HYBRIDQUATS FOR HAIR TREATMENT

Description

Field of the invention

[0001] The invention relates to compositions containing A) at least one hybrid quat and B) at least one fatty alcohol. State of the art

[0002] Alkyl quats and ester quats are used in cosmetic formulations as hair conditioning agents. Both have certain disadvantages: Alkyl quats, especially dialkyl quats, are generally poorly biodegradable and pollute the environment. Ester quats, especially TEA ester quats, are sensitive to hydrolysis and therefore have limited use in aqueous formulations.

[0003] It has now been shown that alkyl ester quats (hybrid quats) consisting of an ammonium salt with at least one fatty alkyl chain and at least one ester group esterified with fatty acid have excellent conditioning properties and at the same time do not have the disadvantages of alkyl quats or ester quats.

[0004] In addition, it was surprisingly found that the alkyl ester quats are able to build up exceptionally high viscosities in formulations containing fatty alcohol.

[0005] DE3623215 discloses hair cosmetic compositions containing highly ethoxylated hybrid quats and fatty alcohol.

[0006] DE2928603 discloses hybridquats and their use as fabric softeners. The DE 0 2010 029 606 A1 and DE10 2010 029 610 A1 also disclose hybrid quats.

[0007] The object of the invention was to provide alternative hair conditioning agents based on quaternized ammonium compounds. Description of the invention

[0008] Surprisingly, it was found that the hybrid quats described below are able to solve the problem set by the invention.

[0009] The present invention therefore relates to compositions containing certain hybrid quats and fatty alcohol.

[0010] Another object of the invention is the use of the specific hybrid quats for conditioning skin and keratin fibers, in particular hair.

[0011] Another object of the invention is the use of the hybrid quats to increase the viscosity of fatty alcohol-containing compositions.

[0012] Another object of the present invention is the use of the hybrid quats as emulsifier, in particular cationic emulsifier, in preferably cosmetic formulations.

[0013] An advantage of the present invention is that the composition according to the invention can be provided predominantly on the basis of natural raw materials.

[0014] A further advantage is that the hybrid quats used have improved hydrolysis stability.

[0015] A further advantage is that the hybrid quats used have improved thermal stability.

[0016] Another advantage of the present invention is that good conditioning performance can be achieved without negative influence on the formulation viscosity.

[0017] Another advantage is that the hybrid quats used are extremely easy to process. They can be used in a wide variety of different formulations.

[0018] A further advantage is that the hybrid quats used significantly increase the viscosities of fatty alcohol-based suspensions, such as those commonly used in conditioner rinse formulations, compared to alkyl quats and ester quats. This allows the fatty alcohol content to be reduced, which lowers the overall cost of the formulation.

[0019] A further advantage is that the hybrid quats used sufficiently stabilize the fatty alcohol-based suspensions even without an additional emulsifier.

[0020] A further advantage is that the hybrid quats used can also be used in shampoos and have a conditioning effect.

[0021] A further advantage is that the hybrid quats used have good biodegradability.

[0022] Another advantage of the present invention is that the shine of the treated keratin fibers is increased.

[0023] A further advantage of the present invention is that the hybrid quats used have a good effect even when used in small quantities.

[0024] A further advantage is that the hybrid quats used have little ecological impact.

[0025] Another advantage is that the hybrid quats used on keratin fibers are easier to rinse out than previously known quaternary ester compounds.

[0026] Another advantage of the present invention is that the hybrid quats used do not crystallize.

[0027] Another advantage of the present invention is that it protects hair dyes from washing out.

[0028] Another advantage of the present invention is that the hybrid quats are easier to formulate.

[0029] Another advantage of the present invention is that it reduces the hybrid quats combing forces on wet and dry hair.

[0030] A further advantage is that the hybrid quats used can be used in high active ingredient concentrations.

[0031] Another advantage of the present invention is that the hybrid quats used as emulsifiers in O / W emulsions provide an excellent skin feel.

[0032] Another advantage of the present invention is that it is particularly economical.

[0033] Another advantage of the present invention is that the formulations containing the hybrid quats have antistatic properties.

[0034] The present invention relates to compositions containing A) at least one hybrid quat of the general formula I) with R 1< a hydrocarbon radical having 10 to 32 carbon atoms, preferably 12 to 22 carbon atoms, in particular 16 to 18 carbon atoms, R 2< and R 4< are independently selected, identically or differently, from the group of divalent hydrocarbon radicals having 1 to 4 carbon atoms, in particular C 2 H 4 and C 3 H 6 , R 3< an acyl radical of a fatty acid with a chain length of 8 to 32 carbon atoms, preferably 12 to 22 carbon atoms, in particular 16 to 22 carbon atoms, particularly preferably 16 to 18 carbon atoms, R 5< H or an acyl radical of a fatty acid with a chain length of 8 to 32 carbon atoms, preferably 12 to 22 carbon atoms, in particular 16 to 22 carbon atoms, particularly preferably 16 to 18 carbon atoms, R 6< selected from the group of hydrocarbon radicals having from 1 to 4 carbon atoms, in particular ethyl and methyl, B) at least one fatty alcohol.

[0035] The compositions according to the invention are preferably aqueous compositions.

[0036] The term "aqueous" in the context of the present invention is understood to mean a composition which contains at least 5% by weight, preferably at least 30% by weight, in particular at least 70% by weight, of water, based on the total composition under consideration.

[0037] The "pH value" in the context of the present invention is defined as the value measured for the corresponding substance at 25 °C after five minutes of stirring with a pH electrode calibrated according to ISO 4319 (1977).

[0038] A "fatty alcohol" in the context of the present invention preferably has 8 to 32 carbon atoms.

[0039] All percentages (%) are by mass unless otherwise stated.

[0040] Compositions preferred according to the invention are characterized in that A) in an amount of 0.1 wt.% to 10 wt.%, preferably from 0.3 wt.% to 5 wt.%, in particular from 0.5 wt.% to 3 wt.%, and B) in an amount of 1 wt.% to 10 wt.%, preferably from 2 wt.% to 8 wt.%, in particular from 3 wt.% to 6 wt.%, is contained, whereby the percentages by weight refer to the total composition.

[0041] It is preferred according to the invention that in the at least one hybrid quat of the general formula I) R 1< represents a hydrocarbon radical of fatty alcohol.

[0042] The term "hydrocarbon residue of fatty alcohol" in the context of this invention refers to the remaining structure after deletion of the OH group of the fatty alcohol. Preferred R 1< residues are hydrocarbon residues of an unbranched or branched monoalcohol with an alkyl group of 10 to 30 carbon atoms, which may also be unsaturated.Preferred radicals R 1< are hydrocarbon radicals of decanol, lauryl alcohol, isolauryl alcohol, anteisolauryl alcohol, myristyl alcohol, isomyristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, anteisostearyl alcohol, eicosanol, petroselinyl alcohol, Guerbet alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, hectacosanol, octacosanol, and melissyl alcohol, as well as mixtures thereof, in particular technical mixtures, preferably technical coconut or tallow fatty alcohols having 12 to 18, preferably having 16 to 18 carbon atoms, as well as monounsaturated fatty alcohols, such as oleyl alcohol, elaidyl alcohol, delta-9-cis-hexadecenol, delta-9-octadecenol, trans-delta-9-octadecenol, cis-Delta-11-Octadecenol, trans-10,cis-12-Hexadecadien-1-ol, Octacosa-10,19-dien-1-ol and polyunsaturated fatty alcohols such asLinoleyl alcohol (9Z, 12Z-octadecadien-1-ol), elaidolinoleyl alcohol (9E, 12E-octadecadien-1-ol), linolenyl alcohol (9Z, 12Z, 15Z-octadecatrien-1-ol), elaidolinolenyl alcohol (9E, 12E, 15-E-octadecatrien-1-ol), with hydrocarbon residues of mixtures of coconut or tallow fatty alcohols with 16 to 18 carbon atoms being particularly preferred.

[0043] Preferably, R 1< is the hydrocarbon radical of a fatty alcohol R 1< -OH, which has a melting point of greater than 25 °C, particularly preferably greater than 50 °C, at 1 bar pressure.

[0044] It is preferred according to the invention that in the at least one hybrid quat of the general formula I) R 1< is a linear alkyl radical having 16 to 18 carbon atoms, R 2< and R 4< are independently selected, identically or differently, from the group C 2 H 4 and C 3 H 6 , R 3< is an acyl radical of a fatty acid having a chain length of 16 to 22, in particular 16 to 18, carbon atoms, R 5< is H or an acyl radical of a fatty acid having a chain length of 16 to 22, in particular 16 to 18, carbon atoms, R 6< is selected from the group ethyl and methyl, is.

[0045] The compositions according to the invention contain at least one fatty alcohol (component B).

[0046] In this context, a fatty alcohol is preferably understood to mean an unbranched or branched monoalcohol with an alkyl group of 8 to 30 carbon atoms, which may also be unsaturated. Preferred fatty alcohols are octanol, decanol, lauryl alcohol, isolauryl alcohol, anteisolauryl alcohol, myristyl alcohol, isomyristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, anteisostearyl alcohol, eicosanol, petroselinyl alcohol, Guerbet alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, hectacosanol, octacosanol, and melissyl alcohol.

[0047] and mixtures thereof, in particular technical mixtures, preferably technical coconut or tallow fatty alcohols with 12 to 18, preferably with 16 to 18 carbon atoms, and the monounsaturated fatty alcohols, such as oleyl alcohol, elaidyl alcohol, delta-9-cis-hexadecenol, delta-9-octadecenol, trans-delta-9-octadecenol, cis-delta-11-octadecenol, trans-10,cis-12-hexadecadien-1-ol, octacosa-10,19-dien-1-ol and polyunsaturated fatty alcohols such as linoleyl alcohol (9Z, 12Z-octadecadien-1-ol), elaidolinoleyl alcohol (9E, 12E-octadecadien-1-ol), linolenyl alcohol (9Z, 12Z, 15Z-octadecatrien-1-ol), elaidolinolenyl alcohol (9E, 12E, 15-E-octadecatrien-1-ol), with mixtures of coconut or tallow fatty alcohols with 16 to 18 carbon atoms being particularly preferred.

[0048] Preferred is a fatty alcohol which has a melting point of greater than 25 °C, particularly preferably greater than 50 °C, at 1 bar pressure.

[0049] The fatty alcohol is preferably present in the composition according to the invention in an amount of 0.5 to 20 wt.%, preferably 1 to 10 wt.%, in particular 2 to 7 wt.%, wherein the weight percentages relate to the total composition.

[0050] It has proven advantageous if the compositions according to the invention additionally contain a component C) emulsifier, in particular in an amount of 0.1 to 10 wt.%, preferably 0.25 to 5 wt.%, in particular 0.5 to 2.0 wt.%, wherein the weight percentages relate to the total composition.

[0051] Preferred emulsifiers are non-ionic emulsifiers.

[0052] In this context, preferred emulsifiers are selected from the group of fatty alcohol alkoxylates, especially fatty alcohol ethoxylates. Particularly preferred fatty alcohol ethoxylates are selected from the group comprising polyoxyethylene ethers of lauryl alcohol, CAS number 9002-92-0, macrogol lauryl ethers, e.g., polyoxyethylene (4) lauryl ether (Laureth-4, INCI), Polyoxyethylen (9) laurylether Laureth-9 (INCI), Polyoxyethylen (23) laurylether Laureth-23 (INCI) Polyoxyethylenether des Cetylalkohols, CAS-Nummer 9004-95-9, z.B. Polyoxyethylen (2) cetylether Ceteth-2 (INCI) Polyoxyethylen (10) cetylether Ceteth-10 (INCI) Polyoxyethylen (20) cetylether Ceteth-20 (INCI) Polyoxyethylenether des Cetylstearylalkohols, CAS-Nummer 68439-49-6, z.B. Polyoxyethylen (6) cetylstearylether Ceteareth-6 (INCI) Polyoxyethylen (20) cetylstearylether Ceteareth-20 (INCI) Polyoxyethylen (25) cetylstearylether Ceteareth-25 (INCI) Polyoxyethylenether des Stearylalkohols, CAS-Nummer 9005-00-9, z.B. Polyoxyethylen (2) stearylether Steareth-2 (INCI) Polyoxyethylen (10) stearylether Steareth-10 (INCI) Polyoxyethylen (20) stearylether Steareth-20 (INCI) Polyoxyethylenether des Oleylalkohols, CAS-Nummer 9004-98-2, z.B.Polyoxyethylene (2) oleyl ether Oleth-2 (INCI) Polyoxyethylene (10) oleyl ether Oleth-10 (INCI) Polyoxyethylene (20) oleyl ether Oleth-20 (INCI) or Polyoxyethylene (10) tridecyl ether (CAS number 24938-91-8) and Trideceth-10 (INCI). .

[0053] Alternatively, preferred emulsifiers are selected from the group of polyol esters, in particular glycerol esters, and polyglycerol esters, in particular polyglycerol esters. Preferably present (poly)glycerol esters are characterized by being partial esters. Particularly preferred polyglycerol partial esters are selected from the group comprising polyglycerol partial esters as described in EP-B-0 835 862, which are obtainable by esterification of a polyglycerol mixture with a degree of esterification of the polyglycerol between 30 and 75% and saturated or unsaturated, linear or branched fatty acids with 12 to 22 C atoms and dimer fatty acids with an average functionality of 2 to 2.4, esters of citric acid such as the O / W emulsifier glyceryl stearate citrate (2-hydroxy-1,2,3-propanetricarboxylic acid-1,2,3-propanetriol monooctadecanoate, INCI Glyceryl Stearate Citrate, CAS 39175-72-9), the citric acid esters of glyceryl stearate, among others.commercially available under the name AXOL C 62, glyceryl stearate citrate as described in WO2006034992 and WO2008092676 and glyceryl oleate citrate as described in WO2004112731, as well as simple polyglycerol esters, such as polyglycerol-3 distearate, polyglyceryl-10 stearate, polyglyceryl-6 distearate, mixed esters of polyglycerol and methylglucose and stearic acid, such as polyglyceryl-3 methylglucose distearate and (poly-)glycerol partial esters with one or more carboxylic acids having 10 to 24 carbon atoms and residues of a polyfunctional carboxylic acid.

[0054] In principle, sorbitan or sucrose esters can also be used as polyol esters. A common combination, for example, is sorbitan stearate and sucrose cocoate.

[0055] In a further alternative, preferably present emulsifiers are selected from the group of modified siloxanes, for example those that carry polyethers in addition to aliphatic groups based on alpha-olefins. Siloxane-based emulsifiers for oil-in-water emulsions must be hydrophilic, which is why they are generally pure polyether siloxanes. Particularly suitable examples are relatively hydrophobic polyether siloxanes as described in EP 1125574, high-molecular-weight polyether siloxanes as described in EP2168564, and organomodified siloxane block copolymers as described in WO2009138306. Preferably present modified siloxanes are characterized by having an HLB value of >8. Particularly preferred modified siloxanes are selected from the group comprising Bis-PEG / PPG-16 / 16 Dimethicone, PEG / PPG-16 / 16 Dimethicone, Bis-PEG / PPG-20 / 5 PEG / PPG-20 / 5 Dimethicone and Methoxy PEG / PPG-25 / 4 Dimethicone.In connection with the present invention, the above-mentioned emulsifiers result in particularly storage-stable formulations.

[0056] Preferred compositions according to the invention are emulsions, preferably oil-in-water emulsions, particularly preferably emulsions in which the oil phase is solid at 25 °C, thus an oil-in-water suspension is present at 25 °C.

[0057] The compositions according to the invention advantageously have a pH of 1 to 6.9, particularly preferably 2 to 6.5, in particular 2.5 to 6, at 25 °C.

[0058] It has proven advantageous if the compositions according to the invention additionally contain a component D) surfactant, in particular in an amount of 0.1 to 10 wt.%, preferably 0.25 to 5 wt.%, in particular 0.5 to 2.0 wt.%, wherein the weight percentages relate to the total composition.

[0059] The term "surfactant" in the context of the present invention refers to organic substances with surface-active properties that have the ability to reduce the surface tension of water to below 45 mN / m at 20°C and at a concentration of 0.5 wt.% based on the total composition. The surface tension is determined here using the DuNoüy ring method at 25°C.

[0060] The surfactants include non-ionic surfactants, anionic surfactants, cationic surfactants and amphoteric (zwitterionic) surfactants.

[0061] Compositions according to the invention are preferred which are characterized in that the surfactant is selected from the group comprising, preferably consisting of: anionic surfactants, cationic surfactants and amphoteric surfactants, with anionic surfactants and cationic surfactants being particularly preferred.

[0062] If the composition according to the invention contains an anionic surfactant, compositions according to the invention are particularly preferred which are characterized in that the anionic surfactant is selected from the group comprising, preferably consisting of: Alkyl sulfates in the form of their alkali, ammonium or alkanolammonium salts, alkyl ether sulfates, alkyl phosphates in the form of their alkali, ammonium or alkanolammonium salts, alkyl ether carboxylates in the form of their alkali or ammonium salts, acyl sarcosinates in the form of their alkali or ammonium salts, sulfosuccinates in the form of their alkali or ammonium salts and acyl glutamates in the form of their alkali or ammonium salts, with alkyl sulfates and alkyl ether sulfates being particularly preferred.

[0063] If the composition according to the invention contains a cationic surfactant, compositions according to the invention are particularly preferred which are characterized in that the cationic surfactant is selected from the group of quaternary ammonium compounds, preferably consisting of alkyltrimethylammonium compounds, with palmitamidopropyltrimonium chloride being particularly preferred.

[0064] If the composition according to the invention contains an amphoteric surfactant, compositions according to the invention are particularly preferred which are characterized in that the amphoteric surfactant is selected from the group comprising, preferably consisting of: Betaines, amphoacetates and amphopropionates, N-alkyl-N,N-dimethylammonium glycinates, for example cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N,N-dimethylammonium glycinates, for example cocoacylaminopropyldimethylammonium glycinate, 2-alkyl-3-carboxylmethyl-3-hydroxyethylimidazolines each having 8 to 18 C atoms in the alkyl or acyl group and cocoacylaminoethylhydroxyethylcarboxymethylglycinate, compounds which, in addition to a C8 / 18 alkyl or acyl group in the molecule, contain at least one free amino group and at least one -COOH- or -SO 3 H- group and are capable of forming inner salts, such as N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each with about 8 to 18 C atoms in the alkyl group, N-coconut alkylaminopropionate,Cocoacylaminoethylaminopropionate and C12 / 18-acylsarcosine, with N-acylaminopropyl-N,N-dimethylammonium glycinate being particularly preferred.

[0065] The compositions according to the invention may, for example, contain at least one further additional component selected from the group of Emollients, co-emulsifiers, thickeners / viscosity regulators / stabilizers, antioxidants, hydrotropes (or polyols), solids and fillers, pearlescent additives, deodorant and antiperspirant active ingredients, insect repellents, self-tanners, preservatives, conditioning agents, perfumes, dyes, cosmetic active ingredients, care additives, superfatting agents, solvents.

[0066] Substances that can be used as exemplary representatives of the individual groups are known to the person skilled in the art and can be found, for example, in German application DE 102008001788.4. This patent application is hereby incorporated by reference and is therefore considered part of the disclosure.

[0067] Regarding further optional components and the amounts of these components used, reference is expressly made to the relevant manuals known to the person skilled in the art, e.g., BK Schrader, "Grundlagen und Rezepturen der Kosmetika," 2nd edition, pages 329 to 341, Hüthig Buch Verlag Heidelberg.

[0068] The amounts of the respective additives depend on the intended use.

[0069] Typical framework formulations for the respective applications are known to be state-of-the-art and can be found, for example, in the brochures of the manufacturers of the respective raw materials and active ingredients. These existing formulations can generally be used unchanged. However, if necessary, the desired modifications for adaptation and optimization can be easily made through simple trials.

[0070] The hybrid quats of the general formula I) contained in the compositions according to the invention as well as the compositions according to the invention can be used according to the invention for the cosmetic treatment of skin or keratinous fibers, in particular for hair treatment, particularly preferably for conditioning hair.

[0071] In this context, preference is given to using those hybrid quats of the general formula I) which are described above as being preferably contained in the compositions according to the invention.

[0072] The use according to the invention leads to an improvement in conditioning, shine, flexibility, resilience, and / or combability as well as a reduction in the probability of breakage of the treated fiber and also reduces the static forces between the fibers.

[0073] Another object of the present invention is the use of the hybrid quats of the general formula I) contained in the compositions according to the invention for viscosity modification, in particular thickening, of a composition containing at least one fatty alcohol.

[0074] In this context, preference is given to using those hybrid quats of the general formula I) which are described above as being preferably contained in the compositions according to the invention.

[0075] Another object of the present invention is the use of the hybrid quats contained in the compositions according to the invention as emulsifiers, in particular cationic emulsifiers, in preferably cosmetic formulations, in particular to obtain O / W emulsions.

[0076] In this context, preference is given to using those hybrid quats of the general formula I) which are described above as being preferably contained in the compositions according to the invention.

[0077] In the examples listed below, the present invention is described by way of example, without the invention, the scope of which emerges from the entire description and the claims, being intended to be limited to the embodiments mentioned in the examples.

[0078] The following images are part of the examples: Figure 1: Combing force measurements Examples:

[0079] Table A: Amines with two hydroxyethyl groups and fatty alcohol residues R 1< Amine R 1< (all % values ​​are mol %) R 2< R 4< Trade name source A1 Stearyl with 93% C18, 5% C16, 2% > C20 with IZ =0-3.0 C2H4 C2H4 Varonic S 202 Evonik Corporation, USA A2 Tallow with 3% C14, 30% C16, 67% C18 with IZ = 38.0-54.0 C2H4 C2H4 Varonic T 202 Evonik Corporation, USA A3 Hydrated tallow with 3% C14, 30% C16, 67% C18 with IZ <= 3.0 C2H4 C2H4 Varonic U202 Evonik Corporation, USA Table B: Fatty acid determining residues R 3< or, where appropriate, R 5< fatty acid source Iodine number FS1 Coconut fatty acid, Wilfarin DC-0818, Wilmar < 12 FS2 Stearic fatty acid, vegetable, Pristeren 4928, Croda < 1,0 FS3 Vegetable oil fatty acid, Nouracid IF 10, Oleon 110 - 125 FS4 12-Hydroxystearic acid, Alberdingk Boley < 5 Example B1 to B6:

[0080] 482.8 g (1.325 mol) of amine A1 were placed in a three-neck flask equipped with a column, distillation still, and stirred motor and heated to 80 °C under a nitrogen atmosphere. 332.8 g (1.59 mol) of fatty acid FS 1 and 0.4 g of 50% aqueous hypophosphorous acid were added. A vacuum of 100 mbar was applied and the mixture was carefully heated to 195 °C, collecting the reaction water in the outlet of the distillation still. After 3 hours, the vacuum was reduced to 20 mbar, and the reaction was continued for 2 hours. The resulting condensation product had an acid number of 1.3 mg KOH / g and an amine number of 94.0 mg KOH / g. The reaction mixture was cooled to 80 °C. While stirring, 155.4 g (1.232 mol) of dimethyl sulfate were added dropwise over one hour, maintaining the temperature between 80 and 95 °C. Subsequently, 103 g of anhydrous ethanol were added, and the mixture was stirred at 80 °C for one hour. The resulting product had an amine number of 3.0 mg KOH / g.

[0081] The other examples B2-B6 and comparative examples were carried out according to this procedure, but with varied starting materials or varied proportions - each as indicated in Table C below. Table C: Example Amine fatty acid Iodine number Moles of fatty acid per mole of amine Experiment number B1 A1 FS1 < 12 1.2 TS 324 / 16 B2 A1 FS2 < 1.0 0.8 AE 323 / / 16 B3 A1 FS3 110 -125 0.8 MK 320 / 16 B4 A1 FS3 110-125 1.5 TS 321 / 16 B5 A3 FS2 < 1.0 1.5 TS 13 / 17 B6 A2 FS4 < 5 1.0 TS 252 / 16 Example B9

[0082] 89.8 g (0.445 mol) of lauric acid, 125.7 g (0.445 mol) of oleic acid, and 209.5 g (0.897 mol) of behenic acid were initially charged at 70 °C. 324.9 g (0.938 mol) of N,N-bis(2-hydroxyethyl)-N-octadecylamine were added dropwise to a three-necked flask fitted with a column attachment. The mixture was slowly heated to 190 °C, and the reaction water was distilled off. After 2 hours, a vacuum of 25 mbar was applied, which was subsequently reduced to 8 mbar. After 8 hours, an acid number of 3.5 mg KOH / g was reached. The reaction mixture was cooled to 60 °C. 771.4 g of the resulting diester were mixed with 448 g of C16 / C18 fatty alcohol. The reaction mixture was gradually treated with 101 g (0.80 mol) of dimethyl sulfate and reacted at 80-90 °C. The resulting product had a total amine value of 2.9 mg KOH / g. Active content: 0.50 meq / g; 34% fatty alcohol. Comparative example VB10 based on DE10210029606:

[0083] 179.5 g (0.89 mol) of lauric acid, 251.4 g (0.89 mol) of oleic acid, and 619 g (1.795 mol) of behenic acid were initially heated to 70 °C. 223.50 g (1.875 mol) of methyldiethanolamine were added dropwise to a three-necked flask fitted with a column attachment. The mixture was slowly heated to 190 °C, and the water of reaction was distilled off. After 2 hours, a vacuum of 25 mbar was applied, which was subsequently reduced to 8 mbar. After 8 hours, an acid number of 4.3 mg KOH / g was reached. The reaction mixture was cooled to 60 °C. 783 g of the resulting diester were mixed with 448 g of C16 / C18 fatty alcohol. The reaction mixture was gradually treated with 146 g (1.159 mol) of dimethyl sulfate and reacted at 90 °C. The resulting product had a total amine value of 2.8 mg KOH / g. Active content: 1.05 meq / g; 32.5% fatty alcohol. Comparison example VB11

[0084] 315.9 g (2.65 mol) of methyldiethanolamine, 666.7 g (3.18 mol) of coconut fatty acid (Wilfarin DC-0818, Wilmar), and 0.5 g of 50% hypophosphorous acid were carefully heated to 195 °C in a three-necked flask fitted with a column under a nitrogen atmosphere. The reaction water was distilled off over a period of 3 hours. A vacuum of 20 mbar was then applied, and the reaction was continued for a further 2 hours until an acid number of 1.6 mg KOH / g was reached. 576 g of the resulting diester were gradually admixed with 199.7 g (1.583 mol) of dimethyl sulfate and stirred at 80-95 °C. Subsequently, 86.2 g of anhydrous ethanol were added and stirred at 80 °C. The resulting product had a total amine number of 3.0 mg KOH / g. Active content: 1.5 meq / g; 10% ethanol, no fatty alcohol Example 2: Application technique of hair treatment products using examples B1, B2 and B6 as well as commercial market products.

[0085] For the application-related evaluation, hair tresses were used that had been pre-damaged by a standardized bleaching treatment. Standard hairdressing products were used for this purpose. The damage to the hair tresses is described in detail in DE10327871.

[0086] For the application-related evaluation, the compounds according to the invention from Examples B1, B2 and B6 were used in a simple cosmetic formulation.

[0087] The commercially available alkylquat (INCI) behentrimonium chloride (VARISOFT ®< BT 85 pellets, Evonik Nutrition & Care) and the commercially available esterquat (INCI) distearoylethyl hydroxyethylmonium methosulfate (VARISOFT ®< EQ F 75, Evonik Nutrition & Care) were used as reference compounds.

[0088] The application properties when used in hair conditioners were tested in the following formulations (Table 1 and 1b): Tab. 1: Hair conditioner formulations for testing hair conditioning properties Formulation examples C0a F1a F2a F5a F6a V7a V8a TEGINACID ®< C, Evonik Industries (INCI: Ceteareth-25) 0,5% 0,5% 0,5% 0,5% 0,5% 0,5% 0,5% TEGO ®< Alkanol 1618, Evonik Nutrition & Care (INCI: cetearyl alcohol) 5% 5% 5% 5% 5% 4,67% 5% Example B1 (90%) 1,1% Example B2 (90%) 1,1% Example B5 (90%) 1,1% Example B6 (90%) 1,1% VARISOFT ®< EQ F 75, (75% in cetearyl alcohol), Evonik Nutrition & Care (INCI: Distearoylethyl Hydroxyethylmonium Methosulfate) 1,33% VARISOFT ®< BT 85, (85% in isopropanol), Evonik Nutrition & Care (INCI: Behentrimonium Chloride) 1,17% demineralized water to 100.0 to 100.0 to 100.0 to 100.0 to 100.0 to 100.0 to 100.0 Citric acid (to pH=4) Tab. 1b: Hair conditioner formulations for testing hair conditioning properties Formulation examples F9a V10a V11a TEGINACID ®< C, Evonik Industries (INCI: Ceteareth-25) 0,5% 0,5% 0,5% TEGO ®< Alkanol 1618, Evonik Nutrition & Care (INCI: cetearyl alcohol) 4,5% 4,5% 5% Example B9 (68% in cetearyl alcohol) 1,5% Comparative example VB10 (66% in cetearyl alcohol) 1,5 Comparative example VB11 (90% in ethanol) 1,1 demineralized water to 100.0 to 100.0 to 100.0 Citric acid (to pH=4)

[0089] The composition of the test formulations was deliberately kept simple to avoid any influence on the test results from (normally present) formulation components. Formulations according to the invention may contain other ingredients in addition to the ingredients mentioned and / or instead of the ingredients mentioned. In particular, the combination with other ingredients can lead to a synergistic improvement in the described effects.

[0090] The hair is pre-treated with a shampoo formulation (Table 2) which does not contain any conditioning agents. Tab. 2: Shampoo formulation for pre-treatment of hair tresses. Texapon NSO ®< , 28%, Cognis (INCI: SodiumLaureth Sulfate) 42,9% NaCl 3% demineralized water to 100.0

[0091] Standardized treatment of pre-damaged hair strands with conditioning samples: The hair strands pre-damaged as described above are washed with the shampoo formulation from Table 2.

[0092] The hair strands are wetted under warm running water. Excess water is gently squeezed out by hand, then shampoo is applied and gently worked into the hair for 1 minute (0.5 ml per 2 g strand). The hair strand is rinsed under warm running water for 30 seconds. This procedure is repeated one more time, but with a final 1-minute rinse.

[0093] Immediately after washing, the hair strands are conditioned with the hair conditioner formulations from Table 1.

[0094] The conditioner is applied and gently worked into the hair (0.5 ml per 2 g strand). After a 1-minute hold, the hair is rinsed for a) 1 minute or b) 3 minutes.

[0095] Before assessing the dryness sensory properties, the hair is dried in air at 50% humidity and 25°C for at least 12 hours. Assessment criteria:

[0096] Sensory evaluations are based on scores awarded on a scale of 1 to 5, with 1 being the worst and 5 being the best. Each individual test criterion receives its own rating.

[0097] The test criteria are: wet combability, wet grip, dry combability, dry grip.

[0098] In the following tables, the results of the sensory assessment of the treatment of the hair strands carried out as described above at a) 1 min rinsing time and at b) 3 min rinsing time are compared with the formulations F1a, F2a, F6a according to the invention, the comparison formulations V7a, V8a and the control formulation C0a (control without test substance). a) 1 min rinsing time

[0099] Tab. 3a: Results of conditioning hair with 1 min rinsing time Wet combability Wet grip Dry combability Dry grip Inventive formulation F1a 4,5 4,5 5 5 Inventive formulation F2a 4 4 5 5 Inventive formulation F3a 4 4 5 5 Inventive formulation F9a 4 4,5 4,5 4,5 Comparative formulation V7a (F 75) 3,5 3,5 3,5 3 Comparative formulation V8a (BT 85) 4 4 4 4 Comparative formulation V10a (F 75) 4 4 4 4 Comparative formulation V11a (F 75) 3 3 3,5 3,5 Control C0a 2 2 3 2,5 b) 3 min rinsing time

[0100] Tab. 3b: Results of conditioning hair with 3 min rinsing time Wet combability Wet grip Dry combability Dry grip Inventive formulation F1a 4 4 5 5 Inventive formulation F2a 4 4 4,5 5 Inventive formulation F3a 4 4 5 5 Inventive formulation F9a 4 4 4 4,5 Comparative formulation V7a (F 75) 3 3 3 3 Comparative formulation V8a (BT 85) 4 4 4 4 Comparative formulation V10a 3 3 3,5 3,5 Comparative formulation V11a 2 2,5 3 3 Control C0a 1,5 2 2,5 2

[0101] The results in Table 3a show that the inventive formulations F1a, F2a, F6a, and F9a each perform better than formulations V7a, V8a, V10a, and V11a in terms of both combability and feel on wet and dry hair. The absolute values ​​of the hybrid quats are particularly excellent on dry hair. Surprisingly, the hybrid quats show hardly any deterioration in results after a 3-minute rinsing time. The conditioning performance remains very high, especially on dry hair. All inventive formulations are rated as significantly better than the comparison formulations. Example 3: Influence of the compounds according to the invention on combing forces of hair Test conditions:

[0102] Measuring device: Diastron MTT 175. Measuring distance: 20 cm. Combing speed: 2000 mm / min. Hair strands used: length = 23 cm; width = 1.5 cm; weight = 2 g. Measuring conditions: T = 22°C.

[0103] The hair strands are measured with a residual moisture content of 60%, determined by weight.

[0104] European, undamaged, dark brown hair was used for the experiments. To conduct the combing force measurements, this hair was permed in the laboratory under standard conditions: 1.) 4 g of perm solution per g of hair, leave on for 15 minutes, rinse for 2 minutes under running tap water (T = 35°C). (Perm solution: Universal Permanent Wave, Basler) 2.) 4 g of fixative (1 part fixative + 3 parts water) per g of hair, leave on for 10 minutes, rinse for 2 minutes. (Fixative solution: Foam Fixative Concentrate, Basler)

[0105] Carrying out the combing force measurement before treatment with the test formulation: The pre-damaged hair strands are conditioned overnight.

[0106] 3.) The hair strand is immersed in a buffer solution (sodium citrate, pH = 6) for 1 minute. 4.) The hair strand is pre-combed by hand until no change in combing resistance is observed. 5.) The hair strand is attached to the measuring device and the first combing force measurement is taken. The measurement is repeated a total of 10 times. Treatment of the strands:

[0107] Apply 0.5 g of the respective test formulation per hair strand (2 g hair / 0.5 g solution). The formulation is massaged into the hair for 30 seconds and then left on for 5 minutes. Rinse under running tap water for 1 minute or 3 minutes, respectively.

[0108] To perform the combing force measurement after treatment with the test formulation, points 3-5 are repeated.

[0109] The combing effort (%) is then calculated before and after treatment with the test formulation. Test formulations used:

[0110] The combing forces when used in hair conditioners were tested in the following formulations (Table 4): Tab. 4: Hair conditioner formulations for testing combing forces and antistatic properties Formulation example e C0b F1b F2b F6b F9b V7b V8b V10b V11 b TEGINACID ®< C, Evonik Industries (INCI: Ceteareth-25) 0,5% 0,5% 0,5% 0,5% 0,5% 0,5% 0,5% 0,5% 0,5 % TEGO ®< Alkanol 1618, Evonik Nutrition & Care (INCI: cetearyl alcohol) 5% 5% 5% 5% 4,25 % 4,5% 5% 4,25 % 5% Example B1 (90%) 1,65 % Example B2 (90%) 1,65 % Example B6 (90%) 1,65 % Example B9 (68% in cetearyl alcohol) 2,25 % VARISOFT ®< EQ F 75, (75% in cetearyl alcohol), Evonik Nutrition & Care (INCI: Distearoylethyl Hydroxyethylmonium Methosulfate) 2% VARISOFT ®< BT 85, (85% in isopropanol), Evonik Nutrition & Care (INCI: Behentrimonium Chloride) 1,75 % Comparative example VB10 (66% in cetearyl alcohol 2,25 Comparative example VB11 (90% in ethanol) 1,65 demineralized water to 100, 0 to 100.0 to 100.0 to 100.0 to 100, 0 to 100.0 Citric acid (to pH=4)

[0111] In the Figure 1 The results of the combing force measurements of the experiments carried out as described above with a rinsing time of 1 min are compared with the formulations F1b, F2b, F6b according to the invention, as well as the control formulation C0b (control without test substance).

[0112] The results in Figure 1 show that the formulations F1b, F2b, F6b according to the invention show a strong reduction in combing forces at a rinsing time of 1 minute. Example 4: Antistatic treatment of keratin fibers

[0113] The shadow silhouette method was used to test the antistatic properties. The pretreated hair strands described above, a plastic comb, a spotlight, and a projection field marked with concentric semicircles were used.

[0114] The tests were conducted under standardized climatic conditions. The hair weft was suspended at a distance of 15 cm from the projection field. The spotlight was positioned at a distance of 145 cm from the hair weft, so that a shadow fell on the projection field.

[0115] Now, comb the hair weft five times in succession with the comb. The electrostatic charge is measured using the shadow silhouette by marking the two outermost points of the shadow and determining their distance. The smaller the shadow area, the more effective the antistatic effect. Result:

[0116] Formulation (see Table 4) Distance C0b 15 cm F1b 7 cm F2b 7.5 cm F6b 6.5 cm F9b 7 cm V7b 9 cm V8b 7.5 cm V10b 7.5 cm V11b 9 cm Example 5: Viscosities of the example formulations Result:

[0117] Formulation (see Table 1) Brookfield viscosity 25°C (Sp. TC, 30 rpm) C0b 5550 F1a 15000 F2a 30000 F5a 32000 F6a 23600 F9a 14000 V7a 11000 V8a 12000 V10a 10000 V11a 7000

[0118] The formulations F1a, F2a, F5a, F6a and F9a according to the invention show significantly higher viscosities compared to the corresponding formulations based on VARISOFT ®< EQ F 75 and VARISOFT ®< BT 85, which are known to be very good emulsifiers. Example 6: Long-term storage stability

[0119] The formulations were stored at 40 °C for 3 months Result:

[0120] Formulation (see Table 1 and 1b) Brookfield viscosity 25°C (Sp. TC, 30 rpm) C0b Phase separation F1a 13000 F2a 25000 F5a 29000 F6a 20000 F9a 12000 V7a Phase separation V10a 5000 V11a 2000

[0121] After three months of storage at 40 °C, the inventive formulations F1aL3, F2aL3, F5aL3, F6aL3, and F9aL3 exhibit significantly lower viscosity reductions compared to the corresponding formulations based on VARISOFT®< EQ F 75, known as a very good emulsifier, and the comparative examples V10aL3 and V11aL3. This particularly demonstrates the positive effect of replacing a methyl group (V10aL3 and V11aL3) on the nitrogen atom with a stearyl group (F1aL3 and F9aL3). c) 1 min rinsing time after 3 months storage at 40 °C

[0122] Tab. 6a: Results of conditioning hair with 1 min rinsing time after 3 months of storage at 40 °C Wet combability Wet grip Dry combability Dry grip Inventive formulation F1a 4 4 4,5 5 Inventive formulation F9a 4 3,5 4 4,0 Comparative formulation V8a (BT 85) 4 4 4 4 Comparative formulation V10a 2 1,5 2 2 Comparative formulation V11a 1,5 2 2,5 2,5 Control C0a (without storage) 1,5 2 2 2

[0123] After three months of storage at 40 °C, the inventive formulations F1aL3, F2aL3, F5aL3, F6aL3, and F9aL3 show hardly any change in conditioning performance (similar stability to comparative example V8aL3 based on an alkyl quat), while the corresponding formulations based on comparative examples V10aL3 and V11aL3 hardly exhibit any conditioning properties. The positive effect of replacing a methyl group (V10aL3 and V11aL3) on the nitrogen atom with a stearyl group (F1aL3 and F9aL3) is particularly evident.

Claims

1. Composition comprising A) at least one hybrid quat of the general formula I) where R1 is a hydrocarbon radical having 10 to 32 carbon atoms, preferably 12 to 22 carbon atoms, in particular 16 to 18 carbon atoms, R2 and R4 are independently the same or different and are selected from the group of divalent hydrocarbon radicals having from 1 to 4 carbon atoms, in particular C2H4 and C3H6, R3 is an acyl radical of a fatty acid having a chain length of 8 to 32 carbon atoms, preferably 12 to 22 carbon atoms, in particular 16 to 22 carbon atoms, especially preferably 16 to 18 carbon atoms, R5 is H or an acyl radical of a fatty acid having a chain length of 8 to 32 carbon atoms, preferably 12 to 22 carbon atoms, in particular 16 to 22 carbon atoms, especially preferably 16 to 18 carbon atoms, R6 is selected from the group of hydrocarbon radicals having from 1 to 4 carbon atoms, in particular ethyl and methyl, B) at least one fatty alcohol.

2. Composition according to Claim 2, characterized in that A) is present in an amount from 0.1% by weight to 10% by weight, preferably from 0.3% by weight to 5% by weight, in particular from 0.5% by weight to 3% by weight, and B) is present in an amount from 1% by weight to 10% by weight, preferably from 2% by weight to 8% by weight, in particular from 3% by weight to 6% by weight, where the percentages by weight are based on the total composition.

3. Composition according to Claim 1 or 2, characterized in that, in the at least one hybrid quat of the general formula I), the radical R1 is a hydrocarbon radical of fatty alcohol.

4. Composition according to at least one of the preceding claims, characterized in that, in the at least one hybrid quat of the general formula I), R1 is a linear alkyl radical having 16 to 18 carbon atoms, R2 and R4 are independently the same or different and are selected from the group of C2H4 and C3H6, R3 is an acyl radical of a fatty acid having a chain length of 16 to 22, in particular 16 to 18, carbon atoms, R5 is H or an acyl radical of a fatty acid having a chain length of 16 to 22, in particular 16 to 18, carbon atoms, R6 is selected from the group of ethyl and methyl.

5. Composition according to at least one of the preceding claims, characterized in that B) the at least one fatty alcohol is selected from the fatty alcohols octanol, decanol, lauryl alcohol, isolauryl alcohol, anteisolauryl alcohol, myristyl alcohol, isomyristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, anteisostearyl alcohol, eicosanol, petroselinyl alcohol, Guerbet alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, hectacosanol, octacosanol, and melissyl alcohol.

6. Use of at least one hybrid quat of the general formula I) as described in at least one of Claims 1 to 5 or of a composition according to at least one of Claims 1 to 5 for conditioning hair.

7. Use of at least one hybrid quat of the general formula I) as described in at least one of Claims 1 to 5 for modifying the viscosity of a composition comprising at least one fatty alcohol.