JPH02103036A - Method for processing silver halide photographic sensitive material - Google Patents

Method for processing silver halide photographic sensitive material

Info

Publication number
JPH02103036A
JPH02103036A JP25763888A JP25763888A JPH02103036A JP H02103036 A JPH02103036 A JP H02103036A JP 25763888 A JP25763888 A JP 25763888A JP 25763888 A JP25763888 A JP 25763888A JP H02103036 A JPH02103036 A JP H02103036A
Authority
JP
Japan
Prior art keywords
group
sensitive material
silver halide
processing
halide photographic
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
JP25763888A
Other languages
Japanese (ja)
Inventor
Minoru Ohashi
稔 大橋
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 JP25763888A priority Critical patent/JPH02103036A/en
Priority to US07/323,873 priority patent/US4920043A/en
Publication of JPH02103036A publication Critical patent/JPH02103036A/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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)

Abstract

PURPOSE:To proceed processing of a silver halide photographic sensitive material without reducing sensitivity of the sensitive material and to generate scarce fog by processing the sensitive material in the presence of a specified antifoggant. CONSTITUTION:A silver halide photographic sensitive material is developed in the presence of a compd. (A) consisting of an N-contg. heterocyclic ring having no condensed aromatic ring, and having a substituent expressed by -NHCOCOOR (wherein R is H or a univalent org. group) as an antifoggant. Suitable example for the compd. (A) is, for example, a compd. expressed by the formula, wherein R<1> is -NHCOCOOH, which can be added to an emulsion layer or other photography constituting layer of the sensitive material or to the developing soln. Another antifoggant may be used in combination.

Description

【発明の詳細な説明】 （Ａ）産業上の利用分野 本発明は、カプリ防止剤を使用するハロゲン化銀写Ｊ４
／ｉ！！ｃ光材料の処理方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION (A) Industrial field of application The present invention is directed to silver halide copy J4 using an anti-capri agent.
/i! ! This invention relates to a method for processing optical materials.

（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、カプリ、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プ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, capri, and color tone change. In addition, in recent years, due to the desire to shorten access times, 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、保存中のカプリの増加と、現像処理中のカプリ
発生を防止、減少するために、多数の安定剤、カプリ防
止剤が見出され、特許として申請されて来ているが、強
力なカプ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、感度の保持とカプリの防止を共
に満足する化合物は今だに見出されていない。To date, many stabilizers and anti-capri agents have been discovered and patented to prevent or reduce the increase of capri during storage and the generation of capri during development processing, but Compounds that exhibit a capri-preventing effect tend to reduce the sensitivity of photosensitive materials, and a compound that satisfies both sensitivity retention and capri prevention has not yet been found.

（Ｃ）発明の目的 本発明の目的は、高感度でカプリの小ないハロゲン化銀
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 low capri.

（Ｄ）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
するカプリ防止剤が上記目的を達成することを見い出し
た。(D) Structure of the Invention As a result of intensive research, the present inventors discovered that an anti-capri agent having a certain type of substituent group achieves the above object.

すなわち、本発明は、縮合芳香環を有しない含窒素複素
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、該化合物が式、−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 heterocyclic compound having no fused aromatic ring, in which the compound has the formula, -NHCOCOO
This treatment method is characterized by having a substituent represented by R (R is a hydrogen atom or a monovalent organic group).

本発明の含窒素′ｖｉ、素環化合物は、ベンゼン環やナ
フタレン環の芳香環が縮合していない、５ないし６負の
含窒素複素環であって、イミダシリン、イミダゾール、
イミダシロン、ピラゾール、オキサゾリン、オキサゾー
ル、オキサシロン、チアゾリン、チアゾール、チアゾロ
ン、セレナゾリン、セレナゾール、セレナゾロン、オキ
サジアゾール、チアジアゾール、トリアゾール、テトラ
ゾール、ピラジン、ピリミジン、ピリダジン、トリアジ
ン。The nitrogen-containing 'vi, monocyclic compound of the present invention is a 5- to 6-negative nitrogen-containing heterocycle in which aromatic rings such as benzene rings and naphthalene rings are not condensed, such as imidacillin, imidazole,
Imidacylone, pyrazole, oxazoline, oxazole, oxacilone, thiazoline, thiazole, thiazolone, selenazoline, selenazole, selenazolone, oxadiazole, thiadiazole, triazole, tetrazole, pyrazine, pyrimidine, pyridazine, triazine.

オキサジン、チアジン、テトラジン、ポリアザインデン
等の複素環が挙げられる。Examples include heterocycles such as oxazine, thiazine, tetrazine, and polyazaindene.

これらの含窒素複素環は、任意の置換基を有していても
よく、例えばメルカプト基、ハロゲン原子ＣＦ−Ｃ１−
Ｂｒなど）、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７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−へキシルオキシ基、フェノキシ基、ｎ−オクチル基
なト）、ヒドロキシル基、スルホニル基（メタンスルホ
ニル基、Ｐ−）ルエンスルホニル基ナト）、スルホンア
ミド基（ｎ−オクタンスルホンアミド基、ｐ−）ルエン
スルホンアミド基なＥ）、ス／Ｌ／ファモイル基（ジエ
チルスルファモイル基、アシルアミド基（アセチルアミ
ド基など）、４−クロロフェニルスルファモイル基など
）、　カルバモイル基（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）、アミノ基、ア
ミド基（ｎ−ヘネサンアミド基、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７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ナト）
、シアノ基、ニトロ基、アルケニル基（アリル基など）
、アルキルまたアリールチオ基（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など）などであ
る。These nitrogen-containing heterocycles may have any substituent, for example, a mercapto group, a halogen atom CF-C1-
Br, etc.), substituted or unsubstituted alkyl groups (methyl group, trifluoromethyl group, ethyl group, n-octyl group,
benzyl group, etc.), substituted or unsubstituted 7-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), hydroxyl group, sulfonyl group (methanesulfonyl group, p-), sulfonamide group (n-octanesulfonamide group, p-) luenesulfonamide group (E), S/L/famoyl group (diethylsulfamoyl group, acylamide group (acetylamide group, etc.), 4-chlorophenylsulfamoyl group, etc.), carbamoyl group (n-butylcarbamoyl group, 4-chlorophenylsulfamoyl group, etc.),
-cyanophenylcarbamoyl group, etc.), amino group, amide group (n-henesanamide group, n-decaneamide 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, etc.), aryl or alkylaminocarbonyloxy group (phenylaminocarbonyloxy group, 1so-butylaminocarbonyloxy group)
, cyano group, nitro group, alkenyl group (allyl group, etc.)
, alkyl or arylthio group (n-octylthio group,
2-methoxycarbonylphenylthio group, etc.).

式−ＮＨＣＯＣＯＯＲで示される置換基は、前記の含窒
素複素環に直接置換していてもよく、また前記した如き
置換基に置換していてもよい。更に−ＮＨＣＯＣＯＯＲ
基は２個以上有していてもよい。The substituent represented by the formula -NHCOCOOR may be directly substituted on the above-mentioned nitrogen-containing heterocycle, or may be substituted with the above-mentioned substituent. Furthermore-NHCOCOOR
The group may have two or more.

本発明のカブリ防止剤は、分子中に少なくとも１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 in that it has at least one in its molecule. 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９２０以下のアルキル基、アルケニル基であって、
ハロゲン原子、シアノ基、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、Ｕ換アミノ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 920 carbon atoms or less,
It may have a substituent such as a halogen atom, a cyano group, a carboxy group, an alkoxy group (including a polyether group), an aryloxy group, a sulfo group, an aryl group, or a U-substituted amino group.

几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、ノーロゲ／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 几 is a phenyl group, a naphthyl group, an alkyl group, an aryl group, an atom, an alkoxy group, an aryloxy group, an alkenyl group, a substituted amine group, an acylamino group, a sulfonamide group, an alkylidene amino group. It may have a substituent such as a group or 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、プテ
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７基、シアン基、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。The heterocyclic group represented by R is a pyridyl group, a pyrazinyl group,
Pyrimidinyl group, pyridazinyl group, quinolyl group, isoquinolyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, pteridinyl group, etc., including alkyl group, aryl group, halogen atom, substituted amino group, cyan group , acylamino group,
It may have a substituent such as a carboxyl group, an alkoxycarbonyl group, or an aryloxycarbonyl group.

Ｒで示される置換アミノ基は、アルキル基、アリール基
、ヘテロ環基などで置換されたアミノ基、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 substituted amino group represented by R includes an amino group substituted with an alkyl group, an aryl group, a heterocyclic group, or the like, or one forming a heterocycle with the nitrogen atom of the amino group.

本発明のカプリ防止剤の代表的な具体例を以下に示す。Typical specific examples of the anti-capri agent of the present invention are shown below.

以下に本発明による代表的な化合物の合成例を示す。Synthesis examples of representative compounds according to the present invention are shown below.

合成例１　（例示化合物４の合成） １−（ｍ−アミノフェニル）−５−メルカプトテトラゾ
ール９．６５Ｆとフェノキサリルクロリド９．３を中に
ベンゼン３００−を加えて室温にて攪拌下にトリエチル
アミン６．９８−を徐々に滴下した。滴下終了後、同温
にて２時間攪拌したのち、加熱還流を更に２時間行った
。Synthesis Example 1 (Synthesis of Exemplified Compound 4) 1-(m-aminophenyl)-5-mercaptotetrazole 9.65F and phenoxalyl chloride 9.3% were added with 300% of benzene, and triethylamine 6% was added with stirring at room temperature. .98- was gradually added dropwise. After the dropwise addition was completed, the mixture was stirred at the same temperature for 2 hours, and then heated under reflux for another 2 hours.

反応後、溶媒を減圧下に留去し、得た残渣に水を加えて
しばらく放置すると、結晶が析出した。After the reaction, the solvent was distilled off under reduced pressure, water was added to the obtained residue, and when it was left to stand for a while, crystals were precipitated.

この粗結晶を戸取したのち酢酸エテル−リグロインにて
再結晶して、目的物を得た。The crude crystals were collected and recrystallized from ethyl acetate-ligroin to obtain the desired product.

収量：　３．３４　ｔ　　　融点：１７５．０〜１７５
．５℃〈元素分析＞ｃ　　　　　ＨＮ 理論値　　５２．７８　　３．２５　　２０．５２測定
値　　５２．９８　　３．２２　　２０．４８合成例２
　（例示化合物１の合成） 合成例１で合成した例示化合物４の１．０３　ｆに１規
定ＫＯＨ水溶液９−を加えて室温にて２．５時間攪拌し
た。Yield: 3.34 t Melting point: 175.0-175
．． 5℃〈Elemental analysis〉c HN Theoretical value 52.78 3.25 20.52 Measured value 52.98 3.22 20.48 Synthesis example 2
(Synthesis of Exemplified Compound 1) A 1N KOH aqueous solution 9- was added to 1.03 f of Exemplified Compound 4 synthesized in Synthesis Example 1, and the mixture was stirred at room temperature for 2.5 hours.

反応混合物に１規定ＨＣｔ水溶液９づを加えて、析出し
た結晶を戸数し、水洗後、メタノールにて洗浄後、乾燥
し、例示化合物１を得た。Nine portions of a 1N HCt aqueous solution were added to the reaction mixture, and the precipitated crystals were collected, washed with water, methanol, and dried to obtain Exemplified Compound 1.

収量：　０．４６　Ｆ　　　融点：１８９℃分解く元素
分析）ＣＨ，Ｎ 理論値　　　４０．７５　　２．６６　　２６．４１測
定値　　　４０．８５　　２．６０　　２６．３３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、穐々の現像液で
現像を行う。Yield: 0.46 F Melting point: 189°C Elemental analysis) CH,N Theoretical value 40.75 2.66 26.41 Measured value 40.85 2.60 26.33 In the processing method of the present invention, exposed A silver halide photographic light-sensitive material is developed in the presence of the antifoggant of the present invention using a developing solution produced by Akio.

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は、水又は水と混和性の溶媒例え
ばり、Ｍ、Ｐｏ、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、
上記ハ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 can be dissolved in water or a water-miscible solvent such as M, Po, methanol, ethanol, or an aqueous alkali solution, and added to the silver halide emulsion or colloidal dispersion before coating. , by mixing
It can be added to the silver halide emulsion or 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
より分散して上記ハ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, it is also possible to disperse the antifoggant of the present invention in latex and add it to the above silver halide emulsion or the above colloidal dispersion using a method as shown in JP-A-53-137131. It is.

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、Ｄ、Ｍ、Ｐ、　、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 D, M, P, 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１０−５〜１
０−２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　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 1 mol, per 1 mol of silver halide.
0-2 mol range, 10-5 when added to processing solution
It can be set in the range of 10-1 mol/l, preferably 10-4 to 10 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−フェニル−３−ピラゾリドン
）、アミンフェノール類、（例えば、Ｎ−メチル−Ｐ−
アミンフェノール）、ヒドロキシルアミン類（例えば、
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トレン
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-phenyl-3-pyrazolidone), aminephenols (e.g., N-methyl-P-
amine phenol), hydroxylamines (e.g.
N,N-diethylhydroxylamine), ascorbic acid, and heterocyclic compounds such as the fused 1,2,3,4-tetrahydroquinoline ring and intrene ring described in U.S. Pat. No. 4,067,872 These 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−Ｎ−β−ヒドロキ
シエチルアニリン、３−メチル−４−アミノ−Ｎ−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−Ｎ−エチル−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−ｘ　ｆ
　／Ｌ／　−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プリ防
止剤以外のカプリ防止剤等を含み、更に必要に応じてハ
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 a developing agent, phenylene diamines (for example, 4-amino-N, N-diethylaniline, 3-methyl-4-amino-N, N-diethylaniline, 4-amino-N-ethyl-N-β-hydroxy Ethylaniline, 3-methyl-4-amino-N-ethyl-N-β-hydroxyethylaniline 5-methyl-
4-amino-N-ethyl-N-β-methanesulfamide ethylaniline, 4-amino-3-methyl-N-x f
/L/ -N-β-methoxyethylaniline, etc.), amine phenols, etc. can be used alone or in combination. The developer generally contains other known preservatives,
Contains an alkaline agent, a PH buffer, an anti-capri agent other than the anti-capri agent used in the present invention, and further contains a silver halide solubilizer, a color toning agent, a development accelerator, a surfactant,
It may also contain antifoaming agents, water softeners, hardening agents, viscosity imparting agents, 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。定着剤としては千オ（νｔｙ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, organic sulfur compounds known to be effective as a fixing agent can be used, in addition to νty salt and thiocyanate.

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.

本発明を適用しつ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、乳剤はオルソクロム型
又はバンクロム型でもよい。Examples of the vine silver halide emulsions to which the present invention is applied include 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 emulsions may be of the orthochrome 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。Silver halide is a common hydrophilic colloid, such as gelatin, casein, polyvinyl alcohol.

カルボキシメチルセルロース等に分散できるが、ゼラチ
ンが有利である。It can be dispersed in carboxymethylcellulose, etc., but gelatin is advantageous.

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。Silver halide emulsions can also be chemically sensitized by ripening in the presence of small amounts of sulfur-containing compounds (eg, aryl thiocyanates, allylthioureas, sodium thiosulfates, etc.).

該乳剤は、又、還元剤（例えば、フランス特許第１，１
４６，９５５号明細書、米国特許第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−
アミノメタンスルフィン酸化合物等）および少量の貴金
属（例えば、金、白金パラジウム、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。The emulsion may also contain reducing agents (e.g. French Patent No. 1,1
No. 46,955, U.S. Pat. No. 2,487°850
tin compounds as described in GB 789,823;
(such as aminomethane sulfinic acid compounds) and small amounts of noble metals (such as gold, platinum palladium, iridium, ruthenium, and rhodium).

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ハロゲ
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.

更に本発明のカプリ防止剤は、他のカプリ防止剤又はカ
プ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。Additionally, the anticapri agents of the present invention can be used in combination with other anticapri agents or anticapri 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) Examples 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プ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 commonly used surfactant and a hardening agent were added to a chloropromide emulsion for photographic paper consisting of silver halide containing 1 mole of silver iodide, 47 mole of silver bromide, and 52 mole of silver chloride to form an emulsion of 6 moles.
Divided into sections.

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４Ｘ１０−３モルの割合で添加した。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．
５麓となるように塗布し試料とした。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 4.times.10@-3 mole per mole of silver halide. All emulsions were placed on a polyethylene coated paper support with a silver content of 1.
A sample was prepared by applying the coating so as to form a base of 5.

それぞれの試料にウェッジ露光を与え、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
。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ＩＪ　６度を測定し下記の結果が得られた
。Each sample was exposed to wedge light, developed with a D-72 developer at 20° C. for 90 seconds, and subjected to sensitometry. Samples that were not exposed to light were treated with D-72 developer at 30°C.
After developing the film, the turnip IJ was measured at 6 degrees, and the following results were obtained.

比較化合物としては次の２種の化合物を用いた。The following two types of compounds were used as comparative compounds.

実施例２ 実施例１の試料１（カプリ防止剤を含まない印画紙〕を
用い、Ｄ−７２現像液にカプリ防止剤を２ＸＩＯ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。Example 2 Sample 1 of Example 1 (photographic paper containing no anti-capri agent) was used, and the anti-capri agent was added to the D-72 developer at 2XIO mol/mol.
The same development process as in Example 1 was carried out using a developer containing the following, and the following results were obtained.

ｌ＼□Ｌ＼ 実施例３ 平均粒径０．３４μｍの立方体塩化銀乳剤を化学増感し
た後、下記の増感色素をノ・ロゲン化銀１モル当り５Ｘ
１０−’モル加え、界面活性剤および２゜４−ジクロロ
−６−ヒドロキシ−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銀ｉ　５　？
／ｎｌとなるように塗布し試料とした。l＼□L＼ Example 3 After chemically sensitizing a cubic silver chloride emulsion with an average grain size of 0.34 μm, the following sensitizing dye was added at 5X per mole of silver chloride.
Added 10-' moles of surfactant and 2°4-dichloro-6-hydroxy-1,3,5-)riazine (Na salt).
Silver i 5 ? on a polyester film support by adding ?
/nl and used as a sample.

増感色素 （Ｆ）発明の効果 本発明のカプリ防止剤は、減感が少なく、有効にカプリ
を防止することが出来る。Sensitizing dye (F) Effect of the invention The anti-capri agent of the present invention has little desensitization and can effectively prevent capri.

１０−５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。Give a wedge exposure of 10-5 seconds and develop at 30°C with PQ developer.
The film was developed for 60 seconds and sensitometry was performed.

カブリ防止剤は、ハロゲン化銀１モル当り２Ｘ１０−５
モノνの割合で添加し、下記の結果を得た。The antifoggant is 2X10-5 per mole of silver halide.
The following results were obtained by adding mono ν at a ratio of ν.

Claims (1)

【特許請求の範囲】[Claims] １、縮合芳香環を有しない含窒素複素環化合物の存在下
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、該化合物が式、−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 of developing a silver halide photographic light-sensitive material in the presence of a nitrogen-containing heterocyclic compound that does not have a fused aromatic ring, the compound has the formula -NHCOCOOR (R is a hydrogen atom or a monovalent organic A treatment method characterized by having a substituent represented by a group).
JP25763888A 1988-03-18 1988-10-12 Method for processing silver halide photographic sensitive material Pending JPH02103036A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP25763888A JPH02103036A (en) 1988-10-12 1988-10-12 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
JP25763888A JPH02103036A (en) 1988-10-12 1988-10-12 Method for processing silver halide photographic sensitive material

Publications (1)

Publication Number Publication Date
JPH02103036A true JPH02103036A (en) 1990-04-16

Family

ID=17309020

Family Applications (1)

Application Number Title Priority Date Filing Date
JP25763888A Pending JPH02103036A (en) 1988-03-18 1988-10-12 Method for processing silver halide photographic sensitive material

Country Status (1)

Country Link
JP (1) JPH02103036A (en)

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