US 4,155,903 AGranted

Asymmetrical 1:2 cobalt complexes of certain substituted phenylazonaphthalenes

AssigneeSandoz Ltd.

InventorJacky Dore

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Abstract

Disclosed are homogeneous complexes of the formula ##STR1## wherein R.sub.1 is hydrogen, alkyl, phenyl or substituted phenyl, ##STR2## WHEREIN ONE Q is hydrogen and the other is sulfo, and N IS 0 OR 1 (THE SULFO GROUP BEING IN THE 5- OR 6-POSITION WHEN N IS 1), R.sub.4 is hydrogen, alkyl, alkoxy, chloro, bromo or nitro, R.sub.5 is hydrogen, alkyl, alkoxy, chloro, bromo, nitro or sulfo, With the proviso that when one of R.sub.4 and R.sub.5 is hydrogen, the other is other than hydrogen and is in the 4- or 5-position and when both are other than hydrogen, one is in the 4-position and the other is in the 5- or 6-position, One of R.sub.6 and R.sub.7 is hydrogen, chloro or nitro and the other is hydrogen, sulfamoyl or substituted sulfamoyl, and ##STR3## wherein one of R.sub.10 and R.sub.11 is hydrogen and the other is hydrogen, chloro, alkyl, alkoxy or trifluoromethyl, R.sub.12 is hydrogen or methyl, R.sub.13 is methyl, chloro or bromo, with the proviso that R.sub.12 is hydrogen when R.sub.13 is chloro or bromo, Y.sub.1 is hydrogen or acylamino, Y.sub.2 is hydrogen, alkyl, alkoxy, chloro or bromo, Y.sub.3 is hydrogen or 5- or 6-sulfamoyl, alkylsulfamoyl or hydroxyalkylsulfamoyl, and M.sup..sym. is hydrogen or a non-chromophoric cation, wherein the asterisks indicate the carbon atom attached to the azo group, with the proviso that the complex contains a single sulfamoyl or substituted sulfamoyl group and a single sulfo group which is in salt form, and mixtures of such complexes. The complexes and mixtures are useful for dyeing and printing nitrogen-containing organic substrates, for example, polyamides such as wool, silk and nylon, polyurethanes and leather.

A homogenous complex of the formula ##STR20## or a mixture of such complexes, wherein R'.sub.1 is hydrogen or ##STR21## wherein R'.sub.3 is hydrogen or --SO.sub.3 M, R'.sub.4 is hydrogen, chloro or nitro,

R'.sub.5 is hydrogen, chloro, nitro or --SO.sub.3 M,
with the proviso that when only one of R'.sub.4 and R'.sub.5 is hydrogen, the one that is other than hydrogen is in the 4- or 5-position, and when both R'.sub.4 and R'.sub.5 are other than hydrogen, they are in the 4,5- or 4,6-positions,
one of R'.sub.6 and R'.sub.7 is --SO.sub.2 NHR'.sub.9 and the other is hydrogen,
wherein R'.sub.9 is hydrogen;
C.sub.1-3 alkyl;
C.sub.2-3 hydroxyalkyl;
methoxy(C.sub.2-4 alkyl);
ethoxy(C.sub.2-4 alkyl);
phenyl;
phenyl monosubstituted by chloro, nitro, methyl, methoxy or ethoxy or phenyl disubstituted by methyl, methoxy or ethoxy, ##STR22## wherein one of R.sub.10 and R.sub.11 is hydrogen, chloro, C.sub.1-2 alkyl, C.sub.1-2 alkoxy or trifluoromethyl and the other is hydrogen,
R.sub.12 is hydrogen or methyl,
R.sub.13 is methyl, chloro or bromo, with the proviso that when R.sub.13 is chloro or bromo, R.sub.12 is hydrogen,
Y.sub.1 is hydrogen, --NHCOR.sub.14, --NHCOOR.sub.15 or --NHSO.sub.2 NR.sub.16 R.sub.17,
wherein each of R.sub.14 and R.sub.15 is C.sub.1-4 alkyl;
C.sub.1-4 alkyl mono-substituted by halo, hydroxy, cyano, phenyl or C.sub.1-4 alkoxy;
phenyl;
phenyl monosubstituted by chloro, nitro, methyl, methoxy or ethoxy or phenyl disubstituted by methyl, methoxy or ethoxy,
R.sub.16 is hydrogen, methyl or ethyl, and
R.sub.17 is methyl or ethyl, and
Y.sub.2 is hydrogen, C.sub.1-2 alkyl, C.sub.1-2 alkoxy, chloro or bromo,
wherein the asterisk indicates the carbon atom attached to the --N.dbd.N-- radical,
M' is 0 or 1,
with the proviso that when m' is 1 the --SO.sub.3 M group is in the 5- or 6-position,
M.sup..sym. is hydrogen or a non-chromophoric cation, and M is a non-chromophoric cation,
with the provisos that (i) the complex contains a single --SO.sub.3 M group, and (ii) the complex is free of ##STR23##

22 more elements

Abstract

Claims24