Dye mixtures containing thienyl and/or thiazolazo dyes

Details Dye mixtures containing thienyl and/or thiazolazo dyes Dye mixtures containing thienyl and/or thiazolazo dyes

1998-09-22

2001-10-16

Hardee, John (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Process of printing permanently on substrate, other than...

Azo dye

C008S467000, C008S639000, C008S643000, C008S691000

Reexamination Certificate

active

06302924

ABSTRACT:

DESCRIPTION
The present invention relates to novel dye mixtures comprising one or more azo dyes (F1) of the formula I
where
K is a radical of the formula
X is nitrogen or C—Z
3
,
Z
1
is nitro, cyano, C
1
-C
6
-alkanoyl, benzoyl, C
1
-C
8
-alkoxycarbonyl, C
1
-C
8
-alkylsulfonyl, unsubstituted or C
1
-C
4
-alkyl-, C
1
-C
4
-alkoxy-, halogen- or nitro-substituted phenylsulfonyl or a radical of the formula —CH═T, where T is a radical of an acidic-CH compound of the formula H
2
T,
Z
2
is hydrogen, C
1
-C
6
-alkyl, unsubstituted or C
1
-C
4
-alkyl-, C
1
-C
4
-alkoxy-, halogen- or nitro-substituted phenyl, cyano, halogen, unsubstituted or phenyl- or C
1
-C
4
-alkoxy-substituted C
1
-C
6
-alkoxy, unsubstituted or phenyl-substituted C
1
-C
8
-alkylthio, unsubstituted or C
1
-C
4
-alkyl-, C
1
-C
4
-alkoxy-, halogen- or nitro- substituted phenylthio, C
1
-C
8
-alkylsulfonyl, unsubstituted or C
1
-C
4
-alkyl-, C
1
-C
4
-alkoxy-, halogen- or nitro-substituted phenylsulfonyl or C
1
-C
8
-alkoxycarbonyl,
Z
3
is C
1
-C
8
-alkoxycarbonyl, cyano, nitro or hydrogen,
Y
1
and Y
2
are independently of each other C
1
-C
10
-alkyl which is unsubstituted or substituted by cyano, hydroxyl, halogen, C
1
-C
4
-alkanoyloxy, C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkoxycarbonyloxy, whose alkyl chains may each be interrupted by 1 oxygen atom in ether function, or phenyl and may be interrupted by from 1 to 4 oxygen atoms in ether function, C
5
-C
7
-cycloalkyl, C
3
-C
4
-alkenyl, unsubstituted or C
1
-C
4
-alkyl-, C
1
-C
4
-alkoxy-, halogen- or nitro-substituted phenyl, or Y
1
and Y
2
together with the nitrogen atom joining them together are a 5- or 6-membered saturated heterocyclic radical with or without further hetero atoms, or else Y
1
is hydrogen,
Y
3
is C
1
-C
10
-alkyl, C
5
-C
7
-cycloalkyl, unsubstituted or C
1
-C
4
-alkyl-, C
1
-C
4
-alkoxy-, halogen- or nitro-substituted phenyl or thienyl,
Y
4
is hydrogen, C
1
-C
10
-alkyl with or without interruption by from 1 to 4 oxygen atoms in ether function, hydroxyl, C
1
-C
6
-alkoxy, in particular methoxy or ethoxy, C
1
-C
4
-alkylsulfonylamino, mono- or di(C
1
-C
8
-alkyl)aminosulfonylamino or the radical —NHCOY
9
or —NHCO
2
Y
9
, where Y
9
is phenyl, benzyl, tolyl or C
1
--C
10
-alkyl with or without interruption by from 1 to 4 oxygen atoms in ether function,
Y
5
is hydrogen, C
1
-C
6
-alkyl or C
1
-C
6
-alkoxy,
Y
6
and Y
7,
a) when X is C—Z
3
, are independently of each other hydrogen, C
1
-C
10
-alkyl which is unsubstituted or substituted by cyano, hydroxyl, halogen, C
1
-C
4
-alkanoyloxy, C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkoxycarbonyloxy, whose alkyl chains may each be interrupted by 1 oxygen atom in ether function, or phenyl and may be interrupted by from 1 to 4 oxygen atoms in ether function, C
5
-C
7
-cycloalkyl, C
3
-C
4
-alkenyl, unsubstituted or C
1
-C
4
-alkyl-, C
1
-C
4
-alkoxy-, halogen- or nitro-substituted phenyl, or Y
6
and Y
7
together with the nitrogen atom joining them together are a 5- or 6-membered saturated heterocyclic radical with or without further hetero atoms, or b) when X is nitrogen, are each C
1
-C
10
-alkyl which is unsubstituted or substituted by phenyl and may be interrupted by 1 oxygen atom in ether function, with the proviso that Y
6
and Y
7
are different in case b), and
Y
8
is hydrogen or Y
1
,
one or more dyes (F2) which have their respective absorption maximum at a wavelength of from 410 to 530 nm and optionally one or more dyes (F3) which have their respective absorption maximum at a wavelength of from 600 to 700 nm, the FWHM value of the absorption maximum of the dyes F2 and F3 being at least 2000 cm
−1
,
to a process for the thermal transfer of these dyes and to a process for dyeing or printing synthetic materials.
In the thermal transfer printing process, a transfer sheet comprising a thermally transferable dye in one or more binders with or without suitable auxiliaries on a support is heated from the back with an energy source for example a thermal head or a laser, for short periods (duration: fractions of a second), which causes the dye to migrate out of the transfer sheet and diffuse into the surface coating of a receiving medium. The essential advantage of this process is that the amount of dye to be transferred (and thus the colour gradation) is easy to control by controlling the energy emitted by the energy source.
In general, color recording is carried out using the three subtractive primaries of yellow, magenta and cyan (with or without black).
It is known to carry out the thermal transfer printing process with individual dyes or else with mixtures of dyes. However, it has been found that the dyes used frequently still have application defects.
It is an object of the present invention to provide novel dye mixtures in the black region of the spectrum which shall be advantageously suitable for thermal transfer.
We have found that this object is achieved by the dye mixtures defined at the beginning.
Any alkyl or alkenyl appearing in the abovementioned formulae may be straight-chain or branched.
Any substituted alkyl appearing in the abovementioned formulae generally contains 1 or 2 substituents.
Any substituted alkyl appearing in the abovementioned formulae generally contains 1 or 2 substituents.
Any substituted phenyl, pyridyl or thienyl appearing in the abovementioned formulae generally contains from 1 to 3, preferably 1 or 2, substituents.
There follows a list of examples of radicals as defined in the formulae. It also includes radicals present in below-stated formulae.
Alkyl is for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl, isodecyl (the designations isooctyl, isononyl and isodecyl are trivial names derived from the oxo process alcohols—cf. Ullmann's Encyclopedia of Industrial Chemistry, 5
th
Edition, Vol. A 1, pages 290 to 293, and also Vol. A 10, pages 284 and 285), 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-butoxyethyl, 2- or 3-methoxypropyl, 2- or 3-ethoxypropyl, 2- or 3- propoxypropyl, 2- or 3-butoxypropyl, 2- or 4-methoxybutyl, 2- or 4-ethoxybutyl, 2- or 4-propoxybutyl, 2- or 4-butoxybutyl, 3,6-dioxaheptyl, 3,6-dioxaoctyl, 4,8-dioxanonyl, 3,7-dioxaoctyl, 3,7-dioxanonyl, 4,7-dioxaoctyl, 4,7-dioxanonyl, 4,8-dioxadecyl, 3,6,8-trioxadecyl, 3,6,9-trioxaundecyl, 3,6,9,12-tetraoxatridecyl, 3,6,9,12-tetraoxatetradecyl, 2-methoxycarbonylethyl, 2-ethoxycarbonylethyl, 2-propoxycarbonylethyl, 2-isopropoxycarbonylethyl, 2-butoxycarbonylethyl, 2- or 3-methoxycarbonylpropyl, 2- or 3-ethoxycarbonylpropyl, 2- or 3-propoxycarbonylpropyl, 2- or 3-butoxycarbonylpropyl, 2- or 4-methoxycarbonylbutyl, 2- or 4-ethoxycarbonylbutyl, 2- or 4-propoxycarbonylbutyl, 2- or 4-butoxycarbonylbutyl, 2-methoxycarbonyloxyethyl, 2-ethoxycarbonyloxyethyl, 2-propoxycarbonyloxyethyl, 2-isopropoxycarbonyloxyethyl, 2-butoxycarbonyloxyethyl, 2- or 3-methoxycarbonyloxypropyl, 2- or 3-ethoxycarbonyloxypropyl, 2or 3-propoxycarbonyloxypropyl, 2- or 3-butoxycarbonyloxypropyl, 2- or 4-methoxycarbonyloxybutyl, 2- or 4-ethoxycarbonyloxybutyl, 2- or 4-propoxycarbonyloxybutyl, 2- or 4-butoxycarbonyloxybutyl, benzyl, 2-phenylethyl, 2-, 3- or 4-methylbenzyl, 2-, 3- or 4-methoxybenzyl, 2-, 3- or 4-nitrobenzyl, 2-hydroxyethyl, 2- or 3-hydroxypropyl or 2- or 4-hydroxybutyl.
Alkenyl is for example prop-1-en-3-yl, but-2-en-4-yl or 2-methylprop-1-en-3-yl.
Cycloalkyl is for example cyclopentyl, methylcyclopentyl, dimethylcyclopentyl, cyclohexyl, methylcyclohexyl or cycloheptyl.
Phenyl is for example phenyl, 2-, 3- or 4-methylphenyl, 2-, 3- or 4-ethylphenyl, 2-, 3- or 4-propylphenyl, 2-, 3- or 4-isopropylphenyl, 2-, 3- or 4-butylphenyl, 2,3-, 2,4- or 2,6-dimethylphenyl, 2-, 3- or 4-methoxyphenyl, 2-, 3- or 4-ethoxyphenyl, 2,3-, 2,4- or 2,6-dimethoxyphenyl, 2-, 3- or 4-fluorophenyl, 2-, 3- or 4-chlorophenyl, 2-, 3- or 4-bromophenyl or 2-, 3- or 4-nitrophenyl.
Carbamoyl is for example mono- or dimethylcarbamoyl, mono- or diethylcarbam

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