JPH01238660A - Method for processing silver halide photographic sensitive material - Google Patents

Method for processing silver halide photographic sensitive material

Info

Publication number
JPH01238660A
JPH01238660A JP6618688A JP6618688A JPH01238660A JP H01238660 A JPH01238660 A JP H01238660A JP 6618688 A JP6618688 A JP 6618688A JP 6618688 A JP6618688 A JP 6618688A JP H01238660 A JPH01238660 A JP H01238660A
Authority
JP
Japan
Prior art keywords
group
sensitive material
silver halide
compd
atom
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
JP6618688A
Other languages
Japanese (ja)
Inventor
Minoru Ohashi
稔 大橋
Matsuichi Horii
堀井　松一
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsubishi Paper Mills Ltd
Original Assignee
Mitsubishi Paper Mills Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Mitsubishi Paper Mills Ltd filed Critical Mitsubishi Paper Mills Ltd
Priority to JP6618688A priority Critical patent/JPH01238660A/en
Priority to US07/323,873 priority patent/US4920043A/en
Publication of JPH01238660A publication Critical patent/JPH01238660A/en
Pending legal-status Critical Current

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Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
    • G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
    • G03C5/29—Development processes or agents therefor
    • G03C5/305—Additives other than developers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/42—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D235/26—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D235/28—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18—Benzotriazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D277/70—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D277/70—Sulfur atoms
    • C07D277/72—2-Mercaptobenzothiazole
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D293/00—Heterocyclic compounds containing rings having nitrogen and selenium or nitrogen and tellurium, with or without oxygen or sulfur atoms, as the ring hetero atoms
    • C07D293/10—Heterocyclic compounds containing rings having nitrogen and selenium or nitrogen and tellurium, with or without oxygen or sulfur atoms, as the ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D293/12—Selenazoles; Hydrogenated selenazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
    • G03C1/346—Organic derivatives of bivalent sulfur, selenium or tellurium

Abstract

PURPOSE:To reduce the generation of a fog in the sensitive material by developing the sensitive material in the presence of a specified anti-fogging agent. CONSTITUTION:The silver halide photosensitive material is developed in the presence of a compd. (a compd. shown by formula I or II) which has a -NHCOCOOR group in a condensed aromatic ring, and has mercapto or thio group in a 5-membered nitrogen contg. heterocyclic ring. In the formula, R is hydrogen atom. or a monovalent org. group, Z is an atomic group necessary for forming an aromatic ring, X is O or S atom., etc., R1 is H atom. or alkyl group which may be substd. The compd. mentioned above may be incorporated in the emulsion layer of the sensitive material, in the upper or under coating layer for the emulsion layer or in a developer or its prebath. When the compd. is incorporated in the sensitive material, the sensitivity and the shelf-life in addition to the anti-fogging property of the sensitive material are improved.

Description

【発明の詳細な説明】 （Ａ）産業上の利用分野 本発明は、カブリ防止剤を使用するハロゲン化銀写真感
光材料の処理方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION (A) Industrial Application Field The present invention relates to a method for processing silver halide photographic materials using an antifoggant.

（Ｂ）従来技術及びその問題点 ハロゲン化銀写真感光材料は、保存中に経時変化して、
感度、カブリ、色調等写真特性が変化することは良く知
られている。又、近年はアクセスタイム短縮化の要望か
ら、従来よりも処理温度を高く、処理時間を短かくした
、いわゆる高温、迅速処理を行う場合が多くなっており
、写真特性の中でも特にカブリが発生し易い状態下にあ
ると言える。(B) Prior art and its problems Silver halide photographic materials change over time during storage.
It is well known that photographic characteristics such as sensitivity, fog, and color tone change. In addition, in recent years, due to the desire to shorten access time, so-called high-temperature, rapid processing, in which processing temperatures are higher and processing times are shorter than in the past, has become more common. It can be said that the situation is easy.

今日迄、保存中のカブリの増加と、現像処理中のカブリ
発生を防止、減少するために、多数の安定剤、カブリ防
止剤が見出され、特許として申請されて来ているが、強
力なカブリ防止効果を示す化合物はど、感光材料の感度
を減殺する傾向があり、感度の保持とカブリの防止を共
に満足する化合物は今だに見出されて暦ない。To date, many stabilizers and antifoggants have been discovered and patented in order to prevent or reduce the increase in fog during storage and the occurrence of fog during development. Compounds that exhibit antifogging effects tend to reduce the sensitivity of photosensitive materials, and no compound has yet been found that satisfies both sensitivity retention and fog prevention.

特開昭５１−３６１３０、同昭５５−１２１４３２、同
昭５５−１２６２３４などには、従来公知のカブリ防止
剤によって増感する技術が開示されているが、ハロゲン
化銀の晶癖や増感色素の種類に依存したり、カブリを増
加したり、軟調化を招く等の欠点を有している。JP-A-51-36130, JP-A-55-121432, JP-A-55-126234, etc. disclose techniques for sensitizing using conventionally known antifoggants; It has drawbacks such as being dependent on the type of image, increasing fog, and causing soft contrast.

（Ｃ）発明の目的 本発明の目的は、高感度でカブリの少ないハロゲン化銀
写真感光材料の処理方法を提供することにある。(C) Purpose of the Invention An object of the present invention is to provide a method for processing silver halide photographic materials with high sensitivity and less fog.

本発明の別の目的は、カブリを防止するとともに増感さ
れたハロゲン化銀写真感光材料を提供することにある。Another object of the present invention is to provide a silver halide photographic material which is sensitized and prevents fogging.

ＣＤ）発明の構成 本発明者等は、鋭意研究した結果、ある種の置換基を有
するカブリ防止剤が上記目的を達成することを見い出し
た。CD) Structure of the Invention As a result of extensive research, the present inventors have discovered that an antifoggant having a certain type of substituent group can achieve the above object.

すなわち、本発明は、縮合芳香環及び２位にメルカプト
基もしくはチオン基を有する含窒素５員環化合物の存在
下でハロゲン化銀写真感光材料を現像する処理方法に於
いて、前記化合物が縮合芳香環に式、−ＮＨＣＯＣＯＯ
Ｒ（Ｒは、水素原子または一価の有機基）で表わされる
置換基を有することを特徴とする処理方法である。That is, the present invention provides a processing method for developing a silver halide photographic light-sensitive material in the presence of a nitrogen-containing five-membered ring compound having a condensed aromatic ring and a mercapto group or a thione group at the 2-position. Formula in the ring, -NHCOCOO
This treatment method is characterized by having a substituent represented by R (R is a hydrogen atom or a monovalent organic group).

本発明のカブリ防止剤は、好ましくは下記一般式（１）
又は（Ｉｔ）で表わされる。The antifoggant of the present invention preferably has the following general formula (1):
or (It).

一般式（ｎ） 式中、Ｚは−ＮＨＣＯＣＯＯＲ以外の置換基を有してイ
テモよいベンゼン環、ナフタレン環等の縮合芳香環を形
成するに必要な原子群を表わす。縮合芳香環のその他の
置換基としては、ハロゲン原子（Ｆ、　ＣＡ、　Ｂｒな
と）、置換または無置換のアルキル基（メチル基、トリ
フルオロメチル基、エチル基、ｎ−オクチル基、ベンジ
ル基など）、置換または無置換のアリール基（フェニル
基、ｐ−クロロフェニル基など）、置換または無置換の
アルコキシ基、アリールオキシ基（メトキシ基、ｎ−へ
キシルオギシ基、フェノキシ基、ｎ−オクチル基ナト）
、スルホニル基（メタンスルホニル基、ｐ−トルエンス
ルホニル基など）、スルホンアミド基（ｎ−オクタンス
ルホンアミド基、ｐ−１ルエンスルホンアミド基など）
、スルファモイル基（ジエチルスルファモイル基、４−
クロロフェニルスルファモイル基など）、カルバモイル
ａ（ｎ−ブチルカルバモイル基、４−シアノフェニルカ
ルバモイル基など）、アミド基（ｎ−ヘキサンアミド基
、ｎ−デカンアミド基、ベンズアミド基など）、ウレイ
ド基（３−ブチルウレイド基、モルホリノカルボニルア
ミノ基など）、アリールまたはアルコキシカルボニルア
ミノ基（エトキシカルボニルアミノ基、１ｓｏ−ブチル
カルボニルアミノ基、フェノキシカルボニルアミノ基な
ど）、アリールまたはアルコキシカルボニル基（エトキ
シカルボニル基、フェノキシカルボニル基など）、アリ
ールまたはアルキルアミノカルボニルオキシ基（フェニ
ルアミノカルボニルオキシ基、１ｓｏ−ブチルアミノカ
ルボニルオキシ基など）、シアン基、アルキルまたはア
リールチオ基（ｎ−オクチルチオ基、２−メトキシカル
ボニルフェニルチオ基すど）などである。General Formula (n) In the formula, Z represents an atomic group having a substituent other than -NHCOCOOR and necessary to form a suitable fused aromatic ring such as a benzene ring or a naphthalene ring. Other substituents on the condensed aromatic ring include halogen atoms (F, CA, Br, etc.), substituted or unsubstituted alkyl groups (methyl group, trifluoromethyl group, ethyl group, n-octyl group, benzyl group, etc.). ), substituted or unsubstituted aryl group (phenyl group, p-chlorophenyl group, etc.), substituted or unsubstituted alkoxy group, aryloxy group (methoxy group, n-hexyloxy group, phenoxy group, n-octyl group)
, sulfonyl group (methanesulfonyl group, p-toluenesulfonyl group, etc.), sulfonamide group (n-octanesulfonamide group, p-1 toluenesulfonamide group, etc.)
, sulfamoyl group (diethylsulfamoyl group, 4-
chlorophenylsulfamoyl group, etc.), carbamoyl a (n-butylcarbamoyl group, 4-cyanophenylcarbamoyl group, etc.), amide group (n-hexanamide group, n-decanamide group, benzamide group, etc.), ureido group (3- butylureido group, morpholinocarbonylamino group, etc.), aryl or alkoxycarbonylamino group (ethoxycarbonylamino group, 1so-butylcarbonylamino group, phenoxycarbonylamino group, etc.), aryl or alkoxycarbonyl group (ethoxycarbonyl group, phenoxycarbonyl group) ), aryl or alkylaminocarbonyloxy groups (phenylaminocarbonyloxy groups, 1so-butylaminocarbonyloxy groups, etc.), cyanogen groups, alkyl or arylthio groups (n-octylthio groups, 2-methoxycarbonylphenylthio groups, etc.) etc.

Ｘは酸素原子、硫黄原子、セレン原子１．　Ｎ−Ｒ２（
Ｒ２は水素原子、置換または無置換のアルキル基）を表
わす。X is an oxygen atom, a sulfur atom, a selenium atom1. N-R2(
R2 represents a hydrogen atom or a substituted or unsubstituted alkyl group.

Ｒ１は水素原子、置換または無置換のアルキル基を表わ
す。R1 represents a hydrogen atom or a substituted or unsubstituted alkyl group.

本発明のカブリ防止剤は、縮合芳香環に少なくとを有す
ることを特徴とする。鼓に、Ｒは水素原子およびアルキ
ル基、アリール基、アルケニル基、複素環基、置換アミ
ノ基などの一価の有機基を表わす。The antifoggant of the present invention is characterized by having at least one fused aromatic ring. In general, R represents a hydrogen atom and a monovalent organic group such as an alkyl group, an aryl group, an alkenyl group, a heterocyclic group, or a substituted amino group.

Ｒで示されるアルキル基、アルケニル基は、好ましくは
炭素数２０以下のアルキル基、アルケニル基であって、
ハロゲン原子、シアン基、カルボキシ基、アルコキシ基
（ポリエーテル基を含む）、アリールオキシ基、スルホ
基、アリール基、置換アミ７基などの置換基を有してい
てもよい。The alkyl group or alkenyl group represented by R is preferably an alkyl group or alkenyl group having 20 or less carbon atoms,
It may have a substituent such as a halogen atom, a cyan group, a carboxy group, an alkoxy group (including a polyether group), an aryloxy group, a sulfo group, an aryl group, or a substituted amino group.

Ｒで示されるアリール基は、フェニル基、ナフチル基で
あって、アルキル基、アリール基、ハロゲン原子、アル
コキシ基、アリールオキシ基、アルケニル基、置換アミ
ン基、アシルアミノ基、スルホンアミド基、アルキリデ
ンアミノ基、ヘテロ環基などの置換基を有していてもよ
い。The aryl group represented by R is a phenyl group, a naphthyl group, an alkyl group, an aryl group, a halogen atom, an alkoxy group, an aryloxy group, an alkenyl group, a substituted amine group, an acylamino group, a sulfonamide group, an alkylidene amino group. , may have a substituent such as a heterocyclic group.

Ｒで示される複素環基は、ピリジル基、ピラジニル基、
ピリミジニル基、ピリダジニル基、キノリル基、イソキ
ノリル基、フタラジニル基、ナフチリジニル基、キノオ
キサリニル基、キナゾリニル基、シンノリニル基、ブテ
リジニル基等であって、アルキル基、アリール基、ハロ
ゲン原子、置換アミノ基、シアノ基、アシルアミノ基、
カルボキシ基、アルコキシカルボニル基、アリールオキ
シカルボニル基などの置換基を有していてもよい、Ｒで
示される置換アミノ基は、アルキル基、アリール基、ヘ
テロ環基なとで置換されたアミン基、あるいはアミノ基
の窒素原子と共に複素環を形成したものを含む。The heterocyclic group represented by R is a pyridyl group, a pyrazinyl group,
A pyrimidinyl group, a pyridazinyl group, a quinolyl group, an isoquinolyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a buteridinyl group, and an alkyl group, an aryl group, a halogen atom, a substituted amino group, a cyano group, acylamino group,
The substituted amino group represented by R, which may have a substituent such as a carboxy group, an alkoxycarbonyl group, or an aryloxycarbonyl group, is an amine group substituted with an alkyl group, an aryl group, a heterocyclic group, etc. Alternatively, it includes a heterocycle formed with the nitrogen atom of an amino group.

本発明のカブリ防止剤の代表的な具体例を以下に示す。Typical specific examples of the antifoggant of the present invention are shown below.

（１０〕 く合成例１〉　（例示化合物１０の合成）６−アミノ−
２−メルカプトベンゾチアゾール３６．４を及びフェニ
ルオキサリルクロリド４０．６２をベンゼン５００ゴ中
にけんだく攪拌しながら、トリエチルアミン３０．７７
！を徐々に滴下したのち室温にて約１時間攪拌後、約１
．５時間加熱還流した。(10) Synthesis Example 1 (Synthesis of Exemplary Compound 10) 6-amino-
While stirring 36.4 ml of 2-mercaptobenzothiazole and 40.62 ml of phenyloxalyl chloride into 500 g of benzene, 30.77 ml of triethylamine was added.
! was gradually added dropwise and stirred at room temperature for about 1 hour.
．． The mixture was heated under reflux for 5 hours.

反応後、反応液を水中にあけ酢酸エチルにて抽出し、得
た有機層を水洗後、無水硫酸ナトリウムにて乾燥した。After the reaction, the reaction solution was poured into water and extracted with ethyl acetate, and the obtained organic layer was washed with water and dried over anhydrous sodium sulfate.

乾燥後、溶媒を減圧下留去したのち、得られた粗結晶を
ジオキサンから再結晶を行って目的とする例示化合物を
得た。After drying, the solvent was distilled off under reduced pressure, and the resulting crude crystals were recrystallized from dioxane to obtain the desired exemplary compound.

収量：３６．５ｆ　　　融点＝３００℃以上元素分析二
　　　〇（％）　　　　Ｈ（％）　　　　Ｎ（％）理論
値　　５４．５３　　３゜０５　　８．４８測定値　　
５４．３３　　３．０８　　８．７６〈合成例２〉　（
例示化合物５の合成〕合成例１で得た、例示化合物１０
を６．６２秤量し、それを１規定力性カリウム水溶液６
〇−中に添加した。Yield: 36.5f Melting point = 300℃ or higher Elemental analysis 20 (%) H (%) N (%) Theoretical value 54.53 3゜05 8.48 Measured value
54.33 3.08 8.76〈Synthesis Example 2〉 (
Synthesis of Exemplified Compound 5] Exemplified Compound 10 obtained in Synthesis Example 1
Weigh 6.62 and add it to 1N potassium aqueous solution 6.
〇- Added inside.

約３時間、室温にて攪拌したのち１規定塩酸を加え、反
応液のＰＨを酸性とした。After stirring at room temperature for about 3 hours, 1N hydrochloric acid was added to make the pH of the reaction solution acidic.

析出した結晶を戸数し、水洗後乾燥して目的とする例示
化合物５を得た。The precipitated crystals were collected, washed with water, and then dried to obtain the desired exemplary compound 5.

収量：４．２ｆ　　　　融点：３００℃以上元以上析：
　　　　　Ｃ（％）　　　　Ｈ（％）　　　Ｎ＠）理論
値　　　４２，５１　　２．３８　　１１．０２測定値
　　　４２．３０　　２．５１　　１１．００本発明の
処理方法では、露光されたハロゲン化銀写真感光材料を
、本発明のカブリ防止剤の存在下、種々の現像液で現像
を行う。Yield: 4.2f Melting point: 300°C or above Original analysis:
C (%) H (%) N@) Theoretical value 42,51 2.38 11.02 Measured value 42.30 2.51 11.00 In the processing method of the present invention, the exposed silver halide photographic light-sensitive material is , development is carried out with various developers in the presence of the antifoggant of the present invention.

現像時に、本発明のカブリ防止剤を存在させる手段は種
々有るが、写真感光材料のハロゲン化銀乳剤層中、又は
該乳剤層と水透過性の関係にあるコロイド層、例えば、
該乳剤層の為の上塗り又は下塗り層中に添加しておくか
、又は現像液中あるいは現像液の前浴中に添加すること
が望ましい。There are various means for making the antifoggant of the present invention present during development, but it may be present in a silver halide emulsion layer of a photographic light-sensitive material or in a colloid layer in a water-permeable relationship with the emulsion layer, for example,
It is desirable to add it to the topcoat or undercoat layer for the emulsion layer, or to the developer or a pre-bath of the developer.

本発明のカブリ防止剤を含有するハロゲン化銀写真感光
材料は、有効にカブリを防止するだけでなく感度を上昇
させるという極めて優れた効果がある。この効果は、通
常の露光のみならず、高照度短時間の露光においても現
われる。The silver halide photographic material containing the antifoggant of the present invention not only effectively prevents fogging but also has extremely excellent effects of increasing sensitivity. This effect appears not only in normal exposure but also in high-intensity, short-time exposure.

本発明のカブリ防止剤は、水又は水と混和性の溶媒、例
えばり、　Ｍ、　Ｆ、メタノール、エタノール又はアル
カリ水溶液等に溶解し、塗布する前に上記ハロゲン化銀
乳剤又は上記コロイド分散液に加え、混合することによ
り、上記ノ・ロゲン化銀乳剤又は上記コロイド分散液中
に添加できる。The antifoggant of the present invention is dissolved in water or a water-miscible solvent, such as M, F, methanol, ethanol, or an aqueous alkali solution, and added to the silver halide emulsion or colloidal dispersion before coating. By adding and mixing, it can be added to the above-mentioned silver halogenide emulsion or the above-mentioned colloidal dispersion.

更に又、特開昭５３−１３７１３１号明細書に示される
様な手法を用い、本発明のカブリ防止剤をラテックスに
より分散して上記ノ・ロゲン化銀乳剤又は上記コロイド
分散液中に添加することも可能である。Furthermore, the antifoggant of the present invention can be dispersed in latex and added to the silver halide emulsion or the colloidal dispersion using a method as shown in JP-A-53-137131. is also possible.

又、処理液中に添加する場合は、そのま＼添加するか、
水と混和性の溶媒、例えばり、Ｍ、Ｆ、、メタノール又
はエタノール等に溶解し添加することができる。Also, when adding it to the processing solution, either add it as is or
It can be added after being dissolved in a water-miscible solvent such as M, F, methanol or ethanol.

ハロゲン化銀写真感光材料中に添加する場合、ハロゲン
化銀１モルに対して、本発明のカブリ防止剤の量は、一
般に１０−６〜１０−２モル、好ましくは、１０−５〜
１０−２モルの範囲、処理液中に添加する場合は１０−
５〜１０−１モル／ｌ、好ましくは１０−４〜１０−２
モル／ｌの範囲に設定することが出来る。When added to a silver halide photographic light-sensitive material, the amount of the antifoggant of the present invention is generally 10-6 to 10-2 mol, preferably 10-5 to 10-2 mol, per 1 mol of silver halide.
10-2 mol range, 10-2 mol range when added to processing solution
5-10-1 mol/l, preferably 10-4-10-2
It can be set within the range of mol/l.

本発明の処理方法は、本発明のカブリ防止剤を存在させ
る以外の点については公知の処理液や処理方法を用いる
ことが出来るが、目的に応じて、銀画像を形成する現像
処理（黒白写真処理及び拡散転写を含む処理）あるいは
、色素像を形成する現像処理（カラー写真処理）のどち
らにも実施することができる。In the processing method of the present invention, known processing solutions and processing methods can be used except for the presence of the antifoggant of the present invention. processing (including processing and diffusion transfer) or development processing (color photographic processing) to form a dye image.

黒白写真処理を行う場合に用いる現像液は、公知の現像
主薬を含むことができる。現像主薬としては、ジヒドロ
キシベンゼン類（例えば、ハイドロキノン）、３−ピラ
ゾリドン類（例えば、１−２エニルー３−ピラゾリドン
）、アミンフェノール類（例えば、Ｎ−メチル−Ｐ−ア
ミノンエノール）、ヒドロキシルアミン類（例工ば、Ｎ
、Ｎ　−ジエチルヒドロキシルアミン）、アスコルビン
酸及び米国特許第４，０６７，８７２号明細書に記載の
１．２，３，４．−テトラヒドロキノリン環とインドレ
ン環とが縮合したような複素環化合物類などを単独もし
くは組合せて用いることができる。The developer used in black-and-white photographic processing can contain a known developing agent. As developing agents, dihydroxybenzenes (e.g., hydroquinone), 3-pyrazolidones (e.g., 1-2 enyl-3-pyrazolidone), aminephenols (e.g., N-methyl-P-aminoneenol), hydroxylamines (e.g., For example, N
, N-diethylhydroxylamine), ascorbic acid and 1.2, 3, 4. as described in US Pat. No. 4,067,872. -Heterocyclic compounds such as those in which a tetrahydroquinoline ring and an indolene ring are condensed can be used alone or in combination.

カラー写真処理を行う場合に用いる現像液は公知の現像
主薬を含むことができる。現像主薬としては、フェニレ
ンジアミン類（例えば、４−アミノ−Ｎ、Ｎ−ジエチル
アニリン、３−メチル−４−アミノ−Ｎ、Ｎ−ジエチル
アニリン、４−アミノ−Ｎ−エチルーベーβ−ヒドロキ
シエチルアニリン、３−メチル−４−アミクーペ−エチ
ル−Ｎ−β−ヒドロキシエチルアニリン、５−メチル−
４−アミノーヘーエチルーＮ−β−メタンスルホアミド
エチルアニリン、４−アミノ−３−メチル−Ｎ−エチル
−Ｎ−β−メトキシエチルアニリン等）、アミンフェノ
ール類などを、単独もしくは組合せて用いることができ
る。現像液には一般にこの他公知の保恒剤、アルカリ剤
、ＰＨ緩衝剤、本発明に使用されるカブリ防止剤以外の
カブリ防止剤等を含み、更に必要に応じてノ・ロゲン化
銀溶解剤、色調剤、現像促進剤、界面活性剤、消泡剤、
硬水軟化剤、硬膜剤、粘性付与剤等を含んでもよい。The developer used in color photographic processing can contain a known developing agent. As the developing agent, phenylenediamines (for example, 4-amino-N, N-diethylaniline, 3-methyl-4-amino-N, N-diethylaniline, 4-amino-N-ethylube β-hydroxyethylaniline, 3-Methyl-4-amicupe-ethyl-N-β-hydroxyethylaniline, 5-methyl-
(4-aminohethyl-N-β-methanesulfamide ethylaniline, 4-amino-3-methyl-N-ethyl-N-β-methoxyethylaniline, etc.), amine phenols, etc. may be used alone or in combination. Can be done. The developing solution generally contains a known preservative, an alkaline agent, a PH buffer, an antifoggant other than the antifoggant used in the present invention, and, if necessary, a silver chloride solubilizer. , color toner, development accelerator, surfactant, antifoaming agent,
It may also contain a water softener, a hardening agent, a viscosity imparting agent, and the like.

定着液としては一般に用いられる組成のものを用いるこ
とができる。定着剤としてはチオ硫酸塩、チオシアン酸
塩のほか、定着剤としての効果が知られている有機硫黄
化合物を用いることができる。As the fixer, one having a commonly used composition can be used. As the fixing agent, in addition to thiosulfates and thiocyanates, organic sulfur compounds known to be effective as fixing agents can be used.

定着液には硬膜剤として水溶性アルミニウム塩を含んで
もよい。The fixing solution may contain a water-soluble aluminum salt as a hardening agent.

本発明の処理方法は公知の種々のハロゲン化銀写真感光
材料に適用することができる。The processing method of the present invention can be applied to various known silver halide photographic materials.

本発明を適用しうるハロゲン化銀乳剤としては、例えば
、スペクトル増感および非増感乳剤、Ｘ線乳剤、感赤外
線乳剤などがあり、又それらは、高感度ネガ乳剤でも低
感度ポジ乳剤でもよく、更に又、乳剤はオルンクロム型
又はバンクロム型でもよい。Silver halide emulsions to which the present invention can be applied include, for example, spectrally sensitized and unsensitized emulsions, X-ray emulsions, and infrared-sensitive emulsions, and they may be high-speed negative emulsions or low-speed positive emulsions. Furthermore, the emulsion may be of the Ornchrome type or Banchrome type.

感光性銀塩としては、各種の銀塩が使用できる。Various silver salts can be used as the photosensitive silver salt.

例えば、臭化銀、沃化銀、塩化銀、又は混合ハロゲン化
銀（塩臭化銀、沃臭化銀等）がある。Examples include silver bromide, silver iodide, silver chloride, or mixed silver halides (silver chlorobromide, silver iodobromide, etc.).

ハロゲン化銀は、普通の親水性コロイド、例えばゼラチ
ン、カゼイン、ポリビニルアルコール、カルボキシメチ
ルセルロース等に分散できるが、−］５− ゼラチンが有利である。The silver halide can be dispersed in common hydrophilic colloids such as gelatin, casein, polyvinyl alcohol, carboxymethylcellulose, etc., but -]5-gelatin is preferred.

ハロゲン化銀乳剤は、化学的にも増感可能であり、少量
の硫黄含有化合物（例えばアリールチオシアネート、ア
リルチオ尿素、チオ硫酸ソーダ等）の存在下に熟成する
ことによって化学的に増感できる、 該乳剤は、又、還元剤（例えは、フランス特許筒１，１
４６，９５５号明細書、米国特許筒２，４８７゜８５０
号明細書に記載されている如きスズ化合物、英国特許筒
７８９．８２３号明細書に記載されている如きイミノ−
アミンメタンスルフィン酸化合物等）および少量の貴金
属（例えは、金−白金、）くラジウム、イリジウム、ル
テニウム、およびロジウム等）によっても増感できる。Silver halide emulsions can also be chemically sensitized by ripening in the presence of small amounts of sulfur-containing compounds (e.g. aryl thiocyanate, allyl thiourea, sodium thiosulfate, etc.). The emulsion may also contain a reducing agent (for example, French Patent Co., Ltd.
No. 46,955, U.S. Patent No. 2,487°850
tin compounds as described in GB 789.823;
amine methanesulfinic acid compounds, etc.) and small amounts of noble metals (eg, gold-platinum, radium, iridium, ruthenium, rhodium, etc.).

他の添加剤、例えば現像促進剤、増感剤、酸化防止剤、
硬膜剤、界面活性剤、増白剤、色像形成カプラー、ＤＩ
Ｒカプラー等の写真分野で公知の種々の添加剤もノ・ロ
ゲン化銀乳剤層又は他の水透過性コロイド層に加えるこ
とができる。Other additives, such as development accelerators, sensitizers, antioxidants,
Hardeners, surfactants, brighteners, color image-forming couplers, DI
Various additives known in the photographic art, such as R couplers, can also be added to the silver halide emulsion layer or other water permeable colloid layer.

更に本発明のカブリ防止剤は、他のカブリ防止剤又はカ
ブリ防止剤プレカーサーと組み合わせて使用することが
できる。Furthermore, the antifoggants of the present invention can be used in combination with other antifoggants or antifoggant precursors.

（Ｅ）実施例 以下に実施例を掲げ本発明を更に詳細に説明する。(E) Example The present invention will be explained in more detail with reference to Examples below.

実施例１ 沃化銀１モルチ臭化銀４７モルチ塩化銀５２モルチのハ
ロゲン化銀よりなるクロロブロマイド印画紙用乳剤に、
通常用いられる界面活性剤、硬膜剤を加え乳剤を６部に
分けた。Example 1 A chlorobromide emulsion for photographic paper consisting of silver halide containing 1 mole of silver iodide, 47 moles of silver bromide, and 52 moles of silver chloride,
A commonly used surfactant and hardener were added to the emulsion and divided into 6 parts.

１部は対照とし、残りに対しては本発明に係る化合物及
び下記の比較化合物をメタノールに溶解し、ハロゲン化
銀１モル当り１．５Ｘ１０　　モルの割合で添加した。One part was used as a control, and to the remaining part, the compound according to the present invention and the following comparative compound were dissolved in methanol and added at a ratio of 1.5 x 10 mol per mol of silver halide.

すべての乳剤をポリエチレンで被覆した紙支持体に銀量
１．５２βとなるように塗布し試料とした。All the emulsions were coated on a paper support coated with polyethylene to give a silver content of 1.52β and used as samples.

それぞれの試料にウエンジ露光を与え、Ｄ−７２現像液
で２０℃９０秒現像しセンシトメトリーをおこなった。Each sample was exposed to wedge light, developed with a D-72 developer at 20° C. for 90 seconds, and subjected to sensitometry.

別に露光を与えない試料をＤ−７２現像液で３０℃５分
現像しカブリ濃度を測定し下記の結果が得られた。A sample which was not exposed to light was developed with a D-72 developer at 30 DEG C. for 5 minutes, and the fog density was measured, and the following results were obtained.

比較化合物としては次の三種の化合物を用いた。The following three compounds were used as comparative compounds.

Ｈ８−Ｃ＝Ｎ 実施例２ 実施例１の試料１（カブリ防止剤を含まない印画紙）を
用い、Ｄ−７２現像液にカブリ防止剤を７．５Ｘ１０　
　モル／を添加した現像液で実施例１と同様の現像処理
をおこない下記の結果を得た。H8-C=N Example 2 Using Sample 1 of Example 1 (photographic paper containing no antifoggant), add 7.5×10 antifoggant to D-72 developer.
The same development process as in Example 1 was carried out using a developer to which mol/mole was added, and the following results were obtained.

実施例３ 平均粒径（１，３４μｍの立方体塩化銀乳剤を化学増感
した後、下記の増感色素を）・ロゲン化銀１モル尚り５
Ｘ１０−５モル加え、界面活性剤および２．４−ジクロ
ロー６−ヒドロキシー１，３．５−　）リアジン（Ｎａ
塩）を加えてポリエステルフィルム支持体上に鋏景５　
？／ｒｒ？となるように塗布し試料とした。Example 3 Average grain size (after chemically sensitizing a cubic silver chloride emulsion of 1.34 μm, use the following sensitizing dye) - 1 mole of silver chloride 5
Added 10-5 moles of X, surfactant and 2,4-dichloro-6-hydroxy-1,3.5-
5. Add salt) to the polyester film support.
? /rr? It was applied as a sample and used as a sample.

増感色素 １　　　ｅ　　　１ （ＣＨ２）３ＳＱ３（ＣＩ（２）５８０３）１１０−５
秒のウェッジ露光を与え、ＰＱ現像液で３０℃６０秒現
像しセンシトメトリーを行った。Sensitizing dye 1 e 1 (CH2)3SQ3 (CI(2)5803) 110-5
A second wedge exposure was applied, and development was performed at 30° C. for 60 seconds using a PQ developer, followed by sensitometry.

カブリ防止剤は、ノ・ロゲン化銀１モル当り２　Ｘ　１
０”３モルの割合で添加し、下記の結果を得た。The antifoggant is 2 x 1 per mole of silver halide.
The following results were obtained by adding 0"3 moles.

（Ｆ）発明の効果 本発明の処理方法は、カブリを有効に防止することが出
来、また保存性に優れた高感度のノ・ロゲン化銀写真感
光材料を提供することが出来る。(F) Effects of the Invention The processing method of the present invention can effectively prevent fogging and can provide a highly sensitive silver halide photographic material with excellent storage stability.

Claims (1)

【特許請求の範囲】[Claims] （１）縮合芳香環及び２位にメルカプト基もしくはチオ
ン基を有する含窒素５員環化合物の存在下でハロゲン化
銀写真感光材料を現像する処理方法に於いて、前記化合
物が縮合芳香環に式、−ＮＨＣＯＣＯＯＲ（Ｒは、水素
原子または一価の有機基）で表わされる置換基を有する
ことを特徴とする処理方法。(1) In a processing method for developing a silver halide photographic light-sensitive material in the presence of a nitrogen-containing five-membered ring compound having a fused aromatic ring and a mercapto group or a thione group at the 2-position, the compound is , -NHCOCOOR (R is a hydrogen atom or a monovalent organic group).
JP6618688A 1988-03-18 1988-03-18 Method for processing silver halide photographic sensitive material Pending JPH01238660A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP6618688A JPH01238660A (en) 1988-03-18 1988-03-18 Method for processing silver halide photographic sensitive material
US07/323,873 US4920043A (en) 1988-03-18 1989-03-15 Method for processing silver halide photographic light-sensitive material

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP6618688A JPH01238660A (en) 1988-03-18 1988-03-18 Method for processing silver halide photographic sensitive material

Publications (1)

Publication Number Publication Date
JPH01238660A true JPH01238660A (en) 1989-09-22

Family

ID=13308561

Family Applications (1)

Application Number Title Priority Date Filing Date
JP6618688A Pending JPH01238660A (en) 1988-03-18 1988-03-18 Method for processing silver halide photographic sensitive material

Country Status (1)

Country Link
JP (1) JPH01238660A (en)

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