# US 9,040,025 B2 · Anti-senstivity, anti-caries, anti-staining, anti-plaque, ultra-mild oral hygiene agent > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,040,025 B2 - Document ID: US9040025B2 - Status: Granted - Kind: B2 - Application number: 12/380,971 - Filed: 2009-03-05 - Published: 2009-07-02 - Granted: 2015-05-26 - Earliest claimed: 2003-02-21 - Assignees: Rhodia Operations - Applicants: Robert Lee Reierson; Todd William Domke - Inventors: Robert Lee Reierson; Todd William Domke - Web page: https://patentgrep.com/patent/US9040025B2 ## CPC - A61K 8/55: Phosphorus compounds - A61Q 11/00: Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS ## Abstract This invention relates to a composition useful as a dentifrice comprising a surfactant agent consisting essentially of monoalkyl and dialkyl phosphate esters, wherein the ratio of monoesters to diesters is greater than 1, and optionally an abrasive agent consisting essentially of siliceous materials. ## Claims ### Claim 1 An oral care composition, comprising: water soluble phosphate ester salts; at least one anti-caries agent selected from the group consisting of sodium fluoride and sodium monofluorophosphate, an abrasive agent, provided that the abrasive agent is not a calcium based abrasive agent, and a peroxide tooth whitening agent, wherein the composition has an absence of calcium compounds; wherein all water soluble phosphate ester salts of the composition consist of one or more water soluble phosphate monoester salts according to structure (I) and one or more water soluble phosphate diester salts according to structure (II), wherein the molar ratio of said one or more monoester salts to said one or more diester salts is from 70:30 to 92:8: wherein the phosphate monoester salt according to structure (I) has a phosphate head group of structure (IA) and a hydrophobic tail of structure (IB) R1O(CnH2nO)a(CmH2mO)b (IB); and wherein the dialkyl phosphate ester salt according to structure (II) has a phosphate head group of structure (IIA) and hydrophobic tails of structures (IIB) and (IIC) R2O(CnH2nO)a(CmH2mO)b (IIB), (OCmH2m)b(OCnC2n)aOR3 (IIC); wherein: R1, R2, and R3 are each individually linear or branched, saturated or unsaturated hydrocarbon groups of from 10 to 22 carbon atoms, n and m are each individually 2 to 4, a and b are each individually 0 to 20, one of Z1 and Z2 is alkali metal, ammonium, protonated alkyl amine, protonated alkanolamine, or protonated basic amino acid, and the other of Z1 and Z2 is hydrogen, alkali metal, ammonium, protonated alkyl amine, protonated alkanolamine, or protonated basic amino acid, and Z3 is alkali metal, ammonium, protonated alkyl amine, protonated alkanolamine, or protonated basic amino acid; wherein the phosphate head groups of the at least one monoalkyl water soluble phosphate ester salt and the at least one dialkyl water soluble phosphate ester salt are for anchoring to calcium hydroxyapatite tooth structure of a tooth, the hydrophobic tails for separating from the respective anchored phosphate head groups by hydrolysis, and the phosphate head groups after hydrolysis for being fixed in place in the calcium hydroxyapatite tooth structure by reaction with calcium in saliva of an oral cavity in which the tooth is located. ### Claim 2 (depends on 1) The composition of claim 1, wherein said molar ratio of the one or more monoester salts to the one or more diester salts is from 70:30 to 91:9. ### Claim 3 (depends on 1) The composition of claim 1, wherein R1, R2, and R3 are each individually linear or branched, saturated or unsaturated hydrocarbon groups of from 10 to 14 carbon atoms, and said phosphate ester salts each have a degree of ethoxylation or propoxylation from 0 to 4. ### Claim 4 (depends on 1) The composition of claim 1, wherein at least one said phosphate ester salt is alkyl ethoxylate phosphate ester salt having a degree of ethoxylation between 1 to 20. ### Claim 5 (depends on 3) The composition of claim 3, wherein at least one of said phosphate ester salts is potassium dodecyl phosphate. ### Claim 6 (depends on 1) The composition of claim 1, wherein the abrasive agent is selected from hydrated silica, colloidal silica, fumed silica, insoluble sodium metaphosphate, insoluble sodium aluminosilicates, sodium bicarbonate and mixtures thereof, wherein said abrasive agent is in amount of from about 5% to about 70% by weight of the composition. ### Claim 7 (depends on 1) The composition of claim 1, wherein said composition is a toothpaste or a tooth cleaning gel. ### Claim 8 (depends on 1) The composition of claim 1, wherein the composition further comprises a liquid selected from water, humectant, binder, and mixtures thereof, wherein said liquid is in an amount of from about 10% to about 90% by weight of the composition. ### Claim 9 (depends on 1) The composition of claim 1, wherein said R1, R2, and R3 are each individually linear or branched, saturated or unsaturated hydrocarbon groups of from 12 to 22 carbon atoms. ### Claim 10 (depends on 9) The composition of claim 9, wherein R1, R2, and R3 are each individually linear or branched, saturated or unsaturated hydrocarbon groups of from 12 to 14 carbon atoms. ### Claim 11 (depends on 10) The composition of claim 10, wherein said phosphate ester salts have a degree of ethoxylation or propoxylation from 0 to 4. ### Claim 12 An oral care composition consisting of: one or more water soluble monoalkyl ester salts and one or more dialkyl phosphate ester salts, wherein the molar ratio of monoester salts to diester salts is from 70:30 to 92:8, wherein from about 0.1 percent by weight to about 10 percent by weight of the composition is one or more of water soluble phosphate monoester salts according to structure (I) and one or more water soluble phosphate diester salts according to structure (II): wherein the phosphate monoester salt according to structure (I) has a phosphate head group of structure (IA) and a hydrophobic tail of structure (IB) R1O(CnH2nO)a(CmH2mO)b (IB); and wherein the dialkyl phosphate ester salt according to structure (II) has a phosphate head group of structure (IIA) and hydrophobic tails of structures (IIB) and (IIC) R2O(CnH2nO)a(CmH2mO)b (IIB), (OCmH2m)b(OCnC2n)aOR3 (IIC); wherein: R1, R2 and R3 are each individually linear or branched, saturated or unsaturated hydrocarbons of from 10 to 22 carbon atoms; n and m of the monoalkyl ester and the dialkyl ester are each individually 2 to 4; a and b of the monoalkyl ester and the dialkyl ester are each individually 0 to 20; one of Z1 and Z2 is alkali metal, an ammonium, protonated alkyl amine, protonated alkanolamine or a protonated basic amino acid; and the other of Z1 or Z2 is hydrogen, alkali metal, ammonium, protonated alkyl amine, protonated alkanolamine, or protonated basic amino acid; Z3 is alkali metal, ammonium, protonated alkyl amine, protonated alkanolamine, or protonated basic amino acid, and an abrasive agent, provided the abrasive agent is not a calcium based abrasive agent, wherein the abrasive agent is selected from at least one member of the group consisting of siliceous materials, insoluble sodium metaphosphate, insoluble sodium aluminosilicates, sodium bicarbonate, hydrated silica, colloidal silica, fumed silica; a peroxide tooth whitening agent; anti-caries agent selected from at least one member of the group consisting of sodium fluoride and sodium monofluorophosphate, wherein sodium trimetaphosphate is an optional additional anti-caries agent; at least one additive selected from the group consisting of flavoring agent, sweetening agent, anti-calculus agent, buffering agent, and flow aids, alcohol, sudsing agent, preservatives, vitamins, anti-plaque agents, anti-staining compounds, anionic polymers, organic binder, inorganic thickener, nonionic surfactants, coloring agents, pigments, and tetrasodium pyrophosphate; wherein the sweetening agent is at least one of saccharin and sorbitol; wherein the anti-calculus agents are at least one of water soluble alkali metal salt of a polyphosphate; wherein the buffering agent is selected from the group consisting of alkali metal orthophosphate, phosphoric acid, alkali metal glycerophosphates, tartrates and citrates; wherein the anti-plaque agents are selected form the group consisting of stannous salts, copper salts, and magnesium salts; wherein the anti-staining agents are silicone polymers; wherein the anionic polymers are selected from at least one member selected from the group consisting of polycarboxylates, polysulfonates, carboxylate and sulfonate copolymers, phosphonate polymers, and polyphosphates; wherein the organic binder is selected from the group consisting of cellulose gum, glycerin, hydroxycellulose, hydroxypropyl cellulose, xanthan gum, Irish moss, and gum tragacanth; wherein the inorganic thickener is silica; wherein the composition has an absence of calcium compounds; optionally a liquid selected from the group consisting of water, humectant, binder, and mixtures thereof, wherein said humectant is at least one member selected from the group consisting of glycerin, sorbitol, polyethylene glycols, polypropylene glycol, and hydrogenated partially hydrolyzed polysaccharides; wherein the phosphate head groups of the at least one monoalkyl water soluble phosphate ester salt and the at least one dialkyl water soluble phosphate ester salt anchor to calcium hydroxyapatite tooth structure of the tooth, the hydrophobic tails separate from the respective anchored phosphate head groups by hydrolysis, and the phosphate head groups after hydrolysis are fixed in place in the calcium hydroxyapatite tooth structure by reaction with calcium in saliva of an oral cavity in which the tooth is located; wherein the composition has an absence of strontium salts; wherein surfactant of the composition consists of the water soluble phosphate ester salts and optional nonionic surfactant. ### Claim 13 (depends on 12) The composition of claim 12, wherein at least one of said water soluble phosphate ester salts is potassium dodecyl phosphate. ### Claim 14 (depends on 1) The oral care composition of claim 1, wherein the peroxide tooth whitening agent comprises carbamide peroxide. ### Claim 15 (depends on 12) The composition of claim 12, wherein the abrasive agent is selected from hydrated silica, colloidal silica, fumed silica, insoluble sodium metaphosphate, insoluble sodium aluminosilicates, sodium bicarbonate, and mixtures thereof. ### Claim 16 (depends on 1) The composition of claim 1, wherein the molar ratio of monoester salts to diester salts is from 80:20 to 90:10. ### Claim 17 (depends on 1) The composition of claim 1, wherein the peroxide tooth whitening agent comprises hydrogen peroxide. ### Claim 18 (depends on 12) The composition of claim 12, wherein at least one of the water soluble phosphate monoester salts and the water soluble phosphate diester salts is an alkyl ethoxylate phosphate ester salt. ### Claim 19 (depends on 12) The composition of claim 12, wherein the molar ratio of water soluble phosphate ester salts according to structure (I) to water soluble phosphate ester salts according to structure (II) is from 80:20 to 91:9. ### Claim 20 (depends on 12) The composition of claim 12, wherein the molar ratio of water soluble phosphate ester salts according to structure (I) to water soluble phosphate ester salts according to structure (II) is from 85:15 to 90:10. ### Claim 21 (depends on 12) The composition of claim 12, wherein R1, R2, and R3 are each individually linear or branched, saturated or unsaturated hydrocarbons of from 10 to 14 carbon atoms. ### Claim 22 (depends on 12) The composition of claim 12, wherein m and n are each 2 and a and b are each from 0 to 4. ### Claim 23 (depends on 12) The composition of claim 12, wherein the oral care composition is a toothpaste or gel, a mouth wash, a chewing gum, a soluble oral care strip, or a lozenge. ### Claim 24 (depends on 12) The composition of claim 12, wherein R1, R2, and R3 are each individually linear or branched, saturated or unsaturated hydrocarbon groups of from 12 to 14 carbon atoms. ### Claim 25 (depends on 12) The composition of claim 12, wherein the monoalkyl phosphate ester salts are selected from water soluble alkali metal or functional amine salts of a monoalkyl phosphate ester; wherein the dialkyl phosphate ester salts are selected from water soluble alkali metal or functional amine salts of a dialkyl phosphate ester. ### Claim 26 (depends on 9) The composition of claim 9, wherein at least one said phosphate ester salt is an alkyl ethoxylate phosphate ester salt having a degree of ethoxylation from between 1 to 20, wherein said molar ratio of the monoester salts to the diester salts is from 70:30 to 91:9, wherein said oral care composition comprises the anti-caries agent selected from at least one member of the group consisting of sodium fluoride and sodium monofluorophosphate to provide fluoride ions at a level of 50 to 3000 ppm. ### Claim 27 (depends on 12) The composition of claim 12, wherein at least one said phosphate ester salt is an alkyl ethoxylate phosphate ester salt having a degree of ethoxylation from between 1 to 20, wherein said molar ratio of the monoester salts to the diester salts is from 70:30 to 91:9, wherein R1, R2, and R3 are each individually linear or branched, saturated or unsaturated hydrocarbon groups of from 10 to 14 carbon atoms; wherein said oral care composition comprises the anti-caries agent selected from at least one member of the group consisting of sodium fluoride and sodium monofluorophosphate to provide fluoride ions at a level of 50 to 3000 ppm. ### Claim 28 (depends on 1) The composition of claim 1, wherein said oral care composition comprises the anti-caries agent selected from at least one member of the group consisting of sodium fluoride and sodium monofluorophosphate to provide fluoride ions at a level of 50 to 3000 ppm. ### Claim 29 (depends on 1) The composition of claim 1, wherein the oral care composition consists of: said one or more water soluble phosphate monoester salts according to structure (I) and said one or more water soluble phosphate diester salts according to structure (II); the abrasive agent, wherein the abrasive agent is at least one member selected from the group consisting of siliceous materials, sodium metaphosphate, insoluble sodium aluminosilicates, sodium bicarbonate, hydrated silica, colloidal silica; the peroxide tooth whitening agent, the anti-caries agent, wherein the anti-caries agent is at least one member selected from the group consisting of sodium fluoride and sodium monofluorophosphate, wherein sodium trimetaphosphate is an optional additional anti-caries agent; and at least one member selected from the group consisting of flavor oil, sweetening agent, an anti-calculus agent, buffering agent, anti-staining compounds, anionic polymers, and alcohol; wherein the sweetening agent is at least one of saccharin and sorbitol; wherein the anti-calculus agent is at least one member selected from water-soluble alkali metal salt of a polyphosphate; wherein the buffering agent is at least one member selected from the group consisting of alkali metal orthophosphates, phosphoric acid, alkali metal glycerophosphates, tartrates, and citrates; wherein the anti-staining compounds are selected from silicone polymers; wherein the anionic polymers are selected from at least one member selected from the group consisting of polycarboxylates, polysulfonates, carboxylate and sulfonate copolymers, phosphonate polymers, and polyphosphates; optionally a liquid selected from the group consisting of water and humectant, wherein said humectant is at least one member selected from the group consisting of glycerin, sorbitol, polyethylene glycols, polypropylene glycol, and hydrogenated partially hydrolyzed polysaccharides; optionally a member selected from the group consisting of organic binder, inorganic thickener selected from the group consisting of silica and hydrated silica; nonionic surfactants, dye coloring agents, vitamin C, vitamin E, plant extracts, titanium dioxide, and tetrasodium pyrophosphate; wherein the organic binder is selected from the group consisting of cellulose gum, glycerin, hydroxyethyl cellulose, hydroxypropyl cellulose, xanthan gum, Irish moss, and gum tragacanth; wherein the composition has an absence of calcium compounds; wherein the composition has an absence of strontium salts; wherein surfactant of the composition consists of the water soluble phosphate ester salts and optional nonionic surfactant. ### Claim 30 (depends on 29) The composition of claim 29, wherein R1, R2, and R3 are each individually linear or branched, saturated or unsaturated hydrocarbon groups of from 12 to 14 carbon atoms. ### Claim 31 (depends on 30) The composition of claim 30, wherein at least one of the water soluble phosphate ester salts of the composition is potassium dodecyl phosphate. ### Claim 32 (depends on 29) The composition of claim 29, wherein R1, R2, and R3 are each individually linear or branched, saturated or unsaturated hydrocarbon groups of from 12 to 14 carbon atoms, wherein said molar ratio of the monoester salts to the diester salts is from 70:30 to 91:9, wherein said phosphate ester salts each have a degree of ethoxylation or propoxylation from 0 to 4, wherein the peroxide tooth whitening agent comprises hydrogen peroxide. ### Claim 33 (depends on 1) The composition of claim 1, wherein a and b are each individually 0. ### Claim 34 (depends on 30) The composition of claim 30, wherein a and b are each individually 0.