Water-soluble phenyl- or naphthyl-azo-carboxypyrazolone compound

Details Water-soluble phenyl- or naphthyl-azo-carboxypyrazolone compound Water-soluble phenyl- or naphthyl-azo-carboxypyrazolone compound

1985-04-15

1990-03-06

Angel, Floyd D.

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

Organic compounds

Azo

534617, 534642, 534598, C09B 6204, C09B 6244, C09B 62443, D06P 138

Patent

active

049067389

ABSTRACT:
Water-soluble monoazo compounds of the general formula (1) ##STR1## in which D is a phenyl radical or naphthyl radical, either of which is substituted and mandatorily contains at least one group which imparts solubility in water and D is substituted, for example by 1, 2 or 3 substituents which can be selected from the set consisting of 1 sulfamoyl, 1 carbamoyl, 1 trifluoromethyl, 1 benzothiazol-2-yl, 1 sulfobenzothiazol-2-yl, 1 methylbenzothiazol-2-yl, 1 methylsulfobenzothiazol-2-yl, 1 styryl, 1 nitrostyryl, 1 sulfostyryl and 1 nitrosulfostyryl group and, preferably, three sulfo groups, two carboxy groups, two alkyl groups of 1-4 C atoms, two alkoxy groups of 1-4 C atoms, 1 bromine atom and two chlorine atoms and one or two groups of the formula --SO.sub.2 --Z with Z of the meaning below, and the group --SO.sub.2 --Z can also be bonded to one of the substituents and Z represents the .beta.-hydroxyethyl group or, preferably a group Y of the meaning indicated below, M is a hydrogen atom or an equivalent of a monovalent, divalent or trivalent metal of the main groups of the periodic system, R is the methyl group, a carboxy group or a carboalkoxy group of 2 to 5 C atoms, R.sup.1 is a hydrogen atom or an alkyl group of 1 to 4 C atoms, R.sup.2 is a hydrogen atom, an alkyl group of 1-4 C atoms, an alkoxy group of 1-4 C atoms or a chlorine atom, R.sup.3 is a hydrogen atom, and alkyl group of 1-4 C atoms or an alkoxy group of 1-4 C atoms, Y is the vinyl group or an ethyl group which contains a radical in .beta.-position which can be eliminated as an anion under alkaline conditions, such as, for example, a .beta.-sulfatoethyl group, and Hal is a chlorine or fluorine atom.
The new monoazo compounds are prepared analogously to known procedures from the components (the diazo component D-NH.sub.2, the pyrazolone coupling component with an aminosulfophenyl radical in the 1-position, cyanuric chloride or cyanuric fluoride, and an aniline compound containing the group --SO.sub.2 --Y) evident from the formula (1). They have very good fiber-reactive dyestuff properties and produce, for example, on cellulose fiber materials deep and fast dyeings and prints.

REFERENCES:
patent: 3223470 (1965-12-01), Boedeker et al.
patent: 3455897 (1969-07-01), Barben

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