Radiation imagery chemistry: process – composition – or product th – Radiation sensitive product – Identified radiation sensitive composition with color...
Reexamination Certificate
2000-03-29
2001-03-13
Letscher, Geraldine (Department: 1752)
Radiation imagery chemistry: process, composition, or product th
Radiation sensitive product
Identified radiation sensitive composition with color...
C430S543000
Reexamination Certificate
active
06200742
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a silver halide photographic light-sensitive material containing therein a coupler which forms a heterocyclic azo dye by a coupling reaction of the coupler and an oxidized developing agent. Further, the present invention relates to a method of preparing a heterocyclic azo dye which can be prepared by this coupling reaction, and to a heterocyclic compound which provides the dye.
2. Description of the Related Art
In a silver halide photographic light-sensitive material (referred to as a “light-sensitive material” in some cases, hereinafter) using a subtractive color process, a color image is formed by dyes of the three primary colors, i.e., yellow, magenta, and cyan. In color photography using an existing p-phenylenediamine-based color-developing agent, a &bgr;-acylacetanilide-based compound is used as the yellow coupler. However, hues of the yellow dye obtained from these couplers become reddish, thus making it difficult to obtain yellow hues of high purity. Further, there have been problems in that, since the molar extinction coefficient of the dye is small, a large amount of coupler or silver halide must be used in order to obtain a desired density of the formed color and the film thickness of the light-sensitive material thus becomes larger, and sharpness of the obtained color image thereby deteriorates. Moreover, since this dye has a tendency to decompose under high temperature and/or high humidity, there are problems in image storage stability after the light-sensitive material has been subjected to developing processing. Accordingly, it is desired to improve problems such as those described above.
In order to solve these problems, improvement of an acyl group and an anlide group has been performed. Recently, the 1-alkylcyclopropylcarbonylacetanilide-based compound disclosed in Japanese Patent Application Laid-Open (JP-A) No. 4-218042, the malon di(cyclic amide) coupler disclosed in Japanese Patent Application Laid-Open (JP-A) No. 5-11416, and the like have been proposed as a coupler obtained by improving a conventional acylacetanilide and derivatives thereof. A dye produced from such a coupler has been improved in respect of hues and molar extinction coefficients over conventional dyes. However, the dye is not improved satisfactorily in respect to image storage stability. In addition, since the structure of the coupler has become complicated, the manufacturing cost of the coupler has become expensive thus causing a problem in that such a coupler is less practical.
Instead of a conventional coupler which produces an azomethine dye, the indazole-based compound disclosed in Great Britain Patent No. 875470 has been proposed as a yellow coupler which forms an azo dye having a high extinction coefficient However, since the dye produced by the coupler has an essential problem in that an intramolecular hydrogen bond occurs under neutral condition and the absorption peak or band thereby shifts to higher wavelength, the dye cannot be used practically. Further, as a yellow coupler which forms an azo dye having a high extinction coefficient, there has been proposed the compounds disclosed in JP-A No. 10-148921. However, there is the problem that the pKa of this coupler is so high that the coupling activity of this coupler is insufficient, and when the pKa is lowered in order to improve the coupling activity, the hues deteriorate. As a result, this coupler cannot be used practically.
Further, there has been a strong demand for using azo dyes, whose molecular extinction coefficient is high and which have excellent hues and storage stability, not only for silver halide photographic light-sensitive materials, but also as a general dye, as well as a dye for images including dyes used in inks for ink jet printers. The development of a simple method of preparing an azo dye and in particular, a method of preparing an azo dye using a coupler have been desired.
SUMMARY OF THE INVENTION
In view of the aforementioned facts, it is an object of the present invention to provide a silver halide photographic light-sensitive material, which has excellent color reproducibility and sharpness and satisfactory light-fastness of color images, by including in the light-sensitive material a coupler that provides a dye which has excellent hues, which has a large molar extinction coefficient, and which can provide excellent image storage stability. Further, an object of the present invention is to provide a simple method of preparing an azo dye having a high molecular extinction coefficient and excellent hues and storage stability, and to provide a compound, a dye forming compound, and a dye forming coupler which can form an azo dye by a coupling reaction with an oxidized p-phenylenediamine derivative.
The present inventors conducted various experiments and found that the aforementioned problems can be solved by using a compound which is represented by the following formula (I):
wherein Z represents an atomic group that comprises a carbon atom and/or a nitrogen atom which, together with N—C═C, form a 5- or 6-member aromatic ring; R represents a substituent, and when there are a plurality of R, the R can be same or different, and may be coupled to each other so as to form a fused ring; m represents an integer of from 1 to 4; and X represents a carbonyl group, a methylene group, or a >C═N—Rn group wherein Rn represents a substituent
Aspects of the present invention are as follows.
(1) A silver halide photographic light-sensitive material comprising a support and at least one light-sensitive layer formed on the support, wherein at least one of the light-sensitive layers contains at least one of couplers represented by following formula (I):
wherein Z represents an atomic group that comprises a carbon atom and/or a nitrogen atom which, together with N—C═C, form a 5- or 6-member aromatic ring; R represents a substituent, and when there are a plurality of R, the R can be same or different, and may be coupled to each other so as to form a fused ring; m represents an integer of from 1 to 4; and X represents a carbonyl group, a methylene group, or a >C═N—Rn group wherein Rn represents a substituent.
(2) The silver halide photographic light-sensitive material described above, wherein the ring formed by Z and N—C═C in the coupler represented by formula (I) is selected from the group consisting of a pyrrole ring, a pyrazole ring, an imidazole ring, a 1,2,3-triazole ring, a pyridine ring a pyridazine ring a pyrimizine ring, a pyrazine ring, an indole ring, an isoindole ring, a benzimidazole ring, a quinoline ring, and an isoquinoline ring.
(3) The silver halide photographic light-sensitive material described above, wherein the coupler represented by the formula (I) is at least one of couplers represented by following formulas (II), (III), (IV), or (V):
(4) The silver halide photographic light-sensitive material described above, wherein X of the coupler represented by formula (I) is a carbonyl group.
(5) The silver halide photographic light-sensitive material described above, wherein the amount of the coupler contained in the silver halide photographic light-sensitive material ranges from 1×10
−3
mol to 1 mol per 1 mol of silver halide.
(6) The silver halide photographic light-sensitive material described above, wherein the coupler represented by formula (I) is selected from the group consisting of couplers represented by formula (III) and couplers represented by formula (V).
(7) A compound represented by following formula (I):
wherein Z represents an atomic group that comprises a carbon atom and/or a nitrogen atom which, together with N—C═C, form a 5- or 6-member aromatic ring; R represents a substituent, and when there are a plurality of R, the R can be same or different, and may be coupled to each other so as to form a fused ring; m represents an integer of from 1 to 4; and X represents a carbonyl group, a methylene group, or a >C═N—Rn group wherein Rn represents a substitu
Aoki Mario
Kato Yasuhiro
Shimada Yasuhiro
Birch & Stewart Kolasch & Birch, LLP
Fuji Photo Film Co. , Ltd.
Letscher Geraldine
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