Oleon A NATURAL CHEMISTRY Personal Care Overview Oil

Oleon : A NATURAL CHEMISTRY Personal Care Overview

Oil cake Biotechnologies Seeds Pesticides Other services for agriculture Animal health and breeding Animal nutrition Growers Collect of oilseeds and protein rich seeds Crushing Food Oils Renewable energies Growers and breeders Oilseeds division Food animal sector division Other Agricultural industries with Sofiprotéol concern Renewable chemicals Breeders Transformation and animal productions

1. Oleon Company 2. Product Overview 3. HLB 4. Emulsifier s 5. Isostearic Esters 6. Formulatio ns Oleon is a leading company in Europe for the production of chemicals based on Natural Oils Oleon is a subsidiary of the Sofiproteol group, Europe’s reference for vegetable oil with activities in food, feed, biofuels and oleochemistry. Oleon has production sites in - Belgium (Ertvelde and Oelegem) Germany (Emmerich) France (Compiègne) Norway (Sandefjord) In 2009 Oleon started Producing natural esters in Malaysia (Port Klang)

Raw Materials 1. Oleon Company 2. Product overview 3. HLB 4. Emulsifier s 5. Isostearic Esters 6. Formulatio ns Rapeseed, Sunflower, Palm, Coconut, Soya, PKO, Linseed, Castor…

1. Oleon Company 2. Product Overview 3. HLB 4. Emulsifier s 5. Isostearic Esters 6. Formulatio ns Oleochemicals are esters, fatty acids, glycerol. . Applications Soap, detergents, Personal Care, Lubricants, Food, …

1. W/O Properties 2. Product Overview 3. HLB 4. Emulsifier s 5. Isostearic Esters 6. 5. Form ulations • Fatty acids (Radiacid) • Glycerine, Propylene Glycol • Radia esters based on PEG, (Poly)glycerol, fatty acids, fatty alcohols, sorbitol, … • Emulsifiers • Emollients • Stabilizers • Opacifying • Bodying agents • …

ar ic o (P Pe PEG m yl oa ly g ly) Fatty alcohols Fatty Acids Is ol r ce l te ito os So rb Is Polyols Radia Esters building blocks nta ery thr ito l

1. 1. W/O Properties Product Overview 3. HLB 4. Emulsifier s 5. Isostearic Esters 6. 5. Form ulations • HLB was invented 60 years ago by William C. Griffin • The letters HLB stand for Hydrophilic Lipophilic Balance Hydrophilic head Lipophilic tail • It was intended as a large scale road map to good emulsification performance. • It was invented for use with NONIONIC surfactants in particular.

1. Oleon Company 2. Product overview 3. HLB 4. Emulsifier s 5. 6. • mixing unlike oils together –use surfactants with HLB’s of 1 to 3 • making water-in-oil emulsions –use surfactants with HLB’s of 4 to 6 • wetting powders into oils –use surfactants with HLB’s of 7 to 9 • making self emulsifying oils –use surfactants with HLB’s of 7 to 10 • making oil-in-water emulsions –use surfactant blends with HLB’s of 8 to 16 • making detergent solutions –use surfactants with HLB’s of 13 to 15 • for solubilizing oils ( micro-emulsifying ) into water –use surfactant blends with HLB’s of 13 to 18 Isostearic Esters Formulatio ns

R 7908: Glyceryl Monolaurate 90% 2. Oleon Company 2. Product Overview 3. HLB 4. Emulsifier s 5. Isostearic Esters 6. Formulatio ns • Our technology has lead to a monoglyceride %> 90%. • (Co)Emulsifier with HLB of ± 5. 0 and super emollient with enhanced skin feel. • Antibacterial properties; good performance on yeasts, moulds and gram +. Addition of a good chelant (EDTA) can increase the performance on gram -. • Viscosity increasing in surfactant systems as hydrophobic thickener where combinations with eg CAPB are made. • Potential of penetration enhancer of active ingredients.

1. Oleon Company 2. Product Overview 3. HLB 4. Emulsifier s 5. Isostearic Esters 6. Form ulations Antibacterial Properties of GML

Radiamuls 2932 1. W/O Properties 1. Product Overview 3. HLB 4. Emulsifier s 5. Isostearic Esters 6. Form ulations PEG free & solid O/W emulsifier Self emulsifying • HLB of 10 -12 • INCI: GLYCERYL STEARATE CITRATE • Gives the skin a soft and smooth appearance • Synergy with Radia 7145 (Sorbitan Stearate) • Formation of gel network in water phase • The natural skin moisture barrier is mimicked • Improved moisturizing performance of O/W emulsion • Enhanced stability of emulsion • Skin pleasant rheological profile

Radiamuls 2990 1. Oleon Company 2. Product overview 3. HLB • HLB of 16. 4. Emulsifier s • INCI: Sodium Stearoyl Lactylate 5. Isostearic Esters 6. Formulatio ns Anionic, PEG free & solid O/W emulsifier Multi functional • Skin conditioning and moisturizing • white fluffy powder • light emulsions rich in water • Can also act as a foam booster in cleansing formulations

1. 2. Oleon Company Saturated Products Product overview No crystallization 3. HLB 4. Emulsifier s 5. 6. Liquid products Isostearic Esters Formulatio ns Branched products Stability, no antioxydant needed Lower melting point compared to straight-chain analogues Cold emulsion process & easy to handle Important for heat sensitive products included in high demanding formulations Non greasy afterfeel, lipid film more substantive, Soft on the skin and glossy aprearance, Excellent emolliency Main products derived from oleic acid can be replaced by the corresponding isostearic derivatives without loss of performance.

Product Range (INCI) Radia • Isostearic Acid 908 / 909 • Neopentylglycol Diisostearate 7687 • Pentaerythrityl Tetraisostearate 7179 • Triisostearin 7373 Isostearic Esters • Trimethylolpropane Triisostearate 7380 Formulatio ns • Isopropyl Isostearate 7739 • Sorbitan isostearate 7758 2. Oleon Company 2. Product Overview 3. HLB 4. Emulsifier s 5. 6.

Radia 7373 1. Oleon Company 2. Product Overview 3. HLB 4. Emulsifier s 5. Isostearic Esters 6. Form ulations Good substantive, rich and non tacky feel emollient Properties and Benefits • INCI: Triisostearin • Functions as dispersant & adhesion promotor of pigments. As solubilizer for active ingredients. • Can help modifying melting points! • Special interest combined with light emollient for long lasting spreadability (no migration). • Comparable to some natural oils but easier to emulsify. Applications • Lipsticks (long lasting) • Colour cosmetics

Radia 7179 1. W/O Properties 2. Product Overview 3. HLB 4. Emulsifier s 5. 6. Isostearic Esters 6. Form ulations Good substantive and rich emollient Properties and Benefits Applications • INCI: Pentaerythrityl Tetraisostearate • Sun care • Functions as emollient, dispersant & water repellent. • Liquid foundations • Provides high gloss film, resists rub off, reduces drag on application. • Substantive and cushion feel. • Good alternative to castor oil. • lipsticks • high solid make up

Radia 7380 1. Oleon Company 2. Product Overview 3. HLB 4. Emulsifier s 5. 6. Isostearic Esters 6. Form ulations Good lubricating and rich film forming emollient Properties and Benefits Applications • INCI: Trimethylolpropane Triisostearate • general skin & hair care • Functions as dispersant for solid ingredients, as potential SPF booster. • Delivers shine and plasticizer properties in hair care. • Non tacky sensorial properties. • Improves skin elasticity. • Mineral oil replacement • depilatory creams, • colour cosmetics, • sun and baby care, • shaving formulations

Radia 7687 1. W/O Properties 2. Product Overview 3. HLB 4. Emulsifier s 5. 6. Isostearic Esters 6. Form ulations Silky and good spreading emollient Properties and Benefits Applications • INCI: Neopentyl Glycol Diisostearate • Sun care • Skin Conditioning • Protective creams • Silky and rich skin feel • Shaving creams

Radia 7739 1. W/O Properties 2. Product Overview 3. HLB 4. Emulsifier s 5. 6. Isostearic Esters 6. Form ulations Light feel emollient with fast absorbtion and excellent spreadability Properties and Benefits • INCI: Isopropyl Isostearate • Functions as overall reducer of tackiness, effective solvent and disperser. • High gloss & low occlusive. • Fast absorption, imperceptible afterfeel on the skin(Better than IPM), low amount of residue. Applications • Unique ingredient for many cosmetic preparations • Face and eyes make up

Radia 7887 Cold Water-in-oil emulsifier

INCI: Polyglycerol-3 Polyricinoleate & Sorbitan Isostearate HLB 4, 2 & Single Emulsifier Liquid & EO Free & Palm Free Amber Coloured

1. W/O Properties 2. W/O Applicatio ns 1. W/O Properties • Skin protection 3. Famous Examples • Long lasting moisturisation 4. R 7887 • Resemblance to the natural skin protective barrier 5. Formulatio ns • Improved spreading and penetration of active ingredients • Reduced preservative concentration

1. W/O Properties 2. W/O Applicatio ns 2. W/O Applications • Sun Screen milks, lotions and creams 3. Famous Examples • Night creams 4. R 7887 • Creams & lotions for dry and sensitive skin 5. Formulatio ns • Skin protective baby creams • Massage milks

1. W/O Properties 2. W/O Applicatio ns 4. R 7887. . • . . . is liquid and allows cold production = reduced cost! 3. Famous examples • . . . is based on natural raw materials & is PEG free. 4. R 7887 • . . . has no need for co-emulsifier single emulsifier 5. Formulatio ns • …is fit for high and low internal face • . . . provides emulsions with a glossy appearance • …functions at low levels (≥ 1%)

1. W/O Properties 2. W/O Applicatio ns 3. Famous examples 4. R 7887 5. 6. 7. 8. • Solid emulsifier requires temperature (=cost) input. T (°C) 1 2 Hot Process +/- 80 a. Cold Process b. Emollients c. Single Emulsifier 5. Form ulations 3 4 = Cost 20 Homogenize 5

1. W/O Properties 2. W/O Applicatio ns 3. 4. 5. 6. 7. 8. • R 7887 doesn’t require heating = possible cost reduction! T(C°) Famous examples 1 R 7887 2 3 4 Homogenize a. Cold Process b. Emollients c. Single Emulsifier 5. Form ulations 20 5

1. W/O Properties 2. W/O Applicatio ns 3. Famous examples • Potential cost reduction thanks to cold proces. Hot Proces vs Cold Proces Weighing and mixing Weighing mixing Heating Homogenisation Addition of other raw materials Cooling & agitation Filling 4. R 7887 5. a. Cold Process b. Emollients C. Single Emulsifier Time loss during cooling / Addition of other raw materials / Cooling to room tempurature / 5. Filling / 6. 7. 8. Form ulations Minutes 20 40 60 80 100 120 140 160

1. W/O Properties 2. W/O Applicatio ns 3. Famous examples 4. R 7887 a. Cold Process b. Emollients c. Single Emulsifier 5. Form ulations b. Emollients influence formulation. • % water => Viscosity Formulation • Viscosity emollients => Viscosity Formulation • Homogenisation => Stability (& Viscosity) Formulation

1. 2. W/O Properties W/O Applicatio ns c. Single Emulsifier. : Test protocol Test formulation W/O Oilphase 3. Famous examples Oil Emulsifier 4. R 7887 Waterphase 5. a. Cold Process b. Emollients c. Single Emulsifier Glycerol 4 Mg. SO 4. 7 H 2 O 0, 7 Preservative q. s. Water to 100% 6. 7. 8. 5. Form ulations 10 or 18 or 30 1 or 3. 5 Low external phase = 10% High external phase = 30% Low surfactant = 1% High surfactant = 3. 5% Centrifuge stability (3 x 15 min @ 4000 rpm) Temperature stability 1 week @ 50°C 2 months@ 40°C 3 months@ RT Viscosity stability ( m. Pas) Brookfield 10 rpm, 1 minute, LVT spindle After 1 day After 3 months appearance Visual aspect

1. W/O Properties 2. W/O Applicatio ns 3. Famous examples 4. R 7887 a. Cold Process b. Emollients c. Single Emulsifier 5. Form ulations c. Single Emulsifier. : Conclusions • 1% emulsifier is stable for MCT and paraffin oils (18%). • 3, 5% emulsfier is stable for MCT, sunflower oil and paraffin oils. Separate esters are being tested. • Highest viscosity and synergy is obtained by using sunflower oil. • Internal phases till 82% were achieved.

5. Formulations Low Cost W/O protective cream HP 11 -22 -2 • Phase • Ingredient • INCI • A • Radia 7887 • Polyglycerol-3 Polyricinoleate & Sorbitan Isostearate • 3. 6 • Radia 7373 • Triisostearin • 0. 5 • Radia 7363 • Triolein (= Sunflower oil) • 18 • Glycerin 4810 • Glycerin • water • Aqua • B • C • % w/w • 4 • To 100 • Mg. SO 4. 7 H 2 O • 0. 8 • preservative • 0. 7 Viscosity : 121000 m. Pa. s (Brookfield RV, spindle 7, rpm 10, 1 min. ) Assessment: Rich protective cream, high viscosity, film forming , good spreading

5. Formulations W/O soft body cream/Lotion HP 03 -54 -3 • Phase • Ingredient • INCI • A • Radia 7887 • Polyglycerol-3 Polyricinoleate & Sorbitan Isostearate • 4 • Radia 7208 • Propylene Glycol Dicaprylate/Dicaprate • 2 • Radia 7732 • Isopropyl Palmitate • B • C • % w/w • 11 • Sweet almond oil • 2 • Avocado oil • 2 • Glycerin 4810 • Glycerin • water • Aqua • 3 • To 100 • Mg. SO 4. 7 H 2 O • 0. 5 • preservative • 0. 7 • Viscosity , 35000 m. Pa. s (Brookfield RV, spindle 6, rpm 10, 1 min. ) • Assessment: Rich day lotion, nice, soft skinfeel, smooth afterfeel , good spreading

5. Formulations Low Cost Protective baby cream • Phase • Ingredient • INCI • A • Radia 7887 • Polyglycerol-3 Polyricinoleate & Sorbitan Isostearate HP 11 -12 -1 • % w/w • 3, 6 • Paraffin Oil • B • C • 15 • Radia 7373 • Triisostearin • 0, 5 • Radia 7500 • Cetyl Palmitate • 2 • Glycerin 4810 • Glycerin • 3 • water • Aqua • To 100 • Mg. SO 4. 7 H 2 O • 0. 5 • preservative • 0. 7 • Zn. O • 10 • Viscosity , 35000 m. Pa. s (Brookfield RV, spindle 6, rpm 10, 1 min. ) • Assessment: Rich day lotion, nice, soft skinfeel, smooth afterfeel , good spreading

Oleon : A NATURAL CHEMISTRY Isoamyl Esters

Isoamyl Esters Biofermentation Isoamyl Alcohol + Vegetable Fatty Acids = Isoamyl Ester Isoamyl esters are the natural alternative to high performance dispersing products.

Isoamyl Esters ü Fully natural : originates from fusel oils coming from the bio fermentation of sugar beets ü Isoamyl alcohol = isobutyl carbinol =isopentyl alcohol ü Vegetable fatty acids : C 8/C 10, C 12, C 14, C 16, C 18 , C 16 C 18, cocoate, oleate ü Oleon isoamyl esters contain only natural building blocks.

Radia 7750: Isoamyl Laurate Very good solvating power Ability to disperse pigments Excellent skin compatibility Low viscosity & Quick absorbing Excellent sensorial profile Sunscreen products & UV filters Colour cosmetics and skin care. Baby care and cleansing formulations Improved spreadability. Silicone like sensorial profile

R 7750 Sensorial Properties During rubbing IPM Dimethicone After rubbing R 7750

Visual evaluation of wetting properties 10 gr Ti. O 2 + C 12 -C 15 A. B. Castor Oil 12 ml 5 13 ml 4 5 5 14 ml 2 5 5 4 15 ml IA Laurate IA Myristate IA Palmitate IA Oleate 1 smooth dispersion 5 5 1 4 4 3 4 4 2 3 4 4 4 1 2 Glossy dispersion slighly Granular 18 ml 3 4 3 3 3 Granular cream 19 ml 3 4 2 2 4 Granular paste 5 Adhesive paste 16 ml 17 ml 20 ml 3 3 21 ml 3 3 1 1 22 ml 3 2 23 ml 24 ml 25 ml 26 ml 1 2 2 2 1 2 Isoamyl esters disperse the same dosage of pigment Ti. O 2 with a small amount of ester.

Analytical evaluation of wetting properties Visually identified as smooth and viscous dispersion Isoamyl esters provide a steady viscosity with increasing Ti. O 2 concentration. This stability translates into easier handling for end formulations.

R 7750 Application Info ü Imparts a dry lubricating feel in the presence of large amounts of mineral oil or vegetable oils; i. e. , “de-oils” mineral oil and “de-greases” vegetable oils. ü Is a short chain ester which acts as a superior solubilizer of lipophilic cosmetic raw materials as eg sunscreen agents. ü Provides high spreading and quick penetration. ü Acts as an anti-tack agent. ü Acts as a wetting agent and auxiliary suspending agent for waterinsoluble powdered products. Ø First choice emollient in natural and conventional cosmetic frame formales

Formulation Data ü Usage level: 4 -80%. Often used as primary oil. ü Higher usage levels 30 -80% in all kind of body oils & bath oils. ü 5 -20% in both O/W and W/O emulsion creams. ü Wet wipes O/W: 0. 5 -2 % ü Natural hair care products: 1 -5%