# US 11,028,216 B2 · Polycarbodiimide copolymer > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,028,216 B2 - Document ID: US11028216B2 - Status: Granted - Kind: B2 - Application number: 16/344,749 - Filed: 2017-11-14 - Published: 2019-09-05 - Granted: 2021-06-08 - Earliest claimed: 2016-11-18 - Assignees: Nisshinbo Chemical Inc. - Applicants: Nisshinbo Chemical Inc. - Inventors: Takahiro Sasaki - Web page: https://patentgrep.com/patent/US11028216B2 ## CPC - C08G 18/095: {oligomerisation to carbodiimide or uretone-imine groups} - C08G 18/36: Hydroxylated esters of higher fatty acids - C08G 18/32: Polyhydroxy compounds; Polyamines; Hydroxyamines - C08G 18/48: Polyethers - C08G 18/69: Polymers of conjugated dienes {(hydrogenated polymers of conjugated dienes C08G18/6208)} - C08G 18/7621: {being toluene diisocyanate including isomer mixtures} - C08G 18/7657: {containing two or more aromatic rings} - C08G 18/7671: {containing only one alkylene bisphenyl group} - C08G 18/7685: {containing two or more non-condensed aromatic rings directly linked to each other} - C08G 18/79: characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates - C08G 18/83: Chemically modified polymers - C08G 18/833: {by nitrogen containing compounds (by azo compounds C08G18/85)} - C08L 33/06: of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical - C08L 67/00: Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain (of polyester-amides C08L77/12; of polyester-imides C08L79/08); Compositions of derivatives of such polymers - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) ## Abstract To provide a polycarbodiimide copolymer and a modified polycarbodiimide copolymer each suitable for a curing agent that can allow a cured product of a carboxy group-containing resin composition to be improved in flexibility without any loss of water resistance, as well as a curing agent of a carboxy group-containing resin composition, and a carboxy group-containing resin composition. The present invention enables a cured product to be enhanced in water resistance due to introduction of a predetermined soft segment into a polycarbodiimide molecule, in use for a curing agent, and also enables a carboxy group-containing resin composition to be enhanced in storage stability due to modification with an aliphatic amine or an aromatic heterocyclic amine. ## Claims ### Claim 1 A polycarbodiimide copolymer comprising: a soft segment comprising a residue in which hydroxyl groups are removed from at least one polyol selected from the group consisting of castor oil, a castor oil-based polyol having 2 to 10 functional groups, and a long-chain aliphatic diol represented by HO-R1-OH wherein R1 represents a linear or branched, saturated or unsaturated alkylene group containing 30 to 150 carbon atoms, and a hard segment composed of polycarbodiimide derived from an aromatic diisocyanate compound, the hard segment bonding to the soft segment through a urethane bond, and wherein an end isocyanate remaining as an end of the hard segment is capped with an end-capping agent, and the polyol is castor oil or a castor oil-based polyol having 2 to 10 functional groups. ### Claim 2 (depends on 1) The polycarbodiimide copolymer according to claim 1, wherein the aromatic diisocyanate is at least one selected from the group consisting of 4,4′-diphenylmethane diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate and 4,4′-diisocyanato-3,3′-dimethylbiphenyl. ### Claim 3 (depends on 1) A curing agent of a carboxy group-containing resin, comprising the polycarbodiimide copolymer according to claim 1. ### Claim 4 (depends on 3) A carboxy group-containing resin composition comprising the curing agent according to claim 3 and a carboxy group-containing resin. ### Claim 5 (depends on 1) A modified polycarbodiimide copolymer obtained by modifying the polycarbodiimide copolymer according to claim 1 with an aliphatic amine or an aromatic heterocyclic amine. ### Claim 6 (depends on 5) The modified polycarbodiimide copolymer according to claim 5, wherein the aliphatic amine is at least one selected from the group consisting of diethylamine, diisopropylamine, tert-butylethylamine, di-n-butylamine, di-sec-butylamine, di-tert-butylamine, dicyclohexylamine, 2-methylpiperidine and 2,6-dimethylpiperidine. ### Claim 7 (depends on 6) The modified polycarbodiimide copolymer according to claim 6, wherein the aliphatic amine is diisopropylamine. ### Claim 8 (depends on 5) The modified polycarbodiimide copolymer according to claim 5, wherein the aromatic heterocyclic amine is at least one selected from the group consisting of 3,5-dimethylpyrazole, imidazole, 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole and 2-phenyl-4-methylimidazole. ### Claim 9 (depends on 5) A curing agent of a carboxy group-containing resin, comprising the modified polycarbodiimide copolymer according to claim 5. ### Claim 10 (depends on 9) A carboxy group-containing resin composition comprising the curing agent according to claim 9 and a carboxy group-containing resin. ### Claim 11 (depends on 1) The polycarbodiimide copolymer according to claim 1, wherein the end-capping agent comprises a monoalcohol, a monophenol, a monoisocyanate or a monoamine. ### Claim 12 (depends on 1) The polycarbodiimide copolymer according to claim 1, wherein the end-capping agent comprises a monoalcohol or a monoisocyanate. ### Claim 13 (depends on 1) The polycarbodiimide copolymer according to claim 1, wherein the end-capping agent comprises an aromatic monoisocyanate. ### Claim 14 (depends on 1) The polycarbodiimide copolymer according to claim 1, wherein the polyol is a castor oil-based polyol having 2 to 3 functional groups.