# US 11,110,038 B2 · Dental polymerizable monomers, compositions, adhesive dental materials and kits > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,110,038 B2 - Document ID: US11110038B2 - Status: Granted - Kind: B2 - Application number: 16/588,283 - Filed: 2019-09-30 - Published: 2020-01-30 - Granted: 2021-09-07 - Earliest claimed: 2015-03-31 - Assignees: Mitsui Chemicals, Inc.; Sun Medical Co., Ltd. - Applicants: Mitsui Chemicals, Inc.; Sun Medical Co., Ltd. - Inventors: Kazuhiko Yoshinaga; Yoshimitsu Tanabe; Shinsuke Kinoshita; Takenori Mitamura; Hiroki Murai; Takeshi Yokoyama; Yoshihisa Kamimoto; Tatsuya Ori; Hirohisa Shimizu; Masami Arata; Masuji Tsuchikawa; Sayaka Miyamori; Yoshiaki Katsura - Web page: https://patentgrep.com/patent/US11110038B2 ## CPC - A61K 6/30: Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives - A61K 6/00: Preparations for dentistry - A61K 6/62: Photochemical radical initiators - A61K 6/887: Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds - C07C 271/20: to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups - C07C 2602/42: the bicyclo ring system containing seven carbon atoms - 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) - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract A dental adhesive curable composition containing a polymerizable monomer including a polymerizable monomer represented by formula (1′) and defined amounts of an acidic group-containing polymerizable monomer, a polymerization initiator containing a peroxide and a photopolymerization initiator, and a reductant containing a sulfinic acid compound and/or a salt thereof, and a filler: wherein the R groups, n and m are defined. A dental adhesive curable kit and a mobile tooth fixing material are also provided. ## Claims ### Claim 1 A dental adhesive curable kit (αc) for preparing a dental adhesive curable composition (c), the dental adhesive curable composition (c) comprising a polymerizable monomer (III) comprising a polymerizable monomer (A) represented by the following general formula (1′) and an acidic group-containing polymerizable monomer (Bc), a polymerization initiator (Cc) comprising a peroxide (Cc1) and a photopolymerization initiator (Cc2), and a reductant (Dc) comprising a sulfinic acid compound (Dc2) and/or a salt thereof, and a filler (Fc), wherein the content of the polymerizable monomer (A) is not less than 0.1 part by weight and not more than 99 parts by weight, and the content of the acidic group-containing polymerizable monomer (Bc) is 0.5 to 30 parts by weight based on the total weight of the polymerizable monomer (III); the content of the peroxide (Cc1) is 0.01 to 20 parts by weight, the content of the photopolymerization initiator (Cc2) is 0.0001 to 15 parts by weight, and the content of the sulfinic acid compound (Dc2) or salt thereof is 0.001 to 15 parts by weight based on the polymerizable monomer (III); and the content of the filler (Fc) is 5 to 95 wt % in the dental adhesive curable composition (c): wherein R1 and R2 are each a hydrogen atom or a C1-3 alkyl group, R7 and R8 are each a hydrogen atom or a methyl group, Rb and Rc are each independently a C2-6 linear alkylene or C2-6 linear oxyalkylene group optionally substituted with a C1-3 alkyl group or a (meth) acryloyloxymethylene group in place of a hydrogen atom, and a moiety of the general formula (2c) below that is interposed between the two carbamoyl groups in the general formula (1′) is a structure represented by any of the general formulas (RA) and (RD) below: the dental adhesive curable kit (αc) comprising at least a first composition and a second composition, at least one of the first composition and the second composition including the polymerizable monomer (A), the first composition including the reductant (Dc), the second composition including the acidic group-containing polymerizable monomer (Bc) and the polymerization initiator (Cc). ### Claim 2 A mobile tooth fixing material (βd) comprising a dental adhesive composition (d), the dental adhesive composition (d) including a polymerizable monomer (A) represented by the following general formula (1″), a polymerizable monomer (Bd) having at least one acidic group in the molecule, and a photopolymerization initiator (Cd): wherein Ra is a divalent C6-9 bridged cyclic hydrocarbon group, R1 and R2 are each a hydrogen atom or a methyl group, R3, R4, R5 and R6 are each a hydrogen atom or a hydrocarbon group, R7 and R8 are each a hydrogen atom, m and n are each independently 0 to 4, and Rb and Rc are each independently a C2-6 linear alkylene or C2-6 linear oxyalkylene group optionally substituted with a C1-3 alkyl group or a (meth)acryloyloxymethylene group in place of a hydrogen atom. ### Claim 3 (depends on 2) A mobile tooth fixing material (βd) according to claim 2, wherein a cured product that is obtained by the following method and that is subjected to a three-point bending test exhibits a breaking energy of not less than 65 mJ, the cured product being obtained by packing the dental adhesive composition (d) into a 2×2×25 mm mold, which is brought into press contact with a polypropylene film and a glass plate, irradiating nine points on each of front and back sides with light for 10 seconds, and polishing a surface of the cured product with #320 waterproof abrasive paper, the three-point bending test being performed such that the obtained cured product is soaked in water at 37° C. overnight, and thereafter is subjected to the test at a crosshead speed of 1.0 mm/min; and wherein a test piece that is obtained by the following method and that is subjected to a tensile adhesion test exhibits a tensile bond strength of not less than 3 MPa, the test piece being obtained by applying the dental adhesive composition (d) on a bonding tooth face and curing the dental adhesive composition (d) by irradiation with light for 10 seconds, the bonding tooth face being obtained from a bovine front lower tooth having its flat enamel face exposed that is washed with water and dried and having a defined circular bonding area 4.8 mm in diameter, the tensile adhesion test being performed such that the obtained test piece is soaked in water at 37° C. overnight, and thereafter is subjected to the test at a crosshead speed of 2 mm/min. ### Claim 4 (depends on 1) The dental adhesive curable kit (αc) according to claim 1, wherein the content of the acidic group-containing polymerizable monomer (Bc) is 1 to 10 parts by weight based on the total weight of the polymerizable monomer (III).