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WO2024193888A1 - Dérivés de catéchol pour le traitement de signes de vieillissement des cheveux et/ou de vieillissement du cuir chevelu - Google Patents

Dérivés de catéchol pour le traitement de signes de vieillissement des cheveux et/ou de vieillissement du cuir chevelu Download PDF

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Publication number
WO2024193888A1
WO2024193888A1 PCT/EP2024/052835 EP2024052835W WO2024193888A1 WO 2024193888 A1 WO2024193888 A1 WO 2024193888A1 EP 2024052835 W EP2024052835 W EP 2024052835W WO 2024193888 A1 WO2024193888 A1 WO 2024193888A1
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Prior art keywords
hair
cosmetic
scalp
compounds
general formula
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German (de)
English (en)
Inventor
Thomas Welss
Christian Kropf
Sabine Gruedl
Gudrun Heinen
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Publication of WO2024193888A1 publication Critical patent/WO2024193888A1/fr
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/002—Preparations for repairing the hair, e.g. hair cure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q7/00—Preparations for affecting hair growth

Definitions

  • the present invention relates to the cosmetic use of specific catechol derivatives to combat age-related changes in the hair follicle, to promote keratin synthesis in the hair and to positively influence the hair structure.
  • the invention further relates to a cosmetic agent which contains 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 the hair structure. Androgenetic hair loss is a widespread phenomenon and often affects the self-esteem of those who suffer from it.
  • Hair follicle cells are subject to a genetically determined cycle of growth, regression and resting phase.
  • the hair follicle is therefore 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 control 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 by the use of a test formulation, it is essential to act specifically on the corresponding mechanisms. Maintaining the youthfulness of the hair or rejuvenating it through suitable active ingredient formulations is a challenge for cosmetic research.
  • Topical applications to treat disorders in the hair structure usually involve physical processes 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 care substances through repeated use.
  • the only way to improve the structure of the hair from the root is through oral application of certain active ingredients.
  • Studies of the molecular and cell-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.
  • hair keratins KRT86 (hhb6), KRT34 (hha4) and KRT33a (hha3) as well as various cytokeratins (e.g. CK1) are affected by age-related changes.
  • Hair keratins are 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 major changes, such as deformation and breakage of the hair fiber (monilethix).
  • the aim of the present invention was therefore to find suitable active ingredients for use in cosmetic hair and/or scalp treatment products that are applied topically to the hair and/or scalp, protect against premature hair loss, activate keratin synthesis and thus counteract hair aging.
  • This aim has been achieved to a large extent by the use of specific catechol derivatives.
  • a first object of the invention is therefore the cosmetic use of compounds of the general formula (I) in which R 1 and R 2 independently of one another represent NR 3 R 4 or OR 5 and R 3 , R 4 and R 5 independently 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.
  • 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 which counteract or reverse the decline in keratin synthesis, the decrease in cell division activity and the decline in cell vitality.
  • 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 becomes thicker again due to increased keratin synthesis).
  • the use according to the invention of compounds according to formula (I) in cosmetic hair treatment agents also counteracts or reverses increased microinflammation and apoptosis.
  • a preferred use in the sense 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.
  • suitable compounds of the general formula (I) those are preferred in which the radicals R 1 and R 2 are identical and represent NR 3 R 4 .
  • R 3 is preferably H
  • R 4 is 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.
  • an alkyl group is particularly preferred and an n-propyl group is very particularly preferred.
  • Particularly preferred is a catechol derivative according to formula (I) known under the name N,N-dipropyl-2,3-dihydroxyterephthalamide (DTA5).
  • the radicals R 1 and R 2 in compounds of the general formula (I) are the same.
  • the radicals R 1 and R 2 in compounds of the general formula (I) are preferably NR 3 R 4 .
  • the radical R 3 in compounds of the general formula (I) is H.
  • the radical R 4 in compounds of the general formula (I) is 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.
  • an alkyl group such as methyl, ethyl, n-
  • the radical R 4 preferably represents an alkyl group and particularly preferably represents an n-propyl group.
  • the compound according to formula (I) is N,N-dipropyl-2,3-dihydroxyterephthaldiamide (DTA5).
  • DTA5 N,N-dipropyl-2,3-dihydroxyterephthaldiamide
  • the use according to the invention of compounds of the general formula (I) in cosmetic hair and/or scalp treatment agents is preferably carried out by using 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 information on "wt.%” refers in each case to the weight of the entire cosmetic hair and/or scalp treatment agent.
  • a second subject of the invention is therefore a cosmetic agent which contains 0.005 - 1 wt.%, in particular 0.01 - 0.5 wt.% of compounds of the general formula (I) in a cosmetic carrier, whereby the preferred embodiments described above or below in connection with the use according to the invention also apply to this subject 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.
  • a cosmetic agent which contains 0.005 - 1 wt.%, in particular 0.01 - 0.5 wt.% of compounds of the general formula (I) in a cosmetic carrier
  • An aqueous or aqueous-alcoholic base can be used as a cosmetic carrier for the cosmetic agents according to the invention.
  • 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 used 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, with values from 3 to 5 being particularly preferred. To adjust this pH, practically any acid or base that can be used for cosmetic purposes can be used.
  • Acids that are usually used are food acids. Food acids are understood to be acids that are ingested as part of normal food intake and have positive effects on the human organism.
  • Food acids are, for example, acetic acid, lactic acid, tartaric acid, citric acid, malic acid, ascorbic acid and gluconic acid.
  • citric acid and/or lactic acid is particularly preferred.
  • Preferred bases are ammonia, alkali hydroxides, monoethanolamine, triethanolamine and N,N,N',N'-tetrakis-(2-hydroxypropyl)-ethylenediamine.
  • Cosmetic agents in the sense of the present invention can be present in solid or liquid embodiments, 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.
  • - 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,
  • - cosmetic compositions for the temporary or permanent shaping or fixing of hair such as hair sprays, permanent wave fixing solutions, hair setting products, hair styling preparations, blow-dry lotions, mousses, hair gels, hair waxes or combinations thereof Combinations, - temporary or permanent hair dyes.
  • Suitable cosmetic agents in the sense of the present invention can be rinsed out with water after the intended application to the scalp and/or hair or can remain therein or on it.
  • 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 are preferably understood to mean 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 solid, as well as sprays, gels or waxes, or hair styling agents, such as hair sprays, hair gels or hair waxes.
  • 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 solid, as well as sprays, gels or waxes, or hair styling agents, such as hair sprays, hair gels or hair waxes.
  • remaining on the scalp and hair means preparations that 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 an hour during the treatment. Rather, the preparations remain on the scalp or hair until the next wash.
  • 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 agent that contains at least a large amount of water after an exposure time; however, they are preferably left on the hair, as explained above.
  • compounds of the general formula (I) can be used in cleaning 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 cleaning compositions such as powders, granules, soap bars, cleaning wipes, porous bodies (solid foams) are preferably moistened with water or soaked in water or dissolved before use, then foamed up by rubbing between the hands or directly on 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, shower gels are mixed with water before use if necessary, lathered on the scalp and/or hair and rinsed with water after use.
  • the agents according to the invention can contain surfactant(s).
  • anionic surfactants In cleaning compositions (usually rinse-off compositions), anionic surfactants have proven particularly useful, in conditioning compositions (rinse-off or leave-on compositions) cationic surfactants are often used ingredients; amphoteric and/or non-ionic surfactants and/or emulsifiers are used with particular advantage in both cleaning 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 cleaning composition for the scalp and/or the 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 - 0.1 - 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 0.5 - 30 wt.%, more preferably 1 - 25 wt.% and in particular 2 - 20 wt.% of
  • Particularly preferred cosmetic agents which are 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 are 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 about 8 to 30 carbon atoms.
  • the molecule can contain glycol or polyglycol ether groups, ester, ether and amide groups as well as hydroxyl groups.
  • 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.
  • alkyl (ether) sulfates of the general formula R-(OCH 2 CH 2 ) n -OSO 3 X, in which R is a straight-chain or branched, saturated or unsaturated alkyl group with 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 which 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 non-ionic 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 have 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. They are also capable of forming internal salts.
  • amphoteric surfactants are betaines such as N-alkyl-N,N-dimethylammonium glycinates, for example cocoalkyl-dimethylammonium glycinate, N-acyl-aminopropyl-N,N-dimethylammonium glycinate, for example cocoacylaminopropyl-dimethylammonium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethyl-imidazolines, each with 8 to 18 C atoms in the alkyl or acyl group, as well as cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • betaines such as N-alkyl-N,N-dimethylammonium glycinates, for example cocoalkyl-dimethylammonium glycinate, N-acyl-aminopropyl-N,N-dimethylammonium glycinate, for example coco
  • amphoteric or zwitterionic surfactants known under the INCI names Cocamidopropyl Betaine Lauramidopropyl Betaine, Cocoampho(di)acetate and/or Lauroapho(di)acetate.
  • Suitable nonionic 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 their salts.
  • amine oxides such
  • compositions according to the invention can contain cationic surfactant(s).
  • Cosmetic agents according to the invention which are formulated as care compositions (hair conditioning agents) 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, in particular 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 the scalp - contain - based on their weight - preferably 0.05 to 10 wt.
  • Cosmetic agents 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 amounts mentioned above.
  • 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.
  • cosmetic agents 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 agent. More preferred are amounts of 0.01 - 30 wt.%, particularly preferably 0.05 - 25 wt.% and in particular 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. Cationic polysaccharide polymers are preferred.
  • 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 in the sense of the invention are those which 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 a water-insoluble Chains.
  • the "side chain" of a cellulose is defined as chemical substituents that bind to the cellulose skeleton and are not part of the native cellulose, since they were subsequently introduced, for example, by chemical synthesis.
  • Preference is given to quaternized cellulose polymers that originate from hydroxy(C 2 -C 4 )alkylcelluloses, particularly preferably from hydroxyethylcelluloses. Such polymers are known to the person skilled in the art and are commercially available from various companies.
  • cationic cellulose derivatives known under the INCI names Polyquaternium-4, Polyquaternium-10, Polyquaternium-24, Polyquaternium-67 and/or Polyquaternium-72.
  • Very particular preference is given to Polyquaternium-10, Polyquaternium-24 and/or Polyquaternium-67 and particularly preference is given to Polyquaternium-10.
  • 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 polymer from the group of polyquaternium-4, polyquaternium-10, polyquaternium-24, polyquaternium-67 and/or polyquaternium-72.
  • Suitable cationic guar derivatives in the sense 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.
  • Particularly preferred are the cationic guar polymers known under the INCI name Guar Hydroxypropyltrimonium Chloride and/or Hydroxypropyl Guar Hydroxypropyltrimonium Chloride with a molecular weight (weight average) of between 200,000 and 1,600,000 Dalton.
  • the cationic charge density of these guar polymers is preferably at least 0.4 meq/g, preferably at least 0.5 meq/g and in particular at least 0.6 meq/g.
  • Their nitrogen content is preferably in the range from 1.1 to 1.8% by weight (based on their total weight).
  • Cationic guar derivatives known under the INCI name Guar Hydroxypropyltrimonium Chloride are known to the person skilled in the art and are available from various suppliers, for example under the trade names Cosmedia ® Guar, N-Hance ® Jaguar ® and/or Polycare ® .
  • 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.
  • 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 agents 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 usually 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 and synthetic hydrocarbons are particularly used as mineral oils.
  • An example of a hydrocarbon that can be used is 1,3-di-(2-ethylhexyl)-cyclohexane (Cetiol ® S), which is available as a commercial product.
  • a dialkyl ether can also serve as a suitable oil component.
  • Dialkyl ethers that can be used are in particular di-n-alkyl ethers with a total of between 12 and 36 C atoms, in particular 12 to 24 C atoms, such as 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-iso-pentyl ether, di-3-ethyldecyl ether, tert-butyl-n-octyl
  • di-n-octyl ether which is commercially available under the name Cetiol ® OE.
  • Silicone compounds are preferred as synthetic oils. Silicones have excellent conditioning properties on keratin fibers, especially on hair. In particular, they make hair easier to comb when wet and dry 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 non-branched; (ii) polysiloxanes which contain in their general structure one or more organofunctional groups which are 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
  • Fats are understood to mean fatty acids, fatty alcohols and natural and synthetic waxes, which can be present both in solid form and liquid in an aqueous dispersion.
  • Fatty acids that can be used are linear and/or branched, saturated and/or unsaturated fatty acids with 6 - 30 carbon atoms, preferably with 10 - 22 carbon atoms.
  • Fatty alcohols that can be used are saturated, mono- or polyunsaturated, e or unbranched fatty alcohols with C 6 - C 30 -, preferably C 10 - C 22 - and very particularly 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, micro waxes made from PE or PP.
  • Other suitable fatty substances are, for example, ester oils, which are esters of C6 - C30 fatty acids with C2 - C30 fatty alcohols.
  • ester oils are isopropyl myristate (Rilanit ® IPM), isononanoic acid C16-18 alkyl esters (Cetiol ® SN), 2-ethylhexyl palmitate (Cegesoft ® 24), stearic acid 2-ethylhexyl ester (Cetiol ® 868), cetyl palmitate, cetyl oleate, glycerol tricaprylate, coconut fatty alcohol caprate/caprylate (Cetiol ® LC), n-butyl stearate, oleyl erucate (Cetiol ® J 600), isopropyl palmitate (Rilanit ® IPP), oleyl oleate (Cetiol ® ), lauric acid hexyl ester (Cetiol ® A), di-n-butyl adipate (Cetiol
  • 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.%.
  • the cosmetic agents according to the invention of the second subject matter of the invention can, 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 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.
  • 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 caprylate - 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 me
  • 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.
  • cosmetic care compositions for hair and/or scalp - in particular leave-on care compositions - which are characterized as follows: - 0.005 - 1% by weight of at least one compound according to formula (I) - 0.05 - 7.5% by weight of at least one cationic surfactant - 0.01 - 30% by weight of at least one conditioning agent for keratin fibers (where the cationic surfactant does not count as a conditioning agent) - 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.
  • compositions were produced for the treatment of hair and/or the scalp (the quantities refer to % 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 alkyl polyglucoside** 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
  • Hepatocyte Growth Factor HGF
  • Keratinocyte Growth Factor KGF
  • HGF Hepatocyte Growth Factor
  • KGF Keratinocyte Growth Factor
  • TGF- ⁇ 1, TGF- ⁇ 2 and IGFBP-3 have a growth-inhibiting effect and are characteristic markers for the catagen phase, in which keratin synthesis in the follicle is switched off. These markers should be repressed in 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 a concentration of 0.00005% and 0.005%.
  • DTA5 N,N-dipropyl-2,3-dihydroxyterephthaldiamide
  • the RNA is first isolated from the dermal papilla cells using the RNeasy Mini Kit from Qiagen and transcribed into cDNA using reverse transcription.
  • the formation of the 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.
  • 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.
  • An age-dependent phenomenon is the thinning and increased fragility of the hair.
  • the strength of the hair and the hair structure depend essentially on the composition of special hair-specific structural proteins, the hair keratins.
  • the age-related change in the composition of these specific proteins influences the hair structure on a biological level.
  • the expression of various hair keratins in organotypic cell cultures can be examined 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. which 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.

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Abstract

L'invention concerne l'utilisation cosmétique de dérivés spécifiques du catéchol pour lutter contre des changements liés à l'âge dans des follicules pileux, pour favoriser la synthèse de kératine dans les cheveux et pour exercer une influence positive sur la structure des cheveux. L'invention concerne en outre un produit cosmétique contenant des quantités spécifiques du dérivé de catéchol dans un véhicule approprié et un procédé cosmétique permettant de stimuler la pousse des cheveux et/ou permettant d'éliminer, de réduire, d'atténuer ou de prévenir la chute des cheveux et/ou permettant de renforcer la structure des cheveux.
PCT/EP2024/052835 2023-03-22 2024-02-06 Dérivés de catéchol pour le traitement de signes de vieillissement des cheveux et/ou de vieillissement du cuir chevelu Pending WO2024193888A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102023202565.5A DE102023202565A1 (de) 2023-03-22 2023-03-22 Catecholderivate zur Behandlung von Alterungserscheinungen der Haare und/oder der Kopfhaut
DE102023202565.5 2023-03-22

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WO2024193888A1 true WO2024193888A1 (fr) 2024-09-26

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PCT/EP2024/052835 Pending WO2024193888A1 (fr) 2023-03-22 2024-02-06 Dérivés de catéchol pour le traitement de signes de vieillissement des cheveux et/ou de vieillissement du cuir chevelu

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10259199A1 (de) * 2002-12-16 2004-06-24 Henkel Kgaa Restrukturierung und Ausrüstung keratinischer Fasern
WO2008020037A1 (fr) * 2006-08-16 2008-02-21 Action Medicines, S.L. Utilisation de dérivés de 2,5-dihydroxybenzène pour le traitement de l'obésité, de l'hirsutisme, de l'hypertricose et des verrues virales
WO2020074143A1 (fr) * 2018-10-11 2020-04-16 Henkel Ag & Co. Kgaa Détergent à plusieurs composants, à complexe métallique-catéchine
CN111991273A (zh) * 2019-05-27 2020-11-27 珀莱雅化妆品股份有限公司 一种具有生发功效的乳液及其制备方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10259199A1 (de) * 2002-12-16 2004-06-24 Henkel Kgaa Restrukturierung und Ausrüstung keratinischer Fasern
WO2008020037A1 (fr) * 2006-08-16 2008-02-21 Action Medicines, S.L. Utilisation de dérivés de 2,5-dihydroxybenzène pour le traitement de l'obésité, de l'hirsutisme, de l'hypertricose et des verrues virales
WO2020074143A1 (fr) * 2018-10-11 2020-04-16 Henkel Ag & Co. Kgaa Détergent à plusieurs composants, à complexe métallique-catéchine
CN111991273A (zh) * 2019-05-27 2020-11-27 珀莱雅化妆品股份有限公司 一种具有生发功效的乳液及其制备方法

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