Hoechst Aktiengesellschaft

Folker Kohlhaas

Theodor Papenfuhs

Fritz Meininger

Hermann Fuchs

Ernst Hoyer

Hans H Steuernagel

Werner Brodt

Peter Hess

Compounds of the formula (1) ##STR1## in which X denotes a sulfur atom or the group ##STR2## in which R denotes a hydrogen atom, an alkylene-C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.6 - or alkyl-C.sub.1 -C.sub.6 - group, each of which can be substituted by hydroxyl, sulfo, carboxyl or cyano groups, R.sub.1 denotes a hydrogen atom or an alkyl-C.sub.1 -C.sub.6 -group which can be substituted by --SO.sub.3 M or COOM groups (where M denotes an H, Li, Na, K or Ca atom), hydroxyl, amino, methylamino, acetylamino, alkyl-C.sub.1 -C.sub.4 -sulfonylamino, methoxy, ethoxy, .beta.-hydroxyethylsulfonyl, phenyl, monosulfophenyl, disulfophenyl, or 4-[.beta.-hydroxyethylsulfonyl]-2-sulfophenyl groups, or represents a phenyl or naphthyl group, each of which can be substituted by --SO.sub.3 M or COOM groups (where M denotes an H, Li, Na, K or Ca atom), alkyl-C.sub.1 -C.sub.4 -, alkoxy-C.sub.1 -C.sub.4 -, amino, methylamino, alkyl-C.sub.1 -C.sub.4 -sulfonylamino or acetylamino groups, and R.sub.2 is hydrogen or oxygen, and process for their preparation by reacting compounds of the formula (2) ##STR3## in which Y denotes a chlorine or bromine atom, with a compound of the formula (3)

Substituted phenyl hydroxyethyl sulfones, and process for their

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.

Water-soluble phenyl- or naphthyl-azo-carboxypyrazolone compounds,

A process for the preparation of 3-(acyl)amino-4-alkoxy-phenyl-.beta.-hydroxyethyl-sulfone (sulfates) of the formula (1) ##STR1## in which R.sub.1 is alkyl having 1-4 carbon atoms and R.sub.2 is hydrogen or one of the groupings ##STR2## with the proviso that n=1 if R.sub.2 =H and n=0 if R.sub.2 =acyl, by converting 2-alkoxyacylanilines of the formula (2) ##STR3## in which R.sub.1 and R.sub.2 have the meanings given, in a known manner to the corresponding sulfochlorides substituted in the p-position relative to the alkoxy group, reducing the sulfochlorides with an alkali metal sulfite or ammonium sulfite in an aqueous medium at pH 7.0-8.5 and at -5 to +40.degree. C. to give the corresponding sulfinates, alkoxylating the latter with ethylene oxide in an aqueous medium at pH 6.0-8.5 and 40.degree.-80.degree. C. to give the 3-acylamino-4-alkoxyphenyl-.beta.-hydroxyethyl-sulfones of the formula (1) (with R.sub.2 =acyl and n=0) and, if appropriate, esterifying the latter, with deacylation, with concentrated sulfuric acid at 70.degree.-150.degree. C. to give the compounds of the said formula (1) (with R.sub.2 H and n=1).

Process for preparation of

Disazo compounds corresponding to the general formula (1) ##STR1## as well as their metal salts, in which D.sub.1 denotes the benzene or naphthalene nucleus, which can be further substituted by one or two substituents from the group of fluorine, chlorine, bromine, carboxy, lower alkyl, lower alkoxy and nitro and/or one, two or three sulfo groups, D.sub.2 is the benzene or naphthalene nucleus, which is substituted by the substituent X defined below and, in addition to the group --SO.sub.2 --Y, can be further substituted by one or two substituents from the group of carboxy, lower alkyl and lower alkoxy and/or by one substituent from the group of fluorine, chlorine, bromine and nitro and/or one, two or three sulfo groups, X denotes a fluorine, chlorine or bromine atom, which is necessarily bonded to D.sub.2 in ortho-position to the azo group, Y denotes the vinyl, .beta.-sulfatoethyl, .beta.-chloroethyl, .beta.-thiosulfatoethyl or a .beta.-acyloxyethyl group with the acyl radical of a lower alkanecarboxylic acid or of a benzoic acid or of a benzenesulfonic acid, and a and b each represent the number zero or 1, the sum of (a+b) being equal to 1 or 2. These compounds (1) are very suitable as fiber-reactive dyes for dyeing, for example natural or regenerated cellulose fiber, wool or synthetic polyamide fibers. They give on these materials intense dyeings and prints of good fastness properties, and are distinguished, in particular, by a good stability to copper ions, when used in printing processes.

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Hochheim am Main, Germany

Folker Kohlhaas