# US 5,344,641 A · Antibacterial antiplaque oral composition > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,344,641 A - Document ID: US5344641A - Status: Granted - Kind: A - Application number: 07/981,723 - Filed: 1992-11-25 - Granted: 1994-09-06 - Earliest claimed: 1987-01-30 - Assignees: Colgate-Palmolive Company - Inventors: Abdul Gaffar; Nuran Nabi; John Afflitto; Orum Stringer - Web page: https://patentgrep.com/patent/US5344641A ## CPC - C08F 230/02: containing phosphorus - A61K 8/24: Phosphorous; Compounds thereof - A61K 8/347: {Phenols} - A61K 8/42: Amides - A61K 8/81: obtained by reactions involving only carbon-to-carbon unsaturated bonds - A61K 8/8164: {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 carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers, e.g. poly (methyl vinyl ether-co-maleic anhydride)} - A61Q 11/00: Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses - A61K 2800/87: Application Devices; Containers; Packaging - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - 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 An oral composition dentifrice comprising an orally acceptable vehicle, about 5-30% by weight of a siliceous polishing agent, a substantially water-insoluble noncationic antibacterial antiplaque agent, such as 2,4,4'-trichloro-2'-hydroxydiphenyl ether (triclosan), and an antibacterial-enhancing agent which enhances the delivery of said antibacterial agent to, and retention thereof on, oral surfaces, wherein said antiplaque agent is substantially completely dissolved in saliva present during tooth and gum cleaning in a solubilizing agent therefor. The solubilizing agent may be a humectant polyol such as propylene glycol, dipropylene glycol and hexylene glycol; a cellosolve such as methyl cellosolve and ethyl cellosolve; a vegetable oil or wax containing at least about 12 carbon atoms in a straight chain such as olive oil, castor oil and petrolatum; or an ester such as ethyl acetate, amyl acetate, glyceryl tristearate and benzyl benzoate. ## Claims ### Claim 1 An oral composition dentifrice for attaching, adhering or bonding a plaque-inhibiting antibacterial agent to oral tooth and gum surfaces comprising in an orally acceptable vehicle about 5-30% by weight of a siliceous polishing agent, an effective antiplaque amount in the range of about 0.01-5% by weight of a substantially water insoluble non-cationic antibacterial agent, about 0.05-5% by weight of an antibacterial-enhancing agent which contains at least one delivery-enhancing functional group and at least one organic retention-enhancing, which delivery-enhancing group enhances delivery of said antibacterial agent to oral tooth and gum surfaces and said retention-enhancing group enhances attachment, adherence or bonding of said antibacterial agent on oral tooth and gum surfaces, and about 0.5-50% by weight of a solubilizing material for said antibacterial agent in amount sufficient to dissolve said antibacterial agent in saliva and permit delivery of said antibacterial agent to soft oral tissues at or near the gum line. ### Claim 2 (depends on 1) The oral composition claimed in claim 1, wherein said antibacterial agent is selected from the group consisting of halogenated diphenyl ethers, halogenated salicylanilides, benzoic esters, halogenated carbanilides and phenolic compounds. ### Claim 3 (depends on 2) The oral composition claimed in claim 2, wherein said antibacterial agent is a halogenated diphenyl ether. ### Claim 4 (depends on 3) The oral composition claimed in claim 3, wherein said halogenated diphenyl ether is 2,4,4'-trichloro-2'-hydroxydiphenyl ether. ### Claim 5 (depends on 2) The oral composition claimed in claim 2, wherein said antibacterial agent is a phenolic compound. ### Claim 6 (depends on 5) The oral composition claimed in claim 5, wherein said phenolic compound is selected from the group consisting of phenol, thymol, eugenol, and 2,2'-methylene bis(4-chloro-6-bromophenol). ### Claim 7 (depends on 1) The oral composition claimed in claim 1, wherein said antibacterial agent is present in amount of about 0.25-5% by weight. ### Claim 8 (depends on 1) The oral composition dentifrice claimed in claim 1, wherein said solubilizing material is selected from the group consisting of propylene glycol, dipropylene glycol, hexylene glycol, methyl cellosolve, ethyl cellosolve, vegetable oil and wax containing at least 12 carbon atoms, amyl acetate, ethyl acetate, glycerol tristearate and benzyl benzoate. ### Claim 9 (depends on 8) The oral composition dentifrice claimed in claim 8, wherein aid solubilizing material is propylene glycol. ### Claim 10 (depends on 1) The oral composition dentifrice claimed in claim 1, wherein said antibacterial-enhancing agent is water soluble or swellable. ### Claim 11 (depends on 10) The oral composition claimed in claim 10, wherein said antibacterial-enhancing agent has an average molecular weight of about 100 to about 1,000,000. ### Claim 12 (depends on 11) The oral composition claimed in claim 11, wherein said delivery-enhancing group is acidic. ### Claim 13 (depends on 12) The oral composition claimed in claim 12, wherein said delivery-enhancing group is selected from the group consisting of carboxylic, phosphonic, phosphinic and sulfonic acids, and their salts, and mixtures thereof, and wherein said organic retention-enhancing group comprises the formula --(X).sub.n --R wherein X is O, N, S, SO, SO.sub.2, P, PO or Si, R is hydrophobic alkyl, alkenyl, acyl, aryl, alkaryl, aralkyl, heterocyclic, or their inert-substituted derivatives, and n is zero or one or more, and wherein said antibacterial-enhancing agent is a monomer or polymer selected from the group consisting of oligomers, homopolymers, copolymers of two or more monomers, ionomers, block copolymers, graft copolymers, and crosslinked polymers and monomers. ### Claim 14 (depends on 13) The oral composition claimed in claim 13, wherein said antibacterial-enhancing agent is an anionic polymer containing a plurality of said delivery-enhancing and retention-enhancing groups. ### Claim 15 (depends on 14) The oral composition claimed in claim 14, wherein said anionic polymer comprises a chain containing repeating units each containing at least one carbon atom. ### Claim 16 (depends on 15) The oral composition claimed in claim 15, wherein each unit contains at least one delivery-enhancing group and at least one organic retention-enhancing group bonded to the same or vicinal or other atoms in the chain. ### Claim 17 An oral composition dentifrice comprising in an orally acceptable vehicle, about 5-30% of a siliceous polishing agent, about 0.01-5% of triclosan, about 0.05-5% of poly(beta-styrenephosphonic acid), poly(alpha-styrenephosphonic acid), or a copolymer of ether styrenephosphonic acid and monomer with the other or with another inert polymerizable ethylenically unsaturated monomer and propylene glycol in amount sufficient to dissolve the triclosan in saliva.