# US 9,518,007 B2 · Urethane (meth) acrylate compound > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,518,007 B2 - Document ID: US9518007B2 - Status: Granted - Kind: B2 - Application number: 14/763,645 - Filed: 2014-01-15 - Published: 2015-12-17 - Granted: 2016-12-13 - Earliest claimed: 2013-01-29 - Assignees: Japan U-Pica Company, Ltd. - Applicants: Japan U-Pica Company, Ltd. - Inventors: Tetsuji Moroiwa; Nozomi Ishine; Hiroshi Hayashi - Web page: https://patentgrep.com/patent/US9518007B2 ## CPC - C07C 271/08: having oxygen atoms of carbamate groups bound to acyclic carbon atoms - C07C 269/02: from isocyanates with formation of carbamate groups - C08F 290/068: {Polysiloxanes} - C08G 18/672: {Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen} - C08G 71/04: Polyurethanes - C08J 5/042: {with carbon fibres} - C08L 63/10: Epoxy resins modified by unsaturated compounds - C08L 75/16: having terminal carbon-to-carbon unsaturated bonds - C08J 2375/16: having terminal carbon-to-carbon unsaturated bonds - C08L 2312/04: with phenolic resin - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - 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) ## Abstract The present invention provides a thermosetting resin which enables the production of a carbon fiber reinforced plastic having a good workability and excellent mechanical properties by hand lay up (HUP) molding, resin transfer molding (RTM) or vacuum assisted resin transfer molding (VaRTM). The urethane (meth) acrylate compound (A) according to the present invention is an urethane (meth) acrylate produced by reacting a compound having two or more isocyanate groups with a monoalcohol compound containing ethylenically unsaturated groups or by reacting a compound having two or more isocyanate groups with a monoalcohol compound containing ethylenically unsaturated groups and an alcohol compound having two or more hydroxyl groups, said urethane (meth) acrylate compound (A) being characterized by having an isocyanate group and ethylenically unsaturated groups. ## Claims ### Claim 1 A resin composition for a carbon fiber reinforced plastic comprising a urethane (meth) acrylate compound (A) characterized by being represented by the following chemical formula [Chemical 1]: XM]n [Chemical 1] (wherein X is a compound residue having two or more isocyanate groups, M contains at least the following formula [Chemical 2]: —NCO [Chemical 2] and M other than the above formula [Chemical 2] is the following formula [Chemical 3]: Q is a monoalcohol compound residue containing ethylenically unsaturated groups in the formula, and “n” is 2 to 7), wherein the isocyanate group existing in the urethane (meth) acrylate compound (A) is present at 0.1 to 12 percent by weight. ### Claim 2 A resin composition for a carbon fiber reinforced plastic comprising a urethane (meth) acrylate compound (A) characterized by being represented by the following chemical formula [Chemical 4]: (wherein X is a compound residue having two or more isocyanate groups, Y is an alcohol compound residue having two or more hydroxyl groups, M contains at least the following formula [Chemical 5]: —NCO [Chemical 5] and M other than the above formula [Chemical 5] is the following formula [Chemical 6]: Q is a monoalcohol compound residue containing ethylenically unsaturated groups in the formula, and “n” is 1 to 5000), wherein the isocyanate group existing in the urethane (meth) acrylate compound (A) is present at 0.1 to 12 percent by weight. ### Claim 3 (depends on 1) A resin composition for a carbon fiber reinforced plastic comprising a urethane (meth) acrylate compound (A) according to claim 1, wherein it is a urethane (meth) acrylate produced by reacting a compound having two or more isocyanate groups with a monoalcohol compound containing ethylenically unsaturated groups, or by reacting a compound having two or more isocyanate groups with a monoalcohol compound containing ethylenically unsaturated groups and an alcohol compound having two or more hydroxyl groups, the urethane (meth) acrylate compound (A) being characterized by having an isocyanate group and ethylenically unsaturated groups. ### Claim 4 (depends on 2) A resin composition for a carbon fiber reinforced plastic comprising a urethane (meth) acrylate compound (A) according to claim 2, wherein the alcohol compound having two or more hydroxyl groups is one or more selected from 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol. ### Claim 5 (depends on 2) A resin composition for a carbon fiber reinforced plastic comprising a urethane (meth) acrylate compound (A) according to claim 2, wherein the alcohol compound having two or more hydroxyl groups is polyester polyol obtained by the polycondensation of dicarboxylic acid or an ester forming derivative thereof with glycol. ### Claim 6 (depends on 2) A resin composition for a carbon fiber reinforced plastic comprising a urethane (meth) acrylate compound (A) according to claim 2, wherein the alcohol compound having two or more hydroxyl groups is polyester polyol obtained by the polycondensation of one or more selected from terephthalic acid, isophthalic acid, an ester forming derivative thereof, with one or more selected from 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol. ### Claim 7 (depends on 1) A resin composition for a carbon fiber reinforced plastic comprising a urethane (meth) acrylate compound (A) according to claim 1, wherein the compound having two or more isocyanate groups is one or more selected from 1,6-hexamethylene diisocyanate, 1,3-bis (isocyanatomethyl) cyclohexane, isophorone diisocyanate, and a prepolymer thereof, polymethylenepolyphenyl polyisocyanate. ### Claim 8 (depends on 1) A resin composition for a carbon fiber reinforced plastic according to claim 1, wherein the resin composition for a carbon fiber reinforced plastic comprises a urethane (meth) acrylate resin (B) characterized by comprising the urethane (meth) acrylate compound (A) and a polymerizable monomer. ### Claim 9 (depends on 8) A resin composition for a carbon fiber reinforced plastic according to claim 8, wherein an isocyanate group existing in the urethane (meth) acrylate resin (B) is present at 0.1 to 8 percent by weight. ### Claim 10 (depends on 1) A resin composition for a carbon fiber reinforced plastic, composed of a thermosetting resin having ethylenically unsaturated groups and a resin composition for a carbon fiber reinforced plastic according to claim 1, wherein an isocyanate group existing in the resin composition is present at 0.1 to 8 percent by weight. ### Claim 11 (depends on 2) A resin composition for a carbon fiber reinforced plastic comprising a urethane (meth) acrylate compound (A) according to claim 2, wherein it is a urethane (meth) acrylate produced by reacting a compound having two or more isocyanate groups with a monoalcohol compound containing ethylenically unsaturated groups, or by reacting a compound having two or more isocyanate groups with a monoalcohol compound containing ethylenically unsaturated groups and an alcohol compound having two or more hydroxyl groups, the urethane (meth) acrylate compound (A) being characterized by having an isocyanate group and ethylenically unsaturated groups.