Catechol derivatives for treatment of signs of hair aging and / or scalp aging

Abstract

The invention relates to the cosmetic use of specific catechol derivatives for combatting age-related changes in hair follicles, for promoting keratin synthesis in hair and for positively influencing hair structure. The invention further relates to a cosmetic product containing specific amounts of the catechol derivative in a suitable carrier and to a cosmetic method for stimulating hair growth and / or for eliminating, reducing, alleviating or preventing hair loss and / or for strengthening hair structure.

Description

[0001] Henkel AG & Co. KGaA Dr. Ludwig “Catechol derivatives for the treatment of signs of aging in the hair and / or scalp” The present invention relates to the cosmetic use of specific catechol derivatives for combating age-related changes in the hair follicle, for promoting keratin synthesis in the hair and for positively influencing the hair structure. The invention further relates to a cosmetic agent which contains specific amounts of the catechol derivative in a suitable carrier, as well as to a cosmetic method for stimulating hair growth and / or for eliminating, reducing, alleviating or preventing hair loss and / or for strengthening the hair structure. Androgenetic alopecia is a widespread phenomenon and often impairs the self-esteem of those suffering from it. Hair follicle cells are subject to a genetically determined cycle of growth, regression and resting phase.The hair follicle is the only organ that constantly renews itself and thus has a unique metabolism, depending on the respective growth phase. The synthesis of the structural keratins is also linked to this cycle. This cycle is controlled by a small, highly specialized cell population in the hair bulb, the dermal papilla cells, which regulate hair growth through a unique, complex system of molecular signals that is specific to each phase of the hair cycle. If the metabolism of these highly specialized cells is to be modulated through the use of a test formulation, it is essential to specifically influence the corresponding mechanisms. Maintaining the youthfulness of hair or rejuvenating it through suitable active ingredient formulations is a challenge for cosmetic research. In topical applications for the treatment of disorders in the hair structure, e.g.Treatments for split ends or hair breakage usually involve physical procedures in which, for example, polymers or structural proteins are applied to the hair. The sustainability of these methods is limited, and here too there is a risk of "overloading" the hair with conditioning substances through repeated use. Furthermore, the only option is to improve the structure of the hair from the root up through the oral application of certain active ingredients. Studies of the molecular and cellular physiological reasons for phenotypic changes during the aging process have shown that, among other things, the synthesis of the structure-giving hair keratins in the aging hair follicle decreases significantly, which is one of the causes of androgenetic hair loss. In particular, the hair keratins KRT86 (hhb6), KRT34 (hha4), and KRT33a (hha3), as well as various cytokeratins (e.g., CK1), are affected by these age-related changes.Hair keratins represent the most important structural component of the hair. The importance of hair keratins for healthy hair fibers is demonstrated by the fact that genetic mutations in the hair keratins lead to significant changes, such as deformation and breakage of the hair fiber (monilethix). There are hardly any cosmetic preparations on the market that can support the synthesis of hair-specific keratins in a biological and thus sustainable way. The aim of the present invention was therefore to find suitable active ingredients for use in cosmetic hair and / or scalp treatment products that, when applied topically to the hair and / or scalp, protect against premature hair loss, activate keratin synthesis, and thus counteract hair aging. This goal was largely achieved through the use of specific catechol derivatives.A first object of the invention is therefore the cosmetic use of compounds of general formula (I). in the R 1 and R 2 independently for NR 3 R 4 or OR 5 stand and R 3 , R 4 and R 5independently of one another represent H or a cyclic or acyclic, straight-chain or branched-chain, aliphatic or aromatic hydrocarbon radical having 1 to 20 carbon atoms, the skeleton of which may be interrupted by one or more non-adjacent heteroatoms, in particular selected from O and / or N, and / or which may be substituted by OH groups or NH2 groups on C atoms not bonded to heteroatoms, in cosmetic hair and / or scalp treatment agents for stimulating hair growth and / or for eliminating, reducing, alleviating or preventing hair loss and / or for strengthening the hair structure.In particular, the use of compounds according to formula (I) enables the development of new product and action concepts for biologically active hair and / or scalp treatment products that counteract or reverse the decline in keratin synthesis, the reduction in cell division activity, and the decline in cell vitality. Furthermore, the use according to the invention improves the feel and combability of the keratin fibers, since the physical properties are improved by the effect on thinning hair (which thickens again due to increased keratin synthesis). The inventive use of compounds according to formula (I) in cosmetic hair treatment agents further counteracts or reverses increased microinflammation and apoptosis.A preferred use within the meaning of the present invention is characterized in that, in particular, the synthesis of the hair keratins KRT86 (hhb6), KRT34 (hha4), and KRT33a (hha3) affected by aging is stimulated. A first preferred embodiment of the use according to the invention is characterized in that cell vitality, cell proliferation, and the release of growth factors are stimulated, thus positively influencing the anagen hair growth phase and inhibiting the activation of catagen-associated parameters. Among suitable compounds of general formula (I), those in which the radicals R. 1 and R 2 are equal and for NR 3 R 4 stand. R 3 is preferably H, and R 4is preferably an alkyl group, such as methyl, ethyl, n-propyl or isopropyl, an alkoxyalkyl group, such as methoxyethyl, methoxypropyl, (2-methoxy)ethoxyethyl, ethoxyethyl, ethoxypropyl or (2-ethoxy)ethoxyethyl, a hydroxyalkyl group, such as hydroxyethyl, hydroxypropyl, 2-hydroxypropyl, 1,2-dihydroxypropyl, 2-hydroxyethoxyethyl, (N-hydroxyethyl)aminoethyl, (N-methoxyethyl)aminoethyl or (N-ethoxyethyl)aminoethyl, or an aromatic group, such as phenyl or benzyl. Particular preference is given to an alkyl group and very particularly preferably to an n-propyl group. Particular preference is given to a catechol derivative according to formula (I) known under the name N,N-dipropyl-2,3-dihydroxyterephthalamide (DTA5). In a preferred embodiment, the radicals R 1 and R 2 in compounds of the general formula (I). Within this embodiment, the radicals R 1 and R 2 in compounds of general formula (I) preferably for NR3 R 4 . In a further preferred embodiment, the radical R 3 in compounds of the general formula (I) H. In a further preferred embodiment, the radical R 4 in compounds of the general formula (I) an alkyl group such as methyl, ethyl, n-propyl or i-propyl, an alkoxyalkyl group such as methoxyethyl, methoxypropyl, (2-methoxy)ethoxyethyl, ethoxyethyl, ethoxypropyl or (2-ethoxy)ethoxyethyl, a hydroxyalkyl group such as hydroxyethyl, hydroxypropyl, 2-hydroxypropyl, 1,2-dihydroxypropyl, 2-hydroxyethoxyethyl, (N-hydroxyethyl)aminoethyl, (N-methoxyethyl)aminoethyl or (N-ethoxyethyl)aminoethyl, or an aromatic group such as phenyl or benzyl. Within this embodiment, the radical R 4preferably represents an alkyl group and particularly preferably represents an n-propyl group. In a particularly preferred embodiment, the compound of formula (I) is N,N-dipropyl-2,3-dihydroxyterephthaldiamide (DTA5). The inventive use of compounds of general formula (I) in cosmetic hair and / or scalp treatment compositions preferably takes place by employing them in an amount of 0.005-1 wt.%, in particular in an amount of 0.01-0.5 wt.%, whereby here and below, the terms "wt.%" refer in each case to the weight of the entire cosmetic hair and / or scalp treatment composition. A second subject of the invention is therefore a cosmetic composition which contains 0.005-1 wt.%, in particular 0.01-0.5 wt.%, of compounds of general formula (I) in a cosmetic carrier.The preferred embodiments described above or below in connection with the use according to the invention also apply to this subject matter of the invention, and conversely, the preferred embodiments described in connection with agents according to the invention also apply to the use aspect of the invention. There are no fundamental restrictions with regard to the type of cosmetic agents in which compounds of general formula (I) are used. Examples of suitable formulations for these agents include creams, lotions, solutions, waters, emulsions such as W / O, O / W, PIT emulsions (emulsions according to the theory of phase inversion, called PIT), microemulsions and multiple emulsions, coarse, unstable, single- or multi-phase shake mixtures, gels, sprays, aerosols, foam aerosols, but also solid forms such as powders,Granules or bars are suitable. A suitable cosmetic carrier for the cosmetic agents according to the invention is, for example, an aqueous or aqueous-alcoholic base. Lower alkanols and polyols such as propylene glycol and glycerin are used as the alcoholic component. Ethanol and isopropanol are preferred alcohols. Water and alcohol can be present in the aqueous-alcoholic base in a weight ratio of 1:20 to 20:1. Water and aqueous-alcoholic mixtures containing up to 50% by weight, in particular up to 25% by weight, of alcohol, based on the alcohol / water mixture, can be preferred bases according to the invention. The pH of these preparations can, in principle, be between 2 and 11. It is preferably between 2 and 7.Values ​​from 3 to 5 are particularly preferred. To adjust this pH, virtually any acid or base suitable for cosmetic purposes can be used. Typically, food acids are used as acids. Food acids are those acids that are ingested as part of normal food intake and have positive effects on the human organism. Food acids include, for example, acetic acid, lactic acid, tartaric acid, citric acid, malic acid, ascorbic acid, and gluconic acid. Within the scope of the invention, the use of citric acid and / or lactic acid is particularly preferred. Preferred bases are ammonia, alkali metal hydroxides, monoethanolamine, triethanolamine, and N,N,N',N'-tetrakis-(2-hydroxypropyl)-ethylenediamine. Cosmetic agents within the meaning of the present invention can be in solid or liquid forms, for example as - cosmetic cleansing compositions for the scalp and / or hair,such as cleansing powders or granules, soap bars, cleansing wipes, porous bodies (solid cleansing foams), hair shampoos, 2-in-1 hair care shampoos, anti-dandruff shampoos, hair coloring shampoos, hair cleansing conditioners, shower gels or combinations thereof, - cosmetic care compositions for the scalp and / or hair, such as hair conditioners, hair treatments, hair packs, hair tonics, hair oils, hair serums, ethanolic or aqueous tinctures, etc. or combinations thereof, - cosmetic compositions for the temporary or permanent shaping or fixing of hair, such as hair sprays, permanent wave fixing solutions, hair setting lotions, hair setting products, hair styling preparations, blow-dry lotions, mousses, hair gels, hair waxes or combinations thereof,- temporary or permanent hair dyes. Suitable cosmetic agents within the meaning of the present invention can be rinsed out with water after the intended application to the scalp and / or hair, or can remain in or on the scalp. In a preferred embodiment, the cosmetic agents according to the invention are rinse-off or leave-on compositions for the treatment of hair and / or the scalp. Rinse-off or leave-on compositions within this embodiment are preferably shampoos or hair conditioners, such as hair rinses, hair treatments, essences, lotions, serums, hair tip fluids, which can be in liquid form or as a powder or solid, as well as sprays, gels or waxes, or hair styling agents, such as hairsprays.Hair gels or hair waxes are to be understood. The use of compounds of general formula (I) in cosmetic compositions that remain on the scalp and / or hair (leave-on preparations) has proven particularly effective and can therefore represent preferred embodiments of the teaching according to the invention. For the purposes of the present invention, "leaving on the scalp and hair" refers to preparations thatwhich are not rinsed off the scalp or out of the hair with water or an aqueous solution after a period of a few seconds to one hour during the treatment. Rather, the preparations remain on the scalp or hair until the next wash. According to a preferred embodiment of the invention, compounds of the general formula (I) are used in hair treatments or the aforementioned hair conditioners. These preparations can be rinsed out with water or an at least predominantly water-containing agent after a contact time; however, they are preferably, as stated above,left on the hair. According to further embodiments, compounds of general formula (I) can be used in cleansing agents for the scalp and hair - such as a shampoo. The cosmetic agents according to the invention preferably contain further ingredients, depending on the intended use. Solid cleansing compositions such as powders, granules, soap bars, cleansing wipes, porous bodies (solid foams) are preferably moistened with water or soaked in water or dissolved in water before use, then foamed by rubbing between the hands or directly onto the scalp and / or hair, and rinsed out with water after use. Liquid cleansing compositions such as hair shampoos, 2-in-1 hair care shampoos, anti-dandruff shampoos, hair coloring shampoos, hair cleansing conditioners, and shower gels are optionally mixed with water before use.foamed onto the scalp and / or hair and rinsed out with water after application. The agents according to the invention may contain surfactant(s). In cleansing compositions (usually rinse-off compositions), anionic surfactants have proven particularly useful, while cationic surfactants are often used ingredients in conditioning compositions (rinse-off or leave-on compositions); amphoteric and / or non-ionic surfactants and / or emulsifiers are used with particular advantage in both cleansing and care compositions due to their advantageous properties. An embodiment of the second subject matter of the invention is characterized in that the cosmetic agent is formulated as a cosmetic cleansing composition for the scalp and / or hair, and in a cosmetic carrier (based on its total weight) - 0.005 - 1 wt.% of at least one compound according to formula (I) and ...1-75 wt.% of at least one anionic, amphoteric, zwitterionic, nonionic surfactant or mixtures thereof, wherein ^ solid cleaning compositions - based on their total weight - preferably contain 10-75 wt.%, more preferably 20-75 wt.% and in particular 25-70 wt.% of at least one anionic, amphoteric, zwitterionic, nonionic surfactant or mixtures thereof, and ^ liquid compositions - based on their total weight - preferably contain 0.5-30 wt.%, more preferably 1-25 wt.% and in particular 2-20 wt.% of at least one anionic, amphoteric, zwitterionic, nonionic surfactant or mixtures thereof. Particularly preferred cosmetic agents formulated as cleaning compositions,Contain > 50% of at least one anionic surfactant (based on the total surfactant content). Suitable anionic surfactants and emulsifiers for the cosmetic agents according to the invention include all anionic surface-active substances suitable for cosmetic use on the human or animal body. These are characterized by a water-solubilizing, anionic group, such as a carboxylate, sulfate, sulfonate, or phosphate group, and a lipophilic alkyl group with approximately 8 to 30 carbon atoms. The molecule may also contain glycol or polyglycol ether groups, ester, ether, and amide groups, as well as hydroxyl groups. The particularly suitable anionic surfactant types that can be used in cosmetic products according to the invention include, for example: - linear and branched fatty acids with 8 to 30 C atoms (soaps), - ether carboxylic acids of the formula RO-(CH2-CH2O)x-CH2-COOH, in which R is a linear or e,saturated or unsaturated alkyl group with 8 to 30 C atoms and x = 0 or 1 to 16, as well as their physiologically acceptable salts, - acylsarcosides with 8 to 24 C atoms in the acyl group (sarcosinate surfactants), - acyltaurides with 8 to 24 C atoms in the acyl group (taurate surfactants), - acyl isethionates with 8 to 24 C atoms in the acyl group (isethionate surfactants), - acylglutamates with 8 to 24 C atoms in the acyl group (glutamate surfactants) - sulfosuccinic acid mono- and / or dialkyl esters with 8 to 24 C atoms in the alkyl group and sulfosuccinic acid mono-alkylpolyoxyethyl esters with 8 to 24 C atoms in the Alkyl group and 1 to 6 oxyethyl groups (sulfosuccinate surfactants), - alpha-olefinsulfonates with 8 to 24 C atoms (alpha-olefinsulfonate surfactants), - alkyl sulfates and / or alkyl ether sulfate salts of the formula R-(OCH2CH2), n-O-SO3X, in which R is preferably a straight-chain or e, saturated or unsaturated alkyl group having 8 to 30 C atoms, x is the number 0 or 1 to 12 and X is an alkali, alkaline earth, ammonium or alkanolamine ion, - sulfonates of unsaturated fatty acids having 8 to 24 C atoms and 1 to 6 double bonds, - esters of tartaric acid and citric acid with alcohols, which are addition products of about 2-15 molecules of ethylene oxide and / or propylene oxide with fatty alcohols having 8 to 22 C atoms, and / or - alkyl and / or alkenyl ether phosphates of the formula O II R 1 -(OCH2CH2)— O— P— OR 2 I OX in the R 1 preferably an aliphatic hydrocarbon radical having 8 to 30 carbon atoms, R 2 for hydrogen, a residue (CH2CH20)nR 1 or X, n for numbers from 0 to 10 and X for hydrogen, an alkali or alkaline earth metal or the group -NR 3 R 4 R 5 R 6 stands, with R 3 to R 6independently of one another represent a C1 to C4 hydrocarbon radical. Very particular preference is given to alkyl sulfate and / or alkyl ether sulfate salts, (salts of) ether carboxylic acids, sarcosinates, isethionates, taurates, sulfosuccinates and / or alpha-olefin sulfonates, in particular alkyl sulfate and / or alkyl ether sulfate salts. Particular preference is given to alkyl (ether) sulfates of the general formula R-(OCH2CH2) n-OSO3X, in which R is a straight-chain or branched, saturated or unsaturated alkyl group having 8 to 24 C atoms, n is the number 0 or 1 to 12, and X is an alkali, alkaline earth, ammonium, or alkanolamine ion. The cosmetic agents according to the invention can contain at least one amphoteric or zwitterionic surfactant and / or at least one nonionic surfactant. Cosmetic agents according to the invention that are formulated as a cleaning composition preferably contain 0-50%, particularly preferably 1-40%, and in particular 5-30% of at least one amphoteric or zwitterionic surfactant and / or 0-50%, particularly preferably 1-40%, and in particular 5-30% of at least one nonionic surfactant (in each case based on the total surfactant content). Suitable zwitterionic or amphoteric surfactants are those that carry both a cationic and an anionic charge in the molecule.Amphoteric surfactants preferably contain at least one quaternary ammonium group and at least one –COO- or –SO3- group, in addition to a preferably C8-C24 alkyl or acyl group, in the molecule. Furthermore, they are capable of forming internal salts. Particularly preferred amphoteric surfactants are betaines such as N-alkyl-N,N-dimethylammonium glycinates, for example cocoalkyl dimethylammonium glycinate, N-acylaminopropyl-N,N-dimethylammonium glycinate, for example cocoacylaminopropyl dimethylammonium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethylimidazolines, each containing 8 to 18 carbon atoms in the alkyl or acyl group, as well as cocoacylaminoethyl hydroxyethylcarboxymethylglycinate. Particularly preferred are the amphoteric or zwitterionic surfactants known under the INCI names Cocamidopropyl Betaine Lauramidopropyl Betaine, Cocoampho(di)acetate and / or Lauroapho(di)acetate.Suitable non-ionic surfactants and / or emulsifiers can be selected from amine oxides such as the compounds known under the INCI names Cocamine Oxide, Lauramine Oxide and Cocamidopropylamine Oxide, fatty acid alkanolamides such as the compounds known under the INCI names Cocamide MEA and Coamide DEA, mixtures of alkyl (oligo) glucosides and fatty alcohols such as the commercially available product Montanov. ®68, sterols such as zoosterols and phytosterols, phospholipids, alkyl (oligo)glycosides such as the compounds known under the INCI names Caprylyl / Capryl Glucoside, Decyl Glucoside, Lauryl Glucoside and Coco Glucoside, alkoxylated esters such as the compounds known under the INCI names PEG-7 Glyceryl Cocoate and PEG-40 Hydrogenated Castor, polyglycerol esters and / or salts thereof. The compositions according to the invention can contain cationic surfactant(s). Cosmetic agents according to the invention which are formulated as care compositions (hair conditioners) preferably contain at least one cationic surfactant. Cationic surfactants of the quaternary ammonium compound type, the esterquats of the amidoamines or mixtures thereof can be used according to the invention.Preferred quaternary ammonium compounds are ammonium halides, especially chlorides and bromides, such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides, and trialkylmethylammonium chlorides. The long alkyl chains of these surfactants preferably have 10 to 18 carbon atoms, such as in cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride, and tricetylmethylammonium chloride. Other preferred cationic surfactants are the imidazolium compounds known under the INCI names Quaternium-27 and Quaternium-83. Particularly preferred cosmetic agents according to the invention - in particular cosmetic agents for the care of hair and / or scalp, contain - based on their weight - preferably 0.05 to 10 wt.%, particularly preferably 0.1 to 7.5 wt.% and in particular 0.25 to 7.5 wt.% cationic surfactant(s).Cosmetic products according to the invention very particularly preferably contain cationic surfactants from the group of quaternary ammonium compounds and / or esterquats and / or amidoamines in the aforementioned amounts. A particularly preferred embodiment of the second subject matter of the invention is characterized in that it is formulated as a cosmetic care composition for the scalp and / or hair, and contains in a cosmetic carrier (based on its total weight) - 0.005 - 1 wt. % of at least one compound according to formula (I) and - 0.05 to 10 wt. % of at least one cationic surfactant. In a further preferred embodiment of the second subject matter of the invention, cosmetic products according to the invention further contain at least one conditioning agent for hair and / or the scalp in a weight proportion of 0 - 50 wt. % of the total weight of the respective product. More preferred amounts are 0.01 - 30 wt.-%, particularly preferably from 0.05 - 25 wt.% and in particular from 0.1 - 20 wt.%. The at least one conditioning agent can preferably be selected from cationic polymers, natural, mineral or synthetic oils, fats or waxes or from mixtures thereof. The cosmetic agents according to the invention of the second subject matter of the invention can contain at least one cationic polymer. Preference is given to cationic polysaccharide polymers. Cationic polysaccharide polymers increase the care performance of the cosmetic agents according to the invention. Suitable cationic polysaccharide polymers can be selected from cationic cellulose compounds and / or from cationic guar derivatives. Particularly preferred cosmetic agents according to the invention of the second subject matter of the invention contain as cationic polysaccharide polymer(s) - based on the weight of the agent - 0.01 to 3 wt.%, particularly preferably 0.05 to 2 wt.% and in particular 0.1 to 1.5 wt.-% of at least one cationic polymer from the group of cationic cellulose polymers and / or cationic guar derivatives. Cationic cellulose compounds within the meaning of the invention are those that carry more than one permanent cationic charge in at least one side chain. Cellulose is composed of beta-1,4-glycosidically linked D-glucopyranose units and forms unbranched, water-insoluble chains. The "side chain" of a cellulose is defined as chemical substituents that bind to the cellulose backbone and are not part of the native cellulose, for example, because they were subsequently introduced by chemical synthesis. Preference is given to quaternized cellulose polymers derived from hydroxy(C2-C4)alkylcelluloses, particularly preferably from hydroxyethylcelluloses. Such polymers are known to the person skilled in the art and are commercially available from various companies.Particularly preferred are the cationic cellulose derivatives known under the INCI names Polyquaternium-4, Polyquaternium-10, Polyquaternium-24, Polyquaternium-67, and / or Polyquaternium-72. Polyquaternium-10, Polyquaternium-24, and / or Polyquaternium-67 are very particularly preferred, and Polyquaternium-10 is especially preferred. Preferred cosmetic agents according to the invention of the second subject matter of the invention contain, as cationic polysaccharide polymer(s), 0.01 to 3 wt.%, particularly preferably 0.05 to 2 wt.%, and in particular 0.1 to 1.5 wt.%, based on the weight of the agent, of at least one polymer from the group consisting of Polyquaternium-4, Polyquaternium-10, Polyquaternium-24, Polyquaternium-67, and / or Polyquaternium-72.Suitable cationic guar derivatives within the meaning of the invention are cationic hydroxyalkyl guar derivatives, preferably cationic hydroxyethyltrimethylammonium guar and / or cationic hydroxypropyltrimethylammonium guar with average molecular weights between 100,000 and 2,000,000 Daltons. Particular preference is given to the cationic guar polymers known under the INCI name Guar Hydroxypropyltrimonium Chloride and / or Hydroxypropyl Guar Hydroxypropyltrimonium Chloride, having a molecular weight (weight average) between 200,000 and 1,600,000 Daltons. The cationic charge density of these guar polymers is preferably at least 0.4 meq / g, more preferably at least 0.5 meq / g, and in particular at least 0.6 meq / g. Their nitrogen content is preferably in the range of 1.1 to 1.8 wt% (based on their total weight).Cationic guar derivatives, known under the INCI name Guar Hydroxypropyltrimonium Chloride, are known to those skilled in the art and are sold, for example, under the trade name Cosmedia. ® Guar, N-Hance ® jaguar ® and / or Polycare ®available from various suppliers. Particularly preferred cosmetic agents according to the invention of the second subject matter of the invention contain as cationic polysaccharide polymer(s) - based on the weight of the agent - 0.01 to 3 wt.%, particularly preferably 0.05 to 2 wt.% and in particular 0.1 to 1.5 wt.% guar hydroxypropyltrimonium chloride and / or hydroxypropyl guar hydroxypropyltrimonium chloride. Further suitable cationic polymers for use in the cosmetic agents according to the invention of the second subject matter of the invention can, for example, be selected from cationic polymers with the INCI names Polyquaternium-2, Polyquaternium-5, Polyquaternium-6, Polyquaternium-7, Polyquaternium-11, Polyquaternium-17, Polyquaternium-18, Polyquaternium-22, Polyquaternium-27, Polyquaternium-37, Polyquaternium-39 and mixtures thereof.The cosmetic products according to the invention of the second subject matter of the invention can contain at least one natural, mineral, or synthetic oil, fat, or wax, or mixtures thereof. Suitable natural (vegetable) oils are typically understood to mean triglycerides and mixtures of triglycerides. Preferred natural oils are coconut oil, (sweet) almond oil, walnut oil, peach kernel oil, apricot kernel oil, avocado oil, tea tree oil, soybean oil, sesame oil, sunflower oil, tsubaki oil, evening primrose oil, rice bran oil, palm kernel oil, mango kernel oil, meadowfoam oil, safflower oil, macadamia nut oil, grape seed oil, amaranth seed oil, tamanu oil, perilla oil, argan oil, bamboo oil, olive oil, wheat germ oil, pumpkin seed oil, mallow oil, hazelnut oil, safflower oil, canola oil, sasanqua oil, jojoba oil, rambutan oil, cocoa butter, murumuru butter, and / or shea butter. Mineral oils, paraffin and isoparaffin oils as well as synthetic hydrocarbons are particularly used as mineral oils.An example of a suitable hydrocarbon is 1,3-di-(2-ethylhexyl)-cyclohexane (Cetiol), which is available as a commercial product. ® S). A dialkyl ether can also serve as a suitable oil component. Suitable dialkyl ethers are, in particular, di-n-alkyl ethers with a total of between 12 and 36 carbon atoms, in particular 12 to 24 carbon atoms, such as, for example, di-n-octyl ether, di-n-decyl ether, di-nonyl ether, di-n-undecyl ether, di-n-dodecyl ether, n-hexyl n-octyl ether, n-octyl n-decyl ether, n-decyl n-undecyl ether, n-undecyl n-dodecyl ether, and n-hexyl n-undecyl ether, as well as di-tert-butyl ether, di-isopentyl ether, di-3-ethyldecyl ether, tert-butyl n-octyl ether, isopentyl n-octyl ether, and 2-methylpentyl n-octyl ether. Particularly preferred is the di-n-octyl ether, which is commercially available under the name Cetiol ®OE is available. Silicone compounds are preferred synthetic oils. Silicones exhibit excellent conditioning properties on keratin fibers, especially on hair. In particular, they improve combability in both wet and dry hair and, in many cases, have a positive effect on the feel and softness of the hair.Suitable silicones can be selected from: (i) polyalkylsiloxanes, polyarylsiloxanes, polyalkylarylsiloxanes, which are volatile or non-volatile, straight-chain or cyclic, branched or unbranched; (ii) polysiloxanes containing in their general structure one or more organofunctional groups selected from: a) substituted or unsubstituted aminated groups; b) (per)fluorinated groups; c) thiol groups; d) carboxylate groups; e) hydroxylated groups; f) alkoxylated groups; g) acyloxyalkyl groups; h) amphoteric groups; i) bisulfite groups; j) hydroxyacylamino groups; k) carboxy groups; l) sulfonic acid groups; and m) sulfate or thiosulfate groups; (iii) linear polysiloxane(A)-polyoxyalkylene(B) block copolymers of type (AB). nwith n > 3; (iv) grafted silicone polymers with a non-silicone-containing, organic backbone, consisting of an organic main chain formed from organic monomers that do not contain silicone, to which at least one polysiloxane macromer has been grafted in the chain and optionally at at least one chain end; (v) grafted silicone polymers with a polysiloxane backbone, to which non-silicone-containing organic monomers have been grafted, having a polysiloxane main chain, to which at least one organic macromer that does not contain silicone has been grafted in the chain and optionally at at least one of its ends; (vi) or mixtures thereof. Fats are understood to mean fatty acids, fatty alcohols and natural and synthetic waxes, which can be in solid form or in liquid form in aqueous dispersion.The fatty acids used can be linear and / or branched, saturated and / or unsaturated fatty acids with 6-30 carbon atoms, preferably with 10-22 carbon atoms. The fatty alcohols used can be saturated, mono- or polyunsaturated, e- or unbranched fatty alcohols with C6-C. 30 -, preferably C 10 - C 22 - and especially preferably C 12 - C 22- carbon atoms. Natural or synthetic waxes that can be used include solid paraffins or isoparaffins, carnauba wax, beeswax, candelilla wax, ozokerite, ceresin, spermaceti, sunflower wax, hardened waxes such as hydrogenated castor oil, fruit waxes such as apple wax or citrus wax, and microwaxes made from PE or PP. Other suitable fatty substances include ester oils, which are esters of C6 - C30 fatty acids with C2 - C30 fatty alcohols. Examples of particularly suitable ester oils are isopropyl myristate (rilanite). ® IPM), isononanoic acid C16-18 alkyl ester (cetiol ® SN), 2-ethylhexyl palmitate (Cegesoft ® 24), 2-ethylhexyl stearate (Cetiol ® 868), cetyl palmitate, cetyl oleate, glycerol tricaprylate, coconut fatty alcohol caprinate / caprylate (cetiol ® LC), n-butyl stearate, oleyl rucate (cetiol ® J 600), isopropyl palmitate (Rilanit ® IPP), Oleyl Oleate (Cetiol® ), lauric acid hexyl ester (Cetiol ® A), Di-n-butyl adipate (Cetiol ® B), myristyl myristate (Cetiol ® MM), Cetearyl Isononanoate (Cetiol ® SN), oleic acid decyl ester (Cetiol ® V) - Dicarboxylic acid esters such as di-n-butyl adipate, di-(2-ethylhexyl) adipate, di-(2-ethylhexyl) succinate and di-isotridecyl acelate as well as diol esters such as ethylene glycol dioleate, ethylene glycol di-isotridecanoate, propylene glycol di(2-ethylhexanoate), propylene glycol di-isostearate, propylene glycol di-pelargonate, butanediol di-isostearate, neopentyl glycol dicaprylate, symmetrical, asymmetrical or cyclic esters of carbonic acid with fatty alcohols such as glycerol carbonate or dicaprylyl carbonate (Cetiol ® CC) - ethoxylated or non-ethoxylated mono-, di- and trifatty acid esters of saturated and / or unsaturated linear and / or ene fatty acids with glycerol, such as monomuls ® 90- O18, Monomuls ® 90-L12, Cetiol ®HE or Cutina ®MD. The weight proportion of the oils, fats and / or waxes in the total weight of the cosmetic agents according to the invention of the second subject matter of the invention is preferably 0 to 50 wt.%, particularly preferably 0.01 to 30 wt.% and in particular 0.05 to 15 wt.%. In addition to the active ingredients described above, the cosmetic agents according to the invention of the second subject matter of the invention may, depending on the embodiment, further contain one or more active ingredients from one or more of the following groups: - Dyes, comprising both dyes for coloring the compositions and dyes for coloring hair, comprising oxidation dye precursors, direct dyes, natural dyes and mixtures thereof, and optionally oxidizing and alkalizing agents, - UV filter substances - Perfumes - Thickeners such as, for example, cellulose ethers, xanthan gum, sclerotium gum, succinoglucans, polygalactomannans, pectins, agar, carrageenan, tragacanth,Gum arabic, karaya gum, tara gum, gellan, gelatin, propylene glycol alginate, alginic acids and their salts, polyvinylpyrrolidones, polyvinyl alcohols, polyacrylamides, physically (e.g. by pregelatinization) and / or chemically modified starches, acrylic acid-acrylate copolymers, acrylic acid-acrylamide copolymers, acrylic acid-vinylpyrrolidone copolymers, acrylic acid-vinylformamide copolymers, polyacrylates and branched polymers of acrylic acid, methacrylic acid and their salts - complexing agents such as EDTA - anti-dandruff agents such as piroctone olamine, zinc pyrithione, climbazole, propanediol caprylates - vitamins, vitamin derivatives or vitamin precursors, preferably from groups A, B, E and H, particularly preferably from group B, such as niacinamide, panthenol, pantolactone, pyridoxine or mixtures thereof - Film-forming polymers such as polymers from the group of copolymers of acrylic acid, copolymers of methacrylic acid,homopolymers or copolymers of acrylic acid esters, homopolymers or copolymers of methacrylic acid esters, homopolymers or copolymers of acrylic acid amides, homopolymers or copolymers of methacrylic acid amides, copolymers of vinylpyrrolidone, copolymers of vinyl alcohol, copolymers of vinyl acetate, homopolymers or copolymers of ethylene, homopolymers or copolymers of propylene, homopolymers or copolymers of styrene, polyurethanes, polyesters and / or polyamides. Specific suitable examples are the commercial products Aculyn, ® 22, Aculyn ® 28, Structure ® 2001, Structure ® 3001, Structure Plus ® , Carbopol ® 1342, 1382, Ultrez 20, Ultrez 21, amphomer ® , Dermacryl ® LT and 79, Luvitol ® HSB, PVP (Luvitech ® 17, 30, 60, 80, 85, 90, K 115), Luviskol ® K 90, Luviskol ® K 85, Luviskol ®VA 64 und 73, Aquaflex ® SF-40 Styleze ®CC-10 - Amino acids, preferably alanine, aspartic acid, cysteine, cystine, glutamic acid, glycine, lysine, proline, serine, methionine, tyrosine and mixtures thereof - pearlescent agents and / or opacifiers - keratin-reducing active ingredients such as mercaptans, thioglycolate salts, optionally in combination with ammonia or amines - organic acids such as citric acid, malic acid, lactic acid, tartaric acid - alkalizing agents - ceramides - propellants - preservatives. Preferred cosmetic agents within the meaning of the present invention are cosmetic care compositions for hair and / or the scalp - in particular leave-on care compositions - which are characterized as follows: - 0.005 - 1 wt. % of at least one compound according to formula (I) - a cosmetic carrier. Further preferred are cosmetic care compositions for hair and / or the scalp - in particular leave-on care compositions - which are characterized as follows: - 0.005 - 1 wt.-% of at least one compound according to formula (I) - 0.05 - 7.5 wt.% of at least one cationic surfactant - a cosmetic carrier. Even more preferred are cosmetic care compositions for hair and / or scalp - in particular leave-on care compositions - which are characterized as follows: - 0.005 - 1 wt.% of at least one compound according to formula (I) - 0.05 - 7.5 wt.% of at least one cationic surfactant - 0.01 - 30 wt.% of at least one conditioning agent for keratin fibers (wherein the cationic surfactant does not count as a conditioning agent) - a cosmetic carrier. Very particular preference is given to cosmetic care compositions for hair and / or scalp - in particular leave-on care compositions - which contain 0.005 - 1 wt.% of N,N-dipropyl-2,3-dihydroxyterephthaldiamide (DTA5) as a compound according to formula (I) in a cosmetic carrier.A third subject matter of the invention is a cosmetic method for stimulating hair growth and / or for eliminating, reducing, alleviating or preventing hair loss and / or for strengthening the hair structure, in which a cosmetic agent of the second subject matter of the invention is applied to the hair and / or the scalp.

[0002] Examples: The present invention will now be illustrated by the following non-limiting examples. It should be noted that various changes and modifications can be made to the following examples and methods without departing from the scope of the invention (which is defined in the claims). Therefore, it should be noted that the following examples are to be interpreted as illustrative only and not in any way limiting. 1. Working Examples The following cosmetic compositions for the treatment of hair and / or scalp were prepared (the amounts are by weight).-%): a) Hair shampoos 1 2 3 Compound according to formula (I)* 0.005 – 1 0.005 – 0.5 0.01 – 0.5 anionic surfactant 5 - 15 Sodium Laureth Sulfate 7 9 amphoteric / zwitterionic surfactant 0 - 5 Disodium Cocoamphodiacetate 0.8 Cocamidopropyl Betaine 1 1.5 non-ionic surfactant 0 - 5 Alkylpolyglucoside** 0.4 Cocamide MEA 0.4 cationic polymer 0 - 2 cationic Guar 0.05 0.15 oil, fat or wax 0 - 3 Apricot kernel oil 0.1 Glyceryl Oleate** 0.4 water and if necessary other active ingredients and ad 100 ad 100 ad 100 excipients * N,N-Dipropyl-2,3-dihydroxyterephthaldiamide (DTA-5) ** as a component of the commercial product Lamesoft. ® PO 65 (INCI name: Aqua, Coco Glucoside, Glyceryl Oleate) b) Hair care products 1 2 3 Compound according to formula (I)* 0.005 – 1 0.005 – 0.5 0.01 – 0.5 cationic surfactant 0.05 – 7.5 Dehyquart ® F 75 T *1 1.5 Behentrimonium Chloride 2 Dehyquart ® A CA *22.5 Fatty alcohol 2 - 10 Cetearyl Alcohol 7 4 Fatty acid esters 0.1 - 5 Isopropyl myristate 2 0.8 Cationic polymer 0 - 2 Cosmedia Triple C *3 0.65 Water and if necessary other active ingredients and ad 100 ad 100 ad 100 excipients N,N-Dipropyl-2,3-dihydroxyterephthaldiamide (DTA-5) * 1 INCI name: Distearoylethyl Hydroxyethylmonium Methosulfate and Cetearyl Alcohol (65-72% AS cationic surfactant); BASF * 2 INCI name: Cetrimonium Chloride (24-26% AS cationic surfactant); BASF * 3 INCI name: Polyquaternium-37 and Dicaprylyl Carbonate and Lauryl Glucoside; BASF c) Hair styling products 1 2 3 Compound according to formula (I)* 0.005 – 1 0.005 – 0.5 0.01 – 0.5 Ethanol 0 - 90 80 AMP-Ultra ® PC 2000 *4 0 - 3 1.5 Amphomer ®*5 0 - 15 7 Hydroxypropyl Starch 0 - 25 17 Dehyquart ® A CA *2 0 - 5 1 Water and other active and ad 100 ad 100 ad 100 excipients N,N-Dipropyl-2,3-dihydroxyterephthaldiamide (DTA-5) * 4INCI name: Aminomethyl Propanol * 5INCI name: Octylacrylamide / Acrylates / Butylaminoethyl Methacrylate Copolymer 2. Evidence of effectiveness Hepatocyte Growth Factor (HGF) and Keratinocyte Growth Factor (KGF) are important growth factors secreted by the dermal papilla to regulate the proliferation of hair keratinocytes, which are responsible for the synthesis of hair keratins. They are also characteristic markers of the anagen phase, during which keratin synthesis is also maximal. Furthermore, it should be noted that with hair aging, the proliferation capacity of hair follicle cells decreases. Therefore, HGF and / or KGF should be induced for a substance potentially activating keratin and counteracting hair aging. TGF-β1, TGF-β2, and IGFBP-3 have growth-inhibiting effects and are characteristic markers of the catagen phase.in which keratin synthesis in the follicle is switched off. These markers should be repressed by a substance that promotes keratin synthesis. Differential gene expression was determined using quantitative RT-PCR. After culturing the dermal papilla cells, they were incubated for 24 hours with N,N-dipropyl-2,3-dihydroxyterephthaldiamide (DTA5) at concentrations of 0.00005% and 0.005%. To perform the PCR, the RNA is first isolated from the dermal papilla cells using the RNeasy Mini Kit from Qiagen and transcribed into cDNA using reverse transcription. In the subsequent PCR reaction, which is carried out using gene-specific primers for the respective hair-relevant genes and serves to amplify the desired gene segments,The formation of PCR products is detected online via a fluorescence signal. The fluorescence signal is proportional to the amount of PCR product formed. The stronger the expression of a particular gene, the greater the amount of PCR product formed and the higher the fluorescence signal. To quantify gene expression, the solvent control is set to 1, and the expression of the genes to be determined is related to this (x-fold expression). Values ​​that are greater than or equal to 2-fold expression or less than or equal to 0.5-fold expression of the untreated control are classified as significantly differentially expressed. An age-dependent phenomenon is the thinning and increased fragility of hair. The strength of the hair and the hair structure depend essentially on the composition of specific hair-specific structural proteins.the hair keratins. The age-related change in the composition of these specific proteins influences the hair structure at the biological level. The expression of various hair keratin organotypic cell cultures can be investigated using the quantitative real-time PCR method described in Example 2. To quantify gene expression, the solvent control is set equal to 1 and the expression of the genes to be determined is related to this (x-fold expression). Values ​​that are greater than or equal to 2-fold expression or less than or equal to 0.5-fold expression of the untreated control are classified as significantly differentially expressed. The following table shows: ^ the influence of DTA5* on the expression of hair-relevant genes (TGF-β1, TGF-β2, IGFBP-3) ^ the detection of the stimulation of growth factors (KGF,HGF) and anagen-typical matrix proteins (Versican) after treatment with DTA5* ^ the evidence of activation of keratin synthesis after treatment with DTA5* can be seen: Substance Versica KGF IGFBP TGFβ1 TGFβ2 KRT86 KRT34 KRT33 (% n 3 (hhb6) (hha4) a DTA5*) (hha3) 1 Control 1.0 1.0 1.0 1.0 1.0 0.005% 0.8 1.7 0.4 0.5 0.3 0.0005% 0.7 2.1 1.5 1.4 0.6 0.00005% 1.6 1.5 1.4 1.4 1.1 2 Control 1.0 1.0 1.0 1.0 0.001% 1.0 0.9 9.5 10.8 0.0005% 1.3 2.2 4.6 5.3 0.00005% 1.4 1.5 1.8 2.0 3 Control 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 0.001% 0.7 0.9 1.4 1.4 1.1 0.5 1.3 1.3 0.0005% 0.7 1.2 1.1 1.1 1.2 1.6 1.2 1.1 0.00005% 1.0 1.3 0.8 1.0 1.1 2.7 2.5 2.5 + 0.1% 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 LM* LM* Propylene carbonate DTA5* N,N-Dipropyl-2,3-dihydroxyterephthaldiamide → DTA5 leads to concentration-dependent differential gene expression of the two investigated catagen-associated marker genes (TGFβ,IGFBP3) → DTA5 leads to an increase in keratin expression (KRT86 (hhb6), KRT34 (hha4), KRT33a (hha3)) in organotypic cell cultures 24 hours after application.

Claims

Claims:

1. Cosmetic use of compounds of general formula (I) in the R 1 and R 2 independently for NR 3 R 4 or OR 5 stand and R 3 , R 4 and R 5independently of one another represent H or a cyclic or acyclic, straight-chain or branched-chain, aliphatic or aromatic hydrocarbon radical having 1 to 20 carbon atoms, the skeleton of which may be interrupted by one or more non-adjacent heteroatoms, in particular selected from O and / or N, and / or which may be substituted by OH groups or NH2 groups on C atoms not bonded to heteroatoms, in cosmetic hair and / or scalp treatment agents for stimulating hair growth and / or for eliminating, reducing, alleviating, or preventing hair loss and / or for strengthening the hair structure.

2. Cosmetic use according to claim 1, characterized in that cell vitality, cell proliferation, and the release of growth factors are stimulated, thus positively influencing the anagen hair growth phase and inhibiting the activation of catagen-associated parameters. 3.Cosmetic use according to one of claims 1 or 2, characterized in that in compounds of the general formula (I) R. 1 and R 2 are equal and for NR 3 R 4 4. Cosmetic use according to one of claims 1 to 3, characterized in that in compounds of the general formula (I) R 3 H.

5. Cosmetic use according to one of claims 1 to 4, characterized in that in compounds of the general formula (I) R 4 represents an alkyl group such as methyl, ethyl, n-propyl or i-propyl, an alkoxyalkyl group such as methoxyethyl, methoxypropyl, (2-methoxy)ethoxyethyl, ethoxyethyl, ethoxypropyl or (2-ethoxy)ethoxyethyl, a hydroxyalkyl group such as hydroxyethyl, hydroxypropyl, 2-hydroxypropyl, 1,2-dihydroxypropyl, 2-hydroxyethoxyethyl, (N-hydroxyethyl)aminoethyl, (N-methoxyethyl)aminoethyl or (N-ethoxyethyl)aminoethyl, or an aromatic group such as phenyl or benzyl.

6. Cosmetic use according to one of claims 1 to 6, characterized in that the compound of general formula (I) is N,N-dipropyl-2,3-dihydroxyterephthaldiamide (DTA5).

7. Cosmetic agent containing, in a cosmetic carrier, 0.005-1 wt. % of compounds of general formula (I) in the R 1 and R 2 independently for NR 3 R 4 or OR 5 stand and R 3 , R 4 and R 5independently of one another represent H or a cyclic or acyclic, straight-chain or branched-chain, aliphatic or aromatic hydrocarbon radical having 1 to 20 carbon atoms, whose skeleton may be interrupted by one or more non-adjacent heteroatoms, in particular selected from O and / or N, and / or which may be substituted by OH groups or NH2 groups on C atoms not bonded to heteroatoms.

8. Cosmetic agent according to claim 7, characterized in that it is in the form of a rinse-off or leave-on composition for the treatment of hair and / or the scalp. 9.Cosmetic agent according to one of claims 7 or 8, characterized in that it is a shampoo or a hair conditioner, such as a hair rinse, a hair treatment, an essence, a lotion, a serum, a hair-tip fluid, and is in liquid form or as a powder or solid, or a spray, gel, or wax, or a hair styling agent, such as a hairspray, a hair gel, or a hair wax.

10. Cosmetic method for stimulating hair growth and / or for eliminating, reducing, alleviating, or preventing hair loss and / or for strengthening the hair structure, characterized in that an agent according to one of claims 7 to 9 is applied to the hair and / or the scalp.

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