Ciba-geigy Corporation

Ciba Specialty Chemicals Corporation

Huntsman Advanced Materials LLC

Paul Herzig

Athanassios Tzikas

Antoine Clement

Anton Andreoli

Peter Aeschlimann

Rolf Deitz

Alfons Arquint

Romeo Dreier

Jurgen Markert

Claudia Carisch

Antoine Clément

Disperse dyes of formula ##STR1## wherein R is nitro or cyano, R.sub.1 is halogen, R.sub.2 is C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by C.sub.1 -C.sub.3 alkoxy, halogen, cyano or phenyl, R.sub.3 is C.sub.1 -C.sub.4 alkyl, R.sub.4 is methyl or ethyl, R.sub.5 is hydrogen, methyl or ethyl, and R6 is methyl or ethyl, with the proviso that R.sub.5 is not hydrogen if R is nitro, R.sub.1 is halogen and R.sub.2 is C.sub.1 -C.sub.4 alkyl. These dyes are particularly suitable for dyeing and printing textile materials consisting of polyester fibres.

Disperse dyes

Disperse azo dyes of formula ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.2 alkyl, halogen, NH--CO--R.sub.5 or O--SO.sub.2 --R.sub.6 ; R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, unsubstituted C.sub.1 -C.sub.8 alkoxy or C.sub.1 -C.sub.8 alkoxy which is substituted by halogen, cyano, phenyl, --Y--C.sub.1 -C.sub.8 alkyl or --Y-phenyl; R.sub.3 is unsubstituted C.sub.1 -C.sub.8 alkyl or C.sub.1 -C.sub.8 alkyl which is substituted by hydroxy, cyano, vinyl, phenyl, halogen, --X-phenyl or --X--C.sub.1 -C.sub.8 alkyl, and --X--C.sub.1 -C.sub.8 alkyl may be substituted by halogen or cyano and --X-phenyl may be substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen; R.sub.4 is hydrogen or, independently of R.sub.3, has the meaning of R.sub.3, and R.sub.3 and R.sub.4, together with the linking nitrogen atom, can also be a heterocyclic radical; R.sub.5 is unsubstituted C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkyl which is substituted by halogen, phenyl, cyano or C.sub.1 -C.sub.3 alkoxy; R.sub.6 is unsubstituted C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkyl which is substituted by halogen, cyano or phenyl, and phenyl in turn may be substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen; Y is a linking group of formula --O--, --S-- or --SO.sub.2 --; and X is a linking group of formula --O--, ##STR2## The novel disperse azo dyes of formula (1) are suitable in particular for dyeing polyester textile material.

Phthalimidylazo dyes, process for their preparation and the use thereof

The present invention describes a process for dyeing or printing fiber material by the pigment dyeing or pigment printing process, which comprises applying to the fiber material, and subsequently fixing, a dyeing liquor or a print paste comprising at least one dye of the formula

Pigment dyeing and pigment printing process

A dye mixture, which comprises as component (A) a dye of formula as component (B) a dye of formula ##STR1## and/or as component (C) a dye of formula ##STR2## wherein D, X and Y are as defined in the specification. These dyes are particularly suitable for dyeing polyester fiber textile material.

Azo dye mixtures

Disperse dyes of formula wherein R is nitro or cyano, R.sub.1 is halogen, R.sub.2 is C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by C.sub.1 -C.sub.3 alkoxy, halogen, cyano or phenyl, R.sub.3 is C.sub.1 -C.sub.4 alkyl, R.sub.4 is methyl or ethyl, R.sub.5 is hydrogen, methyl or ethyl, and R.sub.6 is methyl or ethyl, with the proviso that R.sub.5 is not hydrogen if R is nitro, R.sub.1 is halogen and R.sub.2 is C.sub.1 -C.sub.4 alkyl. These dyes are particularly suitable for dyeing and printing textile materials consisting of polyester fibres.

Disperse dyes of formula ##STR1## wherein R.sub.1 is chloro or bromo,

Described are compounds of formula ##STR1## which are suitable as fibre-reactive dyes for dyeing and printing a very wide range of different fibre materials.

Azo reactive dyes, their preparation and use

Mixtures comprising a compound of the formula ##STR1## and a compound of the formula ##STR2## in which K is the radical of a coupling component, s is the same in the compounds of formulae (16a) and (16b) and is the number 1 or 2, R and R' are each hydrogen, sulfo, hydroxyl, C.sub.1 -C.sub.4 alkoxy, halogen or cyano, A is C.sub.1 -C.sub.6 alkylene which is optionally substituted by halogen, hydroxyl, sulfato, carboxyl, cyano, C.sub.2 -C.sub.4 alkanoyloxy, C.sub.1 -C.sub.4 alkoxycarbonyl or carbamoyl or interrupted by a group --O-- or --NR'--, or is C.sub.1 -C.sub.6 alkylenephenylene which is unsubstituted or substituted in the phenyl part by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen or sulfo, and R' is hydrogen or C.sub.1 -C.sub.4 alkyl, and the ratio of the compounds of formulae (16a) and (16b) is about 1:1, are suitable as fibre-reactive dyes for dyeing or printing widely varying fibre materials.

Mixtures of fibre-reactive ring-opened phthalimidylazo dyes

Compounds of the formula ##STR1## in which the variables are as defined in the claims and which are suitable diazo components for the synthesis of fibre-reactive dyes are described.

Intermediates for reactive dyes

Reactive dyes of the formula ##STR1## where A, K and Z are each as defined in the claims, are especially useful for dyeing or printing cellulosic fiber materials, producing dyeings and prints having good fastness properties in a high yield.

Disazo dyes with a vinylsulfonyl type fiber-reactive radical substituted

The invention relates to compounds of the formula ##STR1## where the variables are each as defined in the claims. The compounds are suitable for use as dyes, in particular for dyeing and printing cellulose-containing fibre materials and produce dyeings and prints having good allround fastness properties.

Fiber-reactive triazine dyes with one AZO chromophore having a

Compounds of the formula ##STR1## in which the variables are as defined in the claims, which are suitable as fibre-reactive dyes for dyeing or printing widely varying fibre materials, are described.

Fiber reactive phthalimidylazo dyes and use thereof

Reactive dyes of the formula ##STR1## in which D, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined in claim 1, are particularly suitable for dyeing or printing cellulosic fiber materials or naturally occurring or synthetic polyamide fiber materials with a high tinctorial yield, and produce dyeings and prints having good fastness properties.

Reactive dyes containing a 2,6-diaminopyridine coupling component

The invention relates to reactive dye mixtures comprising the reactive dyes of the formulae ##STR1## in which X.sub.1, X.sub.2 and X.sub.3 are reactive radicals bonded via a diaminoalkylene bridge and the other substituents are as defined in claim 1. The reactive dye mixtures are suitable for dyeing and printing cellulosic fibre materials and give wet- and light-fast dyeings in luminous blue shades.

Reactive dye mixtures, processes for their preparation and their use:

There is disclosed a process for the preparation of compounds of formula ##STR1## wherein the symbols are as defined in claim 1, which process comprises dissolving a compound of formula ##STR2## in sulfuric acid, adding this solution to oleum and reacting the mixture in the temperature range from 10.degree. to 80.degree. C. until a sulfo group has been completely introduced, and, in an optional further step, subjecting the reaction mixture to further reaction in the temperature range from 100.degree. to 200.degree. C. to introduce a second sulfo group. The compounds of formula (1) obtainable by this process are useful intermediates for the synthesis of dyes and are particularly suitable diazo components for the synthesis of azo dyes.

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Basel, Switzerland

Paul Herzig