# US 10,370,325 B2 · Cyanate ester compound, curable resin composition containing the compound, and hardened product thereof > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,370,325 B2 - Document ID: US10370325B2 - Status: Granted - Kind: B2 - Application number: 15/560,708 - Filed: 2016-02-19 - Published: 2018-04-19 - Granted: 2019-08-06 - Earliest claimed: 2015-03-31 - Assignees: Mitsubishi Gas Chemical Company, Inc. - Applicants: Mitsubishi Gas Chemical Company, Inc. - Inventors: Masayuki Katagiri; Tatsuya Shima; Keita Tokuzumi - Web page: https://patentgrep.com/patent/US10370325B2 ## CPC - C07C 261/02: Cyanates - C08G 14/12: Chemically modified polycondensates - C08G 59/20: characterised by the epoxy compounds used - C08G 61/02: Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes - C08G 65/18: Oxetanes - C08G 73/0644: {Poly(1,3,5)triazines} - C08J 5/04: Reinforcing macromolecular compounds with loose or coherent fibrous material - C08J 5/244: {using glass fibres} - C08L 61/04: Condensation polymers of aldehydes or ketones with phenols only - C08L 61/34: Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C08L61/04, C08L61/18 and C08L61/20 - C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins - C08L 65/00: Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C08L7/00 - C08L57/00, C08L61/00 take precedence); Compositions of derivatives of such polymers - C09J 11/06: organic - C09J 161/06: of aldehydes with phenols - C09J 163/00: Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins - H10W 70/69: Insulating materials thereof - H10W 74/10: characterised by their shape or disposition - H10W 74/40: characterised by their materials - C08G 73/06: Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule - C09J 179/04: Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON 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) - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - 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) - H10W: GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10 ## Abstract The present invention provides a novel cyanate ester compound which has excellent solvent solubility and from which a hardened product having a low coefficiency of thermal expansion and excellent flame retardancy and heat resistance is obtained. The present invention is a cyanate ester compound obtained by cyanating a naphthol-dihydroxynaphthalene aralkyl resin or a dihydroxynaphthalene aralkyl resin. ## Claims ### Claim 1 A cyanate ester compound having one or more structures selected from the group consisting of structures represented by the following formula (1), formula (2), and formula (5): wherein k represents an integer of 1 or larger, and 1 represents an integer of 0 or larger; the compound may be a mixture of compounds differing from each other in k and l; and arrangement of repeating units is arbitrary; wherein m and n represent an integer of 0 or larger, and at least one is 1 or larger; the compound may be a mixture of compounds differing from each other in m and n; and arrangement of repeating units is arbitrary; and wherein m represents an integer of 0 or larger; and the compound is a mixture of compounds differing from each other in m. ### Claim 2 A cyanate ester compound obtained by cyanating one or more resins selected from the group consisting of naphthol-dihydroxynaphthalene aralkyl resins and dihydroxynaphthalene aralkyl resins. ### Claim 3 (depends on 1) The cyanate ester compound according to claim 1 obtained by cyanating one or more resins selected from the group consisting of naphthol-dihydroxynaphthalene aralkyl resins and dihydroxynaphthalene aralkyl resins. ### Claim 4 (depends on 2) The cyanate ester compound according to claim 2, wherein the naphthol-dihydroxynaphthalene aralkyl resin is obtained by reacting 1-naphthol, 2,7-dihydroxynaphthalene, and one or more selected from the group consisting of paraxylene glycol and 1,4-bis(methoxymethyl)benzene in the presence of an acidic catalyst, and the dihydroxynaphthalene aralkyl resin is obtained by reacting 2,7-dihydroxynaphthalene and one or more selected from the group consisting of paraxylene glycol and 1,4-bis(methoxymethyl)benzene in the presence of an acidic catalyst. ### Claim 5 (depends on 1) The cyanate ester compound according to claim 1, wherein the cyanate ester compound has a weight-average molecular weight Mw of 100 to 5000. ### Claim 6 (depends on 1) A curable resin composition comprising a cyanate ester compound according to claim 1. ### Claim 7 (depends on 6) The curable resin composition according to claim 6, further comprising one or more selected from the group consisting of a cyanate ester compound other than the cyanate ester compound, a maleimide compound, a phenol resin, an epoxy resin, an oxetane resin, a benzoxazine compound, and a compound having a polymerizable unsaturated group. ### Claim 8 (depends on 6) A hardened product obtained by curing a curable resin composition according to claim 6. ### Claim 9 (depends on 6) A prepreg for a structural material comprising: a base material, and a curable resin composition according to claim 6 with which the base material is impregnated or coated. ### Claim 10 (depends on 6) A sealing material, comprising a curable resin composition according to claim 6. ### Claim 11 (depends on 6) A fiber-reinforced composite material comprising a curable resin composition according to claim 6. ### Claim 12 (depends on 6) An adhesive comprising a curable resin composition according to claim 6. ### Claim 13 (depends on 3) The cyanate ester compound according to claim 3, wherein the naphthol-dihydroxynaphthalene aralkyl resin is obtained by reacting 1-naphthol, 2,7-dihydroxynaphthalene, and one or more selected from the group consisting of paraxylene glycol and 1,4-bis(methoxymethyl)benzene in the presence of an acidic catalyst, and the dihydroxynaphthalene aralkyl resin is obtained by reacting 2,7-dihydroxynaphthalene and one or more selected from the group consisting of paraxylene glycol and 1,4-bis(methoxymethyl)benzene in the presence of an acidic catalyst. ### Claim 14 (depends on 2) The cyanate ester compound according to claim 2, wherein the cyanate ester compound has a weight-average molecular weight Mw of 100 to 5000. ### Claim 15 (depends on 3) The cyanate ester compound according to claim 3, wherein the cyanate ester compound has a weight-average molecular weight Mw of 100 to 5000. ### Claim 16 (depends on 4) The cyanate ester compound according to claim 4, wherein the cyanate ester compound has a weight-average molecular weight Mw of 100 to 5000. ### Claim 17 (depends on 2) A curable resin composition comprising a cyanate ester compound according to claim 2. ### Claim 18 (depends on 3) A curable resin composition comprising a cyanate ester compound according to claim 3. ### Claim 19 (depends on 17) The curable resin composition according to claim 17, further comprising one or more selected from the group consisting of a cyanate ester compound other than the cyanate ester compound, a maleimide compound, a phenol resin, an epoxy resin, an oxetane resin, a benzoxazine compound, and a compound having a polymerizable unsaturated group. ### Claim 20 (depends on 18) The curable resin composition according to claim 18, further comprising one or more selected from the group consisting of a cyanate ester compound other than the cyanate ester compound, a maleimide compound, a phenol resin, an epoxy resin, an oxetane resin, a benzoxazine compound, and a compound having a polymerizable unsaturated group.