Azo compound having one or two aliphatic or cycloaliphatic groups containing a total of 8 to 40 carbon atoms therein

Claim 2

A compound of the formula: ##STR5## wherein R is selected from H, cadmium, calcium barium, lead, manganese, zinc, magnesium and strontium or a group containing a tetravalent nitrogen atom selected from ammonium, bis(ammonium), guanidinium, biguanidinium, amidinium and a mono- di- or tri-substituted or quaternary ammonium group in which the substituents are selected from C 1-20 -alkyl, C 1-4 -alkoxy-C 1-20 -alkyl, halo-C 1-20 -alkyl, hydroxy-C 1-20 -alkyl, phenyl, C 1-4 -alkyphenyl, C 1-4 -alkoxyphenyl, halophenyl, hydroxyphenyl, benzyl, C 1-4 -alkylbenzyl, C 1-4 -alkoxybenzyl, halobenzyl, hydroxybenzyl, cyclohexyl and C 1-4 -alkyl-cyclohexyl; X is S, O, ##STR6## R 1 is NO 2 , CN, or COOY: Y is selected from H 1 , C 1-4 -alkyl, cadmium, calcium, barium, lead, manganese, zinc, magnesium, and strontium or a group containing a tetravalent nitrogen atom selected from ammonium, bis(ammonium), guanidinium, biguanidinium, amidinium and a mono- di- or tri-substituted or quaternary ammonium group in which the substituents are selected from C 1-20 -alkyl, C 1-4 -alkoxy-C 1-20 -alkyl, halo-C 1-20 -alkyl, hydroxy-C 1-20 -alkyl, phenyl, C 1-4 -alkyphenyl, C 1-4 -alkoxyphenyl, halophenyl, hydroxyphenyl, benzyl, C 1-4 -alkylbenzyl, C 1-4 -alkoxybenzyl, halobenzyl, hydroxybenzyl, cyclohexyl and C 1-4 -alkyl-cyclohexyl; R 2 and R 3 are each independently H or non-hydrophilic aliphatic or cycloaliphatic group containing up to 30 carbon atoms selected from alkyl, alkenyl, cycloalkyl, a mixture thereof and alkyl, alkenyl, cycloalkyl or a mixture thereof interrupted by not more than one oxygen or sulphur for every twelve chain carbon atoms; R 4 and R 5 are each independently H or non-hydrophilic aliphatic or cycloaliphatic group containing up to 30 carbon atoms selected from alkyl, alkenyl, cycloalkyl, a mixture thereof and alkyl, alkenyl, cycloalkyl or a mixture thereof interrupted by not more than one oxygen or sulphur for every twelve chain carbon atoms, each of R 4 and R 5 being attached directly to Ring A or joined thereto by a linking group selected from oxygen, sulphur, nitrogen, --CO--, --SO 2 , --CO.O-- and SO 2 .O; and R 6 and R 7 are each independently H or a non-hydrophilic group containing up to 4 carbon atoms selected from C 1-4 -alkyl, C 1-4 -alkoxy, NH 2 , and mono- and di-C 1-4 -alkylamino; or R 4 and R 6 together with the carbon atoms of Ring A to which they are attached form a benzene, pyrrole, furan, thiazole, isothiazole, thiophene or pyridine ring fused to Ring A and R 5 and R 7 are as hereinbefore defined; or R 5 and R 7 together with the carbon atoms of Ring A to which they are attached form a benzene, pyrrole, furan, thiazole, isothiazole, thiophene or pyridine ring fused to Ring A and R 4 and R 6 are as hereinbefore defined; or R 2 and R 4 together with the N atom and the carbon atom of Ring A to which they are attached form a 2-pyrroline, tetrahydropyridine, 4-oxazoline or 4-thiazoline ring fused to Ring A and R 3 and R 5 are as hereinbefore defined; R 3 and R 5 together with the N atom and the carbon atom of Ring A to which they are attached form a 2-pyrroline, tetrahydropyridine, 4-oxazoline or 4-thiazoline ring fused to Ring A and R 4 and R 6 are as hereinbefore defined; or provided there are, in total, from 8 to 40 carbon atoms in one or two of the groups independently represented by R 2 , R 3 , R 4 and R 5 .

Claim 3

A compound of the formula: ##STR7## wherein R is selected from H, cadmium, calcium barium, lead, manganese, zinc, magnesium and strontium or a group containing a tetravelent nitrogen atom selected from ammonium, bis(ammonium), guanidinium, biguanidinium, amidinium and a mono- di- or tri-substituted or quaternary ammonium group in which the substituents are selected from C 1-20 -alkyl, C 1-4 -alkoxy-C 1-20 -alkyl, halo-C 1-20 -alkyl, hydroxy-C 1-20 -alkyl, phenyl, C 1-4 -alkyphenyl, C 1-4 -alkoxyphenyl, halophenyl, hydroxyphenyl, benzyl, C 1-4 -allkylbenzyl, C 1-4 -alkoxybenzyl, halobenzyl, hydroxybenzyl, cyclohexyl and C 1-4 -alkyl-cyclohexyl; X is S, O, ##STR8## R 1 is NO 2 , CN, or COOY: Y is selected from H 1 , C 1-4 -alkyl, cadmium calcium, barium, lead, manganese, zinc, magnesium, and strontium or a group containing a tetravalent nitrogen atom selected from ammonium, bis(ammonium), guanidinium, biguanidinium, amidinium and a mono- di- or tri-substituted or quaternary ammonium group in which the substituents are selected from C 1-20 -alkyl, C 1-4 -alkoxy-C 1-20 -alkyl, halo-C 1-20 -alkyl, hydroxy-C 1-20 -alkyl, phenyl, C 1-4 -alkylphenyl, C 1-4 -alkoxyphenyl, halophenyl, hydroxyphenyl, benzyl, C 1-4 -alkylbenzyl, C 1-4 -alkoxybenzyl, halobenzyl, hydroxybenzyl, cyclohexyl and C 1-4 -alkyl-cyclohexyl; R 2 and R 3 are each independently H or non-hydrophilic aliphatic or cycloaliphatic group containing up to 30 carbon atoms selected from alkyl, alkenyl, cycloakyl, a mixture thereof and alkyl, alkenyl, cycloalkyl or a mixture thereof interrupted by not more than one oxygen or sulphur for every twelve chain carbon atoms; R 4 and R 5 are each independently H or non-hydrophilic aliphatic or cycloaliphatic group containing up to 30 carbon atoms selected from alkyl, alkenyl, cycloalkyl, a mixture thereof and alkyl, alkenyl, cycloalkyl or a mixture thereof interrupted by not more than one oxygen or sulphur for every twelve chain carbon atoms, each of R 4 and R 5 being attached directly to Ring A or joined thereto by a linking group selected from oxygen, sulphur, nitrogen, --CO--, --SO 2 , --CO.O-- and --SO 2 .O; and R 6 and R 7 are each independently H or a non-hydrophilic group containing up to 4 carbon atoms selected from C 1-4 -alkyl, C 1-4 -alkoxy, NH 2 , and mono- and di-C 1-4 alkylamino; or R 4 and R 6 together with the carbon atoms of Ring A to which they are attached form a benzene, pyrrole, furan, thiazole, isothiazole, thiophene or pyridine ring fused to Ring A and R 5 and R 7 are as hereinbefore defined; or R 5 and R 7 together with the carbon atoms of Ring A to which they are attached form a benzene, pyrrole, furan, thiazole, isothiazole, thiophene or pyridine ring fused to Ring A and R 4 and R 6 are as hereinbefore defined; or R 2 and R 4 together with the N atom and the carbon atom of Ring A to which they are attached form a 2-pyrroline, tetrahydropyridine, 4-oxazoline or 4-thiazoline ring fused to Ring A and R 3 and R 5 are as hereinbefore defined; or R 3 and R 5 together with the N atom and the carbon atom of Ring A to which they are attached form a 2-pyrroline, tetrahydropyridine, 4-oxazoline or 4-thiazoline ring fused to Ring A and R 4 and R 6 are as hereinbefore defined; or provided that there are in total from 8 to 40 carbon atoms in one or both of the groups represented by R 2 and R 3 or that one of the groups represented by R 4 and R 5 contains from 8 to 20 carbon atoms.

Claim 4

A compound of the formula: ##STR7## wherein R is selected from H, cadmium, calcium barium, lead, manganese, zinc, magnesium and strontium or a group containing a tetravelent nitrogen atom selected from ammonium, bis(ammonium), guanidinium, biguanidinium, amidinium and a mono- di- or tri-substituted or quaternary ammonium group in which the substituents are selected from C 1-20 -alkyl, C 1-4 -alkoxy-C 1-20 -alkyl, halo-C 1-20 -alkyl, hydroxy-C 1-20 -alkyl, phenyl, C 1-4 -alkyphenyl, C 1-4 -alkoxyphenyl, halophenyl, hydroxyphenyl, benzyl, C 1-4 -allkylbenzyl, C 1-4 -alkoxybenzyl, halobenzyl, hydroxybenzyl, cyclohexyl and C 1-4 -alkyl-cyclohexyl; X is S, O, ##STR8## R 1 is NO 2 , CN, or COOY: Y is selected from H 1 , C 1-4 -alkyl, cadmium calcium, barium, lead, manganese, zinc, magnesium, and strontium or a group containing a tetravalent nitrogen atom selected from ammonium, bis(ammonium), guanidinium, biguanidinium, amidinium and a mono- di- or tri-substituted or quaternary ammonium group in which the substituents are selected from C 1-20 -alkyl, C 1-4 -alkoxy-C 1-20 -alkyl, halo-C 1-20 -alkyl, hydroxy-C 1-20 -alkyl, phenyl, C 1-4 -alkylphenyl, C 1-4 -alkoxyphenyl, halophenyl, hydroxyphenyl, benzyl, C 1-4 -alkylbenzyl, C 1-4 -alkoxybenzyl, halobenzyl, hydroxybenzyl, cyclohexyl and C 1-4 -alkyl-cyclohexyl; R 2 and R 3 are each independently H or non-hydrophilic aliphatic or cycloaliphatic group containing up to 30 carbon atoms selected from alkyl, alkenyl, cycloakyl, a mixture thereof and alkyl, alkenyl, cycloalkyl or a mixture thereof interrupted by not more than one oxygen or sulphur for every twelve chain carbon atoms; R 4 and R 5 are each independently H or non-hydrophilic aliphatic or cycloaliphatic group containing up to 30 carbon atoms selected from alkyl, alkenyl, cycloalkyl, a mixture thereof and alkyl, alkenyl, cycloalkyl or a mixture thereof interrupted by not more than one oxygen or sulphur for every twelve chain carbon atoms, each of R 4 and R 5 being attached directly to Ring A or joined thereto by a linking group selected from oxygen, sulphur, nitrogen, --CO--, --SO 2 , --CO.O-- and --SO 2 .O; and R 6 and R 7 are each independently H or a non-hydrophilic group containing up to 4 carbon atoms selected from C 1-4 -alkyl, C 1-4 -alkoxy, NH 2 , and mono- and di-C 1-4 alkylamino; or R 4 and R 6 together with the carbon atoms of Ring A to which they are attached form a benzene, pyrrole, furan, thiazole, isothiazole, thiophene or pyridine ring fused to Ring A and R 5 and R 7 are as hereinbefore defined; or R 5 and R 7 together with the carbon atoms of Ring A to which they are attached form a benzene, pyrrole, furan, thiazole, isothiazole, thiophene or pyridine ring fused to Ring A and R 4 and R 6 are as hereinbefore defined; or R 2 and R 4 together with the N atom and the carbon atom of Ring A to which they are attached form a 2-pyrroline, tetrahydropyridine, 4-oxazoline or 4-thiazoline ring fused to Ring A and R 3 and R 5 are as hereinbefore defined; or R 3 and R 5 together with the N atom and the carbon atom of Ring A to which they are attached form a 2-pyrroline, tetrahydropyridine, 4-oxazoline or 4-thiazoline ring fused to Ring A and R 4 and R 6 are as hereinbefore defined; or provided that there are in total from 8 to 40 carbon atoms in one or both of the groups represented by R 2 and R 3 or that one of the groups represented by R 4 and R 5 contains from 8 to 20 carbon atoms.

Claim 5

A compound of the formula ##STR9## wherein R is selected from H, cadmium, calcium barium, lead, manganese, zinc, magnesium and strontium or a group containing a tetravelent nitrogen atom selected from ammonium, bis(ammonium), guanidinium, biguanidinium, amidinium and a mono- di- or tri-substituted or quaternary ammonium group in which the substituents are selected from C 1-20 -alkyl, C 1-4 -alkoxy-C 1-20 -alkyl, halo-C 1-20 -alkyl, hydroxy-C 1-20 -alkyl, phenyl, C 1-4 -alkyphenyl, C 1-4 -alkoxyphenyl, halophenyl, hydroxyphenyl, benzyl, C 1-4 -allkylbenzyl, C 1-4 -alkoxybenzyl, halobenzyl, hydroxybenzyl, cyclohexyl and C 1-4 -alkyl-cyclohexyl; X is S, O, ##STR10## R 1 is NO 2 , CN, or COOY: Y is selected from H 1 , C 1-4 -alkyl, cadmium, barium, lead, manganese, zinc, magnesium, and strontium or a group containing a tetravalent nitrogen atom selected from ammonium, bis(ammonium), guanidinium, biguanidinium, amidinium and a mono- di- or tri-substituted or quaternary ammonium group in which the substituents are selected from C 1-20 -alkyl, C 1-4 -alkoxy-C 1-20 -alkyl, halo-C 1-20 -alkyl, hydroxy-C 1-20 -alkyl, phenyl, C 1-4 -alkylphenyl, C 1-4 -alkoxyphenyl, halophenyl, hydroxyphenyl, benzyl, C 1-4 -alkylbenzyl, C 1-4 -alkoxybenzyl, halobenzyl, hydroxybenzyl, cyclohexyl and C 1-4 -alkyl-cyclohexyl; R 2 and R 3 are each independently H or non-hydrophilic aliphatic or cycloaliphatic group containing up to 30 carbon atoms selected from alkyl, alkenyl, cycloalkyl, a mixture thereof and alkyl, alkenyl, cycloalkyl or a mixture thereof interrupted by not more than one oxygen or sulphur for every twelve chain carbon atoms; R 4 and R 5 are each independently H or non-hydrophilic aliphatic or cycloaliphatic group containing up to 30 carbon atoms selected from alkyl, alkenyl, cycloalkyl, a mixture thereof and alkyl, alkenyl, cycloalkyl or a mixture thereof interrupted by not more than one oxygen or sulphur for every twelve chain carbon atoms, each of R 4 and R 5 being attached directly to Ring A or joined thereto by a linking group selected from oxygen, sulphur, nitrogen, --CO--, --SO 2 , --CO.O-- and --SO 2 .O; and R 6 and R 7 are each independently H or a non-hydrophilic group containing up to 4 carbon atoms selected from C 1-4 -alkyl, C 1-4 -alkoxy, NH 2 , and mono- and di-C 1-4 alkylamino; or R 4 and R 6 together with the carbon atoms of Ring A to which they are attached form a benzene, pyrrole, furan, thiazole, isothiazole, thiophene or pyridine ring fused to Ring A and R 5 and R 7 are as hereinbefore defined; or R 5 and R 7 together with the carbon atoms of Ring A to which they are attached form a benzene, pyrrole, furan, thiazole, isothiazole, thiophene or pyridine ring fused to Ring A and R 4 and R 6 are as hereinbefore defined; or R 2 and R 4 together with the N atom and the carbon atoms of Ring A to which they are attached form a 2-pyrroline, tetrahydropyridine, 4-oxazoline or 4-thiazoline ring fused to Ring A and R 3 and R 5 are as hereinbefore defined; or R 3 and R 5 together with the N atom and the carbon atom of Ring A to which they are attached form a 2-pyrroline, tetrahydropyridine, 4-oxazoline or 4-thiazoline ring fused to Ring A and R 4 and R 6 are as hereinbefore defined; provided that there are in total from 8 to 40 carbon atoms in one or both of the groups represented by R 2 and R 3 .

Claim 6

A compound of the formula ##STR9## wherein R is selected from H, cadmium, calcium barium, lead, manganese, zinc, magnesium and strontium or a group containing a tetravelent nitrogen atom selected from ammonium, bis(ammonium), guanidinium, biguanidinium, amidinium and a mono- di- or tri-substituted or quaternary ammonium group in which the substituents are selected from C 1-20 -alkyl, C 1-4 -alkoxy-C 1-20 -alkyl, halo-C 1-20 -alkyl, hydroxy-C 1-20 -alkyl, phenyl, C 1-4 -alkyphenyl, C 1-4 -alkoxyphenyl, halophenyl, hydroxyphenyl, benzyl, C 1-4 -allkylbenzyl, C 1-4 -alkoxybenzyl, halobenzyl, hydroxybenzyl, cyclohexyl and C 1-4 -alkyl-cyclohexyl; X is S, O, ##STR10## R 1 is NO 2 , CN, or COOY: Y is selected from H 1 , C 1-4 -alkyl, cadmium, barium, lead, manganese, zinc, magnesium, and strontium or a group containing a tetravalent nitrogen atom selected from ammonium, bis(ammonium), guanidinium, biguanidinium, amidinium and a mono- di- or tri-substituted or quaternary ammonium group in which the substituents are selected from C 1-20 -alkyl, C 1-4 -alkoxy-C 1-20 -alkyl, halo-C 1-20 -alkyl, hydroxy-C 1-20 -alkyl, phenyl, C 1-4 -alkylphenyl, C 1-4 -alkoxyphenyl, halophenyl, hydroxyphenyl, benzyl, C 1-4 -alkylbenzyl, C 1-4 -alkoxybenzyl, halobenzyl, hydroxybenzyl, cyclohexyl and C 1-4 -alkyl-cyclohexyl; R 2 and R 3 are each independently H or non-hydrophilic aliphatic or cycloaliphatic group containing up to 30 carbon atoms selected from alkyl, alkenyl, cycloalkyl, a mixture thereof and alkyl, alkenyl, cycloalkyl or a mixture thereof interrupted by not more than one oxygen or sulphur for every twelve chain carbon atoms; R 4 and R 5 are each independently H or non-hydrophilic aliphatic or cycloaliphatic group containing up to 30 carbon atoms selected from alkyl, alkenyl, cycloalkyl, a mixture thereof and alkyl, alkenyl, cycloalkyl or a mixture thereof interrupted by not more than one oxygen or sulphur for every twelve chain carbon atoms, each of R 4 and R 5 being attached directly to Ring A or joined thereto by a linking group selected from oxygen, sulphur, nitrogen, --CO--, --SO 2 , --CO.O-- and --SO 2 .O; and R 6 and R 7 are each independently H or a non-hydrophilic group containing up to 4 carbon atoms selected from C 1-4 -alkyl, C 1-4 -alkoxy, NH 2 , and mono- and di-C 1-4 alkylamino; or R 4 and R 6 together with the carbon atoms of Ring A to which they are attached form a benzene, pyrrole, furan, thiazole, isothiazole, thiophene or pyridine ring fused to Ring A and R 5 and R 7 are as hereinbefore defined; or R 5 and R 7 together with the carbon atoms of Ring A to which they are attached form a benzene, pyrrole, furan, thiazole, isothiazole, thiophene or pyridine ring fused to Ring A and R 4 and R 6 are as hereinbefore defined; or R 2 and R 4 together with the N atom and the carbon atoms of Ring A to which they are attached form a 2-pyrroline, tetrahydropyridine, 4-oxazoline or 4-thiazoline ring fused to Ring A and R 3 and R 5 are as hereinbefore defined; or R 3 and R 5 together with the N atom and the carbon atom of Ring A to which they are attached form a 2-pyrroline, tetrahydropyridine, 4-oxazoline or 4-thiazoline ring fused to Ring A and R 4 and R 6 are as hereinbefore defined; provided that there are in total from 8 to 40 carbon atoms in one or both of the groups represented by R 2 and R 3 .

Claim 7

A compound according to claim 1, 2 or 3 wherein R 2 is C 8-20 -alkyl or C 8-20 -alkenyl.

Claim 8

A compound according to claim 4 wherein R 3 , R 4 and R 5 are selected from H, C 1-4 -alkyl, C 1-4 -alkoxy and NT 2 wherein each T is independently selected from H, C 1-4 -alkyl and phenyl.

Claim 9

A compound according to claim 1 wherein R 4 is selected from C 8-20 -alkyl, C 8-20 -alkenyl, C 8-20 -alkoxy, C 8-20 -alkenoxy, C 8-20 -alkylthio, C 8-20 -alkylamino and C 8-20 -alkoxycarbonyl.

Claim 10

A compound according to claim 6 wherein R 2 , R 3 and R 5 are selected from H, C 1-4 -alkyl, C 1-4 -alkoxy and NT 2 wherein each T is independently selected from H, C 1-4 -alkyl and phenyl.

Claim 11

A compound according to claim 1, 2, or 3 wherein R 2 and R 3 are each independently C 1-19 -alkyl or C 1-19 -alkenyl provided the sum of the carbon atoms in the two groups is from 8 to 20.

Claim 12

A compound according to claim 1, 2, or 3 wherein R 6 and R 7 are independently selected from H, C 1-4 -alkyl, C 1-4 -alkoxy and NT 2 wherein each T is independently selected from H, C 1-4 -alkyl and phenyl.

Claim 13

A compound according to claim 1, 2 or 3 wherein: X is ##STR11##

Claim 14

A compound according to claim 1, 2 or 3 wherein: R is selected from H, Cd, Ca, Ba, Pb, NH 4 and N(CH 3 ) 4 ; R 1 is NO 2 or CN; R 2 is C 8-20 -alkyl; R 3 is H or C 1-4 -alkyl; R 4 to R 7 are each H; and X is ##STR12## .

Claim 15

The compound 4-(4-[N-n-dodecyl-N-methylamino]phenylazo)-3-nitrobenzoic acid.

Claim 16

The compound 4-(4-[N-n-dodecyl-N-methylamino]phenylazo)-3-nitrobenzoic acid.