WO2025113899A1 - Polyepoxysuccinic acid (salts) in cosmetic preparations for treating hair - Google Patents

Abstract

The invention relates to cosmetic preparations for treating hair and scalp which contain, in a cosmetic carrier, polyepoxysuccinic acid or specific salts or derivatives of polyepoxysuccinic acid, and are exceptionally suitable for conditioning and repairing hair damage and for strengthening the inner hair structure.

Description

,Polyepoxysuccinic acid (salts) in cosmetic products for the treatment of hair

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.

It is well known that chemical or excessive treatments of human hair can, in many cases, lead to severe internal structural damage and, in extreme cases, to the breaking of keratin bonds. Chemical treatments that can cause more or less severe damage include perms, repeated cold waves, bleaching and lightening processes, and coloring with oxidative dyes, especially when combined with lightening. Hair damage can also be caused by sun exposure and frequent washing. All of these factors can induce damage at various levels and alter the hair structure, resulting in overall weaker hair. Such damage manifests itself in a loss of natural shine and softness, an unattractive and dull appearance, a brittle and stiff feel, and a tendency toward split ends, breakage, and/or the appearance of small knots in the hair.

Attempts have already been made to improve the structure of hair damaged in this way through various treatments, although no satisfactory solution has yet been found. In recent years, products claiming to repair hair have been launched, but the mechanism of action of the vast majority of these products is unclear or unclear. They are typically based on (synthetic) active ingredients with small molecules, and their effects usually last only for one shampoo. The hair repair effect for the consumer is therefore insufficient.

There is therefore a strong and understandable desire among consumers to prevent internal structural hair damage and/or to permanently restore the properties of healthy hair by continuously repairing the hair from the moment it grows back from the scalp, so that hair breakage is delayed, alleviated and ideally avoided.

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. Ideally, 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.

A first subject of the invention and preferred embodiments of the first

The subject matter of the invention is characterized by the following statements:

wobei in Formel (I) 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 and n stands for integers from 2-100.

2. 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.

3. Cosmetic agent according to one of statements 1 or 2, wherein the at least one compound according to formula (I) is contained in a weight proportion of 0.01 - 7.5 wt.% of the total weight of the cosmetic agent.

4. Cosmetic agent according to one of statements 1 to 3, wherein the at least one compound according to formula (I) is contained in a weight proportion of 0.1 - 5 wt.% of the total weight of the cosmetic agent.

5. Cosmetic agent according to one of statements 1 to 4, wherein in compounds of formula (I) R is -H and M is -H or an alkali metal cation.

6. Cosmetic agent according to one of statements 1 to 5, wherein compounds according to formula (I) have an average molecular weight of 400 to 10,000 g/mol.

7. Cosmetic agent according to one of statements 1 to 6, wherein compounds according to formula (I) have an average molecular weight of 600 to 2000 g/mol.

8. Cosmetic agent according to one of statements 1 to 7, wherein compounds according to formula (I) are polyepoxysuccinic acid (polyepoxysuccinic acid) or a sodium salt of polyepoxysuccinic acid.

b. Verbindungen der nachfolgenden Formel (iii) und/oder 9. 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 care composition for hair and scalp. Cosmetic product according to statement 11, containing at least one cationic surfactant in a weight proportion of 0.1 - 10 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 one of statements 1 to 14, containing at least one hair care active ingredient in a weight proportion of 0.01 to 30 wt.% of the total weight of the cosmetic agent. 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 agent according to one of statements 1 to 16, containing at least one additional repair agent for hair fibers in a weight proportion of 0.01 to 10 wt.% of the total weight of the cosmetic agent. Cosmetic agent according to claim 17, wherein the additional repair agent for hair fibers is selected from a) compounds of the following formulas (i) or (ii)

b. Compounds of the following formula (iii) and/or

R ⁷ -C(O)-CH(X)-R ⁸ (iii) c. inorganic lanthanum salts, wherein in formulas (i), (ii) and (iii) o 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, an alkylaryl group or a heterocyclic group; and o 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, o 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, o 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 by one or more hydroxyl or amino groups, and o X is -OH, -NH2, -CI, -Br, -I or the following groups: -O-(CH2)n-CH3, where n is the number 1, 2, 3 or 4, and -O-(CH2)m-OH, where m is the number 1, 2 or 3.

Compounds according to formula (I), in particular polyepoxysuccinic acids (PESA) or polyepoxysuccinic acids and their derivatives and salts, have so far been used in the field of water treatment and textile cleaning as scale inhibitors. Technical advantages of compounds according to formula (I) which might be of interest for cosmetic purposes have not yet been described in the prior art.

Within the scope of the present invention, it has now been found and demonstrated that with compounds according to formula (I) both the external conditioning of the surface of (damaged) hair fibers and their internal structural repair can be significantly and long-lastingly increased when they are used in suitable cosmetic hair treatment compositions.

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.

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 invention summarized above will now be presented in more detail.

Unless otherwise stated, all amounts expressed in % are % by weight and are expressed relative to the total weight of the respective cosmetic composition.

To optimally achieve the aforementioned effects, it is advantageous if compounds according to formula (I) are used in the cosmetic products either in acidic form, as a salt or in Ci-C4-alkyl-substituted form.

Preferably, in compounds according to formula (I), 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.

Due to the relatively low average molecular weight of compounds according to formula (I) in the previously defined range, they are particularly capable of penetrating the hair fibers and forming bonds with keratin in the cortex. This can restore the inner strength of chemically treated and/or damaged hair.

The above-mentioned effects are particularly pronounced when polyepoxysuccinic acid (polyepoxysuccinic acid) or a sodium salt of polyepoxysuccinic acid is used as the compound(s) according to formula (I).

With regard to the amounts used for compounds according to formula (I), it has been found that the aforementioned effects can be observed starting at a use amount of 0.001 wt.% (based on the total weight of the respective cosmetic hair treatment product). Optimal results can be achieved when compounds according to formula (I) are used in a weight proportion of 0.001-10 wt.%, more preferably 0.01-7.5 wt.%, and especially 0.1-5 wt.%, of the total weight of the cosmetic product.

Polyepoxysuccinic acid (PESA) or a sodium salt of polyepoxysuccinic acid is particularly preferably used in the amounts mentioned above.

There are no fundamental restrictions regarding the type of cosmetic compositions in which compounds according to formula (I) can be used. 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.

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.

To adjust this pH, virtually any acid or base suitable for cosmetic purposes can be used. 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. or combinations thereof, which can be present as both leave-on and rinse-off compositions, cosmetic compositions for the temporary or permanent shaping or fixing of hair, such as hair sprays, permanent wave fixing solutions, hair setting lotions, hair setting agents, Hair styling preparations, blow-dry lotions, mousses, hair gels, hair waxes or combinations thereof, temporary or permanent hair dyes.

Particularly preferred within the meaning of the present invention are cosmetic rinse-off or leave-on compositions comprising compounds according to formula (I) for the care of hair and/or scalp.

These preferably include 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. For the purposes of the present 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.

In a preferred embodiment, the cosmetic agent according to the invention serves to cleanse the hair and/or scalp.

These are particularly preferably 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

Contain 0.1 - 25 wt.% of at least one anionic, amphoteric, zwitterionic, non-ionic surfactant or mixtures thereof.

Particularly preferred cosmetic compositions formulated as a cleansing composition contain > 50% of at least one anionic surfactant (based on the total surfactant content).

All 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),

Ethercarboxylic acids of the formula RO-(CH2-CH2O) _X -CH2-COOH, in which R is a linear or e, saturated or unsaturated alkyl group having 8 to 30 C atoms and x = 0 or 1 to 16, and their physiologically acceptable salts,

Acylsarcosides with 8 to 24 C atoms in the acyl group (sarcosinate surfactants), acyltaurides with 8 to 24 C atoms in the acyl group (taurate surfactants), acyl isethionates with 8 to 24 C atoms in the acyl group (isethionate surfactants), acylglutamates with 8 to 24 C atoms in the acyl group (glutamate surfactants), sulfosuccinic acid mono- and/or dialkyl esters with 8 to 24 C atoms in the alkyl group and sulfosuccinic acid mono-alkylpolyoxyethyl esters with 8 to 24 C atoms in the alkyl group and 1 to 6 oxyethyl groups (sulfosuccinate surfactants),

Alpha-olefin sulfonates with 8 to 24 C atoms (alpha-olefin sulfonate surfactants),

Alkyl sulfates and/or alkyl ether sulfate salts of the formula R-(OCH2CH2)n-O-SO3X, in which R is preferably a straight-chain or e, saturated or unsaturated alkyl group having 8 to 30 C atoms, x is the number 0 or 1 to 12 and X is an alkali, alkaline earth, ammonium or alkanolamine ion,

Sulfonates of unsaturated fatty acids with 8 to 24 C atoms and 1 to 6 double bonds, esters of tartaric acid and citric acid with alcohols, which are addition products of about 2-15 molecules of ethylene oxide and/or propylene oxide with fatty alcohols with 8 to 22 C atoms, and/or

in der R¹ bevorzugt für einen aliphatischen Kohlenwasserstoffrest mit 8 bis 30 Kohlenstoffatomen, R² für Wasserstoff, einen Rest (CH₂CH₂0)_nR¹ oder X, n für Zahlen von 0 bis 10 und X für Wasserstoff, ein Alkali- oder Erdalkalimetall oder die Gruppe -NR³R⁴R⁵R⁶ steht, mit R³ bis R⁶ unabhängig voneinander stehend für einen Ci bis C4- Kohlenwasserstoffrest. Alkyl and/or alkenyl ether phosphates of the formula

in which 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 and 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.

Very particular preference is given to alkyl sulfate and/or alkyl ether sulfate salts, (salts of) ether carboxylic acids, sarcosinates, isethionates, taurates, sulfosuccinates and/or alpha-olefin sulfonates, in particular alkyl sulfate and/or alkyl ether sulfate salts.

Particularly preferred are 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.

Preferably, 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. Particularly preferred amphoteric surfactants are betaines such as N-alkyl-N,N-dimethylammonium glycinates, for example cocoalkyl dimethylammonium glycinate, N-acylaminopropyl-N,N-dimethylammonium glycinate, for example cocoacylaminopropyl dimethylammonium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethylimidazolines, each with 8 to 18 carbon atoms in the alkyl or acyl group, as well as cocoacylaminoethyl hydroxyethylcarboxymethylglycinate. Particularly preferred are the amphoteric or zwitterionic surfactants known under the INCI names Cocamidopropyl Betaine Lauramidopropyl Betaine, Cocoampho(di)acetate and/or Lauroapho(di)acetate.

Suitable non-ionic surfactants and/or emulsifiers can be selected from amine oxides such as 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.

Preferably, cosmetic compositions formulated as care compositions (hair conditioners) 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.

Further preferred 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 (hair conditioners) 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)

0.001 - 10 wt.% polyepoxysuccinic acid (PESA) or a sodium salt of polyepoxysuccinic acid and

Contain 0.1 to 10 wt.% of at least one cationic surfactant. To enhance the care properties, it may also be advantageous if the 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).

The addition of one or more 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, tert-butyl n-octyl ether, isopentyl n-octyl ether, and 2-methylpentyl n-octyl ether. Particular preference is given to di-n-octyl ether, which is commercially available under the name Cetiol® OE.

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;

(ii) polysiloxanes containing in their general structure one or more organofunctional groups selected from: a) substituted or unsubstituted aminated groups; b) (per)fluorinated groups; c) thiol groups; d) carboxylate groups; e) hydroxylated groups; f) alkoxylated groups; g) acyloxyalkyl groups; h) amphoteric groups; i) bisulfite groups; j) hydroxyacylamino groups; k) carboxy groups; l) sulfonic acid groups; and m) sulfate or thiosulfate groups;

(iii) linear polysiloxane(A)-polyoxyalkylene(B) block copolymers of type (AB) _n with n >3;

(iv) 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;

(v) 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;

(vi) or mixtures thereof. 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), di-n-butyl adipate (Cetiol® B), myristyl myristate (Cetiol® MM), cetearyl isononanoate (Cetiol® SN), Oleic acid decyl ester (Cetiol® V)

Dicarboxylic acid esters such as di-n-butyl adipate, di-(2-ethylhexyl) adipate, di-(2-ethylhexyl) succinate and di-isotridecyl 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 unsaturated linear and/or ene fatty acids with glycerol, such as Monomuls® 90-018, Monomuls® 90-L12, Cetiol® HE or Cutina® MD.

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.

For the purposes of the present invention, 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 Serobiologiques.

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. Examples of pearl extracts are the commercial products Pearl Protein Extract BG® or Crodarom® Pearl.

Particularly preferred protein hydrolysates b) are

Hydrolyzed keratin,

Hydrolyzed collagen,

Hydrolyzed silk protein,

Hydrolyzed cashmere protein,

Hydrolyzed wheat protein,

Hydrolyzed soy protein,

Hydrolyzed pea protein,

Hydrolyzed hemp seed protein,

Hydrolyzed cottonseed protein,

Hydrolyzed rice protein.

Furthermore, 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.%.

For the purposes of the present invention, proteolipids c) are compounds of the general

To understand formulas (II) or (III),

R'-X-R" Formula (II)

[R'-XR"] ⁺ Z- Formula (III) where 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 ,

R ¹ " -(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;

R ^v and R ^VI independently represent -H or -(CH2)x-CH3, where x = 0-22; with the proviso that R" represents keratin or a keratin hydrolysate when X represents -C(O)O-.

When X represents -C(O)O- or -N(R'")R ^IV - or -C(O)-N(R ^V )R ^VI , the compound is uncharged and formula (II) applies. When X represents -N ⁺ (R'"2)-R ^IV -, i.e. the nitrogen is quaternized, a counterion is present and formula (III) applies. The counterion is any suitable physiologically acceptable anion such as a halide. A preferred cation is chloride.

wobei More appropriately, the or each proteolipid has the formula (IVA):

where

R', R ¹ ", R" and Z are as previously defined, m = 1 to 10, and

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:

Hydrolyzed steardimonium hydroxypropyl keratin,

Hydrolyzed steardimonium hydroxypropyl collagen,

Hydrolyzed steardimonium hydroxypropyl silk protein,

Hydrolyzed steardimonium hydroxypropyl cashmere protein,

Hydrolyzed steardimonium hydroxypropyl rice protein, Hydrolyzed steardimonium hydroxypropyl wheat protein,

Hydrolyzed steardimonium hydroxypropyl soy protein,

Hydrolyzed steardimonium hydroxypropyl pea protein,

Hydrolyzed steardimonium hydroxypropyl cottonseed protein,

Hydrolyzed steardimonium hydroxypropyl hemp seed protein,

Hydrolyzed cocodimonium hydroxypropyl keratin,

Hydrolyzed Cocodimonium hydroxypropyl collagen,

Hydrolyzed cocodimonium hydroxypropyl silk protein,

Hydrolyzed cocodimonium hydroxypropyl cashmere protein,

Hydrolyzed cocodimonium hydroxypropyl rice protein,

Hydrolyzed cocodimonium hydroxypropyl soy protein,

Hydrolyzed cocodimonium hydroxypropyl wheat protein,

Hydrolyzed cocodimonium hydroxypropyl pea protein

Hydrolyzed cocodimonium hydroxypropyl cottonseed protein, hydrolyzed cocodimonium hydroxypropyl hempseed protein.

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. Examples of 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. Useful derivatives of panthenol 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) o 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 α-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. The term “vitamin F” usually refers to essential fatty acids, in particular linoleic acid, linolenic acid and arachidonic acid. Vitamin H. 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. Preference is given to quaternized cellulose polymers derived from hydroxy(C2-C4)alkylcelluloses, particularly preferably from hydroxyethylcelluloses. Such polymers are known to the person skilled in the art and are commercially available from various companies. 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®.

Further suitable 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.%.

For the purposes of the present invention, 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.

It has been found that 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.

b. Verbindungen der nachfolgenden Formel (III) und/oder Suitable additional repair agents for use in the cosmetic compositions according to the invention can preferably be selected from a. Compounds of the following formulas (i) or (ii)

b. Compounds of the following formula (III) and/or

R ⁷ -C(O)-CH(X)-R ⁸ (iii) c. inorganic lanthanum salts, wherein in formulas (i), (ii) and (iii)

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 R6 are independently hydrogen, an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, an aryl group, an alkylaryl group or a heterocyclic group; and

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.

Preferably, 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. Most preferably, 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.

In particularly suitable compounds of formula (iii), 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.

Most preferably, 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.

Also preferred are alpha-substituted compounds according to formula (iii) in which the substituent X represents a hydroxyl or an amino group.

Particularly preferably, X represents a hydroxyl group.

Particularly preferred are 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.

Very particular preference is given to 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.

Particularly preferred are alpha-hydroxyoctanal, alpha-hydroxyoctanone or mixtures thereof. Cosmetic 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.

Their application to damaged hair—especially hair damaged by oxidative treatments—leads to the repair of hair fibers through chemical cross-linking and the creation of new micro-bonds within the hair fiber. This strengthens the internal structure of the hair fibers.

A particularly preferred embodiment of the cosmetic agents according to the invention is characterized in that they are contained in a cosmetic carrier - based on their total weight

(i) 0.001 - 10 wt.% of at least one compound of formula (I) and

(ii) 0.01 - 10 wt.% of a. a mixture of hydroxypropyl gluconamide and hydroxypropylammonium gluconate or b. alpha-hydroxyoctanal or alpha-hydroxyoctanone or c. lanthanum chloride or d. any mixtures of a., b. and c.

In addition to the active ingredients described above, 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. by pregelatinization) and/or chemically modified starches, acrylic acid-acrylate copolymers, acrylic acid-acrylamide copolymers, acrylic acid-vinylpyrrolidone copolymers, acrylic acid-vinylformamide copolymers, polyacrylates and branched polymers of acrylic acid, methacrylic acid and their salts

Complexing agents such as EDTA Anti-dandruff 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. Specific suitable examples are the commercial products Aculyn® 22, Aculyn® 28, Structure® 2001, Structure® 3001, Structure Plus®, Carbopol® 1342, 1382, Ultrez 20, Ultrez 21, Amphomer®, Dermacryl® LT and 79, Luvitol® HSB, PVP (Luvitech® 17, 30, 60, 80, 85, 90, K 115), Luviskol® K 90, Luviskol® K 85, Luviskol® VA 64 and 73, Aquaflex® SF-40 Styleze® CC-10

Amino acids, preferably alanine, arginine, cysteine, cystine, glutamic acid, glycine, lysine, proline, serine, methionine, tyrosine and mixtures thereof

Pearlescent agents and/or opacifiers

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

Ceramide propellant

Preservatives.

With regard to preferred embodiments of the method according to the invention and the use according to the invention, what has been said about the agent according to the invention applies mutatis mutandis.

Examples:

The following hair treatment products were prepared. The quantities given are by weight unless otherwise stated.

1) Implementation examples

Hair shampoo:

Hair conditioner:

2) Wirkungsnachweis - DSC-Messungen Sulfate-free hair shampoo

2) Proof of effectiveness - DSC measurements

Background:

Hair is a keratin-containing material with a complex morphological microstructure. For mechanical or thermal studies, the structure can be simplified as a biphasic filament/matrix composite material, in which α-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 α-helix. The looser (less cross-linked) the matrix or the smaller the crystals of the α-helical phase, the lower the peak temperature.

Materials:

Hair strands: Alkinco 6634 (USA), natural, dark European hair; DSC pan pretreatment:

Three hair strands were used, each cleaned with SLES (approximately 3% active ingredient in deionized water, pH 6-7). Then, with the exception of the untreated reference strand, all strands were 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 pre-treatment was completed at least 48 hours before the product application.

Composition and method of application of the product:

An 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.

Measurement:

All three hair strands (untreated, bleached, bleached, and treated with solution M1) were each cut into pieces approximately 1 mm long. 12 aliquots per reference were placed in DSC pans. After adding 50 ml of deionized water, each pan was sealed. The measurement was performed in a temperature range of 100–200°C at a heating rate of 10 Kelvin per minute. The denaturation temperature (= peak temperature) was then determined.

Results:

*p<0.05 The hair treatment agent M1 according to the invention containing 1 wt.% polyepoxasuccinic acid (PESA) led to a significant increase in the denaturation temperature of ultra-bleached hair strands.

Claims

Patent claims: 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 and n stands for integers from 2-100. 2. Cosmetic agent 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 agent. 3. Cosmetic agent according to one of claims 1 or 2, wherein compounds according to formula (I) have an average molecular weight of 600 to 2000 g/mol. 4. Cosmetic agent according to one of claims 1 to 3, wherein in compounds of formula (I) R is -H and M is -H or an alkali metal cation. 5. Cosmetic agent according to one of claims 1 to 4, wherein compounds according to formula (I) are polyepoxysuccinic acid (polyepoxysuccinic acid) or a sodium salt of polyepoxysuccinic acid. 6. Cosmetic agent according to one of claims 1 to 5 in the form of a solid or liquid cosmetic cleansing composition for hair and scalp, 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 agent. 7. Cosmetic agent according to one of claims 1 to 5 in the form of a solid or liquid cosmetic care composition for hair and scalp, containing at least one cationic surfactant in a weight proportion of 0.1 - 10 wt.% of the total weight of the cosmetic agent. 8. Cosmetic agent according to one of claims 1 to 7, containing at least one hair care active ingredient in a weight proportion of 0.01 to 30 wt.% of the total weight of the cosmetic agent. 9. Cosmetic agent according to claim 8, wherein the at least one hair care active ingredient is selected from a) oils b) protein hydrolytes c) proteolipids d) vitamins e) cationic polymers f) peptides g) or any mixtures of a) - f). 10. Cosmetic agent according to one of claims 1 to 9, containing at least one additional repair agent for hair fibers in a weight proportion of 0.01 to 10 wt.% of the total weight of the cosmetic agent. 11. Cosmetic agent according to claim 10, wherein the additional hair fiber repair agent is selected from a. Compounds of the following formulas (i) or (ii)

b. Compounds of the following formula (iii) and/or R ⁷ -C(O)-CH(X)-R ⁸ (iii) c. inorganic lanthanum salts, wherein in formulas (i), (ii) and (iii) o 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, an alkylaryl group or a heterocyclic group; and o 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, o 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, o 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 by one or more hydroxyl or amino groups, and o X is -OH, -NH2, -CI, -Br, -I or the following groups: -O-(CH2)n-CH3, where n is the number 1, 2, 3 or 4, and -O-(CH2)m-OH, where m is the number 1, 2 or 3. 12. Cosmetic method for conditioning hair and repairing hair damage and for strengthening the internal structure of the hair, in which a cosmetic product containing, in a cosmetic carrier, at least one compound according to formula (I) in a proportion by weight of at least 0.001% by weight of the total weight of the cosmetic product is applied to the hair and, if appropriate, rinsed out again after a contact time or left on the hair. 13. Cosmetic use of at least one compound according to formula (I) in cosmetic products for repairing hair damage and strengthening the internal hair structure.