Magenta inks comprising copper complex azo dyes based on 1-naphthol-di- or tri-sulfonic acids

A dye of formula (1a)

• wherein
• X is hydroxy, unsubstituted or hydroxy-substituted C1-4alkyl, vinyl or a radical —CH2—CH2—Z, wherein Z is a group removable under alkaline conditions or is C1-C24alkoxy unsubstituted or substituted in the alkyl moiety, which may further be interrupted in the alkyl moiety by oxygen;
• phenoxy unsubstituted or substituted in the phenyl ring;
• C1-C4alkylthio unsubstituted or substituted in the alkyl moiety;
• phenylthio unsubstituted or substituted in the phenyl ring;
• amino;
• N-mono- or N,N-di-C1-C24alkylamino unsubstituted or substituted in the alkyl moiety, which may further be interrupted in the alkyl moiety by oxygen or by a radical —NR1— in which R1 is hydrogen or unsubstituted or further substituted C1-C4alkyl;
• C10-C20terpeneamino;
• C5-C7cycloalkylamino unsubstituted or substituted in the cycloalkyl ring;
• phenyl- or naphthylamino or N—C1-C4alkyl-N-phenyl- or N—C1-C4alkyl-N-naphthyl-amino unsubstituted or substituted in the aryl moiety;
• morpholino;
• piperidin-1-yl;
• or piperazin-1-yl unsubstituted or substituted at the nitrogen atom;
• or X has the same definitions as Z with the exception of a group removable under alkaline conditions;
• R is C1-C4alkyl, C1-C4alkoxy or halogen;
• and
• m and n are each independently of the other the number 0, 1 or 2.

A dye of formula (1b)

• wherein
• X is hydroxy, unsubstituted or hydroxy-substituted C1-C4alkyl or a radical —CH2—CH2—Z, wherein Z is C1-C24alkoxy unsubstituted or substituted in the alkyl moiety, which may further be interrupted in the alkyl moiety by oxygen;
• phenoxy unsubstituted or substituted in the phenyl ring;
• C1-C4alkylthio unsubstituted or substituted in the alkyl moiety;
• phenylthio unsubstituted or substituted in the phenyl ring;
• amino;
• N-mono- or N,N-di-C1-C24alkylamino unsubstituted or substituted in the alkyl moiety, which may further be interrupted in the alkyl moiety by oxygen or by a radical —NR1— in which R1 is hydrogen or unsubstituted or further substituted C1-C4alkyl;
• C10-C20terpeneamino;
• C5-C7cycloalkylamino unsubstituted or substituted in the cycloalkyl ring;
• phenyl- or naphthyl-amino or N—C1-C4alkyl-N-phenyl- or N—C1-C4alkyl-N-naphthyl-amino unsubstituted or substituted in the aryl moiety;
• morpholino;
• piperidin-1-yl;
• or piperazin-1-yl unsubstituted or substituted at the nitrogen atom;
• or X has the same definitions as Z;
• R is C1-C4alkyl, C1-C4alkoxy or halogen;
• and
• m and n are each independently of the other the number 0, 1 or 2.

A dye mixture comprising a dye of formula (1)

• wherein
• X is hydroxy, unsubstituted or hydroxy-substituted C1-C4alkyl, vinyl or a radical —CH2—CH2—Z, wherein Z is a group removable under alkaline conditions or is C1-C24alkoxy unsubstituted or substituted in the alkyl moiety, which may further be interrupted in the alkyl moiety by oxygen;
• phenoxy unsubstituted or substituted in the phenyl ring;
• C1-C4alkylthio unsubstituted or substituted in the alkyl moiety;
• phenylthio unsubstituted or substituted in the phenyl ring;
• amino;
• N-mono- or N,N-di-C1-C24alkylamino unsubstituted or substituted in the alkyl moiety, which may further be interrupted in the alkyl moiety by oxygen or by a radical —NR1— in which R1 is hydrogen or unsubstituted or further substituted C1-C4alkyl;
• C10-C20terpeneamino;
• C5-C7cycloalkylamino unsubstituted or substituted in the cycloalkyl ring;
• phenyl- or naphthyl-amino or N—C1-C4alkyl-N-phenyl- or N—C1-C4alkyl-N-naphthyl-amino unsubstituted or substituted in the aryl moiety;
• morpholino;
• piperidin-1-yl;
• or piperazin-1-yl unsubstituted or substituted at the nitrogen atom;
• or X has the same definitions as Z with the exception of a group removable under alkaline conditions;
• R is C1-C4alkyl, C1-C4alkoxy or halogen;
• and
• m and n are each independently of the other the number 0, 1 or 2;
• together with at least one dye selected from the group consisting of:
• xanthene dyes of formula (6)
• azo dyes of formula (7)
• azo dyes of formula (8)
• wherein
• D1 are D2 are each independently of the other the radical of a diazo component of the benzene or naphthalene series,
• R3, R4, R5 are R6 are each independently of the others C1-C4alkyl or unsubstituted or substituted C5-C7cycloalkyl,
• R7 are R8 are each independently of the other sulfo or carboxy, and
• R9 is hydrogen or an acyl radical.

A dye of formula (1)

• wherein
• X is hydroxy, unsubstituted or hydroxy-substituted C1-C4alkyl, vinyl or a radical —CH2—CH2—Z, wherein Z is a group removable under alkaline conditions or is C1-C24alkoxy unsubstituted or substituted in the alkyl moiety, which may further be interrupted in alkyl moiety by oxygen;
• phenoxy unsubstituted or substituted in the phenyl ring;
• C1-C4alkylthio unsubstituted or substituted in the alkyl moiety;
• phenylthio unsubstituted or substituted in the phenyl ring;
• amino;
• N-mono- or N,N-di-C1-C24alkylamino unsubstituted or substituted in the alkyl moiety, which may further be interrupted in the alkyl moiety by oxygen or by a radical —NR1— in which R1 is hydrogen or unsubstituted or further substituted C1-C4alkyl;
• C10-C20terpeneamino;
• C5-C7cycloalkylamino unsubstituted or substituted in the cycloalkyl ring;
• phenyl- or naphthyl-amino or N—C1-C4alkyl-N-phenyl- or N—C1-C4alkyl-N-naphthyl-amino unsubstituted or substituted in the aryl moiety;
• morpholino;
• piperidin-1-yl;
• or piperazin-1-yl unsubstituted or substituted at the nitrogen atom;
• or X has the same definitions as Z with the exception of a group removable under alkaline conditions;
• R is C1-C4alkyl, C1-C4alkoxy or halogen;
• and
• m and n are each independently of the other the number 0, 1 or 2;
• in the form of a salt of an amine of formula
• wherein the sum of the carbon atoms Ra+Rb+Rc is from 11 to 14.