Antimicrobial compositions for oral care

Abstract

The present invention relates to the use of compound X, selected from the following compounds (I), glyceryl ethers, sorbitan esters, and isosorbide esters, as an antimicrobial agent against microorganisms that cause tooth caries, microorganisms that cause dental plaque, or microorganisms that cause gingivitis. [Formula 1] JPEG2026510223000025.jpg3777 (wherein R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof.)

Description

[Technical Field]

[0001] The present invention relates to the use of specific compounds as antimicrobial agents against microorganisms that cause tooth decay, plaque, or gingivitis, and to oral care formulations. The present invention also relates to specific compounds for use in reducing the effects of microorganisms that cause tooth decay, plaque, or gingivitis, specific compounds for use in the prevention or treatment of tooth decay, plaque, or gingivitis, oral care formulations for use in reducing the effects of microorganisms that cause tooth decay, plaque, or gingivitis, and oral care formulations for use in the prevention or treatment of tooth decay, plaque, or gingivitis. [Background technology]

[0002] Oral care is important for general hygiene and overall health. Oral care includes brushing your teeth with toothpaste and rinsing your mouth with mouthwash. Tooth decay is caused by acids produced by certain bacteria, including Streptococcus mutans (S. mutans). S. mutans produces sticky glucans and fructans from fermentable sugars, especially sucrose, which make it easier for bacteria to adhere to the oral surface. Plaque is a sticky biofilm or collection of bacteria that is usually found on the surface of teeth, along the gum line, and below the gum line. Plaque can cause tooth decay and gingivitis. [Overview of the Initiative] [Problems that the invention aims to solve]

[0003] There is a continuing need for antibacterial agents that can be used in oral care formulations.

[0004] Certain compounds have been found to be useful as antimicrobial agents against microorganisms that cause tooth decay, plaque, or gingivitis. [Means for solving the problem]

[0005] Accordingly, the present invention relates to the use of a compound X selected from the following compounds (I), glyceryl ethers, sorbitan esters, and isosorbide esters as an antimicrobial agent against microorganisms that cause tooth caries, microorganisms that cause dental plaque, or microorganisms that cause gingivitis. [ka] (In the formula, R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof.)

[0006] Advantageously, the compounds used in this invention have a high renewable carbon content and are sustainable. The compounds used in this invention can be incorporated into oral care formulations.

[0007] In the present invention, compound X, selected from the compounds of formula (I), glyceryl ether, sorbitan ester, and isosorbide ester, is used as an antimicrobial agent against microorganisms that cause tooth caries, microorganisms that cause dental plaque, or microorganisms that cause gingivitis. [ka] (In the formula, R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof.)

[0008] In the present invention, compound X is selected from the compound of formula (I), glyceryl ether, sorbitan ester, and isosorbide ester. [ka] (In the formula, R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof.)

[0009] In one embodiment, compound X, selected from the compounds of formula (I), is used as an antimicrobial agent against microorganisms that cause tooth caries, microorganisms that cause plaque, or microorganisms that cause gingivitis. [ka] (In the formula, R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof.)

[0010] In one embodiment, compound X is selected from the compounds of the following formula (I). [ka] (In the formula, R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof.)

[0011] Preferably, R in formula (I) is selected from saturated hydrocarbon chains having 5 to 17 carbon atoms, unsaturated hydrocarbon chains having 5 to 17 carbon atoms, and mixtures thereof.

[0012] More preferably, R in formula (I) is selected from saturated hydrocarbon chains having 5 to 13 carbon atoms, unsaturated hydrocarbon chains having 5 to 13 carbon atoms, and mixtures thereof.

[0013] Particularly preferred, R in formula (I) is selected from saturated hydrocarbon chains having 7 to 9 carbon atoms, unsaturated hydrocarbon chains having 7 to 9 carbon atoms, and mixtures thereof.

[0014] In at least one embodiment, R in formula (I) is selected from -(CH2)6CH3, -(CH2)8CH3, and mixtures thereof; or R in formula (I) is -(CH2) 10 CH3, -(CH2) 12Selected from CH3, and mixtures thereof; or, R in formula (I) is selected from -(CH2)7CH=CH2, -(CH2)7CH=CHCH2CH3, and mixtures thereof; or, the R-C=O residue of formula (I) is derived from soybean fatty acids.

[0015] In at least one embodiment, R in formula (I) is selected from -(CH2)6CH3, -(CH2)8CH3, and mixtures thereof. In at least one embodiment, R in formula (I) is -(CH2) 10 CH3, -(CH2) 12 CH3, and mixtures thereof. In at least one embodiment, R in formula (I) is selected from -(CH2)7CH=CH2, -(CH2)7CH=CHCH2CH3, and mixtures thereof. In at least one embodiment, the R-C=O residue of formula (I) is derived from coconut fatty acids. In at least one embodiment, the R-C=O residue of formula (I) is derived from soybean fatty acids.

[0016] As used herein, the expression "the R-C=O residue of formula (I) is derived from coconut fatty acids" preferably means that the carbon chain length distribution of the R-C=O residue of formula (I) corresponds to the carbon chain length distribution of the fatty acids in coconut oil (e.g., bound as triglycerides).

[0017] As used herein, the expression "the R-C=O residue of formula (I) is derived from soybean fatty acids" preferably means that the carbon chain length distribution of the R-C=O residue of formula (I) corresponds to the carbon chain length distribution of the fatty acids in soybean oil (e.g., bound as triglycerides).

[0018] Preferably, the weight ratio of the compound of formula (I) where R is -(CH2)6CH3 to the compound of formula (I) where R is -(CH2)8CH3 is from 1:9 to 9:1, preferably from 3:7 to 7:3.

[0019] Preferably, the compound of formula (I) where R is -(CH2) 10 CH3 to the compound of formula (I) where R is -(CH2)12 The weight ratio of the compound of formula (I) which is CH3 is 1:9 to 9:1, preferably 3:7 to 7:3.

[0020] Preferably, the weight ratio of the compound of formula (I) where R is -(CH2)7CH=CH2 to the compound of formula (I) where R is -(CH2)7CH=CHCH2CH3 is 1:9 to 9:1, preferably 3:7 to 7:3.

[0021] Advantageously, the compound of formula (I) is soluble in water. Therefore, the compound of formula (I) is suitable for use in mouthwash formulations.

[0022] Compounds of formula (I) are described, for example, in WO2018 / 002100 and European application number EP21200587.0.

[0023] In one embodiment, compound X, selected from glyceryl ethers, is used as an antimicrobial agent against microorganisms that cause tooth decay, microorganisms that cause dental plaque, or microorganisms that cause gingivitis. In one embodiment, compound X is selected from glyceryl ethers. Preferably, the glyceryl ether is a monoether or diether of glycerin and one or more C6-C20 fatty alcohols. More preferably, the glyceryl ether is a monoether or diether of glycerin and one or more C8-C14 fatty alcohols. Particularly preferably, the glyceryl ether is a monoether of glycerin and one or more C8 fatty alcohols.

[0024] In at least one embodiment, the glyceryl ether is selected from ethylhexylglycerin, methylheptylglycerin, caprylyl glyceryl ether, and mixtures thereof.

[0025] In one embodiment, compound X, selected from sorbitan esters and isosorbide esters, is used as an antimicrobial agent against microorganisms that cause tooth caries, microorganisms that cause dental plaque, or microorganisms that cause gingivitis.

[0026] In one embodiment, compound X is selected from sorbitan esters and isosorbide esters.

[0027] In one embodiment, compound X, selected from sorbitan esters, is used as an antimicrobial agent against microorganisms that cause tooth caries, microorganisms that cause plaque, or microorganisms that cause gingivitis.

[0028] In one embodiment, compound X is selected from sorbitan esters. Preferably, the sorbitan ester is a monoester, diester, or triester of sorbitan with one or more C6-C20 fatty acids. More preferably, the sorbitan ester is a monoester or diester of sorbitan with one or more C8-C14 fatty acids. Particularly preferably, the sorbitan ester is a monoester or diester of sorbitan with caprylic acid.

[0029] Preferably, the sorbitan ester is selected from sorbitan caprylate, sorbitan stearate, sorbitan oliveate, sorbitan oleate, sorbitan caprate, sorbitan laurate, sorbitan myristate, sorbitan caproate, and mixtures thereof. Particularly preferably, the sorbitan ester is sorbitan caprylate.

[0030] In one embodiment, compound X, selected from isosorbide esters, is used as an antimicrobial agent against microorganisms that cause tooth caries, microorganisms that cause dental plaque, or microorganisms that cause gingivitis. In one embodiment, compound X is selected from isosorbide esters. Preferably, the isosorbide ester is a monoester or diester of isosorbide and one or more C6-C20 fatty acids. More preferably, the isosorbide ester is a monoester or diester of isosorbide and one or more C8-C14 fatty acids. Particularly preferably, the isosorbide ester is a monoester or diester of isosorbide and caprylic acid.

[0031] Preferably, the isosorbide ester is selected from isosorbide caprylate, isosorbide stearate, isosorbide oliveate, isosorbide oleate, isosorbide caprate, isosorbide laurate, isosorbide myristic acid, isosorbide caproic acid, and mixtures thereof. Particularly preferred is the isosorbide ester being isosorbide caprylate.

[0032] Advantageously, compound X is suitable for use in toothpaste formulations.

[0033] In one embodiment, compound X as defined herein is used as an antimicrobial agent against microorganisms that cause tooth decay, plaque, or gingivitis. Such microorganisms include, for example, Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum, or Porphyromonas gingivalis. Preferred microorganisms are Streptococcus mutans or Lactobacillus acidophilus.

[0034] In a preferred embodiment, the microorganism causing tooth decay is the bacteria that cause tooth decay. In a preferred embodiment, the microorganism causing plaque is the bacteria that cause plaque. In a preferred embodiment, the microorganism causing gingivitis is the bacteria that cause gingivitis.

[0035] In preferred embodiments, compound X as defined herein is used as an antibacterial agent against bacteria that cause tooth decay, bacteria that cause plaque, or bacteria that cause gingivitis. Examples of such bacteria include Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum, or Porphyromonas gingivalis. Preferred bacteria are Streptococcus mutans or Lactobacillus acidophilus.

[0036] Streptococcus mutans, Streptococcus sanguinis, and Streptococcus sobrinus form membranes. Streptococcus goldoni produces acid. They attack tooth enamel. Fusobacterium nucleatum forms membranes. Porphyromonas gingivalis causes periodontal disease.

[0037] Optionally, compound X as defined herein may be used in combination with additional antimicrobial agents.

[0038] In at least one embodiment, the antimicrobial agent is selected from the group consisting of aromatic alcohols, organic acids and their salts, hydroxamic acids and their salts, hydroxyacetophenone, compounds of the following formula (P), alkyldiols, halogen compounds, isothiazolinone, and mixtures thereof. [ka] (In the formula, R1' is hydrogen, unsubstituted or halogen-substituted, branched or unbranched, C1-C 20- an alkyl group, an unsubstituted or halogen-substituted C5-C8-cycloalkyl group, an unsubstituted or halogen-substituted C6-C 10 - aryl group, or an unsubstituted or halogen-substituted, branched or unbranched, C7-C 20 - aralkyl group; R2’ is O or S; R3’ is H or a C1-C4-alkyl group, preferably methyl; X + is a cation.)

[0039] In at least one embodiment, the aromatic alcohol is selected from the group consisting of benzyl alcohol, phenoxyethanol, veratryl alcohol, propylene phenoxyethanol, phenethyl alcohol, phenylpropanol, vanillin, 2-methyl-1-phenyl-2-propanol, and mixtures thereof.

[0040] In at least one embodiment, the organic acid and its salts are selected from the group consisting of benzoic acid, sorbic acid, dehydroacetic acid, lactic acid, salicylic acid, p-anisic acid, undecylenic acid, glycolic acid, propionic acid, levulinic acid, and mixtures thereof.

[0041] In at least one embodiment, the hydroxamic acid is selected from the following formula (III).

Chemical formula

[0042] Preferably, R1 in formula (III) is selected from a saturated hydrocarbon chain having 5 to 17 carbon atoms, an unsaturated hydrocarbon chain having 5 to 17 carbon atoms, and mixtures thereof. More preferably, R1 in formula (III) is selected from saturated hydrocarbon chains having 5 to 13 carbon atoms, unsaturated hydrocarbon chains having 5 to 13 carbon atoms, and mixtures thereof. Particularly preferred, R1 in formula (III) is selected from a saturated hydrocarbon chain having 7 carbon atoms, an unsaturated hydrocarbon chain having 7 carbon atoms, and a mixture thereof.

[0043] Preferred hydroxamic acids are selected from caprylhydroxamic acid, hexanohydroxamic acid, caprohydroxamic acid, laurohydroxamic acid, and mixtures thereof. A particularly preferred hydroxamic acid is caprylhydroxamic acid. Caprylhydroxamic acid is sometimes also called caprylohydroxamic acid or octanohydroxamic acid. Hydroxamic acids are described, for example, in EP2224973.

[0044] Examples of hydroxamic acid salts include alkali metal salts of hydroxamic acid (e.g., sodium salt or potassium salt of hydroxamic acid) or alkaline earth metal salts of hydroxamic acid (e.g., magnesium salt or calcium salt of hydroxamic acid).

[0045] In at least one embodiment, the compound of formula (P) is selected from the group consisting of 2-hydroxypyridine-N-oxide, 2-pyridinethiol-1-oxide and its salts, 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1H)-pyridone and its salts (preferably monoethanolamine salts), and mixtures thereof. Formula (P) discloses and encompasses tautomers of these compounds because equilibrium always exists. In at least one embodiment, the compound of formula (P) is piroctone olamine (octopirox).

[0046] In at least one embodiment, the alkyldiol is selected from the group consisting of 1,2-pentanediol, 1,2-hexanediol, 1,6-hexanediol, 1,2-octanediol, 1,2-heptanediol, 1,2-decanediol, methylpropanediol, and mixtures thereof.

[0047] In at least one embodiment, the halogen compound is selected from the group consisting of chlorhexidine and its salts, triclosan, chlorphenesin, trichlorcarban, chloroxylenol, bronopol, crimbazole, and mixtures thereof.

[0048] In at least one embodiment, the isothiazolinone is selected from the group consisting of methylisothiazolinone, methylchloroisothiazolinone, benzylisothiazolinone, and mixtures thereof.

[0049] In at least one embodiment, the antimicrobial agent is selected from the group consisting of aromatic alcohols, organic acids and their salts, hydroxamic acids and their salts, hydroxyacetophenone, hydroxypyridone, alkyldiols, halogen compounds, isothiazolinone, and mixtures thereof.

[0050] In at least one embodiment, the antimicrobial agent is selected from the group consisting of phenoxyethanol, benzyl alcohol, phenethyl alcohol, benzoic acid and its salts, caprylhydroxamic acid, hydroxyacetophenone, piroctone olamine, and mixtures thereof.

[0051] In a preferred embodiment, the antimicrobial agent is 1,2-octanediol, particularly a bio-based 1,2-octanediol, such as the bio-1,2-octanediol disclosed in WO2019 / 152569.

[0052] Appropriate antimicrobial agents are also listed in Annex V of Regulation (EC) No. 1223 / 2009 of the European Parliament and the Council of November 30, 2009, relating to cosmetics (updated September 28, 2022).

[0053] The weight ratio of compound X to additional antimicrobial agent (if any) as defined herein is preferably 20:1 to 1:20, more preferably 15:1 to 1:15, even more preferably 10:1 to 1:10, particularly preferably 5:1 to 1:5, for example 1:1.

[0054] The present invention also relates to an oral care formulation, the oral care formulation comprising, based on the total weight of the oral care formulation, 0.1 to 20% by weight, preferably 0.2 to 10% by weight, more preferably 0.3 to 5% by weight, even more preferably 0.4 to 3% by weight, and particularly preferably 0.5 to 2% by weight of compound X as defined herein.

[0055] In a preferred embodiment, the oral care formulation is selected from the group consisting of toothpaste, oral gel, mouthwash, toothpaste powder, and chewing gum. In a more preferred embodiment, the oral care formulation is selected from the group consisting of toothpaste and mouthwash. In a particularly preferred embodiment, the oral care formulation is toothpaste. In another particularly preferred embodiment, the oral care formulation is mouthwash.

[0056] In one embodiment, the oral care formulation includes a solvent. The solvent is preferably selected from water, propylene glycol, isopropanol, and mixtures thereof.

[0057] In one embodiment, the oral care formulation includes a humectant. The humectant is preferably selected from sorbitol, glycerin, xylitol, and mixtures thereof. The wetting agent is included, for example, in an amount of 10 to 70% by weight, preferably 30 to 60% by weight, for example 40 to 55% by weight, based on the total weight of the oral care preparation.

[0058] In one embodiment, the oral care formulation includes an abrasive. The abrasive is preferably selected from silica abrasives, hydrated silica, hydrated alumina, calcium abrasives, tricalcium phosphate, hydroxyapatite, dicalcium phosphate dihydrate, calcium pyrophosphate, calcium carbonate, sodium metaphosphate, potassium metaphosphate, aluminum silicate, calcined alumina, bentonite, sodium bicarbonate, and mixtures thereof. The abrasive may be present in an amount of 10 to 30% by weight, preferably 15 to 25% by weight, based on the total weight of the oral care formulation.

[0059] In one embodiment, the oral care formulation includes an anti-calculus agent. The anti-calculus agent is preferably selected from phosphates, polyphosphates, pyrophosphates (e.g., tetrasodium pyrophosphate), polyaminopropanesulfonic acid, hexametaphosphates, zinc citrate trihydrate, polypeptides, polyolefin sulfons, polyolefin phosphates, diphosphonates, and mixtures thereof. The anti-calculus agent may be present in an amount of 0.01 to 20% by weight, preferably 0.1 to 10% by weight, based on the total weight of the oral care formulation.

[0060] In one embodiment, the oral care formulation includes a fluoride source. The fluoride source is preferably selected from stannous fluoride, sodium fluoride, potassium fluoride, sodium monofluorophosphate, sodium fluorosilicate, ammonium fluorosilicate, amine fluoride, ammonium fluoride, calcium fluoride, aluminum fluoride, fluorohydroxyapatite, and mixtures thereof.

[0061] The fluoride source may be present in an amount of 0.01 to 10% by weight, preferably 0.1 to 2% by weight, based on the total weight of the oral care formulation. The fluoride source may be present in an amount of 0.01 to 1% by weight, preferably 0.02 to 0.5% by weight, more preferably 0.03 to 0.3% by weight, even more preferably 0.04 to 0.2% by weight, and particularly preferably 0.05 to 0.15% by weight, based on the total weight of the oral care formulation. The fluoride source may be present in an amount of 0.01 to 0.15% by weight, preferably 0.02 to 0.15% by weight, more preferably 0.03 to 0.15% by weight, even more preferably 0.04 to 0.15% by weight, and particularly preferably 0.05 to 0.15% by weight, based on the total weight of the oral care formulation. In a preferred embodiment, the oral care formulation is toothpaste, and the toothpaste contains the fluoride source.

[0062] In one embodiment, the oral care formulation includes a polymer. The polymer is preferably selected from polyethylene glycol, polysaccharides (e.g., cellulose derivatives, e.g., carboxymethylcellulose, hydroxymethylcellulose, ethylcellulose, microcrystalline cellulose), or polysaccharide gums (e.g., xanthan gum, guar gum, or carrageenan gum), or polyacrylates, or polymers based on N-vinylpyrrolidone, and mixtures thereof. The polymer may be present in an amount of 0.1 to 10% by weight, preferably 0.5 to 5% by weight, based on the total weight of the oral care formulation.

[0063] In one embodiment, the oral care formulation includes an anionic polymer. The anionic polymer is preferably selected from polycarboxylate, polyacrylic acid, polyacrylate, polyphosphonic acid, crosslinked carboxyvinyl copolymer, and mixtures thereof. The anionic polymer may be present in an amount of 1 to 20% by weight, preferably 5 to 15% by weight, based on the total weight of the oral care formulation.

[0064] In one embodiment, the oral care formulation includes a thickening agent. The thickening agent is preferably selected from silica thickeners, carboxyvinyl polymers, carrageenan, hydroxyethylcellulose, cellulose ether salts such as sodium carboxymethylcellulose or sodium carboxymethylhydroxyethylcellulose, karaya, gum arabic, tragacanth gum, colloidal magnesium aluminum silicate, and mixtures thereof. The thickening agent may be present in an amount of 0.1 to 10% by weight, preferably 0.5 to 5% by weight, based on the total weight of the oral care formulation.

[0065] In one embodiment, the oral care formulation includes a foaming agent. The foaming agent is preferably selected from polyethylene glycol, alginate polymer, and mixtures thereof. The foaming agent may be present in an amount of 0.1 to 20% by weight, preferably 1 to 10% by weight, based on the total weight of the oral care formulation.

[0066] In one embodiment, the oral care formulation contains a surfactant. The surfactant may be present in an amount of 0.1 to 20% by weight, preferably 1 to 10% by weight, based on the total weight of the oral care formulation.

[0067] In one embodiment, the surfactant is an anionic surfactant. The anionic surfactant is preferably selected from alkyl sulfates (e.g., sodium lauryl sulfate), alkyl ether sulfates (e.g., sodium laureth-2 sulfate), alkyl allyl sulfonates (e.g., sodium laurylbenzenesulfonate), alkyl sulfoacetates (e.g., sodium lauryl sulfoacetate), and mixtures thereof. In one embodiment, the surfactant is a sulfur-free anionic surfactant. The sulfur-free anionic surfactant is preferably selected from taurates (e.g., sodium cocoyl methyl taurate), glycinates (e.g., sodium cocoyl glycinate), sarcosinates (e.g., sodium lauroyl sarcosinate), quaternary ammonium compounds (e.g., benzalkonium chloride or cetylpyridinium chloride), and mixtures thereof.

[0068] In one embodiment, the surfactant is a nonionic surfactant. In one embodiment, the surfactant is a glucamide. In one embodiment, the surfactant is a glucamide of the following formula X. [ka] (In the formula, R is selected from saturated or unsaturated hydrocarbon chains having 5 to 23 carbon atoms.)

[0069] Preferably, R in formula (X) above is selected from saturated or unsaturated hydrocarbon chains having 7 to 17 carbon atoms. Also preferably, the RC=O residue in formula (X) above is derived from caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, coconut fatty acid, or a mixture thereof. Also preferably, the RC=O residue in formula (X) above is derived from 9-10-hydroxy-2-decenoic acid, 9-dodecenoic acid, or a mixture thereof. Particularly preferred glucamides of formula (X) above are capryloyl / caproyl methylglucamide, lauroyl / myristoyl methylglucamide, cocoyl methylglucamide, oleyl methylglucamide, or a mixture thereof. Such glucamides are commercially available from Clariant (GlucoTain® Clear, GlucoTain® Plus, GlucoTain® Flex, GlucoTain® Care, GlucoTain® Sense). Particularly preferred glucamides of formula (X) are N-9-decenoyl-N-methylglucamine, N-9-dodecenoyl-N-methylglucamine, or mixtures thereof.

[0070] In one embodiment, the surfactant is an alkyl polyglycoside (APG), preferably an alkyl polyglucoside. In another embodiment, the surfactant is an amphoteric surfactant, such as a betaine surfactant, such as cocoamidopropyl betaine. In yet another embodiment, the surfactant is a cationic surfactant.

[0071] In one embodiment, the oral care formulation includes a buffer or a pH adjuster. In a preferred embodiment, the pH of the oral care formulation is in the range of 4 to 8, preferably 4.5 to 7.5, more preferably 5 to 7, particularly preferably 5 to 6, also particularly preferably 5.5 to 6.5, and also particularly preferably 6 to 7. In a preferred embodiment, the oral care formulation is a toothpaste, and the pH of the toothpaste is in the range of 4 to 8, preferably 4.5 to 7.5, more preferably 5 to 7, particularly preferably 5 to 6, also particularly preferably 5.5 to 6.5, and also particularly preferably 6 to 7.

[0072] In one embodiment, the oral care formulation includes a flavoring agent, a sweetener, and / or a pigment or dye. Examples of flavors include mint, peppermint, spearmint, wintergreen, menthol, or strawberry. An example of a sweetener is sodium saccharin. An example of a pigment is titanium dioxide or zinc oxide.

[0073] The oral care preparation can be prepared, for example, by mixing its components.

[0074] The present invention also relates to a compound X selected from the following compounds of formula (I), glyceryl ethers, sorbitan esters, and isosorbide esters, for use in reducing the effects of caries-causing microorganisms, plaque-causing microorganisms, or gingivitis-causing microorganisms. [ka] (In the formula, R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof.)

[0075] Examples of such microorganisms include Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum, or Porphyromonas gingivalis. Preferred microorganisms are Streptococcus mutans or Lactobacillus acidophilus.

[0076] In a preferred embodiment, the microorganism causing tooth decay is the bacteria that cause tooth decay. In a preferred embodiment, the microorganism causing plaque is the bacteria that cause plaque. In a preferred embodiment, the microorganism causing gingivitis is the bacteria that cause gingivitis.

[0077] A preferred embodiment relates to a compound X selected from the following compounds of formula (I), glyceryl ethers, sorbitan esters, and isosorbide esters for use in reducing the effects of caries-causing bacteria, plaque-causing bacteria, or gingivitis-causing bacteria. [ka] (In the formula, R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof.)

[0078] Examples of such bacteria include Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum, or Porphyromonas gingivalis. Preferred bacteria are Streptococcus mutans or Lactobacillus acidophilus.

[0079] The present invention also relates to oral care formulations as defined herein for use in reducing the effects of caries-causing microorganisms, plaque-causing microorganisms, or gingivitis-causing microorganisms.

[0080] Examples of such microorganisms include Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum, or Porphyromonas gingivalis. Preferred microorganisms are Streptococcus mutans or Lactobacillus acidophilus.

[0081] In a preferred embodiment, the microorganism causing tooth decay is the bacteria that cause tooth decay. In a preferred embodiment, the microorganism causing plaque is the bacteria that cause plaque. In a preferred embodiment, the microorganism causing gingivitis is the bacteria that cause gingivitis.

[0082] A preferred embodiment relates to an oral care formulation as defined herein for use in reducing the effects of bacteria that cause tooth decay, bacteria that cause plaque, or bacteria that cause gingivitis.

[0083] Examples of such bacteria include Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum, or Porphyromonas gingivalis. Preferred bacteria are Streptococcus mutans or Lactobacillus acidophilus.

[0084] A preferred embodiment relates to a compound X selected from the compounds of formula (I), glyceryl ethers, sorbitan esters, and isosorbide esters for use in the prevention or treatment of tooth decay, plaque, or gingivitis. [ka] (In the formula, R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof.)

[0085] Examples of such microorganisms include Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum, or Porphyromonas gingivalis. Preferred microorganisms are Streptococcus mutans or Lactobacillus acidophilus.

[0086] In a preferred embodiment, the microorganism causing tooth decay is the bacteria that cause tooth decay. In a preferred embodiment, the microorganism causing plaque is the bacteria that cause plaque. In a preferred embodiment, the microorganism causing gingivitis is the bacteria that cause gingivitis.

[0087] A preferred embodiment relates to a compound X selected from the compounds of formula (I), glyceryl ethers, sorbitan esters, and isosorbide esters for use in the prevention or treatment of tooth decay, plaque, or gingivitis. [ka] (In the formula, R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof.)

[0088] Examples of such bacteria include Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum, or Porphyromonas gingivalis. Preferred bacteria are Streptococcus mutans or Lactobacillus acidophilus.

[0089] The present invention relates to oral care formulations as defined herein for use in the prevention or treatment of tooth decay, plaque, or gingivitis.

[0090] Examples of such microorganisms include Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum, or Porphyromonas gingivalis. Preferred microorganisms are Streptococcus mutans or Lactobacillus acidophilus.

[0091] In a preferred embodiment, the microorganism causing tooth decay is the bacteria that cause tooth decay. In a preferred embodiment, the microorganism causing plaque is the bacteria that cause plaque. In a preferred embodiment, the microorganism causing gingivitis is the bacteria that cause gingivitis.

[0092] A preferred embodiment relates to an oral care formulation as defined herein for use in the prevention or treatment of tooth decay, plaque, or gingivitis.

[0093] Examples of such bacteria include Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum, or Porphyromonas gingivalis. Preferred bacteria are Streptococcus mutans or Lactobacillus acidophilus.

[0094] The present invention also relates to a method for reducing the effects of caries-causing microorganisms, plaque-causing microorganisms, or gingivitis-causing microorganisms, the method comprising the step of contacting caries-causing microorganisms, plaque-causing microorganisms, or gingivitis-causing microorganisms with compound X as defined herein or an oral care formulation.

[0095] Examples of such microorganisms include Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum, or Porphyromonas gingivalis. Preferred microorganisms are Streptococcus mutans or Lactobacillus acidophilus.

[0096] In a preferred embodiment, the microorganism causing tooth decay is the bacteria that cause tooth decay. In a preferred embodiment, the microorganism causing plaque is the bacteria that cause plaque. In a preferred embodiment, the microorganism causing gingivitis is the bacteria that cause gingivitis.

[0097] A preferred embodiment relates to a method for reducing the effects of caries-causing bacteria, plaque-causing bacteria, and gingivitis-causing bacteria, the method comprising the step of contacting caries-causing microorganisms, plaque-causing microorganisms, or gingivitis-causing microorganisms with compound X as defined herein or an oral care formulation as defined herein. Examples of such bacteria include Streptococcus mutans, Streptococcus sanguinis, Streptococcus sobrinus, Streptococcus gordonii, Lactobacillus acidophilus, Fusobacterium nucleatum, or Porphyromonas gingivalis. The preferred bacteria are Streptococcus mutans or Lactobacillus acidophilus.

[0098] The present invention also relates to a method for preventing or treating tooth decay, plaque, or gingivitis, the method comprising the step of bringing compound X as defined herein or an oral care preparation as defined herein into contact with the oral cavity of a person requiring such treatment.

[0099] The present invention also relates to the use of compound X as defined herein or an oral care formulation as defined herein for the prevention or treatment of tooth decay, plaque, or gingivitis.

[0100] In this specification, unless otherwise specified, the following definitions apply: All percentages are based on the total weight (w / w) of the composition. All ratios are weight ratios. "Weight %" means weight percentage.

[0101] "Molecular weight," "M.Wt.," or "MW," and their grammatical equivalents, refer to the number-average molecular weight.

[0102] Viscosity was measured at 25°C using a HAAKE rotational viscometer VT550 equipped with a cooling / heating vessel and a sensor system compliant with DIN53019, at a shear rate of 12.9 s. ‐1 It is measured at [location / location].

[0103] "Water-soluble" refers to any substance that is sufficiently water-soluble at a concentration of 0.1% by weight in water at 25°C to form a transparent solution visible to the naked eye. The term "water-insoluble" refers to any substance that is not "water-soluble."

[0104] "Dry" or "substantially dry" means that any compound or composition in liquid form contains less than 5%, less than 3%, less than 2%, less than 1%, or about 0%, as measured under ambient conditions of 25°C. Such compounds or compositions in liquid form include water, oil, organic solvents, and other wetting agents. "Anhydrous" means that a composition contains less than 5%, less than 3%, less than 2%, less than 1%, or about 0%, of water relative to the total weight of the composition.

[0105] "Substantially free from" or "substantially free of" means less than 1%, less than 0.8%, less than 0.5%, less than 0.3%, or about 0% of the total weight of the composition.

[0106] The term "derivative" includes, but is not limited to, amide, ether, ester, amino, carboxyl, acetyl, acid, salt, and / or alcohol derivatives of a particular compound. In at least one embodiment, "its derivative" means an amide, ether, ester, amino, carboxyl, acetyl, acid, salt, or alcohol derivative. [Examples]

[0107] The following embodiments are intended to illustrate the subject matter of the present invention and are not limiting in any way.

[0108] material Velsan® Flex is marketed by Clariant. Chemical name: Capryloyl / caproylanhydromethylglucamide (and) water, active ingredient: 70% by weight. Capryloyl / caproylanhydromethylglucamide is a mixture of the compound of formula (I) where R is -(CH2)8CH3 and the compound of formula (I) where R is -(CH2)6CH3. Velsan® EHG is marketed by Clariant. Chemical name: Ethylhexylglycerin.

[0109] Example 1: Microbial Testing Microbiological testing was performed in accordance with BSEN1040:2005. Sample solutions of 1.1%, 2%, 3%, and 5% were prepared with sterile tap water. 2. An inoculation suspension using Streptococcus mutans was prepared. 3.10 ml of sterile tap water and 1.0 ml of inoculant were placed in a test tube. 4.8 ml of the sample solution was added, and a stopwatch was started to homogenize the mixture. 5.1 ml of the solution obtained after 5.2 minutes was taken, and plate counting was performed using a standard plate culture method. To prove that only the contained active substances are responsible for the reduction of Streptococcus mutans, this was also done with blank samples.

[0110] [Table 1]

[0111] [Table 2]

[0112] [Table 3]

[0113] [Table 4]

[0114] [Table 5]

[0115] [Table 6]

[0116] [Table 7]

[0117] [Table 8]

[0118] Example 8: Toothpaste for biomembrane-forming bacteria in the oral cavity The reduction effect of toothpaste samples on biofilm-forming bacteria such as Streptococcus was tested over a maximum of 5 minutes. Biofilms of the test bacteria (Streptococcus mutans) were cultured, and then a toothpaste solution (40% toothpaste dissolved in tap water) was applied to the biofilm. The reduction effect was quantified by measuring the bacterial count after the elapsed time. The control experiment using tap water served as a baseline to rule out the influence of tap water on bacteria. The toothpastes used were listed in the table below.

[0119] [Table 9]

[0120] Toothpaste was tested with and without the addition of Velsan Flex (2% and 3%). The table below shows the colony-forming units / ml or g in the sample after 5 minutes:

[0121] [Table 10]

[0122] conclusion The addition of Velsan Flex results in a reduction in the test bacteria.

Claims

1. Use of compound X, selected from the compounds of formula (I), glyceryl ether, sorbitan ester, and isosorbide ester, as an antimicrobial agent against microorganisms that cause tooth caries, microorganisms that cause plaque, or microorganisms that cause gingivitis. 【Chemistry 1】 (In the formula, R is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof.)

2. In formula (I), R is selected from saturated hydrocarbon chains having 5 to 17 carbon atoms, unsaturated hydrocarbon chains having 5 to 17 carbon atoms, and mixtures thereof. Preferably selected from saturated hydrocarbon chains having 5 to 13 carbon atoms, unsaturated hydrocarbon chains having 5 to 13 carbon atoms, and mixtures thereof. Use of claim 1, particularly preferably selected from saturated hydrocarbon chains having 7 to 9 carbon atoms, unsaturated hydrocarbon chains having 7 to 9 carbon atoms, and mixtures thereof.

3. The use of claim 1 or 2, wherein the glyceryl ether is a monoether or diether of glycerin and one or more C6-C20 fatty alcohols, preferably a monoether or diether of glycerin and one or more C8-C14 fatty alcohols, and particularly preferably a monoether of glycerin and one or more C8 fatty alcohols.

4. The sorbitan ester is a monoester, diester, or triester of sorbitan and one or more C6-C20 fatty acids, preferably a monoester or diester of sorbitan and one or more C8-C14 fatty acids, and particularly preferably a monoester or diester of sorbitan and caprylic acid, as described in any of claims 1 to 3.

5. The use of any one of claims 1 to 4, wherein the sorbitan ester is selected from sorbitan caprylate, sorbitan stearate, sorbitan olivete, sorbitan oleate, sorbitan caprate, sorbitan laurate, sorbitan myristate, sorbitan caproate, and mixtures thereof, preferably sorbitan caprylate.

6. The use of any one of claims 1 to 5, wherein the isosorbide ester is a monoester or diester of isosorbide and one or more C6-C20 fatty acids, preferably a monoester or diester of isosorbide and one or more C8-C14 fatty acids, and particularly preferably a monoester or diester of isosorbide and caprylic acid.

7. The use of any one of claims 1 to 8, wherein the isosorbide ester is selected from isosorbide caprylate, isosorbide stearate, isosorbide oliveate, isosorbide oleate, isosorbide caprate, isosorbide laurate, isosorbide myristic acid, isosorbide caproic acid, and mixtures thereof, preferably isosorbide caprylate.

8. Compound X as defined in any of claims 1 to 7, for use in reducing the effects of microorganisms that cause tooth decay, microorganisms that cause plaque, or microorganisms that cause gingivitis.

9. Compound X as defined in any of claims 1 to 7, for use in the prevention or treatment of tooth decay, plaque, or gingivitis.

10. An oral care formulation comprising, based on the total weight of the oral care formulation, 0.1 to 20% by weight, preferably 0.2 to 10% by weight, more preferably 0.3 to 5% by weight, even more preferably 0.4 to 3% by weight, and particularly preferably 0.5 to 2% by weight of compound X as defined in any of claims 1 to 7.

11. The oral care preparation according to claim 10, wherein the oral care preparation is selected from the group consisting of toothpaste, oral gel, mouthwash, toothpaste powder, and chewing gum.

12. An oral care formulation according to claim 10 or 11 for use in reducing the effects of caries-causing microorganisms, plaque-causing microorganisms, or gingivitis-causing microorganisms.

13. An oral care formulation according to claim 10 or 11 for use in the prevention or treatment of tooth decay, plaque, or gingivitis.

14. A method for reducing the effects of microorganisms that cause tooth decay, microorganisms that cause plaque, or microorganisms that cause gingivitis, comprising the step of contacting the microorganisms that cause tooth decay, microorganisms that cause plaque, or microorganisms that cause gingivitis with compound X as defined in any one of claims 1 to 7 or an oral care preparation as defined in claim 10 or 11.

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