Reactive dyes, a process for their preparation and their use

Details Reactive dyes, a process for their preparation and their use Reactive dyes, a process for their preparation and their use

2002-03-29

2003-04-22

Powers, Fiona T. (Department: 1626)

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

Organic compounds

Azo

C008S549000

Reexamination Certificate

active

06552175

ABSTRACT:

The present invention relates to novel reactive dyes, to a process 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 on the quality of the dyeings and the profitability of the dyeing process. As a result, there continues to be 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 colour 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 having the qualities characterised above to a high degree. The novel dyes should especially be distinguished by high fixing yields and high fibre-dye bond stabilities. The dyes should also yield dyeings having good allround properties, for example fastness to light and to wetting.
It has been found that the problem posed is largely solved by the novel dyes defined herein-below, especially when the dyes are used for dyeing synthetic polyamide fibre materials.
The present invention therefore relates to reactive dyes of formula
wherein
R
1
is halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
2
-C
4
alkanoylamino, &agr;,&bgr;-dihalopropionylamino or &agr;-haloacryloylamino,
X is halogen,
n is the number 0, 1 or 2, and
V is a radical of formula
wherein
(R
2
)
l
denotes l identical or different substituents selected from the group halogen, hydroxy, nitro, sulfo, C
1
-C
4
alkyl and C
1
-C
4
alkoxy,
Y is &agr;,&bgr;-dihalopropionylamino, &agr;-haloacryloylamino or a radical —CONH—(CH
2
)
2-3
—SO
2
—Z and
Z is vinyl or a radical —CH
2
CH
2
—U and U is a group removable under alkaline conditions,
m is the number 0 or 1, and
l is the number 0, 1, 2 or 3, with the proviso that
R
1
is not &agr;,&bgr;-dihalopropionylamino or &agr;-haloacryloylamino when V is a radical of formula (2) wherein Y is &agr;,&bgr;-dihalopropionylamino or &agr;-haloacryloylamino.
The dyes of formula (1) according to the invention are fibre-reactive. Fibre-reactive compounds are to be understood as being those which are capable of reacting with the hydroxyl groups of cellulose, with the amino, carboxy, hydroxy or thiol groups in wool and silk or with the amino groups and, possibly, with the carboxy groups of synthetic polyamides, to form covalent chemical bonds.
The sulfo groups present in the dyes of formula (1) are each either in the form of their free acid or preferably in the form of a salt thereof. Salts that come into consideration include, for example, the alkali metal, alkaline earth metal or ammonium salts, salts of an organic amine or mixtures thereof. Examples that may be mentioned are sodium, lithium, potassium and ammonium salts, the salt of mono-, di- or tri-ethanolamine or Na/Li or Na/Li/NH
4
mixed salts.
As C
1
-C
4
alkyl there come into consideration for R
1
and R
2
independently of one another e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl and isobutyl, preferably methyl or ethyl, especially methyl.
As C
1
-C
4
alkoxy there come into consideration for R
1
and R
2
independently of one another e.g. methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy and isobutoxy, preferably methoxy or ethoxy, especially methoxy.
As halogen there come into consideration for R
1
and R
2
independently of one another e.g. fluorine, chlorine and bromine, preferably chlorine or bromine, especially chlorine.
As C
2
-C
4
alkanoylamino there come into consideration for R. e.g. acetylamino and propionylamino, especially acetylamino.
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, more especially —Cl.
Examples of suitable radicals Z are accordingly vinyl, &bgr;-bromo- or &bgr;-chloro-ethyl, &bgr;-acetoxy-ethyl, &bgr;-benzoyloxyethyl, &bgr;-phosphatoethyl, &bgr;-sulfatoethyl and &bgr;-thiosulfatoethyl. Z is preferably vinyl, &bgr;-chloroethyl or &bgr;-sulfatoethyl, especially vinyl or &bgr;-chloroethyl.
The sulfo group on the naphthalene ring of the dye of formula (1) is either in the 3-position or the 4-position, preferably in the 3-position.
X is e.g. fluorine, chlorine or bromine, preferably fluorine or chlorine, especially chlorine.
In the reactive dyes of formula (1) according to the invention, R
1
is preferably &agr;,&bgr;-dihalo-propionylamino or &agr;-haloacryloylamino when V is a radical of formula (3).
n is preferably the number 0 or 1, especially the number 1.
m is preferably the number 0.
The radical of formula (2) in the dye of formula (1) is especially a radical of formula
The radical of formula (3) in the dye of formula (1) is preferably a radical of formula
especially of formula (3a).
(R
2
)
l
preferably denotes l identical or different substituents selected from the group halogen, hydroxy, nitro and sulfo.
l is preferably the number 0, 1 or 2, especially the number 0.
Y as &agr;,&bgr;-dihalopropionylamino or &agr;-haloacryloylamino is preferably &agr;,&bgr;-dibromopropionylamino, &agr;,&bgr;-dichloropropionylamino, &agr;-bromoacryloylamino or &agr;-chloroacryloylamino, especially &agr;,&bgr;-dibromopropionylamino or &agr;-bromoacryloylamino.
Y as a radical of formula —CONH—(CH
2
)
2-3
—SO
2
—Z is preferably a radical of formula —CONH—(CH
2
)
2
—SO
2
—Z, wherein Z has the definitions and preferred meanings given above, and especially a radical of formula —CONH—(CH
2
)
2
—SO
2
—(CH
2
)
2
—Cl or of formula —CONH—(CH
2
)
2
—SO
2
—CH═CH
2
.
Y is especially &agr;,&bgr;-dibromopropionylamino, &agr;,&bgr;-dichloropropionylamino, &agr;-bromoacryloylamino or &agr;-chloroacryloylamino, more especially &agr;,&bgr;-dibromopropionylamino or &agr;-bromoacryloylamino.
R
1
as &agr;,&bgr;-dihalopropionylamino or &agr;-haloacryloylamino is preferably &agr;,&bgr;-dibromopropionylamino, &agr;, &bgr;-dichloropropionylamino, &agr;-bromoacryloylamino or &agr;-chloroacryloylamino, especially &agr;,&bgr;-dibromopropionylamino or &agr;-bromoacryloylamino.
R
1
is preferably methyl, ethyl, methoxy, ethoxy, &agr;,&bgr;-dibromopropionylamino or &agr;-bromoacryloylamino.
R
1
is especially methoxy, ethoxy, &agr;,&bgr;-dibromopropionylamino or &agr;-bromoacryloylamino.
Preference is given to the reactive dyes of formula
especially the reactive dye of formula (1a) wherein the sulfo group is bonded in the 3-position of the naphthalene ring.
Preference is also given to the reactive dyes of formula
especially the reactive dye of formula (1b) wherein the sulfo group is bonded in the 3-position of the naphthalene ring.
The present invention relates also to a process for the preparation of reactive dyes of formula (1) which comprises reacting a compound of formula
and an amine of formula
H
2
N—V  (5)
with a cyanuric halide in any desired order, R
1
, V and n having the definitions and preferred meanings given above.
Since the individual process steps can be carried out in different orders, including, if desired, simultaneously, various process variants are possible. The reaction is usually carried out stepwise, the order in which the single reactions between the individual reaction components is carried out advantageously being governed by the particular conditions. For example, about one molar equivalent of an amine of formula (5) is reacted with about one molar equivalent of a cyanuric halide and the resulting product is then condensed with about one molar equivalent of a compound of formula (4). In another process variant, for

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