Reactive dyes, processes for their preparation and their use

Details Reactive dyes, processes for their preparation and their use Reactive dyes, processes for their preparation and their use

2000-03-09

2003-07-15

Einsmann, Margaret (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Reactive dye composition, process, or product

Alkylene sulfato, halotriazine, halodiazine,...

C008S918000, C544S076000, C534S635000, C534S642000

Reexamination Certificate

active

06592634

ABSTRACT:

The present invention relates to novel unsymmetric dioxazine dyes which are fibre-reactive, processes for their preparation and their use for dyeing or printing 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 demand for novel reactive dyes which have improved properties, in particular in respect of application.
Reactive dyes which have a high degree of exhaustion and a high degree of fixing, in particular no alkaline after-treatment for removal of unfixed dye being necessary, are nowadays required for dyeing. These dyes should furthermore have a good tinctorial yield and a high reactivity. EP-A-0 260 227 and U.S. Pat. No. 4,841,049 disclose unsymmetric, fibre-reactive dioxazine dyes. However, all the properties of the known dyes do not meet the requirements mentioned.
The present invention is therefore based on the object of providing novel, improved fibre-reactive dioxazine dyes for dyeing and printing fibre materials which have the qualities characterized above to a high degree. The novel dyes should have the distinctive features in particular of high degrees of exhaustion, high fixing yields and high fibre-dye bond stabilities. They should furthermore produce dyeings with good all-round properties, for example light- and wet-fastness properties.
It has been found that the stated object is substantially achieved by the reactive dyes defined below.
The present invention thus provides reactive dyes of the formula (1)
in which
R
1
, R
2
, R
3
and R
4
independently of one another are hydrogen or substituted or unsubstituted C
1
-C
4
alkyl,
(R
5
)
0-2
and (R
6
)
0-2
independently of one another are 0 to 2 identical or different substituents from the group consisting of C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
2
-C
4
alkanoylamino, halogen, carboxyl, sulfo, carbamoyl, N-C
1
-C
4
alkylcarbamoyl, N,N-di-C
1
-C
4
alkylcarbamoyl, C
1
-C
4
alkylsulfonyl, sulfamoyl, N-C
1
-C
4
alkylsulfamoyl and N,N-di-C
1
-C
4
alkylsulfamoyl,
A is hydrogen or C
1
-C
4
alkyl which is unsubstituted or substituted by hydroxyl, sulfo, carboxyl or sulfato, phenyl or naphthyl which are unsubstituted or substituted by C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
2
-C
4
alkanoylamino, hydroxyl, carboxyl, carbamoyl, sulfo or halogen, phenyl-C
1
-C
4
alkylene which is unsubstituted or substituted in the phenyl ring by C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
2
-C
4
alkanoylamino, hydroxyl, carboxyl, sulfo, carbamoyl, ureido or halogen, or C
5
-C
7
cycloalkyl which is unsubstituted or substituted by C
1
-C
4
alkyl,
B
1
is an aliphatic or aromatic bridge member,
D
1
is a radical of the aliphatic, aromatic or heterocyclic series which is substituted by at least one fibre-reactive group,
V
1
and V
2
independently of one another are hydrogen, halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, or substituted or unsubstituted phenyl, phenoxy, C
2
-C
6
alkanoylamino or benzoylamino and X
1
is halogen, hydroxyl, C
1
-C
4
alkoxy, C
1
-C
4
alkylthio, substituted or unsubstituted amino or an N-heterocycle which may contain further heteroatoms, with the proviso that
A and R
1
are not hydrogen if B
1
is ethylene, 1,3-propylene, 1,4-butylene, phenylene which is unsubstituted or substituted by sulfo, or 1,4-cyclohexylene, or the radical
 is piperazine and
A is not hydroxyethyl and R
1
is not hydrogen if B
1
is ethylene and X
1
is 2,6-di-sulfophenylamino.
Alkyl radicals R
1
, R
2
, R
3
and R
4
are straight-chain or branched. The alkyl radicals can be further substituted, for example by hydroxyl, sulfo, sulfato, cyano or carboxyl. Examples are the following radicals: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl, and the corresponding radicals substituted by hydroxyl, sulfo, sulfato, cyano or carboxyl. Preferred substituents are hydroxyl, sulfo, sulfato or carboxyl, in particular hydroxyl or sulfato. The radical R
4
is also a radical of the formula —(CH
2
)
2
—SO
2
—(CH
2
)
2
—Cl.
C
1
-C
4
alkyl (R
5
)
0-2
, (R
6
)
0-2
, V
1
and V
2
independently of one another are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl or isobutyl, preferably methyl or ethyl, and in particular methyl, the definitions and preferences also applying to the following C
1
-C
4
alkyl radicals.
C
1
-C
4
alkoxy (R
5
)
0-2
, (R
6
)
0-2
, V
1
, V
2
and X
1
independently of one another are, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy or isobutoxy, preferably methoxy or ethoxy and in particular methoxy, the definitions and preferences mentioned also applying to the following C
1
-C
4
alkoxy radicals.
C
2
-C
4
alkanoylamino (R
5
)
0-2
and (R
6
)
0-2
are, for example, acetylamino or propionylamino, in particular acetylamino, the definitions and preferences mentioned also applying to the following C
2
-C
4
alkanoylamino radicals.
Halogen (R
5
)
0-2
, (R
6
)
0-2
, V
1
and V
2
independently of one another are, for example, fluorine, chlorine or bromine, preferably chlorine or bromine and in particular chlorine.
N-C
1
-C
4
alkylcarbamoyl (R
5
)
0-2
and (R
6
)
0-2
independently of one another are, for example, N-methyl-, N-ethyl-, N-propyl-, N-isopropyl-, N-butyl-, N-sec-butyl-, N-tert-butyl- or N-isobutylcarbamoyl, preferably N-methyl- or N-ethylcarbamoyl and in particular N-methylcarbamoyl.
N,N-di-C
1
-C
4
alkylcarbamoyl (R
5
)
0-2
and (R
6
)
0-2
independently of one another are, for example, N,N-di-methyl-, N,N-di-ethyl-, N,N-di-propyl-, N,N-di-isopropyl-, N,N-di-butyl-, N,N-di-sec-butyl- or N,N-di-isobutylcarbamoyl, preferably N,N-di-methyl- or N,N-di-ethylcarbamoyl and in particular N,N-di-methylcarbamoyl.
C
1
-C
4
alkylsulfonyl (R
5
)
0-2
and (R
6
)
0-2
independently of one another are, for example, methyl-, ethyl-, n-propyl-, isopropyl-, n-butyl-, sec-butyl-, tert-butyl- or isobutylsulfonyl, preferably methyl- or ethylsulfonyl, and in particular methylsulfonyl.
N-C
1
-C
4
alkylsulfamoyl (R
5
)
0-2
and (R
6
)
0-2
independently of one another are, for example, N-methyl-, N-ethyl-, N-propyl-, N-isopropyl-, N-butyl-, N-sec-butyl-, N-tert-butyl- or N-isobutylsulfamoyl, preferably N-methyl- or N-ethylsulfamoyl and in particular N-methylsulfamoyl.
N,N-di-C
1
-C
4
alkylsulfamoyl (R
5
)
0-2
and (R
6
)
0-2
independently of one another are, for example, N,N-di-methyl-, N,N-di-ethyl-, N,N-di-propyl-, N,N-di-isopropyl-, N,N-di-butyl-, N,N-di-sec-butyl- or N,N-di-isobutylsulfamoyl, preferably N,N-di-methyl- or N,N-di-ethylsulfamoyl and in particular N,N-di-methylsulfamoyl.
In a preferred embodiment of the reactive dyes according to the invention, A is C
1
-C
4
alkyl, which is unsubstituted or substituted by hydroxyl, sulfo, carboxyl or sulfato, phenyl or naphthyl which are unsubstituted or substituted by C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
2
-C
4
alkanoylamino, hydroxyl, carboxyl, carbamoyl, sulfo or halogen, in particular phenyl which is unsubstituted or substituted by the radicals mentioned, phenyl-C
1
-C
4
alkylene which is unsubstituted or substituted in the phenyl ring by C
1
-C
4
-alkyl, C
1
-C
4
alkoxy, C
2
-C
4
alkanoylamino, hydroxyl, carboxyl, sulfo, carbamoyl, ureido or halogen, or C
5
-C
7
-cycloalkyl which is unsubstituted or substituted by C
1
-C
4
alkyl.
A in the reactive dyes according to the invention is particularly preferably C
1
-C
4
alkyl which is unsubstituted or substituted by hydroxyl, sulfo, carboxyl or sulfato, preferably hydroxyl or sulfato, and in particular sulfato. The substituted alkyl radicals are preferred.
An aliphatic bridge member B
1
is, for example, a C
2
-C
12
alkylene radical, in particular a C
2
-C
6
alkylene radical, which can be interrupted by 1, 2 or 3 members from the group consisting of —NH—, —N(CH
3
)— and, in particular, —O— and is unsubstituted or substituted by hydroxyl, sulfo, sulfato, cyano or carboxyl. Preferred substituents of the alkylene radicals B
1
are hydroxyl, sulfo or sulfato, in particular hydroxyl or sulfato.
Aliphatic bridge members B
1
are further

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