Surfactants based on Renewable

Resources for Personal Care

and Home Care

Ansgar Behler
Cognis GmbH
RSC Specialty Chemicals Symposium June 2008, Munich
A.Behler RSC June 18 2008 Munich (1)

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 production
sites 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

A.Behler RSC June 18 2008 Munich (2)

The Cognis strategy

Focus on consumer orientation

Our activities are focused on the global

wellness and sustainability trends

Modern high-performance chemicals

produced using predominantly natural source
and renewable raw materials

Cognis enables its customers to develop and

market sustainable solutions that are well
positioned to achieve long-term success in
the marketplace
A.Behler RSC June 18 2008 Munich (3)

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 doesnt stop at the factory gate

A.Behler RSC June 18 2008 Munich (4)

Global Surfactant market (2006)

Worldwide production of surfactants: 12.5 M tonnes/y
Growth rate: appr. 0.5 M tonnes/y
Use of surfactants:
60 %
30 %
7%
6%

Household detergents
Industrial and technical appl.
Industrial and institutional cleaning (I&I)
Personal Care

Source: Focus on surfactants May 2006

A.Behler RSC June 18 2008 Munich (5)

Surfactant market Western Europe (2006)

Consumption of surfactants: 2.99 M tonnes/y

Anionic surfactants
Nonionic surfactants

41.0 %
42.6 %

(ethoxylates)

Cationic Surfactants
Other nonionic surfactants

9.2 %
4.5 %

(e.g. alkanolamides)

Amphoteric surfactants

2.7 %

Source:Cesio

A.Behler RSC June 18 2008 Munich (6)

Surfactant Raw Materials

Crude Oil /
Natural Gas

Fats / Oils

Petrochemicals

Oleochemicals

Surfactants
A.Behler RSC June 18 2008 Munich (7)

Petrochemical Surfactant Raw Materials

Ethylene/
Propylene

N-Paraffins

Benzene

Phenol

-Olefins

LAB

LAB

Alkylphenol

Alcohols
Ethylene Oxide
Propylene Oxide
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Oxo Alcohols

Phenol

World production of oils and fats in 2003

(in million tonnes) and main uses
31.3

Soybean oil
27.8

Palm oil
Rapeseed oil

12.5

(low in erucic acid)

8.9

Sunflower oil
Palm kernel oil/
Coconut oil
other plant oils

6.6
14.9

Tallow
Butter

Animal feed
6.3

8.0

Nutrition
100.9

6.3

other
animal fats

8.2
(source: Oil World)

A.Behler RSC June 18 2008 Munich (9)

Chemicals
17.4

Raw Materials
Natural Generation of Triglycerides
Energy
CO2

H2O
Nutrients

Surfactants
Emollients and Waxes
Lubricants
Various auxiliaries,
e.g. triacetin

O
O

O
O
O

Proteins

O2
Carbohydrates

Triglycerides
Waxes

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New materials for

polymers

Conjugated fatty
acids for nutrition
(CLA)

Fatty Acid Composition of Coconut Oil

and Tallow
Fatty acid
C8
C10
C12
C14
C15
C16
C16:1
C17
C18
C18:1
C18:2
C18:3
C20
0

Coconut oil

weight [%]

10

20

A.Behler RSC June 18 2008 Munich (11)

30

40

50

Fatty acid
C8
C10
C12
C14
C15
C16
C16:1
C17
C18
C18:1
C18:2
C18:3
C20
0

Tallow

weight [%]

10

20

30

40

50

Route to Basic Oleochemicals

Fats/Oils
Glycerine

Fatty Acids

Fatty Acid
Methyl Esters
Fatty
Alcohols

A.Behler RSC June 18 2008 Munich (12)

Industrial processing of natural, renewable

raw materials and selected product derivatives
starch

glucose
fatty acid
methyl
ester

oils
&
fats

fatty
alcohols

glycerine

A.Behler RSC June 18 2008 Munich (13)

guerbet alcohols
alkyl ethers
fatty alcohol ethoxylates
fatty alcohol sulfates
special esters
triacetin
(poly)glycerol esters
fatty acid esters
conjugated fatty acids
alkyl epoxyesters
dimer acids
azelaic/pelargonic acids
acylated amino acids

fatty
acids

protein

alkyl polyglycosides
- derivatives

protein hydrolyzate

protein-fatty acid
condensate

Western Europe Consumption by main

surfactants (2006)
Total: appr. 1.35 mill tonnes

Linear alkylbenzenesulfonate (LAS)

Alkylethoxylates (AE)
Alkylethersulfate (AES)
Alkylsulfate (AS)
Alkylphenolethoxylates (APE)

31 %
35 %
28 %
4%
2%

Source:CAHA

A.Behler RSC June 18 2008 Munich (14)

Major Surfactant Types

Source
LAS

petrochemical

APE

petrochemical

SO3Na

O (CH2CH2O)n H

O (CH2CH2O)n H

O (CH2CH2O)n SO3Na

O SO3Na

A.Behler RSC June 18 2008 Munich (15)

AE

petrochemical/
oleochemical

AES

petrochemical/
oleochemical

AS

petrochemical/
oleochemical

Production of surfactants and examples of

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

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

anionic

Fatty alcohol sulfate (FAS)

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

Fatty alcohol ethoxylate

SO 3 Na
Linear alkyl benzene sulfonate (LAS)

Alkyl benzene

nonionic

Alkyl polyglycoside

Fatty alcohols

Olefins
Methyl esters
Paraffins

Ethene

Petroleum / Natural gas

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

Oils / Fats

Surfactants
Fatty Alcohol Sulfates (FAS)
O

sulfation

OH

anionic surfactant
good foaming power

O
S

O Na

insensitive to water hardness

high cleansing power

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

Fatty Alcohol Ether Sulfates (FAES)

O

sulfation
H
n

anionic surfactant
very good foaming power

O
S

O Na

insensitive to water hardness

very good water-solubility

basic surfactants for home and personal care applications,

e.g. body wash and shampoo

A.Behler RSC June 18 2008 Munich (17)

Production of surfactants and examples of

products
Share of natural based raw materials
Life
Cycle
FAS
based
on Analysis
Carbon (C)of
content
petroleum vs. veg. oils based
Fatty Alcohol Sulfate
100%
results
for vegetable
oils based: 75%
Fatty Alcohol
Ether Sulfate

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

Fatty alcohol sulfate (FAS)

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

Fatty alcohol ethoxylate

Alkyl polyglycoside

70% less use of fossile ressources

Fattyless
Alcohol
Ethoxylate
50-70%
50%
emissions
to the atmosphere
15% less waste

Alkyl Polyglycoside

Alkylmore
Polyglycoside
50%
emission toCarboxylate
water
(low toxic waste water from small,
decentralized oil plants)

A.Behler RSC June 18 2008 Munich (18)

Fatty alcohols

100%
95%

Methyl esters

Oils / Fats

Manufacturing processes for

Alkyl Polyglycosides
Solvent free
process

Glucose
Water

Very low
emissions

Fatty alcohol

Acetalization
Neutralization
Distillation

Water

Fatty alcohol

Dissolution
Bleaching

(aqueous) Alkyl Polyglycoside

A.Behler RSC June 18 2008 Munich (19)

Alkyl Polyglycosides
multifunctional
multifunctional
product
product

in
in cosmetic,
cosmetic,
detergents,
detergents,
agrochemical
agrochemical
formulations
formulations

performance
performance
booster
booster

completely
completely
based
based on
on renewable
renewable
raw
raw materials
materials

A.Behler RSC June 18 2008 Munich (20)

outstanding
outstanding
eco-balance
eco-balance

GDCh 2000:
Whler - Preis
"Ressourcenschonende
Prozesse"

completely
completely
biodegradable
biodegradable

low
low water
water hazard
hazard
class,
class, WGK
WGK II

excellent
excellent skin
skin
compatibility
compatibility

Surfactant based on Glucose and Fatty Alcohol:

Alkyl Polyglycoside Carboxylate
OH
O

HO
HO

OH

Na O

Na O
O

HO
HO

O
OH

A.Behler RSC June 18 2008 Munich (21)

Cl

-HCl

Surfactant based on Glucose and Fatty Alcohol:

Alkyl Polyglycoside Carboxylate
OH
Alkyl Polyglycoside
Carboxylate
O
- Plantapon LGC
HO
HO

INCI:
Appearance:
Na O
Active matter:O
O

O
OH
Sodium
Lauryl Glucose Carboxylate
(and) Lauryl Glucoside
Na Oyellow liquid
clear,
-HCl
Cl
O
28.5 34.0%

O
preserved
with
0.5%
sorbic
acid, foam stable at
HO
HO sensitizing, biodegradable
pH 4-10, non
O
OH

A.Behler RSC June 18 2008 Munich (22)

Foaming behavior of Plantapon LGC

in comparison to APG surfactant
SITA - rotor foam
0.5 g/l AS, 15 gH, 40 C, 1300 rpm, pH 6
1000

Foam volume [ml]

900
800
700
600
500
400
300
200

Plantapon LGC

100
0
0

30

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60

90
stirring time [s]

120

150

180

Lauryl Glucoside

Plantapon LGC - Dermatological effects

Mucous Membrane Compatibility - In vitro test
2.5

[Q] rel. irritation value reaction time method

2
1.5
1
0.5
0
Potassium
Cocoyl
Hydrolyzed
Collagen

Sodium
Cocoamphoacetate

Sodium
Laureth
Sulfate

Texapon ASV 70 with 5%as = 1 [Q] rel. irritation sore

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Disodium
Cocoyl
Glutamate

Plantapon LGC

5% as test
concentration
Report R 0200298
Test 0201826-1
June 2002

Emulsifier based on Aminoacid and Fatty Acid:

Sodium Stearyl Glutamate
O
Sodium
Stearyl Glutamate - Eumulgin SG

HO C CHNH2
INCI:
CH2
Appearance:
CH2
Properties:
O C
OH

Use level:

Sodium Stearoyl Glutamate

+

Cl
free flowing
white powder

high performing O/W emulsifier,

EO-free,
highly
-HClelectrolyte compatible
NaOH
0.25 2.0 %

O
O
HO C CHN
H
CH2
CH2
O C
O-Na+

A.Behler RSC June 18 2008 Munich (25)

Summary of Sodium Stearyl Glutamate - Eumulgin SG

Strong O/W emulsifier at low concentration
High compatibility with electrolytes including water-soluble
UV filters
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 materials
Strong emulsifier for modern Face Care concepts, as well as for Body and
Sun formulations

Eumulgin SG the strength of a diamond

for modern formulations of the cosmetic market
A.Behler RSC June 18 2008 Munich (26)

A.Behler RSC June 18 2008 Munich (27)