# US 11,114,679 B2 · Curable resin composition, and fuel cell and sealing method using the same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,114,679 B2 - Document ID: US11114679B2 - Status: Granted - Kind: B2 - Application number: 16/497,252 - Filed: 2018-04-13 - Published: 2020-10-08 - Granted: 2021-09-07 - Earliest claimed: 2017-04-14 - Assignees: Threebond Co., Ltd. - Applicants: Threebond Co., Ltd. - Inventors: Tetsunori Soga; Masayuki Fukumoto - Web page: https://patentgrep.com/patent/US11114679B2 ## CPC - C08L 23/22: Copolymers of isobutene; Butyl rubber; Homopolymers or copolymers of other iso-olefins - H01M 8/0284: Organic resins; Organic polymers - C08F 236/14: containing elements other than carbon and hydrogen - C08K 5/06: Ethers; Acetals; Ketals; Ortho-esters - C08K 5/54: Silicon-containing compounds {(C08K5/0091 takes precedence)} - C08L 101/02: characterised by the presence of specified groups {, e.g. terminal or pendant functional groups} - C09J 5/06: involving heating of the applied adhesive - C09J 147/00: Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Adhesives based on derivatives of such polymers (C09J145/00 takes precedence; based on conjugated diene rubbers C09J109/00 - C09J121/00) - C09K 3/10: {Materials in mouldable or extrudable form} for sealing or packing joints or covers (filling pastes C09D5/34) - H01M 8/0273: with sealing or supporting means in the form of a frame - H01M 8/10: Fuel cells with solid electrolytes - H01M 8/1004: characterised by membrane-electrode assemblies [MEA] (H01M8/12 takes precedence) - H01M 8/1018: Polymeric electrolyte materials - C08F 2800/20: as weight or mass percentages - C08G 77/48: in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms (C08G77/42 takes precedence) - C09J 2301/416: use of irradiation - C09J 2409/00: Presence of diene rubber - H01M 2008/1095: {Fuel cells with polymeric electrolytes} - H01M 2300/0082: Organic polymers - Y02E 60/50: Fuel cells - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - H01M: PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) - C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H) - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION ## Abstract The present invention aims to provide a curable resin composition which has low viscosity as well as properties such as high elongation property, high tensile strength, and hydrogen gas barrier property. A curable resin composition includes the following ingredients (A) to (D): ingredient (A): a vinyl polymer having one or more alkenyl groups in one molecule; ingredient (B): a compound having one or more hydrosilyl groups in one molecule; ingredient (C): a hydrosilylation catalyst; ingredient (D): a polyfunctional vinyl ether compound. ## Claims ### Claim 1 A curable resin composition comprising the following ingredients (A) to (D): ingredient (A): a vinyl polymer having one or more alkenyl groups in one molecule ingredient (B): a compound having one or more hydrosilyl groups in one molecule ingredient (C): a hydrosilylation catalyst ingredient (D): a polyfunctional vinyl ether compound. ### Claim 2 (depends on 1) The curable resin composition according to claim 1, wherein the ingredient (D) is at least one selected from the group consisting of polyfunctional vinyl ether compounds containing a cycloalkane structure, polyfunctional vinyl ether compounds containing an ether structure, and polyfunctional vinyl ether compounds containing an alkylene structure. ### Claim 3 (depends on 1) The curable resin composition according to claim 1, wherein the ingredient (A) is polyisobutylene having one or more alkenyl groups or an acrylic polymer having one or more alkenyl groups. ### Claim 4 (depends on 1) A curable sealing agent for a fuel cell comprising the curable resin composition according to claim 1. ### Claim 5 (depends on 4) The curable sealing agent for a fuel cell according to claim 4, wherein the curable sealing agent for a fuel cell is a curable sealing agent for a fuel cell for a periphery of any member selected from the group consisting of separators, frames, electrolytes, fuel electrodes, air electrodes, and electrolyte membrane electrode assemblies, which are members in a fuel cell. ### Claim 6 (depends on 4) The curable sealing agent for a fuel cell according to claim 4, wherein the curable sealing agent for a fuel cell is a sealing agent between adjacent separators in a fuel cell or a sealing agent between a frame of a fuel cell and an electrolyte membrane or an electrolyte membrane electrode assembly. ### Claim 7 (depends on 4) The curable sealing agent for a fuel cell according to claim 4, wherein the fuel cell is a solid polymer fuel cell. ### Claim 8 (depends on 4) A cured product obtained by curing the curable sealing agent for a fuel cell according to claim 4. ### Claim 9 (depends on 1) A cured product obtained by curing the curable resin composition according to claim 1. ### Claim 10 (depends on 9) A fuel cell comprising any seal selected from the group consisting of seals between adjacent separators in the fuel cell and seals between a frame and an electrolyte membrane or an electrolyte membrane electrode assembly in the fuel cell, wherein any one of the seals contains the cured product according to claim 9. ### Claim 11 (depends on 10) The fuel cell according to claim 10, wherein the fuel cell is a solid polymer fuel cell. ### Claim 12 (depends on 1) A method for sealing at least part of at least two flanges of seal target components including the at least two flanges, at least one of which is transmissive of heat or active energy rays, the method comprising the steps of: applying the curable resin composition according to claim 1 to a surface of at least one of the flanges; sticking the one flange with the curable resin composition applied thereto onto the other flange with the curable resin composition interposed in between; and sealing the at least part of between the at least two flanges by curing the curable resin composition by heating or irradiation with active energy rays through the light-transmissive flange. ### Claim 13 (depends on 1) A method for sealing at least part of at least two flanges of seal target components including the at least two flanges, the method comprising the steps of: applying the curable resin composition according to claim 1 to at least one of the flanges; heating or irradiating the applied curable resin composition with active energy rays to cure the curable resin composition, thereby forming a gasket composed of a cured product of the curable resin composition; placing the other flange on the gasket, and sealing the at least part of between the at least two flanges in such a way that the other flange and the one flange with the curable resin composition applied thereto are pressure bonded together with the gasket interposed in between. ### Claim 14 (depends on 1) A method for sealing at least part of at least two flanges of seal target components including the at least two flanges, the method comprising the steps of: placing a gasket formation mold on at least one of the flanges; injecting the curable resin composition according to claim 1 into at least part of a cavity formed between the gasket formation mold and the flange on which the mold is placed; heating or irradiating the curable resin composition with active energy rays to cure the curable resin composition, thereby forming a gasket composed of a cured product of the curable resin composition; detaching the mold from the one flange; and sealing the at least part of between the at least two flanges by placing the other flange on the gasket and then pressure bonding the one and the other flanges together with the gasket interposed in between. ### Claim 15 (depends on 1) The curable resin composition according to claim 1, wherein the ingredient (A) is a polyisobutylene having a —[CH2C(CH3)2]- unit. ### Claim 16 (depends on 1) The curable resin composition according to claim 1, wherein the ingredient (B) is a silicone containing a hydrosilyl group in a molecule which is a linear, branched, cyclic, or reticular molecule. ### Claim 17 (depends on 1) The curable resin composition according to claim 1, wherein the ingredient (C) is at least one selected from the group consisting of chloroplatinic acid, the platinum-olefin complexes, and the platinum-vinylsiloxane complexes. ### Claim 18 (depends on 1) The curable resin composition according to claim 1, wherein the ingredient (D) is at least one selected from the group consisting of cyclohexane divinyl ether, triethylene glycol divinyl ether, diethylene glycol divinyl ether, and 1,4-butylene divinyl ether. ### Claim 19 (depends on 1) The curable resin composition according to claim 1 further comprising a plasticizer. ### Claim 20 (depends on 19) The curable resin composition according to claim 19, wherein the plasticizer is a polyalphaolefin-based plasticizer.