Basf Aktiengesellschaft

Gerhard Epple

Wolfgang Elser

Walter Himmele

Manfred Patsch

Helmut Hoch

Reinhold Krallmann

Werner Fliege

Helmut Degen

Wolf-Dieter Kermer

Reinhard Helwig

Uwe Nahr

Helmut Flohr

Siegfried Mensch

Hans Weber

Preparation of triazinyl-bis-anthraquinone dyes by reacting

The useful dye intermediate 1-amino-2-chloro-4-hydroxyanthraquinone is prepared by chlorinating 1-amino-4-hydroxy-2,3-dihydroanthraquinone with chlorine in concentrated sulfuric acid.

Preparation of 1-amino-2-chloro-4-hydroxyanthraquinone

1-Amino-2-bromo-4-hydroxy-anthraquinone (I) ##STR1## is prepared by brominating 1-amino-4-hydroxyanthraquinone (II) ##STR2## in an inert aprotic organic liquid.

Preparation of 1-amino-2-bromo-4-hydroxyanthraquinone

1-Amino-2-chloro-4-hydroxyanthraquinone (I) ##STR1## in prepared by chlorinating 1-amino-4-hydroxyanthraquinone (II) ##STR2## by a process in which the chlorination is carried out in 90-100% strength by weight sulfuric acid or in not more than 2% strength by weight oleum.

A vat dye based on monobromofluoranthene is prepared by a process in which monobromofluoranthene which contains no more than 7% of dibromofluoranthene is reacted with 1-amino-4-benzoylaminoanthraquinone, the reaction product is condensed at from 50.degree. to 70.degree. C. in 83-88% strength sulfuric acid to give the carbazole compound, and the latter is then further brominated to a bromine content of from 20 to 23% by weight. The dyes obtained by the novel process are very useful for dyeing cotton.

Vat dye based on flouranthene

Dyes of the formula ##STR1## where A and B are H and/or ##STR2## Y is unsubstituted or substituted phenyl, ##STR3## or unsubstituted or substituted benzothiazolyl or benzoxazolyl and R is unsubstituted or substituted alkyl, unsubstituted or substituted phenyl, or alkoxy, alkoxyalkoxy, phenalkyl or alkoxycarboalkyl, are suitable for dyeing and printing cellulose swollen with water-miscible swelling agents and cellulose-containing fiber material.

Anthraquinoid dyes

Uniformly dyed water-swellable cellulosic fibers which have been produced by contacting water-swellable cellulosic fibers successively or simultaneously with water, with ethylene glycol, propylene glycol or derivatives of these and with an essentially water-insoluble dye of the formula ##STR1## where Y is unsubstituted or substituted phenyl or naphthyl or an unsubstituted or substituted saturated or unsaturated 5-membered or 6-membered heterocyclic radical, two of the three radicals X are hydroxyl and the remaining radical X is ##STR2## where A is chlorine, bromine, cyano, nitro, an aliphatic, cycloaliphatic, araliphatic or aromatic radical and n is 0, 1, 2 or 3 and where, if n&gt;1, the radicals are identical or different. Deep reddish blue to green dyeings or prints are obtained. The dyeings have very good fastness characteristics.

Uniformly dyed water-swellable cellulosic fibers

A process for the preparation of 1-amino-8-nitro-4,5-dihydroxyanthraquinone by partially reducing the corresponding dinitrohydroxyanthraquinone and isolating the reduction product, in which crude 1,8-dinitro-4,5-dihydroxyanthraquinone obtained by nitrating 4,5-dihydroxyanthraquinone is partially reduced in a phenol-water mixture, which contains from 5 to 50% by weight of water, in the presence of an alkali metal phenolate, by means of a reductone, reductonate or a mixture of these. The product is virtually free from by-products and is suitable for use for the synthesis of dyes.

Production of virtually pure 1-amino-8-nitro-4,5-dihydroxyanthraquinone

Dyes of the formula ##STR1## where Y is alkyl of 3 to 18 carbon atoms or phenyl which is unsubstituted or substituted by chlorine, bromine, alkoxy of 1 to 4 carbon atoms, alkoxycarbonyl (where alkoxy is of 1 to 4 carbon atoms), phenoxy, benzoylamino, trifluoromethyl or alkylcarbonyl (where alkyl is of 1 to 6 carbon atoms), X is hydrogen or ##STR2## where R is alkyl of 1 to 17 carbon atoms, phenylamino, phenyl, alkoxycarbonyl-alkyl (where alkoxy is of 1 to 8 carbon atoms and alkyl of 2 to 4 carbon atoms), alkoxy of 1 to 10 carbon atoms or alkoxyalkyl of a total of 3 to 12 carbon atoms, A is chlorine, bromine, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, B is hydrogen or nitro and n is 0, 1, 2 or 3. On cellulose and cellulose-containing textiles, the dyes, used in the presence of swelling agents, give bluish violet to greenish blue dyeings having very good fastness properties.

Dyes of the formula ##STR1## where X is chlorine or bromine, Y is ##STR2## and n is 0, 1 or 2. On synthetic fiber materials, the dyes give clear blue colorations which are very fast to thermofixing and fast to light.

Anthraquinonoid disperse dyes

The production of aminonitrodihydroxyanthraquinones of the formula: ##STR1## in which one X is OH and the other X is NO.sub.2 by partial reduction of the corresponding dinitrodihydroxyanthraquinone or mixtures thereof by heating at 80.degree.-250.degree. C in the presence of 1/2 to 5 times the weight thereof of an unsubstituted or substituted phenol. The reduction is accelerated by being carried out in the presence of a small amount such as 0.5-20 mol percent of an alkaline-reacting agent. Pure aminonitrohydroxyanthraquinones are obtained which are free from diaminodihydroxyanthraquinones.

Growing community of inventors

Weisenheim, Germany

Gerhard Epple