WO2013189816A1

WO2013189816A1 - Reactive dyes and their metal complexes, process for the production thereof and their use

Info

Publication number: WO2013189816A1
Application number: PCT/EP2013/062200
Authority: WO
Inventors: Vajiravelu Sivamurugan; Roxana Barbieru
Original assignee: Dystar Colours Distribution Gmbh
Priority date: 2012-06-18
Filing date: 2013-06-13
Publication date: 2013-12-27
Also published as: JP2015525280A; EP2904142A1; KR20150032668A; MX2014015534A; CN104487630A; AU2013279555A1

Abstract

The present invention refers to dyes of the formula (I) and mixtures thereof, in which n, A, B and K are defined as given in claim, a process for preparing them, and their use for dyeing and printing hydroxyl-, amino-, and/or carboxamido-containing materials.

Description

Reactive dyes and their metal complexes, process for fhe production thereof and their use The present invention relates to the technical fieldof reactive dyestuffs and their metal complexes for dyeing and printing of hydroxyl-, amino-, and carboxamido-containing material.

Metal complex reactive dyes based on bis and polyazo moiety containing at least one anchor are known from prior art and can be used as colorants in different applications, see for example DE3514969, DE3515407, US5319074, US3450689, US3462409, US3457251 , US3457252, GB1279283, GB1553474, WO2003104335, US5527886, DE3519551 and US4939243. In the context of the dyeing and printing of hydroxyl-, amino-, and/or carboxamido- containing material the known dyes have a number of technical disadvantages such as low fixation, moderate wet fastness and light fastness level. Hence, there is a need for developing new reactive dyes of superior technical performance. Surprisingly, it has now been found that the dyes of the formula (I) as described below show highly advantageous properties over the known dyes. These include superior wet fastness and light fastness, superior ecological profile as well as the possibility to achieve a wide range of shades including dark violets, dark browns, navy and blacks. The present invention refers to dyes of the formula (I) and mixtures thereof

wherein

n is an integer 0 or 1 ;

K is a radical of coupling heterocyclic component as described below;

A is a radical of middle component as described below when n is 1 and has the meaning of B when n is 0;

B is a radical of diazo component as described below;

M is hydrogen, lithium, sodium, potassium, ammonium or mono-, di-, tri- or tetra-(Ci- C₄)-alkylammonium, one equivalent of an alkali earth metal, or a monovalent organic cation;

K is a coupling component of following general formulae (K1 ) to (K3);

(K1 ) (K2) (K3) wherein,

R¹ and R⁴, independent from each other, are hydrogen, alkyl, cycloalkyl,

trifluoromethyl; alkoxy, cyano, carbamoyl, alkoxycarbonyl, COOM, amino; hydroxyl, monocycloalkyl-amino; monoalkyl-amino; di(cyclo)alkyl-amino; dialkyl-amino; monoaryl-amino; diaryl-amino; monocycloalkyl monoarylamino; monoalkyl monoaryl amino; alkylthio; arylthio;

or

are alkyl substituted by one or more substituents selected from the group consisting of hydroxy, cycloalkyl, heteroaryl, heterocycloalkyl, aryl, aryloxy, alkoxy, alkylthio, arylthio, halogen, cyano, COOM, alkoxycarbonyl, acyloxy, carbamoyl, nitro, amino, acylamino, arylcarbonylamino, alkylsulfonylamino, arylsulfonylamino, ureido, alkylureido and phenylureido; R², R⁵ and R¹¹, independent from each other, are cyano, carbamoyl, alkoxycarbonyl, trifluoromethyl, carbonyltrifluoromethyl, halogen, methyl sulfonyl or -SOsM;

R³', R⁶ to R⁹ and R¹², independent from each other are hydrogen, alkyl, alkenyl, cycloalkyl, trifluoromethyl, aryl, heteroaryl, heterocycloalkyl, carbamoyl, N- monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, Ν,Ν-dicycloalkyl-carbamoyl, N,N- dialkyl-carbamoyl, N-monoaryl-carbamoyl, Ν,Ν-diaryl-carbamoyl, N-monocycloalkyl-N- monoarylcarbamoyl, N-monoalkyl-N-monoarylcarbamoyl, sulfamoyi, N-monocycloalkyl- sulfamoyl, N-monoalkyl-sulfamoyl, N,N-dicycloalkylsulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N- monoaryl-sulfamoyl, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N- monoalkyl-N-monoaryl-sulfamoyl, amino, N-acylamino, N-thioacylamino, ureido, alkylureido, phenylureido, N-monoalkylamino, Ν,Ν-dialkyl-amino, N-arylamino, N,N- diarylamino, N-alkyl-N-aryl-amino, N-monocycloalkylamino, N;N-dicycloalkylamino, N- alkyl-N-cycloalkyl-amino, N-aryl-Ncycloalkyl-amino, N-heteroarylamino, N- heterocycloalkylamino or hydroxyakylsulfonylalkyl,

or

are alkyl interrupted by one or more heteroatoms such as oxygen or sulfur;

or

are alkyl substituted by one or more substituents selected from the group consisting of hydroxy, aryl, cycloalkyl, alkoxy, thioalkoxy, amino, N-monoalkyl-amino, N,N-di alkyl amino, N-monoaryl-amino, Ν,Ν-diaryl-amino, N-alkyl-N-aryl-amino, N-monocyclo alkyl- amino, Ν,Ν-dicycloalkyl-amino, N-monoalkyl-monocycloalkyl-amino, N,N-monoaryl- monocycloalkyl-amino, N-acylamino, N-alkylsulfonyl-amino, ureido, alkylureido, phenylureido, halogen, cyano, COOM, nitro, acyl, thioacyl, alkylsulfonyl, aryloyl, trifluoromethyl, heteroaryl, heterocycloalkyl, alkoxycarbonyl, alkoxythiocarbonyl, acyloxy, aryloyloxy, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N-dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N-diaryl- carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N-monoaryl- carbamoyl, sulfamoyi, N-monocycloalkyl-sulfamoyl, N-monoalkyl-sulfamoyl, N,N- dicycloalkyl-sulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl sulfamoyi, N,N-diaryl- sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N-monoalkyl-N-monoarylsulfamoyl or -S0₃M;

or alkyl or aryl substituted by -SO₂X; whereby

X is vinyl or a radical -CH₂CH₂-Y where Y is a group removable under alkaline conditions,which will leave the molecule under alkaline conditions to yield the vinyl sulfone function. Examples of such groups are OS0₃M, SS0₃M, OCOCH₃, OP0₃M and halogen;

and

R¹⁰ is hydroxyl or amino group;

and

whereby, in the general formula K2 the point of attachment and R⁵ can be positioned ortho or para to the amino rest bearing the substituents R⁶ and R⁷, meaning that when the point of attachment is positioned ortho to amino rest bearing the substituents R⁶ and R⁷, R⁵ is positioned para to the same, and vice versa. or

K is a coupling component of the following general formulae (K4) to (K6);

(K4)

(K5)

whereby

T is a reactive anchor of general formulae (T1) to (T3);

(T1) (T2) (T3) wherein

R²⁴and R²⁵, independent from one another are halogen or

R to R independent from one another are halogen;

or each of R²⁴ to R³⁰, independent from one another are substituted by one of the groups selected from general formulae (1 a) to (1 c);

(1 a) (1 b) (1 c) wherein

R³¹, R³², R³³⁹ and R³⁴⁰, independent from one another, are hydrogen, alkyl, phenyl or phenyl substituted by one of the groups selected from alkyl, alkoxy, halogen, or -SOsM; alkenyl, cycloalkyl, trifluoromethyl, aryl, heteroaryl, heterocycloalkyl, carbamoyl, N- monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, Ν,Ν-dicycloalkyl-carbamoyl, N,N- dialkyl-carbamoyl, N-monoaryl-carbamoyl, Ν,Ν-diaryl-carbamoyl, N-monocycloalkyl-N- monoarylcarbamoyl, N-monoalkyl-N-monoarylcarbamoyl, sulfamoyi, N-monocycloalkyl- sulfamoyl, N-monoalkyl-sulfamoyl, N,N-dicycloalkylsulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N- monoaryl-sulfamoyl, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N- monoalkyl-N-monoaryl-sulfamoyl, amino, N-acylamino, N-thioacylamino, ureido, alkylureido, phenylureido, N-monoalkylamino, Ν,Ν-dialkyl-amino, N-arylamino, N,N- diarylamino, N-alkyl-N-aryl-amino, N-monocycloalkylamino, N;N-dicycloalkylamino, N- alkyl-N-cycloalkyl-amino, N-aryl-Ncycloalkyl-amino, N-heteroarylamino, N- heterocycloalkylamino or hydroxyakylsulfonylalkyl,

or

are alkyl interrupted by one or more heteroatoms such as oxygen or sulfur;

or

are alkyl substituted by one or more substituents selected from the group consisting of hydroxy, aryl, cycloalkyl, alkoxy, thioalkoxy, amino, N-monoalkyl-amino, N,N-di alkyl amino, N-monoaryl-amino, Ν,Ν-diaryl-amino, N-alkyl-N-aryl-amino, N-monocyclo alkylamino, Ν,Ν-dicycloalkyl-amino, N-monoalkyl-monocycloalkyl-amino, N,N-monoaryl- monocycloalkyl-amino, N-acylamino, N-alkylsulfonyl-amino, ureido, alkylureido, phenylureido, halogen, cyano, COOM, nitro, acyl, thioacyl, alkylsulfonyl, aryloyl, trifluoromethyl, heteroaryl, heterocycloalkyl, alkoxycarbonyl, alkoxythiocarbonyl, acyloxy, aryloyloxy, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N-dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N-diaryl- carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N-monoaryl- carbamoyl, sulfamoyi, N-monocycloalkyl-sulfamoyl, N-monoalkyl-sulfamoyl, N,N- dicycloalkyl-sulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl sulfamoyi, N,N-diaryl- sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N-monoalkyl- N-monoarylsulfamoyl or S0₃M;

Each of R³³, R³⁴ and R³³⁸, independent from one another, are hydrogen, alkyl, alkoxyl, halogen, trifluoromethyl, cyano, nitro, ester, carbamoyl, SO₃M or-S0₂X;

where M is hydrogen, sodium, potassium, lithium or ammonium;

X is vinyl or a radical -CH₂CH₂-Y where Y is a group removable under alkaline conditions such as OSO₃M, SSO₃M, OCOCH₃, OPO₃M or halogen; p is an integer from 1 to 5 R¹³ and R¹⁵, independent from each other, are hydrogen, alkyl, cycloalkyl,

trifluoromethyl; alkoxy, cyano, carbamoyl, alkoxycarbonyl, COOM, amino; hydroxyl, monocycloalkyl-amino; monoalkyl-amino; di(cyclo)alkyl-amino; dialkyl-amino;

monoaryl-amino; diaryl-amino; monocycloalkyl monoarylamino; monoalkyl monoaryl amino; alkylthio; arylthio;

or

are alkyl substituted by one or more substituents selected from the group consisting of hydroxy, cycloalkyl, heteroaryl, heterocycloalkyl, aryl, aryloxy, alkoxy, alkylthio, arylthio, halogen, cyano, COOM, alkoxycarbonyl, acyloxy, carbamoyl, nitro, amino, acylamino, arylcarbonylamino, alkylsulfonylamino, arylsulfonylamino, ureido, alkylureido or phenylureido;

R¹², R¹⁶ and R²², independent from each other, are cyano, carbamoyl, alkoxycarbonyl, trifluoromethyl, carbonyltrifluoromethyl, halogen, methyl sulfonyl or -SO₃M;

R¹⁴, R¹⁷ to R²⁰ and R²³, independent from each other, are hydrogen, alkyl, alkenyl, cycloalkyl, trifluoromethyl, aryl, heteroaryl, heterocycloalkyl, carbamoyl, N- monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, Ν,Ν-dicycloalkyl-carbamoyl, N,N- dialkyl-carbamoyl, N-monoaryl-carbamoyl, Ν,Ν-diaryl-carbamoyl, N-monocycloalkyl-N- monoarylcarbamoyl, N-monoalkyl-N-monoarylcarbamoyl, sulfamoyi, N-monocycloalkyl- sulfamoyl, N-monoalkyl-sulfamoyl, N,N-dicycloalkylsulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N- monoaryl-sulfamoyl, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N- monoalkyl-N-monoaryl-sulfamoyl, amino, N-acylamino, N-thioacylamino, ureido, alkylureido, phenylureido, N-monoalkylamino, Ν,Ν-dialkyl-amino, N-arylamino, N,N- diarylamino, N-alkyl-N-aryl-amino, N-monocycloalkylamino, N;N-dicycloalkylamino, N- alkyl-N-cycloalkyl-amino, N-aryl-Ncycloalkyl-amino, N-heteroarylamino, N- heterocycloalkylamino or hydroxyakylsulfonylalkyl,

or

are alkyl interrupted by one or more heteroatoms such as oxygen or sulfur;

or are alkyl substituted by one or more substituents selected from the group consisting of hydroxy, aryl, cycloalkyl, alkoxy, thioalkoxy, amino, N-monoalkyl-amino, N,N-di alkyl amino, N-monoaryl-amino, Ν,Ν-diaryl-amino, N-alkyl-N-aryl-amino, N-monocyclo alkyl- amino, Ν,Ν-dicycloalkyl-amino, N-monoalkyl-monocycloalkyl-amino, N,N-monoaryl- monocycloalkyl-amino, N-acylamino, N-alkylsulfonyl-amino, ureido, alkylureido, phenylureido, halogen, cyano, COOM, nitro, acyl, thioacyl, alkylsulfonyl, aryloyl, trifluoromethyl, heteroaryl, heterocycloalkyl, alkoxycarbonyl, alkoxythiocarbonyl, acyloxy, aryloyloxy, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N-dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N-diaryl- carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N-monoaryl- carbamoyl, sulfamoyi, N-monocycloalkyl-sulfamoyl, N-monoalkyl-sulfamoyl, N,N- dicycloalkyl-sulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl sulfamoyi, N,N-diaryl- sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N-monoalkyl- N-monoarylsulfamoyl or SO₃M;

R²¹ is hydroxyl or amino group;

and

whereby, in the general formula K5 the point of attachment and R¹⁶ can be positioned ortho or para to the amino rest bearing the substituents R¹⁷ and R¹⁸, meaning that when the point of attachment is positioned ortho to amino rest bearing the substituents R¹⁷ and R¹⁸, R¹⁶ is positioned para to the same, and vice versa.

A is the phenylene or napthylene middle component and has the general formula (A1 ) or (A2);

(A1 ) (A2) R³⁴¹ to R³⁴⁸, independent from one another, are hydrogen, alkyl, alkyl chain interrupted by one or two heteroatoms, alkoxy, halogen, trifluoromethyl; cycloalkyl;

heterocycloalkyl; cyano; nitro; acyloxy; alkylcarbonyl, acylamino; aryloylamino, cinnamoylamino, alkylsulfonylamino; alkylthio; alkylsulfonyl, alkoxycarbonyl, carbamoyl, sulfamoyl, ureido, alkylureido, S0₃M, COOM;

or

are alkyl substituted by one or more substituents selected from the group consisting of hydroxy, aryl, cycloalkyl, alkoxy, thioalkoxy, amino, N-monoalkyl-amino, N,N- dialkylamino, N-monoaryl-amino, Ν,Ν-diaryl-amino, N-alkyl-N-aryl-amino, N- monocycloalkyl-amino, Ν,Ν-dicycloalkyl-amino, N-monoalkyl-monocycloalkyl-amino, Ν,Ν-monoaryl-monocycloalkyl-amino, N-acylamino, N-alkylsulfonyl-amino, ureido, alkylureido, phenylureido, halogen, cyano, COOM, nitro, acyl, thioacyl, alkylsulfonyl, aryloyl, trifluoromethyl, heteroaryl, heterocycloalkyl, alkoxycarbonyl,

alkoxythiocarbonyl, acyloxy, aryloyloxy, carbamoyl, N-monocycloalkyl-carbamoyl, N- monoalkyl-carbamoyl, N,N-dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl- carbamoyl, Ν,Ν-diaryl-carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N- monoalkyl-N-monoaryl-carbamoyl, sulfamoyl, N-monocycloalkyl-sulfamoyl, N- monoalkyl-sulfamoyl, N,N-dicycloalkyl-sulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N- monoarylsulfamoyl, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N- monoalkyl-N-monoarylsulfamoyl or SO₃M;

or

alkyl interrupted by one or more heteroatoms such as oxygen or sulfur;

or

are alkyl substituted by one or more substituents selected from the group consisting of hydroxy, aryl, cycloalkyl, alkoxy, thioalkoxy, amino, N-monoalkyl-amino, N,N-di alkyl amino, N-monoaryl-amino, Ν,Ν-diaryl-amino, N-alkyl-N-aryl-amino, N-monocyclo alkyl- amino, Ν,Ν-dicycloalkyl-amino, N-monoalkyl-monocycloalkyl-amino, N,N-monoaryl- monocycloalkyl-amino, N-acylamino, N-alkylsulfonyl-amino, ureido, alkylureido, phenylureido, halogen, cyano, COOM, nitro, acyl, thioacyl, alkylsulfonyl, aryloyl, trifluoromethyl, heteroaryl, heterocycloalkyl, alkoxycarbonyl, alkoxythiocarbonyl, acyloxy, aryloyloxy, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, Ν,Ν-dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N-diaryl- carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N-monoaryl- carbamoyl, sulfamoyi, N-monocycloalkyl-sulfamoyl, N-monoalkyl-sulfamoyl, N,N- dicycloalkyl-sulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl sulfamoyi, N,N-diaryl- sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N-monoalkyl- N-monoarylsulfamoyl or SO₃M;

or

a group of formulae (2a) to (2c)

(2a) (2b) (2c)

350

whereby R ^its and R independent from each other are, hydrogen, alkyl, alkyl substituted by SO3M, alkyl chain interrupted by one or two heteroatoms, or T;

whereby T has the same meaning as above;

U is -0-, -S- or -N(R³²⁹)-;

R³²³, R³²⁷ and R³²⁹, independent from one another, are hydrogen, alkyl, alkyl substituted by SO₃M, alkyl chain interrupted by one or two heteroatoms;

R³²⁴, R³²⁵, R³²⁶ and R³²⁸, independent from one another, are hydrogen, alkyl or alkyl chain interrupted by one or two heteroatoms;

r is an integer of 0 to 6;

s is an integer of 1 to 6;

^** refers to attachment point with A1 or A2

^*** refers to attachment point with T

T has the meaning as above;

B is the diazo component and has one of the general formula (B1 ) or (B2);

(B2)

wherein

R to R and R , independent from one another, are hydrogen or alkyi, alkoxy, halogen, cyano, -S0₃M, trifluoromethyl, nitro, ester, NHC(0)R⁴¹, CONH₂, S(0)₂R⁴ SO₂X or aminosubstituted by T or one of the general formulae (E1 ) to (E3);

(E3)

wherein

V is -0-, -S- or -N(R³⁵²)-

R⁴³, R⁴⁷ and R³⁵², independent from one another, are hydrogen, alkyi, alkyi substituted by S0₃M, alkyi chain interrupted by one or two heteroatoms; R⁴⁴, R⁴⁵, R⁴⁶ and R⁴⁸, independent from one another, are hydrogen, alkyl or alkyl chain interrupted by one or two heteroatoms;

R³³⁰ to R³³³, independent from one another, are hydrogen or alkyl, alkoxy, halogen, cyano, -S0₃M, trifluoromethyl, nitro, ester, NHC(0)R³³⁴, CONH₂, S(0)₂R³³⁵ or a group of formula (3a);

(3a)

R³³⁶ and R³³⁷, independent from one another, are hydrogen, alkyl, alkenyl, cycloalkyl, trifluoromethyl, aryl, heteroaryl, heterocycloalkyl, carbamoyl, N-monocycloalkyl- carbamoyl, N-monoalkyl-carbamoyl, Ν,Ν-dicycloalkyl-carbamoyl, N,N-dialkyl- carbamoyl, N-monoaryl-carbamoyl, Ν,Ν-diaryl-carbamoyl, N-monocycloalkyl-N- monoarylcarbamoyl, N-monoalkyl-N-monoarylcarbamoyl, sulfamoyi, N-monocycloalkyl- sulfamoyl, N-monoalkyl-sulfamoyl, N,N-dicycloalkylsulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N- monoaryl-sulfamoyl, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N- monoalkyl-N-monoaryl-sulfamoyl, amino, N-acylamino, N-thioacylamino, ureido, alkylureido, phenylureido, N-monoalkylamino, Ν,Ν-dialkyl-amino, N-arylamino, N,N- diarylamino, N-alkyl-N-aryl-amino, N-monocycloalkylamino, N;N-dicycloalkylamino, N- alkyl-N-cycloalkyl-amino, N-aryl-N-cycloalkyl-amino, N-heteroarylamino, N- heterocycloalkylamino or hydroxyakylsulfonylalkyl, or are alkyl interrupted by one or more heteroatoms such as oxygen or sulfur;

or

are alkyl substituted by one or more substituents selected from the group consisting of hydroxy, aryl, cycloalkyl, alkoxy, thioalkoxy, amino, N-monoalkyl-amino, N,N-dialkyl amino, N-monoaryl-amino, Ν,Ν-diaryl-amino, N-alkyl-N-aryl-amino, N-monocyclo alkyl- amino, Ν,Ν-dicycloalkyl-amino, N-monoalkyl-monocycloalkyl-amino, N,N-monoaryl- monocycloalkyl-amino, N-acylamino, N-alkylsulfonyl-amino, ureido, alkylureido, phenylureido, halogen, cyano, COOM, nitro, acyl, thioacyl, alkylsulfonyl, aryloyl, trifluoromethyl, heteroaryl, heterocycloalkyl, alkoxycarbonyl, alkoxythiocarbonyl, acyloxy, aryloyloxy, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N-dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N-diaryl- carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N-monoaryl- carbamoyl, sulfamoyl, N-monocycloalkyl-sulfamoyl, N-monoalkyl-sulfamoyl, N,N- dicycloalkyl-sulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl sulfamoyl, N,N-diaryl- sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N-monoalkyl- N-monoarylsulfamoyl or SO₃M; or alkyl interrupted by one or more heteroatoms such as oxygen or sulphur; or containing a rest with free valence to link to rest reactive anchor T;

R⁴¹, R⁴², R³³⁴ and R³³⁵, independent from one another are hydrogen, alkyl or alkyl substituted by hydroxy or halogen;

c is an integer of 0 to 6;

d is an integer of 1 to 6;

*^*** refers to attachment point with Bl and B2;

*^**** refers to attachment point with T;

*^*****refers to attachment point with E3;

T and X are the same as defined above;

Preferably hydrogen, lithium, sodium, potassium, ammonium, or one equivalent of an alkali earth metal and particularly preferred hydrogen, sodium, potassium, or lithium ... with the general proviso that the dyes of general formula (I) contain at least one reactive anchor.

This invention refers to all kinds of tautomeric and geometric isomers of the dyes of the formula (I). Alkyl groups appearing in this application may be straight-chain or branched, may have 1 to 12 C-atoms and are for example methyl, ethyl, n-propyl, isopropyl, n-butyl, sec- butyl, tert-butyl, isobutyl, n-pentyl, isopentyl, n-hexyl, 2-ethylhexyl, n-heptyl, n-octyl, n- nonyl, n-decyl, n-undecyl and n-dodecyl, preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, n-pentyl, isopentyl, n-hexyl, 2-ethylhexyl, and particularly preferred methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, isopentyl, n-hexyl, and 2-ethylhexyl,. The same logic applies to alkoxy groups which for example are methoxy and ethoxy.

Cycloalkyl groups are (C₃-C₈)-cycloalkyl groups, preferably (C -C₈)-cycloalkyl, particularly preferred cyclopentyl and cyclohexyl. The term cyloalkyi comprises for the purpose of the present application substituted cycloalklyl groups and unsatured cycloalkyl groups as well. A preferred group of this type is cyclopentenyl. Preferred substituents are alkyl, cycloalkyl, heterocycloalkyl, hydroxyalkyl, halogen, hydroxyl, alkoxy, alkylthio, acyl, nitro, cyano, -S0₃M, -COOM, amino, monoalkylamino, dialkylamino, mono(hydroxyalkyl)amino, bis (hydroxyalkyl)amino, monoalkyl- mono(hydroxyalkyl)amino, carbamoyl, sulfamoyl, acylamino, ureido,

aminosulfonylamino, alkoxycarbonyl or acyloxy. Particularly preferred substitutents alkyl, hydroxyalkyl, halogen, hydroxyl, alkoxy, acyl, nitro, cyano, -S0₃M, -COOM, amino, monoalkylamino, dialkylamino, carbamoyl, sulfamoyl, ureido or acylamino. Alkenyl groups may be straight-chain or branched and are for example vinyl and allyl. The term alkenyl comprises for the purpose of the present application alkynyl groups as well, for example ethynyl and propargyl.

Heterocycloalkyl groups are preferably pyrrolidine, piperidine, morpholine or

piperazine, tetrahydrofuran, imidazole, triazole.

Aryl groups appearing in this application are phenyl or naphthyl. The terms phenyl and naphthyl comprises unsubstituted as well as substituted phenyl and naphthyl.

Preferred substituents are alkyl, cycloalkyl, heterocycloalkyl, hydroxyalkyl, halogen, hydroxyl, alkoxy, alkylthio, acyl, nitro, cyano, -SO₃M, -COOM, amino, monoalkylamino, dialkylamino, mono(hydroxyalkyl)amino, bis (hydroxyalkyl)amino, monoalkyl- mono(hydroxyalkyl)amino, carbamoyl, sulfamoyl, acylamino, ureido,

aminosulfonylamino, alkoxycarbonyl or acyloxy. Particularly preferred substitutents alkyl, hydroxyalkyl, halogen, hydroxyl, alkoxy, acyl, nitro, cyano, -SO₃M, -COOM, amino, monoalkylamino, dialkylamino, carbamoyl, sulfamoyl, ureido or acylamino. Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine and particularly preferred chlorine and bromine

Preferred embodiments of the present invention are dyes of the formulae (la) to (If) and mixtures thereof;

(la)

(lb)

(Id)

(le)

(If)

wherein

R⁴⁹, R⁵⁸, R⁶⁶, R⁷⁴, R⁷⁸ and R⁸⁵, independent from each other, are hydrogen, alkyl, cycloalkyi, trifluoromethyl; alkoxy, cyano, carbamoyl, alkoxycarbonyl, COOM, amino; hydroxyl, monocycloalkyl-amino; monoalkyl-amino; di(cyclo)alkyl-amino; dialkyl-amino; monoaryl-amino; diaryl-amino; monocycloalkyl monoarylamino; monoalkyi monoaryl amino; alkylthio; arylthio; or

R⁵⁰, R⁵⁴, R⁵⁹, R⁶⁷, R⁷⁵ and R⁷⁹, independent from each other, are cyano, carbamoyl, alkoxycarbonyl, trifluoromethyl, carbonyltrifluoromethyl, halogen, methyl sulfonyl or - S0₃M;

R⁵¹, R⁵⁵, R⁶⁰ and R⁶⁸ independent from each other, are hydrogen, alkyl, alkenyl, cycloalkyl, trifluoromethyl, aryl, heteroaryl, heterocycloalkyl, carbamoyl, N- monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, Ν,Ν-dicycloalkyl-carbamoyl, N,N- dialkyl-carbamoyl, N-monoaryl-carbamoyl, Ν,Ν-diaryl-carbamoyl, N-monocycloalkyl-N- monoarylcarbamoyl, N-monoalkyl-N-monoarylcarbamoyl, sulfamoyi, N-monocycloalkyl- sulfamoyi, N-monoalkyl-sulfamoyl, N,N-dicycloalkylsulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N- monoaryl-sulfamoyl, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N- monoalkyl-N-monoaryl-sulfamoyl, amino, N-acylamino, N-thioacylamino, ureido, alkylureido, phenylureido, N-monoalkylamino, Ν,Ν-dialkyl-amino, N-arylamino, N,N- diarylamino, N-alkyl-N-aryl-amino, N-monocycloalkylamino, N;N-dicycloalkylamino, N- alkyl-N-cycloalkyl-amino, N-aryl-Ncycloalkyl-amino, N-heteroarylamino, N- heterocycloalkylamino or hydroxyakylsulfonylalkyl,

or

are alkyl interrupted by one or more heteroatoms such as oxygen or sulfur;

or

R⁵², R⁵³, R⁵⁶, R⁵⁷, R⁶⁴, R⁶⁵, R⁷², R⁷³, R⁷⁶, R⁷⁷, R⁸³ and R⁸⁴, independent from one another, are hydrogen or alkyl, alkoxy, halogen, cyano, -SO₃M, trifluoromethyl, nitro, ester, NHC(0)R⁸⁶, CONH₂, S(0)₂R⁸⁷ or -S0₂X;

R⁸⁶ and R⁸⁷ independent from one another are hydrogen, alkyl or alkyl substituted by hydroxy or halogen;

R⁶¹ to R⁶³, R⁶⁹ to R⁷¹ and R⁸⁰ to R⁸², independent from one another, are hydrogen, alkyl, alkyl substituted, alkyl chain interrupted by one or two heteroatoms, alkoxy, alkoxy substituted, halogen, trifluoromethyl; cycloalkyl; heterocycloalkyl; cyano; nitro; acyloxy; alkylcarbonyl, acylamino; aryloylamino, cinnamoylamino, alkylsulfonylamino; alkylthio; alkylsulfonyl, alkoxycarbonyl, carbamoyl, sulfamoyi, ureido, alkylureido, SO₃M, COOM; or a group of formulae (2a) to (2c) as defined above; In the especially preferred dyes of the present invention,

R⁴⁹, R⁵⁸, R⁶⁶, R⁷⁴, R⁷⁸ and R⁸⁵, are hydrogen or (d-C₄)-alkyl or aryl;

R⁵⁰, R⁵⁴, R⁵⁹, R⁶⁷, R⁷⁵ and R⁷⁹ are cyano, carbamido, alkoxy carbonyl, carbonyl, sulfomethyl, -SO₃M or -COOM;

R⁵¹, R⁵⁵, R⁶⁰ and R⁶⁸ are alkyl or aryl; Aryl substituted by one more substituents selected from alkyl, alkoxy, halogen or -SO₃M;

R⁶¹ to R⁶³, R⁶⁹ to R⁷¹ and R⁸⁰ toR⁸², independent from one another, are hydrogen, (Ci- C )-alkyl, (Ci-C )-alkoxyl, hydroxyl, carbamido, halogen or -SO₃M or contain group of formulae (2a) to (2c);

R⁸⁶ and R⁸⁷ independent from one another are hydrogen, alkyl or alkyl substituted by hydroxyl;

R⁸⁸ and R⁸⁹ independent fro each other, are hydrogen, alkyl, alkyl substituted by SO₃M; T, X and M are the same as defined above.

Further preferred embodiments of the present invention are dyes of the formulae (Ig) and (Ih) and mixtures thereof;

(ig)

(Ih)

wherein

R⁹⁰ and R⁹⁴, independent from each other, are hydrogen, alkyl, cycloalkyl, trifluoromethyl; alkoxy, cyano, carbamoyl, alkoxycarbonyl, COOM, amino; hydroxyl, monocycloalkyl-amino; monoalkyl-amino; di(cyclo)alkyl-amino; dialkyl-amino; monoaryl-amino; diaryl-amino; monocycloalkyl monoarylamino; monoalkyl monoaryl amino; alkylthio; arylthio;

or

R⁹¹ and R⁹⁵, independent from each other, are cyano, carbamoyl, alkoxycarbonyl, trifluoromethyl, carbonyltrifluoromethyl, halogen, methyl sulfonyl or -SOsM;

D¹ and D² independent from each other, are hydrogen, alkyl, alkenyl, cycloalkyl, trifluoromethyl, aryl, heteroaryl, heterocycloalkyl, carbamoyl, N-monocycloalkyl- carbamoyl, N-monoalkyl-carbamoyl, Ν,Ν-dicycloalkyl-carbamoyl, N,N-dialkyl- carbamoyl, N-monoaryl-carbamoyl, Ν,Ν-diaryl-carbamoyl, N-monocycloalkyl-N- monoarylcarbamoyl, N-monoalkyl-N-monoarylcarbamoyl, sulfamoyi, N-monocycloalkyl- sulfamoyl, N-monoalkyl-sulfamoyl, N,N-dicycloalkylsulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N- monoaryl-sulfamoyl, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N- monoalkyl-N-monoaryl-sulfamoyl, amino, N-acylamino, N-thioacylamino, ureido, alkylureido, phenylureido, N-monoalkylamino, Ν,Ν-dialkyl-amino, N-arylamino, N,N- diarylamino, N-alkyl-N-aryl-amino, N-monocycloalkylamino, N;N-dicycloalkylamino, N- alkyl-N-cycloalkyl-amino, N-aryl-Ncycloalkyl-amino, N-heteroarylamino, N- heterocycloalkylamino or hydroxyakylsulfonylalkyl,

or

are alkyl interrupted by one or more heteroatoms such as oxygen or sulfur;

or

R⁹², R⁹³, R⁹⁹ and R¹⁰⁰, independent from one another, are hydrogen or alkyl, alkoxy, halogen, cyano, -SO₃M, trifluoromethyl, nitro, ester, NHC(0)R¹⁰¹, CONH₂, S(0)₂R¹⁰² or

R¹⁰¹ and R¹⁰² independent from one another are hydrogen, alkyl or alkyl substituted by hydroxy or halogen.

R⁹⁶ to R⁹⁸, independent from one another, are hydrogen, alkyl, alkyl substituted, alkyl chain interrupted by one or two heteroatoms, alkoxy, alkoxy substituted,

halogen , trifluoromethyl; cycloalkyl; heterocycloalkyl; cyano; nitro; acyloxy;

alkylcarbonyl, acylamino; aryloylamino, cinnamoylamino, alkylsulfonylamino; alkylthio; alkylsulfonyl, alkoxycarbonyl, carbamoyl, sulfamoyi, ureido, alkylureido, S0₃M, COOM; or a group of formulae (2a) to (2c) as defined above;

with the proviso D¹ and D² contain a rest with free valence to link to rest reactive anchor T;

T and M are the same as defined above;

In the especially preferred dyes of the formula (Ig) and (Ih),

R⁹⁰ and R⁹⁴, indenpendently, is hydrogen or (Ci-C₄)-alkyl or aryl;

R⁹¹ and R⁹⁵, indenpendently, is cyano, carbamido, alkoxy carbonyl, carbonyl, sulfomethyl, -SO₃M or -COOM;

D¹ and D², independently, is alkyl or aryl; alkyl or aryl substituted by one more substituents selected from alkyl, alkoxy, halogen or -SOsM, amino, N-alkyl amino; R⁹⁶ to R⁹⁸, independent from one another are hydrogen, (Ci-C₄)-alkyl, (Ci-C₄)-alkoxyl, hydroxyl, carbamido, halogen or -SOsM or contain group of formulae (2a) to (2c); R¹⁰¹ and R¹⁰² independent from one another are hydrogen, alkyl or alkyl substituted by hydroxyl;

T, X and M are the same as defined above.

Further preferred embodiments of the present invention are dyes of the formulae (li) to (II) and mixtures thereof;

(li)

(II)

wherein

R¹⁰⁵, R¹¹⁰, R¹¹⁵ and R¹²³, independent from each other, are hydrogen, alkyl, cycloalkyl, trifluoromethyl; alkoxy, cyano, carbamoyl, alkoxycarbonyl, COOM, amino; hydroxyl, monocycloalkyl-amino; monoalkyl-amino; di(cyclo)alkyl-amino; dialkyl-amino;

monoaryl-amino; diaryl-amino; monocydoalkyi monoarylamino; monoalkyi monoaryl amino; alkylthio; arylthio;

or

are alkyl substituted by one or more substituents selected from the group consisting of hydroxy, cycloalkyl, heteroaryl, heterocycloalkyl, aryl, aryloxy, alkoxy, alkylthio, arylthio, halogen, cyano, COOM, alkoxycarbonyl, acyloxy, carbamoyl, nitro, amino, acylamino, arylcarbonylamino, alkylsulfonylamino, arylsulfonylamino, ureido, alkylureido or phenylureido; R¹⁰⁶, R¹¹¹, R¹¹⁶ and R¹²⁴, independent from each other, are cyano, carbamoyl, alkoxycarbonyl, trifluoromethyl, carbonyltrifluoromethyl, halogen, methyl sulfonyl or - S0₃M;

R¹⁰⁷, R¹¹², R¹¹⁷ and R¹²⁵, independent from each other, are hydrogen, alkyl, alkenyl, cycloalkyl, trifluoromethyl, aryl, heteroaryl, heterocycloalkyl, carbamoyl, N- monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, Ν,Ν-dicycloalkyl-carbamoyl, N,N- dialkyl-carbamoyl, N-monoaryl-carbamoyl, Ν,Ν-diaryl-carbamoyl, N-monocycloalkyl-N- monoarylcarbamoyl, N-monoalkyl-N-monoarylcarbamoyl, sulfamoyi, N-monocycloalkyl- sulfamoyl, N-monoalkyl-sulfamoyl, N,N-dicycloalkylsulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N- monoaryl-sulfamoyl, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N- monoalkyl-N-monoaryl-sulfamoyl, amino, N-acylamino, N-thioacylamino, ureido, alkylureido, phenylureido, N-monoalkylamino, Ν,Ν-dialkyl-amino, N-arylamino, N,N- diarylamino, N-alkyl-N-aryl-amino, N-monocycloalkylamino, N;N-dicycloalkylamino, N- alkyl-N-cycloalkyl-amino, N-aryl-Ncycloalkyl-amino, N-heteroarylamino, N- heterocycloalkylamino or hydroxyakylsulfonylalkyl,

or

are alkyl interrupted by one or more heteroatoms such as oxygen or sulfur;

or

are alkyl substituted by one or more substituents selected from the group consisting of hydroxy, aryl, cycloalkyl, alkoxy, thioalkoxy, amino, N-monoalkyl-amino, N,N-di alkyl amino, N-monoaryl-amino, Ν,Ν-diaryl-amino, N-alkyl-N-aryl-amino, N-monocyclo alkylamino, Ν,Ν-dicycloalkyl-amino, N-monoalkyl-monocycloalkyl-amino, N,N-monoaryl- monocycloalkyl-amino, N-acylamino, N-alkylsulfonyl-amino, ureido, alkylureido, phenylureido, halogen, cyano, COOM, nitro, acyl, thioacyl, alkylsulfonyl, aryloyl, trifluoromethyl, heteroaryl, heterocycloalkyl, alkoxycarbonyl, alkoxythiocarbonyl, acyloxy, aryloyloxy, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N-dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N-diaryl- carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N-monoaryl- carbamoyl, sulfamoyi, N-monocycloalkyl-sulfamoyl, N-monoalkyl-sulfamoyl, N,N- dicycloalkyl-sulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl sulfamoyi, N,N-diaryl- sulfamoyi, N-monocycloalkyl-N-monoarylsulfamoyl, N-monoalkyl- N-monoarylsulfamoyl or SO₃M;

R¹⁰⁸, R¹⁰⁹, R¹¹³, R¹¹⁴, R¹²¹ , R¹²², R¹²⁹ and R¹³⁰, independent from one another, are hydrogen or alkyl, alkoxy, halogen, cyano, -SO₃M, trifluoromethyl, nitro, ester,

NHC(0)R¹³¹ , CONH2, S(0)₂R¹³² or -S0₂X;

R¹³¹ and R¹³², independent from one another, are hydrogen, alkyl or alkyl substituted by hydroxy or halogen.

_Ri i8 _{10 R}i2o _{and R}126 _{10 R}128_; j_nc|_ep_enc|_ent f_{rom one} another, are hydrogen, alkyl, alkyl substituted, alkyl chain interrupted by one or two heteroatoms, alkoxy, alkoxy substituted, halogen ,trifluoromethyl; cycloalkyi; heterocycloalkyi; cyano; nitro; acyloxy; alkylcarbonyl, acylamino; aryloylamino, cinnamoylamino, alkylsulfonylamino; alkylthio; alkylsulfonyl, alkoxycarbonyl, carbamoyl, sulfamoyi, ureido, alkylureido, S0₃M, COOM; or a group of formulae (2a) to (2c);

E⁴ to E⁷, independent from each other, are a group of general formulae (E1 ) - (E3);

In the especially preferred dyes of the present invention,

R¹⁰⁵, R¹¹⁰, R¹¹⁵ and R¹²³, independent from each other are hydrogen or (Ci-C₄)-alkyl or aryl;

R¹⁰⁶, R¹¹¹, R¹¹⁶ and R¹²⁴, independent from each other are cyano, carbamido, alkoxy carbonyl, carbonyl, sulfomethyl, -SO₃M or -COOM;

R¹⁰⁷, R¹¹², R¹¹⁷ and R¹²⁵, independent from each other are alkyl or aryl; Aryl substituted by one more substituents selected from alkyl, alkoxy, halogen or -SOsM;

_Ri i8 _{10 R}i2o _{and R}126 _{10 R}128_; j_nc|_ep_enc|_ent f_{rom one} another are hydrogen, (C₁-C₄)- alkyl, (Ci-C₄)-alkoxyl, hydroxyl, carbamido, halogen or -SO3M or contain group of formulae (2a) to (2c);

R¹⁰⁸, R¹⁰⁹, R¹¹³, R¹¹⁴, R¹²¹ , R¹²², R¹²⁹ and R¹³⁰, independent from one another are hydrogen or alkyl, alkoxy, halogen, -SO₃M or -SO₂X;

R¹³¹ and R¹³², independent from one another are hydrogen, alkyl or alkyl substituted by hydroxyl;

E⁴ to E⁷, independent from each other, are a group of general formulae (E1 ) to (E3); T, X and M are the same as defined above. Further preferred emodiment of the present invention are dyes of the formulae (Im) to (Ip) and mixtures thereof;

wherein

R¹³⁵, R¹³⁹, R¹⁴³ and R¹⁵⁰, independent from each other, are hydrogen, alkyl, cycloalkyl, trifluoromethyl; alkoxy, cyano, carbamoyl, alkoxycarbonyl, COOM, amino; hydroxyl, monocycloalkyl-amino; monoalkyl-amino; di(cyclo)alkyl-amino; dialkyl-amino;

monoaryl-amino; diaryl-amino; monocycloalkyi monoarylamino; monoalkyi monoaryl amino; alkylthio; arylthio;

or

are alkyl substituted by one or more substituents selected from the group consisting of hydroxy, cycloalkyl, heteroaryl, heterocycloalkyl, aryl, aryloxy, alkoxy, alkylthio, arylthio, halogen, cyano, COOM, alkoxycarbonyl, acyloxy, carbamoyl, nitro, amino, acylamino, arylcarbonylamino, alkylsulfonylamino, arylsulfonylamino, ureido, alkylureido or phenylureido; R¹³⁶, R¹⁴⁰, R¹⁴⁴ and R¹⁵¹, independent from each other, are cyano, carbamoyl, alkoxycarbonyl, trifluoromethyl, carbonyltrifluoromethyl, halogen, methyl sulfonyl or - S0₃M;

D³, D⁴, D⁵ and D⁶ independent from each other, are hydrogen, alkyl, alkenyl, cycloalkyl, trifluoromethyl, aryl, heteroaryl, heterocycloalkyl, carbamoyl, N- monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, Ν,Ν-dicycloalkyl-carbamoyl, N,N- dialkyl-carbamoyl, N-monoaryl-carbamoyl, Ν,Ν-diaryl-carbamoyl, N-monocycloalkyl-N- monoarylcarbamoyl, N-monoalkyl-N-monoarylcarbamoyl, sulfamoyi, N-monocycloalkyl- sulfamoyl, N-monoalkyl-sulfamoyl, N,N-dicycloalkylsulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N- monoaryl-sulfamoyl, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N- monoalkyl-N-monoaryl-sulfamoyl, amino, N-acylamino, N-thioacylamino, ureido, alkylureido, phenylureido, N-monoalkylamino, Ν,Ν-dialkyl-amino, N-arylamino, N,N- diarylamino, N-alkyl-N-aryl-amino, N-monocycloalkylamino, N;N-dicycloalkylamino, N- alkyl-N-cycloalkyl-amino, N-aryl-Ncycloalkyl-amino, N-heteroarylamino, N- heterocycloalkylamino or hydroxyakylsulfonylalkyl,

or

alkyl interrupted by one or more heteroatoms such as oxygen or sulfur;

or

alkyl substituted by one or more substituents selected from the group consisting of hydroxy, aryl, cycloalkyl, alkoxy, thioalkoxy, amino, N-monoalkyl-amino, N,N-dialkyl amino, N-monoaryl-amino, Ν,Ν-diaryl-amino, N-alkyl-N-aryl-amino, N-monocyclo alkylamino, Ν,Ν-dicycloalkyl-amino, N-monoalkyl-monocycloalkyl-amino, N,N-monoaryl- monocycloalkyl-amino, N-acylamino, N-alkylsulfonyl-amino, ureido, alkylureido, phenylureido, halogen, cyano, COOM, nitro, acyl, thioacyl, alkylsulfonyl, aryloyl, trifluoromethyl, heteroaryl, heterocycloalkyl, alkoxycarbonyl, alkoxythiocarbonyl, acyloxy, aryloyloxy, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N-dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N-diaryl- carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N-monoaryl- carbamoyl, sulfamoyi, N-monocycloalkyl-sulfamoyl, N-monoalkyl-sulfamoyl, N,N- dicycloalkyl-sulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl sulfamoyi, N,N-diaryl- sulfamoyi, N-monocycloalkyl-N-monoarylsulfamoyl, N-monoalkyl- N-monoarylsulfamoyl or SO₃M;

R¹³⁷, R¹³⁸, R¹⁴¹, R¹⁴², R¹⁴⁸, R¹⁴⁹, R¹⁵⁵ and R¹⁵⁶, independent from one another, are hydrogen or alkyl, alkoxy, halogen, cyano, -SO₃M, trifluoromethyl, nitro, ester,

NHC(0)R¹⁵⁷, CONH2, S(0)₂R¹⁵⁸ or -S0₂X;

R¹⁵⁷ and R¹⁵⁸, independent from one another, are hydrogen, alkyl or alkyl substituted by hydroxy or halogen.

R¹⁴⁵, R¹⁴⁶, R¹⁴⁷, R¹⁵², R¹⁵³ and R¹⁵⁴, independent from one another, are hydrogen, alkyl, alkyl substituted, alkyl chain interrupted by one or two heteroatoms, alkoxy, alkoxy substituted, halogen ,trifluoromethyl; cycloalkyi; heterocycloalkyi; cyano; nitro; acyloxy; alkylcarbonyl, acylamino; aryloylamino, cinnamoylamino, alkylsulfonylamino; alkylthio; alkylsulfonyl, alkoxycarbonyl, carbamoyl, sulfamoyi, ureido, alkylureido, S0₃M, COOM; or contain a group of formulae (2a) to (2c) as defined above;

E⁸ to E¹¹, independent from each other, are a group of general formulae (E1 ) to (E3) as defined above;

T, X and M are the same as defined above.

In the especially preferred dyes of the formulae (Im) to (Ip),

R¹³⁵, R¹³⁹, R¹⁴³ and R¹⁵⁰, independent from each other are hydrogen or (Ci-C₄)-alkyl or aryl;

R¹³⁶, R¹⁴⁰, R¹⁴⁴ and R¹⁵¹, independent from each other are cyano, carbamido, alkoxy carbonyl, carbonyl, sulfomethyl, -SO₃M or -COOM;

D³, D⁴, D⁵ and D⁶, independent from each other are alkyl or aryl; alkyl or aryl

substituted by one more substituents selected from alkyl, alkoxy, halogen or -SO3M, amino, N-alkyl amino; or amino group substituted by T;

R¹³⁷, R¹³⁸, R¹⁴¹, R¹⁴², R¹⁴⁸, R¹⁴⁹, R¹⁵⁵ and R¹⁵⁶, independent from one another are hydrogen or alkyl, alkoxy, halogen, -SO₃M or -SO₂X;

R¹⁴⁵ to R¹⁴⁷ and R¹⁵² to R¹⁵⁴, independent from one another, are hydrogen, (Ci-C₄)- alkyl, (Ci-C )-alkoxyl, hydroxyl, carbamido, halogen or -SO₃M or contain group of formulae (2a) to (2c);

E⁸ to E¹¹, independent from each other, are a group of general formulae (E1 ) to (E3); T, X and M are the same as defined above.

Further preferred embodiments of the present invention are dyes of the formulae (Iq) to (It) and mixtures thereof;

wherein

each of R¹⁶¹, R¹⁶⁸, R¹⁷⁵ and R¹⁸⁵, independent from each other, are alkyl, cyano, carbamoyl, alkoxycarbonyl, trifluoromethyl, carbonyltrifluoromethyl, halogen, methyl sulfonyl or -S0₃M;

R¹⁶², R¹⁶⁹, R¹⁷⁶ and R¹⁸⁶ independent from each other are hydroxyl or amino;

_R163 _{tQ R}165_{j R}170 _{{q r}172_{> r}177 _{{q r}179 _R187 _{{q r}1∞ j_ndependent f_{rom each otheri} are hydrogen, alkyl, alkenyl, cycloalkyl, trifluoromethyl, aryl, heteroaryl,

heterocycloalkyl, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N-dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N-diaryl- carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N- monoarylcarbamoyl, sulfamoyl, N-monocycloalkyl-sulfamoyl, N-monoalkyl-sulfamoyl, Ν,Ν-dicycloalkylsulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl-sulfamoyl, N,N-diaryl- sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N-monoalkyl-N-monoaryl- sulfamoyl, amino, N-acylamino, N-thioacylamino, ureido, alkylureido, phenylureido, N- monoalkylamino, Ν,Ν-dialkyl-amino, N-arylamino, N,N-diarylamino, N-alkyl-N-aryl- amino, N-monocycloalkylamino, N;N-dicycloalkylamino, N-alkyl-N-cycloalkyl-amino, N- aryl-Ncycloalkyl-amino, N-heteroarylamino, N-heterocycloalkylamino or

hyd roxya ky I s u If o ny I a I ky I ,

or

are alkyl interrupted by one or more heteroatoms such as oxygen or sulfur;

or

are alkyl substituted by one or more substituents selected from the group consisting of hydroxy, aryl, cycloalkyl, alkoxy, thioalkoxy, amino, N-monoalkyl-amino, N,N-di alkyl amino, N-monoaryl-amino, Ν,Ν-diaryl-amino, N-alkyl-N-aryl-amino, N-monocyclo alkyl- amino, Ν,Ν-dicycloalkyl-amino, N-monoalkyl-monocycloalkyl-amino, N,N-monoaryl- monocycloalkyl-amino, N-acylamino, N-alkylsulfonyl-amino, ureido, alkylureido, phenylureido, halogen, cyano, COOM, nitro, acyl, thioacyl, alkylsulfonyl, aryloyl, trifluoromethyl, heteroaryl, heterocycloalkyl, alkoxycarbonyl, alkoxythiocarbonyl, acyloxy, aryloyloxy, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N-dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N-diaryl- carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N-monoaryl- carbamoyl, sulfamoyi, N-monocycloalkyl-sulfamoyl, N-monoalkyl-sulfamoyl, N,N- dicycloalkyl-sulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl sulfamoyi, N,N-diaryl- sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N-monoalkyl- N-monoarylsulfamoyl or SO₃M;

or

alkyl or aryl substituted by -SO₂X; whereby X is vinyl or a radical -CH₂CH₂-Y where Y is a group removable under alkaline conditions such as OSO₃M; or a rest with free valence to link to reactive anchor T;

R¹⁶⁶, R¹⁶⁷, R¹⁷³, R¹⁷⁴, R¹⁸³, R¹⁸⁴, R¹⁹³ and R¹⁹⁴, independent from one another, are hydrogen or alkyl, alkoxy, halogen, cyano, -SO₃M, trifluoromethyl, nitro, ester,

NHC(0)R¹⁹⁵, CONH2, S(0)₂R¹⁹⁶ or -S0₂X; R¹⁹⁵ and R¹⁹⁶, independent from one another, are hydrogen, alkyl or alkyl substituted by hydroxy or halogen;

_R ⁱ⁸o _{t0 R} ¹⁸² _{and R} ⁱ⁹o _{t0 R} ¹⁹² _; j_nc|_ep_enc|_ent f_{rom one} another, are hydrogen, alkyl, alkyl substituted, alkyl chain interrupted by one or two heteroatoms, alkoxy, alkoxy substituted, halogen ,trifluoromethyl; cycloalkyl; heterocycloalkyl; cyano; nitro; acyloxy; alkylcarbonyl, acylamino; aryloylamino, cinnamoylamino, alkylsulfonylamino; alkylthio; alkylsulfonyl, alkoxycarbonyl, carbamoyl, sulfamoyl, ureido, alkylureido, S0₃M, COOM; or contain a group of formulae (2a) to (2c);

X is the same as defined above.

In the especially preferred dyes of the present invention,

R¹⁶¹, R¹⁶⁸, R¹⁷⁵ and R¹⁸⁵ are (Ci-C₄)-alkyl, cyano, carbamido, alkoxy carbonyl, carbonyl or sulfomethyl;

R¹⁶², R¹⁶⁹, R¹⁷⁶ and R¹⁸⁶ are hydroxyl or amino;

R¹⁶³ to R¹⁶⁵, R¹⁷⁰ to R¹⁷², R¹⁷⁷ to R¹⁷⁹ and R¹⁸⁷ to R¹⁸⁹, are independent from one another are hydrogen, (Ci-C )-alkyl, (Ci-C )-alkyloxy, halogen, -S0₃M or -S0₂X or free valence substituted with T;

R¹⁶⁶, R¹⁶⁷, R¹⁷³, R¹⁷⁴, R¹⁸³, R¹⁸⁴, R¹⁹³ and R¹⁹⁴, independent from one another are hydrogen, (Ci-C )-alkyl, (Ci-C )-alkoxyl, halogen or -S0₃M;

R¹⁸⁰ to R¹⁸² and R¹⁹⁰ to R¹⁹², independent from one another, are hydrogen, (Ci-C₄)- alkyl, (Ci-C₄)-alkoxyl, hydroxyl, carbamido, halogen or -S0₃M or contain the group of formulae (2a) to (2c);

T, X and M have the same meaning as above. Further preferred embodiments of the present invention are dyes of the formulae (lu) to (Ix) and mixtures thereof;

(Iw)

R¹⁹⁹, R²⁰⁶, R²¹³ and R²²³, independent from each other, are alkyl, cyano, carbamoyl, alkoxycarbonyl, trifluoromethyl, carbonyltrifluoromethyl, halogen, methyl sulfonyl or - SO₃M;

R²⁰⁰, R²⁰⁷, R²¹⁴ and R²²⁴ independent from each other are hydroxyl or amino; _R2oi _{tQ R}2o_{3i R}208 _{tQ R}2I O_{j R}215 _{tQ r}217 _{and R}225 _{fo R}227_> j_ndepenc|_ent f_rom each other, are hydrogen, alkyl, alkenyl, cycloalkyl, trifluoromethyl, aryl, heteroaryl,

heterocycloalkyl, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N-dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N-diaryl- carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N- monoarylcarbamoyl, sulfamoyi, N-monocycloalkyl-sulfamoyl, N-monoalkyl-sulfamoyl, N,N-dicycloalkylsulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl-sulfamoyl, N,N-diaryl- sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N-monoalkyl-N-monoaryl- sulfamoyl, amino, N-acylamino, N-thioacylamino, ureido, alkylureido, phenylureido, N- monoalkylamino, Ν,Ν-dialkyl-amino, N-arylamino, Ν,Ν-diarylamino, N -a Iky I- N -aryl - amino, N-monocycloalkylamino, N;N-dicycloalkylamino, N-alkyl-N-cycloalkyl-amino, N- aryl-Ncycloalkyl-amino, N-heteroarylamino, N-heterocycloalkylamino or

hydroxyakylsulfonylalkyl,

or

are alkyl interrupted by one or more heteroatoms such as oxygen or sulfur;

or

are alkyl substituted by one or more substituents selected from the group consisting of hydroxy, aryl, cycloalkyl, alkoxy, thioalkoxy, amino, N-monoalkyl-amino, N,N-di alkyl amino, N-monoaryl-amino, Ν,Ν-diaryl-amino, N-alkyl-N-aryl-amino, N-monocyclo alkyl- amino, Ν,Ν-dicycloalkyl-amino, N-monoalkyl-monocycloalkyl-amino, N,N-monoaryl- monocycloalkyl-amino, N-acylamino, N-alkylsulfonyl-amino, ureido, alkylureido, phenylureido, halogen, cyano, COOM, nitro, acyl, thioacyl, alkylsulfonyl, aryloyl, trifluoromethyl, heteroaryl, heterocycloalkyl, alkoxycarbonyl, alkoxythiocarbonyl, acyloxy, aryloyloxy, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N-dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N-diaryl- carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N-monoaryl- carbamoyl, sulfamoyi, N-monocycloalkyl-sulfamoyl, N-monoalkyl-sulfamoyl, N,N- dicycloalkyl-sulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl sulfamoyi, N,N-diaryl- sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N-monoalkyl- N-monoarylsulfamoyl or S0₃M;

or alkyl or aryl substituted by -SO₂X; whereby

X is vinyl or a radical -CH₂CH₂-Y where Y is a group removable under alkaline conditions such as OSO₃M; or contains a rest with free valence to link to rest reactive anchor T;

R²⁰⁴, R²⁰⁵, R²¹¹, R²¹², R²²¹ , R²²², R²³¹ and R²³², independent from one another are hydrogen or alkyl, alkoxy, halogen, cyano, -SO₃M, trifluorom ethyl, nitro, ester,

NHC(0)R²³³, CONH2, S(0)₂R²³⁴ or -S0₂X;

R²³³ and R²³⁴, independent from one another are hydrogen, alkyl or alkyl substituted by hydroxy or halogen;

R²¹⁸ to R²²⁰ and R²²⁸ to R²³⁰, independent from one another are hydrogen, alkyl, alkyl substituted, alkyl chain interrupted by one or two heteroatoms, alkoxy, alkoxy substituted, halogen ,trifluoromethyl; cycloalkyi; heterocycloalkyi; cyano; nitro; acyloxy; alkylcarbonyl, acylamino; aryloylamino, cinnamoylamino, alkylsulfonylamino; alkylthio; alkylsulfonyl, alkoxycarbonyl, carbamoyl, sulfamoyl, ureido, alkylureido, SO₃M, COOM; or a group of formulae (2a) to (2c) as defined above;

E¹² to E¹⁵, independent from each other, are a group of general formulae (E1 ) to (E3) as defined above;

T, X and M have the same meanings as above. In the especially preferred dyes of the present invention,

R¹⁹⁹, R²⁰⁶, R²¹³ and R²²³ independent from each other are (Ci-C₄)-alkyl, cyano, carbamido, alkoxy carbonyl, carbonyl or sulfomethyl;

R²⁰⁰, R²⁰⁷, R²¹⁴ and R²²⁴ independent from each other are hydroxyl or amino;

_R201 _{tQ R}203^ _R208 _{tQ R}210_{j R}215 _{{q r}217 _R225 _{{q r}227 _^ j_{ndependent from Qne an0}ther, are hydrogen, (Ci-C )-alkyl, (Ci-C )-alkyloxy, halogen, -SO₃M or -S0₂X or free valence substituted with T;

R²⁰⁴, R²⁰⁵, R²¹¹, R²¹², R²²¹ , R²²², R²³¹ and R²³², independent from one another are hydrogen, (Ci-C )-alkyl, (Ci-C )-alkoxyl, halogen or -S0₃M;

R218 _{10 R}22o _{and R}228 _{to R}230_; independent from one another are hydrogen, (C₁-C₄)- alkyl, (Ci-C₄)-alkoxyl, hydroxyl, carbamido, halogen or -SOsM or contain the group of formulae (2a) to (2c); E¹² to E¹⁵, independent from each other, are a group of general formulae (E1 ) to (E3); T and X have the same meanings as above.

Further preferred embodiments of the present invention are dyes of the formulae (ly) to (lab) and mixtures thereof;

(lz)

laa)

(lab) wherein

R²³⁷, R²⁴⁵, R²⁵³ and R²⁶⁴, independent from each other, are hydrogen, alkyl, cycloalkyl, trifluoromethyl; alkoxy, cyano, carbamoyl, alkoxycarbonyl, COOM, amino; hydroxyl, monocycloalkyl-amino; monoalkyl-amino; di(cyclo)alkyl-amino; dialkyl-amino;

or are alkyl substituted by one or more substituents selected from the group consisting of hydroxy, cycloalkyl, heteroaryl, heterocycloalkyl, aryl, aryloxy, alkoxy, alkylthio, arylthio, halogen, cyano, COOM, alkoxycarbonyl, acyloxy, carbamoyl, nitro, amino, acylamino, arylcarbonylamino, alkylsulfonylamino, arylsulfonylamino, ureido, alkylureido or phenylureido;

R²³⁸, R²⁴⁶, R²⁵⁴ and R²⁶⁵, independent from each other, are cyano, carbamoyl, alkoxycarbonyl, trifluoromethyl, carbonyltrifluoromethyl, halogen, methyl sulfonyl or - S0₃M;

_R239 _{tQ R}24_{2i R}247 _{{q r}250 ^ _R255 _{to R}258 _R267 _{to R}270_j j_ndepenc|_ent f_r0m each Other, are hydrogen, alkyl, alkenyl, cycloalkyl, trifluoromethyl, aryl, heteroaryl,

heterocycloalkyl, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N-dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N-diaryl- carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N- monoarylcarbamoyl, sulfamoyl, N-monocycloalkyl-sulfamoyl, N-monoalkyl-sulfamoyl, N,N-dicycloalkylsulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl-sulfamoyl, N,N-diaryl- sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N-monoalkyl-N-monoaryl- sulfamoyl, amino, N-acylamino, N-thioacylamino, ureido, alkylureido, phenylureido, N- monoalkylamino, Ν,Ν-dialkyl-amino, N-arylamino, Ν,Ν-diarylamino, N -a Iky I- N -aryl - amino, N-monocycloalkylamino, N;N-dicycloalkylamino, N-alkyl-N-cycloalkyl-amino, N- aryl-Ncycloalkyl-amino, N-heteroarylamino, N-heterocycloalkylamino or

hydroxyakylsulfonylalkyl,

or

are alkyl interrupted by one or more heteroatoms such as oxygen or sulfur;

or

are alkyl substituted by one or more substituents selected from the group consisting of hydroxy, aryl, cycloalkyl, alkoxy, thioalkoxy, amino, N-monoalkyl-amino, N,N-di alkyl amino, N-monoaryl-amino, Ν,Ν-diaryl-amino, N-alkyl-N-aryl-amino, N-monocyclo alkylamino, Ν,Ν-dicycloalkyl-amino, N-monoalkyl-monocycloalkyl-amino, N,N-monoaryl- monocycloalkyl-amino, N-acylamino, N-alkylsulfonyl-amino, ureido, alkylureido, phenylureido, halogen, cyano, COOM, nitro, acyl, thioacyl, alkylsulfonyl, aryloyl, trifluoromethyl, heteroaryl, heterocycloalkyl, alkoxycarbonyl, alkoxythiocarbonyl, acyloxy, aryloyloxy, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N-dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N-diaryl- carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N-monoaryl- carbamoyl, sulfamoyi, N-monocycloalkyl-sulfamoyl, N-monoalkyl-sulfamoyl, N,N- dicycloalkyl-sulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl sulfamoyi, N,N-diaryl- sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N-monoalkyl- N-monoarylsulfamoyl or SO₃M; or alkyl containing a rest with free valence to link to rest reactive anchor T; R²⁴³, R²⁴⁴, R²⁵¹, R²⁵², R²⁶², R²⁶³, R²⁷⁴ and R²⁷⁵, independent from one another, are hydrogen or alkyl, alkoxy, halogen, cyano, -SO₃M, trifluoromethyl, nitro, ester,

NHC(0)R²⁷⁶, CONH2, S(0)₂R²⁷⁷ or -S0₂X;

R²⁷⁶ and R²⁷⁷, independent from one another, are hydrogen, alkyl or alkyl substituted by hydroxy or halogen;

R²⁵⁹ to R²⁶¹ and R²⁷¹ to R²⁷³, independent from one another, are hydrogen, alkyl, alkyl substituted, alkyl chain interrupted by one or two heteroatoms, alkoxy, alkoxy substituted, halogen ,trifluoromethyl; cycloalkyi; heterocycloalkyi; cyano; nitro; acyloxy; alkylcarbonyl, acylamino; aryloylamino, cinnamoylamino, alkylsulfonylamino; alkylthio; alkylsulfonyl, alkoxycarbonyl, carbamoyl, sulfamoyi, ureido, alkylureido, S0₃M, COOM; or contain a group of formulae (2a) to (2c) as defined above; In the especially preferred dyes of the formulae (ly) to (lab),

R²³⁷, R²⁴⁵, R²⁵³ and R²⁶⁴ are hydrogen or (Ci-C₄)-alkyl, aryl, (Ci-C₄)-alkyloxy;

R²³⁸, R²⁴⁶, R²⁵⁴ and R²⁶⁵ are (Ci-C₄)-alkyl, cyano, carbamido, alkoxy carbonyl, carbonyl or sulfomethyl;

_R239 _{tQ R}242^ _R247 _{{q r}250 ^ _R255 _{{q r}258 ^ _R267 _{{q r}270 _^ j_{ndependent from Qne an0}ther, are hydrogen, (Ci-C )-alkyl, (Ci-C₆)-alkyloxy, aryl;

or -Alk-S0₂X,

or aryl substituted by one or more groups selected from halogen, -SO₃M or -SO₂X or free valence substituted with T;

R²⁴³, R²⁴⁴, R²⁵¹, R²⁵², R²⁶², R²⁶³, R²⁷⁴ and R²⁷⁵, independent from one another, are hydrogen, (Ci-C₄)-alkyl, (Ci-C₄)-alkoxyl, halogen or -S0₃M; R²⁵⁹ to R²⁶¹ and R²⁷¹ to R²⁷³, independent from one another, are hydrogen, (C₁ -C4)- alkyl, (Ci-C₄)-alkoxyl, hydroxyl, carbamido, halogen or -SOsM or contain the group of formulae (2a) to (2c);

T, X and M have the same meanings as defined above.

Further preferred embodiments of the present invention are dyes of the formulae (lac) to (laf) and mixtures thereof;

wherein

R , R , R and R , independent from each other, are hydrogen, alkyl, cycloalkyl, trifluoromethyl; alkoxy, cyano, carbamoyl, alkoxycarbonyl, COOM, amino; hydroxyl, monocycloalkyl-amino; monoalkyl-amino; di(cyclo)alkyl-amino; dialkyl-amino;

or

R²⁸¹, R²⁸⁹, R²⁹⁷ and R³⁰⁸, independent from each other, are cyano, carbamoyl, alkoxycarbonyl, trifluoromethyl, carbonyltrifluoromethyl, halogen, methyl sulfonyl or - SO₃M;

_R282 _{tQ R}2∞ _R290 _{{q r}293 ^ _R298 _{{q r}301 _R309 _{{q R}312 j_{ndependent from egch other>} are hydrogen, alkyl, alkenyl, cycloalkyl, trifluoromethyl, aryl, heteroaryl,

heterocycloalkyl, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N-dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N-diaryl- carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N- monoarylcarbamoyl, sulfamoyi, N-monocycloalkyl-sulfamoyl, N-monoalkyl-sulfamoyl, N,N-dicycloalkylsulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl-sulfamoyl, N,N-diaryl- sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N-monoalkyl-N-monoaryl- sulfamoyl, amino, N-acylamino, N-thioacylamino, ureido, alkylureido, phenylureido, N- monoalkylamino, Ν,Ν-dialkyl-amino, N-arylamino, N,N-diarylamino, N-alkyl-N-aryl- amino, N-monocycloalkylamino, N;N-dicycloalkylamino, N-alkyl-N-cycloalkyl-amino, N- aryl-Ncycloalkyl-amino, N-heteroarylamino, N-heterocycloalkylamino or

hyd roxya ky I s u If o ny I a I ky I ,

or

are alkyl interrupted by one or more heteroatoms such as oxygen or sulfur;

or

are alkyl substituted by one or more substituents selected from the group consisting of hydroxy, aryl, cycloalkyl, alkoxy, thioalkoxy, amino, N-monoalkyl-amino, N,N-di alkyl amino, N-monoaryl-amino, Ν,Ν-diaryl-amino, N-alkyl-N-aryl-amino, N-monocyclo alkyl- amino, Ν,Ν-dicycloalkyl-amino, N-monoalkyl-monocycloalkyl-amino, N,N-monoaryl- monocycloalkyl-amino, N-acylamino, N-alkylsulfonyl-amino, ureido, alkylureido, phenylureido, halogen, cyano, COOM, nitro, acyl, thioacyl, alkylsulfonyl, aryloyl, trifluoromethyl, heteroaryl, heterocycloalkyl, alkoxycarbonyl, alkoxythiocarbonyl, acyloxy, aryloyloxy, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N-dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N-diaryl- carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N-monoaryl- carbamoyl, sulfamoyi, N-monocycloalkyl-sulfamoyl, N-monoalkyl-sulfamoyl, N,N- dicycloalkyl-sulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl sulfamoyi, N,N-diaryl- sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N-monoalkyl- N-monoarylsulfamoyl or SO₃M; or alkyl containing a rest with free valence to link to rest reactive anchor T; R²⁸⁶, R²⁸⁷, R²⁹⁴, R²⁹⁵, R³⁰⁵, R³⁰⁶, R³¹⁶ and R³¹⁷, independent from one another, are hydrogen or alkyl, alkoxy, halogen, cyano, -SO₃M, trifluoromethyl, nitro, ester,

NHC(0)R³¹⁸, CONH2, S(0)₂R³¹⁹ or -S0₂X;

R³¹⁸ and R³¹⁹, independent from one another, are hydrogen, alkyl or alkyl substituted by hydroxy or halogen;

R³⁰² to R³⁰⁴ and R³¹³ to R³¹⁵, independent from one another, are hydrogen, alkyl, alkyl substituted, alkyl chain interrupted by one or two heteroatoms, alkoxy, alkoxy substituted, halogen ,trifluoromethyl; cycloalkyi; heterocycloalkyi; cyano; nitro; acyloxy; alkylcarbonyl, acylamino; aryloylamino, cinnamoylamino, alkylsulfonylamino; alkylthio; alkylsulfonyl, alkoxycarbonyl, carbamoyl, sulfamoyl, ureido, alkylureido, SO3M, COOM or contain a group of formulae (2a) to (2c) as defined above;

E¹⁶ to E¹⁹, independent from each other, are a group of general formulae (E1 ) to (E3) as defined above;

T, X and M have the same meanings as defined above. In the especially preferred dyes of the present invention

R²⁸⁰, R²⁸⁸, R²⁹⁶ and R³⁰⁷ independent from each other are hydrogen or (d-C₄)-alkyl, aryl, (Ci-C )-alkyloxy;

R²⁸¹, R²⁸⁹, R²⁹⁷ and R³⁰⁸ independent from each other are (Ci-C₄)-alkyl, cyano, carbamido, alkoxy carbonyl, carbonyl or sulfomethyl;

R²⁸² to R²⁸⁵, R²⁹⁰ to R²⁹³, R²⁹⁸ to R³⁰¹ and R³⁰⁹ to R³¹¹, independent from one another, are hydrogen, (Ci-C )-alkyl, (Ci-C₆)-alkyloxy, aryl;

or -Alk-S0₂X,

R²⁸⁶, R²⁸⁷, R²⁹⁴, R²⁹⁵, R³⁰⁵, R³⁰⁶, R³¹⁶ and R³¹⁷, independent from one another, are hydrogen, (Ci-C )-alkyl, (Ci-C )-alkoxyl, halogen or -S0₃M;

R302 _{10 R}304 _{and R}313 _{to R}315^ j_nc|_ep_enc|_ent f_{rom one} another, are hydrogen, (C₁-C₄)- alkyl, (Ci-C₄)-alkoxyl, hydroxyl, carbamido, halogen or -S0₃M or contain the group of formulae (2a) to (2c);

E¹⁶ to E¹⁹, independent from each other, are a group of general formulae (E1 ) to (E3); T, X and M are the same as defined above.

Examples of the preferred dyes of this invention are the dyes from 1 to 168 (Table 1 ) corresponding to the general formula (II).

(II)

wherein

K⁷ is a radical of heterocyclic coupling component and has the same meaning as described above for K;

A³ is a radical of middle component and has the same meaning as described above for A; B³ is a radical of diazo component and has the same meaning as described above for B; M is hydrogen, sodium, potassium, lithium or ammonium;

Table 1

9^S03^H oso₃H

Further examples of the preferred dyes of this invention are the dyes from 169 to 336 (Table 2 corresponding to the general formula (III).

(III)

wherein

K⁸ is a radical of heterocyclic coupling component and has the same meaning as described above for K;

A⁴ is a radical of middle component and has the same meaning as described above for A; B⁴ is a radical of diazo component and has the same meaning as described above for B; M is hydrogen, sodium, potassium, lithium or ammonium;

Table 2

The present invention also provides a process for the preparation of the dyes of the formula (I) which comprises diazotization of the compounds of the formulae (IV) and reacting the correspondingly obtained diazonium salts with a compound of the formula K to obtain the intermediate of general formula (V).

In a further step the diazo component (B-NH₂) is diazotised and coupled onto the intermediate V to obtain the bisazo of eneral formula (VI).

Alternatively, the diazo component (B-NH₂) can be diazotised and coupled onto the compound (A-NH₂) to obtain intermediate (VII). Further, the intermediate (VII) is diazotised and coupled onto compound (V) to obtain the trisazo dye of general formula (VIII).

(VIII)

Further, the dyes (VI) and (VIII) are reacted with copper salt especially copper sulphate to obtain the copper complex dyes (IX) and (X).

(IX)

Wherein A, B and K have the same meaning as described above.

The diazotization of the compounds of the formulae (IV), B-NH₂ and (VII) can be performed by means of diazotization methods that are known to a person skilled in the art, preferably by using sodium nitrite or nitrosylsulfuric acid in acidic medium using inorganic acids such as hydrochloric acid, sulfuric acid or phosphoric acid or mixtures thereof or organic acids such as acetic acid or propionic acid or mixtures thereof. Also mixtures of inorganic acid with organic acids can be advantageously used.

The coupling reaction of the diazotized compounds of the formulae (IV), B-Nh and (VII) onto the compound of formula (K) and (V) can likewise be performed by known methods. The complexation reaction of the dyes (VI) and (VIII) can likewise be performed by known methods.

The compounds of the formula A, B and K are known and commercially available or can be synthesised by means of common chemical reactions known to a person skilled in the art.

The present invention also provides for the use of the present invention's dyes for dyeing or printing of hydroxyl-, amino-, and/or carboxamido-containing material, or a process for dyeing or printing of hydroxyl- and/or carboxamido-containing material whereby a dye is applied to the material and fixed on the material by usual means, the process utilizing a dye in accordance with the present invention.

Hydroxyl-containing materials can be of natural or synthetic origin. Examples are cellulose fiber materials, preferably cotton, linen, hemp, jute and ramie fibers, regenerated cellulose fibers such as preferably staple viscose and filament viscose, chemically modified cellulose fibers, such as for example aminated cellulose fibers, and also polyvinyl alcohols. Carboxamido-containing materials are for example synthetic and natural polyamides and polyurethanes, for example wool and other animal hairs, silk, leather, nylon-6,6, nylon-6, nylon-1 1 and nylon-4.

The hydroxyl- and/or carboxamido-containing materials mentioned can be present in various forms. For instance in the form of sheetlike structures, such as paper and leather, in the form of films, such as nylon films, or in the form of a bulk mass, for example composed of polyamide and polyurethane, in particular in the form of fibers, for example cellulose fibers. The fibers are preferably textile fibers, for example in the form of woven fabrics or yarns or in the form of hanks or wound packages.

The dyes of the present invention and their salts or mixtures can be used as a single dyeing product in dyeing or printing processes or it can be part of a di/tri or multi- component combination product in dyeing or in printing compositions. Dyes of this invention and their salts or mixtures are highly compatible with other known and/or commercially available dyes and they can be used together with such dyes to obtain specific hues of similarly good technical performance. Technical performance includes build-up, fastness properties and levelness. The dyes according to the invention can be applied to the materials mentioned, especially the fiber materials mentioned, by the application techniques known for water-soluble dyes. This applies to both, dyeing and printing processes.

It applies in particular to the production of dyeings on fiber materials composed of wool or other natural polyamides or of synthetic polyamides and their mixtures with other fiber material. In general, the material to be dyed is introduced into the bath at a temperature of about 40°C, agitated therein for some time, the dyebath is then adjusted to the desired weakly acidic, preferably weakly acetic acid, pH and the actual dyeing is carried out at a temperature between 60 and 98°C. However, the dyeings can also be carried out at the boil or in sealed dyeing apparatus at temperatures of up to 106°C.

Since the water solubility of the dyes according to the invention is very good, they can also be used with advantage in customary continuous dyeing processes.

The dyes of the present invention can also be used in digital printing processes, in particular in digital textile printing. For this the dyes of the present invention need to be formulated in inks. Aqueous inks for digital printing which comprise a dye in

accordance with the present invention likewise form part of the subject matter of the present invention.

The inks of the present invention comprise the dye of the present invention in amounts which preferably range from 0.1 % by weight to 50% by weight, more preferably from 1 % by weight to 30% by weight and most preferably from 1 % by weight to 15% by weight, based on the total weight of the ink.

The inks, as well as the dye of the present invention, may if desired contain further dyes used in digital printing.

For the inks of the present invention to be used in the continuous flow process, a conductivity of 0.5 to 25 mS/m can be set by adding an electrolyte. Useful electrolytes include for example lithium nitrate and potassium nitrate. The inks of the present invention may include organic solvents at a total level of 1 -50% and preferably 5-30% by weight. Suitable organic solvents are for example alcohols, for example methanol, ethanol, 1 -propanol, isopropanol, 1 -butanol, tert-butanol, pentyl alcohol, polyhydric alcohols for example: 1 ,2-ethanediol, 1 ,2,3-propanetriol, butanediol, 1 ,3-butanediol, 1 ,4-butanediol, 1 ,2-propanediol, 2,3-propanediol, pentanediol, 1 ,4-pentanediol, 1 ,5- pentanediol, hexanediol, D,L-1 ,2-hexanediol, 1 ,6-hexanediol, 1 ,2,6-hexanetriol, 1 ,2- octanediol, polyalkylene glycols, for example: polyethylene glycol, polypropylene glycol, alkylene glycols having 1 to 8 alkylene groups, for example: monoethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, thioglycol, thiodiglycol, butyltriglycol, hexylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, low alkyl ethers of polyhydric alcohols, for example: ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol monohexyl ether, triethylene glycol monomethyl ether, triethylene glycol monobutyl ether, tripropylene glycol monomethyl ether, tetraethylene glycol monomethyl ether, tetraethylene glycol monobutyl ether, tetraethylene glycol dimethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, tripropylene glycol isopropyl ether, polyalkylene glycol ethers, such as for example: polyethylene glycol monomethyl ether,

polypropylene glycol glycerol ether, polyethylene glycol tridecyl ether, polyethylene glycol nonylphenyl ether, amines, such as for example: methylamine, ethylamine, triethylamine, diethylamine, dimethylamine, trimethylamine, dibutylamine,

diethanolamine, triethanolamine, N-acetylethanolamine, N-formylethanolamine, ethylenediamine, urea derivatives, such as for example: urea, thiourea, N-methylurea, Ν,Ν'-epsilon dimethylurea, ethyleneurea, 1 , 1 ,3,3-tetramethylurea, amides, such as for example: dimethylformamide, dimethylacetamide, acetamide, ketones or keto alcohols, such as for example: acetone, diacetone alcohol, cyclic ethers, such as for example: tetrahydrofuran, trimethylolethane, trimethylolpropane, 2-butoxyethanol, benzyl alcohol, 2-butoxyethanol, gamma butyrolactone, epsilon-caprolactam, further sulfolane, dimethylsulfolane, methylsulfolane, 2,4-dimethylsulfolane, dimethyl sulfone, butadiene sulfone, dimethyl sulfoxide, dibutyl sulfoxide, N-cyclohexylpyrrolidone, N-methyl-2-pyrrolidone, N-ethylpyrrolidone, 2-pyrrolidone, 1 -(2-hydroxyethyl)- 2-pyrrolidone, 1 -(3-hydroxypropyl)-2-pyrrolidone, 1 ,3-dimethyl-2-imidazolidinone, 1 ,3-dimethyl-2-imidazolinone, 1 ,3-bismethoxymethylimidazolidine, 2-(2- methoxyethoxy)ethanol, 2-(2-ethoxyethoxy)ethanol, 2-(2-butoxyethoxy)ethanol, 2-(2- propoxyethoxy)ethanol, pyridine, piperidine, butyrolactone, trimethylpropane,

1 ,2-dimethoxypropane, dioxane ethyl acetate, ethylenediaminetetraacetate ethyl pentyl ether, 1 ,2-dimethoxypropane and trimethylpropane.

The inks of the invention may further include customary additives, for example viscosity moderators to set viscosities in the range from 1.5 to 40.0 mPas in a temperature range from 20 to 50°C. Preferred inks have a viscosity of 1.5 to 20 mPas and particularly preferred inks have a viscosity of 1 .5 to 15 mPas.

Useful viscosity moderators include rheological additives, for example:

polyvinylcaprolactam, polyvinylpyrrolidone and their copolymers polyetherpolyol, associative thickeners, polyurea, polyurethane, sodium alginates, modified

galactomannans, polyetherurea, polyurethane, nonionic cellulose ethers.

As further additives the inks of the invention may include surface-active substances to set surface tensions of 20 to 65 mN/m, which are adapted if necessary as a function of the process used (thermal or piezo technology). Useful surface-active substances include for example: all surfactants, preferably nonionic surfactants, butyldiglycol, 1 ,2- hexanediol.

The inks of the present invention may further include customary additives, for example substances to inhibit fungal and bacterial growth in amounts from 0.01 to 1 % by weight based on the total weight of the ink.

The inks may be prepared in a conventional manner by mixing the components in water. The inks of the invention are particularly useful in inkjet printing processes for printing a wide variety of pretreated materials, such as silk, leather, wool, polyamide fibers and polyurethanes, and cellulosic fiber materials of any kind. Blend fabrics, for example blends of cotton, silk, wool with polyester fibers or polyamide fibers can similarly be printed. In contrast to conventional textile printing, where the printing ink already contains all necessary chemicals, in digital or inkjet printing the auxiliaries have to be applied to the textile substrate in a separate pretreatment step.

The pretreatment of the textile substrate, for example cellulose and regenerated cellulose fibers and also silk and wool, is effected with an aqueous alkaline liquor prior to printing. In addition there is a need for thickeners to prevent flowing of the motives when the printing ink is applied, for example sodium alginates, modified polyacrylates or highly etherified galactomannans. These pretreatment reagents are uniformly applied to the textile substrate in a defined amount using suitable applicators, for example using a 2- or 3-roll pad, contactless spraying technologies, by means of foam application or using appropriately adapted inkjet technologies, and subsequently dried. The examples below serve to illustrate the invention. Parts and percentages are by weight unless noted otherwise. The relationship between parts by weight and parts by volume is that of the kilogram to the liter.

Synthesizing procedure for example 1

Add 8.0 parts of 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid (a) was dissolved in 50 parts of water. The reaction vessel was cooled down to 0 to 5 °C using ice-salt mixture. After 10 mins 7.5 parts of 37% hydrochloric acid was added to the reaction mixture. The reaction mixture was stirred for 1 to 2 hrs. After completion 0.2 parts of sulfamic acid was added into the reaction mixture.

8.7 parts of coupling component (b) was suspended in 50 parts of water. The pH was adjusted to 4.5. The diazo component was added. The reaction mixture was stirred for 2 hrs. After completion, 16.1 parts of the product (c) was obtained by addition of salt followed by filtration.

(b)

8.6 parts of 2,5-dimethoxyphenyl-4(2-sulfatoethyl)sulfonyl aniline (d) was suspended in 50 parts of water and stirred for 10 mins. 7.5 parts of 37% hydrochloric acid was added to the reaction mixture. The reaction vessel was cooled down to 0 - 5 °C using ice-salt mixture. 5.1 parts of sodium nitrite solution was added into the reaction mixture. The reaction mixture was stirred for 1 to 2 hrs.

After completion 0.2 parts of sulfamic acid was added into the reaction mixture. 17.7 parts of coupler (c) was dissolved in 50 parts of water. To this solution the diazo component was added dropwise during 1 hr. The reaction mixture was stirred for 2 hrs. After completion, 26.3 parts of the example 3 was obtained by addition of salt and followed by filtration.

Dissolve 13.16 parts of the dye (e) in 50 parts of water and adjust the pH to slightly acidic. 4.90 parts of copper sulfate and 8.26 parts of sodium acetate was added into the reaction mixture. The reaction mixture was heated to 100 °C for 1 hr. After completion, the example (1 ) was obtained in 13.76 parts by the addition of salt followed by vacuum filtration.

Dyeing example 1

2 parts of a dye obtained as per formula (I) and 50 parts of sodium chloride were dissolved in 999 parts of water, and 5 parts of sodium carbonate and 1 part of a leveling agent were added. This dyebath was enetered with 100 parts of a woven cotton fabric. The temperature of the dyebath was increased to 30 °C and maintained for 30 mins. Further, the dyebath temperature was increased to 60 °C and maintained for 60 mins at 60 °C. Thereafter the dyed fabric was initially rinsed with water. Then, the dyed fabric was neutralized using 1000 parts of an aqueous solution containing 1 part of 60% acetic acid and heated at 50 °C for 30 to 40 minutes. The dyed fabric was rinsed with water at 70 °C and then soaped off at the boil with the laundry detergent for 30 to 40 minutes, and then rinsed again in water and spun dried.

Dyeing example 2

1 part of the dye of the formula (I) was dissolved in 2000 parts of water and heated to 80 °C. for 20 minutes and 1 part of a leveling agent was added. The pH was then adjusted to 4.5 using acetic acid (60%) and 100 parts of wool fabric entered into the dyebath. The dye bath was heated to 40 °C. for 15 minutes. The temperature was raised to 98 °C. and maintained at 98 °C for 90 minutes. Then dyeing was lowered to 60 °C. and the fabric was removed from dyebath. The dyed fabric was washed with water and spun dried.

Dyeing example 3

1 part of the dye of the formula (I) was dissolved in 2000 parts of water and 1 part of a leveling agent (based on a condensation product of a higher aliphatic amine and ethylene oxide) and 6 parts of sodium acetate were added. The pH was then adjusted to 5 using acetic acid (80%). The dye bath was heated to 50 °C. for 10 minutes and then entered with 100 parts of a woven polyamide fabric. The temperature was raised to 1 10 °C. over the course of 50 minutes and then dyeing was lowered by cooling to 60 °C. and the dyed material was removed. The polyamide fabric was washed with hot and cold water, soaped and spun dried.

Dyeing example 4

A textile fabric consisting of mercerized cotton was padded with a liquor containing 35g/l of calcium sodium carbonate, 100 g/l of urea and 150 g/l of a low-viscosity sodium alginate solution (6%), and then dried. The liquor pickup was 70%. The textile thus pretreated was printed with an aqueous ink containing 2% of the dye of example (I), 20% of sulfolane, 0.01 % of Mergal K9N and 77.99% of water using a drop-on- demand (bubblejet) ink-jet printing head. The print was fully dried. It was fixed by means of saturated steam at 102 °C for 8 minutes. The print was then rinsed warm, subjected to a fastness wash with hot water at 95 °C. Again rinsed with warm water and then dried.

Claims

Claims:

1. Chemical compound according to formula (I)

wherein

n is an integer 0 or 1 ;

K is a radical of coupling heterocyclic component as described below;

B is a radical of diazo component as described below;

M is hydrogen, sodium, potassium, lithium or ammonium;

K is a coupling component of following general formulae (K1 ) to (K3);

(K1 ) (K2) (K3) wherein, R¹ and R⁴, independent from each other, are hydrogen, alkyl, cycloalkyl, trifluoromethyl; alkoxy, cyano, carbamoyl, alkoxycarbonyl, COOM, amino;

hydroxyl, monocycloalkyl-amino; monoalkyl-amino; di(cyclo)alkyl-amino; dialkyl- amino; monoaryl-amino; diaryl-amino; monocycloalkyl monoarylamino;

monoalkyl monoaryl amino; alkylthio; arylthio;

or

are alkyl substituted by one or more substituents selected from the group consisting of hydroxy, cycloalkyl, heteroaryl, heterocycloalkyl, aryl, aryloxy, alkoxy, alkylthio, arylthio, halogen, cyano, COOM, alkoxycarbonyl, acyloxy, carbamoyl, nitro, amino, acylamino, arylcarbonylamino, alkylsulfonylamino, arylsulfonylamino, ureido, alkylureido and phenylureido;

R², R⁵ and R¹¹, independent from each other, are cyano, carbamoyl,

alkoxycarbonyl, trifluoromethyl, carbonyltrifluoromethyl, halogen, methyl sulfonyl or -SO₃M;

R³', R⁶ to R⁹ and R¹², independent from each other are hydrogen, alkyl, alkenyl, cycloalkyl, trifluoromethyl, aryl, heteroaryl, heterocycloalkyl, carbamoyl, N- monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N-dicycloalkyl- carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N-diaryl- carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N- monoarylcarbamoyl, sulfamoyl, N-monocycloalkyl-sulfamoyl, N-monoalkyl- sulfamoyl, N,N-dicycloalkylsulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl- sulfamoyl, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N- monoalkyl-N-monoaryl-sulfamoyl, amino, N-acylamino, N-thioacylamino, ureido, alkylureido, phenylureido, N-monoalkylamino, Ν,Ν-dialkyl-amino, N-arylamino, Ν,Ν-diarylamino, N-alkyl-N-aryl-amino, N-monocycloalkylamino, N;N- dicycloalkylamino, N-alkyl-N-cycloalkyl-amino, N-aryl-Ncycloalkyl-amino, N- heteroarylamino, N-heterocycloalkylamino or hydroxyakylsulfonylalkyl, or are alkyl interrupted by one or more heteroatoms such as oxygen or sulfur; or

are alkyl substituted by one or more substituents selected from the group consisting of hydroxy, aryl, cycloalkyl, alkoxy, thioalkoxy, amino, N-monoalkyl- amino, Ν,Ν-dialkyl amino, N-monoaryl-amino, Ν,Ν-diaryl-amino, N -a Iky I- N -aryl - amino, N-monocyclo alkyl-amino, Ν,Ν-dicycloalkyl-amino, N-monoalkyl- monocycloalkyl-amino, Ν,Ν-monoaryl-monocycloalkyl-amino, N-acylamino, N- alkylsulfonyl-amino, ureido, alkylureido, phenylureido, halogen, cyano, COOM, nitro, acyl, thioacyl, alkylsulfonyl, aryloyl, trifluoromethyl, heteroaryl,

heterocycloalkyl, alkoxycarbonyl, alkoxythiocarbonyl, acyloxy, aryloyloxy, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N- dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N- diaryl-carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N- monoaryl-carbamoyl, sulfamoyl, N-monocycloalkyl-sulfamoyl, N-monoalkyl- sulfamoyl, N,N-dicycloalkyl-sulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl sulfamoyl, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N- monoalkyl-N-monoarylsulfamoyl or -SO₃M;

or

alkyl

or

alkyl or aryl substituted by -SO₂X; whereby

X is vinyl or a radical -CH2CH2-Y where Y is a group removable under alkaline conditions such as OS0₃M; and

R¹⁰ is hydroxyl or amino group;

and whereby, in the general formula K2 the point of attachment and R⁵ can be positioned ortho or para to the amino rest bearing the substituents R⁶ and R⁷, meaning that when the point of attachment is positioned ortho to amino rest bearing the substituents R⁶ and R⁷, R⁵ is positioned para to the same, and vice versa. or K is a coupling component of the following general formulae (K4) to (K6);

(K4)

(K5) (K6) whereby

T is a reactive anchor of general formulae (T1) to (T3);

(T1) (T2) (T3) wherein

R²⁴and R²⁵, independent from one another are halogen or

R²⁶ to R³⁰ independent from one another are halogen;

or

each of R²⁴ to R³⁰, independent from one another are substituted by one of the groups selected from general formulae (1 a) to (1 c);

(1 a) (1 b) (1 c) wherein

R³¹, R³², R³³⁹ and R³⁴⁰, independent from one another, are hydrogen, alky, phenyl or phenyl substituted by one of the group selected from alkyl, alkoxy, halogen, or -SOsM; alkenyl, cycloalkyl, trifluoromethyl, aryl, heteroaryl,

heterocycloalkyl, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl- carbamoyl, N,N-dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl- carbamoyl, Ν,Ν-diaryl-carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N- monoalkyl-N-monoarylcarbamoyl, sulfamoyl, N-monocycloalkyl-sulfamoyl, N- monoalkyl-sulfamoyl, N,N-dicycloalkylsulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N- monoaryl-sulfamoyl, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N- monoarylsulfamoyi, N-monoalkyl-N-monoaryl-sulfamoyl, amino, N-acylamino, N-thioacylamino, ureido, alkylureido, phenylureido, N-monoalkylamino, N,N- dialkyl-amino, N-arylamino, Ν,Ν-diarylamino, N-alkyl-N-aryl-amino, N- monocycloalkylamino, N;N-dicycloalkylamino, N-alkyl-N-cycloalkyl-amino, N- aryl-Ncycloalkyl-amino, N-heteroarylamino, N-heterocycloalkylamino or

hydroxyakylsulfonylalkyl,

or

are alkyl interrupted by one or more heteroatoms such as oxygen or sulfur;

or

are alkyl substituted by one or more substituents selected from the group consisting of hydroxy, aryl, cycloalkyl, alkoxy, thioalkoxy, amino, N-monoalkylamino, Ν,Ν-dialkyl amino, N-monoaryl-amino, Ν,Ν-diaryl-amino, N-alkyl-N-aryl- amino, N-monocyclo alkyl-amino, Ν,Ν-dicycloalkyl-amino, N-monoalkyl- monocycloalkyl-amino, Ν,Ν-monoaryl-monocycloalkyl-amino, N-acylamino, N- alkylsulfonyl-amino, ureido, alkylureido, phenylureido, halogen, cyano, COOM, nitro, acyl, thioacyl, alkylsulfonyl, aryloyl, trifluoromethyl, heteroaryl,

heterocycloalkyl, alkoxycarbonyl, alkoxythiocarbonyl, acyloxy, aryloyloxy, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N- dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N- diaryl-carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N- monoaryl-carbamoyl, sulfamoyl, N-monocycloalkyl-sulfamoyl, N-monoalkyl- sulfamoyl, N,N-dicycloalkyl-sulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl sulfamoyl, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N- monoalkyl- N-monoarylsulfamoyl or SO₃M;

R³³, R³⁴ and R³³⁸, independent from one another, are hydrogen, alkyl, alkoxyl, halogen, trifluoromethyl, cyano, nitro, ester, carbamoyl, SO₃M or-SO₂X;

where M is hydrogen, sodium, potassium, lithium or ammonium;

X is vinyl or a radical -CH₂CH₂-Y where Y is a group removable under alkaline conditions such as OSO₃M, SSO₃M, OCOCH₃, OPO₃M or halogen; p is an integer from 1 to 5

R¹³ and R¹⁵, independent from each other, are hydrogen, alkyl, cycloalkyl, trifluoromethyl; alkoxy, cyano, carbamoyl, alkoxycarbonyl, COOM, amino;

monoalkyl monoaryl amino; alkylthio; arylthio;

or

R¹⁴, R¹⁷ to R²⁰ and R²³, independent from each other, are hydrogen, alkyl, alkenyl, cycloalkyl, trifluoromethyl, aryl, heteroaryl, heterocycloalkyl, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N-dicycloalkyl- carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N-diaryl- carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N- monoarylcarbamoyl, sulfamoyl, N-monocycloalkyl-sulfamoyl, N-monoalkyl- sulfamoyl, N,N-dicycloalkylsulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl- sulfamoyl, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N- monoalkyl-N-monoaryl-sulfamoyl, amino, N-acylamino, N-thioacylamino, ureido, alkylureido, phenylureido, N-monoalkylamino, Ν,Ν-dialkyl-amino, N-arylamino, Ν,Ν-diarylamino, N-alkyl-N-aryl-amino, N-monocycloalkylamino, N;N- dicycloalkylamino, N-alkyl-N-cycloalkyl-amino, N-aryl-Ncycloalkyl-amino, N- heteroarylamino, N-heterocycloalkylamino or hydroxyakylsulfonylalkyl, or

are alkyl interrupted by one or more heteroatoms such as oxygen or sulfur;

or

R²¹ is hydroxyl or amino group;

And whereby, in the general formula K5 the point of attachment and R¹⁶ can be positioned ortho or para to the amino rest bearing the substituents R¹⁷ and R¹⁸, meaning that when the point of attachment is positioned ortho to amino rest bearing the substituents R¹⁷ and R¹⁸, R¹⁶ is positioned para to the same, and vice versa.

(A1 ) (A2)

R³⁴¹ to R³⁴⁸, independent from one another, are hydrogen, alkyl, alkyl chain interrupted by one or two heteroatoms, alkoxy, halogen, trifluoromethyl;

cycloalkyl; heterocycloalkyl; cyano; nitro; acyloxy; alkylcarbonyl, acylamino; aryloylamino, cinnamoylamino, alkylsulfonylamino; alkylthio; alkylsulfonyl, alkoxycarbonyl, carbamoyl, sulfamoyl, ureido, alkylureido, S0₃M, COOM; or

are alkyl substituted by one or more substituents selected from the group consisting of hydroxy, aryl, cycloalkyl, alkoxy, thioalkoxy, amino, N-monoalkyl- amino, Ν,Ν-dialkylamino, N-monoaryl-amino, Ν,Ν-diaryl-amino, N -a Iky I- N -aryl - amino, N-monocycloalkyl-amino, Ν,Ν-dicycloalkyl-amino, N-monoalkyl- monocycloalkyl-amino, Ν,Ν-monoaryl-monocycloalkyl-amino, N-acylamino, N- alkylsulfonyl-amino, ureido, alkylureido, phenylureido, halogen, cyano, COOM, nitro, acyl, thioacyl, alkylsulfonyl, aryloyl, trifluoromethyl, heteroaryl,

heterocycloalkyl, alkoxycarbonyl, alkoxythiocarbonyl, acyloxy, aryloyloxy, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N- dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N- diaryl-carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N- monoaryl-carbamoyl, sulfamoyl, N-monocycloalkyl-sulfamoyl, N-monoalkyl- sulfamoyl, N,N-dicycloalkyl-sulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N- monoarylsulfamoyl, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N- monoarylsulfamoyl, N-monoalkyl-N-monoarylsulfamoyl or SO₃M;

or

are alkyl interrupted by one or more heteroatoms such as oxygen or sulfur; or are alkyl substituted by one or more substituents selected from the group consisting of hydroxy, aryl, cycloalkyl, alkoxy, thioalkoxy, amino, N-monoalkyl- amino, Ν,Ν-dialkyl amino, N-monoaryl-amino, Ν,Ν-diaryl-amino, N -a Iky I- N -aryl - amino, N-monocyclo alkyl-amino, Ν,Ν-dicycloalkyl-amino, N-monoalkyl- monocycloalkyl-amino, Ν,Ν-monoaryl-monocycloalkyl-amino, N-acylamino, N- alkylsulfonyl-amino, ureido, alkylureido, phenylureido, halogen, cyano, COOM, nitro, acyl, thioacyl, alkylsulfonyl, aryloyl, trifluoromethyl, heteroaryl,

heterocycloalkyl, alkoxycarbonyl, alkoxythiocarbonyl, acyloxy, aryloyloxy, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N- dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N- diaryl-carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N- monoaryl-carbamoyl, sulfamoyl, N-monocycloalkyl-sulfamoyl, N-monoalkyl- sulfamoyl, N,N-dicycloalkyl-sulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl sulfamoyl, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N- monoalkyl- N-monoarylsulfamoyl or SO3M;

r a group of formulae 2a) to (2c)

whereby R³⁴⁹ and R³⁵⁰ independent from each other are, hydrogen, alkyl, alkyl substituted by SO₃M, alkyl chain interrupted by one or two heteroatoms, or T; whereby T has the same meaning as above;

U is -O-, -S- or -N(R³²⁹)-;

r is an integer of 0 to 6; s is an integer of 1 to 6;

*^* refers to attachment point with A1 or A2

*^** refers to attachment point with T

T has the meaning as above;

B is the diazo com onent and has one of the general formula (B1 ) or (B2);

(B1 ) (B2)

wherein

R³⁵ to R⁴⁰ and R³⁵¹, independent from one another, are hydrogen or alkyl, alkoxy, halogen, cyano, -SO3M, trifluoromethyl, nitro, ester, NHC(0)R⁴¹, CONH₂,

S(0)₂R⁴², -SO₂X or aminosubstituted by T or one of the general formulae (E1 ) to (E3);

(E3)

wherein

V is -0-, -S- or -N(R³⁵²)-

R⁴³, R⁴⁷ and R³⁵², independent from one another, are hydrogen, alkyl, alkyl substituted by SO₃M, alkyl chain interrupted by one or two heteroatoms; R⁴⁴, R⁴⁵, R⁴⁶ and R⁴⁸, independent from one another, are hydrogen, alkyl or alkyl chain interrupted by one or two heteroatoms;

R³³⁰ to R³³³, independent from one another, are hydrogen or alkyl, alkoxy, halogen, cyano, -SO₃M, trifluoromethyl, nitro, ester, NHC(0)R³³⁴, CONH₂, S(0)₂R³³⁵ or a group of formula (3a);

(3a)

R³³⁶ and R³³⁷, iinnddeeppiendent from one another, are hydrogen, alkyl, alkenyl, cycloalkyi, trifluoromethyl, aryl, heteroaryl, heterocycloalkyi, carbamoyl, N- monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N-dicycloalkyl- carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N-diaryl- carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N- monoarylcarbamoyl, sulfamoyl, N-monocycloalkyl-sulfamoyl, N-monoalkyl- sulfamoyl, N,N-dicycloalkylsulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl- sulfamoyl, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N- monoalkyl-N-monoaryl-sulfamoyl, amino, N-acylamino, N-thioacylamino, ureido, alkylureido, phenylureido, N-monoalkylamino, Ν,Ν-dialkyl-amino, N-arylamino, Ν,Ν-diarylamino, N-alkyl-N-aryl-amino, N-monocycloalkylamino, N;N- dicycloalkylamino, N-alkyl-N-cycloalkyl-amino, N-aryl-N-cycloalkyl-amino, N- heteroarylamino, N-heterocycloalkylamino or hydroxyakylsulfonylalkyl, or

are alkyl interrupted by one or more heteroatoms such as oxygen or sulfur; or

heterocycloalkyl, alkoxycarbonyl, alkoxythiocarbonyl, acyloxy, aryloyloxy, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N- dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N- diaryl-carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N- monoaryl-carbamoyl, sulfamoyl, N-monocycloalkyl-sulfamoyl, N-monoalkyl- sulfamoyl, N,N-dicycloalkyl-sulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl sulfamoyl, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N- monoalkyl- N-monoarylsulfamoyl or SO₃M; or alkyl containing a rest with free valence to link to reactive anchor T;

c is an integer of 0 to 6;

d is an integer of 1 to 6;

*^*** refers to attachment point with Bl and B2;

*^**** refers to attachment point with T;

^******refers to attachment point with E3;

T and X are the same as defined above;

M is hydrogen, lithium, sodium, potassium, ammonium or mono-, di-, tri- or tetra-(Ci-C₄)-alkylammonium, one equivalent of an alkali earth metal, or a monovalent organic cation; ...

with the general proviso that the dyes of general formula (I) contain at least one reactive anchor.

Chemical compound according to claim 1 having formulae (la) to (If): formulae (la) to (If) and mixtures thereof;

(la)

(lb)

(lc)

(Id)

(if)

wherein

R⁴⁹, R⁸⁵, R⁵⁸, R⁶⁶, R⁷⁴ and R⁷⁸, independent from each other, are hydrogen, alkyl, cycloalkyl, trifluoromethyl; alkoxy, cyano, carbamoyl, alkoxycarbonyl, COOM, amino; hydroxyl, monocycloalkyl-amino; monoalkyl-amino;

di(cyclo)alkyl-amino; dialkyl-amino; monoaryl-amino; diaryl-amino;

monocycloalkyi monoarylamino; monoalkyi monoaryl amino; alkylthio; arylthio; or

is alkyl substituted by one or more substituents selected from the group consisting of hydroxy, cycloalkyl, heteroaryl, heterocycloalkyl, aryl, aryloxy, alkoxy, alkylthio, arylthio, halogen, cyano, COOM, alkoxycarbonyl, acyloxy, carbamoyl, nitro, amino, acylamino, arylcarbonylamino, alkylsulfonylamino, arylsulfonylamino, ureido, alkylureido or phenylureido;

R⁵⁰, R⁵⁴, R⁵⁹, R⁶⁷, R⁷⁵ and R⁷⁹, independent from each other, are cyano, carbamoyl, alkoxycarbonyl, trifluoromethyl, carbonyltrifluoromethyl, halogen, methyl sulfonyl or -SOsM;

R⁵¹, R⁵⁵, R⁶⁰ and R⁶⁸ independent from each other, are hydrogen, alkyl, alkenyl, cycloalkyl, trifluoromethyl, aryl, heteroaryl, heterocycloalkyl, carbamoyl, N- monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N-dicycloalkyl- carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N-diaryl- carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N- monoarylcarbamoyl, sulfamoyl, N-monocycloalkyl-sulfamoyl, N-monoalkyl- sulfamoyl, N,N-dicycloalkylsulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl- sulfamoyl, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N- monoalkyl-N-monoaryl-sulfamoyl, amino, N-acylamino, N-thioacylamino, ureido, alkylureido, phenylureido, N-monoalkylamino, Ν,Ν-dialkyl-amino, N-arylamino, Ν,Ν-diarylamino, N-alkyl-N-aryl-amino, N-monocycloalkylamino, N;N- dicycloalkylamino, N-alkyl-N-cycloalkyl-amino, N-aryl-Ncycloalkyl-amino, N- heteroarylamino, N-heterocycloalkylamino or hydroxyakylsulfonylalkyl, or

are alkyl interrupted by one or more heteroatoms such as oxygen or sulfur; or

R⁵², R⁵³, R⁵⁶, R⁵⁷, R⁶⁴, R⁶⁵, R⁷², R⁷³, R⁷⁶, R⁷⁷, R⁸³ and R⁸⁴, independent from one another, are hydrogen or alkyl, alkoxy, halogen, cyano, -SO₃M,

trifluoromethyl, nitro, ester, NHC(0)R⁸⁶, CONH₂, S(0)₂R⁸⁷ or -S0₂X;

R⁸⁶ and R⁸⁷ independent from one another are hydrogen, alkyl or alkyl substituted by hydroxy or halogen; R⁶¹ to R⁶³, R⁶⁹ to R⁷¹ and R⁸⁰ to R⁸², independent from one another, are hydrogen, alkyl, alkyl substituted, alkyl chain interrupted by one or two heteroatoms, alkoxy, alkoxy substituted, halogen, trifluoromethyl; cycloalkyl; heterocycloalkyi; cyano; nitro; acyloxy; alkylcarbonyl, acylamino; aryloylamino, cinnamoylamino, alkylsulfonylamino; alkylthio; alkylsulfonyl, alkoxycarbonyl, carbamoyl, sulfamoyl, ureido, alkylureido, S0₃M, COOM; or a group of formulae (2a) to (2c),

X and M are the same as in claim 1.

Chemical compound according to claim 1 having formulae (Ig) or (Ih):

(ig)

(Ih)

wherein

R and R , independent from each other, are hydrogen, alkyl, cycloalkyl, trifluoromethyl; alkoxy, cyano, carbamoyl, alkoxycarbonyl, COOM, amino;

monoalkyl monoaryl amino; alkylthio; arylthio;

or

R⁹¹ and R⁹⁵, independent from each other, are cyano, carbamoyl,

alkoxycarbonyl, tnfluoromethyl, carbonyltrifluoromethyl, halogen, methyl sulfonyl or -S0₃M;

D¹ and D² independent from each other, are hydrogen, alkyl, alkenyl, cycloalkyl, tnfluoromethyl, aryl, heteroaryl, heterocycloalkyl, carbamoyl, N-monocycloalkyl- carbamoyl, N-monoalkyl-carbamoyl, Ν,Ν-dicycloalkyl-carbamoyl, N,N-dialkyl- carbamoyl, N-monoaryl-carbamoyl, N,N -diary I -carbamoyl, N-monocycloalkyl-N- monoarylcarbamoyl, N-monoalkyl-N-monoarylcarbamoyl, sulfamoyl, N- monocycloalkyl-sulfamoyl, N-monoalkyl-sulfamoyl, N,N-dicycloalkylsulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl-sulfamoyl, Ν,Ν-diaryl-sulfamoyl, N- monocycloalkyl-N-monoarylsulfamoyl, N-monoalkyl-N-monoaryl-sulfamoyl, amino, N-acylamino, N-thioacylamino, ureido, alkylureido, phenylureido, N- monoalkylamino, Ν,Ν-dialkyl-amino, N-arylamino, Ν,Ν-diarylamino, N-alkyl-N- aryl-amino, N-monocycloalkylamino, N;N-dicycloalkylamino, N-alkyl-N- cycloalkyl-amino, N-aryl-Ncycloalkyl-amino, N-heteroarylamino, N- heterocycloalkylamino or hydroxyakylsulfonylalkyl,

or

are alkyl interrupted by one or more heteroatoms such as oxygen or sulfur; or

are alkyl substituted by one or more substituents selected from the group consisting of hydroxy, aryl, cycloalkyl, alkoxy, thioalkoxy, amino, N-monoalkyl- amino, N,N-di alkyl amino, N-monoaryl-amino, Ν,Ν-diaryl-amino, N -a Iky I- N-arylamino, N-monocyclo alkyl-amino, Ν,Ν-dicycloalkyl-amino, N-monoalkyl- monocycloalkyl-amino, Ν,Ν-monoaryl-monocycloalkyl-amino, N-acylamino, N- alkylsulfonyl-amino, ureido, alkylureido, phenylureido, halogen, cyano, COOM, nitro, acyl, thioacyl, alkylsulfonyl, aryloyl, tnfluoromethyl, heteroaryl,

heterocycloalkyl, alkoxycarbonyl, alkoxythiocarbonyl, acyloxy, aryloyloxy, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N- dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N- diaryl-carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N- monoaryl-carbamoyl, sulfamoyi, N-monocycloalkyl-sulfamoyl, N-monoalkyl- sulfamoyl, N,N-dicycloalkyl-sulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl sulfamoyi, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N- monoalkyl- N-monoarylsulfamoyl or SO₃M;

R⁹², R⁹³, R⁹⁹ and R¹⁰⁰, independent from one another, are hydrogen or alkyl, alkoxy, halogen, cyano, -SO₃M, trifluoromethyl, nitro, ester, NHC(0)R¹⁰¹ , CONH2, S(0)₂R¹⁰² or -S0₂X;

R⁹⁶ to R⁹⁸, independent from one another, are hydrogen, alkyl, alkyl substituted, alkyl chain interrupted by one or two heteroatoms, alkoxy, alkoxy substituted, halogen , trifluoromethyl; cycloalkyl; heterocycloalkyl; cyano; nitro; acyloxy;

alkylcarbonyl, acylamino; aryloylamino, cinnamoylamino, alkylsulfonylamino; alkylthio; alkylsulfonyl, alkoxycarbonyl, carbamoyl, sulfamoyi, ureido, alkylureido, SO₃M, COOM; or a group of formulae (2a) to (2c);

with the proviso D¹ and D² contain a rest with free valence to link to reactive anchor T;

T, X and M are the same as defined in claim 1 . 4. Chemical compound according to claiml having one of formulae (li) to (II):

(Ik)

(II)

Wherein

R¹⁰⁵, R¹¹⁰, R¹¹⁵ and R¹²³, independent from each other, are hydrogen, alkyl, cycloalkyi, trifluoromethyl; alkoxy, cyano, carbamoyl, alkoxycarbonyl, COOM, amino; hydroxyl, monocycloalkyl-amino; monoalkyl-amino; di(cyclo)alkyl-amino; dialkyl-amino; monoaryl-amino; diaryl-amino; monocycloalkyl monoarylamino; monoalkyl monoaryl amino; alkylthio; arylthio;

or

R¹⁰⁶, R¹¹¹, R¹¹⁶ and R¹²⁴, independent from each other, are cyano, carbamoyl, alkoxycarbonyl, trifluoromethyl, carbonyltrifluoromethyl, halogen, methyl sulfonyl or -S0₃M;

R¹⁰⁷, R¹¹², R¹¹⁷ and R¹²⁵, independent from each other, are hydrogen, alkyl, alkenyl, cycloalkyl, trifluoromethyl, aryl, heteroaryl, heterocycloalkyl, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N-dicycloalkyl- carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N-diaryl- carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N- monoarylcarbamoyl, sulfamoyl, N-monocycloalkyl-sulfamoyl, N-monoalkyl- sulfamoyl, N,N-dicycloalkylsulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl- sulfamoyl, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N- monoalkyl-N-monoaryl-sulfamoyl, amino, N-acylamino, N-thioacylamino, ureido, alkylureido, phenylureido, N-monoalkylamino, Ν,Ν-dialkyl-amino, N-arylamino, Ν,Ν-diarylamino, N-alkyl-N-aryl-amino, N-monocycloalkylamino, N;N- dicycloalkylamino, N-alkyl-N-cycloalkyl-amino, N-aryl-Ncycloalkyl-amino, N- heteroarylamino, N-heterocycloalkylamino or hydroxyakylsulfonylalkyl, or

alkyl interrupted by one or more heteroatoms such as oxygen or sulfur;

or

alkyl substituted by one or more substituents selected from the group consisting of hydroxy, aryl, cycloalkyl, alkoxy, thioalkoxy, amino, N-monoalkyl-amino, N,N- dialkyl amino, N-monoaryl-amino, Ν,Ν-diaryl-amino, N-alkyl-N-aryl-amino, N- monocyclo alkyl-amino, Ν,Ν-dicycloalkyl-amino, N-monoalkyl-monocycloalkyl- amino, Ν,Ν-monoaryl-monocycloalkyl-amino, N-acylamino, N-alkylsulfonyl- amino, ureido, alkylureido, phenylureido, halogen, cyano, COOM, nitro, acyl, thioacyl, alkylsulfonyl, aryloyl, trifluoromethyl, heteroaryl, heterocycloalkyi, alkoxycarbonyl, alkoxythiocarbonyl, acyloxy, aryloyloxy, carbamoyl, N- monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N-dicycloalkyl- carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N-diaryl- carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N-monoaryl- carbamoyl, sulfamoyi, N-monocycloalkyl-sulfamoyl, N-monoalkyl-sulfamoyl, N,N-dicycloalkyl-sulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl sulfamoyi, N,N- diaryl-sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N-monoalkyl- N- monoarylsulfamoyl or SO3M;

R¹⁰⁸, R¹⁰⁹, R¹¹³, R¹¹⁴, R¹²¹, R¹²², R¹²⁹ and R¹³⁰, independent from one another, are hydrogen or alkyl, alkoxy, halogen, cyano, -SO₃M, trifluoromethyl, nitro, ester, NHC(0)R¹³¹, CONH₂, S(0)₂R¹³² or -S0₂X;

R¹³¹ and R¹³², independent from one another, are hydrogen, alkyl or alkyl substituted by hydroxy or halogen,

_Ri i8 _{t0 R}i2o _{an d R}126 _{10 R}128 j_nc|_ep_enc|_ent f_{rom one} another, are hydrogen, alkyl, alkyl substituted, alkyl chain interrupted by one or two heteroatoms, alkoxy, alkoxy substituted, halogen ,trifluoromethyl; cycloalkyi; heterocycloalkyi; cyano; nitro; acyloxy; alkylcarbonyl, acylamino; aryloylamino, cinnamoylamino, alkylsulfonylamino; alkylthio; alkylsulfonyl, alkoxycarbonyl, carbamoyl, sulfamoyi, ureido, alkylureido, S0₃M, COOM; or a group of formulae (2a) to (2c);

E⁴ to E⁷, independent from each other, are a group of general formulae (E1 ) to (E3)

M is the same as defined in claim 1.

5. Chemical compound according to claim 1 having one of formulae (Im) to (Ip):

(Im)

wherein

or

alkyl interrupted by one or more heteroatoms such as oxygen or sulfur;

or

NHC(0)R¹⁵⁷, CONH2, S(0)₂R¹⁵⁸ or -S0₂X;

R¹⁴⁵, R¹⁴⁶, R¹⁴⁷, R¹⁵², R¹⁵³ and R¹⁵⁴, independent from one another, are hydrogen, alkyl, alkyl substituted, alkyl chain interrupted by one or two heteroatoms, alkoxy, alkoxy substituted, halogen ,trifluoromethyl; cycloalkyi; heterocycloalkyi; cyano; nitro; acyloxy; alkylcarbonyl, acylamino; aryloylamino, cinnamoylamino, alkylsulfonylamino; alkylthio; alkylsulfonyl, alkoxycarbonyl, carbamoyl, sulfamoyi, ureido, alkylureido, SO3M, COOM; or contain a group of formulae (2a) to (2c) as defined above;

T, X and M are the same as defined in claim 1 .

6. Chemical compound according to claim 1 having one of formulae (Iq) to (It):

wherein

R¹⁶², R¹⁶⁹, R¹⁷⁶ and R¹⁸⁶ independent from each other, are hydroxyl or amino; _R163 _{10 R}i 65_{j R}i 7o _{tQ R}M2^ _R177 _{[q R}179 _{a n d R}187 _{tQ R}I∞ j_ndepencj_ent from each other, are hydrogen, alkyl, alkenyl, cycloalkyl, trifluoromethyl, aryl, heteroaryl, heterocycloalkyl, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl- carbamoyl, N,N-dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl- carbamoyl, Ν,Ν-diaryl-carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N- monoalkyl-N-monoarylcarbamoyl, sulfamoyi, N-monocycloalkyl-sulfamoyl, N- monoalkyl-sulfamoyl, N,N-dicycloalkylsulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N- monoaryl-sulfamoyl, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N- monoarylsulfamoyl, N-monoalkyl-N-monoaryl-sulfamoyl, amino, N-acylamino, N-thioacylamino, ureido, alkylureido, phenylureido, N-monoalkylamino, N,N- dialkyl-amino, N-arylamino, Ν,Ν-diarylamino, N-alkyl-N-aryl-amino, N- monocycloalkylamino, N;N-dicycloalkylamino, N-alkyl-N-cycloalkyl-amino, N- aryl-Ncycloalkyl-amino, N-heteroarylamino, N-heterocycloalkylamino or hyd roxya ky I s u If o ny I a I ky I ,

or

are alkyl interrupted by one or more heteroatoms such as oxygen or sulfur; or

or

alkyl or aryl substituted by -SO₂X; whereby

X is vinyl or a radical -CH₂CH₂-Y where Y is a group removable under alkaline conditions such as OSO₃M; or a rest with free valence to link to reactive anchor R¹⁶⁶, R¹⁶⁷, R¹⁷³, R¹⁷⁴, R¹⁸³, R¹⁸⁴, R¹⁹³ and R¹⁹⁴, independent from one another, are hydrogen or alkyl, alkoxy, halogen, cyano, -SO₃M, trifluoromethyl, nitro, ester, NHC(0)R¹⁹⁵, CONH₂, S(0)₂R¹⁹⁶ or -S0₂X;

R¹⁹⁵ and R¹⁹⁶, independent from one another, are hydrogen, alkyl or alkyl substituted by hydroxy or halogen;

_R ⁱ⁸o _{t0 R} ¹⁸² _{and R} ⁱ⁹o _{t0 R} ¹⁹² _; j_nc|_ep_enc|_ent f_{rom one} another, are hydrogen, alkyl, alkyl substituted, alkyl chain interrupted by one or two heteroatoms, alkoxy, alkoxy substituted, halogen ,trifluoromethyl; cycloalkyi; heterocycloalkyi; cyano; nitro; acyloxy; alkylcarbonyl, acylamino; aryloylamino, cinnamoylamino, alkylsulfonylamino; alkylthio; alkylsulfonyl, alkoxycarbonyl, carbamoyl, sulfamoyi, ureido, alkylureido, S0₃M, COOM; or contain a group of formulae (2a) to (2c); X, is the same as defined above,

and M and T are as defined in claim 1 .

7. Chemical compound according to claim 1 having one of the formulae (lu) to (Ix):

(lu)

(Iw)

R¹⁹⁹, R²⁰⁶, R²¹³ and R²²³, independent from each other, are alkyl, cyano, carbamoyl, alkoxycarbonyl, trifluoromethyl, carbonyltrifluoromethyl, halogen, methyl sulfonyl or -SOsM;

R²⁰⁰, R²⁰⁷, R²¹⁴ and R²²⁴ independent from each other, are hydroxyl or amino;

_R201 _{tQ R}203^ _R208 _{tQ R}210_{j R}215 _{{q r}217 _R225 _{{q r}227 _^ j_ndependent f_{rom each} other, are hydrogen, alkyl, alkenyl, cycloalkyl, trifluoromethyl, aryl, heteroaryl, heterocycloalkyl, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl- carbamoyl, N,N-dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl- carbamoyl, Ν,Ν-diaryl-carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N- monoalkyl-N-monoarylcarbamoyl, sulfamoyl, N-monocycloalkyl-sulfamoyl, N- monoalkyl-sulfamoyl, N,N-dicycloalkylsulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N- monoaryl-sulfamoyl, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N- monoarylsulfamoyl, N-monoalkyl-N-monoaryl-sulfamoyl, amino, N-acylamino, N-thioacylamino, ureido, alkylureido, phenylureido, N-monoalkylamino, N,N- dialkyl-amino, N-arylamino, Ν,Ν-diarylamino, N-alkyl-N-aryl-amino, N- monocycloalkylamino, N;N-dicycloalkylamino, N-alkyl-N-cycloalkyl-amino, N- aryl-Ncycloalkyl-amino, N-heteroarylamino, N-heterocycloalkylamino or hyd roxya ky I s u If o ny I a I ky I ,

or

are alkyl interrupted by one or more heteroatoms such as oxygen or sulfur; or

are alkyl substituted by one or more substituents selected from the group consisting of hydroxy, aryl, cycloalkyi, alkoxy, thioalkoxy, amino, N-monoalkyl- amino, Ν,Ν-dialkyl amino, N-monoaryl-amino, Ν,Ν-diaryl-amino, N -alkyl -N -aryl - amino, N-monocyclo alkyl-amino, Ν,Ν-dicycloalkyl-amino, N-monoalkyl- monocycloalkyl-amino, Ν,Ν-monoaryl-monocycloalkyl-amino, N-acylamino, N- alkylsulfonyl-amino, ureido, alkylureido, phenylureido, halogen, cyano, COOM, nitro, acyl, thioacyl, alkylsulfonyl, aryloyl, trifluoromethyl, heteroaryl,

heterocycloalkyi, alkoxycarbonyl, alkoxythiocarbonyl, acyloxy, aryloyloxy, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N- dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N- diaryl-carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N- monoaryl-carbamoyl, sulfamoyi, N-monocycloalkyl-sulfamoyl, N-monoalkyl- sulfamoyl, N,N-dicycloalkyl-sulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl sulfamoyi, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N- monoalkyl- N-monoarylsulfamoyl or SO₃M;

or

alkyl or aryl substituted by -SO₂X; whereby

X is vinyl or a radical -CH₂CH₂-Y where Y is a group removable under alkaline conditions such as OSO₃M; or a rest with free valence to link to reactive anchor

T;

R²⁰⁴, R²⁰⁵, R²¹¹, R²¹², R²²¹ , R²²², R²³¹ and R²³², independent from one another are hydrogen or alkyl, alkoxy, halogen, cyano, -SO₃M, trifluoromethyl, nitro, ester, NHC(0)R²³³, CONH₂, S(0)₂R²³⁴ or -S0₂X;

_R218 _{10 R}22o _{and R}228 _{tQ R}23o _^ j_nc|_ep_enc|_ent f_{rom one} another are hydrogen, alkyl, alkyl substituted, alkyl chain interrupted by one or two heteroatoms, alkoxy, alkoxy substituted, halogen ,trifluoromethyl; cycloalkyi; heterocycloalkyi; cyano; nitro; acyloxy; alkylcarbonyl, acylamino; aryloylamino, cinnamoylamino, alkylsulfonylamino; alkylthio; alkylsulfonyl, alkoxycarbonyl, carbamoyl, sulfamoyi, ureido, alkylureido, S0₃M, COOM; or a group of formulae (2a) to (2c);

E¹² to E¹⁵, independent from each other, are a group of general formulae (E1 ) to

(E3);

T, X and M have the same meanings as in claim 1 . Chemical compound according to one of formulae (ly) to (lab):

(lz)

wherein

R²³⁷, R²⁴⁵, R²⁵³ and R²⁶⁴, independent from each other, are hydrogen, alkyl, cycloalkyi, trifluoromethyl; alkoxy, cyano, carbamoyl, alkoxycarbonyl, COOM, amino; hydroxyl, monocycloalkyl-amino; monoalkyl-amino; di(cyclo)alkyl-amino; dialkyl-amino; monoaryl-amino; diaryl-amino; monocycloalkyi monoarylamino; monoalkyl monoaryl amino; alkylthio; arylthio;

R²³⁸, R²⁴⁶, R²⁵⁴ and R²⁶⁵, independent from each other, are cyano, carbamoyl, alkoxycarbonyl, trifluoromethyl, carbonyltrifluoromethyl, halogen, methyl sulfonyl or -S0₃M;

_R239 _{tQ R}24_{2i R}247 _{{q r}250 ^ _R255 _{to R}258 _R267 _{to R}270_j j_ndepenc|_ent f_r0m each other, are hydrogen, alkyl, alkenyl, cycloalkyl, trifluoromethyl, aryl, heteroaryl, heterocycloalkyl, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl- carbamoyl, N,N-dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl- carbamoyl, Ν,Ν-diaryl-carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N- monoalkyl-N-monoarylcarbamoyl, sulfamoyl, N-monocycloalkyl-sulfamoyl, N- monoalkyl-sulfamoyl, N,N-dicycloalkylsulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N- monoaryl-sulfamoyl, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N- monoarylsulfamoyl, N-monoalkyl-N-monoaryl-sulfamoyl, amino, N-acylamino, N-thioacylamino, ureido, alkylureido, phenylureido, N-monoalkylamino, N,N- dialkyl-amino, N-arylamino, Ν,Ν-diarylamino, N-alkyl-N-aryl-amino, N- monocycloalkylamino, N;N-dicycloalkylamino, N-alkyl-N-cycloalkyl-amino, N- aryl-Ncycloalkyl-amino, N-heteroarylamino, N-heterocycloalkylamino or hyd roxya ky I s u If o ny I a I ky I ,

or

are alkyl interrupted by one or more heteroatoms such as oxygen or sulfur; or

are alkyl substituted by one or more substituents selected from the group consisting of hydroxy, aryl, cycloalkyl, alkoxy, thioalkoxy, amino, N-monoalkylamino, Ν,Ν-dialkyl amino, N-monoaryl-amino, Ν,Ν-diaryl-amino, N-alkyl-N-aryl- amino, N-monocyclo alkyl-amino, Ν,Ν-dicycloalkyl-amino, N-monoalkyl- monocycloalkyl-amino, Ν,Ν-monoaryl-monocycloalkyl-amino, N-acylamino, N- alkylsulfonyl-amino, ureido, alkylureido, phenylureido, halogen, cyano, COOM, nitro, acyl, thioacyl, alkylsulfonyl, aryloyl, trifluoromethyl, heteroaryl, heterocycloalkyl, alkoxycarbonyl, alkoxythiocarbonyl, acyloxy, aryloyloxy, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N- dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N- diaryl-carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N- monoaryl-carbamoyl, sulfamoyi, N-monocycloalkyl-sulfamoyl, N-monoalkyl- sulfamoyl, N,N-dicycloalkyl-sulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl sulfamoyi, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N- monoalkyl- N-monoarylsulfamoyl or SO₃M; or alkyl containing a rest with free valence to link to rest reactive anchor T;

R²⁴³, R²⁴⁴, R²⁵¹, R²⁵², R²⁶², R²⁶³, R²⁷⁴ and R²⁷⁵, independent from one another, are hydrogen or alkyl, alkoxy, halogen, cyano, -SO₃M, trifluoromethyl, nitro, ester, NHC(0)R²⁷⁶, CONH₂, S(0)₂R²⁷⁷ or -S0₂X;

R²⁵⁹ to R²⁶¹ and R²⁷¹ to R²⁷³, independent from one another, are hydrogen, alkyl, alkyl substituted, alkyl chain interrupted by one or two heteroatoms, alkoxy, alkoxy substituted, halogen ,trifluoromethyl; cycloalkyl; heterocycloalkyl; cyano; nitro; acyloxy; alkylcarbonyl, acylamino; aryloylamino, cinnamoylamino, alkylsulfonylamino; alkylthio; alkylsulfonyl, alkoxycarbonyl, carbamoyl, sulfamoyi, ureido, alkylureido, S0₃M, COOM; or contain a group of formulae (2a) to (2c) X, M and T are as defined in claim 1.

9. Chemical compound according to one of formulae (lac) to (laf):

wherein R²⁸⁰, R²⁸⁸, R²⁹⁶ and R³⁰⁷, independent from each other, are hydrogen, alkyl, cycloalkyl, trifluoromethyl; alkoxy, cyano, carbamoyl, alkoxycarbonyl, COOM, amino; hydroxyl, monocycloalkyl-amino; monoalkyl-amino; di(cyclo)alkyl-amino; dialkyl-amino; monoaryl-amino; diaryl-amino; monocycloalkyl monoarylamino; monoalkyl monoaryl amino; alkylthio; arylthio;

or

R²⁸¹, R²⁸⁹, R²⁹⁷ and R³⁰⁸, independent from each other, are cyano, carbamoyl, alkoxycarbonyl, trifluoromethyl, carbonyltrifluoromethyl, halogen, methyl sulfonyl or -SO₃M;

R²⁸² to R²⁸⁵, R²⁹⁰ to R²⁹³, R²⁹⁸ to R³⁰¹ and R³⁰⁹ to R³¹², independent from each other, are hydrogen, alkyl, alkenyl, cycloalkyl, trifluoromethyl, aryl, heteroaryl, heterocycloalkyl, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl- carbamoyl, N,N-dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl- carbamoyl, Ν,Ν-diaryl-carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N- monoalkyl-N-monoarylcarbamoyl, sulfamoyl, N-monocycloalkyl-sulfamoyl, N- monoalkyl-sulfamoyl, N,N-dicycloalkylsulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N- monoaryl-sulfamoyl, N,N -diary I -sulfamoyl, N-monocycloalkyl-N- monoarylsulfamoyl, N-monoalkyl-N-monoaryl-sulfamoyl, amino, N-acylamino, N-thioacylamino, ureido, alkylureido, phenylureido, N-monoalkylamino, N,N- dialkyl-amino, N-arylamino, Ν,Ν-diarylamino, N-alkyl-N-aryl-amino, N- monocycloalkylamino, N;N-dicycloalkylamino, N-alkyl-N-cycloalkyl-amino, N- aryl-Ncycloalkyl-amino, N-heteroarylamino, N-heterocycloalkylamino or hyd roxya ky I s u If o ny I a I ky I ,

or

are alkyl interrupted by one or more heteroatoms such as oxygen or sulfur; or are alkyl substituted by one or more substituents selected from the group consisting of hydroxy, aryl, cycloalkyi, alkoxy, thioalkoxy, amino, N-monoalkyl- amino, Ν,Ν-dialkyl amino, N-monoaryl-amino, Ν,Ν-diaryl-amino, N -a Iky I- N -aryl - amino, N-monocyclo alkyl-amino, Ν,Ν-dicycloalkyl-amino, N-monoalkyl- monocycloalkyl-amino, Ν,Ν-monoaryl-monocycloalkyl-amino, N-acylamino, N- alkylsulfonyl-amino, ureido, alkylureido, phenylureido, halogen, cyano, COOM, nitro, acyl, thioacyl, alkylsulfonyl, aryloyl, trifluoromethyl, heteroaryl,

heterocycloalkyi, alkoxycarbonyl, alkoxythiocarbonyl, acyloxy, aryloyloxy, carbamoyl, N-monocycloalkyl-carbamoyl, N-monoalkyl-carbamoyl, N,N- dicycloalkyl-carbamoyl, Ν,Ν-dialkyl-carbamoyl, N-monoaryl-carbamoyl, N,N- diaryl-carbamoyl, N-monocycloalkyl-N-monoarylcarbamoyl, N-monoalkyl-N- monoaryl-carbamoyl, sulfamoyl, N-monocycloalkyl-sulfamoyl, N-monoalkyl- sulfamoyl, N,N-dicycloalkyl-sulfamoyl, Ν,Ν-dialkyl-sulfamoyl, N-monoaryl sulfamoyl, Ν,Ν-diaryl-sulfamoyl, N-monocycloalkyl-N-monoarylsulfamoyl, N- monoalkyl- N-monoarylsulfamoyl or SO3M; or a rest with free valence to link to reactive anchor T;

R²⁸⁶, R²⁸⁷, R²⁹⁴, R²⁹⁵, R³⁰⁵, R³⁰⁶, R³¹⁶ and R³¹⁷, independent from one another, are hydrogen or alkyl, alkoxy, halogen, cyano, -SO₃M, trifluoromethyl, nitro, ester, NHC(0)R³¹⁸, CONH₂, S(0)₂R³¹⁹ or -S0₂X;

_R302 _{to R}304 _{an d R}313 _{tQ R}315^ j_nc|_ep_enc|_ent f_{rom one} another, are hydrogen, alkyl, alkyl substituted, alkyl chain interrupted by one or two heteroatoms, alkoxy, alkoxy substituted, halogen ,trifluoromethyl; cycloalkyi; heterocycloalkyi; cyano; nitro; acyloxy; alkylcarbonyl, acylamino; aryloylamino, cinnamoylamino, alkylsulfonylamino; alkylthio; alkylsulfonyl, alkoxycarbonyl, carbamoyl, sulfamoyl, ureido, alkylureido, S0₃M, COOM or contain a group of formulae (2a) to (2c); E¹⁶ to E¹⁹, independent from each other, are a group of general formulae (E1 ) to (E3);

T, X and M have the same meanings as defined in claim 1 .

10. Chemical composition consisting of two or more chemical compounds according to any one of claims 1 to 9.

1 1. Chemical composition comprising one or more chemical compounds according to any one of claims 1 to 9.

12. Aqueous solution for dying comprising one or more chemical compounds

according to any one of claims 1 to 9.

13. Process for the production of chemical compounds according to formula (I) comprising steps:

a) diazotizing compounds of formula (IV),

b) reacting the diazonium salts obtained in step a) with a compound of formula K to obtain an intermediate of formula (V)

c) diazotizing component (B-NH₂),

cx1 ) optionally coupling the diazotized product of step c) onto the compound (A- NH₂) and

cx2) diazotizing the coupling product of step cx1 )

d) coupling the diazotized product of step c) onto the intermediate V to obtain the bisazo-product of general formula (VI) in case of step c)

or coupling the diazotized coupling product of cx2) onto the intermediate V to obtain the trisazo-product of general formula (VIII),

.NH_{2 +} .NH₂

(VIII) e) reacting the product of step d) having formula (VI) or (VIII) with copper salt to give the copper complex dyes (IX) in case of (VI) or (X) in case of (VIII):

14. Use of a chemical compound according to any one of claims 1 to 9, a chemical composition according to claim 10 or 1 1 or of an aqueous solution according to claim 12 for dying fibers selected from the group consisting of: vegetable fibres, seed fibres, cotton, kapok, coir from coconut husk; bast fibers, flax, hemp, jute, kenaf, ramie, rattan; leaf fibres, sisal, henequen, banana; stalk fibres, bamboo; fibres from animals, wool, silk, cashmere wool, alpaca fiber, mohair, Angora fibre as well as fur and leather materials; manufactured and fibres, cellulosic fibres; paper and cellulosic regenerated fibres, viscose rayon fibres, acetate and triacetate fibers and Lyocell fibers; and synthetic fiber materials, nylon materials, nylon-6, nylon-6.6 and aramid fibres.

15. Fiber selected from the group consisting of: vegetable fibres, seed fibres, cotton, kapok, coir from coconut husk; bast fibers, flax, hemp, jute, kenaf, ramie, rattan; leaf fibres, sisal, henequen, banana; stalk fibres, bamboo; fibres from animals, wool, silk, cashmere wool, alpaca fiber, mohair, Angora fibre as well as fur and leather materials; manufactured, regenerated, and recycled (pis see the No 17)<clearly definded expression?> fibres, cellulosic fibres; paper and cellulosic regenerated fibres, viscose rayon fibres, acetate and triacetate fibers and Lyocell fibers; and synthetic fiber materials, nylon materials, nylon-6, nylon-6.6 and aramid fibres

comprising one or more chemical compounds according to any one of claims 1 to 9 either in chemically and/or physically bound form.