Sophorolipids –
A new class of Surfactants
SEPAWA Nordic 2015 – May 5th
Oliver Kaumanns
• Introduction to sophorolipids
• Chemical characteristica
• Foam test set up
• Area of applications & results
• Pure sophorolipid
• Sophorolipid in formulation
• ADW (foam and grease removal)
• HSD
• Laundry
• Your take home messages
• Your questions
Page 2
What are sophorolipids?
An introduction
Our economic practices and
our products are always in
accordance with our
responsibility for future
generations.
• Focus on the use phase of
our products
• Energy and water savings
• Waste reduction
• Renewable resources and
recycling
• Affordable
biosurfactants
• Special branding
Sustainability –
A pillar of Evonik’s strategy
Page 4 Sophorolipids – A new class of Surfactants
Decades of experience with industrial fermentation processes
Leading supplier of biotechnologically produced feed amino acids
> 300 MEUR turnover with biotechnologically produced products
Science to Business center (S2B Bio) dedicated to biotechnology in
Evonik’s Strategic Innovation Unit Creavis
Portfolio of fermentation derived ingredients for cosmetic applications
Global production through fermentation network
Page 5
Evonik´s Competitive Advantage
Biosurfactants
Sophorolipids – A new class of Surfactants
Bacteria/Yeast Fermentation (Raw) product(s)
Biosurfactants have a number of advantages:
Unique and sophisticated structures/properties
Produced from renewable resources
Extremely good skin compatibility
Non-toxic and highly biodegradable
Isolation Feedstock
Page 6
Biosurfactants – Surfactants produced by
microorganisms
Sophorolipids – A new class of Surfactants
Fermentation with
Candida Bombicola +
Sophorolipid
(mainly lactonic form)
Page 7
Sophorolipid´s general fermentation
pathway
Sophorolipids – A new class of Surfactants
Highly water soluble
High(er) foaming
Hardly water soluble
Low foaming
Hydrolytic cleavage of the sophorolipid
lactone
Hydrolysis
Lactone Form Acid Form
Page 8 Sophorolipids – A new class of Surfactants
“Sophorolipid” is typically a complex mixture of at least two glycolipids
made by partial hydrolysis of the water insoluble sophorolipid lactone form :
Composition and properties of
“Sophorolipds”
Complex mixture with C16-C18 saturated or (poly)unsaturated carbon chain
with 0 - 2 acetyl group
Properties depend strongly (but not only) on ratio of lactone to acid form
„The“ one and only sophorolipid does not exist
Page 9 Sophorolipids – A new class of Surfactants
A typical composition of a sophorolipid
produced by Evonik
Total Lac.: 39%
Properties Values
Appearance brownish, aqueous
liquid
Dry matter (DM) 40 – 45 w.-%
Active SL > 90% of DM
Lactone : Acid ratio 40 : 60
Free fatty acid < 0.2 w.-%
pH 5 - 6
Viscosity 100 – 150 mPas
Density 1.00 – 1.10 g/mL
Biodegradability Complete (100%)
Other: ~5 w.-%
Acid: 59 w.-%
Lactone: 36 w.-%
(Values based on dry matter)
Page 10 Sophorolipids – A new class of Surfactants
Page 11
Evonik’s Sophorolipid exhibits superior performance
versus other commercially available sophorolipids
Readily biodegradable and produced from renewable
feedstock
Excellent water-hardness tolerance
Superior mildness compared to conventional surfactants
Synergistic effect with other surfactants
Foaming properties can be altered for each application
Excellent grease and oil removal
Unique Performance
Sophorolipids
Sophorolipids – A new class of Surfactants
Results
Page | 13
Manual Dish Wash
Laundry
Hard Surface Cleaning
Areas of application & test results
Sophorolipids – A new class of Surfactants
Foam evolution of pure
sophorolipids
A comparison
Page 14 Sophorolipids – A new class of Surfactants
Consumer perception
“The longer the foam lasts the
better the performance“
Requirements
Sufficient foam during foam creation
(clean conditions)
Persistent foam during cleaning process
(dirty conditions)
Foaming of hand dish wash (HDW)
liquids is highly consumer relevant:
Page 15 Sophorolipids – A new class of Surfactants
Foaming of pure sophorolipid (SL)
without dirt load
0
50
100
150
200
250
300
Evonik SL Market SL
Fo
am
vo
lum
e [
ml]
0 sec
30 sec
60 sec
90 sec
Conditions: pH = 7, c = 0.2 g/L, T = 40 °C
Evonik SL superior to market sophorolipid regarding flash foam
and foam stabiltiy
Page 16 Sophorolipids – A new class of Surfactants
SL composition varies depending on
educts and production process
Other: 7 w.-%
Acid: 67 w.-%
Lactone: 26 w.-%
Evonik SL
Compositions based on dry matter
Other: 5.-w%
Acid: 19 w.-%
Lactone: 20 w.-%
Ester: 56 w.-%
Market SL
Page 17 Sophorolipids – A new class of Surfactants
Evonik SL Market SL
Ratio Lactone/Acid
(rel.-%) 30:70 80/20 (*)
Free oleic acid
(w.-%) 0.2 2.5
Ratio
Lactone/free oleic acid
(based on absolute w.-%) 60 16
(*) Methyl ester and lactone summarized as lactone
Free fatty acid and ratio lactone/oleic
acid influences the foaming behavior
Page 18 Sophorolipids – A new class of Surfactants
Evonik SL shows significantly higher foaming power than market SL
The foaming behavior can be influenced by controlling residual fatty acid content
The higher the excess of lactone the better foaming
R&D SL Evonik Sophorolipid SL acid
Free fatty acid and ratio lactone/oleic
acid influence the foaming behavior
Page 19
Market SL
Sophorolipids – A new class of Surfactants
0
50
100
150
200
250
300
0 20 40 60 80 100 120 140
foam
vo
lum
e [
ml]
lactone : oleic acid
t = 0 sec
t = 30 sec
t = 60 sec
t = 90 sec
Foam evolution of
sophorolipids in
formulation
Page | 21
Laundry
Hard Surface Cleaning
Manual Dish Wash
Areas of application & test results
Page 22
Primary surfactant: ~ 10 – 30 w.-%
Sodium laurylether sulfate (SLES)
Secondary surfactant: ~ 1 – 5 w.-%
Amineoxide
Alkylpolyglycosides (APG)
Cocoamidopropyl betaine (CAPB)
Hand dish wash liquids in Europe
comprise SLES and AO/APG/betaine
Objective
Higher formulation efficiency replacing
betaine (NBA) by Evonik SL
Sophorolipids – A new class of Surfactants
Studies based on formulations with SLES as primary
surfactant
Secondary surfactant: CAPB and/or sophorolipid
Relative ratio of primary and secondary surfactants
70:30
Our target is to show higher efficiency
replacing betaine by sophorolipids
Page 23 Sophorolipids – A new class of Surfactants
700
800
900
1000
1100
1200
0,0 7,5 15,0 22,5 30,0
Fo
am
vo
lum
e [
ml]
rel. percentage Y of sophorolipid
Foam after 30 sec
Foam after 90 sec
Foaming performance in ternary mixtures
SLES/CAPB/SL (70/X/Y) Y = 15% superior
without dirt
Conditions: pH not adjusted, used as is, 0.2 g/L active material
+ 12%
Page 24 Sophorolipids – A new class of Surfactants
0
200
400
600
800
1000
1200
w/o olive oil low fat high fat
Fo
am
vo
lum
e [
ml]
30 sec
Evonik SL Market SL
0
200
400
600
800
1000
1200
w/o olive oil low fat high fat
90 sec
Evonik SL Market SL
Conditions: pH not adjusted, used as is, 0.2 g/L active material
Evonik SL containing formulations
outperform market SL
Page 25 Sophorolipids – A new class of Surfactants
0
200
400
600
800
1000
1200
w/o olive oil low fat high fat
Fo
am
vo
lum
e [
ml]
30 sec
Conditions: pH not adjusted, used as is, 0.2 g/L active material
Evonik SL containing formulations
outperform market SL
Page 26
Evonik SL allows for up to
30 % higher foam evolution
by replacing (relative) 50%
betaine
Evonik SL is superior to
competitor sophorolipid in
formulation without dirt, on
olive oil and high fat soil
Sophorolipids – A new class of Surfactants
Grease removal
0 10 20 30 40 50 60
SLES-CAPB-SL (Market SL)
SLES-CAPB-SL (L30/A70) 70:15:15
SLES-SL (L30/A70) 70:30
SLES-CAPB 70:30
Market HDW (CAPB containing)
grease removal efficiency [%]
Conditions: 40°C, pH not adjusted, internal method
Grease removal efficacy improved over
commercially available HDW
Page 28
- 60%
Up to 30 % grease removal improvement replacing 50% betaine by
Evonik SL
+ 28%
+ 28%
Sophorolipids – A new class of Surfactants
Hand Dish Wash Liquid % w/w
Sodium laurylether sulfate (70%) 15.0
Cocoamidopropyl betaine (47%) 4.8
Evonik SL (42%) 5.4
Xanthan Gum 0.2
Water (Dye, Perfume, Preservative) ad. 100
Page 29
Efficient hand dish wash liquid
formulation with Sophorolipid
Superior foaming behavior than market product
Higher grease removal efficacy than market product
Sophorolipids – A new class of Surfactants
Page 30 Sophorolipids – A new class of Surfactants
New technology (innovation)
Formulation performance improvement (up to 30%)
Flash foam, foam stability, grease removal
100% biodegradability
CLP-free raw material
Value arguments
Page 31 Sophorolipids – A new class of Surfactants
Less severe formulation hazard classification
Use in Ecolabel formulations
New claims and promotion opportunities
Close the “performance” gap to market leaders
Increase market share
Contribution to own corporate responsibility goals
Contribution to sustainability targets
Value arguments
Page | 32
Manual Dish Wash
Laundry
Hard Surface Cleaning
Areas of application & test results
Sophorolipids – A new class of Surfactants
Hard surface cleaning efficacy of
sophorolipid without mechanical impact
0
20
40
60
80
dir
t re
mo
va
l [w
.-%
]
Evonik SL exhibits higher cleaning performance than other secondary
surfactants on stainless steel plates soiled with a motor oil/paraffin mixture
Page 33 Sophorolipids – A new class of Surfactants
Manual Dish Wash
Page | 34
Hard Surface Cleaning
Laundry (& ADW)
Areas of application & test results
The water hardness “issue”
Page 35
Loss of surfactant by lime soap precipitation
Important for regions with high water hardness (e.g.
MENA)
Addition of builder necessary in laundry detergents
Potentially important to ADW formulations
Sophorolipids – A new class of Surfactants
Excellent water hardness tolerance of
sophorolipids
SDS SDBS SL Acid (L0A100) SL (L40A60)
Water hardness: 40° dH (0.8 g CaCl2/L)
Surfactant: 0.5 w.-%
SDS = sodium dodecyl sulfate; SDBS = sodium dodecyl benzene sulfonate
Page 36 Sophorolipids – A new class of Surfactants
0
20
40
60
80
100
SL Acid(L0S100)
SDBS
Su
rfacta
nt
in liq
uo
r [r
el-
%]
Water Hardness 10° dH
Water Temperature 40°C
Surfactant Conc. 0.03 w.-%
Ratio (w/w) liquor/fabric 5:1
Time 30 min.
SL Acid
(L0A100) SDBS
Residual surfactant in liquor
Page 37
No loss of surface active sophorolipid
during washing by precipitation
Method
Fabric (terry towel) was soaked
in washing liquor & squeezed out.
Determination of surfactant conc.
in washing liquor by HPLC
Sophorolipids – A new class of Surfactants
0
20
40
60
80
100
SL Acid(L0S100)
SDBS
Su
rfacta
nt
in liq
uo
r [r
el-
%]
Water Hardness 10° dH
Water Temperature 40°C
Surfactant Conc. 0.03 w.-%
Ratio (w/w) liquor/fabric 5:1
Time 30 min.
SL Acid
(L0A100) SDBS
Residual surfactant in liquor
Page 38
No loss of surface active sophorolipid
during washing by precipitation
Evonik SL potentially allows to
partially / completely replace
conventional builder systems
Sophorolipids – A new class of Surfactants
Your take home messages
Page 39
- There is not „the one and only” Sophorolipid
- (Foam) properties of sophorolipids strongly depend on composition (lactone, acid, free acid)
- The less oleic acid the higher foam volume
- Properties can be fine-tuned especially with regard to foaming
- Proportional betaine replacement (50% CAPB) best choice (synergies)
- Evonik SL superior to market SL w/o soil, olive oil, high fat soil (~28% foam increase at same active)
- High grease removal efficacy (+28 % over SLES/CAPB)
- High grease removal efficacy (3 times larger than market SL)
- Evonik SL exhibits better cleaning performance than other secondary surfactants
- Excellent hard water tolerance
- Potential to exchange existing builder systems
Sophorolipids – A new class of Surfactants
Page 40
Do you have questions?