# US 8,541,500 B2 · Cardanol-based associative polyurethanes, corresponding associative thickeners and uses thereof > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,541,500 B2 - Document ID: US8541500B2 - Status: Granted - Kind: B2 - Application number: 12/859,525 - Filed: 2010-08-19 - Published: 2011-03-10 - Granted: 2013-09-24 - Earliest claimed: 2009-09-10 - Assignees: Coatex - Applicants: Jean-Marc Suau; Denis Ruhlmann - Inventors: Jean-Marc Suau; Denis Ruhlmann - Web page: https://patentgrep.com/patent/US8541500B2 ## CPC - C08G 18/2825: {having at least 6 carbon atoms} - C08G 18/10: Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step - C08G 18/283: {Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds} - C08G 18/2835: {having less than 5 ether groups} - C09D 7/43: Thickening agents - C08L 75/04: Polyurethanes - 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) - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) ## Abstract New associative polyurethanes which are manufactured with cardanol which is potentially oxyethylated. Use of these polyurethanes as thickening agents for aqueous formulations. ## Claims ### Claim 1 A water-soluble polyurethane resulting from the condensation of: a) oxyalkylated cardanol and a polyalkylene glycol, and b) at least one polyisocyanate, wherein said water-soluble polyurethane consists of polymerized units of said oxyalkylated cardanol, said polyalkylene glycol and said at least one polyisocyanate. ### Claim 2 (depends on 1) A polyurethane according to claim 1 which results from the condensation of, expressed as a % by weight of each of the monomers, the sum of these % s being equal to 100%: 90% to 99.5% of oxyalkylated cardanol and a polyalkylene glycol, and 0.5% to 10% of at least one polyisocyanate. ### Claim 3 (depends on 1) A polyurethane according to claim 1, wherein the polyalkylene glycol is polyethylene glycol. ### Claim 4 (depends on 3) A polyurethane according to claim 3, wherein the polyethylene glycol has a molecular mass of 2,000 g/mole-20,000 g/mole. ### Claim 5 (depends on 3) A polyurethane according to claim 3, wherein the polyethylene glycol has a molecular mass of 8,000 g/mole-12,000 g/mole. ### Claim 6 (depends on 2) A polyurethane according to claim 2, wherein the polyalkylene glycol is polyethylene glycol. ### Claim 7 (depends on 6) A polyurethane according to claim 6, wherein the polyethylene glycol has a molecular mass of 2,000 g/mole-20,000 g/mole. ### Claim 8 (depends on 6) A polyurethane according to claim 6, wherein the polyethylene glycol has a molecular mass of 8,000 g/mole-12,000 g/mole. ### Claim 9 (depends on 1) A polyurethane according to claim 1, wherein the polyisocyanate is selected from the group consisting of 1,4-butane di-isocyanate, 1,6-hexane diisocyanate, isophorone diisocyanate, 1,3-cyclohexane diisocyanate, 1,4-cyclohexane diisocyanate, 4,4′diisocyanatodicyclohexylmethane, 1-methyl-2,4-diisocyanatocyclohexane and its mixture with 1-methyl-2,6-diisocyanatocyclohexane, the biuret of hexamethylene diisocyanate, the trimer of hexamethylene diisocyanate, the trimer of isophorone diisocyanate and mixtures thereof. ### Claim 10 (depends on 1) A polyurethane according to claim 1, wherein the oxyalkylated cardanol is oxyethylated with 1-100 ethylene oxide units. ### Claim 11 (depends on 10) A polyurethane according to claim 10, wherein the oxyalkylated cardanol is oxyethylated with 5-60 ethylene oxide units. ### Claim 12 (depends on 1) An aqueous composition comprising a polyurethane according to claim 1. ### Claim 13 (depends on 12) The aqueous composition comprising a polyurethane according to claim 12, wherein said composition is an aqueous paint, a lacquer, a varnish, a paper coating, a cosmetic formulation, or a detergent formulation. ### Claim 14 (depends on 6) A polyurethane according to claim 6, wherein the oxyalkylated cardanol is oxyethylated with 1-100 ethylene oxide units. ### Claim 15 (depends on 14) A polyurethane according to claim 14, wherein the oxyalkylated cardanol is oxyethylated with 5-60 ethylene oxide units. ### Claim 16 (depends on 2) A polyurethane according to claim 2, wherein said water-soluble polyurethane consists of polymerized units of oxyalkylated cardanol oxyethylated with 5-60 ethylene oxide units, polyethylene glycol having a molecular mass of 2,000 g/mole-20,000 g/mole, and isophorone diisocyanate. ### Claim 17 (depends on 6) A polyurethane according to claim 6, wherein the polyisocyanate is selected from the group consisting of 1,4-butane di-isocyanate, 1,6-hexane diisocyanate, isophorone diisocyanate, 1,3-cyclohexane diisocyanate, 1,4-cyclohexane diisocyanate, 4,4′diisocyanatodicyclohexylmethane, 1-methyl-2,4-diisocyanatocyclohexane and its mixture with 1-methyl-2,6-diisocyanatocyclohexane, the biuret of hexamethylene diisocyanate, the trimer of hexamethylene diisocyanate, the trimer of isophorone diisocyanate and mixtures thereof. ### Claim 18 (depends on 15) A polyurethane according to claim 15, wherein the polyisocyanate is selected from the group consisting of 1,4-butane di-isocyanate, 1,6-hexane diisocyanate, isophorone diisocyanate, 1,3-cyclohexane diisocyanate, 1,4-cyclohexane diisocyanate, 4,4′diisocyanatodicyclohexylmethane, 1-methyl-2,4-diisocyanatocyclohexane and its mixture with 1-methyl-2,6-diisocyanatocyclohexane, the biuret of hexamethylene diisocyanate, the trimer of hexamethylene diisocyanate, the trimer of isophorone diisocyanate and mixtures thereof.