Bayer Aktiengesellschaft

Hans-Samuel Bien

Walter Hohmann

Klaus Wunderlich

Helmut Herzog

Erich Klauke

Volker Hederich

Manfred Groll

Reinold Schmitz

Gunter Gehrke

Norbert Majer

Wolfgang Harms

Helmut Judat

Bernd Thelen

Helmut Seidler

Heinrich Leister

Werner Beinert

Reinhold Schmitz

Armin Lieberam

4,4',7,7'-Tetrachlorothioindigo can be obtained in a form directly suitable for use as a pigment if the oxidation of 3-hydroxy-4,7-dichloro-1-thionaphthene is performed in an alkaline medium in the presence of oxygen or an oxygen-containing gas.

Process for the preparation of 4,4',7,7'-tetrachlorthioindigo in pigment

Reactive dyestuffs are disclosed having the formula ##STR1## in which D is the radical of an organic nonanthraquinoid dyestuff; R is hydrogen or lower alkyl; R.sub.1 is amino or substituted amino with substituents attached by a single bond, optionally etherified hydroxy, optionally etherified mercapto or an optionally substituted hydrocarbon radical; Q is an alkylene, aralkylene, arylene, --CO-- or --SO-- which is directly linked to a carbon atom of the ring of the dyestuff D; n is the number 0 or 1 and F is a fluoro substituent. The group --N(R) is directly linked to a carbon atom of the triazine ring and on the other side, the group --N(R) is linked to a carbon atom of the ring of the dyestuff D either directly (if n=0) or (if n=1) via one of the bridge members mentioned above. These dyestuffs are primarily suitable for dyeing of textile materials containing hydroxyl or nitrogen such as natural and regenerated cellulose, wood, silk, polyamide and polyurethane. The fastness properties, particularly wet fastness, are excellent.

Reactive phthalocyanine dyestuffs containing a fluorotriazinyl group

A process for concentrating at least one of (a) individual halogenoanthraquinones (b) binary mixtures of di-halogenoanthraquinones and (c) binary mixtures of trihalogenoanthraquinones, from a mixture containing at least two halogenoanthraquinones, comprising subjecting said mixture containing at least two halogenoanthraquinones to fractional vacuum distillation in a heated rectification column having an efficiency corresponding to about 20 to 50 theoretical stages with an absolute pressure at the top of about 0.5 to 50 mm Hg and a reflux to take-off ratio of about 5/1 to 50/1. Advantageously, distillation is carried out continuously in a cascade of columns, the products withdrawn from the top of the first column being 2-chloroanthraquinone in the first stage, 1-chloroanthraquinone in the second stage, 1,6- and 1,7-dichloroanthraquinone in the third stage and 1,5- and 1,8-dichloroanthraquinone in the fourth stage, 1,4,5- and 1,4,6-trichloroanthraquinone being obtained in the sump of the 4th stage and being separated therefrom by film evaporation. The mixture of halogenoanthraquinones is advantageously a mixture of chloroanthraquinones such as is obtained by the action of chlorine, chloric acid or a chlorate on various industrial mixtures of nitro- or sulfo-anthraquinones.

Process for concentrating halogenoanthraquinones

Reactive dyestuffs are disclosed having the formula ##STR1## in which D is the radical of an organic nonanthraquinoid dyestuff; R is hydrogen or a lower alkyl; R.sub.1 is amino or substrated amino with substituents attached by a single bond, optionally etherified hydroxy, optionally etherified mercapto or an optionally substituted hydrocarbon radical; Q is an alkylene, aralkylene, arylene, --CO-- or --SO-- which is directly linked to a carbon atom of the ring of the dyestuff D; n is the number 0 or 1 and F is a fluoro substituent. The group --N(R) is directly linked to a carbon atom of the triazine ring and on the other side, the group --N(R) is linked to a carbon atom of the ring of the dyestuff D either directly (if n = 0) or (if n = 1) via one of the bridge members mentioned above. These dyestuffs are primarily suitable for dyeing of textile materials containing hydroxyl or nitrogen such as natural and regenerated cellulose, wood silk, polyamide and polyurethane. The fastness properties, particularly wet fastness, are excellent.

Water soluble reactive axodyestuffs containing a fluorotriazinyl group

Process for dyeing and printing synthetic fibre materials using compounds of the formula ##STR1## in which R represents an optionally substituted phenyl radical, as well as special new dyestuffs within the above formula.

Nitroanthraquinones

Dyestuffs are disclosed having the formula ##STR1## in which W is a reactive radical;

Reactive dyestuffs containing urea alkylene linkage between chromophore

Compounds of the formula ##STR1## wherein R represents cycloalkyl or the ##STR2## group wherein R.sub.1 and R.sub.2 denote alkyl and Y denotes hydrogen, chlorine, bromine, amino, alkylamino, cycloalkylamino, aralkylamino, arylamino, acylamino or arylmercapto, with the proviso that the nitro group is in the 5- or 8-position of the anthraquinone nucleus if Y denotes hydrogen

Anthraquinone compounds

The invention relates to a process for the preparation of water-insoluble chlorine-containing diaminodihydroxyanthraquinone dyestuffs. The process consists in that 2,8-dichloro-1,5-dinitroanthraquinone and/or 2,5-dichloro-1,8-dinitroanthraquinone is warmed with sulphur in concentrated sulphuric acid having a maximum SO.sub.3 content of 20% - possibly in the presence of boric acid - the resulting compounds are, if appropriate, post-halogenated and/or alkylated, preferably in the same reaction batch. The main advantage of this process is that it starts from 1,6- and/or 1,7-dichloroanthraquinone, for which there was hitherto no industrial use, but which unavoidably also arise during the synthesis 1,5- and 1,8-dichloroanthraquinones.

Anthraquinone dyestuffs

The invention relates to the preparation of partially known anthraquinone compounds of the formula ##STR1## wherein Z.sub.1 represents an optionally substituted hydrocarbon radical, Z.sub.2 represents hydrogen or alkyl, one X represents a chlorine atom and the other X denotes a hydrogen atom, by subjecting technical chloroanthraquinone mixtures to a fractional vacuum distillation and reacting the 1,6(1,7)-dichloranthraquinone fraction thereby obtained with amines of the formula HNZ.sub.1 Z.sub.2. Moreover the invention relates to novel compounds of the above formula wherein Z.sub.2 is H and Z.sub.1 is alkyl, alkenyl, aralkyl or cycloalkyl. They are good dyestuffs for synthetic fibres or dyestuff intermediates.

Process for the preparation of anthraquinone compounds

The invention relates to mixtures of water-insoluble anthraquinone dyestuffs of the formula ##STR1## in which A and B are amino or hydroxyl

1-Amino-2-(bromophenoxy-alkoxy)-4-hydroxy anthraquinone dyestuffs

Polycyclic dyestuffs free from sulphonic acid groups of the formula ##STR1## in which A denotes an arylene radical and

Polycyclic dyestuffs

Reactive dyestuffs of the formula ##STR1## in which D is the radical of an organic dyestuff, e.g. an azo dyestuff; R is hydrogen or lower alkyl; O is a bridge member, e.g. --SO.sub.2 --; n is the number 0 or 1; R.sub.1 is hydrogen or a substituent; R.sub.2 is hydrogen, optionaly substituted alkyl, alkenyl, aralkyl or aryl; and F is fluoro; are disclosed. These dyestuffs are suitable for dyeing textile materials containing hydroxyl groups or nitrogen, e.g. cellulose and wool. The dyeings have excellent fastness properties especially wet processing fastness.

Azo dyestuffs containing 6-fluoro-pyrimidinyl 4-reactive group

A process for the preparation of a chloroanthraquinone or a bromoanthraquinone comprising treating a molten mixture of at least one nitroanthraquinone and diluent with halogen at a temperature of about 180 to 300.degree. C, the diluent being present in at least about 10% by weight of the mixture and comprising at least one chloroanthraquinone or bromoanthraquinone. The diluent may correspond to the halogenoanthraquinone obtained from the nitroanthraquinone by replacement of the nitro group. A portion of the product can be recycled as diluent for further reaction.

Process for the preparation of halogenoanthraquinones

Compounds of the formula ##SPC1## In which R represents an alkyl, alkenyl, cycloalkyl or aralkyl radical, one X represents a nitro group and the other X represents hydrogen and their mixtures. They are very suitable for the dyeing of synthetic fibres, such as fibres of polyesters.

Process for dyeing and printing synthetic fiber materials using compounds of the formula ##SPC1## In which

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Burscheid, Germany

Hans-Samuel Bien