Dental floss coating compositions

Abstract

Disclosed herein are dental floss coating compositions and a dental floss, comprising an amine chloride, such as a plant-based amine chloride, and a fluoride ion source. Methods for manufacturing and methods of using the dental floss are also disclosed herein.

Description

959322-OO-WO-Ol-OCDENTAL FLOSS COATING COMPOSITIONSCROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This application claims the benefit of priority from U.S. Provisional Patent Application No. 63 / 754,649, filed 6 February 2025, the contents of which are hereby incorporated by reference in their entirety.BACKGROUND

[0002] The use of dental floss and other interdental cleaners is an important part of dental hygiene. Dental floss is used to remove plaque and other particulate matter from between the teeth and the gum line. These are areas in the mouth where a toothbrush typically cannot reach, and if not cleaned regularly and properly, tooth decay and gum disease may result.

[0003] Dental floss typically comprises dental floss coating. Such coating may be, for example, a mineral, animal, or vegetable wax coating, which may provide lubricity, and facilitates movement of the floss between teeth. Wax may also prevent the floss fibers from fraying or breaking while it is in use.

[0004] During manufacturing of the floss, the coating is typically melted, additives as described are generally incorporated into the molten coating, and the floss is immersed in a bath containing the molten coating. It may be desirable to incorporate additives, such as peroxides, flavorants, sweeteners, and active compounds into dental floss coatings to impart further therapeutic or cosmetic benefits or to improve taste.

[0005] 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 CaF: 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.959322-OO-WO-Ol-OC

[0006] While such amine fluorides are effective when used in oral care compositions such as dental floss coatings, their use can be costly due, in part, to the expenses associated with manufacture. Additionally, the current method of synthesizing involves the use of hydrofluoric acid, which is highly corrosive and poses a high safety risk when working with this material. It 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.

[0007] 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 a dental floss coating composition having good oral health properties.BRIEF SUMMARY

[0008] 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.

[0009] Aspects disclosed herein are directed to dental floss coating compositions comprising an amine chloride and a fluoride ion source. In certain embodiments, the dental floss coating 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 polyethyleneglycol amine, such as oleamidopropyl aminoethyl-3 dihydrochloride, and in certain embodiments, the at least one plantbased 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 4 wt.% or from about 2 wt.% to about 4 wt.%, by weight based on the total weight of the dental floss coating composition. In certain embodiments, the dental floss coating composition is a molten liquid at a temperature of about 38 °C or more.959322-OO-WO-Ol-OC

[0010] In certain embodiments, the at least one fluoride ion source is selected from stannous fluoride, sodium fluoride, potassium fluoride, sodium fluorosilicate, or ammonium fluorosilicate, e.g.. sodium fluoride. In certain embodiments, the at least one fluoride ion source is present in the dental floss coating composition in an amount ranging from about 0.005 wt.% to about 2.5 wt.%, preferably from about 0.1 wt.% to about 0.2 wt.%, by weight based on the total weight of the dental floss coating composition.

[0011] In certain embodiments, the dental floss coating 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 dental floss coating composition.

[0012] In certain embodiments, the dental floss coating composition further comprises as least one flavorant, and in certain embodiments, the at least one flavorant is present in an amount ranging from about 1 wt.% to about 25 wt.%, preferably about 5 wt.% to about 20 wt.%, or about 5 wt.% to about 15 wt.%, by weight based on the total weight of the dental floss coating composition.

[0013] In certain embodiments, the dental floss coating composition further comprises at least one sweetener, and in certain embodiments, the at least one sweetener is a saccharin, such as sodium saccharin.

[0014] In certain embodiments of the disclosure, the dental floss coating composition is anhydrous, i.e., substantially free of or free of water, or having less than about 5 wt.% water. In certain embodiments, the anhydrous dental floss coating composition comprises at least one polyethylene glycol polymer, such as a polyethylene glycol polymer having an average molecular weight of about 1500 Daltons. In certain embodiments, the at least one polyethylene glycol polymer is present in the dental floss coating composition in an amount ranging from about 5 wt.% to about 20 wt.%, preferably about 15 wt.% to about 20 wt.%, by weight based on the total weight of the dental floss coating composition.

[0015] In certain embodiments, the dental floss coating composition further comprises at least one non-ionic surfactant, preferably a poloxamer, e.g., poloxamer 407. In certain embodiments, the poloxamer is present in the dental floss coating composition in an amount ranging from about 5959322-OO-WO-Ol-OCwt.% to about 20 wt.%, preferably about 15 wt.% to about 20 wt.%, by weight based on the total weight of the dental floss coating composition.

[0016] In certain embodiments of the disclosure, the dental floss coating composition further comprises a wax, such as a microcrystalline wax, and in certain embodiments, the wax is present in the dental floss coating composition in an amount ranging from about 10 wt.% to about 50 wt.%, preferably from about 20 wt.% to about 40 wt.% or from about 25 wt.% to about 35 wt.%, by weight based on the total weight of the dental floss coating composition.

[0017] According to certain aspects, the dental floss coating composition disclosed herein further comprises water. In certain embodiments, the water is present in an amount ranging from about 5 wt.% to about 50 wt.%, such as from about 20 wt.% to about 30 wt.%, by weight based on the total weight of the dental floss coating composition.

[0018] In certain embodiments, the dental floss coating composition further comprises a vinyl acetate / ethylene polymer, and in certain embodiments, the vinyl acetate / ethylene polymer is present in the dental floss coating composition in an amount ranging from about 10 wt.% to about 80 wt.%, preferably from about 15 wt.% to about 55 wt.% or from about 20 wt.% to about 50 wt.%, by weight based on the total weight of the dental floss coating composition.

[0019] According to certain aspects, the dental floss coating composition disclosed herein further comprises at least one emulsifier, e.g., polylyceryl-4 caprate, and in certain aspects, the dental floss coating composition disclosed herein further comprises polyvinyl pyrrolidone (PVP). In certain embodiments, the dental floss coating 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.

[0020] Also disclosed herein are methods of manufacturing a dental floss comprising the dental floss coating composition as disclosed herein. In certain embodiments, provided herein is a method of manufacturing a dental floss, wherein the method comprises: (1) heating a dental floss coating composition as disclosed herein to a temperature greater than about 38 °C to form a molten composition; (2) applying the molten composition to the dental floss to coat the dental floss; and (3) cooling the composition the molten composition to solidify the composition on the dental floss. In certain aspects, disclosed herein is a dental floss comprising the dental floss coating composition as disclosed herein.959322-OO-WO-Ol-OC

[0021] Also disclosed herein are methods of improving the oral health of a subject, the method comprising contacting the dental floss disclosed herein to an interdental space between teeth or to a space between a tooth surface and a gum tissue of a subject in need thereof.

[0022] 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.DETAILED DESCRIPTION

[0023] 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.

[0024] 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”.959322-OO-WO-Ol-OC

[0025] 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.

[0026] 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.%.

[0027] 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.

[0028] 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 dental floss coating composition. The symbol “°” refers to a degree, such as a temperature degree or a degree of an angle. The symbols “h”, “min”, “mL”. “nm”. and “pm” refer to hour, minute, milliliter, nanometer, and micrometer, respectively. The abbreviation “rpm” means revolutions per minute.

[0029] 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.

[0030] 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.

[0031] 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 the959322-OO-WO-Ol-OCdisclosure 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.

[0032] All components and elements positively set forth in this disclosure can be negatively excluded from the claims. In other words, the dental floss coating 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 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 composition by itself. For example, a dental floss coating 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.

[0033] Some of the various categories of components identified may overlap. In such cases where overlap may exist and the dental floss coating 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 dental floss coating composition includes both a polyol and a sweetener, xylitol will serve only as either a polyol or a sweetener — not both.

[0034] 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.”

[0035] 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.959322-OO-WO-Ol-OC

[0036] As used herein, the term “dental floss coating composition” means a composition for use in coating a dental floss, wherein dental floss is generally a linear strip of material having a diameter sufficient to fit in the distance between teeth. Methods of making dental floss and dental floss coating compositions are known in the art and are further disclosed herein.

[0037] 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, except for carbonyl group carbons. “Amine base” may be used to refer to compounds containing a plurality of primary, secondary and / or tertiary amine groups (e.g., a tertiary polyamine). 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 a dental floss coating 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 a dental floss coating 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.

[0038] 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 dental floss coating composition. For example, the reaction may be a salination reaction earned 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.

[0039] In certain embodiments, the dental floss coating composition disclosed herein is an aqueous solution, and in certain embodiments, the dental floss coating composition is in the form of a solid,959322-OO-WO-Ol-OCsemi-solid, or gel composition. Tn certain embodiments, the dental floss coating composition is in molten or liquid form.Amine Chloride

[0040] Disclosed herein are dental floss coating compositions comprising at least one amine chloride. 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 parts of the plant, such as the stems, roots, leaves, fruits, vegetables, seeds, flowers, etc. (e.g., rapeseed oil).

[0041] In certain embodiments, the dental floss coating composition disclosed herein is prepared by adding an amine chloride to the composition, as discussed herein. In certain embodiments, the amine chloride in the dental floss coating composition may further be combined with a fluoride ion source to form an amine fluoride in situ. In certain embodiments, the dental floss coating composition may be prepared by mixing an amine base (e.g., polyamine base) with an acid and a source of chloride, and forming an amine chloride.

[0042] 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.

[0043] 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 '-octadecyl tri methy lendi amine- N,N,N '- tris(2-ethanol) and N-octadeca-9-enylamine.959322-OO-WO-Ol-OC

[0044] In certain embodiments, the dental floss coating 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. In certain embodiments, oleamidopropyl aminoethyl-3 may have the following structure:wherein x+y+z has an average value of 3.

[0045] In certain embodiments, the amine chloride is present in the dental floss coating 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 4.75 wt.%, about 0.1 wt.% to about 4.5 wt.%, about 0.1 wt.% to about 4.25 wt.%, about 0.1 wt.% to about 4 wt.%, about 0.1 wt.% to about 3.75 wt.%, about 0.1 wt.% to about 3.5 wt.%, about 0.1 wt.% to about 3.25 wt.%, about 0.1 wt.% to about 3 wt.%, about 0.1 wt.% to about 2.75 wt.%; from about 1 wt.% to about 5 wt.%, such as from about 1 wt.% to about 4.75 wt.%, about 1 wt.% to about 4.5 wt.%, about 1 wt.% to about 4.25 wt.%, about 1 wt.% to about 4 wt.%, about 1 wt.% to about 3.75 wt.%, about 1 wt.% to about 3.5 wt.%, about 1 wt.% to about 3.25 wt.%, about 1 wt.% to about 3 wt.%, about 1 wt.% to about 2.75 wt.%; from about 2 wt.% to about 5 wt.%, such as from about 2 wt.% to about 4.75 wt.%, about 2 wt.% to about 4.5 wt.%, about 2 wt.% to about 4 wt.%, about 2 wt.% to about 3.5 wt.%, about 2 wt.% to about 3 wt.%. about 2 wt.% to about 2.75 wt.%, about 2.5 wt.% to about 5 wt.%, about 2.5 wt.% to about959322-OO-WO-Ol-OC4.5 wt.%, about 2.5 wt.% to about 4 wt.%, about 2.75 wt.% to about 3.75 wt.%, or any range or subrange thereof, by weight based on the total weight of the dental floss coating composition.

[0046] As would be appreciated by one of ordinary skill in the art. in embodiments wherein the amine chloride is present in a dental floss, the amine chloride may be present in the dental floss in an amount corresponding to the weight of the dental floss coating composition relative to the uncoated dental floss.Fluoride Ion Source

[0047] In certain embodiments of the disclosure, in addition to the amine chloride, the dental floss coating 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 dental floss coating composition disclosed herein is free of, or substantially free of, N'-octadecyltrimethylendiamine- N,N,N'-tris(2-ethanol)-dihydrofluoride, and in certain embodiments, the dental floss coating composition is free of, or substantially 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.

[0048] The at least one fluoride ion source may be present in the dental floss coating compositions disclosed herein in an amount ranging from about 0.005 wt.% to about 2.5 wt.%, such as from about 0.005 wt.% to about 2 wt.%, about 0.005 wt.% to about 1.5 wt.%, about 0.005 wt.% to about 1 wt.%, about 0.005 wt.% to about 0.5 wt.%, about 0.005 wt.% to about 0.05 wt.%; from about O.05 wt.% to about 1.5 wt.%, about 0.05 wt.% to about 1 wt.%. about 0.05 wt.% to about 0.5 wt.%; about 0.1 wt.% to about 1.5 wt.%, about 0.1 wt.% to about 1 wt.%, about 0.1 wt.% to about 0.5 wt.%, or any range or subrange thereof, by weight based on the total weight of the dental floss coating composition. In certain embodiments, the at least one fluoride ion source may be present in the dental floss coating composition in an amount of about 0.01 wt.%, about 0.05 wt.%, about 0.1 wt.%, about 0.15 wt.%, about 0.2 wt.%, about 0.25 wt.%, or about 0.3 wt.%. In certain embodiments, the total fluoride content of the dental floss coating composition ranges from about959322-OO-WO-Ol-OC50 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.Polymers, Binders, and Waxes

[0049] The dental floss coating compositions disclosed herein may include one or more polymers, binders, and / or waxes.

[0050] The dental floss coating 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.

[0051] In certain embodiments, the coating composition may contain at least one polyethylene glycol polymer. In certain embodiments, the melting point of the polyethylene glycol polymer(s) is below about 50 °C, such as between about 38 °C and about 50 °C. In certain embodiments, the one or more polyethylene glycol polymers have an average molecular weight of from 950 to 9000 Daltons, or from 1000 to 3000 Daltons. For example, the one or more polyethylene glycol polymers may have an average molecular weight of from 1200 to 1600 Daltons or an average molecular weight of 1500 Daltons, e.g., polyethylene glycol 1500.

[0052] In certain embodiments, the dental floss coating compositions disclosed herein may further comprise polyvinyl pyrrolidone (PVP) polymer. PVP is a water-soluble synthetic homopolymer useful in oral care compositions. PVP refers to a polymer containing vinylpyrrolidone (also referred to as N- vinylpyrrolidone and N-vinyl-2-pyrrolidinone) as a monomeric unit. The monomeric unit consists of a polar imide group, four non-polar methylene groups, and a non-polar methane group. The polymers include soluble and insoluble homopolymeric PVPs. Copolymers containing PVP include vinylpyrrolidone / vinyl acetate (also known as Copolyvidone, Copolyvidonum or VP-VAc) and vinyl pyrrolidone / dimethylamino-ethylmethacrylate. Soluble PVP polymers among those useful herein are known in the art, including Povidone, Polyvidone, Polyvidonum, poly(N-vinyl-2-pyrrolidinone), poly (N-vinylbutyrolactam), poly(l-vinyl-2-pyrrolidone) and poly [l-(2-oxo-l pyrrolidinyl)ethylene] . These PVP polymers are not959322-OO-WO-Ol-OCsubstantially cross-linked. Tn some embodiments the polymer comprises an insoluble cross-linked homopolymer. Such polymers include crosslinked PVP (often referred to as cPVP, polyvinylpolypyrrolidone, or cross-povidone).

[0053] For example, in certain embodiments the dental floss coating compositions disclosed herein comprise at least one polymer, such as polyethylene glycol, in an amount ranging from about 1 wt.% to about 50 wt.%. such as about 1 wt.% to about 25 wt.%, about 1 wt.% to about 20 wt.%, about 1 wt.% to about 17 wt.%; from about 5 wt.% to about 25 wt.%, about 5 wt.% to about 20 wt.%, about 5 wt.% to about 17 wt.%; from about 10 wt.% to about 25 wt.%, about 10 wt.% to about 20 wt.%, about 10 wt.% to about 17 wt.%; from about 15 wt.% to about 25 wt.%, about 15 wt.% to about 20 wt.%, or about 17 wt.%, or any range or subrange thereof, by weight relative to the total weight of the dental floss coating composition.

[0054] In certain embodiments, the dental floss coating composition disclosed herein may comprise at least one polymer as a binding agent. Suitable polymers include polyurethanes, polyesters, polyamides such as nylons, vinyl alcohol homopolymers and copolymers, vinyl acetate homopolymers and copolymers. Various polyurethanes can be ultra-violet cured. Useful solvent-based polymers include vinyl acetate copolymers, vinyl alcohol copolymers and nylon dissolved in a water, ethanol, or ethanol / water mixture. When the solvent (e.g., water) is evaporated the polymer may act to keep the filaments locked to the yarn and the yarn in the crosssectioned structure in which the polymer has been set. Suitable water-soluble polymers include vinyl alcohol polymers and copolymers, vinyl acetate polymers and copolymers and copolymers of vinyl acetate / ethylene copolymer. In certain embodiments, the dental floss coating composition comprises a vinyl acetate / ethylene copolymer, e.g., VINNAPAS® EP (Wacker Chemie, Munich). As noted, the coating can be applied by immersion in a bath, by being passed over a coating roller, by being passed through two coating rollers and by being sprayed with the water-soluble polymer.

[0055] In embodiments disclosed herein, the at least one polymer (e.g., a vinyl acetate / ethylene copolymer) is present in the dental floss coating composition in an amount ranging from about 10 wt.% to about 90 wt.%, such as from about 10 wt.% to about 80 wt.%, about 10 wt.% to about 70 wt.%, about 10 wt.% to about 60 wt.%, about 10 wt.% to about 55 wt.%, about 10 wt.% to about 51 wt.%, about 10 wt.% to about 50 wt.%; from about 20 wt.% to about 80 wt.%, about 20 wt.% to about 70 wt.%, about 20 wt.% to about 60 wt.%, about 20 wt.% to about 55 wt.%, about 20 wt.% to about 51 wt.%, about 20 wt.% to about 50 wt.%; from about 30 wt.% to about 80 wt.%,959322-OO-WO-Ol-OCabout 30 wt.% to about 70 wt.%, about 30 wt.% to about 60 wt.%, about 30 wt.% to about 55 wt.%, about 30 wt.% to about 51 wt.%, about 30 wt.% to about 50 wt.%; from about 40 wt.% to about 80 wt.%. about 40 wt.% to about 70 wt.%, about 40 wt.% to about 60 wt.%. about 40 wt.% to about 55 wt.%, about 40 wt.% to about 51 wt.%, about 40 wt.% to about 50 wt.%; from about 45 wt.% to about 80 wt.%, about 45 wt.% to about 70 wt.%, about 45 wt.% to about 60 wt.%, about 45 wt.% to about 55 wt.%, about 45 wt.% to about 51 wt.%, about 45 wt.% to about 50 wt.%; from about 50 wt.% to about 80 wt.%, about 50 wt.% to about 70 wt.%, about 50 wt.% to about 60 wt.%, about 50 wt.% to about 55 wt.%, about 50 wt.% to about 51 wt.%, about 50 wt.%, or about 51 wt.%, based on a total weight of the dental floss coating composition.

[0056] In certain embodiments, the dental floss coating composition disclosed herein comprises as wax. The wax may be any wax known for use in oral care compositions, including, for example, microcrystalline wax. The microcrystalline wax may increase the coefficient of friction so that the strand of floss can be more easily gripped. In embodiments wherein the dental floss coating composition comprises a wax, the wax may be present in the dental floss coating composition in an amount ranging from about 5 wt.% to about 80 wt.%, such as from about 5 wt.% to about 70 wt.%, about 5 wt.% to about 60 wt.%, about 5 wt.% to about 50 wt.%, about 5 wt.% to about 40 wt.%, about 5 wt.% to about 35 wt.%; from about 10 wt.% to about 80 wt.%, about 10 wt.% to about 70 wt.%, about 10 wt.% to about 60 wt.%, about 10 wt.% to about 50 wt.%, about 10 wt.% to about 40 wt.%, about 10 wt.% to about 35 wt.%; from about 15 wt.% to about 80 wt.%, about 15 wt.% to about 70 wt.%, about 15 wt.% to about 60 wt.%, about 15 wt.% to about 50 wt.%, about 15 wt.% to about 40 wt.%, about 15 wt.% to about 35 wt.%; from about 20 wt.% to about 80 wt.%, about 20 wt.% to about 70 wt.%, about 20 wt.% to about 60 wt.%, about 20 wt.% to about 50 wt.%, about 20 wt.% to about 40 wt.%, about 20 wt.% to about 35 wt.%; from about 30 wt.% to about 80 wt.%, about 30 wt.% to about 70 wt.%, about 30 wt.% to about 60 wt.%, about 30 wt.% to about 50 wt.%, about 30 wt.% to about 40 wt.%, or about 30 wt.% to about 35 wt.%, based on a total weight of the dental floss coating composition.Flavorants

[0057] The dental floss coating compositions of the present disclosure may include at least one flavoring agent. 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 of spearmint, peppermint, Wintergreen, sassafras, clove, sage, eucalyptus, marjoram,959322-OO-WO-Ol-OCcinnamon, lemon, lime, grapefruit, and orange. Also useful are 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. Also included are extracts, including in liquid or solid (i.e., powder form) of any of the above-mentioned materials, such as spearmint, peppermint, Wintergreen, sassafras, clove, sage, eucalyptus, marjoram, cinnamon, lemon, lime, vanilla, grapefruit, and orange extract, or a combination thereof.

[0058] The flavoring agent is typically incorporated in the dental floss coating composition at a concentration of about 1 wt.% to about 50 wt.% by weight of the dental floss coating composition. For example, the amount of flavoring agent(s) present in the dental floss coating composition may range from about 1 wt.% to about 40 wt.%, 1 wt.% to about 30 wt.%, 1 wt.% to about 20 wt.%, 1 wt.% to about 10 wt.%; 10 wt.% to about 40 wt.%. 10 wt.% to about 30 wt.%, or about 10 wt.% to about 20 wt.%, including any range or subrange thereof, based on the total weight of the dental floss coating composition.Sweeteners

[0059] The dental floss coating compositions provided herein may optionally comprise at least one sweetener. Sweeteners that may be used in the compositions disclosed herein include artificial sweeteners, such as saccharin (e.g., sodium saccharin), acesulfame, neotame, cyclamate, and sucralose. Also included are natural and high-intensity natural sweeteners such as thaumatin, stevioside, and glycyrrhizin and sugar alcohols such as sorbitol, xylitol, mannitol, and maltitol.Water

[0060] Water may be present in the dental floss coating compositions disclosed herein, and in certain embodiments, the composition is free of water, i.e., anhydrous. Water employed in the preparation of commercial oral care compositions should be deionized and free of organic impurities. Water may make up the balance of the compositions and includes about 1 wt.% to about 50 wt.%, such as from about 10 wt.% to about 50 wt.%, from about 15 wt.% to about 85 wt.%, or about 20 wt.% to about 40 wt.%, or any range or subrange thereof, by weight based on the total weight of the dental floss coating 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 as959322-OO-WO-Ol-OCwith sorbitol or silica or any components of the dental floss composition disclosed herein. The Karl Fischer method is a one measure of calculating free water.

[0061] In certain embodiments, the dental floss coating composition disclosed herein is free of or substantially free of water.Additional Ingredients

[0062] The dental floss coating 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, 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 dental floss coating compositions depending on the specific combination of other ingredients and the form of the dental floss.

[0063] The compositions provided herein optionally incorporate one or more desensitizing agents. These include, without limitation, potassium salts such as potassium nitrate, potassium bicarbonate, potassium chloride, potassium citrate, and potassium oxalate; capsaicin; eugenol, strontium salts; zinc salts; chloride salts and combinations thereof.

[0064] Mouth-feel agents that may be incorporated into the compositions defined herein include materials which impart a desirable texture or other feeling during use of the floss. Such agents include bicarbonate salts, which may impart a “clean feel” to teeth. Any orally acceptable bicarbonate can be used, including, without limitation, alkali metal bicarbonates such as sodium and potassium bicarbonates, ammonium bicarbonate, and mixtures thereof.

[0065] The compositions provided herein may comprise at least one colorant. Colorants herein include pigments, dyes and agents imparting a particular luster or reflectivity such as pearling agents. Any orally acceptable colorant can be used, including without limitation talc, mica, magnesium carbonate, calcium carbonate, magnesium silicate, magnesium aluminum silicate, silica, titanium dioxide, zinc oxide, red, yellow, brown and black iron oxides, ferric ammonium ferrocyanide, manganese violet, ultramarine, titaniated mica, bismuth oxychloride and the like.959322-OO-WO-Ol-OC

[0066] In certain embodiments, anti -microbial agents and preservatives, such as chlorhexidine, triclosan, quaternary ammonium compounds (such as benzalkonium chloride) or parabens (such as methyl or propyl paraben) may be incorporated in the compositions provided herein. In certain embodiments, the dental floss coating composition disclosed herein further comprises at least one antibacterial agent selected from halogenated diphenyl ether (e.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 piperidino derivatives, nicin preparations, chlorite salts; and combinations thereof.

[0067] Thickening agents which may be incorporated into the compositions defined herein include natural and synthetic gums and colloids. Suitable thickening agents include naturally occurring polymers such as carrageenan xanthan gum poly glycols of varying molecular weights sold under the tradename POLYOX®, and polyvinylpyrrolidone (PVP). Compatible inorganic thickening agents include amorphous silica compounds and colloidal silica compounds available under the trade designation ZEODENT® manufactured by Huber Corporation. Other inorganic thickening agents include natural and synthetic clays such as hectorite clays lithium magnesium silicate (laponite) and magnesium aluminum silicate (VEEGUM®). PVP is a particularly preferred thickener since PVP may retard the degradation of peroxide compounds such as PVP-peroxide. Additionally, coating compositions comprising PVP may be more stable with less tendency for sedimentation.

[0068] In some embodiments, the dental floss coating compositions disclosed herein may comprise at least one surfactant, such as surfactants selected from anionic, cationic, zwitterionic, and nonionic surfactants, and mixtures thereof.959322-OO-WO-Ol-OC

[0069] Non-ionic surfactants are known in the art 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® F127 by BASF, Inc. (Parsippany, N.J.). In certain embodiments, the dental floss coating compositions disclosed herein may comprise poloxamer as the at least one surfactant. The non-ionic surfactant may be present in the dental floss coating composition disclosed herein in an amount ranging from about 1 wt.% to about 50 wt.%, such as about 1 wt.% to about 25 wt.%, about 1 wt.% to about 20 wt.%, about 1 wt.% to about 17 wt.%; from about 5 wt.% to about 25 wt.%, about 5 wt.% to about 20 wt.%, about 5 wt.% to about 17 wt.%; from about 10 wt.% to about 25 wt.%, about 10 wt.% to about 20 wt.%, about 10 wt.% to about 17 wt.%; from about 15 wt.% to about 25 wt.%, about 15 wt.% to about 20 wt.%, or about 17 wt.%, or any range or subrange thereof, by weight relative to the total weight of the dental floss coating composition.

[0070] Anionic surfactants that may be used in the 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 (OCFfcCIDOSChNa); (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.

[0071] In some embodiments, the 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 sulfonated959322-OO-WO-Ol-OCmonoglycerides 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 compositions disclosed herein may comprise sodium lauryl sulfate, sodium ether lauryl sulfate, or a mixture thereof. In some embodiments, the compositions disclosed herein may comprise sodium lauryl sulfate.

[0072] In certain embodiments, the dental floss coating composition disclosed herein further comprises at least one whitening agent selected from metal chlorides, perborates, percarbonates, peroxyacids, hypochlorites, and combinations thereof.

[0073] The dental floss coating composition may include one or more pH adjusters to increase or decrease the overall pH of the dental floss coating composition. For example, one or more acids may be included to decrease the pH of the dental floss coating composition. Examples of suitable acids for decreasing the pH of the composition include, but are not limited to, citric acid, acetic acid, and the like. The dental floss coating composition may include one or more bases, such as sodium hydroxide, potassium hydroxide and the like, to increase the pH of the composition. Additional or alternative acids and bases that are suitable for adjusting the pH of the composition are readily known to one of ordinary skill in the art.Methods and Uses

[0074] The dental floss coating compositions defined herein are suitable for coating dental floss. Accordingly, in one arrangement, there is provided a dental floss comprising a coating composition, wherein the coating composition comprises an amine halide, such as a plant-based amine chloride, and a fluoride ion source.

[0075] The dental floss coating composition may be as defined herein. In certain embodiments, the dental floss comprises the dental floss coating composition in an amount of from 10 wt.% to 60 wt.% by total weight of the floss (fibers) and coating composition. For example, in certain embodiments, the dental floss comprises the coating composition in an amount of from 15 wt.% to 55 wt.% by total weight of the floss (fibers) and coating composition. The final concentration of components provided in the coating composition mentioned herein (e.g. amine halide and fluoride ion source), once coated onto the dental floss, may be calculated accordingly. For example, a dental floss coated with a coating composition comprising polyethylene glycol in an amount of about 20 wt.% by total weight of the coating composition, wherein the amount of the coating composition is about 50 wt.% by total weight of the floss (fibers) and coating composition,959322-OO-WO-Ol-OCwill comprise polyethylene glycol in an amount of about 10 wt.% by total weight of the floss (fibers) and coating composition.

[0076] Methods of manufacturing dental floss are well known in the art. For example, dental floss may be produced from nylon. Typically, a nylon salt is polymerized and the resulting polymer is pumped or extruded to form monofilaments. The filaments are allowed to harden, and then combined to form a strand of floss. Dental floss may also be produced from polyretrafluoroethylene (PTFE or Teflon®), polypropylene polyethylene, styrene butadyene copolymers, and combinations thereof. The polymers are typically melted and extruded into thin strands.

[0077] Further provided herein is a method for coating dental floss comprising: a) heating a coating composition to a temperature no greater than about 50 °C to form a molten composition, b) applying the molten composition to the dental floss to coat the dental floss, and c) cooling the composition to solidify the composition on the dental floss. In certain embodiments, depending on the binder / wax material used, there is provided a method for coating dental floss comprising applying a liquid coating composition to the dental floss at room temperature, and allowing the coating composition to solidify. In some embodiments, the floss is coated multiple times. Thus, once coated as described above, the method of coating may be repeated. This serves to increase the amount of coating composition on the floss. In certain embodiments wherein the binder or wax material used is a liquid at room temperature, the composition may optionally be solidified through heating the composition.

[0078] Further provided is a dental floss obtained by the method disclosed herein. The floss may be in the form of a single ribbon (e.g., a Teflon® polyethylene ribbon). Alternatively, it may be bundle of thin filaments, e.g., nylon filaments. The number of filaments will be from about 2 to about 300, e.g., from about 2 to about 200, depending on the denier of the filaments. The filaments are twisted with about 1 to 5 twists per inch to form the floss. The twisting provides integrity of the floss on the spool and during subsequent handling. However, when used the filaments will spread out and splay against tooth surfaces. The floss may also be formed of interlocking fibers. In any case, the final floss product is preferably of a thickness that allows it to fit between the teeth. Where multiple filaments are used, the coating composition may applied before or after twisting, preferably after twisting. Other additives including desensitizing agents, antimicrobial agents, tartar control agents, mouth feel agents, sweeteners, flavorants, colorants, and fluoride959322-OO-WO-Ol-OCsources, if not provided within the coating composition, may instead be applied to the coated floss after coating. The additives can be applied either as a liquid or a solid. For example, the additives may be applied as a spray dried solid. When applied as a liquid, the floss is dried prior to being wound onto a spool. The drying can be by radiant drying or air drying.

[0079] In some embodiments, provided herein is a dental floss comprising a coating composition as defined herein, optionally obtainable by the methods defined herein, wherein the coating composition is provided on the floss in a discontinuous fashion. By “discontinuous,” it is meant that at least one segment of the floss is not coated with the coating composition as defined herein, or at least one segment of the floss is coated with a masking composition that is different from the coating composition. By “discontinuous”, it may also be meant that at least one segment of the floss comprises or is coated by the coating composition as defined herein, and is further coated (or covered) by a masking composition. These types of segments may be referred to as “uncoated segments.” The segments of the floss comprising or coated by the coating composition as defined herein (without any further coating or covering by a masking composition) may be referred to as “coated segments.”

[0080] Dental floss is commonly supplied in plastic dispensers that contain 10 to 50 meters of floss. The dispenser typically has a small, protected blade used to sever the floss when a desired amount is pulled out. Various other devices have been developed to aid a user in flossing their teeth, especially when flossing of the particular tooth is difficult or awkward. Such devices are shaped like wands to hold the floss. The present disclosure contemplates such devices.

[0081] Also disclosed herein are methods of using the dental floss of the present disclosure. In certain embodiments, disclosed herein is a method of improving oral health comprising administering the dental disclosed herein to the oral cavity of a subject in need thereof and contacting the dental floss to an interdental space between two teeth or to a space between a tooth surface and a gum tissue of the subject. 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, including959322-OO-WO-Ol-OCcardiovascular 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.

[0082] According to certain embodiments of the methods disclosed herein, the dental floss may be applied to the oral cavity of the subject and contacted to the interdental space or the space between a tooth surface and the gum tissue of the subject at least once a day, such as at least twice a day or at least three times a day.

[0083] The dental floss coating 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.

[0084] 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.EXAMPLEExample 1 - Preparation of Dental Floss Coating Compositions

[0085] Two amine fluoride dental floss prototypes were prepared as shown below in Table 1 (expanding dental floss) and Table 2 (unwaxed dental floss).

[0086] Table 1 - Preparation of expanding dental floss959322-OO-WO-Ol-OC

[0087] Table 2 - Unwaxed dental flossExample 2 - Preparation of Amine Chloride Solution

[0088] For the compositions prepared in Example 1, the amine chloride solution was prepared as shown below in Table 3.

[0089] Table 3 - Amine chloride solution

[0090] 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 dental floss composition.

Claims

959322-OO-WO-Ol-OCCLAIMSWhat Is Claimed Is:

1. A dental floss coating composition comprising at least one plant-based amine chloride and at least one fluoride ion source.

2. The dental floss coating composition according to claim 1, wherein the at least one plantbased amine chloride is a polyethyleneglycol amine, preferably oleamidopropyl aminoethyl-3 dihydrochloride.

3. The dental floss coating 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 4 wt.% or from about 2 wt.% to about 4 wt.%, by weight based on the total weight of the dental floss coating composition.

4. The dental floss coating composition according to any one of the preceding claims, wherein the dental floss coating composition is a molten liquid at a temperature of about 38 °C or more.

5. The dental floss coating composition according to any one of the preceding claims, 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.

6. The dental floss coating composition according to any one of the preceding claims, wherein the at least one fluoride ion source is present in the dental floss coating composition in an amount ranging from about 0.005 wt.% to about 2.5 wt.%. preferably from about 0.1 wt.% to about 0.2 wt.%, by weight based on the total weight of the dental floss coating composition.

7. The dental floss coating composition according to any one of the preceding claims, further comprising at least one flavorant.959322-OO-WO-Ol-OC8. The dental floss coating composition according to claim 7, wherein the at least one flavorant is present in an amount ranging from about 1 wt.% to about 25 wt.%, preferably about 5 wt.% to about 20 wt.%, or about 5 wt.% to about 15 wt.%, by weight based on the total weight of the dental floss coating composition.

9. The dental floss coating composition according to any one of the preceding claims, further comprising at least one sweetener.

10. The dental floss coating composition according to claim 9, wherein the at least one sweetener is saccharin, preferably sodium saccharin.

11. The dental floss coating composition according to any one of the preceding claims, wherein the dental floss coating composition is anhydrous.

12. The dental floss coating composition according to claim 11, wherein the dental floss coating composition further comprises at least one polyethylene glycol polymer.

13. The dental floss coating composition according to claim 12, wherein the polyethylene glycol polymer has an average molecular weight of about 1500 Daltons.

14. The dental floss coating composition according to claim 11 or 12, wherein the at least one polyethylene glycol polymer is present in the dental floss coating composition in an amount ranging from about 5 wt.% to about 20 wt.%, preferably about 15 wt.% to about 20 wt.%, by weight based on the total weight of the dental floss coating composition.

15. The dental floss coating composition according to any one of claims 11 to 14, wherein the dental floss coating composition further comprises at least one non-ionic surfactant, preferably a poloxamer.

16. The dental floss coating composition according to claim 15, wherein the poloxamer is present in the dental floss coating composition in an amount ranging from about 5 wt.% to about959322-OO-WO-Ol-OC20 wt.%, preferably about 15 wt.% to about 20 wt.%, by weight based on the total weight of the dental floss coating composition.

17. The dental floss coating composition according to any one of claims 11 to 16, further comprising a wax, preferably a microcrystalline wax.

18. The dental floss coating composition according to claim 17, wherein the wax is present in the dental floss coating composition in an amount ranging from about 10 wt.% to about 50 wt.%, preferably from about 20 wt.% to about 40 wt.% or from about 25 wt.% to about 35 wt.%, by weight based on the total weight of the dental floss coating composition.

19. The dental floss coating composition according to any one of claims 1 to 10, wherein the dental floss coating composition further comprises water, preferably in an amount ranging from about 5 wt.% to about 50 wt.%. such as from about 20 wt.% to about 30 wt.%, by weight based on the total weight of the dental floss coating composition.

20. The dental floss coating composition according to any one of the preceding claims, further comprising a vinyl acetate / ethylene polymer.

21. The dental floss coating composition according to claim 20, wherein the vinyl acetate / ethylene polymer is present in the dental floss coating composition in an amount ranging from about 10 wt.% to about 80 wt.%, preferably from about 15 wt.% to about 55 wt.% or from about 20 wt.% to about 50 wt.%, by weight based on the total weight of the dental floss coating composition.

22. The dental floss coating composition according to any one of the preceding claims, wherein the dental floss coating 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.

23. A method of manufacturing a dental floss, wherein the method comprises:959322-OO-WO-Ol-OCheating a dental floss coating composition according to any one of claims 1 to 22 to a temperature greater than about 38 °C to form a molten composition,applying the molten composition to the dental floss to coat the dental floss, and cooling the composition the molten composition to solidify the composition on the dental floss.

24. A dental floss comprising a dental floss coating composition according to any one of claims 1 to 22.

25. A method of improving the oral health of a subject, the method comprising contacting the dental floss according to claim 24 to an interdental space between teeth or to a space between a tooth surface and a gum tissue of a subject in need thereof.

26. The method according to claim 25, 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.

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