Azoxy dyes and copper complexes thereof

A process for preparing copper complex dyes of the formula IX, or mixtures thereof:

• wherein at least one of M1 and M2 is copper (II) and any which is not is hydrogen or methyl, and X is hydrogen, which comprises:
• (1) preparing an azoxy dye of the formula
• wherein R1 is selected from the group consisting of methoxy, hydroxyl and carboxyl, by a process which comprises coupling a coupling component of the formula IV
• wherein n is 1, and R2 is selected from the group consisting of carboxyl, amino, C1-C4-alkylamino, allylamino, benzylamino and methoxycarbonylmethylamino, and the phenyl rings A may additionally be substituted by C1-C8-alkyl, unsubstituted or methyl- or halogen-substituted phenyl, hydroxyl, amino, nitro, halogen, carboxyl, N-benzylcarbamoyl, unsubstituted or nitro-, halogen-, C1-C4-alkoxy- or acetoxy-substituted phenylcarbamoyl and naphthylcarbamoyl or be benzofused,
• with nitroaniline of the formula V
• reducing the resultant nitro monoazo dye, and deacylating in aqueous solution at pH<9;
• and
• (2) reacting the dye obtained in (1) with at least 0.1 mol equivalent of a copper donor.

A process for preparing azoxy dyes of the formula

• where
• R1 is selected from the group consisting of methoxy, hydroxyl and carboxyl, which comprises coupling a coupling component of the formula IV
• with nitroaniline of the formula V
• wherein R2 is selected from the group consisting of carboxyl, amino, C1-C4-alkylamino, allylamino, benzylamino and methoxycarbonylmethylamino, and the phenyl rings A may additionally be substituted by C1-C8-alkyl, unsubstituted or methyl- or halogen-substituted phenyl, hydroxyl, amino, nitro, halogen, carboxyl, N-benzylcarbamoyl, unsubstituted or nitro-, halogen-, C1-C4-alkoxy- or acetoxy-substituted phenylcarbamoyl and naphthylcarbamoyl or be benzofused,
• reducing the resultant nitro monoazo dye, and deacylating in aqueous solution at pH<9.