Conditioner for keratin fibers

Abstract

The present invention relates to a cosmetic formulation containing a dye precursor, at least one tertiary amine or quaternary ammonium compound and an aliphatic hydrocarbon having at least 10 carbon atoms; to the use thereof for dyeing and caring for keratin fibers; and to a corresponding application method. The invention also relates to a kit comprising the cosmetic formulation according to the invention in combination with an additional cosmetic formulation, such as a shampoo.

Description

[0001] 222217PEP

[0002] Dr. Kurt Wolff GmbH & Co. KG

[0003] Conditioner for keratin fibers

[0004] The present invention relates to a cosmetic formulation comprising a dye precursor, a tertiary amine or a quaternary ammonium compound, and an aliphatic hydrocarbon with at least 10 carbon atoms, the use of which for dyeing and conditioning keratin fibers, and a corresponding application method. The invention further relates to a kit comprising the cosmetic formulation according to the invention in combination with an additional cosmetic formulation, such as a shampoo.

[0005] A person's hair color depends on the amount of melanins, eumelanin and pheomelanin, contained in the hair's cortex and produced by melanocytes in the hair follicles. As part of the normal aging process, but also due to certain illnesses, stress, vitamin and mineral deficiencies, or excessive alcohol or nicotine consumption, melanin production can decrease, resulting in hypopigmentation. Such hair appears white or colorless to the observer. The visual impression of gray hair results from the mixture of pigmented and unpigmented hairs.

[0006] The average life cycle of a hair is three to seven years, after which the hair falls out and a new hair grows in its place. Gradually, the proportion of white or unpigmented hairs increases, and the hair turns gray.

[0007] Changing hair color, and in particular the pigmentation or repigmentation of gray hair, represents an important area of ​​modern cosmetics. Good colorfastness, effective gray coverage, and long-lasting results are especially desirable.

[0008] For permanent, intense colorations with good fastness properties and good gray coverage, oxidation dyes are conventionally used. Such dyes typically contain oxidation dye precursors, so-called developer components and coupler components, which, under the influence of oxidizing agents, such as hydrogen peroxide, or atmospheric oxygen, react with each other or with one or more coupler components to form the actual dyes.

[0009] However, the use of oxidative dyes is still associated with impairment or damage to the hair and especially its surface structure.

[0010] Alternatively, precursors of the natural hair pigment melanin can be applied to the hair, which, through oxidative processes within the hair, form practically nature-identical pigments. The coloring process can be carried out using atmospheric oxygen as the sole oxidizing agent, thus eliminating the need for any other oxidizing agents. Such a process, using 5,6-dihydroxyindoline as a pigment precursor, is described, for example, in EP 0 530 229 B1.

[0011] In contrast, temporary hair colors use direct dyes, also known as direct dyes. These are dye molecules that adhere directly to the hair shaft and do not require an oxidative process to develop the color. Compared to oxidative hair coloring, colors achieved with direct dyes are less long-lasting and wash out more quickly. Dyes with direct dyes typically remain on the hair for between 5 and 20 washes.

[0012] WO 99 / 66890 describes a dye for dyeing keratin fibers containing a dye precursor, which may be an indoline or indole derivative, e.g., a derivative of 5,6-dihydroxyindoline or 5,6-dihydroxyindole, as well as an amino acid or an oligopeptide. The color can be formed by air oxidation.

[0013] DE 10 2018 127 182 A1 relates to a two-component system for artificial hair coloring, comprising separately an anhydrous carrier medium consisting of an alkane, a fatty alcohol, and an alcohol, and an aqueous phase containing hydrogen peroxide. An organosilicon compound from the silane group may be included for hair protection and conditioning.

[0014] DE 10 2007 038 484 A1 describes a hair treatment product for protection against external influences, wherein the hair treatment product contains bacterial ferment(s) from Thermus thermophilus.

[0015] WO 2005 / 007615 A1 concerns 2-(amino or substituted amino)-5-(substituted oxymethyl)-phenol compounds and compositions for the oxidative dyeing of keratin fibers.

[0016] EP 4 154 864 describes a cosmetic formulation which contains, in addition to dye precursors, a direct dye.

[0017] The described dyeing compositions usually require quite harsh application conditions, such as a strongly alkaline pH value or strongly oxidizing conditions, which can damage the hair structure.

[0018] Therefore, there is a need for care products that simultaneously pigment the hair with high authenticity properties, good grey coverage and long-lasting color performance.

[0019] Surprisingly, it was found that the results regarding the quality of care and the intensity and duration of the coloring performance are improved when the care formulation contains, in addition to dye precursors, tertiary amines or quaternary ammonium compounds and - possibly functionalized - aliphatic hydrocarbons in a certain ratio.

[0020] The object of the present invention can therefore be seen as providing a cosmetic formulation that is suitable for both conditioning and coloring keratin fibers.

[0021] The problem was surprisingly solved by a cosmetic formulation that

[0022] (i) at least one dye precursor selected from the group consisting of indoline derivatives and indole derivatives, (ii) at least one tertiary amine or quaternary ammonium compound, each comprising at least one N-bonded aliphatic hydrocarbon residue having 10-32 carbon atoms,

[0023] (iii) at least one aliphatic hydrocarbon having at least 10, preferably 10-50, carbon atoms, optionally substituted with at least one functional group selected from -OH and -COOR, wherein R is independently H, a glycerol derivative or a physiologically acceptable cation, wherein the weight ratio of component (ii) to component

[0024] (iii) in the range of 1 :1 - 1 :8, preferably 1 :2-1 :5.

[0025] Surprisingly, it was found that the formulation according to the invention effectively covers gray hair and gradually darkens the hair overall, with the color effect building up subtly. Furthermore, the color hardly fades even after repeated washing, and graying at the roots is reduced. Even with regular use of the formulation according to the invention, the hair does not become straw-like or develop split ends – as is often the case with conventional hair coloring products. The formulation according to the invention gives the hair a beautiful shine and makes it easy to comb.

[0026] The dye precursor contained in the formulation according to the invention, which is an indole derivative and / or indolin derivative, is preferably an indole derivative and / or indolin derivative having a hydroxy or amino group, preferably as a substituent on the six-membered ring. These groups may bear further substituents, e.g., in the form of etherification or esterification of the hydroxy group or alkylation of the amino group. Compounds with two of these groups, in particular two hydroxy groups, one or both of which may be etherified or esterified, are particularly preferred.

[0027] In a preferred embodiment of the invention, the dye precursor is an indole derivative. Preferably, according to the invention, the dye precursor is a derivative of 5,6-

[0028] Dihydroxyindoles of the formula (I), each independently of each other,

[0029] R 1Hydrogen, a Ci-C4 alkyl group, or a Ci-C4 hydroxyalkyl group means,

[0030] R 2 hydrogen or a -COOH group, where the -COOH group can also exist as a salt with a physiologically acceptable cation,

[0031] R 3 Hydrogen or a Ci-C4 alkyl group means

[0032] R 4 Hydrogen, a Ci-C4 alkyl group, an amino group or a group - COR 6 means, in the R 6 a Ci-C4 alkyl group means, and

[0033] R 5 one of the under R 4 The aforementioned groups mean, or a physiologically acceptable salt of these compounds with an organic or inorganic acid.

[0034] Preferred indole derivatives are 5,6-dihydroxyindole, N-methyl-5,6-dihydroxyindole, N-ethyl-5,6-dihydroxyindole, N-propyl-5,6-dihydroxyindole, N-butyl-5,6-dihydroxyindole.

[0035] In a particularly preferred embodiment, the compound of formula (I) is selected from 5,6-dihydroxyindole, N-methyl-5,6-dihydroxyindole and their physiologically acceptable salts.

[0036] The dye precursor used in the formulation according to the invention is particularly preferably 5,6-dihydroxyindole.

[0037] In another preferred embodiment of the invention, the dye precursor is an indoline derivative.

[0038] Preferably, the dye precursor is a derivative of 5,6-dihydroxyindoline of formula (II), each independently of each other,

[0039] R 1 Hydrogen, a Ci-C4 alkyl group, or a Ci-C4 hydroxyalkyl group means,

[0040] R 2 hydrogen or a -COOH group, where the -COOH group can also exist as a salt with a physiologically acceptable cation, R 3Hydrogen or a Ci-C4 alkyl group means

[0041] R 4 Hydrogen, a Ci-C4 alkyl group, an amino group or a group - COR 6 means, in the R 6 a Ci-C4 alkyl group, and R 5 one of the under R 4 The aforementioned groups mean, or a physiologically acceptable salt of these compounds with an organic or inorganic acid.

[0042] Preferred indoline derivatives are 5,6-dihydroxyindoline, N-methyl-5,6-dihydroxyindoline, N-ethyl-5,6-dihydroxyindoline.

[0043] In a particularly preferred embodiment, the compound of formula (II) is selected from 5,6-dihydroxyindoline, N-methyl-5,6-dihydroxyindoline and their physiologically acceptable salts.

[0044] The dye precursor used in the formulation according to the invention is particularly preferably 5,6-dihydroxyindoline.

[0045] In a further particularly preferred embodiment, the dye precursor used in the formulation according to the invention is dihydroxyindole hydrobromide (2,3-dihydro-1 H-indole-5,6-diol hydrobromide).

[0046] The indole and indolin derivatives contained in the compositions according to the invention can be used both as free bases and in the form of their physiologically acceptable salts with inorganic or organic acids, e.g., the hydrochlorides, sulfates, and hydrobromides. The indole or indolin derivative is typically present in the formulation according to the invention in an amount of 0.01–0.5 wt.%, preferably 0.05–0.5 wt.%, preferably 0.05–0.4 wt.%, preferably 0.1–0.3 wt.%, preferably 0.05–0.2 wt.%, more preferably in an amount of 0.05–0.15 wt.%, approximately 0.05 wt.%, or approximately 0.1 wt.%, respectively, based on the total weight of the formulation.

[0047] In a particularly preferred embodiment, the dye precursor is an indole derivative, preferably 5,6-dihydroxyindole, wherein in the formulation according to the invention it is preferably contained in an amount of 0.01–0.2 wt.%, preferably 0.05–0.15 wt.%, in each case based on the total weight of the formulation.

[0048] In a further particularly preferred embodiment, the dye precursor is an indoline derivative, preferably dihydroxyindoline hydrobromide (2,3-dihydro-1 H-indole-5,6-diol hydrobromide), wherein this is preferably contained in the formulation according to the invention in an amount of 0.01–0.2 wt.%, preferably 0.05–0.15 wt.%, in each case based on the total weight of the formulation.

[0049] The formulation according to the invention can also contain more than one indole or indolin derivative or mixtures of indole and indolin derivatives.

[0050] The formation of the pigment from the dye precursor, i.e. the indole or indolin derivative, occurs through reaction with atmospheric oxygen; no additional oxidizing agent is required.

[0051] Furthermore, the cosmetic formulation contains at least one tertiary amine or quaternary ammonium compound, each with at least one N-bonded aliphatic hydrocarbon residue having 10-32 carbon atoms, which may optionally contain a -C(O)O- or -O- group (component (ii)).

[0052] The aliphatic hydrocarbon residue is preferably saturated or unsaturated, in particular saturated.

[0053] The aliphatic hydrocarbon residue is preferably unbranched. Preferably, the aliphatic hydrocarbon residue has 10-23 carbon atoms. Preferably, component (ii) is a quaternary ammonium compound with an N-bonded aliphatic, preferably unbranched, hydrocarbon residue having 10-23 carbon atoms.

[0054] In particular, the aliphatic hydrocarbon residue is a hexadecane, heptadecane, octadecane, eicosan or behenyl residue.

[0055] The nitrogen atom in the tertiary amine has a total of three covalent valences. The nitrogen atom in the quaternary ammonium compound has a total of four valences. At least one valence of the nitrogen atom is occupied by the hydrocarbon group described above. The remaining free valences of the nitrogen atom in the tertiary amine and in the quaternary ammonium compound are preferably occupied by Ci-C4 alkyl groups or Ci-C4 hydroxyalkyl groups, in particular methyl or ethyl groups.

[0056] The positive charge in the quaternary ammonium compound is preferably balanced by physiologically acceptable anions such as halides, especially chloride and bromide, or methosulfate.

[0057] Preferred tertiary amines include, for example, behenyldimethylamine, behenyldiethylamine, eicosandimethylamine and eicosandiethylamine.

[0058] Preferred quaternary ammonium compounds are behentrimonium chloride, cetrimonium chloride, cetyltrimethylammonium bromide, distearoylethyl hydroxyethylmonium methosulfate, distearoylethyl dimonium chloride, bis- (isostearoyl / oleoyl isopropyl) dimonium methosulfate and esterquats.

[0059] Component (ii) is preferably present in the cosmetic formulation at a weight of 0.1–10 wt.%, more preferably 0.5–5 wt.%, even more preferably 1–5 wt.%, even more preferably 1–3 wt.%, and even more preferably 1.5–2.5 wt.%. According to the invention, the cosmetic formulation contains at least one aliphatic hydrocarbon having at least 10 carbon atoms, which may optionally be substituted with at least one functional group selected from -OH and -COOR (component (iii)).

[0060] The aliphatic hydrocarbon is preferably a saturated or unsaturated hydrocarbon, particularly preferably a saturated hydrocarbon. The hydrocarbon preferably has 10-50, more preferably 10-24, carbon atoms. The hydrocarbons according to component (iii) are preferably unbranched. The aliphatic hydrocarbon is preferably an unbranched hydrocarbon with 10-24 carbon atoms, optionally substituted with -OH or -COOR, where RH is or a physiologically acceptable cation, such as Na or K.

[0061] The aliphatic hydrocarbon is preferably a saturated and unbranched hydrocarbon with 10-24 carbon atoms, which may be substituted with -OH.

[0062] Preferred representatives of component (iii) are paraffins, fatty alcohols, fatty acids, glycerol fatty acid esters or their salts, in particular fatty alcohols.

[0063] Preferred paraffins (unsubstituted hydrocarbon) are Cio-24-paraffins, Ci6-24-paraffins are even more preferred.

[0064] Preferred fatty alcohols (substituted with -OH) are lauryl alcohol, myristyl alcohol, cetyl alcohol, margaryl alcohol, stearyl alcohol, cetearyl alcohol and behenyl alcohol, in particular lauryl alcohol, cetyl alcohol, cetearyl alcohol and stearyl alcohol, especially cetearyl alcohol (a mixture of cetyl and stearyl alcohol).

[0065] Preferred fatty acids (R=H) are capric acid, lauric acid, myristic acid, palmitic acid, margaric acid, stearic acid, arachidic acid, and behenic acid, in particular lauric acid, palmitic acid and stearic acid, more preferably palmitic acid and stearic acid.

[0066] In the case of R = glycerol derivative, in particular glycerol residue, glycerol monofatty acid ester residue, or glycerol difatty acid ester residue, the substituted hydrocarbon is a glycerol fatty acid ester. In the present invention, the term "glycerol fatty acid ester" refers to a glycerol mono-, glycerol di-, or glycerol trifatty acid ester. Glycerol difatty acid esters have the formula R'-COO-(CH₂CH(OH)CH₂)-OOCR' or R'-COO-(CH₂CH(OOCR')CH₂)-OH. Glycerol monofatty acid esters have the formula R'-COO-(CH₂CH(OH)CH₂)-OH or HO-(CH₂CH(OOCR')CH₂)-OH. Here, R' is, independently of each other, the aliphatic hydrocarbon as defined above. Glycerol monofatty acid esters contain a glycerol group which is linked to a single fatty acid via an ester bond. Examples include glycerol monostearate, glycerol monobehenate, glycerol monocaprylate, glycerol monocaprate, and glycerol monolaurate. In glycerol trifatty acid esters, all hydroxyl groups of glycerol are esterified with fatty acids.

[0067] Preferably component (iii) is at least a paraffin, fatty alcohol, fatty acid, glycerol fatty acid ester or a mixture thereof, in particular at least a saturated Cw-24 fatty alcohol, at least a saturated Cio-24 fatty acid or a mixture thereof, most preferably at least a saturated C10-24 fatty alcohol.

[0068] According to the invention, the proportion of component (iii) is at least 2 wt.%, preferably 4-20 wt.%, more preferably 3-17 wt.%, more preferably 4-17 wt.%, even more preferably 4-8 wt.%, even more preferably 3-5 wt.%, based on the total mass of the cosmetic formulation.

[0069] The weight ratio of component (ii) to component (iii) is in the range of 1:1 to 1:8, preferably 1:2 to 1:5, preferably 1:2 to 1:4. By adjusting the weight ratio of component (ii) to (iii) in the claimed range, an improved color effect is achieved.

[0070] The combination of components (ii) and (iii) allows a pH value in the range of 4–9, preferably 5–8, more preferably 6–7.5, and most preferably 6–<7, to be achieved. The formulation is stable within this pH range. In some preferred embodiments, the formulation further contains at least one organic acid and / or an organic buffer system and has a pH value in the range of 2.5–7.5, particularly 3–6. Surprisingly, it has been found that, despite an acidic to neutral pH range, the presence of components (ii) and (iii) in the cosmetic formulation leads to faster penetration of dye precursors into the keratin fiber. This increases the color depth and simultaneously improves the duration of the dyeing effect compared to conventional formulations. Furthermore, the processing time can be reduced.

[0071] The acidic or near-neutral pH value of the formulation also has positive effects on the hair's feel, shine, and combability.

[0072] Furthermore, component (iii) ensures a good feel of the formulation and the desired viscosity in order to achieve the strongest possible adhesion of the cosmetic formulation to the keratin fiber.

[0073] Furthermore, the cosmetic formulation according to the invention can contain at least one direct dye, such as a nitrophenylenediamine, nitroaminophenol, nitro dye, azo dye, anthraquinone or indophenol (component (iv)). Component (iv) is preferably present in an amount of 0.001 to 3 wt.%, more preferably in an amount of 0.01 to 2 wt.%, and more preferably in an amount of 0.3 to 0.9 wt.% based on the total mass of the formulation.

[0074] It was found that the color effect of a formulation containing both an indole- or indolin-type dye precursor and a direct dye is more intense than would have been expected based on the color effects of the individual components: the indole- or indolin-type dye precursor and the direct dye. The darkening effects are synergistically enhanced by the combination with direct dyes.

[0075] As mentioned at the outset, direct dyes are dye molecules that adhere directly to the hair and do not require an oxidative process to develop the color. Preferred direct dyes include nitrophenylenediamines, nitroaminophenols, azo dyes, nitro dyes, anthraquinones, and indophenols, and are preferably selected from the group known by the international names [insert names here].Handelsnamen bekannten Farbstoffe HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, HC Yellow 12, Acid Yellow 1 , Acid Yellow 10, Acid Yellow 23, Acid Yellow 36, Basic Yellow 57, Basic Yellow 87, HC Orange i , Disperse Orange 3, Acid Orange 7, Basic Orange 31 , HC Red 1 , HC Red 3, HC Red 10, HC Red 11 , HC Red 13, HC Red BN, Acid Red 33, Acid Red 52, Pigment Red 57:1 , Basic Red 51 , Basic Red 76, HC Blue 2, HC Blue 12, HC Blue 16, Disperse Blue 3, Acid Blue 7, Basic Blue 99, Acid Green 50, HC Violet 1 , Disperse Violet 1 , Disperse Violet 4, Acid Violet 43, Disperse Black 9, Acid Black 1 , Acid Black 52, Basic Brown 16 und Basic Brown 17 sowie 1 ,4-Diamino-2-nitrobenzol, 2-Amino-4-nitrophenol, 1 ,4-Bis-(ß-hydroxyethyl)-amino-2-nitrobenzol, 3-Nitro-4-(ß- hydroxyethyl)-aminophenol, 2-(2-Hydroxyethyl)amino-4,6-dinitrophenol, 1 -(2'-.

[0076] Hydroxyethyl)amino-4-methyl-2-nitrobenzene, 1-Amino-4-(2-hydroxyethyl)-amino-5-chloro-2-nitrobenzene, 4-Amino-3-nitrophenol, 1-(2-Ureidoethyl)amino-4-nitrobenzene, 4-Amino-2-nitrodiphenylamine-2'-carboxylic acid, 6-Nitro-1,2,3,4-tetrahydroquinoxaline, 2-Hydroxy-1,4-naphthoquinone, Hydroxyethyl-2-nitro-toluidine, Picramic acid and its salts, 2-Amino-6-chloro-4-nitrophenol, 4-Ethylamino-3-nitrobenzoic acid and 2-Chloro-6-ethylamino-1-hydroxy-4-nitrobenzene.

[0077] In a preferred embodiment, the direct-drawing dye is selected from the group consisting of 2-Amino-6-chloro-4-nitrophenol, 1,4-Bis-(β-hydroxyethyl)-amino-2-nitrobenzene, Basic Yellow 57, Basic Red 76, Basic Brown 16, Basic Brown 17, Basic Blue 99, HC Blue 2, HC Blue 12, HC Blue 16 and Acid Violet 43.

[0078] In a particularly preferred embodiment of the invention, the direct-drawing dye is HC Blue 2.

[0079] In a preferred embodiment, the formulation according to the invention contains 5,6-dihydroxyindole as a dye precursor and HC Blue 2 as a direct-acting dye. The 5,6-dihydroxyindole is present in an amount of 0.05–0.15 wt.% and the direct-acting dye in an amount of 0.01–0.9 wt.%, each based on the total weight of the formulation. To improve processability and adjust viscosity, the cosmetic formulation may further contain water, in particular purified or distilled water (component (v)). The cosmetic formulation preferably contains 70–95 wt.%, more preferably 80–95 wt.%, and more preferably 85–95 wt.%, water based on the total mass of the formulation.

[0080] Furthermore, the cosmetic formulation according to the invention can contain all additives (i.e., active ingredients, additives and excipients) known in such preparations.

[0081] In one embodiment, the cosmetic formulation comprises a surfactant. The surfactant can be anionic, non-ionic, cationic, or zwitterionic. Preferably, the surfactant is an anionic or non-ionic surfactant, in particular a mild (i.e., especially skin-friendly) anionic or non-ionic surfactant. According to the invention, non-ionic surfactants are used especially because of their very good emulsifying properties and their excellent skin-care properties. Anionic surfactants are preferred because they exhibit particularly high cleaning performance. Therefore, they are especially suitable for cleansing formulations such as shampoos. Cationic surfactants possess excellent hair-care properties and are used according to the invention especially in hair-care formulations such as conditioners, shampoos, and treatments.

[0082] The formulation according to the invention preferably contains surfactants in an amount of 2 to 40 wt.%, in particular 5 to 30 wt.%, preferably 7 to 20 wt.%, and most preferably 10 to 17 wt.%, based on the total weight of the formulation. Suitable amounts of surfactant are: 8 wt.%; 9 wt.%; 10 wt.%; 11 wt.%; 12 wt.%; 13 wt.%; 14 wt.%; 15 wt.%; 16 wt.%; 17 wt.%; 18 wt.%; 19 wt.%; 20 wt.%; 21 wt.%; 22 wt.%; 23 wt.%; 24 wt.%; 25 wt.%, based on the total weight of the formulation. The cosmetic formulation of the invention most preferably contains one or more anionic surfactants in an amount of 0.1 to 20 wt.%, preferably 1 to 17 wt.%, and most preferably 5 to 15 wt.%, in each case based on the total weight of the formulation. Suitable amounts of anionic surfactant are: 1 wt.%; 2 wt.%; 3 wt.%; 4 wt.%; 5 wt.%; 6 wt.%; 7 wt.%; 8 wt.%; 9 wt.%; 10 wt.%; 11 wt.%; 12 wt.%.-%; 13 wt%; 14 wt%; 15 wt%; 16 wt%; 17 wt%; 18 wt%, 19 wt%, 20 wt%, each based on the total weight of the formulation. At these amounts, the surfactants exhibit particularly high cleaning performance and are extremely well-tolerated by skin, scalp, and hair.

[0083] In a preferred embodiment, the surfactant is an anionic surfactant selected from alkyl sulfonates, alkyl sulfates, alkyl ether sulfates, alkyl phosphates, alkyl sarcosinates, alkyl taurates, amino acid surfactants, and mixtures thereof. Particularly preferred is a surfactant selected from alkyl sulfates, alkyl sarcosinates, alkyl taurates, alkyl glutamate (such as sodium cocoyl glutamate / disodium cocoyl glutamate), alkyl glycinate, alkyl alaninate (such as sodium cocoyl alaninate), and mixtures thereof. Also preferred, due to their cleaning performance, are fatty alcohol polyglycerol ether sulfates, monoglyceride sulfates, mono- and / or dialkyl sulfosuccinates, fatty acid isethionates, and α-olefin sulfonates.

[0084] Alkyl sulfates have the generic formula ROSO3M, alkyl sarcosinates have the generic formula RC(O)N(CH3)CH2CO2M, and alkyl taurates have the generic formula RC(O)N(CH3)CH2CH2SO3M, where R is a C4-C26 alkyl or C4-C26 alkenyl and M is a water-soluble cation such as ammonium, sodium, or potassium. Preferably, M is a sodium cation. Preferably, R is a Ci2-Ci6 alkyl or a Ci2-Ci8 alkyl.

[0085] In one embodiment, the surfactant is a nonionic surfactant (also referred to as a nonionic emulsifier). Non-limiting examples include polyoxyethylene ethers of one or more fatty alcohols, alkoxylated fatty acid alkyl esters, polyglycerol ethers of fatty alcohols, polyglycerol esters of fatty acids, polyethylene glycol and / or polypropylene glycol ethers, fatty acid amides, alkylphenol polyglycol ethers, amine oxides, and alkyl polyglucosides.

[0086] In one embodiment, the surfactant is selected from the group consisting of polyoxyethylene ethers of one or more fatty alcohols, polyglycerol ethers of fatty alcohols, polyglycerol esters of fatty acids and mixtures thereof.

[0087] Polyoxyethylene ethers are compounds of the formula R 5 (OC2H3)nOH, where R 5 The polyoxyethylene ether is selected from Ce-C28 alkyl, Ce-C28 alkenyl, substituted and unsubstituted phenoxy groups; and n is an integer greater than 1. Preferably, the polyoxyethylene ether is selected from the group consisting of steareth-2, steareth-21, macrogol cetostearyl ether 12, ceteareth-25, macrogol cetostearyl ether 20, and mixtures of the aforementioned compounds. Even more preferably, the polyoxyethylene ether is a compound selected from the group consisting of ceteareth-25, macrogol cetostearyl ether 20, and mixtures of the aforementioned compounds.

[0088] The term "polyglycerol ether of fatty alcohols" refers to a compound of the formula R 6 O-(C3H6O2)nH, where R 6 The compound is a branched or linear Ce-C28 alkyl or Ce-C28 alkenyl, and n is an integer greater than 1, preferably an integer from 2 to 10. It is preferred that the formulation contains 0.01 to 15.0 wt.%, 0.1 to 10.0 wt.%, or 1 to 5.0 wt.% polyglycerol ethers.

[0089] The term "polyglycerol esters of fatty acids" refers to compounds containing both a polyglycerol unit and at least one Ce-C26 alkyl or C6-C26 alkenylcarboxylic acid unit. These compounds may have the formula R 7 -R 8 - (C3H6O2)nH exhibit, where R 7 a Ce-C26 alkanoate or Ce-C26 alkenoate residue and R 8a suitable linking molecule or a direct bond. Thus, the polyglycerol unit and the Ce-C26 alkyl or C6-C26 alkenyl carboxylic acid unit can be directly linked by an ester bond or contain a linking unit that connects these two units. Non-limiting examples of this group are polyglyceryl-3-methylglucose distearate, polyglycerol polycrinoleate, polyglyceryl dimerate isostearate, polyglyceryl-2-laurate, polyglyceryl-2-sesquiisostearate, polyglyceryl-3-distearate (Cremophor GS 32), polyglyceryl-3-oleate, Polyglyceryl-3-methylglycose distearate, polyglyceryl-4-caprate (polyglycerol caprate T2010190), polyglyceryl-4-diisostearate / polyhydroxystearate / sebacate (Isolan GPS) and polyglyceryl-4-isostearate.

[0090] In one embodiment, the surfactant comprises a cationic surfactant. Advantageous surfactants include alkylamidopropyl betaine and alkylamidopropyl hydroxysulfaine, imidazoline derivatives, and compounds with cationic character such as amine oxides, for example, alkyldimethylamine oxides or alkylaminoethyldimethylamine oxides.

[0091] In the present invention, the surfactant, as defined above, is distinct from component (ii) and component (iii). In a further embodiment, the formulation according to the invention contains at least one additive. Preferably, the additives are those commonly used in shampoos, conditioners, and emulsions for the treatment of the skin, scalp, and hair. In one embodiment, the cosmetic formulation includes caffeine as an additive. The at least one additive can be present in a proportion of 0.01 wt.% to 12.0 wt.%, more preferably from 0.25 wt.% to 10.0 wt.%, and particularly from 0.5 wt.% to 5.0 wt.%.

[0092] The at least one additive may also be selected from the group consisting of hair conditioning agents, emollients, preservatives, stabilizers, perfumes, antioxidants, rheology modifiers, thickeners, conditioning agents, dyes, pearlescent agents, lightening agents, solvents, strengthening compounds, anti-dandruff agents, vitamins, alkalizing agents or pH adjusters and combinations thereof.

[0093] Hair conditioning products can reduce static electricity in the hair by neutralizing the electrical charge on its surface. Examples of hair conditioning products include quaternary ammonium compounds.

[0094] Emollients, also called re-fatting agents or superfatting agents, are lipophilic substances that can prevent a disruptive effect on the epidermal barrier function. Examples of emollients include lanolin, squalene, liquid paraffin, vegetable oils, silicones, and cetyl palmitate.

[0095] In preferred embodiments, the formulation according to the invention contains one or more silicones. Preferred silicones comprise polyalkylsiloxanes, in particular polydimethylsiloxanes such as dimethicone and / or dimethiconol, optionally functionalized with further functional groups. In preferred embodiments, the silicones are functionalized with one or more amine-containing residues, in particular with alkyl residues with primary and / or secondary amino groups. Amodimethicone is particularly preferred according to the invention. It is further preferred that the silicones are terminated with hydroxyl groups.

[0096] It was surprisingly found that the silicones in the formulation significantly improve the combability, softness, and shine of the hair, while maintaining good coloring properties. In preferred embodiments, the formulation according to the invention contains 0.00001–5 wt.%, preferably 0.0001–1 wt.%, more preferably 0.001–0.5 wt.%, and in particular 0.005–0.1 wt.% silicones as described herein.

[0097] Preservatives are substances used for preservation by killing microorganisms that degrade the formulation and / or inhibiting their growth. Preferably, the preservatives can be selected from the group consisting of benzoic acid, benzoic acid derivatives, sorbic acid, sorbic acid derivatives, salicylic acid, salicylic acid derivatives, phenoxyethanol, parabens, and combinations thereof. In a preferred embodiment, sodium benzoate and / or potassium sorbate are used as preservatives in the formulation according to the invention. Sodium benzoate releases benzoic acid and potassium sorbate releases sorbic acid in a slightly acidic environment. Both acids are attributed with antimicrobial properties.

[0098] Stabilizers can protect light-sensitive components from radiation and are preferably UV absorbers such as benzophenone derivatives.

[0099] The addition of fragrances can give the formulation a pleasant scent. Examples include perfumes familiar to professionals.

[0100] An antioxidant is a chemical compound that slows down or completely prevents the oxidation of other components in the formulation according to the invention. Preferred antioxidants include citric acid, ascorbic acid, sodium sulfite, butylhydroxyanisole, tocotrienols, tocopherols, and / or tocopherol derivatives.

[0101] In preferred embodiments, the formulation according to the invention contains tocopherols, tocopherol derivatives, and / or tocotrienols, preferably tocopherols and / or tocotrienols, more preferably tocopherols, particularly as antioxidants. (RRR)-tocopherols and, in particular, (RRR)-α-tocopherol, also known as vitamin E, are preferred as tocopherols. Tocopherol derivatives include, in particular, esters of tocopherols, preferably of (RRR)-α-tocopherol, such as tocopheryl acetate, tocopheryl succinate, tocopheryl nicotinate, and / or tocopheryl linoleate. According to the invention, the antioxidant effect of tocopheryl esters occurs particularly after hydrolysis to tocopherol. (RJ)-tocotrienols are preferred as tocotrienols, in particular (RJ-α-tocotrienol).

[0102] The formulation according to the invention preferably contains at least one antioxidant in an amount of 0.0001–5 wt.%, preferably 0.001–2 wt.%, more preferably 0.01–1 wt.%, and in particular 0.06–1.0 wt.%. Preferably, the at least one antioxidant is selected from tocopherols, tocopherol derivatives, and / or tocotrienols, more preferably from tocopherols and / or tocotrienols, and even more preferably from tocopherols; it is particularly preferred that the at least one antioxidant is (RRR)-α-tocopherol. It is further preferred that the formulation contains antioxidants in a total amount of 0.0001–5 wt.%, preferably 0.001–2 wt.%, more preferably 0.01–1 wt.%, and even more preferably 0.06–1.5 wt.%, and in particular 0.1–1 wt.%. Surprisingly, it was found that the addition of antioxidants, and in particular tocopherol, leads to a stabilization of the dye precursor (i) and to a significant increase in the dyeing effect.

[0103] Rheology modifiers and thickening agents can help to improve the application properties of the formulation according to the invention. The addition of sodium chloride (table salt) can be considered as a rheology modifier and thickening agent. The addition of sodium chloride can influence the flowability of the formulation according to the invention within certain limits and adjust it to the required level. Naturally occurring gelling agents, preferably selected from agar, xanthan gum, cellulose and / or cellulose derivatives, or alginic acid, can also be used as thickeners.

[0104] For the purposes of this application, "care products" are defined as substances that care for the hair and / or scalp. Hydrolyzed wheat protein, panthenol, and allantoin have a conditioning effect on the scalp and hair. Hydrolyzed wheat protein primarily has moisturizing properties.

[0105] The formulation according to the invention may also contain dyes, for example to give the formulation an aesthetically pleasing color. For example, CI 47005 may be included as a suitable dye in the formulation according to the invention.

[0106] A solvent or solvent mixture commonly used by those skilled in the art in this field can be employed. Preferred solvents are ethanol or butylene glycol, in particular 1,4-butylene glycol, propylene glycol, and isopropyl alcohol. Ethanol or propylene glycol is preferred. These solvents may preferably be present in the formulation according to the invention in an amount of 0.1 to 70% by weight. A particularly preferred amount is 0.1 to 5.0% by weight.

[0107] Strengthening compounds are preferably selected from the group consisting of waxes, synthetic polymers, and mixtures thereof. Suitable strengthening compounds are known to those skilled in the art and are described, for example, in Goddard, E. Desmond; Gruber, James V. (1999), “Principles of polymer science and technology in cosmetics and personal care”, Series: Cosmetic science and technology series: v. 22, New York (Marcel Dekker, INC.); Schrader, Karlheinz (1989), “Grundlagen und Rezepturen der Kosmetika” (2nd edition), Chapter 3.7, Heidelberg (Hüthig); and Scott, Richard (2017), “ingredients focus: cosmetic waxes and butters”, Personal Care Europe 10(3), 46-47.

[0108] Anti-dandruff agents are used to control excessive dandruff production on the scalp. Suitable anti-dandruff agents are known to those skilled in the art and are described, for example, in Trüeb, RM (2009). "Successfully treating dandruff." Akt Dermatol 35(01 / 02): 19-24; Trueb, RM (2007). "Shampoos: ingredients, efficacy and adverse effects." J. Dtsch. Dermatol. Ges. 5(5): 356-365; Sanfilippo, A. and J. English (2006). "An overview of medicated shampoos used in dandruff treatment." P AND T 31 (7): 396; and Futterer, E. (1981). "Evaluation of efficacy of antidandruff agents." J Soc Cosmet Chem 32: 327-338.

[0109] Vitamins and minerals such as niacinamide (vitamin B3), vitamin E, and zinc are used to promote hair growth and repair damage. Suitable vitamins and minerals are known to experts and are described, for example, in Pietrzik K, Golly I, Loew D, Handbuch Vitamine (Handbook of Vitamins), Elsevier GmbH, Urban & Fischer Verlag, Munich 2008; H. Lautenschläger, Vitamine in der Kosmetik (Vitamins in Cosmetics), medical Beauty Forum 2020 (3), 14-17; and Martini MC, Chivot M., Peyrefitte G., Lehrbuch Kosmetik: Grundlagen - Grundstoffe - Grundtechniken (Textbook of Cosmetics: Fundamentals - Basic Ingredients - Basic Techniques), Hogrefe AG, Bern 2001.

[0110] Preferably, the formulation according to the invention contains at least one vitamin in an amount of 0.0001–5 wt.%, preferably 0.001–2 wt.%, more preferably 0.01–1 wt.%, and in particular 0.06–1.0 wt.%. Preferably, the at least one vitamin is vitamin E.

[0111] Alkalizing agents or pH adjusters are used to adjust the pH of the formulation to a desired range. Suitable alkalizing agents or pH adjusters include, among others, sodium hydroxide, monoethanolamine (0.1–5%), phosphoric acid, and citric acid.

[0112] In preferred embodiments, the formulation according to the invention contains at least one organic acid and / or an organic buffer system as a pH adjusting agent.

[0113] The organic acid is preferably selected from citric acid, adipic acid, malic acid, succinic acid, tartaric acid, ascorbic acid, phosphoric acid, lactic acid, glycolic acid, and fumaric acid, or mixtures thereof. Citric acid is particularly preferred according to the invention. The organic acid can be added to the formulation as a free acid and / or as a salt thereof, in particular as an alkali metal salt or alkaline earth metal salt, with free acids being preferred. According to the invention, the organic buffer system preferably comprises a mixture of at least one preferred organic acid and at least one salt of a preferred organic acid. The preparation of buffer systems is known to those skilled in the art.

[0114] In preferred embodiments, the formulation according to the invention contains 0.001–15 wt.%, preferably 0.005–10 wt.%, more preferably 0.01–5 wt.%, and in particular 0.05–1 wt.%, organic acids and / or an organic buffer system. The pH of the formulation is preferably 2.5–7.5, and in particular 3–6. It was surprisingly found that by adding an organic acid and / or an organic buffer system, for example, by adding citric acid, the dye precursor (i) can be significantly stabilized, and a good dyeing effect is achieved despite the low pH.

[0115] The compositions according to the invention are preferably conditioner care products.

[0116] Surprisingly, it has been shown that the property profile of the formulation according to the invention is particularly well suited to simultaneously conditioning and coloring hair.

[0117] The cosmetic formulation of the present invention is therefore used in particular for the care and simultaneous coloring of keratin fibers, especially human hair.

[0118] For the purposes of this invention, "keratin fibers" means hair, in particular human hair. The term "human hair" specifically includes head hair and beard hair.

[0119] The cosmetic formulation of the present invention can further be used in combination with at least one additional cosmetic formulation. Typically, the additional cosmetic formulation, which differs from the formulation according to the invention, is a shampoo, a dye, or a tonic. Preferably, the additional cosmetic formulation contains active ingredients, in particular xanthine derivatives such as caffeine and / or a dye precursor (as defined above). Suitable xanthine derivatives are known to those skilled in the art and preferably include naturally occurring xanthines, more preferably caffeine, theophylline, and / or theobromine, and particularly preferably caffeine.

[0120] Shampoos, dyes, etc. are known to those skilled in the art. The cosmetic formulation according to the invention is particularly preferably used in combination with the cosmetic formulation described in EP 4 154 864.

[0121] Accordingly, the present invention also relates to a kit comprising

[0122] (a) a cosmetic formulation of the present invention and

[0123] (b) a cosmetic formulation which in particular contains a xanthine derivative and / or colour precursor (as defined above).

[0124] Components (a) and (b) are different cosmetic formulations. According to the invention, the composition is applied topically. Topical application means external application, in particular local external application, especially directly onto the keratin fiber.

[0125] In another aspect, the present invention relates to a method for dyeing and conditioning keratin fibers, comprising the steps

[0126] (1) Applying the cosmetic formulation of the present invention to the keratin fibers,

[0127] (2) Exposure of the cosmetic formulation to air and, if necessary, conversion of the colorant precursor to the colorant with oxidizing agents and

[0128] (3) Rinse the keratin fibers treated according to step (2) with water.

[0129] Preferably, the cosmetic formulation of the present invention is distributed in step (1) onto the water-damp or dry hair, e.g. as when washing hair.

[0130] In step (2) the formulation according to the invention is preferably allowed to act for 1-30 minutes, more preferably for 2-20 minutes, and even more preferably for 1-5 minutes.

[0131] After step (2) the keratin fiber treated in this way is rinsed with water so that preferably all components of the formulation according to the invention are removed after step (3).

[0132] In a preferred embodiment, the keratin fibers can be treated with an additional cosmetic formulation, preferably a shampoo, before step (1) or after step (3). Preferably, the inventive method is carried out directly after washing the hair while it is still damp. The additional cosmetic formulation is as described above.

[0133] The following formulations are intended to clarify the invention without limiting it to the specific examples. Example formulation 1

[0134] Ingredient wt.%

[0135] Water 91.2

[0136] Niacinamide 1.05

[0137] HC Blue No. 16 0.3

[0138] Basic Red 76 0.35

[0139] Cetyl Alcohol 5

[0140] Behentrimonium chloride 2

[0141] 5,6-Dihydroxyindoles 0.1

[0142] (DHI) pH 6-7.5±0.5

[0143] Example recipe 2

[0144] Ingredient wt.%

[0145] Water 91.15

[0146] Niacinamide 0.1

[0147] Caffeine 1

[0148] HC Blue No. 16 0.3

[0149] Basic Red 76 0.35

[0150] Cetearyl Alcohol 5

[0151] Behentrimonium chloride 2

[0152] 5,6-Dihydroxyindoles 0.1

[0153] (DHI) pH 6-7.5±0.5

[0154] Example recipe 3

[0155] Ingredient wt.%

[0156] Water 89.65

[0157] Niacinamide 0.1

[0158] Caffeine 1

[0159] HC Blue No. 16 0.3

[0160] Basic Red 76 0.35

[0161] Cetyl Alcohol 7

[0162] Behentrimonium chloride 1.5

[0163] 5,6-Dihydroxyindoles 0.1

[0164] (DHI) pH 6-7.5±0.5 Example formulations 4-7

Claims

Claims 1. Cosmetic formulation containing (i) at least one dye precursor selected from the group consisting of indoline derivatives and indole derivatives, (ii) at least one tertiary amine or quaternary ammonium compound, each comprising at least one N-bonded aliphatic hydrocarbon residue having 10-32 carbon atoms, which may optionally contain a -C(O)O- or -O- group, (iii) at least one aliphatic hydrocarbon having at least 10, preferably 10-50, carbon atoms, optionally substituted with at least one functional group selected from -OH and -COOR, wherein R is independently H, a glycerol derivative or a physiologically acceptable cation, wherein the weight ratio of component (ii) to component (iii) is in the range of 1 :1 - 1 :8, preferably 1 :2-1 :

5.

2. Cosmetic formulation according to claim 1, wherein the formulation further contains at least one antioxidant in an amount of 0.0001-5 wt.%, preferably 0.001-2 wt.%, more preferably 0.01-1 wt.%, in particular 0.06-1.0 wt.%, based on the total mass of the cosmetic formulation.

3. Cosmetic formulation according to claim 2, wherein the at least one antioxidant is selected from tocopherols, tocopherol derivatives and / or tocotrienols, more preferably from tocopherols and / or tocotrienols, and even more preferably from tocopherols, wherein the at least one antioxidant is particularly preferably (RRR)-α-tocopherol.

4. Cosmetic formulation according to any one of the preceding claims, wherein the formulation further comprises at least one organic acid and / or an organic buffer system, in particular citric acid, wherein the amount of the organic acid and / or the organic buffer system preferably 0.001-15 wt.%, more preferably 0.005-10 wt.%, even more preferably 0.01-5 wt.%, in particular 0.05-1 wt.%.

5. Cosmetic formulation according to any one of the preceding claims, wherein the dye precursor is an indole derivative, in particular a 5,6-dihydroxyindole derivative according to formula (I) or a physiologically acceptable salt thereof, wherein, independently of each other, R 1 Hydrogen, a Ci-C4 alkyl group, or a Ci-C4 hydroxyalkyl group means, R 2 hydrogen or a -COOH group, where the -COOH group can also exist as a salt with a physiologically acceptable cation, R 3 Hydrogen or a Ci-C4 alkyl group means R 4 Hydrogen, a Ci-C4 alkyl group, an amino group or a group - COR 6 means, in the R 6 a Ci-C4 alkyl group means, and R5 one of the under R 4 This refers to the aforementioned groups.

6. Cosmetic formulation according to any one of claims 1-4, wherein the dye precursor is an indoline derivative, in particular a 5,6-dihydroxyindoline derivative according to formula (II) or a physiologically acceptable salt thereof, wherein, independently of each other, R 1 Hydrogen, a Ci-C4 alkyl group, or a Ci-C4 hydroxyalkyl group means, R 2 hydrogen or a -COOH group, where the -COOH group can also exist as a salt with a physiologically acceptable cation, R 3 Hydrogen or a Ci-C4 alkyl group means R 4 Hydrogen, a Ci-C4 alkyl group, an amino group or a group - COR 6 means, in the R 6 a Ci-C4 alkyl group means, and R 5 one of the under R 4 This refers to the aforementioned groups.

7. Cosmetic formulation according to any of the preceding claims, wherein the component (i) constitutes 0.01-0.5 wt.%, preferably 0.05-0.2 wt.%, based on the total mass of the cosmetic formulation.

8. Cosmetic formulation according to one of the preceding claims, wherein component (ii) is a quaternary ammonium compound with an N-bonded aliphatic, preferably unbranched, hydrocarbon residue having 10-23 carbon atoms and component (ii) preferably constitutes 0.1-10 wt. %, more preferably 1-5 wt. %, based on the total mass of the cosmetic formulation.

9. Cosmetic formulation according to any one of the preceding claims, wherein the aliphatic hydrocarbon in component (iii) comprises 10-24 unbranched has carbon atoms and is substituted with -OH or -COOR, where RH is or a physiologically acceptable cation, such as Na or K.

10. Cosmetic formulation according to any of the preceding claims, wherein the formulation has a pH value in the range of pH 4-9, preferably 5-8, more preferably 6-7.

5.

11. Cosmetic formulation according to any of the preceding claims, further comprising (iv) at least one direct dye, such as a nitrophenylenediamine, nitroaminophenol, nitro dye, azo dye, anthraquinone or indophenol, wherein component (iv) preferably constitutes 0.001-3 wt% based on the total mass of the cosmetic formulation.

12. Use of the cosmetic formulation according to any one of claims 1-11 for coloring and conditioning keratin fibers, in particular hair.

13. Use according to claim 12, in combination with at least one additional cosmetic formulation, which in particular contains at least one xanthine derivative and / or a dye precursor, such as an indolin derivative or indole derivative.

14. Kit including (a) a cosmetic formulation according to any one of claims 1-11 and (b) a cosmetic formulation which in particular contains at least one xanthine derivative and / or a colour precursor, such as an indolin derivative or indole derivative.

15. Method for dyeing and conditioning keratin fibers, comprising the steps (1) applying the cosmetic formulation according to one of the claims 1-11 on the keratin fibers, (2) Exposure of the cosmetic formulation to air and, if necessary, conversion of the colorant precursor to the colorant with oxidizing agents, and (3) Rinse the keratin fibers treated according to step (2) with water.

16. Method according to claim 15, wherein step (1) is carried out by applying to the water-moist keratin fibers, in particular human hair.

17. Method according to claim 15 or 16, wherein step (2) takes 1-5 minutes.

18. Method according to any one of claims 15-17, wherein the keratin fibers are treated before step (1) or after step (3) with an additional cosmetic formulation, which in particular contains a xanthine derivative and / or a dye precursor, such as an indolin derivative or indole derivative.

Images