Ciba-Geigy Corporation

Arnold Wick

Max Jost

Stefan Hari

Hans Altermatt

Joachim Dazzi

Compounds of the formula ##STR1## wherein the symbols D is the radical of a carbocyclic or heterocyclic diazo component, X is hydrogen, halogen, methyl or methoxy, each of A.sub.1 and A.sub.2 independently of the other is unsubstituted phenyl or phenyl which is substituted by halogen, C.sub.1 -C.sub.4 alkyl, methoxy, ethoxy, phenyl or phenoxy, are suitable for the mass coloration of organic polymers.

Process for the mass coloration of polymers

Compounds of the formula I ##STR1## wherein the symbols Z, R.sub.1, R.sub.2, m and n have the meanings defined in claim 1, are suitable, as high-grade pigments, for dyeing high-molecular organic material. They are characterized in particular by good fastness to migration and to cross-lacquering, as well as to weather and light.

Monoazo pigments containing heterocycles, and high-molecular organic

A process for the mass coloration of organic material of high molecular weight, which comprises the use of a mixture of anthraquinone compounds of the formula: ##STR1## wherein n is 1 or 2, R, if n is 1, represents a substituted or unsubstituted anthraquinone radical, and, if n is 2, R represents a radical of the formula: ##STR2## wherein R.sub.1 represents hydrogen, alkyl of 1 to 4 carbon atoms, phenyl or methylmercapto as colorant, having good thermostability, solubility when incorporated in the polymer melt, and resistance to the staining of other material during thermofixation.

Process for coloring organic material of high molecular weight

A process for the mass coloration of thermoplastics with anthraquinonylaminotriazines of the formula ##STR1## wherein each of X.sub.1 and X.sub.2 is an alkylmercapto or arylmercapto group or a group of the formula --NR.sub.1 R.sub.2, in which each of R.sub.1 and R.sub.2 is alkyl, cycloalkyl, aralkyl or aryl, and R.sub.2 can additionally be hydrogen, or R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached and optionally a further heteroatom form a 5- or 6-membered ring, one Y is a hydrogen or chlorine atom, a hydroxy, arylmercapto, alkanoylamino or aroylamino group, or a group of the formula ##STR2## and the other Ys are hydrogen atoms, Hal is a chlorine or bromine atom, and n is 0 or 1. Yellow to orange colored fibres of clear shade, good color strength and fastness properties are obtained.

Process for the mass coloration of thermoplastics with

Process for the dyeing of high-molecular organic material in the melt, in which process there is used as coloring substance an anthraquinone compound of the formula ##STR1## wherein R represents straight-chain or branched-chain alkyl having 1 to 17 C atoms, X.sub.1 and X.sub.2 represent hydrogen or benzoylamino, or X.sub.1 represents hydrogen and X.sub.2 represents benzoylamino.

Process for dyeing high-molecular organic material in the melt

Use of anthraquinone derivatives of the formula ##STR1## wherein X is --NH-- or --S--, one Y is --NHCOR, R being an alkyl, aryl or heterocyclic residue, the other Y are hydrogen, Z is halogen, and n is 0, 1, 2 or 3, whereby Z may be 1 to 3 halogen bound to aryl and/or anthraquinone nucleus and/or the residue R, for dyeing polyesters in the melt.

Process for dyeing polyesters in the melt

Process for the improvement of dyeing properties of pigments of the anilino and arylmercapto anthraquinone series for bulk dyeing linear polyesters by halogenation of unhalogenated or lower halogenated compounds of the formula ##STR1## WHEREIN A is an anthraquinoidal radical being free from nitro groups, X is --NH-- or --S--, n is a number of 1 to 4 and R.sub.1 to R.sub.5 are hydrogen, halogen, alkyl, alkoxy, aryloxy, arylcarbonyl or arylsulphonyl.

Process for the improvement of dyeing properties of pigments of the

An arylaminoanthraquinone of the formula ##STR1## in which one X, in the 5- or 8-position, denote either the radical of the formula ##STR2## or a hydrogen atom, the other X denote hydrogen atoms, alkoxy groups with 1-4 C atoms, aryloxy, arylmercapto or acylamino groups, one Y denotes a nitro group and the other denotes a hydrogen atom, one or two Z which are not adjacent to the nitro group denote chlorine atoms and the remaining Z denote hydrogen atoms, and the Q denote hydrogen or halogen atoms which is useful for coloring high-molecular material.

Arylaminoanthraquinones

Process for bulk dyeing high molecular organic compounds, by using anthrapyrimidines of the formula ##SPC1## As dyestuffs, wherein R denotes a hydrogen atom, an alkyl group or an aromatic radical, one X denotes an arylamino group, or a phenylthio group which is optionally substituted by 1-2 halogen atoms or alkyl groups containing 1-4 carbon atoms, and the other X denotes hydrogen atoms, and X must not be a benzophenonylamino group if R denotes a hydrogen atom.

Process for bulk dyeing high molecular organic compounds

Process for the manufacture of halogen-containing anthraquinoidal compounds being useful for bulk dyeing high molecular organic compounds and having the formula ##SPC1## Wherein A is an anthraquinoidal radical being free from nitro groups, X is --NH-- or --S--, n is a number of 1 to 4. R.sub.1 to R.sub.5 is hydrogen, halogen, alkyl, alkoxy, aryloxy, aroyl or arylsulphonyl, and Hal is halogen, by halogenating compounds of the formula ##SPC2##

Process for the manufacture of halogen-containing anthraquinoidal

Process for the bulk dyeing of polyesters, characterised in that the dyestuffs used are anthraquinone derivatives of the formula ##SPC1## Wherein Q denotes one of the bridge members --O-- or --CO--, R denotes hydrogen or an alkyl group containing 1-4 carbon atoms, Ar denotes an aryl group, n denotes a number from 1 to 4, X, Y and Z denote an amino, hydroxyl, alkoxy, aryloxy, alkylmercapto, arylmercapto, arylamino or aroylamino group or halogen and a, b and c each denote zero or a number from 1 to 4, with the sum of n+a+b+c being a number from 1 to 6.

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Therwil, Switzerland

Arnold Wick