Back to results
US 9,062,208 B2Granted
Fiber-reactive copper complex disazo dyes
AssigneeDyStar Colours Distribution GmbH
InventorsJoachim Eichhorn, Andreas Schrell
Life of this patent
Estimating the term…
Abstract
The present invention relates to dyes of the formula (I), in which R1 to R4, D1, f, and M are defined as indicated in claim 1, to processes for preparing them, and to their use for dyeing and printing hydroxyl- and/or carboxamido-containing materials.
Claims14
A dye of the formula (I)
- in which
- R1 and R2 independently of one another are hydrogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, hydroxyl, sulfo, carboxyl, cyano, nitro, amido, or ureido or are a group of the formula —SO2—Z1, where
- Z1 is —CH═CH2, —CH2CH2G or hydroxyl, and
- G is hydroxyl or an alkali-detachable group;
- R3 is (C1-C4)-alkyl;
- (C1-C4)-alkyl substituted by sulfo, carboxyl, halogen, hydroxyl, amino or acetamido;
- phenyl;
- or phenyl substituted by (C1-C4)-alkyl, (C1-C4)-alkoxy, sulfo, halogen, carboxyl, acetamido or ureido;
- R4 is hydrogen or has one of the definitions of R3;
- f is 0 or 1;
- D1 is a group of the formula (1)
- in which
- R5 and R6 independently of one another are 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—Z2, where Z2 has one of the definitions of Z1;
- D1 is a group of the formula (2)
- in which
- R7 and R8 independently of one another are hydrogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, hydroxyl, sulfo, carboxyl, cyano, nitro, amido, ureido or halogen;
- and
- X2 has one of the definitions of X1;
- or
- D1 is a group of the formula (3)
- in which
- R9 and R10 independently of one another have one of the definitions of R5 and R6;
- R11 is hydrogen, (C1-C4)-alkyl, or phenyl which is unsubstituted or substituted by (C1-C4)-alkyl, (C1-C4)-alkoxy, sulfo, halogen or carboxyl;
- and
- Z3 is a group of the formula (4) or (5) or (6)
- in which
- V is fluorine or chlorine;
- U1 and U2 independently of one another are fluorine, chlorine or hydrogen;
- and
- Q1 and Q2 independently of one another are chlorine, fluorine, cyanamido, hydroxyl, (C1-C6)-alkoxy, phenoxy, sulfophenoxy, mercapto, (C1-C4)-alkylmercapto, pyridino, carboxypyridino or carbamoylpyridino, or are a group of the formula (7) or (8)
- in which
- R12 is hydrogen, (C1-C4)-alkyl, sulfo-(C1-C4)-alkyl, unsubstituted phenyl or phenyl which is substituted by (C1-C4)-alkyl, (C1-C4)-alkoxy, sulfo, halogen, carboxyl, acetamido or ureido;
- R13 and R14 independently of one another have one of the definitions of R12 or together form a group of the formula —(CH2)j— where j is 4 or 5, or a group of the formula —(CH2)2-E-(CH2)2—, in which E is oxygen, sulfur, sulfonyl or —N((C1-C4)-alkyl)-;
- W is unsubstituted phenylene;
- phenylene substituted by 1 or 2 substituents selected from the group consisting of (C1-C4)-alkyl, (C1-C4)-alkoxy, carboxyl, sulfo, chlorine, and bromine;
- unsubstituted naphthylene;
- naphthylene substituted by 1 or 2 sulfo groups;
- (C1-C4)-alkylene-arylene;
- (C1-C4)-alkylene-arylene which is interrupted by oxygen, sulfur, sulfonyl, —NH—, carbonyl, —CONH— or —CON(CH3)—;
- (C2-C6)-alkylene;
- (C2-C6)-alkylene which is interrupted by oxygen, sulfur, sulfonyl, —NH—, carbonyl, —CONH— or —CON(CH3)—;
- phenylene-CONH-phenylene;
- or phenylene-CONH-phenylene, where one or both phenylene groups are substituted each by 1 or 2 substituents selected from the group consisting of (C1-C4)-alkyl, (C1-C4)-alkoxy, hydroxyl, sulfo, carboxyl, amido, ureido, and halogen;
- and
- Z4 has one of the definitions of Z1;
- or
- D1 is a group of the formula (9)
- in which
- R15 is hydrogen, (C1-C4)-alkyl, aryl or an aryl substituted by one, two or three mutually independent groups from the selected from the group consisting of (C1-C4)-alkyl, (C1-C4)-alkoxy, hydroxyl, sulfo, carboxyl, amido, and halogen;
- R16 and R17 independently of one another are hydrogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, hydroxyl, sulfo, carboxyl, cyano, nitro, amido, ureido or halogen;
- A is a group of the formula (10)
- in which
- R18 and R19 independently of one another are hydrogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, hydroxyl, sulfo, carboxyl, cyano, nitro, amido, ureido or halogen;
- or
- A is a group of the general formula (11)
- in which
- R20 and R21 independently of one another are hydrogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, hydroxyl, sulfo, carboxyl, cyano, nitro, amido, ureido or halogen;
- or
- A is a group of the formula (12)
- —(CR22R23)k— (12)
- in which
- k is an integer greater than 1 and
- R22 and R23 independently of one another are hydrogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, hydroxyl, cyano, amido, halogen or aryl;
- and
- X3 has one of the definitions of X1;
- and
- M is hydrogen, an alkali metal or one equivalent of an alkaline earth metal;
- and the dye of the formula (I) comprises at least one fiber-reactive group selected from the group consisting of —SO2—Z1, —SO2—Z2 and Z3.
67 more elements
A dye of the formula (I-1) through (I-67)
Dependencies are inferred from the claim text.