# US 2021/0276943 A1 · Composition, production method for composition, and production method for unsaturated compound > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2021/0276943 A1 - Document ID: US20210276943A1 - Status: Published application - Kind: A1 - Application number: 17/269,059 - Filed: 2019-08-16 - Published: 2021-09-09 - Earliest claimed: 2018-08-20 - Assignees: Showa Denko K.K. - Applicants: Showa Denko K.K. - Inventors: Norihito NISHIMURA; Katsutoshi OHNO - Web page: https://patentgrep.com/patent/US20210276943A1 ## CPC - C07C 249/04: of oximes - C08G 18/4833: {Polyethers containing oxyethylene units} - C07C 231/10: from compounds not provided for in groups C07C231/02 - C07C231/08 - C07C 263/10: by reaction of amines with carbonyl halides, e.g. with phosgene - C07C 263/20: Separation; Purification - C07C 269/02: from isocyanates with formation of carbamate groups - C07D 231/12: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms - C08G 18/3876: {containing mercapto groups} - C08G 18/672: {Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen} - C08G 18/8116: {esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group} - C08K 5/29: Compounds containing {one or more} carbon-to-nitrogen double bonds - C08L 75/04: Polyurethanes - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - 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 The invention is related to a composition excellent in stability during storage and excellent stability during utilization, and related to a method of producing the composition. The composition comprises a compound (A) represented by general formula (1) and a compound (B). The compound (B) is an oligomer in which two or more molecules of the compound (A) are bonded to each other by ethylenically unsaturated groups of each compound (A). The composition contains 0.00002 to 0.2 parts by mass of the compound (B) with respect to 100 parts by mass of the compound (A), (R1—COO)n—R2—(NCO)m (1) wherein in general formula (1), R1 is an ethylenically unsaturated group having 2 to 7 carbon atoms; R2 is a (m+n)-valent hydrocarbon group having 1 to 7 carbon atoms and optionally contain an ether group; and n and in each represent an integer of one or two. ## Claims ### Claim 1 A composition comprising: a compound (A) represented by general formula (1) and a compound (B) wherein the compound (B) is an oligomer in which two or more molecules of the compounds (A) are bonded to each other by an ethylenically unsaturated group of each compound (A); and the composition comprises 0.00002 to 0.2 parts by mass of the compound (B) with respect to 100 parts by mass of the compound (A), (R1—COO)n—R2—(NCO)m (1) wherein in the general formula (1), R1 is an ethylenically unsaturated group having 2 to 7 carbon atoms; R2 is a (m+n)-valent hydrocarbon group having 1 to 7 carbon atoms and optionally comprises an ether group; and n and m each represent an integer of 1 or 2. ### Claim 2 (depends on 1) The composition according to claim 1, wherein the compound (A) is at least one compound selected from the group consisting of 2-methacryloyloxyethyl isocyanate, 2-(isocyanatoethyloxy) ethyl methacrylate, 2-acryloyloxyethyl isocyanate, 2-(isocyanatoethyloxy) ethyl acrylate, and 1,1-bis(acryloyloxymethyl)ethyl isocyanate. ### Claim 3 (depends on 1) The composition of claim 1, wherein a content of the compound (A) in the composition is 95.0% by mass or more. ### Claim 4 A method of producing a composition, comprising steps of: producing a mixture comprising the compound (A) and the compound (B); and purifying the mixture by a distillation process at a reflux ratio of 2.0 to 4.0, a pressure of 1.0 to 10.0 kPa and a distillation temperature of 90 to 140° C., wherein the purifying step comprises: a vacuum breaking step of supplying a gas having a dew point of −30° C. or less in a distillation apparatus after distillation by the distillation process and returning the pressure in the distillation apparatus to atmospheric pressure, wherein the gas comprises nitrogen gas oxygen gas at an oxygen concentration of 1 vol % or more and less than the critical oxygen concentration of compound (A); and a filling step of storing the purified product in the distillation apparatus after distillation in a container and filling a gas phase portion in the container with air having a dew point of −30° C. or lower. ### Claim 5 (depends on 4) The method of producing a composition according to claim 4, wherein the mixture comprises more than 0.2 parts by mass of the compound (B) with respect to 100 parts by mass of the compound (A); and the purified product comprises 0.00002 to 0.2 parts by mass of the compound (B) with respect to 100 parts by mass of the compound (A). ### Claim 6 (depends on 1) A method of producing an unsaturated compound, comprising the steps of: mixing the composition according to claim 1 with a compound having active hydrogen; and reacting the compound (A) contained in the composition with the compound having active hydrogen to obtain a reaction product. ### Claim 7 (depends on 6) The method of producing an unsaturated compound according to claim 6, wherein the compound having the active hydrogen is an alcohol, a thiol, an amine or a carboxylic acid. ### Claim 8 (depends on 6) The method of producing the unsaturated compound according to claim 6, wherein the reaction product is an unsaturated urethane compound, an unsaturated thiourethane compound, an unsaturated urea compound, or an unsaturated amide compound. ### Claim 9 (depends on 6) The method of producing an unsaturated compound according to claim 6, wherein the reaction product is any one selected from the group consisting of 2-butanone oxime-O-(carbamoylethyl-2-methacrylate), 2-butanone oxime-O-(carbamoylethyl-2-acrylate), 2-[(3,5-dimethylpyrazolyl)carbonylamino]ethyl methacrylate, and 2-[(3,5-dimethylpyrazolyl) carbonylamino]ethyl acryl ate.