WO2015094336A1 - Oral care compositions and methods - Google Patents
Oral care compositions and methods Download PDFInfo
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- WO2015094336A1 WO2015094336A1 PCT/US2013/076892 US2013076892W WO2015094336A1 WO 2015094336 A1 WO2015094336 A1 WO 2015094336A1 US 2013076892 W US2013076892 W US 2013076892W WO 2015094336 A1 WO2015094336 A1 WO 2015094336A1
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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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
-
- 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
- A61K8/25—Silicon; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/27—Zinc; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/345—Alcohols containing more than one hydroxy group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/347—Phenols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—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
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8164—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers, e.g. poly (methyl vinyl ether-co-maleic anhydride)
-
- 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
-
- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L43/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium or a metal; Compositions of derivatives of such polymers
- C08L43/02—Homopolymers or copolymers of monomers containing phosphorus
-
- 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
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
- A61K2800/28—Rubbing or scrubbing compositions; Peeling or abrasive compositions; Containing exfoliants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/54—Polymers characterized by specific structures/properties
- A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
- A61K2800/5424—Polymers characterized by specific structures/properties characterized by the charge anionic
-
- 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
- A61K2800/92—Oral administration
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
Definitions
- a tooth is comprised of an inner dentin layer and an outer hard enamel layer that is the protective layer of the tooth.
- the enamel layer of a tooth is naturally opaque, and white or a slightly off-white color.
- the enamel layer is composed of hvdroxyapatite mineral crystals that create a somewhat porous surface. These hvdroxyapatite crystals form microscopic hexagonal rods or prisms that make up the enamel surface. As a result, the surface of the enamel presents microscopic spaces or pores between the prisms. Without limiting the mechanism, function, or utility of the present disclosure, it is believed that this porous nature of the enamel is where discoloring substances permeate the enamel and discolor the teeth.
- Peroxides are generally deemed safe from a physiological standpoint, and can be effective to whiten teeth. Such peroxides include hydrogen peroxide, carbamide peroxide, sodium perborate, and sodium percarbonate. When these peroxides are in appropriate contact wit teeth they will usually oxidize stains, rendering the teeth whiter.
- Current home treatment methods include abrasive toothpastes, toothpastes that produce oxides, whitening gels for use with a dental tray and whitening strips.
- the effectiveness of such techniques depends on a variety of factors including the type and intensity of the stain, the type of bleaching agent, contact time of the bleaching agent on the teeth, the amount of available bleaching active in the composition the ability of the bleaching agent to penetrate the tooth enamel, and consumer compliance. Effectiveness is also dependent on the amount of bleaching active in the composition, the ability of the active to be released during use, and the stability of the active in the product. However, the effectiveness of ma )' of these treatments is adversely affected because of deficiencies in one or more factors relating to the composition and consumer compliance.
- Biofilms form when bacteria adhere to surfaces in some form of watery environment and begin to excrete a slimy, glue-like substance that can stick to all kinds of materials - metals, plastics, soil particles, medical implant materials, biological tissues.
- Biofilms can be formed by a single bacterial species, but biofilms more often consist of many species of bacteria, as well, as fungi, algae, protozoa, debris, and corrosion products. Essentially, a biofilm may form on any surface exposed to bacteria and some amount of water.
- Dental plaque is a yellowish biofilm that builds up on the teeth. Biofilms contain communities of disease-causing bacteria and their uncontrolled accumulation has been associated with cavities and gum disease (both gingivitis and periodontitis).
- an oral care composition comprising a phosphate/acr late co-polymer, a synthetic anionic linear po!yearboxy!ate, and an orally acceptable carrier.
- compositions as a mouth rinse that includes the phosphate/acrylate co-polymer and the synthetic anionic linear poiycarboxyiate polymer as well as a zinc salt and a cationic antibacterial agent comprising: (I) mixing water, surfactant, and a cationic antibacterial agent in a mixing tank to form a main mix;
- an "oral care composition” refers to a composition for which, the intended use can include oral care, oral hygiene, or oral appearance, or for which, the intended method of use can comprise administration to the oral cavity.
- an oral care composition is not intentionally swallowed, but is rather retained in the oral cavity for a time sufficient to effect the intended utility.
- the oral care compositions as disclosed herein may be used in nonhuman mammals such as companion animals (e.g., dogs and cats), as well as by humans. In some embodiments, the oral care compositions as disclosed herein are used by humans.
- phosphate/acrylate co-polymer refers to a polymer made up of acrylate monomers and phosphate-bearing monomers, e.g., a co-pohmerized product of a mixture of aery He acid, methacrylic acid, and 2-hydroxyethy! methacrylate phosphates of Formula 1 :
- the phosphate/acrylate co-polymer is a co- polymerized product of a mixture of acrylic acid, methacrylic acid, and 2-hydroxyethyi methacrylate phosphates of Formula 1 , comprising acrylic acid in a molar percentage of 70-90%, 80-90%, or about 85%; methacrylic acid in a molar percentage of 5-20%, 5-15%, or about 1 1 %, and hydroxyethyl methacrylate phosphates of Formula 1 in a molar percentage of 1-10%, 2-6%, or about 4%,
- the phosphate/acrylate co-polymer has a weight average molecular weight of from 10 to 500 kDa, optionally, 10 to 200 kDa, 10 to 40 kDa, 15 to 25, or 17 to 23 kDa, and the phosphate/acrylate co-polymer is below its glass transition temperature.
- the weight average molecular weight is 10 to 40 kDa. In other embodiments, the weight average molecular weight is 17 to 23 kDa.
- the phosphate/acrylate copolymer is a random copolymer that is the copolymerized product of a mixture of, in the relative amounts set forth in Table 1 below, 2-hydroxyethy methacrylate phosphates, acrylic acid, and methacrylic acid.
- Phosphate/acrylate co-polymers as described include DV8801 (Rhodia).
- synthetic anionic linear polycarboxylate refers to a polymer synthesized by using an oiefmicafly or ethyienicaiiy unsaturated carboxviic acid that contains an activated carbon-to-carbon oiefinic double bond and at least one carboxyl group.
- the acid contains an oiefinic double bond which readily functions in polymerization because of its presence in the monomer molecule either in the alpha-beta position with respect to a carboxyl group or as part of a terminal methylene grouping.
- Such acids are acrylic, methacrylic, ethacryiic, alpha-chloroacryiic, crotonic, beta-acry!oxy propionic, sorbic, alpha- chlorsorbic, cinnamic, beta-styri f acrylic, muconic, itaconic, citraconic, mesaconic, glutaconic, aconitic, aipha-phenyiacrylie, 2-benzyI acrylic, 2-cyclohexylacryiic, angeiic, umbellic, funiaric, maleic acids and anhydrides.
- oiefinic monomers copolymerizable wit such carboxviic monomers include vinyl acetate, vinyl chloride, dimethyl maleate and the like.
- the synthetic anionic linear polycarboxylate is mainly a hydrocarbon with optional halogen and O-containing substituents and linkages as present in for example ester, ether, and OB groups.
- the carboxyls may be in the form of the acid (-COOH) or carboxylate anion (-COG " ).
- the copolymers preferably contain sufficient carboxyl groups for water- solubility and adherence to plaque.
- synthetic and “linear” do not include known thickening or gelling agents comprising carhoxymethy !ce! iulose and other derivatives of cellulose and natural gums, nor Carbopo!s having reduced solubility due to cross-linkages.
- synthetic anionic linear polycarboxyiate refers to 1 :4 to 4: 1 copolymers of maieic anhydride or acid with another polymerizabie ethyienicaiiy unsaturated monomer, e.g., methyl vinyl ether (methoxyethylene), having a molecular weight (M.W.) of about 30,000 to about 2,500,000; for example 1 :4 to 4:1 , e.g.
- orally acceptable carrier refers to any vehicle useful in formulating the oral care compositions disclosed herein.
- the orally acceptable carrier is not harmful to a mammal in amounts disclosed herein when retained in the mouth, without swallowing, for a period sufficient to permit effective contact with a dental surface as required herein, in general, the orally acceptable carrier is not harmful even if unintentionally swallowed.
- Suitable orally acceptable carriers include, for example, one or more of the following: water, a thickener, a buffer, a humeetant, a surfactant, an abrasive, a sweetener, a flavorant, a visual aid (e.g., a pigment, a dye, or a mixture thereof), an anti-caries agent, an anti-bacterial, a whitening agent, a desensitizing agent, a vitamin, a preservative, an enzyme, and mixtures thereof.
- water e.g., water, water, a thickener, a buffer, a humeetant, a surfactant, an abrasive, a sweetener, a flavorant, a visual aid (e.g., a pigment, a dye, or a mixture thereof), an anti-caries agent, an anti-bacterial, a whitening agent, a desensitizing agent, a vitamin, a preservative, an enzyme, and mixtures thereof
- a "tartar control agent” refers to a compound or a mixture of compounds that inhibit the formation of tartar, a mixture of calcium phosphates on organic matrices, and/or the deposition of plaque on teeth to form tartar (calculus).
- dental stain refers to a discoloration of a dental surface caused by adsorption or absorption of a colored agent on or into the surface, or caused by chemical reaction of material of the dental surface (e.g., dental enamel) with a colored or noncolored agent contacting the surface.
- Cosmetic staining herein means formation and/or development of a chemical stain.
- dental surface refers to a surface of a natural tooth or a hard surface of artificial dentition including a denture, dental plate, crown, cap, filling, bridge, dental implant and the like. In some embodiments, the dental surface is a natural tooth.
- Biofilm comprises a diverse microbial community on the tooth surface embedded in a matrix of polymers of bacterial and salivary origin. Once a tooth surface is cleaned, a conditioning film of proteins and glycoproteins may be adsorbed rapidly to the tooth surface. Biofilm formation involves the interaction between early bacterial colonisers and this film. Subsequently, secondary colonisers adhere to the already attached early colonisers (co- aggregation) and this process contributes to the development of a matured biofilm. Inhibiting the growth of biofilm may involve preventing and minimizing the re-attachment of bacteria onto the tooth surfaces.
- the phosphate side group of a phosphate/acrylate co-polymer may function as an anchor to deposit the co-polymer onto the tooth surface thereby forming a physical layer on the tooth surface that may inhibit staining and/or biofilm formation.
- the co-polymer may act by forming a barrier on the tooth surface ultimately lowering the surface energy for bacterial attachment.
- the co-polymer may also prevent bacteria from sticking together.
- composition 1 comprising
- phosphate/acrylate co-polymer a phosphate/acrylate co-polymer, a synthetic anionic linear polycarboxylate polymer, and an orally acceptable carrier.
- Composition 1 as follows:
- composition 1 wherein the composition comprises 0.1 to 10 weight % phosphate/acrylate co-polymer, e.g., 0.2 to 9 weight % phosphate/acrylate copolymer, e.g., 0.3 to 8 weight % phosphate/acrylate co-polymer, e.g., 0.4 to 7 weight % phosphate/acrylate co-polymer, e.g., 0.5 to 6 phosphate/acrylate copolymer, e.g., e.g., 0.5 to 5 weight % phosphate/acrylate co-polymer, e.g., 0.5 to 4 weight % phosphate/acrylate co-polymer, e.g., 0.5 to 3 weigh % phosphate/acrylate co-polymer, e.g., 0.5 to 2 weight % phosphate/acrylate copolymer, e.g., 1 to 10 weight % phosphate/acrylate co-polymer, e.g
- composition 1 or 1.1 wherein the composition comprises 0.01 to 30 weight % synthetic anionic linear polycarboxylate, e.g., 0.1 to 30 weight % synthetic anionic linear polycarboxylate, e.g., 1 to 30 weight % synthetic anionic linear polycarboxylate, e.g., 5 to 30 weight % synthetic anionic linear polycarboxylate, e.g., 10 to 30 weight % synthetic anionic linear polycarboxylate, e.g., 10 to 20 weight % synthetic anionic linear polycarboxylate, e.g., 15 weight % synthetic anionic linear polycarboxylate, e.g., 17 weight % synthetic anionic linear polycarboxylate.
- Composition 1 1.1 , or 1.2, wherein the synthetic anionic linear polycarboxylate is a copolymer of maleie anhydride and methyl vinyl ether.
- composition 1 or 1.1-1.5 wherein the composition further comprises a tartar control agent.
- composition 1.6 wherein the composition comprises 0.1 to 20 weight % tartar control agent, e.g., 0.1 to 15 weight % tartar control agent, e.g., 0.5 to 15 weight % tartar control agent, e.g., 15 to 10 weight % tartar control agent, e.g., 1 to 9 weight % tartar control agent, e.g., 1 to 8 weight % tartar control agent, e.g., 1 to 5 weight % tartar control agent.
- 0.1 to 20 weight % tartar control agent e.g., 0.1 to 15 weight % tartar control agent, e.g., 0.5 to 15 weight % tartar control agent, e.g., 15 to 10 weight % tartar control agent, e.g., 1 to 9 weight % tartar control agent, e.g., 1 to 8 weight % tartar control agent, e.g., 1 to 5 weight % tartar control agent.
- composition 1.6-1.8 wherein the tartar control agent comprises at least one of a pyrophosphate salt, a polyphosphate salt, and a cyclic phosphate salt.
- Composition 1.6-1.9 wherein the tartar control agent comprises at least one of a pyrophosphate salt and a polyphosphate salt.
- composition 1.6-1.10 wherein the tartar control agent comprises at least one pyrophosphate salt.
- composition 1.6-1.11 wherein the tartar control agent comprises 0.1 to 10 weight % of at least one pyrophosphate salt, e.g., 0.5 to 10 weight % of at least one pyrophosphate salt, 0.5 to 6 weight % of at least one pyrophosphate salt, e.g., 0.5 to 5 weight % of at least one pyrophosphate salt, e.g., 0.5 to 4 weight % of at least one pyrophosphate salt, e.g., 0.5 to 3 weight % of at least one pyrophosphate salt, e.g., 1 to 5 weight % of at least one pyrophosphate salt, e.g., 1 to 4 weight % of at least one pyrophosphate salt, e.g., 1 to 3 weight % of at least one pyrophosphate salt, e.g., 1 to 2 weight % of at least one pyrophosphate salt.
- the tartar control agent comprises 0.1 to 10 weight % of
- composition 1.6-1.12 wherein the tartar control agent comprises at least one of a di-alkali metal pyrophosphate salt and a tetra-alkali metal pyrophosphate salt.
- Composition 1.6-1.13 wherein the tartar control agent comprises at least one di- alkali metal pyrophosphate salt.
- composition 1.6-1.14 wherein the tartar control agent comprises at least one tetra- alkali metal pyrophosphate salt.
- composition 1.6-1.15 wherein the tartar control agent comprises 0.1 to 10 weight % of at least one tetra-alkali metal pyrophosphate salt, e.g., 0.1 to 8 weight % of at least one tetra-alkali metal pyrophosphate salt, e.g., e.g., 0.5 to 6 weight % of at least one tetra-alkali metal pyrophosphate salt, e.g., 0.5 to 5 weight % of at least one tetra-alkali metal pyrophosphate salt, e.g., 0.5 to 4 weight % of at least one tetra-alkali metal pyrophosphate salt, e.g., 0.5 to 3 weight % of at least one tetra- alkali metal pyrophosphate salt, e.g., 0.5 to 3 weight % of at least one tetra-alkali metal pyrophosphate salt, e.g., 1 to 5
- P . ⁇ ()- potassium pyrophosphate
- K 4 P 2 0 7 5 disodium dipotassium pyrophosphate ( a 2 2 P 2 0 7 ), disodi m dihydrogen pyrophosphate Na 2 H 2 P 2 0 7 , and dipotassium dihydrogen pyrophosphate
- TSPP, Na 4 P 2 0 7 disodium dipotassium pyrophosphate
- composition 1.6-1.19 wherein the tartar control agent comprises 0.1 to 10 weight % sodium pyrophosphate, e.g., 0.1 to 8 weight % sodium pyrophosphate, e.g., e.g., 0.5 to 6 weight % sodium pyrophosphate, e.g., 0.5 to 5 weight % sodium pyrophosphate, e.g., 0.5 to 4 weight % sodium pyrophosphate, e.g., 0.5 to 3 weight % sodium pyrophosphate, e.g., 0.5 to 3 weight % sodium pyrophosphate, e.g., 1 to 5 weight % sodium pyrophosphate, e.g., 1 to 4 weight % sodium pyrophosphate, e.g., 1 to 3 weight % sodium pyrophosphate, e.g., 1 to 2 weight % sodium pyrophosphate.
- the tartar control agent comprises 0.1 to 10 weight % sodium pyrophosphate, e
- composition 1.6-1.21 wherein the tartar control agent comprises at least one tripolyphosphate salt.
- composition 1.6-1.22 wherein the tartar control agent comprises 0.1 to 20 weight % of at least one tripolyphosphate salt, e.g., 0.5 to 15 weight % of at least one tripolyphosphate salt, e.g., 1 to 15 weight % of at least one tripolyphosphate salt, e.g., 1 to 10 weight % of at least one tripolyphosphate salt, e.g., 2 to 15 weight % of at least one tripolyphosphate salt, e.g., 2 to 11 weight % of at least one tripolyphosphate salt, e.g., 2 to 10 weight % of at least one tripolyphosphate salt, e.g., 2 to 9 weight % of at least one tripolyphosphate salt, e.g., 2 to 8 weight % of at least one tripolyphosphate salt, e.g., 2 to 7 weight % of at least one tripolyphosphate salt, e.g., 3 to 15 weight % of at
- composition 1.6-1.24 wherein the tartar control agent comprises 0.1 to 20 weight % sodium tripolyphosphate, e.g., 0.5 to 15 weight % sodium tripolyphosphate, e.g., 1 to 15 weight % sodium tripolyphosphate, e.g., 1 to 10 weight % sodium tripolyphosphate, e.g., 2 to 15 weight % sodium tripolyphosphate, e.g., 2 to 11 sodium tripolyphosphate, e.g., 2 to 10 weight % sodium tripolyphosphate, e.g., 2 to 9 weight % sodium tripolyphosphate, e.g., 2 to 8 weight % sodium tripolyphosphate, e.g., 2 to 7 weight % sodium tripolyphosphate, e.g., 3 to 15 weight % sodium tripolyphosphate, e.g., 3 to 10 weight % sodium tripolyphosphate, e.g., 3 to 9 weight % sodium tripolyphosphate,
- composition 1.6-1.25 wherein the tartar control agent comprises at least one of sodium hexametaphosphate ((NaP0 3 )6, SHMP), sodium trimetaphosphate ( ⁇ 3 ⁇ 4 ⁇ 3 ⁇ , STMP), and a ⁇ -phase calcium pyrophosphate, such as disclosed in U.S. Patent No. 6,241,974.
- the tartar control agent comprises at least one of sodium hexametaphosphate ((NaP0 3 )6, SHMP), sodium trimetaphosphate ( ⁇ 3 ⁇ 4 ⁇ 3 ⁇ , STMP), and a ⁇ -phase calcium pyrophosphate, such as disclosed in U.S. Patent No. 6,241,974.
- composition 1 or 1.1-1.26 wherein the composition comprises water, a thickener, a buffer, a humectant, a surfactant, an abrasive, a sweetener, a flavorant, a visual aid (e.g. a pigment, a dye, or a mixture thereof), an anti-caries agent, an antibacterial, a whitening agent, a desensitizing agent, a preservative, or a mixture thereof.
- a thickener e.g. a buffer, a humectant, a surfactant, an abrasive, a sweetener, a flavorant, a visual aid (e.g. a pigment, a dye, or a mixture thereof), an anti-caries agent, an antibacterial, a whitening agent, a desensitizing agent, a preservative, or a mixture thereof.
- a visual aid e.g. a pigment, a dye, or a mixture thereof
- composition 1 or 1.1-1.28 wherein the composition comprises a thickener Composition 1 .29 wherein the thickener is a mixture of thickening silica, carrageenan gum, and sodium carboxyrnethylcellulose.
- composition 1 or 1.1-30 wherein the composition comprises a buffer wherein the composition comprises a buffer.
- composition 1.31 wherein the buffer is sodium hydroxide
- composition .1 or 1.1-1.43 wherein the composition comprises an anti-caries agent
- composition 1.44 wherein the anti-caries agent is a fluoride ion source.
- Composition 1.45 wherein the fluoride ion source is stannous fluoride, sodium fluoride, potassium fluoride, sodium rnonofluorophosphate, sodium fluorosilicate, ammonium fluorosilicate, amine fluoride (e.g., ' N'-octadecyltrimethyiendiamine- N, , '-trisi2-etIiaiK)[) ⁇ dihydrofluoride ⁇ , ammonium fluoride, titanium fluoride, hexafluorosulfate, or a mixture thereof.
- the fluoride ion source is stannous fluoride, sodium fluoride, potassium fluoride, sodium rnonofluorophosphate, sodium fluorosilicate, ammonium fluorosilicate, amine fluoride (e.g., ' N'-octadecyltrimethyiendiamine- N, , '-trisi2-e
- Composition 1.46 wherein the anticaries agent is sodium fluoride.
- composition I or 1.1-1.49 wherein the composition comprises an anti-attachment agent selected from Ethyl lauroyl arginate, Delmopinol, chitosan, or a mixture thereof, e.g., wherein the composition comprises Ethyl lauroyl arginate, e.g., wherein the composition comprises Delmopinol, e.g., wherein the composition comprises ciiitosan, e.g., wherein the composition comprises a mixture thereof.
- Composition 1 or 1.1-1.50 wherein the composition comprises a whitening agent.
- Composition 1.51 wherein the whitening agent is hydrogen peroxide.
- composition 1.52 wherein the composition comprises a polymer-peroxide complex, e.g., a cross- linked polyvinylpyrrolidone hydrogen peroxide complex.
- composition 1 or .1.1-1.54 wherein the composition is a mouthwash, toothpaste, tooth gel, tooth powder, non-abrasive gel, mousse, foam, mouth spray, lozenge, oral tablet, dental implement, or pet care product,
- composition 1 or 1.1-1.55 wherein the composition is a mouthwash.
- compositions wherein the phosphate/acrylate co-polymer is a co- polymerized product of a mixture of acrylic acid, methacrylic acid, and 2- hydrox ethyl methacr late phosphates of Formula .1 :
- n 0, 1 or 2.
- compositions wherein the phosphate/acrylate co-polymer is a co- polymerized product of a mixture of acrylic acid, methacrylic acid, and 2- hydroxyethyi methacrylate phosphates of Formula 1 comprising acrylic acid in a molar percentage of 80-90%, e.g., about 85%; methacrylic acid in a molar percentage of 5-15%, e.g., about 1 1 %, and hydroxyethyl methacrylate phosphates of Formula 1 in a molar perce tage of 2-6%, e.g., about 4%. 1.60 Any foregoing compositions wherein the phosphate/acrylate co-polymer has an average molecular weight of from 10 to 40 kDa, e.g., 20 to 30 kDa.
- compositions wherein the phosphate/acrylate copolymer is a random copolymer having a weight average molecular weight of about 20,000 to 30,000 grams per mole that is the copolymerized product of a mixture of acrylic acid, methacrylic acid, and 2-hydroxyethy methacr iate phosphates of Formula 1, e.g., in a molar ratio of about 85 : 11 :4.
- the oral care compositions disclosed herein e.g., Composition 1 , e.g., 1.1-1.61
- the oral care compositions disclosed herein comprise 0 to 90 weight % water, e.g., 0.1 to 90 weight % water, e.g., 1 to 80 weight % water, e.g., 2 to 70 weight % water, 5 to 60 weight % water, e.g., 5 to 50 weight % water, e.g., 20 to 60 weight % water, e.g., 10 to 40 weight % water.
- This amount of water includes the free water which is added plus that amount which is introduced with other components of the oral care composition, such as with sorbitol.
- a thickener provides a desirable consistency and/or stabilizes and/or enhances performance (e.g., provides desirable active release characteristics upon use) of the oral care composition.
- the oral care compositions disclosed herein e.g., Composition 1 , e.g., 1 , 1 -1 ,61 , comprise from 0.01 to .15 weight % of a thickener, 0.1 to 1.5 weight % of a thickener, e.g., 0.1 to 10 weight % of a thickener, e.g., 0.1 to 5 weight % of a thickener, e.g., 0.5 to 10 weight % of a thickener, e.g., 0.5 to 5 weight % of at a thickener, e.g., .1 to 4 weight % of a thickener, e.g., 2 to 5 weight % of a thickener, e.g., 2 to 4 weight % of a thickener, e.g
- Thickeners that may be used in the oral care compositions disclosed herein, e.g., Composition 1, e.g., 1.1-1.61, include, for example, carboxy vinyl polymers, carrageenan (also known as carrageenan gum), hydroxyethyl cellulose (HEC), natural and synthetic clays (e.g., Veegum and laponite), water soluble salts of cellulose ethers (e.g., sodium carboxymethylceilulose (CMC) and sodium carboxymethyl hydroxyethyl cellulose), natural gums (e.g., gum karaya, xanthan gum, gum arable, and gum tragacanth), colloidal magnesium aluminum silicate, silica (e.g., finely divided silica), polyvinyl pyrroHdone, carbowaxes,
- silica e.g., finely divided silica
- polyvinyl pyrroHdone polyvinyl pyrroHdone
- a mixture of thickening si lica and carrageenan gum is used as the thickener in the oral care compositions disclosed herein, e.g., Composition 1, e.g., 1 , 1 -1.61 .
- the oral care compositions disclosed herein, e.g., Composition 1, e.g., 1.1-1.61 comprise from 0.01 to 15 weight % of thickening silica and carrageenan gum, 0.1 to 1 weight % of thickening silica and carrageenan gum, e.g., 0.1 to 1.0 weight % of thickening silica and carrageenan gum, e.g., 0.1 to 5 weight % of thickening silica and carrageena gum, e.g., 0.5 to 10 weight % of thickening silica and carrageenan gum, e.g., 0.5 to 5 weight % of thickening silica and carrageenan gum, e.g.,
- a buffer adjusts the pH of oral care compositions, for example, to a range of about pH 4.0 to about pH 6.0.
- the oral care compositions disclosed herein e.g., Composition 1 , e.g., 1.1.-1.61, comprise from 0.1 to 10 weight % of a buffer, 0.5 to 10 weight % of a buffer, e.g., 0.5 to 5 weight % of a buffer, e.g., 0.5 to 4 weight % of a buffer, e.g., 0.5 to 3 weight % of a buffer, e.g., 0.5 to 2 weight % of a buffer, e.g., 1 to 2 weight % of a buffer.
- Buffers that may be used in the oral care compositions disclosed herei include, for example, sodium bicarbonate, sodium phosphate ⁇ e.g., monosodium phosphate disodium phosphate ( ⁇ , ⁇ ), trisodium phosphate (NasPO,*) ⁇ , sodium, hydroxide, sodium carbonate, sodium acid pyrophosphate, citric acid, sodium citrate, and mixtures thereof.
- sodium hydroxide is used as the buffer in. the oral care compositions disclosed herein, e.g., Composition 1 , e.g., 1.1 - 1.61.
- the oral care compositions disclosed herein comprise from 0.1 to 10 weight % of sodium hydroxide, e.g., 0.5 to 10 weight % of sodium hydroxide, e.g., 0.5 to 5 weight % of sodium hydroxide, e.g., 0.5 to 4 weight % of sodium hydroxide, e.g., 0.5 to 3 weight % of sodium hydroxide, e.g., 0.5 to 2 weight % of sodium hydroxide, e.g., 1 to 2 weight % of sodium hydroxide.
- sodium hydroxide e.g., 0.5 to 10 weight % of sodium hydroxide, e.g., 0.5 to 5 weight % of sodium hydroxide, e.g., 0.5 to 4 weight % of sodium hydroxide, e.g., 0.5 to 3 weight % of sodium hydroxide, e.g., 0.5 to 2 weight % of sodium hydroxide, e.g., 1 to 2 weight % of sodium hydroxide
- a humeciant keeps oral care compositions from, hardening upon exposure to air. Certain, humectants can also impart desirable sweetness or flavor to oral care compositions.
- the oral care compositions disclosed herein e.g., Composition 1 , e.g., 1.1-1.61, comprise, on a pure humectant basis, from 0 to 70 weight % of a humectant, e.g., 10 to 70 weight % of a humectant, e.g., .10 to 65 weight % of a humectant, e.g., 10 to 60 weight % of a humectant, e.g., 10 to 50 weight % of a humectant, e.g., 20 to 50 weight % of at a humectant, e.g., 20 to 40 weight % of a humectant.
- Humectants that may be used in the oral care compositions disclosed herein, e.g., Composition 1, e.g., 1.1-1.61, include, for example, glycerin, sorbitol, xylitol, butylene glycoi, polyethylene glycol, propylene glycol, trirnethyl glycine, and mixtures thereof.
- a mixture of glycerin, sorbitol, and propylene glycol is used as the humectant in the oral care compositions disclosed herein, e.g., Composition. 1 , e.g., 1. 1 -1.61.
- the oral care compositions disclosed herein comprise, on a pure humectant basis, from 0 to 70 weight % of glycerin, sorbitol, and propylene glycol, e.g., 10 to 70 weight % of glycerin, sorbitol, and propylene glycol, e.g., 10 to 65 weight % of glycerin, sorbitol, and propylene glycol, e.g., 10 to 60 weight % of glycerin, sorbitol, and propylene glycol, e.g., 10 to 50 weight % of glycerin, sorbitol, and propylene glycol, e.g., 20 to 50 weight % of glycerin, sorbitol, and propylene glycol, e.g., 20 to 40 weight % of glycerin,
- the oral care compositions disclosed herein e.g., Composition I , e.g., 1 .1-1 .61 , comprise a surfactant, e.g., selected from anionic, cationic, zwitterionic, and nonionic surfactants, and mixtures thereof.
- the surfactant is reasonably stable throughout a wide pH range.
- Surfactants are described in, for example, U.S. Pat. No. 3,959,458, to Agncola et al; U.S. Pat. No. 3,937,807, to Haefele; and U.S. Pat. No. 4,051,234, to Gieske et al.
- the oral care compositions disclosed herein comprise from 0.01 to 10 weight % of a surfactant, e.g., 0.05 to 5 weight % of a surfactant, e.g., 0.1 to 10 weight % of a surfactant, e.g., 0.1 to 5 weight % of a surfactant, e.g., 0.1 to 2 weight % of a surfactant, e.g., 0.5 to 2 weight % of a surfactant.
- a surfactant e.g., 0.05 to 5 weight % of a surfactant, e.g., 0.1 to 10 weight % of a surfactant, e.g., 0.1 to 5 weight % of a surfactant, e.g., 0.1 to 2 weight % of a surfactant, e.g., 0.5 to 2 weight % of a surfactant.
- the oral care compositions disclosed herein comprise from 0.01 to 10 weight % of an anionic surfactant, e.g., 0.05 to 5 weight % of an anionic surfactant, e.g., 0.1 to 10 weight % of an anionic surfactant, e.g., 0.1 to 5 weight % of an anionic surfactant, e.g., 0.1 to 2 weight % of an anionic surfactant, e.g., 0.5 to 2 weight % of an anionic surfactant, e.g., 1.5 weight % of an anionic surfactant.
- an anionic surfactant e.g., 0.05 to 5 weight % of an anionic surfactant, e.g., 0.1 to 10 weight % of an anionic surfactant, e.g., 0.1 to 5 weight % of an anionic surfactant, e.g., 0.1 to 2 weight % of an anionic surfactant, e.g., 0.5 to 2 weight % of
- Anionic surfactants that may be used in the oral care compositions disclosed herein, e.g., Composition 1 , e.g., 1.1-1.61 , include, for example,
- water-soluble salts of higher fatty acid monogiyceride monosuifates such as the sodium salt of the monosulfated monoglyceri.de of hydrogenated coconut oil fatty acids such as sodium -methyl N-cocoy! taurate, sodium cocomonoglyceride sulfate,
- alkyl sulfates such as sodium lauryl sulfate
- n is 1 -6, e.g., 2, 3 or 4
- X is Na or K, for example sodium iaureth-2 sulfate (CH 3 (CH2)ioCH2(OCH 2 CH2)20S03 a),
- alkyl atyl sulfonates such as sodium dodecyl benzene sulfonate (sodium lauryl benzene sulfonate), and
- higher alkyl suifoacetates such as sodium lauryl suifoacetate (dodecyl sodium, sulfoacetate), higher fatty acid esters of 1,2 dihydroxy propane sulfonate, sulfocolaurate (N-2-eth l laurate potassium sulfoacetamide) and sodium lauryl sarcosinate.
- higher alkyl refers to C 6 ⁇ 3 ⁇ 4 alkyl
- the oral care compositions disclosed herein e.g., Composition I , e.g., 1.1-1.61, comprise an anionic surfactant.
- the anionic surfactant is the water soluble salt of alkyl sulfates having from 10 to 18 carbon atoms in the alkyl radical and water soluble salts of sulfonated monoglycerides of fatty acids having from 10 to 18 carbon atoms.
- Sodium lauryl sulfate, sodium lauroyl sarcosinate, and sodium coconut monogiyceride sulfonates are examples of anionic surfactants of that type.
- the oral care compositions disclosed herein e.g., Composition 1 , e.g., 1.1-1.61, comprise sodium lauryl sulfate, sodium ether lauryl sulfate, or a mixture thereof.
- the oral care compositions disclosed herein, e.g., Composition 1, e.g., 1.1 -1 .61 comprise sodium lauryl sulfate.
- the oral care compositions disclosed herein comprise from 0.01 to 10 weight % sodium lauryl sulfate, e.g., 0.05 to 5 weight % sodium lauryl sulfate, e.g., 0.1 to 10 weight % sodium lauryl sulfate, e.g., 0.1 to 5 weight % o sodium lauryl sulfate, e.g., 0.1 to 2 weight % sodium lauryl sulfate, e.g., 0.5 to 2 weight % sodium lauryl sulfate, e.g., 1 .5 weight % sodium lauryl sulfate.
- the oral care compositions disclosed herein e.g., Composition 1 , e.g., 1.1-1.61, comprise 5 to 70 weight % of an abrasive, e.g., 5 to 60 weight % of an abrasive, e.g., 5 to 50 weight % of an abrasive, e.g., 5 to 40 weight % of an abrasive, e.g., 5 to 30 weight % of an abrasive, e.g., .10 to 30 weight % of an abrasive, e.g., 10 to 20 weight % of an abrasive.
- Abrasives that may be used in the oral care compositions disclosed herein, e.g., Composition 1, e.g., 1.1-1.61, include, for example, a calcium phosphate abrasive, e.g., tricalcittm phosphate (Ca 3 (PQ 4 ) 2 ), hydroxyapatite (Ca 10 (PO 4 )6(OH) 2 ), dicalcium phosphate dihydrate (CaHP0 4 23 ⁇ 40, also sometimes referred to herein as DiCal), calcium pyrophosphate, and mixtures thereof.
- Calcium carbonate e.g., precipitated calcium carbonate, may also be employed as an abrasive.
- abrasives that may be used in the oral care compositions disclosed herein, e.g., Composition 1 , e.g., 1.1-1.61, include, for example, silica abrasives such as precipitated silicas having a mean particle size of up to about 20 microns, such as Zeodent 115®, marketed by J. M, Huber, as well as sodium metaphosphate, potassium metaphosphate, aluminum silicate, calcined alumina, bentonite or other siliceous materials, or mixtures thereof.
- silica abrasives such as precipitated silicas having a mean particle size of up to about 20 microns, such as Zeodent 115®, marketed by J. M, Huber, as well as sodium metaphosphate, potassium metaphosphate, aluminum silicate, calcined alumina, bentonite or other siliceous materials, or mixtures thereof.
- Silica abrasives used herein, as well as the other abrasives may have an average particle size ranging between about 0.1 and about 30 microns, e.g., between about 5 and about 15 microns.
- the silica abrasives may be from precipitated silica or silica gels, such as the silica xerogels described in U.S. Patent No. 3,538,230 to Pader et al. and U.S. Patent No. 3,862,307 to Digiulio.
- Particular silica xerogels are marketed under the trade name Syloid® by the W. R. Grace & Co. Davison Chemical Division.
- Precipitated silica materials include those marketed by the J. M. Huber Corp, under the trade name Zeodent®, including the silica carrying the designation Zeodent 115 and 119.
- Those silica abrasives are described in U.S. Patent No. 4,340,583 to Wason.
- abrasives that may be used in the oral care compositions disclosed herein, e.g., Composition 1 , e.g., 1.1-1.61, include silica gels and precipitated amorphous silica having an oil absorption value of about less than about 100 cc/100 g silica and in the range of about 45 cc/100 g to about 70 cc/100 g silica. Oil absorption values are measured using the ASTA Rub-Out Method D281.
- the silica comprises colloidal particles having an average particle size of about 3 microns to about 12 microns, and about 5 to about 10 microns.
- the abrasive comprises a large fraction of very small particles, e.g., having a d50 less than about 5 microns, e.g., small particle silica (SPS) having a d50 of about 3 to about 4 microns, e.g., Sorbosil AC43® (Ineos).
- SPS small particle silica
- Sorbosil AC43® Sorbosil AC43® (Ineos).
- the small particle component may be present in combination with a second larger particle abrasive.
- Low oil absorption silica abrasives that may be used in the oral care compositions disclosed herein, e.g., Composition 1, e.g., 1.1-1.61, are marketed under the trade designation Sylodent WXA ⁇ by Davison Chemical Division of W.R. Grace & Co., Baltimore, Md. 21203.
- Sylodent 650 XWA® a silica hydrogel composed of particles of colloidal silica having a water content of about 29% by weight averaging about 7 to about 10 microns in diameter, and an oil absorption of less than about 70 cc/100 g of silica is an example of a low oil absorption silica abrasive that may be used in the oral care compositions disclosed herein, e.g.. Composition 1, e.g., 1 .1-1.61.
- the oral care composition disclosed herein e.g., Composition 1, e.g, 1 ,1 -1.61
- the oral care compositions disclosed herein, e.g., Composition 1, e.g., 1.1 - 1.61 comprise 5 to 70 weight % high cleaning silica, e.g., 5 to 60 weight % high cleaning silica, e.g., 5 to 50 weight % high cleaning silica, e.g., 5 to 40 weight % high cleaning silica, e.g., 5 to 30 weight % high cleaning silica, e.g., 10 to 30 weight % high cleaning silica, e.g., 10 to 20 weight % high cleaning silica.
- the oral care compositions disclosed herein comprise a sweetener.
- the oral care compositions disclosed herein, e.g., Composition 1 e.g., 1 ,1 -1.61 , comprise 0.005 to 10 weight % of a sweetener, e.g., 0.01 to 10 weight % of a sweetener, e.g., 0.1 to 10 weight % of a sweetener, e.g., from 0.1 to 5 weight % of a sweetener, e.g., from 0.1 to 3 weight % of a sweetener, e.g., f om 0.1 to 1 weight % of a sweetener, e.g., from 0.1 to 0.5 weight % of a sweetener.
- Sweeteners that may be used in the oral care compositions disclosed herein, e.g.. Composition 1 , e.g., 1 .1-1.61 , include, for example, sucrose, glucose, saccharin, sucralose, dextrose, ievulose, lactose, mannitol, sorbitol, fructose, maltose, xylitol, saccharin, salts (e.g., sodium saccharin), thaurnatin, aspartame, D- iryptophan, dihydrochaicones, acesulfame, cyclamate salts, and mixtures thereof.
- sucrose glucose, saccharin, sucralose, dextrose, ievulose, lactose, mannitol, sorbitol, fructose, maltose, xylitol
- saccharin e.g., sodium saccharin
- salts e
- sodium saccharin is used as the sweetener in the oral care compositions disclosed herein, e.g., Composition 1 , e.g., 1.1 -1 .61 .
- the oral care compositions disclosed herein, e.g., Composition I e.g., 1.1-1.61, comprise 0.005 to 10 weight % sodium saccharin, e.g., 0.01 to 10 weight % sodium saccharin, e.g., 0.1 to 10 weight % sodium saccharin, e.g., from 0.1 to 5 weight % sodium saccharin, e.g., from 0.1 to 3 weight % sodium saccharin, e.g., from 0.1 to 1 weight % sodium saccharin, e.g., from 0.1 to 0.5 weight % sodium, saccharin.
- the oral care compositions disclosed herein comprise a flavorant.
- the oral care compositions disclosed herein, e.g., Composition 1 e.g., 1 .1-1.61, comprise 0.1 to 5 weight % of a flavorant, e.g., 0.1 to 4 weight % of a flavorant, e.g., 0.1 to 3 weight % of a flavorant, e.g., 0.1 to 2 weight % of a flavorant, e.g., 0.5 to 2 weight % of a flavorant, e.g., 0.6 to 2 weight % of a flavorant, e.g., 0.7 to 2 weight % of a flavorant, e.g., 0.8 to 2 weight % of a flavorant e.g., 0.9 to 2 weight % of a flavorant, e.g.,
- F!avorants that may be used in the oral care compositions disclosed herein, e.g.. Composition 1, e.g., 1.1-1 .61 , include, for example, essential oils, as well as various flavoring aldehydes, esters, alcohols, and similar materials, as well as menthol, carvooe, and anethoie, as well as mixtures thereof.
- essential oils include oils of spearmint, peppermint, wintergreen, sassafras, clove, sage, eucalyptus, marjoram, cinnamon, lemon, lime, grapefruit, and orange.
- a mixture of peppermint, oil and spearmint oil is used as the flavorant in the oral care compositions disclosed herein, e.g., Compositio 1 , e.g., 1.1-1.61.
- the oral care compositions disclosed herein e.g., Composition 1, e.g., 1.1-1.61, comprise a visual aid, including but not limited to a pigment, a dye, speckles, beads, strips, and mixtures therof.
- the oral, care compositions disclosed herein, e.g., Composition L e.g., 1.1-1.61 comprise 0.001 to 20 weight % of a pigment, e.g., 0.01. to 20 weight % of a visual aid, e.g., 0.01.
- the oral care compositions disclosed herein e.g., Composition I, e.g., 1.1- 1.61 , comprise titanium dioxide.
- the oral care compositions disclosed herein comprise 0.00.1 to 20 weight % titanium dioxide, e.g., 0.01 to 20 weight % titanium dioxide, e.g., 0.01 to 20 weight % titanium dioxide, e.g., 0.1 to 20 weight % titanium dioxide, e.g., 0.1 to .10 weight % titanium dioxide, e.g., 0.1 to 5 weight % titanium dioxide, e.g., 0.1 to 3 weight % titanium dioxide, e.g., 0.1 to I weight % titanium dioxide.
- the oral care compositions disclosed herein e.g., Composition 1, e.g., 1 .1-1.61 , further comprise an anti-caries agent, hi some embodiments, the oral care compositions disclosed herein, e.g., Composition.
- 1, e.g., .1.1-1.61 comprise 0.005 to 10 weight % of the anti-caries agent, e.g., 0.01 to 10 weight % of the anti-caries agent, e.g., 0.01 to 5 weight % of the anti-caries agent, e.g., 0.01 to 1 weight % of the anti-caries agent, e.g., 0.01 to 0.3 weight % of the anti-caries agent, e.g., 0.1 to 10 weight % of the anti-caries agent, e.g., 0.1 to 5 weight % of the anti-caries agent, e.g., 0.1 to 2 weight % of the anti-caries agent, e.g., 0.1 to 1 weight % of the anti-caries agent, e.g., 0.1 to 0.8 weight % of the anti-caries agent, e.g., 0.1 to 0.6 weight % of the anti-caries agent, e.g., 0.1 to 0.5
- the anti -caries agent is a fluoride ion source.
- the oral care compositions disclosed herein e.g., Composition 1, e.g., 1.1-1.61, further comprise 0.005 to 10 weight % of the anti-caries agent which is a fluoride ion source, e.g., 0.01 to 10 weight % of the anti-caries agent which is a fluoride ion source, e.g., 0.01 to 5 weight % of the anti-caries agent which is a fluoride ion source, e.g., 0.01 to 1 weight % of the anti-caries agent which is a fluoride ion source, e.g., 0.01 to 0.3 weight % of the anti-caries agent which is a fluoride ion source, e.g., 0.1 to 10 weight % of the anti-caries agent which is a fluoride ion source, e.g., 0.1
- fluoride ion sources that may be used in the oral compositions disclosed herein, e.g., Composition 1, e.g., 1.1- 1 ,61 , are found m U.S. Patent No. 3,535,421 to Briner et al; U.S. Patent No. 4,885,155 to Parran, Jr. et al,, and U.S. Patent No. 3,678,154 to Widder et al.
- fluoride ion sources include, for example, stannous fluoride, sodium fluoride, potassium fluoride, sodium monofluorophosphate, sodium fluorosilicate, ammonium ffuorosilicate, amine fluoride (e.g., N - octadecyltrimethylendiamine-N,N,N , -tris(2-ethanol)-dihydrofluoride), ammonium fluoride, titanium fluoride, hexafluorosulfate, and combinations thereof.
- the fluoride ion source includes stannous fluoride, sodium fluoride, and sodium monofluorophosphate, as well as mixtures thereof.
- the anti-caries agent is sodium fluoride.
- the oral care compositions disclosed herein e.g., Composition 1, e.g., i .1-1.61 , comprise 0.005 to 10 weight % sodium fluoride, e.g., 0.01 to 10 weight % sodium fluoride, e.g., 0.01 to 5 weight % sodium fluoride, e.g., 0.01 to 1 weight % sodium fluoride, e.g., 0.01 to 0.3 weight % sodium fluoride, e.g., 0.1 to 10 weight % sodium, fluoride, e.g., 0.1 to 5 weight % sodium fluoride, e.g., 0.1 to 2 weight % sodium fluoride, e.g., 0.1 to 1 weight % sodium fluoride, e.g., 0.1 to 0.8 weight % sodium fluoride, e.g., 0.1 to 0.6 weight % sodium fluoride,
- the oral care compositions disclosed herein comprise the anti-caries agent which is a fluoride ion source in an amount sufficient to supply 25 pprn to 25,000 ppm of fluoride ions, e.g., from 100 to 20,000 pprn of fluoride ions, e.g., from 300 to 15,000 ppm of fluoride ions, e.g., from 500 to 10,000 ppm of fluoride ions, e.g., from 500 to 8,000 ppm of fluoride ions, e.g., from 500 to 6,000 ppm of fluoride ions, e.g., from 500 to 4,000 ppm of fluoride ions, e.g., from.
- the anti-caries agent which is a fluoride ion source in an amount sufficient to supply 25 pprn to 25,000 ppm of fluoride ions, e.g., from 100 to 20,000 pprn of fluoride ions, e.g.
- a toothpaste for consumer use comprises the anti-caries agent which is a fluoride ion. source in an amount sufficient to supply from 1,000 to 1,500 ppm of fluoride ions, with pediatric toothpaste having somewhat less.
- a dentifrice or coating for professional application comprises the anti-caries agent which is a fluoride ion source in an amount sufficient to supply from 5,000 to 25,000 ppm of fluoride ions,
- the oral care compositions disclosed herein comprise an anti-bacterial or anti-attachment agent.
- the oral care compositions disclosed herein, e.g., Composition 1, e.g., 1.1-1.61 comprise 0.01 to 10 weight % of an anti-hacteriai, e.g., 0.1 to 10 weight % of an anti-bacterial, e.g., 0.5 to 5 weight % of an anti-bacterial, e.g., 0.01 to 5 weight % of an anti-bacterial, e.g., 0.05 to 4 weight % of an anti-bacterial, e.g., 0.05 to 3 weight % of an anti-bacterial, e.g., 0.05 to 2 weight % of an antibacterial, e.g., 0.05 to 1 weight % of an anti-bacteriai, e.g., 0.1 to 1 weight % of an
- the amount of the anti-bacterial will vary depending on the type of oral care composition, with levels used in toothpaste being, for example, 5 to 15 times greater than used in mouthwash.
- a mouthwash comprising triciosan may comprise, e.g., 0.03 weight % triclosan while a toothpaste comprising triclosan toothpaste may comprise 0.3 weight % triclosan.
- anti-bacteriais that may be used in the oral compositions disclosed herein, e.g., Composition 1 , e.g., 1.1 - 1.61 , include, for example, halogenated diphenyl ether (e.g.
- herbal extracts and essential oils e.g., rosemary extract, tea extract, magnolia extract, thymol, menthol, eucalyptol, geranioi, carvacroi, citral, hinokitoi, catechol, methyl salicylate, epigallocatechin gailate, epigallocatechin, gallic acid, miswak extract, sea-buckthorn extract
- bisguanide antiseptics e.g., chiorhexidine, aiexidine or octenidine
- quaternary ammonium compounds e.g., cetyipyridinium chloride (CPC), benzalkonium chloride, tetradecylpyri ⁇ Htuum chloride (TPC), N ⁇ tetrad.ecyi-4 ⁇ ethylpyridirnurn chloride (TDEPC)
- phenolic antiseptics hexetidine, octenidine, sangumarine, povidone io
- the anti-bacterial is triclosan.
- the oral care compositions disclosed herein comprise 0.01 to 10 weight % triclosan, e.g., 0.1 to 10 weight % triclosan, e.g., 0.5 to 5 weight % triclosan, e.g., 0.01 to 5 weight % triclosan, e.g., 0.05 to 4 weight % triclosan, e.g., 0.05 to 3 weight % triclosan, e.g., 0.05 to 2 weight % triclosan, e.g., 0.05 to 1 weight % triclosan, e.g., 0.1 to 1 weight % triclosan, e.g., 0.1 to 0.5 weight % triclosan.
- a whitening agent whitens a tooth to which it is applied, in some embodiments, the oral care compositions disclosed herein, e.g., Composition 1, e.g., 1.1-1.61 , comprise a whitening agent, hi some embodiments, the oral care compositions disclosed herein, e.g., Composition 1, e.g., i .1-1.61 , comprise a whitening agent in a dental surface-whitening effective amount, e.g., 0.1 to 90 weight % whitening agent, e.g., 0.5 to 50 weight % whitening agent, e.g., 1 to 30 weight % whitening agent, e.g., 2 to 10 weight % whitening agent.
- a dental surface-whitening effective amount e.g., 0.1 to 90 weight % whitening agent, e.g., 0.5 to 50 weight % whitening agent, e.g., 1 to 30 weight % whitening agent, e.g., 2 to 10 weight % whitening
- whitening agents thai may be used in the oral compositions disclosed herein, e.g., Composition 1, e.g., 1.1-1.61, include, for example, peroxides, metal chlorites, perborates, percarbonates, peroxyacids, hypochlorites, and mixtures thereof.
- the whitening agent is hydrogen peroxide or a hydrogen peroxide source, for example, urea peroxide or a peroxide salt or complex (for example, peroxyphosphate, peroxycarbonate, perborate, peroxysilicate, or persulphate salts; for example calcium peroxvphosphate, sodium perborate, sodium carbonate peroxide, sodium peroxvphosphate, and potassium persulfate), or a hydrogen peroxide polymer complex (for example, a peroxide-polyvinyl pyrrolidone polymer complex).
- urea peroxide or a peroxide salt or complex for example, peroxyphosphate, peroxycarbonate, perborate, peroxysilicate, or persulphate salts; for example calcium peroxvphosphate, sodium perborate, sodium carbonate peroxide, sodium peroxvphosphate, and potassium persulfate
- a hydrogen peroxide polymer complex for example, a peroxide-polyvinyl pyrrolidone poly
- an oral care composition disclosed herein comprises:
- Phosphate/acrylate polymer (as a.i.) 0.4 - 2.4
- an oral care composition disclosed herein comprises: ingredient %
- Phosphate/acrylate polymer (as a.i.) 0.4 - 2.4
- an oral care composition disclosed herein comprises:
- compositions wherein the composition is a mouthwash, toothpaste, tooth gel, tooth powder, non-abrasive gel, mousse, foam, mouth spray, lozenge, oral tablet, dental implement, or pet care product.
- composition is a mouthwash.
- composition is a toothpaste.
- Method A for the treatment and/or inhibition of a chemical slain, plaque, and/or tartar on a dental surface, comprising contacting the dental surface with any of the preceding oral care composi tions.
- Method A as follows: A.1 Method A wherein the composition is Composition 1 , e.g., 1.1 - 1.61.
- Method A.2 wherein the method is for the treatment of a chemical stain on the dental surface.
- Method A.2 wherem the method is for the treatment of plaque on the dental surface.
- Method A.2 wherein the method is for the treatment of acid erosion on the dental surface.
- Method A.9 wherein the method is for the inhibition of plaque on the dental surface.
- Method A .10 wherein the method is for the inhibition of acid erosion on the dental surface.
- Method B for the treatment and/or inhibition of gum. disease comprising contacting the oral cavity with any of the preceding oral care compositions.
- composition is Composition 1, e.g., 1 .1-1.61.
- Method C for the treatment and/or inhibition of halitosis comprising contacting the oral cavity with any of the preceding oral care compositions.
- composition is Composition 1, e.g., 1.1-1.61.
- Method D for inhibiting biofi!ni formatio on a dental surface comprising contacting the dental surface with any of the preceding oral care compositions.
- composition is Composition 1 , e.g., 1.1 -1.61.
- Method E for treating and/or inhibiting bacteria from sticking together and growing into bigger colonies in an oral cavity comprising contacting the oral cavity with any of the preceding oral care compositions.
- composition is Composition 1, e.g., 1.1-1.61.
- compositions are Composition 1 , e.g., 1.1-1.61.
- A.2 Use A or A. l wherein the use is for the treatment of a chemical stain, plaque, acid erosion, and/or tartar on the dental surface.
- A.4 Use A.2 wherein the use is for th e treatment of plaque on the dental surface.
- A.5 Use A2 wherein the use is for the treatment of acid erosion on the dental surface.
- a .6 Use A.2 wherein the use is for the treatment of tartar on the dental surface.
- A.7 Use A or A.1 wherem the use is for the inhibition of a chemical stain, plaque, acid erosion, and/or tartar on the dental surface.
- A.10 Use A.7 wherein the use is for the inhibition of acid erosion on the dental surface.
- A.11 Use A.7 wherein the use is for the inhibition of tartar on the dental surface.
- A.12 Use A or A.1-A.1 1 wherein the dental surface is a human tooth.
- A.13 Use A or A.1-A.12 wherein the composition is contacted with the dental surface by brushing.
- composition is Composition 1 , e.g., 1.1 -1 .61.
- B.2 Use B or B.1 wherein the use is for the treatment of gum disease.
- B.3 Use B, B.1 , or B.2 wherein the gum disease is gingivitis.
- B.4 Use B, B.l, or B wherein the gum disease is periodontitis.
- B.6 Use B, B.l , or B.5 wherein the gum disease is gingivitis.
- B.7 Use B, B.l, or B.5 wherein the gum disease is periodontitis.
- B.8 Use B or B. l -B.7 wherein the oral cavity is a human oral cavity.
- B.9 Use B or B.1-B.8 wherem the composition is contacted with the oral cavity by brushing.
- composition is Composition 1, e.g., 1.1-1.61.
- C.2 Use C or C.l wherein the oral cavity is a human oral cavity.
- C.3 Use C, C.l, or C.2 wherein the composition is contacted with the oral cavity by brushing.
- compositions e.g., 1.1-1.61.
- D.2 Use D or D.1 wherein the oral cavity is a human oral cavity.
- D.3 Use D, D.l, or D.2 wherein the composition is contacted with the oral cavity by brushing.
- composition 1 e.g., 1 ,1 -1.61 .
- E.2 Use E or E.l wherein the oral cavity is a human oral cavity
- E.3 Use E, E. l , or E.2 wherem the composition is contacted with the oral cavity by brushing.
- inhibition refers to reduction of stains that would otherwise form or develop subsequent to the time of the treatment. Such inhibition can range from a small but observable or measurable reduction to complete inhibition of subsequent staining, by comparison with an untreated or placebo-treated dental surface.
- Method A e.g., A.1- A.10
- Use B e.g., B.1 -B.10
- Method A e.g., A.1-A.10
- Use B e.g., B.1 -B.10
- Method A e.g., A.1 -A.10
- Use B e.g., B.1-B.10
- the Method A e.g., A.1-A.10
- Use B e.g., B.1-B.10
- a method of forming any of the compositions 1.1-1.61 as a mouth rinse that includes the phosphate/acrylate co-polymer and the synthetic anionic linear pofycarboxyfate polymer as well as a zinc salt and a cationic antibacterial agent.
- the method can form a stable composition thai is stable and transparent.
- the method comprises the following steps:
- Any additional materials such as sweeteners, fluoride, colorants, and preservatives can be added to the main mix prior to the premixes being added.
- Phosphate/acrylate polymer (as a.i.) 0.4 - 2.4
- Tetrasodium Pyrophosphate (sodium 0 - 2
- HAP discs hydroxyapatite discs
- the efficacy is quantified by measuring the light reflected from the surface of the HAP disc after treatment of the HAP disc with a 1 :2 dentifrice/water slurry and subsequent exposure to a staining agent, in this case, coffee. The measurement is taken with a chromameter and L a b value recorded.
- the HAP disc is first soaked in saliva overnight and baseline whiteness is measured, next it is treated with 1 :2 dentifrice/water slurry for 5 minutes and the initial L a b is recorded.
- the HAP disc is then exposed to a coffee for 15 mmutes, rinsed with distilled ionized water and incubated in saliva for 20 minutes.
- the above staining process is repeated for a total of three times and the final L a b is read. This value is compared to the initial L a b to quantif the dentifrice inhibition of the coffee stain formation on the HAP disc. The lower the delta L*, the better stain inhibition effect provided by the dentifrice.
- Table 3 The results are displayed in Table 3.
- Phosphate salts are also formulated together with this phosphate/acrylate polymer into dentifrice to further enhance efficacy.
- the test results are shown in Table 4. The results show phosphate salts further enhance the anti-stain efficacy compared to formulae with phosphate/acrylate polymer only and achieve comparable efficacy to both 2.4% phosphate/acrylate polymer (as a.i.) and 0.4% phosphate/acrylate polymer (as a.i.) plus 2% Gantrez.
- a stable mouthwash as evidenced by low turbidity that contains incompatible ingredients can be prepared.
- a cationic material can be included with the phosphate/acrylate polymer by inclusion of synthetic anionic linear polycarboxylate polymer.
- the cationic material is cetylpyridinium chloride.
- Test mouthwashes are prepared as below in Table 5. Each contain 0.1 weight % CPC and 0.08 weight % zinc chloride.
- the formulas above are prepared by creating three premixes to add to a main mixing tank.
- a main mixing tank water, surfactants, sweeteners, fluoride, CPC, potassium sorbate, and dye are added and mixed.
- a first premix is prepared with the phosphate/acrylate polymer, 15% of the total water, and polyols (glycerin and sorbitol). This premix is added to the main mix tank.
- a second premix is prepared with zinc chloride, 1 % of the total water, and the Gantrez. This premix is added to the main mix tank.
- a third premix is prepared with propylene glycol, cooling agents and/or flavoring agents. This premix is then added to the main mixing tank.
- Turbidity for commercial products is typically 0-13NTU. Turbidity is measured using a Hach turbidity meter at 25°C after 24 hours of making the composition. Turbidity is the cloudiness or haziness of a fluid caused by individual particles (suspended solids) that are generally not perceptible to the naked eye.
- Formulations under A were all turbid.
- Formulations under B were all Turbid.
- Formulations under C had acceptable turbidity, which means that the materials are stable together and do not precipitate out.
- Table 6 below has the turbidity measurements for the representative samples for A, B, and C.
- formulations A without the combination of the phosphate/acrylate polymer and the synthetic anionic linear po!yearboxy!aie polymer were turbid.
- Formulations B with a low level of phosphate/acrylate polymer were also turbid.
- Formulations C with a sufficient amount of phosphate/acrylate polymer with the synthetic anionic linear polycarboxylate polymer were able to stabilize the specific amount of CPC and zinc chloride.
Abstract
Description
Claims
Priority Applications (11)
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BR112016014539A BR112016014539B8 (en) | 2013-12-20 | 2013-12-20 | oral hygiene composition, use and composition formation method |
PCT/US2013/076892 WO2015094336A1 (en) | 2013-12-20 | 2013-12-20 | Oral care compositions and methods |
US15/106,543 US9814666B2 (en) | 2013-12-20 | 2013-12-20 | Oral care compositions and methods |
EP13818944.4A EP3082712B1 (en) | 2013-12-20 | 2013-12-20 | Oral care compositions and methods |
AU2013408265A AU2013408265B2 (en) | 2013-12-20 | 2013-12-20 | Oral care compositions and methods |
MX2016008227A MX355064B (en) | 2013-12-20 | 2013-12-20 | Oral care compositions and methods. |
CN201380081985.9A CN106413668B (en) | 2013-12-20 | 2013-12-20 | Oral care compositions and methods |
CA2934501A CA2934501C (en) | 2013-12-20 | 2013-12-20 | Oral care compositions and methods |
TW103144215A TWI686208B (en) | 2013-12-20 | 2014-12-18 | Oral care compositions and methods |
ARP140104839A AR098898A1 (en) | 2013-12-20 | 2014-12-19 | COMPOSITIONS FOR ORAL CARE AND METHODS |
ZA2016/04695A ZA201604695B (en) | 2013-12-20 | 2016-07-08 | Oral care compositions and methods |
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PCT/US2013/076892 WO2015094336A1 (en) | 2013-12-20 | 2013-12-20 | Oral care compositions and methods |
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US (1) | US9814666B2 (en) |
EP (1) | EP3082712B1 (en) |
CN (1) | CN106413668B (en) |
AR (1) | AR098898A1 (en) |
AU (1) | AU2013408265B2 (en) |
BR (1) | BR112016014539B8 (en) |
CA (1) | CA2934501C (en) |
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TW (1) | TWI686208B (en) |
WO (1) | WO2015094336A1 (en) |
ZA (1) | ZA201604695B (en) |
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US20170151158A1 (en) * | 2015-12-01 | 2017-06-01 | Colgate-Palmolive Company | Oral Care Compositions |
WO2018089394A1 (en) | 2016-11-08 | 2018-05-17 | Colgate-Palmolive Company | Oral care compositions |
WO2018089322A1 (en) | 2016-11-08 | 2018-05-17 | Colgate-Palmolive Company | Oral care compositions |
CN108430436A (en) * | 2015-12-17 | 2018-08-21 | 高露洁-棕榄公司 | Include the oral care composition of at least one phosphate/acrylate copolymer and at least one cationic active constituent |
WO2019027468A1 (en) | 2017-08-04 | 2019-02-07 | Colgate-Palmolive Company | Biphasic oral care compositions |
US20190038545A1 (en) * | 2017-08-04 | 2019-02-07 | Colgate-Palmolive Company | Biphasic Oral Care Compositions |
WO2019118339A1 (en) | 2017-12-13 | 2019-06-20 | Colgate-Palmolive Company | Oral care compositions |
WO2020219323A1 (en) * | 2019-04-26 | 2020-10-29 | The Procter & Gamble Company | Reduction of tooth staining derived from cationic antimicrobials |
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EP3313415B1 (en) * | 2015-06-26 | 2021-10-13 | Eikonic R&D Pty Ltd | Composition for the prevention of microbial growth |
WO2020001864A1 (en) * | 2018-06-26 | 2020-01-02 | Unilever N.V. | A novel polymer, a composition, a method and a kit for whitening teeth |
EP4021585A1 (en) * | 2020-03-27 | 2022-07-06 | Colgate-Palmolive Company | Oral care compositions and methods of use |
WO2022026672A1 (en) * | 2020-07-31 | 2022-02-03 | Colgate-Palmolive Company | Process for producing an oral care composition |
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CN108430436A (en) * | 2015-12-17 | 2018-08-21 | 高露洁-棕榄公司 | Include the oral care composition of at least one phosphate/acrylate copolymer and at least one cationic active constituent |
AU2016371133B2 (en) * | 2015-12-17 | 2019-03-14 | Colgate-Palmolive Company | Oral care compositions comprising at least one phosphate/acrylate copolymer and at least one cationic active ingredient |
EP3389602A4 (en) * | 2015-12-17 | 2019-05-08 | Colgate-Palmolive Company | Oral care compositions comprising at least one phosphate/acrylate copolymer and at least one cationic active ingredient |
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Also Published As
Publication number | Publication date |
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BR112016014539A2 (en) | 2017-08-08 |
TW201538176A (en) | 2015-10-16 |
BR112016014539B1 (en) | 2020-03-10 |
CA2934501C (en) | 2021-05-18 |
EP3082712A1 (en) | 2016-10-26 |
US9814666B2 (en) | 2017-11-14 |
ZA201604695B (en) | 2018-07-25 |
MX2016008227A (en) | 2016-10-14 |
CN106413668A (en) | 2017-02-15 |
MX355064B (en) | 2018-04-04 |
CA2934501A1 (en) | 2015-06-25 |
BR112016014539B8 (en) | 2020-04-28 |
EP3082712B1 (en) | 2019-08-28 |
AR098898A1 (en) | 2016-06-22 |
AU2013408265A1 (en) | 2016-07-14 |
CN106413668B (en) | 2020-02-14 |
US20160331670A1 (en) | 2016-11-17 |
AU2013408265B2 (en) | 2016-12-15 |
TWI686208B (en) | 2020-03-01 |
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