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The Power of "Ene" in Water-Based Cleaners and Removers: A New-to-the-World Metathesis-Based Surfactant Makes Water Work Like An Organic Solvent

The document discusses a new metathesis-based surfactant called N,N-Dimethyl 9-Decenamide. It was created through a metathesis derivatives program that aims to improve performance, reduce costs, stabilize supply, and meet sustainability targets. The molecule has desirable properties like being water soluble, having low toxicity, and high solubility in a range of solvents. These properties give it potential as a cleaning agent and for personal care applications by allowing water to work like an organic solvent.

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pkh29
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0% found this document useful (0 votes)
67 views61 pages

The Power of "Ene" in Water-Based Cleaners and Removers: A New-to-the-World Metathesis-Based Surfactant Makes Water Work Like An Organic Solvent

The document discusses a new metathesis-based surfactant called N,N-Dimethyl 9-Decenamide. It was created through a metathesis derivatives program that aims to improve performance, reduce costs, stabilize supply, and meet sustainability targets. The molecule has desirable properties like being water soluble, having low toxicity, and high solubility in a range of solvents. These properties give it potential as a cleaning agent and for personal care applications by allowing water to work like an organic solvent.

Uploaded by

pkh29
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
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The Power of "ene" in Water-Based

Cleaners and Removers:


A New-to-the-World Metathesis-Based
Surfactant Makes Water Work Like an
Organic Solvent
Ron A. Masters, PhD
Research Associate, Stepan Company
Outline
• Metathesis Derivatives Program
• Molecule: Reaction, Chemistry, Properties
• Solution Behavior
• Applications
– Cleaning
– Personal Care
• Summary and Acknowledgements
Metathesis Derivatives Program: Drivers
• Improve Performance
• Reduce/Stabilize Feedstock Cost
• Stabilize Feedstock Supply
• Meet New Sustainability Targets
• Nobel Prize-winning Technology
• Conversion of Indigenous Vegetable Oils
• Ideal Feeds for Derivatization Competencies
• Large-Scale Supply – Elevance Renewable Sciences
Metathesis Derivatives Program: Drivers
• Improve Performance
• Reduce/Stabilize Feedstock Cost
• Stabilize Feedstock Supply
• Meet New Sustainability Targets
• Nobel Prize-winning Technology
• Conversion of Indigenous Vegetable Oils
• Ideal Feeds for Derivatization Competencies
• Large-Scale Supply – Elevance Renewable Sciences
Metathesis Derivatives Program: Drivers
• Improve Performance
• Reduce/Stabilize Feedstock Cost
• Stabilize Feedstock Supply
• Meet New Sustainability Targets
• Nobel Prize-winning Technology
• Conversion of Indigenous Vegetable Oils
• Ideal Feeds for Derivatization Competencies
• Large-Scale Supply – Elevance Renewable Sciences
Metathesis Derivatives Program: Drivers
• Improve Performance
• Reduce/Stabilize Feedstock Cost
• Stabilize Feedstock Supply
• Meet New Sustainability Targets
• Nobel Prize-winning Technology
• Conversion of Indigenous Vegetable Oils
• Ideal Feeds for Derivatization Competencies
• Large-Scale Supply – Elevance Renewable Sciences
Metathesis Derivatives Program: Overview
Hundreds of Molecules
- Organized Team/Program
- Synthesis
- Properties Characterization
- Performance Tests
- Looking for the “Wow”

N,N-Dimethyl 9-Decenamide
- New to the World, new CAS #
- Short Chain, Monounsaturated
- Solvent ? Surfactant ?
Metathesis Derivatives Program: Overview
Hundreds of Molecules
- Organized Team/Program
- Synthesis
- Properties Characterization
- Performance Tests
- Looking for the “Wow”

N,N-Dimethyl 9-Decenamide
- New to the World, new CAS #
- Short Chain, Monounsaturated
- Solvent ? Surfactant ? “ene”
Outline
• Metathesis Derivatives Program
• Molecule: Reaction, Chemistry, Properties
• Solution Behavior
• Applications
– Cleaning
– Personal Care
• Summary and Acknowledgements
Molecule: Reaction, Chemistry, Properties

Amide 97% minimum (99% Typical)


Water 0.5% maximum (0.0 – 0.1% Typical)
Residual Ester 1.0% maximum (0.2 – 0.6% Typical)
Iodine Value 117 – 137 (g/100g)
Color (Gardner) 1 maximum (0 Typical)
Other Residuals 100ppm maximum each

Boiling Point (C) 297 (LVP-VOC Exempt)


Flash Point (C) 134 (PMCC)
Cloud Point (C) -13 (Low HLB Nonionic)
Kauri-Butanol Value >1000 (ASTM D1133)
Hansen Solubility Parameters D: 16.58, P: 9.58, H: 8.45 (Experimental*)
Estimated HLB 6 (Griffin or Davies)

* Using Hansen software and screening across a large set of test solvents
Molecule: Reaction, Chemistry, Properties

Amide 97% minimum (99% Typical)


Water 0.5% maximum (0.0 – 0.1% Typical)
Residual Ester 1.0% maximum (0.2 – 0.6% Typical)
Iodine Value 117 – 137 (g/100g)
Color (Gardner) 1 maximum (0 Typical)
Other Residuals 100ppm maximum each

Boiling Point (C) 297 (LVP-VOC Exempt)


Flash Point (C) 134 (PMCC)
Cloud Point (C) -13 (Low HLB Nonionic)
Kauri-Butanol Value >1000 (ASTM D1133)
Hansen Solubility Parameters D: 16.58, P: 9.58, H: 8.45 (Experimental*)
Estimated HLB 6 (Griffin or Davies)

* Using Hansen software and screening across a large set of test solvents
Molecule: Reaction, Chemistry, Properties

Amide 97% minimum (99% Typical)


Water 0.5% maximum (0.0 – 0.1% Typical)
Residual Ester 1.0% maximum (0.2 – 0.6% Typical)
Iodine Value 117 – 137 (g/100g)
Color (Gardner) 1 maximum (0 Typical)
Other Residuals 100ppm maximum each

Boiling Point (C) 297 (LVP-VOC Exempt)


Flash Point (C) 134 (PMCC)
Cloud Point (C) -13 (Low HLB Nonionic)
Kauri-Butanol Value >1000 (ASTM D1133)
Hansen Solubility Parameters D: 16.58, P: 9.58, H: 8.45 (Experimental*)
Estimated HLB 6 (Griffin, Davies, Oil)

* Using Hansen software and screening across a large set of test solvents
Molecule: Reaction, Chemistry, Properties
Chemical Stability: As-Is and Formulated
6% Emulsified at 80C, pH 3
Air Headspace
6% Emulsified at 80C, pH 11 For All Data
100% As-Is at 54C
120.00
100.00
% Remaining

80.00
60.00
40.00
20.00
0.00
0 2 4 11 18 25
Days (x3 for As-Is)

Amide is stable between pH 3-12, not beyond. -C=C- bond is stable as well.
Aqueous solutions demonstrate stability with peroxide at pH 3. Avoid NaOCl.
Molecule: Properties: Kauri-Butanol >1000
What does this mean ? Test Solvent

Kauri Resin

Kauri resin is soluble in butanol, less soluble in other solvents


Add test solvent to dilute the butanol solution of resin
At some added amount the resin precipitates due to insolubility
The more added to the endpoint, the higher the Kb value
Resins are common tackifiers for adhesives and coatings
High Kb value = good cleaning and removal performance
Molecule: Properties: Kauri-Butanol >1000
What does this mean ? Test Solvent

Kauri Resin

Kauri resin is soluble in butanol, less soluble in other solvents


Add test solvent to dilute the butanol solution of resin
At some added amount the resin precipitates due to insolubility
The more added to the endpoint, the higher the Kb value
Resins are common tackifiers for adhesives and coatings
High Kb value = good cleaning and removal performance
Molecule: Properties: Kauri-Butanol >1000
What does this mean ? Test Solvent

Kauri Resin

Kauri resin is soluble in butanol, less soluble in other solvents


Add test solvent to dilute the butanol solution of resin
At some added amount the resin precipitates due to insolubility
The more added to the endpoint, the higher the Kb value
Resins are common tackifiers for adhesives and coatings
High Kb value = good cleaning and removal performance
Molecule: Properties: Kauri-Butanol >1000
Saturated Analog, “ane”, ≈ 300 Kb value
What does this mean ? Test Solvent

Kauri Resin

Kauri resin is soluble in butanol, less soluble in other solvents


Add test solvent to dilute the butanol solution of resin
At some added amount the resin precipitates due to insolubility
The more added to the endpoint, the higher the Kb value
Resins are common tackifiers for adhesives and coatings
High Kb value = good cleaning and removal performance
Molecule: Properties: Hansen Map

Large
Hansen
“Radius”
12.9 Units

N,N-Dimethyl 9-Decenamide is fully miscible with solvents within green line area
Molecule: Properties: Hansen Map

“ene”

“ane”
Evidence For
Some Type of
Interaction
Between -C=C-
and Carbonyl

Ethylene Carbonate is miscible with N,N-Dimethyl 9-Decenamide, not Decanamide !


Molecule: Properties: HLB
Calculated for alcohol ethoxylates of similar solubility (Griffin)
Calculated via group contribution (Davies)
Experimentally determined via oil emulsification

Lard Lanolin Oil Rapeseed Oil


HLB Required: 5 9 6

All methods estimate HLB to be ≈6.


Greater than 5, less than 9 based on oil emulsification test
Window of Opportunity: CMC & Solubility
60
CMC calculates ≈ 500 - 1000 ppm
Surface Tension (mN/m)

55
Solubility Limit ≈ 1500 ppm
50

45

40

35

30

25
0.005 0.05 0.5 5 50
Concentration (wt. %)
N,N-Dimethyl 9-Decenamide, although very hydrophobic, can micellize in water
Window of Opportunity: CMC & Solubility
N,N-Dimethyl Decanamide
N,N-Dimethyl N,N-Dimethyl 9-Decenamide
9-Decenamide 80
“ene” 70
60
Is Different 50
From 40
30
N,N-Dimethyl
20
Decanamide
10
“ane” 0
0 5000 10000
Outline
• Metathesis Derivatives Program
• Molecule: Reaction, Chemistry, Properties
• Solution Behavior
• Applications
– Cleaning
– Personal Care
• Summary and Acknowledgements
Solution Behavior
• Soluble in water to about 0.15% (vs. 0.05% for “ane”)
• Can dissolve up to 19% added water, but not hygroscopic
• Formulate similar to a Low-HLB Nonionic
– Use charged (anionic or cationic) or mid/high HLB
cosurfactant(s)
• On its own, at 0.1 wt.%, Draves Wetting (ASTM D2281-
68) is nearly instant
– Better than saturated analog
– Better than similar Low-HLB alkoxylates
– Remarkably fast release of air from the surface
– “Fluffing” of the fibers observed

Let’s Watch
Solution Behavior
• Soluble in water to about 0.15% (vs. 0.05% for “ane”)
• Can dissolve up to 19% added water, but not hygroscopic
• Formulate similar to a Low-HLB Nonionic
– Use charged (anionic or cationic) or mid/high HLB
cosurfactant(s)
• On its own, at 0.1 wt.%, Draves Wetting (ASTM D2281-
68) is nearly instant
– Better than saturated analog
– Better than similar Low-HLB alkoxylates
– Remarkably fast release of air from the surface
– “Fluffing” of the fibers observed

Let’s Watch
Solution Behavior
• Soluble in water to about 0.15% (vs. 0.05% for “ane”)
• Can dissolve up to 19% added water, but not hygroscopic
• Formulate similar to a Low-HLB Nonionic
– Use charged (anionic or cationic) or mid/high HLB
cosurfactant(s)
• On its own, at 0.1 wt.%, Draves Wetting (ASTM D2281-
68) is nearly instant
– Better than saturated analog
– Better than similar Low-HLB alkoxylates
– Remarkably fast release of air from the surface
– “Fluffing” of the fibers observed

Let’s Watch
Before Weighted Skeins Dropped

These are solutions near the specified 0.1 wt%, but at solubility limits:
0.13% 0.05% 0.02% 0.25%
Weighted Skeins Dropped: 0 Seconds

Note the huge volume of air released from the Decenamide


(left-most cylinder), and the skein has sunk due to momentum
Weighted Skeins Dropped: 2 Seconds

Some air remains, buoying the skein for the Decenamide for a brief
moment. All others were buoyant at 0 seconds and remain buoyant.
Weighted Skeins Dropped: 4 Seconds

The Decenamide skein has sunk. All others remain buoyant.


Note the “fluffing” observed for both amides, Decene and Decane.
Weighted Skeins Dropped: 10 Seconds

The Decenamide skein has sunk. All others remain buoyant.


Note the “fluffing” observed for both amides, Decene and Decane.
Weighted Skeins Dropped: 12 Seconds

The Decanamide saturated analog skein begins to sink at 12


seconds, long after the Decenamide. “ene” is different than “ane”
Weighted Skeins Dropped: 16 Seconds

The Decanamide saturated analog skein has sunk at 16 seconds, long


after the Decenamide. C12/C13 EO3 and C6 EO1 remain buoyant.
Weighted Skeins Dropped: 20 Seconds

Still waiting on the other skeins to sink. The C12/13 EO3 will
take more than a minute, and the C6 EO1 does not sink.
Solution Behavior: “ene” faster than “ane”
Cotton
“ane” Cellulose
Fiber

“ene”

Nothing in this view to


suggest a difference
Volume and speed of air displaced depends on strength of adsorption,
diffusion rate, and molecular area1
1 Detergency: Theory and Technology, Surfactant Science Series: v. 20, W. Gale
Cutler and Erik Kisser, 1987, pp 314-5
Solution Behavior: “ene” faster than “ane”
Cotton
“ane” Cellulose
Fiber

Dilute Solution
Looped
Configuration
“enes” could
explain what is
observed

Volume and speed of air displaced depends on strength of adsorption,


diffusion rate, and molecular area1
1 Detergency: Theory and Technology, Surfactant Science Series: v. 20, W. Gale
Cutler and Erik Kisser, 1987, pp 314-5
Solution Behavior: Intra-H-Bonding ?
ATR-FTIR SPECTRA: Dilute Solution, Bulk Water Subtracted
H-O stretch broadened to
lower frequency (cm-1) for
“ene” compared to “ane”

“ene”

“ane”

C=O stretch broadened to


lower frequency (cm-1) for
“ene” compared to “ane”
Solution Behavior: Intra-H-Bonding ?
ATR-FTIR SPECTRA: Dilute Solution, Bulk Water Subtracted
H-O stretch broadened to
lower frequency (cm-1) for
“ene” compared to “ane”

“ene”

“ane”

C=O stretch broadened to


lower frequency (cm-1) for
“ene” compared to “ane”
Solution Behavior: Intra-H-Bonding ?
ATR-FTIR SPECTRA: Dilute Solution, Bulk Water Subtracted
H-O stretch broadened to
lower frequency (cm-1) for
“ene” compared to “ane”

“ene”

“ane”

C=O stretch broadened to


lower frequency (cm-1) for
“ene” compared to “ane”

“Making Water Work Like an Organic Solvent” Let’s Watch


“Making Water Work Like an Organic Solvent”
Chewing Gum: Dissolution/Disintegration

Formulated Aqueous, pH 11.5 As-Is As-Is As-Is As-Is Aqueous Commercial Cleaners
5% w/MEA 3% w/Na2CO3 100% 100% 100% 100% pH 13 pH 10.5

INITIAL

22C
50 hours

N,N-Dimethyl 9-Decenamide d-Limonene NMP DCM Degreaser Cleaner


“Making Water Work Like an Organic Solvent”
Conformational Analysis: Ab-Initio Calculations Pending
N,N-Dimethyl 9-Decenamide - Linear N,N-Dimethyl 9-Decenamide
H-bonded in a hypothesized
looped configuration

N,N-Dimethyl 9-Decenamide H-bonded to H2O

• FTIR, Draves, and Solution Behavior support this hypothesis, or at least a looped conformation
• Unorthodox to suggest H-C=C- H-bond: more positive than H–C-C-, but much less than water H-O-
• Perhaps the lowest energy conformation in dilute aqueous solution for H-C=C- ? TBD
“Making Water Work Like an Organic Solvent”
Solution Behavior: Minimize Hydrophobe Contact with H2O
Hydrophobe in H2O is a high energy condition
- Drives surfactant hydrophobe to surfaces 
- Drives hydrophobe to micelle interior 
- Drives hypothesized monomer conformation by
minimizing hydrophobe surface area contact with H2O
RELATIVE SURFACE AREA EXPOSED TO WATER MOLECULES IN SOLUTION

>
N,N-Dimethyl 9-Decenamide H-bonded to H2O N,N-Dimethyl 9-Decenamide H-bonded
hypothesized cyclic configuration
“Making Water Work Like an Organic Solvent”
Solution Behavior: Minimize Hydrophobe Contact with H2O
Hydrophobe in H2O is a high energy condition
- Drives surfactant hydrophobe to surfaces 
- Drives hydrophobe to micelle interior 
- Drives hypothesized monomer conformation by
minimizing hydrophobe surface area contact with H2O
RELATIVE SURFACE AREA EXPOSED TO WATER MOLECULES IN SOLUTION

>
N,N-Dimethyl 9-Decenamide H-bonded to H2O N,N-Dimethyl 9-Decenamide H-bonded
hypothesized cyclic configuration
“Making Water Work Like an Organic Solvent”
Solution Behavior: Minimize Hydrophobe Contact with H2O
Hydrophobe in H2O is a high energy condition
- Drives surfactant hydrophobe to surfaces 
- Drives hydrophobe to micelle interior 
- Drives hypothesized monomer conformation by
minimizing hydrophobe surface area contact with H2O
RELATIVE SURFACE AREA EXPOSED TO WATER MOLECULES IN SOLUTION

>
N,N-Dimethyl 9-Decenamide H-bonded to H2O N,N-Dimethyl 9-Decenamide H-bonded
hypothesized looped conformation
Applications: Nail Polish Removers
Requires >50% Acetone and/or Ethyl Acetate
Typically contain 90+% Organic Solvent
85% Water
5% N,N-Dimethyl 9-Decenamide
5% MEA

OR

87% Water Patent Pending


3% N,N-Dimethyl 9-Decenamide blend with great
1.5% Citrus Fragrance
0.3% Sodium Carbonate synergy and new
Balance: High HLB co-emulsifier mechanism(s)
WO2013162926(A1)

“Making Water Work Like an Organic Solvent”


Applications: Nail Polish Removers
Requires >50% Acetone and/or Ethyl Acetate
Typically contain 90+% Organic Solvent
85% Water
5% N,N-Dimethyl 9-Decenamide
5% MEA

OR

87% Water Patent Pending


3% N,N-Dimethyl 9-Decenamide blend with great
1.5% Citrus Fragrance
0.3% Sodium Carbonate synergy and new
Balance: High HLB co-emulsifier mechanism(s)
WO2013162926(A1)

“Making Water Work Like an Organic Solvent”


Applications: Nail Polish Removers
Requires >50% Acetone and/or Ethyl Acetate
Typically contain 90+% Organic Solvent
85% Water
5% N,N-Dimethyl 9-Decenamide
5% MEA

OR

87% Water Patent Pending


3% N,N-Dimethyl 9-Decenamide blend with great
1.5% Citrus Fragrance
0.3% Sodium Carbonate synergy and new
Balance: High HLB co-emulsifier mechanism(s)
WO2013162926(A1)

“Making Water Work Like an Organic Solvent”


Applications: “Waterless” Hand Cleaners
Requires >50% Emulsified Petroleum Distillates or Soy Methyl Ester
Typically contain 70+% Organic Solvent
85% Water
5% N,N-Dimethyl 9-Decenamide
5% MEA

OR

87% Water Patent Pending


3% N,N-Dimethyl 9-Decenamide blend with great
1.5% Citrus Fragrance
0.3% Sodium Carbonate synergy and new
Balance: High HLB co-emulsifier mechanism(s)
WO2013162926(A1)

“Making Water Work Like an Organic Solvent”


Applications: “Waterless” Hand Cleaners
Requires >50% Emulsified Petroleum Distillates or Soy Methyl Ester
Typically contain 70+% Organic Solvent
85% Water
5% N,N-Dimethyl 9-Decenamide
5% MEA

OR

87% Water Patent Pending


3% N,N-Dimethyl 9-Decenamide blend with great
1.5% Citrus Fragrance
0.3% Sodium Carbonate synergy and new
Balance: High HLB co-emulsifier mechanism(s)
WO2013162926(A1)

“Making Water Work Like an Organic Solvent”


Applications: “Waterless” Hand Cleaners
Requires >50% Emulsified Petroleum Distillates or Soy Methyl Ester
Typically contain 70+% Organic Solvent
85% Water
5% N,N-Dimethyl 9-Decenamide
5% MEA

OR

87% Water Patent Pending


3% N,N-Dimethyl 9-Decenamide blend with great
1.5% Citrus Fragrance
0.3% Sodium Carbonate synergy and new
Balance: High HLB co-emulsifier mechanism(s)
WO2013162926(A1)

“Making Water Work Like an Organic Solvent”


Applications: Blood Stain Remover
Typically Requires Peroxide or Hypochlorite

Decenamide +
Commercial
Citrus +
Peroxide
Carbonate +
Product
Co-Emulsifier

95% Water Patent Pending


1% N,N-Dimethyl 9-Decenamide blend with great
0.5% Citrus Fragrance synergy and new
0.1% Sodium Carbonate
mechanism(s)
Balance: High HLB co-emulsifier
WO2013162926(A1)

Mechanism: De-Chelation of Chromophores (UV-Vis)


Applications: Blood Stain Remover
Typically Requires Peroxide or Hypochlorite

Decenamide +
Commercial
Citrus +
Peroxide
Carbonate +
Product
Co-Emulsifier

95% Water Patent Pending


1% N,N-Dimethyl 9-Decenamide blend with great
0.5% Citrus Fragrance synergy and new
0.1% Sodium Carbonate
mechanism(s)
Balance: High HLB co-emulsifier
WO2013162926(A1)

Mechanism: De-Chelation of Chromophores (UV-Vis)


Applications: Marker Remover
Typically Requires IPA or Acetone: Not Good for Surfaces

Commercial Decenamide +
Marker Citrus +
Remover Carbonate +
Product Co-Emulsifier

95% Water Patent Pending


1% N,N-Dimethyl 9-Decenamide blend with great
0.5% Citrus Fragrance synergy and new
0.1% Sodium Carbonate mechanism(s)
Balance: High HLB co-emulsifier WO2013162926(A1)
Mechanism: De-Chelation of Chromophores (UV-Vis)
Applications: Marker Remover
Typically Requires IPA or Acetone: Not Good for Surfaces

Commercial Decenamide +
Marker Citrus +
Remover Carbonate +
Product Co-Emulsifier

95% Water Patent Pending


1% N,N-Dimethyl 9-Decenamide blend with great
0.5% Citrus Fragrance synergy and new
0.1% Sodium Carbonate mechanism(s)
Balance: High HLB co-emulsifier WO2013162926(A1)
Mechanism: De-Chelation of Chromophores (UV-Vis)
Applications: Oven Cleaning
Typically Requires Caustic: pH 12-14

Commercial
Oven Cleaner 85% Water
with Caustic 5% Decenamide
and Organic 5% MEA
Solvents pH 11.5
pH 12.5

Some alkalinity required, but not caustic → Safer pH


Applications: Materials Compatibility
• In-Vitro EpiDerm Test
- 6% N,N-Dimethyl 9-Decenamide
SKIN - 3% MEA
- Anionic/Nonionic co-emulsifiers
• 0.60 Hours for ET50, Moderate Irritant
• Similar to other surfactants

• Immersion Tests: ASTM D543-95


Plastics - Neat and formulated
• PET, HDPE, PP all OK
• Avoid PC (any amines/amide), PVC, Nylon
Gaskets • Immersion Tests
and - Neat and formulated
Seals • Teflon, Silicone, Peroxide Cured EPDM OK
• Avoid Viton and Elastomers
Applications: Materials Compatibility
• In-Vitro EpiDerm Test
- 6% N,N-Dimethyl 9-Decenamide
SKIN - 3% MEA
- Anionic/Nonionic co-emulsifiers
• 0.60 Hours for ET50, Moderate Irritant
• Similar to other surfactants

• Immersion Tests: ASTM D543-95


Plastics - Neat and formulated
• PET, HDPE, PP all OK
• Avoid PC (any amines/amide), PVC, Nylon
Gaskets • Immersion Tests
and - Neat and formulated
Seals • Teflon, Silicone, Peroxide Cured EPDM OK
• Avoid Viton and Elastomers
Applications: Materials Compatibility
• In-Vitro EpiDerm Test
- 6% N,N-Dimethyl 9-Decenamide
SKIN - 3% MEA
- Anionic/Nonionic co-emulsifiers
• 0.60 Hours for ET50, Moderate Irritant
• Similar to other surfactants

• Immersion Tests: ASTM D543-95


Plastics - Neat and formulated
• PET, HDPE, PP all OK
• Avoid PC (any amines/amide), PVC, Nylon
Gaskets • Immersion Tests
and - Neat and formulated
Seals • Teflon, Silicone, Peroxide Cured EPDM OK
• Avoid Viton and Elastomers
Outline
• Metathesis Derivatives Program
• Molecule: Reaction, Chemistry, Properties
• Solution Behavior
• Applications
– Cleaning
– Personal Care
• Summary and Acknowledgements
Acknowledgements
• AOCS and SCC
• Professor Bob Lochhead
• Elevance Renewable Sciences
• Stepan Company Team
– Senior Management including Randy Bernhardt, Rob Slone
– Program Manager Bridget Weir
– Sales Management including Nathan Shook
– Consumer Product Development R&D Manager Chris Gariepy
– Project Manager Wilma Gorman
– Synthesis, Analytical, and Applications Lab Colleagues
– Many more too numerous to mention
• Customers who have commercialized products
THANK YOU !
It is nice to have
MET-10U today
POWER OF THE DOUBLE BOND TM
All images and clip art in this presentation are the work of the author and Stepan Company Employees.
Presentation template and AOCS logo provided by AOCS for this presentation.

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