# US 10,478,384 B2 · Dental composition > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,478,384 B2 - Document ID: US10478384B2 - Status: Granted - Kind: B2 - Application number: 14/101,936 - Filed: 2013-12-10 - Published: 2014-06-12 - Granted: 2019-11-19 - Earliest claimed: 2012-12-11 - Assignees: Zimmer Dental, Inc. - Applicants: Zimmer Dental, Inc. - Inventors: Jin Whan Lee; Hai Bo Wen; Jeffrey Bassett; Mike Warner - Web page: https://patentgrep.com/patent/US10478384B2 ## CPC - A61K 6/58: specially adapted for dental implants - A61K 6/56: Apical treatment - 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 Dental compositions are disclosed. A dental composition can include a reaction produce of a reaction mixture comprising a first mixture and a second mixture. The first mixture can include a ceramic based biomaterial, and the second mixture can include mineral trioxide aggregate and a phosphoric acid monomer. ## Claims ### Claim 1 A dental composition for a dental implant insertable into an implant site, comprising: a reaction product of a reaction mixture comprising: a first mixture comprising: a ceramic based biomaterial including hydroxyapatite, a diluent comprising a cross-linking agent, and a first initiator, and a second mixture comprising: mineral trioxide aggregate reacts with moisture at the implant site to form a solid scaffold on the dental implant, a phosphoric acid monomer reacts with the ceramic based biomaterial and the mineral trioxide aggregate to bond the ceramic based biomaterial to the solid scaffold of mineral trioxide aggregate, and a second initiator; wherein the diluent reacts with the phosphoric acid monomer to crosslink at least the phosphoric acid monomer. ### Claim 2 (depends on 1) The dental composition of claim 1, wherein the ceramic based biomaterial further includes one or more of calcium phosphates, strontium phosphates, calcium carbonates, calcium sulfate, and calcium hydroxide. ### Claim 3 (depends on 1) The dental composition of claim 1, wherein about 50 weight percent to about 80 weight percent of the first mixture comprises the ceramic based biomaterial, the weight percent based on a total weight of the first mixture. ### Claim 4 (depends on 1) The dental composition of claim 1, wherein 60 weight percent of the first mixture comprises the ceramic based biomaterial, the weight percent based on a total weight of the first mixture. ### Claim 5 (depends on 1) The dental composition of claim 1, wherein about 5 weight percent to about 50 weight percent of the second mixture comprises the mineral trioxide aggregate, the weight percent based on a total weight of the second mixture. ### Claim 6 (depends on 1) The dental composition of claim 1, wherein the phosphoric acid monomer is chosen from at least one of 1-methacryloyloxydecane-10-phosphate, 1-methacryloyloxyhexane-6-phosphate, 1-methacryloylaminodecane-10-phosphate, 1-acryloylaminohexane-6-phosphate, 1,3-dimethacryloyloxypropane-2-phosphate, and 1,3-dimethacryloylaminopropane-2-phosphate. ### Claim 7 (depends on 1) The dental composition of claim 1, wherein about 1 weight percent to about 15 weight percent of the second mixture comprises the phosphoric acid monomer, the weight percent based on a total weight of the second mixture. ### Claim 8 (depends on 1) The dental composition of claim 1, wherein the first mixture comprises about 15 weight percent to about 55 weight percent of the diluent, the weight percent based on a total weight of the first mixture. ### Claim 9 (depends on 1) The dental composition of claim 1, wherein the first mixture comprises about 2 weight percent to about 8 weight percent of N,N-di(2-hydroxyethyl)-p-toluidine as the first initiator, the weight percent based on a total weight of the first mixture. ### Claim 10 (depends on 1) The dental composition of claim 1, wherein the second mixture further comprises about 10 weight percent to about 50 weight percent of a bioactive glass, the weight percent based on a total weight of the second mixture. ### Claim 11 (depends on 1) The dental composition of claim 1, wherein the second initiator includes a peroxide comprising about 0.5 weight percent to about 6 weight percent of the second mixture, the weight percent based on a total weight of the second mixture. ### Claim 12 (depends on 1) The dental composition of claim 1, wherein the first mixture comprises: 60 weight percent of hydroxyapatite; 35 weight percent of the diluent; and 5 weight percent of the first initiator, wherein the first initiator comprises N,N-di(2-hydroxyethyl)p-toluidine, the weight percent based on a total weight of the first mixture. ### Claim 13 (depends on 12) The dental composition of claim 12, wherein the diluent is tetra-ethylene glycol dimethacrylate. ### Claim 14 (depends on 1) The dental composition of claim 1, wherein the second mixture comprises: 25 weight percent of the mineral trioxide aggregate; 5 weight percent of the phosphoric acid monomer; 3 weight percent of the second initiator, wherein the second initiator comprises a peroxide; and further comprises 37 weight percent of a diluent and 30 weight percent of a bioactive glass, the weight percent based on a total weight of the second mixture. ### Claim 15 (depends on 14) The dental composition of claim 14, wherein the diluent of a second mixture is tetra-ethylene glycol dimethacrylate, the peroxide is benzoyl peroxide, and the bioactive glass has a formulation of 46.1 mole percent of silicon dioxide, 2.6 mole percent of phosphorus pentoxide, 26.9 mole percent of calcium oxide, and 24.4 mole percent of sodium oxide. ### Claim 16 (depends on 1) A method, comprising: obtaining or providing the first mixture of claim 1; obtaining or providing the second mixture of claim 1; and combining the first mixture and the section mixture to form the reaction product of claim 1. ### Claim 17 (depends on 16) The method of claim 16, wherein obtaining or providing the first mixture comprises: combining the ceramic based biomaterial with the diluent and N,N-di(2-hydroxyethyl)-p-toluidine as the first initiator. ### Claim 18 (depends on 17) The method of claim 17, wherein obtaining or providing the first mixture comprises: dissolving the N,N-di(2-hydroxyethyl)-p-toluidine in the diluent to form a first solution; and mixing the first solution with the ceramic based biomaterial to form the first mixture. ### Claim 19 (depends on 18) The method of claim 18, wherein the diluent of the first mixture is a first diluent, and wherein obtaining or providing the second mixture comprises: combining the mineral trioxide aggregate and the phosphoric acid monomer with a second diluent, and a peroxide as the second initiator and further combining with a bioactive glass. ### Claim 20 (depends on 16) The method of claim 16, wherein obtaining or providing the second mixture comprises: dissolving the phosphoric acid monomer and the peroxide in the diluent to form a second solution; and mixing the second solution with the mineral trioxide aggregate and further mixing with a bioactive glass to form the second mixture.