Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Patent
1992-01-10
1994-09-20
Ramsuer, Robert W.
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
534622, 534624, 534625, 534628, 534629, 534634, 534635, 534636, 534638, 534641, 534642, C09B 6208, D06P 138
Patent
active
053490576
DESCRIPTION:
BRIEF SUMMARY
The invention is in the technical field of fiber-reactive dyes.
Azo dyes containing a 2-chloro-4-cyanamido-s-triazin-6-ylamino radical are known from U.S. Pat. No. 3,758,470. However, these known dyes have certain shortcomings in practical application; thus, they are in particular not suitable for dyeing by the cold pad-batch method and the various exhaust methods at lower dyeing temperatures (40.degree. to 60.degree. C.).
Furthermore, dyes are known from European Patent Application Publication No. 0,040,806A, which have a fiber-reactive radical of the vinyl sulfone series at a separate point of the chromophore, and which have as a further fiber-reactive radical a fluoro-s-triazinylamino group, which contains as further substituents, inter alia, an optionally substituted amino group. In Table Example 23 a monoazo dye is named which is said to contain a 2-cyanamido-4-fluoro-s-triazin-6-ylamino group, whose synthesis is however difficult.
By means of the present invention, new water-soluble azo dyes have now been found which are improved in this respect and have the general formula (1) ##STR2## in this formula, the symbols have the following meanings: F is the radical of a monoazo, disazo or polyazo dye or of a heavy metal complex azo dye, such as a 1: copper complex, 1:2 chromium complex or 1:2 cobalt complex azo dye; which can be substituted by halogen, such as chlorine and bromine, hydroxyl, cyano, alkoxy of 1 to 4 carbon atoms, such as methoxy and ethoxy, alkoxycarbonyl of 2 to 5 carbon atoms, carboxyl, sulfamoyl, sulfo or sulfato, and is preferably methyl or ethyl and in particular hydrogen; phenylsulfonyl, preferably chlorine; .beta.-phosphatoethyl, .beta.-alkanoyloxyethyl of 2 to 5 carbon atoms in the alkanoyl radical, such as .beta.-acetyloxyethyl, .beta.-benzoyloxyethyl, .beta.-(sulfobenzoyloxy)ethyl, .beta.-(p-toluenesulfonyloxy)ethyl or .beta.-halogenoethyl, such as .beta.-bromoethyl or .beta.-chloroethyl, preferably vinyl and in particular .beta.-sulfatoethyl;
The groups --SO.sub.2 --Y can be bound to an aromatic carbon atom of F via an alkylene radical of 1 to 4 carbon atoms, such as a methylene group, or via an alkylamino group of 1 to 4 carbon atoms, such as a methylamino or ethylamino group.
F is preferably the radical of a monoazo or disazo dye or the radical of an o,o'-1:1 copper complex monoazo or disazo dye. The radical F can contain the substituents customary for organic dyes, including a fiber-reactive group of a type other than that shown in formula (1), bound to its basic structure. Examples of these substituents are: alkyl groups of 1 to 4 carbon atoms, such as methyl, ethyl, propyl, isopropyl or butyl, of these, preferably ethyl and in particular methyl; alkoxy groups of 1 to 4 carbon atoms, such as methoxy, ethoxy, propoxy, isopropoxy and butoxy, of these, preferably ethoxy and in particular methoxy; acylamino groups of 2 to 8 carbon atoms, such as acetylamino, propionylamino or benzoylamino groups; primary and monosubstituted or disubstituted amino groups, such as, for example, those substituted by alkyl groups of 1 to 4 carbon atoms and/or phenyl groups, such as monoalkylamino and dialkylamino groups of 1 to 4 carbon atoms in the alkyl radical, phenylamino or N-(C.sub.1 -C.sub.4 -alkyl)-N-phenylamino groups, in which the alkyl radicals can be further substituted, for example by phenyl, sulfophenyl, hydroxyl, sulfato, sulfo and carboxyl, and the phenyl groups can be further substituted, such as by chlorine, sulfo, carboxyl, methyl and/or methoxy, for example methylamino, ethylamino, propylamino, isopropylamino, butylamino, N,N-di(.beta.-hydroxyethyl)amino, N,N-di(.beta.-sulfatoethyl)amino, sulfobenzylamino, N,N-di(sulfobenzyl)amino and diethylamino groups and phenylamino and sulfophenylamino groups; alkoxycarbonyl groups having an alkyl radical of 1 to 4 carbon atoms, such as methoxycarbonyl and ethoxycarbonyl; alkylsulfonyl groups of 1 to 4 carbon atoms, such as methylsulfonyl and ethylsulfonyl; trifluoromethyl, nitro and cyano groups; halogen atoms, such as fluorine, chlorine an
REFERENCES:
patent: 3758470 (1973-09-01), Ackermann et al.
patent: 4649193 (1987-03-01), Meininger et al.
patent: 5200512 (1993-04-01), Reiner
Buch Holger M.
Springer Hartmut
Hoechst Aktiengesellschaft
Powers Fiona T.
Ramsuer Robert W.
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