Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Reexamination Certificate
2001-03-19
2003-02-11
Powers, Fiona T. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
C008S549000
Reexamination Certificate
active
06518409
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 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 fiber-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 allround 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,
A is C
2
-C
8
alkylene interrupted by oxygen,
X is halogen, and
Y is a fibre-reactive radical of formula (2)
—SO
2
—Z (2)
wherein
Z is vinyl or a radical —CH
2
—CH
2
—U and U is a group removable under alkaline conditions.
As C
1
-C
4
alkyl for R
1
and R
2
, each independently of the other, there come into consideration, for example, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl and isobutyl, preferably methyl or ethyl, and especially methyl. The alkyl radicals mentioned may be unsubstituted or substituted, for example, by hydroxy, sulfo, sulfato, cyano or by carboxyl.
As halogen for X there come into consideration, for example, fluorine, chlorine and bromine.
As a leaving group U 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, and more especially —Cl.
For A there comes into consideration, for example, a radical of formula —(CH
2
)
2
—O—(CH
2
)
2
—, —(CH
2
)
3
—O—(CH
2
)
2
— or —(CH
2
)
3
—O—(CH
2
)
3
—.
Preference is given to the reactive dyes according to the invention wherein R
1
and R
2
are each independently of the other hydrogen or C
1
-C
4
alkyl, especially hydrogen.
Preference is given to the reactive dyes according to the invention wherein X is fluorine or chlorine, especially chlorine.
A in the reactive dyes according to the invention is preferably a C
2
-C
6
alkylene radical, especially a C
2
-C
4
alkylene radical, interrupted by oxygen, e.g. —(CH
2
)
2
—O—(CH
2
)
2
—.
Preference is given to the reactive dyes according to the invention wherein the radical of formula —A—Y is a radical of formula (3)
—(CH
2
)
2-4
—O—(CH
2
)
2-4
—SO
2
—Z (3),
especially a radical of formula (3a)
—(CH
2
)
2
—O—(CH
2
)
2
—SO
2
—Z (3a),
wherein
Z is vinyl, &bgr;chloroethyl or &bgr;sulfatoethyl, especially vinyl or &bgr;chloroethyl.
The naphthalene coupling component on which the reactive dyes according to the invention are based corresponds, for example, to the formula
preferably formula (4.1) or (4.2), and especially formula (4.1), wherein the definitions and preferred meanings given above apply for R
1
.
Special preference is given to the reactive dye of formula (1a)
The present invention relates also to a process for the preparation of the reactive dyes according to the invention, which process comprises reacting a compound of formula (5)
and cyanuric halide and an amine of formula (6)
with one another in any desired order, wherein the definitions and preferred meanings given above apply for R
1
, R
2
, A and Y.
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 particular reaction components advantageously being determined by the prevailing 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 mixture obtained is then condensed with approximately 1 molar equivalent of an amine of formula (6).
The individual condensation reactions are carried out, for example, using 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 chloride.
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 and capable of conversion into a vinyl group, into its vinyl form by treatment with dilute sodium hydroxide solution, e.g. conversion of the &bgr;-sulfatoethylsulfonyl or &bgr;-chloroethylsulfonyl group into the vinylsulfonyl radical. Such reactions are known per se.
The compounds of formulae (5) and (6) are known or can be prepared analogously to known compounds.
The compounds of formula (1) according to the invention are suitable as dyes for dyeing and printing a wide variety of materials, such as hydroxyl-group-containing or nitrogen-containing fibre materials. Examples of nitrogen-containing fibre materials include silk, leather, wool, polyamide fibres and polyurethanes. The reactive dyes according to the invention are especially suitable for dyeing and printing all types of cellulosic fibre materials. Such cellulosic fibre materials are, for example, natural cellulose fibres, such as cotton, linen and hemp, and cellulose and regenerated cellulose, preferably cotton. The reactive dyes according to the invention are also suitable for dyeing or printing cellulosic blend fabrics, for example blends of cotton and polyamide fibres or especially cotton/polyester blends.
The reactive dyes according to the invention can be applied to the fibre material and fixed to the fibre in a number of ways, especially in the form of aqueous dye solutions or dye print pastes. They are suitable for the exhaust process and also for dyeing using the pad-dyeing process, according to which the goods are impregnated with aqueous, optionally salt-containing, dye solutions and the dyes are fixed, after treatment with an alkali or in the presence of an alkali, optionally under the action of heat or as a result of storage for several hours at room temperature. After fixing, the dyeings or prints are thoroughly rinsed with cold and hot water, optionally with addition of an agent that has a dispersing action and promotes diffusion of unfixed dye.
The reactive dyes according to the invention are distinguished by high reactivity, good fixing characteristics and very good build-up characteristics. They can therefore be used in the exhaust dyeing process at low dyeing temperatures and require only short steaming times in the pad-steam process. The degrees of fixing
Cortese Bruno
Deitz Heidi
Deitz Rolf
Tzikas Athanassios
Ciba Specialty Chemicals Corporation
Deitz Heidi
Mansfield Kevin T.
Powers Fiona T.
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