Ciba-geigy Ag

Ciba-geigy Corporation

Christian Zickendraht

Hansrudolf Schwander

Peter Loew

Siegfried Dengler

Kurt Burdeska

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

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

Naphtholactam dyes

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.

A dyestuff of the formula ##STR1## in which R represents alkyl, alkenyl, cycloalkyl, aralkyl, aryl or, preferably, hydrogen, R.sub.1 represents alkyl, alkenyl, cycloalkyl, aralkyl, a heterocyclic structure or, preferably, aryl, X represents --COOH, --COO.sup..crclbar. cation.sup..sym., a modified carboxyl group, the radical --SO.sub.2 --T or a heterocyclic radical, T being alkyl, alkenyl or aryl, and M represents hydrogen or a cation and A and B can carry non-ionic substituents and/or a --COOH group. The new dyestuffs dye polyester fibers in fast yellow and orange shades.

A 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, Y represents a free or modified carboxyl group, Z represents a non-ionic substituent, n represents 0, 1 or 2, A represents a heterocyclic radical or an aromatic radical having negative substituents and B and C can carry further non-ionic substituents. The dyestuffs give brilliant red and yellow shades on polyester fibers.

Dyestuffs of the formula (I) ##STR1## wherein F represents a ring system with at least 3 rings which are angularly condensed with one another, n is 1, 2 or 3, and R, R.sub.1 and R.sub.2 represent optionally substituted alkyl groups which can be interrupted by heteroatoms and also represent cycloalkyl, aralkyl, aryl or heterocyclic radicals, R and R.sub.1 can also represent hydrogen atoms, R.sub.1 and R.sub.2, together with the nitrogen atom, are able to form a ring with 5 or 6 members, and R and R.sub.2 can combine to form a nitrogen-containing heterocycle.

Novel naphthoylene-perinones disperse dyestuffs

Dyestuffs of the formula (I) ##STR1## in which R represents alkyl, alkenyl, cycloalkyl, aralkyl, aryl or, preferably, hydrogen, M represents hydrogen or a cation, Y represents a free or modified carboxyl group, Z represents a non-ionic substituent and n represents 0, 1 or 2 and A, B and D can carry further non-ionic substituents are disclosed; the sulfo-free dyestuffs are suitable for dyeing semi-synthetic and synthetic fibers, especially polyamides and polyesters, and the sulfo-substituted dyestuffs are suitable for dyeing, for example, wool and synthetic polyamides.

Substituted

A dye of the formula ##STR1## WHEREIN R is alkyl, alkenyl, cycloalkyl, aralkyl or hydrogen,

Dispersion dyestuffs of the naphtholactam series

A dyestuff of the formula ##STR1## in which R represents alkyl, alkenyl, cycloalkyl, aralkyl, aryl or, preferably, hydrogen, M represents hydrogen or a cation, T represents the radical of a thiophene and A and B can carry non-ionic substituents and/or a --COOH group. The new dyestuffs give fast and brilliant yellow shades on polyester fibers.

Disperse dyestuffs

A dyestuff of the formula ##STR1## WHEREIN X.sub.1 represents fluorine, bromine, chlorine or hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, phenyl, phenoxy, thiophenoxy or C.sub.1 -C.sub.4 -alkyl sulphonyl, C.sub.1 -C.sub.4 -alkylthio, each of which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkoxy, hydroxy, cyano, bromine, chlorine, carbo-C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylcarbonyloxy, chloro-C.sub.1 -C.sub.4 -alkylcarbonyloxy or C.sub.1 -C.sub.4 -alkoxy-carbonyloxy, fluorine, bromine, chlorine, COOR, in which R represents C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkyl substituted by C.sub.1 -C.sub.4 -alkoxy, hydroxy, cyano, C.sub.1 -C.sub.4 -alkylcarbonyloxy, chlorine or bromine, --SO.sub.2 NH--C.sub.1 -C.sub.4 -alkyl and ##STR2## (WHEREIN THE C.sub.1 -C.sub.4 -alkyl is unsubstituted or substituted by hydroxy, chlorine, bromine, C.sub.1 -C.sub.4 -alkoxy or phenyl),

Disperse dyes

Dyestuffs of the formula ##STR1## wherein R, R.sub.1, and R.sub.2 represent optionally substituted alkyl groups that can be interrupted by heteroatoms, and also represent cycloalkyl, aralkyl, aryl, or heterocyclic radicals, R and R.sub.1 can also be hydrogen atoms, R.sub.1 and R.sub.2, together with the nitrogen atom, are able to form a 5-membered or 6-membered ring, R and R.sub.2 are able to combine to form a nitrogen-containing heterocycle, B is =O or =NH, and A represents a heterocycle. The new dyestuffs dye synthetic fibers, especially polyester fibers, in greenish yellow shades.

Coumarine dyestuffs of the dispersion series

Dyestuffs of the formula (I) ##EQU1## WHEREIN F represents a ring system with at least 3 rings which are angularly condensed with one another, n is 1, 2 or 3, and R, R.sub.1 and R.sub.2 represent optionally substituted alkyl groups which can be interrupted by heteroatoms and also represent cycloalkyl, aralykyl, aryl or heterocyclic radicals, R and R.sub.1 can also represent hydrogen atoms, R.sub.1 and R.sub.2, together with the nitrogen atom, are able to form a ring with 5 or 6 members, and R and R.sub.2 can combine to form a nitrogen-containing heterocycle.

Growing community of inventors

Binningen, Switzerland

Christian Zickendraht