Reactive dyes, their preparation and use

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

2002-08-16

2003-12-30

Badio, Barbara P. (Department: 1616)

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

Organic compounds

Azo

C534S573000, C534S617000, C534S630000, C534S632000

Reexamination Certificate

active

06670457

ABSTRACT:

The present invention relates to novel reactive dyes, processes 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 economics of the dyeing process. Consequently, there 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 of the non-fixed portions are now required for dyeing. They should furthermore show a good dyeing yield and have a high reactivity, and, in particular, dyeings with high degrees of fixing should be produced. The known dyes do not meet these requirements in all properties.
The present invention is therefore based on the object of discovering novel, improved reactive dyes for dyeing and printing fibre materials which have the qualities described above to a high degree. The novel dyes should be distinguished, in particular, by high fixing yields and high fibre-dye bond stabilities, and furthermore the portions not fixed on the fibre should be easy to wash off. They should furthermore produce dyeings with good allround properties, for example light and wet fastness properties.
It has been found that the set object can be largely achieved with the novel reactive dyes defined below.
The present invention relates to compounds of the formula
in which Z is the radical of a diazo component,
R is substituted or unsubstituted C
1
-C
4
alkyl,
R
1
is hydrogen or substituted or unsubstituted C
1
-C
4
alkyl,
X is halogen, 3-carboxypyridin-1-yl or 3-carbamoylpyridin-1-yl and
D is the radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan or dioxazine chromophore,
with the provisos that (i) at least one of the radicals D and Z carries a fibre-reactive radical —SO
2
—Y or —NHCO—Y
1
, in which
Y is vinyl or a radical —CH
2
—CH
2
—U,
U is a leaving group,
Y
1
is a group —CHX
1
—CH
2
X
1
or —CX
1
═CH
2
and
X
1
is bromine or chlorine,
and that (ii) the radical —NR
1
— is not bonded to a phenylene radical substituted by —NH
2
if D is the radical of a monoazo or disazo chromophore.
The radical —NR— can be bonded to the hydroxynaphthalenesulfonic acid radical in the 7-position or, preferably, in the 6-position.
Substituted or unsubstituted C
1
-C
4
alkyl R or R
1
can be, for example, methyl, ethyl, n- or iso-propyl or n-, sec-, tert- or iso-butyl which are unsubstituted or substituted, for example by hydroxyl, sulfo, sulfato, carboxyl, cyano, halogen, C
1
-C
4
alkoxycarbonyl or carbamoyl.
R is preferably unsubstituted C
1
-C
4
alkyl, particularly preferably methyl or ethyl, and especially preferably methyl.
R
1
is preferably hydrogen or C
1
-C
4
alkyl which is unsubstituted or substituted by hydroxyl, particularly preferably hydrogen, methyl or ethyl, and especially preferably hydrogen.
X is preferably halogen, for example fluorine, chlorine or bromine, and particularly preferably fluorine or chlorine.
Z is, for example, the radical of an aminobenzene, aminonaphthalene, phenylazoaminobenzene or phenylazoaminonaphthalene, which can be further substituted by substituents customary in dyes.
Suitable substituents on the radical Z are, for example, sulfo; C
1
-C
4
alkyl, in particular methyl; hydroxyl; C
1
-C
4
alkoxy, in particular methoxy; C
1
-C
4
alkoxy which is substituted by hydroxyl, methoxy, ethoxy or sulfato, for example &bgr;-hydroxyethoxy, &bgr;-sulfatoethoxy or &bgr;-methoxyethoxy; halogen, in particular chlorine; C
2
-C
4
alkanoylamino, for example acetylamino or propionylamino; ureido; or a fibre-reactive radical of the formula
—SO
2
—Y  (2
a
),
—CONH—(CH
2
)
n
—SO
2
—Y  (2
b
),
—(O)
p
—(CH
2
)
m
—CONH—(CH
2
)
n
—SO
2
—Y  (2
c
),
—NH—CO—Y
1
  (2
d
)
or
in which Y and Y
1
are each as defined above,
X′ is independently as defined and preferred above for X,
T is a non-reactive amino radical,
p is the number 0 or 1 and
m and n independently of one another are each an integer from 1 to 6.
In a radical —CH
2
—CH
2
—U Y, the leaving group U can be, 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 or —OSO
2
—N(C
1
-C
4
alkyl)
2
. U is preferably a group of the formula —Cl, —OSO
3
H, —SSO
3
H, —OCO—CH
3
, —OCO—C
6
H
5
or —OPO
3
H
2
, in particular —Cl or —OSO
3
H, and particularly preferably —OSO
3
H.
Y is preferably vinyl, &bgr;-chloroethyl, &bgr;-sulfatoethyl, &bgr;-thiosulfatoethyl, &bgr;-acetoxyethyl, &bgr;-phenoxyethyl or &bgr;-phosphatoethyl, and particularly preferably &bgr;-sulfatoethyl or vinyl.
Y
1
is a group —CHX
1
—CH
2
X
1
or —CX
1
═CH
2
, in which X
1
is chlorine or, preferably, bromine.
n is preferably the number 2, 3 or 4, particularly preferably the number 2 or 3, and especially preferably the number 2. m is preferably the number 1, 2 or 3, and particularly preferably the number 1 or 2. p is preferably the number 0.
A non-reactive amino radical T can be, for example, amino; N—C
1
-C
4
alkylamino or N,N-di-C
1
-C
4
alkylamino, in which the alkyl can in each case be substituted, for example by sulfo, sulfato, hydroxyl, carboxyl or phenyl; cyclohexylamino; phenylamino or naphthylamino, in which the phenyl or naphthyl can in each case be substituted, for example by C
1
-C
4
alkyl, C
1
-C
4
alkoxy, amino, C
2
-C
4
alkanoylamino, carboxyl, sulfo or halogen; N-C
1
-C
4
alkyl-N-phenylamino, in which the alkyl and phenyl can optionally be substituted as described above, or morpholino.
Examples of suitable non-reactive amino radicals T are amino, methylamino, ethylamino, &bgr;-hydroxyethylamino, N,N-di-&bgr;-hydroxyethylamino, &bgr;-sulfoethylamino, cyclohexylamino, o-, m- or p-methylphenylamino, o-, m- or p-methoxyphenylamino, o-, m- or p-sulfophenylamino, 2,4- or 2,5-disulfophenylamino, 2- or 3-sulfo-4-methoxyphenylamino, 2- or 3-sulfo-4-methylphenylamino, 4-methyl-2,5-disulfophenylamino, o-carboxyphenylamino, 1- or 2-naphthylamino, 1-sulfo-2-naphthylamino, 1,5-disulfo-2-naphthylamino, 6,8-disulfo-2-naphthylamino, 4,8-disulfo-2-naphthylamino, 4,6,8-trisulfo-2-naphthylamino, 1,5,7-trisulfo-2-naphthylamino, 3,6,8-trisulfo-2-naphthylamino, 1,6-disulfo-2-naphthylamino, N-ethyl-N-phenylamino, N-methyl-N-phenylamino, N-&bgr;-sulfoethyl-N-phenylamino, &bgr;-hydroxyethyl-N-phenylamino and morpholino.
T is preferably amino, N-mono- or N,N-di-C
1
-C
2
-alkylamino, which is unsubstituted or substituted by hydroxyl, sulfo or sulfato, cyclohexylamino, phenylamino or naphthylamino, which are unsubstituted or substituted by methyl, methoxy, carboxyl or sulfo, N—C
1
-C
2
alkyl-N-phenylamino or morpholino and particularly preferably amino, N-mono- or N,N-di-C
1
-C
2
alkyl-amino which is unsubstituted or substituted by sulfo, phenylamino which is substituted by 1 to 3 identical radicals from the group consisting of methyl, methoxy and sulfo, or 1- or 2-naphthylamino which carries 1 to 3 sulfo groups.
Examples of preferred radicals Z are:
(a) phenyl which is substituted by one or more identical or different substituents from the group consisting of sulfo, C
1
-C
4
alkyl, C
1
-C
4
alkoxy and reactive radicals of the formulae (2
a
), (2
b
) or (2
d
) defined above;
(b) 1- or 2-naphthyl which is substituted by sulfo or a reactive radical of the formula (2
a
) defined above;
(c) a radical of the formula
in which (R
2
)
0-2
is 0 to 2 identical or different radicals R
2
from the group consisting of sulfo; methyl, methoxy, &bgr;-hydroxyethoxy, &bgr;-sulfatoethoxy, &bgr;-methoxyethoxy, acetylamino and ureido and (R
3
)
0-3
is 0 to 3 identical or different radicals from the group consisting of sulfo, methyl and methoxy; and
(d) a radical of the formula
in which T′ is independently as defined and preferred above for T, X″ is independently as defined and preferred above for X, and (R
4
)
1-2
is 1 or 2 identical or different radicals R
4
from the group consisting of methyl, methoxy, sulfo and react

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