Dye preparations containing azo dyes

Details Dye preparations containing azo dyes Dye preparations containing azo dyes

2000-06-05

2003-03-25

Einsmann, Margaret (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Diffusion transfer dyeing process, transfer sheet and product

Dry heat treatment for penetration

C008S445000, C008S466000, C008S552000, C008S557000, C008S560000, C008S576000, C008S613000, C008S611000, C008S662000, C008S687000, C008S561000

Reexamination Certificate

active

06537331

ABSTRACT:

The present invention relates to novel dye preparations w comprising, based in each case on the weight of the preparation, from 0.1 to 30% by weight of one or more dyes from the class of the mono- or polyazo dyes containing no acidic groups, from 0.1 to 20% by weight of a dispersant based on an arylsulfonic acid-formaldehyde condensate or from 0.1 to 20% by weight of a water-soluble dispersant based on alkoxylated phenols with or without water, and to their use as inks in the inkjet process and for textile sublimation transfer printing.
EP-A-655 527 has already disclosed dye preparations comprising disperse dyes and specific dispersants.
It is an object of the present invention to provide novel dye preparations comprising mono- or polyazo dyes. These novel dye preparations should advantageously be suitable for use in the inkjet process and in textile sublimation transfer printing.
We have found that this object is achieved by the dye preparations detailed at the outset.
Suitable mono- or polyazo dyes are known per se and are described in large numbers in, for example, K. Venkataraman “The Chemistry of Synthetic Dyes”, Vol. VI, Academic Press, New York, London, 1972.
Of particular importance are azo dyes, especially monoazo dyes, having a diazo component which is derived from an aniline or from a five-membered aromatic heterocyclic amine having from one to three heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur in the heterocyclic ring and can be fused with a benzene, thiophene, pyridine or pyrimidine ring.
Examples of important monoazo dyes are those whose diazo component is derived, for example, from an aniline or from a heterocyclic amine from the pyrrole, furan, thiophene, pyrazole, imidazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thiadiazole, benzofuran, benzothiophene, benzimidazole, benzoxazole, benzothiazole, benzisothiazole, pyridothiophene, pyrimidothiophene, thienothiophene or thienothiazole series.
Particular mention may be made of those diazo components which originate from an aniline or from a heterocyclic amine from the pyrrole, thiophene, pyrazole, thiazole, isothiazole, triazole, thiadiazole, benzothiophene, benzothiazole, benzisothiazole, pyridothiophene, pyrimidothiophene, thienothiophene or thienothiazole series.
Also of importance are azo dyes, especially monoazo dyes, having a coupling component from the aniline, aminonaphthalene, aminothiazole, diaminopyridine or hydroxypyridone series.
Particularly important monoazo dyes are of the formula I
D—N═N—K  (I),
where
D is a radical of the formula
K is a radical of the formula
 in which
L
1
is nitro, cyano, C
1
-C
6
-alkanoyl, benzoyl, C
1
-C
6
-alkylsulfonyl, unsubstituted or substituted phenylsulfonyl or a radical of the formula —CH═T, where T is hydroxyimino, C
1
-C
4
-alkoxyimino or the radical of a CH-acidic compound,
L
2
is hydrogen, C
1
-C
6
-alkyl, halogen, hydroxyl, mercapto, unsubstituted, phenyl-substituted or C
1
-C
4
-alkoxy-substituted C
1
-C
6
-alkoxy, unsubstituted or substituted phenoxy, unsubstituted or phenyl-substituted C
1
-C
6
-alkylthio, unsubstituted or substituted phenylthio, C
1
-C
6
-alkylsulfonyl or unsubstituted or substituted phenylsulfonyl,
L
3
is cyano, C
1
-C
4
-alkoxycarbonyl or nitro,
L
4
is hydrogen, C
1
-C
6
-alkyl or phenyl,
L
5
is C
1
-C
6
-alkyl or phenyl,
L
6
is hydrogen, cyano, C
1
-C
4
-alkoxycarbonyl, C
1
-C
6
-alkanoyl, thiocyanato or halogen,
L
7
is nitro, cyano, C
1
-C
6
-alkanoyl, benzoyl, C
1
-C
4
-alkoxycarbonyl, C
1
-C
6
-alkylsulfonyl, unsubstituted or substituted phenylsulfonyl or a radical of the formula —CH═T, in which T is as defined above,
L
8
is hydrogen, C
1
-C
6
-alkyl, cyano, halogen, unsubstituted, phenyl-substituted or C
1
-C
4
-alkoxy-substituted C
1
-C
6
-alkoxy, unsubstituted or phenyl-substituted C
1
-C
6
-alkylthio, unsubstituted or substituted phenylthio, C
1
-C
6
-alkylsulfonyl, unsubstituted or substituted phenylsulfonyl or C
1
-C
4
-alkoxycarbonyl,
L
9
is cyano, unsubstituted or phenyl-substituted C
1
-C
6
-alkyl, unsubstituted or phenyl-substituted C
1
-C
6
-alkylthio, unsubstituted or substituted phenyl, thienyl, C
1
-C
4
-alkylthienyl, pyridyl or C
1
-C
4
-alkylpyridyl,
L
10
is phenyl or pyridyl,
L
11
is trifluoromethyl, nitro, C
1
-C
6
-alkyl, phenyl, unsubstituted or phenyl-substituted C
1
-C
6
-alkylthio or C
1
-C
6
-dialkylamino,
L
12
is C
1
-C
6
-alkyl, phenyl, 2-cyanoethylthio or 2-(C
1
-C
4
-alkoxycarbonyl)ethylthio,
L
13
is hydrogen, nitro or halogen,
L
14
is hydrogen, cyano, C
1
-C
4
-alkoxycarbonyl, nitro or halogen,
L
15
, L
16
and L
17
are identical or different and independently of one another are each hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, halogen, nitro, cyano, C
1
-C
4
-alkoxycarbonyl, C
1
-C
6
-alkylsulfonyl or unsubstituted or substituted phenylsulfonyl,
R
1
and R
2
are identical or different and independently of one another are each hydrogen, unsubstituted or substituted C
1
-C
6
-alkyl, which may be interrupted by 1 or 2 oxygen atoms in ether function, C
5
-C
7
-cycloalkyl or C
3
-C
6
-alkenyl,
R
3
is hydrogen, C
1
-C
6
-alkyl or C
1
-C
6
-alkoxy,
R
4
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylsulfonylamino, unsubstituted or substituted C
1
-C
6
-alkanoylamino or benzoylamino,
R
5
and R
6
are identical or different and independently of one another are each hydrogen or C
1
-C
6
-alkyl,
R
7
is hydrogen, unsubstituted or substituted phenyl or thienyl,
R
8
is hydrogen or C
1
-C
6
-alkyl,
R
9
is cyano, carbamoyl or acetyl,
R
10
, R
11
and R
12
are identical or different and independently of one another are each unsubstituted or substituted C
1
-C
12
-alkyl which may be interrupted by 1 to 3 oxygen atoms in ether function, C
5
-C
7
-cycloalkyl, unsubstituted or substituted phenyl, C
3
-C
6
-alkenyl, unsubstituted or substituted benzoyl, C
1
-C
8
-alkanoyl, C
1
-C
6
-alkylsulfonyl or unsubstituted or substituted phenylsulfonyl or R
11
and R
12
together with the nitrogen atom connecting them are a 5- or 6-membered saturated heterocyclic radical with or without further heteroatoms, and
R
13
is hydrogen or C
1
-C
6
-alkyl.
Also of particular importance are disazo dyes of the formula IVa or IVb
where
A
1
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy or nitro,
A
2
is hydrogen or cyano
A
3
and A
4
are identical or different and independently of one another are each hydrogen, C
1
-C
6
-alkyl or C
1
-C
6
-alkoxy,
A
5
are hydrogen, hydroxyl, C
1
-C
6
-alkoxy, amino or unsubstituted or cyano-substituted C
1
-C
6
-mono- or dialkylamino,
A
6
is hydrogen, methyl or chlorine, and
A
7
is cyano or C
1
-C
4
-alkoxycarbonyl.
All of the alkyl or alkenyl groups appearing in the above formulae can be either straight-chain or branched.
Where substituted phenyl groups appear in the above formulae possible examples of suitable substituents are C
1
-C
4
-alkyl, chlorine, bromine, nitro or C
1
-C
4
-alkoxy. Such phenyl radicals generally have 1 to 3 substituents.
Where substituted alkyl groups appear in the above formulae possible examples of suitable substituents are, unless indicated otherwise, hydroxyl, cyclohexyloxy, phenoxy, C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkanoyloxy, cyano, cyclohexyl or phenyl. Such alkyl radicals generally have 1 or 2 substituents.
Radicals L
2
, L
4
, L
5
, L
8
, L
9
, L
11
, L
12
, L
15
, L
16
, L
17
, R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
8
, R
10
, R
11
, R
12
, R
13
, A
1
, A
3
and A
4
are for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl or 2-methylpentyl.
Radicals L
9
are also for example benzyl or 1- or 2-phenylethyl.
Radicals L
2
, L
8
, L
9
and L
11
are also for example methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, pentylthio, hexylthio, benzylthio or 1- or 2-phenylethylthio.
Radicals L
2
and L
8
are also for example phenylthio, 2-methylphenylthio, 2-methoxyphenylthio or 2-chlorophenylthio.
Radicals A
5
, and also radicals of L
2
, L
8
, L
15
, L
16
, L

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