Oral care composition comprising hops beta acids and tin

Abstract

An oral care composition is provided and includes a hops extract, where the hops extract includes dimethyl disulfide, a stannous ion source, and a stabilizing system including a Michael acceptor. The Michael acceptor has an alpha, beta-unsaturated carbonyl group. The alpha, beta-unsaturated carbonyl group can include an aldehyde, a ketone, a cyclic ketone, or a combination thereof.

Description

Technical Field

[0001] This disclosure relates generally to oral care compositions, and more specifically to oral care compositions comprising hops and tin with improved stability. Background Technology

[0002] Oral care compositions (such as toothpaste and / or dental floss compositions) are applied to the oral cavity to clean and / or maintain the aesthetics and / or health of teeth, gums, and / or tongue. Additionally, many oral care compositions are used to deliver active ingredients directly to oral care surfaces. Natural compounds with antibacterial activity, such as hops, can be incorporated into oral care compositions to provide antibacterial and / or anti-caries activity. Natural antibacterial agents such as hops can comprise mixtures of compounds, oils, flavonoids, and / or other flavoring compounds. The use of hop β-acid extracts in oral care compositions has the potential to deliver enhanced oral care benefits. The incorporation of natural compounds into oral care compositions can affect the storage stability of the composition. There is a need for oral care compositions with improved shelf stability. Summary of the Invention

[0003] In one embodiment, an oral care composition is provided, comprising a hops extract, wherein the hops extract contains a dimethyl disulfide, a stannous ion source, and a stabilizing system comprising a Michael receptor. The Michael receptor has an α,β-unsaturated carbonyl group. This α,β-unsaturated carbonyl group may comprise an aldehyde, a ketone, a cyclic ketone, or a combination thereof.

[0004] In one embodiment, an oral care composition is provided, comprising hop acid, dimethyl disulfide, a stannous ion source, and a stabilizing system comprising a Michael receptor. The Michael receptor has an α,β-unsaturated carbonyl group. This α,β-unsaturated carbonyl group may comprise an aldehyde, a ketone, a cyclic ketone, or a combination thereof. Detailed Implementation

[0005] It has been found that compositions containing hop beta-acid extract and tin can develop an off-flavor over time. Hop beta-acid extract may contain residual dimethyl disulfide (DMDS), also extracted from plant matter. In the presence of stannous ions, the residual DMDS reacts to form methyl mercaptan (MeSH). MeSH produces a pungent, rotten egg odor, which increases over time as more DMDS reacts. This off-flavor can develop during the shelf life of products containing DMDS and stannous ions, making them unappealing to consumers. Without being bound by theory, it is believed that the off-flavor is related to the interaction between residual DMDS from hop beta-acid and stannous or tin ions in the composition. It is important to reduce the amount of MeSH in oral care compositions.

[0006] While not wishing to be bound by theory, MeSH, as a thiol, can theoretically react with Michael acceptors (MAs) (e.g., α,β-unsaturated aldehydes / ketones and cyclic ketones) via a thiol-Michael addition reaction. The thiol-Michael addition reaction is broadly characterized by the reaction of enol-type nucleophiles with α,β-unsaturated carbonyl groups in the presence of a catalyst. Weak thiohydrogen bonds allow for the thiol-Michael addition reaction under mild, solvent-free conditions. Several highly nucleophilic bases and nucleophiles have been reported as potential catalysts for the reaction. This means that the presence of DMDS impurities in oral care compositions containing a combination of hop β-acid extract and stannous ions could jeopardize the odor stability of the product throughout its shelf life, potentially resulting in a product unacceptable to consumers. In the presence of Michael acceptors, product stability should be improved by reacting MeSH with Michael acceptors to reduce off-odor formation.

[0007] Furthermore, to avoid being bound by theory, it is believed that oral care compositions containing stannous ions generate hypoxic active compositions when placed in sealed, low-oxygen-permeability packaging (e.g., toothpaste tubes or mouthwash bottles) because the stannous ions are oxidized to tin ions, consuming residual oxygen within the packaging. When oxygen is dissolved in water, its equilibrium concentration is approximately 1.23 × 10⁻⁶ at 25°C and 1 atm. -3 M. It most likely reacts with stannous ions, as shown in the following reaction equation: O2 + 2Sn 2+ + 4H + 2H2O + 2Sn 4+

[0008] The concentration of stannous ions required for complete reaction with oxygen in a saturated solution is approximately 2.46 × 10⁻⁶. -3 M. This is approximately 300 ppm Sn(II) ions in the water. Hop stability in the presence of stannous ions increases by reducing oxygen activity through decreased formation of peroxides, isoprenyl groups, and isoprenyl thiols. Therefore, the main challenge with such compositions is preventing MeSH formation from DMDS, without requiring management of isoprenyl thiols formation.

[0009] Embodiments of the present invention relate to oral care compositions comprising Michael receptors to reduce the amount of MeSH generated in the oral care composition by the interaction of DMDS from hop β-acid extract with tin ions. The reaction of these Michael receptors with MeSH can lead to a reduction in odor generation in oral care compositions comprising hop β-acid extract, tin, and residual DMDS. definition

[0010] To more clearly define the terms used herein, the following definitions are provided. Unless otherwise indicated, the following definitions apply to this disclosure. If a term is used in this disclosure but is not specifically defined herein, the definition from IUPAC Compendium of Chemical Terminology, 2nd Edition (1997) may be applied, provided that the definition does not conflict with any other disclosure or definition applied herein, or render any claim to which the definition is applied uncertain or unenforceable.

[0011] As used herein, the term "oral care composition" includes products that are not intended for systemic administration of a particular therapeutic agent during ordinary use, but rather to remain in the oral cavity for a sufficient duration to contact the tooth surface or oral tissues. Examples of oral care compositions include dental floss, toothpaste, teething gel, subgingival gel, lotion, mouthwash, mousse, foam, mouth spray, lozenges, chewing tablets, chewing gum, teeth whitening strips, dental floss and floss coatings, breath freshening soluble strips, unit-dose compositions, fiber compositions, or denture care or adhesive products. Oral care compositions may also be incorporated into strips or films for direct application or attachment to oral surfaces (such as teeth whitening strips). Examples of lotion compositions include the lotion composition of U.S. Patent No. 11,147,753, and clogging lotions, such as the clogging oil-in-water emulsion of U.S. Patent No. 11,096,874. Examples of unit-dose compositions include the unit-dose composition of U.S. Patent Application Publication No. 2019 / 0343732.

[0012] Unless otherwise specified, as used herein, the term "dental cleaning composition" includes dental or subgingival pastes, gels, or liquid formulations. A dental cleaning composition may be a monophasic composition or a combination of two or more individual dental cleaning compositions. A dental cleaning composition may be in any desired form, such as deep streaks, light streaks, multilayers, pastes surrounded by gels, or any combination thereof. In a dental cleaning comprising two or more individual dental cleaning compositions, each dental cleaning composition may be contained in a physically separate dispenser compartment and dispensed side-by-side.

[0013] The “active ingredients and other ingredients” used herein may be categorized or described in accordance with their cosmetic and / or therapeutic benefits or their assumed mode of action or function. However, it should be understood that in some cases, the active substances and other ingredients used herein may provide more than one cosmetic and / or therapeutic benefit, or act or function via more than one mode of action. Therefore, the categorization herein is for convenience only and is not intended to limit the ingredients to the specific functions or activities listed.

[0014] The term "orally acceptable carrier" includes one or more compatible solid or liquid excipients or diluents suitable for topical oral administration. As used herein, "compatible" means that the components of a composition are miscible but do not interact with each other, such interactions would significantly reduce the stability and / or efficacy of the composition. Carriers or excipients that can be used in embodiments of the present invention may include common and conventional components of mouthwashes or mouthwashes. Mouthwash or mouthwash carrier materials generally include, but are not limited to, one or more of water, alcohols, humectants, surfactants, and acceptability improvers such as flavoring agents, sweeteners, coloring agents, and / or cooling agents.

[0015] As used herein, the term “substantially free” means that the composition contains no more than 0.05%, preferably no more than 0.01%, and more preferably no more than 0.001% of the specified material on a total weight basis.

[0016] As used herein, the term "substantially free of" means that the indicated material is not intentionally added to the composition, or preferably is not present at an analytically detectable level. This means a composition in which the indicated material is present only as an impurity among other intentionally added materials.

[0017] The term “oral hygiene program” or “program” can be used to describe the use of two or more separate and distinct steps of oral health care, such as toothpaste, mouthwash, dental floss, toothpicks, sprays, rinsing devices, and massagers.

[0018] As used herein, the term "total water content" refers to free water and water not bound to other components in the oral care composition.

[0019] For the purposes of this description, the relevant molecular weight (MW) to be used is the relevant molecular weight of the material added during the preparation of the composition. For example, if the chelating agent is a citrate substance, it may be provided in the form of citric acid, sodium citrate, or virtually any other salt. The MW used is the MW of the specific salt or acid added to the composition, but any water of crystallization that may be present is ignored.

[0020] Unless otherwise stated, although compositions and methods are described herein by way of “comprising” various components or steps, compositions and methods may also “consist of essentially various components or steps” or “comprise various components or steps”.

[0021] As used in this article, the word "or" when used as a conjunction for two or more elements means including either the element alone or a combination of the elements; for example, X or Y means X or Y or both.

[0022] As used herein, the articles “an” and “a” are understood to mean one or more of the materials protected or described in the claims, such as “oral care composition” or “bleaching agent”.

[0023] Unless otherwise specified, all measurements mentioned herein were performed at approximately 23°C (i.e., room temperature).

[0024] Generally, the numbering scheme shown in the version of the periodic table published in Chemical and Engineering News, 63(5), 27, 1985, is used to indicate element groups. In some cases, the common name assigned to the group may be used to indicate the element group; for example, for alkali metals in group 1, for alkaline earth metals in group 2, and so on.

[0025] Several types of scopes are disclosed in respect of embodiments of the present invention. When any type of scope is disclosed or protected by claims, the purpose is to disclose or protect by claims every possible value that such scope can reasonably cover, including the endpoints of the scope and any sub-scopes and combinations thereof covered therein.

[0026] Oral care compositions may be in any suitable form, such as solid, liquid, powder, paste, or combinations thereof. Oral care compositions may be dental cleaning agents, teeth whitening gels, subgingival gels, mouthwashes, mousses, foams, mouth sprays, lozenges, chewing tablets, chewing gum, teeth whitening strips, dental floss and floss coatings, breath freshening soluble strips, or denture care or adhesive products. Components of dental cleaning agent compositions may be incorporated into film, strip, foam, or fiber-based dental cleaning agent compositions.

[0027] Oral care compositions may contain a variety of active and inactive ingredients, such as, but not limited to, hops extract, dicarboxylic acid, tin ion source, calcium ion source, water, fluoride ion source, zinc ion source, one or more polyphosphates, humectants, surfactants, other ingredients, and any combination thereof, as described below. The following section headings are provided for organization and convenience only. In some cases, a compound may fall within one or more sections. For example, stannous fluoride may be a tin compound and / or a fluoride compound. Additionally, oxalic acid or a salt thereof may be a dicarboxylic acid, a polydentate ligand, and / or a whitening agent. sulfur source

[0028] The oral care composition of the present invention may contain a sulfur source. The sulfur source may be a residual sulfur source, which refers to a sulfur source present in the composition but not intentionally added to it. This means including a composition in which the sulfur source is present only as an impurity of one of other intentionally added materials (e.g., hop extract), or enters the composition during the manufacturing process. The sulfur source may include, for example, dimethyl sulfide, dimethyl sulfoxide, dimethyl disulfide (DMDS), or combinations thereof.

[0029] In various embodiments, the composition may include a residual sulfur source in the range of greater than 0 ppm to about 500 ppm, about 1 ppm to about 200 ppm, about 1 ppm to about 100 ppm, or about 1 ppm to about 50 ppm. For example, the composition may include DMDS greater than 0 ppm to about 500 ppm, about 1 ppm to about 200 ppm, about 1 ppm to about 100 ppm, or about 1 ppm to about 50 ppm. Michael receptor

[0030] In organic chemistry, the Michael reaction, or Michael 1,4-addition, is a reaction between a Michael donor (enolide or other nucleophile) and a Michael acceptor (typically an α,β-unsaturated carbonyl group), producing a Michael adduct by creating a carbon-carbon bond at the β-carbon of the acceptor. Typical Michael acceptors include α,β-unsaturated ketones, aldehydes, esters, amides, nitro compounds, and combinations thereof. Suitable Michael acceptors may include, but are not limited to, carvone, bonyl lactone, powdered ketones, cinnamaldehyde, α-ionone, 4-octen-3-one, toffee furanone, β-dihydrodamascone, δ-dihydrodamascone, z-jasmone, dextrorotatory piperonone, piperonone, formic acid, or combinations thereof. In embodiments, the Michael acceptor may not contain carvone.

[0031] The oral care composition may contain about 0.001% to about 1%, about 0.001% to about 0.5%, about 0.01% to about 0.25%, or about 0.05% to about 0.2% of Michael receptors by weight of the oral care composition. The weight percentage ratio of dimethyl disulfide to Michael receptors may, for example, be in the range of about 1:6000 to about 1:6, or about 1:6000 to about 1:60, about 1:6000 to about 1:3000, about 1:1000, or about 1:6, or about 1:500 to about 1:6.

[0032] Nucleophiles, including alcohols, amines, halide ions, and phosphine, have been reported to catalyze thiol-Michael addition reactions. Some Lewis bases frequently used in dental cleaning formulations can also catalyze thiol-Michael addition reactions. Examples of these nucleophiles commonly used in toothpaste include citrates, gluconates, glycine, and phytates. Suitable accelerating nucleophiles include, but are not limited to, sodium citrate, zinc citrate, glycine, sodium gluconate, sodium phytate, or combinations thereof. Hops

[0033] The oral care composition of the present invention may comprise hops. The hops may comprise at least one hop compound of Formula I and / or Formula IV. The compounds of Formula I and / or Formula IV may be provided from any suitable source, such as extracts from hops or hops (Humulus lupulus), hops themselves, their synthetic derivatives and / or salts, prodrugs, or other similar substances. The hop extract may comprise one or more hop α-acids, one or more hop iso-α-acids, one or more hop β-acids, one or more hop oils, one or more flavonoids, one or more solvents, and / or water. Suitable hop α-acids (generally represented by Formula I) may include humulone (Formula II), polyhumulone, humulone-like humulone, post-humulone, pro-humulone, and / or mixtures thereof. Suitable hop iso-α-acids may include cis-isohumulone and / or trans-isohumulone. The isomerization of humulone to trans-isohumulone may be represented by Formula III.

[0034] Formula I. Hops α-acid. A is an acidic hydroxyl functional group at the α-position, B is an acidic hydroxyl functional group at the β-position, and R is an alkyl functional group.

[0035] Formula II. Humulin

[0036] Formula III. Humulone is isomerized to isohylocourne.

[0037] Suitable hop β-acids may include humulone, humulone-like compounds, humulone-added compounds, and / or mixtures thereof. Suitable hop β-acids may include compounds described in formulas IV, V, VI, and / or VII.

[0038] Formula IV. Hops β-acid. B is an acidic hydroxyl functional group at the β-position, and R is an alkyl functional group.

[0039] Formula V. Humulone

[0040] Formula VI. Add hummus

[0041] Formula VII. Humulone

[0042] While hop alpha acids exhibit some antibacterial activity, they also possess a bitter taste. The bitterness provided by hop alpha acids is suitable for beer, but not for oral care compositions. In contrast, hop β acids can be associated with higher antibacterial and / or anti-caries activity, but are less bitter. Therefore, hop extracts with a higher ratio of β to alpha acids than typically found in nature could be suitable for use in oral care compositions as antibacterial and / or anti-caries agents.

[0043] Depending on the type of hops, natural hop sources may contain about 2% to about 12% hop β-acid by weight of the hop source. Hop extracts used in other applications, such as in beer brewing, may contain about 15% to about 35% hop β-acid by weight of the extract. The hop extracts desired herein may contain at least about 35%, at least about 40%, at least about 45%, about 35% to about 95%, about 40% to about 90%, or about 45% to about 99% hop β-acid. Hop β-acid may be in acidic form (i.e., having hydrogen atoms attached to hydroxyl functional groups) or in salt form.

[0044] Suitable hop extracts are described in detail in U.S. Patent No. 7,910,140, ​​the entire contents of which are incorporated herein by reference. The desired hop β-acids may be non-hydrogenated, partially hydrogenated by a non-naturally occurring chemical reaction, or hydrogenated by a non-naturally occurring chemical reaction. Hop β-acids may be substantially free of or substantially free of hydrogenated hop β-acids and / or hop acids. Non-naturally occurring chemical reactions are those involving compounds not present in hops, such as chemical hydrogenation reactions carried out at high temperatures and / or with metal catalysts that are not typically experienced in wild hops.

[0045] Natural hop sources may contain about 2% to about 12% hop alpha acid by weight of the hop source. Hop extracts used in other applications, such as in beer brewing, may contain about 15% to about 35% hop alpha acid by weight of the extract. The hop extracts used herein may contain less than about 10%, less than about 5%, less than about 1%, or less than about 0.5% hop alpha acid by weight of the extract.

[0046] Hop oil may contain terpenes such as myrcene, humulene, caryophyllene, and / or mixtures thereof. The hop extract desired herein may contain less than 5%, less than 2.5%, or less than 2% by weight of the extract of one or more hop oils.

[0047] Flavonoids present in hop extracts may include xanthohumol, 8-isoprene naringenin, isoxanthohumol, and / or mixtures thereof. Hop extracts may be substantially free of, substantially free of, contain no, or have less than 250 ppm, less than 150 ppm, and / or less than 100 ppm of one or more flavonoids.

[0048] Hop extract may be substantially free of, essentially free of, or free of dimethyl disulfide (DMDS). Hop extract may contain less than 250 ppm, less than 150 ppm, less than 100 ppm, and / or less than 50 ppm of dimethyl disulfide (DMDS). Hop extract may contain more than about 0.1 ppm, more than 1 ppm, or more than 10 ppm of DMDS.

[0049] Hops extract may be substantially free of, essentially free of, or contain no ocimene. Hops extract may contain residual ocimene.

[0050] As described in U.S. Patent No. 5,370,863, hop acid has previously been added to oral care compositions. However, the oral care composition taught in U.S. Patent No. 5,370,863 contains only up to 0.01% by weight of the oral care composition. While not wishing to be bound by theory, it is believed that only small amounts of hop acid can be incorporated into U.S. Patent No. 5,370,863 because hop alpha acid has a bitter taste. Hop extracts with low levels of hop alpha acid do not have this problem.

[0051] Hop compounds may be combined with or without extracts or oils from another plant, such as species from the genera *Magnolia*, *Garciniamangostana* L., or *Zizyphus joazeiro*. Oral care compositions may contain less than about 0.5%, less than about 0.1%, or less than about 0.01% of extracts from plants other than hops, such as species from the genera *Magnolia*, *Garciniamangostana*, or *Zizyphus joazeiro*. Hop compounds may be combined with or without nonionic halophenyl ethers.

[0052] Oral care compositions may contain about 0.01% to about 10%, greater than 0.01% to about 10%, about 0.05%, about 10%, about 0.1% to about 10%, about 0.2% to about 10%, about 0.2% to about 10%, about 0.2% to about 5%, about 0.25% to about 2%, about 0.05% to about 2%, or greater than 0.25% to about 2% of hops, such as hop β-acid, as described herein. Hop, such as hop β-acid, may be provided from suitable hop extracts, the hop plant itself, or synthetic derivatives. Hop, such as hop β-acid, may be provided as a neutral, acidic compound and / or as a salt having a suitable counterion such as sodium, potassium, ammonia, or any other suitable counterion.

[0053] Hops may be provided by hop extracts, such as extracts derived from hops, having at least 35% hop β-acid and less than 1% hop α-acid by weight of the extract. Oral care compositions may contain 0.01% to about 10%, greater than 0.01% to about 10%, about 0.05%, about 10%, about 0.1% to about 10%, about 0.2% to about 10%, about 0.2% to about 10%, about 0.2% to about 5%, about 0.25% to about 2%, about 0.05% to about 2%, or greater than 0.25% to about 2%, as described herein. Dicarboxylic acid

[0054] Oral care compositions contain dicarboxylic acids. Dicarboxylic acids include compounds having two carboxylic acid functional groups. Dicarboxylic acids may include compounds defined by formula VIII-A, formula VIII-B, and / or formula VIII-C, or salts thereof.

[0055] Formula VIII-A. dicarboxylic acid

[0056] R can be empty, alkyl, alkenyl, allyl, phenyl, benzyl, acetyl, aliphatic, aromatic, polyethylene glycol, polymer, O, N, P, or combinations thereof. R can also be further functionalized with one or more functional groups, such as -OH, -NH2, and / or alkyl, alkenyl, aromatic, or combinations thereof.

[0057] Formula VIII-B. dicarboxylic acid

[0058] R can be empty, alkyl, alkenyl, allyl, phenyl, benzyl, acetyl, aliphatic, aromatic, polyethylene glycol, polymer, O, N, P, or combinations thereof. R can also be further functionalized with one or more functional groups, such as -OH, -NH2, and / or alkyl, alkenyl, aromatic, or combinations thereof.

[0059] X1 and X2 can be independently H, an alkali metal, an alkaline earth metal, a transition metal, or a combination thereof. Suitable alkali metals include lithium, sodium, potassium, or a combination thereof. Suitable alkaline earth metals include magnesium, calcium, barium, or a combination thereof. Suitable transition metals include titanium, chromium, iron, nickel, copper, zinc, tin, gold, silver, or a combination thereof.

[0060] Formula VIII-C. dicarboxylic acid.

[0061] R1 can be empty, alkyl, alkenyl, allyl, phenyl, benzyl, acetyl, aliphatic, aromatic, polyethylene glycol, polymer, O, N, P, or combinations thereof. R can also be further functionalized with one or more functional groups, such as -OH, -NH2, and / or alkyl, alkenyl, aromatic, or combinations thereof.

[0062] X1 and X2 can be independently H, an alkali metal, an alkaline earth metal, a transition metal, or a combination thereof. Suitable alkali metals include lithium, sodium, potassium, or a combination thereof. Suitable alkaline earth metals include magnesium, calcium, barium, or a combination thereof. Suitable transition metals include titanium, chromium, iron, nickel, copper, zinc, tin, gold, silver, or a combination thereof.

[0063] Dicarboxylic acids can be added to formulations as neutral acids (as shown in Formula VIII-A) or as monosalts of dicarboxylic acids (where one of the carboxylic acid functional groups is a salt and the other is neutral), disalts of dicarboxylic acids (where both carboxylic acid functional groups are salts), or combinations thereof. Furthermore, as is well known to those skilled in the art, whether one or both carboxylic acid functional groups of a dicarboxylic acid are neutral or charged in solution can be affected by the pH of the solution. For example, a neutral dicarboxylic acid can be added to an aqueous solution, and if the pH is below the pKa of the carboxylic acid functional groups, one or both protons from the two carboxylic acid functional groups can be removed, as shown in Formula VIII-D below.

[0064] Acid-base properties of formula VIII-D. dicarboxylic acids, where M is any metal.

[0065] Dicarboxylic acids may include oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, octanoic acid, azelaic acid, sebacic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, hexadecanoic acid, jasminoides, oxalic acid, equisetic acid, malic acid, maleic acid, tartaric acid, phthalic acid, methylmalonic acid, dimethylmalonic acid, hydroxymalonic acid, mesooxalic acid, dihydroxymalonic acid, dihydroxymalonic acid, fumaric acid, terephthalic acid, glutaric acid, their salts, or combinations thereof. Dicarboxylic acids may include suitable salts of dicarboxylic acids, such as, when a dicarboxylic acid includes a salt of oxalic acid: monoalkali metal oxalates, dialkali metal oxalates, monopotassium monohydrooxalate, dipotassium oxalate, monosodium monohydrooxalate, disodium oxalate, titanium oxalate, and / or other metal salts of oxalate. Dicarboxylic acids may also include hydrates of dicarboxylic acids and / or hydrates of salts of dicarboxylic acids.

[0066] Suitable dicarboxylic acid compounds include malonic acid, methylmalonic acid, hydroxymalonic acid, malic acid, dimethylmalonic acid, oxalic acid, dihydroxymalonic acid, oxalic acid, their salts, or combinations thereof. These dicarboxylic acid compounds are particularly suitable because they have shown surprisingly high whitening benefits. While not wishing to be bound by theory, it is believed that certain dicarboxylic acid compounds have a surprisingly high affinity for certain cationic crosslinking agents in the colored matrix commonly present on the hard tissue surfaces of the oral cavity, thereby leading to the removal of stains from the surface.

[0067] Suitable dicarboxylic acid compounds include dicarboxylic acids described by formula VIII-A, wherein R is a methylene or ethylene group that is absent or includes one or two substituents, and / or an acetyl group.

[0068] Unbound by theory, we assume that the whitening effect of dicarboxylic acid and its corresponding anion is driven by the ability of dicarboxylic acid to reach and remove chromophores and tooth surfaces, as well as the cation bridges between chromophores and epidermal proteins. Fluorides

[0069] Oral care compositions may contain fluoride, which may be provided by a fluoride ion source. The fluoride ion source may contain one or more fluoride-containing compounds, such as stannous fluoride, sodium fluoride, titanium fluoride, calcium fluoride, calcium phosphate silicate fluoride, potassium fluoride, amine fluoride, sodium monofluorophosphate, zinc fluoride, and / or mixtures thereof.

[0070] The fluoride ion source and the tin ion source can be the same compound, such as stannous fluoride, which can generate tin ions and fluoride ions. Alternatively, the fluoride ion source and the tin ion source can be separate compounds, such as when the tin ion source is stannous chloride and the fluoride ion source is sodium monofluorophosphate or sodium fluoride.

[0071] The fluoride ion source and the zinc ion source can be the same compound, such as zinc fluoride, which can generate both zinc and fluoride ions. Alternatively, the fluoride ion source and the zinc ion source can be separate compounds, such as when the zinc ion source is zinc phosphate and the fluoride ion source is stannous fluoride.

[0072] The fluoride ion source may be substantially free of stannous fluoride or contain no stannous fluoride. Therefore, oral care compositions may contain sodium fluoride, potassium fluoride, amine fluoride, sodium monofluorophosphate, zinc fluoride, and / or mixtures thereof.

[0073] The oral care composition may contain a fluoride ion source capable of providing about 50 ppm to about 5000 ppm, and preferably about 500 ppm to about 3000 ppm, of free fluoride ions. To deliver the desired amount of fluoride ions, the fluoride ion source may be present in the oral care composition in an amount of about 0.0025% to about 5%, about 0.01% to about 10%, about 0.2% to about 1%, about 0.5% to about 1.5%, or about 0.3% to about 0.6% by weight of the oral care composition. Alternatively, the oral care composition may contain less than 0.1%, less than 0.01%, substantially no, substantially no, or no fluoride ion source. Metal

[0074] Oral care compositions as described herein may contain a metal, which may be provided by a metal ion source comprising one or more metal ions. As described herein, the metal ion source may comprise a tin ion source and / or a zinc ion source, or other than a tin ion source and / or a zinc ion source. Suitable metal ion sources include compounds having metal ions, such as, but not limited to, Sn, Zn, K, Cu, Mn, Mg, Sr, Ti, Fe, Mo, B, Ba, Ce, Al, In, and / or mixtures thereof. The metal ion source may be any compound having a suitable metal and any associated ligands and / or anions.

[0075] Suitable ligands and / or anions that can pair with metal ion sources include, but are not limited to, acetate, ammonium sulfate, benzoate, bromide, borate, carbonate, chloride, citrate, gluconate, glycerophosphate, hydroxide, iodide, oxalate, oxides, propionate, D-lactate, DL-lactate, orthophosphate, pyrophosphate, sulfate, nitrate, tartrate, and / or mixtures thereof.

[0076] Oral care compositions may contain about 0.01% to about 10%, about 1% to about 5%, or about 0.5% to about 15% of a metal and / or metal ion source. tin

[0077] Oral care compositions according to embodiments of the present invention may contain tin, which may be provided by a tin ion source. The tin ion source may be any suitable compound that, when the oral care composition is applied to the oral cavity, provides tin ions in the oral care composition and / or delivers tin ions to the oral cavity. The tin ion source may contain one or more tin-containing compounds, such as stannous fluoride, stannous chloride, stannous bromide, stannous iodide, stannous oxide, stannous oxalate, stannous sulfate, stannous sulfide, tin fluoride, stannous chloride, stannous bromide, stannous iodide, stannous sulfide, and / or mixtures thereof. The tin ion source may contain stannous fluoride, stannous chloride, and / or mixtures thereof. The tin ion source may also be a fluorine-free tin ion source, such as stannous chloride.

[0078] The oral care composition may contain about 0.0025% to about 5%, about 0.01% to about 10%, about 0.2% to about 1%, about 0.4% to about 1%, or about 0.3% to about 0.6% of tin and / or a tin ion source by weight of the oral care composition. Alternatively, the oral care composition may be substantially free of, substantially free of, or free of tin. Antibacterial agents

[0079] Oral care compositions may contain one or more antimicrobial agents. Suitable antimicrobial agents include any molecule that provides antimicrobial activity in the oral cavity. Suitable antimicrobial agents include hop acid, tin ion source, benzyl alcohol, sodium benzoate, menthyl acetate, menthyl lactate, L-menthol, o-menthol, copper chlorophyllin complexes, phenol, hydroxyquinoline, and / or combinations thereof.

[0080] Oral care compositions may contain about 0.01% to about 10%, about 1% to about 5%, or about 0.5% to about 15% of an antimicrobial agent. Bioactive substances

[0081] Oral care compositions may also contain bioactive substances suitable for tooth remineralization. Suitable bioactive substances include bioactive glass and Novamin. ™ Recaldent ™ Hydroxyapatite, one or more amino acids (e.g., arginine, citrulline, glycine, lysine, or histidine), or combinations thereof. Suitable examples of compositions containing arginine can be found in U.S. Patent Nos. 4,154,813 and 5,762,911, the entire contents of which are incorporated herein by reference. Other suitable bioactive materials include any calcium phosphate compound. Other suitable bioactive materials include compounds comprising both a calcium source and a phosphate source.

[0082] Amino acids are organic compounds containing an amine functional group, a carboxyl functional group, and a side chain unique to each amino acid. Suitable amino acids include, for example, amino acids with positive or negative side chains, amino acids with acidic or basic side chains, amino acids with polar, uncharged side chains, amino acids with hydrophobic side chains, and / or combinations thereof. Suitable amino acids also include, for example, arginine, histidine, lysine, aspartic acid, glutamic acid, serine, threonine, asparagine, glutamine, cysteine, selenocysteine, glycine, proline, alanine, valine, isoleucine, leucine, methionine, phenylalanine, tyrosine, tryptophan, citrulline, ornithine, creatine, diaminobutyric acid, diaminopropionic acid, their salts, and / or combinations thereof.

[0083] Bioactive glasses contain calcium and / or phosphate, which may be present in proportions similar to hydroxyapatite. These glasses are tissue-adhesive and biocompatible. Bioactive glasses may contain phosphopeptides, calcium sources, phosphate sources, silica sources, sodium sources, and / or combinations thereof.

[0084] The oral care composition may contain about 0.01% to about 20%, about 0.1% to about 10%, or about 1% to about 10% of bioactive material by weight of the oral care composition. Zinc

[0085] Oral care compositions may contain zinc, which may be provided by a zinc ion source. The zinc ion source may include one or more zinc-containing compounds, such as zinc fluoride, zinc lactate, zinc oxide, zinc phosphate, zinc chloride, zinc acetate, zinc hexafluorozirconate, zinc sulfate, zinc tartrate, zinc gluconate, zinc citrate, zinc malate, zinc glycinate, zinc pyrophosphate, zinc metaphosphate, zinc oxalate, and / or zinc carbonate. The zinc ion source may also be a fluoride-free zinc ion source, such as zinc phosphate, zinc oxide, and / or zinc citrate.

[0086] Zinc and / or a zinc ion source may be present in the total oral care composition in amounts of about 0.01% to about 10%, about 0.2% to about 1%, about 0.4% to about 1%, about 0.5% to about 1.5%, or about 0.3% to about 0.6% by weight of the oral care composition. Alternatively, the oral care composition may be substantially free of, substantially free of, or free of zinc. potassium

[0087] Oral care compositions may contain potassium, which may be provided by a potassium ion source. The potassium ion source may include one or more potassium-containing compounds, such as potassium nitrate, potassium fluoride, potassium chloride, or combinations thereof.

[0088] The oral care composition may contain about 0.01% to about 10%, about 0.2% to about 1%, about 0.4% to about 1%, or about 0.3% to about 0.6% of potassium and / or a potassium ion source by weight of the oral care composition. Alternatively, the oral care composition may be substantially free of, substantially free of, or free of potassium. Quaternary ammonium compounds

[0089] Oral care compositions may contain quaternary ammonium compounds. Quaternary ammonium compounds in compositions of embodiments of the present invention may include those in which one or two substituents on the quaternary nitrogen have a carbon chain length (typically an alkyl group) of about 8 to about 20, typically about 10 to 18 carbon atoms, while the remaining substituents (typically alkyl or benzyl groups) have a lower number of carbon atoms, such as about 1 to about 7, typically those of methyl or ethyl groups. Cetylpyridinium chloride, hexadecyl fluorinated pyridinium, tetradecyl pyridinium chloride, N-tetradecyl-4-ethyl pyridinium chloride, domethacin, benzalkonium chloride, benzyl chloride, methylbenzyl chloride, dodecyltrimethylammonium bromide, dodecyl dimethyl (2-phenoxyethyl)ammonium bromide, benzyl dimethoxystearyl ammonium chloride, quaternized 5-amino-1,3-bis(2-ethylhexyl)-5-methylhexahydropyrimidine, lauryltrimethylammonium chloride, cocoyltrimethylammonium chloride, hexadecyltrimethylammonium bromide, diisobutylphenoxyethyl dimethylbenzylammonium chloride, and dodecyltrimethylammonium bromide are typical examples of quaternary ammonium antimicrobial agents. Other compounds are bis[4-(R-amino)-1-pyridinium]alkanes, as disclosed in U.S. Patent No. 4,206,215 to Bailey. Pyridinium compounds are preferred quaternary ammonium compounds, particularly hexadecylpyridinium or tetradecylpyridinium halide salts (i.e., chlorides, bromides, fluorides, and iodides). Hexadecylpyridinium chloride and fluoride salts are particularly preferred.

[0090] The oral care composition may contain at least about 0.025%, at least about 0.035%, at least about 0.045% to about 1.0%, about 0.025% to about 1%, or about 0.01% to about 10% of a quaternary ammonium compound by weight of the composition. Alternatively, the oral care composition may be substantially free of, substantially free of, or contain no quaternary ammonium compound. pH

[0091] The pH of the oral care compositions described herein may be from about 4 to about 10, from about 7 to about 10, greater than 7 to about 10, greater than 8 to about 10, greater than 7, greater than 7.5, greater than 8, greater than 9, from about 8.5 to about 10, from about 4 to about 7, from about 4 to about 6, from about 4.5 to about 6.5, from about 4.5 to about 5.5, from about 4 to less than 5.5, from about 4.5 to less than 5.5, greater than 4 to less than 5, greater than 4 to about 4.9, from about 4.9, from about 4 to about 5.4, from about 4 to about 5.3, from about 4 to about 5.2, from about 4 to about 5.1, from about 4 to about 5, from about 4 to about 4.9, from about 4 to about 4.8, from about 4 to about 4.7, or from about 4.8 to about 5.3. The pH of the mouthwash solution may be determined to be the pH of the pure solution. The pH of a dental cleaning composition can be determined as a slurry pH, which is the pH of a mixture of the dental cleaning composition and water (such as a 1:4, 1:3, or 1:2 mixture of the dental cleaning composition and water).

[0092] If the oral care composition contains one or more dicarboxylic acids, a pH below about 7 or below about 6 is preferred due to the pKa of the dicarboxylic acids. While not wishing to be bound by theory, it is believed that dicarboxylic acids exhibit unique properties at pH levels below about 7 or below about 6, but surfaces in the oral cavity may also be sensitive to low pH. Additionally, at pH values ​​above about pH 7, metal ion sources can react with water and / or hydroxide ions to form insoluble metal oxides and / or metal hydroxides. The formation of these insoluble compounds can limit the ability of dicarboxylic acids to stabilize metal ions in the oral care composition and / or can limit the interaction between dicarboxylic acids and target metal ions in the oral cavity.

[0093] Furthermore, at pH values ​​less than 4, the likelihood of demineralization increases significantly. Therefore, as described herein, oral care compositions containing dicarboxylic acids may preferably have a pH of about 4 to about 7, about 4 to about 6, about 4.5 to about 6.5, about 4 to about 5, about 4 to less than 5, about 4 to about 4.9, or about 4.5 to less than 5.5 to minimize the formation of metal hydroxides / metal oxides in the oral cavity and any increased demineralization.

[0094] As described herein, the pH of an oral care composition can be measured immediately after mixing, or after aging the composition by placing it under ambient temperature or accelerated temperature and humidity conditions, such as measuring pH for approximately 28 days or longer prior to measurement at temperatures of 25°C, 30°C and / or 40°C and relative humidity of 30%, 60% and / or 75%. buffer

[0095] Oral care compositions may contain one or more buffers. As used herein, a buffer is a reagent that can be used to adjust the pH of the slurry in an oral care composition. Buffers include alkali metal hydroxides, carbonates, sesquicarbonates, borates, silicates, phosphates, imidazoles, carboxylates, and mixtures thereof. Specific buffers include monosodium phosphate, trisodium phosphate, sodium hydroxide, potassium hydroxide, alkali metal carbonates, sodium carbonate, imidazoles, pyrophosphates, citric acid, and sodium citrate. Oral care compositions may contain one or more buffers, each in an amount of about 0.1% to about 30%, about 1% to about 10%, or about 1.5% to about 3% by weight of the composition of the invention. Polyphosphate

[0096] Oral care compositions may contain polyphosphates, which may be provided by a polyphosphate source. A polyphosphate source may contain one or more polyphosphate molecules. Polyphosphates are a class of substances obtained by the dehydration and condensation of orthophosphates to form linear and cyclic polyphosphates of varying chain lengths. Therefore, polyphosphate molecules are typically identified by the average number (n) of polyphosphate molecules, as described below. Although some cyclic derivatives may exist, polyphosphates are generally considered to consist of two or more phosphate molecules arranged primarily in a linear configuration.

[0097] Preferred polyphosphates are those having an average of two or more phosphate groups, so that sufficient unbound phosphate functional groups are generated for effective surface adsorption, which enhances the anionic surface charge and the surface's hydrophilic properties. Preferred polyphosphates include straight-chain polyphosphates having the following formula: XO(XPO3). n X, where X is sodium, potassium, ammonium, or any other alkali metal cation, and n on average is from about 2 to about 21. Alkaline earth metal cations (such as calcium) are not preferred because they tend to form insoluble fluoride salts from aqueous solutions containing fluoride ions and alkaline earth metal cations. Therefore, the oral care compositions disclosed herein may be free of, substantially free of, or substantially free of calcium pyrophosphate.

[0098] Some examples of suitable polyphosphate molecules include, for example, pyrophosphate (n=2), tripolyphosphate (n=3), tetrapolyphosphate (n=4), sodium polyphosphate (n=6), hexapolyphosphate (n=13), phenyl polyphosphate (n=14), and hexametaphosphate (n=21), which is also known as Glass H. Polyphosphates may include those polyphosphate compounds produced by FMC Corporation, ICL Performance Products, and / or Astaris. Other suitable examples of polyphosphates include multidentate polyphosphates (n>2), such as sodium acid pyrophosphate and sodium phytate.

[0099] The oral care composition may contain about 0.01% to about 15%, about 0.1% to about 10%, about 0.5% to about 5%, about 1% to about 20%, or about 10% or less of a polyphosphate source based on the weight of the oral care composition. Alternatively, the oral care composition may be substantially free of, substantially free of, or free of polyphosphates. surfactants

[0100] Oral care compositions may contain one or more surfactants. Surfactants can be used to make the composition more cosmetically acceptable. Surfactants are preferably detergency agents that impart detergency and foaming properties to the composition. Suitable surfactants are anionic, cationic, nonionic, amphoteric, amphoteric, and betaine surfactants in safe and effective amounts.

[0101] Suitable anionic surfactants include, for example, water-soluble salts of alkyl sulfates having 8 to 20 carbon atoms in the alkyl group and water-soluble salts of sulfonated monoglycerides of fatty acids having 8 to 20 carbon atoms. Examples of such anionic surfactants are sodium lauryl sulfate (SLS) and sodium coconut monoglyceride sulfonate. Other suitable anionic surfactants include sarcosine salts (such as sodium lauroyl sarcosine), taurine salts, sodium lauryl sulfoacetate, sodium lauroyl hydroxyethyl sulfonate, sodium lauryl polyoxyethylene ether carboxylate, and sodium dodecylbenzene sulfonate. Combinations of anionic surfactants may also be used.

[0102] Another suitable class of anionic surfactants are alkyl phosphates. These surface-active organophosphate reagents exhibit strong affinity for enamel surfaces and a strong tendency to surface-bind, thereby desorbing surface proteins and maintaining their attachment to the enamel surface. Suitable examples of organophosphate compounds include monoesters, diesters, and trimers represented by the following general formulas:

[0103] Z1, Z2, or Z3 may be the same or different, and at least one of them is an organic moiety. Z1, Z2, or Z3 may be selected from straight-chain or branched alkyl or alkenyl groups of 1 to 22 carbon atoms, optionally substituted with: one or more phosphate groups; alkoxylated alkyl or alkenyl groups, (poly)saccharide groups, polyol groups, or polyether groups. Some other reagents include alkyl phosphates or alkenyl phosphates represented by the following structures:

[0104] Wherein R1 represents a straight-chain or branched alkyl or alkenyl group having 6 to 22 carbon atoms, optionally substituted with one or more phosphate groups; n and m are individually and respectively 2 to 4, and a and b are individually and respectively 0 to 20; Z and Z may be the same or different, each representing hydrogen, alkali metal, ammonium, protonated alkylamine or protonated functionalized alkylamine, such as alkanolamine or R-(OCH2)(OCH)- group. Examples of suitable reagents include alkyl phosphates and alkyl (poly)alkoxy phosphates, such as lauryl phosphate; PPGS cetearyl polyoxyethylene ether-10 phosphate; lauryl polyoxyethylene ether-1 phosphate; lauryl polyoxyethylene ether-3 phosphate; lauryl polyoxyethylene ether-9 phosphate; trilauryl polyoxyethylene ether-4 phosphate; C 12-18 PEG 9 phosphate ester: and dilauryl polyoxyethylene ether-10 sodium phosphate. Alkyl phosphates may be polymers. Examples of polymeric alkyl phosphate esters include those containing repeating alkoxy groups as polymeric moieties, specifically those containing three or more ethoxy, propoxy, isopropoxy, or butoxy groups.

[0105] Other suitable anionic surfactants are sarcosinates, hydroxyethyl sulfonates, and taurines, especially their alkali metal or ammonium salts. Examples include lauroyl sarcosinate, myristoyl sarcosinate, palmitoyl sarcosinate, stearoyl sarcosinate, oleoyl sarcosinate, or combinations thereof.

[0106] Other suitable anionic surfactants include sodium or potassium alkyl sulfates, such as sodium lauryl sulfate, acyl hydroxyethyl sulfonate, acyl methyl hydroxyethyl sulfonate, alkyl ether carboxylates, acyl alanine salts, acyl glutamate salts, acyl glycinate salts, acyl sarcosine salts, sodium methyl acyl taurate, sodium lauryl ether sulfosuccinate, α-olefin sulfonate, alkylbenzene sulfonate, sodium lauroyl lactate, sodium lauryl glucoside hydroxypropyl sulfonate, and / or combinations thereof.

[0107] Suitable taurine surfactants are represented by formula (I):

[0108] Wherein R1 is a saturated or unsaturated straight-chain or branched alkyl chain having 6 to 18 carbon atoms; R2 is H or methyl, and M is H, sodium, or potassium. Preferably, R1 is a saturated or unsaturated straight-chain or branched alkyl chain having 8 to 18 carbon atoms. Optionally, but preferably, the taurine surfactant comprises one or more of the following: potassium cocoyl taurate, potassium methyl cocoyl taurate, sodium hexanoyl methyl taurate, sodium cocoyl taurate, sodium lauroyl taurate, sodium methyl cocoyl taurate, sodium methyl lauroyl taurate, sodium methyl myristoyl taurate, sodium methyl oleoyl taurate, and combinations thereof.

[0109] The zwitterionic surfactants or amphoteric surfactants that can be used herein include derivatives of aliphatic quaternary ammonium, phosphonium, and sulfonium compounds, wherein the aliphatic group can be straight-chain or branched, and one of the aliphatic substituents contains 8 to 18 carbon atoms, and one of the aliphatic substituents contains an anionic water-solubilizing group, such as a carboxyl, sulfonate, sulfate, phosphate, or phosphonate group. Suitable betaine surfactants are disclosed in U.S. Patent No. 5,180,577. Typical alkyl dimethyl betaines include decyl betaine or 2-(N-decyl-N,N-dimethylamine) acetate, cocoyl betaine or 2-(N-cocoyl-N,N-dimethylamine) acetate, tetradecyl betaine, palmityl betaine, lauryl betaine, hexadecyl betaine, hexadecyl betaine, stearyl betaine, etc. Amide betaines can be exemplified by cocamidoethyl betaine, cocamidopropyl betaine (CADB), and lauramidopropyl betaine. Other suitable amphoteric surfactants include betaine, sulfobetaine, sodium lauryl amphoteric acetate, alkyl amphoteric diacetates, and / or combinations thereof.

[0110] Suitable cationic surfactants include, for example, quaternary ammonium compound derivatives having a long alkyl chain containing 8 to 18 carbon atoms, such as lauryltrimethylammonium chloride; cetylpyridinium chloride; hexadecyltrimethylammonium bromide; hexadecylpyridinium fluoride or combinations thereof.

[0111] Suitable nonionic surfactants include, for example, compounds prepared by the condensation of an alkylene group (which is inherently hydrophilic) with an organic hydrophobic compound, which may be aliphatic or alkyl aromatic in nature. Examples of suitable nonionic surfactants may include Pluronics. ® (i.e., poloxamer), alkylphenol polyoxyethylene condensates, products derived from the condensation of ethylene oxide with propylene oxide and ethylenediamine, fatty alcohol ethylene oxide condensates, long-chain tertiary amine oxides, long-chain tertiary phosphine oxides, long-chain dialkyl sulfoxides, and combinations thereof. Other suitable nonionic surfactants include alkyl glucosamides, alkyl glucosides, and / or combinations thereof.

[0112] One or more surfactants may also include one or more natural and / or naturally derived surfactants. Natural surfactants may include surfactants derived from natural products and / or minimally processed or unprocessed surfactants. Natural surfactants may include hydrogenated, non-hydrogenated or partially hydrogenated vegetable oils, olus oil, 23arrageena passionflower oil, candelilla wax, cocoyl caprylate, caprylate, dioctyl ether, lauryl alcohol, tetradecyl myristate, dioctyl ether, caprylic acid, octyl ester, octyl caprylate, octyl caprylate, undecane, tridecane, decyl oleate, decyl oleate, hexadecyl palmitate, stearic acid, palmitic acid, glyceryl stearate, hydrogenated, non-hydrogenated or partially hydrogenated vegetable glycerides, polyglycerol-2-dipolyhydroxystearate, hexadecyl alcohol / octadecanol, sucrose polystearate, glycerin, octadecyl alcohol, hydrolyzed, partially hydrolyzed or unhydrolyzed plant proteins, hydrolyzed, Partially hydrolyzed or unhydrolyzed wheat protein hydrolysates, polyglycerol-3 diisostearate, glyceryl oleate, myristyl alcohol, hexadecyl alcohol, sodium cetearyl sulfate, hexadecyl alcohol / octadecanol, glyceryl laurate, triglycerides caprylate, cocoglyceryl esters, lecithin, dioctyl ether, xanthan gum, sodium cocosulfate, ammonium lauryl sulfate, sodium cocosulfate, sodium cocoglutamate, polyalkyl glucosides (such as decyl glucoside, cetearyl glucoside), hexadecyl stearyl polyglucoside, cocoglycoside and lauryl glucoside and / or combinations thereof. Natural surfactants may include any of the natural ingredients sold by BASF, such as, for example, CegeSoft. ® Cetiol ® Cutina ® Dehymuls ® Emulgade ® Emulgin ® Eutanol ® Gluadin ® Lameform ® LameSoft ® Lanette ® Monomuls ® Myritol ® Plantacare ® Plantaquat ® Platasil ® Rheocare ® Sulfopon ® Texapon ® and / or combinations thereof.

[0113] Other specific examples of surfactants include sodium lauryl sulfate, sodium lauryl hydroxyethyl sulfonate, sodium lauroyl methyl hydroxyethyl sulfonate, sodium cocoyl glutamate, sodium dodecylbenzene sulfonate, alkali metal or ammonium salts of lauroyl sarcosine, myristoyl sarcosine, palmitoyl sarcosine, stearoyl sarcosine, and oleoyl sarcosine; polyoxyethylene sorbitan monostearate, isostearate, and laurate; sodium lauryl sulfoacetate; sodium, potassium, and ethanolamine salts of N-lauroyl sarcosine, N-lauroyl, N-myristoyl, or N-palmitoyl sarcosine; polyoxyethylene condensates of alkylphenols; cocamidopropyl betaine, lauroamideopropyl betaine, palmitoyl betaine, sodium cocoyl glutamate, etc. Additional surfactants desired include fatty acid salts of glutamate, alkyl glucosides, taurine, betaine, caprylate, and / or mixtures thereof. Oral care compositions may also be sulfate-free. The oral care composition may contain one or more surfactants, each surfactant being present in a concentration of about 0.01% to about 15%, about 0.3% to about 10%, or about 0.3% to about 2.5% by weight of the oral care composition. Monodentate ligands

[0114] Oral care compositions may contain a monodentate ligand having a molecular weight (MW) of less than 1000 g / mol. The monodentate ligand has a single functional group capable of interacting with a central atom such as a tin ion. The monodentate ligand must be suitable for use in the oral care composition and may be included in the oral care composition listed on the FDA's Generally Recognized As Safe (GRAS) list or other suitable lists within the jurisdiction of concern.

[0115] As described herein, monodentate ligands may contain a single functional group capable of chelating, associating, and / or bonding with tin. Suitable functional groups capable of chelating, associating, and / or bonding with tin include carbonyl, amine, and other functional groups known to those skilled in the art. Suitable carbonyl functional groups may include carboxylic acids, esters, amides, or ketones.

[0116] Monodentate ligands may contain a single carboxylic acid functional group. Suitable monodentate ligands containing carboxylic acids may include compounds having the formula R-COOH, where R is any organic structure. Suitable monodentate ligands containing carboxylic acids may also include aliphatic carboxylic acids, aromatic carboxylic acids, sugar acids, their salts, and / or combinations thereof.

[0117] 24. Arrageenc Carboxylic acids may contain a carboxylic acid functional group attached to a straight-chain hydrocarbon chain, a branched hydrocarbon chain, and / or a cyclic hydrocarbon molecule. Aliphatic carboxylic acids may be fully saturated or unsaturated and have one or more alkene and / or alkyne functional groups. Other functional groups may be present and bonded to the hydrocarbon chain, including halogenated variants of the hydrocarbon chain. Aliphatic carboxylic acids may also include hydroxy acids, which are organic compounds having an alcohol functional group at the α, β, or γ position relative to the carboxylic acid functional group. Suitable α-hydroxy acids include lactic acid and / or its salts.

[0118] Aromatic carboxylic acids may contain a carboxylic acid functional group attached to at least one aromatic functional group. Suitable aromatic carboxylic acid groups may include benzoic acid, salicylic acid, and / or combinations thereof.

[0119] Carboxylic acids may include formic acid, acetic acid, propionic acid, butyric acid, valeric acid, hexanoic acid, heptanoic acid, octanoic acid, ascorbic acid, benzoic acid, octanoic acid, cholic acid, glycine, alanine, valine, isoleucine, leucine, phenylalanine, linoleic acid, nicotinic acid, oleic acid, propionic acid, sorbic acid, stearic acid, gluconic acid, lactic acid, carbonic acid, chloroacetic acid, dichloroacetic acid, trichloroacetic acid, their salts and / or combinations thereof.

[0120] Oral care compositions may contain about 0.01% to about 10%, about 0.1% to about 15%, about 1% to about 5%, or about 0.0001% to about 25% of monodentate ligands by weight of the composition. Multidentate ligands

[0121] Oral care compositions may contain polydentate ligands with a molecular weight (MW) of less than 1000 g / mol or less than 2500 g / mol. The polydentate ligands have at least two functional groups capable of interacting with a central atom such as a tin ion. Additionally, the polydentate ligands must be suitable for use in oral care compositions and may be included in the oral care composition listed on the FDA's Generally Recognized As Safe (GRAS) list or another suitable list within the jurisdiction of concern.

[0122] As described herein, polydentate ligands may contain at least two functional groups that can chelate, associate, and / or bond with tin. Polydentate ligands may include dipentate ligands (i.e., having two functional groups), tripentate ligands (i.e., having three functional groups), tetradentate ligands (i.e., having four functional groups), etc.

[0123] Suitable functional groups that can chelate, associate, and / or bond with tin include carbonyl, phosphate, nitrate, amine, and other functional groups known to those skilled in the art. Suitable carbonyl functional groups may include carboxylic acids, esters, amides, or ketones.

[0124] Polydentate ligands can contain two or more carboxylic acid functional groups. Suitable polydentate ligands containing carboxylic acids can include compounds having the formula HOOC-R-COOH, where R is any organic structure. Suitable polydentate ligands containing two or more carboxylic acids can also include dicarboxylic acids, tricarboxylic acids, tetracarboxylic acids, etc.

[0125] Other suitable polydentate ligands include compounds containing at least two phosphate functional groups. Therefore, as described herein, polydentate ligands can include polyphosphates.

[0126] Other suitable polydentate ligands include hop β-acids, such as humulone, polyhumulone, polyhumulone, and / or combinations thereof. Hop β-acids can be synthetically derived and / or extracted from natural sources.

[0127] Polydentate ligands may also include phosphate groups as functional groups to interact with tin. Suitable phosphate compounds include phosphates, organophosphates, or combinations thereof. Suitable phosphates include orthophosphates, hydrogen phosphates, dihydrogen phosphates, alkylated phosphates, and combinations thereof. Polydentate ligands may include oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, octanoic acid, azelaic acid, sebacic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, hexadecanoic acid, jasminoides, styracidin, equisetic acid, maleic acid, malic acid, tartaric acid, phthalic acid, citric acid, phytic acid, pyrophosphate, tripolyphosphate, tetrapolyphosphate, hexametaphosphate, their salts, and / or combinations thereof.

[0128] The oral care composition may contain about 0.01% to about 10%, about 0.1% to about 15%, about 1% to about 5%, or about 0.0001% to about 25% of a multidentate ligand by weight of the composition. Thickener

[0129] Oral care compositions may contain one or more thickeners. Thickeners may be used in oral care compositions to provide a gel-like structure that stabilizes the composition and prevents phase separation. Suitable thickeners include polysaccharides, polymers, and / or silica thickeners.

[0130] Thickeners may contain one or more polysaccharides. Some non-limiting examples of polysaccharides include starch; starch glycerol; gums such as carrageenan gum, tragacanth gum, 26arrag gum, solanum, gum arabic, xanthan gum, guar gum, and cellulose gum; magnesium aluminum silicate (colloidal magnesium aluminum silicate); carrageenan; sodium alginate; agar; pectin; gelatin; cellulose compounds such as cellulose, microcrystalline cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxymethyl cellulose, hydroxymethyl carboxypropyl cellulose, methyl cellulose, ethyl cellulose, and sulfated cellulose; natural and synthetic clays, such as lithium montmorillonite clay; and mixtures thereof.

[0131] Other polysaccharides applicable to this article include carrageenan, gellan gum, locust bean gum, xanthan gum, carbomer, poloxamer, modified cellulose, and mixtures thereof. Carrageenan is a polysaccharide derived from seaweed. Several types of 26-arrageenan exist, which can be distinguished by their seaweed origin and / or by their degree and position of sulfation. Thickeners may include κ-carrageenan, modified κ-carrageenan, ι-carrageenan, modified ι-carrageenan, λ-carrageenan, and mixtures thereof. Carrageenan applicable to this article includes those commercially available under the series name "Viscarin" from FMC Company, including but not limited to Viscarin TP 329, Viscarin TP 388, and Viscarin TP 389.

[0132] The thickener may comprise one or more polymers. The polymer may be polyethylene glycol (PEG), polyvinylpyrrolidone (PVP), polyacrylic acid, a polymer derived from at least one acrylic acid monomer, a copolymer of maleic anhydride and methyl vinyl ether, or a crosslinked polyacrylic acid polymer having various weight percentages and a wide range of average molecular ranges in the oral care composition. Alternatively, the oral care composition may be free of, substantially free of, or substantially free of copolymers of maleic anhydride and methyl vinyl ether. The polymer may include a polyacrylate crosslinker, such as polyacrylate crosslinker-6. Suitable sources of polyacrylate crosslinker-6 may include Sepimach Zen, commercially available from Seppic. ™ .

[0133] Thickeners may include inorganic thickeners. Some non-limiting examples of suitable inorganic thickeners include colloidal magnesium aluminum silicate and silica thickeners. Non-limiting examples of silica thickeners that may be used include, for example, amorphous precipitated silica, such as ZEODENT. ® 165% silica. Other non-limiting silica thickeners include ZEODENT. ® 153, 163, and 167, and ZEOFREE ® 177 and 265 silica products (both purchased from Evonik Corporation) and AEROSIL ® Pyrolytic silicon dioxide.

[0134] Oral care compositions may contain one or more thickeners in amounts of 0.01% to about 15%, 0.1% to about 10%, about 0.2% to about 5%, or about 0.5% to about 2%. friction agent

[0135] The oral care composition of embodiments of the present invention may include an abrasive. The abrasive may be added to the oral care formulation to help remove surface stains on the teeth. The oral care formulation may include calcium abrasives and / or non-calcium abrasives, such as silica abrasives.

[0136] Oral care compositions may contain calcium abrasives. The calcium abrasive may be any suitable abrasive compound that, when applied to the oral cavity, provides and / or delivers calcium ions into the oral cavity. Oral care compositions may contain about 5% to about 70%, about 10% to about 60%, about 20% to about 50%, about 25% to about 40%, or about 1% to about 50% of calcium abrasives. The calcium abrasive may contain one or more calcium abrasive compounds, such as calcium carbonate, precipitated calcium carbonate (PCC), ground calcium carbonate (GCC), chalk, dicalcium phosphate, calcium pyrophosphate, and / or mixtures thereof.

[0137] Oral care compositions may contain non-calcium abrasives, such as bentonite, silica gel (alone and of any structure), precipitated silica, amorphous precipitated silica (alone and also of any structure), silica hydrate, perlite, titanium dioxide, calcium pyrophosphate, calcium hydrogen phosphate dihydrate, alumina, alumina hydrate, calcined alumina, aluminum silicate, insoluble sodium metaphosphate, insoluble potassium metaphosphate, insoluble magnesium carbonate, zirconium silicate, particulate thermosetting resins, and other suitable abrasive materials. Such materials may be incorporated into oral care compositions to tailor the polishing properties of the targeted dental cleaning formulation. Oral care compositions may contain approximately 5% to approximately 70%, approximately 10% to approximately 50%, approximately 10% to approximately 60%, approximately 20% to approximately 50%, approximately 25% to approximately 40%, or approximately 1% to approximately 50% of the non-calcium abrasives by weight of the oral care composition.

[0138] Alternatively, the oral care composition may be substantially free of, substantially free of, substantially free of, or free of silica, alumina, or any other non-calcium abrasive. The oral care composition may contain less than about 5%, less than about 1%, less than about 0.5%, less than about 0.1%, or 0% of non-calcium abrasives, such as silica and / or alumina.

[0139] Oral care compositions may also contain silica abrasives, such as silica gel (in its own form or of any structure), precipitated silica, amorphous precipitated silica (in its own form or of any structure), silica hydrates, and / or combinations thereof. Oral care compositions may contain about 5% to about 70%, about 10% to about 60%, about 10% to about 50%, about 20% to about 50%, about 25% to about 40%, or about 1% to about 50% of silica abrasives.

[0140] When an oral care composition contains dicarboxylic acid, the composition may include a low amount of abrasive or contain no abrasive, because dicarboxylic acid can provide sufficiently high whitening benefits without the need for abrasive.

[0141] While mouthwash compositions typically do not contain abrasives, dental cleaning compositions typically do. However, the dental cleaning compositions and / or toothpaste compositions of embodiments of the present invention may contain low amounts of abrasives or none at all. Therefore, oral care compositions or dental cleaning compositions may contain less than about 5%, about 0.5% to about 2%, or less than about 2% of abrasives by weight of the composition. Oral care compositions or dental cleaning compositions may also be substantially free of, substantially free of, or contain no abrasives. Isoprene-modified flavonoids

[0142] Oral care compositions may contain isoprene-modified flavonoids. Flavonoids are a group of natural substances widely found in fruits, vegetables, grains, bark, roots, stems, flowers, tea, and wine. Flavonoids can have a variety of beneficial effects on health, such as antioxidant, anti-inflammatory, antimutagenic, anticancer, and antibacterial effects. Isoprene-modified flavonoids are flavonoids that include at least one isoprene functional group (3-methylbut-2-en-1-yl, as shown in Formula IX), which has previously been identified as promoting binding to cell membranes. Therefore, while not wishing to be bound by theory, it is believed that the addition of an isoprene group (i.e., isoprene modification) to flavonoids can enhance the activity of the original flavonoid by increasing the lipophilicity of the parent molecule and improving the permeability of the isoprene molecule to bacterial cell membranes. Increasing lipophilicity to increase permeability to cell membranes may be a double-edged sword, as isoprene-modified flavonoids tend to be insoluble at high Log P values ​​(high lipophilicity). Log P can be an important indicator of antibacterial efficacy.

[0143] Therefore, the term isoprene flavonoids may include naturally occurring flavonoids having one or more isoprene functional groups, flavonoids having synthetically added isoprene functional groups, and / or isoprene flavonoids having synthetically added additional isoprene functional groups.

[0144] Formula IX. Isoprene functional group, where R represents other parts of the molecule.

[0145] Other suitable functional groups of the parent molecule that improve the structure-activity relationship (e.g., structure-MIC relationship) of the isoprene molecule include additional heterocycles containing nitrogen or oxygen, alkyl amino chains, or alkyl chains substituted to one or more aromatic rings of the parent flavonoid.

[0146] Flavonoids may have a 15-carbon backbone having at least two benzene rings and at least one heterocycle. Some suitable flavonoid backbones may be shown in formula X (flavonoid backbone), formula XI (isoflavone backbone), and / or formula XII (neoflavonoid backbone).

[0147] Formula X. Flavonoid backbone

[0148] Formula XI. Isoflavone backbone

[0149] Formula XII. New flavonoid backbone

[0150] Other suitable flavonoid subgroups include anthocyanins, flavonoids, flavanones, flavanols, flavans, isoflavones, chalcones, and / or combinations thereof.

[0151] Isoprene flavonoids may include naturally isolated isoprene flavonoids or naturally isolated flavonoids, which are synthetically modified by a variety of synthetic methods known to those skilled in the art of synthetic organic chemistry to add one or more isoprene functional groups.

[0152] Other suitable isoprene-based flavonoids may include psoralen chalcone, psoralen dihydroflavonoid, methyl psoralen chalcone, Corylifol A, icariin A, icariin A1, icariin B, icariin C, icariin, icariin I, icariin II, icariin, isopsoralen chalcone, isoflavone, neopsoralen isoflavone, 6-isoprene naringenin, 8-isoprene naringenin, sophoranone G, (-)-stigmocarpin, flavol, quercetin, myristoyl phenol, sophora flavescens chalcone, sophoraecin, morinone G, morinone C, panduratin A, 6-geranyl naringenin, Australone A, 6,8-diisoprene sennaol, dorsmanin C, dorsmanin F, 8-isoprene kaempferol, 7-O-methyl lupin isoflavone, lupin isoflavone, 6-isoprene genistein, isowighteone, yellow lupin veneterone and / or combinations thereof.

[0153] Preferably, isoprene flavonoids are highly likely to have a MIC of less than about 25 ppm against Staphylococcus aureus (a Gram-positive bacterium). Suitable isoprene flavonoids include psoralen dihydroflavonoids, methyl psoralen, Corylifol A, icariin, isoflavone, neopsoralen isoflavone, 6-isoprene naringenin, 8-isoprene naringenin, sophoranone G, (-)-stigmosiderin, matrine, morinone C, pandanatin A and / or combinations thereof.

[0154] Preferably, isoprene flavonoids are highly likely to have a MIC of less than about 25 ppm against *Escherichia coli* (a Gram-negative bacterium). Suitable isoprene flavonoids include methyl psoralen, isoxoflavone, 8-isoprene naringenin, sophoranone G, matrine, pandanatin A, and / or combinations thereof.

[0155] Approximately 1000 isoprene flavonoids have been identified from plants. Based on previously reported numbers of isoprene flavonoids, isoprene flavonoids are the most common subclass, while isoprene flavanols are the rarest. Although natural isoprene flavonoids have been detected with a variety of structural characteristics, their distribution in plants is narrow, unlike the parent flavonoids, which are present in almost all plants. Most isoprene flavonoids are found in the following families: Guttiferae, Leguminosae, Moraceae, Rutaceae, and Umbelliferae. Leguminosae and Moraceae, due to their use as fruits and vegetables, are the most frequently studied families, and many novel isoprene flavonoids have been explored there.

[0156] Isoprene flavonoids can be incorporated into hop extract, added to a standalone extract, or added as a standalone component of the oral care compositions disclosed herein.

[0157] Suitable isoprene-modified flavonoids can possess specific octanol-water partition coefficients. Octanol-water partition coefficients can be used to predict the lipophilicity of compounds. Without wishing to be bound by theory, compounds falling within the scope described herein are believed to be able to enter and / or disrupt the major hydrophobic phospholipid bilayer that constitutes the microbial cell membrane. Therefore, octanol-water partition coefficients can be correlated with the antibacterial activity of isoprene-modified flavonoids. Suitable isoprene-modified flavonoids may have log P values ​​of at least about 2, at least about 4, about 2 to about 10, about 4 to about 10, about 4 to about 7, or about 4 to about 7.

[0158] The oral care composition may contain at least about 0.001%, about 0.001% to about 5%, about 0.01% to about 2%, about 0.0001% to about 2%, or at least about 0.05% of isoprene flavonoids. amino acids

[0159] Oral care compositions may contain amino acids. As described herein, amino acids may include one or more amino acids, peptides, and / or polypeptides.

[0160] As shown in Formula XIII, an amino acid is an organic compound containing an amine functional group, a carboxyl functional group, and a side chain (R in Formula XIII) specific to each amino acid. Suitable amino acids include, for example, amino acids with positive or negative side chains, amino acids with acidic or basic side chains, amino acids with polar, uncharged side chains, amino acids with hydrophobic side chains, and / or combinations thereof. Suitable amino acids also include, for example, arginine, histidine, lysine, aspartic acid, glutamic acid, serine, threonine, asparagine, glutamine, cysteine, selenocysteine, glycine, proline, alanine, valine, isoleucine, leucine, methionine, phenylalanine, tyrosine, tryptophan, citrulline, ornithine, creatine, diaminobutyric acid, diaminopropionic acid, their salts, and / or combinations thereof.

[0161] Suitable amino acids include compounds of formula XIII, naturally occurring or synthetically derived compounds. Based on the R group and the environment, amino acids can be zwitterionic, neutral, positively charged, or negatively charged. The charge of amino acids and whether specific functional groups can interact with tin under specific pH conditions are well known to those skilled in the art.

[0162] Formula XIII. Amino acids. R is any suitable functional group.

[0163] Suitable amino acids include one or more basic amino acids, one or more acidic amino acids, one or more neutral amino acids, or combinations thereof.

[0164] The oral care composition may contain about 0.01% to about 20%, about 0.1% to about 10%, about 0.5% to about 6%, or about 1% to about 10% of amino acids by weight of the oral care composition.

[0165] As used herein, the term "neutral amino acid" includes not only naturally occurring neutral amino acids such as alanine, asparagine, cysteine, glutamine, glycine, isoleucine, leucine, methionine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine, and valine, but also biologically acceptable amino acids with an isoelectric point in the pH range of 5.0 to 7.0. Biologically preferred acceptable neutral amino acids have a single amino group and a carboxyl group in the molecule or its functional derivatives, such as functional derivatives with modified side chains, although having similar or substantially similar physicochemical properties. In another embodiment, the amino acid will be at least partially water-soluble and provide a pH of less than 7 in an aqueous solution of 1 g / 1000 ml at 25°C.

[0166] Therefore, the neutral amino acids suitable for embodiments of the present invention include, but are not limited to, alanine, GABA, asparagine, cysteine, cystine, glutamine, glycine, hydroxyproline, isoleucine, leucine, methionine, phenylalanine, proline, serine, taurine, threonine, tryptophan, tyrosine, valine, their salts, or mixtures thereof. Preferably, the neutral amino acids used in embodiments of the present invention may include asparagine, glutamine, glycine, their salts, or mixtures thereof. Neutral amino acids may have an isoelectric point of 5.0, 5.1, 5.2, 5.3, 5.4, 5.5, 5.6, 5.7, 5.8, 5.9, 6.0, 6.1, 6.2, 6.3, 6.4, 6.5, 6.6, 6.7, 6.8, 6.9, or 7.0 in an aqueous solution at 25°C. Preferably, the neutral amino acid is selected from proline, glutamine, or glycine, more preferably in its free form (i.e., uncoordinated). If the neutral amino acid is in its salt form, suitable salts include those known in the art as pharmaceutically acceptable and considered physiologically acceptable at the provided amounts and concentrations. Preferably, the neutral amino acid is present in amounts from about 0.0001% to about 10%, preferably about 0.05% to about 5%, preferably about 0.1% to about 3%, preferably about 0.5% to about 3%, and preferably about 1% to about 3% by weight of the composition. In one aspect, the neutral amino acid is glutamine (or a salt thereof). In another aspect, the neutral amino acid is proline (or a salt thereof). In yet another aspect, the neutral amino acid is glycine (or a salt thereof).

[0167] The oral care composition may contain about 0.0001% to about 20%, about 0.1% to about 10%, about 0.5% to about 6%, or about 1% to about 10% of neutral amino acids by weight of the oral care composition. Whitening agent

[0168] The oral care composition may contain a whitening agent in amounts of about 0.1% to about 10%, about 0.2% to about 5%, about 1% to about 5%, or about 1% to about 15% by weight of the oral care composition. The whitening agent may be a compound suitable for whitening at least one tooth in the oral cavity. The whitening agent may include peroxides, metal chlorites, perborates, percarbonates, peroxy acids, persulfates, dicarboxylic acids, and combinations thereof. Suitable peroxides include solid peroxides, hydrogen peroxide, urea peroxide, calcium peroxide, benzoyl peroxide, sodium peroxide, barium peroxide, inorganic peroxides, hydroperoxides, organic peroxides, and mixtures thereof. Suitable metal chlorites include calcium chlorite, barium chlorite, magnesium chlorite, lithium chlorite, sodium chlorite, and potassium chlorite. Other suitable whitening agents include sodium persulfate, potassium persulfate, peroxydone complex (polyvinylpyrrolidone and hydrogen peroxide), 6-phthaliminoperoxyhexanoic acid, phthaliminoperoxyhexanoic acid, or mixtures thereof. wetting agent

[0169] Oral care compositions may contain one or more humectants, have low levels of humectants, or be substantially free of, substantially free of, or contain no humectants. Humectants are used to increase the consistency or "texture" of oral care compositions or dental cleanings and to prevent dental cleanings from drying out. Suitable humectants include polyethylene glycol (of various molecular weights), propylene glycol, glycerin, erythritol, xylitol, sorbitol, mannitol, butylene glycol, lactitol, hydrogenated starch hydrolysate, and / or mixtures thereof. Oral care compositions may contain one or more humectants, each in an amount of 0% to about 70%, about 5% to about 50%, about 10% to about 60%, or about 20% to about 80% by weight of the oral care composition. water

[0170] The oral care composition according to embodiments of the present invention may be an anhydrous, low-water, or high-water formulation. Generally, the oral care composition may contain 0% to about 99%, about 5% to about 75%, about 20% or more, about 30% or more, about 50% or more, up to about 45%, or up to about 75% of water by weight of the composition.

[0171] In high-water oral care compositions and / or toothpaste formulations, the oral care composition comprises about 45% to about 75% water by weight of the composition. The high-water oral care composition and / or toothpaste formulation may comprise about 45% to about 65%, about 45% to about 55%, or about 46% to about 54% water by weight of the composition. Water may be added to the high-water formulation, and / or water may enter the composition due to the inclusion of other ingredients.

[0172] In low-water oral care compositions and / or toothpaste formulations, the oral care composition contains about 5% to about 45% water by weight of the composition. The low-water oral care composition may contain about 5% to about 35%, about 10% to about 25%, or about 20% to about 25% water by weight of the composition. Water may be added to the low-water formulation, and / or water may be incorporated into the composition due to the inclusion of other ingredients.

[0173] In anhydrous oral care compositions and / or toothpaste formulations, the oral care composition contains less than about 10% water by weight of the composition. The anhydrous composition contains less than about 5%, less than about 1%, or 0% water by weight of the composition. Water may be added to the anhydrous formulation, and / or water may be incorporated into the composition due to the inclusion of other ingredients.

[0174] Oral care compositions may also be mouthwash formulations. Mouthwash formulations may contain about 75% to about 99%, about 75% to about 95%, or about 80% to about 95% water.

[0175] The dental cleaning composition may also contain other oral-acceptable carrier materials, such as alcohols, humectants, polymers, surfactants, and acceptability improvers (such as flavoring agents, sweeteners, coloring agents, and / or cooling agents). Other ingredients

[0176] Oral care compositions may contain a variety of other ingredients, such as flavoring agents, sweeteners, coloring agents, preservatives, buffers, or other ingredients suitable for use in oral care compositions, as described below.

[0177] Flavoring agents can also be added to oral care compositions. Suitable flavoring agents include wintergreen oil, peppermint oil, spearmint oil, clove bud oil, menthol, p-propenyl anisole, methyl salicylate, eucalyptol, cinnamon, 1-menthol acetate, sage, eugenol, parsley oil, hydroxyphenyl ethyl ketone, α-ionone, oregano, lemon, orange, propenyl ethyl guaiacol, cinnamon, vanillin, ethyl vanillin, heliotrope, 4-cis-heptenal, dimethyl butyl ketone, methyl p-tert-butylphenylacetate, and mixtures thereof. Cooling agents can also be part of the flavoring agent system. Preferred cooling agents in the compositions of the present invention are p-menthanecarbamoyl reagents, such as N-ethyl-p-menthane-3-carboxamide (commercially known as "WS-3") or N-(ethoxycarbonylmethyl)-3-p-menthanecarboxamide (commercially known as "WS-5"), and mixtures thereof. Flavoring systems are typically used in compositions at a concentration of about 0.001% to about 5% by weight of the oral care composition. These flavorings typically contain aldehydes, ketones, esters, phenols, acids, and mixtures of aliphatic, aromatic, and other alcohols.

[0178] Sweeteners can be added to oral care compositions to give the product a pleasant taste. Suitable sweeteners include saccharin (such as sodium saccharin, potassium saccharin, or calcium saccharin), cyclosulfonates (such as sodium, potassium, or calcium salts), acesulfame K, arbutin, neohesperidin dihydrochalcone, aminoglycoside, dextrose, levulose, sucrose, mannose, sucralose, stevia, and glucose.

[0179] Colorants are added to improve the aesthetic appearance of products. Suitable colorants include, but are not limited to, those approved by the relevant regulatory agencies such as the FDA and those listed in the European Food and Drug Directive, and include pigments such as TiO2, as well as colors such as FD&C and D&C dyes.

[0180] Preservatives can also be added to oral care compositions to prevent bacterial growth. Suitable preservatives approved for use in oral compositions, such as methylparaben, propylparaben, benzoic acid, and sodium benzoate, can be added in safe and effective amounts.

[0181] Titanium dioxide may also be added to the compositions of the present invention. Titanium dioxide is a white powder that increases the opacity of the composition. Titanium dioxide typically comprises about 0.25% to about 5% by weight of the oral care composition.

[0182] Other ingredients may be used in oral care compositions, such as desensitizers, rehabilitative agents, other caries prevention agents, chelating agents / polyvalent chelating agents, vitamins, amino acids, proteins, other anti-plaque / anti-tartar agents, light-blocking agents, antibiotics, anti-enzymes, enzymes, pH control agents, oxidants, antioxidants, etc. Oral care composition form

[0183] Suitable compositional forms include emulsion compositions such as the emulsion composition of U.S. Patent No. 11,147,753 (the entire contents of which are incorporated herein by reference), unit-dose compositions such as the unit-dose composition of U.S. Patent Application Publication No. 2019 / 0343732 (the entire contents of which are incorporated herein by reference), no-rinse oral care compositions, clogging emulsions such as the clogging oil-in-water emulsion of U.S. Patent No. 11,096,874 (the entire contents of which are incorporated herein by reference), dental cleaning compositions, mouthwash compositions, mouthwash compositions, teeth whitening gels, subgingival gels, mouthwashes, mousses, foams, oral sprays, tablets, chewing tablets, chewing gum, teeth whitening strips, dental floss and floss coatings, breath freshener dissolving strips, denture care products, denture adhesive products, or combinations thereof. method

[0184] The oral care compositions described herein can produce beneficial effects on oral health, such as treating, reducing, and / or preventing tooth decay, cavities, gingivitis, and / or combinations thereof, and / or whitening teeth, removing stains from teeth, and / or preventing stain buildup when applied to the oral cavity. For example, a user may dispense at least one inch of a suitable oral care composition strip as described herein into an oral care appliance such as a toothbrush, applicator, and / or dental tray, and apply it to the oral cavity and / or teeth.

[0185] It can instruct users to brush their teeth thoroughly for at least 30 seconds, at least one minute, at least 90 seconds, or at least two minutes, at least once, at least twice, or at least three times a day. It can also instruct users to spit out the oral care composition after brushing.

[0186] Users may also be instructed to rinse with the mouthwash and / or mouthwash composition after or in place of brushing. Users may be instructed to rinse thoroughly with the oral care composition for at least 30 seconds, at least one minute, at least 90 seconds, or at least two minutes, at least once, at least twice, or at least three times a day. Users may also be instructed to spit out the oral care composition after the process is complete.

[0187] Oral care compositions according to embodiments of the present invention can be used to treat, reduce, and / or prevent dental caries, cavities, gingivitis, and / or combinations thereof. Oral care compositions according to embodiments of the present invention can be used to provide beneficial whitening effects, such as whitening teeth, removing stains from teeth, and / or preventing stain buildup on teeth. For example, as described herein, hop β-acid can be used as an anti-gingivitis agent. Therefore, adding hops to any oral care composition can provide anti-gingivitis protection.

[0188] Oral care compositions may include primary packaging, such as tubes, bottles, and / or drums. The primary packaging may be placed within secondary packaging, such as cartons, shrink wrap, etc. Instructions for use of the oral care composition may be printed on the primary and / or secondary packaging. The scope of this method is intended to include instructions provided by the manufacturer, distributor, and / or producer of the oral care composition.

[0189] If the oral care composition is toothpaste, the user can be instructed to dispense the toothpaste from the tube.

[0190] The user can be instructed to apply a portion of toothpaste to the toothbrush. This portion of toothpaste can be any suitable shape, such as a strip, a pea-sized amount, or various other shapes that will fit onto any mechanical and / or manual brush head. The user can be instructed to apply a strip of toothpaste at least about 1 inch, at least about 0.5 inches, at least 1 inch, and / or at least 0.5 inches to the bristles of the toothbrush (such as a soft-bristled toothbrush).

[0191] Users can be instructed to apply a pea-sized or rice-grain-sized amount of toothpaste to the bristles of the toothbrush, such as when used by children under 6 years of age and / or under 2 years of age.

[0192] Users can be instructed to brush their teeth for at least approximately 30 seconds, at least approximately 1 minute, at least approximately 90 seconds, at least approximately 2 minutes, at least 30 seconds, at least 1 minute, at least 90 seconds, and / or at least 2 minutes.

[0193] It can instruct users to brush their teeth thoroughly and / or as directed by a doctor and / or dentist.

[0194] Users can be instructed to brush their teeth after each meal. Users can be instructed to brush their teeth at least once, at least twice, and / or at least three times a day. Users can be instructed to brush their teeth no more than three times a day, for example, to prevent Sn staining. Users can be instructed to brush their teeth in the morning and / or before going to bed at night.

[0195] Because the toothpaste composition contains ingredients that are not suitable for ingestion, such as fluoride, the user may be instructed not to swallow it. However, in the case of oral care compositions that contain hops but not fluoride, it may not be necessary to instruct the user not to swallow the toothpaste. The user may be instructed to spit out (or cough up) the toothpaste composition after stopping the brushing cycle.

[0196] If the oral care composition is mouthwash, the user can be instructed to dispense the mouthwash from the bottle containing the mouthwash.

[0197] Users may be instructed to use mouthwash at least once a day, at least twice a day, and / or at least three times a day.

[0198] Users can be instructed to use the mouthwash composition after using toothpaste and / or dental floss.

[0199] The user can be instructed to rinse their mouth with a portion of mouthwash for a period of time, such as between their teeth. The user can also be instructed to rinse vigorously with a portion of mouthwash.

[0200] Users can be instructed to use approximately 5 mL to approximately 50 mL, approximately 10 mL to approximately 40 mL, 10 mL, 20 mL, 25 mL, 30 mL, 40 mL, 2 teaspoons, and / or 4 teaspoons of mouthwash.

[0201] Users may be instructed to rinse their mouths with mouthwash for at least approximately 30 seconds, at least approximately 1 minute, at least approximately 90 seconds, at least approximately 2 minutes, at least 30 seconds, at least 1 minute, at least 90 seconds, and / or at least 2 minutes.

[0202] Because the mouthwash composition contains ingredients that are not suitable for ingestion, such as fluoride, the user may be instructed not to swallow it. However, in the case of oral care compositions that contain hops but not fluoride, it may not be necessary to instruct the user not to swallow the mouthwash. The user may be instructed to spit out (or cough up) the mouthwash composition after stopping the rinsing cycle.

[0203] Instructions for use of oral care compositions such as toothpaste compositions and / or mouthwashes may vary based on age. For example, one set of instructions may be provided for adults and children aged at least 6 years or at least 2 years, while a second set of instructions may be provided for children aged 6 years or less.

[0204] As described herein, oral care compositions containing hops can be used as medicines, such as those for treating cavities and / or gingivitis. Suitable medicines include oral care compositions, toothpaste compositions, mouthwash compositions, dental floss coatings, chewing gum, and / or other suitable compositions to be applied to the oral cavity.

[0205] Additionally, as described herein, oral care compositions can be used to reduce the number and / or intensity of white patches on teeth that may be attributable to the presence of dental caries in the oral cavity. Alternatively, oral care compositions as described herein can be used to reduce redness, swelling, tenderness, and / or edema of the gingiva at the gingival line immediately adjacent to the tooth surface (which may be attributable to the presence of gingivitis in the oral cavity). combination

[0206] A. An oral care composition, the oral care composition comprising: Hops extract, wherein the hops extract contains dimethyl disulfide; Tin ion source; and A stable system comprising a Michael receptor, wherein the Michael receptor has an α,β-unsaturated carbonyl group, preferably wherein the α,β-unsaturated carbonyl group comprises an aldehyde, a ketone, a cyclic ketone, or a combination thereof.

[0207] B. The oral care composition according to A, wherein the Michael receptor comprises carvone, bonyl lactone, powdered ketone, cinnamaldehyde, α-ionone, 4-octen-3-one, toffee furanone, β-dihydrodamascone, δ-dihydrodamascone, z-jasmone, dextrorotatory piperonone, piperonone, formic acid, or combinations thereof, preferably wherein the Michael receptor comprises δ-dihydrodamascone, β-dihydrodamascone, formic acid, carvone, or combinations thereof, more preferably wherein the Michael receptor comprises carvone.

[0208] C. The oral care composition according to any one of A to B, wherein the composition comprises about 0.001% to about 0.05%, preferably about 0.01% to about 0.025%, more preferably about 0.05% to about 0.2% of the Michael receptor by weight of the composition.

[0209] D. The oral care composition according to any one of A to C, wherein the oral care composition has an average peak area of ​​about 10 or greater DMDS, as determined by gas chromatography-sulfur chemiluminescence detector.

[0210] E. The oral care composition according to any one of A to D, wherein the average peak area of ​​the oral care composition is reduced by about 20% or more, as determined by gas chromatography-sulfur chemiluminescence detector, compared with the average peak area of ​​the oral care composition from which the stable system is not contained.

[0211] F. An oral care composition according to any one of A to E, wherein the composition comprises about 0.00001% to about 1%, preferably about 0.0001% to about 0.1%, more preferably about 0.001% to about 0.1% by weight of the oral care composition.

[0212] G. The oral care composition according to any one of A to F, wherein the ratio of dimethyl disulfide to Michael receptor is in the range of about 1:6000 to about 1:6, about 1:6, preferably about 1:6000 to about 1:60.

[0213] H. An oral care composition according to any one of A to G, wherein the composition further comprises a thiol-Michael addition reaction catalyst, preferably wherein the thiol-Michael addition reaction catalyst comprises a nucleophile comprising an alcohol, amine, halide, phosphine, or a combination thereof, more preferably wherein the thiol-Michael addition reaction catalyst comprises a Lewis base, and even more preferably wherein the thiol-Michael addition reaction catalyst comprises a citrate, gluconate, glycine, phytate, or a combination thereof.

[0214] I. The oral care composition according to any one of A to H, wherein the hop extract comprises hop β-acid, preferably at least 35%, more preferably at least about 40%, more preferably about 40% to about 90%, more preferably about 45% to about 99% of the hop extract by weight.

[0215] J. The oral care composition according to any one of A to I, wherein the hop extract contains less than 1%, preferably less than 0.5%, of hop α-acid by weight of the hop extract.

[0216] K. An oral care composition according to any one of A to J, wherein the composition comprises about 0.01% to about 10%, preferably about 0.1% to about 10%, more preferably about 0.2% to about 5%, and more preferably about 0.25% to about 2% of hop extract by weight of the oral care composition.

[0217] L. An oral care composition according to any one of A to K, wherein the stannous ion source comprises stannous fluoride, stannous chloride, or a combination thereof, preferably wherein the stannous ion source comprises stannous fluoride.

[0218] M. An oral care composition according to any one of A to L, wherein the composition comprises about 0.2% to about 1%, preferably about 0.4% to about 1% by weight of the oral care composition.

[0219] N. Use of the oral care composition according to any one of A to M for the treatment and / or prevention of dental caries, cavities, gingivitis, or combinations thereof.

[0220] O. A method for treating and / or preventing dental caries, cavities, gingivitis, or a combination thereof, said method comprising: Apply the oral care composition according to any one of A to M to the oral cavity (by brushing teeth); and Leave the oral care composition in the oral cavity for at least 30 seconds.

[0221] P. According to the method of O, the method further includes depositing the oral care composition according to any one of claims 1 to 14 onto the application device, and then applying the oral care composition to the oral cavity.

[0222] Q. According to the method of P, wherein the application device is a toothbrush, and applying the oral care composition to the oral cavity includes brushing the teeth in the oral cavity.

[0223] R. According to the method of O, the method further includes removing the oral care composition from the oral cavity by spitting it out, and optionally rinsing the oral cavity.

[0224] S. An oral care composition according to any one of A to M, for use according to N, or for a method according to any one of O to R, wherein the oral care composition is substantially free of, essentially free of, or free of ocimene. Example

[0225] The following embodiments further illustrate the invention, and these embodiments should not be construed in any way as limiting the scope of the invention. After reading this specification, various other aspects, modifications, and equivalents thereof may be proposed to those skilled in the art without departing from the spirit of the invention or the scope of the appended claims.

[0226] Table 1 describes the work of Hopsteiner. ® The provided hop β-acid extract is used in the compositions listed in Table 2. The extract contains approximately 45% hop β-acid and approximately 0.4% hop α-acid by weight of the extract. This is significantly different from conventional hop extracts, which typically contain more hop α-acid than hop β-acid. Other trace components may be present in the hop β-acid extract.

[0227] Table 1. Specifications of Hops β-Acid Extract

[0228]

[0229] Because hop β-acid is provided as an extract, the amounts of certain components can be somewhat variable. For this work, two different batches from the manufacturer were considered to determine whether the DMDS content (e.g., based on hop oil content) of the hop β-acid extract varied between batches. The residual DMDS content of eleven batches of raw material conforming to the specifications outlined in Table 1 was analyzed. The average DMDS content of all batches considered was 23 + / - 9 ppm DMDS. The six-sigma upper limit was 77 ppm DMDS. Effects of Michael receptors on headspace DMDS and MeSH concentrations

[0230] The oral care compositions in Table 2 are prepared by mixing one or more humectants, water, sweeteners, and metal salts, buffers, dyes, and / or stabilizers to produce a liquid mixture. The liquid mixture is homogenized at 25°C until homogeneous and completely dissolved. Next, sodium hydroxide (50% solution) is added to the liquid mixture, and the liquid mixture is homogenized at 25°C until homogeneous and completely dissolved. Separate powder mixtures are prepared by mixing the abrasive silica, thickening silica, and opacifier with any thickener such as xanthan gum, Gantrez, and / or sodium carboxymethyl cellulose. The powder mixture is then mixed with the liquid mixture and completely homogenized. Next, surfactants such as sodium lauryl sulfate, flavoring agents, optional Michael receptors (“MA”), and optional hop extracts are added to the mixture. The contents are homogenized at 25°C until homogeneous, and entrained air is removed by vacuum.

[0231] Table 2. Oral Care Compositions

[0232] Headspace measurements of DMDS and MeSH method

[0233] Dental cleaning sample preparation for headspace DMDS and MeSH measurements was performed using a gas chromatography-sulfur chemiluminescence detector (GC-SCD): 0.5 g (+ / - 0.005 g) of dental cleaning sample was weighed into a 20 mL clear GC vial (Gerstel, Linthicum Heights, MD, USA; part number 093640-036-00) using a Mettler Toledo XSE 205 dual-range balance (Mettler Toledo USA, Columbus, OH, USA), which contained 5 borosilicate glass beads (5 mm in diameter) from Millipore (Millipore Sigma, Rockville, MA, USA; part number Z143944). Then, using a 1 mL pipette (Gilson Company, Inc., Lewis Center, OH, USA; Part No. FD10006), add 1 mL of artificial saliva salt solution (see procedure below) to the sample vial and seal the vial tightly with its screw cap (Gerstel, Linthicum Heights, MD, USA; Part No. 093640-040-00). Transfer the mixture to Corning... ® LSE ™ The vortex mixer (Corning, Glendale, AZ, USA; part number 6775) vortexes at high speed for 60 seconds. Immediately place the sample vial on the sample tray of the gas chromatography-sulfur chemiluminescence detector (GC-SCD) and set the single-injection sequence for GC-SCD analysis.

[0234] Preparation of Artificial Saliva Salt Solutions: The compositions of the artificial saliva salt solutions are shown in Table 3. Each salt described in Table 3 was weighed using a Mettler Toledo XSE 205 dual-range balance (Mettler Toledo USA, Columbus, OH, USA) and quantitatively transferred to a 600 mL beaker. The solutions were then transferred from Milli-Q water at 25°C to approximately 300 mL of deionized (DI) water with a resistivity of 18.2 MΩ·cm. ®Dissolve the salt in a direct water purification system (MilliporeSigma, Rockville, MD, USA; Part No. ZR0Q016WW) and transfer the solution to a 1000 mL volumetric flask. Rinse the flask three times with approximately 200 mL of DI water, transferring each rinse to the same 1000 mL flask. Finally, add more DI water to the flask and mix the solution.

[0235] Table 3. Composition of artificial salivary salt solution (1000 mL)

[0236]

[0237] GC-SCD Analysis Method: Headspace volatile sulfur compounds sampled from dental cleaning agents were analyzed using a GC-SCD system equipped with an Agilent 7890N GC, an Agilent 8355 SCD detector (Agilent, Santa Clara, CA, USA), and a Gerstel Multipurpose Sampler (MPS) (Gerstel, Linthicum Heights, MD, USA) under the conditions described in the following sections: (i) headspace volatile sampling by solid-phase microextraction (SPME); (ii) GC separation conditions; (iii) SCD data acquisition; and (iv) SCD data processing.

[0238] i) Headspace volatiles sampling via SPME: Headspace volatiles released from dental cleaning slurry were captured using a 1 cm divinylbenzene / Carboxen / polydimethylsiloxane (DVB / CAR / PDMS) triphase SPME fiber (Sigma-Aldrich Inc., St. Louis, MO, USA; part number 57329-U) as follows: Once the single-injection run sequence began, the Gerstel MPS autosampler moved the sample vial from the GC-SCD sample tray to a Gerstel stirrer at a preset temperature of 50°C. The toothpaste slurry was incubated at 50°C for 5 minutes with stirring at 250 rpm, and then headspace volatiles were extracted using the DVB / CAR / PDMS fiber for 5 minutes with continuous stirring at 50°C and 250 rpm. Headspace volatile sulfur compounds were analyzed immediately after the addition of artificial saliva and vortexing in single-injection sequence mode to minimize variations in sulfur content measurements.

[0239] ii) GC Separation Conditions: After headspace SPME extraction, the Gerstel MPS automated sampler moved the SPME fiber from the stirrer to the GC inlet, which was equipped with a Merlin Microseal diaphragm (Restek, Bellefonte, PA, USA; Part No. 22810) with a glass injector liner measuring 0.75 × 6.35 × 78.5 mm (Restek, Bellefonte, PA, USA; Part No. 85029-1). The SPME fiber was inserted into the GC inlet and desorbed at 250 °C for 5 minutes. Using helium as the carrier gas, the desorbed volatile compounds were transferred to the column in splitless mode at an initial column pressure of 10.804 psi (74.49 kPa) and a column flow rate of 2.937 mL helium / min. GC was performed in constant flow mode throughout the analytical portion of the analysis using a Restek Rxi-1ms (cross-bonded 100% dimethylpolysiloxane) GC capillary column (Restek Corporation, Bellefonte, PA, USA; part number 13396) with dimensions of 30m × 0.32mm ID × 4.0m film thickness. Headspace volatiles separation on the Restek Rxi-1ms column was achieved using the following GC oven procedure: Initially, the GC oven temperature was maintained at 40°C for 1.0 min, then increased to 220°C at a rate of 15°C / min and maintained at 220°C for 1.0 min. The GC run time was 14 minutes. The column oven temperature was then cooled to 40°C in preparation for subsequent sample injection. The column was conditioned according to the manufacturer's recommendations prior to headspace volatile component analysis.

[0240] iii) SCD data acquisition: Effluent from the GC column was directly introduced into the Agilent 8355 SCD for the detection of volatile sulfur compounds under the conditions shown in Table 4.

[0241] Table 4. Agilent 8355 SCD Operating Parameters

[0242]

[0243] iv) SCD Data Processing: The identification of each sulfur substance was confirmed by running standard compounds under identical conditions on the same instrument. Using this method, methyl mercaptan (MeSH) and dimethyl disulfide (DMDS) were identified as key volatile sulfur compounds from the headspace of the dental cleaning agent samples studied. Samples with blank fiber and artificial saliva alone were run separately, and the results showed that both MeSH and DMDS originated from the dental cleaning agent samples, and not from SPME fiber or residues from artificial saliva.

[0244] The peak areas of MeSH and DMDS were obtained using Agilent OpenLab CDS ChemStation (Revision C.01.10

[201] ) with the following peak integration parameters: initial peak width 0.040; shoulder detection off; initial area rejection 100; and initial height rejection 1.70. Optional manual integration may be used when necessary, but its use should be minimized and, when used, must be consistently applied.

[0245] Five sample preparations and five corresponding repeated GC-SCD injections were performed to determine the volatile sulfur compounds in each dental cleaning sample. The reported peak areas for MeSH and DMDS were the average of the data obtained from each of the five measurements. The relative standard deviation of the peak area for each sulfur component was typically less than 15%.

[0246] Peak areas of MeSH and DMDS for each sample are shown in Table 5. Volatile sulfur compounds such as MeSH and DMDS were observed to originate from hop β-acid extract (both batches) and the dental floss matrix. In stannous dental floss, DMDS was also observed to be converted to MeSH. The presence of these volatile sulfur compounds contributes varying intensities of odor to the dental floss due to their low odor detection threshold (ODT). Formulating dental floss with Michael receptors such as δ-dihydrodamascone reduced MeSH levels. The percentage reduction was calculated relative to the corresponding formulation without δ-dihydrodamascone.

[0247] Table 5. Average peak areas of DMDS and MeSH measured from the headspace of dental cleaning agent samples

[0248]

[0249] The data in Table 5 show that, for each sample pair, the presence of δ-dihydrodamascone significantly reduced the headspace levels of both MeSH and DMDS. The reduction in MeSH is due to the reaction of MeSH with δ-dihydrodamascone as discussed above. As the MeSH level decreases, the reaction between DMDS and tin produces more MeSH, thus reducing the amount of DMDS compared to the same composition without δ-dihydrodamascone.

[0250] Table 6 describes the work of Hopsteiner. ®The provided hop α and β acid extracts were measured to determine the DMDS content in the upstream products of the hop β acid extract. Since hop α and β acids are provided in extract form, the amounts of certain components may vary. However, the extract contains approximately 70% hop α and β acids by weight, distributed between α acids (39.8%) and β acids (13.5%). This differs from the β-acid-rich extracts described in Table 1 and is more similar to conventional hop extracts, which typically have more hop α acids than hop β acids. Other trace components may be present in the hop α and β acid extracts. Not wishing to be bound by theory, it is believed that the sulfur reduction strategy works for the hop extracts in Table 6.

[0251] Table 6. Specifications of Hop α and β Acid Extracts

[0252]

[0253] The residual DMDS content of three batches of raw materials conforming to the specifications outlined in Table 6 was analyzed. The average DMDS content of all batches considered was 8 ± 2 ppm DMDS. The Six Sigma upper limit is 20 ppm DMDS.

[0254] The dimensions and values ​​disclosed herein should not be construed as strictly limited to the precise numerical values ​​cited. Rather, unless otherwise specified, each such dimension is intended to represent the stated value and the range surrounding its functional equivalent. For example, a dimension disclosed as “40 mm” is intended to represent “approximately 40 mm”.

[0255] Unless expressly excluded or otherwise limited, every reference cited herein, including any cross-references or related patents or patent applications, and any patent application or patent claiming priority to or benefiting from it, is incorporated herein by reference in its entirety. Reference to any reference is not an endorsement of it as prior art to any disclosed or protected art herein, nor is it an endorsement of any such invention, either on its own or in combination with any one or more references. Furthermore, where any meaning or definition of a term in this invention conflicts with any meaning or definition of the same term in referenced documents, the meaning or definition given to that term in this invention shall prevail.

[0256] While specific embodiments of the invention have been illustrated and described, it will be apparent to those skilled in the art that various other changes and modifications can be made without departing from the spirit and scope of the invention. Therefore, it is intended that all such changes and modifications falling within the scope of the invention be covered by the appended claims.

Claims

1. An oral care composition comprising: Hops acidity; Dimethyl disulfide; Tin ion source; and A stable system comprising a Michael receptor, wherein the Michael receptor has an α,β-unsaturated carbonyl group, preferably wherein the α,β-unsaturated carbonyl group comprises an aldehyde, a ketone, a cyclic ketone, or a combination thereof. Preferably, the oral care composition has an average peak area of ​​about 10 or greater DMDS, as determined by gas chromatography-sulfur chemiluminescence detector.

2. The oral care composition according to claim 1, wherein the Michael receptor comprises carvone, bonyl lactone, powdered ketone, cinnamaldehyde, α-ionone, 4-octen-3-one, toffee furanone, β-dihydrodamascone, δ-dihydrodamascone, z-jasmone, dextrorotatory piperonone, piperonone, formic acid, or combinations thereof, preferably wherein the Michael receptor comprises δ-dihydrodamascone, β-dihydrodamascone, formic acid, carvone, or combinations thereof, more preferably wherein the Michael receptor comprises carvone.

3. The oral care composition according to claim 1 or claim 2, wherein the composition comprises about 0.001% to about 0.05%, preferably about 0.01% to about 0.025%, more preferably about 0.05% to about 0.2% of the Michael receptor by weight of the composition.

4. The oral care composition according to any one of claims 1 to 3, wherein the average peak area of ​​the DMDS of the oral care composition is reduced by about 20% or more, as determined by gas chromatography-sulfur chemiluminescence detector, compared with the average peak area of ​​the oral care composition from which the stable system is not contained.

5. The oral care composition according to any one of claims 1 to 4, wherein the composition comprises about 0.00001% to about 1%, preferably about 0.0001% to about 0.1%, more preferably about 0.001% to about 0.1% by weight of the oral care composition.

6. The oral care composition according to any one of claims 1 to 5, wherein the ratio of dimethyl disulfide to Michael receptor is in the range of about 1:6000 to about 1:6, about 1:6, preferably about 1:6000 to about 1:

60.

7. The oral care composition according to any one of claims 1 to 6, wherein the composition further comprises a thiol-Michael addition reaction catalyst, preferably wherein the thiol-Michael addition reaction catalyst comprises a nucleophile comprising an alcohol, amine, halide, phosphine, or a combination thereof, more preferably wherein the thiol-Michael addition reaction catalyst comprises a Lewis base, and even more preferably wherein the thiol-Michael addition reaction catalyst comprises a citrate, gluconate, glycine, phytate, or a combination thereof.

8. The oral care composition according to any one of claims 1 to 7, wherein the oral care composition further comprises a hops extract, the hops extract comprising the hops acid and the dimethyl disulfide, preferably wherein the hops extract comprises less than 1%, preferably less than 0.5%, of hops α-acid by weight of the hops extract.

9. The oral care composition of claim 8, wherein the hop extract comprises hop β-acid, preferably at least 35%, more preferably at least about 40%, more preferably about 40% to about 90%, more preferably about 45% to about 99% of the hop extract by weight.

10. The oral care composition according to claim 8 or 9, wherein the composition comprises about 0.01% to about 10%, preferably about 0.1% to about 10%, more preferably about 0.2% to about 5%, and more preferably about 0.25% to about 2% of hop extract by weight of the oral care composition.

11. The oral care composition according to any one of claims 1 to 10, wherein the composition comprises about 0.2% to about 1%, preferably about 0.4% to about 1% by weight of the oral care composition, and wherein the stannous ion source comprises stannous fluoride, stannous chloride, or a combination thereof, preferably wherein the stannous ion source comprises stannous fluoride.

12. Use of the oral care composition according to any one of claims 1 to 11 for the treatment and / or prevention of dental caries, cavities, gingivitis, or combinations thereof.

13. A method for treating and / or preventing dental caries, cavities, gingivitis, or a combination thereof, said method comprising: The oral care composition according to any one of claims 1 to 11 is applied to the oral cavity (by brushing teeth). as well as Leave the oral care composition in the oral cavity for at least 30 seconds.

14. The method of claim 13, further comprising depositing the oral care composition onto an application device and then applying the oral care composition to the oral cavity.

15. The method of claim 14, wherein the application device is a toothbrush, and applying the oral care composition to the oral cavity includes brushing the teeth in the oral cavity, and wherein the method further includes removing the oral care composition from the oral cavity by spitting it out, and optionally rinsing the oral cavity.

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