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WO1996016633A1 - Bain de bouche a teneur reduite en alcool - Google Patents

Bain de bouche a teneur reduite en alcool Download PDF

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Publication number
WO1996016633A1
WO1996016633A1 PCT/US1995/012849 US9512849W WO9616633A1 WO 1996016633 A1 WO1996016633 A1 WO 1996016633A1 US 9512849 W US9512849 W US 9512849W WO 9616633 A1 WO9616633 A1 WO 9616633A1
Authority
WO
WIPO (PCT)
Prior art keywords
mouthwash composition
alcohol
reduced alcohol
composition
reduced
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/US1995/012849
Other languages
English (en)
Inventor
Pauline Pan
R. Michael Buch
Frank Volpe
Michael Rubin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Warner Lambert Co LLC
Original Assignee
Warner Lambert Co LLC
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 Co LLC filed Critical Warner Lambert Co LLC
Priority to AU38902/95A priority Critical patent/AU3890295A/en
Publication of WO1996016633A1 publication Critical patent/WO1996016633A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • 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
    • A61K8/347—Phenols
    • 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
    • A61K8/49—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

Definitions

  • the invention relates generally to mouthwashes for the prevention and elimination of bad breath as well as the reduction of oral microorganisms responsible for the development of dental plaque and tooth decay.
  • Dental plaque can lead to the formation of calculus, gingivitis and other related gum diseases.
  • the present invention relates to a reduced alcohol mouthwash that is effective in preventing those problems and is pleasant tasting as well.
  • Oral rinse and mouthwash compositions have been used by people for many years for the prevention of bad breath and for the elimination of bacteria and other oral
  • Alcohol is used both as a disinfectant and as a solvent in which the bactericidal active ingredients and additives such as astringents, fluorides, color additives, flavor oils, bactericidal actives and the like can be dissolved and then dispersed into solution.
  • High levels of alcohol are generally used to provide an antiseptic function since lower concentrations are generally
  • Alcohol also provides a preservative role for the mouthwash during storage and use as well as enhances the flavor oil organoleptic cues.
  • Thymol for example, is a well known antiseptic compound also known as an essential oil which is utilized for its antimicrobial activity in a variety of mouthwash preparations.
  • thymol can be utilized in oral hygiene compositions such as mouth rinses in
  • Listerine ® is a well known
  • antiseptic mouthwash that has been used by millions for over one hundred years and has been proven effective in killing bacteria in the oral cavity that are responsible for plaque, gingivitis and bad breath.
  • Thymol together with other essential oils such as methyl salicylate, menthol and eucalyptol are active ingredients in
  • antiseptic mouth rinses such as Listerine ® . These oils achieve their efficacy although present in minute amounts. Without being restricted to any specific theory, it is now believed that the efficacy and taste of antiseptic
  • Dissolution is also important from an aesthetic point of view since a clear mouthwash solution is certainly preferred by
  • polyoxypropylene block copolymer having about 50% to about 90% ethylene oxide, a humectant and a cationic
  • composition allegedly exhibits a homogeneous, uniform appearance and high degree of bactericidal efficacy.
  • emulsion-containing cleaning and coating compositions consisting of emulsion-containing cleaning and coating compositions that are non-irritating and low foaming for maximum plaque disruption and removal.
  • the cleaning effect is achieved using an aqueous system containing a mouth conditioner comprising polydimethylsiloxane
  • a surfactant such as a block copolymer of polyoxyethylene and polyoxybutylene.
  • the composition consists of sodium
  • an anionic surfactant such as sodium lauryl sulfate (0.05% w/v - 1.0% w/v) a non-ionic surfactant such as Tween (0.01% w/v - 3.0% w/v) and a humectant such as glycerol or sorbitol in amounts of from 30% w/v to 50% w/v.
  • Alcohol may be added up to a level of 15% v/v with water comprising the remainder up to 100% w/v. It is postulated that the high levels of humectant cause the bacterial cell walls to swell causing separation of the cell wall and membrane. This enables the surfactants to enter the cell and deregulate autolysin enzymes which attack the cell wall causing holes and eventual cell lysis.
  • United States Patent No. 5,236,699 to Libin teaches an antimicrobial mouthwash composition comprising two active agents, triclosan and cetylpyridium chloride.
  • Ethanol comprises 15%-20% w/v of the water/alcohol carrier system and sorbitol is added in amounts of about 10%-15% by weight as a humectant.
  • United States Patent No. 4,945,087 to Talwar et. al. discloses an oral antiseptic composition containing thymol, eucalyptol, menthol and methyl salicylate wherein the unpleasant, medicinal taste of thymol is masked using effective amounts of a mixture of a sugar alcohol such as sorbitol and anethole.
  • the ethanol level claimed is 5-35% and levels of about 21.6% are disclosed.
  • a reduced alcohol antibacterial mouthwash in which a substantially water insoluble non-cationic antibacterial/anti-plaque agent such as triclosan is dissolved in a solvent whose water/alcohol ratio is greater than 10:1.
  • a substantially water insoluble non-cationic antibacterial/anti-plaque agent such as triclosan
  • Sorbitol, glycerin and other sugar alcohols may be incorporated as humectants but nothing is attributed to their functioning as solubilizers or active enhancement compounds.
  • U.S. Patent No. 5,100,650 to Carlin et. al. discloses an oral mouthwash with an antibacterial active such as chlorhexidine with non-ionic surfactants and high levels of sorbitol which it is asserted increase the antibacterial activity of the chlorhexidine compounds.
  • Sorbitol solution (70%) is present in amounts of from about 40% w/v to about 60% w/v and the water/alcohol ratio ranges from about 3:1 to about 10:1 by weight.
  • the present invention is a reduced alcohol
  • antibacterial mouthwash composition with a high level of efficacy in the prevention of plaque, gum disease and bad breath.
  • Sugar alcohols such as sorbitol surprisingly enhance the antimicrobial activity of the essential oil actives such as thymol even at these lower alcohol levels.
  • the oral compositions are also pleasant tasting and present a clear, aesthetically appealing product.
  • Figure 1 is a bar graph illustrating the effect of different sugar alcohol levels such as sorbitol on the biofilm critical kill times of essential oil-based mouthwash compositions comprised of about 21.6% v/v
  • the reduced alcohol mouthwash compositions of the present invention provide an unexpected high degree of antiseptic efficacy towards oral microorganisms
  • compositions of the present invention are pleasant tasting and their use leaves the mouth feeling clean and
  • the enhanced antimicrobial efficacy of the reduced alcohol mouthwash compositions of the present invention is attributed to the presence of essential oils, (i.e., minor amounts of thymol, eucalyptol., menthol and methyl
  • Methyl salicylate C 6 H 4 OHCOOCH 3
  • wintergreen oil also known as wintergreen oil, additionally provides flavoring to the mouthwash together with its antimicrobial function.
  • Eucalyptol C 10 H 18 O;
  • cineol is a terpene ether and provides a cooling, spicy taste.
  • Eucalyptol may be used in place of thymol in certain formulations in the same amount if desired.
  • Menthol (CH 3 C 6 H 9 (C 3 H 7 )OH; hexahydrothymol) also is only slightly soluble in alcohol, is fairly volatile, and in addition to any antiseptic properties provides a cooling, tingling sensation.
  • the total amount of essential oils present in a composition of this invention can be from 0.001% to about 0.35% by weight, based on the total weight of the composition, with about 0.16% to about 0.28% by weight of total volume of liquid oral preparation (% w/v) being preferred.
  • the compositions of the present invention may contain thymol, and additionally eucalyptol, menthol, methyl salicylate, and mixtures thereof.
  • the thymol is present in amounts of about 0.001% w/v to about 0.09% w/v by weight and most preferably form about to .04% w/v to about 0.07% w/v, said percent by weight being based on the total weight of the composition.
  • Eucalyptol is present in amounts of about 0.001% w/v to about 0.11% w/v and preferably, from about 0.085% w/v to about 0.10% w/v.
  • Menthol is preferably present in amounts of from about 0.001% to about 0.06% w/v and most preferably from about 0.035 to about 0.05% w.v.
  • methyl salicylate is present in amounts of from about 0.001% to about 0.08% by weight and most preferably from about 0.04% to about 0.07%.
  • the carrier for these essential oils is a water-alcohol
  • Alcohol generally ethanol, serves as both a solvent for the actives, flavor oils, astringents,
  • the alcohol solubilizes the antimicrobial actives and in so doing acts as an active enhancement mechanism.
  • the actives are more readily dispersed throughout the solution and can attack pathogenic bacteria throughout the oral cavity. Reducing the alcohol levels adversely affects this enhancement mechanism.
  • ethanol may be present in amounts of from about 12% v/v to about 22% v/v.
  • the ratio of water to alcohol is in the range of from about 3:1 to about 25:1, preferably about 3.2:1 to about 10:1 by volume.
  • the total amount of water-alcohol mixture in a mouthwash preparation is typically in the range from about 80% to about 99.9% by volume of the total composition.
  • ethanol will be incorporated in amounts of from about 12% v/v to about 22% v/v.
  • Polyols including the sugar alcohols, are selected from the group consisting of sorbitol, xylitol, mannitol, maltitol, inositol,
  • hydrogenated starch hydroslyates, propylene glycol, polyethylene glycol, 1,3,-butanediol, allitol, altritol, dulcitol, galactitol, glucitol, hexitol, iditol, pentitol, ribitol, erythritol and mixtures thereof.
  • Sorbitol is the preferred sugar alcohol in the practice of the present invention.
  • the amount of sugar alcohol employed in the oral compositions of the present invention is directly
  • surfactants are organic materials which aid in the complete dispersion of the ingredients throughout the solution as well as dispersing the preparation throughout the oral cavity.
  • the surfactants incorporated in the compositions of the present invention are a blend of non-ionic and ionic surfactants which act together to solubilize the actives.
  • the non-ionic surfactants are selected from the group known as poly(oxyethylene) poly(oxypropylene) block copolymers. Such copolymers are known commercially as poloxamers and are produced in a wide range of structures and molecular weights with varying contents of ethylene oxide.
  • HLB Hydrophilic-Lipophilic Balance
  • non-ionic surfactants useful in this invention include the following poloxamers:
  • these polymers should constitute from about 0.01% w/v to about 8.0% w/v and preferably from about
  • poloxamer is Poloxamer 407 which is incorporated in an amount of about 0.5% w/v.
  • the poloxamer Due to the reduction of ethanol content the poloxamer is used to solubilize the essential oils and flavor oils otherwise not soluble in aqueous systems.
  • the surfactant also acts to disperse the actives and flavors throughout the solution and enable the compositions to provide a clear, uniform appearance that is aesthetically more appealing.
  • three types of peppermint oil, natural, Far West (Redistilled, terpeneless) and Rose Mitchum are combined to provide a triple blend.
  • This unique blend of flavor oils not only provides a pleasant tasting mouthwash but also serves to taste mask the bitter tasting essential oil actives discussed above.
  • Each peppermint oil is combined in substantially the same amount of from about 0.01% w/v to about 1.0% w/v and preferably, in an amount of from about 0.2% w/v to about 0.3% w/v.
  • the triple blend is incorporated in the mouthwash composition in an amount of approximately 0.1% to about 2.0% and preferably in an amount of from about 0.5% to about 0.9%.
  • the essential oil methyl salicylate not only provides antimicrobial action but, being a wintergreen flavor oil, also adds to the organoleptic flavor tones as well to complement this triple blend taste masking function of the other bitter tasting actives.
  • Other flavor oils may also be added to further modify or magnify the cooling minty taste of the peppermint.
  • Suitable flavors in particular include oil of anise (0.01% to about 0.2% w/v) and benzyl alcohol (0.001% w/v to about 0.1% w/v).
  • the mouthwash is a clear, blue-green color and further includes spearmint oil (0.01% w/v to about 2.0% w/v) as an additional flavorant.
  • Other flavors such as citrus oils, vanillin and the like may be incorporated to provide further taste variations.
  • Additional components may be added as in conventional mouthwashes of the prior art. Whereas some alcohol containing mouthwashes have a pH of about 7.0, removal of the alcohol requires the addition of preservatives which drops the pH to unacceptable levels. Buffer systems are then necessary to control the pH of the composition at optimal levels. This is generally accomplished through the addition of a weak acid and its salt or a weak base and its salt. Useful systems have been found to be sodium benzoate and benzoic acid in amounts of from approximately 0.01% to about 2.0% w/v and sodium citrate and citric acid in amounts of from about 0.001% w/v to about 2.0% w/v and preferably from about 0.1% to about 0.2% w/v respectively. Preferably the buffers are incorporated in amounts that maintain the pH at levels of from approximately 3.5 to about 6.5 and more preferably, from about 4.0 to 5.0.
  • Humectants such as polyethylene glycol may be added as an additional solubilizer for the flavor oils and these also provide texture to the composition. These are incorporated in amounts of approximately 0.3% w/v to about 0.6% w/v and preferably about 0.5% w/v. Softeners such as glycerin may be added to enhance the lubricous
  • Glycerin is incorporated in amounts of approximately 1.0% w/v to about 10.0% w/v and preferably in an amount of about 7.5% w/v.
  • Sweeteners such as aspartame or sodium saccharin may be added for better taste in amounts of from about 0.005% w.v to about 1.0% w.v and preferably in an amount of approximately 0.05% w/v.
  • Zinc chloride may be added as an astringent for an "antiseptic cleaning" feeling in an amount of from about 0.0025% w/v to about 0.0075% w/v.
  • the mouthwash formulations of the present invention may be formulated to be substantially clear and colorless, acceptably approved food dyes are preferably used to color. These may be selected from the long list of acceptable food dyes and in particular may be incorporated to provide the spearmint green formulation discussed infra.
  • Suitable dyes for this purpose include FD & C yellow #5, yellow #10 and FD & C green #3 and these are added in amounts of from about .0003% w/v to about .0005% w/v or preferably from approximately 0.000035% w/v to about 0.00045% w/v.
  • Water is added to q.s. and the formulation may then be bottled and packaged for shipping.
  • the mouthwash composition of the present invention may also be formulated, if desired, as gels, foams, pastes, aerosols and tablets using standard formulations known in the art as appropriate.
  • the mouthwash compositions of the present invention may be formulated in a dry powder or liquid concentrate form.
  • the water is added to q.s. the volume to the necessary total is not added in order to prepare the liquid concentrate or what water is present is removed using standard evaporation procedures known in the art to prepare the dry powder form. Both may then have water added at a later date when ready for use.
  • Such forms are advantageous for storage and shipping.
  • An antibacterial oral composition of the present invention was prepared as follows.
  • the active essential oils and flavor oils were first dissolved in ethanol in the following amounts.
  • the flavor oil/essential oil active solution was combined and mixed with the remaining components as follows.
  • the actives/flavors alcohol solution, benzoic acid and poloxamer 407 were first mixed and to this was added 300 ml. of deionized water and the sorbitol solution as continual mixing blended the ingredients.
  • the sodium saccharin, sodium citrate and citric acid were also then added in order to realize or attain a composition pH of from about 3.9 to about 4.5, and preferably 4.2.
  • the FD & C dyes were then added followed by sufficient deionized water to Q.S. the solution to 1.0 liter.
  • the resulting oral composition was a clear blue-green color and possessed a pleasant, minty taste with little if any noticeable bitterness form the actives and the
  • compositions of the present invention were measured on in-vitro bacterial cultures as a function of the amount of sorbitol incorporated therein. Reduced ethanol levels of about 21.6% w/v were used so that water comprised from about 75% w/v to about 80% w/v of the entire composition. As can be seen from the graph, there is a dramatic drop in the critical kill time of almost two minutes when sorbitol levels are increased from about 8% to about 25%. It has been found that the greater reduction in the critical kill times occurs when the sorbitol comprises from about 17% w/v to about 50% w/v.
  • antibacterial mouthwash compositions were pleasant tasting when these higher sorbitol levels were employed.
  • the antimicrobial mouthwash formulation as set forth in Example I was prepared with different levels of polyol. These were tested as to their efficacy as measured by the amount of endotoxin extracted from in vitro cultures of three Gram negative bacteria, Fusobacterium nucleatum,
  • Actinobacillus actinomycetemcomitans (ATCC #33384) known plaque associated microorganisms. Endotoxin is a
  • the cultures are treated with mouthwash compositions with no sorbitol versus those with 17.5% sorbitol as .the data reflect in Table 1.
  • the cultures are washed with various mouthwash formulations and each mouthwash is then assayed for the amount of endotoxin contained therein which is indicative of each formulations efficacy as an antibacterial. Plus (+) signs indicate whether there has been any clotting of the assay which in turn indicates the presence of endotoxin while minus (-) signs indicate its absence.
  • Table 2 reflects the comparative efficacy of several sorbitol levels in the mouthwash formulation of Example I, again with respect to the amount of endotoxin abstracted. The double signs indicate two assays were conducted for each formulation and dilution.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne un bain de bouche antimicrobien ayant un goût agréable, et qui est utile pour prévenir et combattre la mauvaise haleine, la formation de plaque et des maladies associées des gencives. Ces compositions contiennent une quantité efficace de thymol et d'autres huiles essentielles actives, ainsi que des niveaux accrus de sorbitol, qui améliore l'efficacité des matières actives dans la cavité buccale. Non seulement les matières actives permettent d'augmenter l'efficacité, mais elles sont complètement solubilisées dans des concentrations plus faibles d'alcool, de sorte qu'un produit d'un aspect visuel agréable soit obtenu.
PCT/US1995/012849 1994-12-02 1995-10-05 Bain de bouche a teneur reduite en alcool Ceased WO1996016633A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU38902/95A AU3890295A (en) 1994-12-02 1995-10-05 Reduced alcohol mouthwash

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US35337794A 1994-12-02 1994-12-02
US08/353,377 1994-12-02

Publications (1)

Publication Number Publication Date
WO1996016633A1 true WO1996016633A1 (fr) 1996-06-06

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ID=23388844

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1995/012849 Ceased WO1996016633A1 (fr) 1994-12-02 1995-10-05 Bain de bouche a teneur reduite en alcool

Country Status (2)

Country Link
AU (1) AU3890295A (fr)
WO (1) WO1996016633A1 (fr)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0791362A2 (fr) 1996-02-23 1997-08-27 The Procter & Gamble Company Compositions désinfectantes et procédé de désinfection de surfaces
WO1997030685A1 (fr) * 1996-02-23 1997-08-28 Warner-Lambert Company Bain de bouche a teneur alcoolique reduite
US5830380A (en) * 1997-07-18 1998-11-03 Camco Manufacturing, Inc. Methyl salicylate antifreeze solution method
US5891422A (en) * 1996-10-10 1999-04-06 Warner-Lambert Company Antimicrobial composition containing a C3 -C6 alcohol
US6103683A (en) * 1996-01-12 2000-08-15 The Procter & Gamble Co. Disinfecting compositions and processes for disinfecting surfaces
US6261540B1 (en) * 1997-10-22 2001-07-17 Warner-Lambert Company Cyclodextrins and hydrogen peroxide in dental products
US6348187B1 (en) * 1996-01-24 2002-02-19 Warner-Lambert Company Peroxide/essential oils containing mouthwash compositions and two-part mouthwash systems
WO2002078663A1 (fr) * 2001-03-29 2002-10-10 Curozone Ireland Limited Rinçage contenant un reducteur pour traitement a l'ozone de caries dentaires
EP2433613A3 (fr) * 2010-06-30 2013-05-22 McNeil-PPC, Inc. Solutions de rinçage de la bouche aux huiles essentielles bioactives sans alcool
US8496915B2 (en) * 2006-11-10 2013-07-30 Matsutani Chemical Industry Co., Ltd. Noncarious material and anticarious agent containing rare sugar
RU2582222C2 (ru) * 2010-06-30 2016-04-20 МакНЕЙЛ-ППС, ИНК. Способы получения неспиртовых ополаскивателей для полости рта с биологически активными эфирными маслами
WO2018075384A1 (fr) * 2016-10-20 2018-04-26 Johnson & Johnson Consumer Inc. Formulations de bain de bouche à teneur réduite en éthanol
CN112336663A (zh) * 2020-12-02 2021-02-09 陈倩倩 一种中药漱口水
US20220062196A1 (en) * 2015-03-13 2022-03-03 Nutrition 21, Llc Arginine Silicate For Periodontal Disease
CN116785203A (zh) * 2023-07-14 2023-09-22 威莱(广州)日用品有限公司 一种含有天然植物精油组合物的漱口水及其制备方法

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Publication number Priority date Publication date Assignee Title
FR2106394A1 (fr) * 1970-09-09 1972-05-05 Colgate Palmolive Co
EP0338978A2 (fr) * 1988-03-31 1989-10-25 Warner-Lambert Company Masquage du goût du thymol
EP0497476A2 (fr) * 1991-01-30 1992-08-05 Colgate-Palmolive Company Compositions orales antiplaques
WO1994007477A1 (fr) * 1992-10-07 1994-04-14 Warner-Lambert Company Masquage du gout du thymol
WO1994016674A1 (fr) * 1993-01-27 1994-08-04 Warner-Lambert Company Antiseptique pour bains de bouche a teneur en alcool reduite et preparations
WO1994018939A1 (fr) * 1993-02-19 1994-09-01 Warner-Lambert Company Composition de rinçage utilisee avant le brossage
DE4418796A1 (de) * 1993-06-02 1994-12-15 Colgate Palmolive Co Oral anwendbare und gegen Plaque und Gingivitis wirkende Zusammensetzungen

Patent Citations (8)

* 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
EP0338978A2 (fr) * 1988-03-31 1989-10-25 Warner-Lambert Company Masquage du goût du thymol
US4945087A (en) * 1988-03-31 1990-07-31 Warner-Lambert Company Taste masking of thymol
EP0497476A2 (fr) * 1991-01-30 1992-08-05 Colgate-Palmolive Company Compositions orales antiplaques
WO1994007477A1 (fr) * 1992-10-07 1994-04-14 Warner-Lambert Company Masquage du gout du thymol
WO1994016674A1 (fr) * 1993-01-27 1994-08-04 Warner-Lambert Company Antiseptique pour bains de bouche a teneur en alcool reduite et preparations
WO1994018939A1 (fr) * 1993-02-19 1994-09-01 Warner-Lambert Company Composition de rinçage utilisee avant le brossage
DE4418796A1 (de) * 1993-06-02 1994-12-15 Colgate Palmolive Co Oral anwendbare und gegen Plaque und Gingivitis wirkende Zusammensetzungen

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6103683A (en) * 1996-01-12 2000-08-15 The Procter & Gamble Co. Disinfecting compositions and processes for disinfecting surfaces
US6348187B1 (en) * 1996-01-24 2002-02-19 Warner-Lambert Company Peroxide/essential oils containing mouthwash compositions and two-part mouthwash systems
EP0791362A2 (fr) 1996-02-23 1997-08-27 The Procter & Gamble Company Compositions désinfectantes et procédé de désinfection de surfaces
WO1997030685A1 (fr) * 1996-02-23 1997-08-28 Warner-Lambert Company Bain de bouche a teneur alcoolique reduite
EP0791362A3 (fr) * 1996-02-23 1998-03-04 The Procter & Gamble Company Compositions désinfectantes et procédé de désinfection de surfaces
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