Black-dyeing inks and their use

Details Black-dyeing inks and their use Black-dyeing inks and their use

2000-02-01

2002-12-31

Klemanski, Helene (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C106S031480, C106S031500, C106S031520

Reexamination Certificate

active

06500247

ABSTRACT:

The present invention relates to black-dyeing inks based on navy blue copper complex azo or copper complex formazan dyes, black-dyeing mixtures based on such dyes and novel dyes.
The inks on which the present invention is based are particularly suitable for printing paper, preferably by the ink-jet printing process, and for dyeing or printing fibre materials which contain nitrogen or hydroxyl groups, and give dyeings or prints which are distinguished by a high fastness to light.
The present invention therefore relates to black-dyeing aqueous inks comprising 20 to 95% by weight of at least one dye (A), together with 5 to 80% by weight of at least one dye chosen from the group consisting of (B) and (C), based on the total weight of the dyes (A), (B) and (C) in the ink, and 1 to 40% by weight of a water-miscible organic solvent, based on the total weight of the ink, the dye (A) containing, as the colouring part of the molecule, one or more radicals of the formula (I), (II), (III) or (IV)
the dye (B) containing, as the colouring part of the molecule, one or more mono- or disazo radicals containing sulfo groups or one or more radicals of the formula (V), (VI), (VII) or (VIII)
and the dye (C) containing, as the colouring part of the molecule, one or more mono- or disazo radicals containing sulfo groups or one or more radicals of the abovementioned formula (V), (VI), (VII) or (VII) and one or more radicals of the abovementioned formula (I), (II), (III) or (IV), in which
(G)
0-2
is 0 to 2 identical or different substituents from the group consisting of substituted or unsubstituted amino, hydroxyl and nitro,
L is substituted or unsubstituted amino,
R is halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
2
-C
4
alkanoylamino, hydroxyl, carboxyl, nitro or cyano,
(V)
0-2
is 0 to 2 identical or different substituents from the group consisting of halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, &bgr;-sulfatoethylsulfonyl and sulfo,
(W)
0-1
is an N-acyl radical, if any,
n is the number 0, 1, 2 or 3,
m is the number 1, 2 or 3 and
r and q are the number O or 1.
C
1
-C
4
alkyl R and V is, for example, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl or isobutyl, preferably methyl or ethyl, and in particular methyl.
C
1
-C
4
alkoxy R and V is, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy or isobutoxy, preferably methoxy or ethoxy, and in particular methoxy.
Halogen R and V is, for example, fluorine, chlorine or bromine, preferably chlorine or bromine, and in particular chlorine.
C
2
-C
4
alkanoylamino R is, for example, acetylamino or propionylamino, in particular acetylamino.
R is preferably C
1
-C
4
alkyl, C
1
-C
4
alkoxy, hydroxyl, carboxyl, nitro or cyano, in particular C
1
-C
4
alkyl, C
1
-C
4
alkoxy, hydroxyl or carboxyl, and especially carboxyl.
V is preferably halogen, &bgr;sulfatoethylsulfonyl or sulfo, in particular sulfo.
Substituted or unsubstituted amino G and L is, for example, amino, N-mono- or N,N-di- C
1
-C
4
alkylamino which are unsubstituted or substituted in the alkyl moiety by C
1
-C
4
alkoxy, hydroxyl, sulfato or sulfo, or phenylamino or N-C
1
-C
4
alkyl-N-phenylamino which are unsubstituted or substituted in the phenyl ring by C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
2
-C
4
alkanoylamino, sulfo, carboxyl or halogen, in particular amino or phenylamino.
An N-acyl radical W is, for example, C
2
-C
4
alkanoylamino, for example acetylamino or propionylamino, benzoylamino which is unsubstituted or substituted in the phenyl ring by C
1
-C
4
alkyl, C
1
-C
4
alkoxy, halogen or sulfo, or a radical of the formula
in which T
1
and T
2
independently of one another are fluorine or chlorine, C
1
-C
4
alkylthio which is unsubstituted or substituted in the alkyl moiety by hydroxyl, sulfato, sulfo or carboxyl, hydroxyl, amino, N-mono- or N,N-di-C
1
-C
4
alkylamino which is unsubstituted or substituted in the alkyl moiety by hydroxyl, carboxyl, C
1
-C
4
alkoxy, sulfato or sulfo, morpholino, phenylamino or N-C
1
-C
4
alkyl-N-phenylamino which are unsubstituted or substituted in the phenyl ring by sulfo, carboxyl, acetylamino, chlorine, methyl or methoxy and in which the alkyl is unsubstituted or substituted by hydroxyl, sulfo or sulfato, or naphthylamino which is unsubstituted or substituted by 1 to 3 sulfo groups.
q is preferably the number 1.
m is preferably the number 2 or 3, in particular 2.
If R is carboxyl, the sum of m+n is preferably 3 or 4, and in particular 3.
Inks according to the invention which are preferred are those which contain a radical of the formula (IV) in which
q is the number 1,
n is the number 0 and
m is the number 2 or 3.
The sulfo groups of the dyes (A), (B) and (C) in the inks according to the invention are either in the form of the free sulfonic acid or, preferably, in the salt form thereof, for example as the sodium, lithium, potassium or ammonium salt or as the salt of an organic amine, for example as the triethanolammonium salt.
The dyes (A), (B) and (C) in the inks according to the invention contain no further colouring molecular moieties in addition to the colouring molecular moieties mentioned.
The dye (A) in the inks according to the invention preferably contains, as the colouring molecular moiety (chromophore), one or two radicals of the formula (I), (II), (III) or (IV).
If the dye (A) contains a radical of the formula (I), (II), (III) or (IV), a non-chromophoric radical is bonded to this radical via the free valency drawn in the formulae (I), (II), (III) and (IV).
Examples of a non-chromophoric radical are the following:
C
2
-C
6
alkanoylamino which is unsubstituted or substituted in the alkyl moiety by hydroxyl, sulfo, carboxyl or C
1
-C
4
alkoxy, which can in its turn be substituted in the alkyl moiety by carboxyl, for example acetylamino, hydroxyacetylamino, methoxyacetylamino, carboxymethylenoxyacetylamino, propionylamino or &bgr;-carboxypropionylamino; N-C
1
-C
4
alkylamino which is unsubstituted or substituted in the alkyl moiety by hydroxyl, sulfo, carboxyl or C
1
-C
4
alkoxy, for example 3-sulfopropylamino or 4-sulfobutylamino; benzoylamino which is unsubstituted or substituted in the phenyl moiety by hydroxyl, sulfo, halogen, C
1
-C
4
alkyl or C
1
-C
4
alkoxy; C
2
-C
6
alkoxycarbonylamino which is unsubstituted or substituted in the alkyl moiety by hydroxyl, C
1
-C
4
alkyl or C
1
-C
4
alkoxy; phenoxycarbonylamino which is unsubstituted or substituted in the phenyl moiety by hydroxyl, C
1
-C
4
alkyl or C
1
-C
4
alkoxy; phenylsulfonylamino which is unsubstituted or substituted in the phenyl moiety by C
1
-C
4
alkyl or C
2
-C
4
alkanoylamino, or C
1
-C
4
alkylsulfonylamino, for example methyl- or ethylsulfonylamino, or a radical of the formula
 in which T
3
and T
4
independently of one another are a substituent which is not fibre-reacted, for example C
1
-C
4
alkoxy, C
1
-C
4
alkylthio which is unsubstituted or substituted in the alkyl moiety by hydroxyl, sulfato, sulfo or carboxyl, hydroxyl, amino, N-mono- or N,N-di-C
1
-C
4
alkylamino which is unsubstituted or substituted in the alkyl moiety by hydroxyl, carboxyl, C
1
-C
4
alkoxy, sulfato or sulfo, morpholino, phenylamino or N-C
1
-C
4
alkyl-N-phenylamino, which are unsubstituted or substituted in the phenyl ring by sulfo, carboxyl, acetylamino, chlorine, methyl or methoxy, and in which the alkyl is unsubstituted or substituted by hydroxyl, sulfo or sulfato, or naphthylamino which is unsubstituted or substituted by 1 to 3 sulfo groups.
Non-chromophoric radicals which are bonded via the free valency in the formula (I), (II), (III) or (IV) are also fibre-reactive radicals.
Fibre-reactive radicals are, for example, an alkanoyl or alkylsulfonyl radical substituted by an atom which can be split off or a group which can be split off, an alkenoyl or alkenesulfonyl radical which is unsubstituted or substituted by an atom which can be split off or a group which can be split off, or an alkenoyl or alkenesulfonyl radical which contains a vinyl group. The alkanoyl, alkylsulfonyl and alkenesulfonyl radicals mentioned as a rule contain 2 to 8 carbon atoms and the alkenoyl radicals as

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