Hoechst Aktiengesellschaft

Hoechst Celanese Corporation

Other

Hans H Steuernagel

Fritz Meininger

Ernst Hoyer

Anthony J Corso

Erich Feess

Sienling Ong

Folker Kohlhaas

Glenn A Thompson

Dieter Wagner

Process for the preparation of .beta.-chloroethylsulfonylaryl isocyanates of the formula (1)

Process for the preparation of beta-chloroethylsulfonylaryl isocyanates

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,

This invention is directed to new water-soluble, monoazo dyes having the following general formula: ##STR1## in which: X and Y are independently selected from the group consisting of: ##STR2## R, R.sub.1, R.sub.2 are independently selected from H, lower alkyl of one to four carbons and sulfonated lower alkyl;

Water-soluble, monoazo dyes containing a ureido group and two sulfonyl

This invention is that of an improved process for preparing 1:1 copper complex disazo compounds which comprises treating a disazo compound of the following general formula (2): ##STR1## wherein: M is hydrogen or the equivalent monovalent or divalent metal and

Process for the preparation of the copper complex disazo compounds from

An improved and novel process had been found for the esterification of aminophenol, amino-benzanilide and pyrazolone compounds containing a .beta.-hydroxyethylsulfonyl group, by means of sulfuric acid or sulfur trioxide which improvement is characterized by that the esterification is performed in a machine which is operating with a kneading action and effect, using per mol .beta.-hydroxyethylsulfonyl compound 1 to 2.5 times the equivalent molar amount of concentrated sulfuric acid, oleum or sulfur trioxide. This novel process has the great advantage that great amounts of sulfuric acid are saved which could charge the waste water, also in form of sodium sulfate formed after the required neutralization. Furthermore, the .beta.-sulfatoethylsulfonyl compounds formed as end-products in the esterification process are prepared by this novel process in higher yields, in a higher degree of esterification rate and in a higher purity. They are obtained in form of a powder or plastic mass from the kneading machine, which is well transportable and storable, and can advantageously used in the form of this consistency, without intermediate isolation of the pure .beta.-sulfato compound itself, directly for the preparation of azo dyestuffs which are poor of inert salts, possess a high tinctorial strength and purity.

Process for the preparation of sulfuric acid semiester ethylsulfonyl

Improved process for the sulfatation of the hydroxy group of a .beta.-hydroxy-ethylsulfonyl group present in compounds selected from the dyestuff class which comprises carrying out the reaction in a machine operating with a kneading action and effect and with the use of only 1 to 5 times the equimolar amount of a concentrated sulfuric acid, of oleum or sulfur dioxide itself. The .beta.-sulfatoethylsulfonyl group containing dyestuffs, thus prepared have a high purity and are obtained in a high yield and esterification rate. Above all, the novel process is distinguished by a highly reduced salt and acid content of the waste water.

Process for the production of sulfuric acid semiester compounds by

Water-soluble copper, cobalt and chromium complex monoazo compounds of which the metal-free monoazo compound contains as diazo component an aminophenol or aminonaphthol compound subtituted by a fiber-reactive radical of the vinyl sulfone series, the aminophenol possibly being substituted by a lower alkyl, lower alkoxy, nitro, sulfonic acid group, or a chlorine or bromine atom and the naphthol possibly being substituted by a sulfo group, and as coupling component a 6-sulfonaphthol(8) which may be substituted by a sulfo group in the adjacent aromatic nucleus and must be substituted by the monoamide radical of succinic acid, glutaric acid or adipic acid. They are prepared by diazotization of the corresponding aniline and naphthylamine compounds containing, in o-position to the amino group, a hydrogen atom, a hydroxy group or a lower alkoxy group, with subsequent coupling with the above coupling component and transformation into the metal complex compounds by an agent donating copper, cobalt or chromium, optionally in the presence of an oxidant. The coupling components can be prepared by reacting the corresponding aminonaphthol mono- or disulfonic acids with a dihalide or anhydride of succinic acid, glutaric acid or adipic acid. The metal complex compounds have outstanding dyestuff properties. They have a good solubility in water and are especially suitable for dyeing fiber materials of natural and regenerated cellulose, of natural, regenerated or synthetic polyamides of polyurethanes as well as leather. The dyeings display very good fastness to light and to wet processing, a high color strength and portions of the dyestuff which have not been fixed on the fiber can be washed off easily.

Copper, cobalt or chromium complex monoazo compounds, processes for

An improved and novel process has been found for the esterification of amino-benzoxazolone compounds containing a .beta.-hydroxyethylsulfonyl group, by means of sulfuric acid or sulfur trioxide, with simultaneous or subsequent hydrolytic cleavage of the oxazolone ring, wherein the esterification and optional hydrolytic ring cleavage are performed in a machine which is operating with a kneading action and effect, using per mol of .beta.-hydroxyethylsulfonyl compound 1 to 20 times the equivalent molar amount of concentrated sulfuric acid, oleum or sulfur trioxide. This novel process has the great advantage that great amounts of sulfuric acid are saved which would contaminate the waste-water, also in form of sodium sulfate formed after the required neutralization. Furthermore, the .beta.-sulfatoethylsulfonyl compounds formed as end-products in the esterification process are obtained in higher yields, in a higher esterification rate and in a higher purity. They may be obtained in form of a powder or plastic mass, which is conveniently transportable and storable, and can advantageously be used, if ring cleavage had taken place, without intermediate isolation of the pure sulfato compound itself, directly for the preparation of azo dyestuffs which are low in content of inert salts and possess a high tinctorial strength and purity.

Process for the manufacture of sulfuric acid semi-ester compounds

A process for the pad-dyeing or printing of textile material consisting of cellulose and polyester fibers with fiber-reactive and dispersion dyestuffs which comprises printing or padding the textile material with a printing paste or padding liquor which contains besides the usual printing auxiliaries and the dyestuffs mentioned an alkali salt of the formic acid as well as carriers, levelling and/or dispersing agents, fixing the dyestuffs by dry heat at temperatures above 150.degree.C or by hot steam at temperatures above 140.degree.C, and completing the prints or pad dyeings in usual manner.

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Kelkheim, Germany

Hans H Steuernagel