# US 12,006,382 B2 · (Meth)acrylate, monomer composition for dental material, molded body, composition for dental material, dental material, and method of manufacturing (meth)acrylate > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,006,382 B2 - Document ID: US12006382B2 - Status: Granted - Kind: B2 - Application number: 16/973,576 - Filed: 2019-08-20 - Published: 2021-08-12 - Granted: 2024-06-11 - Earliest claimed: 2018-08-21 - Assignees: Mitsui Chemicals, Inc. - Applicants: Mitsui Chemicals, Inc. - Inventors: Naoyuki Kakinuma; Eri Koizumi - Web page: https://patentgrep.com/patent/US12006382B2 ## CPC - C07C 323/52: the carbon skeleton being acyclic and saturated - C08F 20/38: Esters containing sulfur - A61K 6/887: Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds - C07C 321/14: of an acyclic saturated carbon skeleton - C08F 220/38: Esters containing sulfur - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) ## Abstract A (meth)acrylate includes a reaction product of a thiol compound containing two or more thiol groups, and a (meth)acrylate compound containing two or more (meth)acryloyloxy groups. ## Claims ### Claim 1 A method of manufacturing a (meth)acrylate, the method comprising: preparing a composition comprising a thiol compound containing two or more thiol groups, a (meth)acrylate compound containing two or more (meth)acryloyloxy groups, and an alkylphosphine compound; and producing a (meth)acrylate (A) containing a sulfide bond by reacting the thiol compound and the (meth)acrylate compound, wherein the alkylphosphine compound comprises a trialkylphosphine compound, and wherein the (meth)acrylate (A) comprises a structure formed by reacting the thiol groups contained in the thiol compound and the (meth)acryloyloxy groups contained in the (meth)acrylate compound, and wherein the (meth)acrylate (A) does not contain a thiol group, and contains a (meth)acryloyloxy group. ### Claim 2 (depends on 1) The method of manufacturing the (meth)acrylate according to claim 1, wherein a content of the alkylphosphine compound is 0.2 parts by mass or less with respect to 100 parts by mass of the composition. ### Claim 3 (depends on 1) The method of manufacturing the (meth)acrylate according to claim 1, wherein a reaction temperature of the thiol compound and the (meth)acrylate compound is 50° C. or less when producing the (meth)acrylate (A). ### Claim 4 (depends on 1) The method of manufacturing the (meth)acrylate according to claim 1, wherein the trialkylphosphine compound comprises at least one selected from the group consisting of tri-n-butylphosphine, tri-n-hexylphosphine, tricyclohexylphosphine and tri-n-octylphosphine. ### Claim 5 (depends on 1) The method of manufacturing the (meth)acrylate according to claim 1, wherein the (meth)acrylate (A) comprises a structure represented by the following general formula (B), and two or more (meth)acryloyloxy groups in a molecule: wherein, in the general formula (B), R2 represents a hydrogen atom or a methyl group; and each * represents a binding site. ### Claim 6 (depends on 1) The method of manufacturing the (meth)acrylate according to claim 1, wherein the (meth)acrylate (A) is represented by the following general formula (1): wherein, in the general formula (1), R1 represents a residue of a bifunctional to tetrafunctional thiol compound from which all thiol groups have been removed; R2 represents a hydrogen atom or a methyl group; R3 represents a residue of a di(meth)acrylate from which two (meth)acryloyloxy groups have been removed; n is an integer from 2 to 4; and plural instances of R2 and R3 may be the same or different, respectively. ### Claim 7 (depends on 6) The method of manufacturing the (meth)acrylate according to claim 6, wherein a molecular weight of R1 is from 100 to 500 in the general formula (1). ### Claim 8 (depends on 6) The method of manufacturing the (meth)acrylate according to claim 6, wherein R1 is a group represented by the following formula (2), (3), (4), (5), (6-1), (6-2), (6-3), (7), (8), (9) or (10) in the general formula (1): wherein, in formulae (2), (3), (4), (5), (6-1), (6-2), (6-3), (7), (8), (9) and (10), each * represents a binding site; in formula (8), R5 represents a divalent hydrocarbon group having 1 to 10 carbon atoms; in formula (9), R6, R7, and R8 each independently represent a divalent hydrocarbon group having 1 to 10 carbon atoms; in formula (10), R9, R10, and R11 each independently represent a divalent hydrocarbon group having 1 to 10 carbon atoms; and Y1 and Y2 each independently represent an oxygen atom or a sulfur atom. ### Claim 9 (depends on 6) The method of manufacturing the (meth)acrylate according to claim 6, wherein, in general formula (1), the di(meth)acrylate is neopentyl di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,8-octanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, tricyclodecanedimethanol di(meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, tetrapropylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, 2,2-bis[4-(3-(meth)acryloyloxy-2-hydroxypropoxy)phenyl]propane, ethylene oxide-modified bisphenol A di(meth)acrylate, or propylene oxide-modified bisphenol A di(meth)acrylate. ### Claim 10 (depends on 1) The method of manufacturing the (meth)acrylate according to claim 1, wherein the (meth)acrylate (A) has a viscosity at 25° C. of from 1 mPa·s to 10,000 mPa·s.