EP2046927A1 - Esterquats containing oh groups for improved fragrance effect - Google Patents

Abstract

The invention relates to agents for treating textiles or surfaces, which contain at least one fragrance and at least one esterquat with the general formula (I): [N+ R1 R2 R3 R4] X- that contains an OH group. The invention also relates to the use of agents for treating textiles or surfaces to prolong the fragrant scent of detergents, cleaning agents, fabric softeners, or solid surfaces treated with these agents, and method for producing them.

Description

 "OH-containing esterquats for improved perfume yield"

The invention relates to textile or surface treatment compositions containing at least one fragrance and at least one ester group containing OH groups. The invention also relates to the use of textile or surface treatment agents and to processes for their preparation.

Textile and surface treatment agents usually contain fragrances that give the products a pleasant and fresh smell. The fragrances, which can be both synthetic and natural, usually mask the natural fragrance of the other ingredients in the

Means. Cosmetics, soaps, sanitary ware, textile and surface treatment preparations and others

Products are therefore perfumed to give the consumer a pleasant and clean

Trigger the sensation of smell.

In the detergent sector, fragrances are particularly important components of the composition. The

Laundry should have a pleasant and fresh fragrance both in the wet and in the dry state.

Therefore, it is expedient that fragrances have a good absorption on the fiber and adhere to it, then releasing the fragrances retarding again, so that the

Linger over a long period of time a pleasant fragrance.

The demands on fragrances are therefore quite high.

The fundamental problem with the use of fragrances is that fragrances are volatile substances. This property, however, also causes its scent effect.

It is therefore in the use of fragrances in textile and surface treatment agents before the

Challenge to stabilize these volatile fragrances long enough so that they do not all evaporate within a very short time and no longer produce a fragrance effect. The fragrances should evaporate controlled and thereby cause a long-lasting and constant as possible fragrance effect.

Another problem is the fact that the fragrance of a perfume changes over time, because the fragrances that represent the fresh and light notes of the perfume vaporize faster by their high vapor pressure than the fragrances that represent the heart and base notes.

In the prior art, there are already some proposals to modify fragrances so that they should be released controlled over a longer period of time. For example, perfumes are applied to carrier materials, encapsulated or incorporated into compounds to achieve controlled perfume release.

Another variant is to chemically bind fragrances to other molecules. The bond between perfume and molecule is then split, for example, hydrolytically, whereby the fragrance is then released again delayed. The esterification of perfume alcohols is an example of such chemical modification of perfume molecules. Such compounds are in the state of Technique often referred to as profragrances, pro-accords and the like. There is a wider one

State of the art to the just mentioned different proposals.

Thus, US Pat. No. 6,861,402 describes pro-fragrances which contain a fragrance aldehyde or a fragrance ketone in

Form of an oxazolidine bound. In this case, for example, N-benzene is reacted with a perfume to give a monocyclic oxazolidine

For example, DE-A-1 133 847 relates to the use of the condensation products of aldehydes and ketones with oxiamines in perfumery. These are the aldehydes and ketones with

Implemented ethanolamine or diethanolamine

In the aforementioned patents, the controlled release of perfume over an extended period of time is attempted by the concept of a precursor in the form of so-called profragrances or pro-accords.

However, the Profragrances are quite expensive to synthesize and it is still difficult to control the cleavage kinetics of the substances described therein, so that the release of fragrances is still quite early.

It is therefore an object of the present invention to provide textile or surface treatment agents which induce an improved prolonged fragrance sensation by delayed release (cleavage) of fragrances in the consumer.

Another object of the present invention was to stabilize fragrances so that they better attracted to the fiber and remain adherent, so that the fragrance release over a longer period is made possible.

This object is achieved by textile or surface treatment agents containing at least one fragrance and at least one ester group containing OH groups.

Esterquats have long been known in the art.

The term esterquat stands for a collective name for cationic surface-active

Compounds with two hydrophobic groups that have a quaternized via ester bonds

Di (tri) ethanolamine or an analogous compound are linked.

Esterquats are used as fabric softening agents and have the distearyldimethylammonium chloride, which was previously dominant in this field, because of its unsatisfactory biological

Degradability degraded.

It has now surprisingly been found that OH-containing esterquats according to formula (I) [N ⁺ R ₁ R ₂ R ₃ R ₄ ] X ^'introduced into textile or surface treatment agents, the fragrance yield eg increased to textiles and significantly improves the Duftstoffretardierung , The textile or surface treatment agents according to the invention accordingly comprise at least one fragrance and at least one ester group containing OH groups of the general formula (I) [N ⁺ R ₁ R ₂ R ₃ R ₄ ] X ^" in the

R _{1 is} an alkyl radical having 1 to 4 C atoms or hydroxyalkyl radical having 1 to 4 C atoms, R ₂ , R ₃ , R ₄ are each independently an alkyl radical having 1 to 4 C atoms, hydroxyalkyl radical having 1 to 4 C atoms atoms,

- (CH _{2) m} -A-C (O) -Z or - (CH _{2) m} - C (O) - Z is O, where A is -O, -S-, -NR ₅ - with R ₅ = H or an alkyl radical having 1 to 4 C atoms,

Z is a saturated or unsaturated alkyl radical having 8 to 22 carbon atoms and containing at least one OH group in the side chain, m is an integer in the range from 1 to 3 and X is an anion of an inorganic or organic acid, with the proviso that at least one of R ₂ , R ₃ or R _{4 is} - (CH ₂ ) _m -AC (O) -Z or - (CH ₂ ) _m - C (O) - A-Z.

Preferred hydroxyalkyl radicals here are the hydroxyalkyls with methyl, ethyl, propyl and butyl, most preferably hydroxyethyl or -propyl.

Further preferred compounds are the compounds in the R ₂ , R ₃ and R ₄ , very particularly preferred when R ₂ and R _{3 are} - (CH ₂ ) _m -AC (O) -Z or when only R _{2 is} - ( CH ₂ ) _m -AC (O) -Z, wherein A is preferably -O.

Further preferred compounds are those in which the alkyl radical Z which contains at least one OH group in the side chain is selected from the group consisting of unbranched saturated or unsaturated C ₈ -, C ₉ -, C ₁₀ -, C ₁₁ -, C C ₁₂ , C ₁₃ , C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C ₁₈ , C ₁₉ , C ₂₀ , C ₂₁ , C ₂₂ groups are particularly preferred, but are not branched saturated or unsaturated C ₁₄ , C ₁₅ , C ₁₆ , C ₁₇ , C ₁₈ , C ₁₉ , C ₂₀ , C ₂₁ , C ₂₂ groups, very particularly preferred are non-branched saturated or unsaturated C ₁₆ -, C ₁₇ -, C ₁₈ - groups. In this case, the alkyl radical Z preferably has 0, 1, 2, 3 or 4 double bonds. Most preferably, the alkyl radical Z has 0.1 or 2 double bonds.

In each case, the alkyl chain Z has at least one OH group at any desired point. Particularly preferred are OH groups on a non-branched saturated or unsaturated C ₁₇ - alkyl chain. Preference is given here to OH groups on the C-11 atom of a non-branched saturated or unsaturated C ₁₇ -alkyl chain. In the case of the unsaturated C ₁₇ -alkyl chain, it is most preferred for the double bond to be at the C-8 atom.

Also preferred are OH groups on a non-branched polyunsaturated C ₁₇ - alkyl chain, wherein the double bonds are particularly preferably at the C-8 and C-11 atom. Also preferred are OH groups on a non-branched polyunsaturated C ₁₇ - alkyl chain, wherein the double bonds are particularly preferably at the C-8 and C-11 and C-14 atom. Furthermore, preference is given to OH groups on a non-branched unsaturated C ₂₁ -alkyl chain, particularly preferably the double bond on the C-12 atom.

The OH degree of substitution of the at least one OH group-containing esterquat is thus preferably 1 to 3, very particularly preferably 1.7 to 2.2.

The OH degree of substitution indicates the number of OH groups per side chain in the OH-group-containing esterquat. Preferably, an ester side chain has 1 to 2 OH groups. Accordingly, such an ester quat molecule preferably has six OH groups, more preferably 2 OH groups. Furthermore, such an esterquat molecule can also have a different number of OH groups at different substituents Z. This is especially true in the case where R ₂ , R ₃ and / or R _{4 are} , for example, - (CH ₂ ) _m -AC (O) -Z. Accordingly, the preferred OH substitution degree here is 1.7 to 2.2. The OH degree of substitution in this case represents the average number of OH groups present in the molecule per side chain.

Accordingly, the textile or surface treatment agents according to the invention comprise at least one esterquat which carries an OH group in at least one side chain of the ester. In this case, the total amount of the at least one OH group-containing esterquats zwischent 0.5 to 40 wt.%, Preferably between 2.5 and 30 wt.%, Particularly preferably between 3.5 and 20 wt.% Based on the total amount of the composition.

Preferably, the anion X in formula (I) is an inorganic or organic acid, which may be a halide, sulfate, methosulfate, phosphate, formate, propionate, or acetate. As the halide, the chloride ion is particularly preferred.

Preferred perfumes or perfume oils which can be incorporated into the compositions are not subject to any restrictions. Thus, as perfumes, individual fragrance compounds, both synthetic or natural compounds of the ester type, ethers, aldehydes, ketones, alcohols, hydrocarbons, acids, carbonic esters, aromatic hydrocarbons, aliphatic hydrocarbons, saturated and / or unsaturated hydrocarbons and mixtures thereof can be used. As fragrant aldehydes or Duftketone thereby all usual fragrance aldehydes and fragrance ketones can be used, which are typically used to bring about a pleasant fragrance sensation. Suitable fragrance aldehydes and fragrance ketones are well known to those skilled in the art.

The fragrance ketones can all comprise ketones which can impart a desired fragrance or freshness. It is also possible to use mixtures of different ketones. For example, the ketone may be selected from the group consisting of buccoxime, iso-jasmon, methyl-beta-naphthyl-ketone, musk indanone, tonalid / musk plus, alpha-damascone, beta-damascone, delta-damascone, iso-damascone, damascenone, damarose, Methyl dihydrojasmonate, menthone, carvone, camphor, fenchone, alpha-ion, beta-ionone, dihydro-beta-ionone, gamma-methyl so-called ionone, fleuramon, dihydrojasmon, cis-jasmone, iso-e-super, methyl-cedrenyl ketone or methyl-cedrylon, acetophenone, methyl-acetophenone, para-methoxy-acetophenone, methyl-betaphthyl-ketone, benzyl-acetone, benzophenone, para-hydroxy-phenyl-butanone, Celery ketone or Livescon, 6-isopropyldecahydroxy 2-naphthone, dimethyl octenone, Freskomenth, 4- (1-ethoxyvinyl) -3,3,5,5-tetramethyl cyclohexanone, methyl heptenone, 2- (2- (4-methyl-3-cyclohexene-1 -yl) propyl) cyclopentanone, 1- (p-menthene-6 (2) -yl) -1-propanone, 4- (4-hydroxy-3-methoxyphenyl) -2-butanone, 2-acetyl-3,3 dimethyl norbornane, 6,7-dihydro-1, 1, 2,3,3-pentamethyl-4 (5H) -ind anon, 4-damascol, dulcinyl or cassion, gelson, hexalon, isocyclone E, methyl-cyclocitron, methyl-lavender-ketone, orivone, para-tert-butyl-cyclohexanone, Verdon, Delphon, Muscon, Neobutenon, Plicaton, Velouton, 2 , 4,4,7-Tetramethyl-oct-6-en-3-one, tetrameran, hedione and mixtures thereof. Preferably, the ketones may be selected from alpha Damascon, delta damascone, iso damascone, carvone, gamma-methyl-ionone, iso-E-super, 2,4,4,7-tetramethyl-oct-6-en-3-one, Benzylacetone, Beta Damascone, Damascenone, methyl dihydrojasmonate, methyl cedrylon, hedione and mixtures thereof.

Suitable fragrance aldehydes may be any aldehydes which, in accordance with the fragrance ketones, impart a desired fragrance or sensation of freshness. In turn, they may be individual aldehydes or aldehyde mixtures. Suitable aldehydes are, for example, Melonal, Triplal, Ligustral, Adoxal, Anisaldehyde, Cymal, Ethylvanillin, Florhydral, Floralozon, Helional, Heliotropin, Hydroxycitronellal, Koavon, Laurinaldehyde, Canthoxal, Lyral, Lilial, Adoxal, Anisaldehyde, Cumal Methyl-nonyl-acetaldehyde, Citronellal , Citronellyloxy-acetaldehyde, Cyclamenaldehyde, Bourgeonal, p, t-Bucinal, Phenylacetaldehyde, Undecylenaldehyde, Vanillin; 2,6,10-trimethyl-9-undecenal, 3-dodecene-1-al, alpha-n-amylcinnamaldehyde, 4-methoxybenzaldehyde, benzaldehyde, 3- (4-tert-butylphenyl) -propanal, 2-methyl-3- (para-methoxyphenylpropanal), 2-methyl-4- (2,6,6-trimethyl-2 (1) -cyclohexen-1-yl) butanal, 3-phenyl-2-propenal, cis- / trans-3,7 -Dimethyl-2,6-octadiene-1-al, 3,7-dimethyl-6-octene-1-al, [(3,7-dimethyl-6-octenyl) oxy] acetaldehyde, 4-isopropylbenzyaldehyde, 1, 2 , 3,4,5,6,7,8-octahydro-8,8-dimethyl-2-naphthaldehyde, 2,4-dimethyl-3-cyclohexene-1-carboxyaldehyde, 2-methyl-3- (isopropylphenyl) propanal, Decyl aldehyde, 2,6-dimethyl-5-heptenal; 4- (tricyclo [5.2.1.0.2,6)] decylidene-8) -butanal; Octahydro-4,7-methano-IH-indenecarboxaldehyde; 3-ethoxy-4-hydroxybenzaldehyde, para-ethyl-alpha, alpha dimethylhydrocinnamaldehyde, alpha-methyl-3,4- (methylenedioxy) -hydrocinnamaldehyde, 3,4-methylenedioxybenzaldehyde, alpha-n-hexylcinnamaldehyde, m-cymene-7-carboxaldehyde, alpha-methylphenylacetaldehyde, 7-hydroxy-3,7-dimethyl octanal , Undecenal, 2,4,6-trimethyl-3-cyclohexene-1-carboxaldehyde, 4- (3) (4-methyl-3-pentenyl) -3-cyclohexene-carboxaldehyde, 1-dodecanal, 2,4-dimethylcyclohexene -S-carboxaldehyde, 4- (4-hydroxy-4-methylpentyl) -3-cylohexene-1-carboxaldehyde, 7-methoxy-3,7-dimethyloctan-1-al, 2-methyl undecanal, 2-methyl decanal, 1-nonanal, 1-octanal, 2,6,10-trimethyl-5,9-undecadienal, 2-methyl-3- (4-tert-butyl) propanal, 3- (4-ethylphenyl) -2,2-dimethylpropanal, 3 - (4-methoxyphenyl) -2-methylpropanal, methyl nonylacetaldehyde, 2-phenylpropan-1-al, 3-phenylprop-2-en-1-al, 3-phenyl-2-pentylprop-2-en-1-al, 3-phenyl-2-hexylprop-2-enal, 3- (4-isopropylphenyl) -2-methylpropan-1-al, 3- (4-ethylphenyl) -2,2-dimethylpropan-1-al, 3- (4 tert-butylphenyl) -2-methylpropanal, 3- (3,4-methylenedioxyphenyl) -2-methylpropa n-1-al, 3- (4-ethylphenyl) -2,2-dimethylpropanal, 3- (3-isopropylphenyl) butan-1-al, 2,6-dimethylhept-5-en-1-al, dihydrocinnamaldehyde, 1 -methyl-4- (4-methyl-3-pentenyl) -3-cyclohexene-1-carboxaldehyde, 5 or 6 methoxyhexahydro-4,7-methanoindan-1 or 2-carboxyaldehyde, 3,7-dimethyloctan-1-al, 1-undecanal, 10-undecene-1-al, 4-hydroxy-3-methoxybenzaldehyde, 1-methyl-3- (4-methylpentyl) -3-cyclohexenecarboxyaldehyde, 7-hydroxy-3,7-dimethyl-octanal; trans-4-decenal, 2,6-nonadienal, para-tolylacetaldehyde; 4-methylphenylacetaldehyde, 2-methyl-4- (2,6,6-trimethyl-1-cyclohexen-1-yl) -2-butenal, ortho-methoxycinnamaldehyde, 3,5,6-trimethyl-3-cyclohexenecarboxaldehyde, 3, 7-dimethyl-2-methylene-6-octenal, phenoxyacetaldehyde; 5,9-dimethyl-4,8-decadienal, peony-aldehyde (6,10-dimethyl-3-oxa-5,9-undecadiene-1-al), hexahydro-4,7-methanoindan-1-carboxaldehyde, octanal, 2-methyl octanal, alpha-methyl-4- (1-methylethyl) benzene acetaldehyde, 6,6-dimethyl-2-norpinene-2-propionaldehyde, para methyl phenoxyacetaldehyde, 2-methyl-3-phenyl-2-propene-1 -al, 3,5,5-trimethylhexanal, hexahydro-8,8-dimethyl-2-naphthaldehyde, 3-propyl-bicyclo [2.2.1] -hept-5-ene-2-carbaldehyde, 9-decenal, 3 Methyl 5-phenyl-1-pentanal, methyl nonyl acetaldehyde, 1-p-menthene-q-carboxaldehyde, citral or mixtures thereof, lilial citral, 1-decanal, n-undecanal, n-dodecanal, florhydral, 2,4-dimethyl 3-cyclohexene-1-carboxaldehyde 4-methoxybenzaldehydes, 3-methoxy-4-hydroxybenzaldehydes, 3-ethoxy-4-hydroxybenzaldehydes, 3,4-methylenedioxybenzaldehyde and 3,4-dimethoxybenzaldehyde, and mixtures thereof.

As exemplified above, the fragrance aldehydes and fragrance ketones may have an aliphatic, cycloaliphatic, aromatic, ethylenically unsaturated structure or a combination of these structures. There may also be other heteroatoms or polycyclic structures. The structures may have suitable substituents such as hydroxyl or amino groups.

For other suitable fragrances selected from aldehydes and ketones, see Steffen Arctander Published 1960 and 1969, respectively, Reprinted 2000 ISBN: Aroma Chemicals Vol. 1: 0-931710-37-5, Aroma Chemicals Vol. 2: 0-931710-38 -3, referenced. Suitable fragrance compounds of the ester type are, for example, benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethylbenzylcarbinylacetate (DMBCA), phenylethylacetate, benzylacetate, ethylmethylphenylglycinate, allylcyclohexylpropionate, styrallylpropionate, benzylsalicylate, cyclohexylsalicylate, floramate, melusate and jasmacyclate. Fragrance compounds of the hydrocarbon type are, for example, terpenes such as limonene and pinene. Suitable fragrances of the ether type are, for example, benzyl ethyl ether and ambroxan. Suitable fragrance-containing alcohols are, for example, 10-undecen-1-ol, 2,6-dimethylheptan-2-ol, 2-methylbutanol, 2-methylpentanol, 2-phenoxyethanol, 2-phenylpropanol, 2-tert-butycyclohexanol, 3,5,5- Trimethylcyclohexanol, 3-hexanol, 3-methyl-5-phenylpentanol, 3-octanol, 1-octen-3-ol, 3-phenylpropanol, 4-heptenol, 4-isopropylcyclohexanol, 4-tert-butycyclohexanol, 6,8-dimethyl 2-nonanol, 6-nonen-1-ol, 9-decen-1-ol, alpha-methylbenzylalcohol, alpha-terpineol, amylsalicylate, benzylalcohol, benzylsalicylate, beta-terpineol, butylsalicylate, citronellol, cyclohexylsalicylate, decanol, dihydromyrcenol, dimethylbenzylcarbinol, Dimethylheptanol, dimethyloctanol, ethyl salicylate, ethylvaniline, anethole, eugenol, geraniol, heptanol, hexyl salicylate, isoborneol, isoeugenol, isopulegol, linalool, menthol, myrtenol, n-hexanol, nerol, nonanol, octanol, para-menthane-7-ol, phenylethyl alcohol, Phenol, phenyl salicylate, tetrahydrogeraniol, tetrahydrolinalool, thymol, trans-2-cis-6-nonadienol, trans-2-nonen-1-ol, trans-2-octenol, undecanol, vanillin, cinnamyl alcohol, where, when more fragrance alcohols are present, they may be independently selected.

Fragrances or perfume oils may also be natural fragrance mixtures as are available from vegetable sources, e.g. Pine, citrus, jasmine, patchouly, rose or ylang-ylang oil. Also suitable are Muskateller sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon leaf oil, lime blossom oil, juniper berry oil, vetiver oil, olibanum oil, galbanum oil and labdanum oil and orange blossom oil, neroli oil, orange peel oil and sandalwood oil. essential oils such as angelica root oil, aniseed oil, arnica blossom oil, basil oil, bay oil, champa blossom oil, fir pine oil, pinecone oil, elemi oil, eucalyptus oil, fennel oil, spruce needle oil, galbanum oil, geranium oil, ginger grass oil, guaiac wood oil, guriuri balm oil, helichrysum oil, hol oil, ginger oil, iris oil, cajeput oil, calamus oil , Chamomile oil, camphor oil, kanaga oil, cardamom oil, cassia oil, pine oil, copaϊva balsam, coriander oil, spearmint oil, caraway oil, cumin oil, lavender oil, lemongrass oil, lime oil, tangerine oil, lemon balm oil, musk kernel oil, myrrh oil, clove oil, neroli oil, niaouli oil, olibanum oil, origanum oil, palmarosa oil, patchouli oil , Peruvian balsam oil, Petitgrain oil, Pepper oil, Peppermint oil, Pimento oil, Pine oil, Rose oil, Rosemary oil, Sandalwood oil, Celery oil, Spik oil, Star aniseed oil, Turpentine oil, Thuja oil, Thyme oil, Verbena oil, Vetiver oil, Juniper berry oil, Vermouth oil, Wintergreen oil, Ylang-ylang oil, Hyssop Oil, cinnamon oil, cinnamon oil, lemon oil, Lemon oil and cypress oil.

The total amount of the at least one perfume in the textile or surface treatment agent according to the invention is preferably between 0.01 and 5 wt.%, Particularly preferably between 0.1 and 3% by weight and very particularly preferably between 0.5 and 2

% By weight based on the total amount of the agent.

Preference is given to mixtures of different fragrances (from the various abovementioned

Fragrance classes) which together produce an attractive fragrance note.

In this case, the total amount of the at least one perfume is the amount of all fragrances in the

Blend together based on the total amount of the compound.

In addition to the ester quats already mentioned according to the invention as fabric softening agents, there are further softening components which can likewise be used in the compositions according to the invention.

These include, for example, quaternary ammonium compounds such as

Monoalkyric (s) yltrimethylammonium compounds, dialk (en) yldimethylammonium compounds, mono-,

Di- or triesters of fatty acids with alkanolamines.

Suitable examples of quaternary ammonium compounds are shown, for example, in formulas (II) and (IM):

wherein in (II) R _{5 is} an acyclic alkyl radical having 12 to 24 carbon atoms, R _{6 is} a saturated C ₁ -C ₄ alkyl or hydroxyalkyl radical, R ₇ and R _{8 are} either R ₅ or R ₆ or are an aromatic radical , Y ^" is either a halide, methosulfate, methophosphate or phosphate ion and mixtures of these Examples of cationic compounds of the formula (M) are monotaltrimethylammonium chloride, monostearyltrimethylammonium chloride, didecyldimethylammonium chloride, ditallowdimethylammonium chloride or dihexadecylammonium chloride.

Compounds of formula (IM), (IV) and (V) are so-called ester quats. Esterquats are characterized by excellent biodegradability. In formula (IM) R _{9 is} an aliphatic alk (en) yl radical having 12 to 22 carbon atoms with 0, 1, 2 or 3 double bonds and / or optionally with substituents; R ₁₀ is H, OH or O (CO) Ri ₂ , Rn is, independently of R _10, H, OH or O (CO) Ri ₃ , where Ri ₂ and Ri ₃ are each independently an aliphatic alk (en) yl radical with 12 to 22 carbon atoms with 0, 1, 2 or 3 double bonds, n, p and o can each independently of one another have the value 1, 2 or 3. Y ^~ can either be a halide, Methosulfate, methophosphate or phosphate ion and mixtures of these anions. Preference is given to compounds in which R _{10 is} the group

O (CO) R represents _-I2 . Particularly preferred are compounds in which R _{10 is} the group 0 (CO) R ₁₂ and R ₉ and R _{12 are} alk (en) yl radicals having 16 to 18 carbon atoms. Particular preference is given to compounds in which R 6 additionally represents OH. Examples of compounds of the formula (III) are methyl N- (2-hydroxyethyl) -N, N-di (tallowacyloxyethyl) ammonium methosulfate, bis (palmitoyloxyethyl) -hydroxyethyl-methyl-ammonium methosulfate, 1, 2-bis - [tallowloxy] -3-trimethylammonium propane chloride or methyl N, N-bis (stearoyloxyethyl) -N- (2-hydroxyethyl) ammonium methosulphate.

If quaternized compounds of the formula (III) which have unsaturated alkyl chains are used, the acyl groups whose corresponding fatty acids have an iodine number between 1 and 100, preferably between 5 and 80, more preferably between 10 and 60 and in particular between 15 and 45, are preferred which have a cis / trans isomer ratio (in% by weight) of greater than 30:70, preferably greater than 50:50 and in particular equal to or greater than 60:40. Commercially available examples are the methylhydroxyalkyldialkoyloxyalkylammonium methosulfates sold by Stepan under the trademark Stepantex® or the products from Cognis known under Dehyquart®, the products known from Rewoquat® from Degussa or the products from Kao known from Tetranyl®. Further preferred compounds are the diester quats of the formula (IV) which are obtainable under the name Rewoquat® W 222 LM or CR 3099.

R ₁₄ and R ₁₅ are each independently an aliphatic radical having 12 to 22 carbon atoms with 0, 1, 2 or 3 double bonds.

Instead of the ester group 0 (CO) R, where R is a long-chain alk (en) yl radical, it is possible to use softening compounds which have the following groups: RO (CO), N (CO) R or RN (CO), where of these groups, N (CO) R groups are preferred.

In addition to the quaternary compounds described above, it is also possible to use other compounds as the softening component, for example quaternary imidazolinium compounds of the formula (V),

where R _{16 is} H or a saturated alkyl radical having 1 to 4 carbon atoms, R ₁₇ and R _{18 may} each independently be an aliphatic, saturated or unsaturated alkyl radical having 12 to 18 carbon atoms, R _{17 may} alternatively also be O (CO) R _ig wherein R _{19 is} an aliphatic, saturated or unsaturated alkyl radical having 12 to 18 carbon atoms, and G is an NH group or oxygen and Y ^{~ is} an anion. q can take integer values between 1 and 4.

Further particularly preferred plasticizing compounds are described by formula (VI),

wherein R _20, R ₂₁ and R ₂₂ independently represents a C 1-4 alkyl, alkenyl or hydroxyalkyl group, R ₂₃ and R ₂₄ each selected independently represents a C 8-28 alkyl group, Y is ^an anion and R is an Number is between 0 and 5. A preferred example of a cationic deposition aid according to formula (VI) is 2,3-bis [tallowacyloxy] -3-trimethylammoniumpropane chloride.

Further plasticizing components which can be used according to the invention are quaternized protein hydrolyzates or protonated amines.

Furthermore, cationic polymers are also suitable softening component. Suitable cationic polymers include the polyquaternium polymers as described in the CTFA Cosmetic Ingredient Dictionary (The Cosmetic, Toiletry and Fragrance, Inc., 1997), in particular the Polyquaternium-6, Polyquaternium-7, Polyquaternium, also referred to as Merquats. 10 polymers (Polymer JR, LR and KG series from Amerchol), polyquaternium-4 copolymers such as graft copolymers having a cellulose backbone and quaternary ammonium groups attached via allyldimethylammonium chloride, cationic cellulose derivatives such as cationic guar such as guar hydroxypropyltriammonium chloride, and similar quaternized guar Derivatives (eg Cosmedia Guar from Cognis or the Jaguar series from Rhodia), cationic quaternary sugar derivatives (cationic alkyl polyglucosides), eg the commercial product Glucquat® 100, according to CTFA nomenclature a "Lauryl Methyl Gluceth-10 hydroxypropyl dimonium chlorides", copolymers of PVP and dimethylaminomethacrylate, copolymers of vinylimidazole and vinylpyrrolidone, aminosilicone polymers and copolymers.

Also usable are polyquaternized polymers (eg Luviquat® Care from BASF) and also cationic biopolymers based on chitin and their derivatives, for example the polymer available under the trade name Chitosan® (manufacturer: Cognis). Some of the cited cationic polymers additionally have skin and / or textile care properties.

It is likewise possible to use compounds of the formula (VII)

R ₂₅ can be an aliphatic alk (en) yl radical having 12 to 22 carbon atoms with 0, 1, 2 or 3 double bonds, s can assume values between 0 and 5. R ₂₆ and R ₂₇ are each independently H, C 1-4 alkyl or hydroxyalkyl and Y ^" is an anion.

Other suitable softening components include protonated or quaternized polyamines.

Particularly preferred plasticizing components are alkylated quaternary ammonium compounds of which at least one alkyl chain is interrupted by an ester group and / or amido group. Very particular preference is given to N-methyl-N- (2-hydroxyethyl) -N, N- (ditallowacyloxyethyl) ammonium methosulfate or bis (palmitoyloxyethyl) -hydroxyethyl-methylammonium methosulfate.

The textile treatment agents in the form of fabric softeners may also contain nonionic softening components, especially polyoxyalkylene glycol alkanoates, polybutylenes, long-chain fatty acids, ethoxylated fatty acid ethanolamides, alkyl polyglucosides, in particular sorbitan mono, di- and triesters, and fatty acid esters of polycarboxylic acids,

In the fabric softener according to the invention as a textile treatment agent, the softening component is preferably present in amounts of from 0.1 to 80% by weight, usually from 1 to 40% by weight, preferably from 2 to 20% by weight and in particular from 3 to 15% by weight. , in each case based on the entire textile treatment agent.

As a further component, the textile treatment agents in the form of fabric softeners may optionally contain one or more nonionic surfactants, it being possible to use those which are customarily also used in detergents.

The textile treatment agent may be a detergent, fabric softener, softening detergent or a washing aid, which may be solid or liquid and liquid detergents are preferred. In addition to the fragrances and OH-containing esterquats, the agents according to the invention contain

Form of detergents preferably surfactant (s), wherein anionic, cationic, nonionic, zwitterionic, gemini and / or amphoteric surfactants can be used.

From an application point of view, mixtures of nonionic and cationic are preferred

Surfactants. The total surfactant content of a liquid detergent is preferably below 40

Wt .-% and particularly preferably below 35 wt .-%, based on the total liquid

Laundry detergent.

The nonionic surfactants used are preferably alkoxylated, advantageously ethoxylated, in particular primary, alcohols having preferably 8 to 18 carbon atoms and an average of 1 to 12 moles of ethylene oxide (EO) per mole of alcohol, in which the alcohol residue can be linear or preferably methyl-branched in the 2-position or linear and methyl-branched radicals in the mixture can contain, as they are usually present in Oxoalkoholresten. In particular, however, alcohol ethoxylates with linear radicals of alcohols of native origin having 12 to 18 carbon atoms, for example coconut, palm, tallow or oleyl alcohol, and on average 2 to 8 EO per mole of alcohol are preferred. Examples of preferred ethoxylated alcohols include C12-14 alcohols with 3 EO, 4 EO or 7 EO, C9-1 1 alcohol with 7 EO, C13-15 alcohols with 3 EO, 5 EO, 7 EO or 8 EO, C12-18-alcohols with 3 EO, 5 EO or 7 EO and mixtures of these, such as mixtures of C12-14-alcohol with 3 EO and C12-18-alcohol with 7 EO. The degrees of ethoxylation given represent statistical means which, for a particular product, may be an integer or a fractional number. Preferred alcohol ethoxylates have a narrow homolog distribution (narrow rank ethoxylates, NRE). In addition to these nonionic surfactants, fatty alcohols with more than 12 EO can also be used. Examples of these are tallow fatty alcohol with 14 EO, 25 EO, 30 EO or 40 EO. Nonionic surfactants containing EO and PO groups together in the molecule can also be used according to the invention. Here, block copolymers with EO-PO block units or PO-EO block units can be used, but also EO-PO-EO copolymers or PO-EO-PO copolymers. Of course, it is also possible to use mixed alkoxylated nonionic surfactants in which EO and PO units are not distributed in blocks, but randomly. Such products are available by the simultaneous action of ethylene and propylene oxide on fatty alcohols.

In addition, as further nonionic surfactants and alkyl glycosides of the general formula RO (G) X are used in which R is a primary straight-chain or methyl-branched, especially methyl-branched in the 2-position aliphatic radical having 8 to 22, preferably 12 to 18 carbon atoms, and G is the symbol which represents a glycose unit having 5 or 6 C atoms, preferably glucose. The degree of oligomerization x, which indicates the distribution of monoglycosides and oligoglycosides, is any number between 1 and 10; preferably x is at 1, 2 bis 1, 4. Alkyl glycosides are known, mild surfactants and are therefore preferably used in the surfactant mixture.

Another class of preferred nonionic surfactants used either as the sole nonionic surfactant or in combination with other nonionic surfactants are alkoxylated, preferably ethoxylated or ethoxylated and propoxylated fatty acid alkyl esters, preferably having from 1 to 4 carbon atoms in the alkyl chain, especially fatty acid methyl esters.

Nonionic surfactants of the amine oxide type, for example N-cocoalkyl-N, N-dimethylamine oxide and N-tallowalkyl-N, N-dihydroxyethylamine oxide, and the fatty acid alkanolamides may also be suitable. The amount of these nonionic surfactants is preferably not more than that of the ethoxylated fatty alcohols, especially not more than half thereof.

Further suitable surfactants are polyhydroxy fatty acid amides of the formula (VIII)

R _{28 is} CO for an aliphatic acyl radical having 6 to 22 carbon atoms, R _{29 is} hydrogen, an alkyl or hydroxyalkyl radical having 1 to 4 carbon atoms and [L] is a linear or branched polyhydroxyalkyl radical having 3 to 10 carbon atoms and 3 to 10 hydroxyl groups stands. The polyhydroxy fatty acid amides are known substances which can usually be obtained by reductive amination of a reducing sugar with ammonia, an alkylamine or an alkanolamine and subsequent acylation with a fatty acid, a fatty acid alkyl ester or a fatty acid chloride.

The group of polyhydroxy fatty acid amides also includes compounds of the formula (IX)

R ₃ - _I -O- R ₃₂

IR _3O-CO -N- [M] (IX)

in the R _{30 is} a linear or branched alkyl or alkenyl radical having 7 to 12 carbon atoms, R _{31 is} a linear, branched or cyclic alkyl radical or an aryl radical having 2 to 8 carbon atoms and R _{32 is} a linear, branched or cyclic alkyl radical or a Aryl radical or an oxy-alkyl radical having 1 to 8 carbon atoms, wherein C1-4-alkyl or phenyl radicals are preferred and [M] is a linear polyhydroxyalkyl radical whose alkyl chain is substituted with at least two hydroxyl groups, or alkoxylated, preferably ethoxylated or propoxylated Derivatives of this residue. [M] is preferably obtained by reductive amination of a sugar, for example glucose, fructose, maltose, lactose, galactose, mannose or xylose. The N-alkoxy- or N-aryloxy-substituted compounds can then be converted into the desired polyhydroxy fatty acid amides by reaction with fatty acid methyl esters in the presence of an alkoxide as catalyst.

The content of nonionic surfactants is the textile treatment agents in the form of a liquid detergent preferably 5 to 30 wt .-%, preferably 7 to 20 wt .-% and in particular 9 to 15 wt .-%, each based on the total fabric treatment agent.

As anionic surfactants, for example, those of the sulfonate type and sulfates are used. As surfactants of the sulfonate type, preferably C9-13-alkylbenzenesulfonates, olefin sulfonates, i. Mixtures of alkene and hydroxyalkanesulfonates and disulfonates, as obtained for example from C12-18 monoolefins with terminal or internal double bond by sulfonation with gaseous sulfur trioxide and subsequent alkaline or acidic hydrolysis of the sulfonation products into consideration. Also suitable are alkanesulfonates which are obtained from C12-18-alkanes, for example by sulfochlorination or sulfoxidation with subsequent hydrolysis or neutralization. Likewise suitable are the esters of .alpha.-sulfo fatty acids (ester sulfonates), for example the .alpha.-sulfonated methyl esters of hydrogenated coconut, palm kernel or tallow fatty acids.

Further suitable anionic surfactants are sulfated fatty acid glycerol esters. Fatty acid glycerol esters are to be understood as meaning the mono-, di- and triesters and mixtures thereof, as obtained in the preparation by esterification of a monoglycerol with 1 to 3 moles of fatty acid or in the transesterification of triglycerides with 0.3 to 2 moles of glycerol. Preferred sulfated fatty acid glycerol esters are the sulfonation products of saturated fatty acids having 6 to 22 carbon atoms, for example caproic acid, caprylic acid, capric acid, myristic acid, lauric acid, palmitic acid, stearic acid or behenic acid.

As alk (en) ylsulfate are the alkali and especially the sodium salts of sulfuric acid half esters of C12-C18 fatty alcohols, such as coconut fatty alcohol, tallow, lauryl, myristyl, cetyl or stearyl alcohol or C10-C20 oxo alcohols and those half esters secondary Alcohols of these chain lengths are preferred. Also preferred are alk (en) ylsulfates of said chain length, which contain a synthetic, produced on a petrochemical basis straight-chain alkyl radical, which have an analogous degradation behavior as the adequate compounds based on oleochemical raw materials. Of washing technology interest, C12-C16 alkyl sulfates and C12-C15 alkyl sulfates and C14-C15 alkyl sulfates are preferred. Also 2,3-alkyl sulfates, which as Commercial products of Shell OiI Company under the name DAN® can be obtained are suitable anionic surfactants.

Also, the sulfuric monoesters of ethoxylated with 1 to 6 moles of ethylene oxide straight-chain or branched C7-21 alcohols, such as 2-methyl-branched C9-1 1 alcohols having an average of 3.5 moles of ethylene oxide (EO) or C12-18 fatty alcohols with 1 to 4 EO, are suitable. Due to their high foaming behavior, they are only used in detergents in relatively small amounts, for example in amounts of from 1 to 5% by weight.

Further suitable anionic surfactants are also the salts of alkylsulfosuccinic acid, which are also known as sulfosuccinates or as sulfosuccinic esters and which are monoesters and / or diesters of sulfosuccinic acid with alcohols, preferably fatty alcohols and in particular ethoxylated fatty alcohols. Preferred sulfosuccinates contain C8-18 fatty alcohol residues or mixtures of these. Particularly preferred sulfosuccinates contain a fatty alcohol residue derived from ethoxylated fatty alcohols, which in themselves constitute nonionic surfactants (see description below). Sulfosuccinates, whose fatty alcohol residues are derived from ethoxylated fatty alcohols with a narrow homolog distribution, are again particularly preferred. Likewise, it is also possible to use alk (en) ylsuccinic acid having preferably 8 to 18 carbon atoms in the alk (en) yl chain or salts thereof.

Particularly preferred anionic surfactants are soaps. Suitable are saturated and unsaturated fatty acid soaps, such as the salts of lauric acid, myristic acid, palmitic acid, stearic acid, (hydrogenated) erucic acid and behenic acid and, in particular, soap mixtures derived from natural fatty acids, for example coconut, palm kernel, olive oil or tallow fatty acids.

The anionic surfactants, including the soaps, may be in the form of their sodium, potassium or ammonium salts and as soluble salts of organic bases, such as mono-, di- or triethanolamine. The anionic surfactants are preferably present in the form of their sodium or potassium salts, in particular in the form of the sodium salts.

The content of preferred textile treatment agents in the form of detergents on anionic surfactants is 2 to 30 wt .-%, preferably 4 to 25 wt .-% and in particular 5 to 22 wt .-%, each based on the total fabric treatment agent.

Other suitable surfactants are so-called gemini surfactants. These are generally understood as meaning those compounds which have two hydrophilic groups and two hydrophobic groups per molecule. These groups are usually separated by a so-called "spacer". This spacer is usually a carbon chain that should be long enough that the hydrophilic groups have a sufficient distance so that they can act independently of each other. Such surfactants are generally characterized by an unusually low critical micelle concentration and the ability to greatly reduce the surface tension of the water. In exceptional cases, however, the term gemini surfactants is understood to mean not only dimeric but also trimeric surfactants.

Suitable gemini surfactants are, for example, sulfated hydroxy mixed ethers according to the German patent application DE-A-43 21 022 or dimer alcohol bis- and trimer alcohol tris sulfates and ether sulfates according to the international patent application WO-A-96/23768. End-capped dimeric and trimeric mixed ethers according to the German patent application DE-A-195 13 391 are distinguished in particular by their bi-and multifunctionality. Thus, the end-capped surfactants mentioned have good wetting properties and are low foaming, so that they are particularly suitable for use in machine washing or cleaning processes. However, it is also possible to use gemini-polyhydroxy fatty acid amides or polyoxy-hydroxy fatty acid amides, as described in international patent applications WO-A-95/19953, WO-A-95/199595 and WO-A-95/19955.

Other preferred fabric treatment agents include softening detergents and laundry aids.

Softening detergents are agents that clean and condition textiles treated with them simultaneously. In addition to the surfactants, these also contain a softening component. The softening component may be a cationic or nonionic softening component as defined above, but also a softening clay (eg bentonite).

Detergents are used for targeted pretreatment of the laundry before washing in the event of stains or heavy soiling. The washing aids include, for example, pre-treatment agents, soaking agents, decolorizers and stain remover.

It is further preferred that the agent contains additional conventional ingredients of textile or surface treatment agents.

Thus, in addition to the surfactants and / or softening compounds, the textile treatment agents may contain further ingredients which further improve the performance and / or aesthetic properties of the textile treatment agent. In the context of the present invention, preferred textile treatment agents additionally contain one or more substances from the group of builders, bleaches, bleach activators, enzymes, electrolytes, nonaqueous solvents, pH adjusters, perfumes, perfume carriers, fluorescers, dyes, hydrotopes, foam inhibitors, silicone oils, antiredeposition agents, optical brighteners, grayness inhibitors, anti-shrinkage agents, anti-crease agents, color transfer inhibitors, antimicrobial agents, Germicides, fungicides, antioxidants, preservatives, corrosion inhibitors, antistatic agents, bittering agents, ironing auxiliaries, repellents and impregnating agents, swelling and anti-slip agents, neutral filler salts and UV absorbers.

As builders which may be present in the textile treatment agents, in particular silicates, aluminum silicates (in particular zeolites), carbonates, salts of organic di- and polycarboxylic acids and mixtures of these substances may be mentioned.

Suitable crystalline layered sodium silicates have the general formula NaMSixO2x + 1 .H 2 O, where M is sodium or hydrogen, x is a number from 1, 9 to 4 and y is a number from 0 to 20 and preferred values for x 2, 3 or 4 are. Preferred crystalline layered silicates of the formula given are those in which M is sodium and x assumes the values 2 or 3. In particular, both β- and δ-sodium disilicates Na 2 Si 2 O 5 .yH 2 O are preferred.

It is also possible to use amorphous sodium silicates with a Na 2 O: SiO 2 modulus of from 1: 2 to 1: 3.3, preferably from 1: 2 to 1: 2.8 and in particular from 1: 2 to 1: 2.6, which are delay-delayed and Have secondary washing properties. The dissolution delay compared with conventional amorphous sodium silicates may have been caused in various ways, for example by surface treatment, compounding, compaction / densification or by overdrying. In the context of this invention, the term "amorphous" is also understood to mean "X-ray amorphous". This means that the silicates do not yield sharp X-ray reflections typical of crystalline substances in X-ray diffraction experiments, but at most one or more maxima of the scattered X-rays which have a width of several degrees of diffraction angle. However, it may well even lead to particularly good builder properties if the silicate particles provide blurred or even sharp diffraction maxima in electron diffraction experiments. This is to be interpreted as meaning that the products have microcrystalline regions of size 10 to a few hundred nm, with values of up to a maximum of 50 nm and in particular up to a maximum of 20 nm being preferred. Particularly preferred are compacted / compacted amorphous silicates, compounded amorphous silicates and overdried X-ray amorphous silicates.

The finely crystalline, synthetic and bound water-containing zeolite used is preferably zeolite A and / or P. As zeolite P, zeolite MAP® (commercial product from Crosfield) is particularly preferred. Also suitable, however, are zeolite X and mixtures of A, X and / or P. Commercially available and preferably usable in the context of the present invention is, for example, a cocrystal of zeolite X and zeolite A (about 80% by weight of zeolite X) ) marketed by the company SASOL under the brand name VEGOBOND AX® and by the formula nNa20. (1-n) K20. AI2O3. (2 - 2.5) SiO 2. (3.5 - 5.5) H2O n = 0.90 - 1.0

can be described. The zeolite can be used as a spray-dried powder or else as undried, still moist, stabilized suspension of its preparation. In the event that the zeolite is used as a suspension, it may contain minor additions of nonionic surfactants as stabilizers, for example 1 to 3 wt .-%, based on zeolite, of ethoxylated C12-C18 fatty alcohols having 2 to 5 ethylene oxide groups, C12 C14-fatty alcohols with 4 to 5 ethylene oxide groups or ethoxylated isotridecanols. Suitable zeolites have an average particle size of less than 10 μm (volume distribution, measuring method: Coulter Counter) and preferably contain 18 to 22% by weight, in particular 20 to 22% by weight, of bound water.

Of course, a use of the well-known phosphates as builders is possible, unless such use should not be avoided for environmental reasons. Particularly suitable are the sodium salts of orthophosphates, pyrophosphates and in particular tripolyphosphates.

Organic builders which may be present in the fabric treatment agent include polycarboxylate polymers such as polyacrylates and acrylic acid / maleic acid copolymers, polyaspartates and monomeric polycarboxylates such as citrates, gluconates, succinates or malonates, which are preferably used as the sodium salts.

Among the compounds serving as bleaches in water H2O2, sodium perborate tetrahydrate and sodium perborate monohydrate are of particular importance. Other useful bleaching agents are, for example, sodium percarbonate, peroxypyrophosphates, citrate perhydrates and peroxyacids or peracids which yield H2O2, such as perbenzoates, peroxophthalates, diperazelaic acid, phthaloimino peracid or diperdodecanedioic acid.

In order to achieve an improved bleaching effect during washing at temperatures of 60 ^° C. and below, bleach activators can be incorporated into the detergents and cleaners. As bleach activators, it is possible to use compounds which, under perhydrolysis conditions, give aliphatic peroxycarboxylic acids having preferably 1 to 10 C atoms, in particular 2 to 4 C atoms, and / or optionally substituted perbenzoic acid. Suitable substances are those which carry O- and / or N-acyl groups of the stated C atom number and / or optionally substituted benzoyl groups. Preference is given to polyacylated alkylenediamines, in particular tetraacetylethylenediamine (TAED), acylated triazine derivatives, in particular 1,5-diacetyl-2,4-dioxo hexahydro-1,3,5-triazine (DADHT), acylated glycolurils, in particular tetraacetylglycoluril (TAGU), N-acylimides, in particular N-nonanoylsuccinimide (NOSI), acylated phenolsulphonates, in particular n-nonanoyl or isononanoyloxybenzenesulphonate (n- or iso -NOBS), carboxylic acid anhydrides, especially phthalic anhydride, acylated polyhydric alcohols, especially triacetin, ethylene glycol diacetate and 2,5-diacetoxy-2,5-dihydrofuran.

In addition to the conventional bleach activators or in their place, so-called bleach catalysts can also be incorporated into the fabric treatment agents. These substances are bleach-enhancing transition metal salts or transition metal complexes such as Mn, Fe, Co, Ru or Mo saline complexes or carbonyl complexes. Mn, Fe, Co, Ru, Mo, Ti, V and Cu complexes with nitrogen-containing tripod ligands as well as Co, Fe, Cu and Ru-amine complexes can also be used as bleach catalysts.

A liquid fabric treatment agent may contain a thickener. The thickener may include, for example, a polyacrylate thickener, xanthan gum, gellan gum, guar gum, alginate, carrageenan, carboxymethyl cellulose, bentonites, wellan gum, locust bean gum, agar, tragacanth, gum arabic, pectins, polyoses, starch, dextrins, gelatin and casein include. However, modified natural substances such as modified starches and celluloses, examples which may be mentioned here include carboxymethylcellulose and other cellulose ethers, hydroxyethyl and -propylcellulose and core flour ethers, can be used as thickeners.

Examples of polyacrylic and polymethacrylic thickeners include the high molecular weight homopolymers of acrylic acid crosslinked with a polyalkenyl polyether, in particular an allyl ether of sucrose, pentaerythritol or propylene (INCI name according to the International Dictionary of Cosmetic Ingredients of The Cosmetic, Toiletry and Fragrance Association (CTFA) ": carbomer), also referred to as carboxyvinyl polymers. Such polyacrylic acids are available, inter alia, from 3V Sigma under the trade name Polygel®, for example Polygel DA, and from BF Goodrich under the trade name Carbopol®, for example Carbopol 940 (molecular weight about 4,000,000), Carbopol 941 (molecular weight about 1,250,000) or Carbopol 934 (molecular weight about 3,000,000). Furthermore, the following acrylic acid copolymers are included: (i) Copolymers of two or more monomers from the group of acrylic acid, methacrylic acid and their simple, preferably with C1-4-alkanols formed esters (INCI acrylates copolymer), which include about the copolymers of Methacrylic acid, butyl acrylate and methyl methacrylate (CAS designation according to Chemical Abstracts Service: 25035-69-2) or of butyl acrylate and methyl methacrylate (CAS 25852-37-3) and which are available, for example, from Rohm & Haas under the trade names Aculyn® and Acusol® and from the company Degussa (Goldschmidt) under the trade name Tego® polymer, for example the anionic non-associative polymers Aculyn 22, Aculyn 28, Aculyn 33 (crosslinked), Acusol 810, Acusol 820, Acusol 823 and Acusol 830 (CAS 25852 -37-3); (ii) crosslinked high molecular weight acrylic acid copolymers including such as the crosslinked with an allyl ether of sucrose or pentaerythritol copolymers of C10-30 alkyl acrylates with one or more monomers from the group of acrylic acid, methacrylic acid and their simple, preferably formed with C1-4 alkanols, esters (INCI Acrylates / C 10 -30 alkyl acrylate crosspolymer) and which are available, for example, from BF Goodrich under the trade name Carbopol®, for example the hydrophobic Carbopol ETD 2623 and Carbopol 1382 (INCI acrylates / C 10-30 alkyl acrylate crosspolymer) and Carbopol Aqua 30 ( formerly Carbopol EX 473).

Another preferred polymeric thickener is xanthan gum, a microbial anionic heteropolysaccharide produced by Xanthomonas campestris and some other species under aerobic conditions and having a molecular weight of from 2 to 15 million daltons. Xanthan is formed from a chain of β-1,4-linked glucose (cellulose) with side chains. The structure of the subgroups consists of glucose, mannose, glucuronic acid, acetate and pyruvate, the number of pyruvate units determining the viscosity of the xanthan gum.

In particular, a fatty alcohol is also suitable as thickener. Fatty alcohols may be branched or unbranched, of native origin or of petrochemical origin. Preferred fatty alcohols have a C chain length of 10 to 20 C atoms, preferably 12 to 18. Preference is given to using mixtures of different C chain lengths, such as tallow fatty alcohol or coconut oil fatty alcohol. Examples are Lorol® Spezial (C12-14-ROH) or Lorol® Technical (C12-18-ROH) (both ex Cognis).

Preferred liquid textile treatment agents contain from 0.01 to 3% by weight and preferably from 0.1 to 1% by weight of thickener, based on the total textile treatment agent. The amount of thickener used depends on the type of thickener and the desired degree of thickening.

The fabric treatment agent may contain enzymes in encapsulated form and / or directly in the fabric treatment agent. Suitable enzymes include in particular those from the classes of hydrolases such as proteases, esterases, lipases or lipolytic enzymes, amylases, cellulases or other Glykosylhydrolasen, hemicellulase, cutinases, ß-glucanases, oxidases, peroxidases, perhydrolases and / or laccases and mixtures the enzymes mentioned in question. All of these hydrolases in the wash contribute to the removal of stains such as proteinaceous, greasy or starchy stains and graying. In addition, cellulases and other glycosyl hydrolases may contribute to color retention and to enhancing the softness of the fabric by removing pilling and microfibrils. Oxireductases can also be used for bleaching or inhibiting color transfer. Particularly suitable are from bacterial strains or fungi such as Bacillus subtilis, Bacillus licheniformis, Streptomyceus griseus and Humicola insolens derived enzymatic agents. Preferably, subtilisin-type proteases and in particular proteases derived from Bacillus lentus are used. In this case, enzyme mixtures, for example from protease and amylase or protease and lipase or lipolytic enzymes or protease and cellulase or from cellulase and lipase or lipolytic enzymes or from protease, amylase and lipase or lipolytic enzymes or protease, lipase or lipolytic enzymes and cellulase, but in particular protease and / or lipase-containing mixtures or mixtures with lipolytic enzymes of particular interest. Examples of such lipolytic enzymes are the known cutinases. Peroxidases or oxidases have also proved suitable in some cases. Suitable amylases include in particular α-amylases, iso-amylases, pullulanases and pectinases. As cellulases are preferably cellobiohydrolases, endoglucanases and ß-glucosidases, which are also called cellobiases, or mixtures thereof used. Since different cellulase types differ by their CMCase and avicelase activities, the desired activities can be set by targeted mixtures of the cellulases.

The enzymes may be adsorbed to carriers to protect against premature degradation. The proportion of the enzymes, the enzyme liquid formulation (s) or the enzyme granules directly in the textile treatment agent may, for example, be about 0.01 to 5% by weight, preferably 0.12 to about 2.5% by weight.

However, it may also be preferred, for example in the case of special textile treatment agents for consumers with allergies, that the textile treatment agent contains no enzymes.

As electrolytes from the group of inorganic salts, a wide number of different salts can be used. Preferred cations are the alkali and alkaline earth metals, preferred anions are the halides and sulfates. From a manufacturing point of view, the use of NaCl or MgCl 2 in the textile treatment agents is preferred. The proportion of electrolytes in the textile treatment agent is usually 0.1 to 5 wt .-%.

Non-aqueous solvents which can be used in the liquid textile treatment compositions, for example, from the group of monohydric or polyhydric alcohols, alkanolamines or glycol ethers, provided they are miscible with water in the specified concentration range. The solvents are preferably selected from ethanol, n- or i-propanol, butanols, glycol, propane- or butanediol, glycerol, diglycol, propyl- or butyldiglycol, hexylene glycol, ethylene glycol methyl ether, ethylene glycol ethyl ether, ethylene glycol propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol methyl ether, diethylene glycol ethyl ether, propylene glycol methyl, ethyl or propyl ether, Dipropylene glycol monomethyl or ethyl ether, di-isopropylene glycol monomethyl or ethyl ether, methoxy, ethoxy or butoxy triglycol, 1-butoxyethoxy-2-propanol, 3-methyl-3-methoxybutanol, propylene glycol t-butyl ether and mixtures of these solvents. Non-aqueous solvents may be used in the liquid textile treatment compositions in amounts of between 0.5 and 15 wt .-%, but preferably below 12 wt .-% and in particular below 9 wt .-%.

The viscosity of the textile treatment agents in the form of liquid detergents or fabric softeners can be measured by conventional standard methods (for example Brookfield LVT-II viscosimeter at 20 rpm and 20 ^° C., spindle 3) and is preferably in the range from 500 to 5,000 for liquid detergents mpas. Preferred textile treatment agents in the form of liquid detergents have viscosities of 700 to 4000 mPas, values between 1000 and 3000 mPas being particularly preferred. The viscosity of textile treatment agents in the form of fabric softeners is preferably 20 to 4000 mPas, with values between 40 and 2000 mPas being particularly preferred. The viscosity of fabric softeners is particularly preferably from 40 to 1000 mPas.

In order to bring the pH of the liquid fabric treatment agent in the desired range, the use of pH adjusters may be indicated. Can be used here are all known acids or alkalis, unless their use is not for technical application or environmental reasons or for reasons of consumer protection prohibited. Usually, the amount of these adjusting agents does not exceed 7% by weight of the total formulation.

The pH of the liquid textile treatment agent in the form of a liquid detergent is preferably between 4 and 10 and preferably between 5.5 and 8.5. The pH of the liquid textile treatment agent in the form of a fabric conditioner is preferably between 1 and 6, and preferably between 1, 5 and 3.5.

In order to improve the aesthetic impression of the textile treatment agents, they can be dyed with suitable dyes. Preferred dyes, the selection of which presents no difficulty to the skilled person, have a high storage stability and insensitivity to the other ingredients of the textile treatment agents and to light and no pronounced substantivity to textile fibers so as not to stain them.

Suitable foam inhibitors which can be used in the textile treatment compositions are, for example, soaps, paraffins or silicone oils, which may optionally be applied to support materials.

Suitable soil-release polymers, which are also referred to as "anti-redeposition agents" are, for example, nonionic cellulose ethers such as methyl cellulose and methyl hydroxypropyl cellulose with a proportion of methoxy groups of 15 to 30 wt .-% and of hydroxypropyl groups of 1 to 15 wt .-%, each based on the nonionic cellulose ether and known from the prior art polymers of phthalic acid and / or terephthalic acid or derivatives thereof , in particular polymers of ethylene terephthalates and / or polyethylene and / or polypropylene glycol terephthalates or anionically and / or nonionically modified derivatives of these. Suitable derivatives include the sulfonated derivatives of the phthalic and terephthalic acid polymers.

Optical brighteners (so-called "whiteners") can be added to textile treatment agents to eliminate graying and yellowing of the treated fabrics, which draw on the fiber and cause brightening and fake bleaching action by converting invisible ultraviolet radiation into visible longer wavelength light. wherein the absorbed from sunlight ultraviolet light is radiated as a pale blue fluorescence and the yellow shade of the grayed or yellowed laundry pure white. Suitable compounds originate for example from the substance classes of the 4,4 ^{'diamino-2,2-stilbenedisulfonic} acids ( flavonic), ^'-Distyryl 4,4-biphenylene, Methylumbelliferone, coumarins, dihydroquinolinones, 1, 3- diarylpyrazolines, naphthalimides, benzoxazole, benzisoxazole, and benzimidazole systems, and pyrene derivatives substituted by heterocycles. the optical brighteners are usually added in M tight between 0% and 0.3 wt .-%, based on the finished detergent and cleaner used.

Grayness inhibitors have the task of keeping the dirt detached from the fiber suspended in the liquor and thus preventing the dirt from being rebuilt. Water-soluble colloids of mostly organic nature are suitable for this purpose, for example glue, gelatine, salts of ether sulfonic acids or cellulose or salts of acidic sulfuric acid esters of cellulose or starch. Also, water-soluble polyamides containing acidic groups are suitable for this purpose. It is also possible to use soluble starch preparations and starch products other than those mentioned above, for example degraded starch, aldehyde starches, etc. Polyvinylpyrrolidone is also useful. However, preference is given to using cellulose ethers such as carboxymethylcellulose (Na salt), methylcellulose, hydroxyalkylcellulose and mixed ethers such as methylhydroxyethylcellulose, methylhydroxypropylcellulose, methylcarboxymethylcellulose and mixtures thereof in amounts of from 0.1 to 5% by weight, based on the textile treatment agents.

Since textile fabrics, in particular of rayon, viscose staple, cotton and their mixtures, can tend to wrinkle because the individual fibers are sensitive to bending, buckling, pressing and squeezing transversely to the fiber direction, the detergents and cleaners may contain synthetic crease inhibitors. These include, for example, synthetic products based on fatty acids, fatty acid esters, fatty acid amides, alkylol esters, alkylolamides or fatty alcohols, which are usually reacted with ethylene oxide, or products based on lecithin or modified phosphoric acid esters.

For controlling microorganisms, the textile treatment agents may contain antimicrobial agents. Depending on the antimicrobial spectrum and mechanism of action, a distinction is made between bacteriostats and bactericides, fungistatics and fungicides, etc. Important substances from these groups are, for example, benzalkonium chlorides, alkylarylsulfonates, halophenols and phenolmercuric acetate, and the compounds according to the invention can be completely dispensed with in these detergents and cleaners ,

The textile treatment agents according to the invention may contain preservatives, it being preferred to use only those which have no or only a low skin-sensitizing potential. Examples are sorbic acid and its salts, benzoic acid and its salts, salicylic acid and its salts, phenoxyethanol, 3-iodo-2-propynyl butylcarbamate, sodium N- (hydroxymethyl) glycinate, biphenyl-2-ol and mixtures thereof. A suitable preservative is the solvent-free, aqueous combination of diazolidinyl urea, sodium benzoate and potassium sorbate (available as Euxyl® K 500 ex Schuelke & Mayr), which can be used in a pH range up to 7. In particular, preservatives based on organic acids and / or their salts are suitable for preserving the skin-friendly textile treatment agents according to the invention.

In order to prevent undesirable changes to the textile treatment agents and / or the treated fabrics caused by oxygen and other oxidative processes, the detergents and cleaners may contain antioxidants. This class of compounds includes, for example, substituted phenols, hydroquinones, catechols and aromatic amines, as well as organic sulfides, polysulfides, dithiocarbamates, phosphites, phosphonates and vitamin E.

An increased wearing comfort can result from the additional use of antistatic agents, which are additionally added to the detergents and cleaners. Antistatic agents increase the surface conductivity and thus allow an improved drainage of formed charges. External antistatic agents are generally substances with at least one hydrophilic molecule ligand and give a more or less hygroscopic film on the surfaces. These mostly surface-active antistatic agents can be subdivided into nitrogen-containing (amines, amides, quaternary ammonium compounds), phosphorus-containing (phosphoric acid esters) and sulfur-containing (alkyl sulfonates, alkyl sulfates) antistatic agents. Lauryl (or stearyl) dimethylbenzylammonium chlorides are suitable as antistatics for textile fabrics or as an additive to textile treatment agents, wherein additionally a softening effect is achieved. To improve the rewettability of the treated fabrics and to facilitate the ironing of the treated fabrics, for example, silicone derivatives may be used in the fabric treatment agents. These additionally improve the rinsing behavior of the detergents and cleaning agents by their foam-inhibiting properties. Preferred silicone derivatives are, for example, polydialkyl or alkylaryl siloxanes in which the alkyl groups have one to five carbon atoms and are completely or partially fluorinated. Preferred silicones are polydimethylsiloxanes, which may optionally be derivatized and are then amino-functional or quaternized or have Si-OH, Si-H and / or Si-Cl bonds. The viscosities of the preferred silicones are in the range between 100 and 100,000 mPas at 25 ° C, wherein the silicones in amounts between 0.2 and 5 wt .-%, based on the total washing and cleaning agent can be used.

Finally, the textile treatment agents may also contain UV absorbers which are applied to the treated fabrics and improve the light fastness of the fibers. Compounds having these desired properties include, for example, the non-radiative deactivating compounds and derivatives of benzophenone having substituents in the 2- and / or 4-position. Also suitable are substituted benzotriazoles, phenyl-substituted acrylates (cinnamic acid derivatives) in the 3-position, optionally with cyano groups in the 2-position, salicylates, organic Ni complexes and natural substances such as umbelliferone and the body's own urocanic acid.

In order to avoid the catalyzed by heavy metals decomposition of certain detergent ingredients, substances that complex heavy metals can be used. Suitable heavy metal complexing agents are, for example, the alkali metal salts of ethylenediaminetetraacetic acid (EDTA) or nitrilotriacetic acid (NTA) and alkali metal salts of anionic polyelectrolytes such as polymaleates and polysulfonates.

A preferred class of complexing agents are the phosphonates, which in preferred textile treatment agents in amounts of 0.01 to 2.5 wt .-%, preferably 0.02 to 2 wt .-% and in particular from 0.03 to 1, 5 wt. -% are included. These preferred compounds include in particular organophosphonates such as 1-hydroxyethane-1, 1-diphosphonic acid (HEDP), aminotri (methylenephosphonic acid) (ATMP), diethylenetriamine penta (methylenephosphonic acid) (DTPMP or DETPMP) and 2-phosphonobutane-1,2 , 4-tricarboxylic acid (PBS-AM), which are used mostly in the form of their ammonium or alkali metal salts.

Solid textile treatment agents may additionally contain neutral filler salts such as sodium sulfate. The textile treatment agents according to the invention can be used for cleaning and / or conditioning textile fabrics.

The preparation of the fabric softener as a textile treatment agent can be obtained according to techniques familiar to the person skilled in the art for the preparation of fabric softeners. This can be done for example by mixing the raw materials, optionally using high-shear mixing equipment. It is recommended to melt the softening component (s) and then to disperse the melt in a solvent, preferably water. The other ingredients can be integrated into the softener by simply adding. The preparation of the liquid detergent as a textile treatment agent by means of conventional and known methods and processes in which, for example, the components are simply mixed in stirred tanks, water, non-aqueous solvents and surfactants are conveniently presented and the other ingredients including the OH-containing esterquat are added in portions , Separate heating in the preparation is not required, if desired, the temperature of the mixture should not exceed 80 ^° C.

The textile treatment agents according to the invention are preferably fabric softeners and detergents. Fabric softeners are, in particular, fabric softeners which are used to treat textiles during or after washing.

Detergents can serve the manual or machine washing of particular textiles. It can be detergents or cleaning agents for industrial or household use. Cleaning agents can also be used, for example, for cleaning hard surfaces. These may be, for example, dishwashing detergents used for manual or automatic dishwashing. It can also be common industrial or household cleaners, which are used to clean hard surfaces such as furniture surfaces, tiles, tiles, wall and floor coverings. In addition to tableware, all other hard surfaces, in particular of glass, ceramic, plastic or metal, in household and in trade are also considered hard surfaces.

The textile or surface treatment agents may be solid or liquid formulations, in which case solid formulations may be present as powder, granules, extrudate, in tab form, as tablet or as pressed and / or melted shaped body. Liquid formulations may be solutions, emulsions, dispersions, suspensions, microemulsions, gels or pastes.

As a surface treatment agent, the composition may accordingly contain conventional ingredients of detergents in conventional amounts. For example, surface treatment agents may contain as cleaning agents, alkyl ether sulfates, alkyl and / or aryl sulfonates, alkyl sulfates, amphoteric surfactants, anionic surfactants, nonionic surfactants, cationic surfactants, solvents, thickeners, dicarboxylic (salts) and other auxiliaries and additives.

Some of these additional ingredients have already been explained in detail in the introduction and are also valid for use in detergents (see, for example, nonionic surfactants).

As auxiliaries and additives - especially in hand dishwashing detergents and cleaners for hard surfaces, in particular UV stabilizers, perfume, pearlescing agents (/ Λ / C / Opacifying agents, for example glycol distearate, eg Cutina ^® AGS the company Henkel KGaA, or this containing mixtures, for example the Euperlane ^® from. Henkel KGaA), SRP (soil repellent polymers), PEG-terephthalate, dyes, bleaching agents (eg hydrogen peroxide), corrosion inhibitors, preservatives (for example, the technical also referred to as Bronopol 2-bromo-2-nitropropane -1, 3- diol (CAS 52-51-7) which is commercially available for example as Myacide ^® BT or BT as Boots Bronopol from Boots) as well as skin feel-improving or caring additives (eg dermatologically effective substances, such as vitamin A, Vitamin B2, Vitamin B12, Vitamin C, Vitamin E, D-Panthenol, Sericerin, Collagen Partial Hydrolyzate, Various Vegetable Protein Partial Hydrolyzates, Protein Hydrolyzate Fatty Acid re-condensates, liposomes, polypropylene glycol, Nutrilan ™, chitosan ™, cholesterol, vegetable and animal oils such as lecithin, soybean oil, etc., plant extracts such as aloe vera, azulene, witch hazel extracts, algae extracts, etc., allantoin, AHA complexes) be contained in amounts of usually not more than 5 wt .-%. To increase performance, small amounts of enzymes can be used. Preference is given to proteases (eg BLAP (Henkel), Savinase (NOVO), Durazym (NOVO), Maxapemm, etc.), amylases (eg Fermamyl (NOVO), etc.), lipases (eg Lipolase (NOVO), etc.), Peroxidases, gluconases, cellulases, mannases, etc., in amounts of preferably 0.001 to 1.5%, and more preferably less than 0.5%.

The invention further relates to the use of the textile or surface treatment agent for washing textiles or for cleaning hard surfaces.

Furthermore, the invention relates to the use of the agent for improved perfume yield on textiles or for improved perfume release on textiles or on hard surfaces.

The invention also relates to a method for prolonging the fragrance sensation of detergents or cleaners, fabric softeners or solid surfaces treated with these compositions.

In addition, the invention also relates to a process for the preparation of a textile or surface treatment agent by mixing together at least one fragrance and at least one OH group-containing esterquat according to formula (I). The invention is further illustrated by the following examples.

1. Synthesis of OH-containing Esterquats a) Preparation of Esteramine

Under a nitrogen atmosphere, 0.5 mol of fatty acid with 0.25 mol of diethanolmethylamine (DEMA) in a four-necked flask with KPG stirrer, water and Dimroth condenser and presented with 1 ml

50% hypophosphorous acid added. Subsequently, 25 ml of toluene is added.

In the case of fatty acids, which are solid at room temperature, it is first heated slowly until the

Reaction mixture is melted.

As soon as no more water is separated off, the temperature is raised to 150 ^° C. until the water separation has ended also at this temperature. Then the reaction is stopped and the

Solvent removed under vacuum.

The products solidifying on cooling are filled into a wide beaker. By turning the

Beaker, the product can evenly distribute on solidification on the vessel wall. This is advantageous for the complete removal of the solvent in a vacuum cabinet.

b) quaternization of the esteramine to the esterquat

In a four-necked flask equipped with KPG stirrer, Dimroth condenser, nitrogen inlet tube, temperature sensor and heater mushroom, the esteramine from a) is initially charged and optionally heated to the melt. Subsequently, dimethyl sulfate is added, whereby the reaction temperature rises. As soon as the temperature drops again, stirring is continued at 80 ^° C. for 1 hour. The product subsequently obtained is used without further purification.

2. Analytical determination of the perfume oil yield from detergents a) Perfume oil mixture

It will be a perfume oil mixture

Hexyl acetate, herbbavert, dihydromyrcenol, tetrahydromyrcenol, cyclovertal, linalool, phenylethyl alcohol, citronellol, citral, geraniol, hydroxycitronellal, isobornyl acetate, OTBCA (2-tert-butylcyclohexylacetate), PTBCA (4-tert-butylcyclohexylacetate), aldehyde C12 MNA (2-methylundecanal) , alpha-ionone, acyl, floramate, acetates PA (allylphenoxyacetate), lilial, norlimbanol, hedione, benzophenone, alpha-amylcinnamaldehyde, lyral, Iso E Super (7-acetyl-1, 2,3,4,5,6,7 , 8-octahydro-1, 1, 6,7-tetramethylnaphthalene), cyclohexyl salicylate, habanolides, benzyl salicylate, ethylene brassilate.

All perfume oils are present in equal proportions and can be analytically detected.

b) Textile used:

Terry cloth (bale goods) was used for the textile equipment. 1, 8 kg of the material was mixed with 30 g of commercially available heavy duty detergent in a washing machine from Miele type Novotronic W 363 prewashed at 95 ° C in the Koch program. It was then rinsed 5 times. The toweling was suspended on a leash and dried at 20 ^° C. and 65% relative humidity.

c) Textile equipment:

From the prewashed terry material samples of size 10 x 10 cm were cut (4.8 g

Textile). 3 specimens (moist and dry) per product were prepared.

The liquor ratio substance: treatment solution was 1: 5 whereby the liquor on the

Calculation basis 36 mL fabric softener [15% esterquat, 0.9% above-mentioned perfume oil mixture and 0.2% MgCl 2 ^* 6 H 2 O] / 5 L water.

The prepared specimens were individually placed in flat glass dishes, in the previously 24 g

Treatment liquor was filled and then the treated toweling specimens were spun for one minute in a household laundry spin (1400 revolutions / min.).

The samples, which were to be examined wet, were individually packed in glass bottles immediately after spinning. The rest were stored flat on metal grates, stored in a climate chamber at 20 ⁰ C and 65% relative humidity for 24 hours and then individually packed in glass bottles.

d) analytics:

The wet wipes were directly extracted with pentane using an ASE (accelerated solvent extraction) extraction (ASE). Subsequently, the solution was concentrated at 30 ° C to 2 ml. Thereafter, the samples were analyzed on a 30m DB5MS column (1 micron film thickness) by GC-MS coupling in El mode and parallel FID.

The wipes were then extracted by solid phase extraction (SPE) using the SBSE (Stir Bar Sorptive Extraction) method using a Twister ™ from Gerstel.

The dry cloths were after activation (4h at 80 ⁰ C) extracted in the vapor space

(Enrichment of Twister: 24 h at room temperature).

In the solid phase extraction by adsorption to a solid adsorbent, the concentration of

Analytes in a liquid or in the gas space permanently reduced so that fragrances with very low vapor pressure or very low solubility constantly from the textile fibers in the liquid

/ Gas phase can diffuse after.

The analyzer device here is:

Thermodesorption apparatus (Gerstel) with "TDS 2" autosampler and cold feed system, cooled with liquid nitrogen; #

Gas chromatograph HP 6890 Quadrupole MSD HP 5973 TDS tube: Pyrex glass, 1 = 178 mm, dia = 4 mm Headspace vials: V «22 cm3, aluminum coated Teflon septa After extraction, the samples were thermodisorbed on a 30m DB5MS column (1μm film thickness) by GC-MS coupling in El-mode and parallel FID.

The analytical results are summarized in Table 1.

As can be seen from Table 1, perfumes are better for the textile when treated with agents containing ester groups containing OH groups.

It can be seen from Table 1 that the perfume oil yield on the wet textile by the addition of

OH-containing esterquats according to formula (I) is significantly increased. The content of perfume oil, which then remains on the laundry is accordingly higher than at

Esterquat compounds that do not carry OH groups.

Table I

EQ1 = esterquat of the formula (I) with

R ₂ = -OH ₂ -OH ₂ -OH R ₃ = R ₄ = - (CH ₂ ) _m -AC (O) -Z, where A = -O-, m = 2 and

Z = saturated C ₁₇ -alkyl chain with OH group at the C-11 atom.

EQ2 = esterquat of the formula (I) with

R ₂ ~~ -CH ₂ -CH ₂ -OH Rs = R ₄ = - (CH ₂ ) _m -AC (O) -Z, where A = -O-, m = 2 and

Z = unsaturated C- ₁₇ - alkyl chain with OH group at the C-11-atom, whereby the double bond at the

C-8 atom is located.

3. Olfactory investigations

a) Washing conditions Washing device: Miele Novotronic W 308

Primary wash performance: Single-lye procedure Normal program Cottons

Washing temperature: 40 ⁰ C

Fleet volume: 15 1

Water hardness: 15 ° dH

Linen: 3.5kg of clean linen

Fabric: Terry soap towels

c) Implementation:

The textiles were washed with a detergent, then soft-rinsed with 36 ml softener (composition of the softener: 13% esterquat, 0.9% perfume oil, 0.2%

MgCl ^* 6H 2 O) and dried. A parallel test was carried out with the classic fabric softeners and a fabric softener prepared from the esterquats according to the invention.

For each subject, new rags were made for the initial and 1-week values.

The equipped rags were smelled after drying overnight the next morning

(AW). To assess a long-lasting effect, the lobes were also scented after 7 days. The textiles will be presented to a panel of 30 experts for comparison. The

Evaluation is on a scale of 1-5, where 5 means "very intense odor" and 1 means "barely smell until odorless".

1 no fragrance, barely perceptible

2 little scent perceptible

3 to smell reasonably

4 to smell good

5 to smell very good

Table 2

Rewoquat WE 18 is still comparable to EQ1 and EQ2 in the product and on wet laundry (Table 2). However, after drying Rewoquat WE18 clearly loses to EQ1 and EQ2. The comparison of Rewoquat WE 18 with EQ1 and EQ2 clearly shows here that an OH group on the side chain of the ester of the esterquat leads to an improved fragrance depolymerization in contrast to esterquats without OH groups.

Claims

claims

1. A textile or surface treatment composition containing at least one fragrance and at least one OH-group-containing esterquat of the general formula (I)

[N ⁺ R ₁ R ₂ R ₃ R ₄ ] X ^" in the

R 1 is an alkyl radical having 1 to 4 C atoms or hydroxyalkyl radical having 1 to 4 C atoms,

R2, R3, R4 independently of one another for an alkyl radical having 1 to 4 C atoms, hydroxyalkyl radical having 1 to 4 C atoms or

- (CH _{2) m} -A-C (O) -Z or - (CH _{2) m} - C (O) - Z is O, where A is -O, -S-, -NR ₅ - with R ₅ = H or an alkyl radical having 1 to 4 C atoms,

Z is a saturated or unsaturated alkyl radical having 8 to 22 C atoms, which is at least one

OH group in the side chain contains m for an integer in the range of 1 to 3 and

X represents an anion of an inorganic or organic acid with the proviso that at least one of R2, R3 or R4 represents

- (CH _{2) m} -A-C (O) -Z or - (CH _{2) m} - C (O) - Z is O.

2. Composition according to claim 1, characterized in that the degree of OH-substitution of the at least one OH-group-containing esterquat is 1 to 3, preferably 1, 7 to 2.2.

3. Composition according to one of the preceding claims, characterized in that the alkyl radical Z, which contains at least one OH group in the side chain, is selected from the group consisting of unbranched saturated or unsaturated C ₈ -, Cg-, C ₁₀ - , C ₁₁ -, C ₁₂ -, C ₁₃ -, C ₁₄ -, C ₁₅ -, C ₁₆ -, C _I7 -, C _1S ', C-Ig, C _2O -, C ₂₁ -, C ₂₂ - Groups.

4. Composition according to one of the preceding claims, characterized in that X is selected from the group consisting of halides, sulfates, methosulfates, phosphates, formates, propionates and acetates.

5. Composition according to one of the preceding claims, characterized in that the total amount of the at least one OH-group-containing esterquat between 0.5 and 40 wt.%, Preferably between 2.5 and 30 wt.%, Particularly preferably between 3.5 and 20 wt.% Based on the total amount of the agent.

6. Composition according to one of the preceding claims, characterized in that the total amount of the at least one perfume between 0.01 and 5 wt.%, Preferably between 0.1 and 3 wt.% And particularly preferably between 0.5 and 2 wt. % based on the total amount of the agent.

7. Composition according to one of the preceding claims, characterized in that the perfume is selected from the group consisting of synthetic or natural compounds of the ester type, ethers, aldehydes, ketones, alcohols, hydrocarbons, acids, carbonic acid esters, aromatic hydrocarbons, aliphatic hydrocarbons , saturated and / or unsaturated hydrocarbons and mixtures thereof.

8. Composition according to one of the preceding claims, characterized in that the agent is a detergent, fabric softener, softening detergent or washing aid.

9. Composition according to one of the preceding claims, characterized in that the textile treatment agent is in the form of a detergent or softener and additionally contains at least one surfactant selected from the group consisting of anionic, cationic, nonionic, zwitterionic, amphoteric surfactant or mixtures thereof.

10. Composition according to claim 8, characterized in that the surfactant is a nonionic and / or a cationic surfactant.

11. Composition according to one of the preceding claims, characterized in that the agent contains additional conventional ingredients of textile or surface treatment agents.

12. Composition according to one of the preceding claims, characterized in that the agent is in solid form, preferably as a powder, granules, extrudate, in tab form, as a tablet or as a pressed and / or molten molded body.

13. Composition according to one of the preceding claims, characterized in that the agent is in liquid form, in particular as a solution, emulsion, dispersion, suspension, microemulsion, gel or paste.

14. Use of the agent according to one of the preceding claims for washing textiles.

15. Use of the agent according to one of the preceding claims for cleaning hard surfaces.

16. Use of the agent according to one of the preceding claims for improved perfume yield on textiles.

17. Use of the agent according to one of the preceding claims for improved fragrance release on textiles.

18. A process for preparing an agent according to any one of the preceding claims by at least one fragrance and at least one OH-containing esterquat according to claim 1 are mixed together.