Patent Description:
<CIT> describes quaternary ammonium compounds comprising two <NUM>-acyloxyalkyl groups, the acyl groups of which are derived from saturated or unsaturated carboxylic acids having <NUM> to <NUM> carbon atoms, including dimethyldi(oleoyl-oxyisopropyl)ammonium methosulfate, and the use of such substances in textile-softening formulations.

<CIT> describes similar quaternary ammonium compounds, the corresponding acyl groups of which comprise at most <NUM> carbon atoms, including dimethyldi(palmitoyl-oxyisopropyl)ammonium chloride, and the use of such substances in textile-softening formulations, but also mentions their suitability for hair conditioning agents.

<CIT> discloses a textile softener composition with improved stability and softening performance which comprises a fabric-softening active amount of a quaternary ammonium salt having specific mono-, di- and triester components, where the diester component amounts to more than about <NUM>% by weight and the triester component amounts to less than about <NUM>% by weight based on the total amount of the quaternary ammonium salt.

<CIT> discloses a composition comprising, based on the weight of the composition, about <NUM>% to about <NUM>% by weight of a mixture of one or more ester quats and one or more glycerides, where the mixture comprises about <NUM>% to about <NUM>% by weight of ester quats and about <NUM>% to about <NUM>% by weight of glycerides; and, based on the weight of the composition, optionally <NUM>% to about <NUM>% by weight of a solvent.

<CIT>, <CIT>, <CIT> and <CIT>, respectively, disclose ester quats or mixtures thereof which are structurally different to those presently claimed.

Ester quats obtainable hitherto, which are suitable for use in hair conditioning, are solid substances which are only converted to a formulatable form by using solvents, as a result of which it is stipulated which solvent will be present in the end formulation. This limits the degrees of freedom of the formulation options. Currently available liquid hair conditioning agents exhibit excellent conditioning properties but decrease the viscosity of the formulations as the concentration increases. This limits the use concentration and requires the use of an emulsifier for the fatty alcohol.

It was an object of the invention to provide a composition which exerts excellent conditioning effects on keratin fibres and simultaneously enables a high viscosity and stability.

Surprisingly, it has been found that the compositions described below are able to achieve the object of the invention.

The present invention provides a composition comprising an ester quat of the general formula I)
<CHM>
where.

It is clearly apparent to those skilled in the art from the general formula I) and the chosen wording that the ester quat of the composition according to the invention is a compound composed of multiple distinct molecules, with the numbers a to c stated indicating average values.

In the case where the mixture of acyl radicals does not comprise any unsaturated C16 acyl radicals or saturated C18 acyl radicals, then the respective ratio is greater than <NUM> or greater than <NUM>.

The invention further provides for the use of a composition comprising an ester quat of the general formula I)
<CHM>
where.

One advantage of the present invention is that the ester quats used are liquid at room temperature and can therefore easily be incorporated into a final consumer formulation without the use of solvents and without heating, as a result of which such a solvent does not necessarily have to be present in said formulation.

Another advantage of the present invention is that the shine of the treated keratin fibres is increased.

A further advantage of the present invention is that the compounds used develop a good effect even in small use amounts.

A further advantage is that the compounds used have little impact from an ecological point of view. Another advantage is that the compounds used exhibit an improved conditioning effect on keratin fibres in the case of longer rinse-off times than quaternary ester compounds known hitherto. Another advantage of the present invention is that the compounds used do not crystallize out. Another advantage of the present invention is that the compounds used are effective in relatively low use concentrations.

Another advantage of the present invention is that the compounds used protect hair colourants from being washed out.

Another advantage of the present invention is that the compounds used protect keratin fibres against thermally induced damage.

Another advantage of the present invention is that the compounds used reduce the combing forces on wet and dry hair.

Another advantage of the present invention is that the compounds used are particularly economically viable.

Another advantage of the present invention is that the compounds used can be incorporated into surfactant formulations to give a clear formulation.

Another advantage of the present invention is that the viscosity can be increased depending on the use concentration of the conditioning agent.

Unless stated otherwise, all stated percentages (%) are percentages by mass.

The ester quats used in the context of the invention can be prepared by relevant methods of preparative organic chemistry. Usually, the preparation of ester quats is based on a multistage process in which firstly the esterified alkanolamine is prepared by reacting an alkanolamine with carboxylic acids or corresponding derivatives, and said alkanolamine is then subsequently quaternized with a suitable reagent. In connection with the present invention, the alkanolamine used is triethanolamine or triisopropanolamine or mixtures thereof, in particular triethanolamine.

In connection with suitable preparation processes, reference may be made to <CIT>, according to which trialkanolamine is partially esterified in the presence of hypophosphorous acid with fatty acids, air is passed through and then quaternization is carried out with dimethyl sulfate or ethylene oxide. The compounds listed therein serve as plasticizers for textiles. <CIT> describes the preparation of solid ester quats by carrying out the quaternization of the triethanolamine esters in the presence of suitable dispersants. Overviews on this topic can be found for example under <NPL>), <NPL>), <NPL>) or under <NPL>).

The ester quats present in the compositions according to the invention are characterized by the parameter a with respect to their degree of esterification. The ester quat thus comprises corresponding mono-, di- and/or triesters, which result in a statistical average corresponding to the degree of esterification.

Suitable methods for quantitative determination are HPLC and NMR, with particular emphasis being given to the methodology disclosed in Characterization of quaternized triethanolamine esters (esterquats) by HPLC, HRCGC and NMR by <NPL>.

Compositions that are preferred according to the invention comprise an ester quat of the general formula I) that comprises, based on all ester quats of the general formula I) that are present, less than <NUM>% by weight, preferably less than <NUM>% by weight, especially preferably less than <NUM>% by weight, of triester quat.

Compositions that are preferred according to the invention comprise an ester quat of the general formula I) in which R<NUM> = H, a = <NUM> to <NUM>, in particular <NUM>, and b = <NUM>.

The acyl radicals R<NUM> of the general formula I) are a mixture which has a weight ratio of saturated C16 acyl radicals to unsaturated C16 acyl radicals of greater than <NUM> and a weight ratio of unsaturated C18 acyl radicals to saturated C18 acyl radicals of greater than <NUM>.

Such a distribution can in particular be found in mixed vegetable oils.

Compositions that are preferred according to the invention are characterized in that the mixture of acyl radicals comprises a content of acyl radicals as shown below (mixed vegetable oil fatty acid I).

where the percentages by weight are based on the sum total of all R<NUM> in the ester quat of the general formula I). The iodine number is preferably in the range from <NUM> to <NUM>, particularly preferably <NUM> to <NUM>, gl/<NUM>.

Compositions that are preferred according to the invention are characterized in that the mixture of acyl radicals comprises a content of acyl radicals as shown below (mixed vegetable oil fatty acid II).

Compositions that are preferred according to the invention are characterized in that the mixture of acyl radicals comprises a content of acyl radicals as shown below (tall oil fatty acid).

where the percentages by weight are based on the sum total of all R<NUM> in the ester quat of the general formula I). The iodine number is preferably in the range from <NUM> to <NUM> gl/<NUM>.

In the abovementioned compositions according to the invention, the mixture of acyl radicals may of course comprise a content of other acyl radicals in addition to those specifically named. It is preferable according to the invention if the sum total of the specifically named acyl radicals amounts to at least <NUM>% by weight, in particular at least <NUM>% by weight, particularly preferably at least <NUM>% by weight, based on all acyl radicals present in the mixture.

Compositions that are preferred according to the invention are characterized in that the mixture of acyl radicals has an iodine number of <NUM> to <NUM>, preferably <NUM> to <NUM>, particularly preferably <NUM> to <NUM>, cg I/g.

The charge of the compound I) present in the composition according to the invention must be compensated by corresponding anions; this takes place by means of counteranions present in the composition according to the invention.

Suitable as such counteranions are, for example, the halides, pseudohalides, anions of mineral acids, sulfates, sulfites, hydrogensulfites, sulfonate, alkyl- and arylsulfonates, phosphate, hydrogenphosphates, phosphites, hydrogenphosphites, phosphonites, carboxylates, borates, carbonates, sulfides, hydrogensulfides, lactate, glycolate, formate, acetate and propionate.

These anions are preferably selected from those which are suitable for cosmetic application and are therefore for example nontoxic. Particularly preferably, at least one counteranion to the compound of the general formula I) selected from the group comprising chloride, bromide, iodide, alkyl sulfate, for example methyl sulfate, ethyl sulfate, alkylsulfonate, for example methylsulfonate, triflate, tosylate, phosphate, sulfate, hydrogensulfate, lactate, glycolate, acetate and citrate, preferably chloride and methyl sulfate, is present.

The compositions according to the invention may be processed with further constituents to form formulations, in particular cosmetic formulations, so that the compositions according to the invention are, in particular cosmetic, formulations.

The formulations according to the invention comprise the ester quat preferably in an amount of <NUM>% by weight to <NUM>% by weight, preferably <NUM>% by weight to <NUM>% by weight, in particular <NUM>% by weight to <NUM>% by weight, where the percentages by weight are based on the total composition.

Formulations that are preferred according to the invention are characterized in that they do not comprise any fatty acids or fatty acid salts.

It has proven to be advantageous if the formulations according to the invention additionally comprise <NUM>% by weight to <NUM>% by weight, preferably <NUM>% by weight to <NUM>% by weight, in particular <NUM>% by weight to <NUM>% by weight, of at least one fatty alcohol, where the percentages by weight are based on the total formulation.

In this context, "fatty alcohol" is preferably understood to mean an unbranched or branched monoalcohol having an alkyl group of <NUM> to <NUM> 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, and mixtures thereof, in particular technical-grade mixtures, preferably technical-grade coconut or tallow fatty alcohols having <NUM> to <NUM>, preferably having <NUM> to <NUM>, carbon atoms, and the monounsaturated fatty alcohols, such as oleyl alcohol, elaidyl alcohol, delta-<NUM>-cis-hexadecenol, delta-<NUM>-octadecenol, trans-delta-<NUM>-octadecenol, cis-delta-<NUM>-octadecenol, trans-<NUM>,cis-<NUM>-hexadecadien-<NUM>-ol, octacosa-<NUM>,<NUM>-dien-<NUM>-ol, and polyunsaturated fatty alcohols such as for example linoleyl alcohol (9Z, 12Z-octadecadien-<NUM>-ol), elaidolinoleyl alcohol (9E, 12E-octadecadien-<NUM>-ol), linolenyl alcohol (9Z, 12Z, 15Z-octadecatrien-<NUM>-ol), elaidolinolenyl alcohol (9E, 12E, <NUM>-E-octadecatrien-<NUM>-ol), with particular preference being given to mixtures of coconut or tallow fatty alcohols having <NUM> to <NUM> carbon atoms.

It is preferable according to the invention that the composition according to the invention comprises at least one alkylamidoamine.

Alkylamidoamines preferably present are those of the general formula II)
<CHM>.

R<NUM>CO here is an aliphatic, linear or branched acyl residue having <NUM> to <NUM> carbon atoms and <NUM> and/or <NUM>, <NUM> or <NUM> double bonds, which generally originates from a naturally occurring or synthetically prepared fatty acid.

R<NUM> and R<NUM> are identical or different alkyl radicals which may optionally bear functional groups such as hydroxy groups, ester groups, amines, amides or other polar substituents, with preference however generally being given to unsubstituted hydrocarbon radicals which at most have one or more branches.

However, short-chain hydrocarbon radicals having <NUM> to <NUM> carbon atoms are especially preferred, with very particular preference being given according to the invention to ethyl and methyl radicals.

The number m is an integer from <NUM> to <NUM>, with preference being given to values for m of <NUM> to <NUM>, in particular of <NUM> to <NUM>.

The alkylaminoamines are usually prepared by amidation of natural or synthetic fatty acids and fatty acid cuts with dialkylaminoamines. Typical examples of such fatty acids are caproic acid, caprylic acid, <NUM>-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palm oleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, eleostearic acid, arachidic acid, gadoleic acid, behenic acid and erucic acid, and technical-grade mixtures thereof which are produced for example during the pressurized cleavage of natural fats and oils, during the reduction of aldehydes from the Roelen oxo synthesis or the dimerization of unsaturated fatty acids.

Particular preference is usually given to the fatty acid cuts which are obtainable from coconut oil or palm oil, with the use of stearic acid generally being especially preferred.

Depending on the intended use, the composition according to the invention may comprise the ester quat and the alkylamidoamine in different amounts.

In the treatment of keratin fibres, in particular of human hair, use is generally made of active ingredient concentrations (based on the individual components) of <NUM>% by weight to <NUM>% by weight, preferably <NUM>% by weight to <NUM>% by weight and especially preferably <NUM>% by weight to <NUM>% by weight. Particularly good results can be achieved at active ingredient concentrations of <NUM>% to <NUM>% by weight. The application of the preparations according to the invention to keratin fibres, in particular to human hair, is not however limited to the use of the active ingredients at a low concentration. It is also possible to use concentrates in which the active ingredients are each present in proportions of <NUM>% by weight to <NUM>% by weight or <NUM>% by weight to <NUM>% by weight, in particular at <NUM>% by weight to <NUM>% by weight.

Ester quats and alkylaminoamines are usually present in a weight ratio of <NUM> to <NUM> to <NUM> to <NUM>, in particular of <NUM> to <NUM> to <NUM> to <NUM>, in the preparation according to the invention. Depending on the desired effect, the mixing ratio may also be varied from <NUM> : <NUM> to <NUM> : <NUM> or even from <NUM> : <NUM> to <NUM> : <NUM>.

The formulations according to the invention may comprise for example at least one further, additional component selected from the group of.

Substances which can be used as exemplary representatives of the individual groups are known to those skilled in the art and can be taken, for example, from German patent application <CIT>.

As regards further optional components and also the amounts used of these components, reference is expressly made to the relevant handbooks known to those skilled in the art, for example <NPL>.

The amounts of the respective additives are guided by the intended use.

Typical starting formulations for the relevant applications are known prior art and are contained for example in the brochures of the manufacturers of the relevant base materials and active substances. These existing formulations can generally be adopted unchanged. However, if necessary, for adjustment and optimization, the desired modifications can be made in a straightforward manner through simple tests.

It is preferable according to the invention that the composition according to the invention comprises at least one emulsifier selected from the group of polyglycerol esters.

It is preferable according to the invention if the formulation has a pH of <NUM> to <NUM>, preferably <NUM> to <NUM>.

In connection with the present invention, the "pH" is defined as the value which is measured for the relevant composition at <NUM> after stirring for five minutes using a pH electrode calibrated in accordance with ISO <NUM> (<NUM>).

The compositions according to the invention can be used according to the invention for treating keratin fibres, in particular for treating hair.

In this connection, use is preferably made of those compositions that are described above as preferred compositions.

The use according to the invention leads to the improvement in the conditioning, shine, flexibility, elasticity and/or combability, and to a reduction in the probability of breakage of the treated fibres and, moreover, it reduces the antistatic forces between the fibres.

The use according to the invention leads to the protection of the fibres against heat.

The examples which follow describe the present invention by way of example, without any intention of restricting the invention, the scope of application of which is apparent from the entirety of the description and the claims, to the embodiments cited in the examples.

The following figures are an integral part of the examples:.

<NUM> (<NUM> mol) of mixed vegetable oil fatty acid I (C16 <NUM>%, C16:<NUM><NUM>%, C18 <NUM>%, C18:<NUM><NUM>%, C18:<NUM><NUM> %, C18:<NUM><NUM>%, iodine number <NUM> gl/<NUM>) is mixed with <NUM> (<NUM> mol) of triethanolamine and heated to <NUM> with stirring. Water of reaction is distilled off continuously. After the majority of the water of reaction has been distilled at atmospheric pressure, reduced pressure is applied and the acid number of the reaction mixture is reacted down to < <NUM> KOH/g. The resulting ester amine is cooled to <NUM> and admixed with <NUM> (<NUM> mol) of dimethyl sulfate in such a way that the reaction temperature does not exceed <NUM>.

After cooling to room temperature, the total amine number (TAN) and the active content of the finished product are analysed.

TAN = <NUM> KOH/g; active content <NUM> meq/g (cationic active content according to Epton).

<NUM> (<NUM> mol) of mixed vegetable oil fatty acid II (C16 <NUM>%, C16:<NUM><NUM>%, C18 <NUM>%, C18:<NUM><NUM>%, C18:<NUM><NUM>%, C18:<NUM><NUM>%, iodine number <NUM> gl/<NUM>) is mixed with <NUM> (<NUM> mol) of triethanolamine and heated to <NUM> with stirring. Water of reaction is distilled off continuously.

After the majority of the water of reaction has been distilled at atmospheric pressure, reduced pressure is applied and the acid number of the reaction mixture is reacted down to < <NUM> KOH/g. The resulting ester amine is cooled to <NUM> and admixed with <NUM> (<NUM> mol) of dimethyl sulfate in such a way that the reaction temperature does not exceed <NUM>.

<NUM> (<NUM> mol) of stearic acid (technical-grade quality, approx. <NUM>% pure) is admixed with <NUM> (<NUM> mol) of triethanolamine and esterified as described in Example <NUM>. The ester amine had an acid number of <NUM> KOH/g. This mixture was alkylated with <NUM> (<NUM> mol) of dimethyl sulfate as described in Example <NUM>. At the end of the alkylation, the viscosity increased sharply and the mixture was diluted with <NUM> of isopropanol.

The TAN of the finished product was determined with <NUM> KOH/g, the active content was <NUM> meq/g.

<NUM> (<NUM> mol) of commercial tall oil fatty acid (Sylfat™ <NUM> from Kraton, <NPL>) is mixed with <NUM> (<NUM> mol) of triethanolamine and esterified as described in Example <NUM>. The ester amine had an acid number of <NUM> KOH/g. This mixture was alkylated with <NUM> (<NUM> mol) of dimethyl sulfate as described in Example <NUM>. The TAN of the finished product was determined with <NUM> KOH/g, the active content was <NUM> meq/g.

<NUM> (<NUM> mol) of erucic acid is mixed with <NUM> (<NUM> mol) of triethanolamine and esterified as described in Example <NUM>. The ester amine had an acid number of <NUM> KOH/g. This mixture was alkylated with <NUM> (<NUM> mol) of dimethyl sulfate as described in Example <NUM>. The TAN of the finished product was determined with <NUM> KOH/g, the active content was <NUM> meq/g.

<NUM> (<NUM> mol) of isostearic acid (technical-grade quality) is admixed with <NUM> (<NUM> mol) of triethanolamine and esterified as described in Example <NUM>. The ester amine had an acid number of <NUM> KOH/g. This mixture was alkylated with <NUM> (<NUM> mol) of dimethyl sulfate as described in Example <NUM>.

<NUM> (<NUM> mol) of oleic acid (<NUM>%) is admixed with <NUM> (<NUM> mol) of triethanolamine and esterified as described in Example <NUM>. The ester amine had an acid number of <NUM> KOH/g. This mixture was alkylated with <NUM> (<NUM> mol) of dimethyl sulfate as described in Example <NUM>.

<NUM> (<NUM> mol) of mixed vegetable oil fatty acid is mixed with <NUM> (<NUM> mol) of methyldiisopropanolamine and heated to <NUM> with stirring. Water of reaction is distilled off continuously. After the majority of the water of reaction has been distilled at atmospheric pressure, reduced pressure is applied and the acid number of the reaction mixture is reacted down to < <NUM> KOH/g. The resulting ester amine is cooled to <NUM> and admixed in portions with <NUM> (<NUM> mol) of dimethyl sulfate in such a way that the reaction temperature does not exceed <NUM>. After cooling to room temperature, the total amine number (TAN) and the active content of the finished product are analysed.

For the application-related assessment, use was made of hair tresses which had been predamaged in a standardized manner by way of a bleaching treatment. Standard hairdressing products are used for this purpose. The damage to the hair tresses is described in detail in <CIT>.

For the application-related assessment, the compounds of the examples were used in a simple cosmetic formulation.

As reference compounds, the commercially available ester quat (INCI) Distearoylethyl Hydroxyethylmonium Methosulfate (VARISOFT® EQ F <NUM> Pellets, Evonik Industries) was also used.

The application properties when used in hair rinses were tested in the following formulations (Tab.

The composition of the test formulations is deliberately chosen to be simple in order to avoid the test results being influenced by (normally present) formulation constituents. In addition to the specified ingredients and/or instead of the specified ingredients, formulations according to the invention may also comprise further ingredients. In particular, the combination with further ingredients can lead to a synergistic improvement in the case of the described effects.

The hair is pretreated using a shampoo formulation (Tab. <NUM>) which does not comprise any conditioning agents.

The hair tresses which have been predamaged as described above are washed with the shampoo formulation from Tab.

Here, the hair tresses are wetted under running warm water. The excess water is gently squeezed out by hand, then the shampoo is applied and worked gently into the hair for <NUM> (<NUM>/<NUM> hair tress). The hair tress is rinsed for <NUM> under running warm water. This procedure is repeated once more, except that final rinsing is for <NUM>.

Then, directly after washing, the hair tresses are conditioned with the hair rinse formulations from Tab.

Here, the rinse is applied and gently worked into the hair (<NUM>/<NUM> hair tress). After a residence time of <NUM>, the hair is rinsed for a) <NUM> or for b) <NUM>.

Before the sensory assessment, the hair is dried for at least <NUM> in the air at <NUM>% humidity and <NUM>.

The sensory evaluations are performed using grades awarded on a scale from <NUM> to <NUM>, with <NUM> being the worst evaluation and <NUM> being the best evaluation. The individual test criteria each receive their own evaluation.

The test criteria are:
Wet combability, wet feel, dry combability, dry feel, appearance/shine.

In the tables which follow, the results of the sensory assessment of the treatment of the hair tresses, carried out as described above, in the case of a) <NUM> rinsing time and in the case of b) <NUM> rinsing time, are compared with the inventive formulations 1a and 8a and the comparative formulations and the control formulation C0a (control without test substance).

The results in Table 3a show that the inventive formulations 1a and 8a have very good conditioning properties with <NUM> rinsing time which are at the same level as the comparative formulation V7a and are very significantly superior to the comparative formulations V2a and V6a. The inventive formulations 1a and 8a are noticeably improved in comparison with V5a.

The results in Table 3b show that the inventive formulations 1a and 8a have even more markedly improved conditioning properties with <NUM> rinsing time than after <NUM> than the comparative formulations V2a and V6a. In comparison with the comparative formulation V7a, the results are comparable at a very high level. The comparative formulation V7a comprises an ester quat that is known for its very good conditioning properties even in the case of long rinsing times. The comparative formulation V6a comprises, as conditioning compound, VARISOFT® EQ F <NUM> (<NUM>% strength in C16/<NUM> fatty alcohol, Evonik Industries, INCI: Distearoylethyl Dimonium Chloride, Cetearyl Alcohol), an ester quat that has very good emulsifying properties, but only a moderate conditioning performance with <NUM> rinsing time (see Tab. 3a), and exhibits even worse conditioning with <NUM> rinsing time.

<NUM> of the respective test formulation is used per hair tress (<NUM> hair/<NUM> solution). The formulation is massaged into the hair for <NUM> sec and then left on for <NUM>, then rinsed off under running tap water for <NUM> or <NUM>.

Carrying out the combing force measurement after the treatment with the test formulation:
Points <NUM>-<NUM> are repeated.

The combability (%) is then calculated before and after the treatment with the test formulation. Test formulations used:
The combing forces when used in hair rinses were tested in the following formulations (Tab.

The results are shown in <FIG> (rinsing time of <NUM>) and <NUM> (rinsing time of <NUM>).

To test the antistatic behaviour, the shadow silhouette method was used.

The pretreated hair tresses described above, a plastic comb, a spotlight and a projection field marked with concentric semicircles are used.

The experiments were carried out under standardized climatic conditions. The hair tress is hung up at a distance of <NUM> from the projection field. The spotlight is positioned at a distance of <NUM> from the hair tress so that a shadow falls on the projection field.

The hair tress is then combed five times in succession using the comb. The electrostatic charging is measured via the shadow silhouette by marking the two outer points of the shadow and determining the distance between them. The smaller the shadow area, the more effective the antistatic effect.

Each individual formulation listed below was prepared three times.

For "Inventive Example X", each of Inventive Examples 1a, 1b and <NUM> were used.

Claim 1:
Composition comprising an ester quat of the general formula I)
<CHM>
where
R<NUM> is an acyl radical of a fatty acid,
R<NUM> is independently selected from alkyl radicals having <NUM> to <NUM> carbon atoms and H, in particular H,
where
a = <NUM> to <NUM>, preferably <NUM> to <NUM>, particularly preferably <NUM> to <NUM>, in particular <NUM>, and
b = <NUM> - a,
characterized in that
R<NUM> is a mixture of acyl radicals which has
a weight ratio of saturated C16 acyl radicals to unsaturated C16 acyl radicals of greater than <NUM> and
a weight ratio of unsaturated C18 acyl radicals to saturated C18 acyl radicals of greater than <NUM>.