Basic mono-and bisazo compounds

Compounds of formula (I)

• 508
• wherein
• R1 is H;
• C1-C4alkyl or C1-C4alkyl monosubstituted by —OH,
• X1 and X2 independently of each other are an aliphatic, cycloaliphatic, aromatic or heterocyclic amino group, and at least one amino group comprises a protonatable nitrogen atom or a quaternary ammonium group, and being an aliphatic, cycloaliphatic, aromatic or heterocyclic mono(C1-4alkyl)-amino group, the C1-4alkyl-group being unsubstituted or monosubstituted by halogen, C1-4alkoxy, C1-4alkyl, phenyl or hydroxy;
• an aliphatic, cycloaliphatic, aromatic or heterocyclic di(C1-4alkyl)-amino group, the C1-4alkyl-groups being independently unsubstituted or monosubstituted by halogen, C1-4alkyl, C1-4alkoxy, phenyl or hydroxy;
• a C5-6cycloalkylamino group, the cycloalkyl group being unsubstituted or substituted by one or two C1-2alkyl groups;
• a phenylamino group, the phenyl ring being unsubstituted or substituted by one or two groups selected from halogen, C1-4alkyl, C1-4alkoxy, hydroxy and phenoxy;
• or a 5- or 6-membered ring containing one or two hetero atoms, in addition to N, O or S, which heterocyclic ring is unsubstituted or substituted by one or two C1-4alkyl groups;
• or a group Z, where Z is independently selected from
• 509
• where
• p is 0 or an integer 1, 2 or 3,
• each R2 is independently H;
• unsubstituted C1-4alkyl or C1-4alkyl monosubstituted by hydroxy, halogen, cyano or C1-4alkoxy,
• each R3 and R4 is independently H;
• unsubstituted C1-6alkyl;
• C2-6alkyl monosubstituted by hydroxy or cyano;
• phenyl or phenyl-C1-4alkyl, where the phenyl ring of the latter two groups is unsubstituted or substituted by one to three groups selected from chlorine, C1-4alkyl, C1-4alkoxy, unsubstituted C5-6cycloalkyl or C5-6cycloalkyl substituted by one to three C1-4alkyl groups, or a pyridinium ring, or
• R3 and R4 together with the nitrogen atom to which they are attached, form a 5- or 6-membered ring containing one to three hetero atoms (in addition to N, one or two further N, O or S), which heterocyclic ring is unsubstituted or substituted by one or two C1-14alkyl groups,
• each R5 and R6 has independently one of significances of R3 and R4, except hydrogen,
• R7 is C1-4alkyl or benzyl with the exception that R7 is not benzyl when R5 and R6 have one of the cyclic significations of R3 and R4 or
• R5, R6 and R7 together with the nitrogen atom to which they are attached, form a pyridinium ring which is unsubstituted or substituted by one or two methyl groups,
• Q1 is C2-8alkylene;
• branched C2-8alkylene;
• C2-6alkylene substituted by one or two hydroxy groups;
• C1-6alkylene-1,3-phenylene;
• or C1-6alkylene-1,4-phenylene,
• Q2 is C2-8alkylene;
• branched C2-8alkylene;
• C3-6alkylene substituted by one or two hydroxy groups;
• C1-6alkylene-1,3-phenylene;
• C1-6alkylene-1,4-phenylene;
• 1,3-phenylene or 1,4-phenylene,
• Q3 is C2-8alkylene,
• R8 is H;
• unsubstituted C1-6alkyl or C1-6alkyl monosubstituted by hydroxy, cyano, chlorine or phenyl,
• R9 is unsubstituted C186 alkyl or C1-6alkyl monosubstituted by hydroxy, cyano or chlorine, and
• An0 is a non-chromophoric anion,
• E is NH or a direct bond,
• m is 0 or 1, and if m is 1 the phenyl group is substituted meta or para,
• n is 1 or 2 with the provisos that
• (i) when n is 1 then
• DK is a radical of formula (a)
• 510
• wherein
• R10 is SO2—Y or —O—Y, where Y is a C2-4-alkenyl group or a C2-4alkyl group which is optionally substituted by —CN, —OH, —OSO3H, halogen or —NR11R12, wherein R1 and R12 are independently from one another H, C1-4alkyl or substituted C1-4alkyl, or R11 and R12 together with the nitrogen atom to which they are attached, form a 5- or 6-membered ring containing one to three hetero atoms (in addition to N, one or two further N, O or S), which heterocyclic ring is unsubstituted or substituted by one or two C1-4alkyl groups preferably,
• R′10 and R″10 are independently from one another H;
• C1-2alkyl;
• OC1-2alkyl;
• —SO3H;
• —OH or —CN;
• or DK is a radical of formula (b)
• 511
• wherein
• R13 is H;
• C1-4alkyl;
• substituted C1-4alkyl;
• O—C1-4alkyl;
• substituted O—C1-4alkyl;
• —SO3H;
• —OH;
• —CN;
• —COOR11;
• —NR11R12 or halogen, wherein R11 and R12 have the same meanings as defined above,
• R14 and R15 have the same definition as R13 with exception of hydrogen,
• wherein at least one of the R13, R14 or R15 is —SO3H;
• or DK can be a bicyclic ringsystem wherein each ring is independently from each other a 5- or 6-membered ring and the bicyclic ringsystem is not substituted by further azo groups and
• (ii) when n is 2 then
• DK is a divalent radical B,
• as well as their salts and/or mixtures thereof.