Radiation imagery chemistry: process – composition – or product th – Radiation sensitive product – Identified radiation sensitive composition with color...
Reexamination Certificate
2001-06-11
2003-04-08
Letscher, Geraldine (Department: 1752)
Radiation imagery chemistry: process, composition, or product th
Radiation sensitive product
Identified radiation sensitive composition with color...
C430S543000, C430S558000
Reexamination Certificate
active
06544724
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a coupler having a specific ballasting group, in particular a photographic coupler having the ballasting group, and to a silver halide color photographic light-sensitive material containing said coupler. More specifically, the present invention relates to a coupler that is excellent in solubility; that can generate a dye having improved fastness to light, and that can be inexpensively produced, and to a silver halide color photographic light-sensitive material containing said coupler.
BACKGROUND OF THE INVENTION
As is well known, to improve the sharpness of a color photograph; that is, to make the definition of an image high, it is effective to make the layer of a silver halide color photographic light-sensitive material thin. Recently there has been increased demand for photographic processing to be made simple and rapid. To meet this demand of processing speed enhancement, it is also effective to make the layer of a light-sensitive material thin.
Research on photographic couplers has been eagerly conducted. For example, as a magenta coupler, U.S. Pat. No. 4,540,654 and the like disclose 1H-pyrazolo[1,5-b]-1,2-4-triazole couplers and U.S. Pat. No. 3,725,067 and the like disclose 1H-pyrazolo[1,5-c]-1,2-4-triazole couplers, respectively, that give good magenta dyes. JP-A-1-302249 (“JP-A” means unexamined published Japanese patent application) and JP-A-6-43611 disclose that the color image fastness of a 1H-pyrazolo[1,5-b]-1,2-4-triazole coupler having a tertiary alkyl group in its 6-position, and a phenylene group in its 2-position, is improved compared with conventional couplers. However, when rapid processing suitability is given, and the definition of an image is made higher by making the layer thin, these pyrazolotriazole magenta couplers are not necessarily satisfactory. For example, when the solubility of such a coupler itself in a high-boiling-point organic solvent is low, it is necessary to use this solvent in a large amount. This runs counter to the thinning of such a layer as mentioned in the above. Even if such a coupler can be added to an emulsion layer of a light-sensitive material, the coupler may be precipitated when the light-sensitive material is stored prior to being subjected to development processing with the lapse of time. Thus, the solubility of such a coupler is an important task to be attained.
On the other hand improving the storability of a color image, in particular the fastness of a color image to light, is also an important task for color photographs used for preserving records. For example, U.S. Pat. No. 3,725,067 and the like propose a 1H-pyrazolo[1,5-c]-1,2-4-triazole magenta coupler. However, further improvement in the fastness to light is desired, since the demand for improving fastness to light is intense.
Further, an important task in development of a coupler is whether it is possible or not to produce inexpensively a coupler having both of the above-mentioned solubility and fastness to light.
SUMMARY OF THE INVENTION
The present invention is a coupler represented by the following formula (I):
wherein
R represents an alkyl, alkenyl, alkynyl, aryl or heterocyclic group; L is —CO— or —SO
2
—; and X is a hydrogen atom or a group capable of being split-off upon coupling with an oxidized product of a developing agent.
Further, the present invention is a silver halide color photographic light-sensitive material that contains the coupler represented by formula (I).
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, the following means are provided.
(1) A coupler represented by the following formula (I):
wherein
R represents an alkyl, alkenyl, alkynyl, aryl or heterocyclic group; L is —CO— or —SO
2
—; and X is a hydrogen atom or a group capable of being split-off upon coupling with an oxidized product of a developing agent.
(2) A silver halide color photographic light-sensitive material containing the coupler represented by formula (I).
The present invention will be described in detail hereinafter.
The inventors thought out a concept of making a ballasting group of a coupler to have roles of improving both solubility and fastness to light. We designed various ballasting groups and made eager investigations on various couplers to attain the present invention. Specifically, it has been found out that by introducing a specific,ballasting group to a pyrazolotriazole coupler having a specific structure, the solubility of the coupler is improved and the light-fastness of an azomethine dye which is generated by coupling reaction of the coupler with an oxidized product of a developing agent is notably improved. It has also been found out that the coupler of the present invention can be produced from inexpensive raw materials through short steps.
The compound represented by formula (I) according to the present invention can be synthesized by introduction of an amido group via an amido-bond-forming reaction of a compound a with a compound b. With the coupler of the present invention, the amido group can be worked as a so-called ballasting group.
The coupler represented by formula (I) of the present invention will be described below.
In the formula (I), R represents an alkyl, alkenyl, alkynyl, aryl or heterocyclic group. The alkyl, alkenyl, or alkynyl group may be a straight chain or a branched chain, or cyclic. In the case that the group is cyclic, the group is generally called a cycloalkyl, cycloalkenyl or cycloalkynyl group. In the present invention, alkyl, alkenyl and alkynyl groups include cycloalkyl, cycloalkenyl cycloalkynyl groups. Examples of an unsubstituted alkyl group include methyl, ethyl, n-butyl, t-butyl, n-hexyl, cyclohexyl, 2-ethylbutyl, 2-methylpentyl, n-heptyl, n-octyl, 2-ethylhexyl, n-decyl, n-tetradecyl, and adamanthly. Examples of an unsubstituted alkenyl group include vinyl, ally, 1-butenyl, cis-2-butenyl, trans-2-butenyl, oleyl, and cyclohexenyl. Examples of an unsubstituted alkynyl group include propargyl, 1-butynyl, 2-butynyl and 1-pentynyl. The alkyl, alkenyl and alkynyl groups may be substituted with one or more substituents. Examples of the substituent include the followings: halogen atoms (such as fluorine and chlorine), alkoxy groups (such as methoxy, ethoxy, isopropoxy, dodecyloxy, and 2-methoxyethyoxy), aryl groups (such as phenyl, naphthyl, and anthranyl), aryloxy groups (such as phenoxy, 2-methoxyphenoxy, 4-t-octylphenoxy, and naphthoxy), alkylthio groups (such as methylthio, ethylthio, hexylthio, octylthio, hexadecylthio, 2-ethoxycarbonylpropylthio), arylthio groups (such as phenylthio, 2-pyvaloylamidopheylthio, 2-butoxy-5-t-octylphenylthio, naphthylthio, 2-butoxycarbonylphenylthio), alkylcarbonyl groups (such as methylcarbonyl, ethylcarbonyl, propylcarbonyl, and t-butylcarbonyl), arylcarbonyl groups (such as phenylcarbonyl, naphtylcarbonyl, and p-toluenecarbonyl), alkylcarbonyloxy groups (such as acetyloxy, propionyloxy, heptanoyloxy, 2-ethylhexanoyloxy, cyclohexanoyloxy, and pyvaloyloxy), arylcarbonyloxy groups (such as benzoyloxy, 2-butoxybenzoyloxy, 2,5-dichlorobenzoyloxy, and 3-octyloxycarbonylbenzoyloxy), alkoxycarbonyl groups (such as methoxycarbonyl, ethoxycarbonyl, propyloxycarbonyl, butoxycarbonyl, octyloxycarbonyl, dodecyloxycarbonyl, and 2-ethylhexyloxycarbonyl), carbonamido groups (such as acetoamido, propaneamido, hexadecaneamido, pyvaloylamido, benzamido, 2-ethoxybenzamido, 3-dodecyloxycarbonylpropaneamido, and 4-tetradecyloxycarbonylbutaneamido), sulfonamido groups (such as methanesulfonamido, butanesulfonamido, octanesulfonamido, hexadecanesulfonamido, benzenesulfonamido, p-toluenesulfonamido, and 2-octyloxy-5-t-octylbenzenesulfonamido), alkylamino groups (such as methylamino, N,N-diethylamino, t-butylamino, N,N-di-n-butylamino, methylethylamino, N,N-di-n-octylamino), arylamino groups (such as aminophenyl, and aminonaphthyl), carbamonyl groups (such as N-methylcarb
Nakamine Takeshi
Satoh Hideaki
Seto Nobuo
Shimada Yasuhiro
Yoneyama Hiroyuki
Fuji Photo Film Co. , Ltd.
Letscher Geraldine
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