US2956876A - Mercapto heterocyclic addenda for reversal color development - Google Patents

Mercapto heterocyclic addenda for reversal color development Download PDF

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US2956876A
US2956876A US682636A US68263657A US2956876A US 2956876 A US2956876 A US 2956876A US 682636 A US682636 A US 682636A US 68263657 A US68263657 A US 68263657A US 2956876 A US2956876 A US 2956876A
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color
photographic
developer
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silver halide
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Spath Catherine Marilyn
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to GB26783/58A priority patent/GB898005A/en
Priority to FR1210905D priority patent/FR1210905A/fr
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen 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
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
    • C07D473/36—Sulfur atom
    • C07D473/38—Sulfur atom attached in position 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/407—Development processes or agents therefor
    • G03C7/413—Developers

Definitions

  • This invention relates to color photography, and more particularly, to a method of processing multi-layer color films or papers in such a manner as to reduce color fog and give maximum color density.
  • multi-layer photographic elements used for color photography there are usually three selectively sensitive emulsion layers coated on one side of a single support.
  • the uppermost layer is generally blue-sensitive
  • the next layer is generally greensensitive
  • the emulsion layer adjacent the support is generally redsensitive.
  • a filter layer for absorbing blue radiation which may be transmitted through the blue-sensitive layer.
  • the multi-layer coating can also have other interlayers for specialized purposes.
  • Such multi-layer materials have been previously described in the prior art, such as Mannes et al. US. Patent 2,252,718, issued August 19, 1941. Other arrangements of the sensitive layers are also known.
  • Color materials of the type employed in the instant invention are those intended primarily for reversal processes, wherein the exposed material is given a conventional black-and-white development, followed by a reversal exposure, or exposures, and color development.
  • the color materials used in my invention comprise emulsions which can contain color-forming materials or couplers, or these color couplers can be used instead in the color developers.
  • fog centers are introduced into the unexposed regions, and upon reversal exposure and subsequent color development, these unexposed areas have deposited therein coupled color-forming materials, resulting in severe loss of color quality.
  • color developer containing a cyan coupler results not only in development of the red-sensitive layer, but also in development of cyan fog in the blueand green-sensitive layers.
  • This fog is particularly severe in emulsions which contain conventional chemical sensitizers, such as gold sensitizers, sulfur sensitizers, etc., or polyethyleneglycol type sensitizers.
  • a colored image can be formed by adding to certain color developing solutions, or by incorporating in the silver halide emulsion, a compound which couples during development with the oxidation product of the developing agent, thus forming a colored compound which is deposited adjacent to the silver grains of the silver image during such development.
  • a compound which is employed in conjunction with the developing agent for the silver and which couples with the oxidation product of the developing agent during development is referred to as a color-forming compound or coupler.
  • Such compounds usually belong to one of three widely known types, i.e., pyrazolone couplers, phenol couplers, or open-chain ketomethylene couplers. These couplers produce, respectively, magenta, cyan and yellow images.
  • heterocyclic compounds useful in practicing my invention include tetrazaindenyl and pentazaindcnyl compounds containing a free mercapto (SH) group or an alkali metal salt thereof (e.g., sodium, potassium, etc.).
  • SH free mercapto
  • alkali metal salt thereof e.g., sodium, potassium, etc.
  • R represents a tetrazaindenyl or pentazaindenyl group
  • n represents a positive integer of from 1 to 2
  • M represents a hydrogen atom or an alkali metal atom (e.g., sodium, potassium, etc.).
  • Typical heterocyclic compounds include, for example, the following:
  • heterocyclic compounds employed in the color developers of my invention can be utilized in various concentrations depending upon the particular emulsions employed, the concentration of silver halides in the emulsions, and the concentration of the developing agents in the developers. In general, not less than about 5 mg. per liter of developer of heterocyclic compound should be employed. The most advantageous concentration can be determined by developing a series of test strips of silver halide emulsions wherein the concentration of heterocyclic compound is varied, as well as the concentration of the developing agent.
  • the usual addenda can be employed in the developers, such as strongly alkaline agents, sodium carbonate, potassium carbonate, sodium hydroxide, etc, restraining agents, such as potassium bromide, stain preventives, such as alkali metal sulfites, etc.
  • My invention is primarily directed to the development of the ordinarily employed gelatino-silver-halide developing-out emulsions, e.g., gelatino-silver-chloride, -chlorobromide, -chloroiodide, -chlorobromiodide, -bromide and -bron1iodide developing-out emulsions. While the results in the following examples were obtained using gelatinosilver-bromiodide emulsions, excellent results can also be obtained using other silver halide emulsions. These emulsions can be coated in the usual manner on any suitable support, e.g., glass, cellulose nitrate film, cellulose acetate film, polyvinyl acetal resin film, paper or metal.
  • any suitable support e.g., glass, cellulose nitrate film, cellulose acetate film, polyvinyl acetal resin film, paper or metal.
  • Photographic silver halide emulsions useful in my invention can also contain such addenda as chemical sensitizers, e.g., sulfur sensitizers (e.g., allyl thiocarbamide, thiourea, allyl isothiocyanate, cystine, etc.), various gold compounds (e.g., potassium chloroaurate, auric trichloride, etc.) (see U.S. Patents 2,540,085; 2,597,856 and 2,597,915), various azaindene compounds (such as those disclosed in U.S. Patent 2,716,062), condensation products of alkylene oxides, such as those shown in U.S. Patent 2,400,532, as well as the additives mentioned in Jones et al. U.S. application Serial No. 575,160, filed March 30, 1956 (now U.S. Patent 2,937,089, issued May 17, 1960).
  • chemical sensitizers e.g., sulfur sensitizers (e.g.,
  • Couplers or color-forming compounds which are soluble in the strongly alkaline developing solutions are well known to those skilled in the art.
  • Typical couplers include the following:
  • amylbenzenesulfonylamino)'5- pyrazolone (3 7) 1-phenyl-3 [p- (p'-sec. amylbenzoyl aminobenzoylaminoJ-S-pyrazolone (38) 1-m-tolyl-3-[m (B-phenylpropionyl)aminobenzoylamino] -5-pyrazolone (39) 1- m tolyl 3 (2,4 di tert.
  • Coupler (65) l -hydroxy-2-[A-(2',4-di-tert.amylphenoxy)-nbutyll-naphthamide (U.S. Patent 2,474,293)
  • amylphenoxyacetanilide (77) 4-benzoylacetamido 3 methoXy-2',4'-di-tert.-
  • the color-forming developers useful in my invention have been previously described in the prior art, and my invention is not to be restricted to the use of any particular color-forming developer.
  • the color-forming developers previously mentioned which I have found to be especially useful in my invention comprise aromatic primary amines containing an amino (substituted or not) or hydroxyl substituent. Phenylenediamines and substituted derivatives thereof containing a primary amino group have been found to provide excellent results when employed in combination with the heterocyclic compounds of my invention.
  • Typical of such color-forming developers are the sulfonamido substituted p-phenylenediamines disclosed in Weissberger U.S.
  • Patent 2,548,574 issued April 10, 1951, the substituted p-phenylenediamines disclosed in Weissbe-rger et al. US. Patent 2,566,271, issued August 28, 1951.
  • Other phenylenediamine color-forming developers can be employed to like advantage in the process of my invention.
  • the first developer employed in the process of my invention is generally a rapid developer of the MQ type, i.e., a combination of hydroquinone and Elon (p-N-methylaminophenol) developer.
  • the photographic silver halide emulsions useful in the process of my invention can be prepared according to known methods, such as those described in Hewitson and McClintock U.S. Patent 2,618,556, issued November 18, 1952, for example. Of course, emulsions prepared by other methods can be used to equal advantage in my invention. These emulsions can be chemically sensitized or not, as mentioned above. Additional chemical sensitizers useful in my invention comprise those disclosed in the copending application Serial No. 550,495, filed December 1, 1955 (now U.S. Patent 2,886,437, issued May 12, 1958), in the name of D. E. Piper.
  • Example I A portion of a gelatino-silvcr-bromiodide emulsion which had been sensitized with a sulfur compound and a gold compound as mentioned above was coated on a cellulose acetate support. The coating was then cut into several strips, identified coating series A below.
  • the oleyl ether of a polyethyleneglycol having a molecular weight greater than 300 was added to a second portion of the same emulsion at a concentration of 5 gms. of the oleyl ether per mole of silver halide, and the emulsion coated onto a cellulose acetate support.
  • the dried coating was then cut into several strips, identified as coating series B below.
  • One strip of each coating was exposed for & second to a 500-watt, 3000 K. light source on an Eastman Type Ib sensitometer. The exposed coatings were then developed for 3 minutes in a developer having the following composition:
  • the coatings were then washed for two minutes.
  • the coatings were washed for ten minutes and treated for two minutes in a silver bleach bath having the following composition:
  • the coatings were then treated for two minutes in a fixing bath having the composition given below, washed and dried.
  • Coating Series A Coating Series B Compound No. Cone, g.[liter D-max. Cyan Fog D-max. Cyan Fog none 3. 40 0. l8 3. 30 0. 31 0. 25 3. 20 .02 3. 50 10 .30 2. 70 .08 3. 14 006 2. 90 l3 3. 50 l2 15 3. 40 .06 3. 30 .09 .06 3. 50 12 3. S 0 .23 15 2. 90 1D 3. 2D .14
  • the heterocyclic compounds useful in practicing my invention can also be used during magenta and yellow development, as indicated above.
  • Compound 1 can be employed in color developers containing color-forming compounds for the magenta image, such as Coupler No. 45. Complete directions for such a technique are illustrated in Example 2 of my copending application Serial No. 635,944, filed January 24, 1957 (now US. Patent 2,899,306, issued August 11, 1959).
  • the heterocyclic compounds of my invention, such as Compound 1 can be employed in color developers containing a color-forming compound for the yellow image, such as Coupler No. 64 above. Complete directions for such a technique can be found in Example 3 of my copending application Serial No. 635,- 944 mentioned above.
  • alkylene oxide polymers include polyalkylene glycols and condensation prodnets of alkylene oxides with organic compounds containing an active hydrogen atom, such as alcohols, amines, mercaptans, acids, amides, etc.
  • such aikylene oxide polymers have a molecular weight of at least 300, as shown in US. application Serial No. 550,495, mentioned above. It is to be further understood that the emulsions employed in my invention need not be sensitized, although particularly useful results have been obtained with emulsions which have been sensitized with such alkylene oxide polymers.
  • the solid was collected, washed thoroughly with water, and dried overnight to give eight grams of product (M.P. 300 C.).
  • the 2-mercapto-4,5,6-triarnino pyrimidine sulfate was prepared according to the method described in JACS 70, 3111 (1948).
  • Compounds 1 and 2 were prepared according to the method described in JACS,” vol. 78 (1956), page 159.
  • Compound 5 was prepared according to the method described in JACS, vol. 74 (1952), page 411.
  • Compound 10 was prepared according to the method described in JACS," vol. 77 (1955), page 5105.
  • Compounds 12 and 13 were prepared according to the method described in my copending application Serial No. 602,067, filed August 3, 1956 (now US. Patent 2,860,936, issued November 18, 1958).
  • a photographic developer for color photography comprising an aqueous alkaline solution of an aromatic primary amine developing agent containing, in addition to the primary amine group, a substituent selected from the group consisting of hydroxyl and an amino group, an alkali metal sulfite and at least 5 mg. per liter of solution of an organic heterocyclic compound selected from those represented by the following general formula:
  • R represents a member selected from the group consisting of a tetrazaindenyl group and a pentazaindenyl group
  • n represents a positive integer of from 1 to 2
  • M represents a member selected from the group consisting of a hydrogen atom and an alkali metal atom.
  • a photographic developer for color photography comprising an aqueous alkaline solution of an arylenediamine photographic developing agent, an alkali metal sulfite and at least 5 mg. per liter of solution of a compound selected from those represented by the following general formula:
  • R represents a member selected from the group consisting of a tetrazaindenyl group and a pentazaindenyl group
  • n represents a positive integer of from 1 to 2
  • M represents a member selected from the group consisting of a hydrogen atom and an alkali metal atom.
  • a photographic developer for color photography comprising an aqueous alkaline solution of a p-phenylencdiamine photographic developing agent, an alkali metal sulfitc and at least 5 mg. per liter of solution of a compound selected from those represented by the following general formula:
  • R represents a member selected from the group consisting of a tetrazaindenyl group and a pentazaindenyl group
  • n represents a positive integer of from 1 to 2
  • M represents a member selected from the group consisting of a hydrogen atom and an alkali metal atom.
  • a developing composition for color photography comprising an aqueous alkaline solution of a p-phenylenediamine color developer, an alkali metal sulfite and at least mg. per liter of solution of a compound selected from those represented by the following general formula:
  • R represents a tetrazaindenyl group and M represents a member selected from the group consisting of a hydrogen atom and an alkali metal atom.
  • An aqueous developing solution for color photography comprising a p-phenylenediamine color developer, an alkali metal sulfite, a color-forming compound capable of coupling with the oxidation products of said p-phenylenediamine color developer and at least 5 mg. per liter of solution of a compound selected from those represented by the following general formula:
  • R represents a tetrazaindenyl group and M represents a member selected from the group consisting of a hydrogen atom and an alkali metal atom.
  • a photographic developer for color photography comprising an aqueous alkaline solution of a p-phenylenediamine photographic developing agent, an alkali metal sulfite and at least 5 mg. per liter of 4,7-dihydroxy-2- mercaptol -phenyll ,3 ,5 ,tS-tetrazaindene.
  • a photographic developer for color photography comprising an aqueous alkaline solution of a p-phenylenediamine photographic developing agent, an alkali metal sulfitc and at least 5 mg. per liter of 6-hydr0xy-3-mercapto-4-methyll ,2,3a,7-tetrazaindene.
  • a photographic developer for color photography comprising an aqueous alkaline solution of a p-phenylenediamine photographic developing agent, an alkali metal sulfite and at least 5 mg. per liter of 4-hydroxy-2mercaptomethyl-6-methyll ,3 ,3a,7-tetrazaindene.
  • a photographic developer for color photography comprising an aqueous alkaline solution of a p-phenylenediamine photographic developing agent, an alkali metal sulfite and at least 5 mg. per liter of 7-mercapto-l,3,4,6- tetrazaindene.
  • a photographic developer for color photography comprising an aqueous alkaline solution of a p-phenylenediamine photographic developing agent, an alkali metal sulfite and at least 5 mg. per liter of 7-amino-5-mercaptol,2,3,4,6-pentazaindene.
  • R represents a member selected from the group consisting of a tetrazaindenyl group and a pentazaindenyl group
  • n represents a positive integer of from 1 to 2
  • M represents a member selected from the group consisting of a hydrogen atom and an alkali metal atom.
  • R(CH -SM wherein R represents a member selected from the group consisting of a tetrazaindenyl group and a pentazaindenyl group, n represents a positive integer of from 1 to 2 and M represents a member selected from the group consisting of a hydrogen atom and an alkali metal atom.
  • R represents a member selected from the group consisting of a tetrazaindenyl group and a pentazaindenyl group
  • n represents a positive integer of from 1 to 2
  • M represents a member selected from the group consisting of a hydrogen atom and an alkali metal atom.
  • R represents a tetrazaindenyl group and M represents a member selected from the group consisting of a hydrogen atom and an alkali metal atom.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US682636A 1957-09-09 1957-09-09 Mercapto heterocyclic addenda for reversal color development Expired - Lifetime US2956876A (en)

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Application Number Priority Date Filing Date Title
BE570978D BE570978A (fr) 1957-09-09
US682636A US2956876A (en) 1957-09-09 1957-09-09 Mercapto heterocyclic addenda for reversal color development
GB26783/58A GB898005A (en) 1957-09-09 1958-08-20 Improvements in photographic colour development
FR1210905D FR1210905A (fr) 1957-09-09 1958-09-09 Nouveau révélateur chromogène et nouveau procédé de traitement photographique

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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3137574A (en) * 1959-11-12 1964-06-16 Eastman Kodak Co Stability of rapid-processed photographic prints
US3202512A (en) * 1962-02-23 1965-08-24 Eastman Kodak Co Photographic silver halide emulsions stabilized with tetrazaindene compounds
US3244522A (en) * 1962-09-26 1966-04-05 Gen Aniline & Film Corp Fog reduction in photographic silver halide emulsions
US3326684A (en) * 1962-04-06 1967-06-20 Fuji Photo Film Co Ltd Method for stabilizing developed photosensitive materials
US3462272A (en) * 1964-01-29 1969-08-19 Minnesota Mining & Mfg Tetraazaindenes as antifoggants
DE2112728A1 (de) * 1970-03-20 1971-09-30 Eastman Kodak Co Photographisches Aufzeichnungsmaterial
US3642473A (en) * 1968-01-18 1972-02-15 Polaroid Corp Silver diffusion transfer process with mercapto-purine antifoggant
US3895948A (en) * 1971-12-28 1975-07-22 Fuji Photo Film Co Ltd Silver halide light-sensitive material containing a heterocyclic thione and a polyalkylene oxide
US4021248A (en) * 1974-09-03 1977-05-03 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material
US4717648A (en) * 1985-02-07 1988-01-05 Fuji Photo Film Co., Ltd. Process for processing a color reversal photographic light-sensitive material
US4830955A (en) * 1986-04-24 1989-05-16 Konishiroku Photo Industry Co., Ltd. Silver halide photographic light-sensitive material and method of processing thereof utilizing hydroxy azaindene compounds
US5344750A (en) * 1992-05-12 1994-09-06 Fuji Photo Film Co., Ltd. Color development processing method of silver halide color photographic material using a color developer where the color developing agent concentration and processing temperature are a function of bromide ion concentration
US5508153A (en) * 1992-12-09 1996-04-16 Konica Corporation Composition for developing a black-and-white silver halide photographic light-sensitive material
US5523196A (en) * 1993-10-14 1996-06-04 Konica Corporation Method for replenishing a developer
JP2005517662A (ja) * 2001-12-20 2005-06-16 アプライド リサーチ システムズ エーアールエス ホールディング ナームロゼ フェンノートシャップ オキシトシン・アンタゴニストとしてのトリアゾール類

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4963475A (en) * 1986-04-22 1990-10-16 Konishiroku Photo Industry Co., Ltd. Method for processing silver halide photo-sensitive material
JP2591616B2 (ja) * 1986-04-22 1997-03-19 コニカ株式会社 カブリの防止されたハロゲン化銀写真感光材料の処理方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2675314A (en) * 1951-04-10 1954-04-13 Eastman Kodak Co Antistain agents for photographic color materials
US2713541A (en) * 1953-07-01 1955-07-19 Eastman Kodak Co Stabilized photographic silver halide emulsions
US2743181A (en) * 1954-04-29 1956-04-24 Eastman Kodak Co Stabilized photographic silver halide emulsions

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2675314A (en) * 1951-04-10 1954-04-13 Eastman Kodak Co Antistain agents for photographic color materials
US2713541A (en) * 1953-07-01 1955-07-19 Eastman Kodak Co Stabilized photographic silver halide emulsions
US2743181A (en) * 1954-04-29 1956-04-24 Eastman Kodak Co Stabilized photographic silver halide emulsions

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3137574A (en) * 1959-11-12 1964-06-16 Eastman Kodak Co Stability of rapid-processed photographic prints
US3202512A (en) * 1962-02-23 1965-08-24 Eastman Kodak Co Photographic silver halide emulsions stabilized with tetrazaindene compounds
US3326684A (en) * 1962-04-06 1967-06-20 Fuji Photo Film Co Ltd Method for stabilizing developed photosensitive materials
US3244522A (en) * 1962-09-26 1966-04-05 Gen Aniline & Film Corp Fog reduction in photographic silver halide emulsions
US3462272A (en) * 1964-01-29 1969-08-19 Minnesota Mining & Mfg Tetraazaindenes as antifoggants
US3642473A (en) * 1968-01-18 1972-02-15 Polaroid Corp Silver diffusion transfer process with mercapto-purine antifoggant
DE2112728A1 (de) * 1970-03-20 1971-09-30 Eastman Kodak Co Photographisches Aufzeichnungsmaterial
US3895948A (en) * 1971-12-28 1975-07-22 Fuji Photo Film Co Ltd Silver halide light-sensitive material containing a heterocyclic thione and a polyalkylene oxide
US4021248A (en) * 1974-09-03 1977-05-03 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material
US4717648A (en) * 1985-02-07 1988-01-05 Fuji Photo Film Co., Ltd. Process for processing a color reversal photographic light-sensitive material
US4830955A (en) * 1986-04-24 1989-05-16 Konishiroku Photo Industry Co., Ltd. Silver halide photographic light-sensitive material and method of processing thereof utilizing hydroxy azaindene compounds
US5344750A (en) * 1992-05-12 1994-09-06 Fuji Photo Film Co., Ltd. Color development processing method of silver halide color photographic material using a color developer where the color developing agent concentration and processing temperature are a function of bromide ion concentration
US5508153A (en) * 1992-12-09 1996-04-16 Konica Corporation Composition for developing a black-and-white silver halide photographic light-sensitive material
US5523196A (en) * 1993-10-14 1996-06-04 Konica Corporation Method for replenishing a developer
JP2005517662A (ja) * 2001-12-20 2005-06-16 アプライド リサーチ システムズ エーアールエス ホールディング ナームロゼ フェンノートシャップ オキシトシン・アンタゴニストとしてのトリアゾール類

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BE570978A (fr)
FR1210905A (fr) 1960-03-11
GB898005A (en) 1962-06-06

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