# US 5,348,738 A · Oral composition with active water insoluble polymer

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- Number: US 5,348,738 A
- Document ID: US5348738A
- Status: Granted
- Kind: A
- Application number: 08/006,308
- Filed: 1993-01-22
- Granted: 1994-09-20
- Earliest claimed: 1992-01-27
- Assignees: Sunstar Inc.
- Inventors: Tsutomu Takatsuka; Shigeki Mori; Chiho Makino
- Web page: https://patentgrep.com/patent/US5348738A

## CPC

- A61K 31/785: Polymers containing nitrogen
- 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 8/90: Block copolymers (A61K8/89 takes precedence)
- A61Q 11/00: Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
- A61K 2800/594: Mixtures of polymers
- 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

There is disclosed an oral composition comprising a water-insoluble polymer having quaternary nitrogen atoms as an active component and a polyoxyethylene-polyoxypropylene block copolymer surfactant as a stabilizing agent for the polymer. This composition has high adsorbability of microorganisms in the oral cavity and removes the microorganisms to exhibit improved dental plaque control effect.

## Claims

### Claim 1

An oral composition comprising as an active component a water-insoluble polymer having quaternary nitrogen atoms and as a stabilizing agent for the polymer a polyoxyethylene-polyoxypropylene block copolymer surfactant, wherein the repeating unit of the water-insoluble polymer having quaternary nitrogen atoms is represented by the general formula (I): ##STR15## wherein A is ##STR16## k is an integer of 20 to 2,000, n is an integer of not less than 1,000, X and Y are the same or different and are an anion such as a chloride ion or bromide ion, R.sub.1 is alkyl having 6 to 18 carbon atoms and m is an integer of 2 to 10; vinylpyridinium-type quaternary nitrogen-containing polymers having a repeating unit represented by the formula (II): ##STR17## wherein R' is a compound selected from the group consisting of benzyl, phenethyl, alkyl having 1 to 12 carbon atoms and pentafluorophenylmethyl, X ia an anion such as a chloride ion or bromide ion and p is an integer of 20 to 3,000; or the general formula (III): ##STR18## wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different and are selected from the group consisting of a hydrogen atom, a C.sub.1-20 straight or branched chain saturated or unsaturated aliphatic hydrocarbon group, hydroxyalkyl, alkoxyalkyl, aryloxyalkyl and trialkoxysilylalkyl, X and Y are the same or different and an anion such as a chloride ion or bromide ion, q is an integer of 20 to 2,500 and t is an integer of 1 to 20.

### Claim 2

An oral composition comprising as an active component a water-insoluble polymer having quaternary nitrogen atoms and as a stabilizing agent for the polymer a polyoxyethylene-polyoxypropylene block copolymer surfactant, wherein the repeating unit of the water-insoluble polymer having quaternary nitrogen atoms is represented by the general formula (I): ##STR19## wherein A is ##STR20## k is an integer of 20 to 2,000, n is an integer of not less than 10, X and Y are the same or different and are an anion such as a chloride ion or bromide ion, R.sub.1 is alkyl having 6 to 18 carbon atoms and m is an integer of 2 to 10; vinylpyridinium-type quaternary nitrogen-containing polymers having a repeating unit represented by the formula (II): ##STR21## wherein R' is a compound selected from the group consisting of benzyl, phenethyl, alkyl having 1 to 12 carbon atoms and pentafluorophenylmethyl, X ia an anion such as a chloride ion or bromide ion and p is an integer of 20 to 3,000; or the general formula (III): ##STR22## wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different and are selected from the group consisting of a hydrogen atom, a C.sub.1-20 straight or branched chain saturated or unsaturated aliphatic hydrocarbon group, hydroxyalkyl, alkoxyalkyl, aryloxyalkyl and trialkoxysilylalkyl, X and Y are the same or different and an anion such as a chloride ion or bromide ion, q is an integer of 20 to 2,500 and t is an integer of 1 to 20.

### Claim 3 (depends on 1)

The oral composition according to claim 1, wherein the water-insoluble polymer having quaternary nitrogen atoms is selected from the group consisting of poly(vinylbenzylmethyllaurylammonium chloride), poly(vinylbenzylstearylbetaine), poly(vinylbenzyllaurylpyridylpyridinium chloride), poly(vinylbenzyllauryldiammonium chloride), poly(vinylbenzylcetylammonylhexyl ether), poly crosslinked-N-benzyl-4-vinylpyridinium bromide, poly crosslinked-N-phenethyl-4-vinylpyridinium bromide, poly crosslinked-N-hexadecyl-4-vinylpyridinium bromide, poly crosslinked-N-pentafluorophenylmethyl-4-vinylpyridinium bromide and 1-(N-methyl-N-benzyldodecylammoniopropyl)-4-vinylpyridinium bromide.

### Claim 4 (depends on 1)

The oral composition according to claim 1, wherein the amount of the water-insoluble polymer having quaternary nitrogen is 0.001 to 50% by weight based on the total weight of the composition.

### Claim 5 (depends on 4)

The oral composition according to claim 4, wherein the amount of the water-insoluble polymer having quaternary nitrogen atoms is 0.1 to 10% by weight based on the total weight of the composition.

### Claim 6 (depends on 1)

The oral composition according to claim 1, wherein the polyoxyethylene-polyoxypropylene block copolymer surfactant is composed of polyoxyethylene-polyoxypropylene glycol having the molecular weight of the polyoxypropylene moiety of 1,400 to 4,000 and containing 30 to 80% by weight of the polyoxyethylene moiety based on the total molecular weight.

### Claim 7 (depends on 1)

The oral composition according to claim 1, wherein the amount of the polyoxyethylene-polyoxypropylene block copolymer surfactant is 15 to 80% by weight based on the total weight of the composition.

### Claim 8 (depends on 1)

The oral composition according to claim 1, wherein the amount of the polyoxyethylene-polyoxypropylene block copolymer surfactant is 20 to 50% by weight based on the total weight of the composition.

### Claim 9 (depends on 2)

The oral composition according to claim 2, wherein n is an integer from 10 to 10,000.

### Claim 10 (depends on 2)

The oral composition according to claim 2, wherein the amount of the water-insoluble polymer having quaternary nitrogen is 0.001 to 50% by weight based on the total weight of the composition.

### Claim 11 (depends on 10)

The oral composition according to claim 10, wherein the amount of the water-insoluble polymer having quaternary nitrogen atoms is 0.1 to 10% by weight based on the total weight of the composition.

### Claim 12 (depends on 2)

The oral composition according to claim 2, wherein the polyoxyethylene-polyoxypropylene block copolymer surfactant is composed of polyoxyethylene-polyoxypropylene glycol having the molecular weight of the polyoxypropylene moiety of 1,400 to 4,000 and containing 30 to 80% by weight of the polyoxyethylene moiety based on the total molecular weight.

### Claim 13 (depends on 2)

The oral composition according to claim 2, wherein the amount of the polyoxyethylene-polyoxypropylene block copolymer surfactant is 15 to 80% by weight based on the total weight of the composition.

### Claim 14 (depends on 2)

The oral composition according to claim 2 wherein the amount of the polyoxyethylene-polyoxypropylene block copolymer surfactant is 20 to 50% by weight based on the total weight of the composition.