# US 5,705,581 A · Fluoride ion releasing dental materials > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,705,581 A - Document ID: US5705581A - Status: Granted - Kind: A - Application number: 08/474,162 - Filed: 1995-06-07 - Granted: 1998-01-06 - Earliest claimed: 1995-01-26 - Assignees: Indiana University Foundation - Inventors: Wilmer K. Fife; Martel Zeldin; Slawomir Rubinsztajn - Web page: https://patentgrep.com/patent/US5705581A ## CPC - C07C 233/38: having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton - A61K 6/887: Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds - C08F 220/60: containing nitrogen in addition to the carbonamido nitrogen - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - 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 ## Abstract Described are novel fluoride ion-releasing acrylic or methacrylic acid-based monomers, fluoride ion-releasing dental resin materials prepared from the monomers, and processes for preparing the monomers and dental resin materials. The monomers of the invention are prepared in good yield from readily available starting materials. Dental resin materials of the invention exhibit excellent sustained fluoride ion release. ## Claims ### Claim 1 A dental resin material comprising a solid reaction product of a monomer of the formula: ##STR9## wherein Y.sup.- is a fluoride or fluoride-containing anion, R.sup.1 is --H or methyl, R.sup.2 is a divalent C.sub.1 -C.sub.12 alkylene radical, and each R.sup.3, which may be the same as or may differ from one another, is H, C.sub.1 -C.sub.16 alkyl or hydroxyalkyl, or a group of the formula ##STR10## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined above, n is an integer from 1 to about 12, and each R.sup.4, which may be the same as or may differ from one another, is H, lower alkyl, lower hydroxyalkyl, or an amide group of the formula --CH(CH.sub.2 OH)(CONHCH.sub.2 CH.sub.2 OH); with at least one other polymerizable acrylic or methacrylic monomer, with the proviso that at least one of the reacted monomers is a free radical polymerizable crosslinking agent. ### Claim 2 (depends on 1) The dental resin material of claim 1 wherein Y.sup.- is ((HF).sub.x F).sup.- wherein x=1 to 7. ### Claim 3 (depends on 1, 2) The dental resin material of claim 2 wherein R.sup.1 is --CH.sub.3, R.sup.2 is --(CH.sub.2).sub.3 --, and each R.sup.3 is lower alkyl, lower hydroxy alkyl, or an amide group of formula (IV) as defined in claim 1 wherein each group R.sup.4 is H. ### Claim 4 (depends on 3) The dental resin material of claim 3 wherein two groups R.sup.3 are methyl and the third group R.sup.3 is ethyl or 2-hydroxyethyl. ### Claim 5 A dental resin material comprising a reaction product of a first monomer which is a fluoride ion-releasing polymerizable monomer bearing an anion exchange site carrying a fluoride-containing anion of the formula ((HF).sub.x F).sup.- wherein x is an integer from 1 to 7, with at least one other monomer which is an acrylic or methacrylic monomer, with the proviso that at least on of said monomers is a crosslinking monomer. ### Claim 6 (depends on 5) The dental resin material of claim 5 wherein x is 2 or 3. ### Claim 7 (depends on 5) The dental resin material of claim 5 wherein said first monomer is an acrylic acid or methacrylic acid monomer. ### Claim 8 (depends on 7) The dental resin material of claim 7 wherein said first monomer is an acrylate, methacrylate, acrylamide or methacrylamide monomer. ### Claim 9 (depends on 8) The dental resin material of claim 8 wherein x is 2 or 3. ### Claim 10 (depends on 2) The dental resin material of claim 2, wherein at least one group R.sup.3 is a group of the formula II. ### Claim 11 (depends on 2) The dental resin material of claim 2 wherein at least one group R.sup.3 is a group of the formula III. ### Claim 12 (depends on 2) The dental resin material of claim 2 wherein at least one group R.sup.3 is a group of the formula IV. ### Claim 13 (depends on 1) The dental resin material of claim 1, which comprises a reaction product of said at least one other polymerizable acrylic or methacrylic acid monomer with a monomer selected from the group consisting of: 3-(methacryloylamino)propyldimethylamine polyhydrogen fluoride-fluoride; 3-(methacryloylamino)propyldimethylethylammonium polyhydrogen fluoride-fluoride; 3-(methacryloylamino)propyldimethylhexylammonium polyhydrogen fluoride-fluoride; 3-(methacryloylamino)propyldimethyloctylammonium polyhydrogen fluoride-fluoride; 3-(methacryloylamino)propyldimethyldecylammonium polyhydrogen fluoride-fluoride; 3-(methacryloylamino)propyldimethylhydroxyethylammonium polyhydrogen fluoride-fluoride; 1,4-bis-(3-(methacryloylamino)propyldimethylammonium)butane difluoride; 3-(methacryloylamino)propylethyldimethylammonium fluoride; 3-(methacryloylamino)propyldimethylacetamidoammonium fluoride; and 3-(methacryloylamino)propyltrimethylammonium fluoride. ### Claim 14 (depends on 13) The dental resin material of claim 13 which also comprises an acrylic or methacrylic acid ester. ### Claim 15 (depends on 1) The dental resin material of claim 1, and also including an inorganic filler. ### Claim 16 (depends on 15) The dental resin material of claim 15, which includes a reaction product of said at least one other acrylic or methacrylic acid monomer with 3-(methacryloylamino)propyldimethylethylammonium polyhydrogen fluoride-fluoride.