Hoechst Aktiengesellschaft

Helmut Troster

Ernst Spietschka

Theodor Papenfuhs

Otto Fuchs

Hans-Tobias Macholdt

Alexander Sieber

Walter Deucker

Hans Gattner

Joachim Otten

The invention relates to perylene-3,4,9,10-tetracarboxylic diimides of the formula (I) ##STR1## in which R is a 3'- and/or 4'-methoxybenzyl radical, and their preparation and use as black pigments, inter alia in paint preparations, printing inks or for the dyeing of polymers.

Black peryene-3,4,9,10-tetracarboxylic diimides, their preparation and

Perylenetetracarbimide mix-crystal pigments in the crystal lattice of the .alpha.-modification of N,N'-bis-3',5'-dimethylphenylperylenetetracarbimide of the formula (1) comprising 99-70 mole percent of the symmetrical diimide of the formula (1) and correspondingly 1-30 mole percent of the asymmetrically substituted diimide of the formula (2) ##STR1## process for their preparation and their use for coloring organic polymers.

Mix-crystal pigments based on perylenetetracarbimides, process for their

Process for the preparation of compounds of the formula (1) ##STR1## in which R.sub.1 denotes a phenyl or naphthyl radical which can be substituted by alkyl, cycloalkyl, alkoxy, aryloxy, arylazo or nitro groups or halogen atoms, and R.sub.2 denotes a hydrogen atom or a phenyl or naphthyl radical which can be substituted by alkyl, cycloalkyl, alkoxy, aryloxy, arylazo or nitro groups or halogen atoms, or denotes an alkyl (C.sub.1 -C.sub.8) radical, by condensation, at between 100.degree. C. and 300.degree. C., of perylene-3,4,9,10-tetracarboxylic dianhydride or a monoanhydride monoimide of the formula (2) ##STR2## in which R.sub.2 has the abovementioned meaning, with an arylamine of the formula (3)

Process for the preparation of arylimides of

Colorant for electrophotographic recording processes which is composed of mix-crystals of 99-70 parts of a compound of the following formula I and 1-30 parts of a compound of the following formula II ##STR1## where R in formula II denotes a C.sub.1 -C.sub.4 -alkyl group, and the use thereof for preparing toners or developers which are used for the electrophotographic copying or duplicating of originals and for printing electronically, optically or magnetically stored information.

Pigment for electrophotographic recording processes

Process for preparing perylenetetracarbimide mix-crystal pigments in the crystal lattice of the .alpha.-modification of the N,N'-bis-3',5'-dimethylphenylperylenetetracarbimide of the formula (1) comprising essentially symmetrical N,N'-bis-3',5'-dimethylphenylperylenetetracarbimide of the formula (1) and at least one asymmetrically substituted diimide of the formula (2) in which R stands for methyl or ethyl ##STR1## by condensing 1 mole of perylenetetracarboxylic dianhydride with an excess of up to 30 moles of 3,5-dimethylaniline which contains in total 0.5-6 percent by weight of 4-ethoxyaniline, and their use for coloring organic polymers.

Mix-crystal pigments based on perylenetetracarbimides, process for

Perylenetetracarbimide mix-crystal pigments in the crystal lattice of the .alpha.- Modification of N,N'-bis-3',5'-dimethylphenylperylenetetracarbimide of the formula (1) comprising 98-70 mole percent of the symmetrical diimide of the formula (1) and correspondingly 2-30 mole percent of at least one asymmetrical diimide of the formula (2) ##STR1## in which R denotes a hydrogen atom or a methyl group.

Compounds of the formula ##STR1## in which R denotes hydrogen, hydroxyl, amino or optionally substituted alkyl, X denotes chlorine or bromine and n is a number from zero to 4, are obtained from the corresponding mono-alkali metal salts of perylene-3,4,9,10-tetracarboxylic acid monoanhydrides by reaction with compounds of the formula R-NH.sub.2, in which R has the above meaning, at 0.degree.-130.degree. C. The compounds are colorants or starting materials for colorants.

Process for the preparation of perylene-3,4,9,10-tetracarboxylic acid

Compounds of the formula ##STR1## in which R denotes hydrogen, hydroxyl, amino or optionally substituted alkyl, X denotes chlorine or bromine and n is a number from zero to 4, are obtained from the corresponding mono-alkali metal salts of perylene-3,4,9,10-tetracarboxylic acid monoanhydrides by reaction with compounds of the formula R--NH.sub.2, in which R has the above meaning, at 0.degree.-130.degree. C. The compounds are colorants or starting materials for colorants.

Perylene-3,4,9,10-tetracarboxylic acid monoanhydride monoimides

Compounds of the formula ##STR1## wherein X denotes a chlorine or bromine atom, n denotes a number from zero to 4 and Y denotes an oxygen atom or a nitrogen atom, and A, if Y represents an oxygen atom, is the phenyl radical, which can be substituted by substituents from the group comprising halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, carbalkoxy with 1-4 carbon atoms in the alkyl radical, hydroxyl, carboxyl, CF.sub.3, nitro, phenoxy, phenoxy which is substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy and/or halogen, phenylamino, phenylamino which is substituted in the phenyl radical by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy and/or halogen, phenylazo and phenylazo which is substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -akloxy and/or halogen, or is the pyridyl radical, which can be substituted by halogen and/or C.sub.1 -C.sub.4 -alkyl, or A, if Y represents a nitrogen atom, is the o-phenylene radical, which, together with Y and the other nitrogen atom, forms the benzimidazole ring, it being possible for the benzene nucleus of the benzimidazole ring to be substituted by substituents from the group comprising halogen, C.sub.1 -C.sub.4 -alkyl and C.sub.1 -C.sub.4 -alkoxy, processes for their preparation and their use as colorants or their use as intermediates for the preparation of colorants.

Perylene-3,4,9,10-tetracarboxylic acid monoanhydride monoimide and

Perylene-3,4,9,10-tetracarboxylic acid monoanhydride mono-sodium or mono-potassium salts are obtained from neutral salts of perylene-3,4,9,10-tetracarboxylic acid, if necessary in the presence of at least one molar equivalent of sodium or potassium ions, at 20.degree. to 100.degree. C. by adding three molar equivalents of a sufficiently strong acid. The products are dye precursors, especially for asymmetric N-substituted perylenetetracarboxylic acid diimide pigments.

Monoalkali metal salts of perylene-3,4,9,10-tetracarboxylic acid

Water-soluble dyestuffs of the formula ##STR1## in which Y is oxygen or an imino group, R.sup.1 and R.sup.2 are hydrogen, halogen or lower alkyl or lower alkoxy, n is 1 to 3 and Z is a cation, are useful for fluorescent inks.

Water soluble benzoxanthene dyestuffs for fluorescent inks

When reacting a dyestuff having hydroxy, acyloxy, carboxy or carbalkoxy groups with a polyester derived from terephthalic and/or isophthalic acid and, per mol of dicarboxylic acid, about 0.75 to 1.5 mol of a low-molecular alkanetriol with primary alcohol groups (methylol groups) or, instead of said polyester, with the corresponding starting materials or precondensates, a polyester with chemically linked dyestuff units is obtained which is useful for dyeing plastics, especially polyolefins. The dyed plastic materials are heat resistant, even when containing fluorescent dyestuff units, transparent and uniformly dyed.

Dyed polyesters, process for their preparation and their use for the

Perinones of the formula ##STR1## IN WHICH A represents an ortho- or peri-arylene radical or a heterocyclic radical, and n represents the number 1 or 2 and m = 1 if n = 1 and m = 0 if n = 2, are obtained by reacting a 3,6-dihydroxynaphthalic anhydride with an aromatic or heterocyclic ortho- or peri-diamine or tetramine or the salts thereof. The products are valuable pigments.

Perinone compounds as colorants for polyolefins

Treating compounds of the formula ##STR1## in which the nuclei marked 'A' and 'B' can be substituted by halogen, lower alkyl, lower alkoxy or phenyl, with acid binding agents at elevated temperatures in polar organic solvents yields compounds of the formula ##STR2## in which A and B have the same meaning. The products are dyestuffs of high brillancy, pure shades, high fluorescence, excellent tinctorial strength and good fastness to light.

Benzothioxanthenes

It has been found that dyestuffs of the formula ##STR1## in which p stands for an integer of from 1 to 6, and W represents, as a water-solubilizing group, the sulfo group, the sulfato group (--OSO.sub.3 H), the thiosulfato group (--S--SO.sub.3 H), the carboxyl group, the phosphato group (--OPO.sub.3 H.sub.2), the phosphonic acid group (--PO(OH).sub.2) or the phosphonic acid-semi-ester group of the formula --PO(OR)OH, wherein R represents an alkyl radical of from 1 to 5 carbon atoms, preferably the methyl or ethyl radical, are very suitable in dyeing and printing processes of synthetic polyamide fiber materials and yield brilliant and very fast dyeings and prints on these materials, especially even dyeings of textured polyamide fibers which have differences in stretching.

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Konigstein, Germany

Helmut Troster