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

2001-09-24

2002-05-21

Powers, Fiona T. (Department: 1626)

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

Organic compounds

Azo

C534S642000, C534S643000, C008S549000, C008S918000

Reexamination Certificate

active

06392021

ABSTRACT:

The present invention relates to novel reactive dyes, to processes for their preparation and to their use in the dyeing or printing of textile fibre materials.
The practice of dyeing using reactive dyes has recently led to higher demands being made of the quality of the dyeings and the profitability of the dyeing process. As a result, there is still a need for novel reactive dyes having improved properties, especially in respect of their application.
Dyeing nowadays requires reactive dyes that have sufficient substantivity and at the same time have good ease of washing off of unfixed dye. They should also have a good tinctorial yield and high reactivity, the objective being to provide especially dyeings having high degrees of fixing. The known dyes do not satisfy these requirements in all properties.
The problem underlying the present invention is accordingly to find, for the dyeing and printing of fibre materials, novel improved reactive dyes that possess the qualities characterised above to a high degree. The novel dyes should especially be distinguished by high fixing yields and high fibre-dye binding stability; it should also be possible for dye that is not fixed to the fibre to be washed off easily. The dyes should also yield dyeings having good allround properties, for example fastness to light and to wetting.
It has been shown that the problem posed is largely solved by the novel dyes defined below.
The present invention accordingly relates to reactive dyes of formula (1)
wherein
b is the number 1 or 2,
A is a radical of formula (2) or (3)
D
1
is a radical of formula
 or the radical of an azo dye when b is the number 1 or the radical of an aromatic tetraazo component when b is the number 2,
D
2
is the radical of a diazo component, of the benzene or naphthalene series,
R
1
and R
2
are each independently of the other hydrogen or C
1
-C
4
alkyl,
(R
3
)
0-2
denotes from 0 to 2 substituents selected from the group C
1
-C
4
alkyl, C
1
-C
4
alkoxy, halogen and sulfo,
X
1
is fluorine or chlorine,
Y is vinyl or a radical —CH
2
—CH
2
—U and U is a group removable under alkaline conditions,
l is the number 2, 3, 4, 5 or 6, and
m and n are each independently of the other the number 0 or 1, wherein
when A is a radical of formula (3) and D
1
is the radical of an azo dye, at least one of the radicals D
1
and D
2
contains a fibre-reactive radical of formula (2) with the proviso that A is a radical of formula (2) when D
1
is the radical of an aromatic tetraazo component, and A is a radical of formula (3) when D
1
is a radical of formula (4).
The radicals R
1
and R
2
in a reactive dye of formula (1) are as alkyl radicals straight-chain or branched. The following radicals may be mentioned by way of example: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and tert-butyl.
R
1
, and R
2
are preferably hydrogen or methyl and especially hydrogen.
R
3
as halogen is, for example, fluorine, chlorine or bromine, preferably chlorine or bromine and especially chlorine.
R
3
as C
1
-C
4
alkyl is, for example, methyl, ethyl, n- or iso-propyl or n-, sec-, tert- or iso-butyl, preferably methyl or ethyl and especially methyl.
As C
1
-C
4
alkoxy for R
3
there come into consideration, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy and isobutoxy, preferably methoxy and ethoxy and especially methoxy.
R
3
preferably denotes one or two sulfo radicals, especially one sulfo radical.
As a group U removable under alkaline conditions there come into consideration, for example, —Cl, —Br, —F, —OSO
3
H, —SSO
3
H, —OCO—CH
3
, —OPO
3
H
2
, —OCO—C
6
H
5
, —OSO
2
—C
1
-C
4
alkyl and —OSO
2
—N(C
1
-C
4
alkyl)
2
. U is preferably a group of formula —Cl, —OSO
3
H, —SSO
3
H, —OCO—CH
3
, —OCO—C
6
H
5
or —OPO
3
H
2
, especially —Cl or —OSO
3
H.
Examples of suitable radicals Y are accordingly vinyl, &bgr;-bromo- or &bgr;-chloro-ethyl, &bgr;-acetoxy-ethyl, &bgr;-benzoyloxyethyl, &bgr;-phosphatoethyl, &bgr;-sulfatoethyl and &bgr;-thiosulfatoethyl. Y is preferably vinyl, &bgr;-chloroethyl or &bgr;-sulfatoethyl.
X
1
is preferably chlorine.
l preferably denotes the number 3 or 4 and especially 3.
m preferably denotes the number 1.
The reactive dyes of formula (1) according to the invention preferably correspond to a dye of formula (1a)
wherein
D
1
is the radical of an azo dye when b is the number 1 or the radical of an aromatic tetraazo component when b is the number 2, and
R
1
, Y, b, l and m have the definitions and preferred meanings given above.
In a further preferred embodiment, the reactive dyes of formula (1) according to the invention correspond to a dye of formula (1b)
wherein
D
2
, R
1
, R
2
, X
1
, Y, l, m and n have the definitions and preferred meanings given above.
Suitable substituents of D
1
as a radical of an azo dye and of D
2
include the substituents customary for azo dyes. The following may be mentioned by way of example: C
1
-C
4
alkyl, which is to be understood as being methyl, ethyl, n- or iso-propyl, and n-, iso-, sec- or tert-butyl; C
1
-C
4
alkoxy, which is to be understood as being methoxy, ethoxy, n- or iso-propoxy and n-, iso-, sec- or tert-butoxy; hydroxy-C
1
-C
4
alkoxy; phenoxy; C
2
-C
6
alkanoylamino unsubstituted or substituted in the alkyl moiety by hydroxy or by C
1
-C
4
alkoxy, e.g. acetyl-amino, hydroxyacetylamino, methoxyacetylamino or propionylamino; benzoylamino unsubstituted or substituted in the phenyl moiety by hydroxy, sulfo, halogen, C
1
-C
4
alkyl or by C
1
-C
4
alkoxy; C
1
-C
6
alkoxycarbonylamino unsubstituted or substituted in the alkyl moiety by hydroxy, C
1
-C
4
alkyl or by C
1
-C
4
alkoxy; phenoxycarbonylamino unsubstituted or substituted in the phenyl moiety by hydroxy, C
1
-C
4
alkyl or by C
1
-C
4
alkoxy; amino; N-C
1
-C
4
alkyl- or N,N-di-C
1
-C
4
alkyl-amino unsubstituted or substituted in the alkyl moiety by hydroxy, C
1
-C
4
alkoxy, carboxy, cyano, halogen, sulfo, sulfato, phenyl or by sulfophenyl, e.g. methylamino, ethyl-amino, N,N-dimethylamino, N,N-diethylamino, &bgr;-cyanoethylamino, &bgr;-hydroxyethylamino, N,N-di-&bgr;-hydroxyethylamino, &bgr;-sulfoethylamino, &ggr;-sulfo-n-propylamino, &bgr;-sulfatoethylamino, N-ethyl-N-(3-sulfobenzyl)-amino, N-(&bgr;-sulfoethyl)-N-benzylamino; cyclohexylamino; N-phenylamino or N-C
1
-C
4
alkyl-N-phenylamino unsubstituted or substituted in the phenyl moiety by nitro, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, carboxy, halogen or by sulfo; C
1
-C
4
alkoxycarbonyl, e.g. methoxy- or ethoxy-carbonyl; trifluoromethyl; nitro; cyano; halogen, which is to be understood generally as being, for example, fluorine, bromine or especially chlorine; ureido; hydroxy; carboxy; sulfo; sulfomethyl; carbamoyl; carbamido; sulfamoyl; N-phenylsulfamoyl or N-C
1
-C
4
alkyl-N-phenylsulfamoyl unsubstituted or substituted in the phenyl moiety by sulfo or by carboxy; methyl- or ethyl-sulfonyl.
Suitable substituents of D
1
as a radical of an azo dye and of D
2
also include fibre-reactive radicals.
Fibre-reactive radicals are to be understood as being those which are capable of reacting with the hydroxy groups of the cellulose, with the amino, carboxy, hydroxy and thiol groups in wool and silk or with the amino and possibly carboxy groups of synthetic polyamides to form covalent chemical bonds. The fibre-reactive radicals are generally bonded to the dye radical directly or via a bridge member. Suitable fibre-reactive radicals are, for example, those having at least one removable substituent at an aliphatic, aromatic or heterocyclic radical or those wherein the mentioned radicals contain a radical suitable for reaction with the fibre material, for example a vinyl radical.
A fibre-reactive radical present in D
1
as a radical of an azo dye and in D
2
preferably corresponds to formula (2a), (5a), (5b), (5c), (5d), (5e) or (5f)
wherein
Hal is chlorine or bromine;
X
2
is halogen, carboxypyridin-1-yl or 3-carbamoylpyridin-1-yl;
T
1
has independently the same definitions as X
2
, or is a non-fibre-reactive substituent or a fibre-reactive radical of formula (6a), (6b), (6c), (6d), (6e) or (6f)
 wherein
R
4
an

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