Bleaching and dyeing; fluid treatment and chemical modification – Reactive dye composition – process – or product – Alkylene sulfato – halotriazine – halodiazine,...
Reexamination Certificate
2001-07-05
2003-09-23
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Reactive dye composition, process, or product
Alkylene sulfato, halotriazine, halodiazine,...
C008S918000
Reexamination Certificate
active
06623533
ABSTRACT:
The present invention relates to a simplified method of printing cellulosic fibre materials in which a separate fixing process, such as the steaming of the printed fibre material, is superfluous. The method is simplified by the use of certain reactive dyes which are distinguished by at least three fibre-reactive groups, at least two of the said fibre-reactive groups being halotriazinyl radicals and at least one being especially of the vinylsulfonyl type. The present invention relates also to the novel reactive dyes.
Methods of printing cellulosic fibre materials have been known for a long time. The class of the reactive dyes has been successful in the face of the ever increasing demands in terms of colour fastness. In printing procedures on cellulose fibres that employ reactive dyes, use is made of the particularly stable covalent binding of the dyes to the hydroxy groups of the fibres. The binding of the reactive dyes to the fibres (fixing) is carried out in alkaline medium and requires treatment of the printed fibre material in a separate fixing process, which is usually carried out with saturated steam at relatively high temperatures (steaming), in order to achieve uniform and optimum fixing of the dye. In the hitherto known methods, such a treatment requires an additional device in which the necessary fixing heat and the steam are generated. There is accordingly a need for a simplified printing method that can be used on an industrial scale in which the additional process step of fixing the dye does not need to be carried out and in which uniform and optimum fixing is, for example, achieved directly on drying the printed fibre material. The advantage of such a simplified method is especially that expenditure in terms of time and cost is distinctly lower than in the case of the hitherto customary printing methods, since it is possible to omit the additional process step of fixing the dye and thus dispense with the additional fixing device.
The present invention accordingly relates to a method of printing cellulosic fibre materials in which the fibre material is brought into contact with reactive dyes of formula:
wherein
A is the radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan or dioxazine chromophore,
R
1
, R
2
and R
3
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 an organic bridging member,
T is a reactive radical of formula:
R
4
is hydrogen, C
1
-C
4
alkyl unsubstituted or substituted by hydroxy, sulfo, sulfato, carboxy or by cyano, or a radical
wherein R
5
is as defined hereinbelow,
R
5
is hydrogen, hydroxy, sulfo, sulfato, carboxy, cyano, halogen, C
1
-C
4
alkoxycarbonyl,
C
1
-C
4
alkanoyloxy, carbamoyl or a group —SO
2
—Y,
R
6
is hydrogen or C
1
-C
4
alkyl,
alk and alk
1
are each independently of the other linear or branched C
1
-C
6
alkylene,
arylene is an unsubstituted or sulfo-, carboxy-, hydroxy-, C
1
-C
4
alkyl-, C
1
-C
4
alkoxy- or halo-substituted phenylene or naphthylene radical,
Y is vinyl or a radical —CH
2
—CH
2
—U and U is a leaving group,
Y
1
is a group —CH(Hal)-CH
2
(Hal) or —C(Hal)═CH
2
, wherein Hal is chlorine or bromine,
W is a group —SO
2
—NR
6
—, —CONR
6
— or —NR
6
CO—, wherein R
6
is as defined hereinabove,
Q is a radical —O— or —NR
6
—, wherein R
6
is as defined hereinabove,
n is the number 0 or 1, and
V
1
and V
2
are each independently of the other N, C—H, C—Cl or C—F,
and the fixing of the printed fibre material is carried out without an additional fixing process step.
Within the context of the present invention, “an additional fixing process step” denotes the treatment of the fibre material, after the printing and after the drying immediately subsequent thereto, in a separate fixing device at relatively high temperatures, which step is usually carried out in the presence of saturated steam (steaming).
According to the invention, the fixing of the dye on the fibre material has already been achieved immediately after the printing and also the drying of the fibre material, which is to be carried out anyway.
Preferably, the method according to the invention is carried out industrially on a large scale.
As alkyl radicals in the reactive dye of formula (1), the radicals R
1
, R
2
and R
3
are straight-chain or branched. The alkyl radicals may be further substituted, for example by hydroxy, sulfo, sulfato, cyano or carboxy. The following radicals may be mentioned as examples: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and tert-butyl, and the corresponding radicals substituted by hydroxy, sulfo, sulfato, cyano or carboxy. Preferred substituents are hydroxy, sulfo or sulfato, especially hydroxy or sulfato and preferably hydroxy.
Preferably, R
1
is hydrogen or C
1
-C
4
alkyl, especially hydrogen.
R
2
and R
3
are preferably each independently of the other hydrogen, or C
1
-C
4
alkyl unsubstituted or substituted by hydroxy, sulfo, sulfato, cyano or by carboxy. According to one embodiment of interest, one of the radicals R
2
and R
3
is C
1
-C
4
alkyl substituted by hydroxy, sulfo, sulfato, cyano or by carboxy, especially by hydroxy, and the other of the radicals R
2
and R
3
is hydrogen or C
1
-C
4
alkyl, especially hydrogen.
Especially preferably, R
2
and R
3
are each independently of the other hydrogen or C
1
-C
4
alkyl, especially hydrogen.
X
1
and X
2
are, for example, chlorine, fluorine or bromine.
X
1
and X
2
are preferably each independently of the other chlorine or fluorine. Especially preferably, one of the radicals X
1
and X
2
is fluorine and the other is chlorine, or X
1
and X
2
are both fluorine. More especially, one of the radicals X
1
and X
2
is fluorine and the other is chlorine.
V
1
and V
2
are preferably N.
The organic bridging member B may be, for example, an aliphatic, cycloaliphatic, aromatic or araliphatic bridging member.
As an aliphatic bridging member, B is, for example, a straight-chain or branched C
2
-C
12
-alkylene radical, especially a C
2
-C
6
alkylene radical, that may be interrupted by 1, 2 or 3 members from the group —NH—, —N(CH
3
)— and especially —O— and that is unsubstituted or substituted by hydroxy, sulfo, sulfato, cyano or by carboxy. Hydroxy, sulfo or sulfato, especially hydroxy or sulfato, are preferred as substituents of the alkylene radicals mentioned for B.
As aliphatic bridging members for B there come into consideration also, for example, C
5
-C
9
-cycloalkylene radicals, especially cyclohexylene radicals. The said cycloalkylene radicals may be unsubstituted or substituted by C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
2
-C
4
alkanoylamino, sulfo, halogen or carboxy, especially by C
1
-C
4
alkyl. As aliphatic bridging members for B there may also be mentioned methylenecyclohexylene, ethylenecyclohexylene and methylenecyclohexylenemethylene radicals unsubstituted or substituted in the cyclohexylene ring by C
1
-C
4
alkyl, especially methyl.
For the radical of formula
there comes into consideration, for example, also a radical of formula
wherein alk is C
1
-C
4
alkylene, for example ethylene.
As an aromatic bridging member, B is, for example, unsubstituted or C
1
-C
4
alkyl-, C
1
-C
4
alkoxy-, C
2
-C
4
alkanoylamino-, sulfo-, halo- or carboxy-substituted C
1
-C
6
alkylenephenylene, for example methylenephenylene, C
1
-C
4
alkylenephenylene-C
1
-C
4
alkylene, for example methylenephenylenemethylene, or phenylene, or a radical of formula:
wherein the benzene rings I and II are unsubstituted or substituted by C
1
-C
4
alkyl, C
1
-C
4
-alkoxy, C
2
-C
4
alkanoylamino, sulfo, halogen or by carboxy and L is a direct bond or a C
2
-C
10
-alkylene radical that may be interrupted by 1, 2 or 3 oxygen atoms, or L is a bridging member of formula —CH═CH—, —N═N—, —NH—, —CO—, —NH—CO—, —NH—SO
2
—, —NH—CO—NH—, —O—, —S— or —SO
2
—. As an aromatic bridging member, B is preferably phenylene that may be substituted as indicated above. Preferably, the aromatic bridging members mentioned for B are unsubstituted or sulfo-substituted.
Examples of arom
Klier Herbert
Reichert Hans
Tzikas Athanassios
Ciba Specialty Chemicals Corporation
Einsmann Margaret
Mansfield Kevin T.
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