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WO2025113900A1 - (sels d')acide polyaspartique dans des produits cosmétiques pour le traitement capillaire - Google Patents

(sels d')acide polyaspartique dans des produits cosmétiques pour le traitement capillaire Download PDF

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Publication number
WO2025113900A1
WO2025113900A1 PCT/EP2024/080388 EP2024080388W WO2025113900A1 WO 2025113900 A1 WO2025113900 A1 WO 2025113900A1 EP 2024080388 W EP2024080388 W EP 2024080388W WO 2025113900 A1 WO2025113900 A1 WO 2025113900A1
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Prior art keywords
group
hair
cosmetic composition
formula
compounds
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German (de)
English (en)
Inventor
Volker Scheunemann
Kira NEUBAUER
Jessica Welzel
Christian Kropf
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Publication of WO2025113900A1 publication Critical patent/WO2025113900A1/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
    • A61Q5/12—Preparations containing hair conditioners
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/20—Halogens; Compounds 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
    • A61K8/30—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
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • 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
    • 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 a method for repairing hair damage and strengthening the inner hair structure using a cosmetic composition comprising specific polyamino acid (salts).
  • a cosmetic composition is applied to the hair, optionally massaged in and rinsed out again after an exposure time of 5 seconds to 60 minutes, wherein the cosmetic composition contains one or more compounds of the following formula (i), where the sum of m+n is 2 to 100
  • M stands for a hydrogen, metal or ammonium cation.
  • the method according to the invention has the advantage that compounds according to formula (i) serve as bonding agent(s) in the cosmetic compositions.
  • these are highly effective, non-toxic, and biodegradable.
  • hair treated according to a method defined herein exhibits a stronger internal structure, which is reflected in a higher denaturation temperature, increased tensile strength, and reduced swelling in water. This applies in particular to hair treatment methods according to the invention applied to oxidatively damaged hair.
  • the denaturation temperature reflects the internal structural strength of the cortex proteins.
  • compounds according to formula (i) ensure permanent repair by penetrating deep into the hair fibers and creating new microbonds there through chemical crosslinking.
  • the hair's natural keratin is encased in the fibers, permanently repairing the hair.
  • the process defined herein results in a significant hair repair effect that can be achieved with an active ingredient of biotechnological origin.
  • the present invention also provides the use of compounds according to formula (i) in cosmetic compositions for repairing hair damage and strengthening the internal hair structure.
  • the present invention also provides a cosmetic composition for repairing hair damage and strengthening the internal hair structure, which comprises specific amounts of compounds according to formula (i) and at least one other hair fiber repair agent.
  • Compounds according to formula (i) which are particularly suitable for use in the process according to the invention are preferably understood to mean those in which the sum m+n is 2 to 50 and which have an average molecular weight in the range from 500 to 10,000 g/mol, more preferably 500 to 7,500 g/mol and particularly preferably 1,000 to 7,500 g/mol.
  • M represents a hydrogen or an alkali metal cation, such as a sodium or potassium cation.
  • the sum of m+n is 2 to 50 and M is an H, Na or K cation.
  • Compounds of formula (i) are particularly preferably polyaspartic acid and/or sodium salts of polyaspartic acid. They preferably have the previously defined average molecular weights.
  • Suitable commercial products which can be used in processes according to the invention are known and available, for example under the name Baypure® DS 100 from Lanxess.
  • One or more compounds according to formula (i) can be used in the cosmetic compositions used in the process according to the invention, preferably in weight proportions of 0.01 to 5 wt.% (based on the total weight of the cosmetic Composition). More preferred are weight proportions of 0.05 to 4 wt.% and in particular of 0.1 to 3 wt.%.
  • polyaspartic acid and/or a sodium salt of polyaspartic acid is used in the above-mentioned amounts in the cosmetic compositions of the method according to the invention.
  • 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, 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
  • solid forms such as powders, granules, or bars.
  • Cosmetic compositions suitable for use in the process according to the invention preferably contain compounds according to formula (i) in a cosmetic carrier.
  • a suitable cosmetic carrier for the cosmetic compositions 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 90:1.
  • Water and aqueous-alcoholic mixtures containing up to 50% by weight, especially up to 25% by weight, of alcohol, based on the alcohol/water mixture, can be preferred bases.
  • the pH of the cosmetic compositions 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 compositions in which compounds according to formula (i) can be employed for use in the method according to the invention are present, for example, in solid or liquid embodiments, such 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), 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/or hair, such as hair rinses, hair treatments, hair packs, hair tonics, hair serums, ethanolic or aqueous tinctures, etc.
  • 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.
  • compositions comprising compounds according to formula (i) are used for the care of hair and scalp.
  • this preferably includes 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.
  • 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.
  • leave-on preparations are understood to mean those 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 the treatment. Rather, the preparations remain on the scalp or hair until the next wash.
  • a preferred embodiment comprises methods according to the invention in which compounds according to formula (i) are used in hair conditioners. These preparations can be mixed with water or an at least predominantly water-containing The product should be rinsed out; however, it may be preferable to leave the hair conditioner on the hair as explained above.
  • a further preferred embodiment comprises processes according to the invention in which compounds according to formula (i) are used in cleansing compositions for the scalp and hair
  • the respective cosmetic compositions preferably contain other ingredients depending on the intended use.
  • the cosmetic compositions suitable for use in the method according to the invention may contain surfactant(s).
  • 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 used with particular advantage in both cleansing and care compositions due to their advantageous properties.
  • the method according to the invention or the use according to the invention is characterized in that the cosmetic composition
  • - based on its total weight - contains 0.1 to 25 wt.% of at least one anionic, amphoteric, zwitterionic, non-ionic or cationic surfactant or emulsifier.
  • a particularly preferred embodiment comprises methods according to the invention or uses according to the invention in which cosmetic compositions are used which are in a cosmetic carrier (based on their total weight)
  • 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 C 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),
  • Acyl isethionates with 8 to 24 C atoms in the acyl group (isethionate surfactants), acyl glutamates 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-alkyl polyoxyethyl 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),
  • 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-(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.
  • cosmetic compositions 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 -SO5- 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 C 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 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 as
  • 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 contain cationic surfactants from the group of quaternary ammonium compounds and/or esterquats and/or amidoamines.
  • a particularly preferred embodiment comprises methods according to the invention or uses according to the invention in which cosmetic compositions are used which are in a cosmetic carrier (based on their total weight)
  • a cosmetic composition is used in the process according to the invention which, in addition to compounds according to formula (i), contains at least one hair care active ingredient in a weight proportion of 0-50% by weight of 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 in particular 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 mixtures thereof.
  • Adding one or more hair care substances a) - f) to the cosmetic compositions offers the advantage that the method according to the invention, in addition to repairing damaged hair fibers and strengthening the inner hair structure, can also contribute to increasing 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. Furthermore, it has been demonstrated that the hair treatment method according to the invention, using a shampoo containing at least one previously defined 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 include, in particular, di-n-alkyl ethers with a total of between 12 and 36 carbon atoms, especially 12 to 24 carbon 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: (i) 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-C30 fatty alcohols.
  • 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 (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® B), myristyl myristate (Ce
  • 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.
  • 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 III )R IV - or -C(O)-N(R V )R VI ,
  • R IH -(CH2)X-CH3, where x is 0-22, and R IV represents -CH2-CH(OH)-CH2- or -(CH2)x-, optionally substituted with one or more -OH groups, where x 0-22;
  • 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 present 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 present in cosmetic compositions preferably in amounts of 0.005 to 1% by weight, based on the total composition.
  • o Vitamin B5 pantothenic acid, panthenol and pantolactone. Within this group, panthenol and/or pantolactone are preferably used.
  • Useful derivatives of panthenol are in particular the esters and ethers of panthenol and cationically derivatized panthenols.
  • panthenol triacetate, panthenol monoethyl ether and its monoacetate and cationic panthenol derivatives are, for example, panthenol triacetate, panthenol monoethyl ether and its monoacetate and cationic panthenol derivatives.
  • the aforementioned compounds of the vitamin B5 type 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 B (pyridoxine as well as pyridoxamine and pyridoxal) o Vitamin B7 - cf.
  • Vitamin C (ascorbic acid). Vitamin C can preferably be used in cosmetic compositions in amounts of 0.01 to 3 wt.%, based on the total composition.
  • 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 cosmetic compositions in amounts of 0.005-1 wt.%, based on the total composition.
  • Vitamin F usually refers to essential fatty acids, especially linoleic acid, linolenic acid, and arachidonic acid. Vitamin H.
  • the compound (3aS,4S,6aR)-2-oxohexahydrothienol[3,4-d]imidazole-4-valeric acid is referred to as vitamin H, but the common name biotin has since become established.
  • Biotin can be contained in cosmetic compositions preferably in amounts of 0.0001 to 1.0% by weight, in particular in amounts of 0.001 to 0.01% by weight.
  • 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 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 especially preference is given to Polyquaternium-10.
  • 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 Dalton. Particularly preferred are those known under the INCI name Guar Hydroxypropyltrimonium Chloride and/or Hydroxypropyl Guar Hydroxypropyltrimonium Chloride. known cationic guar polymers having a molecular weight (weight average) between 200,000 and 1,600,000 Dalton.
  • 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 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 be peptides consisting of 3-40, more preferably 5-20 amino acids. Also preferred are peptides f) 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 cosmetic compositions - based on their total weight - in amounts of 0.0001 to 10 wt.%, particularly preferably 0.0005 to 5 wt.% and in particular 0.001 to 1 wt.%.
  • the method according to the invention can be further improved and thus the repair effect of the hair fibers and their internal structural strengthening can be further intensified if the cosmetic compositions contain at least one further repair agent for hair fibers in addition to one or more compounds according to formula (i).
  • a particularly preferred embodiment comprises methods according to the invention or uses according to the invention in which cosmetic compositions are used which contain, in a cosmetic carrier, in addition to at least one previously defined compound according to formula (i), from 0.01 to 10% by weight of at least one additional repair agent for hair fibers, based on their total weight.
  • the cosmetic compositions suitable for use in the method according to the invention may 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
  • 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
  • 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
  • Another object of the invention relates to a cosmetic composition which is contained in a cosmetic carrier (based on its total weight)
  • (ii) contains 0.01 to 10% by weight of at least one additional hair fiber repair agent selected from a. compounds of the following formulas (I) or (II) b. Compounds of the following formula (III) and/or
  • the cosmetic composition is 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 composition comprises in a cosmetic carrier (based on its total weight) a) 0.01 - 5 wt.% of at least one compound of formula (i) and b) 0.01 to 10 wt.% of at least one compound of formula (I) and at least one compound of formula (II).
  • the cosmetic composition comprises in a cosmetic carrier (based on its total weight) a) 0.01 - 5 wt.% of at least one compound of formula (i) and b) 0.01 to 10 wt.% of at least one compound of formula (III).
  • the cosmetic composition comprises in a cosmetic carrier (based on its total weight) a) 0.01 - 5 wt.% of at least one compound according to formula (i) and b) 0.01 to 10 wt.% of lanthanum chloride.
  • Suitable compounds of formulas (I) and (II) are known as mixtures.
  • One possible way of preparing 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 used in a molar ratio of 0.1:1 to 99.9:1, more preferably 1:99 to 99:1, especially 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.
  • R 7 , R 8 represents H or a group -(CH2)o-CH3, where o represents the numbers 3, 4, 5, 6, 7, 8, 9 or 10, and
  • 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.
  • alpha-hydroxyoctanal alpha-hydroxyoctanone or mixtures thereof.
  • a particularly preferred embodiment of the cosmetic composition according to the invention is characterized in that it contains in a cosmetic carrier - based on its total weight - a) 0.01 - 5 wt.% of at least one compound according to formula (i) and b) 0.01 - 10 wt.% of a. a mixture of hydroxypropylgluconamide and hydroxypropylammonium gluconate or b. alpha-hydroxyoctanal or alpha-hydroxyoctanone or c. lanthanum chloride or d. any mixture of a., b. and c.
  • 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:
  • Three hair strands were used, which were cleaned with SLES (approximately 3% active substance in deionized water, pH 6-7). After that, the strands were rinsed with water, except for the strands used for the Untreated reference bleached with Blond Me Lift9+, mixing ratio 1:2 (bleaching powder: developer with 9% H2O2). 5 g of the mixture was applied per g of hair for 45 minutes. The pretreatment was completed at least 48 hours before application of the product.
  • aqueous solution M1 containing 1% polyaspartic acid (Baypure DS 100) was prepared.
  • the pH of the solution was 6.5.
  • One of the bleached hair strands was immersed in the solution 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.
  • the hair treatment procedure with the aqueous solution M1 containing polyaspartic acid resulted in a significant increase in the denaturation temperature of ultra-bleached hair strands.

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Abstract

La présente invention concerne un procédé de réparation de lésions capillaires et de renforcement de la structure capillaire interne à l'aide d'une composition cosmétique contenant des (sels) de polyaminoacides spécifiques.
PCT/EP2024/080388 2023-11-27 2024-10-28 (sels d')acide polyaspartique dans des produits cosmétiques pour le traitement capillaire Pending WO2025113900A1 (fr)

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DE102023211791.6A DE102023211791A1 (de) 2023-11-27 2023-11-27 Verfahren zur Reparatur von Haarschäden und zur Kräftigung der inneren Haarstruktur

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000012054A1 (fr) * 1998-08-31 2000-03-09 Wella Aktiengesellschaft Utilisation d'acide polyaspartique dans des produits de traitement capillaire
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 (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000012054A1 (fr) * 1998-08-31 2000-03-09 Wella Aktiengesellschaft Utilisation d'acide polyaspartique dans des produits de traitement capillaire
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
WO2017011237A1 (fr) * 2015-07-10 2017-01-19 Hercules Incorporated Procédé de renforcement de fibres de cheveux et de protection de couleur de cheveux colorés contre une décoloration ou un lavage

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