Radiation imagery chemistry: process – composition – or product th – Diazo reproduction – process – composition – or product – Composition or product which contains radiation sensitive...
Reexamination Certificate
1999-07-08
2001-05-08
Chu, John S. (Department: 1752)
Radiation imagery chemistry: process, composition, or product th
Diazo reproduction, process, composition, or product
Composition or product which contains radiation sensitive...
C430S138000, C430S171000, C544S287000, C544S293000, C544S282000
Reexamination Certificate
active
06228553
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a pyrrolo[1,2-a]pyrimidine compound useful as a coupler of a heat-sensitive recording material, and to a heat-sensitive recording material using a diazonium salt compound and the pyrrolo[1,2-a]pyrimidine compound coupler as color-developing components.
2. Description of the Related Art
As heat-sensitive recording materials become more high-performance, there is required a heat-sensitive recording material which has cyan-color forming property, excellent color-forming property, long shelf life, improved storability of images and an improved image fixing property.
Diazonium salt compounds are compounds having very high chemical activity, and easily react with compounds called couplers (e.g., phenol derivatives, compounds having an active methylene group) to form an azo dye, and also are light-sensitive and lose their activity when decomposed due to irradiation by light. Therefore, diazonium salt compounds have been used as light recording materials such as bydiazo copies (see, “
Shashin Kogaku no Kiso, Higinen Shashin Hen
(Fundamentals of Photographic Technology, Non-Silver Salt Photography Volume)” edited by Nippon Shashin Gakkai (Japan Photographic Society), Corona Co. (1982), pp. 89 to 117, and 182 to 201).
Further, by utilizing the property of diazonium salt compounds that they lose their activity due to decomposition by light, diazonium salt compounds have recently been used in recording materials which require fixing of images. As an example, there has been proposed a light fixing type heat-sensitive recording material in which a diazonium salt compound and a coupler are heated in accordance with image signals and react to form images, and thereafter, the images are fixed by irradiation of light (Hirotsugu Sato et al., “
GazoDenshi Gakkai Shi
(Journal of the Image Electronics Society)”, Vol. 11, No. 4 (1982), pp. 290-296).
However, these recording materials using as a color-forming element a diazonium salt compound have a drawback in that the activity of the diazonium salt compound is extremely high, and even in dark places, the diazonium salt compound thermally decomposes gradually such that the reactivity thereof is lost, and therefore, its shelf life as a recording material is short. As one means for improving this drawback, there is a method in which a diazonium salt compound is encapsulated in microcapsules. It has become possible by this method to isolate the diazonium salt compound from substances promoting decomposition such as water, bases and the like, and to greatly improve the shelf life as a recording material (Tomomasa Usami et al., “
Denshi Shashin Gakkai Shi
(Journal of the Electronic Photographic Society)”, Vol. 26, No. 2, (1987), pp. 115 to 125).
When the microcapsule is a microcapsule having a wall which has a glass transition temperature and in which the glass transition temperature is somewhat higher than room temperature such as urea resins and urethane resins, this capsule is called a heat-responsive microcapsule and is useful as a heat-sensitive recording material since, at room temperature, the capsule wall exhibits non-permeability with respect to substances and, at glass transition temperature or higher, exhibits permeability with respect to substances. Namely, if a heat-sensitive recording layer comprising heat-responsive microcapsules containing a diazonium salt compound, a coupler and a base is applied onto a substrate to form a recording material, the diazonium salt compound can be kept stable for a long period of time, a color-formed image can be easily formed by heating, and further, the image can be fixed by irradiation by light.
As described above, it has become possible to greatly improve the stability of a diazonium salt compound by encapsulating the compound in microcapsules.
On the other hand, it is known that when 2-hydroxy-3-naphtoic anilides are used as couplers, they are excellent as heat-sensitive recording color-forming materials, and if a coupling reaction is effected with a 4-substituted amino-2-alkoxybenzene diazonium salt compound, a blue dye can be formed (Japanese Patent Application Laid-Open (JP-A) No. 2-225082).
However, when a diazonium salt compound having &lgr;
max
at a longer wavelength side is used, storability before use (ground coloring property during storage before copying) of the recording material deteriorates. Further, in the case of a diazonium salt compound having &lgr;
max
at a shorter wavelength side, when the aforementioned 2-hydroxy-3-naphtoic anilides are used, there are drawbacks in that the fixing property of images when irradiated with light is hindered, the hue extends over a long wavelength even to cyan, and further, storability of color-developed images (light fastness) is not sufficient.
As described above, there has not been obtained a heat-sensitive recording material which has cyan color-forming property, results in excellent color-forming property, and has a saltiscactory shelf life, image storability and image fixing property, until now.
SUMMARY OF THE INVENTION
The present invention has been accomplished in view of the aforementioned, and an object thereof is to provide a pyrrolo[1,2-a]pyrimidine compound which is useful as a coupler providing an excellent color-forming property. Another object of the present invention is to provide a novel cyan color-forming type diazo heat-sensitive recording material which contains the pyrrolo[1,2-a]pyrimidine compound coupler and a diazonium salt compound and has excellent shelf life, image light-resistance and image fixing property in addition to the above-described properties.
The present inventors have studied couplers intensively, and have found that a novel pyrrolo[1,2-a]pyrimidine compound represented by the following general formula (1) is useful as a coupler which provides an excellent color-forming property. Further, the present inventors have found that a heat-sensitive recording material using the pyrrolo[1,2-a]pyrimidine compound and a diazonium salt compound which will be described below has improved shelf life, image light-resistance and image fixing property, and has an excellent cyan color-forming property. Thus, the present inventors invented.
The present invention provides a pyrrolo[1,2-a]pyrimidine compound represented by following general formula (1):
(wherein, in general formula (1), R
1
represents an aryl group, alkyl group, carbamoyl group, alkoxycarbonyl group or aryloxycarbonyl group; R
2
represents an alkoxycarbonyl group, aryloxycarbonyl group or cyano group; R
3
and R
4
each independently represents a hydrogen atom, aryl group, alkyl group, acyl group, carbamoyl group, alkoxycarbonyl group, aryloxycarbonyl group, alkylsulfonyl group, arylsulfonyl group, sulfamoyl group, alkylphosphoryl group or arylphosphoryl group; R
5
represents a hydrogen atom, halogen atom, cyano group, acyl group, carbamoyl group, alkoxycarbonyl group, aryloxycarbonyl group, acyloxy group, sulfamoyl group, alkylsulfonyl group, arylsulfonyl group, alkylphosphoryl group or arylphosphoryl group).
Further, the present invention provides a heat-sensitive recording material comprising a substrate, and on said substrate, a heat-sensitive recording layer containing a diazonium salt compound and a coupler which forms color by reacting with the diazonium salt compound during heating, wherein the coupler contains at least one of the pyrrolo[1,2-a]pyrimidine compounds represented by said general formula (1).
DETAILED DESCRIPTION OF THE INVENTION
The pyrrolo[1,2-a]pyrimidine compound of the present invention will be described in detail hereinafter.
The pyrrolo[1,2-a]pyrimidine compound of the present invention has the feature that when it is coupled as a coupler with a diazonium salt compound, an excellent color-forming property is obtained and a dye having little yellow light absorption can be provided.
Specifically, this compound is a novel compound represented by gene
Matsushita Tetsunori
Takashima Masanobu
Tsurumi Mitsuyuki
Yanagihara Naoto
Chu John S.
Fuji Photo Film Co. , Ltd.
Sughrue Mion Zinn Macpeak & Seas, PLLC
LandOfFree
Pyrrolo [1,2-A] pyrimidine compound and... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Pyrrolo [1,2-A] pyrimidine compound and..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Pyrrolo [1,2-A] pyrimidine compound and... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2439033