US 5,212,313 AGranted

Polycyclic dyes

AssigneeImperial Chemical Industries PLC

InventorsRonald W. Kenyon, David F. Newton, Derek Thorp

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Abstract

Compounds of the Formula VII: ##STR1## Wherein: X.sup.1 and X.sup.2 are each independently selected from --H, cyano, alkyl, alkoxy, aryl, carbamoyl, sulphamoyl, COOH and carboxylic acid ester; Z.sup.2 and Z.sup.2 are both --O--; R.sup.1 and R.sup.2 are each independently selected from H, or an optionally substituted alkyl, alkenyl, cycloalkyl, aryl and aralkyl group; R.sup.4, R.sup.5, R.sup.7 and R.sup.8 are each independently --H, halogen or an optionally substituted alkyl, alkenyl or alkoxy group; or R.sup.1 and R.sup.4 or R.sup.2 and R.sup.5 together with N atom and Ring B from a tetrahydroquinolinyl group; and R.sup.6 is selected from H, halogen or an optionally substituted alkyl or alkoxy group and a group NR.sup.1 R.sup.2 in which each of R.sup.1 and R.sup.2 are independently as hereinbefore described and where R.sup.6 is NR.sup.1 R.sup.2, R.sup.6 is the same or different form the NR.sup.1 R.sup.2 group present in Ring B. These compounds are suitable for the coloration of polyester textile material in shades from green through to reddish-blue.

Claims6

Dependent claims

A compound of Formula VII:

##STR13## wherein;
X.sup.1 and X.sup.2 are each independently selected from H, cyano, C.sub.1-20 -alkyl, C.sub.1-4 -alkoxy, phenyl, carbamoyl, sulphamoyl, COOH and carboxylic acid ester;
Z.sup.1 and Z.sup.2 are both --O--;
R.sup.1 and R.sup.2 are each independently selected from H, C.sub.1-20 -alkyl, C.sub.2-20 alkenyl, C.sub.4-8 -cycloalkyl, phenyl and phenyl-C.sub.1-4 -alkylene each of which is unsubstituted or is substituted by a group selected from C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, nitro, halogen, C.sub.1-4 -alkoxy-C.sub.1-4 -alkoxy, cyclohexyl, phenyl, diphenyl, hydroxy, C.sub.1-4 -alkylcarbonyl, C.sub.1-4 -alkoxycarbonyl, C.sub.1-4 -alkoxy-C.sub.1-4 -alkoxycarbonyl, C.sub.1-4 -alkoxycarbonyloxy, C.sub.1-4 -alkoxy-C.sub.1-4 -alkoxycarbonyloxy, C.sub.1-4 -alkylcarbonyloxy, cyano and amino;
R.sup.1 and R.sup.2 together with the N atom and Ring B form a tetrahydroquinolinyl group;
or
R.sup.2 and R.sup.5 together with the N atom and Ring B form a tetrahydroquinolinyl group;
R.sup.6 is selected from H, halogen, C.sub.1-4 -alkyl, C.sub.3-4 -alkenyl, C.sub.1-10 -alkoxy group and a group NR.sup.1 R.sup.2 in which R.sup.1 and R.sup.2 are each independently as hereinbefore defined;
R.sup.4 and R.sup.5 each independently is --H, halogen, or a group selected from C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, and C.sub.1 -C.sub.10 alkoxy each of which may be substituted by a group selected from alkoxy, hydroxy, alkylcarbonyloxy, alkoxyalkoxycarbonyl, alkoxycarbonyl, halogen and cyano;
R.sup.7 and R.sup.8 each independently is --H, halogen, or a group selected from C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, and C.sub.1 -C.sub.10 alkoxy each of which may be substituted by a group selected from alkoxy, hydroxy, alkylcarbonyloxy, alkoxyalkoxycarbonyl, alkoxycarbonyl, halogen and cyano;
and where R.sup.6 is NR.sup.1 R.sup.2, then R.sup.6 is the same as or different from the NR.sup.1 R.sup.2 group present in Ring B, provided that one of R.sup.4 and R.sup.5 is other than H, and provided either X.sup.1 and X.sup.2 are different or the number or pattern of substituents in Ring A and Ring B are different.

8 more elements

A compound of Formula VII:

##STR14## wherein;
X.sup.1 and X.sup.2 are each independently selected from H, cyano, C.sub.1-20 -alkyl, C.sub.1-4 -alkoxy, phenyl, carbamoyl, sulphamoyl, COOH and carboxylic acid ester;
Z.sup.1 and Z.sup.2 are both --O--;
R.sup.1 is selected from H, or from C.sub.1-20 -alkyl, C.sub.2-20 -alkenyl, C.sub.4-8 -cycloalkyl, phenyl and phenyl-C.sub.1-4 -alkylene each of which is unsubstituted or substituted by a group selected from C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, nitro, halogen, C.sub.1-4 -alkoxy-C.sub.1-4 -alkoxy, cyclohexyl, phenyl, diphenyl, hydroxy, C.sub.1-4 -alkylcarbonyl, C.sub.1-4 -alkoxycarbonyl, C.sub.1-4 -alkoxy-C.sub.1-4 -alkoxycarbonyl, C.sub.1-4 -alkoxycarbonyloxy, C.sub.1-4 -alkoxy-C.sub.1-4 -alkylcarbonyloxy, C.sub.1-4 -alkylcarbonyloxy, cyano and amino;
R.sup.2 is selected from H, C.sub.2-20 -alkenyl, C.sub.4-8 -alkyl, phenyl and phenyl-C.sub.1-4 -alkylene;
or
R.sup.2 is selected from C.sub.1-20 -alkyl, C.sub.2-20 -alkenyl, C.sub.4-8 -cycloalkyl, phenyl and phenyl-C.sub.1-4 -alkylene each of which is unsubstituted or substituted by a group selected from C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, nitro, halogen, C.sub.1-4 -alkoxy-C.sub.1-4 -alkoxy, cyclohexyl, phenyl, diphenyl, hydroxy, C.sub.1-4 -alkylcarbonyl, C.sub.1-4 -alkoxycarbonyl, C.sub.1-4 -alkoxy-C.sub.1-4 -alkoxycarbonyl, C.sub.1-4 -alkoxycarbonyloxy, C.sub.1-4 -alkoxy-C.sub.1-4 -alkoxycarbonyloxy, C.sub.1-4 -alkylcarbonyloxy, cyano and amino;
R.sup.1 and R.sup.4 together with the N atom and Ring B form a tetrahydroquinolinyl group;
or
R.sup.2 and R.sup.5 together with the N atom and Ring B form a tetrahydroquinolinyl group;
R.sup.6 is selected from H, halogen, C.sub.1-4 -alkyl, C.sub.3-4 -alkenyl, C.sub.1-10 -alkoxy group and a group NR.sup.9 R.sup.10 in which R.sup.9 and R.sup.10 are each independently selected from H, C.sub.1-20 -alkyl, C.sub.2-20 -alkenyl, C.sub.4-8 -cycloalkyl, phenyl and phenyl-C.sub.1-4 -alkylene each of which is unsubstituted or is substituted by a group selected from C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, nitro, halogen, C.sub.1-4 -alkoxy-C.sub.1-4 -alkoxy, cyclohexyl, phenyl, diphenyl, hydroxy, C.sub.1-4 -alkylcarbonyl, C.sub.1-4 -alkoxycarbonyl, C.sub.1-4 -alkoxy-C.sub.1-4 -alkoxycarbonyl, C.sub.1-4 -alkoxycarbonyloxy, C.sub.1-4 -alkoxy-C.sub.1-4 -alkoxycarbonyloxy, C.sub.1-4 -alkylcarbonyloxy, cyano and amino;
R.sup.4 and R.sup.5 each independently is --H, halogen, or a group selected from C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, and C.sub.1 -C.sub.10 alkoxy each of which may be substituted by a group selected from alkoxy, hydroxy, alkylcarbonyloxy, alkoxyalkoxycarbonyl, alkoxycarbonyl, halogen and cyano;
R.sup.7 and R.sup.8 each independently is --H, halogen, or a group selected from C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, and C.sub.1 -C.sub.10 alkoxy each of which may be substituted by a group selected from alkoxy, hydroxy, alkylcarbonyloxy, alkoxyalkoxycarbonyl, alkoxycarbonyl, halogen and cyano;
and where R.sup.6 is NR.sup.1 R.sup.2, then R.sup.6 is the same as or different from the NR.sup.1 R.sup.2 group present in Ring B, provided that one of X.sup.1 and X.sup.2 are different or the number or pattern of substituents in Ring A and Ring B are different.

11 more elements

A compound of Formula VII:

##STR15## wherein;
X.sup.1 and X.sup.2 are each independently selected from H, cyano, C.sub.1-20 -alkyl, C.sub.1-4 -alkoxy, phenyl, carbamoyl, sulphamoyl, COOH and carboxylic acid ester;
Z.sup.1 Z.sup.2 are both --O--;
R.sup.1 and R.sup.2 are each independently selected from H, C.sub.1-20 -alkyl, C.sub.2-20 -alkenyl, C.sub.4-8 -cycloalkyl, phenyl and phenyl-C.sub.1-4 -alkylene each of which is unsubstituted or is substituted by a group selected from C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, nitro, halogen, C.sub.1-4 -alkoxy-C.sub.1-4 -alkoxy, cyclohexyl, phenyl, diphenyl, hydroxy, C.sub.1-4 -alkylcarbonyl, C.sub.1-4 -alkoxycarbonyl, C.sub.1-4 -alkoxy-C.sub.1-4 -alkoxycarbonyl, C.sub.1-4 -alkoxycarbonyloxy, C.sub.1-4 -alkoxy-C.sub.1-4 -alkoxycarbonyloxy, C.sub.1-4 -alkylcarbonyloxy, cyano and amino;
R.sup.1 and R.sup.4 together with the N atom and Ring B form a tetrahydroquinolinyl group;
or
R.sup.2 and R.sup.5 together with the N atom and Ring B form a tetrahydroquinolinyl group;
R.sup.6 is selected from H, halogen, C.sub.1-4 -alkyl, C.sub.3-4 -alkenyl, C.sub.1-10 -alkoxy group and a group NR.sup.1 R.sup.2 in which R.sup.1 and R.sup.2 are each independently as hereinbefore defined;
R.sup.4 and R.sup.5 each independently is --H, halogen, or a group selected from C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, and C.sub.1 -C.sub.10 alkoxy each of which may be substituted by a group selected from alkoxy, hydroxy, alkylcarbonyloxy, alkoxyalkoxycarbonyl, alkoxycarbonyl, halogen and cyano
R.sup.7 and R.sup.8 each independently is --H, halogen, or a group selected from C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, and C.sub.1 -C.sub.10 alkoxy each of which may be substituted by a group selectdd from alkoxy, hydroxy, alkylcarbonyloxy, alkoxyalkoxycarbonyl, alkoxycarbonyl, halogen and cyano;
and where R.sup.6 is NR.sup.1 R.sup.2, then R.sup.6 is the same as or different from the NR.sup.1 R.sup.2 group present in Ring B, provided either X.sup.1 and X.sup.2 are different or the number or pattern of substituents in Ring A and Ring B are different, except for the compound in which each of R.sup.1 and R.sup.2 are methyl, and each of R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, X.sup.1 and X.sup.2 is hydrogen.

8 more elements

Dependencies are inferred from the claim text.