Radiation imagery chemistry: process – composition – or product th – Radiation sensitive product – Identified radiation sensitive composition with color...
Reexamination Certificate
2002-03-27
2004-01-13
Letscher, Geraldine (Department: 1752)
Radiation imagery chemistry: process, composition, or product th
Radiation sensitive product
Identified radiation sensitive composition with color...
C430S557000, C430S543000
Reexamination Certificate
active
06677110
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a dye-forming coupler to form an azomethine dye, upon a coupling-reaction with an oxidized product of a developing agent. The present invention also relates to a silver halide photographic light-sensitive material containing the coupler. Further, the present invention relates to an azomethine dye compound, which can be produced by using the above-mentioned coupling reaction.
BACKGROUND OF THE INVENTION
In a silver halide photographic light-sensitive material (hereinafter sometimes referred to simply as “light-sensitive material”) for subtractive color photography, a color image is formed by dyes of three primary colors of yellow, magenta and cyan. In the color photography that uses the current p-phenylenediamine-series color-developing agent, an acylacetoanilide-series compound is used as a yellow coupler. However, the hue of the yellow dye obtained from the yellow coupler is tinted with red, due to inferior sharpness at the foot portion of a peak in interest of the absorption curve at the longer wavelength side (that is, on the absorption curve, the peak in interest has subsidiary absorption at its foot portion at the longer wavelength side), which renders it difficult to obtain a yellow hue of high-purity. Further, there is the problem that, due to the low molecular extinction coefficient of the yellow dyes, large amounts of both the coupler and silver halide are needed to obtain a desired colored density. Therefore, sometimes it results in increasing film thickness of the light-sensitive material, and this consequently reduces the sharpness of the obtained color image. Further, the above-mentioned yellow dyes, which are easily decomposed under the conditions of high temperature and high humidity, or the conditions of light irradiation, have insufficient image stability after development processing. Consequently, improvement of these problems is desired.
In order to solve such problems, the acyl group and the anilido group were improved. Recently, as improved couplers of the conventional acylacetanilide-series, there are proposed, for example, 1-alkylcyclopropanecarbonylacetanilide-series compounds, as described in JP-A-4-218,042 (“JP-A” means unexamined published Japanese patent application); cyclomalonic acid diamide-type couplers, as described in JP-A-5-11416; pyrrole-2 or 3-yl- or indole-2 or 3-yl-carbonylacetanilide-series couplers, as described, for example, in European Patent Nos. 953870A1, 953871A1, 953872A1, 953873A1, 953874A1 and 953875A1. The dyes formed from these couplers were improved in terms of both hue and a molecular extinction coefficient, compared with the conventional ones. However, they are still deficient in image stability. Further, owing to their complicated chemical structure, the synthesis route became longer, and consequently cost of the couplers became higher, causing a practical problem.
Further, U.S. Pat. No. 5,455,149 proposes acetoanilide-series couplers to which N-alkyl-4-pyrimidone is bonded. However, dyes obtained from these couplers are still inferior in hue, especially sharpness at the foot portion of a peak of the absorption curve at the longer wavelength side. Further, they are insufficient in fastness to light. Therefore, there is a need to improve these problems.
SUMMARY OF THE INVENTION
The present invention is a dye-forming coupler represented by the following formula (I):
wherein Q represents a residue that forms, together with the —N—C═N— moiety, a nitrogen-containing 6-membered ring; R
A
represents an aryl group, a heterocyclic group, or an —(R
1
)
r
—(R
4
)
m
group; X represents an aryl group; Y represents a hydrogen atom, or a group that is capable of being split-off upon a coupling reaction with an oxidized product of a developing agent:
wherein, when R
A
represents an —(R
1
)
r
—(R
4
)
m
group, R
1
represents a methylene group, a methine group, or a carbon atom; r represents an integer of 1 to 30, and R
1
s may be the same or different independently, when r is 2 or more; R
4
represents a substituent except for a hydrogen atom; m represents an integer of 1 to 30, and R
4
s may be the same or different independently, or R
4
s may be combined together to form a multiple bond, or alternatively R
4
s may bond with each other to form a ring, when m is 2 or more; and the —(R
1
)
r
—(R
4
)
m
group does not represent a straight-chain alkyl group.
Further, the present invention is a silver halide photographic light-sensitive material, which comprises at least one dye-forming coupler represented by the above formula (I).
Still further, the present invention is an azomethine dye compound represented by the following formula (II):
wherein Q represents a residue that forms, together with the —N—C═N— moiety, a nitrogen-containing 6-membered ring; R
A
represents an aryl group, a heterocyclic group, or an —(R
1
)
r
—(R
4
)
m
group; X represents an aryl group:
wherein, when R
A
represents an —(R
1
)
r
—(R
4
)
m
group, R
1
represents a methylene group, a methine group, or a carbon atom; r represents an integer of 1 to 30, and R
1
s may be the same or different independently, when r is 2 or more; R
4
represents a substituent except for a hydrogen atom; m represents an integer of 1 to 30, and R
4
s may be the same or different independently, or R
4
s may be combine together to form a multiple bond, or alternatively R
4
s may bond with each other to form a ring, when m is 2 or more; and the —(R
1
)
r
—(R
4
)
m
group does not represent a straight-chain alkyl group;
R
5
and R
6
each represent a hydrogen atom or a substituent, or R
5
and R
6
may bond with each other to form a ring; R
7
represents a hydrogen atom or a substituent; n represents 0 (zero) or an integer of 1 to 4, with the proviso that R
7
s may be the same or different independently, or R
7
s may bond with each other to form a condensed ring, when n is 2 or more; or R
7
may bond with R
5
or R
6
to form a condensed ring, when n is 1 or more.
Other and further features and advantages of the invention will appear more fully from the following description.
DETAILED DESCRIPTION OF THE INVENTION
According to the present invention, there is provided the following means:
(1) A dye-forming coupler represented by formula (I):
wherein Q represents a residue that forms, together with the —N—C═N— moiety, a nitrogen-containing 6-membered ring; R
A
represents an aryl group, a heterocyclic group, or an —(R
1
)
r
—(R
4
)
m
group; X represents an aryl group; Y represents a hydrogen atom, or a group that is capable of being split-off upon a coupling reaction with an oxidized product of a developing agent:
wherein, when R
A
represents an —(R
1
)
r
—(R
4
)
m
group, R
1
represents a methylene group, a methine group, or a carbon atom; r represents an integer of 1 to 30, and R
1
s may be the same or different independently, when r is 2 or more; R
4
represents a substituent except for a hydrogen atom; m represents an integer of 1 to 30, and R
4
s may be the same or different independently, or R
4
s may be combined together to form a multiple bond, or alternatively R
4
s may bond with each other to form a ring, when m is 2 or more;
and the —(R
1
)
r
—(R
4
)
m
group does not represent a straight-chain alkyl group.
(2) The dye-forming coupler according to the above item (1), wherein the dye-forming coupler represented by formula (I) is represented by formula (IA):
wherein Q represents a residue that forms, together with the —N—C═N— moiety, a nitrogen-containing 6-membered ring; R
11
represents an aryl group or a heterocyclic group; X represents an aryl group; Y represents a hydrogen atom, or a group that is capable of being split-off upon a coupling reaction with an oxidized product of a developing agent.
(3) The dye-forming coupler according to the above item (2), wherein, in the dye-forming coupler represented by formula (IA), Q is a residue that forms, together with the —N—C═N— moiety, a 4-pyrimidone ring.
(4) The dye-forming coupler according to the above item (2), wherein, in the dye-forming cou
Aoki Mario
Takeuchi Kiyoshi
Uehira Shigeki
Fuji Photo Film Co. , Ltd.
Letscher Geraldine
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