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A.Behler RSC June 18 2008 Munich (1)

Surfactants based on RenewableResources for Personal Care

and Home Care

Ansgar Behler Cognis GmbH

RSC Specialty Chemicals Symposium June 2008, Munich

Surfactants based on RenewableResources for Personal Care

and Home Care

Ansgar Ansgar Behler Behler Cognis GmbHCognis GmbH

RSC Specialty Chemicals Symposium June 2008, Munich




Cognis in Brief

• Leading global specialty chemicals company

headquartered in Monheim, Germany• Sales 2007: €3.518 billion Adjusted EBITDA 2007: €410 million

• Approximately 8,000 employees operating productionsites and/or service centers in about 30 countries

• Over 160 years’ experience in oleochemicals

• Owners since Nov. 30, 2001 are private equity funds

advised by: Permira / GS Capital Partners /SV Life Sciences




Focus on consumer orientation

The Cognis strategy

• Our activities are focused on the global“ wellness” and “ sustainability” trends

• Modern high-performance chemicalsproduced using predominantly natural sourceand renewable raw materials

• Cognis enables its customers to develop and

market sustainable solutions that are wellpositioned to achieve long-term success inthe marketplace




Drivers of the “ sustainability” trend

Consumer needs• Performance and convenience• Natural sourced – renewable raw materials• Biodegradable• Toxicologically harmless• No adverse effect on health, possible even caring properties

Production process• Quality requirements• Safety standards• Environmental protection• (Product) responsibility doesn’t stop at the factory gate




Surfactant market Western Europe (2006)Consumption of surfactants: 2.99 M tonnes/y

Anionic surfactants 41.0 %Nonionic surfactants 42.6 %(ethoxylates)

Cationic Surfactants 9.2 %Other nonionic surfactants 4.5 %(e.g. alkanolamides)

Amphoteric surfactants 2.7 %

Source:Cesio




Surfactant Raw Materials

CrudeCrude Oil / Oil / NaturalNatural GasGas

FatsFats / Oils / Oils

OleochemicalsOleochemicalsPetrochemicalsPetrochemicals

SurfactantsSurfactants




Petrochemical Surfactant Raw Materials

EthyleneEthylene / / PropylenePropylene NN--ParaffinsParaffins BenzeneBenzene PhenolPhenol

AlcoholsAlcohols OxoOxo AlcoholsAlcohols PhenolPhenol

-Olefins LAB LAB Alkylphenol

Ethylene OxidePropylene Oxide




31.3

27.8

12.5

8.9

6.614.9

8.0

6.3

8.2

Butter

Tallow

other plant oils

Palm kernel oil/Coconut oil

Sunflower oil

Rapeseed oil(low in erucic acid)

Palm oil

Soybean oil

other animal fats

Animal feed

6.3

Chemicals

17.4

Nutrition

100.9

World production of oils and fats in 2003(in million tonnes) and main uses

(source: Oil World)




Raw MaterialsNatural Generation of Triglycerides

EnergyCO 2

H2O

TriglyceridesWaxes

Nutrients

ProteinsCarbo-

hydrates

O2

• Surfactants• Emollients and Waxes•

Lubricants• Various auxiliaries,

e.g. triacetin

• New materials for polymers

• Conjugated fattyacids for nutri tion(CLA)

OO

O

O

O

O




Fatty Acid Composition of Coconut Oil

and Tallow

C 8

C 10

C 12

C 14

C 15

C 16C 16:1

C 17

C 18

C 18:1

C 18:2

C 18:3

C 20weight [%]

Fatty acid

0 10 20 30 40 50 0 10 20 30 40 50

weight [%]

Fatty acidCoconut oil TallowC 8

C 10

C 12

C 14

C 15

C 16C 16:1

C 17

C 18

C 18:1

C 18:2

C 18:3

C 20




Route to Basic Oleochemicals

FattyFatty AcidAcidMethyl EstersMethyl Esters

FatsFats /Oils /Oils

FattyFatty AcidsAcids

FattyFattyAlcoholsAlcohols

GlycerineGlycerine




Industrial processing of natural, renewable

raw materials and selected product derivatives

oils&

fats

fattyalcohols

glycerine

fattyacids

fatty acidmethylester

alkyl polyglycosides- derivatives

guerbet alcoholsalkyl ethersfatty alcohol ethoxylatesfatty alcohol sulfatesspecial esters

triacetin(poly)glycerol estersfatty acid estersconjugated fatty acidsalkyl epoxyestersdimer acids

azelaic/pelargonic acidsacylated amino acids

protein

starch glucose

protein hydrolyzateprotein-fatty acidcondensate




Western Europe Consumption by mainsurfactants (2006)

Total: appr. 1.35 mill tonnes

Linear alkylbenzenesulfonate (LAS) 31 % Alkylethoxylates (AE) 35 % Alkylethersulfate (AES) 28 % Alkylsulfate (AS) 4 % Alkylphenolethoxylates (APE) 2 %

Source:CAHA




Major Surfactant Types

Source

SO 3Na

O – (CH 2CH 2O) n – H

LAS petrochemical

O – (CH 2CH 2O) n – SO 3Na

O – (CH 2CH 2O) n – H

O – SO 3Na

APE petrochemical

petrochemical/ oleochemicalAE

petrochemical/ oleochemicalAES

petrochemical/ oleochemicalAS



A.Behler RSC June 18 2008 Munich (16))

Fatty alcoholsFatty alcohols

Methyl esters

Oils / Fats

Alkyl benzene

Olefins

Paraffins

Petroleum / Natural gas

Ethene

anionic

non-ionic

Production of surfactants and examples ofproducts

Linear alkyl benzene sulfonate (LAS)

CH 3 -(CH 2 )n-CH-(CH 2 )m-CH 3

SO 3Na

Fatty alcohol sulfate (FAS)

Fatty alcohol ethoxylate

C H 3 - ( C H 2 ) 1 0 - 1 6 -C H 2 - O - S O 3 N a

C H 3 - ( C H 2 ) 1 0 - 1 6 -C H 2 - O - ( C H 2 C H 2 -O ) n -H

Alkyl polyglycoside




Fatty Alcohol Sulfates (FAS)

Surfactants

Fatty Alcohol Ether Sulfates (FAES)

anionic surfactant

very good foaming power basic surfactants for home and personal care applications,

e.g. body wash and shampoo

insensitive to water hardness

very good water-solubility

anionic surfactantgood foaming power

basic surfactants for home and personal care applications, e.g. detergents

insensitive to water hardnesshigh cleansing power

OS

O

OO

NaOHsulfation

OO

Hn

sulfationO

O

nO

SO

OO

Na




Share of natural based raw materialsbased on Carbon (C) content

Fatty Alcohol Sulfate 100%

Fatty Alcohol Ether Sulfate 75%

Fatty Alcohol Ethoxylate 50-70%

Alkyl Polyglycoside 100%

Alkyl Polyglycoside Carboxylate 95%

Fatty alcohols

Methyl esters

Oils / Fats

Production of surfactants and examples ofproducts

Fatty alcohol sulfate (FAS)

Fatty alcohol ethoxylate

C H 3 - ( C H 2 ) 1 0 - 1 6 -C H 2 - O - S O 3 N a

C H 3 - ( C H 2 ) 1 0 - 1 6 -C H 2 - O - ( C H 2 C H 2 -O ) n -H

Alkyl polyglycoside

Life Cycle Analysis of FASpetroleum vs. veg. oils based

results for vegetable oils based:

70% less use of fossile ressources50% less emissions to the atmosphere

15% less waste

50% more emission to water(low toxic waste water from small,decentralized oi l plants)




(aqueous) Alkyl Polyglycoside

Water

Water

FattyFatty alcoholalcohol

Acetalization

Neutralization

Distillation

Dissolution

Bleaching

Manufacturing processes for

Alkyl Polyglycosides

Glucose Fatty alcoholSolvent freeprocess

Very low

emissions




multifunctionalproduct

multifunctionalproduct

completelybased on renewable

raw materials

completelybased on renewable

raw materials

in cosmetic,detergents,

agrochemicalformulations

in cosmetic,detergents,

agrochemicalformulations

performancebooster

performancebooster

outstandingeco-balanceoutstandingeco-balance

completelybiodegradable

completelybiodegradable

low water hazardclass, WGK I

low water hazardclass, WGK I

excellent skincompatibility

excellent skincompatibility

Alkyl Polyglycosides

GDCh 2000:Wöhler - Preis

"Ressourcen-schonendeProzesse"




OHO

HOOH

O

O

ONaO

OHO

HOOH

OH

O

-HClClONa

O

Surfactant based on Glucose and Fatty Alcohol:

Alkyl Polyglycoside Carboxylate




OHO

HOOH

O

O

ONaO

OHO

HOOH

OH

O

-HClClONa

O

Surfactant based on Glucose and Fatty Alcohol:



- Plantapon ® LGC

INCI: Sodium Lauryl Glucose Carboxylate(and) Lauryl Glucoside

Appearance: clear, yellow liquid Active matter: 28.5 – 34.0%

preserved with 0.5% sorbic acid, foam stable atpH 4-10, non sensitizing, biodegradable




SITA - rotor foam0.5 g/l AS, 15 °gH, 40 °C, 1300 rpm, pH 6

stirring time [s]

0

100200

300

400

500

600

700

800

900

1000

0 30 60 90 120 150 180

F o a m

v o

l u m e

[ m l ]

Lauryl Glucoside

Plantapon LGC

Foaming behavior of Plantapon ® LGCin comparison to APG ® surfactant




Plantapon®

LGC - Dermatological effectsMucous Membrane Compatibility - In vitro test

0

0.5

1

1.5

2

2.5[Q] rel. irri tation value reaction time method

Report R 0200298Test 0201826-1June 2002Texapon ASV 70 with 5%as = 1 [Q] rel. irritation so re

5% as testconcentration

PotassiumCocoyl

HydrolyzedCollagen

SodiumCocoampho-

acetate

SodiumLaurethSulfate

DisodiumCocoyl

Glutamate

Plantapon® LGC




Cl

-HCl

ONH2CHCCH 2

HOO

CH 2

COH

O+

NaOH

NH

CHCCH 2

HOO

CH 2

CO -Na +

O

O

Emulsifier based on Aminoacid and Fatty Acid:

Sodium Stearyl GlutamateSodium Stearyl Glutamate - Eumulgin ® SGINCI: Sodium Stearoyl Glutamate

Appearance: free flowing white powder Properties: high performing O/W emulsifier,

EO-free, highly electrolyte compatible

Use level: 0.25 – 2.0 %




Supports formation of lamellar gels

Low concentration allows easy adjustment of sensorics with emollients,waxes and polymers

High flexibility in formulations regarding commonly used raw materialsStrong emulsifier for modern Face Care concepts, as well as for Body andSun formulations

Summary of Sodium Stearyl Glutamate - Eumulgin ® SG

Eumulgin ® SG – the strength of a diamondfor modern formulations of the cosmetic market

Strong O/W emulsifier at low concentration

High compatibility with electrolytes including water-solubleUV filters

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