# US 10,500,138 B2 · Polyphenols/PEG based hydrogel system for a dental varnish > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,500,138 B2 - Document ID: US10500138B2 - Status: Granted - Kind: B2 - Application number: 15/939,507 - Filed: 2018-03-29 - Published: 2018-10-18 - Granted: 2019-12-10 - Earliest claimed: 2017-03-29 - Assignees: DENTSPLY SIRONA Inc. - Applicants: DENTSPLY SIRONA Inc. - Inventors: Amit Jha; Thomas C. Simonton - Web page: https://patentgrep.com/patent/US10500138B2 ## CPC - A61K 6/20: Protective coatings for natural or artificial teeth, e.g. sealings, dye coatings or varnish - A61K 6/831: comprising non-metallic elements or compounds thereof, e.g. carbon - A61K 6/84: comprising metals or alloys - A61K 6/891: Compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds - A61K 8/042: {Gels} - A61K 8/21: Fluorides; Derivatives thereof - A61Q 11/00: Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses - 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) - A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS ## Abstract Described herein are dental treatment compositions, more particularly, a dental varnish composition useful in effective fluoridation, enhancement of remineralization the tooth enamel, and hypersensitivity through occlusion of dentine tubule. The dental varnish composition includes a hydrogel system and at least one fluoride source, wherein the dental varnish is water soluble. The hydrogel system includes at least one polyphenol having at least one phenol group, at least one polymer, and a metal ion. Described herein are also methods of making such dental varnish composition. ## Claims ### Claim 1 A hydrogel system for use in a dental varnish, said hydrogel system comprising: (a) at least one compound having at least one phenol group; (b) at least one polymer comprising a functional group capable of forming a hydrogen bond with said at least one compound having at least one phenol group; and (c) a metal ion, wherein the at least one compound having at least one phenol group includes both tannic acid and gallic acid; and wherein the hydrogel system is capable of forming a crosslinked film while simultaneously adhering to an enamel surface of a tooth. ### Claim 2 (depends on 1) The hydrogel system according to claim 1, wherein the at least one compound having at least one phenol group further comprises at least one compound selected from the group consisting of resveratrol, isoflavones, flavonols, flavones, isoflavonone, flavanones, hydroxycinnamic acids, tocopherol, anthocyanidins, procyanidin, catechin and combinations thereof. ### Claim 3 (depends on 1) The hydrogel system according to claim 1, wherein the functional group is selected from the group consisting of hydroxy, amine, thiol, carboxyl, carbonyl, ester, imine, amide, and nitrile. ### Claim 4 (depends on 1) The hydrogel system according to claim 1, wherein the at least one polymer is selected from the group consisting of polyethylenegylcol, polyethyleneimine, poly(N-isopropylacrylamide) (PNIPAM), polyacrylonitrile, polyoxazoline, poly(N-vinylpyrrolidone) (PVPON), poly(2-alkyl-2-oxazoline)s, poly(2-methyl-2-oxazoline), poly(2-ethyl-2-oxazoline), polyvinyl alcohol, pluronic, polyacrylic acid, polymethyl meth acrylic acid, poly methyl acrylic acid, Poly(vinylamine) hydrochloride, Poly(L-lysine hydrobromide), Poly(allylamine), Poly(allylamine hydrochloride), Poly(4-aminostyrene), Poly(N-methylvinylamine), poly(ethylene glycol) bis (2-aminoethyl), Poly(diallyldimethylammonium chloride), Poly(2-vinyl-1-methylpyridinium bromide), Poly (N-ethenylformamide), Polyacrylamide (PAM), Chitosan, Poly(benzyl methacrylate), Poly(iso-butyl acrylate), Poly(n-butyl acrylate), Poly(tert-butyl acrylate), Poly(iso-butyl methacrylate), Poly(n-decyl acrylate), Poly(ethyl acrylate), Poly(glycidyl methacrylate), Poly(2-hydroxyethyl methacrylate), Poly(2-hydroxyethyl methacrylic acid), Poly(2-hydroxypropyl methacrylate), Poly(lauryl acrylate), Poly(octadecyl methacrylate), Poly(iso-propyl methacrylate), Poly(β-amino ester), Polyester, Polycarbophil, Poly(acrylamide/acrylic acid), Poly(2-ethyl-2-oxazoline), Poly(hexamethyleneadipamide), Poly(hexamethylenesebacamide), Polymethacrylamide, Polyaniline, Poly(2-methacryloxyethyltrimethylammonium bromide), Poly(lysine), Poly(N-vinylpyrrolidone), Poly(lactic acid), Poly(acryloyl chloride), Poly(ethylene glycol) 2-mercaptoethyl ether acetic acid, and mixtures thereof. ### Claim 5 (depends on 1) The hydrogel system according to claim 1, wherein the metal ion source includes a divalent, trivalent metal ion source, or mixtures thereof. ### Claim 6 (depends on 5) The hydrogel system, according to claim 5, wherein the divalent ion source is selected from the group consisting of a salt of calcium, zinc, magnesium, tin, strontium, chromium, manganese, beryllium, barium, cobalt, nickel, lead and copper. ### Claim 7 (depends on 5) The hydrogel system, according to claim 5, wherein the trivalent ion source is selected from the group consisting of a salt of aluminum, iron, chromium, bismuth, manganese, cobalt and indium. ### Claim 8 (depends on 1) The hydrogel system, according to claim 1, further comprising a solvent. ### Claim 9 (depends on 8) The hydrogel system, according to claim 8, wherein the solvent is selected from the group consisting of water, ethyl alcohol, isopropanol, ethyl acetate, butyl acetate, isoamyl propionate, hexane, heptane, and mixtures thereof. ### Claim 10 (depends on 1) The hydrogel system, according to claim 1, further comprising an anti-oxidant. ### Claim 11 (depends on 10) The hydrogel system, according to claim 10, wherein the anti-oxidant is selected from the group consisting of boric acid, ascorbic acid, borax, sodium tetra borate, 4,4′-Biphenyldiboronic acid, Benzene-1,4-diboronic acid, 2,5-thiophenediylbisboronic acid, sulfur dioxide, uric acid, tocopherol and mixtures thereof. ### Claim 12 A dental varnish composition comprising a hydrogel system and at least one fluoride source; wherein the hydrogel system comprises at least one compound having at least one phenol group; at least one polymer comprising a functional group capable of forming a hydrogen bond with said at least one compound having at least one phenol group, and a metal ion source, wherein the at least one compound having at least one phenol group includes both tannic acid and gallic acid; and, wherein the dental varnish is water soluble. ### Claim 13 (depends on 12) The dental varnish according to claim 12, wherein the at least one compound having at least one phenol group further comprises at least one compound selected from the group consisting of resveratrol, isoflavones, flavonols, flavones, isoflavonone, flavanones, hydroxycinnamic acids, tocopherol, anthocyanidins, procyanidin, catechin and combinations thereof. ### Claim 14 (depends on 12) The dental varnish according to claim 12, wherein the at least one polymer is selected from the group consisting of polyethylenegylcol, polyethyleneimine, poly(N-isopropylacrylamide) (PNIPAM), polyacrylonitrile, polyoxazoline, poly(N-vinylpyrrolidone) (PVPON), poly(2-alkyl-2-oxazoline)s, poly(2-methyl-2-oxazoline), poly(2-ethyl-2-oxazoline), polyvinyl alcohol, pluronic, polyacrylic acid, polymethyl meth acrylic acid, poly methyl acrylic acid, Poly(vinylamine) hydrochloride, Poly(L-lysine hydrobromide), Poly(allylamine), Poly(allylamine hydrochloride), Poly(4-aminostyrene), Poly(N-methylvinylamine), Poly(ethylene glycol) bis (2-aminoethyl), Poly(diallyldimethylammonium chloride), Poly(2-vinyl-1-methylpyridinium bromide), Poly (N-ethenylformamide), Polyacrylamide (PAM), Chitosan, Poly(benzyl methacrylate), Poly(iso-butyl acrylate), Poly(n-butyl acrylate), Poly(tert-butyl acrylate), Poly(iso-butyl methacrylate), Poly(n-decyl acrylate), Poly(ethyl acrylate), Poly(glycidyl methacrylate), Poly(2-hydroxyethyl methacrylate), Poly(2-hydroxyethyl methacrylic acid), Poly(2-hydroxypropyl methacrylate), Poly(lauryl acrylate), Poly(octadecyl methacrylate), Poly(iso-propyl methacrylate), Poly(β-amino ester), Polyester, Polycarbophil, Poly(acrylamide/acrylic acid), Poly(2-ethyl-2-oxazoline), Poly(hexamethyleneadipamide), Poly(hexamethylenesebacamide), Polymethacrylamide, Polyaniline, Poly(2-methacryloxyethyltrimethylammonium bromide), Poly(lysine), Poly(N-vinylpyrrolidone), Poly(lactic acid), Poly(acryloyl chloride), Poly(ethylene glycol) 2-mercaptoethyl ether acetic acid, and mixtures thereof. ### Claim 15 (depends on 12) The dental varnish according to claim 12, wherein the metal ion source includes a divalent, trivalent metal ion source, or mixtures thereof. ### Claim 16 (depends on 12) The dental varnish composition according to claim 12, wherein the at least one fluoride source is selected from the group consisting of aluminum fluoride, indium fluoride, stannous fluoride, titanium fluoride, amine fluoride, sodium fluoride, hydro fluorosilicate, sodium fluorosilicate, potassium fluoride, disodium monofluorophosphate, acidulated phosphate fluoride, potassium fluoride, and mixtures thereof. ### Claim 17 (depends on 16) The dental varnish composition according to claim 16, wherein the amine fluoride is selected from the group consisting of N′,N′-tri- (polyoxyethylene)-N-hexadecylpropylene diamine dihydrofluoride; 9-octadecylamine hydrofluoride, hexadecylamine hydrofluoride and bis-(hydroxyethyl)-aminopropyl-N-hydroxyethyloctadecylamine dihydrofluoride. ### Claim 18 (depends on 16) The dental varnish composition according to claim 16, wherein the fluoride source includes both stannous fluoride and sodium fluoride. ### Claim 19 (depends on 12) The dental varnish composition according to claim 12, wherein the hydrogel system is present in a concentration of from 5 to 95 weight percent based on a total weight of the composition. ### Claim 20 (depends on 12) The dental varnish composition according to claim 12, wherein the fluoride source is present in a concentration of from about 0.01 to about 10 weight percent based on a total weight of the composition. ### Claim 21 (depends on 12) The dental varnish composition according to claim 12, wherein the dental varnish releases fluoride ions in a concentration ranging from 1000 ppm to 30000 ppm. ### Claim 22 (depends on 12) The dental varnish composition according to claim 12, wherein a pH of the composition is in a range of from pH 1 to pH 8. ### Claim 23 (depends on 12) The dental varnish composition according to claim 12, further comprising at least one of a remineralization agent, a flavor additive, a thickening agent, a sweetener, an oxidant or a combination thereof. ### Claim 24 (depends on 12) The dental varnish composition according to claim 12, wherein the hydrogel system is capable of promoting increased adhesion of the varnish composition to a tooth surface. ### Claim 25 (depends on 12) The dental varnish according to claim 12, wherein the hydrogel system is capable of promoting in situ remineralization of a tooth surface. ### Claim 26 (depends on 12) The dental varnish according to claim 12, wherein the hydrogel system is capable of promoting occlusion of dentine tubule. ### Claim 27 A method of preparing a dental varnish comprising: (a) dissolving at least one compound having at least one phenol in a solvent to form a phenolic solution; (b) adding an antioxidant and metal ion source to the phenolic solution; (c) mixing the phenolic solution with a polymer solution to prepare a hydrogel system; (d) removing the solvent from the hydrogel system; and (e) mixing the hydrogel system with a fluoride source to form the dental varnish, wherein the at least one compound having at least one phenol group includes both tannic acid and gallic acid. ### Claim 28 (depends on 27) The method according to claim 27, wherein the compound having at least one phenol is present in the dental varnish in amounts of from about 0.01 mmole/ml to about 50 mmole/ml based on the total volume of the hydrogel system. ### Claim 29 (depends on 27) The method according to claim 27, wherein the antioxidant is present in the dental varnish in amounts of from about 0.003 mmole/ml to about 20 mmole/ml based on the total volume of the hydrogel system. ### Claim 30 (depends on 27) The method according to claim 27, wherein the metal ion source is present in the dental varnish in amounts of from about 0.005 mmole/ml to about 25 mmole/ml based on the total volume of the hydrogel system. ### Claim 31 (depends on 27) The method according to claim 27, wherein the polymer is present in the dental varnish in amounts of from about 0.001 mmole/ml to about 5 mmole/ml based on the total volume of the hydrogel system. ### Claim 32 (depends on 27) The method according to claim 27, wherein the fluoride source is added to the hydrogel system in amounts of from about 0.01 mmole/ml to about 5 mmole/ml based on the total volume of the hydrogel system.