A P R E S E N T A T I O N F R A G R A N C E C O M P A N Y

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1 A P R E S E N T A T I O N by F R A G R A N C E C O M P A N Y

2 Specially prepared for ICPC 2016 Symposium, Izmir, Turkey by Miss Maria Gika & Mr Nikos Santiris

BASICS FRAGRANCE CHEMISTRY FRAGRANCE IN PERSONAL CARE 2 FORMULATING WITH FRAGRANCE MAIN

3 O UT L I N E PART A THIS SMELLS GREAT! INCORPORATING FRAGRANCE SUCCESSFULLY INTO COSMETIC PRODUCTS 1 INTRODUCTION FRAGRANCE BASICS FRAGRANCE CHEMISTRY FRAGRANCE IN PERSONAL CARE 2 FORMULATING WITH FRAGRANCE MAIN CONCERNS QUESTIONS TO BE ANSWERED TYPICAL FUNCTIONAL ISSUES AND SOLUTIONS STABILITY TEST 3 DISCUSSION PART B AN OVERVIEW OF MARKET TRENDS IN FRAGRANCES

4 T H I S S M E L L S G R E A T INCORPORATING FRAGRANCE SUCCESSFULLY INTO COSMETIC PRODUCTS 1 INTRODUCTION FRAGRANCE BASICS FRAGRANCE CHEMISTRY FRAGRANCE IN PERSONAL CARE

5 1 FRAGRANCE BASICS INTRODUCTION Fragrance - Mixture of individual chemicals - Over a hundred compounds - Volatile ingredients - Low Molecular Weight - Three main categories

6 1 FRAGRANCE BASICS INTRODUCTION 1 - Natural - Essential Oils - Absolutes Cold expression Steam distillation Solvent extraction - Concretes - Resins 2 - Nature Identical - Vanillin Coumarin 1868 Vanilla Tonka Beans 3 - Organic synthesis - Galaxolide Galaxolide Musk Deer

7 1 FRAGRANCE BASICS INTRODUCTION Wide range of perfumery notes & categories Fruity Edible - Gourmand Aquatic - Marine Oriental Herbal Citrus

8 1 FRAGRANCE BASICS INTRODUCTION 3 major note characteristics Top notes (Ex. Citrus, Herbs) 5 minutes Middle notes (Ex. Flowers, Spices) minutes Bottom notes (Ex. Vanilla, Woods) hours

9 1 FRAGRANCE CHEMISTRY INTRODUCTION ALCOHOLS ESTERS PHENOLS ETHERS Wide range of functional groups ALDEHYDES NITROGEN COMPOUNDS KETONES SULFUR COMPOUNDS

10 1 FRAGRANCE CHEMISTRY INTRODUCTION Single perfume ingredients modifications Bitter Almond Fragrance Fragrance Interactions

11 1 FRAGRANCE CHEMISTRY INTRODUCTION Reaction rate depends on many factors: - Reactivities of chemical species - Concentration of reactive species - Temperature - Light - ph - Catalysts -

12 1 FRAGRANCE INTRODUCTION IN PERSONAL CARE Affects consumer s perception of product performance Adds emotional benefits Makes the difference between a product and its competitors Key driver for purchasing decision

13 T H I S S M E L L S G R E A T INCORPORATING FRAGRANCE SUCCESSFULLY INTO COSMETIC PRODUCTS MAIN CONCERNS 2 FORMULATING W I T H F R A G R A N C E QUESTIONS TO BE ANSWERED TYPICAL FUNCTIONAL ISSUES AND SOLUTIONS STABILITY TEST

14 2 MAIN CONCERNS F O R M U L A T I N G W I T H F R A G R A N C E Difficult task Chemically reactive additive May lead to undesirable changes Stable Good looking Final Product Performant Safe Cost Effective

15 2 MAIN CONCERNS F O R M U L A T I N G W I T H F R A G R A N C E Fragrance often selected by type of odor How to enhance probability of SUCCESS? Select fragrance according to system & stability requirements Understand both base and fragrance chemistry! Have a detailed brief of the product when NPD starts Take all parameters into account

16 2 F O R M U L A T I N G W I T H F R A G R A N C E QUESTIONS TO BE ANSWERED What is the end product? (Shampoo, Emulsion ) What is the intended use? (Part of the body, Use ) What will it look like? (Clear, Pearlized, Suspended Beads ) What are the components? (Lipophilic, Hydrophilic ) How will it be processed? (Time, Heat, Agitation, Procedure ) What will be the packaging? (Glass, Plastic, Clear, Opaque ) Will it be coloured? (Natural or Synthetic Dyes, Pigments ) What is the intended percentage of use of the fragrance? (Regulations, IFRA ) Are there stability requirements? (ph, Temperature, Color ) What will be the shelf life? (6 months, 2 years )

17 2 F O R M U L A T I N G W I T H F R A G R A N C E TYPICAL FUNCTIONAL ISSUE SOLUBILITY Fragrance = Aroma Chemicals + Solvent Ingredients range in polarity Solvent influence overall polarity Polar solvents - Shampoo (DPG) Non polar solvents - Body Oil (DEP) In Aqueous & Alcoholic systems

2 F O R M U L A T I N G W I T H F R A G R A N C E Pre solubilize with non ionic

Alcohol ) TYPICAL FUNCTIONAL ISSUE SOLUBILITY Benefit & Solution Surfactant:

Modification Minimize Fragrance % HLB: Hydrophilic-Lipophilic balance of a

18 2 F O R M U L A T I N G W I T H F R A G R A N C E Pre solubilize with non ionic surfactant (Ratio, Diversity ) Pre solubilize with additives (Glyerin, Glycols, Alcohol ) TYPICAL FUNCTIONAL ISSUE SOLUBILITY Benefit & Solution Surfactant: compound that lowers the surface tension between two liquids SOLUTION 01 Fragrance Modification Minimize Fragrance % HLB: Hydrophilic-Lipophilic balance of a surfactant (Ex: Polysorbate 20, PEG 40 Hydrogenated castor oil) Surfactant structure Hydrophilic Lipophilic Balance

Opaqueness In aqueous / alcoholic media even with polar

19 2 F O R M U L A T I N G W I T H F R A G R A N C E TYPICAL FUNCTIONAL ISSUE CLARITY Linked to solubility Haziness Opaqueness In aqueous / alcoholic media even with polar solvents In silicone / mineral oil media even with non polar solvents Sensitivity

20 2 F O R M U L A T I N G W I T H F R A G R A N C E In aqueous & alcoholic system TYPICAL FUNCTIONAL ISSUE CLARITY Pre solubilize with non ionic surfactant (Ratio, diversity) Pre solubilize With Additives (Glycerin, Glycols, Alcohol ) Add opacifier, pearlizing agent (ex. styrene acrylates copolymer, glycol distearate) In silicone & mineral oil system Reduce silicon ingredients Pre solubilize With additives (Esters, Emollients) Add emulsifier (non transparent products) SOLUTION 02

21 2 F O R M U L A T I N G W I T H F R A G R A N C E In both systems TYPICAL FUNCTIONAL ISSUE CLARITY SOLUTION 02 Change the packaging Minimize Fragrance % Fragrance modification

2 F O R M U L A T I N G W I T H F R A G R A N C E TYPICAL FUNCTIONAL ISSUE COLOR Dye instability (Chlorophyllin) Oxidation of aroma chemicals (Vanillin, Orange Oil) Fragrance-Fragrance &

22 2 F O R M U L A T I N G W I T H F R A G R A N C E TYPICAL FUNCTIONAL ISSUE COLOR Dye instability (Chlorophyllin) Oxidation of aroma chemicals (Vanillin, Orange Oil) Fragrance-Fragrance & Fragrance-Base interactions (Base Schiff) Fragrance-Dye interaction (Benzaldehyde) Dye = Chromophore + Conjugated system Chromophore: Absorbs light Base-Package interaction (Ess. Oils, Emollients, Aroma chemicals ) Affecting color, strength, flexibility By chemical Attack - Oxidation - Absorption

chelating agents (EDTA, Sodium Phytate, Sodium Gluconate ) Add UV

23 2 F O R M U L A T I N G W I T H F R A G R A N C E Add antioxidants (Tocopherol, Vit E, BHT ) TYPICAL FUNCTIONAL ISSUE COLOR SOLUTION 03 Add chelating agents (EDTA, Sodium Phytate, Sodium Gluconate ) Add UV absorbers in both product & packaging (Benzophenone ) Avoid heat & light exposure Add Color

2 F O R M U L A T I N G W I T H F R A G R A N C E TYPICAL FUNCTIONAL ISSUE VISCOSITY More pronounced as fragrance level rises Gain of viscosity - Surfactant system - Emulsion

24 2 F O R M U L A T I N G W I T H F R A G R A N C E TYPICAL FUNCTIONAL ISSUE VISCOSITY More pronounced as fragrance level rises Gain of viscosity - Surfactant system - Emulsion system (stability) Loss of viscosity - Surfactant system - Emulsion system (breaking) Influenced by typical parameters, Surfactant type/ratio, emulsifier type, Oil phase, additives

in the structure Micelle Micelle: aggregate of surfactant molecules

25 2 F O R M U L A T I N G W I T H F R A G R A N C E TYPICAL FUNCTIONAL ISSUE VISCOSITY Fragrance addition = Migration of individual components in the structure Micelle Micelle: aggregate of surfactant molecules dispersed in a liquid Non polar Polar Two polar groups Polar group & non polar chain

26 2 F O R M U L A T I N G W I T H F R A G R A N C E In surfactant & Emulsion media TYPICAL FUNCTIONAL ISSUE VISCOSITY SOLUTION 04 Thick System Solvents (Glycols )

27 2 F O R M U L A T I N G W I T H F R A G R A N C E In surfactant media TYPICAL FUNCTIONAL ISSUE VISCOSITY SOLUTION 04 Thin System Secondary Surfactant (Amphoteric type CAPB) Expensive Blend Foam booster Lowers Irritation Increases micelle size Inexpensive Blend Minimum surfactant activity Sodium Chloride (0.2 2%) Thickeners (Gums, Acrylic polymers Decreases charge density & Increases micelle size Rearrangement and Impact on Clarity, Solubility & Precipitation

28 2 F O R M U L A T I N G W I T H F R A G R A N C E In emulsion media TYPICAL FUNCTIONAL ISSUE VISCOSITY SOLUTION 04 Thin System Aqueous phase (Gums, Acrylic polymers ) Oily phase (Waxes, Butters, Thickeners ) Cetyl Alcohol Cocoa Butter

29 2 F O R M U L A T I N G W I T H F R A G R A N C E In both systems TYPICAL FUNCTIONAL ISSUE VISCOSITY SOLUTION 04 Minimize Fragrance % Fragrance Modification Check Compatibility (solvents, preservatives, solubilizer, emulsifier )

30 2 F O R M U L A T I N G W I T H F R A G R A N C E TYPICAL FUNCTIONAL ISSUE ph Fragrance addition = Possible chemical reactions ph Alteration - Change in fragrance performance - Product Spoilage (Outside preservative ph range) - Disruption of products functionality (ex. Shampoo) Healthy Hair Damaged Hair

31 2 F O R M U L A T I N G W I T H F R A G R A N C E Check product specification & requirements TYPICAL FUNCTIONAL ISSUE ph SOLUTION 05 Maintain stable and/or neutral ph Buffering Agents (Disodium Phosphate ) Fragrance Modification (Ethers, Acetals) Esters

32 2 F O R M U L A T I N G W I T H F R A G R A N C E TYPICAL FUNCTIONAL ISSUE SEDIMENTS Perfume Ingredients Dispersed in fragrance Oil (Powders, Resins ) Sediment in alcohol base Bad partitioning of fragrance ingredients Precipitation in surfactant base Resin

conditions (Fridge) In surfactant Base Check salinity of water In both

33 2 F O R M U L A T I N G W I T H F R A G R A N C E In alcohol Base TYPICAL FUNCTIONAL ISSUE SEDIMENTS Filtration Store in different conditions (Fridge) In surfactant Base Check salinity of water In both systems Minimize Fragrance % Increase Ethanol % Fragrance Modification SOLUTION 06

(SLES ) - Poor grade emollients (Rancid Oils ) - Preservatives

34 2 F O R M U L A T I N G W I T H F R A G R A N C E TYPICAL FUNCTIONAL ISSUE ODOUR 1- Initial Raw materials - Surfactants (SLES ) - Poor grade emollients (Rancid Oils ) - Preservatives (Phenethyl alcohol ) PET bottle Packaging materials (Residual solvents) PVC Container

2 F O R M U L A T I N G W I T H F R A G R A N C E TYPICAL FUNCTIONAL ISSUE ODOUR 2- After chemical changes Raw materials - Fragrance-Fragrance interaction (Base Schiff) -

35 2 F O R M U L A T I N G W I T H F R A G R A N C E TYPICAL FUNCTIONAL ISSUE ODOUR 2- After chemical changes Raw materials - Fragrance-Fragrance interaction (Base Schiff) - Oxidation of aroma chemicals (Oils, Ess. Oils) - ph alteration Packaging materials - Permeability (Oxidation, Alteration of fragrance performance, Spoilage) - Breakdown Raw materials?

36 2 F O R M U L A T I N G W I T H F R A G R A N C E TYPICAL FUNCTIONAL ISSUE ODOUR SOLUTION 07 Minimize initial smell of the base Use high grade emollients and oils Add Antioxidants & Chelators Add UV absorbers in base and packaging Maintain neutral ph Check packaging permeability & smell

37 2 STABILITY TESTS F O R M U L A T I N G W I T H F R A G R A N C E Extremely important Predict long term stability Unperfumed base should be tested prior to fragranced base Storage conditions UV light, shop light, sun light, dark, oven at stable temperatures, freezer, fridge, freeze thaw cycles

38 T H I S S M E L L S G R E A T INCORPORATING FRAGRANCE SUCCESSFULLY INTO COSMETIC PRODUCTS 3 DISCUSSION LET S TALK ABOUT IT!

fragrances as mixtures of chemicals Take every possible variable into account

is always at your disposal to help you overcome formulation problems!

39 3 LET S TALK ABOUT IT! D I S C U S S I O N Allow adequate time for testing and resolution of problems Treat fragrances as mixtures of chemicals Take every possible variable into account Cooperate between perfumer, formulator, chemist and customer Your fragrance supplier is always at your disposal to help you overcome formulation problems! Know what they are and their properties A lot of other unknown issues & interactions Specific stability requirements? Sensitive base materials? Have defined technical parameters

40 Thank you for your attention! C ONTACT If you require more information, we will be delighted to hear from you. Please write, call or us directly. VIORYL S.A. 28th km Athens - Lamia National Rd, Afidnes, Greece Tel. (+ 30) Fax (+ 30) gkika@vioryl.gr w w w. v i o r y l. g r

Carbonyl Compounds. Copyright Pearson Prentice Hall. What is the structure of a carbonyl group found in aldehydes and ketones?

Carbonyl Compounds. Copyright Pearson Prentice Hall. What is the structure of a carbonyl group found in aldehydes and ketones? Carbonyl Compounds Have you heard of benzaldehyde or vanillin? It is likely that you have eaten these organic molecules, called aldehydes, in ice cream or cookies. You will read about the properties that