Oral care compositions and methods

Abstract

Disclosed herein are oral care compositions, such as mouthwash or mouth rinse compositions, comprising at least a plant-based amine chloride and at least a flavorant. Methods for manufacturing and methods of using the oral care compositions are also disclosed herein.

Description

ORAL CARE COMPOSITIONS AND METHODSCROSS-REFERENCE TO RELATED APPLICATION

[0001] This application claims the benefit of priority from U.S. Provisional Patent Application No. 63 / 567,208, filed 19 March 2024, the contents of which are hereby incorporated herein by reference in their entirety.BACKGROUND

[0002] 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). 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.

[0003] It has therefore been attempted to take steps against the formation of pathological symptoms in the oral cavity using various oral hygiene compositions, including toothpastes, mouthwashes, or dental gels. 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”). Upon oral use of the hygiene composition, the amine fluoride active compounds form a thin hydrophobic film on the tooth enamel, wherein the amine hydrofluoride groups come into contact with the tooth enamel and result in a CaF2 covering layer having long-chain hydrocarbon residues. Thus, the tooth enamel becomes more resistant to acid attacks on account of the CaF2 covering layer formed, and the long-chain hydrocarbon residues form a hydrophobic layer that prevents the formation of deposits and the attack of the acidic degradation products on the tooth enamel.

[0004] While such amine fluorides are effective when used in oral care compositions, their use can be costly due, in pail, to the expenses associated with manufacture. Additionally, the current method of synthesizing involves the use of hydrofluoric acid, which is highly corrosive and posesa high safety risk when working with this material. Tt would therefore be beneficial to synthesize active compounds without the use of hydrofluoric acid, as disclosed, for example in PCT Publication No. WO 2022 / 133441, incorporated herein by reference in its entirety. Additionally, 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.

[0005] It would therefore be beneficial to use fatty acids of plant-derived origin for the production of amine bases, including for example amine chlorides, to produce an oral care composition having good clarity and good oral health properties.BRIEF SUMMARY

[0006] This summary is intended merely to introduce a simplified summary of some aspects of one or more implementations of the present disclosure. Further areas of applicability of the present disclosure will become apparent from the detailed description provided hereinafter. This summary is not an extensive overview, nor is it intended to identify all elements of the present teachings, nor to delineate the scope of the disclosure. Rather, its purpose is merely to present one or more concepts in simplified form as a prelude to the detailed description below.

[0007] Aspects disclosed herein are directed to oral care compositions comprising an amine chloride. In certain embodiments, the oral care composition further comprises at least one flavorant. In certain embodiments, the at least one amine chloride is a plant-based amine chloride, e.g., a polyethylglycol amine, such as oleamidopropyl aminoethyl-3 dihydrochloride, and in certain embodiments, the at least one plant-based amine chloride is present in the composition in an amount ranging from about 0.5 wt.% to about 5 wt.%, preferably from about 1 wt.% to about 3 wt.% or from about 1.5 wt.% to about 2 wt.%, by weight based on the total weight of the oral care composition. In certain embodiments, the oral care composition is a mouthwash or a mouth rinse.

[0008] In various aspects, 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.

[0009] According to certain embodiments, 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 ammoniumfluorosilicate, e.g., sodium fluoride. In certain embodiments, the at least one fluoride ion source is present in the oral care composition in an amount ranging from about 0.005 wt.% to about 2.5 wt.%, preferably from about 0.025 wt.% to about 0.0145 wt.%, by weight based on the total weight of the oral care composition.

[0010] In certain embodiments, 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). In certain embodiments of the oral care composition disclosed herein, the at least one metal ion source (e.g., zinc lactate) 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.

[0011] In certain embodiments, 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.

[0012] According to certain aspects, 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). In certain embodiments, 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.

[0013] Also disclosed herein are methods of manufacturing an oral care composition as disclosed herein. In certain embodiments, provided herein is a method of manufacturing an oral care composition (e.g., a mouthwash or a mouth rinse), wherein 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 carecomposition; and (4) optionally adding polyvinyl pyrrolidone (PVP) to the oral care composition after combining the first solution and the second solution.

[0014] According to certain embodiments of the methods disclosed herein, the at least one plantbased amine chloride is oleamidopropyl aminoethyl-3 dihydrochloride. In certain aspects, 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). In certain aspects of the methods disclosed herein, 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). According to certain embodiments of the methods disclosed herein, 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.

[0015] Also disclosed herein are methods of improving the oral health of a subject, the method 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.

[0016] In certain embodiments, 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.

[0017] According to certain embodiments disclosed herein, 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, andin 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.DETAILED DESCRIPTION

[0018] For illustrative purposes, the principles of the present disclosure are described by referencing various exemplary embodiments thereof. Although certain embodiments of the disclosure are specifically described herein, one of ordinary skill in the art will readily recognize that the same principles are equally applicable to, and can be employed in other compositions and methods. Before explaining the disclosed embodiments of the present disclosure in detail, it is to be understood that the disclosure is not limited in its application to the details of any particular embodiment disclosed herein. The terminology used herein is for the purpose of description and not of limitation.

[0019] As used herein and in the appended claims, the singular forms “a”, “an”, and “the” include plural references unless the context dictates otherwise. The singular form of any class of the ingredients refers not only to one chemical species within that class, but also to a mixture of those chemical species. The terms “a” (or “an”), “one or more” and “at least one” may be used interchangeably herein. The terms “comprising”, “including”, and “having” may be used interchangeably. The term “include” should be interpreted as “include, but are not limited to”. The term “including” should be interpreted as “including, but are not limited to”.

[0020] As used throughout, 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.

[0021] The term “about” when referring to a number means any number within a range of 10% of the number. For example, the phrase “about 2 wt.%” refers to a number between and including 1.8 wt.% and 2.2 wt.%.

[0022] All references cited herein are hereby incorporated by reference in their entireties. In the event of a conflict in a definition in the present disclosure and that of a cited reference, the present disclosure controls.

[0023] The abbreviations and symbols as used herein, unless indicated otherwise, take their ordinary meaning. The abbreviation “wt.%” means percent by weight with respect to the oral carecomposition. 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.

[0024] When referring to chemical structures and names, the symbols “C”, “H”, and “O” mean carbon, hydrogen, and oxygen, respectively. The symbols“=”, and “= ’ mean single bond, double bond, and triple bond, respectively.

[0025] 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.

[0026] The phrases, “a mixture thereof,” “a combination thereof,” or a combination of two or more thereof’ do not require that the mixture include all of A, B, C, D, E, and F (although all of A, B,C, D, E, and F may be included). Rather, it indicates that a mixture of any two or more of A, B, C,D, E, and F can be included. In other words, it is equivalent to the phrase “one or more elements selected from the group consisting of A, B, C, D, E, F, and a mixture of any two or more of A, B, C, D, E, and F.” Likewise, the term “a salt thereof” also relates to “salts thereof.” Thus, where 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.

[0027] All components and elements positively set forth in this disclosure can be negatively excluded from the claims. In other words, 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. In some instances, 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. For example, 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.

[0028] Some of the various categories of components identified may overlap. In such cases where overlap may exist and the oral care composition includes both components (or the composition includes more than two components that overlap), an overlapping compound does not represent more than one component. For example, 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.

[0029] For readability purposes, the chemical functional groups are in their adjective form; for each of the adjectives, the word “group” is assumed. For example, the adjective “alkyl” without a noun thereafter, should be read as “an alkyl group.”

[0030] As used herein, the term “oral care composition” means a composition that is delivered to the oral surfaces. In certain embodiments, 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.

[0031] As used herein, 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. Alternatively, the oral care composition may be dual phase and dispensed from separated compartment dispenser(s). In certain embodiments, the oral care composition disclosed herein is a mouthwash or a mouth rinse.

[0032] As used herein, the term “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, exceptfor 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). In particular, 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.” In methods for the production or manufacture of an oral care composition containing an amine chloride, an amine base may be a precursor to forming the amine chloride. In methods for the production or manufacture of an oral care composition containing an amine fluoride, 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.

[0033] As used herein, 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. For example, 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. In certain embodiments, the reaction may further comprise mixing an amine chloride with a fluoride ion source, such as sodium fluoride, thus creating an amine fluoride.

[0034] In certain embodiments, 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.Amine Chloride

[0035] Disclosed herein are oral care compositions comprising at least one amine chloride. In certain embodiments, the oral care composition is a mouthwash or a mouth rinse composition, and in certain embodiments, the oral care composition is a toothpaste. According to certain embodiments, the at least one amine chloride is a plant-based amine chloride. As used herein, the term “plant based” indicates that the compound originates or is derived from a plant source as opposed to an animal source, e.g., tallow. A plant source may include any part or pails of the plant, such as the stems, roots, leaves, fruits, vegetables, seeds, flowers, etc.

[0036] In certain embodiments, the oral care composition disclosed herein is prepared by adding an amine chloride to the composition, as discussed herein. In certain embodiments, the amine chloride in the oral care composition may further be combined with a fluoride ion source to forman amine fluoride in situ. In certain embodiments, 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.

[0037] In certain embodiments, the amine base is selected from a primary amine, a secondary amine, a tertiary amine, or combinations thereof. In certain embodiments, the amine base is animal derived (e.g., tallow derived, including bovine tallow derived), and in certain embodiments, the amine base is plant derived. In embodiments wherein the amine base is plant derived, the plant- derived amine base may be derived from rapeseed oil, rice bran oil, or a combination thereof. According to certain embodiments, the amine base is a linear or branched fatty amine, poly amine, or mixtures thereof. For example, in certain embodiments, 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. According to certain embodiments, the amine base may be selected from a myristyl, palmityl, linoleyl, oleyl, or steryl amine or polyamine, or mixtures thereof. In certain embodiments, the amine base is an oleyl amine or polyamine.

[0038] In certain embodiments of the disclosure, the amine base is a polyamine, such as a polyamine selected from monoamine bases, diamine bases, triamine bases, and mixtures thereof. In certain embodiments, the amine base is selected from N'-octadccyltrimcthylcndiaminc-N.N.N'- tris(2-ethanol) and N-octadeca-9-enylamine.

[0039] In certain embodiments, 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. In certain embodiments, 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. In certain embodiments, the amine base comprises or is derived from oleic acid. In one embodiment, the amine base is a polyethylene glycol amine. In one embodiments, the amine base is oleamidopropyl aminoethyl-3 dihydrochloride, and in one embodiment, the amine chloride is formed from the addition of hydrogen chloride to oleamidopropyl aminoethyl-3. Oleamidopropyl aminoethyl-3 dihydrochloride is also known as ethanol, 2,2’-((3-((2-hydroxyethyl)oleamino)propyl)imino)bis-,dihydrochloride. Tn certain embodiments, oleamidopropyl aminoethyl-3 may have the following structure:wherein x+y+z has an average value of 3.

[0040] In certain embodiments, 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 about 3 wt.%, about 0.5 wt.% to about 2.5 wt.%, about 0.5 wt.% to about 2 wt.%, or about 0.5 wt.% to about 1.7 wt.%; from about 1 wt.% to about 5 wt.%, such as from about 1 wt.% to about 4.5 wt.%, about 1 wt.% to about 4 wt.%, about 1 wt.% to about 3.5 wt.%, about 1 wt.% to about 3 wt.%, about 1 wt.% to about 2.5 wt.%, about 1 wt.% to about 2 wt.%, or about 1 wt.% to about 1.7 wt.%; from about 1.5 wt.% to about 5 wt.%, such as from 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.%, about 1.5 wt.% to about 2.5 wt.%, about 1.5 wt.% to about 2 wt.%, or about 1.5 wt.% to about 1.7 wt.%, or any range or subrange thereof, by weight based on the total weight of the oral care composition.Fluoride Ion Source

[0041] In certain embodiments of the disclosure, in addition to the amine chloride, 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. In certain embodiments, 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, orsubstantially free of, N-octadeca-9-enylamine hydrofluoride. In certain embodiments, the fluoride ion source is sodium fluoride. In certain embodiments, the amine chloride may react in situ with the fluoride ion source (e.g., sodium fluoride) to form an amine fluoride.

[0042] 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. In certain embodiments, 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.Metal Ion Source

[0043] In certain embodiments, 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. For example, in certain embodiments, the oral care composition may include a zinc ion source selected from zinc oxide, zinc citrate, zinc lactate, zinc phosphate, and combinations thereof. In certain embodiments, 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.

[0044] The oral care compositions disclosed herein may comprise a zinc ion source. In certain exemplary embodiments, 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. For example, 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, based on the totalweight of the oral care composition. Tn at least one embodiment, 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. In certain embodiments, the zinc ion source is zinc lactate.

[0045] In certain embodiments, 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. For example, 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 1.5 to about 5 wt.%, about 1.5 to about 4 wt.%, about 1.5 to about 3 wt.%; from about 2 to about 5 wt.%, about 2 to about 4 wt.%, about 2 to about 3 wt.%; from about 3 to about 5 wt.%, about 4 to about 5 wt.%, or any range or subrange thereof, based on the total weight of the oral care composition. In at least one embodiment, oral care composition includes about 0.4 to about 0.5 wt.% of stannous ion source, such as about 0.45 wt.% of stannous ion source, based on the total weight of the oral care composition.

[0046] 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. In at least one embodiment, the stannous ion source comprises stannous fluoride, and at least one embodiment, the stannous ion source consists of stannous fluoride.

[0047] 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. For instance, 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. In some embodiments, the oral care composition comprises stannous fluoride and stannous pyrophosphate.Additionally or alternatively, the oral care composition may comprise stannous fluoride and stannous chloride.Polymers

[0048] 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. 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.

[0049] Other 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.

[0050] 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.

[0051] In certain embodiments, 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 asN-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. In some embodiments the polymer comprises an insoluble cross-linked homopolymer. Such polymers include crosslinked PVP (often referred to as cPVP, polyvinylpolypyrrolidone, or cross-povidone).

[0052] For example, in certain embodiments 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 2 wt.% to about 3.5 wt.%, about 2 wt.% to about 3 wt.%, about 2.20 wt.% to about 3 wt.%, about 2.4 wt.% to about 3 wt.%, or about 2 wt.% to about 2.5 wt.%; from about 2.2 wt.% to about 2.8 wt.%, about 2.3 wt.% to about 2.5 wt.%, or about 2.4 wt.%, or any range or subrange thereof, by weight relative to the total weight of the oral care composition.

[0053] Humectants

[0054] 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. In certain embodiments of the oral compositions disclosed herein, the composition incorporates at least one humectant to reduce evaporation and / or to contribute towards preservation by lowering water activity. In certain exemplary embodiments, 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 subrangethereof, by total weight of the oral care composition. In certain embodiments, the oral care composition comprises a combination of glycerin and xylitol.Emulsifiers

[0055] 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. In certain embodiments, the emulsifier may be chosen from poloxamers (e.g., PLURONICS®) and other non-ionic emulsifiers. In certain embodiments, 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 about 1.5 wt.%, about 0.2 wt.% to about 1 wt.%, or about 0.2 wt.% to about 0.5 wt.%; from about 0.4 wt.% to about 2 wt.%, such as from about 0.4 wt.% to about 1.8 wt.%, about 0.4 wt.% to about 1.5 wt.%, about 0.4 wt.% to about 1 wt.%, or about 0.4 wt.% to about 0.5 wt.%; or about 0.42 wt.%.Flavorants

[0056] The oral care compositions of the present disclosure may include at least one flavoring agent. The flavoring agent is typically incorporated in the oral care composition at a concentration of about 0.001 to about 3 wt.% by weight of the oral care composition. For example, the amount of flavoring agent(s) present in the oral care composition may range from about 0.01 to about 2 wt.%, about 0.01 to about 1 wt.%, about 0.01 to about 0.5 wt.%, about 0.01 to about 0.1 wt.%; from about 0.015 to about 3 wt.%, about 0.015 to about 2 wt.%, about 0.015 to about 1 wt.%, about 0.015 to about 0.5 wt.%; from about 0.5 to about 3 wt.%, about 0.5 to about 2 wt.%, about 0.5 to about 1 wt.%; from about 1 to about 3 wt.%, about 1 to about 2 wt.%; from about 2 to about 3 wt.%, including any range or subrange thereof, based on the total weight of the oral care composition.

[0057] Suitable flavoring agents include, but are not limited to, essential oils and various flavoring aldehydes, esters, alcohols, and similar materials. Examples of the essential oils include oils ofspearmint, 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

[0058] 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.

[0059] In certain embodiments, the oral care composition disclosed herein is free of or substantially free of ethanol.Additional Ingredients

[0060] The oral care compositions disclosed herein may further comprise additional ingredients as known in the art and as disclosed below. These 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-limiting examples of these ingredients are provided herein. Suitable components, such as those listed herein, 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 theoral care composition. Tn other embodiments, the oral care composition may include two or more phases, such as two, three, four, or five phases.

[0061] 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. In certain embodiments, 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.

[0062] An abrasive removes debris and surface stains. In certain embodiments 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. For example, synthetic amorphous silica. Silica may also be available as a thickening agent, e.g., particle silica. For example, the silica can also be small particle silica.

[0063] In some embodiments, 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. In some embodiments, the surfactant is reasonably stable throughout a wide pH range. In some embodiments, 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. In some embodiments, 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 anonionic 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.

[0064] 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.

[0065] 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(OCH2CH2)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(CH2)IOCH2(OCH2CH2)OSO3Na); (iv) higher alkyl aryl sulfonates such as sodium dodecyl benzene sulfonate (sodium lauryl benzene sulfonate); and (v) higher alkyl sulfoacetates, such as sodium lauryl sulfoacetate (dodecyl sodium sulfoacetate), higher fatty acid esters of 1,2 dihydroxy propane sulfonate, sulfocolaurate (N-2-ethyl laurate potassium sulfoacetamide) and sodium lauryl sarcosinate.

[0066] In some embodiments, the oral care compositions disclosed herein may comprise an anionic surfactant. In some embodiments, 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. In some embodiments, the oral care compositions disclosed herein may comprise sodium lauryl sulfate, sodium ether lauryl sulfate, or a mixture thereof. In some embodiments, the oral care compositions disclosed herein may comprise sodium lauryl sulfate.

[0067] In certain embodiments, 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- tetradecyl-4-ethylpyridinium chloride (TDEPC)), phenolic antiseptics, hexetidine, octenidine, sanguinarine, povidone iodine, delmopinol, salifluor, sanguinarine, propolis and oxygenating agents (e.g., buffered sodium peroxyborate or peroxycarbonate), phthalic acid and salts thereof, monoperthalic acid and salts and esters thereof, ascorbyl stearate, oleoyl sarcosine, alkyl sulfate, dioctyl sulfosuccinate, salicylanilide, domiphen bromide, delmopinol, octapinol and other piperidine derivatives, nicin preparations, chlorite salts; and combinations thereof.

[0068] In certain embodiments, 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.

[0069] 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. In some embodiments, 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, or about 3 wt.% to about 4 wt.% of a thickener. Higher weight percentages may be used for chewing gums, lozenges and breath mints, sachets, non-abrasive gels and subgingival gels. 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. In some embodiments, a mixture of thickening silica and carrageenan gum may be used as the thickener in the oral care compositions disclosed herein. In some embodiments, 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 thickening silica and carrageenan gum, about 2 wt.% to about 5 wt.% of thickening silica and carrageenan gum, about 2 wt.% to about 4 wt.% of thickening silica and carrageenan gum, or about 3 wt.% to about 4 wt.% of thickening silica and carrageenan gum.

[0070] In certain embodiments, the oral care composition disclosed herein further comprises at least one whitening agent selected from metal chlorides, perborates, percarbonates, peroxyacids, hypochlorites, and combinations thereof.

[0071] 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. In some embodiments, 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.

[0072] The oral care composition may include one or more pH adjusters to increase or decrease the overall pH of the oral care composition. For example, one or more acids may be included to decrease the pH of the oral care composition. Examples of 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 alternativeacids 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.

[0073] 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. For example, 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. In some instances, 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.

[0074] The oral care compositions may have a pH from 4.5 to about 10, 4.5 to about 9, 4.5 to about 8, 4.5 to about 7, 4.5 to about 6; from about 5 to about 10, about 5 to about 9, about 5 to about 8, about 5 to about 7, about 5 to about 6; from about 6 to about 10, about 6 to about 9, about 6 to about 8, or about 6 to about 7; from about 7 to about 10, about 7 to about 9, or about 7 to about 8, including any ranges and subranges therebetween.

[0075] In certain embodiments, 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.

[0076] 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.

[0077] The units of turbidity from a calibrated nephelometer are called Nephelometric Turbidity Units (NTU). 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. In certainembodiments, 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. In certain embodiments, 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. In certain embodiments of the disclosure, 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.

[0078] Relative clarity, transparency, and / or translucency of a solution may also be measured by particle size. Notably, 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. In certain embodiments, 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.

[0079] Also disclosed herein are methods of using the oral care compositions of the present disclosure. In certain embodiments, disclosed herein is a method of improving oral health comprising administering the oral care composition disclosed herein to the oral cavity of a subject in need thereof. In certain embodiments, 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 cariogenic bacteria; and / or cleaning the teeth and / or oral cavity.

[0080] According to certain embodiments of the methods disclosed herein, 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. In some embodiments, the oral care compositions may be administered in a form that is maintained in the oral cavity overnight.

[0081] The oral care 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.

[0082] In certain embodiments of the disclosure, provided herein is a method of manufacturing 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. In certain embodiments, 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. In certain embodiments of the method, the first solution does not comprise PVP, and in certain embodiments, the first solution does not comprise amine chloride. As such, 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.

[0083] The examples and other embodiments described herein are exemplary and not intended to be limiting in describing the full scope of compositions and methods of this disclosure. Equivalent changes, modifications and variations of specific embodiments, materials, compositions and methods may be made within the scope of the present disclosure, with substantially similar results.EXAMPLESExample 1 - Preparation of Oral Care Mouthwash Compositions

[0084] Four 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 containingthe 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, and 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.

[0085] Table 1 A - Preparation of Premix 1

[0086] Table IB - Preparation of Premix 2

[0087] Table 1C - Preparation of final mixtureExample 2 - Particle Size and Turbidity of Oral Care Mouthwash Compositions

[0088] Each of the sample batches described in Example 1 underwent turbidity and particle size analysis immediately following preparation (Day 1) and again after 7 days of aging under ambient conditions (Day 7). The turbidity analysis was performed using a Hach 2100Q Turbidimeter, and the particle size analyses were performed using a Malvern Zetasizer Nano series particle size analyzer. The results are shown below in Table 2.

[0089] Table 2 - Particle size and turbidity of mouthwash compositions

[0090] Visually, it was observed that Batch 2 showed less turbidity than Batch 1. The turbidity analysis confirmed this conclusion quantitatively, as Batch 1 showed 792 NTU compared to Batch 2 at 411 NTU on Day 1, while Batch 1 showed 33.3 NTU on Day 7, compared to 9.95 of Batch 2. The particle size analysis on Day 7 also showed a lower particle size for Batch 2 as compared to Batch 1 (376 nm versus 1042.2 nm). These results indicate that the amine fluoride is more effective as an emulsifying agent when added to the flavor premix of Premix 2, as opposed to when it is added after combination of Premix 1 and Premix 2. Thus, early addition of amine fluoride as an emulsifier in the flavor premix allowed for lower turbidity and particle size, and an overall clearer, more transparent mouthwash solution.

[0091] In comparing Batch 2 (tallow-based amine fluoride) with Batch 4 (plant-based amine chloride), visually Batch 4 was observed to be less cloudy and hazy than Batch 2. The turbidity results confirmed this observation quantitatively, as shown in Table 2. Particle size analysis also showed a smaller particle size for Batch 4 compared to Batch 2 (134.51 nm versus 376 nm on Day 7). This result demonstrates that the plant-based amine chloride was more effective as an emulsifying agent than the tallow-based amine fluoride solution. While not wishing to be bound by theory, it is believed that this suggest that the differences in the fatty chains of the plant-based amine chloride improves the oily contents solubilization as compared to the tallow-based amine fluoride.

[0092] Finally, the impact of the order of addition of PVP was evaluated. Visually, Batch 3 appeared less cloudy than Batch 1. Turbidity analysis showed a significantly lower turbidity onDay 1 for Batch 3 compared to Batch 1 (133 NTUs versus 792 NTUs). The particle size analysis on Day 1 also showed a smaller particle size for Batch 3 compared to Batch 1 (436.3 nm versus 837.3 nm). The results of this study suggest that the addition of PVP to the final mixture resulted in a decrease in turbidity and particle size, as demonstrated in Batch 3.

[0093] The foregoing results support the conclusion that use of a plant-based amine halide, e.g., a plant-based amine chloride, can result in a stable composition having low turbidity and good clarity. Furthermore, addition of the plant-based amine chloride together with a flavorant can improve clarity, as can addition of PVP to the final mixture.

Claims

CLAIMSWhat Is Claimed Is:

1. An oral care composition comprising at least one plant-based amine chloride and at least one flavorant.

2. The oral care composition according to claim 1, wherein the at least one plant-based amine chloride is polyethylglycol amine, preferably oleamidopropyl aminoethyl-3 dihydrochloride.

3. The oral care composition according to claim 1 or 2, wherein the at least one plant-based amine chloride is present in the composition in an amount ranging from about 0.5 wt.% to about 5 wt.%, preferably from about 1 wt.% to about 3 wt.% or from about 1.5 wt.% to about 2 wt.%, by weight based on the total weight of the oral care composition.

4. The oral care composition according to any one of the preceding claims, wherein the oral care composition is a mouthwash or a mouth rinse.

5. The oral care composition according to any one of the preceding claims, wherein 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.

6. The oral care composition according to any one of the preceding claims, further comprising at least one fluoride ion source.

7. The oral care composition according to claim 6, wherein the at least one fluoride ion source is selected from stannous fluoride, sodium fluoride, potassium fluoride, sodium fluorosilicate, or ammonium fluorosilicate, preferably sodium fluoride.

8. The oral care composition according to claim 6 or 7, wherein the at least one fluoride ion source is present in the oral care composition in an amount ranging from about 0.005 wt.% to about2.5 wt.%, preferably from about 0.025 wt.% to about 0.0145 wt.%, by weight based on the total weight of the oral care composition.

9. The oral care composition according to any one of the preceding claims, further comprising at least one metal ion source.

10. The oral care composition according to claim 9, wherein 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.

11. The oral care composition according to claim 10, wherein the zine ion source is selected from zinc oxide, zinc citrate, zinc lactate, zinc phosphate, or combinations thereof, preferably zinc lactate.

12. The oral care composition according to any one of claims 9-11, wherein 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.

13. The oral care composition according to any one of the preceding claims, further comprising at least one humectant.

14. The oral care composition according to claim 13, wherein the at least one humectant is selected from glycerin, sorbitol, xylitol, or propylene glycol, preferably glycerin and xylitol.

15. The oral care composition according to claim 13 or 14, wherein 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.

16. The oral care composition according to any one of the preceding claims, further comprising at least one emulsifier, preferably polyglyccryl-4 caprate.

17. The oral care composition according to any one of the preceding claims, further comprising at least one polymer, preferably polyvinyl pyrrolidone (PVP).

18. The oral care composition according to any one of the preceding claims, wherein 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)- 1 ,3-propanediamine dihydrofluoride.

19. A method of manufacturing an oral care composition, wherein the method comprises: preparing a first solution comprising water and at least one humectant; preparing a second solution comprising at least one amine chloride and at least one flavorant; combining the first solution and the second solution to prepare the oral care composition; and optionally adding polyvinyl pyrrolidone (PVP) to the oral care composition after combining the first solution and the second solution.

20. The method according to claim 19, wherein the at least one amine chloride is a plant-based amine chloride, such as a polyethylglycol amine, preferably oleaminopropylamineth-3 hydrochloride.

21. The method according to claim 19 or 20, wherein the first solution further comprises at least one metal ion source, preferably a zinc ion source (e.g., zinc lactate).

22. The method according to any one of claims 19-21, wherein the first solution further comprises at least one fluoride ion source, preferably sodium fluoride.

23. The method according to any one of claims 19-22, wherein the at least one humectant is selected from glycerin, sorbitol, xylitol, or propylene glycol, preferably glycerin and xylitol.

24. The method according to any one of claims 19-22, wherein the second solution further comprises at least one emulsifier.

25. The method according to claim 24, wherein the at least one emulsifier is polyglyceryl-4 caprate.

26. The method according to any one of claims 19-25, wherein 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.

27. A method of improving the oral health of a subject, the method comprising administering the oral care composition according to any one of claims 1-18 to the oral cavity of a subject in need thereof.

28. The method according to claim 27, wherein improving the oral health of the subject comprises 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.

29. The method according to claim 27 or 28, wherein the oral care composition is administered to the oral cavity of the subject at least once a day, preferably at least twice a day.

30. The method according to any one of claims 27-29, wherein the oral care composition is administered to the oral cavity of the subject for about 10 seconds to about 30 minutes, preferably for about 30 seconds to about 2 minutes.

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