High light fastness reactive red dyes
View Patent ↗The present invention refers to dyestuffs of the formula (I) wherein R 1 is H or (C 1 –C 4 )-alkyl; R 2 is H or (C 1 –C 4 )-alkyl; each of X 1 and X 2 , independently, is a labile atom or group; and M is H, an alkali metal, an ammonium ion or the equivalent of an alkaline earth metal, wherein compounds wherein R 1 and R 2 are H are excluded, mixtures of the dyestuffs of the formula (I) with dyestuffs of the formula (II) wherein each of X 3 and X 4 , independently, is a labile atom or group; L is an organic linking group; and M is H, an alkali metal, an ammonium ion or the equivalent of an alkaline earth metal, processes for the preparation of said dyestuffs and said dyestuff mixtures and their use for dyeing and printing hydroxy- and/or carboxamido-containing fiber materials.
1. Dyestuff of the formula I
wherein
R 1 is H or (C 1 –C 4 )-alkyl;
R 2 is H or (C 1 –C 4 )-alkyl;
each of X 1 and X 2 , independently, is a labile atom or group; and
M is H, an alkali metal, an ammonium ion or the equivalent of an alkaline earth metal,
wherein compounds wherein R 1 and R 2 are H are excluded.
2. Dyestuff according to claim 1 , wherein R 1 is H, R 2 is methyl or R 1 and R 2 are methyl, X 1 and X 2 are both chlorine and M is H, sodium or potassium.
3. Dyestuff mixture comprising
a) one or more dyestuffs of the formula (I) and
b) one or more dyestuffs of the formula (II)
wherein
each of X 3 and X 4 , independently, is a labile atom or group;
L is an organic linking group; and
M is H, an alkali metal, an ammonium ion or the equivalent of an alkaline earth metal.
4. Dyestuff mixture according to claim 3 , wherein in the dyestuff of the formula (II) L derives from aminoethylpiperazine, piperazine, 2-methyl-piperazine, ethylenediamine, N-methylethylenediamine, N,N′-dimethylethylenediamine, propylenediamine, N-methylpropylenediamine, N,N′-dimethylpropylenediamine, 2-methylpropylene-diamine, 2,2-dimethylpropylenediamine, 1,2-phenylenediamine, 1,3-phenylene-diamine, 1,4-phenylenediamine or 2-aminoethanethiol.
5. Dyestuff mixture according to claim 3 , wherein in the dyestuff of the formula (II) X 3 and X 4 are both chlorine, L derives from aminoethylpiperazine or ethylenediamine and M is H, sodium or potassium.
6. Dyestuff mixture according to claim 3 , wherein it contains from 50 to 95% by weight of one or more dyestuffs of the formula (I) and from 5 to 50% by weight of one or more of the dyestuffs of the formula (II), based on the weight of the dyestuffs (I) and (II).
7. Dyestuff mixture according to claim 5 , wherein it contains from 70 to 95% by weight of one or more dyestuffs of the formula (I) and from 5 to 30% by weight of one or more of the dyestuffs of the formula (II), based on the weight of the dyestuffs (I) and (II).
8. A process for preparing a dyestuff of formula I as claimed in claim 1 , which comprises reacting an ortho-phenylenediamine of the formula (III)
wherein R 1 and R 2 are defined as given above, with a compound of the formula (IV)
wherein X 1 and M are defined as given in claim 1 and X 5 is a labile atom or a group capable of reaction with an amine,
and with a compound of the formula (V)
wherein X 2 , X 5 and M are defined as given in claim 1 .
9. A process for preparing a dyestuff mixture as claimed in claim 3 , which comprises either
a) mechanically mixing the individual dyes of the formulae (I) and (II) in solid form or in form of aqueous solutions in the required proportions or
b) synthesizing by means of condensation reactions using mixtures of compounds of the formulae (III), (IV), (V) and of a compound of the formula H-L-H, wherein L is defined as given in claim 3 .
10. A process for dyeing and printing hydroxy- and/or carboxamido-containing fibre material which comprises contacting the material with the dyestuff of the formula (I) according to claim 1 .
11. A process for dyeing and printing hydroxy- and/or carboxamido-containing fibre material which comprises contacting the material with the dyestuff of the formula (I) according to claim 2 .
12. A process for dyeing and printing hydroxy- and/or carboxamido-containing fibre material which comprises contacting the material with the dyestuff mixture according to claim 3 .
13. A process for dyeing and printing hydroxy- and/or carboxamido-containing fibre material which comprises contacting the material with the dyestuff mixture according to claim 7 .
14. A process for preparing a dyestuff mixture as claimed in claim 7 , which comprises either
a) mechanically mixing the individual dyes of the formulae (I) and (II) in solid form or in form of aqueous solutions in the required proportions or
b) synthesizing by means of condensation reactions using mixtures of compounds of the formulae (III), (IV), (V) and of a compound of the formula H-L-H, wherein L is defined as given in claim 7 .