WO1997040812A1 - Composition buccale amelioree contenant du zinc - Google Patents

Composition buccale amelioree contenant du zinc Download PDF

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Publication number
WO1997040812A1
WO1997040812A1 PCT/US1997/006758 US9706758W WO9740812A1 WO 1997040812 A1 WO1997040812 A1 WO 1997040812A1 US 9706758 W US9706758 W US 9706758W WO 9740812 A1 WO9740812 A1 WO 9740812A1
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WO
WIPO (PCT)
Prior art keywords
zinc
oral composition
composition
improved oral
essential oils
Prior art date
Application number
PCT/US1997/006758
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English (en)
Inventor
Rita M. Parikh
David Scott Harper
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 AU27390/97A priority Critical patent/AU2739097A/en
Publication of WO1997040812A1 publication Critical patent/WO1997040812A1/fr

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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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/27—Zinc; Compounds thereof
    • 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
    • A61K8/347—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

  • This invention relates to an improved anticalculus and antimicrobial effective oral composition
  • a source of zinc ion in combination with essential oils such as thymol, eucalyptol, menthol, and methyl salicylate.
  • Oral malodor reduction is also improved with the oral composition of this invention.
  • the oral composition of this invention is in the form of a dentifrice, mouthwash and the like.
  • Zinc ions in oral compositions are typically provided as water-soluble zinc salts or suspensions of zinc oxide particles. Oral compositions with zinc ions have enhanced bacteriostatic activity. They also have enhanced anticalculus activity.
  • Essential oils are known to be germicidal. When used in oral compositions they reduce plaque, gingivitis, and oral malodor. Essential oils are aromatic compounds that are either derived from plant sources or are synthesized. Thymol is an essential oil that is well-known and widely used as an antimicrobial in oral compositions. Other essential oils include menthol, methyl salicylate, eucalyptol, anethol and eugenol. For example LISTERINE® antiseptic mouthwash has been marketed for over 100 years, and contains thymol, menthol, eucalyptol, and methyl salicylate More recently, essential oils have been included in formulations of dentifrice
  • U S Patent No 4,022,880 to Vinson et al teaches a composition for inhibiting dental plaque and calculus comprising zinc ions and a non-toxic, organoleptically acceptable antibacterial agent
  • U S Patent No 4,550,018 to Ambike et al teaches an oral composition with zinc chloride and essential oil However, the essential oil is in a flavor amount, not an antibacterial amount
  • U S Patent No 4,568,540 to Asano et al teaches an oral hygiene composition containing an effective concentration of a pharmaceutically acceptable fluoride salt, a pharmaceutically acceptable zinc salt, a specific buffering agent, a suitable vehicle and having a pH of from about 3 5 to 6 0.
  • U S Patent Nos 4,749,561 and 4,749,562 to Lane et al teaches a dentifrice including a substantially water-insoluble non-cationic antimicrobial agent or a zinc salt or a mixture thereof when the dentifrice comprises at least 0 2% by weight of a lamellar liquid crystal surfactant phase
  • Figure 1 is a graph ofthe bacteriostatic efficacy of zinc ion dentrifrice compositions made with and without essential oils
  • the oral composition of this invention comprises an anticalculus and bacteriostatic effective amount of zinc ion, an antimicrobial effective amount of one or more essential oils, and an orally acceptable vehicle or base
  • the oral composition of this invention is preferably a dentifrice, such as toothpaste and gel Other compositions may include mouthwashes, mouthrinses, tooth powders, tooth hardeners, antitartar compositions, anticalculus compositions, gums, tablets, lozenges, troches and the like.
  • the base or the medium for the active components ofthe composition of this invention will be any which is conventionally employed and known to those skilled in the art
  • the zinc ion in the composition of this invention may be provided by a number of zinc-containing compounds
  • the preferred source of zinc ion is one or more water- soluble zinc salts or zinc oxide.
  • Suitable zinc salts include but are not limited to zinc sulphate, zinc chloride, zinc bromide, zinc iodide, zinc nitrate, and carboxylic acid salts of zinc
  • the preferred zmc salt is zinc chloride
  • the dentifrice composition of this invention is formulated to provide at least about 50 ppm of zinc ion, more preferably at least about 1500 ppm of zinc ion.
  • the water-soluble zinc salt or salts are present in the composition of this invention in an amount of up to about 5% by weight ofthe composition (hereinafter "w/w"), preferably about 0 25 to about 3% w/w, and most preferably about 0 5 to about 2% w/w
  • w/w the composition
  • 0 01% zinc chloride by weight provides about 50 ppm zinc ion
  • 0 2% zinc chloride by weight provides about 1000 ppm zinc ion
  • 0 3% zinc chloride provides about 1500 ppm zinc ion.
  • the preferred amount of zinc chloride in the dentifrice composition of this invention is, therefore, about 0 01% w/w; the more preferred amount of zinc chloride is about 0 2% w/w; and the most preferred amount is about 0.5% w/w
  • Zinc ions can also be provided by suspensions of zinc oxide particles
  • the zinc oxide is present in the composition in an amount sufficient to provide at least about 50 ppm zinc ion, preferably at least about 1500 ppm zinc ion
  • Essential oils are volatile aromatic oils that may be synthetic or may be derived from plants by distillation, expression or extraction, and that usually carry the odor or flavor ofthe plant from which they are obtained Essential oils are widely used in oral care products Some essential oils show long-lasting germicidal effectiveness against the most common pathogens in the mouth These pathogens are frequently associated with oral malodor, plaque, and gingivitis
  • the essential oils in the composition of this invention include but are not limited to thymol, methyl salicylate, menthol, eucalyptol, camphor, anethole, carvone, eugenol, isoeugenol, liminene, osimen, n-decyl alcohol, citronel, alpha-salpineol, methyl acetate, chlorothymol, citronellyl acetate, methyl eugenol, cineol, ethyl linalaol, safrola vinillin, spearmint oil,
  • a dentifrice composition of this invention it is desirable that there be at least about 0 075% by weight of each of such four essential oils, preferably at least about 0 125% by weight, and most preferably at least about 0.2% by weight of each essential oil.
  • Thymol also known by the chemical formula 5-methyl 2-( 1 -methylethyl) phenol, may be in the dentifrice composition of this invention in an amount of from about 0 01% w/w to about 1 0% w/w, preferably in an amount of from about 0 1% w/w to about 0 7% w/w, and most preferably in an amount of from about 0 2% w/w to about 0 6% w/w Menthol may be in the dentifrice composition ofthe present invention in an amount of from about 0 01% w/w to about 1 0% w/w, preferably in an amount of from about 0 10% w/w to about 0 7% w/w, and most preferably in an amount of from
  • Eucalyptol may be in the dentifrice composition ofthe present invention in an amount of from about 0 01% w/w to about 1 0% w/w, preferably in an amount of from
  • Methyl salicylate may be in the dentifrice composition ofthe present invention in an amount of from about 0 01% w/w to about 1.0% w/w, preferably in an amount of from about 0 04% w/w to about 0 8% w/w, and most preferably in an amount of from about
  • the dentifrice composition ofthe invention may contain the following essential oils in percentages by weight (a) thymol from about 0 01% w/w to about 1 0% w/w, (b) menthol from about 0 01% w/w to about 1 0% w/w, (c) eucalyptol from about 0 01% w/w to about 1 0% w/w, and (d) methyl salicylate from about 0 01% w/w to about 1 0% w/w
  • the dentifrice composition may contain the following essential oils in percentages by weight, (a) thymol from about 0 1% w/w to about 0 7% w/w, (b) menthol from about 0 1% w/w to about 0.7% w/w, (c) eucalyptol from about 0 05% w/w to about 0 5% w/w, and (d) methyl salicylate from about 0 04% w/w to about 0 8% w/w
  • the dentifrice composition may contain the following essential oils in percentages by weight (a) thymol from about 0 2% w/w to about 0 6% w/w, (b) menthol from about 0.2% w/w to about 0.6% w/w; (c) eucalyptol from about 0.07% w/w to about 1.0% w/w; and (d) methyl salicylate from about 0.2% w/w to about 0.7% w/w.
  • the total concentration by weight ofthe one or more essential oils is from about 0.1% w/w to about 4.0% w/w ofthe dentifrice composition. In the preferred embodiment the total concentration by weight ofthe one or more essential oils is from about 0.5% w/w to about 3.0% w/w. In the most preferred embodiment the total concentration by weight ofthe one or more essential oils from about 0.8% w/w to about 2.5% w/w.
  • the dentifrice composition of this invention also comprises a liquid vehicle containing about 3-60% by weight of water, typically mixed with at least one humectant and a number of other ingredients.
  • the liquid phase comprises about 20-90% by weight ofthe dentifrice and is generally about 25-80% liquid.
  • Suitable humectants in the dentifrice include sorbitol, glycerin, propylene glycol, polyethylene glycol, sorbitan, fructose, mixtures thereof and the like. Humectants, when employed, may be present in amounts of from about 10% to about 50%, by weight ofthe dentifrice composition.
  • the dentifrice also contains a gelling or binding agent as a solid vehicle agent.
  • Gelling or binding agents which may be present include alkali metal carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, xanthan, thickening silicas, Irish moss, iota-carrageenan, gum tragacanth, polyethylene glycol, polyvinyl pyrrolidone, starch and mixtures thereof.
  • any suitable surface active or detergent material may also be included in the dentifrice compositions.
  • These surfactants may be non-ionic, amphoteric, cationic, or anionic.
  • the most preferred surfactants are anionic.
  • These anionic surfactants include but are not limited to sodium lauryl sulfate, sodium lauroyl sarcosinate, and sodium methyl cocoyl taurate, and disodium lauryl sulfosuccinate.
  • the surfactant is the anionic surfactant sodium lauryl sulfate.
  • Suitable nonionic surfactants in the present invention include poly(oxethylene)- poly(oxypropylene) block copolymers, also known commercially as poloxamers. Poloxamer surfactants in the present invention should have a Hydrophilic-Lipophilic Balance (HLB) of between about 10 and about 30, and preferably between about 10 and about 25.
  • HLB Hydrophilic-Lipophilic Balance
  • Amphoteric surfactants have the capacity to behave as either an acid or a base and include quatemized imidazole derivatives useful in the present invention.
  • Preferred amphoteric agents include long chain (alkyl) amino-alkylene aklylated amine derivatives, also known as "Miranol", i.e., Miranol C 2 M, or N-alkyl betaine surfactants.
  • Cationic surfactants are surfactants which carry a positive charge.
  • Cationic surfactants especially useful in the present invention include antimicrobial quaternary ammonium salts.
  • Fluorine-releasing compounds may be used in the dentifrice composition of this invention and may be fully or slightly water soluble.. These are chacterized by their ability to release fluoride ions or fluoride-containing ions in water and by their lack of reaction with other components in the composition..
  • Typical fluorine-releasing compounds are inorganic fluoride salts such as water-soluble alkali metal, alkaline earth metal, and heavy metal salts. Sodium monofluorophosphate, sodium fluoride, stannous fluoride and mixtures thereof are preferred. The most preferred fluorine-releasing compound is sodium monofluorophosphate.
  • the amount of fluorine-releasing compound should be sufficient to provide 800-1500 ppm fluoride ion.
  • Sweeteners well known in the art including natural and artificial sweeteners, may be used in the dentifrice compositions of this invention.
  • the sweetener may be selected from a wide range of materials including naturally occurring water-soluble sweeteners, artificial water-soluble sweeteners and modified water-soluble sweeteners derived from naturally occurring water-soluble sweeteners.
  • an effective amount of sweetener is utilized to provide the level of sweetness desired in any particular embodiment ofthe dentifrice compositions according to the present invention. This amount will vary with the sweetener selected and the final oral hygiene product.
  • flavoring agents include those flavors known to the skilled artisan, such as natural and artificial flavors. Suitable flavoring agents include mints, such as peppermint, citrus flavors such as orange and lemon, artificial vanilla, cinnamon, various fruit flavors, both singly or mixed, and the like. The amount of flavoring agent employed herein is normally a matter of preference subject to such factors as the type of final dentifrice composition, the individual flavor employed, and the strength of flavor desired.
  • the coloring agents (colors, colorants) useful in the present invention are used in amounts effective to produce the desired color. These coloring agents include pigments which may be inco ⁇ orated in amounts up to about 6%, by weight ofthe composition. A preferred pigment, titanium dioxide, may be incorporated in amounts up to about 2%, and preferably less than about 1%, by weight ofthe composition. A full recitation of all F D. & C colorants and their corresponding chemical structures may be found in the Kirk-
  • Suitable abrasives in the dentifrice include hydrated silica, calcium carbonate, calcium pyrophosphate, dicalcium phosphate dihydrate, or alkali metal meta-phosphates.
  • Silica abrasives in the dentifrice composition according to this invention may include among others, ZEODENT® (113), manufactured by J. M. Huber Co ⁇ . and SYLOID® or SYLODENT®, manufactured by W.R. Grace Co. These abrasives may be used in amounts up to about 75.0% w/w ofthe composition, preferably in amounts from about 5.0% w/w to about 40% w/w ofthe composition, and most preferably from about 7.0% w/w to about 30.0% w/w ofthe composition.
  • Suitable buffers include citric acid-sodium citrate, acetic acid-sodium acetate, sodium saccharine-acid saccharine, and benzoic acid and benzoate in amounts up to about 1%, and preferably from about 0.05% to about 0.5%, by weight ofthe composition.
  • the pH for the preferred embodiment ofthe dentifrice ofthe present invention is from 3.0 to about 5.5.
  • Suitable preservatives in this invention include benzoic acid, sodium benzoate, butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), ascorbic acid, methyl paraben, propyl paraben, tocopherols and mixtures thereof.
  • Preservatives when used are generally present in amounts up to about 1.0% w/w, and preferably from about 0.1% w/w to about 1.0% w/w ofthe dental gel composition.
  • Various other materials may be inco ⁇ orated in the dentifrice of this invention. Examples thereof are opacifiers, desensitizing agents, silicones and ammoniated materials such as urea, diammonium phosphate and mixtures thereof. These adjuvants are inco ⁇ orated in the dentifrice in amounts which do not substantially adversely affect the desired properties and characteristics and are suitably selected and used in conventional amounts.
  • the dentifrice composition is in the form of toothpaste or a dental gel.
  • gel means a solid or semisolid colloid which contains considerable quantities of water. The colloid particles in a gel are linked together in a coherent meshwork which immobilizes the water contained inside the meshwork.
  • One skilled in the art would know how to formulate the dentifrice compositions of this invention as a past and a gel.
  • an oral antiseptic dentifrice composition according to the present invention is made by first combining water, a source of zinc ion, part ofthe humectant, one or more sweeteners, buffers and preservatives. If fluorine-releasing compounds are used, they are added in this step. The remainder ofthe humectant is separately combined with one or more gums, and then combined with the first mixture. Titanium dioxide and silicas are separately mixed, and combined with the other mixture previously prepared. Finally, colors, essential oils, flavors, and surfactants are added and mixed.
  • the pH is adjusted to a pH of about 3.0 to about 5.5 with acidifiers. A vacuum is pulled if necessary for deaeration.
  • the pH of a 25.0% w/w aqueous solution ofthe composition is measured using a suitable pH meter (ej ⁇ Orion Research Microprocessor pH/millivolt Meter,
  • the apparatus useful in accordance with the present invention comprises mixing apparatus well known in the dental art, and therefore the selection ofthe specific apparatus will be apparent to the artisan.
  • the present invention is further illustrated by the following examples which are, however, not included to limit the effective scope ofthe claims All parts and percentages in the examples and throughout the specification and claims are by weight ofthe final composition unless otherwise specified.
  • a mouthwash with the ability to prevent the creation of malodors for several hours was prepared by combining the following components in potable water
  • Poloxamer 407 2 0 grams
  • the above composition was prepared by adding the essential oils (thymol, menthol, methyl salicylate and eucalptol), Poloxamer 407, benzoic acid, and 1 -propanol to ethanol, followed by the addition of 250 ml of potable water
  • a dentifrice with zinc chloride and essential oils was formulated.
  • Another component in the dentrifrice was hydroxyethylcellulose (Natrosol 250H.) Natrasol 250H in the dentifrice helps reduce the astringency caused by zinc ions.
  • the relative antimicrobial activity of several oral compositions of this invention was tested using an ex vivo kinetic kill time assay and a Plaque Kill & Growth kinetics (PKGK) assay.
  • kinetic kill time assay saliva suspensions containing natural oral organisms were vigorously mixed with a dentifrice sample in a 3.5: 1 ratio.
  • One ml aliquots of the assay mixture were removed and diluted into a neutralizing broth in a 1:9 ratio at 30 and 60 seconds, which periods represent the length of time typically spent in toothbrushing.
  • 50 ⁇ l aliquots of diluted suspension were plated on nutrient agar plates, which were incubated anaerobically at 37° C and counted to enumerate surviving microbial colonies.
  • Relative antiseptic activity of each dentifrice was determined as a function ofthe number of surviving organisms recovered on agar plates.
  • the PKGK assay determined the in vivo antibacterial efficacy of a single dentifrice use in which product was brushed onto one dental quadrant for 15 seconds, then dispersed throughout the mouth for 45 seconds using the tongue and "swishing" in a manner previously described by White et al (J. Dent. Res. 12 A, #1346, 1993; J. Clin. Dent, special issue IV: 59-71, 1995).
  • Bactericidal and bacteriostatic effects against plaque microorganisms were assessed by 1 ) quantitative culturing of turbidity-adjusted plaque samples, and 2) growth kinetics analysis (lag time) of the plaque bacterial suspensions incubated in nutrient broth.
  • Dentifrice formulations of this invention were prepared using ingredients and quantities as shown in Table 1.
  • Formulas 1.1-1.3 of this invention were formulated with increasing levels of zinc chloride plus a constant level of the essential oils thymol, menthol, methyl salicylate and eucalyptol.
  • Formulas 2.1-2.3 of this invention were formulated with increasing levels of zinc chloride without essential oils.
  • bacteriostatic efficacy of the dentifrice compositions was determined by measuring growth kinetic lag time of the plaque bacterial suspensions incubated in nutrient broth.
  • the combination of zinc chloride and essential oils resulted in a significant increase in bacteriostasis compared to the formulas without essential oils
  • the enhancement in bacteriostasis by the addition of essential oils became more pronounced in later post-treatment phases, indicating long lasting efficacy
  • a clear dose response was observed between zinc chloride levels and bacteriostatic efficacy in the presence of essential oils (formulas 1.1, 1.2 and 1.3).

Abstract

Composition buccale améliorée pouvant être utilisée sous forme de pâte dentifrice, de gel dentifrice, de poudre dentifrice, de durcisseur dentaire, de composition anti-tartre, de chewing-gum ou de pastilles et contenant des ions de zinc dans des quantités suffisantes pour agir de manière efficace contre le tartre et les microbes, ainsi qu'une ou plusieurs huiles essentielles dans des quantités suffisantes pour agir de manière efficace contre les microbes. La composition buccale a un effet durable d'haleine fraîche. La source préférée d'ions de zinc est le chlorure de zinc. Les huiles essentielles préférées sont le thymol, le menthol, l'eucaliptol et le salicylate de méthyle.
PCT/US1997/006758 1996-04-26 1997-04-24 Composition buccale amelioree contenant du zinc WO1997040812A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU27390/97A AU2739097A (en) 1996-04-26 1997-04-24 Enhanced zinc containing oral composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US1680296P 1996-04-26 1996-04-26
US60/016,802 1996-04-26

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WO1997040812A1 true WO1997040812A1 (fr) 1997-11-06

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999020238A1 (fr) * 1997-10-23 1999-04-29 Warner-Lambert Company Produits oraux contenant un ion metallique a astringence reduite
WO1999032075A1 (fr) * 1997-12-22 1999-07-01 Warner-Lambert Company Compositions permettant d'inhiber la gingivite
WO2000000166A2 (fr) * 1998-06-29 2000-01-06 Warner-Lambert Company Compositions orales ameliorees d'elimination et de prevention du tartre, de la fetidite, de la plaque et de la gengivite
WO2000061092A1 (fr) * 1999-04-08 2000-10-19 Warner-Lambert Company Composition de dentifrice contenant du zinc
WO2000071090A1 (fr) * 1999-05-26 2000-11-30 Dentsply International Inc. Compositions orales a base de sel de zinc permettant de controler les odeurs bucco-respiratoires
US6759544B2 (en) 2001-06-22 2004-07-06 Nutrinova Nutrition Specialties & Food Ingredients Gmbh Antimicrobially active acesulfame complexes, process for their preparation and their use
US6861048B2 (en) 1999-04-08 2005-03-01 Warner-Lambert Company Dentifrice compositions having reduced abrasivity
WO2005058364A2 (fr) * 2003-12-12 2005-06-30 Reckitt Benckiser Healthcare (Uk) Limited Systeme de preservation
US8236348B2 (en) 2003-02-04 2012-08-07 Bennes, Inc. Long-lasting, flavored dosage forms for sustained release of beneficial agents within the mouth
WO2016036341A1 (fr) * 2014-09-01 2016-03-10 Colgate-Palmolive Company Compositions à base de zinc et contenant des huiles essentielles
FR3105732A1 (fr) * 2019-12-30 2021-07-02 Ezal Consumer Healthcare Composition comprenant des huiles essentielles ou des composants de celles-ci, pour prévenir ou traiter des pathologies bucco-dentaires
WO2022099182A1 (fr) * 2020-11-09 2022-05-12 Rucker Capital Advisors Rinçage buccal, pulvérisation nasale et méthodes pour la prévention de la covid-19 par réduction de la charge virale de covid-19

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US1435498A (en) * 1920-01-16 1922-11-14 Ernest D Resnik Dentifrice
US1488097A (en) * 1922-03-09 1924-03-25 Henry N Creger Dentifrice
US2527686A (en) * 1945-12-26 1950-10-31 Max H Sandberg Mouthwash
US4170632A (en) * 1977-11-28 1979-10-09 General Mills, Inc. Plaque inhibiting compositions and method
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WO1999020238A1 (fr) * 1997-10-23 1999-04-29 Warner-Lambert Company Produits oraux contenant un ion metallique a astringence reduite
WO1999032075A1 (fr) * 1997-12-22 1999-07-01 Warner-Lambert Company Compositions permettant d'inhiber la gingivite
WO2000000166A2 (fr) * 1998-06-29 2000-01-06 Warner-Lambert Company Compositions orales ameliorees d'elimination et de prevention du tartre, de la fetidite, de la plaque et de la gengivite
WO2000000166A3 (fr) * 1998-06-29 2000-02-10 Warner Lambert Co Compositions orales ameliorees d'elimination et de prevention du tartre, de la fetidite, de la plaque et de la gengivite
US6861048B2 (en) 1999-04-08 2005-03-01 Warner-Lambert Company Dentifrice compositions having reduced abrasivity
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WO2000061092A1 (fr) * 1999-04-08 2000-10-19 Warner-Lambert Company Composition de dentifrice contenant du zinc
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WO2000071090A1 (fr) * 1999-05-26 2000-11-30 Dentsply International Inc. Compositions orales a base de sel de zinc permettant de controler les odeurs bucco-respiratoires
US6759544B2 (en) 2001-06-22 2004-07-06 Nutrinova Nutrition Specialties & Food Ingredients Gmbh Antimicrobially active acesulfame complexes, process for their preparation and their use
US8236348B2 (en) 2003-02-04 2012-08-07 Bennes, Inc. Long-lasting, flavored dosage forms for sustained release of beneficial agents within the mouth
WO2005058364A2 (fr) * 2003-12-12 2005-06-30 Reckitt Benckiser Healthcare (Uk) Limited Systeme de preservation
WO2005058364A3 (fr) * 2003-12-12 2006-02-23 Reckitt Benckiser Healthcare Systeme de preservation
WO2016036341A1 (fr) * 2014-09-01 2016-03-10 Colgate-Palmolive Company Compositions à base de zinc et contenant des huiles essentielles
AU2014405603B2 (en) * 2014-09-01 2018-03-29 Colgate-Palmolive Company Zinc-containing compositions with essential oils
FR3105732A1 (fr) * 2019-12-30 2021-07-02 Ezal Consumer Healthcare Composition comprenant des huiles essentielles ou des composants de celles-ci, pour prévenir ou traiter des pathologies bucco-dentaires
WO2022099182A1 (fr) * 2020-11-09 2022-05-12 Rucker Capital Advisors Rinçage buccal, pulvérisation nasale et méthodes pour la prévention de la covid-19 par réduction de la charge virale de covid-19

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