Ciba-geigy Corporation

Other

Ciba-geigy Ag

Hans U Schutz

Gerhard Back

Arthur Buhler

Fabio Beffa

Ulrich Schlesinger

Gerhard Reinert

Gert Hegar

Visvanathan Ramanathan

Helmut Raisin

Thys Bouwknegt

Angelo Della Casa

Rene De Montmollin

Peter Donath

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

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 monoanionic bidentate complexible organic compound which is bonded to the chromium atom via oxygen atoms, L is a colorless monofunctional ligand, X is halogen-substituted C.sub.1-4 -alkanoyl, C.sub.1-4 -alkenoyl, halogen-substituted C.sub.1-4 -alkenoyl, monohalogenopyrimidinyl, dihalogenopyrimidinyl or trihalogenopyrimidinyl which is bonded to A and/or B via ##STR2## and R.sub.5 is hydrogen or C.sub.1-4 -alkyl, Ka is a cation, m is 1, 2 or 3, n is 1 or 2 and the SO.sub.3.sup..crclbar. Ka group is bonded to A and/or B. 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-reaction 1:1 chromium complex azo or azomethine dyes having a

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

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

A process of dyeing polyamide-containing material is disclosed using dyes of the following formula: ##STR1## wherein Me is cobalt or chromium,

1:2 chromium or cobalt metal complex dyes and use thereof for dyeing

A process for the photochemical stabilization of fibre materials made of synthetic polyamides, which comprises treating the fibre material with at least one water-soluble copper complex dye or with a mixture of copper complex compounds containing at least one copper complex dye, or containing at least one copper complex dye in combination with a water-soluble 1:2 cobalt complex dye, 1:2 chromium complex dye, or an azo, anthraquinone, nitroaryl or dioxazine dye. The fibre materials treated (dyed) by the process of the invention are distinguished by very high tear strength and elongation values after exposure to light or exposure to hot light.

Process for the photochemical stabilization of synthetic polyamide fibre

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

Chromium complex dyes which, in the form of the free acid, have the formula ##STR1## wherein Z is hydrogen, nitro, chlorine or naphthylazo or phenylazo, wherein naphthyl or phenyl is unsubstituted or substituted by nitro, chlorine, bromine, C.sub.1-5 -alkyl or C.sub.1-5 -alkoxy, A is naphthyl or phenyl containing the oxygen atom in o-position to the azomethine and wherein naphthyl or phenyl is unsubstituted or substituted by C.sub.1-5 -alkyl, halogen or naphthylazo or phenylazo wherein naphthyl or phenyl is unsubstituted or substituted by nitro, chlorine, bromine, C.sub.1-5 -alkyl or C.sub.1-5 -alkoxy, D is sulfophenyl which is unsubstituted or substituted by nitro or chlorine, or sulfonaphthyl which is unsubstituted or substituted by nitro, and is bonded to the azo group in the ortho-position to the oxygen atom and R is chloroacetyl, bromoacetyl, .alpha.-chloroacryloyl, .alpha.-bromoacryloyl, .alpha.,.beta.-dichloropropionyl, .alpha.,.beta.-dibromopropionyl, 5-chloro-2,4-difluoropyrimidyl or 2-chloro- or 2-fluorotriazin-6-yl substituted in 4-position by substituted or unsubstituted amino, free or etherified hydroxy or mercapto. These dyes are obtained by chroming the corresponding o,o'-dihydrokyazo compounds and o,o'-dihydroxyazomethine compounds, the reactive radical R being introduced by acylation before or after the chroming. They are suitable for dyeing natural or synthetic polyamide material.

Fibre-reactive chromium complex Azo-azomethine dyes

The present invention relates to a process for the differential dyeing of such polyamide fibres and materials containing polyamide fibres as are made of components which differ in dyeability, or mixtures of polyamide fibres, with dyes or dye mixtures, which comprises using for dyeing these materials an aqueous liquor which contains a dye of the formula ##STR1## in which A.sub.1 is hydrogen or C.sub.1-4 alkyl and R is a C.sub.2-5 -alkanoyl, C.sub.3-6 -alkenoyl, (C.sub.1-4 -alkoxy)carbonyl, phenoxycarbonyl, C.sub.1-4 -alkylsulfonyl or phenylsulfonyl radical which can be substituted in the alkyl, alkenyl, alkoxy, phenoxy or phenyl moiety, or a mixture of a dye of the formula (1) with a monosulfo-containing anthraquinone dye, and to those dyes of the formula (1) in which A.sub.1 is as defined above and R is a C.sub.1-4 -alkylsulfonyl or phenylsulfonyl radical which can be substituted in the phenyl moiety by C.sub.1-4 -alkyl. Even at low dyeing temperatures, the process of the invention gives ombre effects rich in contrast and, on admixture of other suitable acid dyes, multicolor effects on polyamide fibres which are suitable for differential dyeing.

Process for dyeing differential-dyeing polyamide fibres

The present invention relates to copper, nickel, chromium or cobalt complexes of azo or azomethine dyes which contain a group of the formula ##STR1## wherein Z is a bridge Member of the formula

Metalized dyes, their manufacture and use

Chromium complex dyes which, in the form of the free acid, have the formula ##STR1## wherein Z is hydrogen, nitro, chlorine, or an arylazo group, Q is a nitrogen atom or the CH-- group, A is the radical of a coupling component which couples in the ortho-position to the oxygen atom if Q is a nitrogen atom, or is the radical of an o-hydroaldehyde if Q is the CH-- group, D is a sulfophenyl radical which can be substituted by nitro or chlorine, or a sulfonaphthyl radical which can be substituted by nitro and is bonded to the azo group in the orthoposition to the oxygen atom, and R is a reactive group. These dyes are obtained by chroming the corresponding o,o'-dihydroxyazo compounds or o,o'-dihydroxyazomethine compounds, the reactive radical R being introduced by acylation before or after the chroming. They are suitable for dyeing natural or synthetic polyamide material.

Fiber-reactive unsymmetrical 1:2 chromium complex azo dyes

Cobalt and chromium complex dyes which contain, bonded to a metal atom, one molecule of each of the azo compounds of the formula ##STR1## wherein R is methyl or ethyl and the phenyl ring a is unsubstituted or substituted by 1 to 2 chlorine atoms, nd mixtures thereof with the symmetrical 1:2 cobalt or chromium complex dyes of the azo compounds of the formulae (1) and (2), said dyes being useful in the dyeing and printing of a variety of materials, especially nitrogen containing materials such as silk, leather, polyamides, polyurethanes and especially wool to obtain level dyes having good fastness to light, washing, water, hot water, fulling, decatizing and carbonizing.

1:2 Cobalt and chromium complex unsymmetrical azo dyes

The present invention relates to copper, nickel, chromium or cobalt complexes of azo or azomethine dyes which contain a group of the formula

Novel metallized dyes, their manufacture and use

The invention relates to the chromium complex dye of the formula ##STR1## wherein Me.sup..sym. is a cation, useful for dyeing nitrogenous materials to produce dyeings which are level and have good fastness to light, washing, fulling, decatizing and carbonizing.

Sulfo substituted chromium containing azo pyrazolone dyestuff

The present invention relates to copper and nickel complexes of the formula ##STR1## wherein Me is copper or nickel;

Growing community of inventors

Basel, Switzerland

Hans U Schutz