Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Reexamination Certificate
2000-09-25
2001-10-23
Powers, Fiona T. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
C008S549000
Reexamination Certificate
active
06307034
ABSTRACT:
The present invention relates to novel olive-green reactive dyes containing a formazan dye radical and a monoazo dye radical, 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 is still a need for novel reactive dyes having improved properties, for example in respect of their application.
Dyeing nowadays requires reactive dyes that have sufficient substantivity and at the same 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 having the qualities characterised above to a high degree. The novel dyes should especially be distinguished by high fixing yields and high fibre-dye binding 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 fastness to light and to wetting.
It has been shown that the problem posed is largely solved by the novel olive-green reactive dyes defined below.
The present invention accordingly relates to reactive dyes of formula (1)
wherein
R
1
, R
2
, R
3
and R
4
are each independently of the others hydrogen or unsubstituted or substituted C
1
-C
4
alkyl,
X
1
and X
2
are halogen,
B is a C
2
-C
12
alkylene radical which may be interrupted by 1, 2 or 3 —O— members and is unsubstituted or substituted by hydroxy,
A is a formazan radical of formula (2) or (3)
D is a radical of formula (4) or (5)
wherein
m is the number 1 or 2,
n is the number 1, 2 or 3, and
(R
5
)
0-2
denotes from 0 to 2 identical or different substituents from the group C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
2
-C
4
alkanoylamino and halogen.
The radicals R
1
, R
2
, R
3
and R
4
in the reactive dye of formula (1) as alkyl radicals are straight-chain or branched. The alkyl radicals may be further substituted, for example by hydroxy, sulfo, sulfato, cyano or by carboxy. The following radicals may be mentioned by way of example: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and tert-butyl, and also the corresponding hydroxy-, sulfo-, sulfato-, cyano- or carboxy-substituted radicals. Preferred as substituents are hydroxy, sulfo and sulfato, especially hydroxy and sulfato, and preferably hydroxy.
R
1
and R
4
are preferably hydrogen or C
1
-C
4
alkyl, especially hydrogen.
R
2
and R
3
are preferably each independently of the other hydrogen or unsubstituted or hydroxy-, sulfo-, sulfato-, cyano- or carboxy-substituted C
1
-C
4
alkyl. According to an embodiment of interest, one of the radicals R
2
and R
3
is hydroxy-, sulfo-, sulfato-, cyano- or carboxy-substituted C
1
-C
4
alkyl, and the other of the radicals R
2
and R
3
is hydrogen or C
1
-C
4
alkyl, especially hydrogen.
R
2
and R
3
are especially preferably each independently of the other hydrogen or C
1
-C
4
alkyl, especially hydrogen.
As C
1
-C
4
alkyl for R
5
, each independently of any other, there come into consideration, for example, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl or isobutyl, preferably methyl or ethyl and especially methyl.
As C
1
-C
4
alkoxy for R
5
, each independently of any other, there come into consideration, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy or isobutoxy, preferably methoxy or ethoxy and especially methoxy.
As C
2
-C
4
alkanoylamino for R
5
, each independently of any other, there come into consideration, for example, acetylamino or propionylamino and especially acetylamino.
As halogen for R
5
, each independently of any other, there come into consideration, for example, fluorine, chlorine or bromine, preferably chlorine or bromine and especially chlorine.
R
5
is preferably hydrogen or a substituent from the group C
1
-C
4
alkyl, C
1
-C
4
alkoxy and halogen.
X
1
and X
2
are preferably each independently of the other chlorine or fluorine, especially fluorine.
B is preferably a C
2
-C
6
alkylene radical which may be interrupted by 1 or 2 —O— members and is unsubstituted or substituted by hydroxy.
Of particular interest as bridge members B are C
2
-C
6
alkylene radicals, especially those of formula —CH
2
—CH(R
6
)— or —(R
6
)CH—CH
2
—, wherein R
6
is C
1
-C
4
alkyl, especially methyl, and very especially 1,2-propylene.
A suitable formazan radical A of formula (2) is, for example, a radical of formula
A suitable formazan radical A of formula (3) is, for example, a radical of formula
Preference is given to the reactive dyes according to the invention wherein the formazan radical A corresponds to a radical of formula (3.1).
In the reactive dyes according to the invention, D as a radical of formula (4) is, for example, a radical of formula
preferably of formula (4.1), (4.3), (4.6), (4.10), (4.11) or (4.12).
In the dye mixtures according to the invention, D as a radical of formula (5) is, for example, a radical of formula
especially of formula (5.11).
Preference is given to the reactive dyes according to the invention wherein D is a radical of formula (5a)
wherein
n is the number 2 or 3.
In a preferred embodiment of the reactive dyes of formula (1) according to the invention
R
1
, R
2
, R
3
and R
4
are hydrogen,
X
1
and X
2
are chlorine or fluorine,
B is a radical of formula —CH
2
—CH(R
6
)— or —(R
6
)CH—CH
2
—, wherein R
6
is C
1
-C
4
alkyl, especially methyl,
A is a radical of formula (3.1),
D is a radical of formula (5a), wherein n is the number 2 or 3.
In an especially preferred embodiment the reactive dyes of formula (1) according to the invention correspond to a dye of formula (1.1)
The present invention relates also to a process for the preparation of reactive dyes of formula (1), which process comprises condensing a compound of formula (6a)
with a compound of formula (7a)
or condensing a compound of formula (6b)
with a compound of formula (7b)
wherein Hal is halogen, and the definitions and preferred meanings given above for A, B, X
1
, X
2
, R
1
, R
2
, R
3
and R
4
apply.
Compounds of formulae (7a) and (7b) can be obtained, for example, by condensing compounds of formula (8a) or (8b)
with cyanuric chloride or cyanuric fluoride. Compounds of formulae (6a) and (6b) can be obtained by condensing a compound of formula (7b) or (7a) with a diamine of formula R
2
—HN—B—NH—R
3
, an excess of the diamine optionally being used.
The compounds of formulae (8a) and (8b) are known or can be obtained analogously to known compounds.
The individual condensation reactions can be carried out according to processes known per se, for example according to the processes described in GB-A-2 085 908. The condensation reactions are generally carried out in an aqueous solution, at a temperature of, for example, from 0 to 50° and a pH value of, for example, from 4 to 9.
The reactive dyes of formula (1) according to the invention that contain a sulfo or sulfato group are either in the form of the free acid thereof or preferably in the form of the salt thereof. Suitable salts are, for example, alkali metal, alkaline earth metal or ammonium salts or salts of an organic amine. There may be mentioned by way of example sodium, lithium, potassium or ammonium salts or the salt of mono-, di- or tri-ethanolamine.
The reactive dyes according to the invention are suitable for dyeing and printing a wide variety of materials, such as hydroxy-group-containing or nitrogen-containing fibre materials. There may be mentioned by way of example silk, leather, wool, polyamide fibres and polyurethanes, and especially all types of cellulosic fibre materials. Such cellulosic fibre materials are, for example, natural cellulose fibres, such as cotton, linen and hemp,
Ciba Specialty Chemicals Corporation
Mansfield Kevin T.
Powers Fiona T.
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