Natural Oil Polythiols By 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

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

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 6/24/2008 ACS Green Chemistry and Engineering Conference 2008 5

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

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

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

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

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

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 ACS Green Chemistry and Engineering Conference 2008

Polyurethane and Polythiourethane 6/24/2008 ACS Green Chemistry and Engineering Conference 2008

ACS Green Chemistry and Engineering Conference 2008 Soy Polythiourethanes General Mechanical Properties – Tensile vs. Modulus 6/24/2008 ACS Green Chemistry and Engineering Conference 2008

Potential Application Areas for Soy Polythiols Polyurethanes Coatings Adhesives Sealants Epoxy system Feasibility demonstrated 6/24/2008 ACS Green Chemistry and Engineering Conference 2008

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

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

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