# US 8,569,424 B2 · Brominated and epoxidized flame retardants > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,569,424 B2 - Document ID: US8569424B2 - Status: Granted - Kind: B2 - Application number: 12/825,591 - Filed: 2010-06-29 - Published: 2010-12-30 - Granted: 2013-10-29 - Earliest claimed: 2009-06-30 - Assignees: Dow Global Technologies LLC - Applicants: Erin B. Vogel; Shari L. Kram; Daniel J. Murray; Bruce A. King - Inventors: Erin B. Vogel; Shari L. Kram; Daniel J. Murray; Bruce A. King - Web page: https://patentgrep.com/patent/US8569424B2 ## CPC - C08C 19/06: Epoxidation - C08C 19/12: Incorporating halogen atoms into the molecule - C08C 19/14: by reaction with halogens - C08F 8/08: Epoxidation - C08J 9/0061: {characterized by the use of several polymeric components} - C08J 9/12: by a physical blowing agent - C09K 21/14: Macromolecular materials - C08F 2800/20: as weight or mass percentages - C08J 2201/03: Extrusion of the foamable blend - C08J 2205/052: Closed cells, i.e. more than 50% of the pores are closed - C08J 2325/06: Polystyrene - C08J 2453/02: of vinyl aromatic monomers and conjugated dienes - C08C: TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29) - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE ## Abstract Brominated and epoxidized organic compounds are useful flame retardants for polymers such as polystyrene. The organic compounds contain both bromine and oxirane groups, and have molecular weights of at least 1500. The brominated and epoxidized organic compounds can be prepared by sequentially brominating and epoxiding (in either order) a starting compound that contains multiple non-conjugated carbon-carbon double bonds. ## Claims ### Claim 1 A brominated and epoxidized organic compound having a molecular weight of at least 1500, a bromine content of at least 35% by weight and at least one oxirane group per molecule, and which has a 5% weight loss temperature of at least 180° C., wherein the brominated and epoxidized organic compound is a brominated and epoxidized homopolymer or copolymer of butadiene or a brominated and epoxidized ester of a polyol and one or more fatty acids. ### Claim 2 (depends on 1) The brominated and epoxidized organic compound of claim 1, wherein at least one of the oxirane group(s) is terminal. ### Claim 3 (depends on 1) A process for preparing a brominated and epoxidized organic compound of claim 1, comprising (a) brominating a starting compound that has a molecular weight of at least 700 and multiple non-conjugated carbon-carbon double bonds such at least one but less than all of the non-conjugated carbon-carbon double bonds are brominated and the brominated starting compound contains at least 35% by weight bromine, and then (b) epoxidizing at least one remaining non-conjugated carbon-carbon double bond. ### Claim 4 (depends on 3) The process of claim 3, wherein the starting compound is a homopolymer or copolymer of butadiene. ### Claim 5 (depends on 3) The process of claim 3, wherein the starting compound is an ester of a polyol and one or more fatty acids. ### Claim 6 (depends on 3) The process of claim 3, wherein said at least one remaining non-conjugated carbon-carbon double bond is terminal. ### Claim 7 (depends on 1) A process for preparing a brominated and epoxidized organic compound of claim 1, comprising (a) epoxidizing a starting compound that has a molecular weight of at least 700 and multiple non-conjugated carbon-carbon double bonds such at least one but less than all of the non-conjugated carbon-carbon double bonds is epoxidized and then (b) brominating at least a portion of the remaining non-conjugated carbon-carbon double bonds by contacting the compound with a quaternary ammonium tribromide or quaternary phosphonium tribromide, to produce an brominated and epoxidized organic compound that has a molecular weight of at least 1500 and contains at least 35% by weight bromine. ### Claim 8 (depends on 7) The process of claim 7, wherein the starting compound is a homopolymer or copolymer of butadiene. ### Claim 9 (depends on 7) The process of claim 7, wherein the starting compound is an ester of a polyol and one or more fatty acids. ### Claim 10 (depends on 1) A process for preparing a brominated and epoxidized organic compound of claim 1, comprising includes (a) brominating a starting unsaturated compound that contains both internal non-conjugated carbon-carbon double bonds and terminal non-conjugated carbon-carbon double bonds until at least 90% of the internal carbon-carbon double bonds are brominated but no more than 90% of the terminal carbon-carbon double bonds are brominated and (b) epoxidizing at least a portion of the remaining terminal carbon-carbon double bonds, to provide a brominated and epoxidized organic compound that contains at least 35% by weight bromine and from 0.1 to 5 weight percent of oxirane oxygen. ### Claim 11 (depends on 10) The process of claim 10, wherein the starting compound is a homopolymer or copolymer of butadiene. ### Claim 12 (depends on 10) The process of claim 10, wherein step (a) is conducted by contacting the starting compound with a quaternary ammonium tribromide or a quaternary phosphonium tribromide. ### Claim 13 (depends on 10) The process of claim 10, wherein step (b) is conducted by contacting the brominated starting compound with meta-chloroperbenzoic acid. ### Claim 14 A process for preparing a brominated and epoxidized butadiene polymer, comprising (a) brominating a starting butadiene polymer having a molecular weight of at least 700 and which has both 1,4-butadiene units and 1,2-butadiene units, such that at least 90% of the 1,4-butadiene units are brominated and at most 90% of the 1,2-butadiene units are brominated; and then (b) epoxidizing at least one of the remaining unbrominated 1,2-butadiene units to form a brominated and epoxidized butadiene polymer. ### Claim 15 (depends on 14) The process of claim 14, wherein step (a) is conducted by contacting the starting compound with a quaternary ammonium tribromide or a quaternary phosphonium tribromide. ### Claim 16 (depends on 14) The process of claim 14, wherein step (b) is conducted by contacting the brominated starting compound with meta-chloroperbenzoic acid. ### Claim 17 (depends on 1) An organic polymer composition comprising an organic polymer having dissolved or dispersed therein an amount of the brominated and epoxidized organic compound of claim 1 sufficient to impart to the composition at least 0.1 part by weight of bromine per 100 parts by weight of the organic polymer composition.