# US 7,608,336 B2 · Flame-retardant epoxy resin composition and cured product obtained therefrom > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 7,608,336 B2 - Document ID: US7608336B2 - Status: Granted - Kind: B2 - Application number: 11/148,471 - Filed: 2005-06-09 - Published: 2006-01-05 - Granted: 2009-10-27 - Earliest claimed: 2002-11-28 - Assignees: Nippon Kayaku Kabushiki Kaisha - Inventors: Yasumasa Akatsuka; Shigeru Moteki; Makoto Uchida; Kazunori Ishikawa - Web page: https://patentgrep.com/patent/US7608336B2 ## CPC - C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins - Y10T 428/31511: Of epoxy ether - Y10T 428/31681: Next to polyester, polyamide or polyimide [e.g., alkyd, glue, or nylon, etc.] - Y10T 428/31721: Of polyimide - Y10T 428/31725: Of polyamide - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION ## Abstract The invention relates to an epoxy resin composition containing (a) an epoxy resin and (b) a phenolic hydroxy group-containing polyamide resin having the structure represented by Formula (1), a method of curing the composition, a varnish, prepreg, or sheet using the composition, and an epoxy resin composition having the polyamide resin represented by Formula (1) as the active component. Cured products of the epoxy resin composition according to the present invention have a sufficient high flexibility when formed into a thin film, have a flame resistance even though the cured compositions do not contain a halogen flame retardant, an antimony compound, or the like and are superior in heat resistance and adhesiveness, and thus are extremely useful in a wide range of applications, for example, as molded materials, cast materials, laminate materials, paints, adhesives, resists, and the like. (wherein, l and m are averages, satisfying the formula: m/(l+m)=0.01; and l+m is a positive number of 2 to 200. Ar1 represents a bivalent aromatic group; Ar2 represents a phenolic hydroxyl group-containing bivalent aromatic group; and Ar3 represents: -ph(R1)n- or -ph(R2)n-X-ph(R3)n-, wherein, -ph(R1)n-, -ph(R2)n- and -ph(R3)n- represent respectively R1-substituted, R2-substituted and R3-substituted phenylene groups, or an unsubstituted phenylene group; n is an integer of 0 to 3; R1, R2 and R3 each independently represent a C1 to C3 alkyl group or a C1 to C3 alkoxy group; and X represents O, S, CO, SO2 or a single bond). ## Claims ### Claim 1 An epoxy resin composition, comprising an epoxy resin (a) and, as a curing agent, a polyamide resin (b) having the structure represented by the following Formula (1): wherein, l and m are averages, satisfying the following formula: m/(l+m)≧0.01; and l+m is a positive number of 2 to 200; Ar1 represents a bivalent aromatic group; Ar2 represents a phenolic hydroxyl group-containing bivalent aromatic group; Ar3 represents: -ph(R1)n- or -ph(R2)n-X-ph(R3)n-, wherein, -ph(R1)n-, -ph(R2)n- and -ph(R3)n- represent respectively R1-substituted, R2-substituted and R3-substituted phenylene groups; n is an integer of 0 to 3; R1, R2 and R3 each independently represent a C1 to C3 alkyl group or a C1 to C3 alkoxy group; and X represents O, S, CO, SO2 or a single bond, and being prepared by polycondensation of a phenolic hydroxy group containing aromatic dicarboxylic acid corresponding to Formula (1), an aromatic dicarboxylic acid having no phenolic hydroxy group corresponding to Formula (1) and an aromatic diamine corresponding to Formula (1), wherein the equivalence of the active hydrogen in the polyamide resin (b) is 0.7 to 1.2 equivalence relative to 1 equivalence of the epoxy group in the epoxy resin (a). ### Claim 2 (depends on 1) The epoxy resin composition according to claim 1, wherein as said curing agent, the polyamide resin (b) and other curing agents are optionally used in combination in the epoxy resin composition and the content of the polyamide resin of component (b) is 30 wt % or more relative to all curing agents contained in the composition. ### Claim 3 (depends on 1) The epoxy resin composition according to claim 1, comprising the epoxy resin of component (a) in an amount of 2 to 50 wt % and the polyamide resin of component (b) in an amount of 50 to 98 wt % based on the entire composition. ### Claim 4 (depends on 1, 2, 3) The epoxy resin composition according to any one of claims 1 to 3, wherein Ar3 is a group represented by: -ph(R1)n- or -ph(R2)n-O-ph(R3)n-. ### Claim 5 (depends on 1, 2, 3) The epoxy resin composition according to any one of claims 1 to 3, wherein the polyamide resin of component (b) is a compound having the structure represented by the following Formula (3): wherein l and m are the same as those in Formula (1). ### Claim 6 (depends on 1, 2, 3) The epoxy resin composition according to any one of claims 1 to 3, wherein the polyamide resin of component (b) is a compound having the structure represented by the following Formula (4): wherein l and m are the same as those in Formula (1). ### Claim 7 (depends on 1, 2, 3) The epoxy resin composition according to any one of claims 1 to 3, wherein l+m is a positive number of 2 to 20. ### Claim 8 (depends on 7) The epoxy resin composition according to claim 7, wherein the component (a) is a biphenyl skeleton-containing novolak epoxy resin represented by the following Formula (2): (wherein, p is an average having a positive number of 0.1 to 10). ### Claim 9 (depends on 1, 2, 3) The epoxy resin composition according to any one of claims 1 to 3, wherein the component (a) is one or more resins selected from the group consisting of novolak epoxy resins, xylylene skeleton-containing phenolic novolak epoxy resins, biphenyl skeleton-containing novolak epoxy resins, bisphenol A epoxy resins, bisphenol F epoxy resins, tetramethylbiphenol epoxy resins and triphenylmethane epoxy resins. ### Claim 10 (depends on 1, 2, 3) The epoxy resin composition according to any one of claims 1 to 3, further comprising a curing accelerator. ### Claim 11 (depends on 1) A varnish prepared by dissolving the epoxy resin composition according to claim 1 in a solvent. ### Claim 12 (depends on 11) A prepreg, characterized by being prepared by impregnating a base material with the varnish according to claim 11 and drying the resulting base material. ### Claim 13 (depends on 1) A varnish comprising a solvent and the epoxy resin composition according to claim 1, wherein the amount of said solvent is 10 to 70% relative to the total amount of solvent and epoxy resin in said varnish, with the balance being said epoxy resin composition. ### Claim 14 (depends on 13) The varnish according to claim 13, wherein the solvent is a C4 to C6 aliphatic ketone solvent. ### Claim 15 (depends on 1) A sheet, characterized by having a planar backing and one or two layers of the epoxy resin composition according to claim 1 formed on one or two faces thereof. ### Claim 16 (depends on 1) A sheet, characterized by having a cured layer prepared by curing the one or two layers of the epoxy resin composition according to claim 1 formed on one or two faces of a planar backing. ### Claim 17 (depends on 15, 16) The sheet according to claim 15 or 16, wherein the planar backing is a polyimide film, a metal foil, or a release film. ### Claim 18 (depends on 1) A method of curing an epoxy resin composition, characterized by heating the epoxy resin composition according to claim 1. ### Claim 19 (depends on 1) The epoxy resin composition according to claim 1, wherein m/(l+m) is 0.05 or more. ### Claim 20 A curing agent for epoxy resin, containing, as an active ingredient, a polyamide resin having the structure represented by the following Formula (1): (wherein, l and m are averages, satisfying the following formula: m/(l+m)≧0.01; and l+m is a positive number of 2 to 200; Ar1 represents a bivalent aromatic group; Ar2 represents a phenolic hydroxyl group-containing bivalent aromatic group; Ar3 represents: -ph(R1)n- or -ph(R2)n-X-ph(R3)n-, wherein ph(R1)n-, -ph(R2)n- and ph(R3)n- represent respectively, R1-substituted, R2substituted and R3-substituted phenylene groups; n is an integer of 0 to 3; R1, R2 and R3 each independently represent a C1 to C3 alkyl group or a C1 to C3 alkoxy group; and X represents O, S, CO, SO2 or a single bond), and being prepared by polycondensation of a phenolic hydroxy group containing aromatic dicarboxylic acid corresponding to Formula (1), an aromatic dicarboxylic acid having no phenolic hydroxy group corresponding to Formula (1) and an aromatic diamine corresponding to Formula (1). ### Claim 21 (depends on 20) The epoxy resin curing agent according to claim 20, wherein Ar3 is a group represented by: -ph(R1)n- or -ph(R2)n-O-ph(R3)n-. ### Claim 22 (depends on 20) A curing agent for epoxy resin according to claim 20, wherein m/(l+m) is 0.05 or more.