Ciba-geigy Corporation

Ciba-geigy Ag

Hansrudolf Schwander

Christian Zickendraht

Peter Loew

Siegfried Dengler

Kurt Burdeska

Peter Aeschlimann

Rudolf Hurter

Athanassios Tzikas

Rudolf Zink

Haukur Kristinsson

Stefan Koller

Dieter Mausezahl

Horst H Jager

Urs Karlen

Jurgen Markert

Jacques Bersier

Peter Furrer

Reactive dyes which are particularly suitable for dyeing and printing cellulose containing fiber materials by the cold padbatch process and which produce, in high dye yield, dyeings and prints having good fastness properties containing the radical of an amine of the formula ##STR1## in which R is hydrogen, halogen, hydroxyl or sulfo, Z is a radical of the formula --CH.dbd.CH.sub.2 or --CH.sub.2 --CH.sub.2 --Y, Y is a detachable group, R' is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by --COOH, --CN, --OH or --SO.sub.3 H, and E is a radical of the formula ##STR2## in which R' and Z are as defined above, alk, alk' and alk' independently of one another are a C.sub.1 -C.sub.6 alkylene radical, U is hydrogen, halogen, hydroxyl, sulfato, C.sub.1 -C.sub.4 alkanoyloxy, cyano, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, carbamoyl or a radical --SO.sub.2 --Z in which Z is as defined above, V is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 alkyl or a radical of the formula ##STR3## in which Z, alk and U are as defined above, and q, r and s independently of one another are an integer from 1 to 6.

Fiber-reactive dyes containing an aniline radical which carries two

The dyes of formula (1) as indicated in claim 1 are obtained by reacting 1-aminoanthraquinones with malodinitrile in the presence of titanium tetrachloride and a tertiary amine. These dyes are suitable e.g. for dyeing polyester material.

Dicyanobenzanthrone compounds

Novel monoazo compounds of the formula I ##STR1## and mixtures of these compounds with one another are described. The substituents X, R, R.sub.1, R.sub.2 and R.sub.3 are defined as follows: R is a phenyl or naphthyl radical which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, or is a cycloalkyl radical which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, or is a C.sub.1 -C.sub.8 -alkyl radical which is unsubstituted or substituted by cyano, halogen, phenyl or sulfophenyl, or is a propenyl radical which is unsubstituted or substituted by halogen, X is hydrogen or halogen, R.sub.1 is hydrogen or a C.sub.1 -C.sub.4 -alkyl radical, R.sub.2 is C.sub.1 -C.sub.8 -alkyl radical, a C.sub.1 -C.sub.4 -sulfatoalkyl radical, a C.sub.1 -C.sub.4 -sulfoalkyl radical or a cycloalkyl radical and R.sub.3 is a C.sub.1 -C.sub.4 -alkyl radical, or is a cycloalkyl radical which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, or is a ##STR2## radical, in which the phenyl radical can also be substituted, by --SO.sub.3 H, with the condition that the molecule contains a sulfo group in R, R.sub.2 or R.sub.3 or a sulfato group in R.sub.2. The novel monoazo compounds are particularly suitable as dyes for dyeing and printing textile materials, in particular wool and polyamide.

Water soluble phthalimide-azo-aniline dyes and mixtures thereof

Reactive dyes of the formula ##STR1## wherein Y is a --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --X radical, in which X is a leaving group, and Z is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or carboxy, and K is the radical of a coupling component which couples at pH.ltoreq.7, are suitable for dyeing and printing textile fibre material and give dyeings and prints of good fastness properties.

Reactive dyes, process for their preparation and use thereof: bis-vinyl

Monoazo dyes of the formula ##STR1## in which K is a radical of the formula ##STR2## or of the formula ##STR3## in which R.sub.1 and R.sub.2 independently of one another is (sic) hydrogen, C.sub.1-4 -alkyl, which can be substituted by halogen, cyano, hydroxyl, carboxyl, sulfo, sulfato, C.sub.1-4 -alkoxy, C.sub.1-4 -alkoxycarbonyl, C.sub.1-4 -alkanoyloxy, phenyl, sulfophenyl and naphthyl, or cyclohexyl, or C.sub.1-4 -alkenyl, which can be substituted by halogen, or phenyl or naphthyl, or in which R.sub.1 and R.sub.2, together with the nitrogen atom connecting them and where relevant with the inclusion of a further hetero-atom, form a heterocyclic 5-membered or 6-membered ring, R.sub.3 is hydrogen, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, which can be substituted by hydroxyl and C.sub.1-4 -alkoxy, or C.sub.1-4 -alkanoylamino, or benzoylamino, which can be substituted in the benzene nucleus by methyl, ethyl, methoxy, ethoxy, chlorine, carboxyl and sulfo, or ureido, C.sub.1-4 -alkylsulfonylamino, or phenylsulfonylamino, which can be substituted in the benzene nucleus by methyl, ethyl, methoxy, ethoxy, chlorine, carboxyl and sulfo, or naphthylsulfonylamino, R.sub.4 is methyl or phenyl and R.sub.5 is hydrogen or C.sub.1-8 -alkyl, and in which, if K is the radical of the formula (2), R.sub.3 may not be hydrogen if R.sub.1 or R.sub.2 is benzyl, produce, on polyamide material, dyeings with good light fastness and wet fastness.

Azo dyes

There are described novel yellow to red azo compounds of the formula I ##STR1## wherein each D independently of the other is the radical of an aromatic or heterocyclic diazo component, each Z independently of the other is hydrogen or a C.sub.1 -C.sub.4 -alkyl group or an acylamino group, Y is hydrogen or an unsubstituted or substituted C.sub.1 -C.sub.6 -alkyl group, X is either the direct bond or C.sub.1 -C.sub.6 -alkylene, ##STR2## and n is a number from 2 to 6, preferably 2; and the substituent Y, in the case of an unsubstituted or substituted C.sub.1 -C.sub.6 -alkyl group, can also be bonded to the o-position relative to the N atom of the phenylene group to form a six-membered ring, or both Y substituents can be linked together to form a C.sub.1 -C.sub.6 -alkylene bridge; described also are processes for producing the novel compounds, and their use as dyes for dyeing and printing natural and synthetic textile materials, particularly polyamide and wool materials, and also cotton, whereby there are obtained dyeings which are distinguished by good general fastness properties, especially by a good dye build-up, very good fastness to wet processing, good fastness to light, and good resistance to formaldehyde and good stability to hydrolysis.

Bis(4-((chloro substituted phenyl)azo)anilino methylenes

s-Triazine compounds of the formula: ##STR1## in which R.sub.1 and R.sub.2 independently of one another are C.sub.1-4 alkyl, R.sub.3 and R.sub.4 independently of one another are one of the following radicals; C.sub.1-10 alkoxy which is unsubstituted or substituted by alkoxy; N-C.sub.1-10 alkylamino which is unsubstituted or substituted by phenyl; phenylamino which is unsubstituted or substituted by halogen, C.sub.1-4 alkyl or C.sub.1-4 alkoxy; naphthylamino which is unsubstituted or substituted by halogen, C.sub.1-4 alkyl or C.sub.1-4 alkoxy; halogen; N-phenyl-N-alkylamino; dialkylamino; alkylmercapto; cyclohexyloxy; N-alkyl-N-cyclohexylamino and cyclohexylamino; M is hydrogen or one equivalent of a cation and n is 1 or 2. These compounds may be used in the preparation of dyes.

s-Triazines

The patent discloses novel monoazo compounds, and mixtures of monoazo compounds, of the formula ##STR1## in which Hal.sub.1 and Hal.sub.2 independently of one another are each a halogen atom, X is a CF.sub.3, CN or SO.sub.2 --A group, in which A is a substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl group or a di-(C.sub.1 -C.sub.4)-alkyl-amino group, in which the alkyl radicals can be substituted, R is a substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl group or a substituted or unsubstituted C.sub.1 -C.sub.4 -alkoxy group and Y is a substituted or unsubstituted C.sub.1 -C.sub.8 -alkyl group or a substituted or unsubstituted C.sub.3 -C.sub.4 -alkenyl group, as well as processes for their preparation, and their use as dyes for dyeing and printing textile materials which are dyeable with disperse dyes, especially polyester materials. The dyeings obtained in particular have very good light fastness, brilliance, sublimation fastness and freedom from 'catalytic fading'.

Trifluoromethyl-substituted monoazo disperse dyes

The invention provides novel monoazo compounds of the formula I ##STR1## wherein X is hydrogen or halogen, R is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.1 is C.sub.1 -C.sub.8 alkyl, cycloalkyl or ##STR2## wherein the phenyl radical can be monosulfonated, and R.sub.2 is C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by a sulfo group, or is cycloalkyl, with the proviso that either R.sub.1 or R.sub.2 contains a sulfo group. The invention also provides a process for the production of the compounds of the formula I, as well as an intermediate of the formula IIb ##STR3## The novel monoazo compounds can be used as dyes for dyeing and printing textile material, especially wool and polyamide.

Monoazo compounds

An electrochemical process for the production of benzanthrone by reaction of anthraquinone as, starting material, with glycerol, which process comprises reducing anthraquinone, which may additionally contain electronegative substituents, at the cathode in an electrolytic cell in acid medium, and simultaneously cyclizing the reduced semiquinone form with glycerol to produce the corresponding benzanthrone. The novel process affords numerous advantages compared with chemical reduction methods.

Electrochemical process for the production of benzanthrone

A process for producing disperse dyes starting with anthraquinone compounds of the formula I ##STR1## in which one X is bromine and the other X is methylamine, or with mixtures thereof, which process comprises reacting these compounds with sulfuric acid, optionally containing SO.sub.3, in the presence of boric acid, at a temperature of between 100.degree. and 150.degree. C., to give compounds of the formula II ##STR2## in which one Y is hydroxyl and the other Y is methylamine, and n is 0.5 to 2.0, or mixtures thereof.

Process for producing disperse dyes

New Dyes of the formula ##STR1## are described wherein R represents alkyl, alkenyl or preferably hydrogen,

Naphtholactam dyes

An azo dyestuff which is free from groups conferring solubility in water and has the general formula I ##STR1## in which R denotes hydrogen, halogen, a hydrocarbon radical with up to 18 carbon atoms which is bonded by means of a direct bond or a sulphur or oxygen atom and can be substituted, trifluoromethyl, cyano, dichlorocyanomethyl, chlorodicyanomethyl, tribromomethyl or trichloromethyl or denotes a heterocyclic radical containing nitrogen, Hal is a halogen atom, R.sub.1 is an optionally substituted alkyl group and 'acyl' denotes the acyl radical of an organic carboxylic acid, carbamic acid, carbonic acid or sulphonic acid with, preferably up to 0.18 carbon atoms. The new dyestuffs dye polyester fibers in fast red shades.

Azo compounds, containing a 1,2,4-thiadiazole moiety

A naphtholactam dyestuff of the general formula (1) ##STR1## in which R represents C.sub.1 -C.sub.5 -alkyl, C.sub.1 -C.sub.5 -alkenyl, C.sub.6 -C.sub.9 -cycloalkyl, C.sub.6 -C.sub.9 -aralkyl, aryl or, preferably, hydrogen, X represents --COOH, --COO.sup..crclbar. cation.sup..sym., a modified carboxyl group, the radical --SO.sub.2 --T or a heterocyclic radical, T denoting alkyl, alkenyl or, preferably, aryl, M represents hydrogen or a cation, Y represents a free or modified carboxyl group, Z is C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, Cl, Br, NO.sub.2, phenyl sulphonyl C.sub.1 -C.sub.4 -alkyl-S, C.sub.1 -C.sub.4 -alkyl sulphonyl, cyano, CONH.sub.2, CONH-C.sub.1 -C.sub.4 -alkyl, and CON(C.sub.1 -C.sub.4 -alkyl).sub.2, n represents 0, 1 or 2, A represents a heterocyclic radical or --CN and B and C can carry further non-ionic substituents. The new dyestuffs give brilliant yellow and red shades on polyester and polyamide fibers.

Naphtholactam dyestuffs

A naphtholactam dyestuff of the general formula (I) ##STR1## in which R represents alkyl, alkenyl, cycloalkyl, aralkyl, aryl or, preferably, hydrogen, M represents hydrogen or a cation, X represents .dbd.O, .dbd.NH or .dbd.NR', Y represents a free or modified carboxyl group, Z represents a non-ionic substituent, n represents 0, 1 or 2, B represents a group which completes ring A to give a heterocyclic structure, R' represents alkyl, alkenyl, cycloalkyl, aralkyl, aryl, or, preferably, hydrogen and E and F can carry further non-ionic substituents. The new dyestuffs give brilliant yellow and red shades on polyester fibres.

Growing community of inventors

Riehen, Switzerland

Hansrudolf Schwander