Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2002-04-15
2002-12-17
McKane, Joseph K. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C544S132000, C544S366000, C546S199000
Reexamination Certificate
active
06495697
ABSTRACT:
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is based upon and claims the benefit of priority from the prior Japanese Patent Application No. 11-279838, filed Sep. 30, 1999, the entire contents of which are incorporated herein by reference.
BACKGROUND OF THE INVENTION
The present invention relates to a pyrrolotriazole compound having a specific structure and a silver halide color photographic lightsensitive material which improves the color reproduction and dye image stability, suppresses various stains, and increases the processing stability by using the pyrrolotriazole cyan coupler.
It is well known that in silver halide color photographic lightsensitive materials, an aromatic primary amine-based color developing agent oxidized by using an exposed silver halide as an oxidizer reacts with couplers to form dyes such as indophenol, indoaniline, indamine, azomethine, phenoxazine, and phenazine, thereby forming images. This photographic scheme uses subtraction color processes and forms color images by yellow, magenta, and cyan dyes.
To form a cyan dye image, a phenol- or naphthol-based coupler is conventionally used. However, dyes formed from these couplers have unpreferable absorption in regions from yellow to magenta and hence deteriorate the color reproduction. So, solving this problem has been desired.
Especially in recent years, demands on so-called digital photography are increasing by which image information is converted into digital information, image processing is performed, and after that, a silver halide color photographic lightsensitive material is exposed on the basis of the information. In this digital photography, a silver halide color photographic lightsensitive material having a wide color reproduction range, in which formed dyes have no such unpreferable absorption as described above, is desired.
Also, reversal films are desired to have high saturation and a wide color reproduction range. However, a method which emphasizes the interlayer effect has drawbacks such as deterioration of the processing dependency. Therefore, it has been required to realize high saturation and wide color reproduction by couplers superior in hue.
As means for solving this problem, heterocyclic compounds as described in, e.g., U.S. Pat. Nos. 4,728,598 and 4,873,183 and European Patent Publication No. 0249453A2 have been proposed. Unfortunately, these couplers have fatal drawbacks such as low coupling activity and low dye image stability. As couplers which have solved these problems, pyrrolotriazole couplers described in U.S. Pat. No. 5,256,526 and European Patent 0545300 have been proposed. Although these couplers are superior in hue and coupling activity, color photographic lightsensitive materials using these couplers have no sufficient dye image stability. So, the couplers must be further improved. Also, the couplers have the problem (so-called blix fading) that the color generation reduces by leuco conversion of a dye (a dye is partially decolored by reduction) during bleach-fixing. Additionally, diverse cyan stains are produced. Furthermore, conventionally known pyrrolotriazole cyan couplers produce a magenta stain with time when processed using formalin.
BRIEF SUMMARY OF THE INVENTION
It is, therefore, an object of the present invention to provide 1): a novel pyrrolotriazole compound having a specific structure, which is useful as a synthetic intermediate of coupler in a silver halide color photographic lightsensitive material and can be used as a useful intermediate of chemical, medicinal or agrichemical organic compound, and to provide 2): a silver halide color photographic lightsensitive material which improves the color reproduction and dye image stability by the use of the pyrrolotriazole cyan coupler and which reduces a cyan stain produced by the reaction with a residual color developing agent, causes blix fading little, minimizes a magenta stain, and improves the processing stability.
The present inventors extensively studied 2-position substituents and split-off groups of pyrrolotriazole-based couplers having good hue and have found that the above problems can be solved by a coupler, represented by the following formula, having an entirely new structure conventionally unknown. That is, the object of the present invention is achieved by the following means.
(1) A silver halide color photographic lightsensitive material comprising at least one layer on a support, wherein the at least one layer contains a coupler represented by formula (I) below:
wherein X represents a hydrogen atom or a group capable of splitting off by a coupling reaction with an oxidized form of an aromatic primary amine color developing agent; each of R
1
and R
2
represents an electron-attracting group having a Hammett's substituent constant &sgr;p value of not less than 0.20, the sum of the &sgr;p values of R
1
and R
2
being not less than 0.65; and each of G
1
and G
2
represents a nitrogen atom or a substituent represented by formula (II), provided that one of G
1
and G
2
being a nitrogen atom and the other being a substituent represented by formula (II) below:
wherein R
3
represents a member selected from the group consisting of a substituted or nonsubstituted alkyl group, substituted or nonsubstituted alkenyl group, substituted or nonsubstituted alkynyl group, substituted or nonsubstituted cycloalkyl group, substituted or nonsubstituted cycloalkenyl group, substituted or nonsubstituted aryl group, and substituted or nonsubstituted heterocyclic group; R
4
represents a hydrogen atom or a substituent bonded by a carbon atom, R
3
and R
4
being capable of combining to form a ring; R
5
represents a substituent, and n represents an integer of 0 to 4,
provided that a group represented by R
1
, R
2
, R
3
, R
4
, R
5
, or X may be a divalent group, and thereby the coupler represented by formula (I) may form a polymer, which is a dimer or a higher-order polymer, or may form a homopolymer or a copolymer by combining with a polymeric chain.
(2) The lightsensitive material according to (1), characterized in that the coupler represented by formula (I) is represented by formula (III) below:
wherein X represents a hydrogen atom or a group capable of splitting off by a coupling reaction with an oxidized form of an aromatic primary amine color developing agent; each of R
1
and R
2
represents an electron-attracting group having a Hammett's substituent constant &sgr;p value of not less than 0.20, the sum of the &sgr;p values of R
1
and R
2
being not less than 0.65; R
3
represents a member selected from the group consisting of a substituted or nonsubstituted alkyl group, substituted or nonsubstituted alkenyl group, substituted or nonsubstituted alkynyl group, substituted or nonsubstituted cycloalkyl group, substituted or nonsubstituted cycloalkenyl group, substituted or nonsubstituted aryl group, and substituted or nonsubstituted heterocyclic group; R
4
represents a member selected from the group consisting of a hydrogen atom, substituted or nonsubstituted alkyl group, substituted or nonsubstituted alkenyl group, substituted or nonsubstituted alkynyl group, substituted or nonsubstituted cycloalkyl group, substituted or nonsubstituted cycloalkenyl group, substituted or nonsubstituted aryl group, substituted or nonsubstituted acyl group, substituted or nonsubstituted alkyloxycarbonyl group, substituted or nonsubstituted aryloxycarbonyl group and substituted or nonsubstituted carbamoyl group, R
3
and R
4
being capable of combining to form a ring; and each of R
11
to R
14
independently represents a hydrogen atom or a substituent.
(3) A pyrrolotriazole compound represented by formula (I) below:
wherein X represents a member selected from the group consisting of a hydrogen atom, halogen atom, 1- to 32-carbon alkyloxy group, 6- to 32-carbon aryloxy group, 1- to 32-carbon alkylthio group, 6- to 32-carbon arylthio group, 2- to 32-carbon heterocyclic thio group, 2- to 32-carbon alkyloxycarbonyloxy group, 7- to 32-carbon aryloxycarbonyloxy group, 1- to 32-carbon carbamoyloxy group, 3- t
Matsuda Naoto
Mikoshiba Hisashi
Tateishi Keiichi
Anderson Rebecca
Birch & Stewart Kolasch & Birch, LLP
Fuji Photo Film Co. , Ltd.
McKane Joseph K.
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