# US 4,394,494 A · Dental filling material > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,394,494 A - Document ID: US4394494A - Status: Granted - Kind: A - Application number: 06/275,704 - Filed: 1981-06-22 - Granted: 1983-07-19 - Earliest claimed: 1980-07-04 - Assignees: Lion Corporation - Inventors: Mikio Miyake; Shinya Kitoh; Satoshi Hayashi - Web page: https://patentgrep.com/patent/US4394494A ## CPC - A61K 6/887: Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds - A61K 6/893: Polyurethanes - 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 filling material capable of forming a cured product with improved physical properties comprises a polymerizable monomer to be polymerized upon application, characterized in that the polymerizable monomer comprises a reaction product of two moles of a compound selected from the group consisting of hydroxyalkyl diacrylates and hydroxyalkyl dimethacrylates with on mole of an organic diisocyanate alone or in admixture with another polymerizable monomer. The reaction product may be bis(1,3-dimethacryloyloxy-2-propanetriyl)-N,N'-hexamethylene dicarbamate or bis(1,3-diacryloyloxy-2-propanetriyl)-N,N'-hexamethylene dicarbamate. The reaction product may be used in admixture with trimethylolpropane triacrylate and/or trimethacrylate and (mono-, di- or tri-)ethylene glycol diacrylate and/or dimethacrylate. The reaction product may also be used in admixture with bis-oxyethylenic bisphenol-A diacrylate and/or dimethacrylate and (mono-, di- or tri-)ethylene glycol diacrylate and/or dimethacrylate. ## Claims ### Claim 1 A polymerizable monomer having the formula: ##STR6## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each hydrogen or a methyl group and n is equal to a value varying from 2 to 10 . ### Claim 2 A dental filling composition, comprising: a polymerizable monomer having the formula I: ##STR7## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each a hydrogen ora methyl group and n is equal to a value varying from 2 to 10 and a filler material. ### Claim 3 (depends on 2) A dental filling composition according to claim 2, wherein said monomer of formula I is bis(1,3-dimethacryloyl-oxy-2-propanetriyl)-N,N'-hexamethylene dicarbamate. ### Claim 4 (depends on 2) A dental filling composition according to claim 2, wherein said monomer of formula I is bis(1,3-diacryloyloxy-2-propanetriyl)-N,N'-hexamethylene dicarbamate. ### Claim 5 (depends on 2) A dental filling composition according to claim 2, and further including at least one other polymerizable monomer. ### Claim 6 (depends on 2) A dental filling composition according to claim 2, wherein said monomer of formula I is present in admixture with another polymerizable monomer, said monomer of formula I being present in an amount of 5 to 80% by weight of the total weight of the polymerizable monomers. ### Claim 7 (depends on 6) A dental filling composition according to claim 6, wherein said monomer of formula I is present in an amount of 10 to 60% by weight of the total weight of the polymerizable monomers. ### Claim 8 (depends on 2) A dental filling composition according to claim 2, wherein said monomer of formula I is present in admixture with a polymerizable monomer selected from the group consisting of trimethylolpropane triacrylate, trimethylolpropane trimethacrylate and mixtures thereof, and a polymerizable monomer having the general formula II: ##STR8## wherein R is a hydrogen or a methyl group, and m is equal to a value varying from 1 to 3. ### Claim 9 (depends on 8) A dental filling composition according to claim 8, wherein said monomer of formula II is selected from the group consisting of triethylene glycol diacrylate, triethylene glycol dimethacrylate and a mixture thereof. ### Claim 10 (depends on 8) A dental filling composition according to claim 8, wherein said monomer of formula I is present in an amount of 5 to 80% by weight of the total weight of the polymerizable monomers, said monomer selected from the group consisting of trimethylolpropane triacrylate, trimethylolpropane trimethacrylate and a mixture thereof is present in an amount of 10-60% by weight of the total weight of the polymerizable monomers, and said monomer of formula II is present in an amount of 10-60% by weight of the total weight of the polymerizable monomers. ### Claim 11 (depends on 10) A dental filling composition according to claim 10, wherein said monomer of formula I is present in an amount of 10 to 60% by weight of the total weight of the polymerizable monomers, said monomer selected from the group consisting of trimethylolpropane triacrylate, trimethylolpropane trimethacrylate and a mixture thereof is present in a amount of 15-50% by weight of the total weight of the polymerizable monomers, and said monomer of formula II is present in an amount of 15-50% by weight of the total weight of the polymerizable monomers. ### Claim 12 (depends on 2) A dental filling composition according to claim 2, wherein said monomer of formula I is present in admixture with a polymerizable monomer having the general formula II: ##STR9## wherein R is a hydrogen or a methyl group, and m is equal to a value varying from 1 to 3, and a polymerizable monomer having the general formula III: ##STR10## wherein R is a hydrogen or a methyl group, and m is equal to a value varying from 1 to 3. ### Claim 13 (depends on 12) A dental filling composition according to claim 12, wherein said monomer of formula I is bis(1,3-dimethacryloyl-oxy-2-propanetriyl)-N,N'-hexamethylene dicarbamate. ### Claim 14 (depends on 12) A dental filling composition according to claim 12, wherein said monomer of formula I is bis(1,3-diacryloyloxy-2-propanetriyl)-N,N'-hexamethylene dicarbamate. ### Claim 15 (depends on 12) A dental filling composition according to claim 12, wherein said monomer of formula II is selected from the group consisting of triethylene glycol diacrylate, triethylene glycol dimethacrylate and a mixture thereof. ### Claim 16 (depends on 12) A dental filling composition according to claim 12, wherein said monomer of formula I is present in an amount of 5 to 80% by weight of the total weight of the polymerizable monomers, said monomer of formula II is present in an amount of 10-60% by weight of the total weight of the polymerizable monomers, and said monomer of formula III is present in an amount of 10-80% by weight of the polymerizable monomers. ### Claim 17 (depends on 16) A dental filling composition according to claim 16, wherein said monomer of formula I is present in an amount of 10 to 60% by weight of the total weight of the polymerizable monomers, said monomer of formula II is present in an amount of 10-60% by weight of the total weight of the polymerizable monomers, and said monomer of formula III is present in an amount of 10-60% by weight of the total weight of the polymerizable monomers. ### Claim 18 A dental filling composition, comprising: a polymerizable monomer having the formula I: ##STR11## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each a hydrogen or a methyl group, and n is equal to a value varying from 2 to 10; at least one other polymerizable monomer; a filler; and a catalyst. ### Claim 19 (depends on 18) A dental filling composition according to claim 18, wherein said polymerizable monomer I is present in an amount of 5 to 80% by weight of the total weight of the polymerizable monomers.