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WO1986002831A1 - Dentifrice contenant un agent de chelation de calcium d'alginate - Google Patents

Dentifrice contenant un agent de chelation de calcium d'alginate Download PDF

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Publication number
WO1986002831A1
WO1986002831A1 PCT/US1985/002211 US8502211W WO8602831A1 WO 1986002831 A1 WO1986002831 A1 WO 1986002831A1 US 8502211 W US8502211 W US 8502211W WO 8602831 A1 WO8602831 A1 WO 8602831A1
Authority
WO
WIPO (PCT)
Prior art keywords
dentifrice
water
sodium alginate
alginic acid
amount
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/US1985/002211
Other languages
English (en)
Inventor
Alec D. Keith
Thomas C. Usher
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.)
Zetachron Inc
Original Assignee
Zetachron Inc
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 Zetachron Inc filed Critical Zetachron Inc
Publication of WO1986002831A1 publication Critical patent/WO1986002831A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0216—Solid or semisolid forms
    • 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
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/733—Alginic acid; Salts thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/51—Chelating agents

Definitions

  • This invention relates to dentifrice compositions and more particularly to dentifrices containing a chelating agent which facilitates the removal of dental plaque.
  • Dental plaque consists of about 70% bacteria with the remainder being composed of bacterial products such as dextran-type polysaccharides, enzymes, acids and components of the saliva. It is a white or off-white substance of variable thickness and contains specific bacteria which form the polysaccharides that enable the micro-organisms to stick to the teeth and to each other. Consequently, plaque confines the acidic meta ⁇ bolic products of the bacteria, principally lactic acid, in close contact with the tooth surface where they decompose the hydroxyapatite in the enamel, and eventually form a cavity. The plaque also eventually becomes calcified to form calculus, a hard deposit which can irritate the gums and contribute to periodon- tal disease.
  • bacterial products such as dextran-type polysaccharides, enzymes, acids and components of the saliva. It is a white or off-white substance of variable thickness and contains specific bacteria which form the polysaccharides that enable the micro-organisms to stick to the teeth and to each other. Consequently, plaque confines the acid
  • the conventional method of combating plaque forma ⁇ tion on teeth is to mechanically remove it by brushing, usually employing a dentifrice which contains some detergent and a mild abrasive. This type of removal is not entirely effective, because the plaque is very adherent to the teeth and its removal requires careful and prolonged brushing in the proper manner. Such careful brushing is tedious, and neglected by people who eventually end up with tooth decay.
  • a number of chemical anti-microbial materials have been added to dentifrice to aid in combating the forma ⁇ tion of plaque.
  • Chlorhexidine for example, has been incorporated in a dentifrice as an antimicrobial to kill the plaque-forming bacteria.
  • Such techniques have achieved some success in preventing plaque but such anti-microbials have an offensive taste which cannot be masked in dentifrice- or other oral preparations.
  • certain questions have been raised about the long term toxicity of these agents.
  • 29,182 discloses the use of certain polyphosphonic acids and their salts in oral prepara ⁇ tions for retarding the formation of dental calculus. These chemicals have certain drawbacks. Some of them, e.g., EDTA, have too strong a chelating power and may damage the tooth enamel. All of them are synthetic compounds which may have a certain toxicity or a sensi ⁇ tizing effect, especially when the user is exposed to their relatively frequent contact over a long period.
  • a denti ⁇ frice composition which incorporates as an essential ingredient a water-soluble alginate or a mixture of water-soluble alginates which are effective in causing the removal of dental plaque.
  • a water-soluble alginate or a mixture of water-soluble alginates which are effective in causing the removal of dental plaque.
  • the alginates utilized in the invention are preferably low viscosity, water-soluble alkali metal salts of alginic acid or a mixture of low- and medium- viscosity water-soluble salts of such acid.
  • Such algi ⁇ nates are utilized in an amount sufficient to weaken the structure of plaque by forming a complex with cal- cium ions contained in that structure, whereupon the complex is diffused out and washed away with water and saliva.
  • a further object is to provide a dentifrice which contains substances aiding in the removal of dental plaque.
  • a still further object is to provide a dentifrice containing a calcium ion chelating agent.
  • An additional object is to provide a dentifrice containing a calcium ion chelating agent which is essentially non-toxic.
  • Another object is to provide a dentifrice contain- ing a water-soluble alginate or alginate composition in a sufficient amount for the effective removal of dental plaque.
  • the denti ⁇ frice not contain a significant amount of calcium ions, although it may contain conventional materials which are substantially devoid of such ions such as enzymes, sudsing agents, binders, humectants, flavoring and sweetening agents.
  • the dentifrice of this invention will typically contain from about 1.5% to about 15% by weight (based on total weight) of a water-soluble algi ⁇ nate or mixture of such alginates.
  • Alginic acid is a polysaccharide made up of D- mannuronic acid and L-guluronic acid residues. It is produced from brown seaweeds (Phaeophycae) through an extraction process. Depending on the particular species of seaweed and the method used in extraction, alginates of various molecular weights can be prepared. The higher molecular weight alginates form viscous solutions in water at relatively low concentra- tions, e. g. , 1 % by weight, and hence have found utility as viscosity adjusting agents in foods and dentifrices. However, alginates have not been used previously in combatting dental plaque.
  • water-soluble algi- nates are effective calcium ion chelating agents which can be incorporated into a dentifrice in amounts suffi ⁇ cient to remove a significant proportion of calcium ions from the plaque. It is believed that the calcium ions in the plaque contribute to its mechanical strength, and that their removal weakens the plaque so that it will dissolve, or at least can be more easily removed by brushing.
  • the water-soluble alginates used in this invention are generally the alkali metal salts of alginic acid but sodium alginate is used in a preferred embodiment.
  • the lower molecular weight algi ⁇ nates have a smaller viscosity-increasing effect in aqueous solutions and, accordingly, larger amounts of these alginates can be incorporated without excessive increase in viscosity.
  • the term "dentifrice” as used herein is intended to include mouthwash, chewing tablets, lozenge tablets, and chewing gum as well as tooth-paste, -gel, -cream or -powder.
  • the use of such alginates when used in an effec- tive amount, will result in a substantial reduction in dental plaque. Any amount which is sufficient in achieving the desired substantial reduction in plaque is an effective amount.
  • the effective amount of water-soluble alginate used in this invention will be between about 1.5 percent to about 15 percent by weight, based on the total weight of the dentifrice.
  • Alginates of relatively high molecular weight, the so-called medium-viscosity alginates can be incorporated into a dentifrice formulation of this invention, but in amounts in excess of about 1.5 % by weight the viscosity becomes too great for practical utility.
  • the water-soluble alginates should be low- viscosity alginates.
  • up to 15 % by weight of the low-viscosity water-soluble alginates may be incorpo ⁇ rated into the dentifrice of this invention.
  • the alginates represent an essential ingred ⁇ ient of the desired formulation
  • various other materials may be incorporated in the dentifrice preparations of this invention which comprise the so- called carrier composition. Examples thereof are enzymes, sudsing agents, binders, humectants, coloring agents, preservatives, sweetening, and flavoring agents. These adjuvants are incorporated in amounts which do not substantially adversely affect the proper- ties and characteristics desired and are selected and used in proper amounts depending upon the particular type of preparation involved.
  • a dentifrice according to this invention may incorporate a humectant in order to provide a means for preventing the formulation from drying out and becoming too hard, or to provide a moist feel to the mouth in the case of mouthwashes.
  • Typical humectants include glycerol, sorbitol, maltitol, glu ⁇ cose, propylene glycol, polyethylene glycols of various molecular weights and the like.
  • a preferred humectant is glycerol.
  • the humectant can comprise up to 36% by weight of the dentifrice composition.
  • the dentifrice of this invention must be devoid of substantial amounts of compounds which can supply cal- ciu ions or other divalent metal ions which can form chelates with alginates, since such materials would saturate the calcium chelating potential of the algi ⁇ nate and destroy its ability to remove calcium ions from the plaque. Accordingly, in toothpastes according to the invention, many conventional toothpaste abra ⁇ sives such as calcium phosphate, calcium carbonate and the like cannot be used in this invention. However, abrasives such as silica in its various forms, insolu ⁇ ble sodium metaphosphate, hydrated alumina,magnesium carbonate and the like can be effectively used in this invention. The abrasives may be incorporated in amounts up to about 35% by weight.
  • a sudsing agent or surfactant will be included.
  • Suitable surfactants include cationic, nonionic and amphoteric synthetic detergents.
  • Useful cationic synthetic detergents can be broadly defined as quaternary ammonium compounds having 1 long alkyl chain containing from about 8 to about 18 carbon atoms such as lauryl trimethylammonium chloride; cetyl pyridinium chloride; cetyl trimethylam- monium bromide; di-isobutylphenoxyethoxyethyldimethyl- benzylammonium chloride; coconutalkyltrimethylammonium nitrite; cetyl pyridinium fluoride and the like.
  • amphoteric synthetic detergents useful in the present invention can be broadly described as deriva- tives of aliphatic secondary and tertiary amines in which the aliphatic radical can be straight chain or branched and wherein one of the aliphatic substituents contains from about 8 to about 18 carbon atoms and one contains an anionic water-solubilizing group, e.g., carboxylate, sulfonate, sulfate, phosphate, or phospho- nate.
  • anionic water-solubilizing group e.g., carboxylate, sulfonate, sulfate, phosphate, or phospho- nate.
  • Examples of compounds falling within this defi ⁇ nition are sodium 3-dodecylaminopropionate, sodium 3- dodecylaminopropane sulfonate, dodecyl-beta-alanine, N- alkyl-taurines all of which are well-known and prepared by conventional procedures. See, for example, U. S. Patent 2,658,072 to Kosmin.
  • the sudsing agent can be present in the compositions of this invention in an amount from about 0.5% to about 5% by weight of the total composition.
  • a water-soluble fluoride compound may also be present in an amount sufficient to give a fluoride concentration of from about 0.0025% to about 5.0% by weight, preferably from about 0.005% to about 2.0% by weight, to provide additional anticaries effec- tiveness.
  • Suitable fluoride sources are well known in the art. Preferred fluorides are sodium fluoride, stannous fluoride, indium fluoride, and sodium mono- fluorophosphate.
  • U. S. Patent 3,959,458 discloses dentifrice compositions containing such fluoride sources.
  • the plaque combatting effect of the alginate ingredient in the dentifrice composition as previously described is supplemented with an effective amount of an enzyme material selected from any of the enzymes which are known to be useful in dental hygiene.
  • an enzyme material selected from any of the enzymes which are known to be useful in dental hygiene.
  • Such enzymes are well known and comprise a broad spectrum including those which act according to hydrolysis, oxidation or reduction modes of action.
  • Typical of such enzymes are proteases such as pepsin, pancreatin, trypsin and the like or amylases and glucose oxidase.
  • the amount of such enzymes incorporated in dentifrices is rather widely known.
  • a preferred enzyme is dextra- nase which in a typical dentifrice formulation will be present to the extent of 100-200,000 units (1 unit equals enzyme activity needed to produce one milligram equivalent of isomaltose monohydrate in one hour at 40 degrees C.) per gram of formulation.
  • a typical denti ⁇ frice of the invention will contain from about 0.005 % to about 0.05 % by weight of dextranase having an potency of 15,000 units per milligram.
  • Preferred thickening agents are methyl cellu ⁇ lose, hydroxyethyl cellulose and water-soluble salts of cellulose ethers such as sodium carboxymethyl cellulose and sodium carboxymethyl hydroxyethyl cellulose.
  • Natural gums such as gum karaya, gum arabic, and gum tragacanth can also be used.
  • Colloidal magnesium aluminum silicate or finely divided silica can also be used as part of the thickening agent to further improve texture.
  • Thickening agents in an amount from 0.5% to 5.0% by weight of the total composition can be used.
  • a preferrred toothpaste of the invention includes from about 3% to about 15% by weight of polyvinylpyr- rolidone having a molecular weight from about 30,000 to about 90,000, which enhances the adhesion of the tooth- paste to the tooth surface. This adhesion brings the water-soluble alginate chelating agent into better contact with the plaque, thereby increasing its effect on weakening the mechanical structure of the plaque.
  • Flavoring agents are also commonly added to dental compositions and may be added to this invention as well. Suitable flavoring agents include oil of winter- green, oil of peppermint, oil of spearmint, oil of sassafras, and oil of clove. Sweetening agents which can be used include saccharin, dextrose, levulose and sodium cycla ate. Flavoring agents are generally used in dentifrices at levels of from about 0.01% to 2% by weight and sweetening agents at levels of from about 0.05% to about 2% by weight.
  • the dentifrice compositions of this invention may be prepared by any conventional means and with any of the commonly used ingredients, so long as they are substantially devoid of calcium or other divalent ions which form chelates with alginates.
  • mouthwash components can comprise the carrier for the alginate chelators of the present invention.
  • Mouth ⁇ washes generally comprises a water/ethyl alcohol solu ⁇ tion and preferably other ingredients such as flavor, sweeteners, humectants and sudsing agents such as those mentioned above for dentifrices.
  • the humectants, such as glycerine and sorbitol, give a moist feel to the mouth.
  • the mouthwashes of the invention comprise 5% to 60% (preferably 10% to 25%) ethyl alcohol; 0% to 20% (preferably 5% to 20%) glycerine or other humectant; 0% to 2% (preferably 0.1% to 1.5%) sudsing agent; 0% to 0.5% (preferably 0.05% to 0.5%) sweetening agent such as saccarin; and 0% to 0.3% (preferably 0.05% to 0.3%) flavoring agent; and the balance water.
  • the amount of bis-biguanide antibacte ⁇ rial agent in mouthwash is typically from about 0.01% to about 1.2% by weight.
  • EXAMPLE 1 This example depicts a mouthwash composition according to this invention.
  • PAB disodium phosphate O aq. 1.5 % citric acid 1 aq. 1.0 % ethyl alcohol 10.0 % distilled water up to 100.0%
  • EXAMPLE 2 This example depicts a chewing tablet composition according to this invention.
  • carbowax 6000 2.0 % aromatic substances (micro-capsules) 0.5 % coloring matter 0.1 %
  • This example depicts a lozenge tablet composition according to this invention.
  • EXAMPLE 5 This example illustrates the preparation of a toothpaste according to the invention.
  • Solution B which is a rather viscous compositin, 0 must be mixed thoroughly. Solution B is then added to solution A with vigorous stirring. The toothpaste preparation is complete when the two solutions have been uniformly blended.
  • a toothpaste having the following composition was prepared by the process of Example 1:
  • This example illustrates another toothpase accord ⁇ ing to the invention.
  • a toothpaste having the following composition was prepared by the procedure of Example 1: A. glycine 4. 0 % trisodium citrate 1. 0 % sodium dodecyl sulfate 0. 5 % polyethylene glycol (M. W. 8000) 7. 5 % water q. s. p. 100.0 %
  • This example illustrates an additional embodiment of the invention.
  • a toothpaste having the following composition was prepared by the procedure of Example 1:
  • This example illustrates a tooth-gel of the inven- tion containing a magnesium compound.
  • FDC yellow (1% solution) 0.15 % glycerine 15.0 % sodium alginate TCU/53 6.5 % methyl paraben 0.2 % protenal MgF 10/60 2.0 % flavour 0.05 %
  • a preferred toothpaste of the invention includes a quantity of a magnesium conpound, e.g., MgF2, which may be present in amounts from about 0.2 % to about 3 % by weight.
  • MgF2 magnesium conpound

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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)
  • Oral & Maxillofacial Surgery (AREA)
  • Cosmetics (AREA)

Abstract

Une composition dentifrice efficace destinée à affaiblir la structure de la plaque dentaire pour faciliter l'enlèvement de celle-ci; cette composition comprend une quantité efficace d'un sel d'acide alginique soluble dans l'eau pour produire une réduction importante du volume de la plaque dentaire sur les dents d'un utilisateur, et un porteur acceptable permettant son utilisation dans la cavité orale; ledit dentifrice est en outre exempt d'ions calcium.
PCT/US1985/002211 1984-11-08 1985-11-08 Dentifrice contenant un agent de chelation de calcium d'alginate Ceased WO1986002831A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US66968984A 1984-11-08 1984-11-08
US66947684A 1984-11-08 1984-11-08
US669,689 1984-11-08
US669,476 1984-11-08
US79543985A 1985-11-06 1985-11-06
US795,439 1991-11-21

Publications (1)

Publication Number Publication Date
WO1986002831A1 true WO1986002831A1 (fr) 1986-05-22

Family

ID=27418190

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1985/002211 Ceased WO1986002831A1 (fr) 1984-11-08 1985-11-08 Dentifrice contenant un agent de chelation de calcium d'alginate

Country Status (3)

Country Link
EP (1) EP0199806A4 (fr)
AU (1) AU5068985A (fr)
WO (1) WO1986002831A1 (fr)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0286250A1 (fr) * 1987-03-23 1988-10-12 Btg International Limited Composition pour le traitement de maladies parodontales
US4935226A (en) * 1987-08-21 1990-06-19 Lever Brothers Co. Toothpastes
US5093170A (en) * 1990-06-25 1992-03-03 The Procter & Gamble Co. Use of a carboxy-substituted polymer to inhibit plaque formation without tooth staining
US5213789A (en) * 1990-08-02 1993-05-25 The Procter & Gamble Company Use of a carboxy-containing copolymer to inhibit plaque formation without tooth staining
US5292501A (en) * 1990-06-25 1994-03-08 Degenhardt Charles R Use of a carboxy-substituted polymer to inhibit plaque formation without tooth staining
US5320831A (en) * 1992-12-30 1994-06-14 The Procter & Gamble Company Oral compositions
US5320830A (en) * 1992-12-30 1994-06-14 The Procter & Gamble Company Oral compositions
EP0681466A4 (fr) * 1993-01-19 1996-07-31 Gillette Co Bain de bouche.
US5560905A (en) * 1994-05-13 1996-10-01 The Proctor & Gamble Company Oral compositions
US5578294A (en) * 1994-05-13 1996-11-26 The Procter & Gamble Company Oral compositions
US5849271A (en) * 1995-06-07 1998-12-15 The Procter & Gamble Company Oral compositions
US5885552A (en) * 1993-01-19 1999-03-23 Gillette Canada Inc. Mouthrinse
US20130039866A1 (en) * 2010-07-08 2013-02-14 Obshchestvo S Ogranichennoj Otvetstvennostyu "WDS" Composition for the prophylaxis of candidiasis
KR101810140B1 (ko) 2015-08-11 2017-12-19 (주)아모레퍼시픽 프라그 억제용 구강조성물

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE8502540L (sv) * 1984-06-12 1985-12-13 Colgate Palmolive Co Stabilt tandvardsmedel innehallande dextranas

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3947567A (en) * 1970-08-08 1976-03-30 Phoenix Research Inc. Effervescent cleansers
US4466954A (en) * 1981-12-29 1984-08-21 Lion Corporation Oral composition

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE744113C (de) * 1940-08-31 1945-01-26 Klosterfrau Mcm Vetrieb Gmbh Verfahren zur Herstellung von haltbaren kosmetischen und pharmazeutischen Zubereitungen
FR651M (fr) * 1960-06-14 1961-07-03

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3947567A (en) * 1970-08-08 1976-03-30 Phoenix Research Inc. Effervescent cleansers
US4466954A (en) * 1981-12-29 1984-08-21 Lion Corporation Oral composition

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Cosmetics: Science and Technology 2nd Ed. Vol. 1, 1972, S.D. GERSHON et al "Dentrifices" pp. 490-493 *
See also references of EP0199806A4 *

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0286250A1 (fr) * 1987-03-23 1988-10-12 Btg International Limited Composition pour le traitement de maladies parodontales
US5087451A (en) * 1987-03-23 1992-02-11 National Research Development Corporation Treatment of periodontal disease
US4935226A (en) * 1987-08-21 1990-06-19 Lever Brothers Co. Toothpastes
US5093170A (en) * 1990-06-25 1992-03-03 The Procter & Gamble Co. Use of a carboxy-substituted polymer to inhibit plaque formation without tooth staining
US5292501A (en) * 1990-06-25 1994-03-08 Degenhardt Charles R Use of a carboxy-substituted polymer to inhibit plaque formation without tooth staining
US5213789A (en) * 1990-08-02 1993-05-25 The Procter & Gamble Company Use of a carboxy-containing copolymer to inhibit plaque formation without tooth staining
US5437856A (en) * 1992-12-30 1995-08-01 The Procter & Gamble Company Oral compositions
US5320830A (en) * 1992-12-30 1994-06-14 The Procter & Gamble Company Oral compositions
US5320831A (en) * 1992-12-30 1994-06-14 The Procter & Gamble Company Oral compositions
EP0681466A4 (fr) * 1993-01-19 1996-07-31 Gillette Co Bain de bouche.
US5885552A (en) * 1993-01-19 1999-03-23 Gillette Canada Inc. Mouthrinse
US5560905A (en) * 1994-05-13 1996-10-01 The Proctor & Gamble Company Oral compositions
US5578294A (en) * 1994-05-13 1996-11-26 The Procter & Gamble Company Oral compositions
US5620679A (en) * 1994-05-13 1997-04-15 The Procter & Gamble Company Oral compositions
US5622689A (en) * 1994-05-13 1997-04-22 The Procter & Gamble Company Oral compositions
US5849268A (en) * 1994-05-13 1998-12-15 The Procter & Gamble Company Oral compositions
US5849271A (en) * 1995-06-07 1998-12-15 The Procter & Gamble Company Oral compositions
US20130039866A1 (en) * 2010-07-08 2013-02-14 Obshchestvo S Ogranichennoj Otvetstvennostyu "WDS" Composition for the prophylaxis of candidiasis
KR101810140B1 (ko) 2015-08-11 2017-12-19 (주)아모레퍼시픽 프라그 억제용 구강조성물

Also Published As

Publication number Publication date
EP0199806A1 (fr) 1986-11-05
AU5068985A (en) 1986-06-03
EP0199806A4 (fr) 1988-06-13

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