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WO2025199006A1 - Compositions de soins bucco-dentaires et procédés associés - Google Patents

Compositions de soins bucco-dentaires et procédés associés

Info

Publication number
WO2025199006A1
WO2025199006A1 PCT/US2025/020184 US2025020184W WO2025199006A1 WO 2025199006 A1 WO2025199006 A1 WO 2025199006A1 US 2025020184 W US2025020184 W US 2025020184W WO 2025199006 A1 WO2025199006 A1 WO 2025199006A1
Authority
WO
WIPO (PCT)
Prior art keywords
oral care
care composition
ion source
oral
composition according
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/US2025/020184
Other languages
English (en)
Inventor
Golnaz ISAPOURLASKOOKALAYEH
Turan Matur
Hakeem Kimani HENRY
Hongwei SHEN
Erico PRAT
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Colgate Palmolive Co
Original Assignee
Colgate Palmolive Co
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 Co filed Critical Colgate Palmolive Co
Publication of WO2025199006A1 publication Critical patent/WO2025199006A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

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
    • A61K8/41—Amines
    • 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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin

Definitions

  • Oral care compositions by their cleaning action, make a contribution to the hygiene of the oral cavity and thus to the preservation of the health of teeth and gums.
  • the cleaning action of these oral care compositions is customarily supplemented by admixture of active compounds that prevent or control pathological symptoms in the oral cavity, such as the formation of bacterial films on the teeth (i.e., plaque).
  • active compounds that prevent or control pathological symptoms in the oral cavity, such as the formation of bacterial films on the teeth (i.e., plaque).
  • These bacterial films contain polysaccharides, primarily of dextrans, which form a source of nutrition for the plaque bacteria.
  • the plaque bacteria gradually break down the polysaccharides to form acidic degradation products (e.g., pyruvic acid, lactic acid, etc.).
  • the pH decrease resulting therefrom brings about a degradation of the tooth enamel known as caries.
  • Active compounds may include, for example, amine fluorides, such as N-octadeca-9-enylamine hydrofluoride (international non-proprietary name “dectaflur”) and N'-octadecyl-N',N,N-tris(2-hydroxyethyl)- 1 ,3-propanediamine dihydrofluoride (international non-proprietary name “olaflur”).
  • amine fluorides such as N-octadeca-9-enylamine hydrofluoride (international non-proprietary name “dectaflur”) and N'-octadecyl-N',N,N-tris(2-hydroxyethyl)- 1 ,3-propanediamine dihydrofluoride (international non-proprietary name “olaflur”).
  • fatty acids for the synthesis of amine bases and the subsequent production of marketed amine fluorides are typically obtained from bovine tallow, which could have a negative impact on consumer preference in comparison with plant-derived fatty acid sources for the synthesis of amine bases.
  • the oral care composition is a mouthwash or a mouth rinse.
  • the oral care composition has a turbidity of less than about 100 Nephelometric Turbidity Units (NTU) at 25 °C, preferably less than 80 NTU or less than 70 NTU.
  • NTU Nephelometric Turbidity Units
  • the oral care composition further comprises at least one fluoride ion source, and in certain embodiments, the at least one fluoride ion source is selected from stannous fluoride, sodium fluoride, potassium fluoride, sodium fluorosilicate, or ammonium fluorosilicate, e.g., sodium fluoride.
  • the oral care composition further comprises at least one metal ion source, and in certain embodiments, the at least one metal ion source is selected from a zinc ion source, a copper ion source, or a stannous ion source, preferably a zinc ion source (e.g., zinc oxide, zinc citrate, zinc lactate, zinc phosphate, or combinations thereof, preferably zinc lactate).
  • a zinc ion source e.g., zinc oxide, zinc citrate, zinc lactate, zinc phosphate, or combinations thereof, preferably zinc lactate.
  • the at least one metal ion source e.g., zinc lactate
  • the at least one metal ion source is present in an amount ranging from about 0.1 to about 5 wt.%, preferably about 1 to about 3 wt.%, about 1 to about 2 wt.%; or about 0.4 to about 0.7 wt.%, by weight based on the total weight of the oral care composition.
  • the oral care composition disclosed herein further comprises at least one humectant, and in certain embodiments, the at least one humectant is selected from glycerin, sorbitol, xylitol, or propylene glycol, preferably glycerin and xylitol. According to certain embodiments, the at least one humectant is present in an amount ranging from about 10 wt.% to about 40 wt.% preferably from about 15 wt.% to about 30 wt.% or from about 15 wt.% to about 20 wt.%, by weight based on the total weight of the oral care composition.
  • the oral care composition disclosed herein further comprises at least one emulsifier, e.g., polylyceryl-4 caprate, and in certain aspects, the oral care composition disclosed herein further comprises polyvinyl pyrrolidone (PVP).
  • the oral care composition is free of or substantially free of N-octadeca-9-enylamine hydrofluoride and N'- octadecyl-N',N,N-tris(2-hydroxyethyl)-l,3-propanediamine dihydrofluoride, and in certain embodiments, the oral care composition is free of or substantially free of ethanol.
  • an oral care composition as disclosed herein.
  • a method of manufacturing an oral care composition e.g., a mouthwash or a mouth rinse
  • the method comprises; (1) preparing a first solution comprising water and at least one humectant; (2) preparing a second solution comprising at least one amine chloride (e.g., a plant-based amine chloride) and at least one flavorant; (3) combining the first solution and the second solution to prepare the oral care composition; and (4) optionally adding polyvinyl pyrrolidone (PVP) to the oral care composition after combining the first solution and the second solution.
  • PVP polyvinyl pyrrolidone
  • the at least one plantbased amine chloride is oleamidopropyl aminoethyl-3 dihydrochloride.
  • the first solution further comprises at least one metal ion source, preferably a zinc ion source (e.g., zinc lactate), and according to certain aspects, the first solution further comprises at least one fluoride ion source (e.g., sodium fluoride).
  • the at least one humectant is selected from glycerin, sorbitol, xylitol, or propylene glycol (e.g., a combination of glycerin and xylitol), and in certain aspects of the method, the second solution further comprises at least one emulsifier (e.g., polyglyceryl-4 caprate).
  • the oral care composition has a turbidity of less than about 100 Nephelometric Turbidity Units (NTU) at 25 °C, preferably less than 80 NTU or less than 70 NTU, e.g., on the same day as the oral care composition is manufactured, or one day or seven days after manufacturing the oral care composition.
  • NTU Nephelometric Turbidity Units
  • Also disclosed herein are methods of improving the oral health of a subject comprising administering to the oral cavity of a subject in need thereof an effective amount of the oral care compositions disclosed herein, e.g., about 10 mL to about 50 mL, such as about 15 mL to about 30 mL or about 20 mL to about 25 mL.
  • improving the oral health of the subject comprises at least one of reducing or inhibiting formation of dental caries; reducing, repairing, or inhibiting early enamel lesions; reducing or inhibiting demineralization and promoting remineralization of the teeth; reducing hypersensitivity of the teeth; reducing or inhibiting gingivitis; promoting healing of sores or cuts in the mouth; inhibiting microbial biofilm formation in the oral cavity; raising and/or maintaining plaque pH, e.g., at levels of at least pH 5.5; reducing plaque accumulation; treating dry mouth; enhancing systemic health, including cardiovascular health, e.g., by reducing potential for systemic infections via the oral tissues; whitening teeth; preventing or reducing staining of teeth; reducing erosion of teeth; protecting teeth against cariogenic bacteria; and/or cleaning the teeth and/or oral cavity.
  • the oral care composition is administered to the oral cavity of the subject at least once a day, such as at least twice a day, and in certain embodiments, the oral care composition is administered to the oral cavity of the subject for about 10 seconds to about 30 minutes, such as for about 30 seconds to about 2 minutes.
  • ranges are used as shorthand for describing each and every value that is within the range. Any value within the range can be selected as the terminus of the range. Thus, a range from 1-5, includes specifically 1, 2, 3, 4 and 5, as well as subranges such as 2-5, 3-5, 2-3, 2-4, 1-4, etc.
  • the term “about” when referring to a number means any number within a range of 10% of the number.
  • the phrase “about 2 wt.%” refers to a number between and including 1.8 wt.% and 2.2 wt.%.
  • the abbreviation “wt.%” means percent by weight with respect to the oral care composition.
  • the symbol “°” refers to a degree, such as a temperature degree or a degree of an angle.
  • the symbols “h”, “min”, “mL”, “nm”, and “pm” refer to hour, minute, milliliter, nanometer, and micrometer, respectively.
  • the abbreviation “rpm” means revolutions per minute.
  • any member in a list of species that are used to exemplify or define a genus may be mutually different from, or overlapping with, or a subset of, or equivalent to, or nearly the same as, or identical to, any other member of the list of species. Further, unless explicitly stated, such as when reciting a Markush group, the list of species that define or exemplify the genus is open, and it is given that other species may exist that define or exemplify the genus just as well as, or better than, any other species listed.
  • D, E, and F can be included.
  • a salt thereof also relates to “salts thereof.”
  • the disclosure refers to “an element selected from the group consisting of A, B, C, D, E, F, a salt thereof, and a mixture thereof,” it indicates that that one or more of A, B, C, D, and F may be included, one or more of a salt of A, a salt of B, a salt of C, a salt of D, a salt of E, and a salt of F may be included, or a mixture of any two of A, B, C, D, E, F, a salt of A, a salt of B, a salt of C, a salt of D, a salt of E, and a salt of F may be included.
  • the oral care compositions of the instant disclosure can be free or essentially free of all components and elements positively recited throughout the instant disclosure.
  • the oral care compositions of the present disclosure may be substantially free of non-incidental amounts of the ingredient(s) or compound(s) described herein.
  • a non-incidental amount of an ingredient or compound is the amount of that ingredient or compound that is added into the oral care composition by itself.
  • an oral care composition may be substantially free of a non-incidental amount of an ingredient or compound, although such ingredient(s) or compound(s) may be present as part of a raw material that is included as a blend of two or more compounds.
  • an overlapping compound does not represent more than one component.
  • certain compounds may be characterized as both a polyol and a sweetener. If a particular oral care composition includes both a polyol and a sweetener, xylitol will serve only as either a polyol or a sweetener — not both.
  • the chemical functional groups are in their adjective form; for each of the adjectives, the word “group” is assumed.
  • the adjective “alkyl” without a noun thereafter, should be read as “an alkyl group.”
  • oral care composition means a composition that is delivered to the oral surfaces.
  • the oral care composition is further defined as a product which, during the normal course of usage, is not, for the purposes of systemic administration of particular therapeutic agents, intentionally swallowed but rather is retained in the oral cavity for a time sufficient to contact substantially all of the dental surfaces and/or oral tissues.
  • examples of such compositions include, but are not limited to, toothpaste or a dentifrice, a mouthwash or a mouth rinse, a topical oral gel, a denture cleanser, sprays, and the like.
  • the term “dentifrice” means paste, gel, or liquid formulations, unless otherwise specified.
  • the dentifrice composition can be in any desired form such as deep striped, surface striped, multi-layered, having the gel surrounding the paste, or any combination thereof.
  • the oral care composition may be dual phase and dispensed from separated compartment dispenser(s).
  • the oral care composition disclosed herein is a mouthwash or a mouth rinse.
  • amine base may refer to a primary amine base, a secondary amine base or a tertiary amine base.
  • Primary amine base refers to a compound containing at least one amine in which the nitrogen atom is directly bonded to one carbon of any hybridization, except for carbonyl group carbons.
  • Secondary amine base refers to a compound containing at least one amine in which the nitrogen atom is directly bonded to two carbons of any hybridization, except for carbonyl group carbons.
  • “Tertiary amine base” refers to a compound containing at least one amine in which the nitrogen atom is directly bonded to three carbons of any hybridization, except for carbonyl group carbons.
  • “Amine base” may be used to refer to compounds containing a plurality of primary, secondary and/or tertiary amine groups (c.g., a tertiary polyaminc).
  • the term “amine base” excludes acid addition salts (e.g., hydrochloride salts and hydrofluoride salts), and thus refers to the free base form of the molecule.
  • Hydrofluoride derivatives of amine bases are referred to herein as “amine fluorides,” and hydrochloride derivatives of amine bases are referred to herein as “amine chlorides.”
  • an amine base may be a precursor to forming the amine chloride.
  • an amine base may be a precursor to forming an amine chloride, which then may further react with a fluorine ion source in situ to produce an amine fluoride.
  • the term “in situ” is used to refer to the formation of a chemical product (e.g., amine fluoride or amine chloride) in the oral care composition.
  • the reaction may be a salination reaction carried out by mixing an amine with a chloride source and an acid, thus creating an amine chloride and a salt.
  • the reaction may further comprise mixing an amine chloride with a fluoride ion source, such as sodium fluoride, thus creating an amine fluoride.
  • the oral care composition disclosed herein is an aqueous solution, and in certain embodiments, the oral care composition is in the form of a toothpaste, a dentifrice, a mouthwash or mouth rinse, a topical oral gel, a denture cleanser, or a dental spray.
  • the oral care composition disclosed herein is prepared by adding an amine chloride to the composition, as discussed herein.
  • the amine chloride in the oral care composition may further be combined with a fluoride ion source to form an amine fluoride in situ.
  • the oral care composition may be prepared by mixing an amine base (c.g., polyaminc base) with an acid and a source of chloride, and forming an amine chloride.
  • the amine base is selected from a primary amine, a secondary amine, a tertiary amine, or combinations thereof.
  • the amine base is animal derived (e.g., tallow derived, including bovine tallow derived), and in certain embodiments, the amine base is plant derived.
  • the plant- derived amine base may be derived from rapeseed oil, rice bran oil, or a combination thereof.
  • the amine base is a linear or branched fatty amine, poly amine, or mixtures thereof.
  • the amine base is a saturated or unsaturated C12-20 alkyl amine base or a saturated or unsaturated C12-20 alkyl polyamine base, or mixtures thereof.
  • the amine base may be selected from a myristyl, palmityl, linoleyl, oleyl, or steryl amine or polyamine, or mixtures thereof.
  • the amine base is an oleyl amine or polyamine.
  • the amine base is a polyamine, such as a polyamine selected from monoamine bases, diamine bases, triamine bases, and mixtures thereof.
  • the amine base is selected from N'-octadccyltrimcthylcndiaminc-N.N.N'- tris(2-ethanol) and N-octadeca-9-enylamine.
  • the oral care composition disclosed herein comprises at least one amine chloride.
  • the amine chloride may, for example, be formed from the addition of a chloride, e.g., hydrogen chloride, with an amine base.
  • the amine base may be any amine base known in the art and/or described herein.
  • the amine base is a polyamine base, and in certain embodiments, the polyamine base is plant-based, including a plant-based fatty acid. Exemplary plant-based fatty acids that may be envisioned include palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid, and linolenic acid.
  • the amine chloride is present in the oral care composition disclosed herein in an amount ranging from about 0.1 wt.% to about 5 wt.%, such as from about 0.1 wt.% to about 4.5 wt.%, about 0.1 wt.% to about 4 wt.%, about 0.1 wt.% to about 3.5 wt.%, about 0.1 wt.% to about 3 wt.%, about 0.1 wt.% to about 2.5 wt.%, about 0.1 wt.% to about 2 wt.%, or about 0.1 wt.% to about 1.7 wt.%; from about 0.5 wt% to about 5 wt.%, such as from about 0.5 wt.% to about 4.5 wt.%, about 0.5 wt.% to about 4 wt.%, about 0.5 wt.% to about 3.5 wt.%, about 0.5 wt.% to
  • the oral care composition may further include at least one fluoride ion source.
  • the at least one fluoride ion source may be selected from any fluoride ion source known in the art, including, for example, stannous fluoride, sodium fluoride, potassium fluoride, sodium fluorosilicate, ammonium fluorosilicate, amine fluoride such as N'-octadecyltrimethylendiamine-N,N,N'-tris(2-ethanol)- dihydrofluoride (i.e., olaflur) or N-octadeca-9-enylamine hydrofluoride (i.e., dectaflur), ammonium fluoride, and combinations thereof.
  • the oral care composition disclosed herein is free of, or substantially free of, N'-octadecyltrimethylendiamine-N,N,N'-tris(2- ethanol)-dihydrofluoride, and in certain embodiments, the oral care composition is free of, or substantially free of, N-octadeca-9-enylamine hydrofluoride.
  • the fluoride ion source is sodium fluoride.
  • the amine chloride may react in situ with the fluoride ion source (e.g., sodium fluoride) to form an amine fluoride.
  • the at least one fluoride ion source may be present in the oral care compositions disclosed herein in an amount ranging from about 0.005 wt.% to about 2.5 wt.%, such as from about 0.025 wt.% to about 0.0145 wt.%, or any range or subrange thereof, by weight based on the total weight of the oral care composition.
  • the total fluoride content of the oral care composition ranges from about 50 ppm to about 25,000 ppm, such as from about 750 ppm to 7,000 ppm, about 1,000 ppm to about 5,500 ppm, about 250 ppm, about 500 ppm, about 1,000 ppm, about 1,100 ppm, about 1,400 ppm, about 1,450 ppm, about 2,800 ppm, about 5,000 ppm, or about 25,000 ppm.
  • the oral care composition may further include at least one metal ion source, such as a zinc ion source, a copper ion source, or a stannous ion source.
  • the oral care composition may include a zinc ion source selected from zinc oxide, zinc citrate, zinc lactate, zinc phosphate, and combinations thereof.
  • the at least one stannous ion source is selected from the group consisting of stannous fluoride, stannous chloride, stannic fluoride, stannic chloride, stannic acetate, stannous acetate, and combinations thereof.
  • the at least one stannous ion source may be present in the oral care composition in an amount of up to about 0.9 wt.%, such as an amount ranging from about 0.01 wt.% to about 0.9 wt.%, by weight based on the total weight of the oral care composition.
  • the oral care compositions disclosed herein may comprise a zinc ion source.
  • the zinc ion source may be present in the oral care composition in an amount ranging from about 0.1 to about 5 wt.%, based on the total weight of the oral care composition.
  • the amount of zinc ion present in the oral care composition may be from about 0.1 to about 4 wt.%, about 0.1 to about 3 wt.%, about 0.1 to about 2 wt.%; from about 0.3 to about 5 wt.%, about 0.3 to about 4 wt.%, about 0.3 to about 3 wt.%, about 0.3 to about 2 wt.%; from about 0.5 to about 5 wt.%, about 0.5 to about 4 wt.%, about 0.5 to about 3 wt.%, about 0.5 to about 2 wt.%; from about 0.6 to about 5 wt.%, about 0.6 to about 4 wt.%, about 0.6 to about 3 wt.%, about 0.6 to about 2 wt.%; or from about 1 to about 5 wt.%, about 1 to about 4 wt.%, about 1 to about 3 wt.%, about 1 to about 2 wt.%; or any range or subrange thereof
  • oral care composition includes about 0.4 to about 0.7 wt.% of a zinc ion source, such as about 0.6 wt.% of a zinc ion source, based on the total weight of the oral care composition.
  • the zinc ion source is zinc lactate.
  • the oral care compositions disclosed herein may further comprise a stannous ion source, preferably in an effective amount.
  • the stannous ion source may be present in the oral care composition in an amount ranging from about 0.1 to about 5 wt.%, based on the total weight of the oral care composition.
  • the amount of stannous ion present in the oral care composition may be from about 0.1 to about 4 wt.%, about 0.1 to about 3 wt.%, about 0.1 to about 2 wt.%; from about 0.3 to about 5 wt.%, about 0.3 to about 4 wt.%, about 0.3 to about 3 wt.%, about 0.3 to about 2 wt.%; from about 0.6 to about 5 wt.%, about 0.6 to about 4 wt.%, about 0.6 to about 3 wt.%, about 0.6 to about 2 wt.%; from about 0.9 to about 5 wt.%, about 0.9 to about 4 wt.%, about 0.9 to about 3 wt.%, about 0.9 to about 2 wt.%; from about 1.2 to about 5 wt.%, about 1.2 to about 4 wt.%, about 1.2 to about 3 wt.%, about 1.2 to about 2 wt.%; from about 1.2
  • the stannous ion source may be selected from the group consisting of: stannous fluoride, stannous chloride, stannous pyrophosphate, stannous formate, stannous acetate, stannous gluconate, stannous lactate, stannous tartrate, stannous oxalate, stannous malonate, stannous citrate, stannous ethylene glyoxide, and combinations of two or more thereof.
  • the stannous ion source may comprise stannous fluoride, stannous chloride, stannous acetate, and a combination of two or more thereof.
  • the stannous ion source comprises stannous fluoride, and at least one embodiment, the stannous ion source consists of stannous fluoride.
  • the oral care composition may include two or more, three or more, four or more, five or more, or six or more of metal ion sources.
  • oral care composition may comprise 2 to 7, 2 to 6, 2 to 5, 2 to 5, or 2 to 4; 3 to 7, 3 to 6, 2 to 5, or 3 to 5 metal ion sources.
  • the oral care composition comprises stannous fluoride and stannous pyrophosphate. Additionally or alternatively, the oral care composition may comprise stannous fluoride and stannous chloride.
  • the oral care compositions disclosed herein also optionally include one or more polymers, such as polyethylene glycols, polyvinyl methyl ether maleic acid copolymers, polysaccharides (e.g., cellulose derivatives, for example carboxymethyl cellulose, or polysaccharide gums, for example xanthan gum or carrageenan gum), and polyvinyl pyrrolidone (PVP).
  • Acidic polymers for example poly acrylate gels, may be provided in the form of their free acids or partially or fully neutralized water-soluble alkali metal (e.g., potassium and sodium) or ammonium salts.
  • Certain embodiments include 1:4 to 4:1 copolymers of maleic anhydride or acid with another polymerizable ethylenically unsaturated monomer, for example, methyl vinyl ether (methoxyethylene) having a molecular weight (MW) of about 30,000 to about 1,000,000.
  • methyl vinyl ether methoxyethylene
  • MW molecular weight
  • These copolymers are available for example as GANTREZ® AN 139(MW 500,000), AN 1 19 (MW 250,000) and S-97 Pharmaceutical Grade (MW 70,000), of GAF Chemicals Corporation.
  • operative polymers include those such as the 1:1 copolymers of maleic anhydride with ethyl acrylate, hydroxy ethyl methacrylate, N-vinyl-2-pyrollidone, or ethylene, the latter being available for example as Monsanto EMA No. 1 103, MW 10,000 and EMA Grade 61, and 1 : 1 copolymers of acrylic acid with methyl or hydroxy ethyl methacrylate, methyl or ethyl acrylate, isobutyl vinyl ether or N-vinyl-2-pyrrolidone.
  • a further class of polymeric agents includes a composition containing homopolymers of substituted acrylamides and/or homopolymers of unsaturated sulfonic acids and salts thereof, in particular where polymers are based on unsaturated sulfonic acids selected from acrylamidoalykane sulfonic acids such as 2-acrylamide 2 methylpropane sulfonic acid having a molecular weight of about 1,000 to about 2,000,000, described in U.S. Pat. No. 4,842,847, incorporated herein by reference.
  • Another useful class of polymeric agents includes poly amino acids, particularly those containing proportions of anionic surface-active amino acids such as aspartic acid, glutamic acid and phosphoserine, as disclosed in U.S. Pat. No. 4,866,161, incorporated herein by reference.
  • the oral care compositions disclosed herein may further comprise polyvinyl pyrrolidone (PVP) polymer.
  • PVP is a water-soluble synthetic homopolymer useful in oral care compositions.
  • PVP refers to a polymer containing vinylpyrrolidone (also referred to as N-vinylpyrrolidone and N-vinyl-2-pyrrolidinone) as a monomeric unit.
  • the monomeric unit consists of a polar imide group, four non-polar methylene groups, and a non-polar methane group.
  • the polymers include soluble and insoluble homopolymeric PVPs.
  • Copolymers containing PVP include vinylpyrrolidone/vinyl acetate (also known as Copolyvidone, Copolyvidonum or VP-VAc) and vinyl pyrrolidone/dimethylamino-ethylmethacrylate.
  • Soluble PVP polymers among those useful herein are known in the art, including Povidone, Polyvidone, Polyvidonum, poly(N-vinyl-2-pyrrolidinone), poly (N-vinylbutyrolactam), poly(l-vinyl-2- pyrrolidone) and poly [l-(2-oxo-l pyrrolidinyl)ethylene] .
  • These PVP polymers are not substantially cross-linked.
  • the polymer comprises an insoluble cross-linked homopolymer.
  • Such polymers include crosslinked PVP (often referred to as cPVP, polyvinylpolypyrrolidone, or cross-povidone).
  • the oral care compositions disclosed herein comprise at least one polymer, such as PVP, in an amount ranging from about 1 wt.% to about 5 wt.%, such as about 1 wt.% to about 4.5 wt.%, about 1 wt.% to about 4 wt.%, about 1 wt.% to about 3 wt.%, or about 1 wt.% to about 2.5 wt.%; from about 1.5 wt.% to about 5 wt.%, about 1.5 wt.% to about 4.5 wt.%, about 1.5 wt.% to about 4 wt.%, about 1.5 wt.% to about 3.5 wt.%, about 1.5 wt% to about 3 wt.%, or about 1.5 wt.% to about 2.5 wt.%; from about 2 wt.% to about 5 wt.%, about 2 wt.% to about 4.5 wt.%, about 1 wt.% to about 2.5
  • a humectant keeps oral care compositions from hardening upon exposure to air. Certain humectants can also impart desirable sweetness or flavor to oral care compositions.
  • the composition incorporates at least one humectant to reduce evaporation and/or to contribute towards preservation by lowering water activity.
  • the at least one humectant is selected from the group consisting of glycerin, sorbitol, xylitol, propylene glycol, as well as other polyols and combinations thereof.
  • the humectant may be present in the oral care composition in an amount of from about 10 wt.% to about 40 wt.% in one embodiment, such as from about 15 wt.% to about 30 wt.%, from about 15 wt.% to about 20 wt.%, or from about 17 wt.% to about 19 wt.%, or any range or subrange thereof, by total weight of the oral care composition.
  • the oral care composition comprises a combination of glycerin and xylitol.
  • the oral care compositions disclosed herein may comprise one or more emulsifiers. Any emulsifier known in the art for oral care use may be incorporated, including for example, polyglyceryl-4 caprate, polyethylene glycol (PEG), PEG-40 hydrogenated castor oil, alkyl polyglucosides, polysorbates, and combinations thereof.
  • the emulsifier may be chosen from poloxamers (e.g., PLURONICS®) and other non-ionic emulsifiers.
  • the emulsifier is polyglyceryl-4 caprate (TEGOSOFT® PC).
  • the at least one emulsifier may be present in the oral care composition in an amount ranging from about 0.01 wt.% to about 2 wt.%, such as from about 0.01 wt.% to about 1.8 wt.%, about 0.01 wt.% to about 1.5 wt.%, about 0.01 wt.% to about 1 wt.%, or about 0.01 wt.% to about 0.5 wt.%; from about 0.1 wt.% to about 2 wt.%, such as from about 0.1 wt.% to about 1.8 wt.%, about 0.1 wt.% to about 1.5 wt.%, about 0.1 wt.% to about 1 wt.%, or about 0.1 wt.% to about 0.5 wt.%; from about 0.2 wt.% to about 2 wt.%, such as from about 0.2 wt.% to about 1.8 wt.%, about 0.2 wt.% to
  • Suitable flavoring agents include, but are not limited to, essential oils and various flavoring aldehydes, esters, alcohols, and similar materials.
  • the essential oils include oils of spearmint, peppermint, wintergreen, sassafras, clove, sage, eucalyptus, marjoram, cinnamon, lemon, lime, grapefruit, and orange.
  • Also useful arc such chemicals as menthol, carvone, and anethole.
  • Additional flavoring agents may include, but are not limited to menthol, artificial vanilla, cinnamon derivatives, and various fruit flavors, spearmint oil, peppermint oil, cinnamon oil, oil of wintergreen (methylsalicylate), clove oil, bay oil, anise oil, eucalyptus oil, thyme oil, cedar leaf oil, oil of nutmeg, oil of sage, oil of bitter almonds, cassia oil, and a combination of two or more thereof.
  • Water may be present in the oral care compositions disclosed herein. Water employed in the preparation of commercial oral compositions should be deionized and free of organic impurities. Water commonly makes up the balance of the compositions and includes about 5 wt.% to about 99 wt.%, such as from about 10 wt.% to about 90 wt.%, from about 65 wt.% to about 85 wt.%, or about 70 wt.% to about 80 wt.%, or any range or subrange thereof, by weight based on the total weight of the oral care composition. This amount of water includes the free water that is added plus any amount of water that may be introduced with other materials, such as with sorbitol or silica or any components of the oral care composition disclosed herein. The Karl Fischer method is a one measure of calculating free water.
  • the oral care compositions disclosed herein may further comprise additional ingredients as known in the art and as disclosed below.
  • additional ingredients may include, but are not limited to, chelating and anti-calculus agents, abrasives, surfactants, anti-bacterial agents, thickening agents, whitening agents, colorants, diluents, pH modifying agents, foam modulators, sweeteners, antioxidants, anti-hypersensitivity agents, fragrances, emulsifiers, alkaline phosphate salts, and mixtures thereof.
  • additional ingredients may include, but are not limited to, chelating and anti-calculus agents, abrasives, surfactants, anti-bacterial agents, thickening agents, whitening agents, colorants, diluents, pH modifying agents, foam modulators, sweeteners, antioxidants, anti-hypersensitivity agents, fragrances, emulsifiers, alkaline phosphate salts, and mixtures thereof.
  • Such ingredients would be known to those skilled in the art of oral care. However, non-
  • Suitable components may be included or excluded from the formulations for the oral care compositions depending on the specific combination of other ingredients and the form of the oral care compositions. Additionally or alternatively, the oral care compositions may in some embodiments have a single phase, which contains the components and/or ingredients of the oral care composition. Tn other embodiments, the oral care composition may include two or more phases, such as two, three, four, or five phases.
  • the oral care compositions disclosed herein may optionally comprise one or more chelating agents able to complex calcium found in the cell walls of bacteria. Binding of this calcium weakens the bacterial cell wall and augments bacterial lysis.
  • Another group of agents suitable for use as chelating or anti-calculus agents include soluble pyrophosphates.
  • Pyrophosphate salts used in accordance with the present disclosure can be any of the alkali metal pyrophosphate salts.
  • salts include tetra alkali metal pyrophosphate, dialkali metal diacid pyrophosphate, trialkali metal monoacid pyrophosphate and mixtures thereof, wherein the alkali metals are sodium or potassium.
  • the salts are useful in both their hydrated and unhydrated forms.
  • An effective amount of pyrophosphate salt useful in the present composition is generally enough to provide least 0.1 wt.% pyrophosphate ions, e.g., 0.1 to 3 wt.%, 0.1 to 2 wt.%, 0.1 to 1 wt.%, or 0.2 to 0.5 wt.%, by weight relative to the total weight of the oral care composition.
  • an abrasive removes debris and surface stains.
  • the oral care compositions disclosed herein may comprise additional silica abrasives, sodium metaphosphate, potassium metaphosphate, aluminum silicate, calcined alumina, bentonite or other siliceous materials, or combinations thereof.
  • Any silica suitable for oral care compositions may be used, such as precipitated silicas or silica gels.
  • silica gels such as precipitated silicas or silica gels.
  • silica gels such as precipitated silicas or silica gels.
  • synthetic amorphous silica may also be available as a thickening agent, e.g., particle silica.
  • the silica can also be small particle silica.
  • the oral care compositions disclosed herein may comprise at least one surfactant, such as surfactants selected from anionic, cationic, zwitterionic, and nonionic surfactants, and mixtures thereof.
  • the surfactant is reasonably stable throughout a wide pH range.
  • the oral care compositions disclosed herein may comprise from about 0.01 to about 10 wt.% of a surfactant, such as about 0.05 to about 5 wt.% of a surfactant, about 0.1 to about 10 wt.% of a surfactant, about 0.1 to about 5 wt.% of a surfactant, about 0.1 to about 2 wt.% of a surfactant, or about 0.5 to about 2 wt.% of a surfactant.
  • a surfactant such as about 0.05 to about 5 wt.% of a surfactant, about 0.1 to about 10 wt.% of a surfactant, about 0.1 to about 5 wt.% of a surfactant, about 0.1 to about 2 wt.% of a surfactant, or about 0.5 to about 2 wt.% of a surfactant.
  • the oral care compositions disclosed herein may comprise from about 0.01 to about 10 wt.% of a nonionic surfactant, such as about 0.05 to about 5 wt.% of a nonionic surfactant, about 0.1 to about 10 wt.% of a nonionic surfactant, about 0.1 to about 5 wt.% of a nonionic surfactant, about 0.1 to about 2 wt.% of a nonionic surfactant, about 0.4 to about 1 wt.% of a nonionic surfactant, or about 1 wt.% of a nonionic surfactant.
  • a nonionic surfactant such as about 0.05 to about 5 wt.% of a nonionic surfactant, about 0.1 to about 10 wt.% of a nonionic surfactant, about 0.1 to about 5 wt.% of a nonionic surfactant, about 0.1 to about 2 wt.% of a nonionic surfactant, about
  • Non-ionic surfactants arc known in the ail and generally include surfactants that are not electrically charged.
  • An exemplary nonionic surfactant may be poly(oxyethylene)- poly (oxypropylene) block copolymers. Such copolymers are known commercially by the nonproprietary name of poloxamers. The name poloxamer is often used in conjunction with a numeric suffix to designate the individual identification of each copolymer. Poloxamers may have varying contents of ethylene oxide and propylene oxide which results in poloxamers that have a wide range of chemical structures and molecular weights. One poloxamer that may be mentioned is Poloxamer 407, sold under the trade name PLURONIC® Fl 27 by BASF, Inc. (Parsippany, N.J.). In certain embodiments, the oral care compositions disclosed herein may comprise poloxamer as the at least one surfactant.
  • Anionic surfactants that may be used in the oral care compositions disclosed herein include, for example: (i) water-soluble salts of higher fatty acid monoglyceride monosulfates, such as the sodium salt of the monosulfated monoglyceride of hydrogenated coconut oil fatty acids such as sodium N-methyl N-cocoyl taurate, sodium cocomonoglyceride sulfate; (ii) higher alkyl sulfates, such as sodium lauryl sulfate; (iii) higher alkyl-ether sulfates, such as those of formula CH3(CH2)mCH2(OCH 2 CH2)nOSO3X, wherein m is 6-16, e.g., 10, n is 1-6, e.g., 2, 3 or 4, and X is Na or K, for example sodium laureth-2 sulfate (CH3(CH 2 )IOCH 2 (OCH 2 CH 2 )OSO3Na); (iv) higher fatty acid
  • the oral care compositions disclosed herein may 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 monoglyceride sulfonates are examples of anionic surfactants of that type.
  • the oral care compositions disclosed herein may comprise sodium lauryl sulfate, sodium ether lauryl sulfate, or a mixture thereof.
  • the oral care compositions disclosed herein may comprise sodium lauryl sulfate.
  • the oral care composition disclosed herein further comprises at least one antibacterial agent selected from halogenated diphenyl ether (c.g., triclosan), herbal extracts and essential oils (e.g., rosemary extract, tea extract, magnolia extract, thymol, menthol, eucalyptol, geraniol, carvacrol, citral, honokiol, catechol, methyl salicylate, epigallocatechin gallate, epigallocatechin, gallic acid, miswak extract, sea-buckthorn extract), bisguanide antiseptics (e.g., chlorhexidine, alexidine or octenidine), quaternary ammonium compounds (e.g., cetylpyridinium chloride (CPC), benzalkonium chloride, tetradecylpyridinium chloride (TPC), N-
  • halogenated diphenyl ether
  • the oral care composition disclosed herein further comprises at least one thickening agent selected from carboxyvinyl polymers, carrageenan, xanthan, hydroxyethyl cellulose, water-soluble salts of cellulose ethers (e.g., sodium carboxylmethyl cellulose, sodium carboxymethyl hyroxyethyl cellulose), and combinations thereof.
  • at least one thickening agent selected from carboxyvinyl polymers, carrageenan, xanthan, hydroxyethyl cellulose, water-soluble salts of cellulose ethers (e.g., sodium carboxylmethyl cellulose, sodium carboxymethyl hyroxyethyl cellulose), and combinations thereof.
  • a thickener may provide a desirable consistency and/or stabilize and/or enhance performance (e.g., provide desirable active release characteristics upon use) of the oral care compositions disclosed herein.
  • the oral care compositions disclosed herein may comprise from about 0 to about 15 wt.% of a thickener, such as about 0.1 to about 15 wt.% of a thickener, about 0.1 wt.% to about 10 wt.% of a thickener, about 0.1 wt.% to about 5 wt.% of a thickener, about 0.5 wt.% to about 10 wt.% of a thickener, about 0.5 wt.% to about 5 wt.% of at a thickener, about 1 wt.% to about 4 wt.% of a thickener, about 2 wt.% to about 5 wt.% of a thickener, about 2 wt.% to about 4 wt.% of a thickener, about
  • Thickeners that may be used in the oral care compositions disclosed herein 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 carboxymethylcellulose (CMC) and sodium carboxymethyl hydroxyethyl cellulose), natural gums (e.g., gum karaya, xanthan gum, gum arable, and gum tragacanth), colloidal magnesium aluminum silicate, silica (c.g., finely divided silica), polyvinyl pyrrolidone, carbowaxcs, fatty acids and salts thereof, and mixtures thereof.
  • carboxy vinyl polymers also known as carrageenan gum
  • HEC hydroxyethyl cellulose
  • natural and synthetic clays e.g., Veegum and laponite
  • a mixture of thickening silica and carrageenan gum may be used as the thickener in the oral care compositions disclosed herein.
  • the oral care compositions disclosed herein comprise from about 0.01 wt.% to about 15 wt.% of thickening silica and carrageenan gum, such as about 0.1 wt.% to about 1 wt.% of thickening silica and carrageenan gum, about 0.1 wt.% to about 1.0 wt.% of thickening silica and carrageenan gum, about 0.1 wt.% to about 5 wt.% of thickening silica and carrageenan gum, about 0.5 wt.% to about 10 wt.% of thickening silica and carrageenan gum, about 0.5 wt.% to about 5 wt.% of thickening silica and carrageenan gum, about 1 wt.% to about 4 wt.% of thicken
  • the oral care composition disclosed herein further comprises at least one whitening agent selected from metal chlorides, perborates, percarbonates, peroxyacids, hypochlorites, and combinations thereof.
  • the oral care compositions may include one or more colorants.
  • Exemplary colorants can include natural or uncertified colors from natural sources or certified colors for the effect of color.
  • the colorant can include dyes, certified aluminum lakes or colors derived from a natural source.
  • the colorant may be water-based, oil-based or dry.
  • the colorants can be primary colors, blends of colors or discrete mixtures of colors, such as confetti.
  • the concentrations of the colorant in the oral care composition may be from trace amount to about 0.6 wt.%, from about 0.1 to about 0.5 wt.%, about 0.2 to about 0.4 wt.%, or about 0.15 to about 0.35 wt.%, by weight based on the total weight of the oral care composition.
  • the oral care composition may include one or more pH adjusters to increase or decrease the overall pH of the oral care composition.
  • one or more acids may be included to decrease the pH of the oral care composition.
  • suitable acids for decreasing the pH of the oral care composition include, but are not limited to, citric acid, acetic acid, and the like.
  • the oral care composition may include one or more bases, such as sodium hydroxide, potassium hydroxide and the like, to increase the pH of the oral care composition. Additional or alternative acids and bases that are suitable for adjusting the pH of the oral care composition are readily known to one of ordinary skill in the art.
  • the amount of the pH adjuster in the oral care composition may be based on the desired pH of the final oral care composition and/or product.
  • the total amount of the pH adjuster may range from about 0.05 wt.% to about 20 wt.%, based on the total weight of the oral care composition.
  • the total amount of pH adjuster is from about 0.05 wt.% to about 15 wt.%, about 0.1 wt.% to about 10 wt.%, or about 0.12 wt.% to about 5 wt.%, including ranges and sub-ranges therebetween, based on the total weight of the oral care composition.
  • the oral care composition disclosed herein may be clear, translucent, or transparent. Clarity may be considered a characteristic of stability, and in certain embodiments, the clarity of a stable composition may be maintained for lengthy periods of time. For example, clarity of the finished composition may, in certain embodiments, be maintained for a period of at least one day, such as at least two days, at least three days, at least four days, at least five days, at least six days, at least one week, at least two weeks, at least three weeks, at least four weeks, at least one month, at least two months, at least three months, at least four months, at least five months, or at least six months.
  • at least one day such as at least two days, at least three days, at least four days, at least five days, at least six days, at least one week, at least two weeks, at least three weeks, at least four weeks, at least one month, at least two months, at least three months, at least four months, at least five months, or at least six months.
  • Stability of a mouthwash composition may, in certain embodiments, be measured based on the composition's turbidity /clarity.
  • Turbidity is the cloudiness or haziness of a fluid caused by individual particles (i.e., suspended solids) that are generally invisible to the naked eye. The measurement of turbidity may be used as a test of mouthwash cosmetic acceptability for consumer use.
  • NTU Nephelometric Turbidity Units
  • Acceptable turbidity measurements taken using a Hach turbidity meter may, in certain embodiments, range from about 0 to about 100 NTU at 25 °C, such as from about 0 to about 50 NTU, about 0 to about 30 NTU, 0 to about 20 NTU, or about 5 to about 20 NTU. The clarity may also be evaluated visually in certain instances.
  • an acceptable turbidity may be less than or equal to about 25 NTU, such as less than or equal to about 20 NTU, or less than or equal to about 15 NTU at 25 °C.
  • NTU may be evaluated immediately after preparation of the oral care composition, and in certain embodiments, NTU may be evaluated at least an hour after preparation of the composition, such as after at least two hours, at least six hours, at least 20 hours, at least two days, at least three days, at least four days, at least five days, at least six days, or at least seven days.
  • the oral care composition disclosed herein has a turbidity ranging from 0 to about 20 NTU, such as from about 5 to about 20 NTU, when measured seven days after preparation of the oral care composition.
  • Relative clarity, transparency, and/or translucency of a solution may also be measured by particle size.
  • average particle size of solutes in a solution increases linearly with an increase in turbidity. Accordingly, the lower the average particle size of solutes in a solution, the more clear the solution will appear.
  • Average particle size may be measured by any means known in the art, including, for example, a particle size analyzer, e.g., Malvern Zetasizer or Malvern Mastersizer particle size analyzer.
  • the oral care compositions disclosed herein have an average particle size ranging from about 50 nm to about 10,000 nm, such as from about 100 nm to about 5200 nm, about 100 nm to about 1000 nm, or about 250 nm to about 500 nm, or any range or subrange therein.
  • a method of improving oral health comprising administering the oral care composition disclosed herein to the oral cavity of a subject in need thereof.
  • the methods of improving oral health may include, for example, reducing or inhibiting formation of dental caries; reducing, repairing, or inhibiting early enamel lesions; reducing or inhibiting demineralization and promoting remineralization of the teeth; reducing hypersensitivity of the teeth; reducing or inhibiting gingivitis; promoting healing of sores or cuts in the mouth; inhibiting microbial biofilm formation in the oral cavity; raising and/or maintaining plaque pH, e.g., at levels of at least pH 5.5; reducing plaque accumulation; treating dry mouth; enhancing systemic health, including cardiovascular health, e.g., by reducing potential for systemic infections via the oral tissues; whitening teeth; preventing or reducing staining of teeth; reducing erosion of teeth; protecting teeth against cari
  • the oral care composition may be applied to the oral cavity of the subject in need thereof at least once a day, such as at least twice a day or at least three times a day.
  • the methods disclosed herein may include administering the oral care composition to an oral cavity for about 10 seconds to about 30 minutes, e.g., about 15 seconds to about 25 minutes, about 20 seconds to about 15 minutes, about 25 seconds to about 5 minutes, or about 30 seconds to about 2 minutes.
  • the oral care compositions may be administered in a form that is maintained in the oral cavity overnight.
  • compositions disclosed herein may be made according to methods and procedures known to those skilled in the art, including, for example, the methods disclosed in PCT Publication No. WO 2022/133221, incorporated herein by reference in its entirety.
  • an oral care composition as disclosed herein, the method comprising preparing a first solution comprising water and at least one humectant (e.g., xylitol and/or glycerin); preparation a second solution comprising an amine chloride, a flavorant, optionally an emulsifier, and optionally a fragrance, and combining the first and second solutions to form the oral care composition.
  • the method further comprises adding a polymer, such as polyvinyl pyrrolidone (PVP), to the oral care composition after combining the first solution and the second solution.
  • PVP polyvinyl pyrrolidone
  • the first solution does not comprise PVP, and in certain embodiments, the first solution does not comprise amine chloride.
  • the amine chloride is added together with the flavorant and optional fragrance. While not wishing to be bound by theory, it is believed that the amine chloride, which may be plant-based, acts to assist in emulsification of the flavorant and optional fragrance.
  • exemplary batch solutions were prepared as set forth in Tables 1A-1C below. Briefly, two premixes were prepared, a Premix 1 containing the base solution and a Premix 2 containing the flavorant, as shown in Table 1 A and Table IB, respectively. After preparation of Premix 1 and Premix 2, the prcmixturcs were combined to form a final mixture. Batch 1 contained a tallowbased amine fluoride, which was added into the final mixture after Premix 1 and Premix 2 were combined, while Batch 2 contained the same amount of a tallow-based amine fluoride, added into the Premix 2 as an emulsifier prior to combination of Premix 2 with Premix 1.
  • Batch 3 contained a tallow-based amine fluoride added to the Premix 1 prior to combination with the Premix 2
  • Batch 4 contained a plant-based amine chloride added to the Premix 2 as an emulsifier prior to combination of Premix 2 with Premix 1. It is further noted that in Batch 1, PVP was added into the Premix 1 base solution, while in Batch 3, PVP was added into the final mixture after combination of the Premix 1 and Premix 2, as shown in Table 1C below.
  • Example 2 Particle Size and Turbidity of Oral Care Mouthwash Compositions

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Abstract

L'invention concerne des compositions de soins bucco-dentaires, telles que des compositions de bain de bouche ou de rinçage buccal, comprenant au moins un chlorure d'amine à base de plante et au moins un agent aromatisant. L'invention concerne également des procédés de fabrication et des procédés d'utilisation des compositions de soins bucco-dentaires.
PCT/US2025/020184 2024-03-19 2025-03-17 Compositions de soins bucco-dentaires et procédés associés Pending WO2025199006A1 (fr)

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US4842847A (en) 1987-12-21 1989-06-27 The B. F. Goodrich Company Dental calculus inhibiting compositions
US4866161A (en) 1987-08-24 1989-09-12 University Of South Alabama Inhibition of tartar deposition by polyanionic/hydrophobic peptides and derivatives thereof which have a clustered block copolymer structure
WO2022133441A1 (fr) 2020-12-14 2022-06-23 Global Graphene Group, Inc. Séparateur perméable aux ions de lithium pour une batterie secondaire au lithium et procédé de fabrication
WO2022133221A1 (fr) 2020-12-18 2022-06-23 Colgate-Palmolive Company Compositions de soins bucco-dentaires contenant des fluorures d'amine
WO2022133234A1 (fr) * 2020-12-18 2022-06-23 Colgate-Palmolive Company Compositions de soins buccodentaires contenant des fluorures d'amine

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CH630255A5 (en) * 1977-11-03 1982-06-15 Muehlemann Hans R Agent for dental and gingival hygiene
US4866161A (en) 1987-08-24 1989-09-12 University Of South Alabama Inhibition of tartar deposition by polyanionic/hydrophobic peptides and derivatives thereof which have a clustered block copolymer structure
US4842847A (en) 1987-12-21 1989-06-27 The B. F. Goodrich Company Dental calculus inhibiting compositions
WO2022133441A1 (fr) 2020-12-14 2022-06-23 Global Graphene Group, Inc. Séparateur perméable aux ions de lithium pour une batterie secondaire au lithium et procédé de fabrication
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