Process for dyeing or printing and novel reactive dyes

Details Process for dyeing or printing and novel reactive dyes Process for dyeing or printing and novel reactive dyes

2000-04-03

2001-06-05

Einsmann, Margaret (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Dye or potential dye composition, additive, treatment,...

Azo, acridone, or quinone dye

C008S683000, C008S684000, C008S686000, C008S688000, C008S920000, C008S919000, C008S924000, C008S918000, C008S445000, C008S549000, C534S638000, C534S798000, C534S845000

Reexamination Certificate

active

06241789

ABSTRACT:

The present invention relates to a process for dyeing or printing fibre materials containing hydroxyl groups or containing nitrogen with reactive dyes, and to novel reactive dyes. The process on which the present invention is based is also suitable for dyeing or printing paper or films of plastic.
The practice of dyeing and printing with reactive dyes has recently led to increased demands on the quality of the dyeings and prints and on the profitability of the dyeing or printing process. Consequently, there continues to be a need for novel processes which have improved properties in respect of application and in respect of the dyeings or prints obtained.
Processes wherein the reactive dyes have an adequate substantivity and at the same time a good ease of wash off of the non-fixed portions are now required for dyeing and printing. The dyeings and prints furthermore should have a good dyeing yield, high degrees of fixing and good allround properties, such as wet fastness properties and, in particular, light fastness properties. When a combination of reactive dyes is used, the effect of so-called catalytic fading should therefore largely be avoided. By this effect, one of the reactive dyes in combination with other reactive dyes fades significantly more than is the case when it is used by itself, i.e. in an individual shade.
The process should furthermore be suitable for ink jet printing processes jet and ink jet processes).
Ink jet printing processes have already been used in the textile industry for some years. These processes enable the otherwise customary production of a printing screen to be omitted, so that considerable savings in cost and time can be achieved. In the production of pattern samples in particular, changed requirements can be reacted to within a significantly shorter time.
Appropriate ink jet printing processes should have, in particular, optimum use properties. In this connection there may be mentioned properties such as the viscosity, stability, surface tension and conductivity of the inks used. Increased demands are furthermore made on the quality of the resulting prints, for example in respect of colour strength, fibre-dye bond stability and in respect of the wet fastness properties and, in particular, the light fastness properties.
Furthermore, the reactive dyes to be used for the abovementioned processes should be easy to combine and should allow as far as possible all shades of the colour space to be established by combination.
These requirements are not met in all the properties by the known processes.
The present invention is therefore based on the object of discovering novel, improved processes for dyeing and printing fibre materials which have the qualities characterized above to a high degree.
It has been found that the object described is largely achieved by the process defined below.
The present invention relates to a process for dyeing or printing paper, films of plastic or fibre material containing hydroxyl groups or containing nitrogen with reactive dyes, which comprises using at least one reactive dye of the formula (1) from the following group a) and at least one reactive dye from the following groups b), c) and d):
a) green- or blue-dyeing reactive dyes of the formula (1)
 in which
NiPhC is the radical of a nickel phthalocyanine,
R
1
is hydrogen or substituted or unsubstituted C
1
-C
4
alkyl,
V
1
is hydrogen or substituted or unsubstituted C
1
-C
8
alkyl, phenyl or naphthyl and
x is 2 to 4 and y is 1 to 2,
the reactive dye of the formula (1) containing at least one fibre-reactive group;
b) blue-dyeing reactive dyes of the formula (2) or (3)
 in which
(R
2
)
0-3
is 0 to 3 C
1
-C
4
alkyl radicals which are identical or different from one another and
(R
3
)
0-3
is 0 to 3 substituents, which are identical or different from another, from the group consisting of C
1
-C
4
alkyl, C
1
-C
4
alkoxy, halogen, carboxyl and sulfo,
X
1
is chlorine or fluorine and
R4 is hydrogen or C
1
-C
4
alkyl which is unsubstituted or substituted by hydroxyl, sulfo or sulfato,
 in which
R
5
is hydrogen or C
1
-C
4
alkyl which is unsubstituted or substituted by hydroxyl, sulfo or sulfato,
X
2
is chlorine or fluorine,
Y
1
is hydrogen, C
1
-C
8
alkyl which is unsubstituted or substituted by hydroxyl, sulfo or sulfato and uninterrupted or interrupted by oxygen, or phenyl or naphthyl which are unsubstituted or substituted by C
1
-C
4
alkyl, C
1
-C
4
alkoxy, halogen, carboxyl or sulfo, and
the benzene nuclei I, II and III contain no further substituents or are further substituted by C
1
-C
4
alkyl, C
1
-C
4
alkoxy, halogen or carboxyl;
c) red-dyeing reactive dyes of the formula (4)
 in which
R
6
is hydrogen or C
1
-C
4
alkyl which is unsubstituted or substituted by hydroxyl, sulfo or sulfato,
R
7
and R
8
independently of one another are hydrogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, halogen, carboxyl or sulfo,
X
3
is chlorine or fluorine and
Y
2
is hydrogen, C
1
-C
8
alkyl which is unsubstituted or substituted by hydroxyl, sulfo, sulfato or a radical of the formnula —SO
2
—Z and is uninterrupted or interrupted by oxygen, or phenyl or naphthyl which are unsubstituted or substituted by C
1
-C
4
alkyl, C
1
-C
4
alkoxy, halogen, carboxyl, sulfo or a radical of the formula —SO,
2
—Z or —CO—NH—(CH
2
)
2-3
—SO
2
—Z, or the radical —N(R
6
)—Y
2
is morpholino, in which
Z is a radical of the formula —H═CH
2
or —CH
2
—CH
2
—U
1
and U
1
is a leaving group;
d) yellow- or orange-yeing reactive dyes of the formula (5)
 in which
R
9
is hydrogen or C
1
-C
4
alkyl which is unsubstituted or substituted by hydroxyl, sulfo or sulfato,
R
10
and R
11
independently of one another are hydrogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, halogen, carboxyl or sulfo,
X
4
is chlorine or fluorine and
Y
3
is hydrogen, C
1
-C
8
alkyl which is unsubstituted or substituted by hydroxyl, sulfo or sulfato and is uninterrupted or interrupted by oxygen, or phenyl or naphthyl which are unsubstituted or substituted by C
1
-C
4
alkyl, C
1
-C
4
alkoxy, halogen, carboxyl, sulfo or a halogenotriazinylamino radical which is unsubstituted or further substituted, or the radical —N(R
9
)—Y
3
is morpholino, and
K
1
is a radical of the formula
 in which
R
12
is hydroxyl or amino,
R
13
is methyl or carboxyl,
(R
14
)
0-3
is 0 to 3 identical or different substituents from the group consisting of C
1
-C
4
alky, C
1
-C
4
alkoxy, halogen, carboxyl and sulfo,
R
15
and R
17
are C
1
-C
4
alkyl and
R
16
is cyano, carbamoyl or sulfomethyl.
Sulfo groups present in the above reactive dyes can in general be present both as the free add (—SO
3
H) and in any salt form, for example as an alkali metal, alkaline earth metal or ammonium salt or as a salt of an organic amine, for example the sodium, potassium, lithium or ammonium salt, the salt of triethanolamine or the mixed salt of two or more different cations, for example as the Na/Li-, Na/NH
4
- or Na/Li/NH
4
mixed salt
C
1
-C
4
Alkyl R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
, R
8
, R
9
, R
10
, R
11
, R
14
, R
15
and R
17
and the other C
1
-C
4
alkyl radicals mentioned above as substituents are, for example, methyl, ethyl, propyl, isopropyl, butyl, secbutyl, tert-butyl or isobutyl, in particular methyl or ethyl. The methyl radicals are of particular importance here. Substituents of the alkyl radical R
1
are, for example, hydroxyl, sulfo or sulfato. The alkyl radicals R
4
, R
5
, R
6
and R
9
can be substituted as mentioned above. Preferably, the alkyl radicals mentioned are unsubstituted.
C
1
-C
4
Akoxy R
3
, R
7
, R
8
, R
10
, R
11
, and R
14
and the other C
1
-C
4
alkoxy radicals mentioned above as substituents are, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy or isobutoxy, in particular methoxy.
Halogen R
3
, R
7
, R
8
, R
10
, R
11
, and R
14
and the other halogen radicals mentioned above as substituents are, for example, fluorine or, in particular, chlorine.
The leaving group U
1
is, 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

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