Radiation imagery chemistry: process – composition – or product th – Radiation sensitive product – Identified radiation sensitive composition with color...
Reexamination Certificate
2000-06-27
2001-09-04
Letscher, Geraldine (Department: 1752)
Radiation imagery chemistry: process, composition, or product th
Radiation sensitive product
Identified radiation sensitive composition with color...
C430S544000
Reexamination Certificate
active
06284448
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to silver halide light sensitive color photographic materials and in particular, to silver halide color photographic materials containing a novel yellow dye forming coupler exhibiting superior dye forming capability, enhanced solubility in solvents and superiority in crystallization property and dispersion stability.
BACKGROUND OF THE INVENTION
Recently, in silver halide light sensitive color photographic materials (hereinafter, also referred to as color photographic materials), two-equivalent couplers tend to be used, in which an appropriate substituent is introduced to the coupling position of the coupler (also called the active point) to react with an oxidized color developing agent, thereby reducing the number of silver atoms needed to form a dye molecule to two silver atoms, instead of the conventionally used four-equivalent couplers which needed four silver atoms to from a dye molecule.
However, requirements for couplers become more severe along with the progress of color photographic materials. Specifically, further improvements in dye formability are desired in terms of enhancements of sensitivity and image quality as well as rapid access.
Representative yellow dye forming couplers (hereinafter, also referred to as yellow couplers) include pivaloylaceto-anilide type yellow couplers and benzoylacetoanilide type yellow couplers. As is well known in the art, the benzoylacetoanilide type yellow couplers are generally superior in dye formability. However, commonly known benzoylacetoanilide type yellow couplers are inferior in solubility in solvents, producing problems in manufacturing color photographic materials such that a large amount of a solvent is needed in dispersing the coupler, and defects that after being dispersed in the solvent, crystallization of the coupler tends to occur. These defects are made more marked specifically under the condition of thinner coating, making it a barrier for practical application thereof.
Similarly to the benzoylacetoanilide type yellow couplers, their intermediates are also inferior in solubility in solvents so that a large amount of a solvent is needed in synthesis of the coupler, leading to deteriorated productivity thereof and increased manufacturing cost and causing problems when halogenated solvents are employed, which are superior in solubility but not preferred from the point of view of environment protection.
There have been proposed various techniques to overcome such problems. European Patent (hereinafter, denoted as EP) 327,348 discloses a technique of introducing a branched alkyl group into a benzoylacetoanilide type yellow coupler. Although this technique improved solubility, however, it exhibited the defect that dye forming efficiency is lowered when developed at a lower pH. JP-A 3-84546 (hereinafter, the term, JP-A means an unexamined and published Japanese Patent Application) and EP 897,133 also proposed introduction of a branched alkyl group. However, dye formation is still at an insufficient level and further improvements are desired.
SUMMARY OF THE INVENTION
Accordingly, it is an object of the present invention to provide a silver halide color photographic material containing a novel 2-equivalent yellow coupler exhibiting superior dye forming capability.
It is another object of the invention to provide a silver halide color photographic material containing a novel 2-equivalent yellow coupler exhibiting enhanced solubility in a solvent, and superior crystallization property and dispersion stability.
The objects described above can be accomplished by the following constitution:
1. A silver halide light sensitive color photographic material comprising a coupler represented by the following formula (I):
wherein R
1
is a substituent; R
2
is a branched alkyl group having 7 to 20 carbon atoms; R
3
is a hydrogen atom or a halogen atom; m is an integer of 1 to 5; Z
1
is >N—R
4
or —O—, in which R
4
is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a heterocyclic group; Z
2
is >N—R
5
or >C(R
6
)(R
7
), in which R
5
is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a heterocyclic group, and R
6
and R
7
are each a hydrogen atom or a substituent;
2. The silver halide color photographic material described in 1, wherein R
3
is a chlorine atom;
3. A silver halide light sensitive color photographic material comprising a coupler represented by the following formula (II):
wherein R
1
is a substituent; R
8
is an alkyl group, a cycloalkyl group or an aryl group; R
9
is an alkyl group or a cycloalkyl group, provided that the sum of the carbon number of R8 and R9 is 7 to 20; R
3
is a hydrogen atom or a halogen atom; m is an integer of 1 to 5; Z
1
is >N—R
4
or —O—, in which R
4
is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a heterocyclic group; Z
2
is >N—R
5
or >C(R
6
)(R
7
), in which R
5
is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a heterocyclic group, and R
6
and R
7
are each a hydrogen atom or a substituent;
4. The silver halide color photographic material described in 3. above, wherein in formula (II), R
3
is a chlorine atom;
5. A silver halide light sensitive color photographic material comprising a coupler represented by the following formula (III):
wherein R10 is a ballasted alkyl group; R
3
is a hydrogen atom or a halogen atom; Z
1
is >N—R
4
or —O—, in which R
4
is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a heterocyclic group; Z
2
is >N—R
5
or >C(R
6
)(R
7
), in which R
5
is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a heterocyclic group, and R
6
and R
7
are each a hydrogen atom or a substituent;
6. The silver halide color photographic material described in 5 above, wherein in formula (III), R
3
is a chlorine atom;
7. The silver halide color photographic material described in 5 or 6 above, wherein R
10
is an unsubstituted alkyl group having 8 to 21 carbon atom;
8. The silver halide color photographic material described in 5 or 6 above, wherein in formula (III), R
10
is represented by the following formula (IV):
wherein R
11
is a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group; R
12
is an alkyl group or a cycloalkyl group; n is an integer of 1 to 10, provided that when n is 2 or more, plural R
11
's may be the same or different.
DETAILED DESCRIPTION OF THE INVENTION
In formula (I), examples of the substituent represented by R
1
include an alkyl group (e.g., methyl, ethyl, isopropyl, t-butyl, hexyl, dodecyl, etc.), a cycloalkyl group (e.g., cyclopentyl, cyclohexyl, adamantly, etc.), an aryl group (e.g., phenyl, p-t-octylphenyl, etc.), a heterocyclic group (e.g., pyridyl, thiazolyl, oxazolyl, etc.), an alkoxy group (e.g., methoxy, etc.), an aryloxy group (e.g., 2,4-di-t-amylphenoxy, etc.), an alkoxycarbonyl group (e.g., methoxycarbonyl, etc.), an aryloxycarbonyl group (e.g., m-pentadecylphenoxycarbonyl, etc.), a halogen atom (e.g., chlorine, bromine, etc.), a sulfonyl group (e.g., methanesulfonyl, etc.), an acylamino group (e.g., acetylamino, benzoylamino, etc.), a sulfonylamino group (e.g., dodecanesulfonylamino, etc.), nitro, cyano, an amino group (e.g., dimethylamino, anilino, etc.), an alkylthio group (e.g., methylthio, etc.), and hydroxy. Of these, R1 is preferably an alkoxy group, and methoxy is specifically preferred. The substituents represented by R
1
may be further substituted.
In formula (I), representative examples of the branched alkyl group having 7 to 20 carbon atoms, represented by R
2
include the following groups, but are not limited to these:
R
2
may be substituted, and examples of substituents are the same as defined in the substituent for R
1
.
In formulas (I), (II) and (III), R
3
is a hydrogen atom or a halogen atom, preferably a halogen atom, and more preferably a chlorine atom. In formulas (I) and (II), m is an integer of 1 to 5, preferably 1, and more preferably, the substituting position of R1 is the par
Ikesu Satoru
Ota Katsuji
Suzuki Takatugu
Suzuki Takayuki
Ueda Noriko
Bierman Jordon B.
Bierman, Muserlian and Lucas
Konica Corporation
Letscher Geraldine
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