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M AT E R I A L S S C I E N C E

High Modulus Polymers and Composites from Plant Oils Inventors:

Patent Number: Issue Date:

Wool, Richard P.; Kusefoglu, Selim; Palmese, Guideppe; Khot, Shirikant; Zhao, Ralph 6,121,398 September 19, 2000

Docket Number: UD98-01

The synthesis of liquid molding resins derived from plant oils that are capable of curing to high modulus thermosetting polymers and composites is described in this invention. The resins described resemble the unsaturated polyester, vinyl ester and epoxy resins presently used as the polymer matrix material in high performance glass, carbon, aramid and natural fiber reinforced composite materials. The resins disclosed herein are suitable for polymer and composite manufacture by Resin Transfer Molding (RTM), Reaction Injection Molding (RIM), Vacuum Assisted Resin Transfer Molding (VARTM), Seeman’s Composite Resin Infusion Manufacturing Process (SCRIMP), Atmospheric Pressure Molding (APM), open mold casting, spray-up, Sheet Molding Compound (SMC) Bulk Molding Compound (BMC), filament winding, pultrusion, prepregs, lamination and compression molding. The resins in this invention are synthesized predominantly from plant — in particular, from the abundant and cheap, soybean — triglycerides with suitable comonomers and reactants that functionalize and render the plant triglyceride polymerizable. The polymerization reactions involve free radical initiated addition, condensation or ring opening polymerization. The functionalized triglycerides is used in conjunction with reactive diluents, accelerators, viscosity modifiers, cross-linking, toughening and coupling agents. The liquid resins are then mixed with initiators, catalysts and the reinforcing fibers and chain extended or cross-linked to give the final cured composite.

Pressure-Sensitive Adhesives from Plant Oil Inventors:

Patent Number: Issue Date:

Wool, Richard; Bunker, Shana 6,646,033 November 11, 2003

Docket Number: UD01-24

This invention describes the synthesis of monomers and the subsequent polymers that are capable of being used in the pressure-sensitive adhesive (PSA) industry. The starting material is derived from plant oils such as high oleic soybean oil, olive oil, and other oils which are capable of being chemically functionalized. Specifically, the material is a fatty acid methyl ester that is esterified from a triglyceride molecule. This long aliphatic molecule resembles petroleum-based polymers such as 2-ethylhexyl acrylate and n-butyl acrylate, which are currently being used in the PSA market. The monomer and polymer disclosed comprise a new composition of matter and a new use for known and future genetically modified plant oils. Sheet Molding Compound Resins from Plant Oils Inventor:

Patent Number: Issue Date:

Wool, Richard P.; Lu, Jue; Khot, Shrikant N. 6,900,261

Docket Number: UD01-28

May 31, 2005

This present invention concerns the preparation of novel thermosetting resins derived from plant and animal oil triglycerides for use in sheet molding compounds. The starting materials are derived from sources such as, but not limited to, soybean oil, linseed oil, rapeseed oil, cottonseed oil, corn oil, palm oil, fish oil, canola oil, and peanut oil. These resins are produced by suitably functionalizing the triglyceride with chemical groups necessary for the SMC thickening process and polymerization reaction. Specifically, this liquid polymer composition contains a modified polyester oligomer having a carboxylic acid group and ethylenic unsaturation.

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