Polyphenols/PEG based hydrogel system for a dental varnish

Patent metadata

Field	Value
Publication number	US-10500138-B2
Application number	US-201815939507-A
Country	US
Kind code	B2
Filing date	Mar 29, 2018
Priority date	Mar 29, 2017
Publication date	Dec 10, 2019
Grant date	Dec 10, 2019

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.

First claim

We 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.

2. 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.

3. 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.

4. 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.

5. The hydrogel system according to claim 1 , wherein the metal ion source includes a divalent, trivalent metal ion source, or mixtures thereof.

6. 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.

7. 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.

8. The hydrogel system, according to claim 1 , further comprising a solvent.

9. 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.

10. The hydrogel system, according to claim 1 , further comprising an anti-oxidant.

11. 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.

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.

13. 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.

14. 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.

15. The dental varnish according to claim 12 , wherein the metal ion source includes a divalent, trivalent metal ion source, or mixtures thereof.

16. 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.

17. 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.

18. The dental varnish composition according to claim 16 , wherein the fluoride source includes both stannous fluoride and sodium fluoride.

19. The den

Assignees

• Dentsply Sirona Inc

Inventors

• Jha Amit
• Simonton Thomas C

Classifications

• A61K6/84

  comprising metals or alloys · CPC title

• A61K6/891

  Compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• A61K6/20 Primary

  Protective coatings for natural or artificial teeth, e.g. sealings, dye coatings or varnish · CPC title

• A61K6/831 Primary

  comprising non-metallic elements or compounds thereof, e.g. carbon · CPC title

• A61Q11/00

  Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses · CPC title