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WO2025113899A1 - Acide polyépoxysuccinique (sels) dans des préparations cosmétiques pour le traitement des cheveux - Google Patents

Acide polyépoxysuccinique (sels) dans des préparations cosmétiques pour le traitement des cheveux Download PDF

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Publication number
WO2025113899A1
WO2025113899A1 PCT/EP2024/080383 EP2024080383W WO2025113899A1 WO 2025113899 A1 WO2025113899 A1 WO 2025113899A1 EP 2024080383 W EP2024080383 W EP 2024080383W WO 2025113899 A1 WO2025113899 A1 WO 2025113899A1
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Prior art keywords
hair
cosmetic
group
formula
weight
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German (de)
English (en)
Inventor
Volker Scheunemann
Jessica Welzel
Christian Kropf
Kira NEUBAUER
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Publication of WO2025113899A1 publication Critical patent/WO2025113899A1/fr
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    • 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
    • A61Q5/02—Preparations for cleaning the hair
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • 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
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A61K8/65—Collagen; Gelatin; Keratin; Derivatives or degradation products thereof
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86—Polyethers
    • 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
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/004—Preparations used to protect coloured hair

Definitions

  • the invention relates to cosmetic compositions containing specific polyepoxysuccinic acid (salts) for the treatment of hair, a cosmetic method for repairing hair damage and strengthening the inner hair structure using the cosmetic compositions, and the cosmetic use of specific polyepoxysuccinic acid (salts) in cosmetic compositions for repairing hair damage and strengthening the inner hair structure.
  • the aim of the present invention was to find suitable active ingredients for use in cosmetic hair and scalp treatments that can significantly contribute to the permanent repair of internal hair damage and strengthen the internal hair structure.
  • the active ingredients should be of natural origin or based on natural ingredients to provide both more effective and more sustainable products. This object was achieved according to the invention by a means according to claim 1.
  • Cosmetic product for the treatment of hair and scalp containing in a cosmetic carrier at least one compound of the following formula (I) in a weight proportion of at least 0.001% by weight of the total weight of the cosmetic product where in formula (I)
  • R stands for -H or for a straight-chain or branched Ci-C4 alkyl group
  • M stands for a hydrogen, alkali or ammonium cation
  • n stands for integers from 2-100.
  • Cosmetic product according to claim 1 wherein the at least one compound according to formula (I) is contained in a weight proportion of 0.001 - 10 wt.% of the total weight of the cosmetic product.
  • Cosmetic product according to any one of claims 1 to 8 in the form of a solid or liquid cleansing composition for hair and scalp Cosmetic product according to one of statements 1 to 9, containing at least one surfactant selected from anionic, amphoteric, zwitterionic, non-ionic surfactants or mixtures thereof in a weight proportion of 0.1 - 25 wt. % of the total weight of the cosmetic product.
  • Cosmetic product according to one of statements 1 to 8 in the form of a solid or liquid composition for the temporary or permanent shaping or fixing of human hair Cosmetic product according to one of statements 1 to 8 in the form of a solid or liquid composition for the coloring of human hair.
  • Cosmetic agent according to statement 15, wherein the at least one hair care active ingredient is selected from a) oils b) protein hydrolyzates c) proteolipids d) vitamins e) cationic polymers f) peptides g) or any mixtures of a) - f).
  • Cosmetic hair treatment compositions comprising compounds according to formula (I) improve hair strength to its original, healthy state. This has been demonstrated by a very strong increase in the denaturation temperature (see examples).
  • Compounds according to formula (I) ensure permanent repair in cosmetic hair treatment products by penetrating deep into the hair fibers and creating new microbonds through chemical cross-linking.
  • the hair's natural keratin is trapped within the fibers, permanently repairing the hair. This effect is particularly noticeable when the cosmetic products are applied to oxidatively damaged hair.
  • the present invention also provides a cosmetic method for hair conditioning and repairing hair damage and for strengthening the inner hair structure, in which a cosmetic agent which contains in a cosmetic carrier at least one compound according to formula (I) in a weight proportion of at least 0.001% by weight of the total weight of the cosmetic agent is applied to the hair and optionally rinsed out again after a contact time.
  • a cosmetic agent which contains in a cosmetic carrier at least one compound according to formula (I) in a weight proportion of at least 0.001% by weight of the total weight of the cosmetic agent is applied to the hair and optionally rinsed out again after a contact time.
  • the present invention also provides the cosmetic use of at least one compound according to formula (I) in cosmetic compositions for repairing hair damage and strengthening the internal hair structure.
  • the radical R is -H and M is a hydrogen or an alkali metal cation, in particular a sodium cation.
  • Further preferred compounds according to formula (I) are those which have an average molecular weight in the range of 400 - 10,000 g/mol and particularly preferably 600 - 2,000 g/mol.
  • Polyepoxysuccinic acid (PESA) or a sodium salt of polyepoxysuccinic acid is particularly preferably used in the amounts mentioned above.
  • Suitable packaging forms include, for example, creams, lotions, solutions, waters, emulsions such as W/O, O/W, and PIT emulsions (emulsions based on the theory of phase inversion, also known as PIT), microemulsions and multiple emulsions, coarse, unstable, single- or multi-phase shake mixtures, gels, sprays, aerosols, foam aerosols, and also solid forms such as powders, granules, or bars.
  • emulsions such as W/O, O/W
  • PIT emulsions emulsions based on the theory of phase inversion, also known as PIT
  • microemulsions and multiple emulsions coarse, unstable, single- or multi-phase shake mixtures
  • gels gels
  • sprays aerosols
  • foam aerosols foam aerosols
  • solid forms such as powders, granules, or bars.
  • Cosmetic compositions according to the invention preferably contain compounds according to formula (I) in a cosmetic carrier.
  • a suitable cosmetic carrier for the cosmetic products can be, 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 90:1.
  • Water and aqueous-alcoholic mixtures containing up to 50% by weight, in particular up to up to 25% by weight of alcohol, based on the alcohol/water mixture, can be preferred bases.
  • the pH value of cosmetic products can, in principle, be between 2 and 11. It is preferably between 2 and 7, with values of 3 to 5 being particularly preferred.
  • Food acids are commonly 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. Examples of food acids include acetic acid, lactic acid, tartaric acid, citric acid, malic acid, ascorbic acid, and gluconic acid. For the purposes 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 in which compounds according to formula (I) can be used are, for example, in solid or liquid embodiments, e.g. as cosmetic cleansing compositions for the scalp and hair, such as cleansing powders or granules, soap bars, cleansing wipes, porous bodies (solid cleansing foams), liquid hair shampoos, 2-in-1 hair care shampoos, anti-dandruff shampoos, hair coloring shampoos, hair cleansing rinses or combinations thereof, cosmetic care compositions (conditioners) for the scalp and hair, such as hair rinses, hair treatments, hair packs, hair tonics, hair serums, ethanolic or aqueous tinctures, etc.
  • cosmetic cleansing compositions for the scalp and hair such as cleansing powders or granules, soap bars, cleansing wipes, porous bodies (solid cleansing foams), liquid hair shampoos, 2-in-1 hair care shampoos, anti-dandruff shampoos, hair coloring shampoos, hair cleansing rinses or combinations thereof, cosmetic care compositions (conditioners) for the scalp and hair, such as hair rinses, hair treatments, hair packs,
  • compositions for the temporary or permanent shaping or fixing of hair such as hair sprays, permanent wave fixing solutions, hair setting lotions, hair setting agents, Hair styling preparations, blow-dry lotions, mousses, hair gels, hair waxes or combinations thereof, temporary or permanent hair dyes.
  • compositions comprising compounds according to formula (I) for the care of hair and/or scalp.
  • liquid hair care shampoos or hair conditioners such as hair rinses, hair treatments, essences, lotions, serums, tonics, hair tip fluids, which can be in liquid form or as a powder (solid), as well as sprays, gels or waxes understood.
  • Leave-on compositions for the care of hair and/or scalp containing compounds of formula (I) have proven particularly effective and can therefore represent preferred embodiments of the teachings of the invention.
  • "leaving on the scalp and hair” refers to 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 one hour during treatment. Rather, the preparations remain on the scalp or hair until the next wash.
  • a preferred embodiment comprises solid or liquid hair and scalp care compositions (hair conditioners) comprising compounds according to formula (I). These preparations can be rinsed out with water or an at least predominantly water-containing agent after a contact time; however, it may be preferred if they are left on the hair, as explained above.
  • a further preferred embodiment comprises solid or liquid cleansing compositions for the scalp and hair (shampoo) comprising compounds according to formula (I).
  • the respective cosmetic compositions preferably contain other ingredients depending on the intended use.
  • Cosmetic agents according to the invention may contain surfactant(s) in addition to compounds according to formula (I).
  • Anionic surfactants have proven particularly effective in cleansing compositions (usually rinse-off compositions), while cationic surfactants are frequently used ingredients in conditioning compositions (rinse-off or leave-on compositions).
  • Amphoteric and/or nonionic surfactants and/or emulsifiers are particularly advantageously used in both cleansing and care compositions due to their advantageous properties.
  • the cosmetic agent according to the invention serves to cleanse the hair and/or scalp.
  • liquid compositions which, based on their total weight, contain, in addition to compounds according to formula (I), 0.1 to 25% by weight of at least one anionic, amphoteric, zwitterionic, non-ionic or mixtures thereof.
  • a particularly preferred embodiment comprises cosmetic compositions for the treatment of hair which are contained in a cosmetic carrier (based on their total weight) 0.001 - 10 wt.% polyepoxysuccinic acid (PESA) or a sodium salt of polyepoxysuccinic acid and
  • Particularly preferred cosmetic compositions formulated as a cleansing composition contain > 50% of at least one anionic surfactant (based on the total surfactant content).
  • anionic surface-active substances suitable for cosmetic use on the human or animal body are suitable as anionic surfactants and emulsifiers. 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.
  • Particularly suitable anionic surfactant types that can be used in cosmetic compositions include, for example: linear and branched fatty acids with 8 to 30 C atoms (soaps),
  • 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-olefin sulfonates with 8 to 24 C atoms (alpha-olefin sulfonate surfactants),
  • R 1 preferably represents an aliphatic hydrocarbon radical having 8 to 30 carbon atoms
  • R 2 represents hydrogen, a radical (CH 2 CH 2 0) n R 1 or X
  • n represents numbers from 0 to 10
  • X represents hydrogen, an alkali or alkaline earth metal or the group -NR 3 R 4 R 5 R 6 , with R 3 to R 6 independently of one another representing a Ci to C4 hydrocarbon radical.
  • 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 -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.
  • cosmetic compositions according to the invention which are formulated as cleaning compositions contain, in addition to anionic surfactants, 0-15%, particularly preferably 0.25-12.5% and in particular 0.5-10% of at least one amphoteric or zwitterionic surfactant and/or 0-15%, particularly preferably 0.25-12.5% and in particular 0.5-10% of at least one non-ionic surfactant (in each case based on the total weight of the cosmetic composition).
  • 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-acylaminopropyl-N,N-dimethylammonium glycinate, for example cocoacylaminopropyl dimethylammonium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethylimidazolines, each with 8 to 18 carbon atoms in the alkyl or acyl group, as well as cocoacylaminoethyl hydroxyethylcarboxymethylglycinate.
  • betaines such as N-alkyl-N,N-dimethylammonium glycinates, for example cocoalkyl dimethylammonium glycinate, N-acylaminopropyl-N,N-dimethylammonium glycinate, for example cocoacylaminopropyl dimethylam
  • 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 those known under the INCI names Cocamine Oxide, Lauramine Oxide and Compounds known as 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.
  • cosmetic compositions formulated as care compositions 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.
  • Suitable amidoamines include, for example, stearamidopropyl dimethylamine, cocamidopropyl dimethylamine, behenamidopropyl dimethylamine, brassicamidopropyl dimethylamine or mixtures thereof.
  • Suitable esterquats include, for example, distearoylethyl hydroxyethylmonium methosulfate, dicocoylethyl hydroxyethylmonium methosulfate, dipalmitoylethyldimonium chloride, behenoyl PG trimonium chloride, bis-(isostearoyl/oleoyl isopropyl)dimonium methosulfate or mixtures thereof.
  • cationic surfactants are the imidazolium compounds known under the INCI names Quaternium-27, Quaternium-83, Quaternium-87, and/or Quaternium-91.
  • Cosmetic compositions formulated as care compositions particularly preferably contain cationic surfactants from the group of quaternary ammonium compounds and/or esterquats and/or amidoamines.
  • a particularly preferred embodiment comprises cosmetic compositions for the treatment of hair which are contained in a cosmetic carrier (based on their total weight)
  • PESA polyepoxysuccinic acid
  • sodium salt of polyepoxysuccinic acid 0.001 - 10 wt.% polyepoxysuccinic acid (PESA) or a sodium salt of polyepoxysuccinic acid and
  • compositions according to the invention contain, in addition to compounds of formula (I), at least one hair care active ingredient in a proportion of 0-50% by weight based on the total weight of the respective composition. Amounts used are more preferred, ranging from 0.01-30% by weight, particularly preferably from 0.05-25% by weight, and especially from 0.01-20% by weight.
  • the at least one hair care active ingredient can preferably be selected from a) oils b) protein hydrolysates c) proteolipids d) vitamins e) cationic polymers f) peptides g) or any mixtures of active ingredients a) - f).
  • hair care substances a) - f) to cosmetic products offers the advantage that, in addition to repairing damaged hair fibers and strengthening the inner hair structure, it can also contribute to improving the care of the outer hair fibers, which is visually and haptically perceptible. Care of the outer hair fibers is understood, in particular, to mean increased smoothness, shine, suppleness, and volume of the hair fibers. Furthermore, it has been demonstrated that the use of hair treatment products according to the invention, which contain at least one compound according to formula (I) and optionally one or more active ingredients a) - f), leads to a significant reduction in combing force of the hair fibers.
  • Suitable oils a) are understood to mean natural, mineral or synthetic oils, fats, waxes or mixtures thereof.
  • the group of suitable natural (vegetable) oils typically includes 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.
  • An example of a suitable hydrocarbon is the commercially available 1,3-di-(2-ethylhexyl)-cyclohexane (Cetiol® S) or mixtures of medium-chain alkanes (such as Cetiol® Ultimate).
  • 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, especially 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-isopentyl ether, di-3-ethyldecyl ether,
  • 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 hair's grip and softness. Suitable silicones can be selected from:
  • polyalkylsiloxanes polyarylsiloxanes, polyalkylarylsiloxanes, which are volatile or non-volatile, straight-chain or cyclic, branched or unbranched;
  • grafted silicone polymers with a non-silicone-containing organic backbone consisting of an organic main chain formed from organic monomers not containing silicone, to which at least one polysiloxane macromer has been grafted in the chain and optionally at at least one chain end;
  • grafted silicone polymers having a polysiloxane backbone onto which non-silicone-containing organic monomers have been grafted, comprising a polysiloxane main chain onto which at least one organic macromer not containing silicone has been grafted in the chain and optionally at at least one of its ends;
  • Fats include fatty acids, fatty alcohols and natural and synthetic waxes, which can be in solid form or liquid 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.
  • Fatty alcohols that can be used are saturated, mono- or polyunsaturated, branched or unbranched fatty alcohols with C10-C30, preferably C10-C22 and most preferably C12-C22 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 C1-C30 fatty acids with C2-C50 fatty alcohols.
  • Examples of particularly suitable ester oils are isopropyl myristate (Rilanit® IPM), isononanoic acid C16-18-alkyl esters (Cetiol® SN), 2-ethylhexyl palmitate (Cegesoft® 24), 2-ethylhexyl stearate (Cetiol® 868), cetyl palmitate, cetyl oleate, glycerol tricaprylate, coconut fatty alcohol caprylate Z-caprylate (Cetiol® LC), n-butyl stearate, oleyl erucate (Cetiol® J 600), isopropyl palmitate (Rilanit® IPP), oleyl oleate (Cetiol®), lauric acid hexyl ester (Cetiol® A
  • Dicarboxylic acid esters such as di-n-butyl adipate, di-(2-ethylhexyl) adipate, di-(2-ethylhexyl) succinate and di-isotridecyl acylate 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 unsatur
  • the weight proportion of oils, fats and/or waxes in the total weight of the cosmetic compositions may preferably be 0 to 30% by weight, particularly preferably 0.01 to 25% by weight and in particular 0.05 to 15% by weight.
  • protein hydrolysates b) are degradation products of proteins produced by acidic, basic, or enzymatic reactions. Due to the production process, protein hydrolysates exhibit a molecular weight distribution.
  • Suitable protein hydrolysates b) can be of plant, animal, marine or synthetic origin.
  • Preferred protein hydrolysates of plant origin can be selected from the group consisting of soy, almond, pea, moringa, potato, and wheat protein hydrolysates.
  • Such products are available, for example, under the trademarks Gluadin® (Cognis), DiaMin® (Diamalt), Lexein® (Inolex), Hydrosoy® (Croda), Hydrolupin® (Croda), Hydrosesame® (Croda), Hydrotritium® (Croda), Crotein® (Croda), and Puricare® LS 9658 from Laboratoires Serobi unanimouss.
  • Preferred protein hydrolysates of animal origin can be selected from the group consisting of elastin, collagen, keratin, silk, and milk protein hydrolysates, which can also be present in the form of salts.
  • Such products are marketed, for example, under the trademarks Dehylan® (Cognis), Promois® (Interorgana), Collapuron® (Cognis), Nutrilan® (Cognis), Gelita-Sol® (Deutsche Gelatine Fabriken Stoess & Co), Lexein® (Inolex), ProSina® (Croda), and Kerasol® (Croda).
  • Preferred protein hydrolysates of marine origin can be selected from the group consisting of collagen hydrolysates from fish or algae, protein hydrolysates from mussels, and pearl hydrolysates.
  • pearl extracts are the commercial products Pearl Protein Extract BG® or Crodarom® Pearl.
  • Particularly preferred protein hydrolysates b) are
  • cationized protein hydrolysates within the meaning of the present invention are to be counted among the protein hydrolysates b), wherein the underlying protein hydrolysate originates from the same sources as previously explained.
  • the weight proportion of protein hydrolysates b) in the total weight of the cosmetic compositions may preferably be 0 to 10 wt.%, particularly preferably 0.01 to 5 wt.% and in particular 0.01 to 3 wt.%.
  • proteolipids c) are compounds of the general
  • R' represents a straight-chain or branched, saturated or unsaturated functional hydrocarbon group having 8 to 24 carbon atoms (including mixtures of such R' groups as are found, for example, in natural products such as coconut oil).
  • R" represents a protein, a peptide or a protein hydrolysate
  • Z represents a physiologically acceptable anion
  • - X represents -C(O)O- or -N + (R'"2)-R IV - or -N(R'")R IV - or -C(O)-N(R V )R VI ,
  • each proteolipid has the formula (IVA): where
  • Y stands for -H or -OH.
  • R" may be a protein. Alternatively, R" may be a peptide. R" may also be a protein hydrolysate. Preferably, R" is a protein hydrolysate. Such a protein hydrolysate may be keratin-based, i.e., a keratin hydrolysate. Alternatively, R" may be a plant-based hydrolysate.
  • Preferred examples of proteolipids c) include:
  • the weight fraction of proteolipids c) in the total weight of the cosmetic compositions may preferably be 0 to 10 wt.%, particularly preferably 0.01 to 5 wt.% and in particular 0.01 to 3 wt.%.
  • Suitable vitamins d are understood to mean vitamins, provitamins and vitamin precursors as well as their derivatives from groups A, B, C, E, F and H.
  • the group of substances referred to as vitamin A includes retinol (vitamin A1) and 3,4-didehydroretinol (vitamin A2).
  • Beta-carotene is the provitamin of retinol.
  • suitable vitamin A components include vitamin A acid and its esters, vitamin A aldehyde and vitamin A alcohol as well as its esters such as palmitate and acetate.
  • the vitamin A component can preferably be contained in cosmetic compositions in amounts of 0.005-1% by weight, based on the total composition.
  • the vitamin B group or vitamin B complex includes, among others, o vitamin B1 (thiamine) o vitamin B2 (riboflavin) o vitamin B3.
  • the compounds nicotinic acid and nicotinamide (niacinamide) are often listed under this name. Nicotinamide is preferred and can be contained in cosmetic compositions preferably in amounts of 0.005 to 1% by weight, based on the total composition.
  • Vitamin B5 pantothenic acid, panthenol, and pantolactone). Within this group, panthenol and/or pantolactone are preferably used.
  • panthenol useful derivatives include, in particular, the esters and ethers of panthenol, as well as cationically derivatized panthenols. Examples of these include panthenol triacetate, Panthenol monoethyl ether and its monoacetate, as well as cationic panthenol derivatives.
  • the vitamin B5-type compounds mentioned can preferably be present in the cosmetic compositions in amounts of 0.05-5% by weight, based on the total composition. Amounts of 0.1-2% by weight are particularly preferred.
  • o Vitamin B1 pyridoxine, pyridoxamine, and pyridoxal
  • Vitamin B7 - cf Vitamin H. Vitamin C (ascorbic acid).
  • Vitamin C can preferably be used in the cosmetic compositions in amounts of 0.01 to 3% by weight, based on the total composition.
  • Use in the form of the palmitic acid ester, glucosides, or phosphates may be preferred.
  • Use in combination with tocopherols may also be preferred.
  • Vitamin E tocopherols, especially ⁇ -tocopherol.
  • Tocopherol and its derivatives, including in particular the esters such as acetate, nicotinate, phosphate and succinate can preferably be present in the cosmetic compositions in amounts of 0.005-1 wt.%, based on the total composition.
  • Vitamin F can preferably be present in the cosmetic compositions in amounts of 0.005-1 wt.%, based on the total composition.
  • vitamin F usually refers to essential fatty acids, in particular linoleic acid, linolenic acid and arachidonic acid.
  • Vitamin H refers to the compound (3aS,4S,6aR)-2-oxohexahydrothienol[3,4-d]imidazole-4-valeric acid, for which the trivial name biotin has now prevailed.
  • Biotin can preferably be present in the cosmetic compositions in amounts of 0.0001 to 1.0 wt.%, in particular in amounts of 0.001 to 0.01 wt.%.
  • the cosmetic compositions may particularly preferably contain vitamins, provitamins, and vitamin precursors from groups A, B, E, and H. Panthenol, pantolactone, nicotinamide, and vitamin E acetate are particularly preferred and may be added to the cosmetic compositions both individually and in combination in the amounts mentioned above.
  • Suitable cationic polymers e) include, for example, cationic polysaccharide polymers.
  • Suitable cationic polysaccharide polymers can be selected from cationic cellulose compounds and/or cationic guar derivatives.
  • Suitable cationic cellulose compounds carry more than one permanent cationic charge in at least one side chain.
  • 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.
  • Particular preference is given to the cationic polymers known under the INCI names Polyquaternium-4, Polyquaternium-10, Polyquaternium-24, Polyquaternium-67, and/or Polyquaternium-72. Cellulose derivatives. Polyquaternium-10, Polyquaternium-24, and/or Polyquaternium-67 are particularly preferred, and Polyquaternium-10 is especially preferred.
  • Suitable cationic guar derivatives 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 from 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 available from various suppliers, for example, under the trade names Cosmedia® Guar, N-Hance® Jaguar® and/or Polycare®.
  • cationic polymers for use in the cosmetic compositions 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.
  • Cationic polymers e) can be used in the cosmetic compositions - based on their total weight - in amounts of 0.01 to 3 wt.%, particularly preferably 0.05 to 2 wt.% and in particular 0.1 to 1.5 wt.%.
  • suitable peptides f) are preferably understood to mean peptides consisting of 3-40, more preferably 5-20 amino acids. Furthermore, preferred peptides f) are those in which the proportion of amino acids with an amino functionality in the side chain is at least 30%.
  • Peptides f) can be used in the agents according to the invention preferably in a weight proportion of 0.0001 - 10 wt.% (more preferably 0.0005 - 5 wt.% and in particular 0.001 - 1 wt.%) of the total weight of the cosmetic agent.
  • the repair effect of the hair fibers and their internal structural strengthening can be further intensified if the hair treatment compositions according to the invention contain at least one further repair agent for hair fibers in addition to compounds according to formula (I).
  • a particularly preferred embodiment is characterized in that the cosmetic agents in a cosmetic carrier contain, in addition to compounds according to formula (I) - based on their total weight - 0.01 to 10 wt.% of at least one additional hair fiber repair agent.
  • Suitable additional repair agents for use in the cosmetic compositions according to the invention can preferably be selected from a.
  • R1-R4 are independently hydrogen, a hydrocarbon radical having 1 to 10 carbon atoms, a hydroxyl group, an amino group, a sulfhydryl group, an aryl group or a halogen
  • R5 and R6 are independently hydrogen, an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, an aryl group, an alkylaryl group or a heterocyclic group
  • R1 -R4' are independently hydrogen, a hydrocarbon radical having 1 to 10 carbon atoms, a hydroxyl group, an amino group, a sulfhydryl group, an aryl group or a halogen and R5 and Re are independently hydrogen, an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, an aryl group or a heterocyclic group, it being excluded that R5' and Re' are simultaneously hydrogen, the aliphatic hydrocarbon group, the alicyclic hydrocarbon group, the aryl group, the alkylaryl group or the heterocyclic group are substituted by at least one hydroxyl group, one of the radicals R7 or R8 is H and the other is a straight-chain or branched, saturated or unsaturated alkyl group having 1 to 15 carbon atoms, where the carbon chain may optionally be substituted with one or more hydroxyl or amino groups, and
  • X represents -OH, -NH2, -CI, -Br, -I or the following groups: -O-(CH2)n-CH3, where n represents the numbers 1, 2, 3 or 4, and -O-(CH2)m-OH, where m represents the numbers 1, 2 or 3.
  • Suitable compounds of formulas (i) and (ii) are known as mixtures. One possible way to prepare them is disclosed, for example, in patent application US 2017/0007518.
  • At least one compound of formula (i) and at least one compound of formula (ii) are varied in a molar ratio of 0.1:1 to 99.9:1, more preferably 1:99 to 99:1, particularly preferably 20:80 to 80:20.
  • the molar ratio of compounds of formula (i) to compounds of formula (ii) is 40:60 to 60:40.
  • a mixture of hydroxypropyl gluconamide and hydroxypropylammonium gluconate in the aforementioned molar ratios is most preferably used in the cosmetic compositions.
  • Such mixtures are commercially available, for example, from Ashland under the trade name Fiberhance® bm.
  • one of the radicals R 7 , R 8 represents H and the other represents a saturated alkyl group having 1 to 15 carbon atoms.
  • Particularly preferred compounds of formula (iii) are those in which one of the radicals R 7 , R 8 represents H and the other represents a group -(CH2)O-CH3, where O represents the numbers 3, 4, 5, 6, 7, 8, 9 or 10.
  • one of the radicals R 7 or R 8 is H and the other is a butyl, pentyl, hexyl, heptyl or octyl group, in particular a hexyl group.
  • alpha-substituted compounds according to formula (iii) in which the substituent X represents a hydroxyl or an amino group.
  • X represents a hydroxyl group.
  • alpha-substituted compounds of the general formula (iii) in which one of the radicals R 7 , R 8 stands for H or for a group -(CH2)o-CH3, in which 0 stands for the numbers 3, 4, 5, 6, 7, 8, 9 or 10, and
  • X represents a hydroxyl group
  • alpha-substituted compounds of the general formula (III) which are selected from alpha-hydroxybutanal, alpha-hydroxypentanal, alpha-hydroxyhexanal, alpha-hydroxyheptanal, alpha-hydroxyoctanal, alpha-hydroxybutanone, alpha-hydroxypentanone, alpha-hydroxyhexanone, alpha-hydroxyheptanone, alpha-hydroxyoctanone or mixtures thereof.
  • compositions according to the invention are particularly suitable for the treatment of damaged hair, in particular for the treatment of hair damage caused by chemical treatments such as permanent waves, cold waves, bleaching and lightening processes, coloring processes with oxidation dyes, as well as by exposure to sunlight, frequent washing and drying under high heat.
  • the cosmetic products according to the invention may further contain one or more active ingredients from one or more of the following groups:
  • Dyes including both dyes for coloring the compositions and dyes for coloring hair, including 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
  • EDTA Anti-dandruff active ingredients such as Piroctone Olamine, Zinc Pyrithione, Climbazole, Propanediol Caprylate
  • Film-forming polymers such as, for example, 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.
  • Amino acids preferably alanine, arginine, cysteine, cystine, glutamic acid, glycine, lysine, proline, serine, methionine, tyrosine and mixtures thereof
  • Keratin-reducing agents such as mercaptans, thioglycolate salts, if necessary in combination with ammonia or amines, organic acids such as citric acid, malic acid, lactic acid, tartaric acid, alkalizing agents
  • Hair is a keratin-containing material with a complex morphological microstructure.
  • the structure can be simplified as a biphasic filament/matrix composite material, in which ⁇ -helical filaments are embedded in an amorphous matrix. These two dominant compounds largely determine the mechanical properties of human hair. Peak temperature values provide information about the damage or integrity of the matrix and ⁇ -helix. The looser (less cross-linked) the matrix or the smaller the crystals of the ⁇ -helical phase, the lower the peak temperature.
  • Hair strands Alkinco 6634 (USA), natural, dark European hair; DSC pan pretreatment:
  • aqueous agent M1 containing 2.5% of a 40% solution of polyepoxysuccinic acid (equivalent to 1% by weight of the active ingredient PESA) was prepared.
  • the pH of the agent was 6.5.
  • One of the bleached hair strands was immersed in agent M1 for 60 minutes at room temperature. The excess solution was then wiped off, the strand was rinsed with tap water for 1 minute, and finally shampooed twice for 1 minute each with an SLES solution (10%; pH 4.5). After rinsing and drying the strand, DSC measurements were performed on all three hair strands.
  • PESA polyepoxasuccinic acid

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Abstract

L'invention concerne des préparations cosmétiques pour le traitement des cheveux et du cuir chevelu qui contiennent, dans un véhicule cosmétique, de l'acide polyépoxysuccinique ou des sels ou dérivés spécifiques d'acide polyépoxysuccinique, et sont parfaitement adaptés pour conditionner et réparer les cheveux abimés et pour renforcer la structure capillaire interne.
PCT/EP2024/080383 2023-11-27 2024-10-28 Acide polyépoxysuccinique (sels) dans des préparations cosmétiques pour le traitement des cheveux Pending WO2025113899A1 (fr)

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DE102023211792.4 2023-11-27
DE102023211792.4A DE102023211792A1 (de) 2023-11-27 2023-11-27 Polyepoxysuccinsäure(salze) in kosmetischen Mitteln für die Behandlung von Haaren

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WO2025113899A1 true WO2025113899A1 (fr) 2025-06-05

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016188691A1 (fr) * 2015-05-22 2016-12-01 Unilever Plc Compositions de traitement capillaire
US20170007518A1 (en) 2015-07-10 2017-01-12 Hercules Incorporated Method of strengthening hair fibers and protecting dyed hair color from fading or wash-out

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016188691A1 (fr) * 2015-05-22 2016-12-01 Unilever Plc Compositions de traitement capillaire
US20170007518A1 (en) 2015-07-10 2017-01-12 Hercules Incorporated Method of strengthening hair fibers and protecting dyed hair color from fading or wash-out

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