Dyes, a process for their preparation and their use

Details Dyes, a process for their preparation and their use Dyes, a process for their preparation and their use

2000-03-15

2002-03-05

Powers, Fiona T. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Azo

C008S549000

Reexamination Certificate

active

06353094

ABSTRACT:

The present invention relates to novel dyes, in particular reactive dyes, a process for their preparation and their use for dyeing or printing textile fibre materials.
The practice of dyeing using reactive dyes has recently led to increased requirements regarding the quality of the dyeings and the profitability of the dyeing process. There consequently continues to be a need for novel reactive dyes which have improved properties in particular in respect of application.
Reactive dyes which have an adequate substantivity and at the same time a good ease of washing off for the unfixed portions are required nowadays for dyeing. They should furthermore have a good tinctorial yield and a high reactivity, and in particular dyeings with high degrees of fixing should be produced. These requirements are not met in all properties by the known dyes.
The present invention is therefore based on the object of discovering novel improved dyes, in particular reactive dyes, which are used for dyeing and printing fibre materials and have the qualities characterized above to a high degree. The novel dyes should have the distinctive features in particular of high fixing yields and high fibre-dye bond stabilities, and furthermore the portions not fixed to the fibre should be easy to wash out. They should furthermore produce dyeings with good all-round properties, for example light- and wetfastness properties.
It has been found that the object described is substantially achieved with the novel dyes defined below.
The present invention therefore relates to dyes of the formula (1)
in which
Me is Cu or Ni,
R
1
is hydrogen or substituted or unsubstituted C
1
-C
4
alkyl or R
1
is as defined for A,
X
1
is halogen, hydroxyl, C
1
-C
4
alkoxy, substituted or unsubstituted C
1
-C
4
alkylthio or amino or
is an N-heterocyclic radical which may contain further heteroatoms,
u is the number 1, 2, 3 or 4,
q is the number 0 or 1,
the benzene rings I, II or III are unsubstituted or further substituted and
A is a radical of the formula (2a), (2b) or (3)
in which
B
1
and B
2
independently of one another are an aliphatic bridge member,
D
1
and D
2
independently of one another are the radical of a diazo component of the benzene or naphthalene series,
R
2
is hydrogen or substituted or unsubstituted C
1
-C
4
alkyl,
R
3
and R
6
independently of one another are hydrogen, cyano, carbamoyl or sulfomethyl,
R
4
is hydrogen, C
1
-C
4
alkyl or amino,
R
5
is amino or N-mono- or N,N—di—C
1
-C
4
alkylamino which are unsubstituted or substituted in the alkyl moiety and
R
7
is hydrogen or C
1
-C
4
alkyl.
The dyes of the formula (1) contain at least two, preferably 2 to 6, and in particular 2 to 4 sulfo groups, each of which is either in the form of its free acid or, preferably, salts thereof. Salts are, for example, the alkali metal, alkaline earth metal or sodium salts, salts of an organic amine or mixtures thereof. Examples are sodium, lithium, potassium or ammonium salts, the salt of mono-, di- or triethanolamine or Na/Li- or Na/Li/NH
4
mixed salts.
Me is preferably Cu.
Substituted or unsubstituted C
1
-C
4
alkyl R
1
and R
2
can be methyl, ethyl, n- or i-propyl or n-, sec-, tert- or isobutyl which are unsubstituted or substituted, for example by hydroxyl, sulfo, sulfato, carboxyl, cyano, halogen, C
1
-C
4
alkoxycarbonyl or carbamoyl, in particular by hydroxyl, sulfo, sulfato or carboxyl.
R
1
is preferably hydrogen, C
1
-C
4
alkyl which is unsubstituted or substituted by hydroxyl, or a radical A, particularly preferably hydrogen, methyl, ethyl or &bgr;-hydroxyethyl or a radical A, and especially preferably hydrogen or a radical A.
Halogen X
1
is, for example, fluorine, chlorine or bromine.
C
1
-C
4
alkoxy X
1
, is, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy or isobutoxy, preferably methoxy or ethoxy, and in particular methoxy.
C
1
-C
4
alkylthio X
1
is, for example, methylthio, ethylthio, n-propylthio, isopropylthio or n-butylthio, in particular ethylthio or n-propylthio. The radicals mentioned are unsubstituted or substituted in the alkyl moiety by hydroxyl, carboxyl or sulfo. The substituted radicals are preferred.
Substituted or unsubstituted amino X
1
is amino which is unsubstituted or substituted on the N atom, for example the following radicals:
N-mono- or N,N- di- C
1
-C
4
alkylamino, which includes both the unsubstituted radicals and the radicals substituted in the alkyl moiety, for example by C
1
-C
4
-alkoxy, hydroxyl, carboxyl, sulfo or sulfato; the radicals substituted in the alkyl moiety are preferred;
C
5
-C
7
-cycloalkylamino, which includes both the unsubstituted radicals, and the radicals substituted in the cycloalkyl ring, for example by C
1
-C
4
alkyl, in particular methyl; the corresponding cyclohexyl radicals are preferred such radicals;
phenylamino or N—C
1
-C
4
-alkyl-N-phenylamino, which includes both the unsubstituted radicals and the radicals substituted in the phenyl ring, for example by C
1
-C
4
alkyl, C
1
-C
4
alkoxy, halogen, carboxyl or sulfo; these radicals are preferably unsubstituted in the phenyl ring or substituted by sulfo.
N-heterocyclic radicals X
1
which may contain further heteroatoms are, for example, morpholino or piperidin-1-yl.
X
1
is preferably fluorine or chlorine.
u is preferably the number 1, 2 or 3, in particular 2 or 3.
q is preferably the number 1.
Aliphatic bridge members B
1
and B
2
are, independently of one another, for example, straight-chain or branched C
2
-C
12
alkylene which is unsubstituted or substituted by hydroxyl, C
1
-C
4
alkoxy, sulfato or sulfo and/or interrupted once or several times by —O— or —NR′—, in which R′ is hydrogen or C
1
-C
4
alkyl, preferably hydrogen, methyl or ethyl, and particularly preferably hydrogen. B
1
and B
2
independently of one another are preferably straight-chain or branched C
2
-C
6
alkylene, which is unsubstituted or substituted by hydroxyl, sulfo or sulfato, and particularly preferably unsubstituted straight-chain or branched C
2
-C
6
-alkylene. Examples of particularly preferred radicals B
1
and B
2
are 1,2-ethylene, 1,3-propylene, 2-hydroxy-1,3-propylene, 1,4-butylene, 2-methyl-1,5-pentylene and 1,6-hexylene, in particular 1,2-propylene and 1,2-ethylene, and especially 1,2-ethylene.
Substituents which are customary in dyes are suitable for D
1
and D
2
. Examples are the following: C
1
-C
4
alkyl, which is to be understood as meaning methyl, ethyl, n- or isopropyl or n-, iso-, sec- or tert-butyl; C
1
-C
4
alkoxy, which is to be understood as meaning methoxy, ethoxy, n- or isopropoxy or n-, iso-, sec- or tert-butoxy; hydroxy-C
1
-C
4
alkoxy; phenoxy; C
2
-C
6
alkanoylamino which is unsubstituted or substituted in the alkyl moiety by hydroxyl or C
1
-C
4
alkoxy, for example acetylamino, hydroxyacetylamino, methoxyacetylamino or propionylamino; benzoylamino which is unsubstituted or substituted in the phenyl moiety by hydroxyl, sulfo, halogen, C
1
-C
4
alkyl or C
1
-C
4
alkoxy; C
1
-C
6
alkoxycarbonylamino which is unsubstituted or substituted in the alkyl moiety by hydroxyl, C
1
-C
4
alkyl or C
1
-C
4
-alkoxy; phenoxycarbonylamino; which is unsubstituted or substituted in the phenyl moiety by hydroxyl, C
1
-C
4
alkyl or C
1
-C
4
alkoxy; amino; N—C
1
-C
4
alkyl- or N,N- di- C
1
-C
4
alkylamino which are unsubstituted or substituted in the alkyl moiety by hydroxyl, C
1
-C
4
alkoxy, carboxyl, cyano, halogen, sulfo, sulfato, phenyl or sulfophenyl, for example methylamino, ethylamino, N,N-dimethylamino, N,N-diethylamino, &bgr;-cyanoethylamino, &bgr;-hydroxyethylamino, N,N-di-&bgr;-hydroxyethylamino, &bgr;-sulfoethylamino, &ggr;-sulfo-n-propylamino, &bgr;-sulfatoethylamino, N-(3-sulfobenzyl)amino or N-ethyl-N-(3-sulfobenzyl)amino, N-(&bgr;-sulfoethyl)-N-benzylamino; cyclohexylamino; N-phenylamino or N—C
1
-C
4
alkyl-N-phenylamino which are unsubstituted or substituted in the phenyl moiety by nitro, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, carboxyl, halogen or sulfo; C
1
-C
4
alkoxycarbonyl, for example methoxy- or ethoxycarbonyl; trifluoromethyl; nitro; cyano; halogen, which is to be understoo

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