WO2017194331A1

WO2017194331A1 - Use of polyimidazolium salts as dye transfer inhibitors

Info

Publication number: WO2017194331A1
Application number: PCT/EP2017/060180
Authority: WO
Inventors: Catharina WOHLMUTH; Jean-Pierre Berkan LINDNER
Original assignee: Basf Se
Priority date: 2016-05-12
Filing date: 2017-04-28
Publication date: 2017-11-16

Abstract

The use of at least one polymeric, ionic compound comprising imidazolium groups (imidazolium compound), obtainable by reacting • a) at least one a-dicarbonyl compound, • b) at least one aldehyde with one aldehyde group, • c) at least one amino compound having at least two primary amino groups, • d) optionally an amino compound having only one primary amino group and • e) at least one protic acid, and optionally subjecting the reaction product to an anion exchange, wherein the components a) and b) the aldehyde carbonyl groups may also be present as hemiacetal or acetal and the ketone carbonyl groups may also be present as hemiketal or ketal; as dye transfer inhibitor agent. Method for preventing dye transfer during laundry. Method for the preparation of a laundry composition by mixing at least one polymeric, ionic compound which comprises imidazolium groups with a laundry detergent in liquid or solid form.

Description

Use of polyimidazolium salts as dye transfer inhibitors

The present invention relates to the use of polymeric, ionic compounds comprising imidazolium groups as dye transfer inhibitor. Additionally, the invention relates to a method for preventing dye transfer by using polymeric, ionic compounds comprising imidazolium groups.

WO 2010/072571 relates to a method for producing polymeric, ionic imidazolium compounds, characterized in that an a-dicarbonyl compound, an aldehyde, at least one amino compound hav- ing at least two primary amino groups, optionally an amino compound having only one primary amino group, and a protic acid are reacted with each other. It also relates to the use of polymeric, ionic imidazolium compounds as dispersing agents.

PCT/EP2012/055136 relates to compositions and use of compositions comprising at least one polymeric, ionic compound comprising imidazolium groups as biocide, antimicrobial, fungicidal, personal care, and cosmetic composition as well as to methods for combating harmful organisms or fungi. It also relates to use of compositions comprising at least one polymeric, ionic compound comprising imidazolium groups as auxiliary in pharmacy, as surface-active compound, as or in an adhesive or coating for textile, paper, printing and leather industry.

DTI (dye transfer inhibiting) polymers have long been an important constituent of state of the art laundry detergents and cleaners for textiles.

Today, DTI polymers are used in all types of laundry detergents, for example color detergents, heavy-duty detergents, mild detergents, specialty detergents for black textiles, detergents for jeans, and wool detergents. The use concentration of DTI polymers is generally between 0.01 % and 10.0 % by weight, particularly between 0.1 % and 5 % by weight and especially between 0.2 % and 2.0 % by weight of DTI polymer based on the laundry detergent. The laundry detergents in which DTI polymers are used can be in solid form, for example in the form of powders, granules, pellets, tablets, bar soaps, in semi-liquid form, for example in the form of gels or pastes, or in liquid form.

To use the DTI polymers in laundry detergent and cleaner compositions, as well as in other fields of use, they are on offer as aqueous solutions or in solid form, as powders or granules.

The function of DTI polymers is to bind dyes which bleed during the washing of coloured textiles and so prevent their redeposition on white or differently coloured textiles also present in the wash, and thereby protect the latter from tainting or staining. The problem of textile dyeing's bleeding arises particularly in the case of intensively coloured textiles and here more particularly from the use of direct or substantive dyes. But other classes of dyes, such as reactive dyes, can also be the cause of bleeding if, for cost reasons for example, the dyeing operation is not concluded with an adequate after treatment of the textile (washing off, application of dye fixatives). Some textile dyes such as diazo-dyes like Acid Blue 1 13 (CAS Number 3351 -05-1 ; formula (I)) are known to be especially hard to prevent from redepositioning.

It is an object of the present invention to identify DTI polymers which can be used for dye transfer inhibition in laundry applications with improved dye transfers inhibiting properties, especially with improved dye transfer inhibiting properties towards diazo-dyes such as Acid Blue 1 13. Such DTI polymers need to be applicable in laundry compositions in both liquid and solid dosage form.

Based on these objectives the methods and uses of the following compositions were identified.

Generally, as used herein, the term "obtainable by" means that corresponding products do not necessarily have to be produced {i.e. obtained) by the corresponding method or process de- scribed in the respective specific context, but also products are comprised which exhibit all features of a product produced (obtained) by said corresponding method or process, wherein said products were actually not produced (obtained) by such method or process. However, the term "obtainable by" also comprises the more limiting term "obtained by", i.e. products which were actually produced (obtained) by a method or process described in the respective specific context.

In a first aspect, the invention relates to the use of a composition, comprising at least one polymeric, ionic compound comprising imidazolium groups (imidazolium compound), obtainable by reacting a) at least one a-dicarbonyl compound,

b) at least one aldehyde with one aldehyde group,

c) at least one amino compound having at least two primary amino groups, d) optionally an amino compound having only one primary amino group and

e) at least one protic acid, and optionally subjecting the reaction product to an anion exchange, wherein the components a) and b) the aldehyde carbonyl groups may also be present as hemi- acetal or acetal and the ketone carbonyl groups may also be present as hemiketal or ketal; where the main chain of the at least one compound comprising imidazolium groups does not contain 1 ,4-bound phenylene rings and specifically does not contain phenylene rings.

In one embodiment the amino compound having at least two primary amino groups is not 1 ,3- diamino-2-hydroxy-propane or 1 ,3-diamino-2-hydroxy-2-methyl-propane. In a further embodiment, the main chain of the at least one imidazolium compound does not contain quaternary ammonium groups of the formula -(N⁺R^AR^B)-, wherein R^A and R^B may have the same or different meanings, selected from alkyl, monohydroxyalkyl and polyhydroxyalkyl.

In another aspect the invention relates to a method for preventing dye transfer during laundry, wherein at least one polymeric, ionic compound is used which comprises imidazolium groups (imidazolium compound), obtainable by reacting a) at least one a-dicarbonyl compound,

b) at least one aldehyde with one aldehyde group,

c) at least one amino compound having at least two primary amino groups,

d) optionally an amino compound having only one primary amino group and

e) at least one protic acid, and optionally subjecting the reaction product to an anion exchange, where in the components a) and b) the aldehyde carbonyl groups may also be present as hemi- acetal or acetal and the ketone carbonyl groups may also be present as hemiketal or ketal; by bringing the polymeric, ionic compound in contact with laundry.

In another aspect the invention relates to a method for preparation of a laundry composition by mixing at least one polymeric, ionic compound which comprises imidazolium groups (imidazolium compound), obtainable by reacting a) at least one a-dicarbonyl compound, b) at least one aldehyde with one aldehyde group,

c) at least one amino compound having at least two primary amino groups,

d) optionally an amino compound having only one primary amino group and

e) at least one protic acid, and optionally subjecting the reaction product to an anion exchange, where in the components a) and b) the aldehyde carbonyl groups may also be present as hemi- acetal or acetal and the ketone carbonyl groups may also be present as hemiketal or ketal; with a laundry detergent, wherein the laundry composition has dye transfer inhibiting properties. In the context of the present invention, the expression "alkyi" comprises straight-chain or branched alkyi groups. Alkyi is preferably Ci-C3o-alkyl, more preferably Ci-C2o-alkyl even more preferably Ci-Ci2-alkyl and in particular Ci-C6-alkyl. Examples of alkyi groups are especially methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, neo-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-hex- adecyl, n-octadecyl and n-eicosyl.

Examples for Ci-C6-alkyl are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert- butyl, n-pentyl, neo-pentyl, n-hexyl, and position isomers thereof. Examples for Ci-Ci2-alkyl are, apart those mentioned above for Ci-C6-alkyl, n-heptyl, n-octyl, 2- ethylhexyl, n-nonyl, n-decyl, 2-propylheptyl, n-undecyl, n-dodecyl and position isomers thereof.

Examples for Ci-C2o-alkyl are, apart those mentioned above for Ci-Ci2-alkyl, n-tridecyl, n-tetradecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl and position iso- mers thereof.

Examples for Ci-C3o-alkyl are, apart those mentioned above for Ci-C2o,-alkyl, n-henicosyl, n-do- cosy, n-tricosyl, n-tetracosy, n-pentacosyl, n-hexacosyl, n-octacosy, n-nonacosyl, n-triacontyl and position isomers thereof.

The expression alkyi also comprises alkyi radicals whose carbon chains may be interrupted by one or more nonadjacent groups which are selected from -0-, -S-, -NR^b- , -C(=0)-, -S(=0)- and/or -S(=0)2-. R^b is preferably hydrogen, alkyi, cycloalkyl aryl or a group -f CH2CH₂-0}y-R^c- wherein y is 1 , 2, 3, 4, 5 or 6 and R^c is hydrogen or Ci-C4-alkyl. Preferably how- ever, the term alkyi does not comprise alkyi radicals whose carbon chains may be interrupted by one or more nonadjacent groups which are selected from -0-, -S-, -NR^b- , -C(=0)-, -S(=0)- and/or -S(=0)2- unless explicitly specified. Substituted alkyi groups may, depending on the length of the alkyi chain, have one or more (e.g. 1 , 2, 3, 4, 5 or more than 5) substituents. These are preferably each independently selected from cycloalkyl, aryl, fluorine, chlorine, bromine, hydroxyl, mercapto, cyano, nitro, nitroso, formyl, acyl, COOH, carboxylate, alkylcarbonyloxy, carbamoyl, SO3H, sulfonate, sulfamino, sul- famide, amidino, NE¹E², where E¹ and E² are each independently hydrogen, alkyi, cycloalkyl or aryl. Cycloalkyl and aryl substituents of the alkyi groups may in turn be unsubstituted or substituted; suitable substituents are the substituents mentioned below for these groups.

The above remarks regarding alkyi also apply to the alkyi moiety in alkoxy (an alkyi radical bound via an oxygen atom to the remainder of the molecule) and alkylthio (= alkylsulfanyl; an alkyi radical bound via a sulfur atom to the remainder of the molecule).

Examples for Ci-C6-alkoxy are methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, neo-pentoxy, n-hexoxy, and position isomers thereof.

Examples for Ci-C2o-alkoxy are, apart those mentioned above for Ci-C6-alkoxy, n-heptoxy, n- octyloxy, n-nonyloxy, n-decyloxy, n-undecyloxy, n-dodecyloxy, n-tridecyloxy, n-tetradecyloxy, n- pentadecyloxy, n-hexadecyloxy, n-heptadecyloxy, n-octadecyloxy, n-nonadecyloxy, n-do- cosyloxy and position isomers thereof.

Examples for Ci-C6-alkylthio are methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, n-pentylthio, neo-pentylthio, n-hexylthio, and position isomers thereof. Examples for Ci-C2o-alkylthio are, apart those mentioned above for Ci-C6-alkyl, n-heptylthio, n- octylthio, 2-ethylhexylthio, n-nonylthio, n-decylthio, 2-propylheptylthio, n-undecylthio, n-do- decylthio, n-tridecylthio, n-tetradecylthio, n-hexadecylthio, n-heptadecylthio, n-octadecylthio, n- nonadecylthio, n-eicosylthio and position isomers thereof. In the context of the present invention, the term "cycloalkyl" denotes a mono-, bi- or tricyclic hydrocarbon radical having usually from 3 to 20 ("C3-C2o-cycloalkyl"), preferably 3 to 12 ("C3-C12- cycloalkyl"), more preferably 3 to 10 ("C₃-Cio-cycloalkyl"), in particular 3 to 8 ("C₃-C₈-cycloalkyl"), e.g. 5 to 8 ("C₅-Cs-cycloalkyl"), carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl, cyclo- hexyl, cycloheptyl, cyclooctyl, cyclododecyl, cyclopentadecyl, norbornyl, bicyclo[2.2.2]octyl or adamantyl.

Preferably, the term cycloalkyl denotes a monocyclic hydrocarbon radical.

Examples for Cs-Cs-cycloalkyl are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. Substituted cycloalkyi groups may, depending on the ring size, have one or more (e.g. 1 , 2, 3, 4, 5 or more than 5) substituents. These are preferably each independently selected from alkyl, alkoxy, alkylthio, cycloalkyi, aryl, fluorine, chlorine, bromine, hydroxyl, mercapto, cyano, nitro, nitroso, formyl, acyl, COOH, carboxylate, alkylcarbonyloxy, carbamoyl, SO3H, sulfonate, sul- famino, sulfamide, amidino, NE³E⁴, where E³ and E⁴ are each independently hydrogen, alkyl, cycloalkyi or aryl. In the case of substitution, the cycloalkyi groups preferably bear one or more, for example one, two, three, four or five, Ci-C6-alkyl groups.

The above remarks regarding cycloalkyi also apply to the cycloalkyi moiety in cycloalkoxy (a cy- cloalkyl radical bound via an oxygen atom to the remainder of the molecule) and cycloalkylthio (= cycloalkylsulfanyl; a cycloalkyi radical bound via a sulfur atom to the remainder of the molecule).

Examples for Cs-Cs-cycloalkoxy are cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexoxy, cy- cloheptoxy and cyclooctoxy.

Examples for Cs-Cs-cycloalkylthio are cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohex- ylthio, cycloheptylthio and cyclooctylthio. In the context of the present invention, the term "aryl" refers to mono- or polycyclic aromatic hydrocarbon radicals. Aryl usually is an aromatic radical having 6 to 24 carbon atoms, preferably 6 to 20 carbon atoms, especially 6 to 14 carbon atoms as ring members. Aryl is preferably phenyl, naphthyl, indenyl, fluorenyl, anthracenyl, phenanthrenyl, naphthacenyl, chrysenyl, pyrenyl, coro- nenyl, perylenyl, etc., and more preferably phenyl or naphthyl. Specifically, aryl is phenyl.

Substituted aryls may, depending on the number and size of their ring systems, have one or more (e.g. 1 , 2, 3, 4, 5 or more than 5) substituents. These are preferably each independently selected from alkyl, alkoxy, alkylthio, cycloalkyi, aryl, fluorine, chlorine, bromine, hydroxyl, mercapto, cyano, nitro, nitroso, formyl, acyl, COOH, carboxylate, alkylcarbonyloxy, carbamoyl, SO3H, sulfonate, sulfamino, sulfamide, amidino, NE⁵E⁶, where E⁵ and E⁶ are each independently hydrogen, alkyl, cycloalkyi, heterocycloalkyl, aryl or hetaryl. The alkyl, alkoxy, alkylthio, cycloalkyi and aryl substituents on the aryl may in turn be unsubstituted or substituted. Reference is made to the substituents mentioned above for these groups. The substituents on the aryl are preferably selected from alkyl and alkoxy. Substituted aryl is more preferably substi- tuted phenyl which generally bears 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, substituents.

Substituted aryl is preferably aryl substituted by at least one alkyl group ("alkaryl", also referred to hereinafter as alkylaryl). Alkaryl groups may, depending on the size of the aromatic ring system, have one or more (e.g. 1 , 2, 3, 4, 5, 6, 7, 8, 9 or more than 9) alkyl substituents. The alkyl substituents may be unsubstituted or substituted. In this regard, reference is made to the above statements regarding unsubstituted and substituted alkyl. In a preferred embodiment, the alkaryl groups have exclusively unsubstituted alkyl substituents. Alkaryl is preferably phenyl which bears 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, more preferably 1 or 2, alkyl substituents.

Aryl which bears one or more radicals is, for example, 2-, 3- and 4-methylphenyl, 2,4-, 2,5-, 3,5- and 2,6-dimethylphenyl, 2,4,6-trimethylphenyl, 2-, 3- and 4-ethylphenyl, 2,4-, 2,5-, 3,5- and 2,6- diethylphenyl, 2,4,6-triethylphenyl, 2-, 3- and 4-propylphenyl, 2,4-, 2,5-, 3,5- and 2,6-di- propylphenyl, 2,4,6-tripropylphenyl, 2-, 3- and 4-isopropylphenyl, 2,4-, 2,5-, 3,5- and 2,6-diiso- propylphenyl, 2,4,6-triisopropylphenyl, 2-, 3- and 4-butylphenyl, 2,4-, 2,5-, 3,5- and 2,6-dibu- tylphenyl, 2,4,6-tributylphenyl, 2-, 3- and 4-isobutylphenyl, 2,4-, 2,5-, 3,5- and 2,6-diisobu- tylphenyl, 2,4,6-triisobutylphenyl, 2-, 3- and 4-sec-butylphenyl, 2,4-, 2,5-, 3,5- and 2,6-di-sec- butylphenyl, 2,4,6-tri-sec-butylphenyl, 2-, 3- and 4-tert-butylphenyl, 2,4-, 2,5-, 3,5- and 2,6-di- tert-butylphenyl and 2,4,6-tri-tert-butylphenyl; 2-, 3- and 4-methoxyphenyl, 2,4-, 2,5-, 3,5- and 2,6-dimethoxyphenyl, 2,4,6-trimethoxyphenyl, 2-, 3- and 4-ethoxyphenyl, 2,4-, 2,5-, 3,5- and 2,6-diethoxyphenyl, 2,4,6-triethoxyphenyl, 2-, 3- and 4-propoxyphenyl, 2,4-, 2,5-, 3,5- and 2,6-dipropoxyphenyl, 2-, 3- and 4-isopropoxyphenyl, 2,4-, 2,5-, 3,5- and 2,6-diisopropoxyphenyl and 2-, 3- and 4-butoxyphenyl.

The above remarks regarding aryl also apply to the aryl moiety in aryloxy (an aryl radical bound via an oxygen atom to the remainder of the molecule) and arylthio (= arylsulfanyl; an aryl radical bound via a sulfur atom to the remainder of the molecule).

The term alkylene refers to a linear or branched diradical of an alkane (or, in other words, a divalent alkyl radical). C2-C3-Alkylene is a linear or branched divalent alkyl radical having 2 or 3 carbon atoms. Examples are 1 ,1-ethylene [CH(CH₃)], 1 ,2-ethylene (CH₂CH₂), 1 ,1-propylene [CH(CH₂CH₃)], 2,2-pro- pylene [ -C(CH₃)₂-], 1 ,2-propylene [CH₂CH(CH₃)] or 1 ,3-propylene (CH₂CH₂CH₂).

Ci-C₃-Alkylene is a linear or branched divalent alkyl radical having 1 , 2 or 3 carbon atoms. Ex- amples are, apart those mentioned above for C₂-C₃-alkylene, also methylene (CH₂).

C₂-C6-Alkylene is a linear or branched divalent alkyl radical having 2, 3, 4, 5 or 6 carbon atoms. Examples are, apart those mentioned above for C₂-C₃-alkylene, n-butylene [(CH₂)₄],

[(CH₂)₃CH(CH₃)], (CH₂CH(CH₃)CH₂), [CH(CH₂CH₂CH₃)], [CH₂CH(CH₂CH₃)], [-C(CH₃)₂CH₂-], n- pentylene [(CH₂)₅], n-hexylene [hexamethylene; (CH₂)6] and position isomers thereof.

Ci-C6-Alkylene is a linear or branched divalent alkyl radical having 1 , 2, 3, 4, 5 or 6 carbon atoms. Examples are, apart from the examples mentioned above for C₂-C6-alkylene, also methylene (CH₂).

Ci-C₃o-Alkylene is a linear or branched divalent alkyl radical having 1 to 30 carbon atoms. Examples for Ci-C₃o-alkylene are, apart from the examples mentioned above for Ci-C6-alkylene, diradicals (CH2)x, wherein x is an integer from 7 to 30, such as heptamethylene, octamethylene, nonamethylene, decamethylene and the like, and position isomers thereof.

C₄-Ci2-Alkylene is a linear or branched divalent alkyl radical having 4 to 12 carbon atoms. Ex- amples for C₄-Ci₂-alkylene are n-butylene [(CH₂)₄], [(CH₂)₃CH(CH₃)], (CH₂CH(CH₃)CH₂),

[CH(CH₂CH₂CH₃)], [CH₂CH(CH₂CH₃)], [-C(CH₃)₂CH₂-], n-pentylene [(CH₂)₅], n-hexylene [hexa- methylene; (CH₂)6], heptamethylene, octamethylene, nonamethylene, decamethylene, undeca- methylene, dodecamethylene, and position isomers thereof. C₄-C₂o-Alkylene is a linear or branched divalent alkyl radical having 4 to 20 carbon atoms. Examples for C₄-C₂o-alkylene are, apart from the examples mentioned above for C₄-Ci₂-alkylene, diradicals (CH₂)_X, wherein x is an integer from 13 to 20, and position isomers thereof.

C₃-C₂o-Alkylene is a linear or branched divalent alkyl radical having 3 to 20 carbon atoms. Ex- amples for C₃-C₂o-alkylene are, apart from the examples mentioned above for C₄-C₂o-alkylene, 1 ,1 -propylene [CH(CH₂CH₃)], 2,2-propylene [ -C(CH₃)₂-], 1 ,2-propylene [CH₂CH(CH₃)] or 1 ,3- propylene (CH₂CH₂CH₂).

Alkenylene is a linear or branched aliphatic mono- or poly-, e.g. mono- or di-, olefinically unsatu- rated divalent radical having, for example, 2 to 20 or 2 to 10 or 4 to 8 carbon atoms. If the radical comprises more than one carbon-carbon double bond, these are preferably not vicinal, i.e. not allenic.

Alkynylene is a linear or branched aliphatic divalent radical having, for example, 2 to 20 or 2 to 10 or 4 to 8 carbon atoms which comprises one or more, e.g. 1 or 2, carbon-carbon triple bonds.

Cs-Cs-Cycloalkylene is a divalent monocyclic, saturated hydrocarbon group having 5 to 8 carbon ring members. Examples are cyclopentane-1 ,2-diyl, cyclopentane-1 ,3-diyl, cyclohexane-1 ,2-diyl, cyclohexane-1 ,3-diyl, cyclohexane-1 ,4-diyl, cycloheptane-1 ,2-diyl, cycloheptane-1 ,3-diyl, cyclo- heptane-1 ,4-diyl, cyclooctane-1 ,2-diyl, cyclooctane-1 ,3-diyl, cyclooctane-1 ,4-diyl and cyclooc- tane-1 ,5-diyl.

Carboxylate and sulfonate respectively represent a derivative of a carboxylic acid function and a sulfonic acid function, especially a metal carboxylate or sulfonate, a carboxylic ester or sulfonic ester function or a carboxamide or sulfonamide function.

In context of the radical A (see below) being an alkylene group which may be substituted by a carboxylate group, this term is limited to a carboxylate anion (COO).

The expression "halogen" denotes in each case fluorine, bromine, chlorine or iodine, particularly chlorine, bromide or iodine. Imidazolium compound

Suitable imidazolium compounds for the use as dye transfer inhibitor agent according to the invention and methods for dye transfer inhibition during laundry and for preparation of a laundry composition are described in WO 2010/072571 , which is incorporated herein by reference. Accordingly, the imidazolium compounds can be obtained by a polycondensation reaction of at least one a-dicarbonyl compound, at least one aldehyde with one aldehyde group, at least one amino compound having at least two primary amino groups and at least one protic acid as essential starting materials. In a polycondensation, polymerization occurs with elimination of a low molecular weight compound, such as water or alcohol. In the present case, water is eliminated. When the carbonyl groups of the α-dicarbonyl compound are present completely or partly as ketal and/or the aldehyde group of the aldehyde is present as acetal or hemiacetal, an alcohol is correspondingly eliminated instead of water. a) α-dicarbonyl compound

The α-dicarbonyl compound is preferably selected from compounds of the formula (II)

R¹-CO-CO-R² (II)

wherein

R¹ and R² are independently selected from hydrogen and in each case unsubstituted or substituted alkyl, alkoxy, alkylthio, cycloalkyl, cycloalkoxy, cycloalkylthio, aryl, aryloxy, arylthio. Preferably, R¹ and R² are independently selected from hydrogen and in each case unsubstituted or substituted alkyl, cycloalkyl and aryl and more preferably from hydrogen and in each case unsubstituted or substituted Ci-C2o-alkyl, Cs-Cs-cycloalkyl and aryl.

The α-dicarbonyl compound a) preferably is selected from the group consisting of glyoxal, a hemiacetal, and acetal thereof. Thus, in particular R¹ and R² are hydrogen.

The aldehyde or keto group of the compound a) can also be present as hemiacetal, acetal, hemiketal or ketal, preferably of a lower alcohol, in particular a Ci-Cio-alkanol. In this case, the alcohol is eliminated in the condensation reaction forming the imidazolium compound. Preferably, the compound a) is not employed in form of a hemiacetal, acetal, hemiketal or ketal. b) Aldehyde

The aldehyde with one aldehyde group b) is different from the α-dicarbonyl compound a) and is preferably selected from compounds of the formula (III)

R³-CHO (III) wherein

R³ is selected from hydrogen, alkyl, cycloalkyl and aryl. Preferably, R³ is selected from hydrogen, Ci-C2o-alkyl, Cs-Cs-cycloalkyl, optionally substituted aryl and a radical of the formula -Chb-fO-ChbCHzfx-OR³, wherein x is 1 , 2, 3, 4, 5 or 6 and R^a is hydrogen or Ci-C4-alkyl, and is more preferably selected from hydrogen, Ci-C2o-alkyl, a group - CH2-fO-CH₂CHzfx-OR^a, wherein x is 1 , 2, 3, 4, 5 or 6 and R^a is hydrogen or Ci-C₄-alkyl and phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals selected from Ci-C2o-alkyl, Ci-C6-haloal- kyl, Ci-C2o-alkoxy, Ci-C6-haloalkoxy and NR'R", where R' and R'R" are, independently of each other, selected from hydrogen and Ci-C6-alkyl.

Suitable aldehydes are e.g. formaldehyde, acetaldehyde, propionaldehyde, butanal, pentanal, hexanal, heptanal, octanal, nonanal, decanal, undecanal, dodecanal, tridecanal, tetradecanal and the higher homologs with up to 20 carbon atoms, benzaldehyde, substituted benzalde- hydes, such as 2-, 3- or 4-methylbenzaldehyde, 2-, 3- or 4-trifluoromethylbenzaldehyde or 2-, 3- or 4-methoxybenzaldehyde, and aldehydes of formula

wherein x is 1 , 2, 3, 4, 5 or 6 and R^a is hydrogen or Ci-C₄-alkyl, derived from a polyethylene glycol or polythyleneglycol monoether of formula HOCH₂CH2-fO-CH2CHzfx-OR^a, wherein x is 1 , 2, 3, 4, 5 or 6 and R^a is hydrogen or Ci-C₄-alkyl, in which one CH2OH group in oxidized to a CHO group.

The single aldehyde group of the aldehyde b) can also be present as hemiacetal or acetal, preferably as hemiacetal or acetal of a lower alcohol, in particular a Ci-Cio-alkanol. In this case, the alcohol is eliminated in the condensation reaction forming the imidazolium compound.

The aldehyde group is preferably not present as hemiacetal or acetal.

Preferably, component b) comprises or consists of a formaldehyde source. Thus, in particular R³ is hydrogen. Suitable formaldehyde sources are formaldehyd, formaldehyde oligomers (e.g. trioxane) and polymers of formaldehyde (e.g. paraformaldehyde). More preferably, component b) comprises or consists of formaldehyde. In a suitable embodiment, the formaldehyde is employed as an aqueous solution (formalin solution).

Alternatively, the aldehyde is preferably selected from benzaldehyde and an aldehyde of for- mula R³-CHO, where R³ is Ci-C2o-alkyl, more preferably from acetaldehyde, propionaldehyde, butanal, pentanal, hexanal, heptanal, octanal, nonanal, decanal, undecanal, dodecanal, tridecanal, tetradecanal and the higher homologs with up to 20 carbon atoms, and benzaldehyde.

Specifically, the aldehyde is selected from formaldehyde (or a formaldehyde source), dodecanal and benzaldehyde and is very specifically formaldehyde (or a formaldehyde source). c) Amino compound having at least two primary amino groups The amino compound is preferably selected from compounds of the formula (IV)

wherein m is an integer greater than or equal to 2, and A is an m-valent organic radical.

In the formula (IV), m indicates the number of primary amino groups bound to the group A. m can assume very large values, e.g. m can be an integer from 2 to 10 000, in particular from 2 to 5000. Very high values of m are present, e.g. if the compound c) of the formula (IV) comprises a nitrogen-comprising polymer.

If only amino compounds c) of the formula (IV) are employed, wherein m is 2 (diamines), the obtained imidazolium compounds are linear.

If at least one amino compound c) of the formula (IV) is employed, wherein m is greater than 2, the obtained imidazolium compounds are branched.

In a preferred embodiment, m is an integer from 2 to 6, in particular from 2 to 4. More preferably, m is 2 (diamine) or m is 3 (triamine). In particular, m is 2. In alternative embodiment, component c) comprises at least one amino compound having two primary amino groups and at least one amino compound having three primary amino groups. In this embodiment, m is a real number in a range of greater than 2 and less than 3.

The group A can be, in particular, a hydrocarbon group, which can be substituted or interrupted by functional groups comprising heteroatoms.

In a preferred embodiment, component c) is selected from

- amines of the formula 1 H2N-A-N H2 (1 )

wherein

A is a divalent aliphatic, alicyclic, aliphatic-alicyclic, aromatic or araliphatic radical, where the aliphatic moieties in the aforementioned aliphatic, aliphatic-alicyclic or araliphatic radicals may be interrupted by one or more nonadjacent groups which are selected from -0-, -S- and -N(R^b)-, where R^b is selected from hydrogen, Ci-C2o-alkyl and a group

R^c, wherein y is 1 , 2, 3, 4, 5 or 6 and R^c is hydrogen or Ci-C4-alkyl; where alicyclic or aromatic moieties in the aforementioned alicyclic, aliphatic-alicyclic, aromatic or araliphatic radicals may be substituted by 1 , 2, 3 or 4 radicals selected from Ci-C2o-alkyl, C1-C20- alkoxy, a radical of the formula -0-fCH2CH20]_z-R^d, where R^d is hydrogen or Ci-C4-alkyl and z is 1 , 2, 3, 4, 5 or 6; carboxyl and carboxylate, and where the aliphatic moieties in the aforementioned aliphatic, aliphatic-alicyclic or araliphatic radicals may be substituted by 1 , 2, 3 or 4 radicals selected from Ci-C2o-alkoxy, a radical of the formula -0-fCH2CH20]_z-R^d, where R^d is hydrogen or Ci-C4-alkyl and z is 1 , 2, 3, 4, 5 or 6, carboxyl and carboxylate.

In one embodiment the aromatic or araliphatic radicals do not contain 1 ,4-bound phe- nylene rings;

- amines of the formula 2

in which

Y is CR^C, N, C₂-C₆-alkyl or C₃-C₆-cycloalkyl;

Ei, E2 and E3, independently of each other, are a single bond, Ci-Cio-alkylene, -NR^D-C2-Cio- alkylene or -0-Ci-Cio-alkylene, with the proviso that Ei, E2 and E3 are not a single bond and are not -NR^D-C2-Cio-alkylene when Y is N;

R^c is H, Ci-C4-alkyl, C2-C4-hydroxyalkyl or Ci-C4-alkoxy and is preferably H, Ci-C4-alkyl or Ci-C4-alkoxy; and

R^B and R^D, independently of each other, are H, Ci-C4-alkyl, C2-C4-hydroxyalkyl or C1-C4- alkoxy and are preferably H, Ci-C4-alkyl or Ci-C4-alkoxy; and

- mixtures thereof.

Divalent aliphatic radicals are those which comprise no cycloaliphatic, aromatic or heterocyclic constituents. Examples are alkylene, alkenylene and alkynylene radicals.

Divalent alicyclic radicals can comprise one or more, e.g. one or two, alicyclic radicals; however, they comprise no aromatic or heterocyclic constituents. The alicyclic radicals can be substituted by aliphatic radicals, but bonding sites for the NH₂ groups are located on the alicyclic radical. Divalent aliphatic-alicyclic radicals comprise not only at least one divalent aliphatic radical but also at least one divalent alicyclic radical, it being possible for the two bonding sites for the NH2 groups to both either be located on the alicyclic radical(s) or both on the aliphatic radical(s) or one on an aliphatic radical and the other on an alicyclic radical. Divalent aromatic radicals can comprise one or more, e.g. one or two, aromatic radicals; however, they comprise no alicyclic or heterocyclic constituents. The aromatic radicals can be substituted by aliphatic radicals, but both bonding sites for the NH₂ groups are located on the aromatic radical(s).

Divalent araliphatic radicals comprise not only at least one divalent aliphatic radical but also at least one divalent aromatic radical, it being possible for the two bonding sites for the Nhb groups to be located either both on the aromatic radical(s) or both on the aliphatic radical(s) or one on an aliphatic radical and the other on an aromatic radical.

Preferably, the divalent aliphatic radicals A are selected from linear and branched Ci-C3o-al- kylene which may be interrupted by one or more nonadjacent groups which are selected from - 0-, -S- and -N(R^b)-, where R^b is selected from hydrogen, Ci-C2o-alkyl and a group -f-ChbChb- 0}_y-R^c, wherein y is 1 , 2, 3, 4, 5 or 6 and R^c is hydrogen or Ci-C4-alkyl; and/or may be substi- tuted by 1 , 2, 3 or 4 radicals selected from Ci-C2o-alkoxy, a radical of the formula -O- fCH2CH20]z-R^d, where R^d is hydrogen or Ci-C4-alkyl and z is 1 , 2, 3, 4, 5 or 6, carboxyl and carboxylate.

More preferably, the divalent aliphatic radical A is linear or branched C2-C2o-alkylene, even more preferably linear or branched C3-C2o-alkylene, particularly preferably linear or branched C4-C2o-alkylene and in particular linear or branched C4-Ci2-alkylene; specifically a linear C4-C12- alkylene. The alkylene chain may carry a carboxyl or carboxylate group. Preferably, the alkylene biradical is linear. Examples of suitable amines in which the radical A has this meaning (C2-C20- alkylene) are 1 ,2-ethylenediamine, 1 ,2- and 1 ,3-propylenediamine, 2,2-dimethyl-1 ,3-propanedi- amine, 1 ,4-butylenediamine, 1 ,5-pentylenediamine, hexamethylenediamine, heptamethylenedi- amine, octamethylenediamine, nonamethylenediamine, decamethylenediamine, undecameth- ylenediamine, dodecamethylenediamine, tridecamethylenediamine, tetradecamethylenedia- mine, pentadecamethylenediamine, hexadecamethylenediamine, heptadecamethylenediamine, octadecamethylenediamine, nonadecamethylenediamine, eicosamethylenediamine, 2-butyl-2- ethyl-1 ,5-pentamethylenediamine, 2,2,4- or 2,4,4-trimethyl-1 ,6-hexamethylenediamine, 1 ,5-dia- mino-2-methylpentane, 1 ,4-diamino-4-methylpentane and the like. Among these, preference is given to 1 ,4-butylene diamine, 1 ,5-pentylene diamine, 1 ,6-hexylene diamine, 1 ,8-octylene diamine, 1 ,12-dodecylenediamine and mixtures thereof. Also preferred are the carboxyl- or carbox- ylate-substituted alkylene diamines of formulae N H2-CH(COOH)CH2CH₂CH2-NH2 and

NH₂-CH(COO-)CH2CH₂CH2-NH2.

In an alternatively more preferred embodiment, the divalent aliphatic radical A is a group -fB-X}k- B- in which each X independently is -0-, -S- or -N(R^b)-, where R^b is selected from hydrogen, Ci- C2o-alkyl and a group -f-C bChb-OJy- ⁰, wherein y is 1 , 2, 3, 4, 5 or 6 and R^c is hydrogen or Ci- C4-alkyl, preferably O, each B independently is C2-C6-alkylene, preferably C2-C3-alkylene; and k is an integer from 1 to 100, preferably 1 to 10 and more preferably 2 to 4. Examples of suitable amines in which the radical A has this meaning are amine-terminated polyoxyalkylene polyols, for example Jeff-Amines, such as 1 ,8-diamino-3,6-dioxaoctan, 1 ,13-diamino-4,7,10-trioxatride- can, 4,9-dioxadodecane-1 ,12-diamine and 4,7,10-trioxatridecane-1 ,13-diamine, or else more regular amine-terminated polyoxyalkylenediols (amine-terminated polyalkylene glycols; amine- terminated polyalkylene oxides), such as amine-terminated polyethylene glycols, amine-terminated polypropylene glycols or amine-terminated polybutylene glycols. The three last-mentioned amines (amine-terminated polyalkylene glycols) preferably have a molecular weight of from 100 to 3000 g/mol. Among these, preference is given to amines N H2-[CH2CH20]x-CH2CH2-N H2 with x being 2 or 3, preferably 2, and

N H2-CH2CH2CH2-[CH2CH20]x-CH2CH₂CH2-N H2 with x being 2 or 3, preferably 2.

Preferably, the divalent alicyclic radicals A are selected from Cs-Cs-cycloalkylene which may carry 1 , 2, 3 or 4 Ci-C4-alkyl radicals. Examples of suitable amines in which the radical A has this meaning are cyclopentylenediamine, such as 1 ,2-diaminocyclopentane or 1 ,3-diaminocyclo- pentane, cyclohexylenediamine, such as 1 ,2-diaminocyclohexane, 1 ,3-diaminocyclohexane or 1 ,4-diaminocyclohexane, 1 -methyl-2,4-diaminocyclohexane, 1-methyl-2,6-diaminocyclohexane, cycloheptylenediamine, such as 1 ,2-diaminocycloheptane, 1 ,3-diaminocycloheptane or 1 ,4-dia- minocycloheptane, and cyclooctylenediamine, such as 1 ,2-diaminocyclooctane, 1 ,3-diaminocy- clooctane, 1 ,4-diaminocyclooctane or 1 ,5-diaminocyclooctane. The amino groups (N H2 groups) may be in the cis or trans position relative to one another.

Preferably, the divalent aliphatic-alicyclic radicals A are selected from Ci-C4-alkylene-C5-C8-cy- cloalkylene, C₅-C8-cycloalkylene-Ci-C4-alkylene-C5-C8-cycloalkylene and Ci-C4-alkylene-Cs-C8- cycloalkylene-Ci-C4-alkylene, where the cycloalkylene radicals may carry 1 , 2, 3 or 4 Ci-C4-alkyl radicals. Examples of suitable amines in which the radical A has this meaning are diaminodicy- clohexylmethane, such as bis(4-aminocyclohexyl)methane or bis(3-aminocyclohexyl)methane; isophoronediamine, bis(aminomethyl)cyclohexane, such as 1 ,1-bis(aminomethyl)cyclohexane,

1 .2- bis(aminomethyl)cyclohexane, 1 ,3-bis(aminomethyl)cyclohexane or 1 ,4-bis(aminomethyl)cy- clohexane, 2-aminopropylcyclohexylamine, 3(4)-aminomethyl-1 -methylcyclohexylamine, 2-(2- amino-propyl)-cyclohexylamine and the like. The groups bonded to the alicyclic radical can in each case assume any desired position (cis/trans) relative to one another.

Preferably, the divalent aromatic radicals A are selected from 1 ,2-phenylene, 1 ,3-phenylene, naphthylene and biphenylene, with the phenylene radicals possibly carrying 1 , 2, 3 or 4 radicals selected from Ci-C2o-alkyl, Ci-C2o-alkoxy and a radical of the formula -0-{CH2CH20]_z-R^d, where R^d is hydrogen or Ci-C4-alkyl and z is 1 , 2, 3, 4, 5 or 6. Examples of suitable amines in which the radical A has this meaning are o-phenylenediamine, m-phenylenediamine, tolylenediamine, such as 0-, m- and p-tolylenediamine, xylylenediamine, and naphthylenediamine, such as 1 ,2-,

1.3- , 1 ,4-, 1 ,5-, 1 ,8-, 2,3-, 2,6- and 2,7-naphthylene. Preferably, the divalent araliphatic radicals A are selected from phenylene-Ci-C4-alkylene, phe- nylene-Ci-C4-alkylene-phenylene and Ci-C4-alkylene-phenylene-Ci-C4-alkylene, with the phe- nylene radicals possibly carrying 1 , 2, 3 or 4 radicals selected from Ci-C2o-alkyl, Ci-C2o-alkoxy and a radical of the formula -0-{CH2CH20]_z-R^d, where R^d is hydrogen or Ci-C4-alkyl and z is 1 , 2, 3, 4, 5 or 6. Examples of suitable amines in which the radical A has this meaning are dia- minodiphenylmethane, such as 2,2'-, 3,3'- and 4,4'-diaminodiphenylmethane, 3-aminomethyl- benzylamine and the like.

Examples for amines 2 are

compounds of the formula (2.A)

(2.A) wherein R⁵, R⁶ and R⁷ are each, independently of one another, a C1-C10 alkylene group, particularly preferably a C2-C6-alkylene group;

such as N,N-bis(3-aminopropyl)ethylenediamine, N,N-bis(3-aminopropyl)propane-1 ,3-diamine, N,N-bis(3-aminopropyl)butane-1 ,4-diamine, tris(2-aminoethyl)amine, tris(2-aminopropyl)amine, tris(3-aminopropyl)amine, tris(2-aminobutyl)amine, tris(3-aminobutyl)amine, tris(4-aminobu- tyl)amine, tris(5-aminopentyl)amine and tris(6-aminohexyl)amine. In a preferred embodiment, R⁵, R⁶ and R⁷ have the same meaning. A preferred compound (2.A) is tris(2-aminoethyl)amine (R⁵ = R⁶ = R⁷ = ethylene).

Further examples of amines 2 are trisaminohexane, trisaminononane, 4-aminomethyl-1 ,8-oc- tamethylenediamine and the like.

Further examples of amines 2 are the compounds of following structures (2.B) or (2.C):

(2.B) (2.C) Further examples of amines 2 are amines of the formula 2, wherein Y is CR^C, where R^c is H or Ci-C4-alkyl, and Ει , E2 and E3, independently of each other, are -0-Ci-C6-alkylene, preferably - 0-CH2CH2CH(CH3)-. Among these, preference is given to a compound wherein Y is CR^C, where R^c is ethyl, and Ει , E2 and E3 are

-0-CH₂CH₂CH(CH₃)-.

Among the above compounds 2, preference is given to the amine of the formula 2, wherein Y is CR^C, where R^c is ethyl, and Ei , E₂ and E₃ are -0-CH₂CH₂CH(CH₃)-. In particular, the amine c) is selected from:

compounds of the formula H2N-(CH2)m-N H2, wherein m is an integer of 3 to 20, preferably 4 to 20, more preferably 4 to 12, where a CH2 group may be substituted by a carboxyl or carboxylate group, such as 1 ,3-propylenediamine, 1 ,4-butylenediamine, 1 ,5-pentylenedia- mine, hexamethylenediamine, heptamethylenediamine, octamethylenediamine, nonamethylenediamine, decamethylenediamine, undecamethylenediamine, dodecameth- ylenediamine, tridecamethylenediamine, tetradecamethylenediamine, pentadecameth- ylenediamine, hexadecamethylenediamine, heptadecamethylenediamine, octadecameth- ylenediamine, nonadecamethylenediamine, eicosamethylenediamine, the carboxyl- or car- boxylate-substituted alkylene diamines of formulae

NH₂-CH(COOH)CH2CH₂CH2-NH2 or NH₂-CH(COO-)CH2CH₂CH2-NH2; especially 1 ,4-butyl- ene diamine, 1 ,5-pentylene diamine, 1 ,6-hexylene diamine, 1 ,8-octylene diamine, 1 ,12- dodecylenediamine and the carboxyl- or carboxylate-substituted alkylene diamines of formulae NH₂-CH(COOH)CH2CH₂CH2-NH2 or

NH₂-CH(COO-)CH2CH2CH2-NH₂;;

- compounds of the formula Nhb-fB-XJk-B-NI-b; in which each X independently is

-0-, -S- or -N(R^b)-, where R^b is selected from hydrogen, Ci-C2o-alkyl and a group CH2CH2-0}y-R^c, wherein y is 1 , 2, 3, 4, 5 or 6 and R^c is hydrogen or Ci-C4-alkyl, preferably O; each B independently is C2-C6-alkylene, preferably C2-C3-alkylene; and k is an integer from 1 to 100, preferably 1 to 10, more preferably 2 to 4, such as 1 ,8-diamino-3,6-di- oxaoctan, 1 ,13-diamino-4,7,10-trioxatridecan, 4,9-dioxadodecane-1 ,12-diamine and

4,7,10-trioxatridecane-1 ,13-diamine, or else more regular amine-terminated polyoxy- alkylenediols (amine-terminated polyalkylene glycols; amine-terminated polyalkylene oxides), such as amine-terminated polyethylene glycols, amine-terminated polypropylene glycols or amine-terminated polybutylene glycols; especially N H2-[CH2CH20]x-CH2CH2- NH₂ with x being 2 or 3, preferably 2, and N H2-CH2CH2CH2-[CH2CH20]x-CH2CH₂CH2-N H2 with x being 2 or 3, preferably 2;

bis(4-aminocyclohexyl)methane, bis(3-aminocyclohexyl)methane, isophoronediamine, 1 ,1 - bis(aminomethyl)cyclohexane, 1 ,2-bis(aminomethyl)cyclohexane, 1 ,3-bis(aminomethyl)cy- clohexane, 1 ,4-bis(aminomethyl)cyclohexane, 2-aminopropylcyclohexylamine, 3(4)-ami- nomethyl-1 -methylcyclohexylamine, 2-(2-amino-propyl)-cyclohexylamine; especially bis(4- aminocyclohexyl)methane, bis(3-aminocyclohexyl)methane, isophoronediamine; 3-aminomethyl-benzylamine;

amines of the formula 2, wherein Y is CR^C, where R^c is H or Ci-C4-alkyl, and Ει , E2 and E₃, independently of each other, are -0-Ci-C6-alkylene, preferably

-0-CH2CH2CH(CH3)-; especially the amine of the formula 2, wherein Y is CR^C, where R^c is ethyl, and Ei , E₂ and E₃ are -0-CH2CH₂CH(CH3)-; and

mixtures thereof.

It is of course also possible to use for dye transfer inhibition according to the present invention imidazolium compounds that are obtained from a mixture of two or more than two different amino compounds c). If an amine of formula 2 is used, it is even preferred to use it in combination with a diamine A(NH₂)_m with m being 2. In a preferred embodiment, the mixture of amino compounds c) comprises at least two amino compounds having different numbers of primary amino groups. The use of diamines (m = 2) in admixture with amino compounds having more than two primary amino groups (m > 2), e.g. triamines, enables the desired degree of crosslink- ing or degree of branching to be set via the proportion of amines with m = 2 to amines m > 2.

Preferred amino compounds c) are the following:

1 ,4-butylenediamine

- 1 ,6-hexylene diamine

1 ,8-octylene diamine

1 ,12-dodecylene diamine

4,4'-diaminodicyclohexyl methane

Xylylendiamin

In a preferred embodiment, the amino compound c) has a molecular weight of less than

10 000 g/mol, particularly preferably less than 5000 g/mol, very particularly preferably less than

1000 g/mol, in particular less than 500 g/mol. Possible diamines and triamines are, in particular, compounds having a molecular weight of from 60 to 500 g/mol or from 60 to 250 g/mol.

In a further preferred embodiment, component c) is selected from nitrogen-comprising polymers. Preferably, component c) is selected from polyvinylamine polymers.

Suitable polyvinylamine polymers are obtainable by free radical polymerization of ethylenically unsaturated monomers having a nitrogen containing group that can be transferred into a primary amino group. In particular, such monomers are selected from vinylcarboxamides which comprise amido groups that are capable of hydrolysis under formation of primary amino groups.

Suitable polyvinylamine polymers c) are described inter alia in US 4,421 ,602, US 5,334,287, EP-A 216 387, US 5,981 ,689, WO 00/63295, US 6,121 ,409 and US 6,132,558. The teaching of those documents is incorporated herein by reference. They are prepared in general by hydrolysis of polymers comprising N-vinylcarboxamide units. These polymers contain in polymerized form monomers selected from e.g. N-vinylformamide, N-vinyl-N-methylformamide, N-vinyla- cetamide, N-vinyl-N-methylacetamide, N-vinyl-N-ethylacetamide, N-vinylpropionamide and mix- tures thereof. It is possible to use comonomers from different monomer classes. Preferred poly- vinylamines polymers c) are homopolymers of N-vinylformamide.

The homo- and copolymers which comprise N-vinylcarboxamide units incorporated in the form of polymerized units can be partly or completely hydrolyzed by known methods. The degree of hydrolysis is generally in a range from 1 to 100 mol%, preferably from 10 to 99 mol%, particularly preferably from 20 to 95 mol% and especially preferably from 30 to 90 mol%. The degree of hydrolysis corresponds to the content of primary vinylamine groups in the polymers, in mol%. The hydrolysis of the polymers described above is effected by known processes, by the action of acids (e.g. mineral acids, such as sulfuric acid, hydrochloric acid or phosphoric acid, carbox- ylic acids, such as formic acid or acetic acid, or sulfonic acids or phosphonic acids), bases or enzymes, as described, for example, in DE-A 31 28 478 and U.S. Pat. No. 6,132,558. With the use of acids as hydrolysis agents, the vinylamine units of the polymers are present as an ammonium salt, while the free amino groups form in the hydrolysis with bases. Suitable polyvinylamine polymers c) preferably have a number average molecular weight in a range of from 220 to 1 000 000, preferably from 440 to 100 000 and in particular 750 to 50 000.

Suitable poly(alkyleneimines) polymers c) include the homopolymers of ethyleneimine (aziri- dine) or its higher homologues, the copolymers of ethyleneimine or its higher homologues with further monomers, and also the graft polymers, e.g. of polyamidoamines or polyvinylamines, with ethyleneimine or its higher homologues. The poly(alkyleneimines) can be crosslinked or uncrosslinked. They can be modified, e.g. by reaction with alkylene oxides, dialkyl or alkylene carbonates or Ci- to C4-carboxylic acids or derivatives of Ci- to C4-carboxylic acids. Suitable poly(alkyleneimines) are obtainable by customary processes known to the person skilled in the art and are commercially available. Suitable poly(alkyleneimine)s are all polymers which are obtainable by cationically initiated polymerization of alkyleneimines and/or N-substituted alkyleneimines. Preferred poly(alkyleneimines) are polyethyleneimines. They are obtainable by cationically initiated polymerization of ethyleneimine (aziridine) and/or N-substituted aziri- dines.

Poly(alkyleneimines) useful as component c) also include the polymers of higher homologues of ethyleneimine, such as propyleneimine (2-methylaziridine), 1- or 2-butyleneimine (2-ethylaziri- dine or 2,3-dimethylaziridine). The poly(alkyleneimines) are preferably homopolymers of eth- yleneimine. Catalysts which can be used for the cationic polymerization of alkyleneimines are, for example, Br0nsted acids, such as sulfuric acid, phosphoric acid, p-toluenesulfonic acid, or carboxylic acids, such as formic acid, acetic acid or propionic acid, or Lewis acids, such as halides, for example zinc chloride or alkyl halides, such as methyl chloride, ethyl chloride, benzyl chloride or eth- ylene chloride. Suitable polyethyleneimines can also be obtained by reaction of ethylene chloride with ammonia and amines. Polymers of this type are commercial products.

Useful poly(alkyleneimines) c) also include alkyleneimine polymers obtainable by grafting poly- vinylamines with at least one alkyleneimine. Preferred are the graft polymers of ethyleneimine. Suitable polyvinylamines and poly(amidoamines) are mentioned before and in the following.

Suitable poly(alkyleneimines) c) preferably have a number average molecular weight in the range of from 150 to 1 000 000, more preferably 250 to 10 000. Further suitable nitrogen containing polymer c) are poly(amidoamines). Poly(amidoamines) in the sense of for the use of imidazolium compounds according to the present invention comprise nitrogen atoms in the form of amide groups and nitrogen atoms in the form of amine groups. Poly(amidoamines) are obtainable, for example, by condensing polycarboxylic acids with poly- amines.

Suitable polycarboxylic acids for the preparation of poly(amidoamines) are e.g. aliphatic and ali- cyclic acids. Those aliphatic and alicyclic acids may have e.g. 2 to 30 carbon atoms. Preferred are dicarboxylic acids, for example, oxalic acid, malonic acid, succinic acid, maleic acid, adipic acid, glutaric acid, suberic acid, sebacic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, undecane-a,co-dicarboxylic acid, dodecane-a,co-dicarboxylic acid, cis- and trans-cyclohex- ane-1 ,2-dicarboxylic acid, cis and trans cyclohexane-1 ,3-dicarboxylic acid, cis and trans cyclo- hexane-1 ,4-dicarboxylic acid, cis and trans cyclopentane-1 ,2-dicarboxylic acid, cis and trans cy- clopentane-1 ,3-dicarboxylic acid. In particular, the poly(amidoamines) c) do not contain aromatic dicarboxylic acids, e.g. phthalic acid, isophthalic acid or terephthalic acid.

Suitable tricarboxylic acids or polycarboxylic acids for the preparation of poly(amidoamines) c) are e.g. 1 ,2,3-propanetricarboxylic acid or 1 ,3,5-cyclohexanetricarboxylic acid.

The carboxylic acids can also be employed for the preparation of poly(amidoamines) in the form of derivatives. Such derivatives are preferably anhydrides, acyl chlorides and esters. In the polycarboxylic acids all or only a part of the acid groups may be derivatised. Preferred esters are esters of Ci-Ce-alcanols, especially the methyl ester or ethyl ester.

Suitable polyamines for the preparation of poly(amidoamines) contain at least two primary or secondary nitrogen atoms capable of forming amide groups. The total number of basic nitrogen atoms in the polyamines is preferably in the range of from 3 to 100, more preferably 3 to 25, e.g. 4 to 10. In the preparation of the poly(amidoamines), it is possible to use mixtures of two or more polycarboxylic acids as well as mixtures of two or more polyamines. Examples of suitable polyamines are diethylenetriamine, triethylenetetramine, tetraethylene pentamine, dipropylene triamine, tripropylene tetramine, dihexamethylene triamine, aminopropylethylenediamine and bisaminopropylethylenediamine. Suitable polyamines are also polyalkylenepolyamines. The polyamines can be present in a mixture with diamines. Useful diamines include for example 1 ,2- diaminoethane, 1 ,3-diaminopropane, 1 ,4-diaminobutane, 1 ,5-diaminopentane, 1 ,6-diaminohex- ane, 1 ,8-diaminooctane, isophoronediamine, 4,4'-diaminodiphenyl-methane, 1 ,4-bis(3-ami- nopropyl)piperazine, 4,9-dioxadodecane-1 ,12-diamine, 4,7,10-trioxatridecane-1 ,13-diamine or α,ω-diamino compounds of polyalkylene oxides.

Lactones or lactams of carboxylic acids having 4 to 8 carbon atoms may also be used in the condensation for the preparation of poly(amidoamines).

Suitable poly(amidoamines) have at least two terminal amino groups (-NH, -NH₂) or both.

Suitable as poly(amidoamines) are also poly(amidoamines) grafted with at least one alkyleneimine, e.g. grafted with ethyleneimine. Grafted poly(amidoamines) are obtainable from the above-described poly(amidoamines) by reaction with at least one alkyleneimine in the presence of Br0nsted acids or Lewis acids, such as sulfuric acid or boron trifluoride etherates. The reaction temperature is preferably in the range of from 80 to 100 °C. Compounds of this type are described, for example, in US 4,144,123 and DE-B-24 34 816. The teaching of these documents is incorporated by reference. Suitable poly(amidoamines) grafted with ethyleneimine have, for ex- ample, an average molecular weight of from 3000 to 1 000 000 daltons. The graft polymers generally contain from 10 to 90% by weight of polyamidoamines as a grafting base and from 90 to 10% by weight of alkyleneimine as a graft.

Suitable poly(amidoamines) c) preferably have a number average molecular weight in the range of from 150 to 1 000 000, more preferably 250 to 10 000. d) Other starting materials

The polymeric, ionic compounds comprising imidazolium groups can be produced in a process in which it is possible to use further compounds, e.g. in order to introduce specific end groups into the polymer or bring about additional crosslinking by means of further functional groups, to set defined properties or to make further reactions on the resulting polymer (polymer-analogous reactions) at a later point in time possible. Thus, if desired, it is possible to make concomitant use of, for example, compounds having only one primary amino group (= component d)) in order to influence the molecular weight of the polymeric imidazolium compounds. The compound having only one primary amino group leads to chain termination and then forms the end group of the polymer chain concerned. The higher the proportion of compounds having only one primary amino group, the lower the molecular weight. Based on 100 mol of amino compounds having at least two primary amino groups, it is possible, in a preferred embodiment, to use, for example, from 0 to 10 mol of compounds having only one primary group. e) Protic acid

The anions of the imidazolium compound are derived from the anions of the protic acid(s) em- ployed as component e). It is also possible to subject the imidazolium compound to an anion exchange. This allows the preparation of imidazolium compounds with anions for which no corresponding stable protic acid exists. The anion exchange can be effected by known methods, e.g. transprotonation, reaction with a metal salt, ion exchange chromatography, electrolytically or by means of a combination of these measures.

The imidazolium compound employed according to the use according to the present invention comprises anions that act as counterions to the imidazolium cations. The anions are selected from anions of the formula Y^n", wherein n is the valency of the anion. The corresponding protic acid can be represented by the formula Yⁿ- (H⁺)_n.

In a first embodiment, the anions of the formula Y^n_ are selected from anions of inorganic acids and low molecular weight organic acid. In this embodiment, m is preferably an integer from 1 to 6, more preferably an integer from 1 to 4, in particularly 1 or 2. In a special embodiment, n is 1. In a second embodiment, the anions of the formula Yⁿ- are selected from anions of polymeric protic acids, e.g. polyacrylic acid. In this embodiment, n can assume very high values. Suitable polymeric protic acids comprise at least one ethylenically unsaturated organic acid in polymerized form. Preferred ethylenically unsaturated organic acid are selected from acrylic acid, methacrylic acid, maleic acid, fumaric acid, itaconic acid, etc. and mixtures thereof. Especially pre- ferred are the homo- and copolymers of acrylic acid and/or methacrylic acid. Suitable polymeric protic acids are also the copolymers of at least one ethylenically unsaturated organic acid, preferably selected from acrylic acid methacrylic acid, maleic acid, fumaric acid, itaconic acid with at least one copolymerizable comonomer, e.g. selected from (meth)acrylates, vinyl esters or aromatic monomers such as styrene and mixtures thereof.

The anions of the imidazolium compound (= anions of the formula Y^n_) and the anions of the corresponding protic acid (= Yⁿ- (H⁺)_n) are preferably selected from: the group of halides and halogen-comprising anions of the general formulae:

F-, CI-, Br, I-, BF₄-, PF₆ ^", AlC , AI2CI7-, A Cho^", AIBr₄-, FeCk, BCk, SbF₆ ^", AsF₆,-ZnCI₃-, SnC ^",

CuCI₂-; the group of pseudohalides and other nitrogen-containing anions of the formulae:

CN-, SCN-, OCN-, NO2-, NO3-, N(CN)- ; the group of sulfates, sulfites and sulfonates of the general formulae:

S0₄ ²-, HSO4-, SO3²-, HSO3-, R^aOS0₃-, R^aS0₃-; the group of phosphates of the general formulae:

PO4³-, HPO4²-, H2PO4-, R^aP0₄ ²-, HR^aP0₄-, R^aR^bP0₄-; the group of phosphonates and phosphinates of the general formulae:

R^aHP0₃-,R^aR^bP0₂-, R^aR^bP0₃-; the group of phosphites of the general formulae:

P0₃ ³-, HPOs²-, H2PO3-, R^aP0₃ ²-, R^aHP0₃-, R^aR^bP0₃-; the group of phosphonites and phosphinites of the general formulae:

R^aR P0₂ ^", R^aHP0₂-, R^aR^bPO-, R^aHPO^"; the group of carboxylates and polybasic carboxylic acids of the formulae:

R^aCOO; R^e(COO )_f; the group of borates of the general formulae:

BO3³-, HBO3²-, H2BO3-, R^aR B0₃ ^", R^aHB0₃-, R^aB0₃ ^2", B(OR^a)(OR )(OR^c)(OR^d)-, B(HS0₄)-, B(R^aS0₄)- ; the group of boronates of the general formulae:

R^aB0₂ ²-, R^aR^bBO-; the group of halogenated hydrocarbons of the general formulae:

CF3SO3-, (CF₃S0₃)₂N-, CF3CO2-, CCI3CO2-; the group of carbonates and carbonic esters of the general formulae:

the group of silicates and silicic esters of the general formulae:

S1O4⁴-, HS1O4³-, H2S1O4²-, H3S1O4-, R^aSi0₄ ³-, R^aR Si0₄ ²-, R^aR R^cSi0₄-, HR^aSi0₄ ²-, H₂R^aSi0₄-, HR^aR^bSi0₄-; the group of alkylsilane and arylsilane salts of the general formulae:

R^aSi0₃ ³-, R^aR Si0₂ ²-, R^aR R^cSiO^", R^aR R^cSi0₃-, R^aR R^cSi0₂-, R^aR^bSi0₃ the group of carboximides, bis(sulfonyl)imides and sulfonylimides of the general formulae:

the group of methides of the general formula:

S0₂-R^a

I .

R^b-0₂S S0₂-R^c

the group of alkoxides and aryloxides of the general formula:

R^aO-; the group of halometalates of the general formula:

[M_rHal_t]^s-,

where M is a metal and Hal is fluorine, chlorine, bromine or iodine, r and t are positive integers and indicate the stoichiometry of the complex and s is a positive integer and indicates the charge on the complex;

the group of sulfides, hydrogensulfides, polysulfides, hydrogenpolysulfides and thiolates of the general formulae:

S²-, HS-, [Sv]²-, [HSv]-, [R^aS]-,

where v is a positive integer from 2 to 10; the group of complex metal ions such as Fe(CN)6^3", Fe(CN)6^4", MnCv, Fe(CO)₄.

In the above formulae, R^a, R^b, R^c and R^d are each, independently of one another, nonacidic hydrogen, Ci-C3o-alkyl and aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxy-, amino-, carboxy-, formyl-, -0-, -CO-, -CO-O- or -CO-N<substituted derivatives thereof, for example methyl, ethyl, 1 -propyl, 2-propyl, 1 -butyl, 2-butyl, 2-methyl-1 -propyl (isobutyl), 2-methyl-2-propyl (tert-butyl), 1 - pentyl, 2-pentyl, 3-pentyl, 2-methyl-1 -butyl, 3-methyl-1 -butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2, 2-dimethyl-1 -propyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-1 -pentyl, 3-methyl-1 -pentyl, 4-methyl- 1 -pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3- pentyl, 2,2-dimethyl-1 -butyl, 2,3-dimethyl-1 -butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1 -butyl, 2,3-dime- thyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, phenyl- methyl (benzyl), diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl, cyclopentylme- thyl, 2-cyclopentylethyl, 3-cyclopentylpropyl, cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohex- ylpropyl, methoxy, ethoxy, formyl, acetyl or C_qF₂(_q-a)+(i-b)H2a+b where q < 30, 0 < a < q and b = 0 or 1 (for example CF₃, C₂F₅, CH₂CH2-C(_q-2)F2(q-2)₊i , C₆Fi₃, C₈Fi₇, C10F21 , C12F25);

C3-Ci2-cycloalkyl and aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxy-, amino-, carboxy-, formyl-, -0-, -CO- or -CO-O-substituted derivatives thereof, for example cyclopentyl, 2-methyl- 1 -cyclopentyl, 3-methyl-1 -cyclopentyl, cyclohexyl, 2-methyl-1-cyclohexyl, 3-methyl-1-cyclohexyl, 4-methyl-1-cyclohexyl or C_qF2(q-a)-(i-b)H₂a-b, where q < 30, 0 < a < q and b = 0 or 1 ;

C2-C3o-alkenyl and aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxy-, amino-, carboxy-, formyl-, - 0-, -CO- or -CO-O-substituted derivatives thereof, for example 2-propenyl, 3-butenyl, cis-2-bu- tenyl, trans-2-butenyl or C_qF2(q-a)-(i-b)H₂a-b where q < 30, 0 < a < q and b = 0 or 1 ;

C3-Ci2-cycloalkenyl and aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxy-, amino-, carboxy-, formyl-, -0-, -CO- or -CO-O-substituted derivatives thereof, for example 3-cyclopentenyl, 2-cy- clohexenyl, 3-cyclohexenyl, 2,5-cyclohexadienyl or

CqF₂(q-a)-3(i-b)H2a-3b where q < 30, 0 < a < q and b = 0 or 1 ;

aryl or heteroaryl having from 2 to 30 carbon atoms and alkyl-, aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxy-, amino-, carboxy-, formyl-, -0-, -CO- or -CO-O-substituted derivatives thereof, for example phenyl, 2-methylphenyl (2-tolyl), 3-methylhenyl (3-tolyl), 4-methylphenyl, 2- ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dime- thylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 4-phenylphenyl, 1 - naphthyl, 2-naphthyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl or C6F(₅- a)H_a, where 0 < a < 5; or

two radicals form an unsaturated, saturated or aromatic ring which may optionally be substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and/or heterocycles and may optionally be interrupted by one or more oxygen and/or sulfur atoms and/or one or more substituted or unsubstituted imino groups.

Particular preference is given to R^a, R^b, R^c and R^d each being, independently of one another, hydrogen and particularly preferably a Ci-Cio-alkyl group, preferably a Ci-C4-alkyl group.

R^e (see above formula for the polybasic carboxylic acid) is an organic radical to which a plurality of carboxylic acid groups are bound. Correspondingly, f is an integer of at least 2. Preferably, f is an integer of 2 to 100 000, more preferably, 2 to 10 000. Such polybasic carboxylic acids can be, for example, maleic acid or itaconic acid, phthalic acid, isophthalic acid or terephthalic acid; other possibilities are polymeric compounds which can be obtained, for example, by free-radical polymerization of ethylenically unsaturated compounds using, possibly among others, monomers having one or two carboxylic acid groups, e.g. (meth)acrylic acid.

Particular preference is given to carboxylic acids, i.e. protic acids of the above carboxylates of the general formulae:

R^aCOO and R^e(-COO )_f As such carboxylic acids or carboxylates, particular mention may be made of organic compounds which have from 1 to 20 carbon atoms and comprise one or two carboxylate groups, preferably one carboxylate group.

The carboxylic acids or carboxylates can be aliphatic or aromatic compounds. Here, aromatic compounds are compounds comprising aromatic groups. Particular preference is given to aliphatic or aromatic compounds which, apart from the oxygen atoms of the carboxylate group, comprise no further heteroatoms or at most comprise one or two hydroxyl groups, carbonyl groups or ether groups. Very particular preference is given to aliphatic or aromatic compounds which comprise no further heteroatoms in addition to the oxygen atoms of the carboxylate group.

As compounds having two carboxylate groups, mention may be made of, for example, the ani- ons of phthalic acid, of isophthalic acid, of C2-C6-dicarboxylic acids, e.g. oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid.

As compounds having one carboxylate group, mention may be made of the anions of aliphatic, aromatic, saturated or unsaturated Ci-C2o-carboxylic acids, in particular alkanecarboxylic acids, alkenecarboxylic acids, alkynecarboxylic acids, alkadienecarboxylic acids, alkatrienecarboxylic acids, hydroxycarboxylic acids or ketonecarboxylic acids or aromatic carboxylic acids such as benzoic acid or phenylacetic acid. Suitable alkanecarboxylic acids, alkenecarboxylic acids and alkadienecarboxylic acids are also known as fatty acids. As anions Y-, mention may be made of, in particular, the anions of Ci-C2o-alkanecarboxylic acids, which may optionally be substituted by one or two hydroxy groups, preferably one hydroxy group.

Further preferred protic acids or preferred anions of protic acids are, apart from carboxylic acids (carboxylates), also sulfonic acid, phosphoric acid or phosphonic acid, with the acid groups of the sulfonic acid, phosphoric acid or phosphonic acid being able to be partially esterified.

As phosphoric acid and esters thereof, mention may be made of, in particular, compounds of the formula VII

O II

HO— P— OR"

I

OR' where R' and R" are each, independently of one another, hydrogen or a C1-C10-, preferably Ci- C₄-alkyl group. As phosphonic acid and esters thereof, mention may be made of, in particular, compounds of the formula VIII

0

HO-P— R"

I

OR' where R' and R" are each, independently of one another, hydrogen or a C1-C10-, preferably Ci- C₄-alkyl group.

Preferably, the at least one protic acid e) is not a hydrohalic acid. Accordingly, the imidazolium compound employed for the use as dye transfer inhibitor according to the invention does essentially not comprise anions of a hydrohalic acid (F-, Ch, Br and I^"). In the context of the invention, an imidazolium compound which does essentially not comprise anions of a hydrohalic acid denotes an imidazolium compound that comprises at the most 1 mole%, preferably at the most 0.1 mole%, more preferably at the most 0.01 mole, in particular at the most 0.001 mole%, based on the total anion content anions of a hydrohalic acid.

Preferably, the anions are selected from:

the group of carboxylates and polybasic carboxylic acids

the group of sulfates, sulfites and sulfonates,

the group of phosphates, and

the group of halogenated hydrocarbons.

In particular, the anions are selected from formate, acetate, propionate, butyrate, pentanoate, hexanoate, heptanoate, octanoate, glycolate (hydroxyacetate), adipate, succinate, phthalate, terephthalate, methoxyacetate, (Ci-C₄-alcoxy)(CH2CH20)_xCH2COO^" with x being 1-4, benzoate, hydrogenphosphate, sulfate, hydrogensulfate and methanesulfonate.

In another embodiment the anions of the at least one protic acid e) and/or the anions of the imidazolium compound can additionally be selected from chloride, bromide and iodide.

The polymeric ionic compound comprising imidazolium groups preferably has a weight average molecular weight M_w (determined according to the methods described in the examples) of from 300 bis 500000, more preferably of from 500 to 300000, even more preferably of from 1000 to 200000, in particular 2000 to 150000 and specifically 3500 to 120000 . The dispersity PDI (M_w/M_n; Mn = number-average molecular weight) is preferably in the range from 1 .1 to 20, more preferably from 1.5 to 15.

In one embodiment of the present invention, the polymeric ionic compound comprising imidazolium groups is used in combination with one or more dye transfer inhibiting polymers which may be constructed on the basis of nitrogenous monomers polymerizable via vinyl or allyl groups. Examples thereof are N-vinylpyrrolidone, N-vinylimidazole, N-vinylcaprolactam, 4-vinylpyridine, N-vinylpyridine, diallyldimethylammonium chloride, N-vinylformamide, N-vinylacetamide, vinyla- mine, allylamine, acrylamide, N-substituted and also N, N-substituted acrylamides. The nitrogen atoms in the homo- or copolymers may also be present therein in derivatized form. This derivati- zation is preferably carried out after the polymerization and comprises for example quaterniza- tions, for example with methyl chloride, benzyl chloride, dimethyl sulfate; betainizations for example with chloracetic acid, propanesultone or oxidations for example with hydrogen peroxide. An example thereof is poly(4-vinylpyridine) which is used as a dye transfer inhibiton polymer following derivatization in the form of the N-carboxymethylbetaine, the N-sulfopropylbetaine or the N-oxide. The copolymers may comprise units derived from further nitrogen-free monomers. Examples thereof are vinyl acetate (which after polymerization may be completely or partially hydrolyzed to the vinyl alcohol unit); C2 - C24 olefins, preferably ethylene, propylene, butylene; diisobutene; vinylbenzene (styrene); vinyl chloride; acrylic acid and also its esters with aliphatic, alicyclic, ar- omatic alcohols R-OH where R = Ci- to Cis-alkyl, benzyl, ethylphenyl, cyclohexyl or phenyl, preferably with methanol, ethanol or propanol, polyethylene glycols (PEGs) and one-sidedly endblocked polyethylene glycols (methyl polyethylene glycols, MPEGs); methacrylic acid, and also its esters with aliphatic, alicyclic or aromatic alcohols R-OH where R = Ci- to Cis-alkyl, benzyl, ethylphenyl, cyclohexyl or phenyl, preferably with methanol, ethanol or propanol, polyeth- ylene glycols (PEGs) and one-sidedly endblocked polyethylene glycols (methyl polyethylene glycols, MPEGs); amides of acrylic acid or of methacrylic acid with primary or secondary amines which may have aliphatic (Ci- to C22-alkyl), alicyclic (e.g., hexyl) or aromatic (e.g., phenyl, benzyl) substituents; vinylsulfonic acid; allylsulfonic acid; 2-acrylamido-2-methylpropylsulfonic acid (AMPS).

Examples of dye transfer inhibiting polymers which may be constructed on the basis of nitrogenous monomers include polyvinylpyrrolidone (e.g., Sokalan® HP 50/ BASF, PVP-K-Typen®/ ISP), vinylpyrrolidone-vinylimidazole copolymer (e.g., Sokalan® HP 56/ BASF), poly(4-vinylpyri- din N-oxide) (e.g., Chromabond® S-403E / ISP), poly(4-vinylpyridine N-carboxymethylbetaine (e.g., Chromabond® S 400/ ISP).

In one embodiment of the present invention, the dye transfer inhibiting polymer which may be constructed on the basis of nitrogenous monomers polymerizable via vinyl or allyl groups is selected from the group consisting of vinyl-pyridinyl-N-oxide, vinylpyrrolidon polymers, vinylimidazol polymers, and copolymer of vinylpyrrolidon and vinylimidazol, and mixtures thereof. In another embodiment the dye transfer inhibiting polymer which may be constructed on the basis of nitrogenous monomers polymerizable via vinyl or allyl groups is a copolymer of vinylpyrrolidon and vinylimidazol. In one embodiment of the present invention, the dye transfer inhibiting polymer which may be constructed on the basis of nitrogenous monomers polymerizable via vinyl or allyl groups is a copolymers comprising vinylpyrrolidon and/or vinylimidazol may have a weight average molecular weight of 1000 to 200000 g/mol. In another embodiment of the present invention, the copolymers comprising vinylpyrrolidon and/or vinylimidazol may have a weight average molecular weight of 5000 to 150000 g/mol. In another embodiment of the present invention, the copolymers comprising vinylpyrrolidon and/or vinylimidazol may have a weight average molecular weight of 20000 to 100000 g/mol. In another embodiment of the present invention, the copolymers comprising vinylpyrrolidon and/or vinylimidazol may have a weight average molecular weight of 5000 to 90000 g/mol. In another embodiment of the present invention, the copolymers comprising vinylpyrrolidon and/or vinylimidazol may have a weight average molecular weight of 70000 g/mol.

In one embodiment of the present invention, the dye transfer inhibiting polymer which may be constructed on the basis of nitrogenous monomers polymerizable via vinyl or allyl groups is a copolymer comprising vinylpyrrolidon and vinylimidazol in a weight ratio in the range of from 5:1 to 1 :5. In another embodiment the weight ratio of vinylpyrrolidon and vinylimidazol is in the range of from 2.5 :1 to 1 :2.5. In another embodiment the weight ratio of vinylpyrrolidon and vinylimidazol is 1 :1.

The copolymer comprising vinylpyrrolidon and/or vinylimidazol may be used in amounts in the range of from 0.1 to 5 % of weight based on the weight of the laundry detergent. In one embodiment, the copolymer comprising vinylpyrrolidon and/or vinylimidazol may be used in amounts in the range of from 0.2 to 2.5 % of weight based on the weight of the laundry detergent. In one embodiment the copolymer comprising vinylpyrrolidon and/or vinylimidazol may be used in amounts in the range of from 0.3 to 1.0 % of weight based on the weight of the laundry detergent. copolymer comprising vinylpyrrolidon and/or vinylimidazol may be used in amounts of 0.5 % of weight based on the weight of the laundry detergent.

Method for preventing dye transfer during laundry In another aspect the invention relates to a method for preventing dye transfer during laundry, wherein at least one polymeric, ionic compound is used which comprises imidazolium groups (imidazolium compound), obtainable by reacting a) at least one a-dicarbonyl compound,

b) at least one aldehyde with one aldehyde group,

c) at least one amino compound having at least two primary amino groups,

d) optionally an amino compound having only one primary amino group and

Method for preparation of laundry composition In another aspect the invention relates to a method for preparation of a laundry composition by mixing at least one polymeric, ionic compound which comprises imidazolium groups (imidazolium compound), obtainable by reacting a) at least one a-dicarbonyl compound,

b) at least one aldehyde with one aldehyde group,

c) at least one amino compound having at least two primary amino groups,

d) optionally an amino compound having only one primary amino group and

e) at least one protic acid, and optionally subjecting the reaction product to an anion exchange, where in the components a) and b) the aldehyde carbonyl groups may also be present as hemi- acetal or acetal and the ketone carbonyl groups may also be present as hemiketal or ketal; with a laundry detergent, wherein the laundry composition has dye transfer inhibiting properties. Imidazolium compounds used for the method for preparation of a laundry composition according to the present invention are usually prepared as aqueous solutions or in solid form, as powders or granules. The use concentration of the imidazolium compound of the present invention is based on the laundry detergent between 0.1 % and 10.0 % by weight, preferably between 0.2 % and 5 % by weight and most preferably between 0.3 % and 3.0 % by weight based on the laundry detergent. Typical powder-shaped materials have a particle size in the range from 1 μηη to 0.1 mm, granule-shaped materials have a particle size in the range from 0.1 mm to 2 mm and pellet-shaped particles have a particle size in the range from 2 mm to 5 mm.

For preparation of a laundry composition, additional suitable additives may be added to the laundry composition. Suitable additives are for example fatty acids, particularly C16-C22 fatty acids, such as tallow fatty acid, stearic acid, behenic acid and salts thereof, preferably alkaline earth metal ions, more preferably with Ca2+ and Mg2+; fatty alcohols; cellulose; waxes, for example montan waxes, paraffin waxes, ester waxes and polyolefin waxes; magnesium oxide; kaolin; talc, tricalcium phosphate and silicas.

The aforementioned additives can be used not only individually but also as mixtures.

Preferred additives include the Ca2+ and Mg2+ salts of C16-C22 fatty acids, especially calcium stearate and magnesium stearate. Particularly preferred additives are synthetic, colloidal, pyrog- enous silicas and synthetic, colloidal, precipitated silicas. Pyrogenous silicas are obtained by high-temperature flame hydrolysis of silicon tetrachloride in the detonating gas flame. Precipitated silicas are obtained wet-chemically from alkali metal silicate solutions by addition of acids. Pyrogenous silicas as well as precipitated silicas are amorphous in structure, not crystalline. Examples of pyrogenous silicas are the Aerosil® brands (from Evonik), particularly Aerosil® 200, and examples of the precipitated silicas are the Sipernat® brands (from Evonik), particularly Sipernat® 320, Sipernat® 320 DS, Sipernat® 360, Sipernat® 500 LS, Sipernat® 2200, Sipernat® 22, Sipernat® 22 S, Sipernat® 22 LS, Sipernat® 50, Sipernat® 50 S, Sipernat® C 600, Sipernat® C 630, Sipernat® 820 A and Sipernat® 880. The present invention mixtures of DTI polymer and additive can utilize not only the aforementioned hydrophilic silicas but also hydrophobically modified silicas. Hydrophobic silicas are for example Sipernat® D 10, Sipernat® D 17 and Aerosil® R 812 and R 972. Hydrophobically modified, colloidal, synthetic precipitated silicas and hydrophobically modified, colloidal, pyrogenously produced silicas are very particularly preferred additives. Colloidal, synthetic precipitated silicas are characterized by a high specific surface area of 30- 500 m2/g, preferably 150-450 m2/g. Hydrophobically modified precipitated silicas have a high specific surface area of preferably 75-125 m2/g. (Determination as per area meter method ISO 5794-1 Annex D). The tamped density is 50-300 g/L, preferably 75-200 g/L and even more preferably 90-150 g/L. (Determined to DIN ISO 787/1 1 after tamping under defined conditions). The colloidal pyrogenous silicas preferably have specific surface areas of 100-400 m2/g and particle sizes of 1 nm-50 nm. Tamped density is about 50-150 g/L.

In one embodiment, the method for preparation of a laundry composition results in a solid laun- dry composition. Solid mixtures are produced by mixing the imidazolium compound, present as a powder, pellet or granules, with the finely divided additive.

The typical particle size of the imidazolium compound is in the range from 10 to 2500 μηη, preferably in the range from 20 to 1500 μηη, more preferably in the range from 50 to 1000 μηη and most preferably in the range from 100 to 700 μηη.

By "finely divided" in reference to the additive is meant a particle size in the range from 1 to 500 μπι. In the case of the colloidal pyrogenous silicas the additives preferably have a size in the range from 1 to 50 nm. In the case of the precipitated silicas the additives preferably have a size in the range from 1 to 200 μηη preferably in the range from 5 to 150 μηη and more preferably in the range from 8 to 120 μηη. Each determined by light scattering as per IS013320-1. The mixing operation can be carried out in the customary mixing assemblies, for example drum mixers, V-blenders, tumble or Turbula mixers, cone mixers (e.g., Nauta mixers), plowshare mixers (Lodige mixer, Eirich mixer). In one preferred embodiment, the mixing operation takes place in mixers that exert low shearing forces on the material being mixed, for example tumble mixers, cone mixers and plowshare mixers.

Typically, the imidazolium compound is initially charged, then the additive is added and this is followed by mixing. In order to ensure gentle mixing, the shortest possible mixing times are employed. For example, a mixing time of 3 minutes is completely sufficient to produce 100 g of the mixture of the present invention in a Turbula mixer.

When the imidazolium compounds in powder form are produced via spray drying, the additive is advantageously metered directly to the spray tower separately from the aqueous solution of the polymer. Possible points for addition are the upper end of the spray dryer, a metering terminal via a sight glass or the metered addition via the hot air stream. The same holds in principle for spray granulation. When metered addition of the additive into the spray tower is not possible, it can be added in a separate mixing assembly, as previously described.

Should the additive to be admixed to the imidazolium compound not be sufficiently finely divided because, for example, it is only available as a material which has been melted by heating and has resolidified after filling into drums, as may be the case with fatty acids, fatty alcohols or waxes for example, the imidazolium compound can be ground together with the additive, likewise ensuring commixing of the components. Any grinding apparatus is suitable for this in principle, such as impact mills and cutting mills for example.

In another embodiment the method for preparation of a laundry composition results in a liquid laundry composition, laundering gel or laundering paste. This will preferably be the case when long transits to the user make it desirable to supply the imidazolium compound in a highly concentrated form and hence not as an aqueous solution, and the protection of the product from caking due to moisture absorption in the course of transportation (on a ship for example) is to be improved.

Dyes The imidazolium compound according to the present invention is active in inhibiting transfer of direct dyes and/or acid dyes. Examples for direct dyes are the stilbene based Direct Orange 39 (CAS number 1325-54-8), and polyazo-based Direct Black 22 (CAS number 6473-13-8). An example for an acid dye is diazo-based Acid Blue 1 13 (CAS Number 3351 -05-1 ). Active inhibition of transfer of dyes is defined as measuring a colour difference of at least one ΔΕ unit less for the white acceptor textile when the imidazolium compound was used according to the present invention compared to the test without said compound being present.

ΔΕ is calculated as CIE 1976 color difference according to DIN EN ISO 1 1664-4 (June 2012). AEinitiai is calculated with L^*, a^*, b^* values measured on white acceptor fabric before washing. AEwashed is calculated with L^*, a^*, b^* values measured on the white acceptor fabrics after washing in presence and absence of polymer. Standard colorimetric measurement was used to obtain L^*, a^* and b^* values. The molecular weight of the polymeric imidazolium compounds is determined by Size-exclusion chromatographie (SEC) using poly(2-vinylpyridine as standard and water comprising 0.1 w/w% trifluoracetic acid and 0.1 mol/l NaCI as effluent. The temperature of the column is 25°C, the injected volume 100 μΙ_ ^liter), the concentration 1 .5 mg/mL and the flow rate 0.8 mL/min. The present invention is further demonstrated and exemplified in the following examples, however, without being limited to the embodiments described in the examples.

Examples

Sokalan HP56 K (available from BASF SE, Ludwigshafen) is a vinylpyrrolidon/vinylimidazol co- polymerisate with an weight average molecular weight of 70000 g/mol

Chromabond S400 (formerly available from Ashland, now marketed from Vertellus as Reilline 4140) is a Poly-(4-vinyl-pyridin-N-oxid) with an average molecular weight of 30000g/mol.

Direct Orange 39 is available as color transfer monitor on cotton from Swissatest (Empa 134) Direct Black 22 is available as color transfer monitor on cotton from Swissatest (Empa 132) Direct Red 83.1 is available as color transfer monitor on cotton from Swissatest (Empa 130) Direct Blue 71 is available as color transfer monitor on cotton from Swissatest (Empa 133)

Acid Blue 1 13 is available as color transfer monitor on polyamide from Swissatest (Empa 131 )

The following polymeric, ionic compounds comprising imidazolium groups have been tested: Table 1 . Polymeric, ionic compounds comprising imidazolium groups.

1. Use of imidazolium compounds in liquid detergent formulation The following liquid model composition was prepared:

Linear alkyl benzene sulfonic acid 5.5

Alcohol ethoxylated (C13-C15 alcohol with 7 moles of EO) 5.5

Fatty alcohol ether sulfate (C12-C14, sodium salt) 5.5 1 ,2 propylene glycol 6

Soap 2.5

Ethanol 2

Water to 100

1.1 Experiments using imidazolium compound without additional dye transfer inhibiting polymer Imidazolium compounds were added to a laundry liquor comprising a liquid model detergent without dye transfer inhibitor, in the amounts given in the Table 2 (% on weight of detergent, owod). White acceptor textiles made of either cotton (wfk 10A) or polyamide (Empa 406) were washed therein in the presence of a poorly dyed textile (bleeder). Washing conditions were: 5 g/L detergent, liquor 250 mL, 20 min, 60°C. After wash the fabrics were rinsed for 5 min at 30°C with 250 mL water, centrifuged and ironed. The fabrics were instrumentally assessed with a Datacolor reflection spectrometer Model Type SF500 before and after wash. From the reflection data readings L^*,a^*,b^* were derived and further expressed in ΔΕ values. The higher values of ΔΕ are observed for the acceptor fabrics in comparison to the initial whiteness before the test, the higher discoloration and dye transfer is found, respectively. For visual discrimination vs the reference fabric without any dye transfer inhibitor values of ΔΕ > 1 are required.

Table 2. Results of dye transfer inhibition using different white acceptor fabrics.

1.2 Experiments using imidazolium compound with additional dye transfer inhibiting polymer

Imidazolium compounds were added to a laundry liquor comprising a liquid model detergent with- out dye transfer inhibitor, in the amounts given in the Table 3 to 12 (% on weight of detergent, owod) and additionally added 0.5 % owod (25 ppm) Sokalan HP56K. White acceptor textiles made of either cotton (wfk 10A) or polyamide (Empa 406) were washed therein in the presence of a poorly dyed textile (bleeder). Washing conditions were: 5 g/L detergent, liquor 250 mL, 20 min, 60°C. After wash the fabrics were rinsed for 5 min at 30°C with 250 mL water, centrifuged and ironed. The fabrics were instrumentally assessed with a Datacolor reflection spectrometer Model Type SF500 before and after wash. From the reflection data readings L^*,a^*,b^* were derived and further expressed in ΔΕ values. The higher values of ΔΕ are observed for the acceptor fabrics in comparison to the initial whiteness before the test, the higher discoloration and dye transfer is found, respectively. For visual discrimination vs the reference fabric without any dye transfer inhibitor values of ΔΕ > 1 are required.

Table 3. Results of dye transfer inhibition in the presence/absence of Sokalan HP56K for Direct Orange 39.

Table 4. Results of dye transfer inhibition in the presence/absence of Sokalan HP56K for Direct Black 22.

Dye bleeder fabric Direct Black 22

ΔΕ

White acceptor fabric wfk10A

ComDosage of compound 10% (500ppm) 3% (150ppm) 0.5% (25ppm) pounds [% owod (ppm)]

C14 alone 5,5 8,9 10,4

C14 + 0.5% (25ppm) Sokalan HP56K 4,5 6,1 7,4

C1 1 alone 3,9 8,2 10,0

C1 1 + 0.5% (25ppm) Sokalan HP56K 5,1 6,1 7,6

C12 alone 4,6 10,0 11 ,2

C12 + 0.5% (25ppm) Sokalan HP56K 4,4 5,8 7,6

C13 alone 3,7 8,4 10,0

C13 + 0.5% (25ppm) Sokalan HP56K 5,8 6,1 7,7

Nil 12,9

Sokalan 0.5% (25ppm) only 9,0

HP56 only Table 5. Results of dye transfer inhibition in the presence/absence of Sokalan HP56K for Direct Red 83.1 .

Table 6. Results of dye transfer inhibition in the presence/absence of Sokalan HP56K for Direct Blue 71 .

Dye bleeder fabric Direct Blue 71

ΔΕ

White acceptor fabric wfk10A

C14 alone 11 ,6 17,1 18,0

C14 + 0.5% (25ppm) Sokalan HP56K 3,6 1 J 1 ,6

C1 1 alone 7,6 14,8 17,5

C1 1 + 0.5% (25ppm) Sokalan HP56K 2,7 1 ,6 1 J

C12 alone 4,4 18,5 17,7

C12 + 0.5% (25ppm) Sokalan HP56K 2,0 1 ,4 1 J

C13 alone 7,2 15,6 17,6

C13 + 0.5% (25ppm) Sokalan HP56K 2,6 1 ,5 1 ,8

Nil 18,5

Sokalan 0.5% (25ppm) only 2,2

HP56 only Table 7. Results of dye transfer inhibition in the presence/absence of Sokalan HP56K for Acid Blue 1 13.

Table 8. Results of dye transfer inhibition in the presence/absence of Chromabond S400 for Direct Orange 39.

Dye bleeder fabric Direct Orange 39

ΔΕ

White acceptor fabric wfk10A

ComDosage of compound 3% (150ppm) 1.5% (75ppm) 0.5% (25ppm) pounds [% owod (ppm)]

C14 alone

C14 + 0.5% (25ppm) Chromabond S400

C1 1 alone 6,0 5,9 7,7

C1 1 + 0.5% (25ppm) Chromabond S400 2,0 2,0 2,0

C12 alone 6,3 7,3 8,0

C12 + 0.5% (25ppm) Chromabond S400 2,0 2,1 2,2

C13 alone 5,5 7,3 8,2

C13 + 0.5% (25ppm) Chromabond S400 1 ,8 2,0 2,2

Nil 1 1 ,8

S400 only 0.5% (25ppm) only 2,4 Table 9. Results of dye transfer inhibition in the presence/absence of Chromabond S400 for Direct Black 22.

Table 10. Results of dye transfer inhibition in the presence/absence of Chromabond S400 for Direct Red 83.1.

Dye bleeder fabric Direct Red 83.1

ΔΕ

White acceptor fabric wfk10A

C14 alone

C14 + 0.5% (25ppm) Chromabond S400

C1 1 alone 7,9 1 1 ,2 10,6

C1 1 + 0.5% (25ppm) Chromabond S400 3,3 3,2 3,3

C12 alone 1 1 ,3 10,6 11 ,3

C12 + 0.5% (25ppm) Chromabond S400 3,3 3,3 3,3

C13 alone 10,4 10,5 11 ,6

C13 + 0.5% (25ppm) Chromabond S400 3,2 3,3 3,2

Nil 14,4

S400 only 0.5% (25ppm) only 3,3 Table 1 1 . Results of dye transfer inhibition in the presence/absence of Chromabond S400 for Direct Blue 71.

Table 12. Results of dye transfer inhibition in the presence/absence of Chromabond S400 for Acid Blue 1 13.

For all tested compounds C1 to C14 significantly lower values of ΔΕ are found compared to the blank value containing no dye transfer inhibitor. Thus, strong dye transfer inhibition properties are observed.

Mixtures of Sokalan HP56K with compounds C1 1 to C14 show an additional, synergistic effect with regard to dye transfer inhibition which is significantly improved compared to the dye transfer inhibitor properties of compounds C1 1 to C14 as well as compared to Sokalan HP56K alone. As comparative example, Chromabond S400 was used, showing no significant synergistic effect when used in mixtures with compounds C1 1 to C14.

2. Use of imidazolium compounds in powder detergent formulation

The following commercially available powder model composition ECE2 from wfk was used:

Linear sodium alkyl benzene sulfonate 9.7 %

Ethoxylated fatty alcohol C12-18 (7 EO) 5.2 %

Sodium soap 3.6 %

Anti foam DC2-4248S 4.5 %

Sodium aluminium silicate zeolite 4A 32.5 %

Sodium carbonate 1 1 .8 %

Sodium salt of a copolymer from acrylic and maleic acid 5.2%

Sodium silicate (Si02:Na20 = 3,3:1 ) 3.4 %

Carboxymethylcellulose 1.3 %

Diethylene triamine penta (methylene phosphonic acid) 0.8 %

Sodium sulfate 9.8 %

Water 12.2 %

2.1 Experiments using imidazolium compound without additional dye transfer inhibiting polymer

Compounds as shown in Table 1 were added to a laundry liquor comprising a powder detergent (without dye transfer inhibitor, in the amounts given in Table 13 (% on weight of detergent, owod). White acceptor textiles made of either cotton (wfk 10A) or polyamide (Empa 406) were washed therein in the presence of a poorly dyed textile (bleeder). Washing conditions were: 5g/L detergent, liquor 250 ml_, 20 min, 60 °C. After wash the fabrics were rinsed for 5min at 30°C with 250ml_ water, centrifuged and ironed. The fabrics were instrumentally assessed with a Datacolor reflection spectrometer Model Type SF500 before and after wash. From the reflection data read- ings on L^*,a^*,b^* were derived and further expressed in ΔΕ values. The higher values of ΔΕ are observed for the acceptor fabrics in comparison to the initial whiteness before the test, the higher discoloration and dye transfer is found, respectively. For visual discrimination vs the reference fabric without any dye transfer inhibitor values of ΔΕ > 1 are required. Table 13. Results of dye transfer inhibition in a powder detergent formulation.

2.2 Experiments using imidazolium compound without additional dye transfer inhibiting polymer

Imidazolium compounds were added to a laundry liquor comprising a powder detergent formulation without dye transfer inhibitor, in the amounts given in the Table 15 (% on weight of detergent, owod) and additionally added 0.5% owod (25ppm) Sokalan HP56K. White acceptor textiles made of either cotton (wfk 10A) or polyamide (Empa 406) were washed therein in the presence of a poorly dyed textile (bleeder). Washing conditions were: 5 g/L detergent, liquor 250 mL, 20 min, 60°C. After wash the fabrics were rinsed for 5 min at 30°C with 250 mL water, centrifuged and ironed. The fabrics were instrumentally assessed with a Datacolor reflection spectrometer Model Type SF500 before and after wash. From the reflection data readings L^*,a^*,b^* were derived and further expressed in ΔΕ values. The higher values of ΔΕ are observed for the acceptor fabrics in comparison to the initial whiteness before the test, the higher discoloration and dye transfer is found, respectively. For visual discrimination vs the reference fabric without any dye transfer inhibitor values of ΔΕ > 1 are required.

Table 15. Results of dye transfer inhibition in the presence/absence of Sokalan HP56K for different dyes.

For all tested compounds C1 1- to C13 significantly lower values of ΔΕ are found compared to the blank value containing no dye transfer inhibitor. Thus, strong dye transfer inhibition properties are observed.

Mixtures of Sokalan HP56K with compounds C1 1 to C14 show an additional, synergistic effect with regard to dye transfer inhibition which is significantly improved compared to the dye transfer inhibitor properties of compounds C1 1 to C14 as well as compared to Sokalan HP56K alone.

Claims

1. The use of at least one polymeric, ionic compound comprising imidazolium groups (imidazolium compound), obtainable by reacting a) at least one a-dicarbonyl compound,

b) at least one aldehyde with one aldehyde group,

c) at least one amino compound having at least two primary amino groups,

d) optionally an amino compound having only one primary amino group and

e) at least one protic acid, and optionally subjecting the reaction product to an anion exchange, wherein the components a) and b) the aldehyde carbonyl groups may also be present as hemiacetal or acetal and the ketone carbonyl groups may also be present as hemiketal or ketal; as dye transfer inhibitor agent.

2. A method for preventing dye transfer during laundry, wherein at least one polymeric, ionic compound is used which comprises imidazolium groups (imidazolium compound), obtainable by reacting a) at least one a-dicarbonyl compound,

b) at least one aldehyde with one aldehyde group,

c) at least one amino compound having at least two primary amino groups,

d) optionally an amino compound having only one primary amino group and

e) at least one protic acid, and optionally subjecting the reaction product to an anion exchange, where in the components a) and b) the aldehyde carbonyl groups may also be present as hemiacetal or acetal and the ketone carbonyl groups may also be present as hemiketal or ketal; by bringing the polymeric, ionic compound in contact with laundry.

3. A method for preparation of a laundry composition by mixing at least one polymeric, ionic compound which comprises imidazolium groups (imidazolium compound), obtainable by reacting a) at least one a-dicarbonyl compound,

b) at least one aldehyde with one aldehyde group,

c) at least one amino compound having at least two primary amino groups,

d) optionally an amino compound having only one primary amino group and

e) at least one protic acid, and optionally subjecting the reaction product to an anion exchange, where in the components a) and b) the aldehyde carbonyl groups may also be present as hemiacetal or acetal and the ketone carbonyl groups may also be present as hemiketal or ketal; with a laundry detergent in liquid or solid form, wherein the laundry composition has dye transfer inhibiting properties.

The use or method as of claims 1 to 3, wherein component a) is selected from glyoxal, a hemiacetal, and acetal thereof.

The use or method as of claims 1 to 4, wherein component b) is a formaldehyde source.

The use or method as of claims 1 to 5, wherein component c) is selected from amines of the formula H2N-A-NH2, wherein A is a divalent aliphatic, cyclic, aromatic, alicyclic, arali- phatic or aliphatic-alicyclic radical which may be interrupted by one or more nonadjacent groups which are selected from -0-, -S- and -N(R^b)-, where R^b is selected from hydrogen, Ci-C2o-alkyl and a group +CH₂CH2-0}y-R^c, wherein y is 1 , 2, 3, 4, 5 or 6 and R^c is hydrogen or Ci-C4-alkyl; where alicyclic or aromatic moieties in the aforementioned alicyclic, aliphatic-alicyclic, aromatic or araliphatic radicals may be substituted by 1 , 2, 3 or 4 radicals selected from Ci-C2o-alkyl, Ci-C2o-alkoxy, a radical of the formula -0-fCH2CH20]_z-R^d, where R^d is hydrogen or Ci-C4-alkyl and z is 1 , 2, 3, 4, 5 or 6; carboxyl and carboxylate, and where the aliphatic moieties in the aforementioned aliphatic, aliphatic-alicyclic or araliphatic radicals may be substituted by 1 , 2, 3 or 4 radicals selected from Ci-C2o-alkoxy, a radical of the formula -0-fCH2CH20]_z-R^d, where R^d is hydrogen or Ci-C4-alkyl and z is 1 , 2, 3, 4, 5 or 6, carboxyl and carboxylate.

The use or method as of claims 1 to 6, wherein component c) is selected from compounds of formula H2N-(CH2)m-NH2, wherein m is an integer of 3 to 20.

8. The use or method as of claims 1 to 7, wherein the polymeric, ionic compound of claim 1 is used in combination with a detergent.

9. The use or method as of claim 8, wherein the amount of polymeric, ionic compound of claim 1 is 0.01 to 10.0 % of weight based on weight of laundry detergent.

10. The use or method as of claims 8 or 9, wherein the detergent is a liquid detergent.

1 1. The use or method as of claims 1 to 10, wherein the dye inhibitor agent is active in inhibit- ing transfer of direct dyes and/or acid dies.

12. The use or method as of claims 1 to 1 1 , wherein the dye inhibitor agent is active in inhibiting transfer of Acid Blue 1 13, Direct Orange 39, and/or Direct Black 22.

13. The use or method as of claims 1 to 12, wherein the polymeric, ionic compound of claim 1 is used in combination with one or more dye transfer inhibiting polymers which may be constructed on the basis of nitrogenous monomers polymerizable via vinyl or allyl groups.

14. The use or method as of claim 13, wherein the polymeric, ionic compound of claim 1 is used in combination with one or more dye transfer inhibiting polymers which may be constructed on the basis of nitrogenous monomers which are a copolymer of vinylpyrrolidon and vinylimidazol.