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WO1996015770A1 - Compositions antimicrobiennes orales - Google Patents

Compositions antimicrobiennes orales Download PDF

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Publication number
WO1996015770A1
WO1996015770A1 PCT/US1995/012850 US9512850W WO9615770A1 WO 1996015770 A1 WO1996015770 A1 WO 1996015770A1 US 9512850 W US9512850 W US 9512850W WO 9615770 A1 WO9615770 A1 WO 9615770A1
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WO
WIPO (PCT)
Prior art keywords
composition
oral composition
mixture
oral
poly
Prior art date
Application number
PCT/US1995/012850
Other languages
English (en)
Inventor
Sau-Hung S. Leung
Robert Leone
Original Assignee
Warner-Lambert 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
Application filed by Warner-Lambert Company filed Critical Warner-Lambert Company
Priority to AU38903/95A priority Critical patent/AU3890395A/en
Publication of WO1996015770A1 publication Critical patent/WO1996015770A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/90—Block copolymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses

Definitions

  • This invention relates generally to oral compositions such as mouthwashes, oral rinses, toothpastes and the like. More specifically, this invention relates to oral compositions comprising unpleasant, bitter tasting antimicrobial agents for the prevention of periodontal disease, gingivitis, plaque, bad breath and other associated oral problems wherein the unpleasant tasting antimicrobial agents are effectively taste masked.
  • Mouthwash and oral rinse compositions have been used for many years, and the art is replete with various formulations. Ordinarily, mouthwashes have been designed to clean the oral cavity, provide fresh breath, and kill harmful bacteria that contribute to oral malodor or secrete acidic residues which are harmful to teeth and aid in the development of gingivitis and periodontal disease.
  • Plaque for example, contains a number of pathogenic strains of microorganisms which are a major cause of gingivitis, periodontal disease, and other gum infections. Plaque is also a precursor of calculus, the hard encrustation of calcium deposits and other debris which if left unchecked will cause further complications. Once developed, it can only be removed by strenuous and often painful scraping.
  • the reduction of harmful oral bacteria can be achieved by rinsing the oral cavity with a liquid composition containing antimicrobials to wash the tooth and gum surfaces for 15 seconds to over a minute. This rinsing may be done just prior to brushing using a pre-brush rinse, which chemically loosens and breaks up existing plaque or tartar which is then removed by the mechanical and abrasive action of brushing. Other oral rinse compositions are used after brushing. Antibacterial toothpaste can also help reduce oral bacteria.
  • Conventional mouthwashes typically comprise a water/alcohol carrier within which other components are dissolved or emulsified. These compositions generally contain ethyl alcohol ranging from about 0% to about 30% by volume of the total composition (hereinafter referred to as "% v/v") . This alcohol is used as a solvent in which water-insoluble ingredients, including antimicrobials as well as additives such as flavoring oils, color additives, fluorides and astringents, are dissolved and dispersed into an aqueous solution. Over 95% of the commercial mouthwash compositions available contain more than 15% by volume alcohol.
  • Water-insoluble essential oils including, but not limited to, thymol, menthol, methyl salicylate, and eucalyptol, as well as quaternary ammonium compounds such as CPC are used as antimicrobials in oral compositions. Unlike essential oils, quaternary ammonium compounds are water soluble. Like some essential oils, they taste bitter.
  • United States Patent No. 3,164,524 to Fund et. al. discloses oral antiseptic compositions comprising a water/alcohol carrier containing menthol, methyl salicylate, thymol and eucalyptol. Additionally, these compositions contain benzoic acid, boric acid and chlorophenol derivatives. Although a highly effective antimicrobial mouthwash, these compositions are extremely bitter tasting and consumer compliance is not easily achieved.
  • U.S. Patent No. 4,945,087 to Talwar et. al. discloses an aqueous/alcohol mouthwash composition in which a sugar alcohol such as sorbitol or xylitol is used in combination with anethole to taste mask the bitter, biting astringent taste of the antimicrobial active, thymol.
  • the composition assertedly masks the taste to such an extent that additional flavors or flavorants are not necessary but may be added if desired.
  • U.S. Patent No. 5,292,527 to Konopa claims a non- alcohol mouthwash comprised of a water insoluble flavor oil, and an effective amount of a dispersion system consisting of a non-ionic surfactant selected from either a hydrogenated castor oil or a polyoxyethylene polypropylene block copolymer having 50%-90% ethylene oxide, a humectant and an effective amount of one or more cationic antimicrobial agents.
  • a non-ionic surfactant selected from either a hydrogenated castor oil or a polyoxyethylene polypropylene block copolymer having 50%-90% ethylene oxide, a humectant and an effective amount of one or more cationic antimicrobial agents.
  • One such antimicrobial agent is a mixture of cetylpyridinium chloride and domiphen bromide.
  • U.S. Patent No. 5,236,699 to Libin claims an anti- plaque mouth rinse containing a combination of two antimicrobial agents, triclosan, and cetylpyridinium chloride. The two assertedly provide a coactive antimicrobial action thereby giving a superior oral hygiene regime.
  • U.S. Patent No. 4,323,511 to Parran also discloses mouthwash compositions for plaque and calcium control comprising two active agents, a quaternary ammonium compound and a pyrophosphate salt.
  • Cetylpyridinium chloride is listed as one of a number of the quaternary ammonium compounds and the actives are dissolved in a water-alcohol carrier using a pluronics emulsifier system at a pH of 7.0 to 9.5.
  • U.S. Patent Nos. 4,971,788 and 5,130,122 to Tabibi et. al. both disclose the use of a microemulsion system in oral mouthwashes and other dental products. Uniform, submicron- sized oil particles containing antimicrobials, antifungals, fluorides, preservatives, and a vast list of other active compounds derived from vegetable and animal oils are dispersed in an aqueous phase.
  • Cetylpyridinium chloride is listed as a suitable emulsifying agent but not as an antimicrobial active. The oil droplets are proposed to do away with the unpleasant aspects of the bitter tasting actives.
  • U.S. Patent No. 4,590,061 to Southard discloses oral rinse compositions comprising a water/alcohol solution, an active comprising a sanguinarine chloride or sulfate salt, non-ionic and cationic synthetic detergents such as CPC, a humectant, flavors and sweeteners.
  • the invention allegedly not only allows for the visual detection of plaque formation in the oral cavity but provides an antimicrobial active that is effective in reducing plaque colonies.
  • the invention is directed to antimicrobial oral compositions for the prevention of plaque, gum disease, and oral malodor. More specifically the invention is directed to antimicrobial oral compositions comprising an effective amount of a bactericidal compound, essential oils and a non-ionic surfactant in a suitable carrier solvent wherein the unpleasant taste of the composition is masked.
  • the invention is further directed to a method for preparing an antimicrobial oral composition for the prevention of plaque, gum disease, and oral maloder comprising an effective amount of a bactericidal compound, essential oils, and a non-ionic surfactant in a suitable carrier solvent wherein the unpleasant taste of the composition is masked.
  • This invention relates to oral compositions including, but not limited to, mouthwashes, oral rinses, pre-brushing rinses, toothpaste, toothpowder, and the like.
  • the oral compositions of this invention are formulated to provide an antimicrobial composition for the prevention of plaque, gum disease, and oral malodor in which the unpleasant, bitter tasting antimicrobials are effectively taste-masked.
  • the oral compositions of this invention incorporate effective amounts of antimicrobial agents dispersed in an aqueous/alcohol carrier with the use of non-ionic surfactants.
  • the compositions of this invention are prepared by first combining in the alcohol phase one or more quaternary ammonium salts and one or more essential oils with a surfactant.
  • the aqueous phase of the compositions, comprising water and water soluble components is then combined with the alcohol phase. This results in a composition wherein the unpleasant, bitter tasting antimicrobials are effectively taste masked.
  • the antimicrobial agents in this invention are quaternary ammonium salts and essential oils. These antimicrobial agents are the active ingredients, or actives, of this invention. Quaternary ammonium salts used in this invention are bacteriostatic in low concentrations and bactericidal in high concentrations. They are water and alcohol soluble, foam strongly when shaken, and are very bitter tasting. Quaternary ammonium salts that may be used in this invention include, but are not limited to, cetylpyridinium chloride, benzethonium chloride, benzalkonium chloride and domiphen bromide.
  • the quaternary ammonium salt that is used is cetylpyridinium chloride (C 2 ⁇ H3gClN-H 2 0) , or CPC.
  • CPC is the monohydrate of the quaternary salt of pyridine and cetyl chloride.
  • CPC is cationic, highly soluble in water and alcohol, and is an effective antibacterial agent.
  • An effective antimicrobial oral rinse, mouthwash or toothpaste with CPC does not require high levels of alcohol to solubilize the CPC.
  • CPC may be incorporated in the compositions of this invention in amounts of from approximately 0.01% to about 5.0% and preferably from about 0.03% to about 1.0% v/v and most preferably from about 0.05% to 0.15%.
  • CPC is readily perceived as bitter and metallic tasting.
  • the unpleasant, bitter metallic taste of CPC discourages consumer use of compositions containing it.
  • Essential oils provide additional antimicrobial antiseptic activity in the compositions of this invention.
  • the essential oils in this invention include, but are not limited to, thymol, methyl salicylate, eucalyptol, menthol and the like. These essential oils are generally incorporated in the mouthwash and toothpaste compositions of this invention in amounts of from about 0.005% v/v to about 3.0% v/v, preferably from about 0.02% to about 2.0%, and most preferably from about 0.1% to about 1.0%.
  • thymol is incorporated in an amount of from about 0.005% to about 3.0% v/v, preferably from about 0.01% to about 1.0% v/v, and most preferably from about 0.04% to about 0.15% w/v; menthol is incorporated in an amount of from about 0.005% to about 3.0% w/v, preferably from about 0.01% to about 1.0% w/v, and most preferably from about 0.04% to about 0.15% w/v; and methyl salicylate is incorporated in an amount of from about 0.005% to about 3.0% w/v, preferably from about 0.01% to about 1.0% w/v, and most preferably from about 0.04% to about 0.15% w/v.
  • Anethole may also be incorporated into this composition of this invention in an amount of from about .005% w/v to about 3.0% w/v, preferably from about 0.005% to about 1.0%; and most preferably from about 0.01% to about 0.15% w/v.
  • essential oils Like quaternary ammonium salts, some essential oils have an unpleasant, bitter, taste. Thymol, for example, is unpleasant even when incorporated in small amounts. Unlike CPC, however, essential oils are water insoluble.
  • This invention further comprises an aqueous/alcohol carrier for the dissolution and dispersion of the active ingredients.
  • the aqueous/alcohol carrier in this invention comprises generally from about 80-95% v/v of the total composition.
  • Ethanol is generally the alcohol of choice and can be used in amounts of from about 0% to about 30% v/v, preferably from about 5% to about 26% v/v, and most preferably from about 15% to about 26% v/v.
  • This invention further comprises at least one non-ionic surfactant to aid in the dispersion of the active ingredients.
  • suitable surfactants in oral rinse compositions are the water soluble salts of higher fatty acids and block copolymers. Surfactants, however, may inhibit the bactericidal activity of many antimicrobial agents.
  • the oral compositions of this invention are formulated such that the antimicrobial activity of the active ingredients is not inhibited.
  • Micelles are electrically charged colloidal particles that are generally organic in nature. They are often comprised of aggregates of large, polymer molecules that have a hydrophobic portion and a hydrophilic portion.
  • the active ingredients in this invention are encapsulated within micelles, whereby the hydrophobic portion of the polymer points in towards the center of the micelle and the hydrophilic portion points outward. It is believed such encapsulation effectively taste masks unpleasant-tasting active ingredients in this composition. Additionally, the active ingredients remain in solution.
  • the surfactants of this invention include, but are not limited to, poly(oxyethylene) -poly(oxypropylene) block copolymers, known commercially as poloxamers. There is a wide variety of poloxamers with different molecular weights, reactive side chains and the like. These poloxamers form micelles that encapsulate the active ingredients as described above.
  • the surfactant is incorporated in amounts of from about 0.01% to about 5.0% w/v, preferably from about 0.02% to about 2.0% w/v, and most preferably from about 0.05% to about 1.0% w/v.
  • Suitable poloxamer surfactants useful in the practice of the present invention include,
  • poloxamer 407 is used. Poloxamer 407 tends to produce the best micellar formation.
  • Buffer systems are used and added to optimize the pH of this invention. This is accomplished generally through the addition of a weak acid and its salt or a weak base and its salt.
  • Useful buffer systems have been found to be sodium benzoate and benzoic acid in amounts of from approximately 0.05% to about 1.5% w/v and sodium citrate and citric acid in amounts of from about 0.0025% to about 1.0% w/v.
  • Buffers are incorporated in amounts that maintain the pH at levels of from approximately 3.0% to about 5.0%, more preferably from about 4.0% to about 4.5%.
  • Flavor oils in this invention including, but not limited to, peppermint, spearmint, eugenol, citrus flavors and mixtures thereof all may be used in this invention. Flavor oils are present in amounts of from about 0.005% w/v to about 3.0% w/v; preferably from about 0.1% w/v to about 2.0%, and most preferably from about 0.1% to about 1.0%.
  • Co-solvents are generally needed to dissolve the flavor oils used in this invention, as they do not readily dissolve in water or ethanol alone.
  • Polyhydric alcohols such as glycerin, and glycols such as propylene and polyethylene glycol are necessary to dissolve the flavor oils into the aqueous phase and thereby provide a clear, non-cloudy solution.
  • These co-solvents, alone or in combination, are incorporated into the composition in an amount of from about 0.05% w/v to approximately 30% w/v, preferably from about 0.1% to about 20% w/v, and most preferably from about 0.5% to about 15% w/v.
  • Water and ethyl alcohol are the major constituents of this invention.
  • Ethanol (95%) is used in amounts of from about 1.0% to about 30% w/v. After all the ingredients are mixed, the water is added in an amount sufficient to bring the total volume up to 1.0 liters.
  • coloring agents may be added in amounts of from about 0.0008% to about 0.001%, again according to ones personal tastes.
  • compositions of this invention are prepared such that the unpleasant, bitter tasting active ingredients are effectively taste masked. This is accomplished by adding to alcohol the following ingredients in the following order: surfactant, quaternary ammonium compound, one or more essential oils, one or more flavor oils, one or more weak acids, one or more co-solvents. The solution is constantly stirred during this process to assure proper mixing of the components. Sodium salts, sweeteners, and colors are dissolved separately in water, which is then added to the alcohol mixture and mixed well. Water is then added to q.s. and the pH adjusted to about 4.2 through the addition of acid or base to the final composition.
  • Mint Flavored Antimicrobial Mouthwash The following ingredients were collected and are given in their respective amounts.
  • Citric Acid USP .1450 1.4500 gm. granular fine anhydrous
  • Vanillin NF (Lignin) q.s. q.s.
  • the following ingredients are added to alcohol during continuous mixing in the following order: CPC, poloxamer 407, methyl salicylate, thymol, menthol, anethole, eugenol, peppermint oil, benzoic acid, and citric acid.
  • CPC CPC
  • poloxamer 407 methyl salicylate
  • thymol thymol
  • menthol anethole
  • eugenol peppermint oil
  • benzoic acid benzoic acid
  • citric acid citric acid
  • sodium citrate, sodium benzoate, saccharin and FD & C dyes are dissolved in water. After thorough mixing, this water phase is added to the alcohol phase with continued mixing. Depending upon the resulting pH of the solution, the sodium hydroxide or hydrochloric acid was added to bring the pH of the system to approximately 4.0-4.4. Water is then added to bring the total volume to one liter.
  • the mouthwash thus produced had a minty, slightly sweet taste with a barely noticeable astringent bite from the actives. Effective in killing and controlling bacterial colonies in the oral cavity, the composition lacks the bitter burning sensation that otherwise detracts from patient compliance.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Emergency Medicine (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne une composition améliorée antimicrobienne orale à goût masqué et son procédé de préparation. Cette composition comprend au moins un sel quaternaire d'ammonium amer et au moins une huile essentielle amère, combinés à un agent tensio-actif dans un solvant porteur approprié, de telle sorte que les éléments amers sont masqués efficacement au goût.
PCT/US1995/012850 1994-11-17 1995-10-05 Compositions antimicrobiennes orales WO1996015770A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU38903/95A AU3890395A (en) 1994-11-17 1995-10-05 Antimicrobial oral compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US34092194A 1994-11-17 1994-11-17
US08/340,921 1994-11-17

Publications (1)

Publication Number Publication Date
WO1996015770A1 true WO1996015770A1 (fr) 1996-05-30

Family

ID=23335487

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1995/012850 WO1996015770A1 (fr) 1994-11-17 1995-10-05 Compositions antimicrobiennes orales

Country Status (4)

Country Link
AU (1) AU3890395A (fr)
PE (1) PE52196A1 (fr)
WO (1) WO1996015770A1 (fr)
ZA (1) ZA959764B (fr)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997030685A1 (fr) * 1996-02-23 1997-08-28 Warner-Lambert Company Bain de bouche a teneur alcoolique reduite
WO1998023250A1 (fr) * 1996-11-26 1998-06-04 The Procter & Gamble Company Systeme d'aromatisation pour produits d'hygiene buccale
US5891422A (en) * 1996-10-10 1999-04-06 Warner-Lambert Company Antimicrobial composition containing a C3 -C6 alcohol
WO2004073671A1 (fr) * 2003-02-18 2004-09-02 Quest International Services B.V. Composition aromatisee d'eau dentifrice
WO2005002535A1 (fr) * 2003-07-03 2005-01-13 Betafarma S.P.A. Bain de bouche antibacterien
US8283135B2 (en) 2000-06-30 2012-10-09 The Procter & Gamble Company Oral care compositions containing combinations of anti-bacterial and host-response modulating agents
JP2012201632A (ja) * 2011-03-25 2012-10-22 Lion Corp 液体口腔用組成物及び該組成物へ成分を安定化配合する方法
WO2013192382A3 (fr) * 2012-06-21 2014-09-04 The Procter & Gamble Company Émulsions de bain de bouche
US9241885B2 (en) 2004-01-29 2016-01-26 The Procter & Gamble Company Oral care compositions comprising increased bioavailable levels of quaternary ammonium antimicrobials
RU2686698C2 (ru) * 2013-02-26 2019-04-30 Джонсон энд Джонсон Консьюмер Инк. Композиции для ухода за полостью рта
RU2728833C2 (ru) * 2013-02-26 2020-07-31 Джонсон энд Джонсон Консьюмер Инк. Композиции для ухода за полостью рта

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2106394A1 (fr) * 1970-09-09 1972-05-05 Colgate Palmolive Co
US3876759A (en) * 1973-01-04 1975-04-08 Colgate Palmolive Co Method of making clear lemon-flavored mouthwash
FR2379508A1 (fr) * 1977-02-07 1978-09-01 Zambeletti Spa L Derive de benzalconium a action desinfectante et compositions pharmaceutiques renfermant ce compose
FR2440189A1 (fr) * 1978-11-01 1980-05-30 Unilever Nv Produits a usage buccal contenant un germicide cationique de gout amer, avec un arome masquant, et leur preparation
US4367219A (en) * 1981-11-25 1983-01-04 Schole Murray L Fluoride containing dentifrice
US4476107A (en) * 1983-06-13 1984-10-09 Basf Wyandotte Corporation Mouthwash composition
US4574081A (en) * 1984-09-25 1986-03-04 Colgate-Palmolive Co. Antiplaque dentifrice having improved flavor
EP0439335A1 (fr) * 1990-01-24 1991-07-31 Colgate-Palmolive Company Composition pour l'application topique
WO1994018939A1 (fr) * 1993-02-19 1994-09-01 Warner-Lambert Company Composition de rinçage utilisee avant le brossage
WO1995034277A1 (fr) * 1994-06-10 1995-12-21 The Procter & Gamble Company Compositions de solution pour bain de bouche

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2106394A1 (fr) * 1970-09-09 1972-05-05 Colgate Palmolive Co
US3876759A (en) * 1973-01-04 1975-04-08 Colgate Palmolive Co Method of making clear lemon-flavored mouthwash
FR2379508A1 (fr) * 1977-02-07 1978-09-01 Zambeletti Spa L Derive de benzalconium a action desinfectante et compositions pharmaceutiques renfermant ce compose
FR2440189A1 (fr) * 1978-11-01 1980-05-30 Unilever Nv Produits a usage buccal contenant un germicide cationique de gout amer, avec un arome masquant, et leur preparation
US4367219A (en) * 1981-11-25 1983-01-04 Schole Murray L Fluoride containing dentifrice
US4476107A (en) * 1983-06-13 1984-10-09 Basf Wyandotte Corporation Mouthwash composition
US4574081A (en) * 1984-09-25 1986-03-04 Colgate-Palmolive Co. Antiplaque dentifrice having improved flavor
EP0439335A1 (fr) * 1990-01-24 1991-07-31 Colgate-Palmolive Company Composition pour l'application topique
WO1994018939A1 (fr) * 1993-02-19 1994-09-01 Warner-Lambert Company Composition de rinçage utilisee avant le brossage
WO1995034277A1 (fr) * 1994-06-10 1995-12-21 The Procter & Gamble Company Compositions de solution pour bain de bouche

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997030685A1 (fr) * 1996-02-23 1997-08-28 Warner-Lambert Company Bain de bouche a teneur alcoolique reduite
US5891422A (en) * 1996-10-10 1999-04-06 Warner-Lambert Company Antimicrobial composition containing a C3 -C6 alcohol
WO1998023250A1 (fr) * 1996-11-26 1998-06-04 The Procter & Gamble Company Systeme d'aromatisation pour produits d'hygiene buccale
US6042812A (en) * 1996-11-26 2000-03-28 The Procter & Gamble Company Flavor systems for oral care products
US8283135B2 (en) 2000-06-30 2012-10-09 The Procter & Gamble Company Oral care compositions containing combinations of anti-bacterial and host-response modulating agents
WO2004073671A1 (fr) * 2003-02-18 2004-09-02 Quest International Services B.V. Composition aromatisee d'eau dentifrice
WO2005002535A1 (fr) * 2003-07-03 2005-01-13 Betafarma S.P.A. Bain de bouche antibacterien
US9241885B2 (en) 2004-01-29 2016-01-26 The Procter & Gamble Company Oral care compositions comprising increased bioavailable levels of quaternary ammonium antimicrobials
JP2012201632A (ja) * 2011-03-25 2012-10-22 Lion Corp 液体口腔用組成物及び該組成物へ成分を安定化配合する方法
WO2013192382A3 (fr) * 2012-06-21 2014-09-04 The Procter & Gamble Company Émulsions de bain de bouche
RU2686698C2 (ru) * 2013-02-26 2019-04-30 Джонсон энд Джонсон Консьюмер Инк. Композиции для ухода за полостью рта
RU2728833C2 (ru) * 2013-02-26 2020-07-31 Джонсон энд Джонсон Консьюмер Инк. Композиции для ухода за полостью рта

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PE52196A1 (es) 1996-12-25
ZA959764B (en) 1996-05-29
AU3890395A (en) 1996-06-17

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