US3640716A - Method of preventing color mixing in multilayer-type reversal color photographic light-sensitive materials - Google Patents

Method of preventing color mixing in multilayer-type reversal color photographic light-sensitive materials Download PDF

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US3640716A
US3640716A US826283A US3640716DA US3640716A US 3640716 A US3640716 A US 3640716A US 826283 A US826283 A US 826283A US 3640716D A US3640716D A US 3640716DA US 3640716 A US3640716 A US 3640716A
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group
coupler
color
sensitive
emulsion layer
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Tadashi Nagae
Yasushi Oishi
Jun Hayashi
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Fujifilm Holdings Corp
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Fuji Photo Film Co Ltd
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    • 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
    • G03C7/32—Colour coupling substances
    • G03C7/36—Couplers containing compounds with active methylene groups
    • G03C7/362—Benzoyl-acetanilide couplers

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  • ABSTRACT Primary Examiner-Norman G. Torchin Assistant Examiner-John L. Goodrow Attorney-Sughrue, Rothwell, Mion, Zinn & Macpeak [57] ABSTRACT
  • the invention is directed to a method for preventing color mixing in multilayer-type color photographic light-sensitive materials developed by the coupler-indeveloper process.
  • the multilayer light-sensitive materials used herein comprise a film base coated with a red-sensitive emulsion layer, a green-sensitive emulsion layer, and a blue-sensitive emulsion layer respectively.
  • Cyan and magenta dye formation is prevented in the blue emulsion layer by addition thereto of a ballasted yellow coupler having the general formula wherein R represents a tertiary alkyl group, an unsubstituted cycloalkyl group, a substituted cycloalkyl group, an unsubstituted dicycloalkyl group, a substituted dicycloalkyl group, an unsubstituted aryl group or a substituted aryl group; R represents an unsubstituted aryl group. a substituted aryl group, an unsubstituted heterocyclic group, or a substituted heterocyclic group; and X represents hydrogen atom or a group capable of being split off during the coupling reaction.
  • the present invention relates to a method of preventing color mixing in a multilayer-type color photographic light-sensitive material.
  • a multilayer-type color photographic light-sensitive material having on a support a red-sensitive emulsion layer, a green-sensitive emulsion layer, and a blue-sensitive emulsion layer
  • the photographic emulsion layers contain couplers capable of forming dyes by the reaction with the oxidation product of a silver halide and an aromatic amino developing agent
  • the photographic emulsion layers do not contain such couplers therein.
  • the latter-type color photographic lightsensitive material is, after exposure, processed in color-forming developers containing the coupler, the latter type of light-sensitive material is superior in image sharpness to the former type in which the photographic emulsion layers contain the couplers.
  • the emulsion layer there is formed in the emulsion layer, besides a desired dye, other undesirable dyes, which cause color mixing and degrades the color reproduction of the color photographic light-sensitive material thus developed.
  • a reversal color photographic light-sensitive material of the latter type having on a support a red-sensitive emulsion layer, a greensensitive emulsion layer, and a blue-sensitive emulsion layer in this order is subjected to a black and white development, a cyan color-forming development, a yellow color-forming development and a magenta color-forming development (hereinafter, these procedures are called coupler-indeveloper-type reversal color process")
  • coupler-indeveloper-type reversal color process there is formed in the blue-sensitive emulsion layer, besides a yellow dye, a cyan dye or magenta dye, whereby the yellow image has a slight tinge of green or orange and hence a yellow color having a high color purity cannot be obtained.
  • a development fog i.e., when an emulsion layer is subjected to a color-forming development, a silver halide grain in the unexposed portions of another emulsion layer is developed to produce an undesirable dye.
  • Still another cause for the color mixing is that exposed silver halide grains having a latent image are not activated in a color-forming developer containing a coupler capable of giving a dye image, that is, left undeveloped and finally developed in a subsequent color-forming developer containing a coupler capable of giving another dye.
  • the blue-sensitive layer to be developed in a yellow color-forming developer is brought into contact with a cyan color-forming developer before it is developed in the yellow color-formin g developer, which tends to cause the formation of cyan fog and then the formation of cyan color mixing.
  • the blue-sensitive emulsion layer is, after the development in the yellow color-forming developer, brought into contact with a magenta color-forming developer, the silver halide grains in the blue-sensitive emulsion layer which have not completely been developed in the yellow color-forming developer are subjected to the magenta color-forming development in the magenta color-forming developer, which tends to cause magenta color mixing.
  • a development accelerator may be added to the yellow color-forming developer for preventing the formation of magenta color mixing but when the yellow color-forming developer is activated by the addition of development accelerator, the grains to be coupled into magenta in the greensensitive emulsion layer tends to be fog-developed. which tends to cause yellow color mixing in the green-sensitive emulsion layer.
  • an object of the present invention is to provide a process for preventing the formation of cyan color mixing or magenta color mixing in the yellow color-forming emulsion layer after development by the coupler-in-developer-type reversal color process and providing a yellow dye image having a high color purity.
  • Another object of the present invention is to provide a multilayer color photographic light-sensitive material capable of forming a yellow dye image having a high color density after development by the coupler-in-developer-type reversal color process.
  • the oxidation product of the developing agent is surprisingly caused to react predominantly with the ballasted yellow coupler present in the blue-sensitive emulsion layer rather than with the cyan coupler supplied from the developer and hence the cyan color mixing is remarkably reduced.
  • the ballasted yellow coupler in the bluesensitive emulsion layer the development in the yellow colorforming developer is markedly accelerated and no undeveloped silver halide grains are left, which results in reducing the formation of magenta color mixing in yellow.
  • the inventors have at the same time found that by incorporating the ballasted yellow coupler in the blue-sensitive emulsion layer, the density of the yellow dye image formed after development is increased. Therefore, by these effects, a desirable yellowimage having a high color density and less color mixing can be obtained.
  • the ballasted yellow coupler used in the present invention can be selected from yellow couplers having the general formula where R, is a tertiary alkyl group, an unsubstituted or substituted cycloalkyl group, an unsubstituted or substituted dicycloalkyl group, or an unsubstituted or substituted aryl group; R is an unsubstituted or substituted aryl or heterocyclic group; and X is a hydrogen atom or a group capable of being split off at coupling.
  • Examples of a suitable R group in general formula l are a tertiary alkyl group having from four to 32 carbon atoms such as an a-pivalyl group, a l,l-dimethylpropyl group, a l,l-dibutylheptadecyl group, a l,l-diisobutylheptadecyl group, a l,ldi-tert-butylheptadecyl group and the like; an unsubstituted cycloalkyl group or a cycloalkyl group substituted with an alkyl group, an alkoxy group, an alkoxyalkyl group, or an aryl group, in which the alkyl radical may have from one to l8 carbon atoms, such as, a cyclohexyl group, a l-methylcyclohexyl group, a l-butylcyclohexyl group, a l
  • a 3-ethylcyclohexyl group a l-ethoxycyclohexyl group, a l-nonoxycyclohexyl group, a 2- butoxycyclohexyl group, a l-methoxyethylcyclohexyl group, a 3-methoxymethylcyclohexyl group, a l-phenylcyclohexyl group, a l-toluylcyclohexyl group, and the like; an unsaturated dicycloalkyl group or a dicycloalkyl group substituted with an alkyl group having one to 18 carbon atoms, an alkoxyl group, an alkoxyalkyl group, or an aryl group, such as, a 7,7- dimethylnorbornyl group, a 2-methyl-7,7-dimethylnorbornyl group, a 2-octadecyl-7,7-dimethylnorbornyl group,
  • Examples of a suitable R group in formula (1) are an unsubstituted aryl group or an aryl group substituted with a halogen atom, an alkyl group, an alkoxyl group, an aryloxyl group, an acyl group, an alkoxy-carbonyl group, in which the alkyl radical may have from one to 18 carbon atoms, an amino group, a carbonamido group, a sulfonamido group, a ureido group, a carbamyl group, a sulfamyl group, a carboxyl group or a sulfone group, such as, a phenyl group, a 2-chlorophenyl group, a 2,4-dichlorophenyl group, a 2,4,6-trichlor ophenyl group, a 2-bromophenyl group, a Z-fluorophenyl group, a 4- methylphenyl group, a 4-trifluoro
  • phenyl group a 4-phenylureidophenyl group, a 2- (2,4-di-tert-amylphenoxy)-5-(3,5-dimethoxycarbonylphenylcarbamyl)-phenyl group, a 3,5-dicarbamylphenyl group, a 4- [N-(phenylethyl)-N-(p-toluyl)sulfamyl] phenyl group, a 4- carboxyphenyl group, a 3,5-dicarboxyphenyl group, a 2- methoxy-S-carboxyphenyl group, a 2-chloro-5-carboxyphenyl group, a 2-(N-methyl-N-octylamino)-5-carboxyphenyl group, a 2-sulfophenyl group, a Z-methoxy-S-sulfophenyl group, a 2- chloro-S-sulfopheny
  • a suitable X-group are a hydrogen atom or a group capable of being split off at coupling, such as, a halogen atom, e.g., a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, on SCN group, -OR group, --SR group, 0COR group, and -OSO R group (wherein R represents an alkyl group, an aryl group, or a heterocyclic group), a halogen atom, e.g., a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, on SCN group, -OR group, --SR group, 0COR group, and -OSO R group (wherein R represents an alkyl group, an aryl group, or a heterocyclic group), a
  • Coupler 10 s omumm Q-c 0 011,0 ONH- COClsHai O 0 0 CuHu om-Goocrnoomr Coupler (13):
  • ballasted yellow couplers shown above may be prepared by well-known methods as disclosed in, for example, British Pat. Nos. 595,314; 800,108; 1,045,633 and l.052,488; U.S. Pat. No. 3,265,506; Belgian-Pat. 692,947; and Japanese Pat. application No. 3985/66.
  • the ballasted coupler used in this invention may be added to a photographic emulsion by such conventionally known methods.
  • the yellow coupler may be added directly to the photographic emulsion as an alkali solution thereof, or it may be dissolved in an organic solvent such as dibutyl phthalate or tricresyl phosphate and after dispersing the solution in an aqueous medium such as an aqueous gelatin solution, the resulting dispersion is added to a photographic emulsion (cf., e.g., C. F. K. Mees and T. H. James, The Theory of the Photographic Process, 3rd Ed., Macmillan Co., p. 393 1966)), or it may be first fused by heating and the fused coupler directly added to a photographic emulsion or an aqueous medium.
  • a photographic emulsion cf., e.g., C. F. K. Mees and T. H. James, The Theory of the Photographic Process,
  • the ballasted yellow coupler may be incorporated in a photographic emulsion in any step before coating but is desirably added at a step between the end of post ripening and coating.
  • the amount of the yellow coupler depends on the properties of a photographic silver halide emulsion to be used but in general is suitably 00005-05 mole per mole of the silver halide emulsion in the blue-sensitive emulsion layer.
  • 00005-05 mole per mole of the silver halide emulsion in the blue-sensitive emulsion layer is suitably 00005-05 mole per mole of the silver halide emulsion in the blue-sensitive emulsion layer.
  • the amount of the coupler is not limited to the above range.
  • ballasted yellow couplers mentioned above may be used alone or in combinations of two or more.
  • a silver iodobromide emulsion is desirable but other silver halide emulsions such as a silver chloride emulsion, a silver chlorobromide emulsion, and a silver bromide emulsion can be employed.
  • the silver halide emulsion used in this invention may have been sensitized by well-known methods, e.g., with a compound containing an unstable sulfur such as ammonium thiosulfate or allylthiocarbamide, a gold compound such as a complex salt of monovalent gold and thiocyanic acid, a reducing agent such as stannous chloride, a polyalkylene oxide derivative, or a combination thereof.
  • a compound containing an unstable sulfur such as ammonium thiosulfate or allylthiocarbamide
  • a gold compound such as a complex salt of monovalent gold and thiocyanic acid
  • a reducing agent such as stannous chloride, a polyalkylene oxide derivative, or a combination thereof.
  • the silver halide emulsion may contain a stabilizer such as benzimidazole, lphenyI-S-mercaptotetrazole, and the like; a hardening agent such as formaldehyde, much-bromic acid, and the like; and a wetting agent such as saponine.
  • a stabilizer such as benzimidazole, lphenyI-S-mercaptotetrazole, and the like
  • a hardening agent such as formaldehyde, much-bromic acid, and the like
  • a wetting agent such as saponine.
  • a yellow filter layer Between the blue-sensitive emulsion layer and the greensensitive emulsion layer there may be inserted a yellow filter layer.
  • the function of the yellow filter layer is to absorb remaining blue light which the blue-sensitive layer does not absorb.
  • the blue-sensitive emulsion layer containing the ballasted yellow coupler is desirably positioned at the uppermost position as silver halide emulsion layer, that is, it is desirable that the red-sensitive emulsion layer, the green-sensitive emulsion layer, the yellow filter layer, and the blue-sensitive emulsion layer containing the yellow coupler be formed on a support in that order.
  • the red-sensitive emulsion layer and the green-sensitive emulsion layer contain desirably no couplers in general but one of them may contain a ballasted cyan coupler and a ballasted magenta coupler respectively.
  • the multilayer color photographic light-sensitive material containing the yellow coupler in this invention is desirably processed by a usual coupler-in-developer-type reversal color process.
  • Each of the cyan, magenta and yellow color-forming developers contains at least a color-forming developing agent and a diffusible coupler coupling into a cyan, magenta or yellow dye respectively.
  • color-forming developing agent As the color-forming developing agent are employed wellknown p-phenylene diamine derivatives such as 4-amino-N,N- diethylaniline, 4-amino-3-methyl-N-methyl-N(fi-methylsulfonamidoethyl )-aniline, 4-amino-3-methyl-N-ethyl-N-( B- hydroxyethyl) aniline, and the like (of, e.g., C. F. K. Mees and T. H. James, The Theory of the Photographic Process," 3rd Ed., page 387).
  • p-phenylene diamine derivatives such as 4-amino-N,N- diethylaniline, 4-amino-3-methyl-N-methyl-N(fi-methylsulfonamidoethyl )-aniline, 4-amino-3-methyl-N-ethyl-N-( B- hydroxyethyl) aniline, and the like (
  • the diffusible cyan couplers there are employed generally known phenolic couplers such as 2-chloro-lnaphthol, 2,4-dichloro-l-naphthol, l-hydroxy-N-butyLZ- naphthamide, l-hydroxy-N-( Z-acetamidophenethyl )-2- naphthamide, etc. (cf. ibid, page 387).
  • the diffusible magenta couplers there are open-chain methylene couplers such as acylaceto-nitriles, 2-cyanoethylbenzofuran, benzylacetonitrile, and the like, cyclic methylene couplers such as l-phenyl-3-methyl-5-pyrazolone, l-phenyl-3-(4- chlorobenzamido)-5-pyrazolone. l-phenyl-3-(3-nitrobenzoylamino)-5-pyrazolone, l-(2,4,6-trichlorophenyl )-3( 4- nitroanilino )-5-pyrazolone, and the like.
  • the diffusible yellow couplers there are acylacetarnide-type openchain methylene couplers such as Z-acetanilide, 2-aceto-2',
  • EXAMPLE I A highly sensitive gelatino silver iodobromide reversal color photographic emulsion subjected to a sulfur sensitization and a gold sensitization was melted by heating and divided into several parts. Each emulsion was mixed with an aqueous a1- kaline solution of the yellow coupler shown in table 1 and then the pH of the emulsion was adjusted to 7.0 with the addition of citric acid.
  • Potassium bromide 2.0 g. 0.1% Aq.so1n. of potassium iodide m1.
  • Potassium thiocyanate 3 g. Sodium sulfite (anhydrous) 10 g. Sodium carbonate (mono-hydrate) 30 g.
  • EXAMPLE 2 The gelatino silver iodobromide reversal color photographic emulsion same as in example 1 was melted by heating and divided into several parts. Five grams of the coupler shown in table 2 was dissolved in a mixed solution of 10 g. of dibutyl phthalate and 10 g. of ethyl acetate, the solution was dispersed in 50 g. of an aqueous 10 percent gelatin solution together with a surface active agent, the dispersion of the coupler thus obtained was added to the aforesaid silver halide emulsion in an amount shown in table 2, and the pH of the resulting emulsion was adjusted to 7.0.
  • the blue-sensitive reversal color photographic emulsion containing the aforesaid coupler was applied to a photographic film having on a cellulose triacetate film a red-sensitive reversal color photographic emulsion layer, a green-sensitive reversal color photographic emulsion layer, a yellow filter layer, and a blue-sensitive emulsion layer such that the amount of Ag was 16.5 g./l00 cm. in the blue-sensitive layer and dried.
  • the sample thus dried was exposed and processed as in example 1 and the density was measured as in the example, the results shown in table 2. The results show that the yellow density was increased and the cyan density and the magenta density were extremely reduced.
  • the dried sample was exposed and developed as in example i except that different kinds of diffusuble couplers were used in the cyan, yellow, and magenta color developers respectively and 3 5 the density of each dye image was measured, the results of which are shown in table 3 together with the diffusable couplers used.
  • the values in table 3 are the differences in yellow density, cyan density and magenta density between the case of adding the diffusible yellow coupler to the emulsion and the case of adding no such yellow coupler to the emulsion. When the value was plus it means that the density was increased by the addition of the ballasted yellow coupler to the emulsion layer, while minus value means that the density was reduced by the addition thereof.
  • a blue-sensitive emulsion layer said developing being carried out with color developers containing a diffusable cyan, yellow and magenta couplers, respectively, said blue emulsion layer containing a ballasted yellow coupler of the formula 0 .l Ri- (3IIC-NH-R:
  • R represents a member selected from the group consisting of a tertiary alkyl group, an unsubstituted cycloalkyl group, a substituted cycloalkyl group, an unsubstituted -dicycloalkyl group, a substituted dicycloalkyl group, an unsubstituted aryl group and a substituted aryl group;
  • R represents a member selected from the group consisting of an unsubstituted aryl group, a substituted aryl group, an unsubstituted heterocyclic group, and a substituted heterocyclic group;
  • X represents a member selected from the group consisting of a hydrogen atom and a group capable of being split off during the coupling reaction.
  • a multilayer-type reversal color photographic material of the type to be developed in color developers containing couplers which comprises a support having thereon,
  • a blue-sensitive emulsion layer said blue-sensitive emulsion layer containing a ballasted yellow coupler of the formula where R represents a member selected from the group consisting of a tertiary alkyl group, an unsubstituted cycloalkyl TABLE 3 Difiusible coupler used in the color developer Difference in density of yellow images 4 Yellow Cyan Magenta Experiment No. Cyan coupler (g./l.) Yellow coupler (g./l.) Magenta coupler (g./l.) density density density density 2-4-diehloro-1-naphthol (2). 2-benzoylacetanllide (1.8) 1-phenyl-3-(4-ch1orobenzamldo)-5- +0. 15 0. 12 0. 10
  • R represents NHCOCHzCHzN a member selected from the group consisting of an unsub- 5 G 4 stituted aryl group, a substituted aryl group, an unsubstituted a 2 hctcrocyclic group, and a substituted heterocyclic group
  • X represents a member selected from the group consisting of a hydrogen atom and a group capable of being split off during Coupler (9):
  • Coupler (10) 1 wherein said blue-sensitive silver halide emulsion containing S OZNHOIIID the ballasted yellow coupler is a gelatino silver iodobromide emulsion.
  • Q-COCHzCONH- 5 5.
  • Coupler (11) :
  • ballasted yellow coupler is a member selected from the group consisting of C O CHQC QNH- CH; Coupler (1):
  • said derivative 15 a member selected from the group consisting of 4-amino-N,N-diethylaniline, 4-amino-3-methyl C O CHzC ONH- N-methyl-N-([3-methyl-sulfonamidoethyl)-aniline, and 4- amino-3-methyl-N-ethyl-N-(B-hydroxy-ethyl)-aniline.
  • said coupler is a member selected from the group consisting of 2-chloro-l-naphthol, 2,4-dichloroJ-naphthol, lhydroxy-N-butyl-2-naphthamide and l-hydroxy-N-t 2- acetamidophenethyl)-2-naphthamide.
  • said diffusable magenta coupler is a member selected from the group consisting of open-chain methylene couplers and cyclic methylene couplers.
  • said open-chain methylene coupler is a member selected from the group consisting of acylacetonitriles, 2- eyanoethylbenzofuran, and benzylacetonitrile and said cyclic methylene coupler being a member selected from the group consisting of l-phenyl-3-methyl-S-pyrazolone, l-phenyl-3-(4- chlorobenzamido)-5-pyrazolone, 1-phenyl-3-(3-nitrobenzoylamino)-5-pyrazolone, and l-(2,4,6-trichlorophenyl)-3-(4- nitroanilino)-5-pyrazolone.
  • said coupler is a member selected from the group consisting of 2-acetanilide, 2-aceto-2,4-dichloroacetanilide, 2-benzoylacetanilide, 2-benzoyl-2'-methoxyacetanilide, and Z-benzoyl(4-p-toluene-sulfonamido) acetanilide.
  • a process for the prevention of color mixing for a multilayer-type reversal photographic light-sensitive material of the type developed in color forming developers, each containing a coupler which comprises developing said multilayertype reversal photographic light-sensitive material having on a support,
  • a blue-sensitive emulsion layer said developing being carried out with color.
  • developers containing a diffusabie cyan, yellow and magenta couplers, respectively, said blue emulsion layer containing a ballasted yellow coupler of the formula wherein R represents a member selected from the group consisting of a tertiary alkyl group, an unsubstituted cycloulkyl group, a substituted cycloalkyl group, an unsubstituted dicycloilkyl group, a substituted dicycloalkyl group, an unsubstituted aryl group and a substituted aryl group; R represents a member selected from the group consisting of an unsubstituted aryl group, a substituted aryl group, an unsubstituted heterocyclic group, and a substituted heterocyclic group; and
  • X represents a member selected from the group consisting of a hydrogen atom and a group capable of being split off during wherein R represents a member selected from the group consisting of a tertiary alkyl group, an unsubstituted cycloalkyl group, a substituted cycloalkyl group, an unsubstituted dicycloalkyl group, a substituted dicycloalkyl group, an unsubstituted aryl group and a substituted aryl group; R represents a member selected from the group consisting of an unsubstituted aryl group, a substituted aryl group, an unsubstituted heterocyclic group, and a substituted heterocyclic group; and X represents a member selected from the group consisting of a hydrogen atom and a group capable of being split off during the coupling reaction, said ballasted yellow coupler being present in an amount of from 0.0005 to 0.5 mols 0 per mol of blue-sensitive silver halide

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US826283A 1968-05-20 1969-05-20 Method of preventing color mixing in multilayer-type reversal color photographic light-sensitive materials Expired - Lifetime US3640716A (en)

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FR (1) FR2009919A1 (enrdf_load_stackoverflow)
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4015988A (en) * 1974-03-04 1977-04-05 Fuji Photo Film Co., Ltd. Multilayer color photographic light-sensitive material
US9045524B2 (en) 2009-05-21 2015-06-02 Novagenesis Foundation Selective caspase inhibitors and uses thereof
US9562069B2 (en) 2008-05-21 2017-02-07 Genesis Technologies Limited Selective caspase inhibitors and uses thereof
US9944674B2 (en) 2011-04-15 2018-04-17 Genesis Technologies Limited Selective cysteine protease inhibitors and uses thereof

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3114559A1 (fr) 2020-09-29 2022-04-01 Psa Automobiles Sa Dispositif de controle de redemarrage d’un moteur a combustion d’un vehicule hybride

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3180734A (en) * 1959-11-05 1965-04-27 Gevaert Photo Prod Nv Light sensitive photographic color element
US3265506A (en) * 1964-05-04 1966-08-09 Eastman Kodak Co Yellow forming couplers

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3180734A (en) * 1959-11-05 1965-04-27 Gevaert Photo Prod Nv Light sensitive photographic color element
US3265506A (en) * 1964-05-04 1966-08-09 Eastman Kodak Co Yellow forming couplers

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4015988A (en) * 1974-03-04 1977-04-05 Fuji Photo Film Co., Ltd. Multilayer color photographic light-sensitive material
US9562069B2 (en) 2008-05-21 2017-02-07 Genesis Technologies Limited Selective caspase inhibitors and uses thereof
EP2288615B1 (en) * 2008-05-21 2017-06-21 Genesis Technologies Limited Selective caspase inhibitors and uses thereof
US10167313B2 (en) 2008-05-21 2019-01-01 Genesis Technologies Limited Selective caspase inhibitors and uses thereof
US9045524B2 (en) 2009-05-21 2015-06-02 Novagenesis Foundation Selective caspase inhibitors and uses thereof
US9944674B2 (en) 2011-04-15 2018-04-17 Genesis Technologies Limited Selective cysteine protease inhibitors and uses thereof
US10975119B2 (en) 2011-04-15 2021-04-13 Genesis Technologies Limited Selective cysteine protease inhibitors and uses thereof

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DE1925391B2 (de) 1976-06-10
JPS4818256B1 (enrdf_load_stackoverflow) 1973-06-05
GB1247786A (en) 1971-09-29
FR2009919A1 (enrdf_load_stackoverflow) 1970-02-13
BE733260A (enrdf_load_stackoverflow) 1969-11-03
SE358484B (enrdf_load_stackoverflow) 1973-07-30
DE1925391A1 (de) 1969-12-11

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