IP Library Granted Patent US 8,840,918
Granted Patent B2
US 8,840,918 · App. 10/359,548 · Granted Sep 23, 2014

Hydrogel compositions for tooth whitening

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Quick Facts
Patent No.
US 8,840,918
App. No.
10/359,548
Granted
Sep 23, 2014
Kind
B2
Abstract

A composition is provided, wherein the composition comprises a water-swellable, water-insoluble polymer, a blend of a hydrophilic polymer and a complementary oligomer capable of hydrogen bonding to the hydrophilic polymer, and a whitening agent, preferably a peroxide. The composition finds utility as a tooth whitening composition and is applied to the teeth in need of whitening, and then removed when the degree of whitening has been achieved. In certain embodiments, the composition is translucent. Methods for preparing and using the compositions are also disclosed.

Claims (49)

1. An in-vivo film forming liquid teeth whitening composition comprising:

(a) 2-6 wt % of a water-swellable, water-insoluble acrylate-based polymer or copolymer comprising monomers selected from acrylic acid, methacrylic acid, methyl acrylate, ethyl acrylate, methyl methacrylate, and ethyl methacrylate;

(b) 4-10 wt % of a poly(N-vinyl lactam);

(c) 0.5-10 wt % of a polyalkylene glycol having a molecular weight ranging from about 300 to about 600 daltons, and

(d) 1-30 wt % of a whitening agent,

dissolved in a solvent mixture comprising water and a lower alcohol,

wherein, the liquid composition upon application to the surface of the teeth and evaporation of the lower alcohol, forms a hydrogel film that is insoluble or slowly soluble in saliva at body temperature to thereby remain on the teeth surface for a period of over at least 10 minutes.

2. The composition of claim 1 wherein the water-swellable, water-insoluble copolymer is a copolymer of methacrylic acid and methyl methacrylate or is a copolymer of methacrylic acid and ethyl acrylate.

3. The composition of claim 1 , wherein the acrylate-based polymer or copolymer is selected from the group consisting of (dimethylaminoethyl methacrylate-butyl methacrylate-methyl methacrylate copolymers, methacrylic acid-methyl methacrylate copolymers, 1:1, methacrylic acid-methyl methacrylate copolymers, 1:2, ethyl acrylate-methyl methacrylate-methacrylic acid ester with quaternary ammonium groups copolymers, 1:2:0.2, ethyl acrylate-methyl methacrylate-methacrylic acid ester with quaternary ammonium groups copolymers, 1:2:0.1 and ethyl acrylate-methyl methacrylate copolymers, 2:1).

4. The composition of claim 3 , wherein the acrylate-based polymer or copolymer is a methacrylic acid-methyl methacrylate copolymer.

5. The composition of claim 4 , wherein the copolymer has a ratio of free carboxyl groups to ester groups in the range of about 1:1 to 1:2.

6. The composition of claim 1 , wherein the poly(N-vinyl lactam) is selected from the group consisting of polyvinyl pyrrolidone, polyvinyl caprolactam, and blends thereof.

7. The composition of claim 6 , wherein the poly(N-vinyl lactam) is polyvinyl pyrrolidone.

8. The composition of claim 6 , wherein the poly(N-vinyl lactam) is polyvinyl caprolactam.

9. The composition of claim 1 , wherein the poly(N-vinyl lactam) has a number average molecular weight in the range of approximately 100,000 to 2,000,000.

10. The composition of claim 9 , wherein the poly(N-vinyl lactam) has a number average molecular weight in the range of approximately 500,000 to 1,500,000.

11. The composition of claim 1 , wherein the polyalkylene glycol has a molecular weight of about 400.

12. The composition of claim 1 , wherein the polyalkylene glycol is selected from the group consisting of carboxyl-terminated polyalkylene glycols and amino-terminated polyalkylene glycols.

13. The composition of claim 12 , wherein the polyalkylene glycol is selected from the group consisting of polyethylene glycol and carboxyl-terminated polyethylene glycol.

14. The composition of claim 13 , wherein the polyalkylene glycol is polyethylene glycol.

15. The composition of claim 1 , wherein the whitening agent is selected from the group consisting of peroxides, metal chlorites, perborates, percarbonates, peroxyacids, and combinations thereof.

16. The composition of claim 15 , wherein the whitening agent is a peroxide selected from the group consisting of hydrogen peroxide, calcium peroxide, carbamide peroxide, and mixtures thereof.

17. The composition of claim 15 , wherein the peroxide is an organic peroxide.

18. The composition of claim 17 , wherein the organic peroxide is selected from the group consisting of dialkyl peroxides, diacyl peroxides, peresters, perdicarbonates, ketone peroxides, and hydroperoxides.

19. The composition of claim 18 , wherein the dialkyl peroxide is t-butyl peroxide or 2,2 bis(t-butylperoxy)propane.

20. The composition of claim 18 , wherein the diacyl peroxide is benzoyl peroxide or acetyl peroxide.

21. The composition of claim 18 , wherein the perester is t-butyl perbenzoate or t-butyl per-2-ethylhexanoate.

22. The composition of claim 18 , wherein the perdicarbonate is dicetyl peroxy dicarbonate or dicyclohexyl peroxy dicarbonate.

23. The composition of claim 18 , wherein the ketone peroxide is cyclohexanone peroxide or methylethylketone peroxide.

24. The composition of claim 18 , wherein the hydroperoxide is cumene hydroperoxide or tert-butyl hydroperoxide.

25. The composition of claim 1 , further comprising a flavorant.

26. The composition of claim 25 , wherein the flavorant is selected from the group consisting of wintergreen, peppermint, spearmint, menthol, fruit flavors, vanilla, cinnamon, spices, flavor oils and oleoresins, and combinations thereof.

27. The composition of claim 1 , further comprising a sweetener selected from the group consisting of sucrose, fructose, aspartame, xylitol and saccharine.

28. The composition of claim 1 , further comprising at least one additive selected from the group consisting of fillers, preservatives, pH regulators, softeners, thickeners, colorants, pigments, dyes, refractive particles, flavorants, sweeteners, stabilizers, toughening agents, detackifiers, and permeation enhancers.

29. The composition of claim 1 , wherein the composition is translucent.

30. The composition of claim 28 , which further comprises an absorbent filler.

31. A method for whitening teeth comprising: applying the composition of claim 1 to at least a portion of the surface of one or more teeth, and maintaining the composition on the surface of the one or more teeth for a desired period of time, to thereby achieve a desired degree of whitening.

32. The method of claim 31 , wherein the desired period of time is predetermined.

33. The method of claim 32 , wherein the predetermined period of time is from about 10 minutes to about 24 hours.

34. The method of claim 33 , wherein the predetermined period of time is from about 10 minutes to about 8 hours.

35. The method of claim 34 , wherein the predetermined period of time is about 30 minutes to 1 hour.

36. The method of claim 31 , wherein the composition is applied by the user.

37. The method of claim 31 , wherein the composition is applied by finger, directly from a container comprising the composition, by brush or by applicator.

38. The composition of claim 1 , wherein the composition forms a continuous integrated viscous swollen gel coating separated from a liquid solution by a sharp phase boundary upon contact with aqueous media when characterized in-vitro by wedge microinterferometry.

39. The composition of claim 1 , wherein the solvent mixture comprises water and ethanol.

40. The method of claim 31 , further comprising, after the maintaining step, removing the hydrogel film composition from the surface of the one or more teeth.

41. The method of claim 40 , wherein the removing is by dissolution of the hydrogel film composition in saliva over time.

42. The method of claim 40 , wherein the removing is by conventional tooth cleansing methods.

43. The liquid composition of claim 1 , wherein components of the composition are miscible upon solvent evaporation.

Assignments (19)
CORRECTIVE ASSIGNMENT TO CORRECT THE APPLICATION NUMBER PREVIOUSLY RECORDED AT REEL: 61852 FRAME: 207. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 30, 2025
From: CORIUM, INC.
To: CORIUM PHARMA SOLUTIONS, INC.
Reel/Frame 071915/0691 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 24, 2022
From: CORIUM, INC.
To: CORIUM PHARMA SOLUTIONS, INC.
Reel/Frame 062760/0731 →
RELEASE OF SECURITY INTEREST Recorded Oct 19, 2022
From: HERCULES CAPITAL, INC., AS AGENT
To: CORIUM, INC.
Reel/Frame 061713/0557 →
RELEASE OF SECURITY INTEREST Recorded Oct 17, 2022
From: HERCULES CAPITAL, INC.
To: CORIUM, INC.
Reel/Frame 061687/0281 →
SECURITY INTEREST Recorded Oct 17, 2022
From: CORIUM PHARMA SOLUTIONS, INC.
To: SILICON VALLEY BANK, AS ADMINISTRATIVE AGENT
Reel/Frame 061689/0581 →
CHANGE OF NAME Recorded Oct 14, 2022
From: CORIUM, INC.
To: CORIUM PHARMA SOLUTIONS, INC.
Reel/Frame 061852/0207 →
SECURITY INTEREST Recorded Sep 24, 2021
From: CORIUM, INC.
To: HERCULES CAPITAL, INC., AS AGENT
Reel/Frame 057597/0907 →
CHANGE OF NAME Recorded Apr 9, 2019
From: CORIUM INTERNATIONAL, INC.
To: CORIUM, INC.
Reel/Frame 048841/0324 →
RELEASE OF SECURITY INTEREST Recorded Mar 6, 2018
From: CAPITAL ROYALTY PARTNERS II L.P.; CAPITAL ROYALTY PARTNERS II - PARALLEL FUND "A" L.P.; CAPITAL ROYALTY PARTNERS II - PARALLEL FUND "B" (CAYMAN) L.P.; CAPITAL ROYALTY PARTNERS II (CAYMAN) L.P.; PARALLEL INVESTMENT OPPORTUNITIES PARTNERS II L.P.
To: CORIUM INTERNATIONAL, INC.
Reel/Frame 046909/0855 →
RELEASE OF SECURITY INTEREST Recorded Mar 6, 2018
From: CAPITAL ROYALTY PARTNERS II L.P.; CAPITAL ROYALTY PARTNERS II - PARALLEL FUND "A" L.P.; CAPITAL ROYALTY PARTNERS II - PARALLEL FUND "B" (CAYMAN) L.P.; CAPITAL ROYALTY PARTNERS II (CAYMAN) L.P.; PARALLEL INVESTMENT OPPORTUNITIES PARTNERS II L.P.
To: CORIUM INTERNATIONAL, INC.
Reel/Frame 045513/0686 →
RELEASE OF SECURITY INTEREST Recorded Nov 27, 2017
From: SILICON VALLEY BANK
To: CORIUM INTERNATIONAL, INC.
Reel/Frame 044229/0054 →
RELEASE OF SECURITY INTEREST Recorded Nov 27, 2017
From: SILICON VALLEY BANK
To: CORIUM INTERNATIONAL, INC.
Reel/Frame 044810/0026 →
SECURITY INTEREST Recorded Dec 4, 2014
From: CORIUM INTERNATIONAL, INC.
To: CAPITAL ROYALTY PARTNERS II L.P.; CAPITAL ROYALTY PARTNERS II ? PARALLEL FUND ?A? L.P.; CAPITAL ROYALTY PARTNERS II ? PARALLEL FUND ?B? (CAYMAN) L.P.; CAPITAL ROYALTY PARTNERS II (CAYMAN) L.P.
Reel/Frame 034535/0238 →
CORRECTIVE ASSIGNMENT TO CORRECT THE NAME AND ADDRESS OF ONE OF THE ASSIGNEES PREVIOUSLY RECORDED ON REEL 013531 FRAME 0007. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNEE'S NAME IS CORIUM INTERNATIONAL, INC. AND THE ADDRESS IS 235 CONSTITUTION DRIVE, MENLO PARK CA 94025. Recorded Oct 31, 2013
From: SINGH, PARMINDER; CLEARY, GARY W.; MUDUMBA, SRI
To: CORIUM INTERNATIONAL, INC.
Reel/Frame 031531/0447 →
SECURITY AGREEMENT Recorded Sep 10, 2012
From: CORIUM INTERNATIONAL, INC.
To: SILICON VALLEY BANK
Reel/Frame 028927/0365 →
SECURITY AGREEMENT Recorded Sep 4, 2012
From: CORIUM INTERNATIONAL, INC.
To: CAPITAL ROYALTY PARTNERS II L.P.; CAPITAL ROYALTY PARTNERS II - PARALLEL FUND "A" L.P.; PARALLEL INVESTMENT OPPORTUNITIES PARTNERS II L.P.
Reel/Frame 028895/0961 →
RELEASE OF SECURITY INTEREST Recorded Aug 30, 2012
From: OXFORD FINANCE LLC
To: CORIUM INTERNATIONAL, INC.
Reel/Frame 028884/0179 →
SECURITY AGREEMENT Recorded Dec 20, 2011
From: CORIUM INTERNATIONAL, INC.
To: OXFORD FINANCE LLC, AS COLLATERAL AGENT
Reel/Frame 027422/0717 →
SECURITY AGREEMENT Recorded May 5, 2009
From: CORIUM INTERNATIONAL, INC.
To: SILICON VALLEY BANK
Reel/Frame 022634/0119 →