Ciba-geigy Corporation

Ciba Specialty Chemicals Corporation

Ciba-geigy Ag

Rudolf Hurter

Harald Walter

Jean-Marie Adam

Hansrudolf Schwander

Dieter Mausezahl

Alfred Fasciati

Francine Casi

Dye mixtures, which comprise at least one dye of formula ##STR1## and at least one dye of formulae (2) and (3) ##STR2## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 R.sub.5, R.sub.6 R.sub.7, X.sub.1, X.sub.2, A.sub.1, A.sub.2, A.sub.3 and A.sub.4 are as defined in claim 1. The dye mixtures according to this invention are particularly suitable for dyeing or printing natural or synthetic polyamide fiber material.

Dye mixtures, process for their preparation and the use thereof

A process for dyeing or printing natural or synthetic polyamide fiber material by the trichromatic technique, which comprises using at least one blue-dyeing dye of formula ##STR1## together with at least one red-dyeing dye of formula ##STR2## together with at least one yellow- or orange-dyeing dye of formula ##STR3##

Process for trichromatic dyeing or printing

Azo dyes of the formula ##STR1## in which R.sub.1 is hydrogen or substituted or unsubstituted phenylamino,

Diazo dyes having a phenylene group as the middle component and a

Azo dyes of the formula (1) ##STR1## in which R.sub.1 and R.sub.2 are hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkanoylamino, ureido or halogen, X is chlorine or fluorine, B.sub.1 is phenyl, naphthyl or heterocyclic radical, and A.sub.1 is a radical of the formula (2) ##STR2## in which R.sup.7 is hydrogen, amino, N-mono- or N,N-di-C.sub.1 -C.sub.4 alkylamino or optionally substituted phenylamino and R.sub.8 is hydrogen or hydroxyl, or A.sub.1 is a radical of the formula (3) ##STR3## in which R.sub.9 is hydrogen, C.sub.1 -C.sub.8 alkyl or phenyl which is optionally substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.2 -C.sub.4 alkanoylamino, ureido, halogen or sulfo, R.sub.10 is hydrogen or C.sub.1 -C.sub.8 alkyl and R.sub.11 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkanoylamino, ureido, halogen or sulfo, and the azo dyes of the formula (1) contain at least one and not more than two sulfo groups, with the proviso that the radical of the formula (2) is not 6-sulfonaphth-2-yl, are particularly suitable for dyeing or printing cellulosic fibre materials or naturally occurring or synthetic polyamide fibre materials.

Azo dyes having two monoazo-chromophores bound to a halotriazinyl

The invention relates to azo dyes of formula ##STR1## wherein A, B and R.sub.1 are as defined in claim 1. The azo dyes of formula (1) give dyeings of good fastness properties on nitrogen-containing or hydroxy group-containing fibre materials, paper or leather.

Azo dyes and preparation and use thereof

Azo dyes of the formula ##STR1## where A and B are each independently of the other substituted or unsubstituted phenyl or naphthyl and X is --N(R.sub.1)--SO.sub.2 --, --O--SO.sub.2 -- or --SO.sub.2 --N(R.sub.1)--, where R.sub.1 is hydrogen or C.sub.1 -C.sub.8 alkyl, produce very fast dyeings on nitrogen-containing or hydroxyl-containing fibre materials, paper or leather.

Disazo dyes which contain 2-hydroxynaphthyl moiety

A compound of the formula ##STR1## in which R.sub.1 and R.sub.2 independently of one another are each C.sub.1 -C.sub.10 alkyl which is unsubstituted or substituted by hydroxyl, C.sub.1 -C.sub.4 alkoxy, phenyl, sulfo, sulfato, thiosulfato, cyano or halogen, C.sub.5 -C.sub.7 cycloalkyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, or C.sub.1 -C.sub.4 alkoxy, or phenyl or naphthyl which both are unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkanoylamino, benzoylamino, halogen or sulfo, R.sub.3 is hydrogen, halogen, C.sub.1 -C.sub.10 alkyl which is unsubstituted or substituted by hydroxyl, C.sub.1 -C.sub.4 alkoxy, phenyl, sulfo, sulfato, thiosulfato, cyano or halogen, C.sub.1 -C.sub.10 alkoxy which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkoxy, or phenoxy which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkanoylamino, benzoylamino, halogen or sulfo, X is --CO-- or --SO.sub.2 --, n is the number 1,2,3,4,5 or 6 and M is a cation.

Compounds containing a 3-sulfoalkanoylamino or

The present invention relates to azo dyes of the formula ##STR1## wherein X is an aryloxy radical or an unsubstituted or substituted C.sub.1 -C.sub.12 alkyl radical, a cycloalkyl radical or an aryl radical or a group of the formula ##STR2## wherein R.sub.1 is hydrogen, unsubstituted or substituted lower alkyl, cycloalkyl or aryl, and R.sub.2 is hydrogen or unsubstituted or substituted lower alkyl, or wherein R.sub.1 and R.sub.2, together with the nitrogen atom to which they are attached, form a 5- or 6-membered heterocyclic ring which may contain a further hetero-atom, Y is halogen, low molecular alkyl or low molecular alkoxy, and K is the radical of a coupling component of the benzene or naphthalene series or of the heterocyclic series. These dyes yield dyeings of good light- and wetfastness on polyamide material.

Azo dyes and the production and use thereof

Monoazo dyes of the formula ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, C.sub.2 -C.sub.4 alkanoylamino or is an unsubstituted or substituted arylsulfonyl, aryloxy or arylcarbonyl radical; R.sub.2 is hydrogen, halogen, an unsubstituted or substituted alkyl, aryloxy or aryloxysulfonyl radical or a radical of the formula ##STR2## R.sub.3 is an unsubstituted or substituted alkyl or aryl radical; R.sub.4 is hydrogen or alkyl; and R.sub.5 and R.sub.6 are each independently hydrogen or an unsubstituted or substituted alkyl, cycloalkyl or aryl radical, with the proviso that R.sub.1 may not be hydrogen or halogen if R.sub.2 is an unsubstituted or substituted aryloxysulfonyl radical, a radical of the formula ##STR3## or the trifluoromethyl group, and the sulfo group is attached to the benzene ring of the indole radical, produce dyeings of good light- and wetfastness properties on polyamide material. In particular, the dyeings obtained have shade constancy when subjected to increases in temperature.

Substituted phenylazosulfoindole dyes

The azo dyes of the formula ##STR1## in which D is a diazo component, R.sub.1 and R.sub.2 independently of one another are each a C.sub.1 -C.sub.10 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl or naphthyl radical each of which is substituted or unsubstituted, or R.sub.1 and R.sub.2, together with the nitrogen atom linking them, are a 5-membered, 6-membered or 7-membered ring each of which is unsubstituted or substituted by heteroatoms, R.sub.3 is hydrogen, halogen or a C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxy or phenoxy radical each of which is substituted or unsubstituted, X is --CO-- or --SO.sub.2 --, n is the number 1, 2, 3, 4, 5 or 6 and M is a cation, produce dyeings of good fastness properties on fibre materials containing nitrogen or containing hydroxyl groups. This application also relates to the preparation and use of said azo dyes and to intermediates utilized in the preparation of said azo dyes.

Monoazo dyes containing a 3-sulfoalkanoylamino or

Monoazo dyes containing sulfoindole coupling components

The invention relates to monoazo dyes of the formula ##STR1## wherein K is the radical of a coupling component of the benzene, naphthalene or heterocyclic series, and R is hydrogen, halogen, carboxy, a C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.2 -C.sub.6 alkanoylamino, C.sub.1 -C.sub.6 alkylsulfonylamino, C.sub.1 -C.sub.6 alkylsulfonyl, phenyl(C.sub.1 -C.sub.4)alkylsulfonyl or naphthyl(C.sub.1 -C.sub.4)alkylsulfonyl or benzoyl radical, which radicals may be further substituted, or is a ##STR2## group, wherein each of R.sub.1 and R.sub.2 independently of the other is hydrogen or a C.sub.1 -C.sub.6 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl or naphthyl radical, which radicals may be further substituted, and wherein X is hydrogen, halogen or a C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.2 -C.sub.6 alkanoylamino or C.sub.1 -C.sub.6 alkylsulfonylamino radical, which radicals may be further substituted. These dyes give dyeings of good light- and wetfastness properties on polyamide material.

Monoazo dyes, process for their preparation, and the use thereof

The present invention relates to monoazo dyes which dye polyamide material with good light- and wet-fastness and which have the formula ##STR1## in which K is the radical of an amino- or alkoxy-benzene, amino- or alkoxy-naphthalene, naphthol, aminonaphthol, pyrazolone, aminopyrazole, indole, naphthimidazole, diphenylamine, tetrahydroquinoline or acetoacetamide and can be further substituted, R is hydrogen, halogen, C.sub.1-6 -alkyl, trifluoromethyl, carboxyl or a --SO.sub.2 --C.sub.1-6 --alkyl, --SO.sub.2 --R.sub.1, ##STR2## --CO--R.sub.4 group, in which R.sub.1 is a substituted or unsubstituted phenyl- or naphthyl-C.sub.1-4 -alkyl radical, R.sub.2 and R.sub.3 independently of one another are hydrogen or a substituted or unsubstituted C.sub.1-6 -alkyl or C.sub.5-7 -cycloalkyl radical and R.sub.4 is a substituted or unsubstituted phenyl radical, and X is hydrogen, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy or halogen, and in which R in formula (1) may not be hydrogen or chlorine if the radical --N.dbd.N--K is bonded to the phenyl ring in the o-position relative to the --SO.sub.2 -- group and K is the radical of an aminonaphthalenesulfonamide or a 2-amino-8-hydroxynaphthalene-6-sulfonic acid.

Monoazo dyes containing as the azo component A phenylsulfonylphenyl

The monoazo dyes of the formula ##STR1## wherein R.sub.1 is N-ethylanilino or anilino which is substituted by C.sub.2 -C.sub.5 alkanoylamino, R.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl and R.sub.3 is halogen or C.sub.1 -C.sub.4 alkyl, produce dyeings and prints of good lightfastness and wetfastness properties on polyamide fibre materials.

3-methyl-1-phenyl-5-pyrozolone-4-azo-1'-(3'-chloro-S-tri

The monoazo dyes of the formula ##STR1## in which K is the radical of a coupling component of the aminobenzene, alkoxybenzene, hydroxybenzene, pyrazolone, aminopyrazole, pyrimmidine, indole, diphenylamine or acetoacetamide series, R is a substituted or unsubstituted C.sub.1-12 alkyl, cycloalkyl, aralkyl or aryl radical, X is a --CO-- or --SO.sub.2 -- group, a --COO-- group, R being attached to the oxygen atoms, or an --SO.sub.2 NH-- or ##STR2## group, R being attached to the nitrogen atom and Y being hydrogen or C.sub.1-4 alkyl, and Z is hydrogen or C.sub.1-4 alkyl, produce dyeings having good fastness to light and wet processing on polyamide material.

Growing community of inventors

Basel, Switzerland

Rudolf Hurter