WO1998010738A1 - Compositions de soins buccaux antimicrobienne - Google Patents

Compositions de soins buccaux antimicrobienne Download PDF

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Publication number
WO1998010738A1
WO1998010738A1 PCT/US1997/016015 US9716015W WO9810738A1 WO 1998010738 A1 WO1998010738 A1 WO 1998010738A1 US 9716015 W US9716015 W US 9716015W WO 9810738 A1 WO9810738 A1 WO 9810738A1
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Prior art keywords
phthalic acid
composition
acid compound
group
compositions
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PCT/US1997/016015
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English (en)
Inventor
Duane Larry Charbonneau
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The Procter & Gamble Company
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Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to AU41853/97A priority Critical patent/AU4185397A/en
Publication of WO1998010738A1 publication Critical patent/WO1998010738A1/fr

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    • 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
    • A61K8/22—Peroxides; Oxygen; Ozone
    • 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
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings

Definitions

  • compositions including therapeutic rinses, especially mouth rinses, as well as toothpastes, gels, tooth powders, chewing gums, mouth sprays, lozenges, and sachets, comprising a phthalic acid compound or salts/esters thereof, alone, or with a peroxide compound such as hydrogen peroxide, urea peroxide, calcium peroxide, and/or carbamate peroxide.
  • a peroxide compound such as hydrogen peroxide, urea peroxide, calcium peroxide, and/or carbamate peroxide.
  • These compositions are useful for treating or preventing topically-treatable microbial infections, especially diseases of the oral cavity, and/or breath malodor, in humans or other animals.
  • This invention further relates to a method for treating or preventing topically-treatable microbial infections, especially diseases of the oral cavity, such as gingivitis, plaque, periodontal disease, and oral malodor, in humans or other animals.
  • Bacteria are a part of the normal flora of the body. They also are prevalent on all mucous membrane surfaces as indigenous flora. Given the proper circumstances and opportunity to penetrate tissues, microbes from the indigenous flora set up infections.
  • Periodontal disease is believed to be associated with anaerobic bacterial infections. Periodontal disease affects the periodontum, which is the investing and supporting tissues surrounding a tooth (i.e., the periodontal ligament, the gingiva, and the alveolar bone). Gingivitis and periodontitis are inflammatory disorders of the gingiva and the periodontal ligament, respectively. Gingivosis and periodontosis are more severe conditions involving degenerative disorders of the tissue. Combinations of inflammatory and degenerative conditions are termed periodontitis complex.
  • Periodontal disease is a major cause of tooth loss in adults. Tooth loss from periodontal disease is a significant problem beginning at age 35. Even by age 15, it is estimated that about 4 out of 5 persons already have gingivitis and 4 out of 10 have periodontitis.
  • BACKGROUND REFERENCES Peroxy acids including monoperphthaiate, are known in the art as bleaching agents in laundry applications and for tooth staining as well as for disinfecting/sterilizing hard surfaces, cloth diapers, removable orthodontic appliances, etc.
  • European Patent Application No. 27,693, published April 29, 1981, Interox are known in the art as bleaching agents in laundry applications and for tooth staining as well as for disinfecting/sterilizing hard surfaces, cloth diapers, removable orthodontic appliances, etc.
  • Chemicals Limited discloses the magnesium salts of peroxycarboxylic acids, including the magnesium salt of monoperphthalic acid, and processes for preparing these compounds.
  • the compounds are used as bleaching agents in washing compositions.
  • U.S. Pat. No. 4,490,269 issued Dec. 25, 1984, Galiopo, discloses cleansing compositions comprising an effervescent agent and a monope ⁇ hthalate, or an effervescent agent and potassium monopersulfate and a monope ⁇ hthalate, as bleaching agents. These compositions are used to clean removable orthodontic appliances such as false teeth, dental plates and bridges.
  • a "singlet oxygen generating organic peroxy acid compound” includes monope ⁇ hthalic acid.
  • a preferred embodiment is the magnesium salt of the monope ⁇ hthalic acid in a pharmaceutically acceptable carrier including toothpaste, mouth rinse, chewing gum, mouth spray, lozenge and sachets.
  • the present invention relates to the su ⁇ rising discovery that when a phthalic acid compound or salts/esters thereof is used alone, or is used in combination with a peroxide compound, die compositions will be effective against plaque, gingivitis, periodontal disease, and oral malodor.
  • the present invention encompasses oral care compositions, including therapeutic rinses, especially mouth rinses, as well as toothpastes, gels, tooth powders, chewing gums, mouth sprays, lozenges, and sachets.
  • These compositions comprise a phthalic acid compound, or pharmaceutically-acceptable salts or esters thereof, alone, or combined with a peroxide compound.
  • compositions are effective in killing, and for a period of time suppressing the growth of, the microorganisms which cause topically- treatable infections, especially diseases of the oral cavity, such as plaque, gingivitis, periodontal disease, and breath malodor.
  • diseases of the oral cavity such as plaque, gingivitis, periodontal disease, and breath malodor.
  • the present invention relates to topical, oral care compositions and methods of treating or preventing topically-treatable microbial infections, especially diseases of the oral cavity, such as plaque, gingivitis, periodontal disease, and oral breath malodor in humans or other animals.
  • the methods comprise topically applying to the infected tissue or the at-risk tissue, a safe and effective amount of a phthalic acid compound or a salt or ester thereof, either alone, or combined with a safe and effective amount of a peroxide compound, including hydrogen peroxide, urea peroxide, calcium peroxide, and/or carbamate peroxide.
  • a phthalic acid compound has the general structure:
  • R is any substituent compatible with the carboxylate functionality of the aromatic ring, preferably hydrogen, substituted and unsubstituted saturated alkyl having from 1 to 20 carbon atoms (e.g., methyl, ethyl), substituted and unsubstituted aryl (e.g., phenyl, naphthyl), substituted and unsubstituted benzyl, chloro, fluoro, nitro, sulphonate, trifluoromethyl, trialkylammonium (e.g., trimethylammonium; triethylammonium), cyano, carboxylate (e.g., -OCOCH3), and alkoxy (e.g., methoxy, ethoxy).
  • R is any substituent compatible with the carboxylate functionality of the aromatic ring, preferably hydrogen, substituted and unsubstituted saturated alkyl having from 1 to 20 carbon atoms (e.g., methyl, ethyl), substituted and
  • R groups are hydrogen, saturated alkyl having from 1 to 20 carbon atoms, aryl, benzyl, chloro, fluoro, and alkoxy, and even more preferably R is hydrogen.
  • the present invention further relates to toothpastes, gels, tooth powders, mouth rinses, chewing gums, mouth sprays, lozenges, and sachets, as well as other therapeutic rinse compositions, which contain a safe and effective amount of a phthalic acid compound, alone or combined with a peroxide compound including hydrogen peroxide, urea peroxide, calcium peroxide, and/or carbamate peroxide.
  • the present invention relates to compositions and methods of treating or preventing topically-treatable microbial infections, especially diseases of the oral cavity (e.g. plaque, gingivitis, periodontal disease), and breath malodor, in humans or other animals by topically applying to the tissue, a safe and effective amount of either a phthalic acid compound or salts or esters thereof, alone, or combined with a peroxide compound.
  • the phthalic acid compound has the general structure: or its pharmaceutically-acceptable salts or esters, wherein the compound has one to four R groups, preferably two R groups, more preferably one R group; wherein R is any substituent compatible with the carboxylate functionality of the aromatic ring.
  • substituteduents compatible with the carboxylate functionality of the aromatic ring is meant substituents on the ring which do not react with carboxylate groups, thereby reducing the stability and effectiveness of the compounds, for the treatment of diseases of die oral cavity and breath malodor.
  • R is hydrogen, substituted and unsubstituted saturated alkyl having from 1 to 20 carbon atoms (e.g., methyl, ethyl), substituted and unsubstituted aryl (e.g., phenyl, naphthyl), substituted and unsubstituted benzyl, chloro, fluoro, nitro, sulphonate, trifluoromethyl, trialkylammonium (e.g., trimethylammonium; triethylammonium), cyano, carboxylate (e.g., -OCOCH3), alkoxy (e.g., metJioxy, ethoxy), iodo, bromo, substituted or unsubstituted arnino, or amido group.
  • alkyl having from 1 to 20 carbon atoms
  • aryl e.g., phenyl, naphthyl
  • substituted and unsubstituted benzyl chloro,
  • R groups are hydrogen, saturated alkyl having from 1 to 20 carbon atoms, aryl, benzyl, chloro, fluoro, and alkoxy. Particularly preferred is where R is hydrogen, or pharmaceutically-acceptable salts or esters thereof. Phthalic acid, isophthalic acid, and terephthalic acid are most preferred.
  • compositions comprising phthalic acid compound (or salts/esters thereof), alone or in combination with a peroxide compound, are very effective against anaerobic bacteria, especially the anaerobic bacteria found in the oral cavity.
  • the present invention is also the result of the su ⁇ rising discovery of the effectiveness of phthalic acid compounds, which are believed to make this specific class of compounds very desirable for treating anaerobe infections, especially diseases' of the oral cavity. Further, phthalate is relatively stable to enzymatic decomposition, especially to the enzymes found in the oral cavity, thereby allowing an effective amount of the phthalate compound to exert its antibacterial activity jn vivo.
  • the compositions and methods comprise a peroxide compound selected from the group consisting of hydrogen peroxide, calcium peroxide, urea peroxide, carbamate peroxide and mixtures thereof; more preferably calcium peroxide, urea peroxide, carbamate peroxide and mixtures thereof.
  • compositions and methods of treatment of the present invention are believed to be safe for chronic treatment of topically-treatable microbial infections, especially diseases of the oral cavity.
  • diacyl peroxides i.e. benzoyl peroxide
  • an aqueous decomposition of phthalate alone or with hydrogen peroxide, urea peroxide, calcium peroxide, and/or carbamate peroxide does not involve the generation of significant free radicals. This property is especially relevant for safety reasons, since free radicals are known to have detrimental effects on tissues and can lead to severe inflammatory responses. Long-term treatment with free radical generators is therefore not desirable.
  • the absence of free radical mechanisms for the decomposition of phthalate strongly indicates that long-term treatment with phthalate should be more safe and pose less significant health hazards.
  • esters and salts of the substituted or unsubstituted phthalic acid compounds which have the same general antimicrobial properties, and which are acceptable from a toxicity viewpoint.
  • Nonlimiting examples of pharmaceutically-acceptable salts include alkali metal (e.g., sodium, potassium), alkaline earth metal (e.g., calcium, magnesium), non-toxic heavy metal, and trialkyl ammonium (e.g., trimethylammonium).
  • Preferred salts include divalent cations (e.g., magnesium, calcium).
  • topically-treatable microbial infections is meant oral tissue infections or oral conditions which are caused by or involve anaerobic bacteria, and may be treated by topical application.
  • the tissues that may be treated by topical application are oral external membranes and mucocutaneous orifices.
  • infections or conditions mat may be treated by topical application include anaerobe infections of the oral cavity (e.g., Vincent's disease, periodontal disease, periodontitis complex, etc.), and conditions such as breath malodor.
  • diseases of the oral cavity is meant diseases which are initiated and/or pe ⁇ etuated by bacteria in the oral cavity, especially anaerobic bacteria, and includes such diseases as, for example, periodontal disease, gingivitis, periodontitis, gingivosis, periodontosis, periodontitis complex, and other inflammatory and or degenerative conditions of the tissues within the oral cavity, plus caries, Vincent's disease, trench mouth, and oral malodor.
  • dentoalveolar infections e.g., cellulitis of the jaw; osteomyelitis of the jaw), acute necrotizing ulcerative gingivitis (i.e., Vincent's infection), infectious stomatitis (i.e., acute inflammation of the buccal mucosa), and Noma (i.e., gangrenous stomatitis or cancrum oris).
  • dental abscesses e.g., cellulitis of the jaw; osteomyelitis of the jaw
  • acute necrotizing ulcerative gingivitis i.e., Vincent's infection
  • infectious stomatitis i.e., acute inflammation of the buccal mucosa
  • Noma i.e., gangrenous stomatitis or cancrum oris
  • Oral and dental infections are more fully disclosed in Finegold, ⁇ naerobic Bacteria in Human Diseases, chapter 4, pp 78-104, and chapter 6, pp 115-154 (Academic Press,
  • safe and effective amount as used herein is meant an amount of a phthalic acid compound, or a pharmaceutically-acceptable salt or ester thereof, or peroxide compound (hydrogen peroxide, calcium peroxide, urea peroxide, carbamate peroxide) high enough to significantly (positively) modify the infection to be treated, but low enough to avoid serious side effects (at a reasonable benefit/risk ratio), within the scope of sound medical judgment.
  • peroxide compound hydrogen peroxide, calcium peroxide, urea peroxide, carbamate peroxide
  • a phthalic acid compound or its pharmaceutically-acceptable salt or ester, and of the peroxide compound will vary with the particular infection (e.g., disease of the oral cavity) being treated, the age and physical condition of the patient being treated, the severity of the infection, the duration of treatment, the nature of concurrent therapy, the specific form (i.e., acid, salt, and/or ester) of the phthalic acid or peroxide compound employed, and the particular vehicle from which the phthalic acid or peroxide compound is applied.
  • the safe and effective amount of phthalic acid compound for the oral cavity is from about 1 mg to about 1000 mg, more preferably from about 1 mg to about 600 mg, and even more preferably from about 10 mg to about 300 mg.
  • the level of phthalic acid in the topical, oral compositions of the present invention comprise from about 0.01% to about 25%, preferably from about 0.01% to about 5%, more preferably from about 0.05% to about 3% by weight of the composition, even more preferred from about 0.1% to about 2%, by weight.
  • mouth rinse compositions have a concentration of phthalic acid compound in the range of from about 0.05% to about 5%, with from about 0.05% to about 3% more preferred, and from about 0.1% to about 2% by weight most preferred.
  • Mouth sprays preferably have phthalic acid compound concentrations of from about 0.1 % to about 25%, with from about 0.5% to about 10% by weight most preferred.
  • the concentration of phthalic acid compound is in the range of from about 0.1% to about 10%, with from about 0.1% to about 2% by weight preferred.
  • Chewable tablets, chewing gums, lozenges, and sachets are generally formulated into compositions of individual unit size preferably containing from about 20 mg to about 500 mg of phthalic acid compound, preferably from about 10 mg to about 100 mg, per unit used in the oral cavity.
  • the level of peroxide compound in the compositions of the present invention is from about 0.3% to about 6%, preferably from about 0.3% to about 3%, more preferable from about 1% to about 2%, even more preferably about 1.5%, by weight of the composition.
  • the urea and carbamate peroxide can be mixed directly into the composition and maintain storage stability.
  • hydrogen peroxide preferably, is stored separately or packaged separately from the composition until just prior to use of the composition by the consumer.
  • the safe and effective amount of the phthalic acid and peroxide compound may be topically applied to the gingival tissue of the oral cavity in several conventional ways.
  • the gingival tissue may be rinsed with a solution (e.g., mouth rinse, mouth spray) containing the phthalic acid alone or with the peroxide compound; or if the phthalic acid, alone, or with the peroxide compound is included in a dentifrice (e.g., toothpaste, gel or tooth powder), the gingival tissue is bathed in the liquid and/or lather generated by brushing the teeth.
  • a solution e.g., mouth rinse, mouth spray
  • a dentifrice e.g., toothpaste, gel or tooth powder
  • Non-limiting examples include applying a gel or paste, which contains the phthalic acid alone, or with the peroxide compound, directly to the gingival tissue; chewing gum or chewing tablets, that contain the phthalic acid alone, or with the peroxide compound; and sucking on a lozenge or sachet which contains the phthalic acid alone, or with the peroxide compound.
  • Preferred methods of applying the phthalic acid and peroxide compound to the gingival tissue are via rinsing with a mouth rinse solution and via brushing with a dentifrice.
  • Other methods of topically applying the phthalic acid and peroxide compound to the gingival tissue are apparent to those skilled in the art.
  • the treatment be done in such a way that the pH, particularly the pH of the oral cavity, during treatment is maintained at a pH of from about 5 to about 8, more preferably from about 6.5 to 7.5, even more preferably about 7.0 to about 7.5.
  • buffering e.g., the oral cavity
  • Non-limiting examples of pharmaceutically-acceptable buffers include citrate, citrate/bicarbonate and phosphate buffers. It is also preferred that, in the method of treating diseases of the oral cavity of the present invention, the phthalic acid and peroxide compound not be intentionally ingested.
  • the concentration of the phthalic acid and peroxide compound in the composition of the present invention depends on the type of composition (e.g., toothpaste, mouth rinse, lozenge) used to apply the phthalic acid and peroxide compound to the gingival tissue, due to differences in efficiency of the compositions contacting the tissue, and due also to the amount of the composition generally used.
  • type of composition e.g., toothpaste, mouth rinse, lozenge
  • compositions of the present invention comprising phthalic acid compound, without a peroxide compound, preferably these compositions are either essentially free of benzoic acid or water soluble salts thereof, of have greater than 1%, preferably 1.25% of benzoic acid, or water soluble salts thereof, especially when the phthalic acid compound is potassium biphthalate.
  • a safe and effective amount of phthalic acid and peroxide compound is preferably applied to the gingival tissue preferably for at least about 10 seconds, preferably from about 20 seconds to about 10 minutes, more preferably from about 30 seconds to about 60 seconds.
  • the method often involves expectoration of most of the compositions following such contact, preferably followed with rinsing, e.g. with water.
  • the frequency of such contact is preferably from about once per week to about four times per day, more preferably from about thrice per week to about three times per.day, even more preferably from about once per day to about twice per day.
  • the period of such treatment typically ranges from about one day to a lifetime.
  • the duration of treatment is preferably from about 3 weeks to about 3 months, but may be shorter or longer depending on the severity of the oral disease being treated, the particular delivery form utilized and the patient's response to treatment.
  • the present invention further relates to compositions for use in d e methods of treatments according to the present invention.
  • the present invention further relates to rinses, especially mouth rinses, as well as toothpastes, gels, tooth powders, mouth sprays, chewing gums, lozenges, and sachets comprising: ( 1) a safe and effective amount of a phthalic acid compound, or pharmaceutically- acceptable salts or esters thereof; and (2) a pharmaceutically-acceptable topical, oral carrier; or
  • compositions which may be used in these compositions are as described above (preferred being the unsubstituted aromatic ring (i.e., where R is hydrogen). These compositions are topically applied to infected tissue of the oral cavity, and retained there in such a way and for such time as to be effective for treating or preventing diseases of the oral cavity according to the method of the present invention. It is preferred that these compositions not be intentionally ingested. Toothpaste (including gels) and mouth rinses are preferred.
  • pharmaceutically-acceptable excipient or “pharmaceutically-acceptable topical, oral carrier”, as used herein, is meant one or more compatible solid or liquid filler diluents or encapsulating substances which are suitable for topical, oral administration.
  • compatible is meant that the components of the composition are capable of being commingled without interaction in a manner which would substantially reduce the composition's stability and or efficacy for treating or preventing topically-treatable anaerobe infections, especially diseases of the oral cavity, according to the method of the present invention.
  • the carrier be buffered, or contain a buffer, capable of maintaining the pH of the oral cavity during use from about pH 5 to about pH 8, more preferred being pH from about 7.0 to about 7.5.
  • buffers include citrate, citrate/bicarbonate and phosphate buffers.
  • the carriers of the present invention can include the usual and conventional components of toothpastes (including gels and tooth powders), mouth rinses, mouth sprays, chewing gums, lozenges, and sachets as more fully described hereinafter.
  • toothpastes including gels and tooth powders
  • mouth rinses including mouth rinses
  • mouth sprays including chewing gums
  • lozenges lozenges
  • sachets as more fully described hereinafter.
  • the carriers are limited to materials which are free of hydroxyl groups and normally also to materials which do not contain reactive sites, such as ammo, amido, iodo, bromo, and sulfhyryl groups, and unsaturated, imino, and thioether linkages when the composition of the present invention is to be stored for any appreciable period of time.
  • Toothpaste compositions conventionally contain abrasives, sudsing agents, binders, humectants, flavoring and sweetening agents, which generally cannot be stored with the hydrogen peroxide compound. Therefore, toothpaste of the present invention which include hydrogen peroxide, will normally be two component compositions in separate containers or chambers, to be combined just prior to use and thereafter the composition is used immediately after preparation.
  • the choice of a carrier to be used is basically determined by the way the composition is to be introduced into the oral cavity.
  • a toothpaste including gels
  • a "toothpaste carrier” is chosen as disclosed in, e.g., U.S. Pat. No. 3,988,433, to Benedict, the disclosure of which is inco ⁇ orated herein by reference (e.g., abrasive materials, sudsing agents, binders, humectants, flavoring and sweetening agents, etc.).
  • a mouth rinse carrier is chosen, as disclosed in, e.g., U.S. Pat. No. 3,988,433 to Benedict (e.g., water, flavoring and sweetening agents, possibly an organic solvent such as ethanol, etc.).
  • a mouth spray carrier is chosen or if a lozenge is to be used, then a "lozenge carrier” is chosen (e.g., a candy base), candy bases being disclosed in, e.g., U.S. Pat. No. 4,472,373, to Ryan, and in U.S. Pat. No. 4,083,955, to Grabenstetter et al., both of which are inco ⁇ orated herein by reference; if a chewing gum is to be used, then a "chewing gum carrier” is chosen, as disclosed in, e.g., U.S. Pat. No. 4,472,373 to Ryan, and in U.S. Pat. No.
  • compositions of the subject invention are in the form of dentifrices, such as toothpastes, tooth gels and tooth powders.
  • Components of such toothpaste and tooth gels generally include one or more of a dental abrasive (from about 10% to about 50%), a surfactant (from about 0.5% to about 10%), a thickening agent (from about 0.1% to about 5%), a humectant (from about 10% to about 55%), a flavoring agent (from about 0.04% to about 2%), a sweetening agent (from about 0.1% to about 3%), a coloring agent (from about 0.01% to about 0.5%) and water (from about 2% to about 45%).
  • a dental abrasive from about 10% to about 50%
  • a surfactant from about 0.5% to about 10%
  • a thickening agent from about 0.1% to about 5%
  • a humectant from about 10% to about 55%)
  • a flavoring agent from about 0.04% to about 2%
  • Such toothpaste may also include one or more of an anticarie agent (from about 0.05% to about 0.3% as fluoride ion), and an anticalculus agent (from about 0.1% to about 13%). Tooth powders, of course, contain substantially all non-liquid components.
  • compositions of the subject invention are mouthwashes and mouth sprays.
  • Components of such mouthwashes and mouth sprays typically include one or more of water (from about 45% to about 95%), ethanol (from about 0% to about 25%), a humectant (from about 0% to about 50%), a surfactant (from about 0.01% to about 7%), a flavoring agent (from about 0.04% to about 2%), a sweetening agent (from about 0.1% to about 3%), and a coloring agent from about 0.001% to about 0.5%).
  • Such mouthwashes and mouth sprays may also include one or more of an anticaries agent (from about 0.05% to about 0.3% as fluoride ion), and an anticalculus agent (from about 0.1% to about 3%).
  • compositions of the subject invention are dental solutions.
  • Components of such dental solutions generally include one or more of water (from about 90% to about 99%), preservative (from about 0.01 % to about 0.5%), thickening agent (from 0% to about 5%), flavoring agent (from about 0.04% to about 2%), sweetening agent (from about 0.1% to about 3%), and surfactant (from 0% to about 5%).
  • Oral gel compositions typically include one or more of water (from 0% to about 99%), a humectant such as glycerin, (from 0% to about 99%), a thickening agent (from about 0.1% to about 5%), a flavoring agent (from about 0.04% to abut 2%), and a sweetening agent (from about 0.01% to about 0.5%).
  • a humectant such as glycerin
  • a thickening agent from about 0.1% to about 5%
  • a flavoring agent from about 0.04% to abut 2%
  • a sweetening agent from about 0.01% to about 0.5%).
  • Chewing gum compositions typically include one or more of a gum base (from about 50% to about 99%), a flavoring agent (from about 0.4% to about 2%) and a sweetening agent (from about 0.01% to about 20%).
  • compositions of the present invention are: A. Abrasives
  • Dental abrasives useful in the topical, oral carriers of the compositions of the subject invention include many different materials.
  • the material selected must be one which is compatible within the composition of interest and does not excessively abrade dentin.
  • Suitable abrasives include, for example, silicas including gels and precipitates, insoluble sodium poly etaphosphate, hydrated alumina, and resinous abrasive materials.
  • a class of preferred abrasives for use in the subject compositions is the paniculate thermo- setting polymerized resins as described in U.S. Pat. No. 3,070,510 issued to Cooley & Grabenstetter on Dec. 25, 1962.
  • Suitable resins include, for example, melamines, phenolics, ureas, melamine- ureas, melamine-formaldehydes, urea-formaldehyde, melamine-urea-formaldehydes, cross-linked epoxides, and cross-linked polyesters.
  • Silica dental abrasives are also preferred in the compositions of the subject invention.
  • the silica abrasive polishing material generally has an average particle size ranging between about 0.1 and about 30 microns, preferably between about 5 and about 15 microns.
  • the abrasive can be precipitated silica or silica gels such as the silica xerogels described in U.S. Pat. No. 3,538,230 issued to Pader & Wiesner on Mar. 2, 1970, and in U.S. Pat. No. 3,862,307 issued to DiGuilio on Jan. 21 , 1975.
  • Preferred precipitated silica materials are those marketed by the J. M. Huber Co ⁇ oration under the tradename Zeodent®, particularly the silica carrying the designation Zeodent 1 19®. These silica abrasives are described in U.S. Pat. No. 4,340.583 issued to Wason on Jul. 29, 1982.
  • abrasives can be used. All of the above patents regarding dental abrasives are incorporated herein by reference.
  • the total amount of abrasive in dentifrice compositions of the subject invention preferably range from about 10% to about 70% by weight; toothpastes preferably contain from about 10% to about 50% by weight of abrasives.
  • Solution, mouth spray, mouthwash and oral gel compositions of the subject invention typically contain no abrasive.
  • Suitable sudsing agents are those which are reasonably stable and form foam throughout a wide pH range, preferably nonsoap anionic organic synthetic detergents.
  • examples of such agents are water-soluble salts of alkyl sulfate having from 10 to 18 carbon atoms in the alkyl radical, such as sodium lauryl sulfate.
  • Other somewhat more reactive detergents include water-soluble salts of sulfonated monoglycerides of fatty acids having from 10 to 18 carbon atoms, such as sodium monoglyceride sulfonates; salts of C J to C j g fatty acid amides of taurine, such as sodium N- methyl-N-palmitoyl tauride; salts of C JQ to C
  • Nonionic synthetic detergents containing reactive hydroxyl groups which can be used with the oral compositions of the present invention should not be part of the compositions to be stored for long periods of time containing the hydrogen peroxide.
  • Nonionic synthetic detergents may be broadly defined as compounds produced by the condensation of alkylene oxide groups (hydrophilic in nature) with an organic hydrophobic compound which may be aliphatic or alkyl- aromatic in nature. The length of the hydrophilic or polyoxyalkylene radical which is condensed with any particular hydrophobic group can be readily adjusted to yield a water-soluble compound having the desired degree of balance between hydrophilic and hydrophobic elements.
  • nonionic synthetic detergent is made available on the market under the trade name of "Pluronic.” These compounds are formed by condensing ethylene oxide with a hydrophobic base formed by the condensation of propylene oxide with propylene glycol.
  • the hydrophobic portion of the molecule which, of course, exhibits water insolubility, has a molecular weight of from about 900 to about 5,000.
  • the addition of polyoxyethylene radicals to this hydrophobic portion tends to increase the water solubility of the molecule as a whole and the liquid character of the products is retained up to the point where polyoxyethylene content is about 50% of the total weight of the condensation product.
  • the sudsing agent can be present in the dentifrice compositions of this invention in an amount from about 0.5% to about 10%, preferably from about 1 % to about 5%, by weight of the total compositions.
  • Preferred fluorides are sodium, indium, and stannous fluorides, and sodium monofluorophosphate. Suitable fluorides are disclosed in U.S. Pat. No. 3,535,421, Briner & Widder, issued Oct. 20, 1979, which is inco ⁇ orated herein by reference.
  • D. Thickening Agents are disclosed in U.S. Pat. No. 3,535,421, Briner & Widder, issued Oct. 20, 1979, which is inco ⁇ orated herein by reference.
  • thickening material In preparing toothpaste or gels, it is necessary to add some thickening material to provide a desirable consistency.
  • polymeric polyester compounds e.g., polyethylene or polypropylene oxide (M.W. 300 to 1,000,000), capped with alkyl or acyl groups containing 1 to about 18 carbon atoms will react with the hydrogen peroxide.
  • preferred thickening agents are 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 of finely divided silica can be used as part of the thickening agent to further improve texture.
  • Thickening agents in an amount from about 0.5% to about 5.0% by weight of the total toothpaste or gel composition can be used. Higher concentrations can be used for chewing gums, lozenges and sachets.
  • humectant Another optional component of the topical, oral carriers of the compositions of the subject invention is a humectant.
  • the humectant serves to keep toothpaste compositions from hardening upon exposure to air, and to give compositions a moist feel to the mouth.
  • Certain humectants can also impart desirable sweetness of flavor to the subject compositions.
  • the humectant, on a pure humectant basis generally comprises from about 0% to about 70%, preferably from about 2% to about 55%, by weight of the compositions herein.
  • Suitable humectants for use in compositions of the subject invention include edible polyhydric alcohols such as glycerin, sorbitol, xylitol, polyethylene glycol, and propylene glycol, especially sorbitol and glycerin.
  • edible polyhydric alcohols such as glycerin, sorbitol, xylitol, polyethylene glycol, and propylene glycol, especially sorbitol and glycerin.
  • Suitable flavoring agents include menthol, oil of wintergreen, oil of peppermint, oil of spearmint, oil of sassafras, and oil of clove.
  • Sweetening agents which can be used include sucrose, glycose, saccharin, dextrose, levulose, saccharin salts, thaumatin, aspadame, D-tryptophan, dihydrochalcones, acesulfame and cyclamate salts, especially sodium cyclamate and sodium saccharin.
  • a composition preferably contains from about 0.1% to about 10% of those agents.
  • the hydrogen peroxide will be formulated into a composition consisting essentially of an inert organic or inorganic carrier selected for its limited reactivity with the oxidizing material. The primary function of the inert material is to support the hydrogen peroxide either in a single composition or as part of a two-component composition.
  • the organic carrier can either be a liquid or a soft wax, preferably a liquid.
  • the organic carrier can desirably be a saturated nonionic synthetic detergent of the ethoxylated nonionic type capped with an alkyl or acyl group to eliminate the reactive hydroxy group.
  • Nonionic synthetic detergents can be broadly defined as compounds produced by the condensation of alkylene oxide groups (hydrophilic in nature) with an organic hydrophobic compound, which may be aliphatic or alkyl aromatic in nature. The length of the hydrophilic or polyoxyalkylene radical which is condensed with any particular hydrophobic group can be readily adjusted to yield a water-soluble compound having the desired degree of balance between hydrophilic and hydrophobic elements. Another class has semipolar characteristics.
  • Preferred classes of nonionic synthetic detergents are as follows:
  • the hydrophobic portion of the molecule which, of course, exhibits water insolubility, has a molecular weight of from about 900 to 5,000.
  • the addition of polyoxyethylene radicals to this hydrophobic portion tends to increase the water solubility of the molecule as a whole and the liquid character of the product is retained up to the point where the polyoxyethylene content is about 50% of the total weight of the condensation product.
  • the polyethylene oxide condensates of alkyl phenols e.g., the condensation products of alkyl phenols having an alkyl group containing from about 6 to 12 carbon atoms in either a straight-chain or branched-chain configuration with ethylene oxide, the said ethylene oxide being present in amounts equal to 5 to 25 moles of ethylene oxide per mole of alkyl phenol.
  • the condensates are "capped” as with group 1.
  • the alkyl substituent in such compounds may be derived from polymerized propylene, diisobutylene, octene, or nonene, for example. 3.
  • Those nonionic synthetic detergents derived from the condensation of ethylene oxide with the product resulting from the reaction of propylene oxide and ethylene diamine.
  • the condensates are "capped" as in group 1.
  • compounds containing from about 40% to about 80% polyoxyethylene by weight and having a molecular weight of from about 5,000 to about 11 ,000 resulting from the reaction of ethylene oxide groups with a hydrophobic base constituted of the reaction product of ethylene diamine and excess propylene oxide, said base having a molecular weight of the order of 2,500 to 3,000 are satisfactory. 4.
  • ethylene oxide e.g., a coconut alcohol ethylene oxide condensates having from 5 to 40 moles of ethylene oxide per mole of coconut alcohol, the coconut alcohol fraction having from 10 to 14 carbon atoms.
  • saturated fatty acids containing from 8 to 22 carbon atoms such as coconut fatty acid, lauric acid, cetic acid (also called cetylic), and stearic acid
  • SSF
  • Especially preferred organic carriers include mineral oil, saturated aliphatic hydrocarbons, diesters of propylene glycol and triesters of glycerine.
  • a thickened form of the mineral oil or aliphatic hydrocarbon is used as the organic diluent, the thickening agent being selected from a group of specific types of organic waxes.
  • These thickening agents have excellent compatibility and, when used in proper proportions with the mineral oil or hydrocarbons, are effective in producing a composition which has a viscosity within the range of normal toothpaste compositions, i.e., a Brookfield viscosity at 75°F of from about 15 to about 100.
  • Such composition can be spread from a squeezable tube onto a toothbrush and brushed upon the teeth in the conventional manner of toothpaste usage.
  • the thickening agents are selected from the group consisting of:
  • saturated fatty acid triglycerides having melting points of from about 130° to about 250°F;
  • microcrystalline waxes having a melting point of from about 130° to about 250°F and a penetration value of from about 0.5 to about 20 as determined by ASTM Test D-1321 ;
  • polyethylene waxes having a melting point of from about 130° to about 250°F and a penetration value at 77°F of from about 0.5 to about 20 as determined by ASTM Test D-1321.
  • any particular thickening agent in these compositions is selected so as to produce the desired Brookfield viscosity. Generally a level of thickening agent within the range of from about 5% to about 30% by weight of the composition is used.
  • the Brookfield viscosities quoted herein are determined on a Brookfield RVT 1/2 Heliopath Viscometer using an E spindle set at 2.5 ⁇ m rotational speed.
  • Type 1 thickening agents are triglycerides such as myristic acid triglyceride, stearic acid triglyceride, and palmitic acid triglyceride. Mixtures of saturated fatty acid triglycerides such as those which make up hydrogenated tallow, hydrogenated soybean oil and hydrogenated cottonseed oil are also suitable.
  • Type 2 thickening agents are White Micro Wax (melting point 163° to 169°F, penetration value 9) sold by International Wax Refining Company, Petrolite C-1035 (melting point 197° to 202°F, penetration 4-5), Be Square 195 (melting point 193° to 198°F, penetration 6-7), Ceramer 67 (melting point 200° to 215°F, penetration 2.5-3.5) and Petrolite C-8500 (melting point 200° to 210°F, penetration 4-7), all sold by Bareco Division of Petrolite Co ⁇ oration.
  • Type 3 thickening agents are Polywax 655 (melting point 215°F, penetration 3.0), Polywax 500 (melting point 185°F, penetration 5.0) and Polywax E2020 (melting point 242°F, penetration 1.0), all sold by Bareco Division of Petrolite Co ⁇ oration.
  • Inorganic carriers which can be present in the compositions of the present invention include alkaline earth and alkali metal surfaces.
  • Disperse carboxymethylcellulose in glycerine Dissolve disodium phosphate, potassium phthalate, sodium fluoride, and sodium saccharin in purified water. Add sorbitol solution and sodium alkylsulfate solution followed by flavor. Disperse silica and titanium dioxide in resulting solution. Add binder/glycerine dispersion and mix.
  • Dissolve disodium phosphate, potassium phthalate, sodium saccharin, and urea peroxide in purified water Add polysorbate 80 followed by glycerin and ethanol. Add flavor and mix.
  • Example 4 Dissolve disodium phosphate, potassium phthalate, sodium saccharin, and urea peroxide in purified water. Add polysorbate 80 followed by glycerin and ethanol. Add flavor and mix. Example 4
  • Paste Disperse carboxymethylcellulose in sorbitol solution. Add purified water followed by sodium phthalate, sodium fluoride, sodium saccharin, polyethylene glycol 32, sodium alkyl sulfate, ethanol and flavor. Disperse sodium bicarbonate and silica.
  • Gel Combine glycerine and water. Add poloxamer followed by flavor and phosphoric acid. Add hydrogen peroxide and mix.
  • Example 4 The toothpaste composition of Example 4 is formed by mixing, by co-extrusion from separate chambers of a toothpaste tube, Phases I and II, in a 1 : 1 ratio just prior to use.
  • Example S
  • Dissolve disodium phosphate, potassium phthalate, and sodium saccharin in purified water Add polysorbate 80 followed by glycerin and ethanol. Add flavor and mix.
  • Disperse carboxymethylcellulose in sorbitol solution Add purified water followed by sodium phthalate, sodium fluoride, sodium saccharin, polyethylene glycol 32, sodium alkyl sulfate, ethanol and flavor. Disperse sodium bicarbonate and silica.

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Abstract

L'invention a pour objet des compositions de soins buccaux dont des produits de rinçage thérapeutiques, notamment des produits de rinçage buccaux, ainsi que des pâtes et des poudres dentifrices, des gels, des chewing-gums, des sprays buccaux, des pastilles et des sachets qui comprennent un composé d'acide phtalique et leurs sels ou esters, utilisés seuls ou conjointement avec un composé peroxyde tel que le peroxyde d'hydrogène, le peroxyde de calcium, le peroxyde d'urée et/ou le peroxyde de carbamate. Ces compositions sont utiles dans le traitement ou la prévention d'infections microbiennes pouvant être traitées localement, en particulier des maladies de la cavité buccale, et/ou pour lutter contre la mauvaise haleine chez des personnes ou des animaux. L'invention se rapporte également à une méthode de traitement ou de prévention des infections microbiennes pouvant être traitées localement, en particulier des maladies de la cavité buccale telles que la gingivite, la plaque dentaire, la parodontolyse, ainsi que pour lutter contre la mauvaise haleine chez des personnes ou des animaux.
PCT/US1997/016015 1996-09-16 1997-09-10 Compositions de soins buccaux antimicrobienne WO1998010738A1 (fr)

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AU41853/97A AU4185397A (en) 1996-09-16 1997-09-10 Antimicrobial oral care compositions

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US08/714,669 1996-09-16

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US5972374A (en) * 1998-04-02 1999-10-26 Theisen; Thomas Chewing gum with teeth whitener
WO2008024006A2 (fr) * 2006-08-21 2008-02-28 Przedsiebiorstwo Produkcji Farmaceutycznej Gemi Préparation pharmaceutique
WO2011006263A1 (fr) * 2009-07-17 2011-01-20 Klox Technologies Inc. Composition orale antibactérienne
US8632822B2 (en) 2008-11-07 2014-01-21 Klox Technologies Inc. Combination of an oxidant and a photoactivator for the healing of wounds
US8986719B2 (en) 2005-11-09 2015-03-24 Klox Technologies Inc. Teeth whitening compositions and methods
US9345648B2 (en) 2006-11-09 2016-05-24 Klox Technologies Inc. Photoactivatable oxygen-evolving compositions and methods for teeth whitening
US9655829B2 (en) 2012-09-14 2017-05-23 Valeant Pharmaceuticals International, Inc. Compositions and methods for teeth whitening
US10130706B2 (en) 2013-03-14 2018-11-20 Klox Technologies Inc. Biophotonic materials and uses thereof
US10207029B2 (en) 2014-04-01 2019-02-19 Klox Technologies Inc. Tissue filler compositions and methods of use
US10213373B2 (en) 2012-04-20 2019-02-26 Klox Technologies, Inc. Chromophore combinations for biophotonic uses
US10881736B2 (en) 2013-07-03 2021-01-05 Klox Technologies Inc. Biophotonic compositions comprising a chromophore and a gelling agent for treating wounds
US11116841B2 (en) 2012-04-20 2021-09-14 Klox Technologies Inc. Biophotonic compositions, kits and methods
US11421349B2 (en) 2014-10-31 2022-08-23 Klox Technologies Inc. Photoactivatable fibers and fabric media

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JPS4843869A (fr) * 1971-10-06 1973-06-25
FR2220270A1 (en) * 1973-03-10 1974-10-04 Leach Samuel Dental plaque inhibiting agents - which prevent deposition of calcium hydroxyapatite from saliva
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EP0083285A1 (fr) * 1981-12-23 1983-07-06 Société LE THERMOGENE Composition analgésique comprenant au moins un phtalate acide d'alcool neutralisé par une base
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US5972374A (en) * 1998-04-02 1999-10-26 Theisen; Thomas Chewing gum with teeth whitener
US8986719B2 (en) 2005-11-09 2015-03-24 Klox Technologies Inc. Teeth whitening compositions and methods
WO2008024006A2 (fr) * 2006-08-21 2008-02-28 Przedsiebiorstwo Produkcji Farmaceutycznej Gemi Préparation pharmaceutique
WO2008024006A3 (fr) * 2006-08-21 2008-08-07 Przed Produkcji Farmaceutyczne Préparation pharmaceutique
US9345648B2 (en) 2006-11-09 2016-05-24 Klox Technologies Inc. Photoactivatable oxygen-evolving compositions and methods for teeth whitening
US10485986B2 (en) 2008-11-07 2019-11-26 Klox Technologies Inc. Methods and compositions for treatment of pigmented lesions
US9597349B2 (en) 2008-11-07 2017-03-21 Klox Technologies Inc. Combination of an oxidant and a photoactivator for the healing of wounds
US10384072B2 (en) 2008-11-07 2019-08-20 Klox Technologies Inc. Combination of an oxidant and a photoactivator for the healing of wounds
US8911791B2 (en) 2008-11-07 2014-12-16 Klox Technologies Inc. Method for acne treatment using an oxidative-photoactivated composition
US8974833B2 (en) 2008-11-07 2015-03-10 Klox Technologies Inc. Combination of an oxidant and a photoactivator for the healing of wounds
US8637086B2 (en) 2008-11-07 2014-01-28 Klox Technologies Inc. Method for acne treatment using an oxidative-photoactivated composition
US8986745B2 (en) 2008-11-07 2015-03-24 Klox Technologies Inc. Oxidatitive photoactivated skin rejeuvenation composition comprising hyaluronic acid, glucosamine, or allantoin
US10758744B2 (en) 2008-11-07 2020-09-01 Klox Technologies Inc. Combination of an oxidant and a photoactivator for the wounds
US8632822B2 (en) 2008-11-07 2014-01-21 Klox Technologies Inc. Combination of an oxidant and a photoactivator for the healing of wounds
US9375446B2 (en) 2008-11-07 2016-06-28 Klox Technologies Inc. Oxidatitive photoactivated skin rejeuvenation composition comprising hyaluronic acid, glucosamine, or allantoin
US8658219B2 (en) 2008-11-07 2014-02-25 Klox Technologies Inc. Oxidatitive photoactivated skin rejeuvenation composition comprising hyaluronic acid, glucosamine, or allantoin
US11020609B2 (en) 2008-11-07 2021-06-01 Klox Technologies Inc. Methods and compositions for treatment of pigmented lesions
US10149985B2 (en) 2008-11-07 2018-12-11 Klox Technologies Inc. Methods and compositions for treating rosacea
US11691025B2 (en) 2008-11-07 2023-07-04 Klox Technologies Inc. Methods and compositions for reversing or mitigating skin aging
US11141482B2 (en) 2009-07-17 2021-10-12 Klox Technologies Inc. Combination of an oxidant, a photosensitizer and a wound healing agent for oral disinfection and treatment of oral disease
US9603929B2 (en) 2009-07-17 2017-03-28 Klox Technologies Inc. Combination of an oxidant, a photosensitizer and a wound healing agent for oral disinfecton and treatment of oral disease
WO2011006263A1 (fr) * 2009-07-17 2011-01-20 Klox Technologies Inc. Composition orale antibactérienne
EA025022B1 (ru) * 2009-07-17 2016-11-30 Клокс Текнолоджиз Инк. Антибактериальная композиция для ротовой полости
US10322179B2 (en) 2009-07-17 2019-06-18 Klox Technologies Inc. Combination of an oxidant, a photosensitizer and a wound healing agent for oral disinfection and treatment of oral disease
US8986746B2 (en) 2009-07-17 2015-03-24 Klox Technologies Inc. Combination of an oxidant, a photosensitizer and a wound healing agent for oral disinfection and treatment of oral disease
US8685466B2 (en) 2009-07-17 2014-04-01 Klox Technologies Inc. Combination of an oxidant, a photosensitizer and a wound healing agent for oral disinfection and treatment of oral disease
US10471147B2 (en) 2009-07-17 2019-11-12 Klox Technologies Inc. Combination of an oxidant, a photosensitizer and a wound healing agent for oral disinfection and treatment of oral disease
US10213373B2 (en) 2012-04-20 2019-02-26 Klox Technologies, Inc. Chromophore combinations for biophotonic uses
US10376455B2 (en) 2012-04-20 2019-08-13 Klox Technologies Inc. Biophotonic compositions and methods for providing biophotonic treatment
US11116841B2 (en) 2012-04-20 2021-09-14 Klox Technologies Inc. Biophotonic compositions, kits and methods
US11331257B2 (en) 2012-04-20 2022-05-17 Klox Technologies Inc. Biophotonic compositions and methods for providing biophotonic treatment
US11723854B2 (en) 2012-04-20 2023-08-15 Fle International S.R.L. Biophotonic compositions and methods for providing biophotonic treatment
US9655829B2 (en) 2012-09-14 2017-05-23 Valeant Pharmaceuticals International, Inc. Compositions and methods for teeth whitening
US10130706B2 (en) 2013-03-14 2018-11-20 Klox Technologies Inc. Biophotonic materials and uses thereof
US11324823B2 (en) 2013-03-14 2022-05-10 Klox Technologies Inc. Biophotonic materials and uses thereof
US10881736B2 (en) 2013-07-03 2021-01-05 Klox Technologies Inc. Biophotonic compositions comprising a chromophore and a gelling agent for treating wounds
US10772990B2 (en) 2014-04-01 2020-09-15 Klox Technologies Inc. Tissue filler compositions and methods of use
US10207029B2 (en) 2014-04-01 2019-02-19 Klox Technologies Inc. Tissue filler compositions and methods of use
US11421349B2 (en) 2014-10-31 2022-08-23 Klox Technologies Inc. Photoactivatable fibers and fabric media

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