1. Natural Oil PolythiolsBy
Chad W. Brown
Chevron Phillips Chemical Co., LP
ACS Green Chemistry & Engineering Conference
June 24-26, 2008
6/24/2008
ACS Green Chemistry and Engineering Conference 2008

2. ACS Green Chemistry and Engineering Conference 2008
Outline
Background – why natural oil polythiols?
Soybean oil polythiols
Polythiourethane bulk polymer properties
Application performance summary of soybean oil polythiol-based polythiourethanes
Adhesives
Coatings
6/24/2008
ACS Green Chemistry and Engineering Conference 2008

3. Company Structure Chevron Chevron Phillips Chemical Company LLC
$93 billion assets
$137 billion revenues04
$93 billion assets
$155 billion revenues
Chevron Phillips Chemical Company LLC
$7 billion assets
$11 billion in sales
5150 Employees, 31 Plants in Eight Countries
Six Research and Technology Centers
Olefins/Polyolefins SBU
Ethylene – Propylene
HDPE – LDPE – LLDPE
PP – NAO – PAO
Performance Pipe
Specialty Products SBU
Specialty Chemicals
Ryton® PPS
Aromatics/Styrenics
Styrene – Polystyrene
Paraxylene – Cyclohexane
Benzene
K-Resin® SBC
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ACS Green Chemistry and Engineering Conference 2008 5

4. Core Competency H2S/Mercaptan Technology
Specialty Chemicals
Core Competency H2S/Mercaptan Technology
Halide Displacement
H2S
Epoxide Ring Opening
R-X
X-R-X
Hydroxy
Displacement
(R-OH)
(Olefin)
Diolefin
Olefin Addition
Regioselective
6/24/2008
ACS Green Chemistry and Engineering Conference 2008

5. Polythiols (or Polymercaptans)
Thiol? Mercaptan? What’s that?
6/24/2008
ACS Green Chemistry and Engineering Conference 2008

6. ACS Green Chemistry and Engineering Conference 2008
Why Polythiols?
Review of sulfur containing polymer literature suggest the following benefits:
Adhesion characteristics
Weathering, UV stability, antioxidant properties
Hydrophobicity
Chemical & corrosion resistance
Improved refractive index
6/24/2008
ACS Green Chemistry and Engineering Conference 2008

7. Soy Polythiols – MSO (polymercaptan 358)
6/24/2008
ACS Green Chemistry and Engineering Conference 2008

8. Soy Polythiols – MHSO (Polymercaptan 407)
6/24/2008
ACS Green Chemistry and Engineering Conference 2008

9. ACS Green Chemistry and Engineering Conference 2008
Soy Polythiols – General Properties
PM 358: pale yellow to yellow in color
PM 407: colorless to pale tan color
Acid # for each consistent with starting soybean oil feedstock
6/24/2008
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10. Polyurethane and Polythiourethane
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11. ACS Green Chemistry and Engineering Conference 2008
Soy Polythiourethanes General Mechanical Properties – Tensile vs. Modulus
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12. Potential Application Areas for Soy Polythiols
Polyurethanes
Coatings
Adhesives
Sealants
Epoxy system
Feasibility demonstrated
6/24/2008
ACS Green Chemistry and Engineering Conference 2008

13. ACS Green Chemistry and Engineering Conference 2008
Natural Oil Polythiol Polythiourethane Application Performance Conclusions
PM 358-based moisture cure one part polythiourethane adhesives form high strength bonds to both wood and CRS (~1000 psi full cure strength on wood)
PM 358-based adhesives retain strong bonds upon exposure to high temperature and humidity and are higher than those obtained by commercial comparisons
Adhesives can be formulated with different catalysts (tin or amine)
2K polythiourethane coatings system based on PM 407 performed well compared to commercial, fully formulated exterior coating
Less yellowing
Gloss retention
Chemical resistance
Hydrophobicity
6/24/2008
ACS Green Chemistry and Engineering Conference 2008

14. Future Work & Additional Comments
Registration status
TSCA complete
Canadian DSL complete for PM 358
Working with key development partners
Assisting customers in starting point formulations
Next generation products are in planning stages
6/24/2008
ACS Green Chemistry and Engineering Conference 2008

15. ACS Green Chemistry and Engineering Conference 2008
Acknowledgements
ACS
Chevron Phillips Chemical Company LP
Specialty Chemicals Research Team
Bartlesville, OK Specialty Chemicals Pilot Plant
Specialty Chemicals Marketing Team
6/24/2008
ACS Green Chemistry and Engineering Conference 2008