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WO2021140437A1 - Composant sulfate d'alkyle anionique pour le traitement des caries - Google Patents

Composant sulfate d'alkyle anionique pour le traitement des caries Download PDF

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Publication number
WO2021140437A1
WO2021140437A1 PCT/IB2021/050047 IB2021050047W WO2021140437A1 WO 2021140437 A1 WO2021140437 A1 WO 2021140437A1 IB 2021050047 W IB2021050047 W IB 2021050047W WO 2021140437 A1 WO2021140437 A1 WO 2021140437A1
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WO
WIPO (PCT)
Prior art keywords
component
alkyl sulphate
lactic acid
anionic alkyl
aas
Prior art date
Application number
PCT/IB2021/050047
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English (en)
Inventor
Ingo R. Haeberlein
Brenda Schmid
Melanie N. HAUKE
Ajmal SAFI
Original Assignee
3M Innovative Properties Company
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Filing date
Publication date
Application filed by 3M Innovative Properties Company filed Critical 3M Innovative Properties Company
Publication of WO2021140437A1 publication Critical patent/WO2021140437A1/fr

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    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • 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
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits
    • A61K2800/882—Mixing prior to application
    • 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
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits
    • A61K2800/884—Sequential application

Definitions

  • the invention relates to oral care compositions containing certain anionic alkyl sulphate components.
  • the oral care compositions and in particular the anionic alkyl sulphate components contained therein were found to be effective in treating caries or reducing the risk of getting caries lesions by reducing the lactic acid release of lactic acid producing bacteria in an oral biofilm in the mouth of a living human being or animal.
  • Dental plaque which may include bacteria such as Streptococcus mutans, comprises a biofilm that forms on surfaces in the oral cavity. Dental plaque is at least partly responsible for dental caries, gingivitis, and periodontal diseases.
  • Dental plaque Bacteria in dental plaque metabolize carbohydrates (for example, simple sugars) in the mouth and produce organic acids that can etch tooth enamel, dentin, and cement. Dental plaque can serve as a substrate for the deposition of tartar or calculus. Build-up of dental plaque and calculus can lead to gingivitis and, ultimately, to periodontal disease.
  • carbohydrates for example, simple sugars
  • a currently available method to remove dental plaque from teeth is mechanical removal with, for example, dental floss or a toothbrush.
  • a toothbrush can aid in removing dental plaque from exposed surfaces of a tooth, and dental floss can aid in removing dental plaque from, for example, interproximal and subgingival surfaces.
  • Proper and regular use of dental floss and a toothbrush can mechanically remove or reduce dental plaque, and can reduce the incidence of dental caries, gingivitis, and periodontal disease.
  • Certain antimicrobial formulations are available (in the form of mouthwashes, rinses, and toothpastes, for example) to aid in the control and treatment of dental plaque, dental caries, gingivitis, and periodontal disease.
  • dental caries results from an imbalance of the metabolic activity in the individual dental biofilm This reflects the daily clinical experiences that only a small fraction of dental plaque might end up in tooth demineralization. Even more, certain studies with dental biofilm revealed that the bacterial composition of dental plaque does not necessarily indicate the prevailing metabolic (caries) activity of the individual dental plaque.
  • WO 00/27438 (University de Montreal) relates to compositions for removing biofdm from contaminated surfaces.
  • the composition comprises an effective dislodging amount or a detergent and an effective dislodging amount of an acid or salt of an acid.
  • SDS sodium dodecyl sulphate
  • US 2009/0202456 Al (Prencipe et al.) describes an oral care composition comprising a salt of arginine in combination with a one or more of the following conjugate acids: acidic polymer, a conjugate acid of an anionic surfactant salt, a polyphosphoric or polyphosphomc acid or an acidic antimicrobial agent.
  • the composition is said to be useful to protect the teeth by facilitating repair and remineralisation.
  • EP 0 086 290 Al (Warner-Lambert) describes a dental hygiene composition containing as an antiplaque active ingredient a highly pure alkali metal dodecyl (lauryl) sulphate.
  • the composition may also contain in addition anticaries agents such as sodium fluoride or sodium monofluorophosphate.
  • anticaries agents such as sodium fluoride or sodium monofluorophosphate.
  • a pH of about 2 is suggested.
  • US 2016/0175208 Al (Matin et al.) relates to a liquid mouthwash containing electrolyzed water having a positive oxidation-reduction potential, a menthol, an anionic surfactant, and a water- soluble organic solvent and having a pH of 6 to 8. It is outlined that the anionic surfactant prevents the promotion of decomposition of electrolyzed water accompanied by the addition of menthol and the metal corrosion of the electrolyzed water.
  • SLS sodium lauryl sulfate
  • Such components should be easy in administering and simple in use.
  • the components should be easy to obtain or prepare and reasonable in price of manufacturing or purchase.
  • the components should not have undesired side effects like bad taste or being astringent.
  • the components of the respective composition should in particular be active if used and/or applied in a permanent treatment.
  • the invention features an anionic alkyl sulphate component and salts thereof as described in the present text and claims for use in a method of treating caries or reducing the risk of getting caries by reducing the lactic acid release of lactic acid producing bacteria in an oral biofilm in the mouth of a human being or animal, the anionic alkyl sulphate component having the formula kOSCL with R 1 being C 9 -C 18 alkyl, in particular n-alkyl.
  • the invention also relates to a kit of parts as described in the present text and claims for use in a method of treating caries or reducing the risk of getting caries by reducing the lactic acid release of lactic acid producing bacteria in an oral biofdm containing lactic acid producing bacteria in an oral biofdm in the mouth of a human being or animal, the kit of parts comprising Part A comprising the anionic alkyl sulphate component as described in the present text, Part B comprising water, optionally in combination with a carrier component as described in the present text, and optionally Part C comprising an application device.
  • a further aspect of the invention is directed to the use of the anionic alkyl sulphate component as active agent for treating caries or reducing the risk of getting caries as described in the present text and claims for producing an oral care composition containing the anionic alkyl sulphate component, or a kit of parts as described in the present text.
  • Described is also a method of using the anionic alkyl sulphate component or the kit of parts as described in the present text and claims for the production of an oral care composition.
  • the treatment is particular effective, if the oral care composition is applied to marginal regions of hard dental tissue.
  • marginal regions of hard dental tissue are interproximal areas of teeth, e.g. the area between two neighbouring teeth, fissures being present on the surface of a tooth, marginal gap between a dental restoration (e.g. dental filling or dental crown) and the tooth substance.
  • a dental restoration e.g. dental filling or dental crown
  • composition is understood to be a mixture of two or more components.
  • a “dental or oral care composition” is a composition which is to be used in the dental field including the orthodontic area.
  • the composition should be not detrimental to the patient ' s health and thus free of hazardous and toxic components being able to migrate out of the composition.
  • Commercially available dental products have to fulfil certain requirements such as those given in DIN EN ISO 1942:2011-03.
  • a "dental surface” or “hard dental tissue” refers to tooth structures (e.g., enamel, dentin, and cementum) and bone.
  • a “tooth structure” is any tooth structure, prepared or ready for preparation by the dentist. It can be a single tooth or two or more teeth. A tooth structure is also referred to as hard dental tissue in contrast to soft dental tissue (e.g. gingival).
  • Distal plaque is understood as is a biofilm or mass of bacteria that grows on surfaces within the mouth.
  • a “paste” is a substance that behaves as a solid until a sufficiently large load or stress is applied, at which point it flows like a fluid.
  • Pastes typically consist of a suspension of granular material in a background fluid. The individual grains are jammed together like sand on a beach, forming a disordered, glassy or amorphous structure, and giving pastes their solid-like character. Pastes can be classified by their viscosity or their consistency comparable to dental impression material.
  • a “toothpaste” (dentifrice) is a cleaning agent for the daily individual care. It is typically used as a prophylactic measure against caries, gingivitis or periodontitis.
  • a “prophylaxis paste” is a product which is used by a profession such as a dentist or a dental hygienist to remove adherent deposits such as stain, plaque or tartar which may stick to the surface of a natural tooth, artificial tooth crown or bridge or filling material.
  • a prophylaxis paste is therefore typically used on slowly rotating paste carrier (sometimes also referred to as prophy cups). Most of the commercially available prophylaxis pastes have a different viscosity compared to toothpastes.
  • a “gel” is typically a colloidal system in which a porous matrix of interconnected particles spans the volume of a liquid medium.
  • gels are apparently solid, jelly-like materials. Both by weight and volume, gels are mostly liquid in composition and thus exhibit densities similar to liquids, however, have the structural coherence of a solid.
  • An example of a common gel is edible gelatine. Many gels display thixotropy, that is, they become fluid when agitated, but re-solidify when resting.
  • a “solvent” means a liquid which is able to at least partially disperse or dissolve a component at ambient conditions (e.g. 23 °C).
  • a solvent typically has a viscosity below 5 or below 1 or below 0.1 Pa*s at 23 °C.
  • the mean particle size of a powder can be obtained from the cumulative curve of the grain size distribution and is defined as the arithmetic average of the measured grain sizes of a certain powder mixture. Respective measurements can be done using commercially available granulometers (e.g. CILAS Laser Diffraction Particle Size Analysis Instrument).
  • AAS component anionic alkyl sulphate component
  • AAS component also comprise salts of the AAS component, in particular the alkaline metal salts.
  • Ambient conditions mean the conditions which the inventive solution or composition is usually subjected to during storage and handling.
  • Ambient conditions may, for example, be a pressure of 900 to 1100 mbar, a temperature of 10 to 40 °C and a relative humidity of 10 to 100 %. In the laboratory ambient conditions are adjusted to 20 to 25 °C and 1,000 to 1,025 mbar (at maritime level).
  • “And/or” means one or both.
  • the expression component A and/or component B refers to a component A alone, component B alone, or to both component A and component B.
  • anionic alky sulphate components having a shorter alkyl chain e.g. less than 9 C-units are not effective in reducing the lactic acid release of lactic acid releasing bacteria in an oral biofilm.
  • anionic alkyl sulphate component also includes a composition containing the AAS component. It was observed that by using the AAS component, the caries activity of the oral biofilm can significantly be lowered.
  • the composition described in the present text provides an effective means for treating caries or reducing the risk of getting caries lesions.
  • an in-vitro human saliva derived microcosm biofilm was used to apply the AAS component described in the present text using different treating schemes.
  • the AAS component functions either as a biofilm metabolism control agent or as an agent for modifying the structure of the biofilm or as a kind of cell membrane modifying agent. Independent of the mechanism, the AAS component is effective for treating caries or reducing the risk of getting caries lesions.
  • the cell membrane modifying agent primarily refers to the cell membrane of the cells of the bacteria forming the biofdm and of the extra-cellular membranes constituting the biofdm.
  • the AAS components seem to be able to break down membrane-like structures in oral biofdms and/or may be able to remove enzyme(s) located at these membrane-like structure.
  • the oral care composition described in the present text containing an AAS component as agent for treating caries or reducing the risk of getting caries is designed to move from a plaque formation inhibition composition or dental plaque removal composition or biofdm reducing composition to a composition allowing the control of the metabolic balance on dental plaque.
  • the invention shows that AAS components are effective to accomplish caries activity control in a dental biofdm, i.e. being able to influence the metabolic balance of the dental biofdm. Further, compared to previously used active components, the AAS component proposed in the present text is easily available at reasonable costs and not harmful to the patient.
  • AAS component such as sodium lauryl sulphate have been used in oral care compositions before, however, in those oral care compositions the AAS component was added as surfactant (e.g. US 2009/0202456 Al), but not for the purpose of treating caries, in particular for treating caries by reducing the lactic acid release of lactic acid releasing bacteria in the mouth of a human being or animal.
  • the AAS component is used for a different purpose.
  • the AAS component contained in the oral care composition described in the present text is for use in a method or therapy of treating caries or reducing the risk of caries by reducing the lactic acid release of lactic acid producing bacteria in an oral biofdm of a human or animal being.
  • AAS anionic alkyl sulphate component
  • RLOSCL with R 1 being Cg-Cie alkyl or C10-C14.
  • the AAS component is typically provided in salt form.
  • Medically acceptable salts include the Li, Na, K and ammonium salts (such as NH 4 + ) of the alkyl sulphate component.
  • a preferred anionic alkyl sulphate component is sodium lauryl sulphate (SLS) having the following formula:
  • mixtures of AAS components can be used as well.
  • the AAS component can also be charactenzed by its molecular weight which is typically within a range of 240 to 350 g /mol.
  • the AAS component is typically present in the oral care composition in an amount being effective for reducing the lactic acid release of lactic acid releasing bacteria by at least 40 or at least 45 or at least 50% or more compared to a control composition not containing the AAS component.
  • the AAS component is used in combination with water.
  • the oral care composition comprises one or more of the AAS components and water.
  • An AAS component containing oral care composition may comprise water in the following amounts:
  • the ratio of AAS component to water is typically at least 0.01 / 100, or at least 0.1 / 100 with respect to weight.
  • the ratio of AAS component to water can be in a range of 0.01 / 100 to 5 / 100, or in a range of 0.1 / 100 to 3 / 100 with respect to weight.
  • the AAS component may also be used in combination with a carrier component.
  • the oral care composition may comprise one or more AAS components, one or more carrier components and optionally water.
  • Carrier components may help to adjust the rheological properties of the AAS component containing composition to support the application and/or to trigger the release of the active agent(s) contained in the composition.
  • the carrier component is typically present in the following amount(s):
  • the carrier component is a fdm-forming agent.
  • the molecular weight is typically provided by the manufacturer of the respective film-forming component. If desired, the molecular weight can be determined by GPC technology, using e.g. a polystyrene standard.
  • the film forming component might not be able to form a sufficiently durable film or coating. Thus, the effect of a delayed release of the AAS component might not be obtained.
  • Film formers or film-forming agents can be classified as natural film former, semi-synthetic film formers, cellulose derivatives, poly(meth)acrylates and vinyl polymers.
  • poly(meth)acrylates examples include copolymers of (meth)acrylic esters and amino functional (meth)acrylates, copolymers of (meth)acrylic acid and methyl methacrylate, polyacrylamide, polyacrylic acid and salts thereof, in particular partial salts thereof, including sodium salts.
  • vinyl polymers include polyvinyl pyrrolidon, polyvinyl acetate phthalate (e.g. hydroxypropyl- and hydroxypropyl-methylcellulose), homo- and copolymers of polyvinylacetate, homo- and copolymers of polyvinylpropionate, styrene acrylics, ethylene vinyl acetate, poly(hydroxyethyl methacrylate, poly(vinylethylene glycol acrylate, polyvinyl alcohol(s).
  • polyvinyl pyrrolidon polyvinyl acetate phthalate (e.g. hydroxypropyl- and hydroxypropyl-methylcellulose), homo- and copolymers of polyvinylacetate, homo- and copolymers of polyvinylpropionate, styrene acrylics, ethylene vinyl acetate, poly(hydroxyethyl methacrylate, poly(vinylethylene glycol acrylate, polyvinyl alcohol(s).
  • fdm -forming agent(s) include (e.g. fully or partially hydrolyzed) polyvinylalcohol, polymethylvinylether, polyvinylpyrrolidone, (e.g. aqueous) acrylic resin dispersions (e.g. EudragitTM, commercially available from Rohm), gelatine, polysaccharides (e.g. agarose), polyacrylamide, copolymers of vinylpyrrolidinone and acrylamide, hydrophilic cellulose derivatives (e.g.
  • hydroxyethylcellulose hydroxypropylcellulose, methylcellulose
  • homo- and copolymers of polyvinylacetate homo- and copolymers of polyvinylpropionate, styrene acrylics, ethylene vinyl acetate, polyurethanes, hydroxylated acrylates such as poly(hydroxyethyl methacrylate), poly(vinylethylene glycol acrylate), and combinations and mixtures thereof.
  • a film-forming agent is present, it is typically present in the following amounts:
  • abrasive particles examples include perlite, bentonite, silica, alumina, aluminium hydroxide, ilmenite (FeTiO,), zircon oxide, zircon silicate, calcium carbonate, sodium bicarbonate, titanium dioxide , precipitated lime, chalk, flour of pumice, zeolites, talcum, kaolin, kieselguhr, aluminium oxide, silicates and mixtures thereof.
  • the AAS component is used in combination with certain amino acids.
  • the AAS component(s) are used for modifying the structure of the oral biofilm and thus have an influence on the overall environment where the lactic acid producing bacteria are located.
  • the amino acid(s) may have a direct impact on the metabolism of the lactic acid releasing bacteria.
  • amino acids were found to be useful for achieving the desired results: glycine, leucine, isoleucine, methionine, phenylalanine, serine, threonine, valine, tryptophan and mixtures thereof, with the following amino acids being sometimes preferred: glycine, phenylalanine, serine, isoleucine, leucine, methionine, with glycine and phenylalanine being sometimes being even more preferred.
  • the amino acids may be natural or synthetic.
  • amino acids were found to be not effective for reducing the lactic- acid release of bacteria in a biofilm: proline, arginine, histidine, aspartic acid, glutamine, tyrosine. These amino acids are therefore not suggested for this particular use.
  • the amino acids contained in the oral care composition are used in a therapeutically effective amount being sufficient to influence the lactic acid release metabolism of lactic acid releasing bacteria in an oral biofilm.
  • the AAS component containing oral care composition and the amino acids contained therein are used for a time period being sufficient to influence the lactic acid release metabolism of lactic acid releasing bacteria in an oral biofilm.
  • amino acid(s) are typically present in the following amounts:
  • Upper limit utmost 15 or utmost 12 or utmost 10 wt.%; Range: 0.1 to 15 or 1 to 12 or 2 to 10 wt.%; wt.% with respect to the whole composition.
  • glycine in an amount of 0.1 to 10 wt.%; or leucine in an amount of 0.1 to 5 wt.%; or isoleucine in an amount of 0.1 to 5 wt.%; or methionine in an amount of 0.1 to 10 wt.%; or phenylalanine in an amount of 0.1 to 5 wt.%; or serine in an amount of 0.1 to 10 wt.%; or threonine in an amount of 0.1 tolO wt.%; or valine in an amount of 0.1 to 8 wt.%; or tryptophan in an amount of 0.1 to 2 wt.%; wt.% with respect to the whole composition.
  • glycine in an amount of 1 to 10 wt.%; or leucine in an amount of 1 to 5 wt.%; or isoleucine in an amount of 2 to 5 wt.%; or methionine in an amount of 2 to 10 wt.%; or phenylalanine in an amount of 1 to 5 wt.%; or serine in an amount of 1 to 10 wt.%; or threonine in an amount of 6 to 10 wt.%; or valine in an amount of 3 to 8 wt.%; or tryptophan in an amount of 0.5 to 2 wt.%; wt.% with respect to the whole composition.
  • the ratio of amino acid(s) to water is typically at least 0.1 / 100, or at least 1.5 / 100, or at least 2 / 100 with respect to weight.
  • the ratio of amino acid(s) to water can be in a range of 0.1 / 100 to 15 / 100, or in a range / 1.5 to 100 to 12 / 100, or in a range of 2 to 100 to 10 to 100 with respect to weight.
  • the ratio of AAS component to amino acid(s) is typically at least 1 / 100 or at least 1 / 50 or at least 1 / 20.
  • the ratio of AAS component to amino acid(s) can be in a range of 1 / 100 to 1 / 1, or in a range 1 / 50 to 1 / 2, or in a range of 1 / 20 to 1 / 5 with respect to weight.
  • the AAS component is used in combination with an N- acetyl amino acid component selected from the acetyl components of alanine, valine, cysteine, glutamic acid, glycine, leucine, proline, tyrosine, iso-leucine, tryptophan, phenylalanine and mixtures thereof.
  • N-acetyl amino acid component there is no need for an N-acetyl amino acid component to be present, however, the presence of an N-acetyl amino acid component in combination with the AAS component may further help or even improve the efficacy or capacity of the oral care composition described in the present text.
  • N-acetyl amino acid component is typically used in excess.
  • a ratio of N-acetyl amino acid component to AAS component in the range of 30 : 1 to 5 : 1 or 20 : 1 to 5 : 1 with respect to weight was found to be useful.
  • the N-acetyl amino acid component may function as a biofilm metabolism control agent, whereas the AAS component may function as an agent for modifying the structure of the biofilm or as a kind of cell membrane modifying agent.
  • N-acetyl component of glycine, proline, or phenylalanine with an anionic alkyl sulphate component having the formula: R'-OSO, with R 1 being Cio-Cu n-alkyl, in particular lauryl sulfate.
  • N-acetyl amino acid component for use in a method of treating caries or reducing the risk of caries is described in EP application No. 19215475.5. The content of this reference is herewith incorporated by reference.
  • the presence of a synergistic effect can be shown by comparing the lactic acid release of a biofilm which has not been treated with a lactic acid reducing composition (control; lactic acid release value set as 100%) with the lactic acid release of a biofdm having been treated by either of the following: a) a composition comprising an N-acetyl amino acid, b) a composition comprising an AAS component, and c) a composition comprising an N-acetyl amino acid and an AAS component.
  • the synergistic effect becomes in particular visible if only small amounts of these components are tested (e.g. a composition comprising N-acetyl amino acids in an amount in the range of 0.01 to 0.2 wt.% and a composition comprising AAS components in an amount of 0.001 to 0.005 wt.%).
  • the AAS component containing oral care composition described in the present text may also comprise additive(s).
  • additive(s) can be present, if desired. If present, additive(s) are typically present in the following amount(s):
  • Additive(s) which might be present include stabilizer(s), colourant(s), phosphate releasing agent(s), calcium releasing agent(s), anti-microbial agent(s), buffer(s), humectant(s), preservative agent(s), flavour additive(s) and mixtures thereof.
  • the composition might contain one or more stabilizer(s) as an additive.
  • the storage stability of the oral care composition might be improved. That is, the individual components of the composition do not separate over time.
  • a composition is defined as storage-stable, if the components do not separate from each other within 6 months or 12 months or 24 months or 36 months at ambient conditions.
  • a stabilizer is present, it is typically, present in a low amount.
  • Amounts, found to be useful, include 0.01 to 3 wt.% or 0.1 to 1 wt.% with respect to the weight of the whole composition.
  • stabilizer(s) examples include copolymers of 2,5-furandione with 1,9-decadiene and methoxyethene (e.g. StabilizeTM, International Specialty Products (ISP) Comp.) and carboxy vinyl polymers (e.g. CarbopolTM, Lubrizol Advanced Materials Comp.).
  • Stabilizers typically have a mean particle size below 500 pm or below 250 pm or below 100 pm.
  • the composition comprises one or more colourants.
  • a colourant is present, it is typically present in an amount of at most 5 wt.% or of at most 3 wt.% or of at most 1 wt.% with respect to the whole composition. Typical ranges include 0.01 wt.% to 5 wt.% or 0.1 wt.% to 3 wt.% with respect to the whole composition.
  • a colourant may allow an easy detection in a patient's mouth (especially compared to oral tissue and/or tooth substance) and control whether after the treatment all residues of the composition have been removed.
  • a blue, green or violet colour may be suitable.
  • Colouring of the dental composition can be achieved by incorporating colorants or pigments (organic and inorganic) into the composition.
  • colourants include red iron oxide 3395, BayferroxTM 920 Z Yellow, NeazoponTM Blue 807 (copper phthalocyanine-based dye) or Helio Fast Yellow ER and mixtures thereof.
  • the composition comprises one or more phosphate releasing agent(s) as an additive.
  • a phosphate releasing agent there is no need for a phosphate releasing agent to be present at all. If a phosphate releasing agent is present, it is typically present in an amount of at most 5 wt.% or of at most 3 wt.% or of at most 2 wt.% with respect to the whole composition. Typical ranges include 0.01 wt.% to 5 wt.% or 0.1 wt.% to 3 wt.% with respect to the whole composition.
  • phosphate and/or calcium releasing agent(s) examples include calcium pyrophosphate, calcium carbonate, dicalcium phosphate dehydrate, amorphous calcium phosphate, casein phosphopeptide, calcium sodium phosphosilicate, trimetaphosphate, and mixtures thereof.
  • composition comprises anti-microbial agent(s).
  • an anti-microbial agent is present, it is typically present in an amount of at most 2 wt.% or of at most 1 wt.% or of at most 0.5 wt.% with respect to the whole composition. Typical ranges include 0.01 wt.% to 2 wt.% or 0.1 wt.% to 1 wt.% with respect to the whole composition.
  • an anti-microbial agent might help reducing health risks for professionals in the dental offices and laboratories as well as for patients.
  • Useful anti-microbial agents include chlorhexidine or derivatives thereof and aldehydes (glutaraldyde, phthalaldehyde) and chlorhexidine or its derivatives and salts of phenolics or acids. It can also be preferred to use acid adducts of chlorhexidine or its derivatives like e.g., acetates, gluconates, chlorides, nitrates, sulphates or carbonates.
  • Chlorhexidine and its derivatives are commercially available in water-based solutions (e.g. a 20 % aqueous solution of CHX digluconate, CAS 18472-51-0) or as a pure compound or as a salt.
  • water-based solutions e.g. a 20 % aqueous solution of CHX digluconate, CAS 18472-51-0
  • pure Chlorohexidine compound CAS 55-56-1
  • CHX salts like CHX diacetate monohydrate (CAS 56-95-1) or CHX dihydrochloride (CAS 3697-42-5) are preferred.
  • CHX also seems to be especially suited as an additive due in part to its well-known and proven anti-microbial action against Gram-positive and Gram-negative microorganisms including the oral Streptococci and Lactobacilli.
  • CHX is bacteriostatic for Mycobaterium.
  • CHX is also active against yeasts including Candida albicans and viruses including HIV, HBV, HCV, Influenza- and Herpes vims.
  • a further advantage of CHX is its low toxicity.
  • Preferred anti-microbial agents include hexitidin, cetypyridiniumcloride (CPC), chlorhexidin (CHX), triclosan, stannous chloride, benzalkonium chloride, non-ionic or ionic surfactants (e.g. quaternary ammonium compounds), alcohols [monomeric, polymeric, mono-alcohols, poly-alcohols (e. g. xylitol, sorbitol), aromatic (e. g. phenol)], antimicrobial peptides (e. g. histatins), bactericins (e. g. nisin), antibiotics (e. g. tetracycline), aldehydes (e.
  • inorganic and organic acids e. g. benzoic acid, salicylic acid, fatty acids
  • derivative of such acids such as esters (e. g. p-hydroxy benzoate or other parabenes, laurizcidin), enzymes (e. g. lysozyme, oxidases), proteins (e. g. enamel matrix protein, proline rich proteins), fluoride, EDTA, essential oils (e. g. thymol).
  • composition can comprise one or more buffer(s) as an additive.
  • a buffer there is no need for a buffer to be present at all. If a buffer is present, it is typically present in an amount of at most 5 wt.% or of at most 3 wt.% or of at most 2 wt.% with respect to the whole composition. Typical ranges include 0.1 wt.% to 5 wt.% or 1 wt.% to 3 wt.% with respect to the whole composition.
  • buffers examples include acetic acid/acetate, tris(hydroxymethyl)- aminomethane (TRIS), N-(2-acetamido)-2-aminoethane sulfonic acid (ACES), N-(2-acetamido)- imminodiacetate (ADA), N,N-bis(2-hydroxyethyl)-2-aminoethane sulfonic acid (BES), 2,2-bis- (hydroxyethyl)-iminotris(hydroxylmethyl)methane (BIS-TRIS), 2-(cyclohexylamino)ethane sulfonic acid (CHES), 2-[4-(2-hydroxyethyl-l-piperazine)]ethane sulfonic acid (HEPES), 3-[4-(2- hydroxyethyl-l-piperazinyl)] propane sulfonic acid (HEPPS), 2-morpholinoethane sulfonic acid (MES), 3-morpholinopropyl, tris(
  • composition might contain one or more humectant(s) as an additive.
  • a humectant is present, it is typically present in an amount of at most 5 wt.% or of at most 3 wt.% or of at most 2 wt.% with respect to the whole composition. Typical ranges include 0.01 wt.% to 5 wt.% or 0.1 wt.% to 3 wt.% with respect to the whole composition.
  • humectant(s) examples include glycerine, sorbitol, mannitol, xylitol, propylene glycol, polyethylene glycol and mixtures thereof.
  • preservative agent(s) examples include sodium benzoate, citric acid and its salts, and combinations thereof.
  • flavour additive(s) examples include peppermint, spearmint, and combinations thereof.
  • an AAS component containing oral care composition comprises or essentially consists of or consists of:
  • Component A in an amount of 0.01 to 5 wt.%;
  • Component B (water) in an amount of 5 to 98 wt.%;
  • Component C (carrier component) in an amount of 0 to 90 wt.%
  • Component D (amino acid) in an amount of 0 to 15 wt.%
  • Component E additive in an amount of 0 to 10 wt.%; wt.% with respect to the whole composition.
  • an AAS containing oral care composition comprises or essentially consists of or consists of:
  • Component A in an amount of 0.01 to 5 wt.%;
  • Component B (water) in an amount of 5 to 98 wt.%;
  • Component C carrier component in an amount of 1 to 90 wt.%
  • Component D amino acid in an amount of 0 to 15 wt.%
  • Component E additive in an amount of 0 to 10 wt.%; wt.% with respect to the whole composition.
  • an AAS containing oral care composition comprises or essentially consists of or consists of:
  • Component A in an amount of 0.01 to 5 wt.%;
  • Component B (water) in an amount of 5 to 98 wt.%;
  • Component C (carrier component) in an amount of 1 to 90 wt.%;
  • Component D (amino acid) in an amount of 0.1 to 15 wt.%;
  • Component E additive in an amount of 0 to 10 wt.%; wt.% with respect to the whole composition.
  • the composition typically has a pH value in the range of 6 to 8. Thus, the composition is essentially neutral.
  • the composition can also be characterized by its viscosity. Depending on its chemical formulation, the viscosity may vary over a huge range.
  • the viscosity is typically in a range of 1 to 10 mPa*s or 1 to 1,000 mPa*s at 23°C.
  • the viscosity is typically in a range of 2,000 to 200,000 mPa*s at 23°C.
  • the viscosity of pastes can be determined using a Physica MCR 301 Rheometer (Anton Paar, Graz, Austria) with a plate/plate geometry (PP15) at a constant shear rate of 1 s 1 in rotation at 28 °C.
  • the diameter of the plates is 10 mm and the gap between the plates is set to 2.0 mm.
  • Providing the components of the composition in separated parts can be beneficial to improve the storage stability.
  • AAS component containing oral care composition described in the present text for use of the AAS component containing oral care composition described in the present text in combination with a dental tray, mouth guard or clear tray aligner, providing the AAS composition in the form of a paste or gel was found to be advantageous.
  • the size and shape of the packaging device typically depends on the form how the composition is provided.
  • Suitable packaging devices include sealable bottles, tubes, vessels or foil bags (including glass or plastic bottles, e.g. equipped with a screw cap), blisters, syringes, etc.
  • the packaging device might be designed for single-use or repeated use.
  • the AAS component is provided in a liquid, e.g. in the form of an oral rinse or a mouth wash.
  • the composition is provided as part of a gel.
  • the composition is provided as part of a paste, e.g. in the form of a toothpaste.
  • the composition is provided as part of a gum, e.g. in the form of a chewing gum.
  • the composition is provided in a form which results in a coating after application.
  • Such an application typically contains a film forming agent.
  • preventive care products where the AAS component described in the present text can be used include prophy pastes, prophy powder, varnishes, coatings, etc.
  • the AAS component has to be brought in contact with the oral biofilm or hard dental tissue.
  • the oral biofilm is typically located on tooth surfaces, in particular hard dental tissue.
  • the bringing into contact can be achieved by different means, including rinsing, spraying, brushing, swabbing, coating or combinations thereof.
  • the bringing into contact is typically done for a time period being sufficient for causing the desired effect.
  • the bringing into contact is typically done for a duration of at least 1 min or of at least 2 min or at least 3 min or at least 4 min.
  • the oral care composition is applied in periodic application scheme.
  • Possible daily repeating schemes for a periodic application scheme are: at least 2-times for 1 to 5 min within 24 hours; at least 3-times for 1 to 5 min within 24 hours.
  • the oral care composition is applied in a continuous application scheme.
  • Possible daily repeating schemes for a continuous application scheme are: at least 1 hour within 24 hours; at least 5 hours within 24 hours.
  • AAS component is provided in the form of a gel or varnish to be applied either directly on the surface of the tooth structure or with the help of an application device.
  • the AAS component described in the present text is applied to form a coating or fdm which can persist on a tooth surface for at least 1, 2, 3 or 5 or 10 days up to 12 months or even longer.
  • the AAS component is applied together with film-forming agent(s).
  • Suitable film-forming agents are described above.
  • the oral care composition containing the AAS component described in the present text does typically not comprise the following components alone or in combination: oxidizing components in an amount of more than 0.5 wt.%; heavy metal components comprising Zn, Sn or Cu in an amount of more than 0.1 wt.%; fluoride anions in an amount of more than 0.1 wt.%; wt.% with respect to the whole composition.
  • composition described in the present text are essentially free of abrasive particles, in particular free of the abrasive particles described in the text above.
  • Essentially free means less than 1 or less than 0.5 or less than 0.1 wt.% or do not contain abrasive particles at all. Common to most of these substances is typically a comparable high hardness, e g. above about Mohs 4 or above about 5.
  • Oxidizing component(s) which are typically not present are peroxide, hypochlorite, perborate, persulphate, peroxyphosphate, peroxycarbonate.
  • the signal-producing solution contains the following components: 0.1 ml of NAD solution (30 mmol/1 NAD in Glygly buffer 50 mmol/1, pH 9.0), 0.1 ml of MTT (1.5 mmol/1 MTT in Glygly buffer 50 mmol/1, pH 9.0), 0.1 ml of PMS solution (1.0 mmol/1 PMS in Glygly buffer 50 mmol/1, pH 9.0), 0.1 ml of LDH solution (lactate dehydrogenase (LDH) 60 units/ml in Glygly buffer 50 mmol/l, pH 9.0) and 0.1 ml of pymvate solution (25 mmol/l in Glygly buffer 50 mmol/l, pH 9.0), with MTT: 3- (4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide, NAD: nicotinamide adenine dinucleotide, PMS: phenazine
  • the AAS component described in the present text for use in a method of treating caries or reducing the risk of getting caries by reducing the lactic acid release of lactic acid producing bacteria in an oral biofilm in the mouth of a living human or animal, the AAS component being applied in combination with water, the AAS component being contained in an amount of at least 0.01 wt.% with respect to the weight of the whole composition, the composition having a pH in the range of 6 to 8 and having a viscosity of 1 to 1,000 mPa*s at 23°C.
  • the AAS component as described in the present text for use in a method of treating caries or reducing the risk of getting caries by reducing the lactic acid release of lactic acid producing bacteria in an oral biofilm in the mouth of a living human or animal, the AAS component being applied in combination with water and amino acid(s), the ratio of the AAS component to water being in a range of 0.01:100 to 5:100 with respect to weight, the amino acid(s) being selected from glycine, leucine, isoleucine, methionine, phenylalanine, serine, threonine, valine, tryptophan and mixtures thereof, the method of treating caries or reducing the risk of getting caries by reducing the lactic acid release comprising the step of applying the composition being applied to the oral biofilm for at least 1 min.
  • the AAS as described in the present text for use in a method of treating caries or reducing the risk of getting caries by reducing the lactic acid release of lactic acid producing bacteria in an oral biofilm in the mouth of a living human or animal, the AAS component being applied in combination with water, the ratio of the AAS component to water being in a range of 0.01:100 to 5:100 with respect to weight, the composition having a pH in the range of 6 to 8, the method of treating caries or reducing the risk of getting caries by reducing the lactic acid release comprising the steps of applying AAS to the oral biofdm and/or hard dental tissue according to either of the following application schemes: at least 2 times for at least 1 min within 24 hours, for at least 1 hour within 24 hours, or for at least 2 days.
  • the AAS component as described in the present text for use in a method of treating caries or reducing the risk of getting caries by reducing the lactic acid release of lactic acid producing bacteria in an oral biofilm in the mouth of a human being or animal, the AAS component being selected from sodium nonyl sulphate, sodium decyl sulphate, sodium dodecyl sulphate, sodium tetradecyl sulphate, and mixtures thereof, and being used in combination with water in a ratio of 0.05 to 2% with respect to weight, the method of treating caries or reducing the risk of getting caries comprising the step of bringing the AAS component into contact with the oral biofilm according to either of the following application schemes: at least 2 times for at least 1 min within 24 hours, or for at least 1 hour within 24 hours, or for at least for 2 days.
  • the AAS component as described in the present text for use in a method of treating caries or reducing the risk of getting caries by reducing the lactic acid release of lactic acid producing bacteria in an oral biofilm in the mouth of a living human or animal, the AAS component being applied in combination with water and N-acetyl amino acid(s), the N-acetyl amino acid(s) being selected from the N-acetyl component of glycine, proline, phenylalanine, and mixtures thereof, in particular N-acetyl proline, the N-acetyl amino acid component being used in excess compared to the amount of AAS component the N-acetyl amino acid(s) being used preferably in an amount in the range of 0.01 to 0.2 wt.%, the AAS components being used preferably in an amount in the range of 0.001 to 0.005 wt.%, wt.% with respect to the whole composition.
  • compositions can be used in a method or therapy described in the present text.
  • the accumulation of lactic acid in the supernatant was measured by using the Lactic acid dehydrogenase (LDH)- Nicotinamide-adenine-dinucleotide (NAD)- Phenazine Methosulphate (PMS) - Thiazolyl blue tetrazolium bromide (MTT) - enzyme assay.
  • LDH Lactic acid dehydrogenase
  • NAD Nicotinamide-adenine-dinucleotide
  • PMS Phenazine Methosulphate
  • MTT Thiazolyl blue tetrazolium bromide
  • the biofdm samples were washed four times with 1.0 ml PBS solution for 30 sec each. After 30 min the accumulated amount of lactic acid in the supernatant was measured by analyzing 50 pi of the supernatant.
  • lactic acid was quantified by the lactic acid specific enzyme assay described above. Known correlation between measured enzyme activity and amount of lactic acid was used to translate measured enzyme activity into the amount of lactic acid present in sample of the supernatant.
  • a compound should lower the lactic acid release in permanent application of at least 40 or at least 45 or at least 50 % in comparison to the untreated biofdm control and should also lower lactic acid release in the periodic application of at least 5 %.
  • Bovine sample disks of about 10 x 10 mm (+/- 2mm) were incubated in a 24 well plate containing 1.8 ml medium in an incubator at 37°C and 60 rpm circular movement.
  • the treatment composition described below were added by pipetting and removed by a suction pump.
  • Biofilms were grown in an MCM (mucine containing medium plus 1 % sucrose) human derived saliva biofilm system.
  • Fresh medium (MCM-1% sucrose and Treatment Composition) for storage for about 14h at 37 °C.
  • Bovine sample disks were incubated in a 24 well plate containing 1.8 ml medium in an incubator at 37°C and 60 rpm circular movement.
  • the Treatment Compositions described below were added by pipetting and removed by a suction pump.
  • Biofilms were grown in a MCM (mucine containing medium plus 1 % sucrose) human derived saliva biofilm system.
  • Fresh medium (MCM-1% sucrose) for about 14h at 37 °C.
  • the reduction in the lactic acid release should be at least 5 or at least 8%.
  • TCx Treatment Compositions to be used for the Permanent Exposure Procedure and the Periodic Exposure Procedure were prepared by dissolving the respective AAS components in a liquid carrier medium (MCM or PBS) in the amounts given below in Table 2.
  • MCM or PBS liquid carrier medium
  • the AAS component was dissolved in PBS.
  • the Treatment Compositions (TCx) had the following compositions: Table 2

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Abstract

L'invention concerne un composant sulfate d'alkyle anionique et ses sels respectifs destinés à être utilisés dans un procédé de traitement des caries par réduction de la libération d'acide lactique de bactéries produisant de l'acide lactique dans un biofilm buccal dans la bouche d'un être humain ou d'un animal, le composant sulfate d'alkyle anionique ayant la formule R1-OSO3, R1 représentant un groupe alkyle en C9-C18. L'invention concerne également un kit d'éléments destiné à être utilisé dans un procédé de traitement des caries par réduction de la libération d'acide lactique de bactéries produisant de l'acide lactique dans un biofilm buccal dans la bouche d'un être humain ou d'un animal, le kit d'éléments comprenant un élément A comprenant le composant sulfate d'alkyle anionique, un élément B comprenant de l'eau, et éventuellement un élément C comprenant un dispositif d'application.
PCT/IB2021/050047 2020-01-08 2021-01-05 Composant sulfate d'alkyle anionique pour le traitement des caries WO2021140437A1 (fr)

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Citations (10)

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Publication number Priority date Publication date Assignee Title
EP0086290A1 (fr) 1982-02-15 1983-08-24 Warner-Lambert Company Compositions d'hygiène dentaire et leur production
US5019373A (en) 1988-12-01 1991-05-28 Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. Oral composition
WO2000027438A1 (fr) 1998-11-06 2000-05-18 Universite De Montreal Solutions bactericides et non bactericides servant a eliminer des films biologiques
US7435558B2 (en) 2001-02-23 2008-10-14 3M Espe Ag Ascertaining the patient related risk of caries
US20090202456A1 (en) 2008-02-08 2009-08-13 Colgate-Palmolive Company Novel salts and their uses
KR20100117262A (ko) * 2009-04-24 2010-11-03 한성희 항균성 치약 조성물
US20150313822A1 (en) 2012-12-19 2015-11-05 Colgate-Palmolive Company Zinc amino acid complex with cysteine
US20160175208A1 (en) 2013-08-07 2016-06-23 Hychlotech Medical Japan Co., Ltd. Liquid mouthwash
WO2017000837A1 (fr) 2015-07-01 2017-01-05 Colgate-Palmolive Company Compositions de soins bucco-dentaires et leurs méthodes d'utilisation
WO2020016713A1 (fr) 2018-07-16 2020-01-23 3M Innovative Properties Company Composition de soin buccal contenant un acide aminé pour le traitement des caries par réduction de la libération d'acide lactique dans des biofilms buccaux

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Publication number Priority date Publication date Assignee Title
EP0086290A1 (fr) 1982-02-15 1983-08-24 Warner-Lambert Company Compositions d'hygiène dentaire et leur production
US5019373A (en) 1988-12-01 1991-05-28 Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. Oral composition
WO2000027438A1 (fr) 1998-11-06 2000-05-18 Universite De Montreal Solutions bactericides et non bactericides servant a eliminer des films biologiques
US7435558B2 (en) 2001-02-23 2008-10-14 3M Espe Ag Ascertaining the patient related risk of caries
US20090202456A1 (en) 2008-02-08 2009-08-13 Colgate-Palmolive Company Novel salts and their uses
KR20100117262A (ko) * 2009-04-24 2010-11-03 한성희 항균성 치약 조성물
US20150313822A1 (en) 2012-12-19 2015-11-05 Colgate-Palmolive Company Zinc amino acid complex with cysteine
US20160175208A1 (en) 2013-08-07 2016-06-23 Hychlotech Medical Japan Co., Ltd. Liquid mouthwash
WO2017000837A1 (fr) 2015-07-01 2017-01-05 Colgate-Palmolive Company Compositions de soins bucco-dentaires et leurs méthodes d'utilisation
WO2020016713A1 (fr) 2018-07-16 2020-01-23 3M Innovative Properties Company Composition de soin buccal contenant un acide aminé pour le traitement des caries par réduction de la libération d'acide lactique dans des biofilms buccaux

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CAS , no. 18472-51-0
CAS, no. 56-95-1
GIERTSEN E ET AL: "PLAQUE INHIBITION BY A COMBINATION OF ZINC CITRATE AND SODIUM LAURYL SULFATE", CARIES RESEARCH, S. KARGER AG, BASEL, CH, vol. 23, no. 4, 1 January 1989 (1989-01-01), pages 278 - 283, XP009058690, ISSN: 0008-6568 *
GIERTSEN ET AL.: "reports an additive inhibitory effect of ZnCh and sodium lauryl sulfate (SLS) on in vitro growth of Streptococcus sobrinus and of Streptococcus sanguis as the solubility of zinc citrate in increased in the presence of SLS", CARIES RES, vol. 23, 1989, pages 278 - 283

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