Fiber-structure-enhancing agents for keratin fibers, having a selected acid combination and a structure-enhancing ketone compound

Abstract

The invention relates to treatment agents for keratin fibers, in particular for hair, for enhancing the fiber structure, containing, in a cosmetically acceptable carrier, the combination of succinic acid and citric acid in selected amounts and weight ratios to each other in combination with at least one active ingredient selected from at least one ketone compound of the formula R1-C(O)-CH2OH, in which R1 is a straight-chain or branched, saturated or unsaturated alkyl group having 2 to 15 carbon atoms. The invention also relates to a method for enhancing the fiber structure of keratin fibers using said treatment agents, and to the use of agents containing the combination of succinic acid and citric acid in selected amounts and weight ratios to each other, in combination with at least one active ingredient selected from one of the aforementioned ketone compounds, for enhancing the fiber structure of keratin fibers.

Description

[0001] Henkel AG & Co. KGaA 2024P00123DE 04.09.2025

[0002] Fiber structure improving agents for keratin fibers with a selected acid combination and a structure-improving ketone compound

[0003] The invention relates to treatment agents for keratin fibers, in particular for hair, for improving the fiber structure, comprising in a cosmetically compatible carrier the combination of succinic acid and citric acid in selected amounts and weight ratios to each other, in combination with at least one structural agent selected from at least one ketone compound of formula R 1 -C(O)-CH2OH, wherein the residue R 1for a straight-chain or branched, saturated or unsaturated alkyl group with 2 to 15 carbon atoms, as well as a method for improving the fiber structure of keratinous fibers using these treatment agents and the use of agents containing the combination of succinic acid and citric acid in selected amounts and weight ratios to each other, in combination with at least one structural agent selected from ketone compounds with the general formula R 1 -C(O)- CH2OH, wherein the residue R 1 stands for a straight-chain or branched, saturated or unsaturated alkyl group with 2 to 15 carbon atoms, for improving the fiber structure of keratin fibers.

[0004] Keratinous fibers, especially hair, are an integral part of the human body and a key component of clothing and home textiles, playing a vital role in everyday life. Treatment with washing, cleaning, styling, and coloring products, as well as exposure to environmental factors such as ozone, salt and chlorinated water, IR, UV, and heat radiation (e.g., from hairdryer), leads to cumulative damage to the fibers over time, thus reducing their quality. For example, both shampooing and styling hair through coloring or perming are processes that affect the natural structure and properties of the hair. Consequently, after such treatment, the hair's wet and dry combability, hold, volume, shine, and feel may be unsatisfactory.

[0005] Not least due to the significant stress placed on hair, for example by coloring or perming, as well as by shampooing and environmental pollution, the importance of hair care products with a sufficiently strong and long-lasting effect is increasing. Such products influence the surface of the keratin fibers and thus certain properties of the hair. For example, after such treatments, the hair's wet and dry combability, hold, and volume can be improved, or the hair can be protected from increased split ends. It has therefore long been common practice to subject the hair to a special after-treatment. This usually involves treating the hair with special active ingredients, such as quaternary ammonium salts or special polymers, in the form of a conditioner. Depending on the formulation, this treatment improves combability, the 2024P00123WC

[0006] 2

[0007] Improves hold and volume of the hair and reduces split ends.

[0008] Conditioning agents and film formers are frequently added to perming solutions, but these do not significantly improve hair structure. For example, high-molecular-weight polymers are used, which adhere to the outermost layer of the hair, creating a superficially noticeable improvement in the hair's feel. However, this does not reduce the structural damage within the hair, which is primarily caused by the reduction process during perming, because the substances are too large to penetrate the hair shaft.

[0009] In summary, the sustainability of the effects of hair structure-improving additives is often unsatisfactory, as these only adhere to the surface of the hair.

[0010] State of the art

[0011] Attempts have been made to address this problem by polymerizing monomeric compounds directly on the hair. According to US 5,362,486, certain urethane oligomers with terminal bisulfite or acrylate groups are applied to the hair and then polymerized, forming polymers that adhere to the hair in situ. This process favorably influences the surface properties of hair, such as volume, shine, hold, combability, as well as resistance to moisture and atmospheric pollutants and to hair color fading. However, this process involves radical polymerization on the hair, meaning the hair must be treated with radical initiators such as benzoyl peroxide, which could be counterproductive for improving the keratin structure.Patent application WO 2005 / 115314A1 discloses a process for restructuring keratin fibers, in which the keratin fibers are contacted with cystine and with at least one dicarboxylic acid having 2 to 10 carbon atoms, wherein preferred dicarboxylic acids are selected from oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, azelaic acid, maleic acid, fumaric acid, and sorbic acid, with succinic acid being particularly preferred. The addition of citric acid is not disclosed.

[0012] Patent application DE 10051774 A1 describes the use of short-chain carboxylic acids with a molecular weight below 750 g / mol in cosmetic products as an active ingredient for restructuring keratin fibers. Succinic acid is explicitly disclosed, while citric acid is not.

[0013] Patent application EP 1174112 A2 discloses hair treatment compositions which, in addition to an organic acid, in particular a dicarboxylic acid or a hydroxycarboxylic acid, contain as further essential components an organic solvent, a cationic surfactant, and a higher alcohol, and which serve to repair pores in hair. Both succinic acid and citric acid are disclosed as suitable acids, but are not among the preferred acids.

[0014] Patent applications FR3132839A1 and US2023210736A1 disclose aqueous hair treatment compositions with a pH of 3-10, which, in addition to a surfactant, also contain 0.25 to 10 wt% citric acid. These compositions improve the quality and 2024P00123WC

[0015] 3

[0016] The durability of hair, especially chemically treated hair, is significantly improved. Damage that occurs during or as a result of chemical treatment is repaired, minimized, and / or compensated for, and the keratin fibers of the hair are restructured, strengthened, and / or protected. The presence of succinic acid is optional and is only disclosed in connection with the neutralization of dialkyl omega surfactants.

[0017] Patent application WO 2023076449 A1 discloses aqueous hair treatment compositions that, for improving emulsion stability and the haptic properties of the hair, contain fatty alcohol(s), cation surfactant(s), cation polymer(s), niopolymer(s), and 0.1 to 5 wt% citric acid (salt), as well as a pH value in the range of 3 to 6, wherein the cation polymer and niopolymer are present in specific weight ratios. The presence of succinic acid is optional and is disclosed only in connection with the neutralization of dialkyl fatty amine surfactants. Patent applications W02017011237A1 and DE102020206653A1 disclose methods for strengthening hair fibers using a hair composition containing an amide and / or an alkylammonium carboxylate salt. The amide can be a monoamide and / or a diamide.

[0018] The object of the invention was to provide a method for restructuring keratin fibers that offers advantages over the prior art and enables sufficient efficacy and duration of action. The method should not only be feasible under fiber-friendly conditions, but also be physiologically safe and, for example, require no reactive monomers.

[0019] Surprisingly, it was found that a treatment agent containing a combination of succinic acid and citric acid, wherein each of these acids can be present independently in salt form and wherein the total amount of succinic acid and citric acid is 1 to 5 wt%, converted to the free acid content and based on the weight of the treatment agent, wherein succinic acid (BS) and citric acid (CS) are present in a weight ratio BS / CS of 0.400 to 2.500, in combination with at least one compound selected from ketone compounds of formula R 1 -C(O)-CH2OH, wherein the residue R 1The invention states that the melting temperature of keratin fibers can be increased and their strength enhanced by the presence of a straight-chain or branched, saturated or unsaturated alkyl group with 2 to 15 carbon atoms. Within the scope of the present invention, it was found that the synergistic combination of succinic acid and citric acid within the concentration limits specified above, in combination with a ketone compound of the formula (I) according to claim, resulted in a synergistic effect in the restructuring of keratin fibers that could not be observed with the individual acids or compounds. The fiber treatment agents, uses, and methods according to the invention strengthen the internal and external structure of keratin fibers, i.e., they enable the restructuring of keratin fibers.In the context of the present invention, restructuring refers in particular to fiber reinforcement, increased tensile strength, and / or a reduction of damage to keratin fibers caused by various influences. Restoring natural strength plays a crucial role in this process. Restructured fibers may, for example, exhibit an increased melting point (measured by differential scanning calorimetry (DSC)), increased tensile strength, increased elasticity, and / or increased volume, which can manifest, for instance, as greater fullness in a hairstyle. Furthermore, the keratin fibers may display improved luster, improved feel, and / or easier combability.

[0020] According to the invention, keratinous fibers are to be understood as furs, wool, feathers, silk and hair, but in particular human hair.

[0021] The problem according to the invention is solved by compositions, uses and methods according to the claims.

[0022] A first object of the present invention is a treatment agent for keratin fibers, in particular for hair, for improving the fiber structure, containing succinic acid and citric acid in a cosmetically compatible carrier, wherein each of these acids can be present independently of one another in salt form and wherein the total amount of succinic acid and citric acid 1 to

[0023] 5 wt.%, converted to the free acid content and based on the weight of the fiber treatment agent, characterized in that succinic acid (BS) and citric acid (CS) are present in a weight ratio BS / CS to each other of 0.400 to 2.500, preferably 0.70 to 2.20, particularly preferably 0.80 to 1.60, each converted to the free acids, and further characterized in that additionally at least one compound selected from at least one ketone compound of formula (I),

[0024] R 1 -C(O)-CH2OH (I), wherein the residue R 1 for a straight-chain or branched, saturated or unsaturated alkyl group with 2 to 15, preferably with 3 to 8, particularly preferably with 5 to 6, extremely preferably with

[0025] It contains 6 carbon atoms.

[0026] Preferred treatment agents for keratin fibers according to the invention are characterized in that the total amount of succinic acid and citric acid, including any salts of these acids, is 1.2 to 3.5 wt.%, preferably 1.5 to 3.0 wt.%, more preferably 1.7 to 2.5 wt.%, particularly preferably 1.8 to 2.4 wt.%, and most preferably 1.9 to 2.2 wt.%, in each case converted to the free acid content and based on the weight of the fiber treatment agent.

[0027] Further treatment agents for keratin fibers preferred according to the invention are characterized in that the total amount of succinic acid, including any salts of succinic acid contained, is 0.3 to 2.5 wt.%, preferably 0.5 to 2.0 wt.%, more preferably 0.7 to 1.7 wt.%, particularly preferably 0.9 to 1.6 wt.%, and more preferably 1.0 to 1.5 wt.%. 2024P00123WC

[0028] 5 most preferably 1.3 to 1.5 wt.%, in each case converted to the free acid content and based on the weight of the fiber treatment agent.

[0029] Further treatment agents for keratin fibers preferred according to the invention are characterized in that the total amount of citric acid, including any salts of citric acid contained, is 0.1 to 4.0 wt.%, preferably 0.3 to 3.0 wt.%, more preferably 0.5 to 1.5 wt.%, particularly preferably 0.6 to 1.3 wt.%, extraordinarily preferably 0.7 to 1.2 wt.%, and extraordinarily preferably 0.8 to 1.0 wt.%, in each case converted to the content of free acid and based on the weight of the fiber treatment agent.

[0030] In the keratin fiber treatment agents preferred according to the invention, the succinic acid is present at least partially in salt form. Succinic acid is a dibasic acid with pKa values ​​of 4.16 (pKa1) and 5.61 (pKa2). The extent to which succinic acid is present in salt form in the aqueous environment of the keratin fiber treatment agents preferred according to the invention therefore depends, among other things, on the pH value of the fiber treatment agent.The at least one salt of succinic acid is selected from the alkali metal, alkaline earth metal, zinc, lanthanum, cerium, ammonium, alkylammonium, alkanolammonium, and glucammonium salts, in particular the mono-, di-, and trimethyl, -ethyl, and -hydroxyethylammonium salts, furthermore the salts with amino-Ci-Ce alkanols, in particular with monoethanolamine, and amino-Ci-Ce alkanediols, in particular with 2-amino-2-methylpropan-1-ol, 2-amino-2-methylpropan-1,3-diol, 2-aminopropan-1-ol, 3-aminopropan-1-ol, 1-aminopropan-2-ol (MIPA), and 2-amino-2-(hydroxymethyl)propan-1,3-diol (TRIS), as well as the salts with alkali-reacting amino acids, such preferably arginine, lysine, ornithine, and histidine. Mixtures of these salts.Particularly preferred salts of succinic acid according to the invention are selected from the lithium, sodium, potassium, magnesium, calcium, and lanthanum salts, as well as mixtures thereof; most preferably selected from the sodium, potassium, magnesium, and lanthanum salts, as well as mixtures thereof. Disodium succinate is particularly preferred according to the invention.

[0031] In further keratin fiber treatment agents preferred according to the invention, the citric acid is present at least partially in salt form. Citric acid is a tribasic acid with pKa values ​​of 3.13 (pKa1), 4.76 (pKa2), and 6.4 (pKass). The extent to which citric acid is present in salt form in the aqueous environment of keratin fiber treatment agents preferred according to the invention therefore depends, among other things, on the pH value of the fiber treatment agent.The at least one salt of citric acid is selected from the alkali metal, alkaline earth metal, zinc, lanthanum, cerium, ammonium, alkylammonium, alkanolammonium and glucammonium salts, in particular the mono-, di- and trimethyl-, -ethyl and -hydroxyethylammonium salts, furthermore the salts with amino-Ci-Ce alkanes, in particular with monoethanolamine, and amino-Ci-Ce alkanediols, in particular with 2-amino-2-methylpropan-1-ol, 2-amino-2-methylpropan-1,3-diol, 2-aminopropan-1-ol, 3-aminopropan-1-ol, 1-aminopropan-2-ol (MIPA) and 2-amino-2-(hydroxymethyl)propan-1,3-diol (TRIS), 2024P00123WC.

[0032] 6, as well as salts containing alkali-reacting amino acids, preferably arginine, lysine, ornithine, and histidine, and mixtures of these salts. Particularly preferred salts of citric acid according to the invention are selected from the lithium, sodium, potassium, magnesium, calcium, and lanthanum salts, and mixtures thereof; most preferably selected from the sodium, potassium, magnesium, and lanthanum salts, and mixtures thereof. Trisodium citrate is particularly preferred according to the invention.

[0033] In summary, preferred treatment agents for keratin fibers according to the invention are characterized in that they contain at least one salt of succinic acid and / or citric acid, selected from the alkali metal, alkaline earth metal, zinc, lanthanum, cerium, ammonium, alkylammonium, alkanolammonium, and glucammonium salts, in particular the mono-, di-, and trimethyl, -ethyl, and -hydroxyethylammonium salts, furthermore the salts with amino-Ci-Ce alkanes, in particular with monoethanolamine, and amino-Ci-Ce alkane diols, in particular with 2-amino-2-methylpropan-1-ol, 2-amino-2-methylpropan-1,3-diol, 2-aminopropan-1-ol, 3-aminopropan-1-ol, 1-aminopropan-2-ol (MIPA), and 2-amino-2-(hydroxymethyl)propan-1,3-diol (TRIS), as well as the salts with alkali-reacting amino acids, such preferably arginine, lysine, ornithine and histidine, as well as mixtures of these salts, most preferably selected from the sodium, potassium, magnesium and lanthanum salts, as well as mixtures thereof.

[0034] In addition to citric acid and succinic acid in the specified quantitative ratios, the hair treatment products according to the invention contain at least one ketone compound of formula (I), R 1 -C(O)-CH2OH (I), wherein the residue R 1 for a straight-chain or branched, saturated or unsaturated alkyl group with 2 to 15, preferably with 3 to 8, particularly preferably with 5 to 6, extremely preferably with 6 carbon atoms.

[0035] Particularly preferred ketone compounds of general formula (I) according to the invention are linear. Further particularly preferred ketone compounds of general formula (I) according to the invention are selected from the linear compounds 1-hydroxy-2-pentanone, 1-hydroxy-2-hexanone, 1-hydroxy-2-heptanone, 1-hydroxy-2-octanone, 1-hydroxy-2-nonanone, 1-hydroxy-2-decanone, and mixtures thereof. Further particularly preferred ketone compounds of general formula (I) according to the invention are selected from 1-hydroxy-2-heptanone, 1-hydroxy-2-octanone, and mixtures thereof. 1-Hydroxy-2-octanone is especially preferred according to the invention.

[0036] Further treatment agents preferred according to the invention for keratin fibers are characterized in that the at least one compound selected from ketone compounds of formula (I), R 1 -C(O)-CH2OH (I), wherein the residue R 1for a straight-chain or branched, saturated or unsaturated alkyl group with 2 to 15, preferably with 3 to 8, particularly preferably with 5 to 6, extremely preferably with 6 carbon atoms, in a total amount of 0.01 to 5 wt.%, further preferably 0.05 to 2 wt.%, particularly preferably 0.1 to 1 wt.%, most preferably 2024P00123WG

[0037] 7 contains 0.2 to 0.7 wt.% and, most preferably, 0.2 to 0.5 wt.%, in each case based on the weight of the treatment agent.

[0038] According to the invention, the exceptionally preferred treatment agents for keratin fibers contain, based on their weight, 0.01 to 5 wt.%, more preferably 0.05 to 2 wt.%, particularly preferably 0.1 to 1 wt.%, most preferably 0.2 to 0.7 wt.% and exceptionally preferably 0.2 to 0.5 wt.% 1-hydroxy-2-octanone.

[0039] Water content

[0040] Further keratin fiber treatment agents preferred according to the invention contain, based on their weight, 40 to 95 wt.% water, particularly preferably 50 to 90 wt.%, more preferably 60 to 87 wt.%, more preferably 70 to 85 wt.%, and most preferably 75 to 80 wt.% water.

[0041] Further keratin fiber treatment agents preferred according to the invention contain, based on their weight, 0.01 to 40 wt.%, preferably 0.05 to 30 wt.% and in particular 0.1 to 25 wt.% of at least one alcohol. Suitable alcohols include, for example, ethanol, ethyl diglycol, 1-propanol, 2-propanol, isopropanol, 1,2-propylene glycol, glycerin, diglycerin, triglycerin, 1-butanol, 2-butanol, 1,2-butanediol, 1,3-butanediol, 1-pentanol, 2-pentanol, 1,2-pentanediol, 1,5-pentanediol, 1-hexanol, 2-hexanol, 1,2-hexanediol, 1,6-hexanediol, polyethylene glycols, sorbitol, sorbitan, benzyl alcohol, or mixtures of these alcohols. Water-soluble alcohols are particularly preferred. Ethanol, 1,2-propylene glycol, glycerin, benzyl alcohol, and mixtures of these alcohols are especially preferred.

[0042] The technical teaching according to the invention can be integrated into a variety of treatment products for keratin fibers. The acid-active ingredient combination used according to the invention can particularly preferably be included in rinse-off fiber treatment products for cleaning and care, such as shampoos, conditioners, hair rinses, hair masks, hair treatments, hair styling products, and hair dyes.

[0043] The aforementioned fiber treatment agents typically have an acidic pH value, which, on the one hand, smooths the outer scale layer of the keratin fibers, the cuticle, and on the other hand, also supports the improvement of the internal fiber structure of the keratin fibers and the repair of structural damage to the fibers. According to the invention, keratin fiber treatment agents, particularly those used solely for cleaning and / or conditioning the keratin fibers, are therefore most preferably to have a pH value in the range of 3.0 to 7.0, preferably 3.5 to 6.5, particularly preferably 4.0 to 6.0, further particularly preferably 4.5 to 5.5, and most preferably 4.9 to 5.2, in each case measured at 20°C.

[0044] Furthermore, it may be preferred that the acid-active ingredient combination used according to the invention is contained in a hair shaping agent or a hair dye. Hair shaping agents and most hair dyes, especially oxidative hair dyes, are also rinse-off fiber treatment agents and typically have a pH value in the weakly acidic to strongly alkaline range, since they work best when the cuticle is open. Further keratin fiber treatment agents that are particularly preferred according to the invention, especially hair shaping agents and hair dyes, particularly oxidative hair dyes, therefore have a pH value in the range of 6.5 to 11.0, preferably 7.0 to 10.5, particularly preferably 7.5 to 10.0, further particularly preferably 8.0 to 9.5, and most preferably 8.5 to 9.0, in each case measured at 20°C.

[0045] Furthermore, it may be preferred that the acid combination used according to the invention is contained in a permanent hair shaping agent. Permanent hair shaping agents are also rinse-off fiber treatments and typically have a pH value in the weakly acidic to strongly alkaline range, as they work best when the cuticle is open. Further keratin fiber treatment agents, particularly permanent hair shaping agents, that are especially preferred according to the invention therefore have a pH value in the range of 6.5 to 11.0, preferably 7.0 to 10.5, particularly preferably 7.5 to 10.0, further particularly preferably 8.0 to 9.5, and most preferably 8.5 to 9.0, in each case measured at 20°C.

[0046] Other preferred fiber treatment agents are non-oxidative dyes containing color pigments or direct dyes. These also frequently have a pH value in the range of 3.0 to 7.0, preferably 3.5 to 6.5, particularly preferably 4.0 to 6.0, further particularly preferably 4.5 to 5.5, and extremely preferably 4.9 to 5.2, in each case measured at 20°C.

[0047] In addition to rinse-out treatments for keratin fibers, there are also dosage forms that remain on the keratin fibers for at least several hours after application (leave-on), in particular hair treatments, leave-on treatments, hair serums, hair care sprays, leave-on conditioners, hairsprays, or hair styling products. Such leave-on fiber treatments also typically have an acidic pH. According to the invention, keratin fiber treatments that remain on the keratin fibers for at least several hours after application (leave-on), in particular hair treatments, hairsprays, and hair styling products, therefore preferably have a pH in the range of 3.0 to 7.0, preferably 3.5 to 6.5, particularly preferably 4.0 to 6.0, further particularly preferably 4.5 to 5.5, and most preferably 4.9 to 5.2, each measured at 20°C.

[0048] In summary, keratin fiber treatment agents preferred according to the invention are characterized in that they have a pH value in the range of 3.0 to 11.0, preferably 3.5 to 10.5, particularly preferably 4.0 to 10.0, further particularly preferably 4.5 to 9.5, and extraordinarily preferably 4.9 to 8.5, each measured at 20°C.

[0049] The terms "no-rinse" and "rinse-in" mean that the formula either remains in the hair for a relatively short time, for example, less than a minute if needed, or for a few minutes or an hour before being rinsed out, or that the formula stays in the hair until the next shampoo, which can be several days. Both have certain advantages. If the formula remains on the hair for a longer period, the 2024P00123WÖ

[0050] 9. The full conditioning potential of all ingredients is utilized, whereas a composition that is rinsed out quickly may also contain ingredients that have a good conditioning effect, but whose prolonged residence in the hair would be unpleasant. For the purposes of the present invention, rinse-out compositions are preferred.

[0051] Further keratin fiber treatment compositions preferred according to the invention are characterized in that they additionally contain at least one conditioning agent selected from natural oils, synthetic oils, mineral oils, natural cation polymers, in particular cationic guar, as well as mixtures of these conditioning agents. Particularly preferred keratin fiber treatment compositions according to the invention are characterized in that the at least one conditioning agent is contained in an amount of 0.0001 to 20 wt.%, preferably 0.001 to 15 wt.%, particularly preferably 0.01 to 10 wt.%, and most preferably 0.1 to 5 wt.%, in each case based on the weight of the treatment composition.

[0052] Natural oils

[0053] According to the invention, preferred natural oils are in particular selected from vegetable oils and vegetable butters. Particularly preferred vegetable oils according to the invention are selected from Abyssinian oil, amaranth seed oil, apricot kernel oil, argan oil, avocado oil, babassu oil, bamboo oil, cottonseed oil, borage seed oil, oamelina oil, safflower kernel oil, safflower oil, peanut oil, pomegranate seed oil, grapefruit seed oil, hemp oil, hazelnut oil, elderberry seed oil, blackcurrant seed oil, jojoba oil, cocoa butter, prickly pear oil, crambe seed oil, pumpkin seed oil, linseed oil, macadamia nut oil, corn germ oil, mallow oil, almond oil, mango kernel oil, marula oil, evening primrose oil, olive oil, orange oil, palm oil, peach kernel oil, quinoa oil, rambutan oil, rapeseed oil, rice bran oil, castor oil, sea buckthorn pulp oil, sea buckthorn kernel oil, Sasanquana oil, sesame oil, and shea butter. Soybean oil, sunflower oil, grapeseed oil, and mixtures thereof.

[0054] Particularly preferred are apricot kernel oil, argan oil, coconut oil, almond oil, marula oil, olive oil, the liquid components of (sweet) coconut oil, macadamia nut oil, olive oil, peach kernel oil, shea butter, sunflower oil or mixtures thereof.

[0055] According to the invention, preferred fiber treatment agents contain at least one natural oil in a weight fraction of 0.02 - 75 wt.%, more preferably 0.03 - 70 wt.%, particularly preferably 0.04 - 65 wt.%, more preferably 0.05 - 60 wt.%, more preferably 0.1 - 10 wt.% and extraordinarily preferably 0.2 - 1 wt.%, in each case based on the weight of the fiber treatment agent.

[0056] Synthetic oils and mineral oils

[0057] Preferred synthetic oils according to the invention are selected from silicone oils and from branched or unbranched alkanes with 10 to 30 carbon atoms, as well as mixtures thereof. Particularly preferred silicone oils according to the invention are selected from: 2024P00123WÖ

[0058] 10

[0059] (i) Polyalkylsiloxanes, polyarylsiloxanes, polyalkylarylsiloxanes, whether volatile or non-volatile, straight-chain, branched or cyclic, cross-linked or non-cross-linked;

[0060] (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) carboxyl groups; l) sulfonic acid groups; and m) sulfate or thiosulfate groups;

[0061] (iii) linear polysiloxane(A)-polyoxyalkylene(B) block copolymers of type (AB) n with n > 3;

[0062] (iv) grafted silicone polymers with a non-silicone organic backbone consisting of an organic main chain formed from organic monomers that do not contain silicone, onto which at least one polysiloxane macromer has been grafted in the chain and optionally at at least one chain end;

[0063] (v) grafted silicone polymers with a polysiloxane backbone onto which non-silicone-containing organic monomers have been grafted, the monomers having a polysiloxane main chain onto which at least one organic macromer, which does not contain silicone, has been grafted in the chain and optionally at at least one of its ends;

[0064] (vi) or mixtures thereof.

[0065] According to the invention, particularly preferred branched or unbranched alkanes with 10 to 30 carbon atoms are selected from isodecane, isosoundecane, isododecane, isotridecane, isotetradecane, C12-17 alkane and mixtures thereof.

[0066] According to the invention, particularly preferred mineral oils are selected from mineral oils, paraffin and isoparaffin oils, and synthetic hydrocarbons. Paraffins, especially liquid paraffins, and preferably paraffins with the INCI name Paraffinum Liquidum, are particularly preferred.

[0067] Preferred fiber treatment agents according to the invention contain at least one oil selected from synthetic oils and mineral oils, as well as mixtures thereof, in a weight fraction of 0.02–75 wt.%, more preferably 0.03–70 wt.%, particularly preferably 0.04–65 wt.%, more preferably 0.05–60 wt.%, more preferably 0.1–10 wt.%, and most preferably 0.2–1 wt.%, in each case based on the weight of the fiber treatment agent. 2024P00123WC

[0068] 11

[0069] Natural cation polymers, especially cationic guar

[0070] Suitable natural cation polymers within the meaning of the present invention include, for example, cationic polysaccharide polymers.

[0071] Cationic polysaccharide polymers can further enhance the conditioning performance of the hair treatment products according to the invention. Suitable cationic polysaccharide polymers can be selected from cationic cellulose compounds and / or from cationic guar derivatives.

[0072] Cationic cellulose compounds within the meaning of the invention are those that carry more than one permanent cationic charge in at least one side chain. Cellulose is composed of β-1,4-glycosidically linked D-glucopyranose units and forms unbranched, water-insoluble chains. A "side chain" of cellulose is defined as a chemical substituent that binds to the cellulose backbone and is not part of the native cellulose, as it was subsequently introduced, for example, by chemical synthesis.

[0073] Quaternized cellulose polymers derived from hydroxy (C2-C4) alkyl celluloses, particularly hydroxyethyl celluloses, are preferred. Such polymers are known to those skilled in the art and are commercially available from various companies. The cationic cellulose derivatives known under the INCI names Polyquaternium-4, Polyquaternium-10, Polyquaternium-24, Polyquaternium-67, and / or Polyquaternium-72 are particularly preferred. Polyquaternium-10, Polyquaternium-24, and / or Polyquaternium-67 are especially preferred, and Polyquaternium-10 is particularly preferred.

[0074] Suitable cationic guar derivatives according to the invention are cationic hydroxyalkyl guar derivatives, preferably cationic hydroxyethyltrimethylammonium guar and / or cationic hydroxypropyltrimethylammonium guar with average molecular weights between 100,000 and 2,000,000 Daltons. Particularly preferred are the cationic guar polymers known under the INCI names Guar Hydroxypropyltrimonium Chloride and / or Hydroxypropyl Guar Hydroxypropyltrimonium Chloride, with a molecular weight (average weight) 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 particularly at least 0.6 meq / g. Their nitrogen content is preferably in the range of 1.1 to 1.8 wt.% (based on their weight).

[0075] Cationic guar derivatives, known under the INCI names Guar Hydroxypropyltrimonium Chloride and Hydroxypropyl Guar Hydroxypropyltrimonium Chloride, are available from various suppliers under trade names such as Cosmedia® Guar, N-Hance®, Jaguar® and / or Polycare®.

[0076] Hair treatment products preferred according to the invention contain one or more natural cation polymer(s) - based on the weight of the product - in an amount of 0.01 to 5 wt.%, particularly preferably 0.02 to 3 wt.% and particularly 0.05 to 1 wt.%.

[0077] According to the invention, preferred hair treatment compositions may contain surfactant(s). In cleansing compositions (usually rinse-off compositions), anionic surfactants have proven particularly effective, while in conditioning compositions (rinse-off or leave-on) 2024P00123WC

[0078] 12

[0079] In compositions, cationic surfactants are frequently used ingredients; amphoteric and / or non-ionic surfactants and / or emulsifiers are used to particular advantage in both cleaning and care compositions due to their beneficial properties.

[0080] A preferred embodiment is characterized in that the hair treatment agent according to the invention is formulated as a cosmetic cleansing composition for the scalp and / or the hair and contains 0.1 - 75 wt.% of at least one anionic, amphoteric, zwitterionic, non-ionic surfactant or mixtures thereof.

[0081] Particularly preferred hair treatment products formulated as cleansing compositions contain > 50% of at least one anionic surfactant, based on the total surfactant content.

[0082] Further treatment agents for keratin fibers that are particularly preferred according to the invention are characterized in that the agent contains at least one surfactant, selected from anionic, nonionic, amphoteric and zwitterionic surfactants and mixtures thereof, in a total amount of 0.5 to 50.0 wt.%, preferably 1.0 to 30 wt.%, more preferably 2.0 to 25 wt.%, more preferably 4.0 to 20 wt.%, more preferably 5.5 to 15 wt.%, more preferably 7.0 to 10 wt.%, in each case based on the weight of the treatment agent.

[0083] All anionic surfactants suitable for cosmetic use on the human or animal body are suitable as anionic surfactants and emulsifiers for the hair treatment products according to the invention. These are characterized by a water-soluble anionic group, such as a carboxylate, sulfate, sulfonate, or phosphate group, and a lipophilic alkyl group with approximately 8 to 30 carbon atoms. Additionally, the molecule may contain glycol or polyglycol ether groups, ester, ether, and amide groups, as well as hydroxyl groups.

[0084] Particularly suitable anionic surfactant types that can be used in cosmetic products according to the invention include, for example: linear and branched fatty acids with 8 to 30 carbon atoms (soaps),

[0085] Ethercarboxylic acids of the formula RO-(CH2-CH2O) X-CH2-COOH, in which R is a linear or branched, saturated or unsaturated alkyl group with 8 to 30 C atoms and x = 0 or 1 to 16,

[0086] Acyl sarcosides with 8 to 24 carbon atoms in the acyl group (sarcosinate surfactants), acyl taurides with 8 to 24 carbon atoms in the acyl group (taurate surfactants), acyl isethionates with 8 to 24 carbon atoms in the acyl group (isethionate surfactants), acyl glutamates with 8 to 24 carbon atoms in the acyl group (glutamate surfactants), sulfosuccinic acid mono- and / or dialkyl esters with 8 to 24 carbon atoms in the alkyl group, and sulfosuccinic acid monoalkyl polyoxyethyl esters with 8 to 24 carbon atoms in the alkyl group and 1 to 6 oxyethyl groups (sulfosuccinate surfactants), 2024P00123WÖ

[0087] 13

[0088] Alpha-olefin sulfonates with 8 to 24 carbon atoms (alpha-olefin sulfonate surfactants),

[0089] Alkyl sulfates and / or alkyl ether sulfate salts of the formula R-(OCH2-CH2)nO-SO3X, in which R preferably represents a straight-chain or e, saturated or unsaturated alkyl group with 8 to 30 C atoms, x the number 0 or 1 to 12 and X an alkali, alkaline earth, ammonium or alkanolamine ion,

[0090] Sulfonates of unsaturated fatty acids with 8 to 24 carbon atoms and 1 to 6 double bonds,

[0091] Esters of tartaric acid and citric acid with alcohols, which are addition products of approximately 2-15 molecules of ethylene oxide and / or propylene oxide to fatty alcohols with 8 to 22 carbon atoms, and / or

[0092] Alkyl and / or alkenyl ether phosphates of the formula in the R 1 preferably for an aliphatic hydrocarbon residue with 8 to 30 carbon atoms, R 2 for hydrogen, a residue (CH2CH20) n R 1 or X, n for numbers from 0 to 10 and X for hydrogen, an alkali or alkaline earth metal or the group -NR3 R 4 R 5 R 6 stands, with R 3 to R 6 Independently representing a C1 to C4 hydrocarbon residue.

[0093] Particularly preferred are alkyl sulfate and / or alkyl ether sulfate salts, (salts of) ether carboxylic acids, sarcosinates, isethionates, taurates, sulfosuccinates and / or alpha-olefin sulfonates, especially alkyl sulfate and / or alkyl ether sulfate salts.

[0094] Particularly preferred are alkyl(ether) sulfates of the general formula R-(OCH2-CH2) n -OSO3X, in which R is a straight-chain or e, saturated or unsaturated alkyl group with 8 to 24 C atoms, n is the number 0 or 1 to 12, and X is an alkali, alkaline earth, ammonium or alkanolamine ion.

[0095] Other particularly suitable anionic surfactant types that can be used in cosmetic products according to the invention include biosurfactants. These are substances produced by microorganisms and often also secreted from the cell. Like conventional surfactants, biosurfactants are surface-active substances that reduce the surface tension of liquids and thereby promote the mixing of aqueous (hydrophilic) and water-repellent (hydrophobic) phases. Biosurfactants can be produced under mild production conditions that require low energy consumption. They are generally readily biodegradable and have a very high level of environmental compatibility. Furthermore, they are non-toxic, and no toxic byproducts are generated during their production. Carbohydrates, especially sugars such as, for example, [examples of sugars], are used as raw materials for their microbial production.Glucose and / or lipophilic carbon sources such as fats, oils, partial glycerides, fatty acids, fatty alcohols, and long-chain saturated or unsaturated hydrocarbons are used. According to the invention, the biosurfactants are preferably those produced by fermentation. Biosurfactants include glycolipids, lipopeptides, lipoproteins, fatty acids, phospholipids, neutral lipids, and polymeric surfactants (e.g., Emulsan), all of which can also be used in the present invention.

[0096] Glycolipids that can be used in the present invention are compounds in which one or more monosaccharide units are glycosidically linked to a lipid moiety. Examples of glycolipids that can be used as biosurfactants according to the invention are rhamnolipids, sophorolipids, mannosylerythritol lipids, and trehalose lipids. Among these, rhamnolipids, sophorolipids, mannosylerythritol lipids, and combinations thereof are preferred.

[0097] Biosurfactants include the group of substances known as lipids and lipid derivatives, which particularly include lipopeptides. Lipopeptides are typically synthesized non-ribosomally by microorganisms, such as Gram-positive bacteria, especially those of the genera Bacillus and Streptomyces; Gram-negative bacteria, especially those of the genus Pseudomonas and Myxobacteria; and filamentous fungi. The peptide chains usually consist of two to forty amino acids and can be linear, cyclic, or branched. Unlike ribosomally synthesized peptide chains, their monomeric building blocks often consist not only of proteinogenic L-amino acids, but also of D-amino acids, carboxylic acids, and / or alpha-hydroxy acids of all kinds. The amino acids are mostly La- or D-alpha-amino acids, but β-, γ-, or δ-amino acids may also be present, which can likewise exist in D- or L-configuration.The peptide chains can also exhibit further chemical modifications; in particular, they can be glycosylated, hydrolyzed, N-methylated, or N-formylated. Frequently occurring structural elements also include thiazoline and / or oxazoline rings in various oxidation states. A well-known lipopeptide biosurfactant is surfactin.

[0098] Further treatment agents for keratin fibers that are particularly preferred according to the invention are characterized in that the agent contains at least one anionic surfactant in a total amount of 0.5 to 50.0 wt.%, preferably 1.0 to 30 wt.%, more preferably 2.0 to 25 wt.%, more preferably 4.0 to 20 wt.%, more preferably 5.5 to 15 wt.%, more preferably 7.0 to 10 wt.%, in each case based on the weight of the treatment agent.

[0099] The hair treatment products according to the invention can contain at least one amphoteric or zwitterionic surfactant and / or at least one non-ionic surfactant.

[0100] Preferably, hair treatment products according to the invention, which are formulated as a cleaning composition, contain 0-50%, particularly preferably 1-40% and in particular 5-30% of at least one amphoteric or zwitterionic surfactant and / or 0-50%, particularly preferably 1-40% and in particular 5-30% of at least one non-ionic surfactant, in each case based on the total surfactant content.

[0101] Suitable zwitterionic or amphoteric surfactants are those that carry both a cationic and an anionic charge in the molecule. Preferably, amphoteric surfactants have at least one quaternary ammonium group and at least one -COO' or -SOs' group, in addition to a preferred 2024P00123WC

[0102] 15 incorporates a C8-C24 alkyl or acyl group into the molecule. Furthermore, they are capable of forming internal salts. Particularly preferred amphoteric surfactants are betaines such as the N-alkyl-N,N-dimethylammonia glycinates, for example, cocoalkyldiethylammonium glycinate, N-acylaminopropyl-N,N-dimethylammonium glycinate, for example, cocoacylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethyl-imidazolines, each with 8 to 18 carbon atoms in the alkyl or acyl group, as well as cocoacylaminoethylhydroxyethylcarboxymethyl glycinate. Particularly preferred are the amphoteric or zwitterionic surfactants known under the INCI names cocamidopropyl betaine, lauramidopropyl betaine, cocoampho(di)acetate, and / or lauroampho(di)acetate.

[0103] Further treatment agents for keratin fibers that are particularly preferred according to the invention are characterized in that the agent contains at least one zwitterionic or amphoteric surfactant in a total amount of 0.1 to 30.0 wt.%, preferably 0.5 to 15.0 wt.%, more preferably 1.0 to 10.0 wt.%, more preferably 2.0 to 8.0 wt.%, more preferably 3.0 to 6.0 wt.%, in each case based on the weight of the treatment agent.

[0104] Suitable non-ionic surfactants and / or emulsifiers may be selected from amine oxides such as the compounds known under the INCI names Cocamine Oxide, Lauramine Oxide and Coc- amidopropylamine oxide, fatty acid alkanolamides such as the compounds known under the INCI names Cocamide MEA and Coamide DEA, mixtures of alkyl l-(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.

[0105] Further treatment agents for keratin fibers that are particularly preferred according to the invention are characterized in that the agent contains at least one non-ionic surfactant in a total amount of 0.1 to 30.0 wt.%, preferably 0.5 to 15.0 wt.%, more preferably 1.0 to 10.0 wt.%, more preferably 2.0 to 8.0 wt.%, more preferably 3.0 to 6.0 wt.%, in each case based on the weight of the treatment agent.

[0106] The hair treatment products according to the invention may contain cationic surfactant(s).

[0107] Preferably, hair treatment products according to the invention, which are formulated as care compositions (hair conditioners), contain at least one cationic surfactant.

[0108] According to the invention, cationic surfactants of the type of quaternary ammonium compounds, esterquats, amidoamines, or mixtures thereof can be used. Preferred quaternary ammonium compounds are ammonium halides, in particular chlorides and bromides, such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides, and trialkylmethylammonium chlorides. The long alkyl chains of these surfactants preferably have 10 to 18 carbon atoms, as in cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride, and tricetylmethylammonium chloride. Other preferred cationic surfactants are the imidazolium compounds known under the INCI names Quaternium-27 and Quaternium-83.

[0109] Particularly preferred hair treatment compositions according to the invention – especially cosmetic compositions for the care of hair and / or scalp – contain – based on their weight – preferably 0.05 to 10 wt.%, more preferably 0.1 to 7.5 wt.%, and more preferably 0.25 to 5.0 wt.% cationic surfactant(s). Hair treatment compositions according to the invention most preferably contain cationic surfactants from the group of quaternary ammonium compounds and / or esterquats and / or amidoamines in the aforementioned amounts. Further particularly preferred treatment compositions for keratin fibers according to the invention are characterized in that the composition contains at least one cationic surfactant in a total amount of 0.05 to 10.0 wt.%, preferably 0.1 to 7.5 wt.%, more preferably 0.25 to 5.0 wt.%, and more preferably 0.5 to 3.5 wt.%, in each case based on the weight of the treatment composition.

[0110] The repairing and restructuring effect of the acid-active ingredient combinations according to the invention also occurs in the presence of oxidizing agents, in particular in the presence of peroxide compounds commonly used as oxidizing agents in hair treatment products, which are different from atmospheric oxygen. However, for the purposes of the present invention, treatment products for keratin fibers that are free of peroxide compounds different from atmospheric oxygen are preferred. Peroxide compounds commonly used as oxidizing agents in hair cosmetics include hydrogen peroxide, persulfates, perbromates, percarbonates, perborates, and percarbamides. The oxygen contained in ambient air does not constitute an oxidizing agent in the context of the invention.

[0111] The repairing and restructuring effect of the acid-active ingredient combinations according to the invention also occurs in the presence of reducing agents, in particular in the presence of compounds commonly used as reducing agents in hair treatment products. Compounds commonly used as reducing agents in hair cosmetics include thioglycolic acid, thiolactic acid, L-cysteine, N-acetylcysteine, cysteamine and the salts of the aforementioned compounds, as well as sulfites, in particular sodium sulfite, hydrogen sulfites, in particular sodium hydrogen sulfite, and metabisulfites, in particular sodium metabisulfite, and mixtures of these keratin-reducing compounds.

[0112] A further object of the present invention is a method for improving the fiber structure of keratin fibers, in particular of hair, in particular for increasing the melting temperature of the keratin fiber, in particular of hair, as measured by differential scanning calorimetry (DSC), in which a treatment agent for keratin fibers, containing in a cosmetically compatible carrier 2024P00123WC

[0113] 17 a) Succinic acid and citric acid, wherein each of these acids may be present independently in salt form and wherein the total amount of succinic acid and citric acid is 1 to 5 wt.%, converted to the free acid content and based on the weight of the fiber treatment agent, and wherein succinic acid (BS) and citric acid (CS) are present in a weight ratio BS / CS to each other of 0.400 to 2.500, preferably 0.70 to 2.20, particularly preferably 0.80 to 1.60, in each case converted to the free acids, in combination with b) at least one compound selected from at least one ketone compound of formula (I), R 1 -C(O)-CH2OH(I), wherein the residue R 1for a straight-chain or branched, saturated or unsaturated alkyl group with 2 to 15, preferably with 3 to 8, particularly preferably with 5 to 6, extraordinarily preferably with 6 carbon atoms, is applied to the keratin fibers and is optionally rinsed out of the keratin fibers after an exposure time of one second to 4 hours, preferably after an exposure time of 1 to 60 minutes, more preferably after 5 to 45 minutes, particularly preferably after 10 to 30 minutes, extraordinarily preferably after 15 to 20 minutes.

[0114] The present invention also relates to a method for improving the fiber structure of keratin fibers, particularly hair, comprising the application of a treatment agent for keratin fibers according to the invention to keratin fibers. The method includes applying the treatment agent disclosed herein to keratin fibers, preferably to the hair. A preferred method involves dispensing the treatment agent disclosed herein directly from a container, such as a spray dispenser or a bottle with or without a metering attachment, onto the keratin fibers, particularly the hair. Another preferred method involves dispensing the treatment agent disclosed herein onto the user's hand and from the user's hand onto the keratin fibers, preferably the hair. The method may additionally include rubbing or massaging the keratin fibers, preferably the hair.The procedure may involve the user distributing the treatment agent in their hand or hands before applying it to the keratin fibers, preferably the hair.

[0115] The method disclosed herein may also include additional, optional steps. For example, such steps may include air-drying the hair, drying the hair using heat, styling the hair, and any other suitable step known to a professional in the field of hair treatment.

[0116] Preferred treatment agents for keratin fibers according to the invention serve for the surfactant treatment of the keratin fibers, for example in a process for cleaning the keratin fibers. Further preferred treatment agents according to the invention serve for the oxidative treatment of the keratin fibers, for example in a process for fixing a permanent corrugation or permanent- 2024P00123WG

[0117] 18. The treatment agents preferred according to the invention are used for the smoothing of keratin fibers or for the permanent coloring or lightening of keratin fibers. Further treatment agents preferred according to the invention serve for the reducing treatment of keratin fibers, for example in a process for permanent crimping or for the permanent smoothing of keratin fibers. In addition, treatment agents preferred according to the invention can be used immediately before, during or immediately after an oxidative, reducing or surfactant treatment of keratin fibers.In the context of the invention, the expression "immediately before an oxidative, reducing or surfactant hair treatment" is understood as an application immediately preceding the oxidative, reducing or surfactant hair treatment, i.e., within a period of one second to 60 minutes, wherein in a first embodiment the fiber treatment agent according to the invention was rinsed out of the keratin fibers, preferably from the hair, before the application of the oxidative, reducing or surfactant agent, or in a further embodiment preferably left in the keratin fibers, preferably in the hair, before the application of the oxidative, reducing or surfactant agent, and wherein the keratin fibers, preferably the hair, are preferably still moist.

[0118] In the context of the invention, the expression "immediately after an oxidative, reducing or surfactant hair treatment" is understood as an application immediately following the oxidative, reducing or surfactant hair treatment, i.e., within a period of one second to four hours, wherein in a first embodiment the fiber treatment agent according to the invention is rinsed out of the keratin fibers, preferably from the hair, after application, or in a further embodiment preferably remains in the keratin fibers, preferably in the hair.

[0119] In the context of the invention, the expression "during an oxidative, reducing, or surfactant hair treatment" is understood to mean that the fiber treatment agent according to the invention is applied to the keratin fibers, preferably from the hair, simultaneously with the oxidative, reducing, or surfactant hair treatment. In a first such embodiment, a fiber treatment agent according to the invention and an oxidative, reducing, or surfactant hair treatment agent are applied simultaneously to the keratin fibers, preferably to the hair. In a further embodiment, a fiber treatment agent according to the invention is first mixed with an oxidative, reducing, or surfactant hair treatment agent, and then this mixture is applied to the keratin fibers, preferably to the hair.

[0120] The method disclosed herein may also include additional, optional steps. For example, such steps may include air-drying the keratin fibers, preferably the hair; drying the keratin fibers, preferably the hair, using heat; styling the keratin fibers, preferably the hair; and any other suitable step known to a person skilled in the field of keratin fiber treatment, preferably hair treatment. 2024P00123WC

[0121] 19

[0122] The statements made regarding the treatment agents for keratin fibers according to the invention and those preferred according to the invention apply mutatis mutandis to the aforementioned method according to the invention for improving the fiber structure of keratin fibers.

[0123] A further object of the present invention is the use of a treatment agent for keratin fibers, in particular a hair treatment agent, containing in a cosmetically compatible carrier a) succinic acid and citric acid, wherein each of these acids may be present independently of one another in salt form and wherein the total amount of succinic acid and citric acid is 1 to 5 wt.%, converted to the free acid content and based on the weight of the fiber treatment agent, and wherein succinic acid (BS) and citric acid (CS) are present in a weight ratio BS / CS to each other of 0.400 to 2.500, preferably 0.70 to 2.20, particularly preferably 0.80 to 1.60, in each case converted to the free acids, in combination with b) at least one compound selected from at least one ketone compound of formula (I), R 1 -C(O)-CH2OH(I), wherein the residue R 1for a straight-chain or branched, saturated or unsaturated alkyl group with 2 to 15, preferably with 3 to 8, particularly preferably with 5 to 6, extraordinarily preferably with 6 carbon atoms, for improving the fiber structure of keratin fibers, in particular for increasing the melting temperature of the keratin fiber measured by means of Differential Scanning Calorimetry (DSC), in particular the melting temperature of the hair.

[0124] What has been said about the treatment agents for keratin fibers according to the invention and the treatment agents preferred according to the invention applies mutatis mutandis to the aforementioned use according to the invention.

[0125] The following examples are intended to describe the invention in concrete terms, without limiting it to this.

[0126] Examples

[0127] Unless otherwise stated, all quantities are given as % active substance by weight.

[0128] All pH values ​​were determined at 20°C.

[0129] 1. Proof of efficacy a) Pretreatment

[0130] Strands of hair from Alkinco (0.5g, code 6634, natural dark European hair, A25) were cleaned with a 3 wt% solution of sodium laureth sulfate (2 EO) in deionized water with a pH of 6-7. 2024P00123WC

[0131] 20

[0132] Subsequently, all strands except those for the untreated reference (hereinafter referred to as "untreated") were bleached with a strong bleaching agent for 45 minutes, then washed, dried, and stored for at least 48 hours before the next treatment. b) Treatment with the test compositions b)i) aqueous acid solution as test composition

[0133] The strands were each immersed in the test composition for 15 minutes at a temperature of 23°C. Afterwards, each strand was rinsed with warm tap water for 20 seconds, blow-dried at 70°C, and left to rest for 16 hours. b)ii) Conditioner or shampoo as test composition

[0134] One gram of the product under test (conditioner or shampoo) per gram of hair was applied to the damp strands and thoroughly worked in. After two minutes, the hair strands were rinsed with warm tap water for 20 seconds and finally blow-dried at 70°C for 15 minutes. c) Demonstration of the hair-structuring effect using HP-DSC (Differential Scanning Calorimetry) c)i) Background

[0135] Hair is a keratin material with a complex morphological microstructure. For mechanical or thermal analyses, the structure can be simplified to a two-phase filament-matrix composite, in which α-helical filaments are embedded in an amorphous matrix. These two dominant compounds largely determine the mechanical properties of human hair and play a crucial role in the performance and effectiveness of cosmetic hair treatments.

[0136] An indicator of damage to or integrity of both the matrix and the α-helix is ​​the melting temperature of the hair, determined by DSC. The looser (less cross-linked) the matrix or the smaller the crystals of the α-helical phase, the lower the melting temperature of the keratin. c)ii) Test procedure

[0137] To determine the DSC peak temperature, all strands were cut into approximately 1 mm long pieces. Twelve aliquots per product and per reference were placed in the DSC crucibles. After adding 50 L of deionized water, each crucible was sealed. The measurement was performed in a temperature range of 100–190°C at a heating rate of 10 Kelvin per minute. The denaturation temperature was determined in °C. 2024P00123WC

[0138] 21 c)iii) Results

[0139] The DSC peak temperatures shown in the following tables were determined using DSC analysis (Perkin Eimer DSC 8000).

[0140] Table 1: Results of the DSC measurements

[0141] Results:

[0142] Strands damaged by ultra-bleaching have the lowest melting point. All acids, including hydrochloric acid, cause at least a slight increase in the melting point. This means that all acids improve the keratin structure of the damaged strands. However, only with the inventive mixtures of succinic acid and citric acid is at least the melting point of undamaged hair achieved. With the mixtures of succinic acid and citric acid, higher keratin melting points are achieved than with the individual acids at the same concentration; that is, there is a synergistic enhancement of the effect. The melting point achieved with 3.2 wt% succinic acid can also be achieved with mixtures of succinic acid and citric acid whose total acid concentration is significantly lower at 2.2 wt%. This also demonstrates the surprising synergistic effect.

[0143] Table 2: Results of the DSG measurements

[0144] The series of measurements shown in Table 2 demonstrates that all tested aliphatic organic acid mixtures in aqueous solution caused an extraordinary increase in the melting temperature compared to both damaged and untreated hair. This proves the absolute strengthening of the undamaged keratin structure of the hair by the acid mixtures according to the invention.

[0145] Table 3: Results of the DSC measurements

[0146] The measurement series shown in Table 3 demonstrates that all tested aliphatic organic acids in the shampoo base resulted in a significant increase in the melting temperature compared to hair damaged by ultra-bleaching. All tested organic acids thus exhibited a repair effect. The mixtures of succinic and citric acids achieve higher keratin melting temperatures than the individual acids at the same concentration, indicating a synergistic enhancement of the effect and increased structural improvement of the keratin fibers. 2024P00123WC

[0147] 23

[0148] In particular, a synergistic effect of succinic acid and citric acid is evident, as the succinic acid / citric acid mixtures with a total acid content of 2.2 wt.% achieve higher melting temperatures than 2.2 wt.% succinic acid as a single substance or 2.2 wt.% citric acid as a single substance.

[0149] Table 4: Composition of the tested conditioner base (amounts in wt% active substance)

[0150] Table 5: Composition of the tested shampoo base (wt% active substance) Tables 6 and 7 show hair treatment products according to the invention.

[0151] Table 6: Conditioner (amounts in wt% active substance)

[0152] Table 7: Shampoo (amounts in wt% active substance)

Claims

2024P00123WC 25 Patent claims 1. Treatment agent for keratin fibers, in particular for hair, for improving the fiber structure, containing succinic acid and citric acid in a cosmetically compatible carrier, wherein each of these acids may be present independently of one another in salt form and wherein the total amount of succinic acid and citric acid is 1 to 5 wt.%, converted to the free acid content and based on the weight of the fiber treatment agent, characterized in that succinic acid (BS) and citric acid (CS) are present in a weight ratio BS / CS to each other of 0.400 to 2.500, preferably 0.70 to 2.20, particularly preferably 0.80 to 1.60, in each case converted to the free acids, further characterized in that additionally at least one compound, selected from at least one ketone compound of formula (I), R 1 -C(O)-CH2OH (I), wherein the residue R 1represents a straight-chain or branched, saturated or unsaturated alkyl group with 2 to 15 carbon atoms.

2. Treatment agent for keratin fibers according to claim 1, characterized in that the total amount of succinic acid and citric acid, including any salts of these acid(s) contained, is 1.2 to 3.5 wt.%, preferably 1.5 to 3.0 wt.%, more preferably 1.7 to 2.5 wt.%, particularly preferably 1.8 to 2.4 wt.%, and most preferably 1.9 to 2.2 wt.%, in each case converted to the free acid content and based on the weight of the fiber treatment agent.

3. Treatment agent for keratin fibers according to one of claims 1 or 2, characterized in that the total amount of succinic acid, including any salts of succinic acid contained, is 0.3 to 2.5 wt.%, preferably 0.5 to 2.0 wt.%, more preferably 0.7 to 1.7 wt.%, particularly preferably 0.9 to 1.6 wt.%, more preferably 1.0 to 1.5 wt.%, and most preferably 1.3 to 1.5 wt.%, in each case converted to the free acid content and based on the weight of the fiber treatment agent.

4. Treatment agent for keratin fibers according to any one of claims 1 to 3, characterized in that the total amount of citric acid, including any salts of citric acid contained, is 0.1 to 4.0 wt.%, preferably 0.3 to 3.0 wt.%, more preferably 0.5 to 1.5 wt.%, particularly preferably 0.6 to 1.3 wt.%, extraordinarily preferably 0.7 to 1.2 wt.%, and extraordinarily preferably 0.8 to 1.0 wt.%, in each case converted to the free acid content and based on the weight of the fiber treatment agent.

5. Treatment agent for keratin fibers according to any one of claims 1 to 4, characterized in that it contains at least one salt of succinic acid and / or citric acid, 2024P00123WC 26 selected from the alkali metal, alkaline earth metal, zinc, lanthanum, cerium, ammonium, alkylammonium, alkanolammonium and glucammonium salts, in particular the mono-, di- and trimethyl-, -ethyl- and -hydroxyethylammonium salts, furthermore the salts with amino-Ci-Ce alkanols, in particular with monoethanolamine, and amino-Ci-Ce alkanediols, in particular with 2-amino-2-methylpropan-1-ol, 2-amino-2-methylpropan-1,3-diol, 2-aminopropan-1-ol, 3-aminopropan-1-ol, 1-aminopropan-2-ol (MIPA) and 2-amino-2-(hydroxymethyl)propan-1,3-diol (TRIS), as well as the salts with alkali-reacting amino acids, such preferably arginine, lysine, ornithine and histidine, as well as mixtures of these salts, exceptionally preferred selected from the sodium, potassium, magnesium and lanthanum salts and mixtures thereof.

6. Treatment agent for keratin fibers according to any one of claims 1 to 5, characterized in that the ketone compound of formula R 1-C(O)-CH2OH is selected from the linear compounds 1-hydroxy-2-pentanone, 1-hydroxy-2-hexanone, 1-hydroxy-2-heptanone, 1-hydroxy-2-octanone, 1-hydroxy-2-nonanone, 1-hydroxy-2-decanone and mixtures thereof, preferably selected from 1-hydroxy-2-heptanone, 1-hydroxy-2-octanone and mixtures thereof, most preferably selected from 1-hydroxy-2-octanone.

7. Treatment agent for keratin fibers according to any one of claims 1 to 6, characterized in that the at least one compound selected from ketone compounds of formula (I) is contained in a total amount of 0.01 to 5 wt.%, more preferably 0.05 to 2 wt.%, particularly preferably 0.1 to 1 wt.%, very preferably 0.2 to 0.7 wt.% and extraordinarily preferably 0.2 to 0.5 wt.%, in each case based on the weight of the treatment agent.

8. Treatment agent for keratin fibers according to any one of claims 1 to 7, characterized in that the agent has a pH value in the range of 3.0 to 11.0, preferably 3.5 to 10.5, particularly preferably 4.0 to 10.0, further particularly preferably 4.5 to 9.5, extraordinarily preferably 4.9 to 8.5, each measured at 20°C.

9. Treatment composition for keratin fibers according to any one of claims 1 to 8, characterized in that it is selected from rinse-off hair treatment compositions, such preferably a shampoo, a conditioner, a hair rinse, a hair mask, a hair treatment, a hair shaping agent or a hair coloring agent, and from leave-on hair treatment compositions, such preferably a hair treatment, a leave-on conditioner, a hair serum, a hair care spray, a leave-on conditioner, a hair fixative or a hair styling agent.

10. Treatment agent for keratin fibers according to any one of claims 1 to 9, characterized in that the agent comprises at least one surfactant selected from anionic, nonionic, 2024P00123WC 27 amphoteric and zwitterionic surfactants and mixtures thereof, in a total amount of 0.5 to 50.0 wt.%, preferably 1.0 to 30 wt.%, more preferably 2.0 to 25 wt.%, more preferably 4.0 to 20 wt.%, more preferably 5.5 to 15 wt.%, more preferably 7.0 to 10 wt.%, in each case based on the weight of the treatment agent.

11. Treatment agent for keratin fibers according to any one of claims 1 to 10, characterized in that the agent contains at least one cationic surfactant in a total amount of 0.05 to 10.0 wt.%, preferably 0.1 to 7.5 wt.%, particularly preferably 0.25 to 5.0 wt.%, in each case based on the weight of the treatment agent.

12. Treatment agent for keratin fibers according to any one of claims 1 to 11, characterized in that the agent is free of peroxide compounds that are different from atmospheric oxygen.

13. Method for improving the fiber structure of keratin fibers, in particular hair, especially for increasing the melting temperature of the keratin fiber, in particular hair, as measured by differential scanning calorimetry (DSC), in which a treatment agent for keratin fibers, containing in a cosmetically compatible carrier a) succinic acid and citric acid, wherein each of these acids may be present independently in salt form and wherein the total amount of succinic acid and citric acid is 1 to 5 wt.%, converted to the free acid content and based on the weight of the fiber treatment agent, and wherein succinic acid (BS) and citric acid (CS) are present in a weight ratio BS / CS to each other of 0.400 to 2.500, preferably 0.70 to 2.20, particularly preferably 0.80 to 1.60, in each case converted to the free acids, in combination with b) at least one compound selected from at least one ketone compound of formula (I), R1 -C(O)-CH2OH (I), wherein the residue R 1 stands for a straight-chain or branched, saturated or unsaturated alkyl group with 2 to 15 carbon atoms, is applied to the keratin fibers and optionally rinsed out of the keratin fibers after an exposure time of one second to 4 hours.

14. Use of a treatment agent for keratin fibers, in particular a hair treatment agent, containing in a cosmetically compatible carrier a) succinic acid and citric acid, wherein each of these acids may be present independently of one another in salt form and wherein the total amount of succinic acid and citric acid is 1 to 5 wt.%, converted to the free acid content and based on the weight of the treatment agent, and wherein succinic acid (BS) and citric acid (CS) are present in a weight ratio BS / CS to each other of 0.400 to 2.500, preferably 2024P00123WC 28 0.70 to 2.20, particularly preferably 0.80 to 1.60, are present, each converted to the free acids, in combination with b) at least one compound selected from at least one ketone compound of formula (I), R 1 -C(O)-CH2OH (I), wherein the residue R 1 stands for a straight-chain or branched, saturated or unsaturated alkyl group with 2 to 15 carbon atoms, for improving the fiber structure of keratin fibers, in particular for increasing the melting temperature of the keratin fiber measured by Differential Scanning Calorimetry (DSC), especially the melting temperature of the hair.

15. Method according to claim 13 or use according to claim 14, characterized in that the fiber treatment agent is designed as in any one of claims 2 - 12.

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