Azo dye compound having 1,2,4-triazole as the azo component

Details Azo dye compound having 1,2,4-triazole as the azo component Azo dye compound having 1,2,4-triazole as the azo component

2000-09-29

2002-10-01

Klemanski, Helene (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C534S752000, C008S690000, C008S691000

Reexamination Certificate

active

06458194

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a dye compound excellent in hue, and in color fastness against light, moisture and heat; and more specifically to a dye compounds in particular as a yellow dye, preferably used for full-color image producing system such as ink-jet system, direct digital thermal transfer system or fused thermal transfer system.
2. Description of Related Art
Azo dye is a kind of dye obtained by azo coupling of a so-called coupler component and a diazonium salt (so-called diazo component); in which the coupler component is such as an active hydrogen-containing compound, phenols or p-dialkylaminobenzenes; and the diazonium salt is derived from aminoaryl compound or aminohetero-aromatic compound. Azo dye holds a representative position in the field of dyes, since it is affordable of a wide variety of color tones by virtue of wide selection of the coupler and azo components. Among these, there are known popular yellow dyes such as of pyridone azo-base, aminopyrazole azo-base, pyrazolone azo-base and active methylene azo-base.
In recent years researches are extensively carried on in the fields of color photograph, color electronic photograph, ink-jet system, direct digital thermal transfer system (DDTT), fused thermal transfer system, printing ink and silver photograph based on the diffusion transfer system, in which the azo dye is applied as an image producing dye. The azo dye is also becoming a major issue of investigation as a filter dye in the field of electronics, since demands for filters for solid-state image pickup tube and color liquid crystal television set increases
There are a variety of proposed yellow dyes for use in ink-jet color copying machine, direct digital thermal transfer (DDTT) proofer, and fused thermal transfer proofer. In particular, a pyrazolotriazole-base azo dye disclosed in JP-A-1-275187 (the code “JP-A-” as used herein means an “unexamined published Japanese patent application”) is preferable for its sharp absorption waveform and relatively high color fastness against light. The color fastness against light is, however, not fully satisfiable yet and is still on the way to further improvement. On the other hand, JP-A-2-24191 discloses 1,2,4-thiadiazolyl azo dye, wherein the coupler of which consists of aminopyrazole or pyrazolo[5,1-c]triazole.
There is also well-known color diffusion transfer photographic method using an azo dye image producing compound which can release an azo dye differing in the diffusivity from the image producing compound per se under a basic development condition. The image producing compound used in such method suffers from a low transfer property and poor color fastness of an obtained image, so that the improvement thereof has been desired.
SUMMARY OF THE INVENTION
It is therefore an object of the present invention to solve the foregoing problems in the prior art.
That is, the present invention is to provide a dye compound excellent in transfer property and color fastness against light. It is another object of the present invention to provide a yellow dye compound excellent in light absorption property, It is again another object of the present invention to provide a yellow dye compound for thermal transfer dye donating material excellent in solubility. It is still another object of the present invention to provide a dye compound which can be synthesized with ease from readily-available source materials.
The present inventors found out from our extensive investigations on the azo component of pyrazolo[1,5-b]triazole azo dyes that those having 1,2,4-triazole as the azo component were preferable since they were particularly high in the color fastness against light, and such finding led us to complete the present invention.
While the compound of the present invention is a structural isomer of the dye disclosed JP-A-2-24191 or JP-A-1-275187, the compound of the present invention was found to exhibit an excellent solubility beyond our expectation when made into an ink and to show a good yield in the synthesis.
That is, the present invention is to provide a dye compound expressed by the general formula (1):
or a salt thereof, wherein
R
1
, R
2
, R
3
and R
4
independently represent a hydrogen atom or a substituent.
More preferably, R
1
, R
2
, R
3
and R
4
of the general formula (1) are independently any of the substituents selected from the group comprising hydrogen atom, halogen atom, aliphatic group, aryl group, heterocyclic group, cyano group, hydroxyl group, nitro group, carboxyl group, alkoxy group, aryloxy group, silyloxy group, heterocyclic oxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, amino group (including anilino group), acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkyl and arylsulfonylamino groups, alkylthio group, arylthio group, heterocyclic thio group, sulfamoyl group, sulfo group, alkyl and arylsulfinyl group, alkyl and arylsulfenyl groups, alkyl and arylsulfonyl groups, acyl group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, azo group, imide group and phosphoryl group.
Still more preferably, R
1
of the general formula (1) is any one of alkyl group, aryl group, acylamino group, heterocyclic group or alkoxy group: R
2
is either of alkyl group or aryl group; R
3
is any one of hydrogen atom, halogen atom, cyano group, aliphatic group, alkylthio group, alkylsulfonyl group, alkylsulfinyl group, alkoxycarbonyl group, carbamoyl group, alkoxy group, arylthio group, arylsulfonyl group, arylsulfinyl group, aryloxy group or aryl group; and R
4
is any one of hydrogen atom, aliphatic group or aryl group.
Other aspects of the present invention are to provide a filter, an ink sheet, a thermal transfer dye donating material and an ink composition containing the compound expressed by the general formula (1) or a salt thereof.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
Mode of implementation and embodiment of the present invention will be detailed hereinafter.
The compound of the present invention is characterized in that being expressed by the general formula (1).
In the formula, R
1
, R
2
, R
3
and R
4
independently represent a hydrogen atom or a substituent.
Specific examples of the substituent represented by R
1
, R
2
, R
3
or R
4
include halogen atom, aliphatic group, aryl group, heterocyclic group, cyano group, hydroxyl group, nitro group, carboxyl group, alkoxy group, aryloxy group, silyloxy group, heterocyclic oxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, amino group (including anilino group), acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkyl and arylsulfonylamino groups, alkylthio group, arylthio group, heterocyclic thio group, sulfamoyl group, sulfo group, alkyl and arylsulfinyl groups, alkyl and arylsulfenyl groups, alkyl and arylsulfonyl groups, acyl group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, azo group, imide group and phosphoryl group, while being not limited thereto.
More preferably, R
1
, R
2
and R
3
independently represent hydrogen atom; halogen atom (e.g., chlorine atom, bromine atom, iodine atom); aliphatic group [straight-chained or branched substituted or unsubstituted alkyl group (preferably alkyl group having 1 to 30 carbon atoms, and specifically methyl, ethyl, n-propyl, isopropyl, t-butyl, n-octyl, eicosyl, 2-chloroethyl, 2-cyanoethyl and 2-ethylhexyl groups), substituted or unsubstituted alkenyl group (preferably substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, and specifically allyl, prenyl, geranyl and oleyl groups), substituted or unsubstituted alkynyl group (preferably substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, and specifically ethynyl and propargyl groups), substituted or unsubstituted cycloalkyl group (preferably substituted or unsubstituted cycloalkyl group

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