Radiation imagery chemistry: process – composition – or product th – Radiation sensitive product – Identified radiation sensitive composition with color...
Reexamination Certificate
2001-08-08
2002-12-10
Letscher, Geraldine (Department: 1752)
Radiation imagery chemistry: process, composition, or product th
Radiation sensitive product
Identified radiation sensitive composition with color...
C430S387000, C430S378000, C430S379000
Reexamination Certificate
active
06492100
ABSTRACT:
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is based upon and claims the benefit of priority from the prior Japanese Patent Applications No. 2000-245812, filed Aug. 14, 2000; and No. 2001-020183, filed Jan. 29, 2001, the entire contents of both of which are incorporated herein by reference.
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a silver halide color photographic lightsensitive material and a novel color coupler compound used therein.
2. Description of the Related Art
Many photographic couplers are used as they are dispersed in high-boiling organic solvents such as phosphoric ester and phthalic ester. On the other hand, lightsensitive materials for photographing are required to be thin in order to improve the sharpness. Therefore, couplers used in lightsensitive materials for photographing are dispersed by emulsification by using no high-boiling organic solvents (so-called oilless dispersion) or by using only slight amounts of high-boiling organic solvents. Compared to a case in which high-boiling organic solvents are used, the color forming efficiency lowers, and the absorption spectrum broadens.
Also, silver halide color photographic lightsensitive materials are strongly required to have faithful color reproducibility in addition to high sensitivity, high sharpness, and high granularity.
In the field of silver halide color photographic lightsensitive materials, a 1-phenyl-5-pyrazolone coupler has been conventionally widely used as a magenta coupler. On the other hand, some pyrazoloazole-based couplers having little side absorption and good hue, which are favored as image forming dyes, have been put into practical use.
Pyrazolotriazole magenta couplers are excellent compounds in that they have good hue. However, when introduced into lightsensitive materials, they pose various problems such as low color forming efficiency, low resistance against processing variations, and low color image storage stability.
In particular, a 4-equivalent pyrazolotriazole magenta coupler which couples with an oxidized form of an aromatic primary amine developing agent in the position of hydrogen atom substitution has low color forming efficiency, although it has high granularity, and has a large degree of yellow coloration which occurs by the lapse of time after development. On the other hand, a 2-equivalent coupler whose coupling position is substituted by a split-off group (e.g., a halogen atom) except for a hydrogen atom generates a color with a smaller silver amount than a 4-equivalent coupler. Although this 2-equivalent coupler does not easily cause yellow coloration, the granularity lowers, and this degrades the image quality.
To solve these problems, couplers in which substituents on pyrazoloazole rings are variously improved have been proposed. For example, U.S. Pat. No. 4,882,266 and European Patent Publication No. 183,445 disclosed improvements of the light fastness of a color image by couplers in which the bulkiness of a 6-position substituent is increased. Jpn. Pat. Appln. KOKAI Publication No. (hereinafter referred to as JP-A-)1-102557 disclosed improvements of the color forming efficiency in oilless processing by couplers in which carboxylic acid is introduced as a dissociation group into coupler molecules. JP-A-5-150419 describes a coupler having a sulfonamide bond. JP-A-63-291058 also describes a coupler similar to the present invention. Unfortunately, when the present inventors attempted to apply these techniques, they newly found that improvements of yellow coloration and color image storage stability by these techniques during the lapse of time after processing were still unsatisfactory. Also, they newly found that the couplers increased the cost and deteriorated the crystallinity and hence could not be used in industrial applications. Furthermore, they newly found that the sensitivity decreased when the couplers were retained before coating after they were mixed in color-sensitized silver halide emulsions.
Most pyrazoloazole-based couplers currently put into practical use are 2-equivalent couplers having a split-off group except for a hydrogen atom in a portion where these couplers react with an oxidized form of a color developing agent. Color reversal photographic lightsensitive materials are subjected to first development, reversal processing, and color development in this order. 2-equivalent couplers have an essential problem that since they have high color forming efficiency per mol of silver, they decrease the sensitivity compared to 4-equivalent couplers. Therefore, when pyrazoloazole magenta couplers are to be applied to color reversal photographic lightsensitive materials, 4-equivalent couplers are preferred in respect of sensitivity. From this viewpoint, the couplers described in JP-A's-5-150419 and 63-291058 are unfavorable because they are primarily 2-equivalent couplers. Applications of 4-equivalent pyrazoloazole magenta couplers to color reversal photographic lightsensitive materials are described in, e.g., JP-A's-5-100382 and 63-153548. However, these techniques have not solved the above-mentioned problem of yellow coloration caused by the lapse of time after processing. In addition, the problem of the absorption spectrum of a generated dye in oilless dispersion remains unsolved.
BRIEF SUMMARY OF THE INVENTION
It is the first object of the present invention to provide a silver halide color photographic lightsensitive material which has high color reproducibility and high image stability and produces stains little. It is the second object of the present invention to provide a coupler which achieves high color forming efficiency even when the use amount of a high-boiling organic solvent is reduced. It is the third object of the present invention to provide a novel pyrazolotriazole-based compound which can be manufactured at low cost and has high manufacturing suitability. It is the fourth object of the present invention to provide a silver halide color photographic lightsensitive material which lowers the sensitivity little when stored and changes photographic properties little by variations in processing compositions.
The present inventors made extensive studies on the structure and photographic properties of pyrazolotriazole couplers. As a consequence, the present inventors have found couplers solving the above problems and thereby completed the present invention.
That is, the objects of the present invention were achieved by the following lightsensitive material and compound.
(1) A silver halide color photographic lightsensitive material comprising at least one photosensitive silver halide emulsion layer on a support, wherein the emulsion layer contains a magenta coupler represented by formula (M-1) below:
wherein R
1
represents a substituted or nonsubstituted alkyl group; each of L
1
and L
2
independently represents a substituted or nonsubstituted alkylene group, or substituted or nonsubstituted arylene group; in —L
3
—G, L
3
represents —NH—SO
2
— or —SO
2
—NH—CO— (in these representations, bonding direction is not defined) and G represents a substituted or nonsubstituted alkyl group or substituted or nonsubstituted aryl group, alternatively —L
3
—G represents —COOH or OH; X represents a hydrogen atom or a group which splits off when coupling with an oxidized form of a developing agent; n represents 1 or 2, when L
2
is an alkylene group, or n represents an integer from 1 to 5, when L
2
is an arylene group; and a plurality of —L
3
—G's can be the same or different, when n is 2 or more.
(2) A silver halide color photographic lightsensitive material comprising at least one photosensitive silver halide emulsion layer on a support, wherein the emulsion layer contains a magenta coupler represented by formula (M-2) below:
wherein R
11
represents a 1- to 6-carbon nonsubstituted alkyl group; L
11
represents a 1 to 6-carbon nonsubstituted alkylene group; each of G
1
and G
2
independently represents a substituted or nonsubstituted alkyl group, substituted or nonsubstituted alkoxy grou
Fukuzawa Hiroshi
Matsuda Naoto
Mikoshiba Hisashi
Shimura Yoshio
Birch & Stewart Kolasch & Birch, LLP
Fuji Photo Film Co. , Ltd.
Letscher Geraldine
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