Ciba-geigy Corporation

Stefan Hari

Georg Cseh

Olof Wallquist

Rudolf Mory

Jost Von Der Crone

Armand Roueche

Fridolin Babler

Francois L'Eplattenier

Fritz Herren

Thomas Eichenberger

Andreas Burkhard

James M McCrae

Arnold Wick

Laurent Vuitel

Rolf Muller

Karl Ronco

Alexander M Irvine

Arnold Grubenmann

Josef Somlo

Ernesto Rinaldi

Compounds of formula ##STR1## wherein R is hydrogen or a group ##STR2## M.sub.1 and M.sub.2 are each independently of the other an alkali metal or alkaline earth metal or aluminum or a group of formula ##STR3## wherein n is 1, 2 or 3, and R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are hydrogen or C.sub.1 -C.sub.8 alkyl,

Bisazo, bisazomethine and azo-azomethine compounds derived from

Mixed crystals of at least two different compounds of formula ##STR1## wherein A and B are each independently of the other a cation of formula ##EQU1## or N.sup.+ H(R.sub.1)(R.sub.2)(R.sub.3) M is a mono-, di- or trivalent metal cation, n is 1, 2 or 3, R.sub.1, R.sub.2 and R.sub.3 are each independently of one another hydrogen, C.sub.1 -C.sub.22 alkyl, C.sub.7 -C.sub.24 aralkyl, C.sub.5 -C.sub.6 cycloalkyl or C.sub.6 -C.sub.18 aryl, m is 0 or 1, and R is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, in which compounds of formula I that form the mixed crystals the cations A and B constitute a composite structure ##EQU2## wherein x is a value from 0.2 to 0.8, and the X-ray diffraction pattern of said mixed crystals differs from that of the corresponding compounds in which x is 1 or 0. These mixed crystals can be used as pigments for colouring organic material of high molecular weight and have exceptional properties, especially dispersibility, heat- and lightfastness.

Mixed crystals of sulfonated diketopyrrolopyrroles

Compounds of formula I ##STR1## wherein R is a radical of formula --OR.sub.3 or --NHR.sub.3, A is a radical of formula II or III ##STR2## and B is a radical of formula ##STR3## wherein n is 1 or 2,

Disazo compounds containing cycloalkyl ester or cycloalkylamide groups

Compounds of formula ##STR1## wherein R is C.sub.7 -C.sub.21 alkyl, C.sub.4 -C.sub.18 alkenyl, C.sub.5 -C.sub.12 cycloalkyl or C.sub.5 -C.sub.6 cycloalkyl-substituted C.sub.1 -C.sub.4 alkyl,

Perylenetetracarboxylic acid diimides containing long-chain

Compounds of formula ##STR1## wherein a and b are each independently of the other halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OC.sub.2 H.sub.5 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, c and d are each independently of the other hydrogen, halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OCH.sub.3, --OC.sub.2 H.sub.5 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, and R.sup.1 is --CH.sub.3, phenyl, --COOCH.sub.3, --COOC.sub.2 H.sub.5, --NHCO--C.sub.1 -C.sub.4 alkyl or --CONH--C.sub.1 -C.sub.4 alkyl, and R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl, unsubstituted or substituted by a chlorine atom or a --OH group, or are C.sub.7 -C.sub.9 aralkyl, C.sub.5 -C.sub.8 cycloalkyl, phenyl or phenyl which is substituted by 1 to 3 halogen atoms or methyl or methoxy groups, or is a heterocyclic radical of the benzimidazole, benzoxazole, benzthiazole or pyridine series, or R.sup.3 and R.sup.4, together with the linking nitrogen atom, are a pyrrolidine, imidazolidine, piperidine, piperazine or morpholine radical, or R.sup.3, R.sup.4 and R.sup.5, together with the linking nitrogen atom, are a pyrrole, pyridine, picoline, pyrazine, quinoline or isoquinoline radical, are most suitable for coloring high molecular organic material.

Amine salts of azo pigments based on pyrazolone derivatives

Compounds of the formula I ##STR1## in which R is a radical of the formula --OR.sub.5 or --NHR.sub.5, A is a radical of the formula II or III ##STR2## in which B is a radical of the formula ##STR3## in which n is the number 1 or 2, R.sub.1 and R.sub.3 independently of one another are --H or Cl, R.sub.2 and R.sub.4 independently of one another are --H, halogen, --NO.sub.2, --CN, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, --CF.sub.3, C.sub.2 -C.sub.5 alkoxycarbonyl, or --CONH-phenyl, --NHCO-phenyl or phenyloxy which is unsubstituted or substituted on the phenyl nucleus by one or two chlorine atoms or one or two methyl, methoxy or ethoxy groups, R.sub.5 is alkyl having at least 10 C atoms, R.sub.6 and R.sub.7 independently of one another are --H, halogen, --NO.sub.2, --CN, --CF.sub.3, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, R.sub.8 is --H, --Cl, --Br, --CH.sub.3 or --OCH.sub.3 and X is --H, --Br, --OCH.sub.3, --CN or --NO.sub.2, are particularly suitable as pigments for coloring polyolefins.

Disazo compounds containing long-chain alkyl ester radicals or

Compounds of the formulae I and II ##STR1## in which A is a radical of the formulae III, IV or V ##STR2## R.sub.1 and R.sub.4 are --H or --Cl, R.sub.2 and R.sub.5 are --H, halogen, --NO.sub.2, --CN, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 alkoxy, --CF.sub.3 or phenyloxy which is unsubstituted or substituted by one or two chlorine atoms and/or one or two methyl or methoxy groups, and R.sub.3 is alkyl having at least 10 C atoms, X is a radical of the formulae --NH--, --O--, ##STR3## n is the number 1 or 2, Y is the radical of the formulae --COO--, --OOC--, --CONH-- or --NHCO-- or a radical of the formulae ##STR4## in which R.sub.1 and R.sub.2 are as defined above, D is an aromatic heterocyclic 5- or 6-membered ring, in which the ring contains 1 or 2 N atoms and may additionally contain an O atom or S atom, Z is --H, --Br, --OCH.sub.3, --CN or --NO.sub.2 and X.sub.1 and X.sub.2, independently of one another, are --H, halogen, --CH.sub.3, --OCH.sub.3, --OC.sub.2 H.sub.5 or --NO.sub.2 and X.sub.3 is --H, --NHCO--C.sub.1 -C.sub.4 alkyl, benzoylamino or phenylcarboxamide which are each unsubstituted or substituted on the phenyl ring by one or two chlorine atoms and/or one or two methyl or methoxy groups or an --NHCO--C.sub.1 -C.sub.4 alkyl group, or X.sub.2 and X.sub.3 together with the carbon atom to which they are bound are an aromatic carbocyclic 6-membered ring or an aromatic heterocyclic 5- or 6-membered ring, in which the heterocyclic ring contains 1 or 2 N atoms and can additionally have an O atom or S atom, and Y.sub.1 is --H, --OCH.sub.3, --OC.sub.2 H.sub.5 or --NHCOCH.sub.3, with the proviso that X.sub.3 must not be H, if X is --O-- or --NH--, are highly suitable for the mass coloration of plastics, in particular of polyolefins.

Monoazo compounds containing long-chain alkyl radicals

Compounds of formula ##STR1## wherein a and b are each independently of the other halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OCH.sub.3, --OC.sub.2 H.sub.5 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, c and d are each independently of the other hydrogen, halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OCH.sub.3, --OC.sub.2 H.sub.5 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, and R.sup.1 is --CH.sub.3, phenyl, --COOCH.sub.3, --COOC.sub.2 H.sub.5, --NHCO--C.sub.1 -C.sub.4 alkyl or --CONH--C.sub.1 -C.sub.4 alkyl, and R.sup.2, R.sup.3, R.sub.4 and R.sub.5 are each independently hydrogen, C.sub.1 -C.sub.4 alkyl, unsubstituted or substituted by a chlorine atom or a --OH group, or are C.sub.7 -C.sub.9 aralkyl, C.sub.5 -C.sub.8 cycloalkyl, phenyl or phenyl which is substituted by 1 to 3 halogen atoms or methyl or methoxy groups, or is a heterocyclic radical of the benzimidazole, benzoxazole, benzthiazole or pyridine series, or R.sup.3 and R.sup.4, together with the linking nitrogen atom, are a pyrrolidine, imidazolidine, piperidine, piperazine or morpholine radical, or R.sup.3, R.sup.4 and R.sup.5, together with the linking nitrogen atom, are a pyrrole, pyridine, picoline, pyrazine, quinoline or isoquinoline radical, are most suitable for coloring high molecular organic material.

Process for coloring high-molecular weight organic material using amine

Mixed crystals of at least two different compounds of formula I ##STR1## wherein R is --CH.sub.3, phenyl, --COOCH.sub.3, --COOCH.sub.3, --COOC.sub.2 H.sub.5, --NHCO--C.sub.1 -C.sub.4 alkyl or --CONH--C.sub.1 -C.sub.4 alkyl, M.sup.+ and M.sub.1.sup.+ are each independently of the other an alkali metal cation, an alkaline earth metal cation or a heavy metal cation or NH.sub.4.sup.+ ; wherein X, Y, X' and Y' are each independently hydrogen, halogen, --CH.sub.3, --C.sub.2 H.sub.5, --OCH.sub.3, --OC.sub.2 H.sub.5, --NO.sub.2 or the group of formula --NHCO--C.sub.1 -C.sub.4 alkyl, wherein at least two of the cations M.sup.+ and M.sub.1.sup.+ in the compounds forming the mixed crystals of formula I are different and the X-ray diffraction patterns of the mixed crystals differ from the X-ray diffraction patterns of the individual components and of their sum. Such mixed crystals are most suitable as pigments for coloring high molecular organic material and are distinguished in particular by surprisingly high color strength and pure shade.

Mixed sodium, ammonium and/or calcium salt crystals of laked monoazo

Compounds of formula I: ##STR1## wherein R is a radical of the formula --OR.sub.3 or --NHR.sub.3, A is a radical of formula II or III: ##STR2## B is a radical of the formula ##STR3## n is the number 1 or 2, R.sub.1 is --H or --Cl, R.sub.2 is --H, halogen, --NO.sub.2, --CN, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, --CF.sub.3, C.sub.2 -C.sub.5 alkoxycarbonyl or --CONH-phenyl, --NHCO-phenyl or phenoxy which is unsubstituted or substituted on the phenyl ring by one or two chlorine atoms or one or two methyl, methoxy or ethoxy groups, R.sub.3 is alkyl containing at least 10 C atoms, R.sub.4 and R.sub.5 are each independently of the other --H, halogen, --NO.sub.2, --CN, --CF.sub.3, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, R.sub.6 is --H, --Cl, --Br, --CH.sub.3 or --OCH.sub.3 and X is --H, --Br, --OCH.sub.3, --CN or --NO.sub.2, are suitable as pigments, especially for coloring polyolefins, as well as novel intermediates of the formula ##STR4## wherein n is the number 1 or 2, R is a radical of the formula --OR.sub.3 or --NHR.sub.3, R.sub.1 is --H or --Cl, R.sub.2 is --H, halogen, --NO.sub.2, --CN, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, --CF.sub.3, C.sub.2 -C.sub.5 alkoxycarbonyl or --CONH-phenyl, --NHCO-phenyl or phenoxy which is unsubstituted or substituted on the phenyl ring by one or two chlorine atoms or one or two methyl, methoxy or ethoxy groups, R.sub.3 is alkyl containing at least 10 C atoms, X is --H, --Br, --OCH.sub.3, --CN or --NO.sub.2 and Q is --OH or halogen.

Mono and disazo compounds based on b-hydroxy-naphthoic acid derivatives

Azo compounds of the formula I ##STR1## wherein X is --H, --CH.sub.3, --CF.sub.3, --NO.sub.2, --COOR.sub.1, --NHCOR.sub.2 or --COHN.sub.2, and R.sub.1 and R.sub.2 are as defined in claim 1, are suitable for pigmenting high-molecular organic material.

Phenyl-azo-hydroxynaphthoic acid amide pigments containing at least one

A process for pigmenting high molecular weight organic material, which comprises using, as pigment, a monoazo compound of the formula ##STR1## wherein A is a carbocyclic aromatic radical, R is an aliphatic, cycloaliphatic, araliphatic or aromatic radical or an alkoxy group, and Q is a hydrogen or a halogen atom or a methyl group. The colorations obtained, for example in plastics, filaments, lacquers and prints, have very high color strength, high saturation, good dispersibility, good fastness to overspraying, migration, heat, light and atmospheric influences, and good gloss.

Process for pigmenting high molecular weight organic material

Monoazo pigment compounds of the formula ##STR1## wherein X is a group of the formula ##STR2## R is hydrogen or methyl, R.sub.1 and R.sub.2 are hydrogen, chlorine, methyl or methoxy, Y is methyl or phenyl, or Y is --O, --S--, --N(R.sub.3)-- or --C(R.sub.4).dbd.CH--, each of which is bound on the ring A in the ortho-position with respect to the --NHCO-- group to form a benzoxazolone, benzothiazolone, benzimidazolone or quinolone-2, with R.sub.3 and R.sub.4 being hydrogen or methyl, and m and n independently of one another are each 1 or 2, are useful as high-grade pigments, for pigmenting high-molecular weight organic material. The pigments are distinguished in particular by good fastness to light, migration and weather.

Monoazo pigments derived from aminophthalimides and substituted

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

Monoazo pigments of the formula I ##STR1## in which R is the radical of a carbocyclic or heterocyclic aromatic amine and R.sub.1, R.sub.2 and R.sub.3 are hydrogen, halogen, alkyl, alkoxy, alkoxycarbonyl, substituted or unsubstituted aminocarbonyl, nitro, cyano or trifluoromethyl. These pigments are suitable for coloring high molecular weight organic material and are distinguished by their easy accessibility and good general fastness properties and in particular by high clarity of color shade.

Growing community of inventors

Allschwil, Switzerland

Stefan Hari