Oral care composition
By using an oral care composition containing amphoteric surfactants, cationic antibacterial agents, and copolymers, the challenges of existing products in preventing dental diseases and reducing tooth staining are solved, achieving effective protection and cleaning of teeth.
Patent Information
- Application Number
- CN202080041503.7
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2019-06-05
- Filing Date
- 2020-06-04
- Publication Date
- 2025-11-11
- Estimated Expiration
- 2040-06-04
AI Technical Summary
Existing oral care products are ineffective in preventing dental diseases such as tooth decay, tartar, gingivitis, and tooth staining. In addition, some antibacterial agents may cause tooth enamel staining or yellowing.
Oral care compositions containing amphoteric surfactants, oral-acceptable cationic antimicrobial agents, and copolymers form a protective film through the combined use of these ingredients, reducing bacterial adhesion and tooth discoloration.
It effectively prevents tooth decay, plaque, and gingivitis, while reducing tooth staining, providing an antibacterial and protective film, and enhancing dental health.
Smart Images

Figure BDA0003391688650000021 
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Figure BDA0003391688650000041
Abstract
Description
[0001] Cross-references to related applications
[0002] This application claims the benefit of priority to U.S. Provisional Application Serial No. 62 / 857,425, filed June 5, 2019, pursuant to 35 U.S. SC §119(e), and the entire disclosure of that application is incorporated herein by reference. Technical Field
[0003] This disclosure relates to oral care compositions and methods of using such compositions. In particular, this disclosure relates to an oral care composition comprising an amphoteric surfactant or betaine, a copolymer, and an orally acceptable cationic antimicrobial agent, and a method of using the oral composition. Background Technology
[0004] Teeth suffer from a variety of diseases and problems, including cavities, plaque, tartar, gingivitis, whitening practices resulting from the misuse of concentrated hydrogen peroxide, dentin hypersensitivity, and enamel staining.
[0005] Most oral health problems originate from a thin protein membrane that deposits on the tooth surface. This membrane acts as a base for bacteria and mineral deposits (which harden into plaque and eventually tartar). Bacterial colonies, sheltered within, absorb and metabolize nutrients from substances passing through the mouth (especially sucrose) and produce carboxylic acids. These acids are not easily washed away by oral fluids because the colonies are protected by the plaque membrane and remain very close to the tooth surface. The resulting acids remain adhered to the tooth surface, where they slowly erode minerals and destroy the hydroxyapatite crystal structure, leading to cavities. Tartar and tartar deposits cause the gum tissue to separate from the teeth, leading to inflammation and the formation of "pockets," which provide even more concealed, difficult-to-clean areas for the destructive process. Receding gums eventually expose the dentinal tubules, resulting in dentin hypersensitivity.
[0006] Antimicrobial or antibacterial agents are already used in dental or oral care products to inhibit bacterial activity in the oral cavity. However, some of these agents cause enamel staining or yellowing in teeth. Therefore, there remains a need for improved oral care products, such as those designed to prevent bacterial growth and tooth staining in the teeth or oral cavity. Summary of the Invention
[0007] Among other things, this document provides an oral care composition (e.g., an oral care product) and a method of using the composition.
[0008] In one aspect, an oral care composition is provided, the composition comprising an oral-acceptable carrier, an amphoteric surfactant, an oral-acceptable cationic antimicrobial agent, and a copolymer (e.g., an anionic copolymer).
[0009] Amphoteric surfactants have the structure of formula (I):
[0010]
[0011] Where L is a substituted or unsubstituted (C2-C4) alkylene group,
[0012] n is an integer from 1 to 10.
[0013] R a and R b It is independently a C1-C4 alkyl group.
[0014] R c Is it substituted or unsubstituted C1-C? 20 Alkyl, and
[0015] Y is an anionic group.
[0016] The copolymer is a copolymer of the following:
[0017] i) an allyl phosphate compound; and ii) one or more α,β-olefinically unsaturated comonomers, wherein at least one is not an allyl-functional comonomer. The allyl phosphate compound has formula (A):
[0018] [CH2=CH-CH2-O(R 1 O) a (R 2 O) b ] x P(O)(OM) 3-x (A)
[0019] in
[0020] R 1 It is a substituted or unsubstituted (C2-C4) alkylene moiety;
[0021] R 2 It is a substituted or unsubstituted (C2-C4) alkylene moiety;
[0022] M can be the same or different, and can be hydrogen, alkali metal, ammonium, protonated alkylamine, protonated alkanolamine, or protonated basic amino acid;
[0023] X is 1 or 2; a is from 1 to 20; and b is from 0 to 20.
[0024] In some embodiments, Y is -C(O)O or -S(O)2O. In some embodiments, n is 2, 3, or 4. In some embodiments, R a and R b It is either methyl or ethyl.
[0025] In some embodiments, the amphoteric surfactant is selected from the group consisting of: cocamidopropyl betaine, lauramidopropyl betaine, cocamidopropyl betaine, cocamidopropyl hydroxysulfonate betaine, and combinations thereof.
[0026] In some embodiments, R 1 and R 2 It can be independently substituted by hydroxyl, alkoxy, or aryl groups.
[0027] In some embodiments, one or more α,β-olefinic unsaturated comonomers include portions selected from the group consisting of maleic anhydride, maleic acid, itaconic anhydride, itaconic acid, and combinations thereof.
[0028] In some embodiments, oral-acceptable cationic antimicrobial agents are selected from the group consisting of chlorhexidine gluconate, cetylpyridinium chloride, quaternary ammonium surfactants, cationic amino acids, metal cations, and combinations thereof.
[0029] In some embodiments, the copolymer is polymerized from a mixture comprising one or more α,β-olefinically unsaturated maleimide phosphate comonomers and one or more α,β-olefinically unsaturated comonomers.
[0030] In some embodiments, one of the α,β-olefinic unsaturated maleimide phosphate comonomers has formula (B).
[0031]
[0032] in
[0033] R 1’ It is a substituted or unsubstituted (C2-C4) alkylene moiety;
[0034] R 2’ It is a substituted or unsubstituted (C2-C4) alkylene moiety;
[0035] M' can be the same or different, and can be hydrogen, alkali metal, ammonium, protonated alkylamine, protonated alkanolamine, or protonated basic amino acid;
[0036] X' is 1 or 2;
[0037] a' is from 1 to 20; and
[0038] b' is from 0 to 20.
[0039] In some embodiments, R 1’ and R 2’ Each is independently substituted by a hydroxyl, alkoxy, or aryl group.
[0040] In some embodiments, one of the α,β-olefinic unsaturated comonomers has the formula (E):
[0041] CH2=C(R 2” OR 3” SO3M (E)
[0042] in
[0043] R 2” It is H or alkyl;
[0044] R 3” It is a straight-chain or branched divalent aliphatic group that can be replaced by a hydroxyl group; and
[0045] "M" is an alkali metal, ammonium, protonated alkylamine, protonated alkanolamine, or protonated basic amino acid.
[0046] In some embodiments, one or more of the α,β-olefinic unsaturated comonomers are selected from the group consisting of: allyl ethoxylates, allyl polyethoxylates, methyl allyl ethoxylates, methyl allyl polyethoxylates, sodium 1-allyloxy-2-hydroxypropyl sulfonate, sodium 2-acrylamido-2-methylpropane sulfonate, sodium vinyl sulfonate, sodium styrene sulfonate, acrylic acid, methacrylic acid, vinyl acetate, acrylates, methacrylates, maleic esters, styrene, and combinations thereof.
[0047] In some embodiments, one of the α,β-olefinic unsaturated comonomers is a maleimide phosphate compound having the following structure:
[0048]
[0049] In some embodiments, allyl phosphate compounds have formula (A-1)
[0050]
[0051] Where n' is from 1 to 20.
[0052] In some embodiments, the oral care composition further comprises an abrasive polishing material selected from the group consisting of: silica, alumina, orthophosphate, polyphosphate, hexametaphosphate, and combinations thereof.
[0053] In some embodiments, the oral care composition further comprises one or more additives selected from the group consisting of: polishing agents, foaming agents, binders, humectants, pharmaceuticals, sweeteners, flavorings, hydrogen peroxide sources, alkali metal bicarbonates, thickeners, xylitol, sorbitol, colorants, sodium carbonate, and combinations thereof.
[0054] Oral care compositions may be in the form of toothpaste, tooth gel, dental cleaning agent, tooth powder, dental paste, mouthwash, rinse, dental mousse, dental floss, chewing gum, soluble oral care strips or films, or tablets for direct application or adhesion to the oral cavity surface.
[0055] In one aspect, a method for treating dental caries, tooth erosion, dentin hypersensitivity, and / or tooth staining is provided, the method comprising using an oral care composition as described herein.
[0056] In another aspect, a method is provided for treating or preventing dental caries, tooth erosion, dentin hypersensitivity, and / or tooth staining, the method comprising using an oral care composition as described herein.
[0057] Other aspects of the invention are disclosed below. Detailed Implementation
[0058] definition
[0059] As used herein, and unless otherwise specified, the terms “about” or “approximately” mean an acceptable error as determined by one of ordinary skill in the art for a particular value, depending in part on how the value is measured or determined. In some embodiments, the terms “about” or “approximately” mean within 1, 2, 3, or 4 standard deviations. In some embodiments, the terms “about” or “approximately” mean within 50%, 20%, 15%, 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1%, 0.5%, or 0.05% of a given value or range.
[0060] While compositions and methods are described as “comprising,” “containing,” or “including” various components or steps, they may also be described as “consistently comprising” or “comprises of various components, substances, and steps.” As used herein, the term “consistently comprising” should be understood to mean including the listed components, substances, or steps, as well as any additional components, substances, or steps that do not materially affect the fundamental and novel characteristics of the composition or method. In some embodiments, a composition “consistently comprising” according to embodiments of this disclosure is defined as including the listed components or substances, excluding any additional components or substances that alter the fundamental and novel characteristics of the composition.
[0061] The abbreviations used in this article have their conventional meanings in the fields of chemistry and biology. The chemical structures and formulas listed in this article are constructed according to the standard rules of chemical valence known in the field of chemistry.
[0062] When substituents are specified by their conventional chemical formula written from left to right, they also contain chemically identical substituents produced by structures written from right to left, for example, -CH2O- is equivalent to -OCH2-.
[0063] As used herein, the term “a / an” means one or more. For example, as used herein, the phrase “substituted by [n]” means that the specified group can be substituted by one or more of any or all named substituents. For example, when the group (such as alkyl) is “unsubstituted C1-C”, it means that the specified group can be substituted by one or more of any or all named substituents. 20 When "alkyl-substituted", the group may contain one or more unsubstituted C1-C groups. 20 alkyl.
[0064] Unless otherwise specified, the term "alkyl" itself, or as part of another substituent, means a straight (i.e., unbranched) or branched carbon chain (or carbon) or combination thereof, which may be fully saturated, monounsaturated, or polyunsaturated, and may include monovalent, divalent, and polyvalent groups. Alkyl groups may contain a specified number of carbons (e.g., C1-C1). 10 (This refers to one to ten carbons). An alkyl group is an uncyclic chain. Examples of saturated hydrocarbon groups include, but are not limited to, the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl, methyl, their homologues and isomers such as n-pentyl, n-hexyl, n-heptyl, n-octyl, etc. An unsaturated alkyl group is an alkyl group having one or more double or triple bonds. Examples of unsaturated alkyl groups include, but are not limited to, vinyl, 2-propynyl, crotonyl, 2-isopentenyl, 2-(butadienyl), 2,4-pentadienyl, 3-(1,4-pentadienyl), ethynyl, 1-propynyl and 3-propynyl, 3-butynyl, and higher homologues and isomers. An alkoxy group is an alkyl group that is attached to the remainder of the molecule via an oxygen linker (-O-). The alkyl moiety can be an alkenyl moiety. The alkyl moiety can be an alkynyl moiety. The alkyl moiety can be fully saturated. In addition to one or more double bonds, an alkenyl group may also include more than one double bond and / or one or more triple bonds. In addition to one or more triple bonds, an alkynyl group may also include more than one triple bond and / or one or more double bonds.
[0065] Unless otherwise specified, the term "alkylene" itself, or as part of another substituent, refers to a divalent group derived from an alkyl group, exemplified but not limited to -CH2CH2CH2CH2-. Typically, the alkyl (or alkylene) group will have from 1 to 24 carbon atoms, with those having 10 or fewer carbon atoms preferred herein. "Lower alkyl" or "lower alkylene" is a shorter-chain alkyl or alkylene group that typically has eight or fewer carbon atoms. Unless otherwise specified, the term "alkenyl" itself, or as part of another substituent, refers to a divalent group derived from an olefin.
[0066] A charged portion refers to a functional group that has a high electron density (i.e., negatively charged or negatively polarized) or a low electron density (i.e., positively charged or positively polarized). Non-limiting examples of charged portions include carboxylic acids, alcohols, phosphate groups, aldehydes, and sulfonamides. In the embodiments, the charged portions are capable of forming hydrogen bonds or ionic bonds.
[0067] The term "solution" is used accordingly and refers to a liquid mixture in which a minor component (e.g., a solute or compound) is uniformly distributed within a major component (e.g., a solvent).
[0068] As used herein, the term "salt" refers to an acid salt or base salt of a compound used in the methods described herein. Illustrative examples of acceptable salts are salts of inorganic acids (hydrochloric acid, hydrobromic acid, phosphoric acid, etc.), salts of organic acids (acetic acid, propionic acid, glutamic acid, citric acid, etc.), and salts of quaternary ammonium compounds (methyl iodide compounds, ethyl iodide compounds, etc.).
[0069] The term "silicon dioxide" is used according to its simple and general meaning and refers to a composition (e.g., a solid composition, such as crystals, nanoparticles, or nanocrystals) containing an oxide of silicon (e.g., Si atoms, e.g., tetrahedral coordinated) with four oxygen atoms surrounding a central Si atom. Nanoparticles can be composed of at least two different materials, one material (e.g., an insoluble drug) forming the core and another material forming a shell (e.g., silicon dioxide) surrounding the core; when the shell contains Si atoms, the nanoparticle can be called a silicon dioxide nanoparticle. Silicon dioxide nanoparticles can also refer to particles containing a silicon-oxygen bond matrix, wherein the longest diameter is typically less than or equal to 1000 nanometers.
[0070] As used herein, functionalized silica nanoparticles can refer to post-conjugation to the hydroxyl surface of the nanoparticles (i.e., post-conjugation of the silica nanoparticles). For example, silica nanoparticles can be further functionalized to include additional atoms (e.g., nitrogen) or chemical entities (e.g., polymeric portions or bio-conjugating groups). For instance, when silica nanoparticles are further functionalized with a nitrogen-containing compound, one of the surface oxygen atoms surrounding the Si atoms can be replaced by a nitrogen-containing portion.
[0071] The term "polymer" refers to a molecule that contains repeating subunits (e.g., polymeric monomers). For example, polymer molecules can be based on polyethylene glycol (PEG), poly[amino(1-oxo-1,6-hexadiyl)], poly(oxy-1,2-ethylenedioxycarbonyl-1,4-phenylenecarbonyl), tetraethylene glycol (TEG), polyvinylpyrrolidone (PVP), poly(xylene), or poly(p-xylene). See, for example, “Chemistry of Protein Conjugation and Cross-Linking,” Shan S. Wong, CRC Press, Boca Raton, FL, USA, 1993; “BioConjugate Techniques,” Greg T. Hermanson, Academic Press, San Diego, CA, USA, 1996; “Catalog of Polyethylene Glycol and Derivatives for Advanced PEGylation,” 2004, Nektar Therapeutics, Huntsville, Alabama, USA. These are incorporated in their entirety by reference for all purposes.
[0072] The phrase “average molecular weight” refers to the weight-average molecular weight of a polymer determined by gel permeation chromatography (also known as GPC or size exclusion chromatography (SEC)) using a tetrahydrofuran (THF) aqueous buffer solution at pH 7 as a solvent and light scattering detection.
[0073] If there is any conflict in the use of words or terms in this specification or in one or more patents or other documents that may be incorporated herein by reference, the definitions consistent with those in this specification shall prevail.
[0074] Oral care composition
[0075] Although some exemplary embodiments have been discussed, this specification is illustrative only and not restrictive. Many variations of this disclosure will become apparent to those skilled in the art upon review of this specification.
[0076] In one aspect, an oral care composition is provided. The oral care composition may be or be included in an oral care product, which may be in, but is not limited to, the following forms: toothpaste, tooth gel, dental floss, tooth powder, dental paste, mouthwash, rinsing agent, dental mousse, dental floss, chewing gum, soluble oral care strips or films, or tablets for direct application or adhesion to the oral cavity surface.
[0077] Oral care compositions include oral-acceptable carriers; amphoteric surfactants; oral-acceptable cationic antimicrobial agents; and copolymers (e.g., anionic copolymers).
[0078] Amphoteric surfactants can be betaine compounds. As used herein, the term "betaine" refers to any compound that is generally neutral but has both a cationic and anionic functional moiety. In exemplary embodiments, the amphoteric surfactant or betaine comprises a quaternary ammonium cation (positively charged group) and a carboxylic acid anion (negatively charged group). In exemplary embodiments, the amphoteric surfactant or betaine comprises a quaternary ammonium cation (positively charged group) and a sulfite anion (negatively charged group). In exemplary embodiments, the amphoteric surfactant or betaine comprises a quaternary ammonium cation (positively charged group) and a sulfate anion (charged group). In exemplary embodiments, the amphoteric surfactant or betaine comprises a quaternary ammonium cation (positively charged group) and a phosphate anion (negatively charged group).
[0079] Amphoteric surfactants have the structure of formula (I):
[0080]
[0081] Where L is a substituted or unsubstituted (C2-C4) alkylene group;
[0082] n is an integer from 1 to 10;
[0083] R a and R b It is independently a C1-C4 alkyl group;
[0084] R c Is it substituted or unsubstituted C1-C? 20 Alkyl; and
[0085] Y is an anionic group.
[0086] In some embodiments, Y is -C(O)O or -S(O)2O. In an exemplary embodiment, Y is -C(O)O. In an exemplary embodiment, Y is -S(O)2O.
[0087] In some embodiments, n is 2, 3, or 4. In an exemplary embodiment, n is 2.
[0088] In an exemplary embodiment, n is 3. In an exemplary embodiment, n is 4.
[0089] In some embodiments, R a and R b It is independently methyl or ethyl. In an exemplary embodiment, R a It is a methyl group. In an exemplary embodiment, Ra It is ethyl. In an exemplary embodiment, R b It is a methyl group. In an exemplary embodiment, R b It is an ethyl group.
[0090] In some embodiments, L is an unsubstituted (C2-C4) alkylene. In an exemplary embodiment, L is ethylene. In an exemplary embodiment, L is propylene. In an exemplary embodiment, L is isopropylene. In an exemplary embodiment, L is butylene. In an exemplary embodiment, L is isobutylene. In an exemplary embodiment, L is tert-butylene.
[0091] In some embodiments, L is a substituted (C2-C4) alkylene. In an exemplary embodiment, L is an OH-substituted (C2-C4) alkylene. In an exemplary embodiment, L is an OH-substituted ethylene. In an exemplary embodiment, L is an OH-substituted propylene. In an exemplary embodiment, L is an OH-substituted isopropylene. In an exemplary embodiment, L is an OH-substituted butylene. In an exemplary embodiment, L is an OH-substituted isobutylene. In an exemplary embodiment, L is an OH-substituted tert-butylene.
[0092] In some embodiments, R c It is unsubstituted C1-C 20 Alkyl group. In an exemplary embodiment, R c It is unsubstituted C4-C 20 Alkyl group. In an exemplary embodiment, R c It is unsubstituted C4-C 12 Alkyl group. In an exemplary embodiment, R c It is the unreplaced C8-C 12 Alkyl group. In an exemplary embodiment, R c It is an unsubstituted C8 alkyl group. In an exemplary embodiment, R c It is an unsubstituted C9 alkyl group. In an exemplary embodiment, R c It is unreplaced C 10 Alkyl group. In an exemplary embodiment, R c It is unreplaced C 11 Alkyl group. In an exemplary embodiment, R c It is unreplaced C 12 alkyl.
[0093] In some embodiments, the amphoteric surfactant has the following structure:
[0094]
[0095] In some embodiments, the amphoteric surfactant has the following structure:
[0096]
[0097] In some embodiments, the amphoteric surfactant has the following structure:
[0098]
[0099] In some embodiments, the amphoteric surfactant is selected from cocamidopropyl betaine, lauramidopropyl betaine, cocoyl betaine, cocamidopropyl hydroxysulfonate betaine, and combinations thereof.
[0100] Orally acceptable cationic antimicrobial agents can include agents that are present in an aqueous solution in cationic form at physiological pH (e.g., pH ranging from about 6.5 to 7.8, from 7.0 to 7.5, or from 7.35 to 7.45) and provide specific benefits (e.g., reducing or inhibiting microbial activity in a physiological atmosphere or environment). For example, cationic antimicrobial agents can provide anti-gingivitis, anti-carious, and / or anti-dental erosion activity against teeth, gums, or the oral cavity. Cationic antimicrobial agents can be soluble or substantially soluble in aqueous solutions (e.g., water, saliva, or solutions of oral care products). In some embodiments, cationic antimicrobial agents can be incorporated into formulations prepared in free or salt form.
[0101] In some embodiments, the cationic antimicrobial agent may be selected from one or more of quaternary ammonium surfactants (e.g., cetylpyridinium chloride (CPC)), biguanides (e.g., chlorhexidine digluconate), cationic amino acids (e.g., arginine), metal cations (e.g., zinc (Zn), calcium (Ca), or stannous (Sn) ions), or combinations thereof. In some embodiments, the cationic antimicrobial agent may cause or enhance staining, for example, due to the deposition of pigments or their salt forms.
[0102] The copolymer includes, or is made from, the following: i) an allyl phosphate compound; and ii) one or more α,β-olefinic unsaturated comonomers, at least one of which is not an allyl functional comonomer.
[0103] Allyl phosphate compounds have formula (A):
[0104] [CH2=CH-CH2-O(R 1 O) a (R 2 O) b ] x P(O)(OM) 3-x (A)
[0105] in
[0106] R 1 It is a substituted or unsubstituted (C2-C4) alkylene moiety;
[0107] R 2 It is a substituted or unsubstituted (C2-C4) alkylene moiety;
[0108] M can be the same or different, and can be hydrogen, alkali metal, ammonium, protonated alkylamine, protonated alkanolamine, or protonated basic amino acid;
[0109] X is 1 or 2.
[0110] a is from 1 to 20; and
[0111] b ranges from 0 to 20.
[0112] In some embodiments, R 1 and R 2 It can be independently substituted by hydroxyl, alkoxy, or aryl groups.
[0113] In exemplary embodiments, allyl phosphate compounds having formula (A) can be prepared by various methods. For example, U.S. Patent No. 8,653,181 (in its entirety incorporated herein by reference) describes a method for preparing an allyl ethoxylated phosphate having formula (A).
[0114] The α,β-olefinically unsaturated comonomer can be any such compound, but is preferably a monomer that copolymerizes well with an allyl monomer, and may include those different from monomer (A) but still containing phosphate esters or other functional groups such as carboxylates or sulfonates. In some embodiments, one or more of the α,β-olefinically unsaturated comonomers are allyl-functionalized sulfonate monomers, such as sodium 1-allyloxy-2-hydroxypropyl sulfonate or a non-allyl monomer, sodium 2-acrylamido-2-methylpropane sulfonate, sodium vinyl sulfonate, sodium styrene sulfonate, acrylic acid or methacrylic acid, maleic acid, maleic anhydride (optionally, as an anhydride polymerized after its hydrolysis), fumaric acid, itaconic acid and their water-soluble salts, especially their alkali metal salts or ammonium salts, as described in U.S. Patent No. 9,115,236 (incorporated herein by reference).
[0115] In some embodiments, the allyl phosphate compound (A) has the structure of formula (A-1).
[0116]
[0117] Where n is between 1 and 20.
[0118] In some embodiments, n' is 1 to 10. In an exemplary embodiment, n' is 2 to 8. In an exemplary embodiment, n' is 3 to 6. In an exemplary embodiment, n' is 3 to 5. In an exemplary embodiment, n' is 3 to 4.
[0119] In some embodiments, one or more of the α,β-olefinically unsaturated comonomers are allyl ethoxylates or methanallyl ethoxylates. In some embodiments, one or more of the α,β-olefinically unsaturated comonomers are compounds according to formula (B) as described below. In some embodiments, one or more of the α,β-olefinically unsaturated comonomers are selected from any combination of the comonomers described above.
[0120] In some embodiments, one or more α,β-olefinically unsaturated comonomers include a portion selected from maleic anhydride, maleic acid, itaconic anhydride, itaconic acid, and combinations thereof. In an exemplary embodiment, one or more α,β-olefinically unsaturated comonomers include a maleic anhydride portion. In an exemplary embodiment, one or more α,β-olefinically unsaturated comonomers include a maleic acid portion. In an exemplary embodiment, one or more α,β-olefinically unsaturated comonomers include an itaconic anhydride portion. In an exemplary embodiment, one or more α,β-olefinically unsaturated comonomers include an itaconic acid portion.
[0121] In some embodiments, one or more of the α,β-olefinic unsaturated comonomers include or have an α,β-olefinic unsaturated maleimide phosphate compound of formula (B):
[0122]
[0123] in
[0124] R 1’ It is a substituted or unsubstituted (C2-C4) alkylene moiety;
[0125] R 2’ It is a substituted or unsubstituted (C2-C4) alkylene moiety;
[0126] M' can be the same or different, and can be hydrogen, alkali metal, ammonium, protonated alkylamine, protonated alkanolamine, or protonated basic amino acid;
[0127] X' is 1 or 2.
[0128] a' is from 1 to 20; and
[0129] b' is from 0 to 20.
[0130] In some embodiments, R in a compound having formula (B) 1’ and R2’ It can be independently substituted by hydroxyl, alkoxy, or aryl groups.
[0131] In some embodiments, the copolymer is polymerized from a mixture comprising an allyl phosphate compound and one or more α,β-encapsulated unsaturated comonomers (e.g., a monomer mixture). In some embodiments, the copolymer is polymerized from a mixture comprising an allyl phosphate compound and one or more α,β-encapsulated unsaturated comonomers (e.g., one or more α,β-encapsulated unsaturated maleimide phosphate comonomers) (e.g., a monomer mixture). In some embodiments, the copolymer is polymerized from a mixture comprising an allyl phosphate compound, one or more α,β-encapsulated unsaturated comonomers, and one or more α,β-encapsulated unsaturated maleimide phosphate comonomers (e.g., a mixture). In some embodiments, the copolymer is polymerized from a mixture comprising an allyl phosphate compound and one or more α,β-encapsulated unsaturated maleimide phosphate comonomers (e.g., a monomer mixture). In some embodiments, the copolymer is polymerized from a mixture (e.g., a monomer mixture) comprising one or more α,β-olefinically unsaturated comonomers and one or more α,β-olefinically unsaturated maleimide phosphate comonomers.
[0132] The α,β-ene-bonded unsaturated maleimide phosphate compound having formula (B) can be prepared by several methods. In an example, according to a modified version of the method described in Example 1 of U.S. Patent No. 2,980,652, 2-hydroxyethyl-2-oxoethylamine (diethylene glycolamine, available from Huntsman Corporation) is reacted with an approximately equimolar amount of maleic anhydride in chloroform, wherein the diethylene glycolamine replaces the 1-(2-aminoethyl)imidazolinone-2 used in the example. According to a modified version of the method of Example 5 of U.S. Patent No. 2,980,652, the resulting compound is then cyclically closed. In this modified version of the method, the resulting compound contains -CH2CH2OCH2CH2OH instead of the imidazolinone-2 ring in column 10, lines 40-44 of the '652 patent. The resulting closed-ring hydroxyl-functional maleimide compound is then phosphorylated by reacting it with polyphosphate and phosphoric anhydride according to a modified method of Example 1 of U.S. Patent No. 5,550,274, wherein the hydroxyl-functional maleimide compound replaces lauryl alcohol, and the molar amount of the phosphorylating agent is adjusted to the specific requirements of the method.
[0133] In some embodiments, the maleimide phosphate compound having formula (B) is a compound having formula (B-1):
[0134]
[0135] In some embodiments, the copolymer may be polymerized from a monomer mixture comprising one or more α,β-olefinic unsaturated maleimide phosphate compounds having formula (B) and one or more α,β-olefinic unsaturated comonomers, wherein at least one of the one or more α,β-olefinic unsaturated comonomers is not a maleimide functional comonomer.
[0136] In some embodiments, one or more of the α,β-olefinically unsaturated comonomers polymerized with one or more compounds having formula (B) are allyl functional sulfonate monomers, such as sodium 1-allyloxy-2-hydroxypropyl sulfonate or non-allyl monomers, sodium 2-acrylamido-2-methylpropane sulfonate, sodium vinyl sulfonate, sodium styrene sulfonate, acrylic acid or methacrylic acid, maleic acid, maleic anhydride (optionally, as an anhydride polymerized after its hydrolysis), fumaric acid, itaconic acid and their water-soluble salts, particularly their alkali metal salts or ammonium salts, as described in U.S. Patent No. 9,115,236 (incorporated herein by reference). In some embodiments, one or more α,β-olefinically unsaturated comonomers may comprise allyl ethoxylates (or polyethoxylates) or methanallyl ethoxylates (or polyethoxylates). In some embodiments, one or more α,β-olefinically unsaturated comonomers may be compounds according to formula (A) as described above.
[0137] In some embodiments, one or more of the α,β-olefinically unsaturated comonomers are selected from: allyl ethoxylates, allyl polyethoxylates, methyl allyl ethoxylates, methyl allyl polyethoxylates, sodium 1-allyloxy-2-hydroxypropyl sulfonate, sodium 2-acrylamido-2-methylpropane sulfonate, sodium vinyl sulfonate, sodium styrene sulfonate, acrylic acid, methacrylic acid, vinyl acetate, acrylates, methacrylates, maleic esters, styrene, and combinations thereof. In some embodiments, one or more of the α,β-olefinically unsaturated comonomers may include one or more combinations selected from any of the comonomers described above.
[0138] In some embodiments, the copolymer has a selected molecular weight and functionality such that it forms a film that protects the tooth surface from the adhesion of bacteria, plaque, and colorants, while enhancing the deposition and retention of fluoride, antibacterial agents, and / or mild tooth whitening agents on the tooth surface.
[0139] Although acidic ionic monomers can be copolymerized either in acid or salt form, it should be understood that what will be needed is to adjust the pH of the final copolymer to a physiological pH (e.g., a pH range of about 6.5 to 7.8, 7.0 to 7.5, or 7.35 to 7.45), thus at least partially converting the acidic groups to salt form.
[0140] In some embodiments, comonomers as used herein are selected, and polymerization methods are chosen to maximize monomer bonding to the copolymer according to a desired distribution: random, alternating, or block polymerization. In some respects, the "-mer" units are distributed as uniformly as possible along the polymer chain.
[0141] In some embodiments, nonionic monomers are used to balance the reactivity of the selected monomer mixture and influence the bulk properties of the copolymer, such as water solubility, To, etc. g The copolymer may exhibit properties such as toughness, durability, or cost. These will include vinyl acetate, acrylates, methacrylates, maleate and diesters, fumarate diesters, and styrene. In some embodiments, the copolymer may further comprise one or more nonionic monomers.
[0142] For example, at least one of the comonomers is a nonionic maleimide alkoxylated comonomer compound having formula (C):
[0143]
[0144] in
[0145] R 11 It is a substituted or unsubstituted (C2-C4) alkylene moiety;
[0146] R 12 It is a substituted or unsubstituted (C2-C4) alkylene moiety;
[0147] a1 is from 1 to 20; and
[0148] b1 ranges from 0 to 20.
[0149] In some embodiments, R in equation (C) 11 and R 12 Each is an independent (C2-C4) alkylene moiety that is partially substituted by hydroxyl, alkoxy, or aryloxy groups.
[0150] Examples of suitable nonionic maleimide alkoxylated comonomer compounds have the formula (C-1):
[0151]
[0152] Maleimide derivatives can be prepared by reacting a suitable primary amine with maleic anhydride, as reported in U.S. Patent No. 5,306,828. The monomer (C-1) can be reserved from the bulk of the maleimide for later use, or a portion of the total feed can be phosphorylated with a reduced phosphorylating agent feed, leaving an excess of (C-1) in the phosphate ester product mixture as a "nonionic" monomer compatible with other comonomers, possessing similar polymerization reactivity and terminal hydroxyl groups. If desired, it will act as a "diluent" monomer that can reduce the phosphate ester monomer content in the copolymer.
[0153] In some embodiments, copolymers (e.g., trimers) comprising additional olefinically unsaturated monomers and allyl alkoxylated phosphates of formula (A) and / or maleimide polyalkoxylated phosphates of formula (B) can be prepared by the synthetic method described in U.S. Patent No. 9,115,236.
[0154] In some embodiments, one or more of the α,β-olefinically unsaturated comonomers polymerized with one or more compounds having formula (B) are allyl functional sulfonate monomers, such as sodium 1-allyloxy-2-hydroxypropyl sulfonate or non-allyl monomers, sodium 2-acrylamido-2-methylpropane sulfonate, sodium vinyl sulfonate, sodium styrene sulfonate, acrylic acid or methacrylic acid, maleic acid, maleic anhydride (optionally, as an anhydride polymerized after its hydrolysis), fumaric acid, itaconic acid and their water-soluble salts, particularly their alkali metal salts or ammonium salts, as described in U.S. Patent No. 9,115,236 (incorporated herein by reference). In some embodiments, one or more of the α,β-olefinically unsaturated comonomers are allyl ethoxylates (or polyethoxylates) or methanallyl ethoxylates (or polyethoxylates). In some embodiments, one or more of the α,β-olefinically unsaturated comonomers are compounds according to formula (A) as described above. In some embodiments, one or more of the α,β-olefinic unsaturated comonomers are selected from any combination of the aforementioned comonomers.
[0155] In some embodiments, nonionic monomers are used to balance the reactivity of the selected monomer mixture and influence the bulk properties of the copolymer, such as water solubility, To, etc. g Toughness, durability, or cost are all factors to consider. Suitable nonionic monomers include, for example, vinyl acetate, acrylates, methacrylates, maleates and diesters, fumarate diesters, and styrene.
[0156] Although acidic ionic monomers can copolymerize either in acid or salt form, it should be understood that what will be needed is to adjust the pH of the final copolymer to a physiological pH, thus at least partially converting the acidic groups to salt form.
[0157] In some embodiments, the comonomers are selected such that the copolymer is an alternating copolymer that is substantially non-homogeneous. In some embodiments, the comonomers are selected such that the copolymer is an alternating copolymer exhibiting homopolymerity.
[0158] In some embodiments, one or more of the α,β-olefinic unsaturated comonomers are one or more allyl functional monomers, which may be homologues of the polyoxyolefin monoallyl ether starting material of formula (A). The allyl functional monomer has formula (D):
[0159] [CH2=CH-CH2-O(R1O) a (R2O) b ] x H(D),
[0160] R1, R2, a, b, and X are defined as in equation (A).
[0161] In some embodiments, the α,β-olefinic unsaturated phosphate comonomer is an allyl compound having formula (D-1):
[0162] CH2=CH-CH2-O(CH2CH2O) a -H (D-1)
[0163] Where a is from 1 to 20.
[0164] In some embodiments, one or more of the α,β-olefinic unsaturated comonomers are allyl functional monomers having formula (E):
[0165] CH2=C(R 2” CH2O(R) 3” (OH)SO3M” (E)
[0166] in
[0167] R 2” It is H or alkyl;
[0168] R 3” It is a straight-chain or branched substituted or unsubstituted divalent aliphatic group; and
[0169] "M" is an alkali metal, ammonium, protonated alkylamine, protonated alkanolamine, or protonated basic amino acid.
[0170] In some embodiments, one or more of the α,β-olefinic unsaturated comonomers are selected from any combination of the aforementioned comonomers.
[0171] Oral care compositions comprising one or more of any phosphate copolymers according to this disclosure are also presented. The compositions according to this disclosure are suitable for use in humans and non-human mammals. As used herein, the term "oral care composition" means a product that, for oral activity purposes, remains in the oral cavity for a sufficient period of time during normal use to contact part or all of the tooth surfaces and / or oral tissues. As used herein, "tooth surface" means the surface of natural teeth or the hard surface of artificial dentition (including dentures, dental plates, crowns, caps, fillings, bridges, implants, and the like).
[0172] In some embodiments, the oral care composition is selected from toothpaste, tooth gel, dental floss, tooth powder, dental paste, mouthwash, rinse, dental mousse, dental floss, chewing gum, soluble oral care strips or films for direct application or adhesion to the oral cavity surface, or lozenges. In some embodiments, the oral care composition includes at least one copolymer having a selected molecular weight and functionality such that the copolymer forms a film that adheres to the tooth surface and protects the tooth surface from tooth erosion, dentin hypersensitivity, bacterial, plaque, and staining agent adhesion caused by acidic beverages or acid reflux, while enhancing the deposition and retention of fluoride, antibacterial agents, or mild whitening agents on the tooth surface.
[0173] In some embodiments, the oral care composition includes an orally acceptable carrier. In various embodiments, the carrier is a liquid, a semi-solid, or a solid. A “liquid” can be a liquid with low or high viscosity. A liquid can be such that its flow is imperceptible under ambient conditions. A liquid can be a thixotropic liquid. As used herein, a “semi-solid” can be a gel, colloid, or gum. As used herein, semi-solids and liquids are fluids distinguished based on viscosity: semi-solids are high-viscosity fluids, while liquids have lower viscosity. There is no clear boundary between these two types of fluids. In some embodiments, a semi-solid can have a viscosity up to several thousand mPas. Carriers among those useful herein include liquids, pastes, ointments, and gels, and can be transparent, translucent, or opaque. In some embodiments, an orally acceptable carrier includes water. For example, one or more copolymers (e.g., in a soluble form) are present in the liquid carrier.
[0174] In some embodiments, the oral care composition includes an abrasive polishing material. In some embodiments, the abrasive polishing material is selected from silica, alumina, orthophosphate, polyphosphate, hexametaphosphate, and combinations thereof. In some embodiments, the oral care composition includes an abrasive selected from one or more of hydrated silica, colloidal silica, fumed silica, and combinations thereof. In some embodiments, the oral care composition includes insoluble sodium hexametaphosphate, insoluble sodium aluminosilicate, sodium bicarbonate, and combinations thereof.
[0175] In some embodiments, the oral care composition includes one or more additives. In some embodiments, the one or more additives are selected from polishing agents, foaming agents, binders, humectants, pharmaceuticals, sweeteners, flavorings, peroxide sources, alkali metal bicarbonates, thickeners, xylitol, sorbitol, colorants, sodium carbonate, and combinations thereof.
[0176] In some embodiments, the oral care composition includes a safe and effective amount of fluoride source. The fluoride source may be sufficient to provide anti-caries effectiveness. A wide variety of fluoride-generating materials can be used as sources of soluble fluoride in the oral care compositions of the present invention. Representative fluoride ion sources include sodium fluoride, potassium fluoride, sodium monofluorophosphate, and combinations thereof.
[0177] In some embodiments, the oral care composition further comprises a phosphate surfactant. Suitable phosphate surfactants include those described in U.S. Patent No. 9,040,025 (the disclosure of which is incorporated herein by reference in its entirety).
[0178] In some embodiments, the oral care composition is a dental cleaning product comprising one or more copolymers as described herein and an amphoteric surfactant (betaine). In some embodiments, the dental cleaning product further comprises an abrasive. In some embodiments, the dental cleaning product is free of calcium and other divalent ions, surfactants, phosphate salts, and optionally liquids.
[0179] Methods for using the oral care composition described herein for treating dental caries, tooth erosion, dentin hypersensitivity, and / or tooth staining are also provided. The methods used herein include contacting the tooth surfaces and / or oral mucosa of a subject with the oral care composition according to this disclosure. In some embodiments, the oral care composition is deposited as a protective film. Treatment methods may include brushing and / or rinsing. Other methods include contacting toothpaste, dental gel, dental floss, tooth powder, dental paste, mouthwash, rinse, dental mousse, dental floss, chewing gum, soluble oral care strips or films, or lozenges or other forms with the tooth surfaces and / or oral mucosa of a subject. According to this embodiment, the oral care composition may be used as frequently as toothpaste, or it may be used less frequently, such as often once a week, or by a professional in the form of a dental paste or other fortifying treatment.
[0180] A further method is provided for treating or preventing dental caries, tooth erosion, dentin hypersensitivity, and / or tooth staining, the method comprising using an oral care composition as described herein. The method used herein includes contacting the tooth surfaces and / or oral mucosa of a subject with the oral care composition according to this disclosure. In some embodiments, the oral care composition is deposited as a protective film. The treatment method may be by brushing and / or rinsing. Other methods include contacting toothpaste, dental gel, dental floss, tooth powder, dental paste, mouthwash, rinse, dental mousse, dental floss, chewing gum, soluble oral care strips or films, or lozenges or other forms with the tooth surfaces and / or oral mucosa of a subject. According to this embodiment, the oral care composition may be used as frequently as toothpaste, or may be used less frequently, such as often once a week, or by a professional in the form of a dental paste or other fortifying treatment.
[0181] It should be understood that any numerical ranges listed herein are intended to include all subranges contained therein. For example, the range “1 to 10” is intended to include all subranges between the listed minimum value of 1 and the listed maximum value of 10, and including all endpoints; that is, a minimum value equal to or greater than 1 and a maximum value equal to or less than 10. Because the disclosed numerical ranges are continuous, they include every value between the minimum and maximum values. Unless otherwise clearly indicated, the various numerical ranges specified in this application are approximate values.
[0182] This disclosure will be further described with reference to the following examples. These examples are illustrative only and are not intended to be limiting. Unless otherwise specified, all percentages are by weight of the total composition.
[0183] Example
[0184] Chlorhexidine gluconate (“CHX”) is a cationic chemical used as an antimicrobial agent to treat periodontitis, gingivitis, and other oral care and gum diseases. Despite its effectiveness as an antimicrobial agent, its main side effect is enamel yellowing or staining. The stain-preventing efficacy of anionic polymers in dental applications has been tested. However, the polymer is anionic and, by itself, incompatible with cationic antimicrobial agents. It was observed that the antimicrobial agent is soluble in the blend by adding an amphoteric surfactant (such as lauramidopropyl betaine) to the polymer. The stain-preventing efficacy of this blend was then tested and compared with a control containing only chlorhexidine and an amphoteric surfactant. It was observed that the addition of the polymer / ampholyte blend significantly reduced tooth staining compared to chlorhexidine and an amphoteric solution alone.
[0185] Example 1: Copolymer Synthesis
[0186] Poly(maleic acid-co-PAM5000) (“P(MA-co-PAM5000)”)
[0187] 62.40 g of 43 wt.% aqueous maleic acid was introduced at room temperature into a 1-liter reactor equipped with a mechanical stirrer and condenser; 37.60 g of 73.9 wt.% aqueous solution of SIPOMER PAM5000 (Solvay, CAS No. 60497-09-08) was added. After deoxygenation by bubbling with nitrogen for 30 minutes, the mixture was brought to 80°C with stirring. Then, 10 g of 25 wt.% aqueous solution of sodium persulfate was added. After 60 minutes of reaction, 10.03 g of 25 wt.% aqueous solution of sodium persulfate was added in one batch. The mixture was then maintained at 80°C for 4 hours with stirring. After a total reaction time of 6 hours at 80°C, the mixture was cooled to room temperature and neutralized with 34.1 g of 50 wt.% aqueous sodium hydroxide with stirring. The average molecular weight was 12,000 g / mol. The measured solids (after 60 minutes at 120°C) were 51.48 wt.%.
[0188] Poly(acrylic acid-co-PAM5000) (“P(AA-co-PAM5000)”)
[0189] 92.10 g of a 29.4 wt.% aqueous solution of SIPOMER PAM5000 (Solvay, CAS No. 60497-09-08) was introduced into a 1-liter reactor equipped with a mechanical stirrer and condenser at room temperature; 211.92 g of purified water was added. After deoxygenation by bubbling with nitrogen for 60 minutes, the mixture was brought to 80°C for more than 60 minutes. Then, the following were added simultaneously over 180 minutes: 67.69 g of a 39.3 wt.% aqueous solution of acrylic acid and 17.10 g of a 2.82 wt.% aqueous solution of sodium hypophosphite, and over 195 minutes, 41.32 g of a 10.06 wt.% aqueous solution of sodium persulfate. The mixture was then maintained at 80°C for 1 hour with stirring. After a total reaction time of 4 hours at 80°C, the mixture was cooled to room temperature for 60 minutes and then neutralized with 35.88 g of a 50 wt.% aqueous solution of sodium hydroxide. The number-average molecular weight is between 10,000 and 200,000 g / mol. The measured solid content (115 °C; 60 min) is 15.24 wt.%.
[0190] Example 2: Method for Formulating Blends
[0191] Prepare a polymer / ampholy blend in a 1:1 ratio. Measure water in a beaker and add 0.5%–10% of an amphoteric surfactant (cocamidopropyl betaine; lauramidopropyl betaine; cocoyl betaine; cocamidopropyl hydroxysulfonate betaine, etc.) and mix. Then add 0.5%–10% of the polymer and mix to form a homogeneous blend. Accurately weigh 0.12% chlorhexidine gluconate while stirring and add it to the beaker, allowing mixing until a completely homogeneous and clear solution is obtained. Measure the pH of the formulation and adjust to 5–8 (target 6.5).
[0192] Staining prevention measures
[0193] Preparation of artificial saliva
[0194] 1. Soak hydroxyapatite (HAP) discs in artificial saliva (Table 1) overnight to promote membrane formation.
[0195] 2. Prepare a solution from the following: 1% of a polymer / ampholy mixture with 0.12% chlorhexidine gluconate in a 0.3M salt solution; and 0.12% chlorhexidine in 1% of an amphoteric surfactant in a 0.3M salt solution.
[0196] 3. Treat each HAP dish with 30 ml of one of the test solutions for 15 minutes. Obtain the L*a*b values using a colorflex EZ spectrophotometer. Then immerse the HAP dish in 30 ml of a 10% coffee / tea staining solution for one hour. Rinse with deionized (DI) water for 10 seconds and soak in 30 ml of artificial saliva for one hour. Repeat this cycle three times. At the end of the third cycle, record the L*a*b readings and calculate ΔL.
[0197] Table 1: Artificial Saliva
[0198] Element 1000ml Beef extract (Lab Lemco) 1 Moon-shaped peptone 5 Yeast extract 2 NaCl 0.35 <![CDATA[CaCl2]]> 0.2 KCl 0.2 porcine mucin type II 2.5 40% w / v urea 1.3 water Appropriate amount
[0199] plan
[0200] 1. Soak hydroxyapatite (HAP) discs in artificial saliva overnight to promote membrane formation.
[0201] 2. Apply 30 ml of 1% test solution to the HAP plate and let it sit for 15 minutes.
[0202] 3. Take the first L*a*b reading.
[0203] 4. Soak the HAP dish in 30 ml of 10% staining solution (5% coffee and 5% tea) for 60 minutes.
[0204] 5. Rinse the HAP tray with water for 10 seconds.
[0205] 6. Incubate the dish in 30ml of artificial saliva at 37°C for 60 minutes.
[0206] 7. Repeat steps 4-6 for 3 cycles.
[0207] 8. At the end of the third cycle, take the final L*a*b reading and calculate ΔL.
[0208] 9. Calculate the percentage of staining prevention using the following equation.
[0209] Staining inhibition % = {(ΔL treated / ΔL untreated) x 100} - 100
[0210] Example 3: Compatibility and staining prevention data
[0211] Table 2: Compatibility:
[0212]
[0213] (CHX = Chlorhexidine Gluconate)
[0214] Table 3: Stain prevention %
[0215]
[0216]
[0217] It was observed that the addition of the polymer / ampholy blend to chlorhexidine gluconate significantly reduced tooth staining compared to a combination of chlorhexidine and an amphoteric surfactant. Furthermore, additional testing showed that the polymer / ampholy blend did not interfere with the antimicrobial efficacy of chlorhexidine.
[0218] In light of the above examples, it is anticipated that everyday oral care compositions (e.g., in the form of toothpaste, tooth gel, dental floss, tooth powder, dental paste, mouthwash, rinse, dental mousse, dental floss, chewing gum, soluble oral care strips or films, or tablets) will provide a powerful, consumer-friendly, and easy-to-use supply of arsenal to correct or prevent a wide variety of common oral diseases in both humans and other mammals.
[0219] The disclosed subject matter has been described in detail with reference to its specific embodiments. Such details are not intended to be considered as a limitation on the scope of the disclosed subject matter, except to the extent that they are included in the appended claims.
[0220] Therefore, the exemplary embodiments described herein are well suited to achieving the stated purposes and advantages, as well as those inherent therein. The specific embodiments disclosed above are merely illustrative, as the exemplary embodiments described herein can be modified and practiced in ways that are obvious to those skilled in the art, different but equivalent, to the teachings herein. Furthermore, no limitation is intended to be made on the details of the structures or designs shown herein, except as described in the following claims. It is therefore apparent that the specific illustrative embodiments disclosed above can be changed, combined, or modified, and all such changes are considered to be within the scope and spirit of the exemplary embodiments described herein. The exemplary embodiments described herein, illustratively disclosed herein, can be appropriately practiced in the absence of any elements not specifically disclosed herein and / or any optional elements disclosed herein.
Claims
1. An oral care composition comprising: Oral-acceptable carriers; Lauramide propyl betaine; An orally acceptable cationic antimicrobial agent, wherein the orally acceptable cationic antimicrobial agent is selected from chlorhexidine gluconate; and The following copolymers: i) An allyl phosphate compound, wherein the allyl phosphate compound has the formula (A-1) Where n is from 1 to 20; and ii) One or more α,β-olefinic unsaturated comonomers, wherein at least one of them is not an allyl functional comonomer. The one or more α,β-olefinic unsaturated comonomers are selected from maleic anhydride, maleic acid, or acrylic acid.
2. The oral care composition of claim 1, further comprising an abrasive polishing material selected from the group consisting of: silica, alumina, orthophosphate, polyphosphate, hexametaphosphate, and combinations thereof.
3. The oral care composition of claim 1, further comprising one or more additives selected from the group consisting of: polishing agents, foaming agents, binders, humectants, sweeteners, flavorings, peroxide sources, thickeners, colorants, and combinations thereof.
4. The oral care composition of claim 1, further comprising one or more additives selected from the group consisting of alkali metal bicarbonates, xylitol, sorbitol, sodium carbonate, and combinations thereof.
5. The oral care composition of claim 1, wherein, The oral care composition is in the form of toothpaste, tooth gel, tooth powder, dental paste, mouthwash, rinse, dental mousse, dental floss, chewing gum, soluble oral care strips or films, or tablets for direct application or adhesion to the oral cavity surface.
6. Use of the oral care composition of any one of claims 1-5 in the preparation of a medicament for treating dental caries, tooth erosion, dentin hypersensitivity, and / or tooth staining.
7. Use of the oral care composition according to any one of claims 1-5 in the preparation of a medicament for treating and preventing dental caries, tooth erosion, dentin hypersensitivity and / or tooth staining.
Citation Information
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