P. 1
Perfumery as Science (Steeve Herman)

Perfumery as Science (Steeve Herman)

|Views: 324|Likes:
Published by SpiceandWood
Perfumery as Science
Perfumery as Science

More info:

Published by: SpiceandWood on Apr 01, 2011
Copyright:Attribution Non-commercial

Availability:

Read on Scribd mobile: iPhone, iPad and Android.
download as PDF, TXT or read online from Scribd
See more
See less

09/12/2015

pdf

text

original

Perfumery as a Science

Steve Herman

FRAGRANCE CREATION

VOLATILITY

For a molecule To have odor, MW<300 for appreciable vapor pressure at RT

BASIC COMPOSITION
FRAGRANCE TRIANGLE
25%

TOP

25% 50%

MIDDLE BOTTOM

Jean Carles: Evaluate volatility Construct accords Build from bottom up

CARLES BASE ACCORD
Oakmoss Ambergris 9 8 7 6 5 1 2 3 4 5

Selects 6:4, needed musk for chypre character: 6 Oakmoss 4 Ambergris 1 Musk Ketone

ADD MIDDLE
Adds floral and animal notes: 3 1 6 4 1 Absolute Rose Absolute Civit 10% Oakmoss Ambergris Musk Ketone

TOP ADDED
Pleasant, highly volatile notes for sparkle: 4 Sweet Orange Oil 1 Bergamot 3 Absolute Rose 1 Absolute Civit 10% 6 Oakmoss 4 Ambergris 1 Musk Ketone

FRAGRANCE CHEMICALS

CHEMICAL TYPES
• • • • • • • • Alcohols Aldehydes & Ketones Aliphatic & Aromatic Esters Nitriles Ethers Lactones Heterocyclics Terpenes

ALCOHOLS
R-OH Aliphatic OH

Aromatic

ALDEHYDES & KETONES H C=O R R’ C=O R Ketone Aldehyde

TERPENES #1
Isoprene Units Joined Head To Tail
(C5H8)n C I C=C-C=C

TERPENES #2
n 2 3 4 6 8 Name Monoterpene Sesquiterpene Diterpene Triterpene Tetraterpene Formula C10H16 C15H24 C20H32 C30H48 C40H64

ACYCLIC TERPENES

β-Myrcene

MONOCYCLIC TERPENES

Limonene

BICYCLIC TERPENES

Pinene

SESQUITERPENE

γ-Bisabolene

NITRILES
R-C=N C=N Aliphatic

Aromatic

BASIC HETEROCYCLIC STRUCTURES

N

O +

S +

N H

O

S

HETEROCYCLICS

N H

Indole

LACTONE
A Cyclic Ester
γ or δ Hydroxy Acid forms 5 or 6 member ring by intramolecular esterfication -Na+ RCHCH2CH2COO

I OH

LACTONES

O

O

Coumarin

NITROMUSKS
C((CH)3)3 NO2 NO2 CH3 NO2 NO2 C((CH)3)3 NO2 NO2

CH3

CH3 C=O I CH3

CH3

Musk Xylene

Musk Ketone

POLYCYCLIC MUSKS

O

Galaxalide

FRAGRANCE DILUENTS 1
CH3CHCH2-O-CH2CHCH 3 I I OH 0H

Dipropylene Glycol (DPG)
CH3CHCH2OH I OH

Propylene Glycol (PG)

FRAGRANCE DILUENTS 2
HOCH2CH2CHCH3 I OH CH3 I CH3CCH2CHCH3 I I OH OH Butylene Glycol

Hexylene Glycol

SCHIFF BASE #1
Aldehyde + Amine
H 2N CHO + OH COOCH3

HydroxyCitronellal

Methyl Anthranilate

SCHIFF BASE #2
COOCH3 CH=N OH + H 2O

Aurantiol

CHEMICAL REACTIONS
HELPFUL REACTIONS Part of the natural maturing process HARMFUL REACTIONS Occur in isolated perfume oils or in reaction with base environment

STORAGE EFFECTS
• • • • Elevated Temperatures UV Radiation Moisture Oxidation Accelerate change or deterioration

AUTOOXIDATION
CHO COOH

Benzaldehyde

Benzoic Acid

POLYMERIZATION
Aldehydes can Solidify OH I CH2CH-CHCHO

CH2CHO 2

Phenylacetaldehyde

HEMIACETALS
Aldehyde/Ketone + Alcohol

O II I C +- C- OH
Loose, reversible aging hydroalcoholics

OH I C O C

ESTER HYDROLYSIS
O OH -OH

O

Benzyl Acetate

Benzyl Alcohol

LACTONE HYDROLYSIS
O -OH O O HO OH

Epsilon Hexalactone

6-Hydroxy Hexanoic Acid

FRAGRANCE APPLICATIONSPERSONAL CARE

CHEMICAL EXAMPLES 1
PEA
.

CH2CH2OH
β-Pinene

CHEMICAL EXAMPLES 2
Hydroxycitronellal OH CH3
I I

CH3CCH2CH2CH2CHCH2CH I II CH3 O

CH3 HOCH2CH2CH CH3 Amyl Alcohol

SOLUBILITY PARAMETER
Measure of all the cohesive forces in a molecule Refinement of “polar” “nonpolar” division

CLOG P
Calculated LOGarithm of the octanol/water Partition Coefficient
Trinh et al 5,783,544, 1998

SMILES SIMPLIFIED MOLECULAR INPUT LINE ENTRY SYSTEM
Allows entry of chemical structures into computer programs to predict properties

EXAMPLE SMILES
Case ImportantAliphatic Upper Case Aromatic Lower Case Hydrogen Not Included SINGLE BOND C-C DOUBLE BOND C=C TRIPLE BOND C#C Rings- # at start and end e.g. c1ccccc1Br is Bromobenzene

CLOG P VANILLIN
SMILES: COc1cc(C=O)ccc1O

HO

H3C

O

CH O

CONSEQUENCE

Fragrance will partition in phases of finished product

FUNCTIONAL FRAGRANCE
• Economics • Stability • Translation

TEA-STEARATE EMULSION
Air
CH2CH2OH

PEA
O

Stearyl alcohol
Amyl alcohol

TEA-Stearate
O

Hydroxycitronellal Pinene

SURFACTANTS
More stable than emulsions, but viscosity more important, often color problems

MICELLE EFFECTS
Water-Micelle Interface Between Surfactant Molecules Core of Micelle

SURFACTANT VISCOSITY
Water Sodium Laureth Sulfate (A) Cocamidopropyl Betaine (B) 1. Unperfumed 2. 2% Hydroxycitronellal 3. 2% Phenylethyl Alcohol A. Standapol ES-2 (COGNIS) B. Velvetex BK-35 (COGNIS) 67.0 18.0 15.0

VISCOSITY
1,000 800

600

400

200

0

1

2

3

FRAGRANCE APPLICATIONSHOUSEHOLD PRODUCTS

EVAPORATION CURVE

Wt Loss Days Typical Fragrance Evaporation Curve

FREE EVAPORATION
Weight 1

2 Time

3

4

LINEAR FRAGRANCE
4 3 2 1 Time

Weight

BLEACH
Bleach unstable, affected by fragrance, solubilizer, oxygen, temperaturemust test chlorine and fragrance.

DECOMPOSITION AT 100°F
5.6 5.4 5.2 5.0 4.8 4.6 4.4 4.2 4.0 3.8 3.6 3.4 3.2 3.0 2.8
0 10 20 30

% NaOCl

Days

40

50 60

70

80

90 100 110 120 130 140 150

DOWFAX STRUCTURE
SO3-X+ O R SO3-X+

TITRATION
0.1 N Sodium Thiosulfate

Titrate until clear Stirring Bar Magnetic Stirrer Bleach Test Mixture

MASKING/MALODOR
Foul odors from bacterial decomposition or unpleasant molecules

FAMOUS MALODORS
putrescine cadaverine spermidine

spermine

SKUNK ODOR
H C=C CH3 H CH2SH E-2-buten-1-thiol 38-44%

CH3 I CH3CHCH2CH2SH

3-methyl-1-butanethiol 18-26%

ALDEHYDE ACTION
3-mercapto-3-methyl-1-butanol

OH

aldehyde

+
SH R

R-CHO

Alkylated 1,3-oxathiane

O

S

METAZENE

H C=C-C H CH3

O

O-R

R=mixture from C 8H17 to C14H29

GRILLOCIN
O II C O C7H14 C6H13 I C-C2H3= CH O C 7H14

H Zn H O O C II O

CH=C2H3 -C I C6H13

CYCLODEXTRIN
A B
a ß ? A 0.57nm 0.78nm 0.95mn B 1.37nm 1.53nm 1.69nm

FRAGRANCE & COLOR
Product is formulated, fragrance is chosen, color is added, time is short…

CHROMOPHORES
Configurations which can alter the energy of delocalized systems Benzene absorbs around 200 nm We see between 400-700 nm

VISIBLE STRUCTURES
Conjugated double bonds

-C=C-C=CAZO chromophore

-N=NN=N

BENZALDEHYDE + UV
HC=0 -C=0

UV

Free radical

SYNESTHESIA

Relation of two senses, such as smell and color

Name _______________________

A ____ B ____ C ____ D ____ E ____ F ____ G ____ H ____ I ____ J ____ K ____ L ____ M ____ N ____

1

2

3

4

5

6 9 11

7

8 10

CINNAMIC ALDEHYDE

RIFM/IFRA
For thirty years, the fragrance industry has had a continuous program of safety testing, and the process has no end in sight.

PHYSIOLOGICAL CONSIDERATIONS
• • • • Skin irritation Phototoxicity Carcinogens Allergens

NON-SKIN CONTACT
• Solid air fresheners • Plug-in air fresheners • Insecticides • Toilet blocks • Incense sticks • Candles • Plastic articles

SKIN CONTACT
• • • • • • Aerosols Detergents Potpourri Carpet powders Household cleaning products Liquid refills for air fresheners

Hydroxycitronellal (Laurine, Hydronal, Phixia, Laurinal)
Last Amendment First Issued April 28, 2000 March 01, 1987

CAS # Recommendation Skin Contact Non-Skin Contact 107-75-5 Restricted 1% 10%
Hydroxycitronellal should not be used such that the level in consumer products exceeds 1%. This is equivalent to 5% in a fragrance compound used at 20% in the consumer product. This recommendation is based on a no-effect level of 10% in diethyl phthalate and on a no-effect level of 2.5% in ethanol/diethyl phthalate in standard Human Repeated Insult Patch Tests (R.A. Ford and A.M. Api, Fd. Chem. Toxic. Vol. 26, p. 921-926, 1988). The RIFM Expert Panel reviewed these data in September 1999 and concluded that no further actions were required.

CHEMICAL GROUPINGS
• A means to defend structurally related materials, without having to test every material in the group – ~ 2,000 chemically defined fragrance ingredients – 22 Groups (e.g. Acids, Acetals, Alcohols) – > 60 Subgroups (e.g. Straight chain saturated, straight chain unsaturated etc.)

RESPIRATORY SAFETY
• Selected fragrance ingredients – Benzyl acetate – Eugenol – α-Hexyl cinnamic aldehyde (HCA) – HHCB – Hydroxycitronellal – β-ionone – d-limonene – Linalool – Methyl dihydrojasmonate

CHANDLER BURR

2002

www.stephen-herman.com

Questions or Comments?

You're Reading a Free Preview

Download
scribd
/*********** DO NOT ALTER ANYTHING BELOW THIS LINE ! ************/ var s_code=s.t();if(s_code)document.write(s_code)//-->