WO1993002658A1 - Oral compositions effective against plaque and gingivitis - Google Patents

Oral compositions effective against plaque and gingivitis Download PDF

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Publication number
WO1993002658A1
WO1993002658A1 PCT/US1992/006164 US9206164W WO9302658A1 WO 1993002658 A1 WO1993002658 A1 WO 1993002658A1 US 9206164 W US9206164 W US 9206164W WO 9302658 A1 WO9302658 A1 WO 9302658A1
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Prior art keywords
composition
oral
according
antibacterial
preferably
Prior art date
Application number
PCT/US1992/006164
Other languages
French (fr)
Inventor
Nigel John Leeves
Original Assignee
The Procter & Gamble Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to US740,740 priority Critical
Priority to US74074091A priority
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Publication of WO1993002658A1 publication Critical patent/WO1993002658A1/en

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q11/00Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • A61K8/347Phenols
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/72Cosmetics or similar toilet preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toilet preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141Compositions 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8147Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers

Abstract

Disclosed are oral compositions which are effective against plaque and gingivitis and contain a noncationic water insoluble antibacterial agent.

Description

ORAL COMPOSITIONS EFFECTIVE AGAINST PLAQUE AND GINGIVITIS

TECHNICAL FIELD The present invention relates to oral compositions which provide antiplaque and antigingivitis benefits as well as being effective against other anaerobic infections of the mouth.

Plaque induced diseases, including periodontitis and gingivitis, are believed to involve anaerobic bacterial infections. Periodontal disease affects the periodontium, which is the investing and supporting tissue surrounding a tooth (i.e., the periodontal ligament, the gingiva, and the alveolar bone). Gingivitis and periodontitis are inflammatory disorders of the gingiva and the periodontal ligament, respectively. Gingivosis and periodontosis are more severe conditions involving degenerative disorders of the tissue. Combinations of inflammatory and degenerative conditions are termed periodontitis complex.

Periodontal disease is a major cause of tooth loss in adults.

Tooth loss from periodontal disease is a significant problem beginning at age 35, but even by age 15 it is estimated that about

4 out of 5 persons already have gingivitis and 4 out of 10 have periodontitis.

While good oral hygiene, as achieved by brushing the teeth with a cleansing dentifrice, may help reduce the incidence of periodontal disease, it does not necessarily prevent or eliminate its occurrence. This is because microorganisms contribute to both the initiation and progress of periodontal disease. Thus, in order to prevent or treat periodontal disease, these micro¬ organisms must be suppressed by some means other than simple mechanical scrubbing. Towards this end, there has been a great deal of research aimed at developing therapeutic dentifrices, mouthwashes, and methods of treating periodontal disease which are effective in suppressing these microorganisms. The use of noncationic, water-insoluble antibacterial agents in oral products is disclosed in a number of references. One such reference is U.S. Patent 4.022.889 to Vinson et al. Vinson describes compositions containing zinc salts and antibacterial agents such as halogenated salicylanilides and halogenated hydroxydiphenyl ethers.

Another reference disclosing noncationic water-insoluble antibacterial agents is U.K. Patent Application GB 2.200.551. published August 10, 1988. In addition to the antibacterial, the compositions contain a olecularly dehydrated polyphosphate salt. The salt is stated to improve the effectiveness of the antibac¬ terial. Another reference disclosing noncationic water-insoluble antibacterials in oral compositions is U.S. 4.894.220. January 16, 1990 to Nabi et al. This reference teaches the use of solvents and polymers to enhance the antibacterial's effect.

Still another reference disclosing such antibacterials combined with polyethylene glycols in oral compositions is European Patent Application 02.220.890. May 6, 1987. All prior art references are incorporated herein by reference in total. It has now been found that the bioavailability and effective¬ ness of the antibacteri l can be improved by incorporating a carboxyvinyl polymer into the composition.

It is therefore an object of the present invention to provide improved oral care products containing specific antibacterial agents.

It is a further object of the present invention to provide more effective products for treating diseases of the oral cavity.

It is still a further objective to provide methods for treating diseases of the oral cavity. These and other objects will become readily apparent from the detailed disclosure which follows.

All percentages and ratios used herein are by weight unless otherwise specified. Also, all measurements referred to herein are made at 25*C in the composition unless otherwise specified. SUMMARY OF THE INVENTION The present invention, in certain aspects, embraces oral care products containing water-insoluble, noncationic antibacterial agents, and a carboxyvinyl polymer having a molecular weight of 3,000,000 or greater.

The present invention also encompasses a method for treating diseases of the oral cavity using noncationic water insoluble antibacterial agents.

By "oral compositions" as used herein means a product which in the ordinary course of usage is not intentionally swallowed for purposes of systemic administration of particular therapeutic agents, but is rather retained in the oral cavity for a time sufficient to contact substantially all of the dental surfaces and/or oral tissues for purposes of oral activity. By "safe and effective amount" as used herein means suffi¬ cient amount of material to provide the desired benefit while being safe to the hard and soft tissues of the oral cavity.

By the term "comprising", as used herein, is meant that various additional components can be conjointly employed in the compositions of this invention as long as the listed materials perform their intended functions.

By the term "carrier", as used herein, is meant a suitable vehicle which is pharmaceutically acceptable and can be used to apply the present compositions in the oral cavity. DETAILED DESCRIPTION OF THE INVENTION

The present invention in certain aspects involves the use of water-insoluble, noncationic antibacterials with a carboxyvinyl polymer having a molecular weight of 3,000,000 or greater. The essential and optional components of the compositions are made using the process described in detail below.

Antibacterial Agents Given below are examples of antibacterial agents useful in the compositions of the present invention which are water insoluble and noncationic.

Figure imgf000006_0001
Methyl - o-Chlorophenol

Ethyl - o-Chlorophenol n-Propyl - o-Chl orophenol n-Butyl - o-Chl orophenol n-Amyl - o-Chl orophenol tert-A yl - o-Chl orophenol n-Hexyl - o-Chl orophenol n-Heptyl - o-Chlorophenol o-Benzyl - p-Chl orophenol o-Benxyl -m-methyl - p-Chl orophenol o-Benzyl - , m-dimethyl - p-Chlorophenol o-Phenyl ethyl - p-Chl orophenol o- Phenyl ethyl -m-methyl - p-Chl orophenol

3-Methyl - p-Chlorophenol

3,5-Dimethyl - p-Chl orophenol

6-Ethyl-3-methyl - p-Chl orophenol

6-n-Propyl-3-methyl - p-Chl orophenol

6-iso-Propyl-3-methyl - p-Chlorophenol

2-Ethyl-3,5-dimethyl - p-Chlorophenol

6-sec-Butyl-3-methyl - p-Chl orophenol

2-iso-Propyl-3,5-dimethyl - p-Chlorophenol

6-Diethylmethyl-3-methyl - p-Chl orophenol

6-iso-Propyl-2-ethyl-3-methyl - p-Chlorophenol '

2-sec-Amyl-3,5-dimethyl - p-Chlorophenol

2-Diethylmethyl-3,5-dimethyl - p-Chl orophenol

6-sec-0ctyl-3-methyl - p-Chl orophenol p-Bromophenol

Methyl - p-Bromophenol

Ethyl - p-Bromophenol n-Propyl - p-Bromophenol n-Butyl - p-Bromophenol n-Amyl - p-Bromophenol sec-Amyl - p-Bromophenol n-Hexyl - p-Bromophenol cyclohexyl - p-Bromophenol o-Bromophenol tert-A yl - o-Bromophenol n-Hexyl - o-Bromophenol n-Propyl-m,mDimethyl - o-Bromophenol 2-Phenyl Phenol 4-Chloro-2-methyl phenol 4-Chloro-3-methyl phenol 4-Chloro-3,5-dimethyl phenol 2, -dichloro-3,5-dimethylphenol 3,4,5,6-terabromo-2-methylphenol 5-methyl-2-pentylphenol 4- sopropyl-3-methylphenol 5-Chloro-2-hydroxydiphenylmethane Resorcinol and its Derivatives

Figure imgf000008_0001
bis (2-hydroxy-3,5-dichlorophenyl) sulphide bis (2-hydroxy-5-chlorobenzyl) sulphide

Halogenated Salicylanilides 4',5-dibromosalicylanilide 3,4',5-trichlorosalcylanilide 3,4',5-tribromosalicylanilide 2,3,3',5-tetrachlorosalicylanilide 3,3',5-trichlorosalicylanilide 3,5-dibromo-3'-trif1uoromethyl salicylani1ide 5-n-octanoyl-3'-trifluoromethyl salicylanilide 3,5-dibromo- '-trif1uoromethyl salicyl ni1ide 3,5-dibromo-3'-trifluoromethyl salicylanilide (Fluorophene) Benzoic Esters p-Hydroxybenzoic Acid

Methyl - p-Hydroxybenzoic Acid

Ethyl - p-Hydroxybenzoic Acid

Propyl - p-Hydroxybenzoic Acid

Butyl - p-Hydroxybenzoic Acid Halogenated CarbaniTides 3,4,4'-trichlorocarbanilide 3-trifluoromethyl-4,4'-dichlorocarbaniTide 3,3',4-trichlorocarbanilide

The antibacterial agent is present in the oral compositions of the present invention in an effective antiplaque amount, typically about 0.01-5% by weight, preferably about 0.03-1%. The antibacterial agent is substantially water-insoluble, meaning that its solubility is less than about 1% by weight in water at 25βC and may be even less than about 0.1%. If an ionizable group is present solubility is determined at a pH at which ionization does not occur. Carboxyvinyl Polymer

The term "carboxyvinyl polymer" as used herein describes a family of compounds disclosed and claimed in U.S. Pat. No. 2,798,053 issued on July 2, 1957, to Brown, the specification of which is hereby incorporated by reference. Methods for making carboxyvinyl polymers are also disclosed in Brown. A carboxyvinyl polymer is an interpolymer of a monomeric mixture comprising a monomeric olefinically unsaturated carboxylic acid, and from about 0.1% to about 10% by weight of the total monomers of a polyether of a polyhydric alcohol, which poTyhydric aTcohoT contains at least four carbon atoms to which are attached at least three hydroxyT groups, the polyether containing more than one alkenyT group per molecule. Other onoolefinic monomeric materials may be present in the monomeric mixture if desired, even in predominant proportion. Carboxyvinyl polymers are substantially insoluble in liquid, volatile organic hydrocarbons and are dimensionalTy stabTe on exposure to air.

Preferred poTyhydric alcohols used to produce carboxyvinyl polymers include polyols selected from the class consisting of oligosaccarides, reduced derivatives thereof in which the carbonyT group is converted to an aTcohoT group, and pentaerythritol ; more preferred are oligosaccharides, most preferred is sucrose. It is preferred that the hydroxyl groups of the polyol which are modified be etherified with allyl groups, the polyol having at least two allyl ether groups per polyol molecule. When the polyol is sucrose, it is preferred that the sucrose have at least about five ally! ether groups per sucrose molecule. It is preferred that the polyether of the polyol comprise from about 0.1% to about 4% of the total monomers, more preferably from about 0.2% to about 2.5%. Preferred monomeric olefinically unsaturated carboxylic acids for use in producing carboxyvinyl polymers used herein include monomeric, polymerizable, alpha-beta monoolefinically unsaturated lower aliphatic carboxylic acids; more preferred are monomeric monoolefinic acrylic acids of the structure R

I

I

CH2=C-C00H where R is a substituent selected from the group consisting of hydrogen and lower alkyl groups; most preferred is acrylic acid. The carboxyvinyl polymers used in formulations of the present invention have a molecular weight of at least about 3,000,000. Various carboxyvinyl polymers are commercially available from B. F Goodrich Company, New York, N.Y., under the tradename Carbopόl . Carbopols 934 and 940 having molecular weights of about 3,000,000 and 4,000,000 respectively are examples of such materials. The quantity of carboxyvinyl polymer generally used in the composition of this invention is from about 0.1% to about 1%. A preferred range of usage is from about 0.3% to about 0.8%.

The compositions of the present invention may contain in addition to the above-listed components many others which will be somewhat dependent on the type of composition (mouthwashes, toothpastes, topical gels, prophylaxis pastes and the like). Toothpastes and mouthwashes are the preferred systems with toothpastes being the most preferred.

Toothpastes contain as a major component an abrasive. The abrasive polishing material contemplated for use in the present invention can be any material which does not excessively abrade dentin. These include, for example, silicas including gels and precipitates, calcium' carbonate, dicalcium orthophosphate dihy- drate, calcium pyrophosphate, tricalcium phosphate, calcium poly etaphosphate, insoluble sodium polymetaphosphate, hydrated alumina, and resinous abrasive materials such as particulate condensation products of urea and formaldehyde, and others such as disclosed by Cooley et al . in U.S. Patent 3.070.510. December 25, 1962, incorporated herein by reference. Mixtures of abrasives may also be used.

Silica dental abrasives, of various types, can provide the unique benefits of exceptional dental cleaning and polishing performance without unduly abrading tooth enamel or dentin. Silica abrasive materiaTs are also exceptionally compatible with sources of soluble fluoride and other ion sources. For these reasons they are preferred for use herein.

The silica abrasive polishing materials useful herein, as well as the other abrasives, generally have an average particle size ranging between about 0.1 and 30 microns, preferably 5 and 15 microns. The silica abrasive can be precipitated silica or silica gels such as the silica xerogels described in Pader et al., U.S. Patent 3.538.230. issued March 2, 1970 and DiGiulio, U.S. Patent 3.862.307. June 21, 1975, both incorporated herein by reference. Preferred are the silica xerogels marketed under the tradename "Syloid" by the W.R. Grace & Company, Davison Chemical Division. Preferred precipitated silica materials include those marketed by the J.M. Huber Corporation under the tradename, "Zeodent", parti- cularTy the silica carrying the designation "Zeodent 119". These silica abrasive are described in U.S. Patent 4.340.583. July 29, 1982, incorporated herein by reference.

The abrasive in the toothpaste compositions described herein is present at a level of from about 6% to about 70%, preferably from about 15% to about 30%.

Flavoring agents, as was noted earlier, can also be added to the dentifrice and other compositions of the present invention. Suitable flavoring agents include oil of wintergreen, oil of peppermint, oil of spearmint, oil of sassafras, and oil of clove. Sweetening agents are also useful and include aspartame, acesulfame, saccharin, dextrose, levulose and sodium cyclamate. Flavoring and sweetening agents are generally used in the compo¬ sitions herein at levels of from about 0.005% to about 2% by weight and may be used as a solvent for the antibacterials hereinbefore indicated.

It is also desirable to include a hu ectant in a toothpaste to keep it from hardening. Suitable humectants include glycerin, sorbitol, and other edible polyhydric alcohols at a combined level of from about 10% to about 70%. Another preferred embodiment of the present invention is a mouthwash composition. Mouthwashes generally comprise from about 20:1 to about 2:1 of a water/ethyl alcohol solution and preferably other ingredients such as flavor, sweeteners, humectants and c sudsing agents such as those described above. The humectants, such as glycerin and sorbitol give a moist feel to the mouth. Generally, on a weight basis the mouthwashes of the invention comprise 5% to 60% (preferably 10% to 25%) ethyl alcohol, 0% to 20% (preferably 5% to 20%) of a humectant, 0% to 2% (preferably 0 0.01% to 0.5%) emulsifying agent, 0% to 0.5% (preferably 0.005% to 0.06%) sweetening agent such as saccharin, 0% to 0.3% (preferably from 0.03% to 0.3%) flavoring agent, and the balance water.

Another optional component is a fluoride ion source. The sources of fluoride ions, or fluoride-providing compounds, are 5 well known in the art as anticaries agents and also act as such agents in the practice of this invention, as well as to inhibit pyrophosphatase. These compounds may be slightly soluble in water or may, preferably, be fully water-soluble. They are charac¬ terized by their ability to release fluoride ions in water and by 0 freedom from undesired reaction with other compounds of the oral preparation. Among these materials are inorganic fluoride salts, such as soluble alkali metal, alkaline earth metal salts, for example, sodium fluoride, barium fluoride, sodium fluorsilicate, ammonium fluorosilicate, sodium fluorozirconate, sodium mono- 5 fluorophosphate, aluminum mono- and di-fluorophosphate, and fluorinated sodium calcium pyrophosphate. Alkali metal and tin fluorides, such as sodium and stannous fluorides, sodium mono- fluorophosphate (MFP) and mixtures thereof, are preferred.

The amount of fluoride-providing compound is dependent to 0 some extent upon the type of compound, its solubility, and the type of oral preparation, but it must be a nontoxic amount, generally about 0.005 to about 3.0% in the preparation. In a dentifrice preparation, e.g. dental gel, toothpaste (including cream), an amount of such compound which releases up to about 5 5,000 ppm of F ion by weight of the preparation is considered satisfactory. Any suitable minimum amount of such compound may be used, but it is preferable to employ sufficient compound to release about 300 to 2,000 ppm, more preferably about 800 to about 1,500 ppm of fluoride ion. Typically, in the cases of alkali metal fluorides and stannous fluoride, this component is present in an amount up to about 2% by weight, based on the weight of the preparation, and preferably in the range of about 0.05% to 1%. In the case of sodium monofluorophosphate, the compound may be present in an amount of about 0.1-3%, more typically about 0.76%. Still another optional component for use in the compositions of the present invention is an anticalculus agent. These agents include any which are effective against calculus such as pyro¬ phosphate salts as disclosed in U.S. Patent 4.515.772. May 7, 1985 incorporated herein by reference. The preferred agents are mono, di, tri and tetra alkali metal and ammonium pyrophosphate. Such agents are used in amounts sufficient to reduce calculus. These amounts are preferably in an amount of at least about 1% P2O7, most preferably at least about 1.3%, most preferably at least about 1.5%. Other anticalculus agents are metal ions such as zinc disclosed in U.S. Patent 4.022.880. May 10, 1977 to Vinson incorporated herein by reference. Still others are polymers such as those described in U.S. Patent 4.661.341. April 28, 1987 to Benedict and U.S. Patent 3.429.963. February 25, 1969 to Shed- lovsky, both of which are incorporated herein by reference. Such metals are used in an amount of from about 0.05% to about 5%, preferably about 0.5% to about 2%, while such polymers are used in amounts of from about 0.01% to about 10%, preferably from about 0.1% to about 5%. Surfactants are also useful in the composition of this invention include many different materials. Suitable surfactants include any which are reasonably stable and function over a wide pH range. Included are non-soap anionic, nonionic, cationic, zwitterionic and amphoteric organic synthetic surfactants. Many of these are disclosed by Gieske et al . in U.S. Patent 4.051.234. September 27, 1988 incorporated herein in total by reference. Preferred surfactants include alkyl sulfates. Any surfactant used is at a level of from about 0.2% to about 6%, preferably from about 0.6% to about 2% in a toothpaste and from about 0.01% to about 5%, preferably from about 0.1% to about 0.5% in a mouthwash. The pH of the present compositions and/or its pH in the mouth can be any pH which is safe for the mouth's hard and soft tissues. Such pH's are generally from about 3 to about 10, preferably from about 4 to about 9.

Given below are non-limiting examples which illustrate the compositions of the present invention.

EXAMPLES I - IV

Figure imgf000015_0001
. . . . EXAMPLES V - VI

Figure imgf000015_0002
The above compositions are made in a conventional manner.

The performance of the above compositions of this present invention are superior due to the improved bioavailability of the triclosan antibacterial.

Claims

WHAT IS CLAIMED IS:
1. An oral composition comprising a noncationic water insoluble antibacterial agent and a carboxyvinyl polymer having a molecular weight of at least three million.
2. A composition according to Claim 1 wherein said antibacterial is a phenolic compound.
3. A composition according to either of Claims 1 or 2 wherein said composition is a toothpaste or a outhwash.
4. A composition according to any of Claims 1-3 wherein said composition is a toothpaste which in addition contains an abrasive and a binder.
5. A composition according to any of Claims 1-4 wherein said tooth¬ paste also contains triclosan as the antibacterial agent.
6. A composition according to any of Claims 1-5 wherein said tooth¬ paste contains a soluble fluoride ion source.
7. Use of a noncationic water insoluble antibacterial agent in the manufacture of an oral composition for reducing the incidence of plaque on dental enamel, the composition additionally containing a carboxyvinyl polymer having a molecular weight of at least three million.
8. A manufacture according to Claim 7 wherein said antibacterial is a phenolic compound.
9. A manufacture according to either of Claims 7 or 8 wherein said composition is a toothpaste.
10. A manufacture according to any of Claims 7-9 wherein said anti bacterial agent is triclosan.
11. A manufacture according to any of Claims 7-10 wherein said composition also contains a soluble fluoride ion source.
PCT/US1992/006164 1991-08-06 1992-07-27 Oral compositions effective against plaque and gingivitis WO1993002658A1 (en)

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US74074091A true 1991-08-06 1991-08-06

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994022417A1 (en) * 1993-04-02 1994-10-13 Smithkline Beecham Plc An oral hygiene pretreatment composition

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1956016A1 (en) * 1969-11-07 1971-05-13 Blendax Werke Schneider Co Of preparation for oral or dental hygiene
FR2160403A1 (en) * 1971-11-17 1973-06-29 Colgate Palmolive Co
US4150106A (en) * 1978-02-16 1979-04-17 Cooper S.A. Toothpaste permitting of controlling the tooth brushing time
GB2200551A (en) * 1987-01-30 1988-08-10 Colgate Palmolive Co Antibacterial antiplaque, anticalculus oral composition
GB2208600A (en) * 1987-08-12 1989-04-12 G C Dental Ind Corp Dental cleaner material
WO1992010991A1 (en) * 1990-12-19 1992-07-09 The Procter & Gamble Company Methods for making oral compositions
WO1992010994A1 (en) * 1990-12-18 1992-07-09 The Procter & Gamble Company Oral compositions effective against plaque and gingivitis

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1956016A1 (en) * 1969-11-07 1971-05-13 Blendax Werke Schneider Co Of preparation for oral or dental hygiene
FR2160403A1 (en) * 1971-11-17 1973-06-29 Colgate Palmolive Co
US4150106A (en) * 1978-02-16 1979-04-17 Cooper S.A. Toothpaste permitting of controlling the tooth brushing time
GB2200551A (en) * 1987-01-30 1988-08-10 Colgate Palmolive Co Antibacterial antiplaque, anticalculus oral composition
GB2208600A (en) * 1987-08-12 1989-04-12 G C Dental Ind Corp Dental cleaner material
WO1992010994A1 (en) * 1990-12-18 1992-07-09 The Procter & Gamble Company Oral compositions effective against plaque and gingivitis
WO1992010991A1 (en) * 1990-12-19 1992-07-09 The Procter & Gamble Company Methods for making oral compositions

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
S.T.N., File Supplier, KARLSRUHE DE, File Chemical Abstracts, vol106, nØ 55809h, *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994022417A1 (en) * 1993-04-02 1994-10-13 Smithkline Beecham Plc An oral hygiene pretreatment composition

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PT100761A (en) 1994-01-31

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