Dye mixtures, 1:2 cobalt complex formazan dyes and their use

Details Dye mixtures, 1:2 cobalt complex formazan dyes and their use Dye mixtures, 1:2 cobalt complex formazan dyes and their use

2001-02-22

2003-04-22

Einsmann, Margaret (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Dye or potential dye composition, additive, treatment,...

Azo, acridone, or quinone dye

C008S687000, C008S918000, C008S924000, C534S652000, C534S653000, C534S654000, C534S656000

Reexamination Certificate

active

06551364

ABSTRACT:

The present invention relates to mixtures of 1:2 cobalt complex formazan dyes with anthraquinone dyes or 1:2 chromium or 1:2 cobalt complex azo dyes, which are particularly suitable for dyeing or printing natural or synthetic textile polyamide fibre materials and in particular have very good fastness properties. The present invention furthermore relates to the novel 1:2 cobalt complex formazan dyes.
The present invention relates to dye mixtures which comprise at least one 1:2 cobalt complex dye of the formazan compound of the formula
in which X is substituted or unsubstituted C
1
-C
8
alkyl, phenyl, naphthyl, furyl or thienyl,
R
1
and R
2
independently of one another are hydrogen or substituted or unsubstituted C
1
-C
8
alkyl, phenyl or naphthyl,
m is a number from 1 to 4 and
the rings I, II, III and IV may be further substituted,
together with at least one anthraquinone dye of the formula (2)
in which Y is hydrogen or substituted or unsubstituted C
1
-C
8
alkyl, cyclohexyl, phenyl or 1,2,3,4-tetrahydronaphthyl and
Z is substituted or unsubstituted C
1
-C
8
alkyl, cyclohexyl, phenyl or 1,2,3,4-tetrahydronaphthyl,
and in which the ring V of the anthraquinone dye of the formula (2) may be further substituted by one or two hydroxyl groups,
or together with at least one 1:2 chromium or 1:2 cobalt complex dye of two identical or different azo compounds from the group comprising compounds of the formulae (3), (4), (5) and (6)
in which R
3
, R
4
, R
5
, R
6
, R
7
, R
8
, R
9
, R
10
, R
11
, R
12
, R
13
, R
14
, R
15
and R
16
independently of one another are hydrogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
2
-C
4
alkanoylamino, halogen, sulfo, hydroxyl, nitro, sulfamoyl or N—C
1
-C
4
alkylsulfamoyl, which is unsubstituted or further substituted in the alkyl moiety part by hydroxyl or C
1
-C
4
alkoxy.
The 1:2 cobalt complex formazan dyes of the formula (1) are preferably symmetric cobalt complex dyes.
Substituents of a phenyl, naphthyl, furyl or thienyl radical X and of rings I, II, III and IV of the formazan compound of the formula (1) are, in addition to the radical of the formula —SO
2
N(R
1
)R
2
, independently of one another, for example, C
1
-C
4
alkyl, for example methyl or ethyl; C
1
-C
4
alkoxy, for example methoxy or ethoxy; unsubstituted or halogen-substituted C
2
-C
4
alkanoylamino, for example acetylamino, propionylamino or &agr;,&bgr;-dibromopropionylamino; hydroxyl; sulfo; nitro; carboxyl; cyano; amino; halogen, for example fluorine, chlorine or bromine; C
1
-C
4
alkylsulfonyl which is unsubstituted or substituted in the alkyl moiety by hydroxyl or C
1
-C
4
alkoxy; vinylsulfonyl; &agr;-halogenoacryloylamino; radicals of the formulae —OR, —NHCOR′, —COOR″, CONHR′″ and SO
2
R″″, in which R, R′, R″, R′″ and R″″ independently of one another are phenyl or naphthyl and R′ can additionally be C
1
-C
4
alkyl; or triazinylamino, which can be further substituted by halogen, C
1
-C
4
alkylamino, phenylamino or N-C
1
-C
4
alkyl-N-phenylamino. The phenyl or naphthyl radicals mentioned can be substituted as defined above for X and the rings I, II, III and IV, in particular by C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
2
-C
4
alkanoylamino, hydroxyl, sulfo, nitro, carboxyl, cyano, halogen or C
1
-C
4
alkylsulfonyl which is unsubstituted or further substituted in the alkyl moiety by hydroxyl or C
1
-C
4
alkoxy.
In addition to the radical of the formula —SO
2
N(R
1
)R
2
, preferred substituents for X and the rings I, II, III and IV of the formazan compound of the formula (1) are C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
2
-C
4
alkanoylamino, C
1
-C
4
alkylsulfonyl, C
1
-C
4
hydroxyalkylsulfonyl, halogen, sulfo, hydroxyl, carboxyl and nitro.
X is preferably phenyl, which can be substituted, for example, as defined above.
Phenyl or naphthyl radicals R
1
and R
2
can be unsubstituted or substituted. Examples of such substituents are C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
2
-C
4
alkanoylamino, C
1
-C
4
alkylsulfonyl, halogen, sulfo, hydroxyl, carboxyl, nitro, sulfamoyl and N—C
1
-C
4
alkylsulfamoyl which is unsubstituted or further substituted in the alkyl moiety by hydroxyl or C
1
-C
4
alkoxy.
C
1
-C
8
alkyl radicals X, R
1
and R
2
independently of one another are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl or octyl, and the corresponding radicals which are substituted, for example, by hydroxyl, C
1
-C
4
alkoxy or halogen. C
1
-C
4
alkyl, which can be substituted as defined, is preferred here.
R
1
and R
2
are preferably independently of one another hydrogen, C
1
-C
8
alkyl or phenyl, where the alkyl and phenyl radicals can be substituted as defined above.
R
1
and R
2
are preferably independently of one another hydrogen, C
1
-C
4
alkyl which is unsubstituted or substituted by hydroxyl or C
1
-C
4
alkoxy, or phenyl which is unsubstituted or substituted by C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
2
-C
4
alkanoylamino, C
1
-C
4
alkylsulfonyl, C
1
-C
4
hydroxyalkylsulfonyl, halogen, sulfo, hydroxyl, carboxyl, nitro, sulfamoyl or N—C
1
-C
4
alkylsulfamoyl which is unsubstituted or further substituted in the alkyl moiety by hydroxyl or C
1
-C
4
alkoxy. In particular, one of the radicals R
1
and R
2
is hydrogen here.
R
1
and R
2
are particularly preferably hydrogen, C
1
-C
4
alkyl which is unsubstituted or substituted by hydroxyl, or phenyl which is unsubstituted or substituted by sulfo, carboxyl or sulfamoyl. In particular, one of the radicals R
1
and R
2
is hydrogen here. R
1
and R
2
are especially preferably independently of one another hydrogen or C
1
-C
4
alkyl, in particular hydrogen or methyl.
m is preferably the number 1 or 2, in particular the number 2.
Substituents of phenyl radicals Y and Z are, for example: C
1
-C
12
alkyl; C
1
-C
4
alkoxy; C
2
-C
4
alkanoylamino; hydroxyl; sulfo; nitro; carboxyl; cyano; amino; halogen; benzoylaminomethyl; chloroacetylamino; chloroacetylaminomethyl; &agr;-chloroacryloylaminomethyl; acryloylaminomethyl; or phenoxy, phenylcarbonylamino, phenylsulfonyloxy, phenylsulfonylamino, phenylsulfonylaminomethyl or N-methyl-phenylsulfonylaminomethyl, where the phenyl radicals can be further substituted as defined above for Y and Z. The radical Z furthermore can be an anthraquinone dye radical bonded via a bridge member, examples of these are the anthraquinone dyes of the following formula (11).
C
1
-C
8
alkyl radicals Y and Z independently of one another are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl or octyl, where the alkyl radicals can be substituted by phenyl and the phenyl radical can be further substituted as defined above for phenyl radicals Y and Z. Preferred substituents of the phenyl radical here are C
1
-C
12
alkyl, C
1
-C
4
alkoxy, C
2
-C
4
alkanoylamino, hydroxyl, sulfo, nitro, carboxyl, cyano, amino, halogen, benzoylaminomethyl, chloroacetylamino, chloroacetylaminomethyl, a-chloroacryloylaminomethyl or acryloylaminomethyl.
Cyclohexyl radicals Y and Z independently of one another are, in addition to unsubstituted cyclohexyl, cyclohexyl substituted, for example, by C
1
-C
4
alkyl, phenylsulfonylamino or benzyl, where the phenyl radicals can be further substituted, for example, by C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
2
-C
4
alkanoylamino, sulfo or halogen.
1,2,3,4-Tetrahydronaphthyl radicals Y and Z independently of one another are, in addition to unsubstituted 1,2,3,4-tetrahydronaphthyl, the radical substituted, for example, by sulfo.
If the anthraquinone dye of the formula (2) contains one or two hydroxyl groups in ring V, these are as a rule bonded in the 1- and/or 2-position.
The total number of sulfo groups in the anthraquinone dye of the formula (2) is one or two.
C
1
-C
4
alkyl radicals R
3
to R
16
independently of one another are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl, in particular methyl.
C
1
-C
4
alkoxy radicals R
3
to R
16
independently of one another are methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-b

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