Fiber-reactive dyes which contain a ureidoalkylene group

Details Fiber-reactive dyes which contain a ureidoalkylene group Fiber-reactive dyes which contain a ureidoalkylene group

1992-07-17

1994-01-11

Lee, Mark C.

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

Organic compounds

Azo

534617, 534622, 534629, 534632, 534638, 534642, 534643, 540132, 540133, 540134, 544 76, 552231, 8549, C09B 62503, C09B 43124, D06P 1384

Patent

active

052782921

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to the field of fiber-reactive dyes.
U.S. Pat. No. 3,419,542 and European Patent Application Publications Nos. 0 174 909 Al and 0 265 857 Al disclose dyes whose fiber-reactive group of the vinyl sulfone series is bonded to the dye chromophore via a phenylureido or alkylureido radical. However, these dyes appear to be in need of improvement, partly in respect of their degrees of fixation if deep shades are to be achieved by the exhaust method, partly in respect of their solubility if they are to be applied in the short-time pad-batch process.
The present invention, then, makes available dyes which possess fiber-reactive properties and thus are interesting for economical dyeing, of the formula (1) ##STR2## in which F is the radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, formazan, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye; ethyl, preferably hydrogen; or in particular methyl, alkoxy of 1 to 4 carbon atoms, such as ethoxy or in particular methoxy, or chlorine, but preferably hydrogen; substituent which is eliminable by alkali to form a vinyl group;
Preferably, F is the radical of a monoazo or disazo dye or the radical of a metal complex azo dye, such as an o,o'-1:1 copper complex azo dye, or of a triphendioxazine or of an anthraquinone or of a phthalocyanine dye, such as a copper phthalocyanine dye, or of a copper formazan dye.
The radical F may contain bonded to its basic skeleton the substituents customary in organic dyes, including fiber-reactive groups, for example those of the above-defined formula --SO.sub.2 --Y. Such substituents are for example: alkyl groups of 1 to 4 carbon atoms, such as methyl, ethyl, propyl, isopropyl or butyl, preferably ethyl and in particular methyl; alkoxy groups of 1 to 4 carbon atoms, such as methoxy, ethoxy, propoxy, isopropoxy and butoxy, preferably ethoxy and in particular methoxy; acylamino groups of 2 to 8 carbon atoms, such as acetylamino, propionylamino or benzoylamino; primary and mono- or disubstituted amino groups, for example by alkyl groups of 1 to 4 carbon atoms and/or phenyl groups, such as monoalkylamino and dialkylamino groups having 1 to 4 carbon atoms in the alkyl moiety, phenylamino or N-(C.sub.1 -C.sub.4 -alkyl)-N-phenylamino groups, wherein the alkyl moiety may be further substituted, for example by phenyl, sulfophenyl, hydroxyl, sulfato, sulfo and carboxyl, and the phenyl groups may be further substituted, for example by chlorine, sulfo, carboxyl, methyl and/or methoxy, e.g. 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 also phenylamino and sulfophenylamino groups; alkoxycarbonyl groups having one alkyl moiety of 1 to 4 carbon atoms, such as methoxycarbonyl and ethoxycarbonyl; alkylsulfonyl groups of 1 to 4 carbon atoms, such as methylsulfonyl and ethylsulfonyl groups; trifluoromethyl, nitro and cyano groups; halogen atoms, such as fluorine, chlorine or bromine; carbamoyl groups which may be monosubstituted or disubstituted by alkyl of 1 to 4 carbon atoms, which alkyl may in turn be substituted, for example by hydroxyl, sulfato, sulfo, carboxyl, phenyl and sulfophenyl, e.g. N-methylcarbamoyl and N-ethylcarbamoyl; sulfamoyl groups which may be monosubstituted or disubstituted by alkyl groups of 1 to 4 carbon atoms, and N-phenyl-N-alkylsulfamoyl groups having an alkyl group of 1 to 4 carbon atoms, wherein these alkyl groups may in turn be substituted by hydroxyl, sulfato, sulfo, carboxyl, phenyl and sulfophenyl, e.g. N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-butylsulfamoyl, N-(.beta.-hydroxyethyl)sulfamoyl and N,N-di(.beta.-hydroxyethyl)sulfamoyl; N-phenylsulfamoyl, ureido, hydroxyl, carboxyl, sulfomethyl and sulfo groups; .beta.-sulfatoethylsulfonyl, .beta.-thiosulfatoethylsulfonyl, .be

REFERENCES:
patent: 3419542 (1968-12-01), Meininger et al.
patent: 3647827 (1972-03-01), Sigiyama et al.
patent: 4818814 (1989-04-01), Schlafer
patent: 4841028 (1989-06-01), Aeschilmann et al.

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