Active substances for cleaning compositions

Abstract

The present invention relates to a composition Z which comprises at least one quaternary ammonium compound. The compositions Z can be used as active substances for cleaning and active-substance compositions, especially softener compositions. The compositions Z have good softening properties and are at the same time characterized by an improved rewetting power.

Description

[0001] Active ingredients for

[0002] The present invention relates to a composition Z comprising at least one quaternary ammonium compound. Compositions Z can be used as active ingredients for cleaning and active ingredient compositions, in particular fabric softener compositions. Compositions Z exhibit good softening properties and are simultaneously characterized by improved rewetting properties.

[0003] Fabric softeners based on quaternary ammonium compounds give textiles and fibers a pleasant, soft feel. Quaternary ammonium compounds containing two long-chain hydrocarbon residues are typically used as fabric softening compounds in the production of aqueous fabric softeners. Such quaternary ammonium compounds can be used to produce stable aqueous dispersions that are suitable as fabric softeners for textiles and achieve a good softening effect. Such fabric softeners are described, for example, in US Pat. No. 4,439,331.

[0004] In the prior art, fatty acid esters of alkanolamines, especially triethanolamine, are also frequently used as quaternary ammonium salts, so-called "esterquats." Esterquats have the advantage over quaternary ammonium compounds with primarily long-chain alkyl groups that they are more biodegradable.

[0005] Also described in the prior art are fabric softener compositions containing quaternary ammonium compounds based on di- or polyamines. For example, US Pat. No. 2,878,144 A describes that quaternary ammonium salts based on alkylenediamines and alkylenepolyamines have good softening properties and good thermal stability. US Pat. No. 3,170,938 A discloses surface-active properties, in particular antistatic effects, of alkylenediamines and alkylenepolyamines. Example 14 of US Pat. No. 3,170,938 A describes the preparation of an ammonium salt. EP 0 803 498 A1 discloses fabric softener compositions containing quaternary ammonium compounds based on polyamines with improved color stability. Such fabric softeners are also described in GB 808,265 A and US Pat. No. 2,878,144 A.Example 16 of GB 808,265 A discloses the preparation of a monoquaternary ammonium salt from N,N,N',N'-tetrakis(2-hydroxyethyl)ethylenediamine dioleate and dimethyl sulfate.

[0006] CN 115 745 816 A discloses, in Process Example 2, the preparation of a gemini ester in the form of a quaternary ammonium salt based on tetrahydropropxylethylenediamine and oleic acid using dimethyl sulfate as the quaternization reagent (degree of esterification 3). CN 115 745 816 A also discloses the use for treating synthetic fabrics and cotton, as well as for increasing softness. A typical disadvantage of such fabric softener compositions is that the rewetting capacity or water absorption capacity (synonym: "rewetting capacity") of synthetic fabrics is negatively impaired by the fabric softener. For example, if a cotton fabric is treated together with a synthetic fabric with a prior art fabric softener, the softness of the cotton fabric is improved, but the rewetting capacity of the synthetic fabric is simultaneously impaired.

[0007] This problem is described in WO 2016 / 121307 A1 with regard to non-quaternized amine compounds. This document discloses tertiary amine compounds that are suitable as plasticizers and for which the reduction in rewetting capacity is limited. It also reveals that this combination of desired properties (plasticizer / good rewetting capacity) cannot be satisfactorily achieved with quaternary ammonium compounds and therefore presents a particular challenge for this class of compounds.

[0008] US 2007 / 0265469 A1 discloses quaternary ammonium compounds, primarily those based on ethylenediamine with polymerization products of ethylene oxide. According to US 2007 / 0265469 A1, these compounds also exhibit advantageous rewetting properties when used as plasticizers.

[0009] In light of the state of the art, there continues to be a need for new active substances which make it possible to produce fabric softener compositions which, when conditioning fabric blends containing cotton fabrics and synthetic fabrics, in particular polyester and polyester blend fabrics, simultaneously ensure a good soft feel of the cotton fabric and a good rewetting capacity of the synthetic fabric.

[0010] The object of the present invention was therefore to provide novel active ingredients, novel active ingredient compositions, and novel cleaning compositions, in particular fabric softener compositions, which do not exhibit the disadvantages of the prior art or exhibit them only to a reduced extent. These active ingredients should, in particular, be quaternary ammonium compounds.

[0011] A specific task was to provide new active substances, new active substance compositions for fabric softeners and new fabric softener compositions, in particular based on quaternary ammonium compounds, which make it possible to impart a good soft feel to the cotton in a common washing cycle of cotton fabrics or fibres and synthetic fabrics or fibres, in particular polyester and polyester blend fabrics or fibres, and at the same time to have as little negative an impact as possible on the rewetting capacity of the synthetic fabric or fibres.

[0012] Another specific task can be seen in the provision of new active substances, in particular based on quaternary ammonium compounds, which can be used in all types of cleaning compositions in which other quaternary ammonium compounds have previously been used.

[0013] It was also an object of the present invention to provide new active substances, in particular based on quaternary ammonium compounds, which can be easily incorporated into cleaning compositions, in particular fabric softener compositions, and lead to stable dispersions.

[0014] The inventors have surprisingly discovered that compositions Z according to claim 1, which comprise at least one quaternary ammonium compound of formula (I), achieve the stated objectives. The active substances according to the invention, ie the quaternary ammonium compounds of formula (I), are distinguished by the fact that they are quaternary ammonium compounds based on tetraalcohol diamines whose hydroxyl groups are only partially esterified with fatty acids.In addition, they are characterized in that the iodine number of the fatty acid residues in the composition Z which are esterified with the quaternary ammonium compounds of the formula (I) is at least 100, preferably in the range from 100 to 200, more preferably in the range from 100 to 190, more preferably in the range from 100 to 180, more preferably in the range from 100 to 170, more preferably in the range from 100 to 160, even more preferably in the range from 100 to 150, even more preferably in the range from 100 to 140, even more preferably in the range from 100 to 130, even more preferably in the range from 100 to 125, even more preferably in the range from 100 to 120. In this context, “fatty acid residues” are understood to mean.

[0015] Connection all residues other than hydrogen R 4 , R 7 , R 10 , R 13 understood.

[0016] Without being bound to a specific theory, the inventors are of the opinion that by using tetraalcohol diamines in combination with specific fatty acid residues and the fact that when using mixtures of the active substances according to the invention at least one free hydroxyl group is contained in the quaternary ammonium compounds of the formula (I) according to the invention, active substances with an optimal polarity are obtained, thus solving the stated problems.

[0017] With the compositions Z according to the invention, it was possible in particular to produce fabric softener compositions which produce a good soft feel on cotton fabrics and at the same time have an improved rewetting capacity on synthetic fabrics compared to fabric softeners of the prior art.

[0018] The compositions Z according to the invention can also be used in other cleaning compositions in which other quaternary ammonium compounds, in particular esterquats, have previously been used. The ammonium compounds according to the invention also exhibit advantageous biodegradability and, due to their advantageous viscosity, can be handled without the need for additional solvents.

[0019] Detailed description of the invention

[0020] The present invention therefore relates to compositions Z comprising at least one quaternary ammonium compound of the formula (I) according to claim 1, active substance compositions according to claim 8, cleaning compositions according to claim 9 and the use of the compositions Z according to the invention according to claims 13 and 15.

[0021] 1. Terms

[0022] In the context of the present invention, “active ingredient” is understood to mean a quaternary ammonium compound of the formula (I) according to the invention.

[0023] For the purposes of the present invention, "active ingredient composition" or "concentrate" refers to a composition Z that is used either as a cleaning composition itself, in particular as a fabric softener, or for its production. If an active ingredient composition is used to produce cleaning compositions, the active ingredient composition is diluted during production and, as a rule, additional additives are added. Dilution is preferably carried out with water and / or an organic solvent.

[0024] The active ingredient compositions according to the invention can contain the active ingredients according to the invention, but can also consist solely of these. In addition to the active ingredients according to the invention, they usually also contain at least one perfume oil and water and / or an organic solvent.

[0025] "Cleaning compositions" refers to all types of cleaning compositions in which esterquats are commonly used. These are preferably fabric softener compositions.

[0026] All percentages (%) are by mass unless otherwise stated.

[0027] All conditions such as pressure and temperature are standard conditions (20 °C, 1 bar) unless otherwise stated.

[0028] The terms "fabric softener" and "fabric softener composition" are used synonymously in the present invention. The terms "quaternary ammonium compound," "ammonium compound," and "ammonium salt" are also used synonymously.

[0029] "Propylene" encompasses all isomers of propylene, preferably propylene = n-propylene. "Butylene" encompasses all isomers of butylene, preferably butylene = n-butylene. "Propyl" encompasses all isomers of propyl, i.e., n-propyl and / so-propyl.

[0030] “Butyl” includes all isomers of butyl, preferably butyl = n-butyl.

[0031] 2. Composition Z

[0032] The present invention relates to a composition Z comprising at least one quaternary ammonium compound of the general formula (I):

[0033] Where R 1 a divalent, saturated or unsaturated, straight-chain, branched or cyclic

[0034] Hydrocarbon radical having 1 to 6, preferably 2 to 6 carbon atoms.

[0035] In a preferred embodiment, R 1 a divalent, saturated, straight-chain hydrocarbon radical having 1 to 6, preferably 2 to 6 carbon atoms.

[0036] Even more preferred is R 1 selected from the group consisting of butylene, propylene, ethylene, most preferably selected from the group consisting of propylene and ethylene, and most preferably R 1 = Ethylene.

[0037] R 2 , R 5 , R 8 , R 11 are each independently selected from the group consisting of divalent, saturated or unsaturated, straight-chain, branched or cyclic hydrocarbon radicals having 1 to 6, preferably 2 to 6, carbon atoms. In a preferred embodiment, R 2 , R 5 , R 8 , R 11independently of one another are each selected from the group consisting of divalent, saturated, straight-chain hydrocarbon radicals having 1 to 6, preferably 2 to 6, carbon atoms.

[0038] Preferred are R 2 , R 5 , R 8 , R 11 are each independently selected from the group consisting of methylene, ethylene, propylene, butylene, more preferably selected from the group consisting of methylene, ethylene, propylene, even more preferably selected from the group consisting of methylene, ethylene, and most preferably each methylene.

[0039] R 3 , R 6 , R 9 , R 12are each independently selected from the group consisting of hydrogen and alkyl radicals having 1 to 6 carbon atoms, preferably selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, / so-propyl, particularly preferably selected from the group consisting of hydrogen and methyl, and most preferably each methyl.

[0040] R 4 , R 7 , R 10 , R 13 are each independently selected from the group consisting of hydrogen and acyl radicals of straight-chain or branched, saturated or unsaturated, preferably at least monounsaturated, fatty acids with a chain length of 16 to 24 carbon atoms, which optionally have at least one OH group. The proviso applies that one, two or three, preferably one or two, more preferably one, of the radicals R 4 , R 7 , R 10 , R 13 is equal to hydrogen.

[0041] In a preferred embodiment, R 4 , R 7 , R 10 , R 13 are each independently selected from the group consisting of hydrogen, acyl radicals of ricinoleic acid, acyl radicals of straight-chain or branched, saturated or unsaturated, preferably at least monounsaturated, fatty acids with a chain length of 16 to 24 carbon atoms. The proviso is that one, two or three, preferably one or two, more preferably one, of the radicals R 4 , R 7 , R 10 , R 13 is equal to hydrogen.

[0042] In a more preferred embodiment of the present invention, the at least one quaternary ammonium compound of the formula (I) is characterized in that the radicals R 4 , R 7 , R 10 , R 13which are other than hydrogen, are selected from the acyl residues of the acids selected from ricinoleic acid, isostearic acid, palmitic acid, palmitoleic acid, oleic acid, elaidic acid, vaccenic acid, gadoleic acid, icosenoic acid, gondoic acid, cetoleic acid, erucic acid, margaric acid, stearic acid, arachnic acid, linoleic acid, α-linolenic acid, γ-linolenic acid, calendulic acid, punicic acid, α-elaeostearic acid, β-elaeostearic acid, arachidonic acid, stearidonic acid, preferably are selected from the acyl residues of the acids selected from palmitic acid, stearic acid, oleic acid, linoleic acid, α-linolenic acid, γ-linolenic acid.

[0043] R 14 , R 15, if present, are each independently selected from the group consisting of hydrogen, alkyl radical having 1 to 6 carbon atoms, preferably selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, / so-propyl, most preferably selected from the group consisting of ethyl, methyl, and most preferably they are each methyl.

[0044] “If present” means that in the case that a = 0, the nitrogen atom in question only has the bonds to R 5 , R 2 and R 1 The nitrogen atom in question is then not quaternized and instead of bonding to R 14 an electron pair; in the case that b = 0, the nitrogen atom in question only has the bonds to R 8 , R 11 and R 1 The nitrogen atom in question is then not quaternized and instead of bonding to R 15an electron pair.

[0045] X m - is a counteranion. "Counteranion" means an anion that balances the single or double positive charge of the quaternary ammonium cation.

[0046] X m - is preferably selected from the group consisting of chloride, bromide, iodide, alkyl sulfate, where the alkyl sulfate is preferably methyl sulfate or ethyl sulfate, alkylsulfonate, where the alkylsulfonate is preferably methylsulfonate, triflate, tosylate, phosphate, sulfate, hydrogen sulfate, lactate, glycolate, acetate, citrate, where X m- preferred is methyl sulfate. a and b are the same or different, a = 0 or 1 . b = 0 or 1 . The proviso is that a + b = 1 or a + b = 2. n is equal to the sum of a + b, i.e. n = a + b. m is the number of negative charges of X m- .

[0047] The quaternary ammonium compounds according to the invention are characterized in that one to three, preferably one or two, particularly preferably one, of the radicals R 4 , R 7 , R 10 , R 13 is equal to hydrogen.

[0048] Another essential property of the present invention is that the iodine number of all radicals R other than hydrogen 4 , R 7 , R 10 , R 13 comprised by the quaternary ammonium compounds of formula (I) in composition Z is at least 100, preferably in the range from 100 to 200, more preferably in the range from 100 to 150, even more preferably in the range from 100 to 120.

[0049] The quats disclosed in the prior art all have a lower corresponding iodine number: Example 14 of US Pat. No. 3,170,938 A discloses a monooleate ester. Example 16 of GB 808,265 A discloses a dioleate ester. Process Example 2 of CN 115 745 816 A discloses a trioleate ester. These three quats are thus esterified only with oleate. Thus, for a composition comprising each of these three prior art compounds, the corresponding iodine number of oleic acid is ~89. The compositions according to the invention exhibit better rewetting capacity with comparable plasticizing ability compared to these prior art quats, as shown in the examples.

[0050] It was therefore surprisingly found that, under this condition, composition Z has an improved rewetting capacity compared to the quaternary ammonium compounds of the prior art, which does not come at the expense of the plasticizing capacity.

[0051] “The iodine number of all radicals R other than hydrogen 4 , R 7 , R 10 , R 13 , which are comprised of the quaternary ammonium compounds of formula (I) in the composition Z" means, for a given composition Z, the iodine value of a fatty acid mixture MFA consisting of the free fatty acids R 4 -EAR 7 -EAR 10 -EAR 13 -OH, where for each radical other than hydrogen R 4 , R 7 , R 10 , R 13 in the composition Z the corresponding fatty acid R 4 -EAR 7 -EAR 10 -EAR 13 -OH is present in MFA.

[0052] The iodine number is the amount of iodine in g that is absorbed by the double bonds of the fatty acid mixture MFA, based on 100 g of the mixture MFA-

[0053] For a given composition Z, the iodine number can be determined as follows:

[0054] The compounds of formula (I) comprised in composition Z are completely saponified to form a mixture MFA consisting of the fatty acids of formula R 4 -EAR 7 -EAR 10 -EAR 13 -OH is obtained. The amount of iodine absorbed by the total MFA mixture is determined according to DIN 53241-1:1995-05 and expressed as g iodine per 100 g of fatty acid mixture MFA-

[0055] The number of residues R 4 , R 7 , R 10 , R 13which are hydrogen and which are an acyl residue of a fatty acid, is always equal to four per molecule of a quaternary ammonium compound of formula (I). This means, for example, that if in a molecule of a quaternary ammonium compound of formula (I) two of the residues R 4 , R 7 , R 10 , R 13 are each hydrogen, and the other two residues must each be acyl residues of a fatty acid. The same applies to other combinations.

[0056] Preference is given to quaternary ammonium compounds according to formula (I) in which two, three or four, more preferably three or four, most preferably all four of the groups R 2 , R 5 , R 8 , R 11 are identical. This results in advantages in the preparation of the compounds, since only one alkylating agent and not a mixture of several alkylating agents needs to be used. Particularly preferred are all four of the R groups. 2 , R 5, R 8 , R 11 identical and selected from the group consisting of methylene, ethylene, propylene, butylene, most preferably selected from the group consisting of methylene, ethylene, propylene and most preferably methylene, ethylene. Most preferably, R 2 , R 5 , R 8 , R 11 each methylene.

[0057] For the same reasons, preference is given to quaternary ammonium compounds according to formula (I) in which two, three or four, particularly preferably three or four and very particularly preferably all four of the radicals R 3 , R 6 , R 9 , R 12 are identical. If R 14 , R 15 If both are present, they can be the same or different, but preferably they are identical.

[0058] For the reasons of production efficiency described above, preference is also given to quaternary ammonium compounds according to formula (I) in which two, three or four, particularly preferably three or four, and very particularly preferably all four of the radicals R 3 , R 6 , R 9 , R 12 are identical. Even more preferably, all four of the residues R 3 , R 6 , R 9 , R 12 the same alkyl radical having 1 to 6 carbon atoms. Most preferably, R 3 , R 6 , R 9 , R 12 each methyl.

[0059] In the preparation of compositions Z, mixtures of fatty acids known to the person skilled in the art can be used.

[0060] The preferred vegetable and animal fatty acid mixtures are fatty acids produced from natural raw materials, e.g., tallow or vegetable oils. These are generally present as a mixture of several fatty acids, each having an average of 16 to 24 carbon atoms and the iodine number according to the invention.

[0061] Fatty acid mixtures can be used in their original form, provided the mixture has the required iodine value and number of carbon atoms, or they can be treated, e.g. hydrogenated or mixed with other fatty acids, to obtain the required iodine value and number of carbon atoms.

[0062] The quaternary ammonium compounds according to the invention can be prepared by relevant methods of preparative organic chemistry. The preparation is usually based on a multi-step process in which an alkanolamine of the general formula (II)

[0063] where R 1 , R 2 , R 3 , R 5 , R 6 , R 8 , R 9 , R 11 , R 12 defined analogously to formula (I), by reacting a commercially available diamine of the general formula (III): H2N-R 1 -NH2, where R 1 as defined for formula (I), with an alkoxylating reagent such as ethylene oxide, propylene oxide or butylene oxide, preferably

[0064] Propylene oxide. This reaction is known to those skilled in the art and is described, for example, in JP 4,213,236 B2.

[0065] In a second step, an esterified alkanolamine is prepared by reacting an alkanolamine of general formula (II) with the fatty acids or mixtures of fatty acids defined above. This reaction is also known to the person skilled in the art and is described, for example, in

[0066] US 2015 / 0080286A1.

[0067] Preferably, 1 mol of an alkanolamine of the general formula (II) is reacted with 1 to < 4 mol, preferably with 2.3 to 3.2 mol, particularly preferably 2.5 to 3.0 mol of fatty acids or mixtures of fatty acids. In the last step, the esterified alkanolamine is reacted with a suitable quaternizing reagent R 14 X or R 15 X, or a mixture thereof, where X is the counter anion with m times the negative charge, R 14 and R 15 as defined for formula (I), quaternized by methods customary in the technical field, as described, for example, in US 2015 / 0080286 A1.

[0068] In the quaternization, 1 mol of esterified alkanolamine is preferably reacted with 1.0 to 1.6 mol, particularly preferably 1.2 to 1.4 mol of quaternizing reagent,

[0069] The compositions Z according to the invention can be used as cleaning compositions, in particular fabric softener compositions, and as active ingredient compositions, in particular as fabric softener active ingredient compositions.

[0070] The present invention relates to compositions Z as cleaning compositions, preferably for cleaning fibers and fabrics, particularly preferably fabric softener compositions, and active ingredient compositions containing at least one quaternary ammonium compound of the formula (I).

[0071] In the preparation of the compositions Z according to the invention comprising at least one quaternary ammonium compound of the formula (I), mixtures of several quaternary ammonium compounds of the formula (I) according to the invention are generally formed.The composition Z according to the invention therefore preferably comprises at least two, more preferably at least three, even more preferably at least four, even more preferably at least ten different quaternary ammonium compounds of the formula (I), wherein optionally this composition Z additionally comprises at least one, preferably at least two, more preferably at least three, even more preferably at least four, even more preferably at least ten different tetraesterquats (these are described below) and optionally this composition Z additionally comprises at least one, more preferably at least two, even more preferably at least three, even more preferably at least four, even more preferably at least ten different compounds of the formula (I)* (also described below).

[0072] These compositions Z are preferably used to produce the cleaning or active ingredient compositions.

[0073] A further reason why mixtures are formed during the preparation of the quaternary ammonium compounds of formula (I) according to the invention is that during esterification of the alkanolamine of general formula (II) with fatty acids or mixtures of fatty acids, sometimes one, sometimes two, sometimes three, and sometimes all four hydroxyl groups are esterified. In other words, a mixture of monoesteramine, diesteramine, triesteramine, and tetraesteramine is formed. These, in turn, become monoesterquats, diesterquats, triesterquats, and tetraesterquats after quaternization, respectively. The composition Z according to the invention, which is in particular a cleaning composition, preferably a fabric softener composition, preferably contains monoesterquats, diesterquats, and triesterquats, but may also contain tetraesterquats.

[0074] Monoesterquats are quaternary ammonium compounds of formula (I) in which three of the radicals R 4 , R 7 , R10 , R 13 each is hydrogen. Diesterquats are quaternary ammonium compounds of formula (I) in which two of the radicals R 4 , R 7 , R 10 , R 13 is hydrogen. Triesterquats are quaternary ammonium compounds of formula (I) in which one of the radicals R 4 , R 7 , R 10 , R 13 is equal to hydrogen.

[0075] The composition Z according to the invention optionally also comprises tetraesterquats. Tetraesterquats are compounds which have a structure of formula (I), but in which each of the radicals R 4 , R 7 , R 10 , R 13are each independently selected from the group consisting of acyl radicals of straight-chain or branched, saturated or unsaturated, preferably at least monounsaturated, fatty acids having a chain length of 16 to 24 carbon atoms, wherein the acyl radicals optionally have at least one OH group; preferably selected from the acyl residues of the acids selected from ricinoleic acid, isostearic acid, palmitic acid, palmitoleic acid, oleic acid, elaidic acid, vaccenic acid, gadoleic acid, icosenoic acid, gondoic acid, cetoleic acid, erucic acid, margaric acid, stearic acid, arachnic acid, linoleic acid, α-linolenic acid, γ-linolenic acid, calendulic acid, punicic acid, α-elaeostearic acid, β-elaeostearic acid, arachidonic acid, stearidonic acid, more preferably selected from the acyl residues of the acids selected from palmitic acid, stearic acid, oleic acid, linoleic acid, α-linolenic acid, γ-linolenic acid.

[0076] In the embodiments of the present invention in which the composition Z also comprises tetraesterquats, the ratio of the molar amount of all tetraesterquats in the composition Z to the sum of the molar amount of mono-, di-, and triesterquat in the composition Z is preferably in the range 99:1 to 1:99, more preferably 4:1 to 1:4, even more preferably 51:49 to 49:51, most preferably 50:50.

[0077] Finally, a further reason why mixtures of the quaternary ammonium compounds of formula (I) are formed during the preparation of composition Z can be seen in the fact that one or both nitrogen atoms can be quaternized during quaternization. Depending on the molar ratio of esterified alkanolamine and quaternization reagent, incomplete quaternization can also occur overall, ie, part of the esterified alkanolamine is not quaternized. In this preferred embodiment, composition Z according to the invention also comprises at least one compound of formula (I)*, where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 which have the meaning given for formula (I).

[0078] It is particularly preferred that, when Z also comprises at least one compound of formula (I)*, the ratio of the amount of all compounds of formula (I) comprised by composition Z to the amount of all compounds of formula (I)* comprised by composition Z is in the range 99:1 to 1:99, preferably in the range 3:2 to 2:3, more preferably in the range 4:3 to 3:4, even more preferably in the range 1:3:1 to 1:1.

[0079] 3. Cleaning composition

[0080] If the composition Z is a cleaning composition, the at least one quaternary ammonium compound of formula (I) is preferably dispersed in water and / or another water-miscible organic solvent for its preparation.

[0081] If composition Z is a cleaning composition, the proportion of all quaternary ammonium compounds of formula (I), based on the total weight of composition Z, is preferably in the range from 2 to 30 wt.%, preferably 3 to 19 wt.%, more preferably 5 to 15 wt.%. The remaining mass to 100 wt.% preferably consists of water and / or at least one additive and / or auxiliary and / or organic solvents.

[0082] If composition Z is a fabric softener composition, it optionally comprises additives and auxiliaries, in particular perfume, dyes, viscosity regulators, defoamers, preservatives, organic solvents, and non-siloxane-containing polymers. In particular, the fabric softener compositions according to the invention can then contain, based on the total weight of composition Z, between 0.001 and 15, particularly preferably 0.01 to 5, wt. % of one or more different additives or auxiliaries. If composition Z is a fabric softener composition, all fragrances or fragrance mixtures known from the prior art to be suitable for fabric softeners can be used as the perfume, preferably in the form of a perfume oil. Examples of fragrances or odorants are disclosed, inter alia, in DE 197 51 151 A1, page 4, lines 11-17.

[0083] In particular, the composition Z according to the invention can then contain, based on the total weight of the composition Z, from 0.01 to 10% by weight, particularly preferably 0.1 to 5% by weight, of one or more perfumes.

[0084] All dyes known to be suitable for fabric softeners from the prior art can be used as dyes, with water-soluble dyes being preferred. Examples of suitable water-soluble commercially available dyes are SANDOLAN® Walkblau NBL 150 (manufacturer: Clariant) and Sicovit® Azorubin 85 E122 (manufacturer: BASF). In particular, the composition Z according to the invention can contain, based on the total weight of the composition Z, from 0.001 to 0.1 wt. %, particularly preferably from 0.002 to 0.05 wt. %, of one or more dyes.

[0085] As a viscosity regulator for reducing the viscosity, the composition Z may contain an alkali metal or alkaline earth metal salt, or mixtures thereof, preferably calcium chloride, preferably in an amount of 0.05 to 2 wt.%, based on the total weight of the composition Z.

[0086] As a viscosity regulator to increase the viscosity, composition Z may contain a thickener known from the prior art, with the polyurethane thickeners known from WO 2007 / 125005 A1 being preferred. Examples of suitable thickeners are TEGO® Visco Plus 3030 (manufacturer: Evonik Resource Efficiency GmbH), Acusol® 880 and 882 (manufacturer: Rohm & Haas), Rheovis® CDE (manufacturer: BASF), Rohagit® KF 720 F (manufacturer: Evonik Performance Materials GmbH), and Polygel® K100 from Neochem GmbH.

[0087] All defoamers known to be suitable from the prior art can be used as defoamers in composition Z. Examples of suitable commercially available defoamers are Dow Corning® DB-110A and TEGO® Antifoam® 7001 XP. In particular, the compositions Z according to the invention can contain, based on the total weight of composition Z, from 0.0001 to 0.05 wt. %, preferably from 0.001 to 0.01 wt. %, of one or more different defoamers.

[0088] The term “preservative” in the context of the present invention is understood to mean an agent which preserves against microbial, in particular bacterial, growth. As a preservative, for example, composition Z, if it is a fabric softener, can contain bactericidal and / or fungicidal active ingredients known from the prior art as suitable, with water-soluble active ingredients being preferred. Examples of suitable commercially available bactericides are methylparaben, 2-bromo-2-nitro-1,3-propanediol, 2-methyl-4-isothiazolin-3-one and 5-chloro-2-methyl-4-isothiazolin-3-one, or phenoxyethanol, sodium benzoate, or lactic acid. Likewise, if composition Z is an aqueous fabric softener, it can contain an antioxidant as a preservative.Examples of suitable commercially available antioxidants are ascorbic acid, 2,6-di-tert-butyl-4-methylphenol (BHT), butylhydroxyanisole (BHA), tocopherol, and propyl gallate. In particular, the composition Z according to the invention can contain from 0.0001 to 0.5 wt. %, particularly preferably from 0.001 to 0.2 wt. %, based on the total weight of the composition Z, of one or more different preservatives. In particular, the composition Z according to the invention can contain from 0.001 to 0.1 wt. %, preferably from 0.001 to 0.01 wt. %, based on the total weight of the composition Z, of one or more different antioxidants.

[0089] If the composition Z is, for example, a cleaning and active ingredient composition, in particular a fabric softener, this composition Z may contain short-chain alcohols, glycols and glycol monoethers as organic solvents, with ethanol, 2-propanol, 1,2-propanediol and dipropylene glycol being preferred. In particular, the composition Z according to the invention can contain, based on the total weight of the composition Z, between 0.1 and 10 wt.%, particularly preferably 0.2 to 5 wt.%, of one or more different organic solvents. The active ingredient composition Z according to the invention can contain between 0.01 and 30 wt.%, particularly preferably 0.01 to 15 wt.%, based on the total weight of the composition Z, of one or more different organic solvents.

[0090] Particularly when composition Z is a cleaning composition, in particular a fabric softener, composition Z may contain one or more non-siloxane-containing polymers. Examples include carboxymethylcellulose, polyethylene glycol, polyvinyl alcohol, poly(meth)acrylates, polyethyleneimines, or polysaccharides. In particular, composition Z according to the invention may contain between 0.01 and 25 wt. %, particularly preferably 0.1 to 10 wt. %, of one or more different non-siloxane-containing polymers.

[0091] The amounts of the respective additives and excipients depend on the intended use. Typical framework formulations for the respective applications are well-known 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 compositions can generally be used unchanged. However, if necessary, the desired modifications for adaptation and optimization can be easily carried out through simple experiments.

[0092] 4. Active ingredient composition

[0093] In a particular embodiment, composition Z is an active ingredient composition.

[0094] An active ingredient composition is preferred for cleaning fibers and fabrics. A particularly preferred active ingredient composition is a fabric softener active ingredient composition.

[0095] In an active ingredient composition Z according to the invention, the proportion of all quaternary ammonium compounds of formula (I), based on the total weight of composition Z, is preferably at least 50 wt.%, preferably 50 to 100 wt.%, more preferably 80 to 100 wt.%, even more preferably 90 to 100 wt.%. The remaining mass to 100 wt.% preferably consists of water and / or at least one additive and / or excipient and / or organic solvents.

[0096] As already described above, the compositions Z according to the invention comprising at least one quaternary ammonium compound according to formula (I) are suitable as cleaning compositions, in particular fabric softener compositions, and active substance compositions, in particular for the treatment of synthetic fabrics and fibers, in particular polyester fabrics and / or polyester blend fabrics or corresponding fibers, since the rewetting capacity of the synthetic fabrics and fibers is significantly less negatively affected than in the case of compositions containing esterquats of the prior art, compared to the untreated fabrics and fibers.

[0097] In addition, the quaternary ammonium compounds according to formula (I) according to the invention have a good softening effect, in particular of cotton fabric.

[0098] The composition Z according to the invention is therefore preferably used to increase the softness of fabrics or fibers, preferably cotton, compared to untreated fabrics. The invention therefore further relates to the use of the composition Z according to the invention to increase the softness of fabrics or fibers, preferably cotton, compared to untreated fabrics or fibers.

[0099] The composition Z according to the invention is also particularly suitable for treating mixtures of different fabrics or fibers, in particular mixtures comprising cotton fabrics and / or fibers and synthetic fabrics or synthetic blended fabrics and / or corresponding fibers. This applies in particular to polyester fabrics and / or polyester blended fabrics or corresponding fibers. Particularly preferred mixtures or blended fabrics are, for example, polyester / elastane or polyester / cotton blended fabrics.

[0100] The use of the quaternary ammonium compounds according to the invention or the fabric softener and active ingredient compositions containing them in the previously described mixtures of different fabrics or fibers has the particular advantage that at the same time the softness, e.g. of cotton, is increased compared to the untreated fabric and the rewetting capacity of the synthetic fabric or synthetic blended fabric is maintained or even improved compared to the untreated fabric.

[0101] A further subject of the invention is therefore the use of the inventive

[0102] Composition Z for the treatment of synthetic fabric, preferably polyester fabric and / or polyester blend fabric. Preferably, the synthetic fabric and a cotton-containing fabric are treated simultaneously.

[0103] Measurement methods:

[0104] Determination of the iodine number

[0105] The iodine number indicates how many grams of halogen, calculated as iodine, are bound by 100 g of sample under the conditions of a specific method. The Wijs measurement method according to DIN 53241-1:1995-05 is used in the present invention.

[0106] Determination of the amine number

[0107] The total basicity is determined by potentiometric titration in anhydrous medium with perchloric acid according to AOCS method Tf 2a-64.

[0108] Determination of the hydroxyl number

[0109] The hydroxyl number is determined according to the method of the German Fat Chemical Society DGF CV 17a.

[0110] Determination of the acid number

[0111] The acid number is determined in accordance with DIN EN ISO 2114.

[0112] Examples

[0113] 1. Materials used Table 1 : Fatty acid mixtures used

[0114] Table 2: other materials

[0115] Table 3: State-of-the-art esterquat used in the comparative examples 2. Inventive examples

[0116] 2.1 nq of the Formula (I) using

[0117] Example A

[0118] For esterification, 292 g (1 mol) of tetra-(2-hydroxypropyl)ethylenediamine ("THPED") was mixed with 823 g (3.0 mol) of FS1 at 80 °C in a three-neck flask equipped with a stirrer, distillation column, and distillation head. 0.4 g of hypophosphorous acid (50 wt.% in water) was added. The flask was evacuated and the vacuum broken with nitrogen. The mixture was then heated to 195 °C, and water was distilled off at atmospheric pressure for three hours. A vacuum of 20 mbar was applied, and the reaction was continued for 5 hours until the mixture had an acid number of 3.3 mg KOH / g and a total amine number of 104 mg KOH / g. During the esterification, 21 g of samples were taken. In the second step, the resulting esteramine was treated with 159 g (1.26 mol) of dimethyl sulfate ("DMS") so that the temperature did not exceed 70 °C. The reaction was then continued for 5 hours at 80 °C until the total amine content fell to 32.7 mg KOH / g.

[0119] Example B

[0120] For esterification, 292 g (1 mol) of THPED were mixed with 686 g (2.5 mol) of FS1 at 80 °C in a three-neck flask equipped with a stirrer, distillation column, and distillation head. 0.35 g of hypophosphorous acid (50 wt.% in water) was added. The flask was evacuated and the vacuum broken with nitrogen. The mixture was then heated to 195 °C, and water was distilled off at atmospheric pressure for three hours. A vacuum of 20 mbar was applied, and the reaction was continued for 5 hours until the mixture had an acid number of 3.0 mg KOH / g and a total amine number of 119 mg KOH / g. A 21 g sample was taken during the esterification.

[0121] In the second step, the resulting esteramine was treated with 159 g (1.26 mol) of DMS, ensuring that the temperature did not exceed 70 °C. The reaction was then continued for 5 hours at 80 °C until the total amine content fell to 36 mg KOH / g.

[0122] Example C

[0123] For esterification, 292 g (1 mol) of THPED were mixed with 856 g (3.0 mol) of FS2 at 80 °C in a three-neck flask equipped with a stirrer, distillation column, and distillation head. 0.4 g of hypophosphorous acid (50 wt.% in water) was added. The flask was evacuated and the vacuum broken with nitrogen. The mixture was then heated to 195 °C, and water was distilled off for three hours at atmospheric pressure. A vacuum of 20 mbar was applied, and the reaction was continued for 5 hours until the mixture had an acid number of 5 mg KOH / g and a total amine number of 100 mg KOH / g. During the esterification, 12 g of sample was taken. In the second step, the resulting esteramine was admixed with 159 g (1.26 mol) of DMS, ensuring that the temperature did not exceed 70 °C. The reaction was then continued for 5 hours at 80 °C until the total amine number had fallen to 32 mg KOH / g.

[0124] Example D

[0125] For esterification, 384 g (1.32 mol) of THPED were mixed with 932 g (3.29 mol) of FS2 at 80 °C in a three-neck flask equipped with a stirrer, distillation column, and distillation head. 0.5 g of hypophosphorous acid (50 wt.% in water) was added. The flask was evacuated and the vacuum broken with nitrogen. The mixture was then heated to 195 °C, and water was distilled off at atmospheric pressure for three hours. A vacuum of 20 mbar was applied, and the reaction was continued for 5 hours until the mixture had an acid number of less than 4.9 mg KOH / g and a total amine number of 115.5 mg KOH / g. During the esterification, 17 g of samples were taken.

[0126] In the second step, the resulting esteramine was treated with 209 g (1.66 mol) of DMS, ensuring that the temperature did not exceed 70 °C. The reaction was then continued for 5 hours at 80 °C until the total amine content fell to 34.5 mg KOH / g.

[0127] Comparison examples:

[0128] REWOQUAT® WE 18, which has good softness but low rewetting capacity (“EQ2”; comparative example V2), and comparative example V1 were used as comparisons.

[0129] Comparative Example V1 concerns quaternary ammonium compounds of formula (I) whose fatty acid residues have a non-inventive, low iodine number of 34.

[0130] Comparative Examples E and F are quaternary ammonium compounds of formula (I) whose fatty acid residues have a non-inventive, low iodine number of 80 and 57, respectively.

[0131] Comparative Example V1 - not according to the invention

[0132] For esterification, 343 g (1.18 mol) of THPED were mixed with 804 g (2.94 mol) of FS5 at 80 °C in a three-neck flask equipped with a stirrer, distillation column, and distillation head. 0.4 g of hypophosphorous acid (50 wt.% in water) was added. The flask was evacuated and the vacuum broken with nitrogen. The mixture was then heated to 195 °C, and water was distilled off for three hours at atmospheric pressure. A vacuum of 20 mbar was applied, and the reaction was continued for 5 hours until the mixture had an acid number of 4.4 mg KOH / g and a total amine number of 118 mg KOH / g. During the esterification, 15 g of samples were taken. In the second step, the resulting esteramine was treated with 185 g (1.47 mol) of dimethyl sulfate (DMS) so that the temperature did not exceed 70 °C. The reaction was then continued for 8 hours at 80 °C until the total amine number had fallen to 35.5 mg KOH / g.

[0133] Example E - not according to the invention

[0134] For esterification, 292 g (1 mol) of THPED were mixed with 582 g (2.5 mol) of FS3 at 80 °C in a three-neck flask equipped with a stirrer, distillation column, and distillation head. 0.4 g of hypophosphorous acid (50 wt.% in water) was added. The flask was evacuated and the vacuum broken with nitrogen. The mixture was then heated to 195 °C, and water was distilled off at atmospheric pressure for three hours. A vacuum of 20 mbar was applied, and the reaction was continued for 5 hours until the mixture had an acid number of 4 mg KOH / g and a total amine number of 117 mg KOH / g. During the esterification, 14 g of samples were taken.

[0135] In the second step, the resulting esteramine was treated with 161 g (1.28 mol) of DMS, ensuring that the temperature did not exceed 70 °C. The reaction was then continued for 8 hours at 80 °C until the total amine content fell to 34.8 mg KOH / g.

[0136] Example F - not according to the invention

[0137] For esterification, 299 g (1.02 mol) of THPED were mixed with 714 g (2.55 mol) of FS6 at 80 °C in a three-neck flask equipped with a stirrer, distillation column, and distillation head. 0.4 g of hypophosphorous acid (50 wt.% in water) was added. The flask was evacuated and the vacuum broken with nitrogen. The mixture was then heated to 195 °C, and water was distilled off at atmospheric pressure for three hours. A vacuum of 20 mbar was applied, and the reaction was continued for 5 hours until the mixture had an acid number of 3.2 mg KOH / g and a total amine number of 117 mg KOH / g. During the esterification, 12 g of samples were taken.

[0138] In the second step, the resulting esteramine was treated with 163 g (1.29 mol) of DMS, ensuring that the temperature did not exceed 70 °C. The reaction was then continued for 8 hours at 80 °C until the total amine content fell to 35.9 mg KOH / g.

[0139] 2.2. Production of fabric softener dispersions

[0140] The quaternary ammonium compounds prepared as described in section 2.1 were processed into 6 wt% fabric softener dispersions as follows:

[0141] 750.4 g of water were placed in a 1 l beaker and heated to 55 °C using a hot plate.

[0142] Then, 1.6 g of a dye solution (standard Sandolan Walk Blue) was pipetted in. At a stirring speed of 760 rpm, the respective esterquat, heated to 65 °C, was slowly added. After 20 minutes of stirring, the composition was cooled to <30 °C using an ice-water solution. After 10 minutes, 1.6 g of perfume oil was pipetted in. The pH was adjusted to 2 using 20 wt% hydrochloric acid.

[0143] 2.3 Testing of the

[0144] Cotton terry cloth fabric (company “WFK”; test fabric “WFK 12 A”) with a size of 80 cm x 50 cm and a surface weight of approximately 350 g / m 2were washed twice with heavy-duty detergent at 40°C, rinsed twice, spun, and air-dried in a single layer on a line. The fabric softener dispersions, prepared as described in Section 2.2, were each diluted with cold tap water to form a rinsing solution containing 0.025 wt.% of the respective esterquat. The cotton towels were immersed in two liters of the rinsing solution for 10 minutes. Care was taken to ensure that the towels were evenly wetted by the rinsing solution. The towels were then spun and dried in a single layer on a line at room temperature. The cotton terry towels treated in this way were cut into ten equal pieces measuring 16 cm by 25 cm. To assess the softness, an experienced team of ten testers was assembled to evaluate the anonymized handle samples using a hand panel test. Each tester received their own cotton towel.The assessment was made on a scale from 0 (hard and unpleasant to the touch) to 5 (soft and pleasant to the touch), with the possibility of whole numbers between the two. To assess the softness of the grip, the individual ratings were summed, resulting in a maximum softness of 50 for ten test subjects. In addition, a non-obviously labeled, untreated sample (blank value) was always included with the grip samples. A difference of > 4 between the softness levels was considered significant. The results are summarized in Table 4.

[0145] 2.4 Determination of the re-network capacity

[0146] The rewetting capacity of polyester ("PES") and polyester / cotton ("PES / CO") was determined according to a modified DIN method (53924). The rewetting capacity is expressed as a percentage from 0 to 100.

[0147] 2.4. 1 Principle

[0148] Treating textile fibers with fabric softeners results in a hydrophobic treatment of the fiber surface. This results in a reduced water absorption capacity of the fabric. The aim of the test is to investigate the change in water absorption. The measure of hydrophobic treatment is the height of water rise in the fabric within a specified period of time. The test setup allows for the qualitative comparison of differently treated fabrics from a test series that were prepared and evaluated under the same conditions. Comparisons of results from different test series are not permitted. 2.4.2 General Preparation

[0149] 2.4.2.1 Devices

[0150] • Washing machine

[0151] • Laboratory washer (Linitest)

[0152] • Drying rack

[0153] • Immersion device (own design)

[0154] • Plastic tray (25 x 40 x 10 cm)

[0155] • water-soluble felt-tip pen

[0156] • Precision balance / e.g. Mettler PE 4800

[0157] • Stopwatch

[0158] • 600 ml beakers

[0159] • Magnetic stirrer with stirring bars

[0160] The following test fabric from WFK was used to determine the rewetting capacity:

[0161] Polyester (“PES”)

[0162] Polyester / cotton (“PES / CO”) in a weight ratio of 65% PES to 35% CO.

[0163] The fabric was cut into pieces 25 cm long and 9 cm wide in the warp and weft directions, ensuring that all test pieces in a test series had the same thread orientation. Each test fabric was labeled with a waterproof marker before the start of the test.

[0164] 2.4.2.3. Setting the

[0165] The fabric softener dispersion obtained in Section 2.2 was diluted with hardened water (16°dH) in a beaker so that the concentration of the respective esterquat in the resulting diluted solution was 0.01 wt.%. The solution was homogenized by stirring.

[0166] This diluted solution is the fabric softener.

[0167] 2.4.3 Implementation

[0168] The following are placed in the washing containers of the laboratory washer one after the other:

[0169] 10 steel balls 0 6 mm

[0170] 100 ml fabric softener (stock solution)

[0171] Test fabric 25 x 9 cm (approx. 5 g)

[0172] The blank test was conducted using hardened water. The containers were immediately sealed, placed in the laboratory washer, and rotated for 10 minutes in the laboratory washer's cold water bath. The wet tissues were then removed and left to dry at room temperature for one day.

[0173] The dried test rags are cut into five strips of 25 x 1.5 cm each and then a line is drawn on the smooth side of each strip with a water-soluble felt-tip pen, parallel to the long outer edges.

[0174] The test strips (blank value + test product) were then attached to the immersion device. The lower end of the strip was clamped centrally along the entire length of the clamp. The upper end of the strip was secured with the corresponding clamp on the back so that the strip did not stretch. The immersion device with the strips was inserted into the test tube to a height of 8 cm (approx.

[0175] 10 l) was placed in a tub filled with tap water and left there for five minutes. Ten minutes after removing the immersion device from the tub, the height of the water rise, which was determined by the felt-tip pen ink running, was determined in mm.

[0176] 5. Evaluation

[0177] Experience has shown that slight variations may occur with this method, which must be taken into account in the calculation by specifying the standard deviation.

[0178] Climbing height A in mm x 100% renet capacity (%) = -

[0179] Riser height BW in mm

[0180] BW rise height (mm) of the blank samples in the arithmetic mean

[0181] A Rise height (mm) of the samples of a fabric softener in the arithmetic mean

[0182] Table 4:

[0183] Abbreviations used in Table 4:

[0184] “Ex.” = example;

[0185] “FS / EQ” = fatty acid mixture or esterquat;

[0186] “IZ” = “iodine number;

[0187] “FS / THPED” = moles of fatty acid mixture per mole of THPED;

[0188] “Eq. DMS” = moles of DMS per mole of esterified alkanolamine;

[0189] “WG” = soft grip;

[0190] “RVZZ PES” = return net capacity in % for PES;

[0191] “RVZZ PES ZCO 65Z35” = Re-netting capacity in % for PESZCO 65Z35.

[0192] The results summarized in Table 4 show the following:

[0193] 1) The compositions according to the invention exhibit better rewetting capacity for both PES and PESZCO than all prior art quats. This improvement is achieved, and at the same time, the softness of the compositions according to the invention (with increased rewetting capacity) is in the same range as that of the prior art quats. Thus, the compositions according to the invention exhibit a surprising and significant increase in efficiency as an active ingredient composition or fabric softener composition.

[0194] 2) A comparison of the inventive examples A to D with comparative example E shows that this effect is only achieved with quat compositions in which the iodine number across all esterified fatty acid residues in the composition is at least 100 or higher. Quats or quat compositions with a corresponding iodine number below this, such as those with an iodine number of 89 described in the prior art (US 3,170,938 A, GB 808,265 A, CN 115 745 816 A), exhibit a lower rewetting capacity and are thus less efficient than the compositions according to the invention.

Claims

Claims 1 . Composition Z comprising at least one quaternary ammonium compound of formula (I): where R 1 a divalent, saturated or unsaturated, straight-chain, branched or cyclic hydrocarbon radical having 1 to 6, preferably 2 to 6 carbon atoms, R 2 , R 5 , R 8 , R 11 are each independently selected from the group consisting of divalent, saturated or unsaturated, straight-chain, branched or cyclic hydrocarbon radicals having 1 to 6, preferably 2 to 6, carbon atoms, R 3 , R 6 , R 9 , R 12 independently of each other from the group consisting of hydrogen and alkyl radicals having 1 to 6 carbon atoms, R 4 , R 7 , R 10 , R 13independently of one another from the group consisting of hydrogen and acyl radicals of straight-chain or branched, saturated or unsaturated, preferably at least monounsaturated, fatty acids with a chain length of 16 to 24 carbon atoms, wherein the acyl radicals optionally have at least one OH group, R 14 , R 15 , if present, are independently selected from the group consisting of hydrogen, alkyl radicals having 1 to 6 carbon atoms, X m - is a counter anion which is preferably selected from the group consisting of chloride, bromide, iodide, alkyl sulfate, where the alkyl sulfate is preferably methyl sulfate or ethyl sulfate, alkyl sulfonate, where the alkyl sulfonate is preferably methyl sulfonate, triflate, tosylate, phosphate, sulfate, hydrogen sulfate, lactate, glycolate, acetate, citrate, where X m-more preferably methyl sulfate, where a and b are the same or different, and a = 0 or 1, and b = 0 or 1, with the proviso that a + b = 1 or 2, where n is equal to the sum of a + b, where m is the number of negative charges of X m- is characterized in that one, two, or three, preferably one or two, particularly preferably one, of the radicals R 4 , R 7 , Rio, R13 j ewe j| s is hydrogen, and the iodine number of all radicals R other than hydrogen 4 , R 7 , R 10 , R 13 comprised by the quaternary ammonium compounds of formula (I) in composition Z is at least 100, preferably in the range from 100 to 200, more preferably in the range from 100 to 150, even more preferably in the range from 100 to 120.

2. Composition Z according to claim 1, wherein the at least one quaternary ammonium compound of the formula (I) is characterized in that two, three or four, preferably three or four, particularly preferably all four, of the radicals R 2 , R 5 , R 8 , R 11 are identical, and / or, preferably and, that two, three or four, preferably three or four, particularly preferably all four, of the radicals R 3 , R 6 , R 9 , R 12 are identical.

3. Composition Z according to claim 1 or 2, wherein the at least one quaternary ammonium compound of formula (I) is characterized in that R 1 is selected from the group consisting of butylene, propylene, ethylene, preferably is selected from the group consisting of propylene, ethylene, most preferably R 1 = ethylene.

4. Composition Z according to any one of claims 1 to 3, wherein the at least one quaternary ammonium compound of formula (I) is characterized in that R 2 , R 5 , R 8 , R 11 are each independently selected from the group consisting of butylene, propylene, ethylene, methylene, preferably are each independently selected from the group consisting of propylene, ethylene, methylene, particularly preferably are each methylene.

5. Composition Z according to any one of claims 1 to 4, wherein the at least one quaternary ammonium compound of formula (I) is characterized in that R 3 , R 6 , R 9 , R 12 are each independently selected from the group consisting of methyl, ethyl, propyl, preferably each methyl.

6. Composition Z according to any one of claims 1 to 5, wherein the at least one quaternary ammonium compound of formula (I) is characterized in that R 14 , R 15 are each independently selected from the group consisting of methyl, ethyl, propyl, preferably are each independently selected from the group consisting of ethyl, methyl, particularly preferably are each methyl.

7. Composition Z according to one of claims 1 to 6, wherein the at least one quaternary ammonium compound of formula (I) is characterized in that the radicals R 4 , R 7 , R 10 , R 13which are other than hydrogen, are selected from the acyl residues of the acids selected from ricinoleic acid, isostearic acid, palmitic acid, palmitoleic acid, oleic acid, elaidic acid, vaccenic acid, gadoleic acid, icosenoic acid, gondoic acid, cetoleic acid, erucic acid, margaric acid, stearic acid, arachnic acid, linoleic acid, α-linolenic acid, γ-linolenic acid, calendulic acid, punicic acid, α-elaeostearic acid, β-elaeostearic acid, arachidonic acid, stearidonic acid, preferably are selected from the acyl residues of the acids selected from palmitic acid, stearic acid, oleic acid, linoleic acid, α-linolenic acid, γ-linolenic acid.

8. Composition Z according to one of claims 1 to 7, which is an active ingredient composition, preferably for cleaning fibers and fabrics, particularly preferably a fabric softener active ingredient composition, in which the proportion of all quaternary ammonium compounds of the formula (I), based on the total weight of the composition Z, is at least 50% by weight, preferably 50 to 100% by weight, more preferably 80 to 100% by weight, even more preferably 90 to 100% by weight.

9. Composition Z according to any one of claims 1 to 7, which is a cleaning composition, preferably for cleaning fibers and fabrics, particularly preferably a fabric softener composition, in which the proportion of all quaternary ammonium compounds of the formula (I), based on the total weight of the composition Z, is in the range from 2 to 30% by weight, preferably 3 to 19% by weight, more preferably 5 to 15% by weight.

10. Composition Z according to one of claims 1 to 9, containing at least two different quaternary ammonium compounds of formula (I).

11. Composition Z according to any one of claims 1 to 10, comprising at least one compound of formula (I)*: (IF where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 have the meaning given for formula (I).

12. Composition Z according to claim 11, wherein the ratio of the molar amount of all compounds of formula (I) comprised by composition Z to the molar amount of all compounds of formula (I)* comprised by composition Z is in the range 99:1 to 1:99, preferably in the range 3:2 to 2:3, more preferably in the range 4:3 to 3:4, even more preferably in the range 1:3:1 to 1:

1.

13. Use of a composition Z according to any one of claims 1 to 12 for the treatment of synthetic fabric, preferably polyester fabric and / or polyester blend fabric.

14. Use according to claim 13, characterized in that the synthetic fabric and a cotton-containing fabric are treated therewith simultaneously.

15. Use of a composition Z according to any one of claims 1 to 12 for increasing the softness of fabric or fibers, preferably cotton, compared to the untreated fabric or fiber.

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