Ciba-geigy Corporation

Ciba-geigy Ag

Ulrich Schlesinger

Gerhard Back

Hans U Schutz

Fabio Beffa

Alois Puntener

Visvanathan Ramanathan

Peter Loew

Rene De Montmollin

Fabic Beffa

A metal complex suitable as dyes for the dyeing of a wide range of textile and non-textile materials, particularly leather and fur, said metal complex of a compound of the formula ##STR1## in which D and D.sub.1, independently of one another, are each the radical of a diazo component of the benzene or naphthalene series and M is a phenylene radical which may be further substituted.

Polyazo dyes containing resorcinol as middle component and metal

A process for the preparation of azo dyes of the formula ##STR1## in which X is --NH.sub.2 or --OH, A is a benzene or naphthalene radical which can be substituted by nitro, halogen, sulfo, C.sub.2 -C.sub.6 alkanoylamino, C.sub.1 -C.sub.6 -alkoxycarbonylamino, sulfonamido and sulfone groups and B is a benzene radical which is monosubstituted or disubstituted by C.sub.1 -C.sub.6 alkyl, or a naphthalene radical which can be substituted by amino, phenylamino, C.sub.1 -C.sub.6 alkylamino and sulfo, or a 1-phenyl-3-methyl-5-pyrazlone radical which can be substituted by halogen, C.sub.1 -C.sub.6 alkyl and C.sub.1 -C.sub.6 alkoy, these radicals being bound to the azo group in the o-position with respect to the hydroxyl or amino groups, comprises diazotizing in aqueous solution an amine of the formula ##STR2## in the presence of at least one ketone of the formula ##STR3## in which R.sub.1 and R.sub.2, independently of one another, are each C.sub.1 -C.sub.4 alkyl, and coupling the product on to a coupling component of the formula ##STR4## in which A, B and X in formulae (2) and (4) are as defined in formula (1). The present invention makes it possible to prepare the azo dyes mentioned in high yields.

Process for the preparation of metallizable monoazo dyes in the presence

The invention relates to chromium complexes of the formula ##STR1## in which L is H.sub.2 O, NH.sub.3, R.sub.2 --OH, R.sub.2 --NH.sub.2, (R.sub.2).sub.2 NH, (R.sub.2).sub.3 N or pyridine, wherein R.sub.2 is C.sub.1-6 -alkyl unsubstituted or substituted by halogen, C.sub.1-4 -alkoxy or amino, B is 8-hydroxyquinoline, 5-chloro-8-hydroxyquinoline, 5-hydroxyacridine, 6-hydroxy-4,7-phenanthroline, pyridine-2-carboxylic acid, 8-carboxyquinoline, 5,7-dibromo-8-hydroxyquinoline, o-hydroxyaniline, o-hydroxynaphthylamine, proline, glycine, serine, aspartic acid or R.sub.1 --CH(NH.sub.2)--COOH, wherein R.sub.1 is C.sub.1-6 -alkyl unsubstituted or substituted by halogen, C.sub.1-4 -alkoxy or amino, D is benzene or naphthalene, Y is the nitrogen atom or the CH group, K, in the event that Y is the nitrogen atom, is naphthol, naphthylamine, 5-pyrazolone, 5-aminopyrazole, 1-phenyl- or 1-naphthyl-5-aminopyrazole, 1-phenyl- or 1-naphthyl-5-pyrazolone, 2,6-dihydroxy-3-cyano- or -3-carboxamido-4-alkylpyridine, 6-hydroxypyrid-2-one, acetoacetanilide, benzoylacetanilide or phenol, or, in the event that Y is the CH group K is o-hydroxybenzaldehyde or o-hydroxynaphthaldehyde, D and K independently of each other are unsubstituted or substituted by C.sub.1-5 -alkyl, C.sub.1-4 -alkoxy, acylamino having 1 to 6 carbon atoms, benzoylamino, amino, monoalkylamino or dialkylamino each having 1 to 4 carbon atoms, phenylamino, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy, radical, nitro, cyano, trifluoromethyl, halogen, sulfamoyl, carbamoyl, ureido, hydroxyl, C.sub.1-4 -alkylsulfonyl, carboxyl, sulfomethyl, phenylazo or naphthylazo, and D and K contain the --(CO).sub.0-1 --O-- and --[O or N(R)]-- adjacent to the --N.dbd.Y-- and R is hydrogen, C.sub.1-4 -alkyl or phenyl, Ka is a cation, X is acryloyl, monohalogenoacryloyl, dihalogenoacryloyl, trihalogenoacryloyl, monohalogenomethacryloyl, dihalogenomethacryloyl, trihalogenomethacryloyl, monohalogenopropionyl, dihalogenopropionyl, phenylsulfonylpropionyl, methylsulfonylpropionyl, vinylsulfonyl, .beta.-chloroethylsulfonyl, .beta.-sulfatoethylsulfonyl, monohalogenopyrimidyl, dihalogenopyrimidyl, trihalogenopyrimidyl, monohalogenotriazinyl, dihalogenotriazinyl, X is bonded to D, K or B, D and K, D and B or K and B directly or via ##STR2## or --CH.sub.2 --N(R)--, m is 1, 2 or 3 and n is 1 or 2. These chromium complexes are suitable for dyeing nitrogen-containing or hydroxy-containing materials and they produce level dyeings having good all-round fastness properties.

Fibre-reactive 1:1 chromium complex azo or azomethine dyes having a

Dyes suitable for dyeing wool, polyamide and leather in orange, brown or olive-brown shades are disclosed, the dyes having the formula ##STR1## wherein A and D are each independently of the other a benzene or napththalene radical of a diazo component, which component carries the hydroxyl or carboxyl group in the ortho-position to the azo group;

Asymmetric 1:2-chromium complex dyes containing two azo dyes, one

The invention relates to chromium complexes of the formula ##STR1## in which A is the radical of a dicyclically metallizable azo or azomethine dye, B is the radical of a potentially at least bidentate bianionic complexible organic compound which contains no azo or azomethine group, L is a colorless monofunctional ligand, X is a fibre-reactive radical, Ka is a cation, K is 0 or 1, m is 1, 2 or 3, n is 1 or 2, and the X radical and the SO.sub.3.sup..crclbar. Ka group are each bonded to the radicals A and B, to a process for preparing the chromium complexes of the formula (1), and to a combined preparation and dyeing process.

Fiber-reactive chromium complexes and their preparation and use for

Condensates of an azo compound of the formula ##STR1## wherein n is 1 or 2, with the stilbene compound of the formula ##STR2## in the molar ratio of 1:1 to 2:1, dye leather in a yellowish-brown shade, which penetrate deeply into the leather, and give fast dyeings.

Azo-stibene condensates as leather dyes

The invention relates to chromium complexes of the formula ##STR1## in which B is the radical of a bidentate bianionic compound, L is H.sub.2 O, NH.sub.3, alkanol, alkylamine, dialkylamine, trialkylamine or pyridine, D is a benzene or naphthalene diazo component, Y is the nitrogen atom or the CH group, K is a coupling component, R is hydrogen, alkyl or phenyl, X is a fibre-reactive group,Ka is a cation, m is 1, 2 or 3, n is 1 or 2 and k is 0 or 1. These chromium complexes are suitable for dyeing nitrogen-containing or hydroxy-containing materials and they produce level dyeings having good all-round fastness properties.

Fibre-reactive chromium complexes and their preparation and use

Metal complex dyes that produce level, fast dyeings on textile materials are provided according to the formula ##STR1## wherein: D is a benzene, naphthalene or heterocyclic radical of a diazo component;

Metal dye complexes containing an azo or azomethine dye and a colorless

Disclosed are chrome complex dyes of the formula ##STR1## and of the formula ##STR2## wherein Z and Z' independently of one another are each nitrogen or --CH--;

Bis 1:2 chromium complexes of disazo and azo or azomethine dyes

1:2 chromium complex dyes suitable for dyeing nitrogen-containing materials and materials which contain hydroxyl groups, are disclosed which, in the form of the free acid, have the formula ##STR1## wherein each of the symbols independently has the following meanings: Z is nitrogen or a --CH,

A process for the manufacture of 2,4,6-triamino-5-nitro-pyridines of the general formula ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 represents a hydrogen atom, a substituted or unsubstituted aryl, aralkyl or cycloalkyl group or an aliphatic group, and R.sub.1 and R.sub.2, R.sub.3 and R.sub.4, and R.sub.5 and R.sub.6 together can form a ring which contains the amino-nitrogen, which process comprises

Process for the manufacture of nitroaminopyridines

An azo dyestuff of the formula ##STR1## wherein two of the radicals Z denote groups of the formula --NR'R' and one radical Z denotes a group of the formulae --NR'R', --OR' or --S-R', and R' and R' and R' each denote hydrogen, aryl, aralkyl, cycloalkyl or an aliphatic radical and R' and R' can form a ring containing the amine nitrogen and the radicals --NR'R' can be identical to, or different from, one another, Z.sub.3 is also a hydrogen, chlorine or bromine atom or an optionally substituted hydrocarbon radical and D is the radical of an aromatic or heterocyclic diazo component. The new dyestuffs dye synthetic fibers, such as polyester and acrylic fibers in fast yellow, and red shades.

Growing community of inventors

Binzen, Germany

Ulrich Schlesinger