# US 12,214,061 B2 · Adhesive composition for dental use > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,214,061 B2 - Document ID: US12214061B2 - Status: Granted - Kind: B2 - Application number: 17/415,802 - Filed: 2019-12-20 - Published: 2022-03-10 - Granted: 2025-02-04 - Earliest claimed: 2018-12-21 - Assignees: Kuraray Noritake Dental Inc. - Applicants: Kuraray Noritake Dental Inc. - Inventors: Yamato Nojiri; Naoki Nishigaki; Mitsunobu Kawashima - Web page: https://patentgrep.com/patent/US12214061B2 ## CPC - A61K 6/30: Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives - A61K 6/887: Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds - C08F 230/02: containing phosphorus - C08K 5/521: Esters of phosphoric acids, e.g. of H3PO4 - 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) - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) ## Abstract A dental adhesive composition may exhibit high bond strength, e.g., initial bond strength and bond durability, to sandblasted zirconia. Such a dental adhesive composition may include (A) a dihydrogen phosphate monoester group-containing polymerizable monomer of formula (1): and (B) a dihydrogen phosphate monoester group-containing compound of formula (2): R1 may be H or a methyl group, and X1 and X2 may be an optionally substituted, linear or branched hydrocarbon group having 8 to 16 carbon atoms. The hydrocarbon group of X1 and/or X2 may have a hydrocarbon chain comprising an —O—, —S—, and/or a phenylene group. ## Claims ### Claim 1 A dental adhesive composition, comprising: (A) a dihydrogen phosphate monoester group-containing polymerizable monomer of formula (1): R1 being H or a methyl group, and X1 being an optionally substituted, linear or branched hydrocarbon group having 8 to 16 carbon atoms; and (B) a dihydrogen phosphate monoester group-containing compound of formula (2): being an optionally substituted, linear or branched hydrocarbon group having 8 to 16 carbon atoms, wherein the hydrocarbon group of X1 and/or X2 optionally has a hydrocarbon chain comprising an —O—, —S—, and/or a phenylene group, and wherein the dihydrogen phosphate monoester group-containing compound (B) is present in a range of from 0.05 to 5.0 parts by mass, relative to 100 parts by mass of the dihydrogen phosphate monoester group-containing polymerizable monomer (A). ### Claim 2 (depends on 1) The dental adhesive composition of claim 1, further comprising: (C) a polymerizable monomer that is copolymerizable with the dihydrogen phosphate monoester group-containing polymerizable monomer (A). ### Claim 3 (depends on 1) The dental adhesive composition of claim 1, further comprising: (D) a polymerization initiator. ### Claim 4 (depends on 1) The dental adhesive composition of claim 1, wherein X1 and X2 are the same. ### Claim 5 (depends on 1) The dental adhesive composition of claim 1, comprising the dihydrogen phosphate monoester group-containing compound (B) in a range of from 0.2 to 1.0 parts by mass, relative to 100 parts by mass of the dihydrogen phosphate monoester group-containing polymerizable monomer (A). ### Claim 6 (depends on 1) The dental adhesive composition of claim 1, wherein X1 and X2 are each independently an unsubstituted, linear alkylene group having 8 to 16 carbon atoms. ### Claim 7 (depends on 1) The dental adhesive composition of claim 1, further comprising: (C) a polymerizable monomer that is copolymerizable with the dihydrogen phosphate monoester group-containing polymerizable monomer (A), wherein the polymerizable monomer (C) comprises a hydrophobic polymerizable monomer (C-1) having no acidic group. ### Claim 8 (depends on 1) The dental adhesive composition of claim 1, further comprising: (C) a polymerizable monomer that is copolymerizable with the dihydrogen phosphate monoester group-containing polymerizable monomer (A), wherein the dihydrogen phosphate monoester group-containing compound (B) is present in a range of from 0.2 to 1.0 parts by mass, relative to 100 parts by mass of the dihydrogen phosphate monoester group-containing polymerizable monomer (A). ### Claim 9 (depends on 1) The dental adhesive composition of claim 1, further comprising: (D) a polymerization initiator, wherein the dihydrogen phosphate monoester group-containing compound (B) is present in a range of from 0.2 to 1.0 parts by mass, relative to 100 parts by mass of the dihydrogen phosphate monoester group-containing polymerizable monomer (A). ### Claim 10 (depends on 1) The dental adhesive composition of claim 1, comprising the dihydrogen phosphate monoester group-containing compound (B) in a range of from 0.2 to 1.0 parts by mass, relative to 100 parts by mass of the dihydrogen phosphate monoester group-containing polymerizable monomer (A), wherein X1 and X2 are the same. ### Claim 11 (depends on 1) The dental adhesive composition of claim 1, further comprising: (C) a polymerizable monomer that is copolymerizable with the dihydrogen phosphate monoester group-containing polymerizable monomer (A); and (D) a polymerization initiator, wherein the dihydrogen phosphate monoester group-containing compound (B) is present in a range of from 0.2 to 1.0 parts by mass, relative to 100 parts by mass of the dihydrogen phosphate monoester group-containing polymerizable monomer (A). ### Claim 12 (depends on 1) The dental adhesive composition of claim 1, further comprising: (C) a polymerizable monomer that is copolymerizable with the dihydrogen phosphate monoester group-containing polymerizable monomer (A); and (D) a polymerization initiator, wherein the dihydrogen phosphate monoester group-containing compound (B) is present in a range of from 0.2 to 1.0 parts by mass, relative to 100 parts by mass of the dihydrogen phosphate monoester group-containing polymerizable monomer (A), and wherein X1 and X2 are the same. ### Claim 13 (depends on 1) The dental adhesive composition of claim 1, further comprising: (C) a polymerizable monomer that is copolymerizable with the dihydrogen phosphate monoester group-containing polymerizable monomer (A), wherein the dihydrogen phosphate monoester group-containing compound (B) is present in a range of from 0.2 to 1.0 parts by mass, relative to 100 parts by mass of the dihydrogen phosphate monoester group-containing polymerizable monomer (A), and wherein the polymerizable monomer (C) comprises a hydrophobic polymerizable monomer (C-1) having no acidic group. ### Claim 14 (depends on 1) The dental adhesive composition of claim 1, further comprising: (C) a polymerizable monomer that is copolymerizable with the dihydrogen phosphate monoester group-containing polymerizable monomer (A), wherein the dihydrogen phosphate monoester group-containing compound (B) is present in a range of from 0.2 to 1.0 parts by mass, relative to 100 parts by mass of the dihydrogen phosphate monoester group-containing polymerizable monomer (A), and wherein X1 and X2 are each independently an unsubstituted, linear alkylene group having 8 to 16 carbon atoms. ### Claim 15 (depends on 1) The dental adhesive composition of claim 1, further comprising: (C) a polymerizable monomer that is copolymerizable with the dihydrogen phosphate monoester group-containing polymerizable monomer (A), wherein the dihydrogen phosphate monoester group-containing compound (B) is present in a range of from 0.2 to 1.0 parts by mass, relative to 100 parts by mass of the dihydrogen phosphate monoester group-containing polymerizable monomer (A), wherein the polymerizable monomer (C) comprises a hydrophobic polymerizable monomer (C-1) having no acidic group, and wherein X1 and X2 are each independently an unsubstituted, linear alkylene group having 8 to 16 carbon atoms. ### Claim 16 (depends on 1) The dental adhesive composition of claim 1, further comprising: (C) a polymerizable monomer that is copolymerizable with the dihydrogen phosphate monoester group-containing polymerizable monomer (A), wherein the dihydrogen phosphate monoester group-containing compound (B) is present in a range of from 0.2 to 1.0 parts by mass, relative to 100 parts by mass of the dihydrogen phosphate monoester group-containing polymerizable monomer (A), wherein the polymerizable monomer (C) comprises a hydrophobic polymerizable monomer (C-1) having no acidic group, and wherein X1 and X2 are the same. ### Claim 17 (depends on 1) The dental adhesive composition of claim 1, further comprising: (C) a polymerizable monomer that is copolymerizable with the dihydrogen phosphate monoester group-containing polymerizable monomer (A), wherein the dihydrogen phosphate monoester group-containing compound (B) is present in a range of from 0.2 to 1.0 parts by mass, relative to 100 parts by mass of the dihydrogen phosphate monoester group-containing polymerizable monomer (A), and wherein X1 and X2 are an identical unsubstituted, linear alkylene group having 8 to 16 carbon atoms. ### Claim 18 (depends on 1) The dental adhesive composition of claim 1, further comprising: (C) a polymerizable monomer that is copolymerizable with the dihydrogen phosphate monoester group-containing polymerizable monomer (A), wherein the dihydrogen phosphate monoester group-containing compound (B) is present in a range of from 0.2 to 1.0 parts by mass, relative to 100 parts by mass of the dihydrogen phosphate monoester group-containing polymerizable monomer (A), wherein the polymerizable monomer (C) comprises a hydrophobic polymerizable monomer (C-1) having no acidic group, and wherein X1 and X2 are an identical unsubstituted, linear alkylene group having 8 to 16 carbon atoms. ### Claim 19 (depends on 1) The dental adhesive composition of claim 1, further comprising: (C) a polymerizable monomer that is copolymerizable with the dihydrogen phosphate monoester group-containing polymerizable monomer (A); and (D) a polymerization initiator, wherein the dihydrogen phosphate monoester group-containing compound (B) is present in a range of from 0.2 to 1.0 parts by mass, relative to 100 parts by mass of the dihydrogen phosphate monoester group-containing polymerizable monomer (A), and wherein the polymerizable monomer (C) comprises a hydrophobic polymerizable monomer (C-1) having no acidic group. ### Claim 20 (depends on 1) The dental adhesive composition of claim 1, further comprising: (C) a polymerizable monomer that is copolymerizable with the dihydrogen phosphate monoester group-containing polymerizable monomer (A); and (D) a polymerization initiator, wherein the dihydrogen phosphate monoester group-containing compound (B) is present in a range of from 0.2 to 1.0 parts by mass, relative to 100 parts by mass of the dihydrogen phosphate monoester group-containing polymerizable monomer (A), and wherein X1 and X2 are each independently an unsubstituted, linear alkylene group having 8 to 16 carbon atoms.