatic feel
c) Fresh ozonic; reminds me of sea shore,
shells, fish, marine life
d) Ocean, salty, fishy; matt, wet; reminds me
of a smelly beach, not pleasant
35
Influence of Synthetics in 20th Century Perfumery
Calone
IUPAC name
7-Methylbenzo(1,4)dioxepin-3-one
Functional group
Cyclic diether and ketone
Occurrence
Not found in nature
Odour Family
Aquatic
Perfumery uses
Fresh ozonic, marine note and water
melon. Calone is evident throughout
the fragrance profile
Trend setter
Calone was patented in 1966 but
waited until the 1990s to create a new
fashion in fragrance:
New West for him,
Aramis, 1988
36
Influence of Synthetics in 20th Century Perfumery and beyond
Fragrances containing Calone
New West for him
Aramis, 1988
Escape for women
Calvin Klein, 1991
Acqua di Giò
Giorgio Armani 1996
L’Eau d’Issey
Issey Miyake
1992
Boss Pure
Hugo Boss
2008
L’Eau par Kenzo pour Homme
Kenzo 1999
37
Find out about fragrance on the web
• www.osMoz.com
• www.fragrantica.com
• www.basenotes.net
38
Fragrance Exam Question 2013
a) Answer all parts:
Part 1
State which extraction technique would be used in each of the following
scenarios to produce ingredients for the fragrance industry and briefly give
your reasons:
a) Scenario 1: You are a poor farmer trying to supplement your income with a 2 marks
cash crop. You grow vetivert to create terracing on your land. How would you
process the vetivert root with limited capital resources?
b) Scenario 2: Jasmin is a delicate flower the odour is destroyed at high
2 marks
temperatures. With fellow farmers and the aid of a fragrance raw material
producer you create a cooperative to process jasmin flowers. What extraction
method/s would you use to make a product that can be used in alcoholic
perfumery?
c) Scenario 3: You are a flavour/fragrance raw materials producer. There is a 2 marks
huge demand for natural vanilla flavours. What equipment might you invest
in to produce a vanilla extract eligible for natural accreditation by COSMOS or
Ecocert?
Part 2
9 marks
Describe in detail the extraction techniques used in scenario 2 above.
39
Fragrance Exam Question 2013
a) Answer all parts:
Part 1
State which extraction technique would be used in
each of the following scenarios to produce
ingredients for the fragrance industry and briefly
give your reasons:
a) Scenario 1: You are a poor farmer trying to
supplement your income with a cash crop. You
grow vetivert to create terracing on your land.
How would you process the vetivert root with
limited capital resources?
2 marks
40
Vetivert oil
INCI name
Vetiveria Zizanoides
Geographic Origins Indonesia, Haiti, Bourbon, India
Botanical part
Root
Extract
Oil
Odour family
Woody
Vetivert root
Vetivert bundles
Vetivert Distillation
41
Vetivert oil
INCI name
Vetiveria Zizanoides
Geographic Origins Indonesia, Haiti, Bourbon, India
Botanical part
Root
Extract
Oil
Odour family
Woody
Vetivert is a grass
above ground with
a deep odorous
root system
Vetivert being planted for terracing
Vetivert is used here to help protect
the more delicate crop basil
42
Water Distillation
• Distillation is mentioned as early as 200-300 AD
• A still with a more efficient condensing system was invented
by Arab chemists around 11th or 12th century AD
Arabic manuscript in the British Library
43
Stem Distillation
44
Fragrance Exam Question 2013
a) Answer all parts:
Part 1
State which extraction technique would be used in
each of the following scenarios to produce
ingredients for the fragrance industry and briefly
give your reasons:
b) Scenario 2: Jasmin is a delicate flower the odour 2 marks
is destroyed at high temperatures. With fellow
farmers and the aid of a fragrance raw material
producer you create a cooperative to process
jasmin flowers. What extraction method/s would
you use to make a product that can be used in
alcoholic perfumery?
45
46
Jasmine
Jasminum Officinale
• Solvent extraction with a
hydrocarbon solvent
produces jasmine concrete
• 30°C process temperatures
do not destroy the delicate
odour
• Concretes contain waxes
and pigments as well as the
odorous materials that are
not soluble in alcohol
• Further extraction with
alcohol makes the absolute
47
Fragrance Exam Question 2013
a) Answer all parts:
Part 1
State which extraction technique would be used in
each of the following scenarios to produce
ingredients for the fragrance industry and briefly
give your reasons:
c) Scenario 3: You are a flavour/fragrance raw
2 marks
materials producer. There is a huge demand for
natural vanilla flavours. What equipment might
you invest in to produce a vanilla extract eligible
for natural accreditation by COSMOS or Ecocert?
48
CO2 Extraction
Extraction
columns
charged with
botanical
Condenser – Evaporator
Containing heat exchangers
Liquid CO2
storage tank
Sump collecting crude
extraction product
49
CO2 Extraction
The Process
• The liquid CO2 is passed over the botanical in a series of extraction
columns
• The liquid CO2 laden with extract passes into the evaporator where
the CO2 is allowed to vaporise and removed from the extract
• The CO2 is condensed and passed into the storage tank to be used
again
• The extract drains out of the evaporator and is collected
Costs
• The pressures involved to maintain the liquid CO2 are very high
• The equipment is made of thick stainless steel
• Capital costs are high
50
CO2 Extraction
Extraction
columns
containing
raw material
Condenser – Evaporator
Containing heat exchangers
Liquid CO2
storage tank
Sump collecting crude
extraction product
51
Below are photographs of some of the
botanicals extracted using CO2
Vanilla
Green tea
Coffee
Pink Pepper
52
Fragrance Exam Question 2013
a) Answer all parts:
Part 1
State which extraction technique would be used in each of the following scenarios to
produce ingredients for the fragrance industry and briefly give your reasons:
b) Scenario 2: Jasmin is a delicate flower the odour is
2 marks
destroyed at high temperatures. With fellow farmers and
the aid of a fragrance raw material producer you create a
cooperative to process jasmin flowers. What extraction
method/s would you use to make a product that can be used
in alcoholic perfumery?
Part 2
Describe in detail the extraction techniques used
in scenario 2 above.
9 marks
53
Solvent extraction
• Charge the vessel with the botanical in this case
rose petals
54
This shows the spent
rose petals after
extraction
Also the perforated
plates separating the
petals allowing the
solvent to penetrate
55
56
Diagram without labels to help with revision:
Solvent Extraction
57
Solvent
SolventExtraction
Extraction
58
Solvent Extraction
The Process
• The extraction vessel is charged with the botanical
• Perforated plates allow for thorough contact between the solvent and
the botanical
• The hydrocarbon solvent is added to the vessel
• Process temperatures around 30°C are typical
• After some time the hydrocarbon extract solution is tapped off
• The solvent is removed from the extract by vacuum distillation
• The recovered solvent is often reused in future batches
• The extraction vessel needs to be cleaned removing all the spent
charge
• Steam is used to clean the vessel but is not part of the extraction
process
59
Solvent Extraction
Concrètes
• The hydrocarbon solvent extracts non-odorous materials from the
botanical as well as the odorous materials
• The non-odorous materials are mainly waxes and colours
• Concrètes are insoluble in alcohol (ethanol) or water based systems
• They can be used directly in soap perfumery and non-aqueous
balms
• Concrètes are the starting point for further extraction with ethanol
to produce absolutes
Absolutes
•
•
•
•
An absolute is made by mixing ethanol with the concrète
Tapping off the ethanol solution from the waxes
Distilling off the alcohol under vacuum
Absolutes are soluble in alcohol (ethanol) but still contain colour
60
Comparison of extraction techniques
Extract
Temp of
process
Hydrolysis
Protein
degradation
“stilly”odours
Cold Pressed
essential oil
from
citrus fruit
Ambient
Essential oil 100°C
Contains
waxes
Contains
colour
Sometimes if
there is
contact with
juice
X
√
√
√
√
X
Low levels
Capital
investment
for
equipment
Certified
Natural by
COSMOS
Low to
Medium
√
Low
√
(Higher for
vacuum and dry
steam)
by
Steam
distillation
(lower if
vacuum
applied)
(less if dry
steam used)
Concrete
ca 30°C
X
X
√
High levels
Medium
X
Absolute
ca 30°C
X
X
X
High levels
Medium
X
Sub critical
10-20°C
typical
X
X
X
Medium
Very high
√
Super critical
31°C+
X
X
X
Medium
Very high
√
CO2 extract
61
STABILITY of PERFUME in the PRODUCT BASE
62
ACCELERATED PERFUME STABILITY TESTING IN FRAGRANCED END-PRODUCT
General Principle:
The rate of reaction doubles for every 10°C rise in temperature
Thus 24 months stability @ 20°C ≈ 6 months @ 40°C
Typical Test Conditions
•
•
•
•
•
Fridge (3°C) Control
Room Temperature (20°C) 6 months
40°C Oven 3 months and 6 months
55°C Oven 1 week
UV light (over night)
63
ACCELERATED PERFUME STABILITY TESTING IN FRAGRANCED END-PRODUCT
CONTROLS
Typical Test Conditions
•
•
•
•
•
Fridge (3°C) Control
Room Temperature (20°C) 6 months
40°C Oven 3 months and 6 months
55°C Oven 1 week
UV light (over night)
Unperfumed control
• Always include an unperfumed control in accelerated
stability testing kept at all the conditions above
• The unperfumed control base must include all additives for
the variant accept the fragrance
• If problems arise in the unperfumed base they are then not
caused by the fragrance
• The unperfumed control helps in odour assessment
64
STABILITY
TYPICAL PH FOR VARIOUS PRODUCTS:
pH
1
Product base
Acid cleaners: Limescale removers
2
3
ACID
4
Anti-perspirant roll-on / Self tanning creams
5
Anti-perspirant deodorants aerosol
5.5
Alcoholic perfumes: Eau de Toilettes etc
6
NEUTRAL
7
Creams / Lotions / Shampoos / Shower gels / Bath foams
8
9
ALKALINE
10-11
Soaps
Low cost soaps / Perm lotions / Depilatories
12
13
14
Alkaline cleaners
65
STABILITY
PERFUME INGREDIENTS AFFECTED by pH of PRODUCT
For example:
• Esters may be affected by pH of product
• De-esterification to acids and alcohols
• If the acid involved has an unpleasant odour, such as
acetic acid found in vinegar, de-esterification will usually
lead to a failed stability test
• If the acid involved is odourless such as salicylic acid the
odour character after de-esterification is often acceptable
• Sterically hindered esters tend to be more stable
66
STABILITY
PERFUME INGREDIENTS AFFECTED by pH of PRODUCT
What types of personal care products will encourage deesterification reactions?
• Answer: Aqueous products with acid pH
• Such as: Antiperspirant deodorant roll-on pH 4
67
Terpenes and Terpenoids
•
•
•
Isoprene is the building block of essential oil chemistry
Monoterpenes can be considered as two isoprene units together “head to tail”
Sequiterpenes can be considered as three isoprene units joined together
Isoprene
2-Methylbut-1,3-diene
“head”
“tail”
Isoprene unit
Isoprene units joining up to make d-limonene
Is d-limonene a monoterpene or a
sesquiterpene?
68
Monoterpenes
•
•
•
•
•
•
•
Strictly speaking monoterpenes are hydrocarbons
Hydrophobic
Very volatile
Easily oxidised to peroxides at double bonds
Top notes
D-Limonene is the major constituent of citrus oils (99% of orange oil)
Pure D-Limonene is very low in odour
69
Sequiterpenes
• “Sequi” is a Latin prefix which means half as much again
• Terpenes have 10 carbons and sesquiterpenes 15
• Sesquiterpenes are less volatile and contribute to the heart of
the fragrance
• Patchouli oil contains a complex mixture of sesquiterpenes
including beta selenine below (and its main constituent
patchoulol a sequiterpenoid)
Isoprene units (in red) joining up to make
beta selenine
Beta selenine
70
Sequiterpenes
• “Sequi” is a Latin prefix which means half as much again
• Terpenes have 10 carbons and sesquiterpenes 15
• Sesquiterpenes are less volatile and contribute to the heart of
the fragrance
• Patchouli oil contains a complex mixture of sesquiterpenes
including beta selenine below (and its main constituent
patchoulol a sequiterpenoid)
71
Aims
• To inspire your interest in fragrance
• To encourage an understanding of
the chemistry of perfumery
• To help prepare you for the SCS
distance learning diploma
examination
72
Learner Outcomes
by the end of the session learners will be able to:
• Describe at least one extraction
techniques for fragrance
ingredients of natural origin
• Build a perfume molecule
• Describe the use of at least one
synthetic and one natural
ingredient in modern perfumery
• Use a smelling blotter
73
• Good luck with your studies
:
• The average person
takes about
3 million breaths a year
• Enjoy your sense of smell
Thank you
74