# US 2011/0217677 A1 · Single-part, light-curable, self-adhering dental restorative composition and method of using the same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2011/0217677 A1 - Document ID: US20110217677A1 - Status: Published application - Kind: A1 - Application number: 13/110,253 - Filed: 2011-05-18 - Published: 2011-09-08 - Earliest claimed: 2008-08-13 - Assignees: Kerr Corporation - Inventors: Xuejun Qian - Web page: https://patentgrep.com/patent/US20110217677A1 ## CPC - A61K 6/887: 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 dental restorative composition comprises: (A) polymerizable monomer(s) selected from hydroxyethyl (meth)acrylate phosphate, hydroxypropyl (meth)acrylate phosphate, hydroxybutyl (meth)acrylate phosphate, dipentaerythritol penta(meth)acrylate phosphate, pentaerythritol tri(meth)acrylate phosphate, phenyl (meth)acryloxyethyl phosphate, and a combination thereof; (B) polymerizable monomer(s) having a molecular weight of 100-250, at least one hydroxyl group, and at least one ethylenically unsaturated group; (C) polymerizable monomer(s) having a molecular weight of 270-900, at least two ethylenically unsaturated groups and no acidic functional group; (D) photo-initiator(s); and (E) filler(s) each having a mean particle size of more than 0.005 microns and less than 70 microns. The weight ratio of (A+B):(C) ranges from 30:70 to 90:10, and the composition has a shear bond strength of at least 10 MPa to both dentin and enamel after being light-cured. ## Claims ### Claim 1 A single-part, light-curable, self-adhering dental restorative composition consisting essentially of: (A) one or more first polymerizable monomers selected from the group consisting of hydroxyethyl (meth)acrylate phosphate, hydroxypropyl (meth)acrylate phosphate, hydroxybutyl (meth)acrylate phosphate, dipentaerythritol penta(meth)acrylate phosphate, pentaerythritol tri(meth)acrylate phosphate, phenyl (meth)acryloxyethyl phosphate, and a combination thereof; (B) one or more second polymerizable monomers having a molecular weight of 100-250, at least one hydroxyl group, and at least one ethylenically unsaturated group; (C) one or more third polymerizable monomers having a molecular weight of 270-900, at least two ethylenically unsaturated groups and no acidic functional group; (D) a photo-initiator system having at least one photo-initiator; (E) one or more fillers each having a mean particle size of more than 0.005 microns and less than 70 microns; (F) optionally one or more ingredients selected from the group consisting of: a colorant, a stabilizer, a UV absorber, a solvent, a fluoride-releasing compound, an antimicrobial additive, and a surfactant; wherein the weight ratio of (A+B):(C) ranges from 30:70 to 90:10; and the composition has a shear bond strength of at least 10 MPa to both dentin and enamel after being light-cured. ### Claim 2 (depends on 1) The self-adhering dental restorative composition of claim 1 wherein the weight ratio of (A+B):(C) ranges from 45:55 to 75:25. ### Claim 3 (depends on 1) The self-adhering dental restorative composition of claim 1 wherein the concentration of component (A) in the restorative composition, excluding fillers, is in the range of 15-40% by weight, and the concentration of component (B) in the restorative composition, excluding fillers, is in the range of 20-50% by weight. ### Claim 4 (depends on 1) The self-adhering dental restorative composition of claim 1 wherein the ethylenically unsaturated groups in (B) and (C) are each selected from the group consisting of acrylate, methacrylate, acrylamide, methacrylamide, and vinyl groups, or any combination thereof. ### Claim 5 (depends on 1) The self-adhering dental restorative composition of claim 1 wherein the one or more first polymerizable monomers (A) further comprise glyceryldi(meth)acrylate phosphate, bis{hydroxyethyl (meth)acrylate} phosphate, or a combination thereof. ### Claim 6 (depends on 5) The self-adhering dental restorative composition of claim 5 wherein the concentration of component (A) in the restorative composition, excluding fillers, is in the range of 10-50% by weight, and the concentration of component (B) in the restorative composition, excluding fillers, is in the range of 15-60% by weight. ### Claim 7 (depends on 1) The self-adhering dental restorative composition of claim 1 wherein the one or more fillers are non-reactive towards the one or more first polymerizable monomers. ### Claim 8 (depends on 1) The self-adhering dental restorative composition of claim 1 wherein component (E) comprises: (E1) one or more first fillers having a mean particle size of more than 4.5 microns and less than 70 microns; (E2) one or more second fillers having a mean particle size of more than 0.25 microns, but no more than 4.5 microns; and (E3) one or more third fillers having a mean particle size of 0.005-0.25 microns. ### Claim 9 (depends on 8) The self-adhering dental restorative composition of claim 8 wherein the one or more first fillers (E1) have a mean particle size of more than 10 microns. ### Claim 10 (depends on 8) The self-adhering dental restorative composition of claim 8 wherein the one or more first fillers (E1) are a polymeric filler comprising 5-100% by weight of a polymeric matrix and 0-95% by weight of at least one inorganic filler. ### Claim 11 (depends on 10) The self-adhering dental restorative composition of claim 10 wherein the polymeric filler comprises 10-50% by weight of the polymeric matrix and 50-90% by weight of the at least one inorganic filler. ### Claim 12 (depends on 11) The self-adhering dental restorative composition of claim 11 wherein the polymeric matrix comprises crosslinked (meth)acrylate(s), and wherein the mean particle size of the inorganic filler(s) is in the range of 0.005-20 microns. ### Claim 13 (depends on 12) The self-adhering dental restorative composition of claim 12 wherein the mean particle size of the inorganic filler(s) is in the range of 0.01-4.5 microns. ### Claim 14 (depends on 8) The self-adhering dental restorative composition of claim 8 wherein the one or more second fillers (E2) have a mean particle size of 0.3-2.0 microns. ### Claim 15 (depends on 1) The self-adhering dental restorative composition of claim 1 wherein the total concentration of the one or more fillers in the restorative composition is in the range from 40-95% by weight. ### Claim 16 (depends on 1) The self-adhering dental restorative composition of claim 1 wherein the shear bond strength is at least 12 MPa to both dentin and enamel. ### Claim 17 (depends on 1) A method of using the self-adhering dental restorative composition of claim 1 comprises: (i) applying the self-adhering dental restorative composition to tooth structure without first treating the tooth structure with an etchant, a primer and/or an adhesive; and (ii) subsequently hardening the composition by light-curing the composition. ### Claim 18 (depends on 1) A dental restorative kit comprising the self-adhering dental restorative composition of claim 1 and an instruction of how to use the composition, wherein the instruction teaches to restore a dental cavity by first applying the single-part, light-curable, self-adhering dental restorative composition directly to the dental cavity without first treating the dental cavity with an etchant, a primer and/or an adhesive. ### Claim 19 A single-part, light-curable, self-adhering dental restorative composition consisting essentially of: (A) one or more first polymerizable monomers selected from the group consisting of hydroxyethyl (meth)acrylate phosphate, hydroxypropyl (meth)acrylate phosphate, hydroxybutyl (meth)acrylate phosphate, dipentaerythritol penta(meth)acrylate phosphate, pentaerythritol tri(meth)acrylate phosphate, phenyl (meth)acryloxyethyl phosphate, and a combination thereof; (B) one or more second polymerizable monomers having a molecular weight of 100-250, at least one hydroxyl group, and at least one ethylenically unsaturated group; (C) one or more third polymerizable monomers having a molecular weight of 270-900, at least two ethylenically unsaturated groups and no acidic functional group; (D) a photo-initiator system having at least one photo-initiator; (E1) one or more first fillers that are a polymeric filler having a mean particle size of more than 4.5 microns and less than 70 microns comprising 5-100% by weight of a crosslinked polymeric matrix and 0-95% by weight of at least one inorganic filler having a mean particle size in the range of 0.005-20 microns; (E2) one or more second fillers having a mean particle size of more than 0.25 microns, but no more than 4.5 microns; and (E3) one or more third fillers having a mean particle size of 0.005-0.25 microns; (F) optionally one or more ingredients selected from the group consisting of: a colorant, a stabilizer, a UV absorber, a solvent, a fluoride-releasing compound, an antimicrobial additive, and a surfactant; wherein the weight ratio of (A+B):(C) ranges from 30:70 to 90:10; the concentration of component (A) in the restorative composition, excluding fillers, is in the range of 10-50% by weight; the concentration of component (B) in the restorative composition, excluding fillers, is in the range of 15-60% by weight; and the composition has a shear bond strength of at least 10 MPa to both dentin and enamel after being light-cured. ### Claim 20 (depends on 19) The self-adhering dental restorative composition of claim 19 wherein: (E1) the polymeric filler has a mean particle size of more than 10 microns and less than 60 microns comprising 10-30% by weight of a crosslinked poly(meth)acrylate polymeric matrix and 70-90% by weight of at least one inorganic filler having a mean particle size in the range of 0.01-4.5 microns; the weight ratio of (A+B):(C) ranges from 30:70 to 80:20; and the concentration of component (A) in the restorative composition, excluding fillers, is in the range of 10-45% by weight. ### Claim 21 (depends on 20) The self-adhering dental restorative composition of claim 20 wherein: (E1) the at least one inorganic filler has a mean particle size in the range of 0.01-2.0 microns; (E2) the one or more second fillers have a mean particle size of more than 0.25 microns, but no more than 2.0 microns; and (E3) the one or more third fillers have a mean particle size of 0.01-0.25 microns. ### Claim 22 (depends on 19) The single-part, light-curable, self-adhering dental restorative composition of claim 19 wherein the one or more first polymerizable monomers (A) further comprise glyceryldi(meth)acrylate phosphate, bis{hydroxyethyl (meth)acrylate} phosphate, or a combination thereof. ### Claim 23 (depends on 19) A method of using the self-adhering dental restorative composition of claim 19 comprises: (i) applying the self-adhering dental restorative composition to tooth structure without first treating the tooth structure with an etchant, a primer and/or an adhesive; and (ii) subsequently hardening the composition by light-curing the composition.