# US 8,568,889 B2 · Aqueous polymer compositions obtained from epoxidized natural oils > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,568,889 B2 - Document ID: US8568889B2 - Status: Granted - Kind: B2 - Application number: 12/918,216 - Filed: 2009-02-16 - Published: 2010-12-30 - Granted: 2013-10-29 - Earliest claimed: 2008-02-19 - Assignees: Lubrizol Advanced Materials, Inc. - Applicants: Anthony D. Pajerski; Svetlana N. Lerner - Inventors: Anthony D. Pajerski; Svetlana N. Lerner - Web page: https://patentgrep.com/patent/US8568889B2 ## CPC - C08F 283/006: {on to polymers provided for in C08G18/00 (C08F283/004 takes precedence)} - C08F 290/147: {Polyurethanes; Polyureas} - C08G 18/0823: {containing carboxylate salt groups or groups forming them} - C08G 18/12: using two or more compounds having active hydrogen in the first polymerisation step - C08G 18/36: Hydroxylated esters of higher fatty acids - C08G 18/6659: {with compounds of group C08G18/34} - C09D 175/04: Polyurethanes - Y10T 428/31551: Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.] - Y10T 428/31591: Next to cellulosic - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D) - Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION ## Abstract Aqueous polyurethane dispersions are made from urethane prepolymers comprising one or more polyhydroxy compounds from ketone functional molecules derived from an epoxidized natural oil. Addition of a hydrazine functional moiety to the prepolymer dispersion can further provide a crosslinking mechanism resulting in the formation of azomethine linkages in the resulting polyurethane during drying. When the ketone functional molecule is derived from levulinic acid and epoxidized vegetable oil, the resulting urethane dispersion can also be converted into a hybrid polyurethane-vinyl dispersion by adding and polymerizing one or more vinyl monomers in the polyurethane prepolymer or polyurethane dispersion. ## Claims ### Claim 1 An aqueous polyurethane dispersion comprising at least one polyol obtained from the reaction of an epoxidized natural oil having an oxirane oxygen content of about 7 to 12% by weight with an organic acid forming a residue that is co-reacted with di or other polyisocyanates to form a portion of the polyurethane wherein said residue of said epoxidized natural oil is at least 20 wt. % of the polyurethane portion of the polyurethane dispersion. ### Claim 2 (depends on 1) An aqueous polyurethane dispersion according to claim 1, wherein said polyol is also co-reacted with a dispersing diol and/or a dispersing polyol. ### Claim 3 (depends on 1) An aqueous polyurethane dispersion according to claim 1, wherein said polyol contains reactive carbonyl groups derived from said organic acid. ### Claim 4 (depends on 3) An aqueous polyurethane dispersion according to claim 3 wherein the organic acid is either levulinic or pyruvic acid and that imparts ketone functionality to the resulting polyol derived from the epoxidized natural oil. ### Claim 5 (depends on 3) An aqueous polyurethane dispersion according to claim 3 wherein the epoxidized natural oil is either soybean or linseed oil. ### Claim 6 (depends on 3) An aqueous polyurethane dispersion according to claims 3, wherein the residue of said epoxidized natural oil is at least 30 wt. % of the polyurethane portion of said polyurethane dispersion. ### Claim 7 (depends on 3) An aqueous polyurethane dispersion according to claim 3, further comprising a hydrazine functional moiety capable of reacting with said carbonyl groups forming azomethine linkages. ### Claim 8 (depends on 3) An aqueous polyurethane dispersion according to claim 3, wherein an ethylenically unsaturated co-monomer(s) is added to said polyurethane, while said polyurethane was either in the form of a prepolymer or dispersion of the prepolymer in water, and thereafter said ethylenically unsaturated comonomer(s) is free radically polymerized to form a hybrid polymer of poly(vinyl monomer(s)) and polyurethane. ### Claim 9 (depends on 1) An aqueous polyurethane dispersion according to claim 1, further comprising at least one polyketone functional oligomer or polymer. ### Claim 10 (depends on 9) An aqueous polyurethane dispersion according to claim 9, wherein said polyketone oligomer is derived from the reaction of epoxidized natural oil with an organic acid. ### Claim 11 An aqueous polyurethane dispersion according to claim l, further comprising at least one vinyl polymer having ketone functional moiety(ies). ### Claim 12 (depends on 1) A coated substrate comprising a substrate and the aqueous polyurethane dispersion according to claim 1. ### Claim 13 (depends on 12) A coated substrate according to claim 12, wherein said substrate comprises cellulose or is wood.