Fiber-reactive AZO dyes, preparation thereof and use thereof

Reactive dyes as per the hereinbelow indicated and defined general formula (I),

• where
• D1 and D2 are independently a group of the general formula (1)
• where
• R1 and R2 are independently hydrogen, (C1–C4)-alkyl, (C1–C4)-alkoxy, hydroxyl, sulfo, carboxyl, cyano, nitro, amido, ureido or halogen;
• and
• X1 is hydrogen or a group of the formula —SO2-Z, where
• Z is —CH═CH2, —CH2CH2Z1 or hydroxyl, where
• Z1 is hydroxyl or an alkali-detachable group;
• or
• D1 and D2 are independently a naphthyl group of the general formula (2)
• where
• R3 and R4 are independently hydrogen, (C1–C4)-alkyl, (C1–C4)-alkoxy, hydroxyl, sulfo, carboxyl, cyano, nitro, amido, ureido or halogen;
• and
• X2 has one of the meanings of X1;
• or
• D1 and D2 are independently a group of the general formula (3)
• where
• R5 and R6 independently have one of the meanings of R1 and R2;
• R7 is hydrogen, (C1–C4)-alkyl, unsubstituted or (C1–C4)-alkyl-, (C1–C4)-alkoxy-, sulfo-, halogen- or carboxyl-substituted phenyl;
• and
• Z2 a group of the general formula (4) or (5) or (6);
• where
• V is fluorine or chlorine;
• U1, U2 are independently fluorine, chlorine or hydrogen;
• and
• Q1, Q2 are independently chlorine, fluorine, cyanamido, hydroxyl, (C1–C6)-alkoxy, phenoxy, sulfophenoxy, mercapto, (C1–C6)-alkymercapto, pyridino, carboxypyridino, carbamoylpyridino or a group of the general formula (7) or (8)
• where
• R8 is hydrogen or (C1–C6)-alkyl, or phenyl unsubstituted or substituted by (C1–C4)-alkyl, (C1–C4)-alkoxy, sulfo, halogen, carboxyl, acetamido, ureido;
• R9 and R10 independently have one of the meanings of R8 or combine to form a cyclic ring system of the formula —(CH2)i—, where i is 4 or 5, or alternatively —(CH2)2-E-(CH2)2—, where E is oxygen, sulfur, sulfo, —NR11 where R11=(C1–C6)-alkyl;
• W is phenylene which is unsubstituted or substituted by 1 or 2 substituents, such as (C1–C4)-alkyl, (C1–C4)-alkoxy, carboxyl, sulfo, chlorine, bromine, or is (C1–C4)-alkylene-arylene or (C2–C6)-alkylene, which can be interrupted by oxygen, sulfur, sulfo, amino, carbonyl, carboxamido, or is phenylene-CONH-phenylene, which is unsubstituted or substituted by (C1–C4)-alkyl, (C1–C4)-alkoxy, hydroxyl, sulfo, carboxyl, amido, ureido or halogen, or is naphthylene which is unsubstituted or substituted by 1 or 2 sulfo groups;
• and
• Z is as defined above;
• or
• D1 and D2 are independently a group of the general formula (9)
• where
• R12 is hydrogen, (C1–C4)-alkyl, aryl or a substituted aryl radical;
• R13 and R14 are independently hydrogen, (C1–C4)-alkyl, (C1–C4)-alkoxy, hydroxyl, sulfo, carboxyl, cyano, nitro, amido, ureido or halogen;
• and
• A is a phenylene group of the general formula (10)
• where
• R15 and R16 are independently hydrogen, (C1–C4)-alkyl, (C1–C4)-alkoxy, hydroxyl, sulfo, carboxyl, cyano, nitro, amido, ureido or halogen;
• or
• a naphthylene group of the general formula (11)
• where
• R17 and R18 are independently hydrogen, (C1–C4)-alkyl, (C1–C4)-alkoxy, hydroxyl, sulfo, carboxyl, cyano, nitro, amido, ureido or halogen;
• or
• a polymethylene group of the general formula (12)
• —(CR19R20)k— (12)
• where
• k is a whole number greater than 1 and
• R19 and R20 are independently hydrogen, (C1–C4)-alkyl, (C1–C4)-alkoxy, hydroxyl, cyano, amido, halogen or aryl;
• and
• X3 has one of the meanings of X1;
• and
• R, R* are independently hydrogen, (C1–C4)-alkyl or sulfomethyl;
• and
• M is hydrogen, an alkali metal or one equivalent of an alkaline earth metal, with the proviso that the dyes of the general formulae (I) contain at least one fiber-reactive heterocyclic group of the general formula (4) or (6).