WO2020081051A1 - Compositions de soin buccodentaire et procédés pour celles-ci - Google Patents

Compositions de soin buccodentaire et procédés pour celles-ci Download PDF

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Publication number
WO2020081051A1
WO2020081051A1 PCT/US2018/055972 US2018055972W WO2020081051A1 WO 2020081051 A1 WO2020081051 A1 WO 2020081051A1 US 2018055972 W US2018055972 W US 2018055972W WO 2020081051 A1 WO2020081051 A1 WO 2020081051A1
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WIPO (PCT)
Prior art keywords
weight
film forming
forming composition
copolymer
teeth
Prior art date
Application number
PCT/US2018/055972
Other languages
English (en)
Inventor
Rong Dong
Irene PETROU
Paloma Pimenta
Stacey Lavender
Shira Pilch
Original Assignee
Colgate-Palmolive Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Colgate-Palmolive Company filed Critical Colgate-Palmolive Company
Priority to CN201880098293.8A priority Critical patent/CN113226272A/zh
Priority to BR112021006656-0A priority patent/BR112021006656B1/pt
Priority to MX2021004167A priority patent/MX2021004167A/es
Priority to PCT/US2018/055972 priority patent/WO2020081051A1/fr
Priority to EP18797335.9A priority patent/EP3849508A1/fr
Priority to CA3112967A priority patent/CA3112967A1/fr
Priority to AU2018445624A priority patent/AU2018445624B2/en
Publication of WO2020081051A1 publication Critical patent/WO2020081051A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/731—Cellulose; Quaternized cellulose derivatives
    • 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
    • A61K8/72—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
    • A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers

Definitions

  • Dentin or dentinal hypersensitivity is a common clinical condition associated with exposed dentin surfaces of teeth.
  • Dentin contains a large numbers of pores or dentin tubules that extend from outer surfaces of the teeth to nerves within the teeth.
  • external stimuli e.g., temperature, pressure, etc.
  • conventional oral care products or compositions thereof may often attempt to numb the nerve or incorporate filling or occluding agents to ameliorate the sensitivity of the teeth.
  • conventional oral care compositions may incorporate filling or occluding agents to physically block or fill the dentin tubules, thereby shielding the nerve from the external stimuli.
  • conventional methods may often require treatment for several days or weeks before any appreciable reduction or improvement in sensitivity is observed.
  • conventional methods may utilize occluding agents in dentifrices (e.g., toothpastes), which may rinse of throughout the day, thereby reducing the effectiveness.
  • the foregoing and/or other aspects and utilities embodied in the present disclosure may be achieved by providing a film forming composition for occluding dentin tubules of teeth.
  • the film forming composition may include a hydrophobic copolymer, a rosin, and an orally acceptable solvent.
  • the hydrophobic copolymer may include an acrylate.
  • the hydrophobic polymer may be or include an acryl ate/octylacryl amide copolymer.
  • the acrylate/octyl acrylamide copolymer may be 2-prope oic acid, 2-methyl-, 2 -methyl propyl ester, polymer with 2-propenoic acid and N-(l, 1,3,3- tetramethylbutyl)-2-propenamide.
  • the hydrophobic copolymer may also include at least one of octylacrylamide/acrylates/butylaminoethyl methacrylate copolymer, VA/butyl maieate/isobornyi acrylate copolymer, acrylates/T-butylacrylamide copolymer, polyvinylpyrrolidone/vinyl acetate copolymer, triacontanyl PVP copolymer, acrylates/dimethylaminoethyl methacrylate copolymer, or mixtures thereof.
  • the film forming composition may further include one or more desensitizing agents with various modes of action.
  • the desensitization agents could physically occlude, depolarize the nerve, and/or provide an analgesic effects to reduce pain.
  • the desensitizing agents may include one or more of a potassium salt, arginine, participated calcium carbonate, small particle silicas, eugenol, strontium salts, zinc salts, chloride salts, and mixtures or combinations thereof.
  • the orally acceptable solvent may include one or more of ethanol, methanol, isopropanol, butanol, water, acetone, methyl ethyl ketone, ethyl acetate, butyl acetate, cyclohexanone, cyclohexane, methylene chloride, chloroform, carbon tetrachloride, trichloroethylene, perchloroethylene, methyl glycol acetate, toluene, benzene, diethyl ether, and benzyl alcohol.
  • the orally acceptable solvent includes ethanol.
  • the film forming composition may include an adhesive.
  • the adhesive may include one or more of a polyvinyl acetaldehyde, a polyvinyl alcohol, a polyvinyl acetate, a polyethylene oxide), a polyacrylate, a polyvinylpyrolidone, a polyvinylpyrolidone/vinyl acetate copolymer, a polyoxyethylene/polyoxopropylene block copolymer, a silicone resin, and combinations thereof.
  • the film forming composition may include a cellulose derivative.
  • the cellulose derivative may include an alkyl cellulose ether.
  • the cellulose derivative may include ethyl cellulose.
  • the cellulose derivative is the ethyl cellulose, and the ethyl cellulose inlcudes an average substitution value of about 2.25 to about 2.60 ethoxy 1 groups per anhydroglucose unit.
  • the film forming composition may further include one or more fatty acids, optionally, the fatty acids is oleic acid.
  • the rosin is at least partially hydrogenated. In another implementation, the rosin is fully hydrogenated.
  • the foregoing and/or other aspects and utilities embodied in the present disclosure may be achieved by providing a method for at least partially occluding dentin tubules of teeth in a subject.
  • the method may include contacting any one of the film forming composition disclosed herein with the teeth of the subject in need thereof.
  • the foregoing and/or other aspects and utilities embodied in the present disclosure may be achieved by providing a method for reducing dental sensitivity of teeth of a subject.
  • the method may include applying any one of the film forming composition disclosed herein with the teeth of the subject in need thereof
  • the method may further include treating the teeth with a toothpaste.
  • the film forming composition may be applied after treating the teeth with the toothpaste.
  • the foregoing and/or other aspects and utilities embodied in the present disclosure may be achieved by providing a method for preparing any one of the film forming compositions disclosed herein.
  • the method may include contacting the hydrophobic copolymer, the rosin, and the orally acceptable solvent with one another.
  • the term“about,” as used herein, in conjunction with a numeral refers to a value that may be ⁇ 0.01% (inclusive), ⁇ 0.1% (inclusive), ⁇ 0.5% (inclusive), ⁇ 1% (inclusive) of that numeral, ⁇ 2% (inclusive) of that numeral, ⁇ 3% (inclusive) of that numeral, ⁇ 5% (inclusive) of that numeral, ⁇ 10% (inclusive) of that numeral, or ⁇ 15% (inclusive) of that numeral. It should further be appreciated that when a numerical range is disclosed herein, any numerical value falling within the range is also specifically disclosed.
  • the present inventors have surprisingly and unexpectedly discovered that applying a film forming composition including a hydrophobic polymer (e.g., a acrylate/octylacrylamide copolymer) and/or a rosin to surfaces of teeth enhances the occlusion of dentin tubules thereof
  • a film forming composition including the hydrophobic polymer and/or the rosin after treatment with a toothpaste for sensitivity maintains, enhances, and/or facilitates the occlusion of dentin tubules, even after an acid challenge.
  • compositions disclosed herein may be or include an oral care product or a film forming composition thereof.
  • the compositions disclosed herein may be an oral care product including the film forming composition, or the film forming composition thereof.
  • the film forming composition may include one or more hydrophobic polymers and/or one or more rosins.
  • the film forming composition may include an acrylate/octyl acrylamide copolymer and/or a rosin, such as an at least partially hydrogenated rosin.
  • the film forming compositions and/or one or more components thereof may be capable of or configured to enhance, facilitate, and/or maintain occlusion of dentin tubules of teeth when applied to surfaces thereof.
  • the film forming compositions and/or one or more components thereof may be configured to at least partially occlude the dentin tubules of teeth to reduce the sensitivity of the teeth.
  • the film forming compositions disclosed herein may also be configured to enhance, facilitate, and/or maintain the occlusion of the dentin tubules treated with a toothpaste.
  • the film forming compositions disclosed herein may be applied prior to, along with, and/or after treatment with a toothpaste to enhance, facilitate, and/or maintain the ability of the toothpaste to occlude dentin tubules.
  • the one or more hydrophobic polymers of the film forming composition may he or include, but are not limited to, hydrophobic film forming polymers, such as hydrophobic film forming polymers having functional groups with properties that provide relatively increased adhesion to surfaces of the oral cavity (e.g., surfaces of teeth).
  • Illustrative functional groups may include, but are not limited to, carboxyl groups, phosphate groups, hydroxyl groups, amines, disulfides, nitro groups, or the like, and combinations thereof.
  • the hydrophobic polymer may be or include a copolymer.
  • the hydrophobic polymer may be or include a carboxylated acrylic copolymer.
  • the hydrophobic polymer may be a copolymer of octylacrylamide and one or more monomers, where the one or more monomers may include one or more of acrylic acid, methacrylic acid, and any one or more simple esters thereof.
  • the hydrophobic polymer may be a polymer formed from octylacrylamide, t-butylaminoethyl methacrylate, and one or more monomers of acrylic acid, methacrylic acid, or any one or more simple esters thereof.
  • carboxylated acrylic copolymers may be or include, but are not limited to, those sold under the trade names DERMACRYL®, AMPHOMER®, BALANCE®, and VERSACRYL®, which are commercially available from AkzoNobel Company, Surface Chemistry of Amsterdam, Netherlands
  • the carboxylated acrylic copolymers may be or include, but are not limited to, AMPHOMER 6, 4961, AMPHOMER' 8 ’ HC, DERMACRYL ® 2.0, RESYN’ "" XP, a hydrophobic copolymer selected from octylacrylamide/acrylates/butylaminoethyl methacrylate copolymer, such as AMPHOMER® LV-71, AMPHOMER®, AMPHOMER® EDGETM, BALANCE® 47, or the like, and combinations thereof!, all of which are commercially available from AkzoNobe!
  • the hydrophobic copolymer may be selected from VA/butyl maleate/isobomyl acrylate copolymer, such as ADVANTAGETM PLUS from Ashland Global Specialty Chemicals Inc. of Covington, KY.
  • the hydrophobic copolymer may be selected from acrylates/t-butylacrylamide copolymer, such as ULTRAHOLD® STRONG and ULTRAHOLD®8 from BASF SE of Ludwigshafen, Germany
  • the hydrophobic copolymer may be selected from acrylates/dimethylaminoethyl methacrylate copolymer, such as the EUDRAGIT® range of polymers fro Evonik Industries of Essen, Germany, such as EUDRAGIT ®E 100, EUDRAGIT® E PO, EUDRAGIT® RS 100, EUDRAGIT® RS PO, EUDRAGIT® RL PO, EUDRAGIT® RL 100, or the like, and combinations thereof.
  • the hydrophobic copolymer may be selected from poiyvinyipyrrolidone/vinyl acetate, such as the PVP/VA series of polymers from Ashland Global Specialty Chemicals Inc of Covington, KY.
  • the hydrophobic copolymer may be selected from triacontanyl PVP, such as GANEXTM WP- 660 from Ashland Global Specialty 7 Chemicals Inc of Covington, KY.
  • the hydrophobic copolymer may be selected from at least one of octylacrylamide/aaylates/butylaminoethyl methacrylate copolymer, VA/butyl maleate/isobomyl acrylate copolymer, acrylates/t- butylacrylamide copolymer, polyvinylpyrrolidone/vinyl acetate copolymer, triacontanyl PVP copolymer, acrylates/dimethylaminoethyi methacrylate copolymer, or mixtures thereof.
  • the hydrophobic polymer may be a copolymer of 2-Propenoic acid, 2- methy!-, 2-methylpropyl ester, polymer with 2-propenoic acid and N-(l,l,3,3-tetramethyihuty!)- 2-propenamide or 2-propenoic acid, 2-methyl-, 2-methylpropyl ester, 2-propenoic acid, N- (l,l ,3,3-tetramethylbutyl) -2-propenamide copolymer (CAS 129702-02-9).
  • the hydrophobic polymer may be or include, but is not limited to, DERMACRYL® 79, which is commercially available fro AkzoNobe! Company, Surface Chemistry of Amsterdam, Netherlands.
  • the amount or concentration of the one or more hydrophobic polymers present in the oral care product or the film forming composition thereof may vary widely.
  • the amount of the one or more hydrophobic polymers present may be from about 1 weight % to about 50 weight %, based on a total weight of the oral care product or the film forming composition thereof.
  • the amount of the one or more hydrophobic polymers present may be from about 1 weight %, about 5 weight %, about 10 weight %, about 15 weight %, about 20 weight %, or about 25 weight % to about 30 weight %, about 35 weight %, about 40 weight %, about 45 weight %, or about 50 weight %.
  • the amount of the one or more hydrophobic polymers present may be from about 1 weight % to about 50 weight %, about 5 weight % to about 45 weight %, about 10 weight % to about 40 weight %, about 15 weight % to about 35 weight %, about 20 weight % to about 30 weight %, or about 22.5 to about 28.5, or about 25 weight %. In at least one implementation, the amount of the one or more hydrophobic polymers present may be from about 10 weight % to about 30 weight %, based on a total weight of the oral care product or the film forming composition thereof.
  • the amount of the one or more hydrophobic polymers present may be from about 10 weight %, about 12 weight %, about 14 weight %, about 16 weight %, about 18 weight %, about 19 weight %, or about 19.5 weight % to about 20.5 weight %, about 21 weight %, about 22 weight %, about 24 weight %, about 26 weight %, about 28 weight %, or about 30 weight %, based on a total weight of the oral care product or the film forming composition thereof.
  • the amount of the one or more hydrophobic polymers present may be from about 10 weight % to about 30 weight %, about 12 weight % to about 28 weight %, about 14 weight % to about 26 weight %, about 16 weight % to about 24 weight 3 ⁇ 4, about 18 weight % to about 22 weight %, about 19 weight % to about 21 weight %, or about 19.5 weight % to about 20.5 weight %, based on a total weight of the oral care product or the film forming composition thereof.
  • the amount of the one or more hydrophobic polymers present may be from about 19 weight % to about 21 weight %, about 19.5 weight % to about 20.5 weight %, or about 20 weight %, based on a total weight of the oral care product or the film forming composition thereof.
  • the oral care product or the film forming composition thereof may include one or more desensitizing agents.
  • desensitizing agents may be or include, but are not limited to, potassium salts (e.g., potassium nitrate, potassium bicarbonate, potassium chloride, potassium citrate, potassium oxalate, etc.); arginine, other occluding agents, such as calcium carbonate, and/or other small particle occlusive agents such as amorphous silicas, camphor, eugenol, strontium salts; zinc salts, AC43; chloride salts, and the like, and mixtures or combinations thereof.
  • potassium salts e.g., potassium nitrate, potassium bicarbonate, potassium chloride, potassium citrate, potassium oxalate, etc.
  • arginine, other occluding agents such as calcium carbonate, and/or other small particle occlusive agents such as amorphous silicas, camphor, eugenol, strontium
  • the amount or concentration of the one or more desensitizing agents present in the oral care product or the film forming composition thereof may vary widely.
  • the desensitizing agents may be presented in an effective amount to at least partially reduce or maintain sensitivity of teeth.
  • the desensitizing agent may be present in an amount of from about 0.01 weight % to about 20 weight %, based on a total weigh of the oral care composition or the film forming composition thereof.
  • the desensitizing agent may be present in an amount of from about 0.01 weight %, about 1 weight %, about 2 weight 3 ⁇ 4, about 4 weight %, about 6 weight %, about 8 weight %, or about 10 weight % to about 12 weight %, about 14 weight %, about 16 weight %, about 18 weight %, or about 20 weight %, based on a total weigh of the oral care composition or the film forming composition thereof.
  • the oral care product or the film forming composition thereof may indude one or more rosins.
  • the one or more rosins may be at least partially hydrogenated.
  • the one or more rosins may be completely or fully hydrogenated.
  • Hydrogenated rosins may he rosin acids or resin acids that have at least some of their carbon-carbon double bonds hydrogenated. It should be appreciated that the relatively greater degree in which the rosins are hydrogenated, the more colorless they appear to the human eye.
  • the oral care product or the fdm forming composition thereof may include a fully hydrogenated rosin that may be transparent or substantially transparent.
  • Illustrative rosins may be or include, but are not limited to, rosins from the class of rosins known in the art as the colophonium class.
  • Members of the colophonium class are non-synthetic naturally-derived sticky resins (e.g., typically derived from various species of pine).
  • Colophonium may include a substantial fraction of resin acid components that are isomeric with abietic acid (C20H30O2). Examples of colophonium may also include dihydrobietic acid (C 20 H 32 O 2 ) and/or dehydroabietic acid (CxoftisO ).
  • Colophonium may range from black to substantially colorless, although resins from this class may typically be pale yellow to amber in color and have a density of about 1.07 to about 1.09 g/cmf
  • Various materials that are individually referred to as“co!ophonium” include Canadian balsam, Olibanum balsam, Elemi resin, Opopanax resin, Tolu balsam, Peruvian balsam, and POLY -PALETM resin which is a partially dimerized rosin commercially available from Eastman Chemical Company of Kingsport, TN.
  • Illustrative rosins may also be or include, but are not limited to, wood rosin, gum rosin, tall oil rosin and mixtures thereof. The rosins may be in a crude state or a refined state.
  • the one or more rosins of the film forming composition when present, may be or include, but is not limited to, FORALTM AX-E, a fully hydrogenated tree rosin that has been distilled and dimerized, which is commercially available from Eastman Chemical Company FORALTM AX-E is nearly colorless and in some implementations is more stable than colophonium components. FORALTM AX-E resists oxidation and retains its substantially colorless characteristics over time.
  • Other suitable commercially available rosins include STAYBELITETM Resin-E, a partially hydrogenated rosin available front Eastman Chemical Company, which also exhibits good oxidation resistance and pale color.
  • Suitable commercially available rosins include P AMITETM (tall oil rosin), DYMEREXTM (dimerized rosin), POLYSTIX® 90 (partially dimerized rosin), DRESINATETM (rosin soap) and PERMALYNTM NC-11 (noncrystalline rosin), all of which are commercially available from Eastman Chemical Company.
  • the amount or concentration of the one or more rosins present in the oral care product or the film forming composition thereof may vary widely. In at least one implementation, the amount of the rosins present in the film forming composition may be from about 1 weight % to about 9 weight %, based on a total weight of the oral care product or the film forming composition thereof.
  • the amount of the rosins present in the film forming composition may be from about 1 weight %, about 2 weight %, about 3 weight %, about 4 weight 3 ⁇ 4, or about 4.5 weight % to about 5.5 weight 3 ⁇ 4, about 6 weight 3 ⁇ 4, about 7 weight 3 ⁇ 4, about 8 weight %, or about 9 weight %, based on a total weight of the oral care product or the film forming composition thereof
  • the amount of the rosins present in the film forming composition may be from about 1 weight % to about 9 weight %, about 2 weight % to about 8 weight %, about 3 weight % to about 7 weight %, about 4 weight % to about 6 weight %, or about 4.5 weight % to about 5.5 weight %.
  • the amount of the rosins present may be from about 4 weight % to about 6 weight %, about 4.5 weight % to about 5.5 weight %, or more preferably about 5 weight %.
  • the oral care product or the film forming composition thereof may include one or more derivatives of cellulose or cellulose derivatives.
  • the cellulose derivatives mav be or include, but is not limited to, an alkyl cellulose ether.
  • the expression“alkyl cellulose ether” may refer to a lower alkyl ether of cellulose, such as an ethyl cellulose.
  • the cellulose derivative is ethyl cellulose.
  • the degree of ethoxylation and/or the viscosity of the ethyl cellulose may vary .
  • the ethyl cellulose may have a degree of ethoxylation of about 45% to about 50% and a viscosity of about 3 cP to about 70 cP (5% solution at 25° C measured in a Ubbelohde viscometer).
  • the ethyl cellulose may have an average substitution value of about 2.25 to about 2.60 ethoxyl groups per anhydroglucose unit, or about 44% to about 52% ethoxyl content.
  • the ethyl cellulose may have an average substitution value of about 2.46 to about 2.58 ethoxyl groups per anhydroglucose unit, corresponding to an ethoxyl content of about 48% to about 49.5%.
  • Illustrative ethyl celluloses may be or include, but are not limited to, AQUALQN® N100 ethyl cellulose, commercially available from Hercules Inc. of Wilmington, DE , ETHOCEL® Standard 100, ETHOCELTM E7, ETHOCELTM E22, ETHOCELTM E50, or the like, and mixtures thereof, all of which are commercially available from the Dow Corning Company.
  • the amount or concentration of the cellulose derivatives present in the oral care product or the film forming composition thereof may van, ' widely.
  • the amount of the cellulose derivatives present in the film forming composition may be from about 0.01 weight % to about 50 weight %, based on a total weight of the oral care product or the film forming composition thereof.
  • the amount of the cellulose derivatives present in the film forming composition may be from about 0.01 weight %, about 0.1 weight %, about 0.2 weight %, about 0.3 weight %, about 0.4 weight %, about 0.5 weight %, about 0.6 weight %, about 0.7 weight %, about 0.8 weight %, about 0.9 weight %, about 1 weight %, about 5 weight %, about 10 weight %, about 15 weight %, about 20 weight %, or about 25 weight % to about 30 weight %, about 35 weight %, about 40 weight %, about 45 weight %, or about 50 weight %.
  • the amount of the cellulose derivative present may be from about 0.01 weight %, about 0.1 weight %, about 0.2 weight %, about 0.3 weight %, about 0.4 weight %, about 0.5 weight %, about 0.6 weight %, about 0.7 weight %, or about 0.8 weight % to about 0.9 weight %, about 1 weight %, about 1.1 weight %, about 1.2 weight %, about 1.3 weight %, about 1.4 weight %, about 1.5 weight 3 ⁇ 4, about 1.6 weight %, or about 1.7 weight %.
  • the amount of the cellulose derivatives present in the film forming composition may be from about 1 weight % to about 50 weight %, about 5 weight % to about 45 weight %, about 10 weight % to about 40 weight %, about 15 weight % to about 35 weight %, about 20 weight % to about 30 weight %, or about 22.5 to about 28.5, or about 25 weight %. In another implementation, the amount of the cellulose derivatives present in the film forming composition may be from about 10 weight % to about 16 weight %.
  • the amount of the cellulose derivatives present in the film forming composition may be from about 10 weight %, about 1 1 weight %, about 12 weight %, or about 12.5 weight % to about 13.5 weight %, about 14 weight %, about 15 weight %, or about 16 weight %, based on a total weight of the oral care product or the film forming composition thereof.
  • the amount of the cellulose derivatives present in the film forming composition may be from about 10 weight % to about 16 weight %, about 1 1 weight % to about 15 weight %, about 12 weight % to about 14 weight %, or about 12.5 weight % to about 13.5 weight 3 ⁇ 4.
  • the amount of the cellulose derivative, such as ethyl cellulose, present in the film forming composition may be from about 12 weight % to about 14 weight %, or about 13 weight 3 ⁇ 4.
  • the oral care product or the film forming composition thereof may optionally include one or more fatty acids configured to serve as a plasticizer and/or improve durability of the film formed from the film forming composition.
  • Illustrative faty acids may be or include, but are not limited to, one or more food grade fatty acids, such as, for example, stearic acid and oleic acid.
  • Illustrative oleic acids may include EMERSOL® oleic acid, commercially available from DeWolf Chemical of Warwick, RL, and PAMOLYN® oleic acid, commercially available from Eastman Chemical Company of Kingsport, TN.
  • the fatty acids may be present in the oral care product or the film forming composi tion thereof in an amount from about 0.01 weight % to about 2 weight %, based on a total weight of the oral care product or the film forming composition thereof.
  • the oral care product or the film forming composition thereof may optionally include one or more adhesives configured to improve, maintain, and/or facilitate the adhesion of the film formed from the film forming composition to surfaces of the oral cavity.
  • the one or more adhesives may also be configured to increase the hydrophobicity of the film formed from the film forming composition, thereby allowing the film to withstand external challenges, such as abrading, rubbing, or brushing.
  • Illustrative adhesives may be or include, but are not limited to, alkyd resins, polyvinyl acetaldehydes, polyvinyl alcohols, polyvinyl acetates, poly(ethylene oxide), polyaerylates, ketone resins, polyvinyipyrolidone, polyvinyipyrolidone/vinyl acetate copolymer, polyethylene glycols of 200 to 1000 molecular weight, polyoxyethyiene/polyoxopropylene block copolymers (Polyox), silicon resins, or the like, and mixtures or combinations thereof.
  • alkyd resins polyvinyl acetaldehydes, polyvinyl alcohols, polyvinyl acetates, poly(ethylene oxide), polyaerylates, ketone resins, polyvinyipyrolidone, polyvinyipyrolidone/vinyl acetate copolymer, polyethylene glycols of 200 to 1000 molecular weight, polyoxyethyiene/
  • the one or more adhesives may include siloxane polymers, which are also generally known in the art as“silicone” polymers.
  • Illustrative silicone-based hydrophobic polymers may be or include, but are not limited to, polyorganosiloxane, polydiorganosiloxane, and the like, and combinations thereof.
  • the adhesion enhancing agent includes at least one silicon pressure sensitive adhesive (PSA).
  • PSAs may be pressure sensitive hydrophobic polymers specifically designed for pharmaceutical use and are permeable to many drug compounds and find application for the transderma! application of various compounds.
  • the silicone polymers are the copolymer product of mixing a silanoi terminated polydiorganosiloxane, such as polydimethyl siloxane, with a silanol-containing silicone resin, whereby the silanoi groups of the polydiorganosiloxane undergo a condensation reaction with the silanoi groups of the silicone resin such that the polydiorganosiloxane is lightly crosslinked by the silicone resin (that is, the polydiorganosiloxane chains are bonded together through the resin molecules to give chain branching and entanglement and/or a small amount of network character) to form the silicone hydrophobic polymers.
  • a silanoi terminated polydiorganosiloxane such as polydimethyl siloxane
  • silicone resin that is, the polydiorganosiloxane chains are bonded together through the resin molecules to give chain branching and entanglement and/or a small amount of network character
  • the adhesion enhancing agents are available under the trade name BIO-PSA from the Dow Corning Company of Midland, ML
  • BIO-PSA commercially available from Dow-Coming
  • the adhesion enhancing agent may include Silicone Adhesive 8-7016, commercially available from Dow Corning Corporation of Midland, MI.
  • the adhesive is a natural resin.
  • Illustrative natural resins may be or include, but are not limited to, shellac, rosins, or the like, and mixtures or combinations thereof.
  • Shellac is commercially available and may be provided with a solvent (e.g. ethanol).
  • a solvent e.g. ethanol
  • One such commercially available shellac known as Refined Pharmaceutical Glaze, is available from Mantrose-Haeuser Co., Inc. of Westport, €T.
  • Hie adhesive may also be or include any one or more of the rosins disclosed herein.
  • the amount or concentration of the adhesion enhancing agents present in the oral care product or the film forming composition thereof may vary widely.
  • the amount of the adhesion enhancing agents present in the film forming composition may he from about 1 weight % to about 5 weight %.
  • the amount of the adhesion enhancing agents present in the film forming composition may be from about 1.0 weight %, about 1.5 weight %, about 2.0 weight %, about 2.5 weight %, or about 3.0 weight % to about 3.5 weight %, about 4.0 weight %, about 4.5 weight %, or about 5.0 weight %.
  • the amount of the adhesion enhancing agents present in the film forming composition may be from about 1.0 weight % to about 5.0 weight %, about 1.5 weight % to about 4.5 weight %, about 2.0 weight % to about 4.0 weight %, or about 2.5 weight % to about 3.5 weight %.
  • the amount of the adhesion enhancing agents present in the film forming composition may be greater than or equal to greater than or equal to 1.0 weight %, greater than or equal to 1.5 weight %, greater than or equal to 2.0 weight %, greater than or equal to 2.5 weight %, greater than or equal to 3.0 weight %, greater than or equal to 3 5 weight %, greater than or equal to 4 0 weight %, or greater than or equal to 4.5 weight %.
  • the amount of the adhesion enhancing agents present in the film forming composition may be less than or equal to 1.0 weight %, less than or equal to 1.5 weight %, less than or equal to 2.0 weight %, less than or equal to 2.5 weight %, less than or equal to 3.0 weight %, less than or equal to 3.5 weight %, less than or equal to 4.0 weight %, less than or equal to 4.5 weight %, or less than or equal to 5.0 weight %.
  • the amount of the adhesion enhancing agents present in the film forming composition is about 3.0 weight %.
  • the oral care product or the film forming composition thereof may optionally include a thickening system having one or more thickeners.
  • the one or more thickeners may be any orally acceptable thickener or thickening agent.
  • Illustrative thickeners may be or include, but are not limited to, colloidal silica, fumed silica, a cross-linked polyvinylpyrrolidone (PVP) polymer, cross-linked polyvinylpyrrolidone (PVT), and the like, and mixtures or combinations thereof.
  • the thickening system may include a cross-linked polyvinylpyrrolidone (PVP) polymer.
  • the thickening system may also include POLYPLASDONE ® XL 10F, which is commercially available from Ashland Inc. of Covington, KY.
  • Additional illustrative thickeners may include, but are not limited to, carbomers (e g., carboxyvinyl polymers), carrageenans (e.g., Irish moss, carrageenan, iota-carrageenan, etc.), high molecular weight polyethylene glycols (e.g , CARBOWAX®, which is commercially available from The Dow Chemical Company of Midland, MI), cellulosic polymers, hydroxy ethyl cellulose, carboxymethy 1 cellul ose, and salts thereof (e.g., CMC sodium), natural gums (e.g., karaya, xanthan, gum arabic, and tragacanth), colloidal magnesium aluminum silicate, hydrophilic polymers, such as carbomers, such as carboxymethylene polymers, such as
  • Carboxypolymethylene is a slightly acidic vinyl polymer with active carboxyl groups.
  • One such carboxypolymethylene is CARBOPOL® 974 and/or 980, commercially available from Noveon, Inc. of Cleveland, OH.
  • the one or more thickeners may be or include a cellulose ether, selected from one or more of hydroxyal yl cellulose polymers, such as hydroxypropyl methyl cellulose (HPMC), hydroxypropyl cellulose, hyrdoxyethy! cellulose, methyl cellulose, ethylcellulose, carboxymethy! cellulose, and mixtures or combinations thereof [0041]
  • the thickening system may include a single thickener.
  • the thickening system may include the cross-linked polyvinylpyrrolidone (PVT) polymer.
  • the thickening system may include a plurality of thickeners.
  • the thickening system may include the cross-linked PVP polymer and a silica thickener.
  • the thickening system may include a plurality of silica thickeners.
  • the amount or concentration of the thickening system and/or the thickeners thereof present in the oral care product or the film forming composition thereof may vary widely.
  • the amount of the thickening system and/or the thickeners thereof present in the oral care product or the film forming composition thereof may be from about 10 wt% to about 30 wt% based on the total weight of the oral care product or the film forming composition thereof
  • the amount of the thickening system and/or the thickeners thereof present in the oral care product or the film forming composition thereof may be from about 10 wt%, about 11 wt%, about 12 wt%, about 13 wt%, about 14 wt%, about 15 wt%, about 16 wt%, about 17 wt%, about 18 wt%, about 19 wt%, about 20 wt%, or about 21 wt% to about 22 wt%, about 23 wt%, about 24 wt%, about 25 wt%, about 26 wt
  • the amount of the thickening system and/or the thickeners thereof present in the oral care product or the film forming composition thereof may be from about 12 wt% to about 30 wt%, about 13 wt% to about 29 wt%, about 14 wt% to about 28 wt%, about 15 wt% to about 27 wt%, about 16 wt% to about 26 wt%, about 17 wt% to about 25 wt%, about 18 wt% to about 24 wt%, about 19 wd% to about 23 wt%, or about 20 wt% to about 22 wt%.
  • the amount of the thickening system and/or the thickeners thereof present in the oral care product or the film forming composition thereof may be from about 20 wt% to about 22 wt%, more typically about 21 wt%.
  • the film forming composition may also include one or more flavoring agents.
  • flavoring agents that may be utilized in the film forming composition may be or include, but are not limited to, essential oils and various flavoring aldehydes, esters, alcohols, and similar materials, as well as sweeteners such as sodium saccharin, and the like, and mixtures or combinations thereof.
  • Illustrative essential oils may include, but are not limited to, oils of spearmint, peppermint, wintergreen, sassafras, clove, sage, eucalyptus, marjoram, cinnamon, lemon, lime, grapefruit, and orange. Also useful are chemicals such as menthol, carvone, anethole, and the like, and mixtures or combinations thereof.
  • the flavoring agents include oils of peppermint and spearmint.
  • the amount or concentration of the one or more flavoring agents present in the oral care product or the film forming composition thereof may vary widely.
  • the amount of the one or more flavoring agents present may be from about 0.01 weight % to about 50 weight %, based on a total weight of the oral care product or the film forming composition thereof.
  • the amount of the one or more flavoring agents present may be from about 0.01 weight %, about 1 weight %, about 5 weight %, about 10 weight %, about 15 weight %, about 20 weight %, or about 25 weight % to about 30 weight %, about 35 weight %, about 40 weight %, about 45 weight %, or about 50 weight %.
  • the film forming composition may be dispersed or dissolved in an orally acceptable vehicle.
  • the expression“orally acceptable vehicle” may refer to a suitable vehicle, ingredient, or combination of ingredients, which can be used to form and/or apply the film forming composition or one or more components thereof to surfaces of the oral cavity in a safe and effective manner.
  • the orally acceptable vehicle may be a suitable solvent, and the film forming composition may be dispersed, dissolved, mixed, or otherwise contacted with the suitable solvent to prepare or form the oral care product.
  • Illustrative solvents may be or include, but are not limited to, ethanol, methanol, isopropanol, butanol, water, acetone, methyl ethyl ketone, ethyl acetate, butyl acetate, cyclohexanone, cyclohexane, methylene chloride, chloroform, carbon tetrachloride, trichloroethylene, perchloroethylene, methyl glycol acetate, toluene, benzene, diethyl ether, benzyl alcohol, or the like, and mixtures or combinations thereof.
  • the orally acceptable vehicle is ethanol.
  • the orally acceptable vehicle may include materials such as, but not limited to, one or more antibacterial agents, anticalculus agents, buffers, sources of peroxide (e.g., hydrogen peroxide), alkali metal bicarbonate salts, thickening materials, humectants, water, surfactants, titanium dioxide, cooling agents, coloring agents, and the like, and combinations thereof.
  • the film forming composition or the orally acceptable vehicle thereof may exclude any of the aforementioned materials.
  • the film forming composition or the orally acceptable vehicle thereof may exclude titanium dioxide (e.g., titanium dioxide particles for aiding and facilitating occlusion of dentin tubules)
  • the orally acceptable vehicle may make up the balance of the oral care product.
  • the orally acceptable vehicle e.g., ethanol
  • the orally acceptable vehicle may be present in an amount of at least 60 weight %, at least 62 weight %, at least 64 weight %, at least 66 weight %,
  • the oral care products and/or the film forming compositions thereof may include other additional ingredients/components.
  • the oral care products and/or the film forming compositions thereof may include desensitizing agents, viscosity modifiers, diluents, surface active agents (e.g , emulsifiers, foam modulators, etc.), pH modifying agents (e.g., acids and bases), humectants, mouth feel agents, sweetening agents, flavor agents, colorants, preservatives, and the like, and combinations and mixtures thereof.
  • desensitizing agents e.g., viscosity modifiers, diluents, surface active agents (e.g , emulsifiers, foam modulators, etc.), pH modifying agents (e.g., acids and bases), humectants, mouth feel agents, sweetening agents, flavor agents, colorants, preservatives, and the like, and combinations and mixtures thereof.
  • surface active agents e.g , e
  • compositions described herein should be orally acceptable.
  • “orally acceptable” may refer to any ingredient that is present in a composition as described in an amount and form that does not render the composition unsafe for use in the oral cavity.
  • the present disclosure may provide methods for reducing dental sensitivity of teeth in a human or animal subject in need thereof, and methods for at least partially occluding dentin tubules of teeth in human or animal subjects in need thereof.
  • animal subject may include higher order non-human mammals such as canines, felines, and horses.
  • the method may include contacting any one of the film forming compositions disclosed herein with surfaces of the oral cavity, such as surfaces of teeth.
  • Contacting the surface of the teeth with the film forming composition may include applying the film forming composition directly to the teeth using a delivery device, such as a pen, (e.g., a COLGATE ⁇ whitening pen or a COLGATE® ACTISTM whitening pen, Colgate-Palmolive Company, New York, NY), a liquid stick having an applicator, such as a felt tip, brush, spray, roller bail, or non-woven pad, or the like.
  • a delivery device such as a pen, (e.g., a COLGATE ⁇ whitening pen or a COLGATE® ACTISTM whitening pen, Colgate-Palmolive Company, New York, NY), a liquid stick having an applicator, such as a felt tip, brush, spray, roller bail, or non-woven pad, or the like.
  • Contacting the surface of the teeth with the film forming composition may also include disposing the film forming composition in a dental tray (e.g., reservoir of a dental tray) and disposing the dental tray
  • the method may also include evaporating a solvent or orally acceptable vehicle from the film forming composition to form a film on the surfaces of the teeth.
  • the resulting film, formed in situ may at least partially occlude dentin tubules of the teeth to at least partially reduce sensitivity of the teeth.
  • the method may also include maintaining the film on the surfaces of the teeth for at least 12 hours, at least one day, at least two days, at least three days, at least four days, or more.
  • the method may also include applying the film forming composition to surfaces of the teeth during or after treatment with a toothpaste, such as a toothpaste for treating sensitive teeth (e.g., Colgate ⁇ Sensitive Pro-ReliefTM).
  • a toothpaste such as a toothpaste for treating sensitive teeth (e.g., Colgate ⁇ Sensitive Pro-ReliefTM).
  • the method may include applying or contacting the oral care product and/or the film forming composition thereof with the surfaces of the teeth at predetermined intervals.
  • the method may include applying or contacting the oral care product and/or the film forming composition thereof with the surfaces of the teeth after brushing, on a daily basis, every other day, once or twice a week, or once a month.
  • the method may include applying or contacting the oral care product and/or the film forming composition thereof with the surfaces of the teeth at least once a day, at least once every two days, at least once every? three davs, at least once every five davs. at least once a week, at least once every two weeks or at least once a month.
  • the oral care product and/or the film forming composition thereof may be utilized for up to 2 weeks, up to 3 weeks, up to 4 weeks, up to 6 weeks, up to 8 weeks, or greater.
  • the present disclosure may further provide methods for preparing a film forming composition.
  • the method may include mixing, dissolving, combining, or otherwise contacting each component of the film forming composition with one another.
  • the method may include contacting an acrylate/octyl acrylamide copolymer, a rosin (e.g , a hydrogenated rosin), an orally acceptable vehicle or solvent, a cellulose derivative, and/or a fatty acid with one another.
  • the components or ingredients of the film forming composition may be homogenized via any acceptable mixing technique or method.
  • All ingredients for use in the compositions described herein should be orally acceptable.
  • “orally acceptable” may refer any ingredient that is present in a composition as described in an amount and form which does not render the composition unsafe for use in the oral cavity.
  • the efficacy of exemplar ⁇ ' film forming compositions (l)-(3) for reducing sensitivity was evaluated in vitro. Particularly, the efficacy of the film forming compositions (l)-(3) for plugging or occluding dentin tubules was evaluated.
  • the test or exemplary film forming compositions (l)-(3) were prepared by combining the ingredients/components according to Table 1. Particularly, the ingredients/components of each of the test film forming (l)-(3) were combined or otherwise contacted with one another in a spin mix jar and mixed at about 3540 rpms for about 5 minutes or until a homogenous suspension was obtained.
  • each of the test film forming compositions (l)-(3) provided significant occlusion of the dentin tubules.
  • the first and second film forming compositions (1) and (2) provided 40.20% and 43.60% occlusion of the dentin tubules, respectively.
  • the film forming composition that did not include titanium dioxide, which is properly sized to aid or facilitate in the occlusion of the dentin tubules exhibited relatively increased occlusion of the tubules, as compared to the test composition (1) including the titanium dioxide.
  • the film forming composition (3) containing arginine/PCC provided the best occlusion result.
  • the polymer coating was able to deliver arginine/PCC into dentine tubules and block the tubules. More surprisingly and unexpectedly, the polymer was able to protect the blocked dentine tubules from coke/acid challenge and provided a longer lasting sensitivity relief benefit than toothpaste (See Table 3) These results demonstrated the ability of the film forming compositions (l)-(3) for reducing sensitivity and/or occlude dentin tubules.
  • Example 1 The efficacy of the exemplary film forming composition (1) of Example 1 for maintaining, facilitating, and/or enhancing the occlusion of dentin tubules in conjunction with a commercial toothpaste for sensitivity (i.e., Colgate ® Sensitive Pro-ReliefTM) was evaluated on dentin slices.
  • the study was conducted by preparing a slurry of the commercial toothpaste and a phosphate buffered saline (PBS) in a 3: 1 ratio. The slurry was applied to the dentin surface by brushing with a soft, nail polish type of brush for 30 seconds, followed by 15 minutes of PBS treatment. This procedure was repeated five times.
  • PBS phosphate buffered saline

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  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Cosmetics (AREA)
  • Medicinal Preparation (AREA)

Abstract

L'invention concerne des compositions filmogènes et des procédés d'occlusion des tubules dentinaires de dents pour traiter l'hypersensibilité dentinaire des dents. Les compositions filmogènes peuvent comprendre un copolymère hydrophobe, une colophane et un solvant acceptable par voie orale. Le copolymère hydrophobe peut comprendre un copolymère acrylate/octylacrylamide, tel que le polymère ester 2-méthyl-,2-méthylpropylique de l'acide 2-propénoïque, avec l'acide 2-propénoïque et le N-(1,1,3,3-tétraméthylbutyl)-2-propénamide. Des méthodes de traitement de l'hypersensibilité dentinaire peuvent consister à mettre en contact la composition filmogène avec des surfaces des dents.
PCT/US2018/055972 2018-10-16 2018-10-16 Compositions de soin buccodentaire et procédés pour celles-ci WO2020081051A1 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
CN201880098293.8A CN113226272A (zh) 2018-10-16 2018-10-16 口腔护理组合物和其方法
BR112021006656-0A BR112021006656B1 (pt) 2018-10-16 Composição formadora de película e seu uso
MX2021004167A MX2021004167A (es) 2018-10-16 2018-10-16 Composiciones y metodos para el cuidado bucal.
PCT/US2018/055972 WO2020081051A1 (fr) 2018-10-16 2018-10-16 Compositions de soin buccodentaire et procédés pour celles-ci
EP18797335.9A EP3849508A1 (fr) 2018-10-16 2018-10-16 Compositions de soin buccodentaire et procédés pour celles-ci
CA3112967A CA3112967A1 (fr) 2018-10-16 2018-10-16 Compositions de soin buccodentaire et procedes pour celles-ci
AU2018445624A AU2018445624B2 (en) 2018-10-16 2018-10-16 Oral care compositions and methods for the same

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Citations (6)

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Publication number Priority date Publication date Assignee Title
US20050281757A1 (en) * 2004-06-17 2005-12-22 Sayed Ibrahim Oral care film
US20140242001A1 (en) * 2011-11-07 2014-08-28 Colgate-Palmolive Company Tooth film formulations
US20160074290A1 (en) * 2012-10-17 2016-03-17 The Procter & Gamble Company Strip for the Delivery of an Oral Care Active and Methods for Applying Oral Care Actives
US20160220472A1 (en) * 2013-09-11 2016-08-04 3M Innovative Properties Company Oral compositions
US20170128346A1 (en) * 2015-11-05 2017-05-11 Colgate-Palmolive Company Durable Dental Film-Forming Composition and Uses Thereof
US20180193247A1 (en) * 2017-01-12 2018-07-12 Colgate-Palmolive Company Oral Care Composition for Long-Lasting Peroxide Delivery

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI395595B (zh) * 2009-04-01 2013-05-11 Colgate Palmolive Co 用於治療牙齒敏感之口腔用組成物及其使用方法與製造
ES2529216T3 (es) * 2010-06-23 2015-02-18 Colgate-Palmolive Company Composición oral terapéutica

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050281757A1 (en) * 2004-06-17 2005-12-22 Sayed Ibrahim Oral care film
US20140242001A1 (en) * 2011-11-07 2014-08-28 Colgate-Palmolive Company Tooth film formulations
US20160074290A1 (en) * 2012-10-17 2016-03-17 The Procter & Gamble Company Strip for the Delivery of an Oral Care Active and Methods for Applying Oral Care Actives
US20160220472A1 (en) * 2013-09-11 2016-08-04 3M Innovative Properties Company Oral compositions
US20170128346A1 (en) * 2015-11-05 2017-05-11 Colgate-Palmolive Company Durable Dental Film-Forming Composition and Uses Thereof
US20180193247A1 (en) * 2017-01-12 2018-07-12 Colgate-Palmolive Company Oral Care Composition for Long-Lasting Peroxide Delivery

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AU2018445624A1 (en) 2021-05-06
CN113226272A (zh) 2021-08-06
AU2018445624B2 (en) 2022-11-10
EP3849508A1 (fr) 2021-07-21
BR112021006656A2 (pt) 2021-07-13
CA3112967A1 (fr) 2020-04-23

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