# US 8,541,021 B2 · Hydrogel compositions demonstrating phase separation on contact with aqueous media

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- Number: US 8,541,021 B2
- Document ID: US8541021B2
- Status: Granted
- Kind: B2
- Application number: 10/848,538
- Filed: 2004-05-17
- Published: 2004-12-23
- Granted: 2013-09-24
- Earliest claimed: 2001-05-01
- Assignees: A.V. Topchiev Institute of Petrochemical Synthesis; Corium International, Inc.
- Applicants: Parminder Singh; Gary W. Cleary; Sri Mudumba; Mikhail M. Feldstein; Danir R. Bairamov
- Inventors: Parminder Singh; Gary W. Cleary; Sri Mudumba; Mikhail M. Feldstein; Danir R. Bairamov
- Web page: https://patentgrep.com/patent/US8541021B2

## CPC

- A61K 8/042: {Gels}
- A61C 19/063: {Medicament applicators for teeth or gums, e.g. treatment with fluorides}
- A61C 19/066: {Bleaching devices; Whitening agent applicators for teeth, e.g. trays or strips}
- A61K 6/69: Medicaments
- A61K 8/22: Peroxides; Oxygen; Ozone
- A61K 8/731: {Cellulose; Quaternized cellulose derivatives}
- A61K 8/8152: {Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers}
- A61K 8/817: {Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)}
- A61K 8/8176: {Homopolymers of N-vinyl-pyrrolidones. Compositions of derivatives of such polymers}
- A61K 8/86: Polyethers
- A61L 15/60: Liquid-swellable gel-forming materials, e.g. super-absorbents
- A61Q 11/00: Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
- A61K 2800/262: Transparent; Translucent
- A61K 2800/54: Polymers characterized by specific structures/properties
- A61K 2800/5422: nonionic
- A61K 2800/5424: anionic
- 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)
- A61C: DENTISTRY; APPARATUS OR METHODS FOR ORAL OR DENTAL HYGIENE (non-driven toothbrushes A46B; {tongue scrapers A61B17/24;} preparations for dentistry A61K6/00; preparations for cleaning the teeth or mouth A61K8/00, A61Q11/00)
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS

## Abstract

A composition is provided, wherein the composition comprises a water-swellable, water-insoluble polymer or a water-soluble polymer, a blend of a hydrophilic polymer and a complementary oligomer capable of hydrogen bonding to the hydrophilic polymer. The composition also includes a second water-swellable, water-insoluble polymer that provides for a phase separating film forming composition. Active ingredients, such as a whitening agent, may be included. The composition finds utility as an oral dressing, for example, a tooth whitening composition that is applied to the teeth in need of whitening, and 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

### Claim 1

A body surface contacting composition comprising:
(a) a first water-swellable acrylate-based polymer having a pH-dependent solubility and insoluble in water at a pH less than about 5.5,
(b) a blend of a poly(N-vinyl lactam) and a complementary oligomer capable of hydrogen bonding to the poly(N-vinyl lactam); and
(c) a second water-swellable acrylate-based polymer that is insoluble in water independent of pH;
in a solvent or mixture of solvents,
wherein the weight ratio of the first to second water-swellable acrylate-based polymers is in a range of about 1.5:1 to 2:1 and the poly(N-vinyl lactam) represents about 1-30 weight percent of the composition, such that when the composition is placed in an aqueous environment at a pH of from about 6-8, the second water-swellable acrylate-based polymer forms a film over the remainder of the composition.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the first water-swellable, acrylate-based polymer includes acrylate-based polymers and copolymers.

### Claim 3 (depends on 2)

The composition of claim 2, wherein the first acrylate-based polymer or copolymer is selected from polymers and copolymers of acrylic acid, methacrylic acid, methyl acrylate, ethyl acrylate, methyl methacrylate, or ethyl methacrylate.

### Claim 4 (depends on 3)

The composition of claim 3, wherein the first acrylate-based copolymer is a copolymer of methacrylic acid and methyl methacrylate.

### Claim 5 (depends on 1)

The composition of claim 1, further comprising an active agent.

### Claim 6 (depends on 1)

The composition of claim 1, wherein the second water-swellable acrylate-based polymer includes acrylate-based polymers and copolymers.

### Claim 7 (depends on 6)

The composition of claim 6, wherein the second acrylate-based polymer or copolymer is selected from polymers and copolymers of acrylic acid, methacrylic add, methyl acrylate, ethyl acrylate, methyl methacrylate, and ethyl methacrylate.

### Claim 8 (depends on 7)

The composition of claim 7, wherein the second acrylate-based copolymer is a copolymer of methacrylic acid and methyl methacrylate.

### Claim 9 (depends on 1)

The composition of claim 1, wherein the poly(N-vinyl lactam) is a poly(N-vinyl lactam) homopolymer.

### Claim 10 (depends on 1)

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

### Claim 11 (depends on 10)

The composition of claim 10, wherein the poly(N-vinyl lactam) is polyvinyl pyrrolidone.

### Claim 12 (depends on 10)

The composition of claim 10, wherein the poly(N-vinyl lactam) has a number average molecular weight in the range of approximately 10,000 to 2,000,000.

### Claim 13 (depends on 1)

The composition of claim 1, wherein the complementary oligomer has a molecular weight in the range of about 45 to 800.

### Claim 14 (depends on 13)

The composition of claim 13, wherein the complementary oligomer has a molecular weight in the range of about 45 to 600.

### Claim 15 (depends on 13)

The composition of claim 13, wherein the complementary oligomer is selected from the group consisting of polyalcohols, alkylene glycols, polyalkylene glycols, carboxyl-terminated polyalkylene glycols, amino-terminated polyalkylene glycols, ether alcohols, alkane dials and carbonic diacids.

### Claim 16 (depends on 15)

The composition of claim 15, wherein the complementary oligomer is selected from the group consisting of polyalkylene glycols and carboxyl-terminated polyalkylene glycols.

### Claim 17 (depends on 16)

The composition of claim 16, wherein the complementary oligomer is selected from the group consisting of polyethylene glycol and carboxyl-terminated polyethylene glycol.

### Claim 18 (depends on 16)

The composition of claim 16, wherein the complementary oligomer is polyethylene glycol.

### Claim 19 (depends on 5)

The composition of claim 5, wherein the active agent is a whitening agent selected from the group consisting of peroxides, metal chlorites, perborates, percarbonates, peroxyacids, and combinations thereof.

### Claim 20 (depends on 19)

The composition of claim 19, wherein the whitening agent comprises a peroxide selected from the group consisting of hydrogen peroxide, calcium peroxide, carbamide peroxide, and mixtures thereof.

### Claim 21 (depends on 19)

The composition of claim 19, wherein the whitening agent comprises a peroxide selected from the group consisting of dialkyl peroxides, diacyl peroxides, peresters, perdicarbonates, ketone peroxides, and hydroperoxides.

### Claim 22 (depends on 19)

The composition of claim 19, wherein the metal chlorite is selected from the group consisting of calcium chlorite, barium chlorite, magnesium chlorite, lithium chlorite, sodium chlorite, and potassium chlorite.

### Claim 23 (depends on 1)

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.

### Claim 24 (depends on 1)

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

### Claim 25 (depends on 5)

The composition of claim 5, which comprises about 0.1-60 wt % of an active agent.

### Claim 26 (depends on 1)

The composition of claim 1, which comprises about 0.1-20 wt % of the first water-swellable acrylate-based polymer and the second water-swellable acrylate-based polymer.

### Claim 27 (depends on 26)

The composition of claim 26, wherein the complementary oligomer represents about 1-85 wt % of the poly(N-vinyl lactam)/complementary oligomer blend.

### Claim 28 (depends on 1)

The composition of claim 1, which comprises about 1-30 wt % of the first water-swellable acrylate-based polymer and the second water-swellable acrylate-based polymer; and about 0.1-20 wt % of the poly(N-vinyl lactam).

### Claim 29 (depends on 28)

The composition of claim 28, wherein the complementary oligomer represents about 1-85 wt % of the poly(N-vinyl lactam)/complementary oligomer blend.

### Claim 30 (depends on 1)

The composition of claim 1, which comprises about 1-20 wt % of the first water-swellable acrylate-based polymer and the second water-swellable acrylate-based polymer; and about 5-25 wt % of the poly(N-vinyl lactam).

### Claim 31 (depends on 30)

The composition of claim 30, wherein the complementary oligomer represents about 10-80 wt % of the poly(N-vinyl lactam)/complementary oligomer blend.

### Claim 32 (depends on 1)

The composition of claim 1, which comprises about 4-15% wt % of the first water-swellable acrylate-based polymer and the second water-swellable acrylate-based polymer; and about 5-25 wt % of the per poly(N-vinyl lactam).

### Claim 33 (depends on 32)

The composition of claim 32, wherein the complementary oligomer represents about 10-80 wt % of the poly(N-vinyl lactam)/complementary oligomer blend.

### Claim 34 (depends on 19)

A method for whitening teeth comprising:
applying the composition of claim 19 to at least a portion of the surface of one or more teeth such that upon exposure to the aqueous environment of the oral cavity, phase separation occurs, resulting in formation of an outer water-insoluble film layer;
maintaining the composition on the surface of the one or more teeth for a period of time to thereby achieve a desired degree of whitening, and
removing the composition.

### Claim 35 (depends on 34)

The method of claim 34, wherein the desired degree of whitening is achieved after a predetermined period of time.

### Claim 36 (depends on 35)

The method of claim 35, wherein the predetermined period of time is from about 10 minutes to about 24 hours.

### Claim 37 (depends on 36)

The method of claim 36, wherein the predetermined period of time is from about 10 minutes to about 8 hours.

### Claim 38 (depends on 37)

The method of claim 37, wherein the predetermined period of time is about 30 minutes to 1 hour.

### Claim 39 (depends on 1)

The composition of claim 1, which comprises about 1-25 wt % of the first water-swellable acrylate-based polymer and the second water-swellable acrylate-based polymer; and about 5-25 wt % of the poly(N-vinyl lactam).

### Claim 40 (depends on 1)

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

### Claim 41

A method of manufacturing a composition, comprising admixing in a mixture of solvents:
(a) a first water-swellable acrylate-based polymer having a pH dependent solubility and insoluble in water at a pH less than about 5.5,
(b) poly(N-vinyl lactam),
(c) a complementary oligomer capable of hydrogen bonding to the poly(N-vinyl lactam),
(d) a second water-swellable acrylate-based polymer that is insoluble in water independent of pH, and
(e) an active agent;
wherein the weight ratio of the first to second water-swellable acrylate-based polymers is in a range of about 1.5:1 to 2:1, the poly(N-vinyl lactam) represents about 1-30 weight percent of the composition and the active agent represents about 1-40 weight percent of the composition including the solvents, to thereby form a liquid composition which, upon contact with a moist body surface, undergoes phase separation such that the second water swellable acrylate-based polymer forms a film over the remainder of the composition.

### Claim 42 (depends on 41)

The composition of claim 41, wherein the active agent is a tooth whitening agent.

### Claim 43 (depends on 6)

The composition of claim 6, wherein the second acrylate-based polymer is a copolymer of ethyl acrylate, methyl methacrylate, and trimethylammonioethyl methacrylate chloride.