Antibacterial combinations

Abstract

The present invention relates to a combination comprising: (A) at least one compound selected from the group consisting of a compound of formula (I), a sorbitan ester, an isosorbide ester, a glyceryl ether, and a glyceryl ester; and [Case 1] JPEG2025537107000036.jpg3877 (wherein R is selected from a saturated hydrocarbon chain having 5 to 23 carbon atoms, an unsaturated hydrocarbon chain having 5 to 23 carbon atoms, and mixtures thereof.) (B) at least one hydroxyacetophenone;

Description

[Technical Field]

[0001] The present invention relates to an antibacterial combination, its use as an antibacterial agent, and formulations containing said antibacterial combination. [Background technology]

[0002] Preserving household and cosmetic formulations extends their shelf life, thus providing greater value to consumers. Additionally, preservatives prevent consumers from spreading microorganisms around the home or on themselves, thus providing health benefits. Antimicrobial agents are well documented in the art, and many are available that offer excellent performance.

[0003] However, there is a need to provide advanced preservative systems that minimize the level of preservative active ingredients while still providing excellent antimicrobial performance. Many well-known preservative active ingredients with excellent efficacy are disfavored due to low consumer acceptance, health concerns, or regulatory restrictions. For similar reasons, the levels of such active ingredients may also be (legally) limited. Furthermore, there is a need for all elements of preservative systems to meet sustainability goals, ensuring that household and cosmetic formulations are as environmentally friendly as possible. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] WO2018 / 002100 [Patent Document 2] European Patent Application No. 21200587.0 Summary of the Invention [Problem to be solved by the invention]

[0005] Therefore, there is a need to provide more advanced preservative systems that provide excellent antimicrobial efficacy, have high consumer acceptance, do not raise health or regulatory concerns, and have excellent sustainability and environmentally friendly properties.

[0006] The present invention relates to a combination comprising: (A) at least one compound selected from the group consisting of compounds of the following formula (I), sorbitan esters, isosorbide esters, glyceryl ethers, and glyceryl esters; (A) at least one compound selected from the group consisting of compounds of the following formula (I), sorbitan esters, isosorbide esters, glyceryl ethers, and glyceryl esters; and [ka] 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. (B) at least one hydroxyacetophenone;

[0007] Advantageously, the combination of the present invention exhibits synergistic effects against a wide range of microorganisms. This allows formulations, such as cosmetic and household formulations, to be preserved with fewer preservatives, reducing the potential for adverse effects from antimicrobial active ingredients and conserving resources. Advantageously, the combination of the present invention has a high renewable carbon content. The combination of the present invention is sustainable.

[0008] The combination of the present invention comprises (A) at least one compound selected from the group consisting of compounds of formula (I) below, sorbitan esters, isosorbide esters, glyceryl ethers, and glyceryl esters. [ka] 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.

[0009] In one embodiment, the combination of the present invention comprises (A) at least one compound selected from compounds of formula (I): [ka] 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.

[0010] Preferably, R in formula (I) is selected from a saturated hydrocarbon chain having 5 to 17 carbon atoms, an unsaturated hydrocarbon chain having 5 to 17 carbon atoms, and a mixture thereof. More preferably, R in formula (I) is selected from a saturated hydrocarbon chain having 5 to 13 carbon atoms, an unsaturated hydrocarbon chain having 5 to 13 carbon atoms, and a mixture thereof.

[0011] Particularly preferably, R in formula (I) is selected from saturated hydrocarbon chains having 5 to 9 carbon atoms, unsaturated hydrocarbon chains having 5 to 9 carbon atoms and mixtures thereof.

[0012] In at least one embodiment, R of formula (I) is selected from —(CH2)6CH3, —(CH2)8CH3, and mixtures thereof; or R of formula (I) is —(CH2) 10 CH3, -(CH2) 12 or R in formula (I) is selected from -(CH2)7CH=CH2, -(CH2)7CH=CHCH2CH3, and mixtures thereof; or the R C=O residue in formula (I) is derived from coconut fatty acid; or the R C=O residue in formula (I) is derived from soybean fatty acid.

[0013] 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) 12In 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 in formula (I) is derived from coconut fatty acid. In at least one embodiment, the R C=O residue in formula (I) is derived from soybean fatty acid.

[0014] As used herein, the phrase "the RC=O residue of formula (I) is derived from a coconut fatty acid" preferably means that the carbon chain length distribution of the RC=O residue of formula (I) corresponds to the carbon chain length distribution of the fatty acids (e.g., bound as triglycerides) in coconut oil.

[0015] As used herein, the phrase "the R═O residue of formula (I) is derived from soybean fatty acids" preferably means that the carbon chain length distribution of the R═O residue of formula (I) corresponds to the carbon chain length distribution of the fatty acids (e.g., bound as triglycerides) in soybean oil.

[0016] Preferably, the weight ratio of the compound of formula (I) wherein R is (CH2)6CH3 to the compound of formula (I) wherein R is -(CH2)8CH3 is from 1:9 to 9:1, preferably from 3:7 to 7:3.

[0017] Preferably, R is (CH2) 10 Compounds of formula (I) where R is -(CH) 12 The weight ratio of the compound of formula (I) that is CH3 is from 1:9 to 9:1, preferably from 3:7 to 7:3.

[0018] Preferably, the weight ratio of the compound of formula (I) wherein R is -(CH2)7CH=CH2 to the compound of formula (I) wherein R is -(CH2)7CH=CHCH2CH3 is from 1:9 to 9:1, preferably from 3:7 to 7:3.

[0019] Compounds of formula (I) are described, for example, in patent document WO2018 / 002100 and patent document 2 (European Patent Application No. 21200587.0).

[0020] In one embodiment, the combination of the present invention comprises (A) at least one compound selected from sorbitan esters and isosorbide esters.

[0021] In one embodiment, the combination of the present invention comprises (A) at least one compound selected from sorbitan esters.

[0022] Preferably, the sorbitan ester is a monoester, diester, or triester of sorbitan and one or more C6-C20 fatty acids. More preferably, the sorbitan ester is a monoester or diester of sorbitan and one or more C8-C14 fatty acids. Particularly preferably, the sorbitan ester is a monoester or diester of sorbitan and caprylic acid.

[0023] Preferably, the sorbitan ester is selected from sorbitan caprylate, sorbitan stearate, sorbitan olivate, sorbitan oleate, sorbitan caprate, sorbitan laurate, sorbitan myristate, sorbitan caproate, and mixtures thereof. Particularly preferably, the sorbitan ester is sorbitan caprylate.

[0024] In one embodiment, the combination of the present invention comprises (A) at least one compound selected from isosorbide esters.

[0025] Preferably, the isosorbide ester is a mono- or diester of isosorbide and one or more C6-C20 fatty acids. More preferably, the isosorbide ester is a mono- or diester of isosorbide and one or more C8-C14 fatty acids. Particularly preferably, the isosorbide ester is a mono- or diester of isosorbide and caprylic acid.

[0026] Preferably, the isosorbide ester is selected from isosorbide caprylate, isosorbide stearate, isosorbide olivate, isosorbide oleate, isosorbide caprate, isosorbide laurate, isosorbide myristate, isosorbide caproate, and mixtures thereof. Particularly preferably, the isosorbide ester is isosorbide caprylate.

[0027] In one embodiment, the combination of the present invention includes (A) at least one compound selected from glyceryl ethers. Preferably, the glyceryl ether is a mono- or di-ether of glycerin and one or more C6-C20 fatty alcohols, more preferably a mono- or di-ether of glycerin and one or more C8-C14 fatty alcohols. Particularly preferably, the glyceryl ether is a mono- or di-ether of glycerin and one or more C8 fatty alcohols. In at least one embodiment, the glyceryl ether is selected from ethylhexylglycerin, methylheptylglycerin, caprylyl glyceryl ether, and mixtures thereof.

[0028] In one embodiment, the combination of the present invention includes (A) at least one compound selected from glyceryl esters. In at least one embodiment, the glyceryl ester is selected from glyceryl caprylate, glyceryl caprate, and mixtures thereof. In one embodiment, the glyceryl ester is glyceryl caprylate / caprate.

[0029] In one embodiment, the combination of the present invention comprises (A) at least one compound selected from sorbitan esters, and the hydroxyl value of the at least one compound selected from sorbitan esters is preferably 320 or less, more preferably 285 or less, even more preferably 245 or less, and particularly preferably 225 or less.

[0030] In one embodiment, the combination of the present invention comprises (A) at least one compound selected from isosorbide esters, and the hydroxyl value of the at least one compound selected from isosorbide esters is preferably 320 or less, more preferably 285 or less, even more preferably 245 or less, and particularly preferably 225 or less.

[0031] In one embodiment, the combination of the present invention comprises (A) a mixture of at least one compound selected from sorbitan esters and at least one compound selected from isosorbide esters. In one embodiment, the combination of the present invention comprises (A) a mixture of at least one compound selected from sorbitan esters and at least one compound selected from isosorbide esters, wherein the hydroxyl value of the mixture is preferably 320 or less, more preferably 285 or less, even more preferably 245 or less, and particularly preferably 225 or less. The hydroxyl value of a substance refers to the number of mg of KOH that will bind to the amount of acetic acid upon acetylation of 1 g of the substance.

[0032] Suitable methods for determining the hydroxyl number are, for example, DGF CV 17 a (53), Ph. Eur. 2.5.3 Method A and DIN 53240.

[0033] The following procedure is suitable: weigh out 1 g (accurate to 0.1 mg) of the homogenized sample to be measured. Add 20.00 ml of acetylation mixture (acetylation mixture: 50 ml of acetic anhydride stirred in 1 liter of pyridine). Completely dissolve the sample in the acetylation mixture with appropriate stirring and heating. Add 5 ml of catalyst solution (catalyst solution: 2 g of 4-dimethylaminopyridine dissolved in 100 ml of pyridine). Close the reactor and place it in a preheated water bath at 55 °C for 10 minutes with stirring. Then, add 10 ml of fully deionized water to the reaction solution, close the reactor again, and let the mixture react again in the water bath for 10 minutes with stirring. Allow the sample to cool to room temperature (25 °C). Then, add 50 ml of 2-propanol and 2 drops of phenolphthalein. Titrate this solution with aqueous sodium hydroxide (aqueous sodium hydroxide solution c = 0.5 mol / l) (Va). Under the same conditions, but without adding any sample, the effectiveness of the acetylation mixture is determined (Vb).

[0034] The hydroxyl value (OHV) is calculated from the amount of aqueous sodium hydroxide consumed in the potency measurement and sample titration using the following formula:

number

[0035] (Vb-Va) is the volume (ml) of aqueous sodium hydroxide solution used, which corresponds to the amount of acetic acid bound during the acetylation of the sample being measured.

[0036] The combinations of the present invention include (B) at least one hydroxyacetophenone.

[0037] Preferably, the hydroxyacetophenone is selected from 2-hydroxyacetophenone, 3-hydroxyacetophenone, 4-hydroxyacetophenone, and mixtures thereof.

[0038] As used herein, 2-hydroxyacetophenone refers to a compound having the formula: [ka]

[0039] As used herein, 3-hydroxyacetophenone refers to a compound having the formula: [ka]

[0040] As used herein, 4-hydroxyacetophenone refers to a compound having the following formula: [ka]

[0041] Particularly preferably, the hydroxyacetophenone is 4-hydroxyacetophenone, which is described, for example, in WO2014 / 135650 A1.

[0042] Preferably, the weight ratio of (A) at least one compound selected from the group consisting of compounds of formula (I), sorbitan esters, isosorbide esters, glyceryl ethers, and glyceryl esters to (B) at least one hydroxyacetophenone is from 20:1 to 1:5, more preferably from 15:1 to 1:2, even more preferably from 12:1 to 1:1, particularly preferably from 10:1 to 3:1, for example from 6:1 to 7:1.

[0043] In a preferred embodiment, the combination of the present invention comprises: (A) at least one compound selected from the group consisting of compounds of formula (I): [ka] 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. (B) at least one hydroxyacetophenone;

[0044] In a preferred embodiment, the combination of the present invention comprises: (A) at least one compound selected from the group consisting of compounds of formula (I): [ka] wherein R is selected from saturated hydrocarbon chains having 5 to 13 carbon atoms, unsaturated hydrocarbon chains having 5 to 13 carbon atoms, and mixtures thereof. (B) at least one hydroxyacetophenone, wherein the hydroxyacetophenone is selected from 2-hydroxyacetophenone, 3-hydroxyacetophenone, 4-hydroxyacetophenone, and mixtures thereof.

[0045] In a particularly preferred embodiment, the combination of the present invention comprises: (A) at least one compound selected from the group consisting of compounds of formula (I): [ka] wherein R is selected from —(CH)CH, —(CH)CH, and mixtures thereof. (B) at least one hydroxyacetophenone, wherein the hydroxyacetophenone is 4-hydroxyacetophenone.

[0046] In at least one embodiment, the combination of the present invention is a blend comprising, based on the total weight of the blend, 25 to 99 wt. %, preferably 40 to 80 wt. %, more preferably 55 to 70 wt. %, and most preferably 60 to 65 wt. % of (A) at least one compound selected from the group consisting of compounds of formula (I), sorbitan esters, isosorbide esters, glyceryl ethers, and glyceryl esters; and 1 to 50 wt. %, preferably 2 to 20 wt. %, more preferably 5 to 15 wt. %, and most preferably 8 to 12 wt. % of (B) at least one hydroxyacetophenone.

[0047] In at least one embodiment, the blend is an aqueous solution. In at least one embodiment, the blend includes a solvent. In at least one embodiment, the blend includes a solvent, the solvent including water and / or alcohol. The solvent is useful for providing the compounds used in the present invention in liquid form. In at least one embodiment, the solvent is cosmetically acceptable. In at least one embodiment, the blend includes at least 10% by weight, preferably at least 20% by weight, more preferably at least 30% by weight, and even more preferably at least 50% by weight of water. Water is useful for economic reasons, but is also useful for cosmetically acceptable reasons. Optionally, the blend includes a water-miscible or water-soluble solvent, such as a lower alkyl alcohol. In at least one embodiment, the blend includes a C1-C5 alkyl monohydric alcohol, preferably a C2-C3 alkyl monohydric alcohol. The alcohol that may be present is preferably a lower monohydric or polyhydric alcohol having 1 to 4 carbon atoms, such as ethanol and isopropanol, which are commonly used for cosmetic purposes.

[0048] Optionally, the blend includes a water-soluble polyhydric alcohol. In at least one embodiment, the water-soluble polyhydric alcohol is a polyhydric alcohol having two or more hydroxyl groups in the molecule. In at least one embodiment, the water-soluble polyhydric alcohol is a dihydric alcohol such as ethylene glycol, propylene glycol, trimethylene glycol, 1,2-butylene glycol, 1,3-butylene glycol, 1,4-butylene glycol, tetramethylene glycol, 2,3-butylene glycol, pentamethylene glycol, 2-butene-1,4-diol, hexylene glycol, octylene glycol, etc.; a trihydric alcohol such as glycerin, trimethylolpropane, 1,2,6-hexanetriol, etc.; a tetrahydric alcohol such as pentaerythritol; a pentahydric alcohol such as xylitol; a hexahydric alcohol such as sorbitol, mannitol; diethylene glycol, dipropylene glycol, polyethylene glycol, poly Polyhydric alcohol polymers such as propylene glycol, tetraethylene glycol, diglycerin, polyethylene glycol, triglycerin, tetraglycerin, and polyglycerin; dihydric alcohol alkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monophenyl ether, ethylene glycol monohexyl ether, ethylene glycol mono-2-methylhexyl ether, ethylene glycol isoamyl ether, ethylene glycol benzyl ether, ethylene glycol isopropyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, and ethylene glycol dibutyl ether;Dihydric alcohol alkyl ethers such as diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol butyl ether, diethylene glycol methyl ethyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol isopropyl ether, dipropylene glycol methyl ether, dipropylene glycol ethyl ether, and dipropylene glycol butyl ether; ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, ethylene glycol Dihydric alcohol ether esters such as diethylene glycol monophenyl ether acetate, ethylene glycol diadipate, ethylene glycol disuccinate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, and propylene glycol monophenyl ether acetate; glycerin monoalkyl ethers such as xyl alcohol, selachyl alcohol, and batyl alcohol; sorbitol, maltitol, maltotriose, mannitol, sucrose, erythritol, glucose, fructose, starch sugar, maltose, xylitose, starch sugar reducing alcohol, glysolid, tetrahydrofurfuryl alcohol, POE tetrahydrofurfuryl alcohol, POP butyl ether, and POP Sugar alcohols such as POE butyl ether, tripolyoxypropylene glycerin ether, POP glycerin ether, POP glycerin ether phosphate, POP POE pentaneerythritol ether, and mixtures thereof;

[0049] In a preferred embodiment, the blend comprises a solvent selected from the group consisting of water, glycol, ethanol, and mixtures thereof. In a preferred embodiment, the blend comprises water.

[0050] In a preferred embodiment, the blend comprises an aqueous, alcoholic or aqueous-alcoholic solvent, wherein the aqueous, alcoholic or aqueous-alcoholic solvent comprises water, ethanol, propanol, isopropanol, 1,2-propylene glycol, 1,3-propylene glycol, isobutanol, butanol, butyl glycol, butyl diglycol, glycerol, or a mixture thereof; preferably, the aqueous, alcoholic or aqueous-alcoholic solvent comprises water, ethanol, propanol, isopropanol, 1,2-propylene glycol, 1,3-propylene glycol, glycerol, or a mixture thereof; more preferably, the aqueous, alcoholic or aqueous-alcoholic solvent comprises water, isopropanol, 1,2-propylene glycol, 1,3-propylene glycol, or a mixture thereof; even more preferably, the aqueous, alcoholic or aqueous-alcoholic solvent consists of water or a mixture of water and an alcohol, wherein the alcohol is selected from the group consisting of isopropanol, 1,2-propylene glycol and 1,3-propylene glycol.

[0051] The combination of the present invention optionally comprises (c) at least one additional antibacterial agent.

[0052] The blends of the present invention optionally include (c) at least one additional antimicrobial agent.

[0053] 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, compounds of formula (P), alkyl diols, halogenated compounds, isothiazolinones, and combinations thereof, wherein formula (P) is as follows: [ka] (wherein R1′ is H, unsubstituted or halogen-substituted, branched or unbranched C1-C 20 Alkyl groups, unsubstituted or halogen-substituted C5-C8 cycloalkyl groups, unsubstituted or halogen-substituted C6-C 10 Aryl group, or unsubstituted or halogen-substituted, branched or unbranched C7-C 20 aralkyl groups, R2' is O or S, R3' is H or a C1-C4 alkyl group, X + is a cation.) Preferably, R3' is methyl.

[0054] 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.

[0055] In at least one embodiment, the organic acids and their 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.

[0056] In at least one embodiment, the hydroxamic acid is selected from hydroxamic acids of formula (III): [ka] (In the formula, R 1 is selected from saturated hydrocarbon chains having 5 to 23 carbon atoms, unsaturated hydrocarbon chains having 5 to 23 carbon atoms, and mixtures thereof.

[0057] Preferably, R in formula (III) 1is selected from saturated hydrocarbon chains having 5 to 17 carbon atoms, unsaturated hydrocarbon chains having 5 to 17 carbon atoms, and mixtures thereof. More preferably, R in formula (III) 1 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 preferably, R in formula (III) 1 is selected from saturated hydrocarbon chains having 7 carbon atoms, unsaturated hydrocarbon chains having 7 carbon atoms, and mixtures thereof.

[0058] Preferred hydroxamic acids are selected from caprylhydroxamic acid, hexanohydroxamic acid, caprohydroxamic acid, laurohydroxamic acid, and mixtures thereof. Particularly preferred hydroxamic acids are caprylhydroxamic acid. Caprylhydroxamic acid is also called caprylohydroxamic acid or octanohydroxamic acid. Hydroxamic acids are described, for example, in EP2224973. Examples of hydroxamic acid salts include alkali metal salts of hydroxamic acid (e.g., sodium salts of hydroxamic acid or potassium salts of hydroxamic acid) or alkaline earth metal salts of hydroxamic acid (e.g., magnesium salts of hydroxamic acid or calcium salts of hydroxamic acid).

[0059] In at least one embodiment, the compound according to formula (P) is selected from the group consisting of 2-hydroxypyridine-N-oxide, 2-pyridinethiol-1-oxide and their salts, 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1H)-pyridone and their salts (preferably monoethanolamine salts), and mixtures thereof. Because an equilibrium always exists, formula (P) discloses and encompasses the tautomeric equivalents of these compounds. In at least one embodiment, the compound according to formula (P) is piroctone olamine (octopirox).

[0060] In at least one embodiment, the alkyl diol 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.

[0061] In at least one embodiment, the halogenated compound is selected from the group consisting of chlorhexidine and its salts, triclosan, chlorphenesin, trichlorcarban, chloroxylenol, iodoproprinyl butylcarbamate, bronopol, climbazole, and mixtures thereof.

[0062] In at least one embodiment, the isothiazolinone is selected from the group consisting of methylisothiazolinone, methylchloroisothiazolinone, benzylisothiazolinone, and mixtures thereof.

[0063] 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, hydroxypyridones, alkyldiols, halogenated compounds, isothiazolinones, and mixtures thereof.

[0064] 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, piroctone olamine, and mixtures thereof.

[0065] In a preferred embodiment, the antimicrobial agent is 1,2-octanediol, in particular bio-based 1,2-octanediol, such as bio-1,2-octanediol as disclosed in WO2019 / 152569.

[0066] Suitable antimicrobial agents are also listed in Annex V of Regulation (EC) No 1223 / 2009 of the European Parliament and of the Council of 30 November 2009 on cosmetic products (updated 28 September 2022).

[0067] The combination of this invention can be prepared by methods known in the art, such as by mixing the ingredients.

[0068] The blends of the present invention can be prepared by methods known in the art, such as by mixing the components thereof.

[0069] The present invention also relates to a formulation comprising: (A) at least one compound selected from the group consisting of a compound of formula (I), a sorbitan ester, an isosorbide ester, a glyceryl ether, and a glyceryl ester; and [ka] 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. (B) at least one hydroxyacetophenone;

[0070] In one embodiment, the present invention relates to a formulation comprising: (A) 0.1 to 10% by weight, preferably 0.2 to 3% by weight, particularly preferably 0.3 to 1.5% by weight, based on the total weight of the formulation, of at least one compound selected from the group consisting of a compound of the following formula (I), a sorbitan ester, an isosorbide ester, a glyceryl ether, and a glyceryl ester; and [ka] 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. (B) 0.01 to 1.5% by weight, preferably 0.05 to 0.5% by weight, particularly preferably 0.1 to 0.3% by weight, of at least one hydroxyacetophenone, based on the total weight of the formulation.

[0071] In at least one embodiment, the formulation is selected from the group consisting of cosmetic formulations and household cleaning formulations.

[0072] In at least one embodiment, the formulation is selected from the group consisting of shampoo, body wash, facial cleanser, face mask, bubble bath, intimate wash, bath oil, cleansing milk, micellar water, makeup remover, cleansing wipes, hair mask, perfume, liquid soap, shaving soap, shaving foam, cleansing foam, day cream, anti-aging cream, body milk, body lotion, body mousse, face serum, eye cream, sunscreen lotion, sun cream, face cream, aftershave lotion, pre-shave cream, hair removal cream, whitening gel, self-tanning cream, acne gel, mascara, foundation, primer, concealer, blush, bronzer, BB cream, eyeliner, night cream, eyebrow gel, highlighter, lip stay the product is selected from the group consisting of: face wash, hand sanitizer, hair oil, nail polish remover, conditioner, hair styling gel, hair styling cream, anti-frizz serum, scalp treatment, hair color, split end solution, deodorant, antiperspirant, baby cream, insect repellent, hand cream, sunscreen gel, foot cream, exfoliant, body scrub, cellulite treatment, bar soap, cuticle cream, lip balm, hair treatment, eye shadow, bath salts, body mist, eau de toilette, mouthwash, toothpaste, lubricating gel, moisturizer, serum, toner, aqua sorbet, cream gel, styling mousse, dry shampoo, lipstick, lip gloss, hydroalcoholic gel, body oil, shower milk, illuminator, lip crayon, hairspray, combing cream, sunblock.

[0073] In at least one embodiment, the formulation is a cosmetic formulation for cleansing hair and / or skin.

[0074] In at least one embodiment, the formulation is a cosmetic formulation, preferably a skin care formulation, more preferably a Revon skin care formulation.

[0075] In at least one embodiment, the formulation is an aqueous solution.

[0076] In at least one embodiment, the formulation includes a solvent. In at least one embodiment, the formulation includes a solvent, the solvent comprising water and / or alcohol. The solvent is useful for providing the compounds used in the present invention in liquid form. In at least one embodiment, the solvent is cosmetically acceptable. In at least one embodiment, the formulation includes at least 10% by weight, preferably at least 20% by weight, more preferably at least 30% by weight, and even more preferably at least 50% by weight of water. Water is useful for economic reasons, but is also useful for cosmetically acceptable reasons. Optionally, the formulation includes a water-miscible or water-soluble solvent, such as a lower alkyl alcohol. In at least one embodiment, the formulation includes a C1-C5 alkyl monohydric alcohol, preferably a C2-C3 alkyl monohydric alcohol. Alcohols that may be present are lower monohydric or polyhydric alcohols having 1 to 4 carbon atoms, particularly those commonly used in cosmetic applications, preferably ethanol and isopropanol.

[0077] Optionally, the formulation includes a water-soluble polyhydric alcohol. In at least one embodiment, the water-soluble polyhydric alcohol is a polyhydric alcohol having two or more hydroxyl groups in the molecule. In at least one embodiment, the water-soluble polyhydric alcohol is a dihydric alcohol such as ethylene glycol, propylene glycol, trimethylene glycol, 1,2-butylene glycol, 1,3-butylene glycol, 1,4-butylene glycol, tetramethylene glycol, 2,3-butylene glycol, pentamethylene glycol, 2-butene-1,4-diol, hexylene glycol, octylene glycol, etc.; a trihydric alcohol such as glycerin, trimethylolpropane, 1,2,6-hexanetriol, etc.; a tetrahydric alcohol such as pentaerythritol; a pentahydric alcohol such as xylitol; a hexahydric alcohol such as sorbitol, mannitol; diethylene glycol, dipropylene glycol, polyethylene glycol, poly Polyhydric alcohol polymers such as propylene glycol, tetraethylene glycol, diglycerin, polyethylene glycol, triglycerin, tetraglycerin, and polyglycerin; dihydric alcohol alkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monophenyl ether, ethylene glycol monohexyl ether, ethylene glycol mono-2-methylhexyl ether, ethylene glycol isoamyl ether, ethylene glycol benzyl ether, ethylene glycol isopropyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, and ethylene glycol dibutyl ether;Dihydric alcohol alkyl ethers such as diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol butyl ether, diethylene glycol methyl ethyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol isopropyl ether, dipropylene glycol methyl ether, dipropylene glycol ethyl ether, and dipropylene glycol butyl ether; ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, ethylene glycol Dihydric alcohol ether esters such as diethylene glycol monophenyl ether acetate, ethylene glycol diadipate, ethylene glycol disuccinate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, and propylene glycol monophenyl ether acetate; glycerin monoalkyl ethers such as xyl alcohol, selachyl alcohol, and batyl alcohol; sorbitol, maltitol, maltotriose, mannitol, sucrose, erythritol, glucose, fructose, starch sugar, maltose, xylitose, starch sugar reducing alcohol, glysolid, tetrahydrofurfuryl alcohol, POE tetrahydrofurfuryl alcohol, POP butyl ether, and POP Sugar alcohols such as POE butyl ether, tripolyoxypropylene glycerol ether, POP glycerin ether, POP glycerin ether phosphate, POP POE pentaerythritol ether, and mixtures thereof;

[0078] In a preferred embodiment, the formulation is selected from the group consisting of water, glycol, ethanol, and mixtures thereof. In a preferred embodiment, the formulation comprises water.

[0079] In a preferred embodiment, the formulation comprises an aqueous, alcoholic or aqueous-alcoholic solvent, wherein the aqueous, alcoholic or aqueous-alcoholic solvent comprises water, ethanol, propanol, isopropanol, 1,2-propylene glycol, 1,3-propylene glycol, isobutanol, butanol, butyl glycol, butyl diglycol, glycerol, or a mixture thereof; preferably, the aqueous, alcoholic or aqueous-alcoholic solvent comprises water, ethanol, propanol, isopropanol, 1,2-propylene glycol, 1,3-propylene glycol, glycerol, or a mixture thereof; more preferably, the aqueous, alcoholic or aqueous-alcoholic solvent comprises water, isopropanol, 1,2-propylene glycol, 1,3-propylene glycol, or a mixture thereof; even more preferably, the aqueous, alcoholic or aqueous-alcoholic solvent consists of water or a mixture of water and an alcohol, wherein the alcohol is selected from the group consisting of isopropanol, 1,2-propylene glycol and 1,3-propylene glycol.

[0080] In at least one embodiment, the formulation comprises additives common in cosmetology, pharmacy, and dermatology, hereinafter referred to as auxiliaries, which are selected from the group consisting of oily substances, emulsifiers, co-emulsifiers, cationic polymers, film-forming agents, superfatting agents, stabilizers, active biological ingredients, glycerol, preservatives, pearlizing agents, dyes and fragrances, solvents, opacifiers, functional acids, and also protein derivatives such as gelatin, collagen hydrolysates, natural or synthetic polypeptides, egg yolk, lecithin, lanolin and lanolin derivatives, fatty alcohols, silicones, deodorants, substances with keratolytic and keratinogenic action, enzymes, and / or carriers / solvents.

[0081] In at least one embodiment, the formulation comprises water-soluble vitamins and derivatives thereof, water-soluble amino acids and salts and / or derivatives thereof, viscosity modifiers, dyes, non-volatile solvents or diluents (water-soluble and water-insoluble), pearlizing aids, thickeners, foam boosters, additional surfactants or non-ionic co-surfactants, pediculocides, pH adjusters, fragrances, preservatives, chelating agents, proteins, skin active agents, sunscreens, UV absorbers, vitamins, niacinamide, caffeine, minoxidil, and combinations thereof. In at least one embodiment, the formulation comprises 0 wt% to 5 wt% of vitamins and amino acids by total weight of the formulation. The formulations can also include pigment materials such as inorganic, nitroso, monoazo, diazo, carotenoid, triphenylmethane, triarylmethane, xanthene, quinoline, oxazine, azine, anthraquinone, indigoid, thioindigoid, quinacridone, phthalocyanine, vegetable dyes, natural dyes, etc., including water-soluble components such as those with CI names. The formulations can include 0 wt % (preferably 0.0001 wt %) to 5 wt % pigment materials.

[0082] In at least one embodiment, the formulation comprises an oily substance (a fatty substance that is liquid at room temperature, 25° C.). In at least one embodiment, the formulation comprises a silicone oil, which may be volatile or non-volatile, linear, branched, or cyclic, and optionally organically modified; phenylsilicones; silicone resins and gums; mineral oils, such as paraffin oil or petrolatum oil; oils of animal origin, such as perhydrosqualene, lanolin; oils of plant origin, such as liquid triglycerides, for example, sunflower oil, corn oil, soybean oil, rice oil, jojoba oil, babassu oil, pumpkin oil, grape seed oil, gum oil, etc. oil, walnut oil, apricot oil, macadamia oil, avocado oil, sweet almond oil, cardamom oil, castor oil, caprylic / capric triglyceride, olive oil, peanut oil, rapeseed oil, argan oil, Abyssinian oil, and coconut oil; synthetic oils, such as Purcellin oil, isoparaffin, linear and / or branched fatty alcohols and fatty acid esters having 6 to 18, preferably 8 to 10, carbon atoms, preferably Guerbet alcohols; linear (C6-C 13 ) fatty acids and straight chain (C6-C 20 ) Esters of fatty alcohols; branched (C6-C 13 ) carboxylic acids and straight chain (C6-C 20 ) Esters of fatty alcohols, linear (C6-C 18 ) Esters of fatty acids and branched alcohols, in particular 2-ethylhexanol; esters of linear and / or branched fatty acids and polyhydric alcohols (e.g., dimerdiol or, for example, trimerdiol) and / or Guerbet alcohols; (C6-C 10 ) fatty acid-based triglycerides; esters such as dioctyl adipate, diisopropyl dilinoleate dimer, etc.; propylene glycol / dicaprylate or waxes such as beeswax, paraffin wax or microcrystalline wax, alone or in combination with, for example, hydrophilic waxes, such as cetylstearyl alcohol; fluorinated and perfluorinated oils; fluorinated silicone oils; and oily substances selected from the group consisting of mixtures of the foregoing compounds.

[0083] In at least one embodiment, the formulation includes a non-ionic co-emulsifier, which may be an adduct of 0-30 mol ethylene oxide and / or 0-5 mol propylene oxide with a linear fatty alcohol having 8-22 carbon atoms, a fatty acid having 12-22 carbon atoms, an alkylphenol having 8-15 carbon atoms in the alkyl group, and a sorbitan or sorbitol ester; an adduct of 0-30 mol ethylene oxide with glycerol (C 12 ~C 18 ) fatty acid monoesters and diesters; saturated and unsaturated fatty acid glycerol monoesters and diesters and sorbitan monoesters and diesters having 6 to 22 carbon atoms and, where appropriate, their ethylene oxide adducts; adducts of 15 to 60 moles of ethylene oxide with castor oil and / or hydrogenated castor oil; polyol esters, such as polyglyceryl polyricinoleate and polyglyceryl poly-12-hydroxystearate, and in particular polyglycerol esters. Also suitable are mixtures of compounds from one or more of these classes of substances. Examples of suitable ionogenic coemulsifiers include anionic emulsifiers, such as mono-, di-, or triphosphate esters, but also cationic emulsifiers, such as mono-, di-, and trialkyl quats and their polymeric derivatives.

[0084] In at least one embodiment, the formulation comprises a cationic polymer. Suitable cationic polymers include those known under the INCI name "Polyquaternium", in particular Polyquaternium-31, Polyquaternium-16, Polyquaternium-24, Polyquaternium-7, Polyquaternium-22, Polyquaternium-39, Polyquaternium-28, Polyquaternium-2, Polyquaternium-10, Polyquaternium-11, and also Polyquaternium-37 & mineral oil & PPG trideceth (Salcare SC95), PVP-dimethylaminoethyl methacrylate copolymer, guar hydroxypropyltriammonium chloride, and also calcium alginate and ammonium alginate. It is further possible to use cationic cellulose derivatives; cationic starch; copolymers of diallylammonium salts and acrylamide; quaternized vinylpyrrolidone / vinylimidazole polymers; condensation products of polyglycols and amines; quaternized collagen polypeptides; quaternized wheat polypeptides; polyethyleneimine; cationic silicone polymers such as, for example, amidomethicone; copolymers of adipic acid and dimethylaminohydroxypropyldiethylenetriamine; polyaminopolyamides and cationic chitin derivatives such as, for example, chitosan.

[0085] In at least one embodiment, the formulation contains a superfatting agent. Examples of such superfatting agents include polyethoxylated lanolin derivatives, lecithin derivatives, polyol fatty acid esters, monoglycerides, or fatty acid alkanolamides. The latter also function as foam stabilizers. Suitable moisturizing agents include, for example, isopropyl palmitate, glycerol, and / or sorbitol.

[0086] In at least one embodiment, the formulation includes a stabilizer, which can be, for example, a metal salt of a fatty acid, such as magnesium, aluminum, and / or zinc stearate.

[0087] In at least one embodiment, the formulation includes a care additive, which may be combined with conventional ceramides, pseudoceramides, fatty acid N-alkyl polyhydroxyalkylamides, cholesterol, cholesterol fatty acid esters, fatty acids, triglycerides, cerebrosides, phospholipids, panthenol, and similar substances as care additives.

[0088] In at least one embodiment, the formulation includes an antifungal agent. In at least one embodiment, the antifungal agent is selected from the group consisting of ketoconazole, oxiconazole, bifonazole, butoconazole, cloconazole, clotrimazole, econazole, enilconazole, fenticonazole, isoconazole, miconazole, sulconazole, tioconazole, fluconazole, itraconazole, terconazole, naftifine, terbinafine, zinc pyrithione, piroctone olamine (octopirox), and combinations thereof. In at least one embodiment, the formulation includes 0.1 wt% to 1 wt% total amount of the antifungal agent in the formulation. In at least one embodiment, the formulation includes pyridinethione antidandruff microparticles. For example, 1-hydroxy-2-pyridinethione salts are highly preferred microparticle antidandruff agents. The concentration of pyridinethione anti-dandruff microparticles can be in the range of 0.1 wt% to 4 wt%, preferably 0.1 wt% to 3 wt%, more preferably 0.3 wt% to 2 wt% of the weight of the formulation. Preferred pyridinethione salts include those formed from heavy metals such as zinc, tin, cadmium, magnesium, aluminum, or zirconium, preferably zinc, more preferably the zinc salt of 1-hydroxy-2-pyridinethione (known as "zinc pyridinethione" or "ZPT"), more preferably the 1-hydroxy-2-pyridinethione salt in platelet particle form. Salts formed from other cations, such as sodium, may also be suitable.

[0089] Functional acids are acidic substances used to impart clinical functionality to skin or hair upon application. Suitable functional acids include alpha hydroxy acids, beta hydroxy acids, lactic acid, retinoic acid, and similar substances.

[0090] In at least one embodiment, the formulation includes an astringent selected from the group consisting of magnesium oxide, aluminum oxide, titanium dioxide, zirconium dioxide, zinc oxide, oxide hydrates, aluminum oxide hydrate (boehmite), and hydroxides and chlorohydrates of calcium, magnesium, aluminum, titanium, zirconium, or zinc. In at least one embodiment, the formulation includes 0.001 wt% to 10 wt%, or 0.01 wt% to 9 wt%, or 0.05 wt% to 8 wt%, or 0.1 wt% to 5 wt% of the astringent.

[0091] In at least one embodiment, the formulation includes a deodorant. In at least one embodiment, the deodorant is selected from the group consisting of allantoin, bisabolol, and combinations thereof. In at least one embodiment, the formulation includes 0.001 wt% to 10 wt%, or 0.01 wt% to 9 wt%, or 0.05 wt% to 8 wt%, or 0.1 wt% to 5 wt% of the deodorant.

[0092] In at least one embodiment, the formulation comprises a sunscreen and / or UV filter. Suitable sunscreens and UV filters are disclosed in WO 2013 / 017262 A1, page 32, line 11 to the end of page 33. In at least one embodiment, the sunscreen and / or UV filter is 4-aminobenzoic acid, 3-(4'-trimethylammonium)-benzylide-boran-2-one-methylsulfate, camphorbenzalkonium methosulfate, 3,3,5-trimethyl-cyclohexyl salicylate, 2-hydroxy-4-methoxybenzophenone, 2-phenylbenzimidazole-5-sulfonic acid and its potassium, sodium salts. and triethanolamine salts, 3,3'-(1,4-phenylenedimethine)-bis-(7,7-dimethyl-2-oxobicyclo[2.2.1]-heptane-1-methanesulfonic acid) and its salts, 1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)propane-1,3-dione, 3-(4'-sulfo)-benzylidene-bornan-2-one and its salts, 2-cyano-3,3-diphenyl-acrylate-(2-ethylhexyl) ester), polymer of N-[2(and 4)-(2-oxoborn-3-ylidenemethyl)benzyl]-acrylamide, 4-methoxy-cinnamic acid-2-ethyl-hexyl ester, ethoxylated ethyl-4-amino-benzoate, 4-methoxy-cinnamic acid-isoamyl ester, 2,4,6-tris-[p-(2-ethylhexyloxycarbonyl)anilino]-1,3,5-triazine, 2-(2H-benzotriazol-2-yl)-4 -Methyl-6-(2-methyl-3-(1,3,3,3-tetramethyl-1-(trimethylsilyloxy)-disiloxanyl)-propyl)phenol, 4,4'-[(6-[4-((1,1-dimethylethyl)-amino-carbonyl)phenylamino]-1,3,5-triazin-2,4-yl)diimino]bis-(benzoic acid-2-ethylhexyl ester), 3-benzophenone, 4-benzophenone, 3(4'-methylbenzylidene)-D,L-camphor, 3-benzylidene-camphor, salicylic acid-2-ethylhexyl ester, 4-dimethylaminobenzoic acid-2-ethylhexyl ester, hydroxy-4-methoxy-benzophenone-5-sulfonic acid and its sodium salt, 4-isopropylbenzyl salicylate, N,N,N-trimethyl-4-(2-oxoborn-3-ylidenemethyl)anilium methyl sulfate, homosalate (INN), oxybenzone (INN), 2-phenylbenzimidazole-5-sulfonic acid and its sodium, potassium, and triethyl esters Alkylamine salt, octyl methoxycinnamic acid, isopentyl-4-methoxycinnamic acid, isoamyl-p-methoxycinnamic acid, 2,4,6-trianilino-(p-carbo-2'-ethylhexyl-1'-oxy)-1,3,5-triazine (octyltriazone) phenol, 2,2(2H-benzotriazol-2-yl)-4-methyl-6-(2-methyl-3-(1,3,3,3-tetramethyl-1-(trimethylsilyl)oxy)-disiloxanyl)propyl(drometrizole trisiloxane)benzoate, 4,4-((6-(((1,1-dimethylethyl (1,1-dimethylethyl)amino)carbonyl)phenyl)amino)-1,3,5-triazine-2,4-diyl)diimino)bis,bis(2-ethylhexyl)ester)benzoic acid, 4,4-((6-(((1,1-dimethylethyl)amino)-carbonyl)phenyl)amino)-1,3,5-triazine-2,4-diyl)diimino)bis,bis(2-ethylhexyl)ester), 3-(4'-methylbenzylidene)-D,L-camphor (4-methylbenzylidene camphor), benzylidene-camphor-sulfonic acid, octocrylene, polyacrylamidomethyl- Benzylidene-camphor, 2-ethylhexyl salicylate (octyl salicylate), 4-dimethyl-aminobenzoic acid ethyl-2-hexyl ester (octyldimethyl PABA), PEG-25 PABA, 2-hydroxy-4-methoxybenzo-phenone-5-sulfonic acid (5-benzophenone) and its sodium salt, 2,2'-methylene-bis-6-(2H-benzotriazol-2-yl)-4-(tetramethyl-butyl)-1,1,3,3-phenol, 2-2'-bis-(1,4-phenylene)1H-phenylbenzimidazole-4,Sodium salt of 6-disulfonic acid, (1,3,5)-triazine-2,4-bis((4-(2-ethyl-hexyloxy)-2-hydroxy)-phenyl)-6-(4-methoxyphenyl), 2-ethylhexyl-2-cyano-3,3-diphenyl-2-propenoate, glyceryl octanoate, di-p-methoxycinnamic acid, p-amino-benzoic acid and its esters, 4-tert-butyl-4'-methoxydibenzoylmethane, 4-(2-β-glucopyranoxy)propoxy-2-hydroxybenzophenone, octyl salicylate, methyl-2,5-diisopropylcinnamate, cinoxate, dihydroxy-dimethoxybenzophenone, 2,2'-dihydro Disodium salt of oxy-4,4'-dimethoxy-5,5'-disulfobenzophenone, dihydroxybenzophenone, 1,3,4-dimethoxyphenyl-4,4-dimethyl-1,3-pentanedione, 2-ethylhexyl-dimethoxybenzylidene-dioxoimidazolidinepropionate, methylene-bis-benztriazolyltetramethylbutylphenol, phenyl dibenzimidazole tetrasulfonate, bis-ethylhexyloxyphenol-methoxyphenol-triazine, tetrahydroxybenzophenone, terephthalidenedicamphor-sulfonic acid, 2,4,6-tris[4,2-ethylhexyloxycarbonyl)anilino]-1,3,5-triazine, methyl-bis(trimethylsiloxy)silyl-isopentyltrimethoxycinnamate, amyl-p-dimethylaminobenzoate, amyl-p-dimethylaminobenzoate, 2-ethylhexyl-p-dimethylaminobenzoate, isopropyl-p-methoxycinnamate / diisopropylcinnamate, 2-ethylhexyl-p-methoxycinnamic acid, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and trihydrate, 2-hydroxy-4-methoxybenzophenone-5-sulfonate sodium salt, phenyl-benzimidazole sulfonic acid, and combinations thereof. In at least one embodiment, the formulation comprises 0.001 wt% to 10 wt%, preferably 0.05 wt% to 5 wt%, even more preferably 0.1 wt% to 3 wt%, and most preferably 0.05 wt% to 1 wt% of sunscreen and / or UV filters. In at least one embodiment, the formulation contains a photoprotective agent in an amount of 0.01 to 10 wt %, or 0.1 to 5 wt %, more preferably 0.2 to 2 wt %. Suitable photoprotective agents include, in particular, all of the photoprotective agents specified in EP 1 084 696 A1, which is incorporated herein by reference. In a preferred embodiment, the photoprotective agent is selected from the group consisting of 2-ethylhexyl 4-methoxycinnamate, methyl methoxycinnamate, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid, polyethoxylated p-aminobenzoates, and combinations thereof.

[0093] In at least one embodiment, the formulation comprises an antioxidant selected from the group consisting of amino acids, peptides, sugars, imidazole, carotenoids, carotenes, chlorogenic acid, lipoic acid, thiols, thiol glycosyl esters, thiol N-acetyl esters, thiol methyl esters, thiol ethyl esters, thiol propyl esters, thiol amyl esters, thiol butyl esters, thiol lauryl esters, thiol palmitoyl esters, thiol oleyl esters, thiol linoleyl esters, thiol cholesteryl esters, thiol glyceryl esters, dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid, metal chelators, hydroxy acids, fatty acids, folic acid, vitamin C, tocopherol, vitamin A, stilbenes, derivatives thereof, and combinations thereof. In at least one embodiment, the antioxidant is selected from the group consisting of glycine, histidine, tyrosine, tryptophan, urocanic acid, D,L-carnosine, D-carnosine, L-carnosine, beta-carotene, alpha-carotene, lycopene, dihydrolipoic acid, aurothioglucose, propylthiouracil, thioredoxin, glutathione, cysteine, cystine, cystamine, buthionine sulfoximine, homocysteine ​​sulfoximine, buthionine sulfone, penta-, hexa-, heptathionine sulfoximine, hydroxy fatty acids, palmitic acid, phytic acid, lactate, and the like. In at least one embodiment, the antioxidant is selected from the group consisting of: ferrin, citric acid, lactic acid, malic acid, humic acid, bile acid, bilirubin, biliverdin, EDTA, EGTA, linoleic acid, linolenic acid, oleic acid, butylhydroxyanisole, trihydroxybutyrophenone, ubiquinone, ubiquinol, ascorbyl palmitate, Mg-ascorbyl phosphate, ascorbyl acetate, vitamin E acetate, vitamin A palmitate, carnosine, mannose, ZnO, ZnSO4, selenium methionine, stilbene, superoxide dismutase, and combinations thereof. In at least one embodiment, the antioxidant is selected from the group consisting of vitamin A, vitamin A derivatives, vitamin E, vitamin E derivatives, and combinations thereof.In at least one embodiment, the formulation comprises 0.001 wt% to 10 wt%, preferably 0.05 wt% to 5 wt%, particularly preferably 0.1 wt% to 3 wt%, especially preferably 0.05 wt% to 1 wt% of antioxidant.

[0094] In at least one embodiment, the formulation comprises a dye or pigment. In at least one embodiment, the formulation comprises at least one pigment. Suitable dyes and pigments are disclosed in the tables on pages 36-43 of WO 2013 / 017262 A1. These may be color pigments that impart a color effect to the product mass or hair, or they may be shine effect pigments that impart a shine effect to the product mass or hair. The color or shine effect on hair is preferably temporary, i.e., it lasts until the next wash and can be removed again by washing with a conventional shampoo. In at least one embodiment, the formulation comprises a total amount of pigments of 0.01 wt% to 25 wt%, preferably 5 wt% to 15 wt%. In at least one embodiment, the pigment has a particle size of 1 micron to 200 microns, preferably 3 microns to 150 microns, more preferably 10 microns to 100 microns. The pigment is a colorant that is practically insoluble in the application medium and may be inorganic or organic. Mixed inorganic-organic pigments are also possible. Inorganic pigments are preferred. The advantage of inorganic pigments is their excellent resistance to light, weather, and temperature. The inorganic pigments may be of natural origin. In at least one embodiment, the inorganic pigment is selected from the group consisting of chalk, ochre, umber, green earth, burnt sienna, graphite, and combinations thereof. The pigments may be white pigments, such as titanium dioxide or zinc oxide; black pigments, such as black iron oxide; colored pigments, such as ultramarine or red iron oxide; luster pigments; metallic effect pigments; pearlescent pigments; and fluorescent or phosphorescent pigments, preferably in which at least one pigment is a colored, non-white pigment. In at least one embodiment, the pigment is selected from the group consisting of metal oxides, hydroxides and oxide hydrates, mixed-phase pigments, sulfur-containing silicates, metal sulfides, complex metal cyanides, metal sulfates, chromates and molybdates, and metals themselves (bronze pigments), and combinations thereof.In at least one embodiment, the pigment is selected from the group consisting of titanium dioxide (CI 77891), black iron oxide (CI 77499), yellow iron oxide (CI 77492), red and brown iron oxide (CI 77491), manganese violet (CI 77742), ultramarine (sodium aluminum sulfosilicate, CI 77007, Pigment Blue 29), chromium oxide hydrate (CI 77289), Prussian blue (ferric ferrocyanide, CI 77510), carmine (cochineal), and combinations thereof. In at least one embodiment, the pigment is selected from the group consisting of pearlescent pigments and colored pigments based on mica coated with metal oxides or metal oxychlorides, such as titanium dioxide or bismuth oxychloride, and optionally further color-imparting substances, such as iron oxides, Prussian blue, ultramarine, carmine, etc., and the color can be determined by varying the layer thickness. Such pigments are sold, for example, by Merck under the trade names Rona®, Colorona®, Dichrona®, and Timiron®. In at least one embodiment, the pigment is selected from the group consisting of organic pigments such as sepia, gunbody, bone ash, Cassel brown, indigo, chlorophyll, and other plant pigments. In at least one embodiment, the pigment is selected from the group consisting of azo pigments, anthraquinoids, indigoids, dioxazines, quinacridones, phthalocyanines, isoindolinones, perylenes and perinones, metal complexes, alkali blues, and synthetic organic pigments such as diketopyrrolopyrrole pigments.

[0095] In at least one embodiment, the formulation contains 0.01 wt% to 10 wt%, preferably 0.05 wt% to 5 wt%, of at least one particulate material. Suitable materials are, for example, those that are solid at room temperature (25°C) and in particulate form. In at least one embodiment, the particulate material is selected from the group consisting of silica, silicates, aluminates, clay earth, mica, insoluble salts, particularly insoluble inorganic metal salts, metal oxides such as titanium dioxide, minerals, and insoluble polymer particles are suitable. The particles may be present in the formulation in an undissolved form, preferably a stably dispersed form, and can be deposited in solid form on the substrate after application to the keratin substrate and evaporation of the solvent. A stable dispersion can be achieved by providing the formulation with a yield large enough to prevent the solid particles from settling. A sufficient yield can be achieved using a suitable gel-based formulation in an appropriate amount. In at least one embodiment, the particulate material is selected from the group consisting of silica (silica gel, silicon dioxide) and metal salts, particularly inorganic metal salts, with silica being particularly preferred. The metal salts are, for example, alkali metal or alkaline earth metal halides, such as sodium chloride or potassium chloride; or alkali metal or alkaline earth metal sulfates, such as sodium sulfate or magnesium sulfate.

[0096] In at least one embodiment, the formulation comprises a direct dye. Preferred direct dyes are the following compounds, alone or in combination with one another: hydroxyethyl-2-nitro-p-toluidine, 2-hydroxyethylpicramic acid, 4-nitrophenylaminourea, tri(4-amino-3-methylphenyl)carbenium chloride (Basic Violet 2), 1,4-diamino-9,10-anthracenedione (Disperse Violet 1), 1-(2-hydroxyethyl)amino-2-nitro-4-[di(2-hydroxyethyl)amino]benzene (HC Blue No. 2), 4-[ethyl-(2-hydroxyethyl)amino]-1-[(2-hydroxyethyl)amino]-2-nitrobenzene hydrochloride (HC Blue No. 12), 1-amino-4-[di(2-hydroxyethyl)amino]-2-nitrobenzene hydrochloride (HC Red No. 13), 4-amino-1-[(2-hydroxyethyl)amino]-2-nitrobenzene (HC Red No. 14). No. 3), 4-amino-3-nitrophenol, 4-[(2-hydroxyethyl)amino]-3-nitrophenol, 1-amino-5-chloro-4-[(2,3-dihydroxypropyl)amino]-2-nitrobenzene (HC Red No. 10), 5-chloro-1,4-[di(2,3-dihydroxypropyl)amino]-2-nitrobenzene (HC Red No. 11), 2-chloro-6-ethylamino-4-nitrophenol, 2-amino-6-chloro-4-nitrophenol, 4-[(2-hydroxyethyl)amino]-3-nitro-1-trifluoromethylbenzene (HC Yellow No. 13), 8-amino-2-bromo-5-hydroxy-4-imino-6-{[3-(trimethylammonio)-phenyl]amino}-1(4H)-naphthalenone chloride (CI 56059; Basic Blue) No. 99), 1-[(4-aminophenyl)azo]-7-(trimethylammonio)-2-naphthol chloride (CI 12250; Basic Brown No. 16), 1-[(4-amino-2-nitrophenyl)azo]-7-(trimethylammonio)-2-naphthol chloride (Basic Brown No.17), 2-hydroxy-1-[(2-methoxyphenyl)azo]-7-(trimethylammonio)naphthalene chloride (CI 12245; Basic Red No. 76), 3-methyl-1-phenyl-4-{[3-(trimethylammonio)phenyl]azo}pyrazol-5-one chloride (CI 12719; Basic Yellow No. 57), and 2,6-diamino-3-[(pyridin-3-yl)azo]pyridine, and their salts. Among the direct dyes, the following compounds are particularly preferred, alone or in combination with one another: hydroxyethyl-2-nitro-p-toluidine, 2-hydroxyethylpicramic acid, 4-nitrophenylaminourea, tri(4-amino-3-methylphenyl)carbenium chloride (Basic Violet 2), 1,4-diamino-9,10-anthracenedione (Disperse Violet 1), 1-(2-hydroxyethyl)amino-2-nitro-4-[di(2-hydroxyethyl)amino]benzene (HC Blue No. 2), 4-[ethyl-(2-hydroxyethyl)amino]-1-[(2-hydroxyethyl)amino]-2-nitrobenzene hydrochloride (HC Blue No. 12), 1-amino-4-[di(2-hydroxyethyl)amino]-2-nitrobenzene hydrochloride (HC Red No. 13), 4-amino-1-[(2-hydroxyethyl)amino]-2-nitrobenzene (HC Red No. 14). No. 3), 4-amino-3-nitrophenol, 4-[(2-hydroxyethyl)amino]-3-nitrophenol, 1-amino-5-chloro-4-[(2,3-dihydroxypropyl)amino]-2-nitrobenzene (HC Red No. 10), 5-chloro-1,4-[di(2,3-dihydroxypropyl)-amino]-2-nitrobenzene (HC Red No. 11), 2-chloro-6-ethylamino-4-nitrophenol, 2-amino-6-chloro-4-nitrophenol, 4-[(2-hydroxyethyl)amino]-3-nitro-1-trifluoromethylbenzene (HC Yellow No. 13), 8-amino-2-bromo-5-hydroxy-4-imino-6-{[3-(trimethylammonio)-phenyl]amino}-1(4H)-naphthalenone chloride (CI56059; Basic Blue No. 99), 1-[(4-aminophenyl)azo]-7-(trimethylammonio)-2-naphthol chloride (CI 12250; Basic Brown No. 16), 1-[(4-amino-2-nitrophenyl)azo]-7-(trimethylammonio)-2-naphthol chloride (Basic Brown No. 17), 2-hydroxy-1-[(2-methoxyphenyl)azo]-7-(trimethylammonio)naphthalene chloride (CI 12245; Basic Red No. 76), 3-methyl-1-phenyl-4-{[3-(trimethylammonio)phenyl]azo}pyrazol-5-one chloride (CI 12719; Basic Yellow No. 57), and 2,6-diamino-3-[(pyridin-3-yl)azo]pyridine, and salts thereof. In at least one embodiment, the total amount of direct dyes in the formulation totals 0.01 to 15 wt%, preferably 0.1 to 10 wt%, and most preferably 0.5 to 8 wt%.

[0097] In at least one embodiment, the formulation includes a conditioning agent. In at least one embodiment, the conditioning agent is a water-insoluble, water-dispersible, non-volatile liquid that forms emulsified droplets. In at least one embodiment, the conditioning agent is a silicone (e.g., silicone oil, cationic silicone, silicone gum, high refractive index silicone or silicone resin), an organic conditioning oil (e.g., hydrocarbon oil, polyolefin or fatty ester), a cationic conditioning surfactant, a high melting point fatty compound, or a combination thereof.

[0098] In at least one embodiment, the conditioning agent is a silicone, and the formulation comprises 0.01% to 10%, or 0.1% to 5%, of the silicone conditioning agent, based on the total weight of the formulation. Suitable silicone conditioning agents, and optional suspending agents for silicones, are described in U.S. Pat. No. 5,104,646. In at least one embodiment, the formulation comprises a silicone gum selected from the group consisting of polydimethylsiloxane, (polydimethylsiloxane)(methylvinylsiloxane) copolymer, poly(dimethylsiloxane)(diphenylsiloxane)(methylvinylsiloxane) copolymer, and mixtures thereof.

[0099] In at least one embodiment, the composition comprises a terminal amino silicone, by which is meant herein a silicone containing one or more amino groups at one or both ends of the silicone backbone. In at least one embodiment, the formulation is substantially free of silicone compounds containing pendant amino groups. In one embodiment, the formulation is substantially free of silicone compounds other than terminal aminosilicones. In at least one embodiment, the amino group at at least one end of the silicone backbone of the terminal aminosilicone is selected from the group consisting of primary amines, secondary amines, and tertiary amines.

[0100] In at least one embodiment, the formulation comprises a terminal amino silicone according to formula (S): (R F ) a G 3-a -Si-(-OSiG2) n -O-SiG3- a (R F ) a (S) wherein G is hydrogen, phenyl, hydroxy, or C1-C8 alkyl, preferably methyl; a is an integer having a value of 1 to 3, preferably 1; b is 0, 1, or 2, preferably 1; n is a number from 0 to 1,999; and R F is represented by the general formula C q H2q L, where q is an integer having a value of 2 to 8, and L is selected from the group consisting of: -N(R T )CH2-CH2-N(R T )2;-N(R T )2;-N(R T )3A - ;-N(R T )CH2-CH2-NR T H2A - , where R T is hydrogen, phenyl, benzyl, or a saturated hydrocarbon group, preferably an alkyl group having 1 to 20 carbon atoms; A - is a -halide ion.)

[0101] In at least one embodiment, the terminal amino silicone corresponding to formula (S) has a=1, q=3, G=methyl, n is 1000-2500, alternatively 1500-1700, and L is -N(CH3)2. Suitable terminal amino silicones corresponding to formula (III) have a=O, G=methyl, n is 100-1500, alternatively 200-800, and L is selected from the group consisting of -N(R T )CH2-CH2-N(R T )2;-N(R T )2;-N(R T )3A-;-N(R T )CH2-CH2-NR T H2A-(wherein, R T is hydrogen, phenyl, benzyl, or a saturated hydrocarbon group, preferably an alkyl group having 1 to 20 carbon atoms; A -is a -halide ion, or L is -NH2. In at least one embodiment, the terminal aminosilicone is selected from the group consisting of bis-aminomethyl dimethicone, bis-aminoethyl dimethicone, bis-aminopropyl dimethicone, bis-aminobutyl dimethicone, and mixtures thereof. In one embodiment, the viscosity of the terminal aminosilicone is 1,000 to 30,000 cPs, or 5,000 to 20,000 cPs measured at 25°C. In at least one embodiment, the formulation comprises 0.1% to 20%, or 0.5% to 10%, or 1% to 6% of the terminal aminosilicone by total weight of the formulation.

[0102] In at least one embodiment, the formulation comprises a high melting point fatty compound. The high melting point fatty compound has a melting point of 25° C. or higher. In at least one embodiment, the composition comprises a high melting point fatty compound. The high melting point fatty compound has a melting point of 25° C. or higher. In at least one embodiment, the high melting point fatty compound is selected from the group consisting of fatty alcohols, fatty acids, fatty alcohol derivatives, fatty acid derivatives, and mixtures thereof. Non-limiting examples of high melting point compounds are found in the International Cosmetic Ingredient Dictionary, 5th Edition, 1993, and the CTFA Cosmetic Ingredient Handbook, 2nd Edition, 1992. The formulation may comprise 0.1% to 40%, or 1% to 30%, or 1.5% to 16%, or 1.5% to 8% of the high melting point fatty compound by total weight of the formulation. This is advantageous in providing improved conditioning benefits, such as smoothness during application to wet hair and softness and moisturization on dry hair. In at least one embodiment, the fatty alcohol is selected from the group consisting of cetyl alcohol, stearyl alcohol, behenyl alcohol, and mixtures thereof. In at least one embodiment, the formulation includes a linear fatty alcohol contained in a lamellar gel matrix. The lamellar gel matrix is ​​suitable for providing various conditioning benefits, such as a smooth feel during application to wet hair and a soft and moisturized feel on dry hair. The linear fatty alcohol may contain 8 to 24 carbon atoms. In one embodiment, the linear fatty alcohol is selected from the group consisting of cetyl alcohol, stearyl alcohol, and mixtures thereof. In one embodiment, the weight ratio of total linear fatty alcohol to terminal aminosilicone is 0.5:1 to 10:1, or 1:1 to 5:1, or 2.4:1 to 2.7:1.

[0103] In at least one embodiment, the lamellar gel matrix comprises a cationic conditioning surfactant and a high melting point fatty compound, wherein the cationic conditioning surfactant to high melting point fatty compound weight ratio in providing the lamellar gel matrix is ​​in the range of 1:1 to 1:10, or 1:1 to 1:6.

[0104] In at least one embodiment, the formulation comprises a cationic conditioning surfactant. In at least one embodiment, the formulation comprises 0.05% to 3.0%, or 0.075% to 2.0%, or 0.1% to 1.0% of the cationic conditioning surfactant by total weight of the formulation. In at least one embodiment, the cationic conditioning surfactant is contained in a lamellar gel matrix. In other words, the formulation comprises a lamellar gel matrix, and the lamellar gel matrix comprises the cationic conditioning surfactant. In one embodiment, the cationic conditioning surfactant is represented by formula (C): [ka] (In the formula, R 71 , R 72 , R 73 , and R 74 at least one of R is selected from an aliphatic group having 8 to 30 carbon atoms, an aromatic group having up to 22 carbon atoms, an alkoxy, a polyoxyalkylene, an alkylamido, a hydroxyalkyl, an aryl, or an alkylaryl group; 71 , R 72 , R 73 and R 74 the remainder are independently selected from the group consisting of aliphatic groups of 1 to 22 carbon atoms and aromatic, alkoxy, polyoxyalkylene, alkylamido, hydroxyalkyl, aryl, or alkylaryl groups having up to 22 carbon atoms; X is selected from the group consisting of halogen, acetic acid, citric acid, lactic acid, glycolic acid, phosphoric acid, nitric acid, sulfonic acid, sulfuric acid, alkyl sulfate, alkyl sulfonic acid, and combinations thereof.

[0105] In at least one embodiment, the cationic conditioning surfactant is selected from the group consisting of behenyltrimethylammonium chloride, methyl or ethyl sulfate, and stearyltrimethylammonium chloride, methyl or ethyl sulfate.It is believed that longer alkyl groups improve the smoothness and softness of wet and dry hair compared to cationic surfactants with shorter alkyl groups.It is also believed that such cationic surfactants can reduce irritation compared to those with shorter alkyl groups.

[0106] In at least one embodiment, the cationic surfactant is a dialkyl (C 14 ~C 18 ) a di-long chain alkyl quaternized ammonium salt selected from the group consisting of dimethyl ammonium chloride, di-tallow alkyl dimethyl ammonium chloride, dihydrogenated tallow alkyl dimethyl ammonium chloride, distearyl dimethyl ammonium chloride, dicetyl dimethyl ammonium chloride, and mixtures thereof.

[0107] In at least one embodiment, the cationic surfactant is a tertiary amidoamine having an alkyl group of 12 to 22 carbon atoms. The tertiary amidoamine may be selected from the group consisting of stearamidopropyl dimethyl, stearamidopropyl diethyl, stearamidoethyl diethyl, stearamidoethyl dimethyl, palmitamidopropyl dimethyl, palmitamidopropyl diethyl, palmitamidoethyl diethyl, palmitamidoethyl dimethyl, behenamidopropyl dimethyl, behenamidopropyl diethyl, behenamidoethyl diethyl, behenamidoethyl dimethyl, arachidamidopropyl dimethyl, arachidamidopropyl diethyl, arachidamidoethyl diethyl, and arachidamidoethyl dimethylamine, diethylaminoethyl stearamide, and mixtures thereof. The tertiary amidoamine may be used in combination with an acid. The acid is typically used as a salt-forming anion. In one embodiment, the acid is selected from the group consisting of lactic acid, malic acid, hydrochloric acid, 1-glutamic acid, acetic acid, citric acid, and mixtures thereof.

[0108] In at least one embodiment, the cationic surfactant is selected from the group consisting of cetyltrimonium chloride (CTAC), stearyltrimonium chloride (STAC), behentrimonium methosulfate, stearoylamidopropyldimethylamine (SAPDMA), distearyldimethylammonium chloride, and mixtures thereof.

[0109] In at least one embodiment, the formulation comprises a surfactant system. In at least one embodiment, the surfactant system comprises a surfactant selected from the group consisting of anionic surfactants, cationic surfactants, nonionic surfactants, zwitterionic surfactants, and / or amphoteric surfactants. In at least one embodiment, the formulation comprises a total amount of surfactants between 0.01 wt% and 70 wt%, between 0.1 wt% and 40%, between 1 wt% and 30%, or between 2 wt% and 20 wt%.

[0110] In at least one embodiment, the formulation comprises an anionic surfactant. In at least one embodiment, the anionic surfactant is 10 ~C 20 )-alkyl and alkylene carboxylates, alkyl ether carboxylates, fatty alcohol sulfates, fatty alcohol ether sulfates, alkylamide sulfates and sulfonates, fatty acid alkylamide polyglycol ether sulfates, alkane sulfonates and hydroxyalkane sulfonates, olefin sulfonates, acyl esters of isethionates, α-sulfofatty acid esters, alkylbenzene sulfonates, alkylphenol glycol ether sulfonates, sulfosuccinates, sulfosuccinic acid monoesters and diesters, fatty alcohol ether phosphates, protein / fatty acid condensation products, alkyl monoglyceride sulfates and sulfonates, alkyl glyceride ether sulfonates, fatty acid methyl taurides, fatty acid sarcosinates, sulforicinoleates, acyl glutamates, and mixtures thereof. The anionic surfactants (and mixtures thereof) may be used in the form of their water-soluble or water-dispersible salts, such as sodium, potassium, magnesium, ammonium, mono-, di-, and triethanolammonium, and similar alkylammonium salts. In at least one embodiment, the anionic surfactant is a salt of an anionic surfactant containing 12 to 14 carbon atoms. In at least one embodiment, the anionic surfactant is selected from the group consisting of sodium lauryl sulfate, sodium laureth sulfate, sodium tridecyl sulfate, sodium trideceth sulfate, sodium myristyl sulfate, sodium myreth sulfate, and mixtures thereof.

[0111] In at least one embodiment, the formulation includes an acylglycinate surfactant, hi at least one embodiment, the acylglycinate surfactant conforms to formula (Y): [ka] (In the formula, R 1a is a linear or branched, saturated alkyl group having 6 to 30, preferably 8 to 22, particularly preferably 8 to 18 carbon atoms, or a linear or branched, mono- or polyunsaturated alkyl group having 6 to 30, preferably 8 to 22, particularly preferably 12 to 18 carbon atoms, Q a + is a cation.)

[0112] In at least one embodiment, Q a + Li + , Na + , K. + , Mg ++ , Ca ++ , Al +++ , NH4 + In at least one embodiment, the acyl glycinate surfactant is selected from the group consisting of sodium cocoyl glycinate and potassium cocoyl glycinate. In at least one embodiment, the acyl glycinate surfactant is represented by the formula (Y) where R is C 12 Alkyl or C 14 In at least one embodiment, the acyl glycinate surfactant is selected from those according to formula (Y) where R is C 16 Alkyl or C 18 is alkyl.

[0113] In at least one embodiment, the formulation comprises a glutamate surfactant corresponding to formula (Z) or a salt thereof: [ka] (wherein R' is HOOC-CH2-CH2- or M+-OOC-CH2-CH2-, where M+ is a cation; R is a linear or branched, saturated alkenyl group having 6 to 30, preferably 8 to 22, and more preferably 8 to 18 carbon atoms, or a linear or branched, mono- or polyunsaturated alkenyl group having 6 to 30, preferably 8 to 22, and more preferably 12 to 18 carbon atoms.) In at least one embodiment, M + is a metal cation. In at least one embodiment, M + Li + , Na + , K. + , Mg ++ , Ca ++ , Al +++ , N.H. 4+ , monoalkylammonium ions, dialkylammonium ions, trialkylammonium ions and tetraalkylammonium ions, or combinations thereof.

[0114] In at least one embodiment, the glutamic acid surfactant is selected from sodium cocoyl glutamate and potassium cocoyl glutamate. In at least one embodiment, the glutamic acid surfactant is represented by formula (Z), where R is C 12 Alkyl or C 14 In at least one embodiment, the glutamic acid surfactant is selected from those according to formula (Z), where R is C 16 Alkyl or C 18 The group is selected from the group consisting of alkyl, aryl, aryl, aryl ...

[0115] In at least one embodiment, the formulation comprises 0.01 wt% to 30 wt%, or 1 wt% to 25 wt%, preferably 5 wt% to 20 wt%, more preferably 12 wt% to 18 wt% of anionic surfactant.

[0116] In at least one embodiment, the formulation includes a nonionic surfactant. In at least one embodiment, the nonionic surfactant has an HLB (hydrophilic lipophilic balance) greater than 12. Optionally, the nonionic surfactant is selected from the group consisting of ethoxylated or ethoxylated / propoxylated fatty alcohols having a fatty chain containing 12 to 22 carbon atoms, ethoxylated sterols such as stearyl or lauryl alcohol (EO-7), PEG-16 soy sterol or PEG-10 soy sterol, polyoxyethylene polyoxypropylene block polymers (poloxamers), and mixtures thereof.

[0117] In at least one embodiment, the nonionic surfactant is an ethoxylated fatty alcohol, fatty acid, fatty acid glyceride, or alkylphenol, particularly a C8-C 22 to fatty alcohols, C 12 ~C 22 Adducts of 2 to 30 mol of ethylene oxide and / or 1 to 5 mol of propylene oxide to fatty acids or to alkylphenols having 8 to 15 carbon atoms in the alkyl group, and C of adducts of 1 to 30 mol of ethylene oxide to glycerol 12 ~C 22 Fatty acid mono- and diesters, adducts of 5 to 60 moles of ethylene oxide onto castor oil or hydrogenated castor oil, fatty acid sugar esters, especially sucrose and one or two C8-C 22 Esters of fatty acids, INCI: sucrose cocoate, sucrose dilaurate, sucrose distearate, sucrose laurate, sucrose myristate, sucrose oleate, sucrose palmitate, sucrose ricinoleate, sucrose stearate, sorbitan and one, two or three C8-C 22 Fatty acids and esters with an ethoxylation degree of 4 to 20, polyglyceryl fatty acid esters (especially those with one, two or more C8 to C 22 of fatty acids and preferably polyglycerols having 2 to 20 glyceryl units), C8 to C 22The alkyl group is selected from the group consisting of alkyl glucosides, alkyl oligoglucosides and alkyl polyglucosides, such as decyl glucoside or lauryl glucoside, and mixtures thereof.

[0118] In at least one embodiment, the nonionic surfactant is selected from the group consisting of fatty alcohol ethoxylates (alkyl polyethylene glycols), alkylphenol polyethylene glycols, alkyl mercaptan polyethylene glycols, fatty amine ethoxylates (alkylamino polyethylene glycols), fatty acid ethoxylates (acyl polyethylene glycols), polypropylene glycol ethoxylates (e.g., Pluronics®), fatty acid alkylolamides, (fatty acid amide polyethylene glycols), N-alkyl fatty acid amides, N-alkoxy polyhydroxy fatty acid amides, sucrose esters, sorbitol esters, polyglycol ethers, and mixtures thereof.

[0119] In at least one embodiment, the formulation comprises a fatty acid N-methyl-N-glucamide surfactant, wherein the fatty acid N-methyl-N-glucamide surfactant conforms to the following formula (X): [ka] (Wherein, R is selected from saturated or unsaturated hydrocarbon chains having 5 to 23 carbon atoms; preferably, R is selected from saturated or unsaturated hydrocarbon chains having 7 to 17 carbon atoms. Also, preferably, in the formula, the RC=O residue 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, in the formula, the RC=O residue is derived from 9-decenoic acid, 9-dodecenoic acid, or a mixture thereof.)

[0120] Particularly preferably, the N-methyl-N-acylglucamine of formula (X) is capryloyl / caproyl methyl glucamide, lauroyl / myristoyl methyl glucamide, cocoyl methyl glucamide, oleyl methyl glucamide, or mixtures thereof. Such N-methyl-N-acylglucamines are commercially available from Clariant (GlucoTain® Clear, GlucoTain® Plus, GlucoTain® Flex, GlucoTain® Care, GlucoTain® Sense).

[0121] Particularly preferably, the N-methyl-N-acylglucamine of formula (X) is N-9-decenoyl-N-methylglucamine, N-9-dodecenoyl-N-methylglucamine, or a mixture thereof.

[0122] In at least one embodiment, the formulation comprises between 1 wt% and 20 wt%, more preferably between 2 wt% and 10 wt%, and even more preferably between 3 wt% and 7 wt% of a non-ionic surfactant.

[0123] In at least one embodiment, the amphoteric surfactants are N—(C) as alkali metal salts and mono-, di-, and trialkylammonium salts. 12 ~C 18 )-Alkyl-β-aminopropionates and N-(C 12 ~C 18 )-Alkyl-β-iminodipropionates; N-Acylaminoalkyl-N,N-dimethylacetobetaines, preferably N-(C 18 )-Acylaminopropyl-N,N-dimethylacetobetaine, (C 12 ~C 18 )-Alkyl-dimethyl-sulfopropyl betaines, imidazoline-based amphoteric surfactants (e.g. Miranol®, Steinapon®), preferably the sodium salt of 1-(β-carboxymethyloxyethyl)-1-(carboxymethyl)-2-laurylimidazolinium; amine oxides, e.g. (C 12 ~C18 )-alkyl-dimethyl-amine oxides, fatty acid amide alkyl dimethyl amine oxides, and mixtures thereof.

[0124] In at least one embodiment, the formulation comprises a betaine surfactant. Optionally, the betaine surfactant is a C8-C 18 In at least one embodiment, the betaine surfactant is selected from the group consisting of cocodimethylcarboxymethyl betaine, lauryldimethylcarboxymethyl betaine, lauryldimethyl alphacarboxyethyl betaine, cetyldimethylcarboxymethyl betaine, oleyldimethyl gammacarboxypropyl betaine, and laurylbis(2-hydroxypropyl)alphacarboxyethyl betaine, and combinations thereof. Optionally, the betaine surfactant is selected from the group consisting of C8-C 18 In at least one embodiment, the betaine surfactant is selected from the group consisting of cocodimethylsulfopropyl betaine, stearyldimethylsulfopropyl betaine, lauryldimethylsulfoethyl betaine, laurylbis(2-hydroxyethyl)sulfopropyl betaine, and combinations thereof. Optionally, the betaine surfactant is a carboxyl derivative of imidazole, C8-C 18 Alkyldimethylammonium acetate, C8-C 18 Alkyldimethylcarbonylmethylammonium salts, and C8-C 18 Optionally, the alkylaminobetaine is selected from C8 to C6 fatty acid alkylamide betaines, and mixtures thereof. 18 The fatty acid alkylamidobetaine is selected from coconut fatty acid amidopropyl betaine, N-coconut fatty acid amidoethyl-N-[2-(carboxymethoxy)ethyl]glycerol (CTFA name: Cocoamphocarboxyglycinate), and mixtures thereof.

[0125] In at least one embodiment, the formulation comprises 0.5 wt% to 20 wt%, preferably 1 wt% to 10 wt%, of an amphoteric surfactant.

[0126] In at least one embodiment, the formulation includes a surfactant system. In at least one embodiment, the surfactant system includes at least one surfactant selected from the group consisting of lauryl sulfate, laureth sulfate, cocoamidopropyl betaine, sodium cocoyl glutamate, lauroamphoacetate, and mixtures thereof. In at least one embodiment, the surfactant system includes sodium laureth sulfate, sodium lauryl sulfate, and optionally cocamidopropyl betaine. In at least one embodiment, the surfactant system includes sodium laureth sulfate, potassium cocoyl glutamate, and cocamidopropyl betaine.

[0127] In at least one embodiment, the formulation further comprises a hair styling polymer. In at least one embodiment, the hair styling polymer is selected from the group consisting of amphoteric hair styling polymers, zwitterionic hair styling polymers, anionic hair styling polymers, nonionic hair styling polymers, cationic hair styling polymers, and mixtures thereof. In at least one embodiment, the formulation comprises 0.01% to 20%, or 0.01% to 16%, or 0.01% to 10%, or 1% to 8%, or 2% to 6% of the hair styling polymer. Preferred hair styling polymers are disclosed in WO 2018 / 002100 (pages 55-63).

[0128] In at least one embodiment, the formulation has a viscosity of 0 cPs to 20,000 cPs. In at least one embodiment, the formulation has a viscosity of 0.1 cPs to 10,000 cPs, or 1 cPs to 5,000 cPs, or 5 cPs to 3,500 cPs. Viscosity measurement conditions are defined in the definitions section above. Viscosity can be important for reasons of preventing dripping, which can be inconvenient for the user. Additionally, more viscous formulations can be useful for metered dispensing. In at least one embodiment, the formulation has a viscosity of 0 cPs to 1,000 cPs. This viscosity range is advantageous in terms of the need for spreading on the skin and the ability to be rinsed off when the formulation is in the form of a facial cleanser.

[0129] In at least one embodiment, the formulation further comprises a viscosity modifier, which is preferably a thickening polymer.

[0130] In at least one embodiment, the thickening polymer is a polymer based on acrylamidomethylpropanesulfonic acid (AMPS®, Lubrizol). These polymers exhibit good thickening properties even at pH values ​​below 7. Particularly preferably, the thickening polymer is selected from the group consisting of homopolymers or copolymers of acrylamidomethylpropanesulfonic acid and its salts. Among the just-mentioned polymers, preference is next given to polymers having at least 20 mol % of units based on acrylamidomethylpropanesulfonic acid and / or its salts, and particular preference is given to polymers having at least 50 mol % of units based on acrylamidomethylpropanesulfonic acid and / or its salts (molar amounts in each case relating to the entire polymer). In the case of copolymers, as well as structural units based on acrylamidomethylpropanesulfonic acid and / or its salts, preferably one or more structural units based on the following comonomers are present in the copolymer: acrylic acid, methacrylic acid, acrylamide, dimethylacrylamide, vinylpyrrolidone (VP), hydroxyethyl acrylate, hydroxyethyl methacrylate, ethoxylated alcohol RO-(CHCHO). mH (wherein R is an alkyl group having 12 to 30 carbon atoms, m is a number from 3 to 30, and CH═CH—COO—(CHCH—COO) n X (where n is a number from 0 to 10, and X is a counter ion, preferably H + , Na + and / or NH4 + The polymers selected from the group consisting of homopolymers or copolymers of acrylamidomethylpropanesulfonic acid and its salts may be crosslinked or non-crosslinked. In the case of crosslinking, they contain structural units for monomers having two or more olefinic double bonds. In the case of crosslinking, preferably 0.1 to 10 mol % of such structural units are present in the homopolymer or copolymer, based on the total polymer. One or more structural units for acrylamidomethylpropanesulfonic acid and / or its salts in the homopolymer or copolymer of acrylamidomethylpropanesulfonic acid and / or its salts are H + If the compound has one or more counterions other than Na, these other counterions may be + and NH4 +Suitable polymers are preferably selected from the group consisting of: Suitable polymers are mentioned in publications including EP 0 816 403, EP 1 069 142, EP 1 116 733 and DE 10 2009 014877 (Clariant), EP 1 347 736 (L'Oreal) or EP 1 496 081 (Seppic). Examples include Aristoflex® AVC (ammonium acryloyldimethyl taurate / VP copolymer), Aristoflex® AVS (sodium acryloyldimethyl taurate / VP crosspolymer), Aristoflex® TAC (ammonium acryloyldimethyl taurate carboxyethyl acrylate crosspolymer), Hostacerin® AMP5 (ammonium polyacryloyldimethyl taurate), Aristoflex® HMB (ammonium acryloyldimethyl taurate / beheneth-25 methacrylate crosspolymer), Aristoflex® BLV ...

[0039] Examples of suitable hydroxyethyl acrylate crosspolymers include Aristoflex® HMS (ammonium acryloyldimethyl taurate / steareth-25 methacrylate crosspolymer), Aristoflex® SNC (ammonium acryloyldimethyl taurate / steareth-8 methacrylate copolymer), Aristoflex® LNC (ammonium acryloyldimethyl taurate / laureth-7 methacrylate copolymer) or Sepinov® EMT10 (hydroxyethyl acrylate / sodium acryloyldimethyl taurate copolymer), Sepigel® 305.

[0131] In at least one embodiment, the thickening polymer is a copolymer of at least one first monomer type selected from acrylic acid and methacrylic acid, and at least one second monomer type selected from esters of acrylic acid and ethoxylated fatty alcohols; crosslinked polyacrylic acid; at least one first monomer type selected from acrylic acid and methacrylic acid, and C 10 ~C30 Crosslinked copolymers of at least one second monomer type selected from esters of acrylic acid with alcohols; copolymers of at least one first monomer type selected from acrylic acid and methacrylic acid and at least one second monomer type selected from esters of itaconic acid and ethoxylated fatty alcohols; copolymers of at least one first monomer type selected from acrylic acid and methacrylic acid, esters of itaconic acid and ethoxylated fatty alcohols. 10 ~C 30 Copolymers of at least one second monomer type selected from alcohols and a third monomer type selected from C1-C4 aminoalkyl acrylates; copolymers of two or more monomers selected from acrylic acid, methacrylic acid, acrylic esters, and methacrylic esters; copolymers of vinylpyrrolidone and ammonium acryloyldimethyl taurate; copolymers of ammonium acryloyldimethyl taurate and monomers selected from esters of methacrylic acid and ethoxylated fatty alcohols; hydroxyethyl cellulose; hydroxypropyl cellulose; hydroxypropyl guar; glyceryl polyacrylate acrylate; glyceryl polymethacrylate; copolymers of at least one C2-, C3-, or C4 alkylene and styrene; polyurethane; hydroxypropyl starch phosphate; polyacrylamide; copolymers of maleic anhydride and methyl vinyl ether crosslinked with decadiene; carob seed flour; guar gum; xanthan; dehydroxanthan; carrageenan; karaya gum; hydrolyzed corn starch; copolymers of polyethylene oxide, fatty alcohol, and saturated methylene diphenyl diisocyanate (e.g., PEG-150 / stearyl alcohol / SMDI copolymer); and mixtures thereof.

[0132] In at least one embodiment, the formulation has a pH value of 2.0 to 12.0, preferably 3.0 to 9.0, more preferably 4.5 to 7.5. Varying the pH value allows formulations to be available that are suitable for a variety of applications.

[0133] In at least one embodiment, the formulation includes an alkalizing or pH adjusting agent. In at least one embodiment, ammonia or caustic soda are preferred, although water-soluble, physiologically acceptable salts of organic or inorganic bases are also contemplated. Optionally, the pH adjusting agent is selected from ammonium bicarbonate, ammonia, monoethanolamine, and ammonium carbonate. In at least one embodiment, the alkalizing agent is selected from the group consisting of 2-amino-2-methyl-1-propanol, 2-amino-2-methyl-1,3-propanediol, 2-amino-2-ethyl-1,3-propanediol, tris(hydroxyl-methyl)-aminomethane, 2-amino-1-butanol, tris-(2-hydroxypropyl)-amine, 2,2-iminobisethanol, lysine, iminourea (guanidine carbonate), tetrahydro-1,4-oxazine, 2-amino-5-guanidine-valeric acid, 2-aminoethanesulfonic acid, diethanolamine, triethanolamine, N-methylethanolamine, isopropanolamine, diisopropanolamine, triisopropanolamine, glucamine, sodium hydroxide, potassium hydroxide, lithium hydroxide, magnesium oxide, and mixtures thereof.

[0134] An acid can be included to establish an acidic pH. In at least one embodiment, the formulation includes an acid selected from the group consisting of hydrochloric acid, phosphoric acid, acetic acid, formic acid, sulfuric acid, citric acid, and mixtures thereof. Citric acid is most preferred due to its high consumer acceptance. In at least one embodiment, the acidic pH is adjusted with a buffer solution such as a phosphate buffer, a TRIS buffer, or a citrate buffer. The buffer solution can be used alone or in combination with the acid.

[0135] In at least one embodiment, the formulation is in liquid form. In an alternative embodiment, the formulation is in solid form. Optionally, the formulation is in powder or granular form. This is advantageous in that it typically does not require transporting heavy liquids over long distances, which has economic and environmental benefits. A solid form can be achieved by spray-drying the formulation or using a rotary evaporator. After transportation, the formulation can be converted into a liquid form, for example, by adding water.

[0136] In at least one embodiment, the formulation is a household cleaning formulation.

[0137] In at least one embodiment, the formulation is a hand dishwashing formulation. In at least one embodiment, the hand dishwashing formulation comprises an anionic surfactant. In at least one embodiment, the hand dishwashing formulation comprises 5 wt% to 25 wt% anionic surfactant. In at least one embodiment, the hand dishwashing formulation comprises at least one anionic surfactant and an additional surfactant selected from a nonionic surfactant, an amphoteric surfactant, a zwitterionic surfactant, and combinations thereof.

[0138] Preferably, the hand dishwashing formulation comprises cocoamidopropyl betaine or an amine oxide. Preferably, the amine oxide is lauryl amine oxide, cocoyl amine oxide, or a combination thereof. In at least one embodiment, the hand dishwashing formulation has a pH value between pH 5.0 and pH 10, preferably between pH 5.5 and pH 9.0. For hand dishwashing formulations comprising an amine oxide, the hand dishwashing formulation preferably has a pH between pH 7.5 and pH 9.5, most preferably between pH 8.0 and pH 9.0.

[0139] In at least one embodiment, the formulation is a hard surface cleaner. In at least one embodiment, the hard surface cleaner comprises an anionic surfactant. In at least one embodiment, the hard surface cleaner comprises 1 wt % to 10 wt % anionic surfactant. In at least one embodiment, the hard surface cleaner comprises a nonionic surfactant. In at least one embodiment, the hard surface cleaner comprises 1 wt % to 10 wt % nonionic surfactant. In at least one embodiment, the hard surface cleaner comprises a surfactant system comprising at least one anionic surfactant and an additional surfactant selected from nonionic surfactants, amphoteric surfactants, zwitterionic surfactants, and combinations thereof. Preferably, the hard surface cleaner comprises a linear alkyl benzene sulfonate and a fatty alcohol ethoxylate. In at least one embodiment, the hard surface cleaner has a pH value between pH 5.0 and pH 11, preferably pH 6.0 to pH 9.0.

[0140] In at least one embodiment, the formulation is a liquid laundry detergent formulation comprising one or more surfactants. Preferably, the one or more surfactants in the liquid laundry detergent formulation are selected from the group consisting of anionic, nonionic, cationic, and zwitterionic surfactants, and more preferably the group consisting of anionic, nonionic, and zwitterionic surfactants.

[0141] Anionic surfactants In at least one embodiment, the formulation includes an anionic surfactant. Anionic surfactants are particularly useful in cleaning formulations, such as household cleaning formulations. Preferred anionic surfactants are alkyl sulfonates and alkyl ether sulfates. Preferred alkyl sulfonates are alkyl benzene sulfonates, especially C8-C 15 , preferably C 12 ~C 14The preferred alkyl ether sulfates (AES) are linear alkyl benzene sulfonates (LAS) having an alkyl chain length of 1000 to 15000. Possible counterions to the concentrate lye are ammonium ions (e.g., those produced by neutralizing alkyl benzene sulfonic acid with one or more ethanolamines, such as monoethanolamine (MEA) and triethanolamine (TEA)), or alternatively, alkali metal ions (e.g., those resulting from neutralizing alkyl benzene sulfonic acid with an alkali hydroxide). The preferred alkyl ether sulfates (AES) are alkyl polyethoxylate sulfate anionic surfactants.

[0142] Nonionic surfactants In at least one embodiment, the formulation includes a nonionic surfactant, including primary and secondary alcohol ethoxylates, particularly C8-C8 ethoxylated with an average of 1 to 20 moles of ethylene oxide per mole of alcohol. 20 Aliphatic alcohols, and more specifically C ethoxylated with an average of 1 to 10 moles of ethylene oxide per mole of alcohol 10 ~C 15 These include primary and secondary fatty alcohols. Non-ethoxylated nonionic surfactants include alkyl polyglycosides, glycerol monoethers, and polyhydroxyamides (glucamides). Mixtures of nonionic surfactants may also be used.

[0143] When included therein, household cleaning formulations, particularly liquid laundry detergent formulations, preferably contain 0.2 wt % to 40 wt %, more preferably 1 wt % to 20 wt %, of a nonionic surfactant such as alcohol ethoxylates, nonylphenol ethoxylates, alkyl polyglycosides, alkyl dimethylamine oxides, ethoxylated fatty acid monoethanolamides, fatty acid monoethanolamides, polyhydroxyalkyl fatty acid amides, N-acyl N-alkyl derivatives of glucosamine (glucamides), or combinations thereof. Nonionic surfactants that may be used include primary and secondary alcohol ethoxylates, particularly C8-C6 ethoxylates ethoxylated with an average of 1 to 35 moles of ethylene oxide per mole of alcohol. 20 Aliphatic alcohols, and more specifically C ethoxylated with an average of 1 to 10 moles of ethylene oxide per mole of alcohol 10 ~C 15 Primary and secondary aliphatic alcohols are included.

[0144] Zwitterionic surfactants In at least one embodiment, the formulation comprises a zwitterionic surfactant. The liquid laundry detergent formulation may comprise a zwitterionic surfactant, such as an amine oxide or a betaine, preferably in an amount of up to 10 wt % based on the total weight of the liquid laundry detergent formulation. Betaines may comprise an alkyl group having a C 12 ~C 18 It may be a chain-containing alkyldimethylbetaine or alkylamidobetaine.

[0145] Additional surfactants In at least one embodiment, the liquid laundry detergent formulation comprises a surfactant selected from the group consisting of anionic surfactants, nonionic surfactants, and mixtures thereof; preferably, the surfactant is selected from the group consisting of linear alkylbenzene sulfonates, alkyl ether sulfates, nonionic surfactants, amine oxides, and betaines; more preferably, the surfactant is selected from the group consisting of linear alkylbenzene sulfonates, alkyl ether sulfates, and nonionic surfactants. Surfactants other than the preferred LAS, AES, and nonionic surfactants may also be added. Less preferred are alkyl sulfate surfactants, particularly non-ethoxylated C 12 ~C 15 Primary and secondary alkyl sulfates may be used. Soaps may also be used. The soap level is preferably less than 10 wt%.

[0146] Preferably, the surfactant(s) in the liquid laundry detergent formulation are present in an amount of at least 5 wt %, preferably 5 wt % to 65 wt %, more preferably 6 to 60 wt %, and especially preferably 7 wt % to 55 wt %, in each case based on the total weight of the liquid laundry detergent formulation.

[0147] Further optional ingredients The household cleaning formulation may contain one or more optional ingredients, for example, the household cleaning formulation may contain conventional ingredients commonly used in detergent compositions, particularly laundry detergent compositions. Examples of optional ingredients include, but are not limited to, builders, bleaches, bleach active compounds, bleach activators, bleach catalysts, photobleaches, color transfer inhibitors, color inhibitors, anti-resoiling agents, dispersants, softeners and antistatic agents, optical brighteners, enzymes, enzyme stabilizers, foam regulators, defoamers, malodor reducers, preservatives, bactericides, hydrotropes, fiber lubricants, shrink inhibitors, buffers, fragrances, processing aids, colorants, dyes, pigments, anti-corrosion agents, fillers, stabilizers, or other conventional ingredients for cleaning or laundry detergent compositions.

[0148] polymer For enhanced detergency, it may be advantageous to use a polymer in household cleaning formulations, particularly liquid laundry detergent formulations. The polymer is preferably polyalkoxylated polyethyleneimine (EPEI). Polyethyleneimine is a material consisting of ethyleneimine units -CHCHNH-, and when branched, the hydrogen on the nitrogen is replaced by another chain of ethyleneimine units. These polyethyleneimines can be prepared, for example, by polymerizing ethyleneimine in the presence of a catalyst such as carbon dioxide, sodium bisulfite, sulfuric acid, hydrogen peroxide, hydrochloric acid, acetic acid, etc. Specific methods for preparing these polyamine backbones are disclosed in US 2,182,306, US 3,033,746, US 2,208,095, US 2,806,839, and US 2,553,696.

[0149] Household cleaning formulations, particularly liquid laundry detergent formulations, may contain other polymeric materials, such as color transfer inhibiting polymers, anti-resoiling polymers, or cotton soil release polymers, particularly those based on modified cellulose materials. In particular, when EPEI is not present, the formulation may further contain a polymer of polyethylene glycol and vinyl acetate, such as a light graft copolymer described in WO2007 / 138054. Such amphiphilic graft polymers based on a graft base formed by polymerization of vinyl ester components and a water-soluble polyalkylene oxide as a side chain have the ability to reduce the surfactant level while maintaining a high level of oily soil removal.

[0150] Hydrotrope In at least one embodiment, the formulation includes a hydrotrope. As used herein, a "hydrotrope" is a solvent that is neither water nor a conventional surfactant, but that helps solubilize surfactants and other ingredients in a liquid, particularly any polymers and / or sequestering agents, and makes the liquid isotropic. Hydrotropes are particularly useful in household cleaning formulations. Among suitable hydrotropes, the following are noteworthy: monopropylene glycol (MPG), glycerol, sodium cumene sulfonate, ethanol, other glycols such as dipropylene glycol, diethers, and urea. MPG and glycerol are preferred hydrotropes.

[0151] enzyme In at least one embodiment, the formulation, particularly a liquid laundry detergent formulation, includes an enzyme. In at least one embodiment, the enzyme is selected from the group consisting of proteases, mannanases, pectate lyases, cutinases, esterases, lipases, amylases, cellulases, and combinations thereof. Less preferred additional enzymes may be selected from peroxidases and oxidases. The enzymes are preferably present together with a corresponding enzyme stabilizer. The total enzyme content in the formulation is preferably 0 wt% to 5 wt%, more preferably 0.5 wt% to 5 wt%, and even more preferably 1 wt% to 4 wt% by total weight of the formulation.

[0152] Sequestering Agents Sequestering agents are preferably included in formulations, especially household cleaning formulations. Preferred sequestering agents include organic phosphonates, alkanehydroxyphosphonates, and carboxylates, available, for example, from Thermophos under the trademark DEQUEST. Preferred sequestering agent levels are less than 10 wt. % and preferably less than 5 wt. % by total weight of the formulation. A particularly preferred sequestering agent is HEDP (1-hydroxyethylidene-1,1-diphosphonic acid), sold, for example, as Dequest 2010. Also suitable is Dequest 2066 (diethylenetriaminepenta(methylene-phosphonic acid) or Heptasodium DTPMP).

[0153] buffer In at least one embodiment, the formulation, particularly a liquid laundry detergent formulation, contains a buffer. The presence of a buffer, in addition to optional agents for the production of anionic surfactants, such as LAS or fatty acid-derived surfactants, is preferred for pH control. Possible buffers include one or more ethanolamines, such as monoethanolamine (MEA) or triethanolamine (TEA). These are preferably used at levels of 1.0 to 15 wt% in the formulation. Other suitable aminoalcohol buffering materials can be selected from the group consisting of compounds having a molecular weight above 61 g / mol, including MEA. Suitable materials also include, in addition to those already mentioned, monoisopropanolamine, diisopropanolamine, triisopropanolamine, monoaminohexanol, 2-[(2-methoxyethyl)methylamino]-ethanol, propanolamine, N-methylethanolamine, diethanolamine, monobutanolamine, isobutanolamine, monopentanolamine, 1-amino-3-(2-methoxyethoxy)-2-propanol, 2-methyl-4-(methylamino)-2-butanol, or mixtures thereof.

[0154] The present invention also relates to the use of the combination of the invention as an antibacterial agent.

[0155] In at least one embodiment, the antimicrobial agent is an antibacterial agent or an antifungal agent. In at least one embodiment, the antimicrobial agent is an antibacterial agent. In at least one embodiment, the antimicrobial agent is an antifungal agent.

[0156] The present invention also relates to a method for reducing the impact of microorganisms in a formulation, said method comprising the step of adding to the formulation a combination of the present invention.

[0157] In at least one embodiment, the microorganism is a bacterium or a fungus. In at least one embodiment, the microorganism is a bacterium. In at least one embodiment, the microorganism is a fungus. The fungus may be, for example, a yeast or a mold.

[0158] As used herein, including all embodiments of all aspects of the invention, the following definitions apply unless otherwise stated: All percentages are weight percent (w / w) of the total composition. All ratios are by weight. "wt%" means percent by weight. "Parts" is by weight, e.g., "a mixture of 1 part X and 3 parts Y." "QS" or "QSP" means a quantity sufficient for 100% or 100 g. + / - indicates standard deviation. All ranges are inclusive and combinable. The number of significant digits does not imply a limitation on the stated amount or the precision of the measurements. All measurements were made at 23°C and ambient conditions, where "ambient conditions" means conditions of 1 atmosphere (atm) pressure and 50% relative humidity. "Relative humidity" refers to the ratio (expressed as a percentage) of the moisture content of air compared to the saturation moisture level at the same temperature and pressure. Relative humidity can be measured with a hygrometer, particularly a VWR® International probe hygrometer. As used herein, "min" means "minute(s)." As used herein, "mol" means mole. As used herein, "g" after a number means "gram." As used herein, "comprising" means that other steps and other ingredients can be added. "Comprising" encompasses the terms "consisting of" and "consisting essentially of."

[0159] The compositions, formulations, methods, uses, and processes of the present invention can include, consist of, or consist essentially of the inventive elements and limitations described herein, as well as any additional or optional components, steps, or limitations described herein. The embodiments and aspects described herein can include or be combined with elements, features, or components of other embodiments and / or aspects, even if not explicitly exemplified in combination, unless incompatibility is stated.

[0160] "In at least one embodiment" means that one or more embodiments of the invention, optionally all embodiments or a larger subset of the embodiments, have the characteristics described thereafter. When amount ranges are given, they should be understood as the total amount of that component in the composition, or, if multiple species are included within a component definition, as the total amount of all components in the composition that fit that definition.

[0161] "Molecular weight" or "M.Wt." or "MW" and grammatical equivalents means number average molecular weight.

[0162] "Viscosity" is 12.9s -1 at a shear rate of 1000 rpm and at 25°C using a HAAKE Rotation Viscometer VT 550 with a cooling / heating vessel and sensor system according to DIN 53019.

[0163] "Water-soluble" refers to any substance that is sufficiently soluble in water to form a solution that is clear to the naked eye at a concentration of 0.1% by weight of the substance in water at 25° C. The phrase "water-insoluble" refers to any substance that is not "water-soluble."

[0164] "Dry" or "substantially dry" means containing less than 5%, less than 3%, or less than 2%, less than 1%, or about 0% of any compound or composition in liquid form when measured at 25°C under ambient conditions. Such compounds or compositions in liquid form include water, oils, organic solvents, and other humectants. "Anhydrous" means that the composition contains less than 5%, less than 3%, or less than 2%, less than 1%, or about 0% water, based on the total weight of the composition.

[0165] "Substantially free from" or "substantially free of" means less than 1%, or less than 0.8%, or less than 0.5%, or less than 0.3%, or about 0% by weight of the composition or formulation.

[0166] "Derivatives" include, but are not limited to, amide, ether, ester, amino, carboxyl, acetyl, acid, salt, and / or alcohol derivatives of a given compound. In one embodiment, "derivatives thereof" refers to amide, ether, ester, amino, carboxyl, acetyl, acid, salt, and alcohol derivatives. [Example]

[0167] The following examples are intended to illustrate the subject matter of the present invention without limiting it.

[0168] material Velsan® Flex is commercially available from Clariant. Chemical name: capryloyl / caproyl anhydromethyl glucamide (and) water. Active ingredient: 70 wt%. Capryloyl / caproyl anhydromethyl glucamide 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® SC is commercially available from Clariant Chemical name: sorbitan caprylate. Velsan® CGE is commercially available from Clariant Chemical name: Caprylyl glyceryl ether. 4-Hydroxyacetophenone is commercially available from Sigma Aldrich.

[0169] Example 1 Velsan Flex, 4-hydroxyacetophenone, and a combination of both were investigated for their antibacterial properties against bacteria, yeast, and mold. To test for bacterial growth inhibition, Velsan Flex, 4-hydroxyacetophenone, or a combination of both were diluted with butyl polyglycol and added at different concentrations to liquid Cazo agar medium at 50°C and buffered to pH 7 (+ / - 0.2). To test for inhibition of yeast and mold growth, Velsan Flex, 4-hydroxyacetophenone, or a combination of both was diluted with butyl polyglycol and added at different concentrations to liquid Sabouraud 4% dextrose agar at 50°C and buffered to pH 5.6 (+ / - 0.2). Each solution was poured into Petri dishes and inoculated with equal amounts of bacteria, yeast, or mold. The minimum inhibitory concentration (MIC) is the lowest concentration of each compound that inhibits the growth of the respective microorganism, and is the concentration below which the growth of that microorganism cannot be inhibited. The experiments were conducted under scientifically sound conditions to allow for appropriate comparisons and conclusions to be drawn. The results are shown in the following table.

[0170] [Table 1]

[0171] The combination of two components exhibits a synergistic effect, as evidenced by a lower MIC for the combination compared to the MIC for the single components. This effect was observed against a wide range of microorganisms, including both bacteria and fungi. This offers the advantage of allowing formulations, such as cosmetic and household preparations, to be preserved with smaller amounts of a single preservative, reducing the potential for adverse effects from antimicrobial active ingredients and saving resources.

[0172] In a similar experiment to that described above, the antimicrobial properties of Velsan SC, 4-hydroxyacetophenone, and their combination were investigated against bacteria, yeast, and mold. The results are shown in the following table.

[0173] [Table 2]

[0174] The MICs of the combination of Velsan SC and 4-hydroxyacetophenone were lower than those of the individual components, confirming a synergistic effect. This effect was observed against a wide range of microorganisms, including both bacteria and fungi. This has the advantage of allowing formulations such as cosmetic and household products to be preserved with smaller amounts of a single preservative, reducing the potential for adverse effects from antimicrobial active substances and saving resources.

[0175] Example 2 Challenge test demonstrates antiseptic efficacy: The synergistic effect and ability to preserve common leave-on cosmetic products were also demonstrated. The following examples show the results of challenge tests conducted in accordance with Chapter 5.1.3 of the European Pharmacopoeia, 10th Edition. The following test strains were used as representative microorganisms: Pseudomonas aeruginosa (Gram-negative bacterium, abbreviated as "Pa"), Staphylococcus aureus (Gram-positive bacterium, abbreviated as "Sa"), Escherichia coli (Gram-negative bacterium, abbreviated as "Ec"), Candida albicans (yeast, abbreviated as "Ca"), and Aspergillus brasiliensis (mold, abbreviated as "Ab"). Criterion A represents the recommended efficacy to be achieved. In justified cases where criterion A cannot be achieved due to reasons such as an increased risk of side effects, criterion B must be met. Criterion A is associated with excellent protection of the formulation, while criterion B is necessary to demonstrate sufficient protection, but additional risk elimination measures related to packaging and raw material quality must be applied. If criterion F is achieved for any of the tested organisms, the entire challenge test will fail and the formulation will be insufficiently preserved / protected. As a reference, an unpreserved sample of each formulation was also tested. A difficult-to-preserve formulation was used as the test system.

[0176] [Table 3]

[0177] The results of the challenge test of the formulations at pH 7 are shown in the following table.

[0178] [Table 4]

[0179] The preservative-free test system fails the challenge test against all test organisms at pH 7 (entry 7). Hydroxyacetophenone at a 0.5% use level is not sufficient to preserve the formulation, failing Ec (entry 6) and achieving only a B for Sa. Velsan SC, Velsan Flex, or Velsan CGE alone are also not sufficient to preserve the formulation (entries 8–11). In contrast, the combination of Velsan Flex and hydroxyacetophenone at 0.5% and 0.5% use levels (entry 1) achieves an A rating against all test organisms, demonstrating excellent formulation preservation. The same formulation, when used with Velsan SC and hydroxyacetophenone at 0.5% and 0.5% (entry 2), also achieves an A rating against all test organisms at pH 7, demonstrating excellent formulation preservation. A similar effect is observed with the combination of Velsan CGE and hydroxyacetophenone at 0.25% and 0.5%, which also achieves an A rating against all organisms (entry 4). Using 0.5% Velsan CGE in combination with hydroxyacetophenone, it is possible to reduce the amount of hydroxyacetophenone to 0.25% (entry 3), resulting in an A standard for all test organisms, whereas using 0.25% hydroxyacetophenone as the sole preservative (entry 5) only results in an F standard for all test organisms.

[0180] The results presented in Example 2 demonstrate that the combination of hydroxyacetophenone with Velsan Flex, Velsan SC, or Velsan CGE exhibits a synergistic effect, as evidenced by the ability to pass a challenge test at a use concentration of only 0.5%, even though hydroxyacetophenone alone, or Velsan Flex, Velsan SC, or Velsan CGE alone, is insufficient to adequately protect the cosmetic formulation at this concentration. This has the advantage of allowing formulations, such as cosmetic and household formulations, to be preserved with a smaller amount of a single preservative, potentially reducing the potential for adverse effects from antimicrobial actives.

[0181] Example 3 Combination examples of the present invention (wt%)

[0182] [Table 5] Legend * = Compound of formula (I) (wherein R is -(CH2)8CH3) # = Compound of formula (I) (wherein R is -(CH2)6CH3)

[0183] The combination is prepared by mixing the ingredients at room temperature.

[0184] Example 4 Combination examples of the present invention (wt%)

[0185] [Table 6]

[0186] The combination is prepared by mixing the ingredients at room temperature.

[0187] Example 5 Combination examples of the present invention (wt%)

[0188] [Table 7]

[0189] The combination is prepared by mixing the ingredients at room temperature.

[0190] Example 6 Formulation examples of the present invention (wt%)

[0191] [Table 8]

[0192] Example 7 Formulation examples of the present invention (wt%)

[0193] [Table 9]

[0194] Example 8 Formulation examples of the present invention (wt%)

[0195] [Table 10]

[0196] [Table 11]

[0197] Example 9 Formulation examples of the present invention (wt%)

[0198] [Table 12]

[0199] Example 10 Formulation examples of the present invention (wt%)

[0200] [Table 13]

[0201] Example 11 Formulation examples of the present invention (wt%)

[0202] [Table 14]

Claims

1. (A) at least one compound selected from the group consisting of a compound of formula (I), a sorbitan ester, an isosorbide ester, a glyceryl ether, and a glyceryl ester; and 【Chemistry 1】 wherein R is selected from saturated hydrocarbon chains having from 5 to 23 carbon atoms, unsaturated hydrocarbon chains having from 5 to 23 carbon atoms, and mixtures thereof. (B) at least one hydroxyacetophenone; A combination including:

2. 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; Preferably, the hydrocarbon chain 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 are saturated hydrocarbon chains having 5 to 9 carbon atoms, unsaturated hydrocarbon chains having 5 to 9 carbon atoms and mixtures thereof. The combination of claim 1.

3. 3. The combination of claim 1 or 2, wherein the sorbitan ester is a mono-, di- or tri-ester of sorbitan and one or more C6-C20 fatty acids (preferably a mono- or diester of sorbitan and one or more C8-C14 fatty acids, particularly preferably a mono- or diester of sorbitan and caprylic acid).

4. 4. The combination of any one of claims 1 to 3, wherein the sorbitan ester is selected from sorbitan caprylate, sorbitan stearate, sorbitan olivate, sorbitan oleate, sorbitan caprate, sorbitan laurate, sorbitan myristate, sorbitan caproate, and mixtures thereof, preferably sorbitan caprylate.

5. 5. The combination of any one of claims 1 to 4, wherein the isosorbide ester is a mono- or diester of isosorbide and one or more C6-C20 fatty acids, preferably a mono- or diester of isosorbide and one or more C8-C14 fatty acids, particularly preferably a mono- or diester of isosorbide and caprylic acid.

6. 6. The combination of any one of claims 1 to 5, wherein the isosorbide ester is selected from isosorbide caprylate, isosorbide stearate, isosorbide olivate, isosorbide oleate, isosorbide caprate, isosorbide laurate, isosorbide myristate, isosorbide caproate, and mixtures thereof, preferably isosorbide caprylate.

7. 7. The combination of any one of claims 1 to 6, wherein the glyceryl ether is a mono- or di-ether of glycerin and one or more C6-C20 fatty alcohols, preferably a mono- or di-ether of glycerin and one or more C8-C14 fatty alcohols, particularly preferably a mono- or di-ether of glycerin and one or more C8 fatty alcohols.

8. The combination of any one of claims 1 to 7, wherein the hydroxyacetophenone is selected from 2-hydroxyacetophenone, 3-hydroxyacetophenone, 4-hydroxyacetophenone, and mixtures thereof.

9. 9. The combination of claim 8, wherein the hydroxyacetophenone is 4-hydroxyacetophenone.

10. 10. The combination of any one of claims 1 to 9, wherein the weight ratio of (A) at least one compound selected from the group consisting of compounds of formula (I), sorbitan esters, isosorbide esters, glyceryl ethers, and glyceryl esters to (B) at least one hydroxyacetophenone is from 20:1 to 1:5, preferably from 15:1 to 1:2, more preferably from 12:1 to 1:1, particularly preferably from 10:1 to 3:1, for example from 6:1 to 7:

1.

11. The combination of any one of claims 1 to 10, wherein the combination is a blend.

12. The blend is 25 to 99 wt. %, preferably 40 to 80 wt. %, more preferably 55 to 70 wt. %, and particularly preferably 60 to 65 wt. %, based on the total weight of the blend, of (A) at least one compound selected from the group consisting of compounds of formula (I), sorbitan esters, isosorbide esters, glyceryl ethers, and glyceryl esters; and 12. The combination of claim 11, comprising 1 to 50 wt. %, preferably 2 to 20 wt. %, more preferably 5 to 15 wt. %, and especially preferably 8 to 12 wt. % of (B) at least one hydroxyacetophenone, based on the total weight of the blend.

13. Use of any one of the combinations of claims 1 to 12 as an antibacterial agent.

14. A method for reducing the impact of microorganisms in a formulation, comprising the step of adding to the formulation a combination according to any one of claims 1 to 12.

15. (A) 0.1 to 10% by weight, preferably 0.2 to 3% by weight, particularly preferably 0.3 to 1.5% by weight, of at least one compound selected from the group consisting of a compound of formula (I), a sorbitan ester, an isosorbide ester, a glyceryl ether, and a glyceryl ester, based on the total weight of the formulation; and 【Chemistry 1】 wherein R is selected from saturated hydrocarbon chains having from 5 to 23 carbon atoms, unsaturated hydrocarbon chains having from 5 to 23 carbon atoms, and mixtures thereof. (B) 0.01 to 1.5% by weight, preferably 0.05 to 0.5% by weight, particularly preferably 0.1 to 0.3% by weight, of at least one hydroxyacetophenone, based on the total weight of the formulation; A formulation comprising:

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