# US 10,865,272 B2 · Thermosetting resin composition > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,865,272 B2 - Document ID: US10865272B2 - Status: Granted - Kind: B2 - Application number: 16/292,708 - Filed: 2019-03-05 - Published: 2019-06-27 - Granted: 2020-12-15 - Earliest claimed: 2014-09-11 - Assignees: Teijin Limited - Applicants: Teijin Limited - Inventors: Shinichiro Shoji; Kouhei Endo; Masaya Shibano - Web page: https://patentgrep.com/patent/US10865272B2 ## CPC - C08G 59/4042: {Imines; Imides} - C07D 491/113: with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring - C08G 59/5033: {aromatic} - C08G 59/686: {containing nitrogen} - C08K 5/18: with aromatically bound amino groups - C08K 5/29: Compounds containing {one or more} carbon-to-nitrogen double bonds - C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) ## Abstract A thermosetting resin composition which produces no free isocyanate even when a carbodiimide compound is used and provides a cured resin having high heat resistance. The thermosetting resin composition makes it possible to reduce the curing temperature, cures in a short time and provides a cured rein having a high glass transition temperature. The thermosetting resin composition includes: (A) an epoxy resin (component A); and (B) a cyclic carbodiimide compound (component B) including a cyclic structure having one carbodiimide group in which first nitrogen and second nitrogen are bonded together by a bond group and having 8 to 50 atoms forming the cyclic structure and/or (b) a polyvalent amine-based curing agent (component b). ## Claims ### Claim 1 A thermosetting resin composition comprising: (A) an epoxy resin (component A); (B) a cyclic carbodiimide compound (component B) including a cyclic structure having one carbodiimide group and represented by the following formula (B-i) in which first nitrogen and second nitrogen are bonded together by a bond group and having 8 to 50 atoms forming the cyclic structure: wherein Q is bivalent to tetravalent bond group which is an aliphatic group, alicyclic group, aromatic group or a combination of these groups, and may contain a hetero atom or substituent; and (b) a polyvalent amine-based curing agent (component b) represented by the following formula (b-i): wherein Ar1 to Ar4 are each independently a phenylene group or naphthalene-diyl group which may be substituted by a substituent. ### Claim 2 (depends on 1) The thermosetting resin composition according to claim 1, wherein the component B is a polyvalent cyclic carbodiimide compound having at least two carbodiimide groups in one molecule. ### Claim 3 (depends on 1) The thermosetting resin composition according to claim 1, wherein the component B is a compound represented by the following formula (B-ii): wherein X is a tetravalent group represented by the following formula (B-iii); Ar1 to Ar4 are each independently an orthophenylene group or 1,2-naphthalene-diyl group which may be substituted by an alkyl group having 1 to 6 carbon atoms or phenyl group; ### Claim 4 (depends on 1) The thermosetting resin composition according to claim 1, wherein the content of the cyclic carbodiimide compound (component B) is 0.01 to 50 parts by weight based on 100 parts by weight of the epoxy resin (component A). ### Claim 5 (depends on 1) The thermosetting resin composition according to claim 1, wherein the glass transition temperature of a cured resin is 2° C. or more higher than the glass transition temperature of a cured resin obtained by curing a thermosetting resin composition comprising no component B under the same conditions. ### Claim 6 (depends on 1) The thermosetting resin composition according to claim 1, further comprising a curing agent (component C). ### Claim 7 (depends on 1) The thermosetting resin composition according to claim 1, further comprising a curing accelerator (component D). ### Claim 8 A thermosetting resin composition comprising: (A) an epoxy resin (component A); and (b) a polyvalent amine-based curing agent (component b) represented by the following formula (b-i): wherein Ar1 to Ar4 are each independently a phenylene group or naphthalene-diyl group which may be substituted by a substituent. ### Claim 9 (depends on 8) The thermosetting resin composition according to claim 8, comprising 10 to 50 parts by weight of the polyvalent amine-based curing agent (component b) based on 100 parts by weight of the epoxy resin (component A). ### Claim 10 (depends on 8) The thermosetting resin composition according to claim 8, comprising 10 to 45 parts by weight of the polyvalent amine-based curing agent (component b) based on 100 parts by weight of the epoxy resin (component A). ### Claim 11 (depends on 8) The thermosetting resin composition according to claim 8, wherein the difference between the glass transition temperature (Tg·2H) of a cured resin after 2 hours of curing and the glass transition temperature (Tg·4H) of a cured resin after 4 hours of curing is less than 10° C. at a thermal curing temperature of 160° C. to 200° C. ### Claim 12 (depends on 8) The thermosetting resin composition according to claim 8, wherein the glass transition temperature (Tg·160° C./4H) of a cured resin obtained after 4 hours of curing at a thermal curing temperature of 160° C. is 175° C. or higher. ### Claim 13 (depends on 8) The thermosetting resin composition according to claim 8, wherein the glass transition temperature (Tg·180° C./2H) of a cured resin obtained after 2 hours of curing at a thermal curing temperature of 180° C. is 175° C. or higher. ### Claim 14 (depends on 8) The thermosetting resin composition according to claim 8, wherein the epoxy resin (component A) is a bisphenol type epoxy resin.