Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Reexamination Certificate
2001-11-13
2003-01-07
Powers, Fiona T. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
C534S598000, C008S549000
Reexamination Certificate
active
06504016
ABSTRACT:
The present invention relates to novel reactive dyes, to processes for the preparation thereof and to the use thereof in dyeing or printing textile fibre materials.
The practice of dyeing using reactive dyes has recently led to higher demands being made in terms 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 bond 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 all-round fastness properties, for example light-fastness and wet-fastness properties.
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
R
1
and R
2
are each independently of the other hydrogen or unsubstituted or substituted C
1
-C
4
alkyl,
R
3
and R
4
are each independently of the other hydrogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, halogen, carboxy or sulfo,
R
5
and R
6
are each independently of the other hydrogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, halogen, nitro, C
2
-C
4
alkanoylamino, benzoylamino, ureido, carboxy or sulfo,
D is a radical of formula
wherein
(R
7
)
0-2
denotes from 0 to 2 identical or different substituents selected from the group halogen, C
2
-C
4
alkanoylamino, C
1
-C
4
alkyl and C
1
-C
4
alkoxy,
X is halogen,
A—Y is a radical of formula
wherein
Y
1
is &agr;,&bgr;-dibromopropionylamino or &agr;-bromoacryloylamino and
Z
1
and Z
2
are each independently of the other vinyl, &bgr;-chloroethyl or &bgr;-sulfatoethyl,
m is the number 1, 2 or 3, and
n is the number 1 or 2, with the proviso that
D is a radical of formula (3) when A—Y is a radical of formula (4b).
As C
1
-C
4
alkyl for R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
, each independently of the others, there come into consideration, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl and isobutyl, preferably methyl or ethyl, and especially methyl. The alkyl radicals R
1
and R
2
mentioned may be unsubstituted or substituted, for example, by hydroxy, sulfo, sulfato, cyano or by carboxyl. Preference is given to the corresponding unsubstituted alkyl radicals.
As C
1
-C
4
alkoxy for R
3
, R
4
, R
5
, R
6
and R
7
, each independently of the others, there come into consideration, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy and isobutoxy, preferably methoxy or ethoxy, and especially methoxy.
As halogen for R
3
, R
4
, R
5
, R
6
and R
7
, each independently of the others, there come into consideration, for example, fluorine, chlorine and bromine, preferably chlorine or bromine, and especially chlorine.
As C
2
-C
4
alkanoylamino for R
5
, R
6
and R
7
, each independently of the others, there come into consideration, for example, acetylamino and propionylamino, especially acetylamino.
As a radical of formula (2), D in the reactive dyes of formula (1) according to the invention is, for example, a radical of formula
preferably of formula (2.14), (2.15) or (2.16), and especially of formula (2.14).
As a radical of formula (3), D in the reactive dyes of formula (1) according to the invention is, for example, a radical of formula
preferably of formula (3.11) or (3.12), and especially of formula (3.12).
For X there come into consideration, for example, fluorine, chlorine and bromine. R
1
and R
2
are preferably, each independently of the other, hydrogen or C
1
-C
4
alkyl, especially hydrogen or methyl, and more especially hydrogen.
R
3
and R
4
are preferably, each independently of the other, hydrogen, C
1
-C
4
alkyl, C
1
-C
4
-alkoxy or sulfo, especially hydrogen, C
1
-C
4
alkyl or C
1
-C
4
alkoxy, and more especially hydrogen.
R
5
and R
6
are preferably, each independently of the other, hydrogen, C
1
-C
4
alkyl, C
1
-C
4
-alkoxy, C
2
-C
4
alkanoylamino, benzoylamino, ureido or sulfo, especially hydrogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, ureido, C
2
-C
4
alkanoylamino, and more especially hydrogen.
R
7
in radical D of formula (3) preferably denotes from 0 to 2 identical or different substituents selected from the group C
1
-C
4
alkyl and C
1
-C
4
alkoxy and is especially hydrogen.
X is preferably fluorine or chlorine, especially fluorine.
m in radical D of formula (2) is preferably the number 2 or 3 and especially the number 3.
n in radical D of formula (3) is preferably the number 2.
Preference is given to the reactive dyes according to the invention wherein
m is the number 2 or 3,
n is the number 2, and
R
7
is hydrogen.
Z
1
and Z
2
are preferably, each independently of the other, vinyl or &bgr;-chloroethyl. In the radicals of formula (4b), the fibre-reactive group —CO—NH—(CH
2
)
2
—SO
2
—Z
2
is preferably in the 3-position. Preferably, the radical of formula (4b) does not contain a sulfo group on the benzene ring.
In an especially preferred embodiment of the reactive dyes of formula (1) according to the invention, the radical of formula —A—Y is a radical of formula (4a) or (4b), especially of formula (4a).
In a preferred embodiment of the present invention, the reactive dye of formula (1) is a reactive dye of formula
especially of formula (1a).
The present invention relates also to a process for the preparation of the reactive dyes according to the invention, wherein a compound of formula
cyanuric halide and an amine of formula
are reacted with one another in any order, the definitions and preferred meanings given above applying for R
1
, R
2
, R
3
, R
4
, R
5
, R6, A—Y and D.
Because the process steps mentioned above may be carried out in different orders as well as, where appropriate, simultaneously, different process variants are possible. The reaction is generally carried out stepwise, the order of the simple reactions between the individual reaction components advantageously being determined by the particular conditions. For example, approximately 1 molar equivalent of an amine of formula (6) is reacted with approximately 1 molar equivalent of cyanuric halide and the product obtained is then condensed with approximately 1 molar equivalent of a compound of formula (5). In another process variant, for example, approximately 1 molar equivalent of a compound of formula (5) is reacted with approximately 1 molar equivalent of cyanuric halide and the condensation product obtained is then condensed with approximately 1 molar equivalent of an amine of formula (6). Instead of the dye of formula (5), it is also possible to use its precursor and to complete its preparation in the course of the subsequent process by diazotisation followed by a coupling reaction.
The individual condensation reactions are carded out, for example, according to methods known per se, generally in aqueous solution, at a temperature of, for example, from 0 to 50° C., especially from 0 to 10° C., and at a pH of, for example, from 3 to 10, especially from 3 to 7.
As cyanuric halide there are suitable, for example, cyanuric chloride and cyanuric fluoride, especially cyanuric fluoride.
The end product may optionally be subjected to a further transformation reaction. Such a transformation reaction is, for example, conversion of a reactive group, present in Y, that is to say in Z
1
, Z
2
or Y
1
, and capable of conversion into a vinyl group, into its vinyl form by treatment wit
Cortese Bruno
Tzikas Athanassios
Ciba Specialty Chemicals Corporation
Mansfield Kevin T.
Powers Fiona T.
LandOfFree
Reactive dyes, processes for the preparation thereof and the... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Reactive dyes, processes for the preparation thereof and the..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Reactive dyes, processes for the preparation thereof and the... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3049416