US3476563A - Photographic silver halide elements containing two equivalent cyan couplers - Google Patents

Photographic silver halide elements containing two equivalent cyan couplers Download PDF

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US3476563A
US3476563A US483807A US3476563DA US3476563A US 3476563 A US3476563 A US 3476563A US 483807 A US483807 A US 483807A US 3476563D A US3476563D A US 3476563DA US 3476563 A US3476563 A US 3476563A
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coupler
group
hydroxy
couplers
color
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Anthony Loria
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Eastman Kodak Co
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Eastman Kodak Co
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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
    • G03C7/305—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers
    • G03C7/30511—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers characterised by the releasing group
    • G03C7/30517—2-equivalent couplers, i.e. with a substitution on the coupling site being compulsory with the exception of halogen-substitution
    • G03C7/30523—Phenols or naphtols couplers

Definitions

  • Couplers containing at least one 4-hydroxy-3-carbamyll-naphthyl group wherein the hydrogen atom of the one position of said naphthyl group has been replaced with an aryloxy group are used advantageously in color photography to form cyan dye images.
  • the immediate couplers that are diffusible are used to advantage in cyan color developer solutions while the immediate couplers that are nondiffusible are advantageously incorporated in cyan dye-forming photographic emulsion layers.
  • This invention relates to color photography and more particularly to new and improved cyan dye-forming coupler compounds for use in image-forming systems and processes utilizing such couplers for the formation of images.
  • my invention relates to two-equivalent coupler compounds for forming cyan dye images in color photography.
  • the color-forming couplers may be either in the developer solution or incorporated in the light-sensitive photographic emulsion layer so that, during development, it is available in the emulsion layer to react with the color developing agent that is oxidized by silver image development.
  • Ditfusible couplers are used in color developer solutions.
  • Nondiffusing couplers are incorporated in photographic emulsion layers.
  • couplers which have been used in the various color photographic systems described above are fourequivalent couplers, that is, they require reduction of 4 mols of silver halide for the formation of 1 molof dye.
  • Certain of the prior art couplers are two-equivalent couplers, i.e., they require reduction of only 2 mols of silver halide for the formation of 1 mol of dye.
  • some of the prior art couplers exhibit serious disadvantages such as low reactivity, formation of an unacceptably high level of color fog, and other undesirable side reactions.
  • the couplers of my invention include those represented by the Formula I:
  • R represents a 4-hydroXy-3carbamyl-l-naphthyl group and R represents an aryl or an arylene (i.e., a divalent organic aromatic radical) group.
  • R represents an aryl or an arylene (i.e., a divalent organic aromatic radical) group.
  • couplers of my invention may be further represented by the following Formula II:
  • n represents an integer of from 1 to 2
  • R and R represent any combination of hydrogen, an alkyl radical, either straight or branched chain of from 1 to 30 carbon atoms, a monoor bicyclic alkyl radical such as cyclohexyl, terpenyl, e.g., a norbornyl radical, etc., an aryl radical such as phenyl, naphthyl, etc., a heterocyclic radical such as benzimidazolyl, benzothiazolyl, etc., or the non-metallic atoms necessary to complete a heterocyclic ring such as morpholine, pyridine, etc.
  • These groups may contain substituent groups such as halogen, nitro, hydroxyl, carboxyl (such that the coupler contains ballasting groups with at least 12 carbon atoms or equivalent in a non-coupling position) amino, an aryl, a substituted amino (e.g., alkylamino, dialkylamino, anilino, N-alkylanilino, etc.), a carboxyl ester (e.g., carboalkoxy, carboaryloxy, etc.), an amido (e.g., acetamido, butyramido, ethylsulfonamido, N-methylbenzamido, N-propylbenzamido, 4-t-butylbenzamido, etc.), a carbamyl (e.g., carbamyl, N-octadecylcarbamyl, N,N-d
  • R represents, when n represents the integer 1, an aryl group such as phenyl, naphthyl, pyridyl, quinolyl, etc., and when n represents the integer 2, R represents an arylene group such as 1,2-phenylene, 1,3-phenylene, 1,4- phenylene, 1,5-naphthylene, 2,5-pyridylene, ethylene bis (1,4-pheny1ene), 4,4'-diphenylene sulfone, etc.
  • aryl and arylene may also contain substituent groups (e.g., halogen, nitro, hydroxyl, carboxyl, amino, substituted amino, carboxyl esters, amido, carbamyl, sulfamyl, alkoxy, aryloxy, sulfo, sulfonyl, etc.) as defined for alkyl, aryl, and heterocyclic in R and R above and phenylazo and substituted phenylazo groups.
  • substituent groups e.g., halogen, nitro, hydroxyl, carboxyl, amino, substituted amino, carboxyl esters, amido, carbamyl, sulfamyl, alkoxy, aryloxy, sulfo, sulfonyl, etc.
  • My novel couplers are characterized by having an aryloxy group on the coupling position of the coupler which gives them good coupling reactivity and other valuable properties. These couplers are particularly characterized by the low levels of unwanted color fog, high reactivity, and good stability. Excellent coupling reactivity is obtained with couplers of my invention when incorporated in emulsion layers without the use of high-boiling coupler solvents. When high-boiling solvents are used to disperse these couplers, high dye yield and low color fog are attained over a wide range of coupler-to-solvent ratios. When the difiusible couplers of my invention are used in color developing solution, excellent reactivity and good dye yield are achieved.
  • the aryloxy group provides a means of attaching other substituents to my couplers such as, for example, preformed dyes useful in color correction, dye transfer processes and the like. Additional ballasting groups can conveniently be introduced via the aryloxy group; these ballasting groups are then eliminated during the coupling reaction with oxidized color developer which forms the image dyes.
  • Couplers 1, 4, 5, 6, 7, 19, 20, 23, 26, 27, and 28 are used to advantage in color developer solutions used to color develop light-sensitive elements used for color photography which do not contain the color-forming coupler.
  • Any of the well-known primary aromatic amino colorforming silver halide developing agents such as the phenylenediamines, e.g., diethyl p phenylenediamine hydrov chloride, dimethyl-p-phenylenediamine hydrochloride, 2-
  • amino-S-diethylaminotoluene hydrochloride Z-amino-S- (N-ethyl-N-laurylamino)toluene, N-ethyl-N-(B-methanesulfonamidoethyl) -3-methyl-4-aminoaniline, 4- [N-ethyl- N 3 hydroxyethyl)amino]aniline, etc.
  • the p-aminophenols and their substitution products where the amino group is unsubstituted may be used in the alkaline developer solution with my couplers.
  • Various other materials may be included in the developer solutions depending upon the particular requirements, for example, an alkali metal sulfite, carbonate, bisulfite, bromide, iodide, etc., and the thickening agents used in viscous developer compositions such as carboxymethyl cellulose, carboxyethyl cellulose, gelatin, etc.
  • an alkali metal sulfite, carbonate, bisulfite, bromide, iodide, etc. and the thickening agents used in viscous developer compositions such as carboxymethyl cellulose, carboxyethyl cellulose, gelatin, etc.
  • the following is a typical developer solution given to illustrate but not limit my invention.
  • Couplers such as 2, 12, 14, 15, 16, 17, 18, 24, and 25 illustrate those that are incorporated as Fischer-type couplers.
  • the other nondiifusing couplers e.g., 3, 8, 9, 10, 11, 13, 21, and 22, are incorporated in emulsion layers by methods such as are described by Mannes et al., US. Patent 2,304,939, issued December 15, 1942, Jelley et al. US. Patent 2,322,027, issued June 15, 1943, etc., in which high-boiling organic solvents are used to dissolve the coupler, and by methods described in Vittum et al. US.
  • the use of such coupler dispersions permits thinner emulsion layers. These thinner layers are very desirable because they cause less light scattering, consequently they produce sharper images.
  • Coupler 17 contains a preformed dye attached to the coupler on the aryloxy group. This dye is eliminated on the coupling of the coupler with an oxidized color developer and diffuses out of the film.
  • This coupler can be used as a yellow-colored coupler for the purpose of correcting for the unwanted blue absorption of the cyan image dyes, i.e., that formed from the coupler itself as well as that formed from other cyan couplers. Generally, such a coupler as this would be used in combination with another image-forming cyan coupler in the same layer.
  • My couplers are used to advantage in the color development of photographic hydrophilic colloid-silver halide emulsion layers of the developing-out type in the emulsion layer or a contiguous layer.
  • the emulsions may contain silver chloride, silverbromide, silver iodide, silver chlorobromide, silver bromoiodide, silver ehlorobromoiodide, etc., as the light-sensitive material.
  • hydrophilic colloids used in photographic elements are used to advantage, including gelatin, colloidal albumin, a cellulose derivative, or a synthetic resin, for instance, a polyvinyl compound, etc.
  • the emulsions used in the photographic element of my invention can be chemically or optically sensitized.
  • the couplers of my invention may also be used to advantage in image-forming layers, either alone or with image-forming compounds other than silver halide, such as ZnO, ZnS, CdS, CdSe, NiS, etc., either with or without binders such as gelatin, polyvinyl alcohol, etc.
  • image-forming compounds other than silver halide such as ZnO, ZnS, CdS, CdSe, NiS, etc.
  • binders such as gelatin, polyvinyl alcohol, etc.
  • my emulsions are coated on photographic supports in the form of multilayer color photographic elements wherein at least three differently sensitized emulsion layers are coated over one another on the support.
  • the support is coated in succession with a redsensitive layer, a green-sensitive layer, and a blue-sensitive layer either with or without a Carey Lea silver yellow filter layer between the blue-sensitive and green-sensitive layers.
  • the three differently color sensitized layers may be arranged in any other order over one another that is desirable; however, the Carey Lea filter layer obviously would not be put over the blue-sensitive layer.
  • these light-sensitive layers are arranged on the same side of the support.
  • Example 1 Samples of a single layer relatin silver bromo-iodide coating were exposed (i.e., for -second on a 1B intensity scale sensitometer). These strips were then processed to color positives by the following process; all process temperatures were 6 8".
  • Example 2 Single layer gelatin silver bromoiodide coatings were prepared containing Couplers 3, 8, 9*, 10, 11, 13, 21, and 22, respectively. Each of these couplers were dispersed in said coatings in the from of a finely-dispersed solution of the coupler in coupler solvent, di-n-butylphthalate. These coatings contained 10 parts of gelatin, 5 parts of silver, 2 parts of coupler, and 1 part of coupler solvent. Samples of the above-mentioned coatings were given 3 second exposure on a 1B intensity scale sensitometer and processed in a conventional manner to color negatives, respectively, using the following developer solution.
  • Each of the processed strips contained high quality cyan dye images having good heat and light stability and low fog.
  • couplers of my invention are used to advantage in color photography as illustrated previously with representative couplers.
  • the couplers of my invention are valuable as cyan image-forming couplers in multilayer photographic color films containing other classes of couplers in the other layers of said film.
  • Such other couplers are, for example, yellow image-forming couplers containing a methylene or substituted methylene group having two carbonyl groups directly attached thereto, and magenta image-forming couplers such as S-pyrazolones, cyanoacetyl coumarones, etc.
  • my couplers are the product of the reaction of a 1-hydroxy-4-aryloxy-2-naphthoyl chloride with the appropriately substituted amine.
  • my couplers may be prepared by reacting 1-hydroxy-4-acetoxy-2-naphthoyl chloride with an amine, converting the resultant 1-hydroxy-4-acetoxy-2- naphthamide to the 1-benzyloxy-4-acetoxy-2-naphthamide, hydrolyzing to the corresponding 4-hydroxy compound, the sodium salt of which is then reacted with the fluorobenzene.
  • This 1-benzyloxy-4-aryloxy-2-naphthamide is then converted to the corresponding 1-hydroxy-4- aryloxy-Z-naphthamide by hydrogenolysis of the l-benzyloxy group.
  • Coupler 2 1-hydroxy-4- ⁇ 4-[a-(3-pentadecylphenoxy) butyramido] phenoxy ⁇ -N-octadecyl-3,5'- dicarboxy-Z-naphthanilide
  • Intermediate 1--1-hydroxy 4 (4-nitrophenoxy)-2- naphthoic acid To a solution of 20 g. of 1,4-dihydroxy- Z-naphthoic acid in 150 ml. of dimethyl formamide was added 20 g. of aqueous 40% sodium hydroxide solution and 14 g. of 4-nitrofluorobenzene over a period of 5 minutes with stirring under a nitrogen atmosphere. The reaction mixture was stirred for a total of 2 hours, after which time it was poured into dilute hydrochloric acid whereupon a solid separated, was collected, recrystallized twice from methyl alcohol, to yield the product.
  • the solid was recrystallized
  • the other pl rs of my ention were each prepared f a i t f hexane d benzene t i ld th in accordance with the procedure used to prepare Coud g pler 3 using the respective intermediates given in the fol.-
  • Coupler 24 1-hydroxy-4-(4-acetam1dophenoxy) -N-octadecyl-3,5 -dicarb oxy-2-naphthanilide
  • Intermediate-1 hydroxy 4 (4-acetamidophenoxy)- N-octadecyl-3,5'-dicarbomethoxy-Z-naphthanilide:
  • To 21 TABLE Acid Chloride
  • Intermediate Amine Intermediate Coupler No. 1-hydroxy-4-(4-acetam1dophenoxy) -N-octadecyl-3,5 -dicarb oxy-2-naphthanilide
  • N-octadecyl-4-Su1ioaniline sodium salt N-octadecyl-3,5-dicarbomethoxyaniline.
  • Coupler 7 The nitro product was catalytically reduced and the two amino groups were acetylated using acetic anhydride to yield Coupler 7.
  • Coupler 8 The nitro intermediate was then catalytically reduced and the resultant amino compound was acylated with a-(2,4-di-t-amylphenoxy)- acetyl chloride to yield Coupler 8.
  • Coupler 13 The nitro intermediate was catalytically reduced and aeylated with a-(3-pentadecylphenoxy)-butyryl chloride to yield Coupler 13.
  • the nitro intermediate was catalytically reduced and acylated with 2-(2,4-dit-amylphenoxy)-5-nitrobenzoyl chloride.
  • the second nitro intermediate was also catalytically reduced and acylated with 3,5-di chlorosultonylbenzoyl chloride.
  • the chlorosulionyl groups were hydro lyzed to the sulfonic acid sodium salts to yield Coupler 16.
  • Coupler 22 The nitro intermediate was catalytically reduced and ecetylated with acetic anhydride to yield Coupler 22.
  • Coupler 23 The intermediate containing the chlorosulfonyll group was hydrolyzed (1.e., by alkaline hydrolysis) to yield Coupler 23.
  • the two-equivalent image-forming couplers of my invention are distinguished from other two-equivalent couplers by having an aryloxy group substituted on the coupling position of the coupler molecule.
  • My couplers are characterized by not producing color fog, a problem with certain prior art two-equivalent couplers, and by having very good coupling reactivity.
  • my novel couplers form dye images which exhibit very good heat and light stability when they are incorporated into photographic coatings relative to that exhibited by many of the prior art couplers.
  • My couplers are dispersed readily in emulsion layers as a coupler solvent solution having a wide range of couplerto-solvent ratios.
  • My couplers are not only valuable for the reasons cited, but because photographic emulsion layers coor developed with them require only one-half the amount of siver halide required by four-equivalent couplers. Of particular value are certain of my nondiffusing couplers which have high coupling reactivity when dispersed in photographic emulsion layers without any high-boiling solvent. These couplers are coated to advantage in particularly thin layers that produce good sharp images.
  • the couplers of my invention may be used in emulsion layers or color developer solutions either alone or admixed with other couplers, either fouror two-equivalent couplers, competing cou' plers, and the like.
  • R go ON K/ wherein n represents an integer of from 1 to 2;
  • R and R each represents a group selected from the class consisting of the hydrogen atom, an alkyl radical, an aryl radical, a heterocyclic radical, and, together, the nonmetallic atoms necessary to complete a heterocyclic ring;
  • R represents an aryl group selected from the class consisting of a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, a phenylene group, a naphthylene group, a pyridylene group and a quinolylene group such that when n represents the integer 1,
  • R represents an aryl group selected from the class consisting of a phenyl group, a naphthyl group, a pyridyl group and a quinolyl group in which a carbon atom in a ring of said aryl group is attached directly to the oxygen atom attached to the
  • the 1mprovement wherein at least one such coupler comprises a cyan-dye-forming coupler which is capable of forming a cyan dye on coupling with the oxidation product of an aromatic amino developing agent, said cyan-dye-forming coupler being selected from those having the formula:
  • R represents a 4-hydroxy-3-carbamyl-1-naphthyl group
  • n represents an integer of from 1 to 2
  • R represents an aryl group selected from the class consisting of a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, a phenylene group, a naphthy-.
  • R represents an aryl group selected from the class consisting of a phenyl group, a naphthyl group, a pyridyl group and a quinolyl group, in which a carbon atom in a ring of said aryl group is attached directly to the oxygen atom in said formula, and such that when n represents the integer 2, R represents an aryl group selected from the class consisting of a phenylene group, a naphthylene group, a pyridylene group and a quinolylene group in which one carbon atom in a ring of said aryl group is attached directly to one of the oxygen atoms of said formula and in which another carbon atom in a ring of said aryl group is attached directly to the other oxygen atom of said formula.
  • n represents an integer of from 1 to 2;
  • R and R each represents a group selected from the class consisting of the hydrogen atom, an alkyl radical, an aryl radical, a heterocyclic radical, and, together, the nonmetallic atoms necessary to complete a heterocyclic ring;
  • R represents an aryl group selected from the class consisting of a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, a phenylene group, a naphthylene group, a pyridylene group and a quinolylene group such that when n represents the integer 1,
  • R represents an aryl group selected from the class consisting of a phenyl group, a naphthyl group, a pyridyl group and a quinolyl group in which a carbon atom in a ring of said aryl group is attached directly to the oxygen atom attached to the 4 carbon atom of the 1-
  • R represents a 4-hydroxy-3-carbamyl-1-naphthyl group; n represents an integer of from 1 to 2; and R represents an aryl group selected from the class consisting of a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, a phenylene group, a naphthylene group, a pyridylene group and a quinolylene group, such that when n represents the integer l, R represents an aryl group selected from the class consisting of a phenyl group, a naphthyl group, a pyridyl group and a quinolyl group, in which a carbon atom in a ring of said aryl group is attached directly to the oxygen atom in said formula, and such that when n represents the integer 2, R represents an aryl group selected from the class consisting of a phenylene group, a naphthylene
  • n represents an integer of from 1 to 2;
  • R and R each represents a group selected from the class consisting of the hydrogen atom, an alkyl radical, and aryl radical, a heterocyclic radical, and, together, the nonmetallic atoms necessary to complete a heterocyclic ring;
  • R represents an aryl group selected from the class consisting of a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, a phenylene group, a naphthylene group, a pyridylene group and a quinolylene group such that when n represents the integer l, R represents an aryl group selected from the class consisting of a phenyl group, a naphthyl group, a pyridyl group and a quinolyl group in which a carbon atom in a ring of said aryl group is attached directly to the oxygen atom attached to the 4 carbon atom of the

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DE2538323A1 (de) * 1974-08-28 1976-03-11 Fuji Photo Film Co Ltd Farbenphotographisches material
US4004929A (en) * 1974-03-04 1977-01-25 Eastman Kodak Company Color corrected photographic elements
DE2634694A1 (de) * 1975-08-02 1977-02-17 Konishiroku Photo Ind Photographischer kuppler und dessen verwendung zur erzeugung von photographischen bildern
US4138258A (en) * 1974-08-28 1979-02-06 Fuji Photo Film Co., Ltd. Multi-layered color photographic materials
US4157919A (en) * 1978-03-31 1979-06-12 Eastman Kodak Company Silver halide emulsions containing yellow-dye-forming couplers
US4178183A (en) * 1978-07-27 1979-12-11 Eastman Kodak Company Thiazolyl coupler compositions and photographic elements suited to forming integral sound tracks
US4264722A (en) * 1978-11-14 1981-04-28 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive material
US4296200A (en) * 1979-08-13 1981-10-20 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive material
US4296199A (en) * 1979-06-19 1981-10-20 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive material
JPS57138636A (en) * 1981-02-19 1982-08-27 Konishiroku Photo Ind Co Ltd Silver halide color photographic material
US4433046A (en) * 1981-06-03 1984-02-21 Konishiroku Photo Industry Co., Ltd. Silver halide photographic material
US4438193A (en) 1980-12-27 1984-03-20 Konishiroku Photo Industry Co., Ltd. Silver halide photosensitive color photographic material
US4450222A (en) * 1982-12-20 1984-05-22 Eastman Kodak Company Use of carbon adsorption deactivating compounds in image transfer elements
EP0112162A2 (en) 1982-12-13 1984-06-27 Konica Corporation Light-sensitive silver halide photographic material
US4471047A (en) * 1982-12-20 1984-09-11 Eastman Kodak Company Use of carbon adsorption deactivating compounds in image transfer elements
EP0147854A2 (en) 1983-12-29 1985-07-10 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive materials
EP0201033A2 (en) 1985-04-30 1986-11-12 Konica Corporation A method for processing silver halide color photographic materials
EP0202616A2 (en) 1985-05-16 1986-11-26 Konica Corporation Method for color-developing a silver halide photographic light-sensitive material
EP0204530A2 (en) 1985-05-31 1986-12-10 Konica Corporation Method for forming direct positive color image
EP0228914A2 (en) 1985-12-28 1987-07-15 Konica Corporation Method of processing lightsensitive silver halide color photographic material
US4743595A (en) * 1984-06-14 1988-05-10 Fuji Photo Film Co., Ltd. Process for preparing 2-amino-5-nitrophenol derivatives
US4818668A (en) * 1984-08-24 1989-04-04 Fuji Photo Film Co., Ltd. Silver halide color photographic materials
JPH02118572A (ja) * 1988-10-27 1990-05-02 Konica Corp ハロゲン化銀カラー写真感光材料の処理方法
EP0429098A1 (en) 1987-03-09 1991-05-29 Eastman Kodak Company Photographic silver halide materials and process comprising a pyrazoloazole coupler
US5030544A (en) * 1984-09-28 1991-07-09 Agfa-Gevaert, N.V. Photographic elements comprising thiazolyl couplers capable of forming infrared-absorbing dyes for integral sound track
EP0574090A1 (en) 1992-06-12 1993-12-15 Eastman Kodak Company One equivalent couplers and low pKa release dyes
USRE34697E (en) * 1982-11-30 1994-08-16 Konishiroku Photo Industry Co., Ltd. Silver halide photographic light-sensitive material
US5354646A (en) * 1986-03-26 1994-10-11 Konishiroku Photo Industry Co., Ltd. Method capable of rapidly processing a silver halide color photographic light-sensitive material
US5376484A (en) * 1992-09-01 1994-12-27 Konica Corporation Photographic information recording method
US5427898A (en) * 1992-12-04 1995-06-27 Eastman Kodak Company Yellow couplers having an arloxy coupling-off group which contains an ortho polarizable functional group
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EP0690345A1 (en) 1994-06-23 1996-01-03 Eastman Kodak Company Two-equivalent magenta photographic couplers with activity-modifying ballasting groups
EP0690344A1 (en) 1994-06-29 1996-01-03 Konica Corporation Silver halide color photographic light-sensitive material
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EP0711804A2 (de) 1994-11-14 1996-05-15 Ciba-Geigy Ag Kryptolichtschutzmittel
EP0779543A1 (en) 1995-12-11 1997-06-18 Eastman Kodak Company Photographic element containing an improved pyrazolotriazole coupler
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US7601030B2 (en) 2007-02-16 2009-10-13 Hammond Power Solutions, Inc. Method and apparatus for directly mounting fuses to transformer terminals
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JPS57111537A (en) * 1980-12-27 1982-07-12 Konishiroku Photo Ind Co Ltd Color photographic sensitive silver halide material
JPS61250643A (ja) 1985-04-30 1986-11-07 Konishiroku Photo Ind Co Ltd ハロゲン化銀写真感光材料
US4725529A (en) 1985-04-30 1988-02-16 Konishiroku Photo Industry Co., Ltd. Developing inhibitor arrangment in light-sensitive silver halide color photographic materials

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Cited By (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4004929A (en) * 1974-03-04 1977-01-25 Eastman Kodak Company Color corrected photographic elements
DE2538323A1 (de) * 1974-08-28 1976-03-11 Fuji Photo Film Co Ltd Farbenphotographisches material
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GB1084480A (en) 1967-09-20
DE1547730A1 (de) 1970-04-16
BE685935A (OSRAM) 1967-02-01

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