Hoechst Aktiengesellschaft

Klaus Filzinger

Hermann Fuchs

Water-soluble disazo compounds of the formula (1) ##STR1## and diamino compounds serving as starting compounds (tetrazo components), of the formula (4) ##STR2## in which the formulae moieties occurring twice, namely Z, K and X, in each case have a meaning identical to one another and the groups Z are bonded to the two benzene nuclei in each case in the ortho- or in each case in the para-position relative to the ethylenedioxy substituent, and the azo groups or amino groups and the groups Z in the benzene nuclei are in each case bonded in the meta-position relative to one another and K is the radical of a coupling component containing a sulfato, carboxy or sulfo group, X denotes a hydrogen atom or a fiber-reactive group and Z is a group of the formula --SO.sub.2 --CH.dbd.CH.sub.2 or --SO.sub.2 --CH.sub.2 --CH.sub.2 --Y in which Y denotes a radical which can be eliminated in aqueous medium under alkaline or acidic conditions or the hydroxy group. Disazo compounds of the formula (1) can be used as dyestuffs having fiber-reactive properties for dyeing, for example, cellulose fiber material and wool and be prepared by tetrazotizing diamines of the formula (4) and coupling with coupling components evident from the formula (1). Diamino compounds of the formula (4) are obtained by acetylating a 1,2-di-(o- or p-aminophenoxy)-ethane, chlorosulfonating this bis-acetylamino compound and reducing the sulfonyl chloride groups to sulfinic acid groups, which are then oxyethylated to give .beta.-hydroxyethylsulfonyl groups, which, after deacetylation of acetylamino groups, can be converted in a manner which is in itself known into one of the abovementioned groups Z, for example into the .beta.-sulfatoethylsulfonyl group by means of a sulfating agent.

Water-soluble disazo compounds and new bis-(aminophenoxy)-ethane

New water-soluble anthraquinone-azo compounds of the general formula ##STR1## and their salts; in this formula the R.sub.1 s both are sulfo groups, or one of the two is a hydrogen atom and the other is a sulfo group, R is hydrogen or lower alkyl and D, as the radical of a diazo component, is the benzene or naphthalene nucleus, which is monosubstituted or disubstituted by a fiber-reactive group Z, corresponding to the index n being 1 or 2, and which furthermore can be substituted by 1 to 3 substituents selected from lower alkyl, lower alkoxy, halogen, nitro and sulfo. The new azo compounds are very suitable as dyestuffs for dyeing fiber materials containing hydroxy groups or carbonamide groups, such as natural or synthetic polyamide fibers or polyurethane fibers and cellulose fibers, yielding deep dyeing and prints with very good fastness properties to wet processing and very good fastness properties to light. The new compounds of the above formula are obtained by diazotizing a 1-amino-2-sulfo-4-(4'-aminophenyl)-aminoanthraquinone compound, which is substituted by sulfo in the 2'- and/or 5'-position, by means of an equivalent amount of sodium nitrite in the presence of a mineral acid, coupling this diazonium salt with an acetylsuccinic acid ester of a lower alkanol, cyclizing this radical of the coupling component to the pyrazolone ring and coupling the pyrazolono-phenylamino-anthraquinone compound, thus obtained, with a diazonium compound of an amine of the formula

1-Amino-2-sulfo-(4'-pyrazolonyl-phenyl)-aminoanthraquinone compounds and

Water-soluble disazodyestuffs of the formula ##STR1## in which R.sub.1 and R.sub.2 are identical or different and each is hydrogen, methyl, ethyl or methoxy, and R.sub.3 is hydrogen, chlorine, nitro or alkyl of 1 to 4 carbon atoms, and their salts have been found which possess very good dyeing characteristics and are very well suitable for dyeing of synthetic polyamides and yield dyeings on these fibers with good to very good wet fastnesses and fastnesses to processing and to use. In accordance with this, an improved process had been found for coloring synthetic polyamide fibres by applying the above dyestuffs of the invention on said fibres in usual dyeing and printing methods and fixing them on the fibre by methods as usual in the art.

Water-soluble disazo dyestuffs and process for coloring synthetic

Novel, valuable unsymmetrical 1:2-cobalt complex dyestuffs of an azo compound and an azomethine compound have been found which are well suited for the dyeing of natural and synthetic polyamide fibres, yielding even dyeings of high fastnesses to wet processing and use as well as to light. The novel dyestuffs can be prepared either by cobalting the equimolar mixture of the metalfree azo and azomethine dyestuffs with a cobalt-yielding compound at a pH of 5 to 10 at 60 .degree. to 150.degree. C., or by first cobalting the azomethine compound and then reacting it with the equimolar amount of the metalfree azo compound. The compounds are 1:2-cobalt complex compounds of the compounds ##STR1## in which R.sub.1 is chlorine, lower alkyl or nitro, R.sub.2 is hydrogen, lower alkyl or lower alkoxy, R.sub.3 is hydrogen, chlorine, nitro or lower alkyl, Z is ##STR2## in which R.sub.4 is hydrogen, lower alkyl or lowr alkoxy, R.sub.5 is hydrogen, lower alkyl or lower alkoxy, X is hydroxy, sulfoalkyl of from 1 to 4 carbon atoms, or ##STR3## R.sub.9 is hydrogen or lower alkyl, and R.sub.6 and R.sub.7 are different from each other and each is nitro or sulfo.

Water-soluble 1:2-cobalt complex dyestuffs of an azomethine and of an

Valuable 1:2-cobalt complex dyestuffs of the disazo compound of formula (1) ##STR1## had been found, in which R.sub.1 is hydrogen, halogen, nitro, lower alkyl or lower alkoxy, R.sub.2 is hydrogen, lower alkyl or lower alkoxy, R.sub.3 is hydrogen, lower alkyl or lower alkoxy, X is hydroxy or .beta.-sulfoethyl or a group of the formula ##STR2## wherein R.sub.4 is hydrogen or lower alkyl. The novel dyestuffs are well suitable for the dyeing of natural and synthetic polyamide fibres, especially in admixture with hydrophobic fibres, and also especially advantageously with other 1:2-chromium or 1:2 cobalt complex dyestuffs containing one or two sulfonic acid groups per dyestuff molecule, and yield even, strong dyeings of high fastness to wet processing and to use as well as to light. The novel cobalt complex dyestuff can be prepared by cobalting the above disazo compound (1) by means of a cobalt yielding agent.

1:2 Cobalt complex phenol-acetoacetanilide benzene disazo dyestuffs

Novel, valuable 1:2-cobalt-complex dyestuffs of the monoazo compound of formula ##STR1## had been found, in which R.sub.1 is halogen, nitro, lower alkyl, a sulfonamide radical or a carbonamide radical, and R.sub.2 and R.sub.3 are alternatively a nitro and sulfo group. These novel dyestuffs are well suitable for the dyeing of natural and synthetic polyamide fibers, especially in admixture with hydrophobic fibers, and also especially advantageously with other 1:2-chromium or 1:2-cobalt-complex dyestuffs containing one or two sulfonic acid groups per dyestuff molecule, yielding even, strong dyeings of high fastnesses to wet processing and to use as well as to light. -- The novel cobalt complex dyestuffs can be prepared by cobalting the above monoazo compound (1) by means of a cobalt yielding agent.

1:2-Cobalt-complex azo dyestuffs having an acetoacetylamino

Use of a water-soluble disazo dyestuff of the formula ##STR1## in which R.sub.1 represents a hydrogen atom or the sulfonic acid group, R.sub.2 represents a chlorine atom or the methoxy group, and R.sub.3 and R.sub.4 each represents a hydrogen atom or a methoxy group, for the dyeing or printing of synthetic textile material consisting of or containing polyamide or polyurethane fibers, the dyestuff used yielding on the said fibrous material excellent, clear golden-yellow to orange dyeings or prints being distinguished by very good properties as to fastness to light and to wetting.

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Hofheim, Germany

Klaus Filzinger