Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Reexamination Certificate
2001-08-02
2002-09-24
Powers, Fiona T. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
C534S775000, C534S792000, C534S793000, C106S031450, C106S031480, C106S031500
Reexamination Certificate
active
06455679
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a novel heterylaniline azo dye, an ink-jet recording ink containing the dye, and an ink-jet recording method.
2. Description of the Related Art
Image-recording materials containing specific dyes are mainly materials for forming images, and in particular color images. More specifically, these materials include ink-jet recording materials, heat-sensitive transfer-type image recording materials, pressure-sensitive recording materials, electrophotography recording materials, transfer-type silver halide photosensitive materials, printing inks, and recording pens. Preferably, these materials are ink-jet recording materials, heat-sensitive transfer-type image recording materials, and electrophotography recording materials. Further preferably, these materials are inkjet recording materials.
Because of inexpensive material costs, capability of high-speed recording, reduced noise in recording operations, and ease in color recording, ink-jet recording has rapidly come into wide use and is being further developed.
The ink-jet recording methods include a method in which liquid droplets, pressed by a piezoelectric element, are ejected, a method in which liquid droplets are ejected by bubbles generated in the ink by heat, a method in which ultrasonic waves are used, and a method in which liquid droplets are suction-ejected by electrostatic force. In these methods, water-based ink, oil-based ink, and solid (fusion-type) ink are used.
The properties required for the jet printing ink are high solubility in a solvent, capability of high-density recording, excellent hue, excellent durability with respect to light, heat, air (in particular NO
x
, SO
x
, and ozone), water, and chemicals, excellent fixation and little blur on image-receiving materials, excellent storability as ink, freedom from toxicity, high purity, and being inexpensive. However, it is very difficult to obtain a dye that highly satisfies these requirements. In particular, there is a strong demand for a dye that has a good magenta hue and exhibits excellent lightfastness and ozone gas resistance. Heretofore, various dyes have been disclosed as pyrazole azo dyes in Japanese Patent Application Laid-Open (JP-A) Nos. 55-161856, 61-36362, 61-152768, 6-145543, and 7-224230, U. S. Pat. Nos. 4,650,861 and 4,301,070, PCT National Publication No. 11-504958, and so on. However, none of these dyes meets the requirements of hue and fastness at the same time.
Further, pyrazole dyes are conventionally synthesized according to methods described in U. S. Pat. Nos. 3,336,285 and 3,639,384 and U.K. Patent 1,566,985. The above-mentioned U.S. Patents disclose a method in which a 1-alkyl-4-cyano-pyrazol-5-yl azo dye is synthesized by diazotization of 1-alkyl-4-cyano-5-aminopyrazole followed by coupling. However, since the diazonium salt in this method is very unstable, it is difficult to obtain the dye with high yield and high purity by this diazotization and coupling (Weaver and Shuttleworth, Dyes and Pigments 3, 81 (1982)). Japanese Patent Application Publication (JP-B) No. 6-19036 discloses a synthesis method in which 1-alkyl-3-(secondary or tertiary alkyl)-4-cyano-pyrazol-5-yl-azo dyes are obtained. These azo dyes are not preferable as magenta dyes, because their hues are in the short wavelength range.
In the method disclosed in U.K. Patent No. 1,566,985, a 1-alkyl-3-alkyl or aryl-4-cyano-pyrazol-5-yl-azo dye is synthesized by dizaotization of 1-alkyl-3-alkyl or aryl-4-halogeno-5-aminopyrazole with an aromatic coupling component, followed by coupling, and then substitution of halogen in the 4-position with cyanide. However, this method uses a harmful heavy metal cyanide such as CuCN and Zn(CN)
2
, and so there are problems with disposal of waste and purification of the resulting dye.
SUMMARY OF THE INVENTION
It is accordingly the task of the present invention to overcome the problems in the prior art and to achieve the following objective. That is, the objective of the present invention is (1) to provide a novel heterylaniline azo dye derivative having a specific structure which is useful as a dye for ink jet printing ink or as an intermediate for synthesis of the dye and can also be an intermediate for useful chemical, medical, or agricultural organic chemical compounds and (2) to provide an ink-jet recording ink and an ink-jet recording method which, by use of the heterylaniline azo dye derivative, enable the formation of images having excellent hue and excellent durability with respect to light and ozone gas.
The present inventors have carefully studied the heterylaniline azo dye derivative having excellent hue and excellent lightfastness. As a result, they have found that the above-mentioned problems can be solved by the azo dye which is represented by the following general formula (I) and has a dye structure bearing a specific substituent hitherto unknown. Based on this finding, they have achieved the present invention. The means for solving the above-mentioned problems are as follows.
That is, the first aspect of the present invention is an ink-jet recording ink containing the azo dye represented by the following general formula (I):
In the general formula (I), R
1
represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group; R
2
represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted heterocyclic group; R
3
, R
4
, R
5
, and R
6
each independently represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aryl group, a heterocyclic group, a cyano group, a hydroxyl group, a nitro group, an amino group, an alkylamino group, an alkoxy group, an aryloxy group, an amide group, an arylamino group, a ureido group, a sulfamoylamino group, an alkylthio group, an arylthio group, an alkoxycarbonylamino group, a sulfonamide group, a carbamoyl group, a sulfamoyl group, a sulfonyl group, an alkoxycarbonyl group, a heterocyclooxy group, an azo group, an acyloxy group, a carbamoyloxy group, a silyloxy group, an aryloxycarbonyl group, an aryloxycarbonylamino group, an imide group, a heterocyclothio group, a sulfinyl group, a phosphoryl group, an acyl group, or an ionic hydrophilic group, which groups may each have a substituent; any of R
1
and R
2
, R
3
and R
1
, and R
2
and R
5
may be bonded to form a ring; and W represents a group of atoms necessary for forming a nitrogen-containing 5- to 6-membered heterocycle which may be condensed with other ring to form a condensed ring.
Any one group of R
1
and R
2
, R
3
and R
1
, and R
2
and R
5
in the general formula (I) may form a ring indicated by one of the following formulae:
In the ink-jet recording ink according to the first aspect, the azo dye represented by the general formula (I) is preferably an azo dye represented by the general formula (II):
In the general formula (II), R
1
, R
2
, R
3
, R
4
, R
5
, and R
6
are defined in the same way as R
1
, R
2
, R
3
, R
4
, R
5
, and R
6
in the general formula (I), respectively; X represents an electron-withdrawing group having a Hammett's constant &sgr;
p
of 0.20 or greater; Y represents a substituted or unsubstituted secondary or tertiary alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; and A represents a group made up of nonmetallic atoms necessary for forming a 5- to 8-membered ring which may have a substituent and may be a saturated ring or may have an unsaturated bond.
In an ink-jet recording ink, A in the general formula (II) is preferably represented by any one of the following general formulae (III):
In the general formulae (III), Z
1
, Z
2
, Z
3
, Z
4
, Z
5
, Z
7
, Z
8
, Z
10
, Z
11
, Z
12
, Z
13
, Z
14
, Z
15
, Z
16
, Z
17
, Z
18
, Z
19
, Z
20
, Z
21
, Z
2
Azuma Yasushi
Fujiwara Toshiki
Tateishi Keiichi
Burns Doane , Swecker, Mathis LLP
Fuji Photo Film Co. , Ltd.
Powers Fiona T.
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