US2521908A - 1-hydroxy-2-naphthamide colored couplers - Google Patents

1-hydroxy-2-naphthamide colored couplers Download PDF

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US2521908A
US2521908A US734548A US73454847A US2521908A US 2521908 A US2521908 A US 2521908A US 734548 A US734548 A US 734548A US 73454847 A US73454847 A US 73454847A US 2521908 A US2521908 A US 2521908A
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hydroxy
compound
coupler
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Dudley B Glass
Paul W Vittum
Weissberger Arnold
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to BE476362D priority patent/BE476362A/xx
Priority to US613456A priority patent/US2428054A/en
Priority to FR950288D priority patent/FR950288A/en
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to US734548A priority patent/US2521908A/en
Priority to GB18258/47A priority patent/GB627814A/en
Priority to FR950228D priority patent/FR950228A/en
Priority to CH283456D priority patent/CH283456A/en
Priority to CH285169D priority patent/CH285169A/en
Priority to FR980372D priority patent/FR980372A/en
Priority to ES0183158A priority patent/ES183158A1/en
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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
    • G03C7/333—Coloured coupling substances, e.g. for the correction of the coloured image
    • G03C7/3335—Coloured coupling substances, e.g. for the correction of the coloured image containing an azo chromophore
    • C—CHEMISTRY; METALLURGY
    • C21—METALLURGY OF IRON
    • C21D—MODIFYING THE PHYSICAL STRUCTURE OF FERROUS METALS; GENERAL DEVICES FOR HEAT TREATMENT OF FERROUS OR NON-FERROUS METALS OR ALLOYS; MAKING METAL MALLEABLE, e.g. BY DECARBURISATION OR TEMPERING
    • C21D9/00—Heat treatment, e.g. annealing, hardening, quenching or tempering, adapted for particular articles; Furnaces therefor
    • C21D9/70—Furnaces for ingots, i.e. soaking pits

Definitions

  • This invention relates to color photography and particularly to color couplers for use in photographic processes.
  • Color-forming compounds which react with the development product of aromatic amino developing agents to form colored images "upon photographic development'are well known.
  • these color-forming-compounds of couplers are colorless or substantially colorless. This lack of color is usually desirable where the coupler is to be incorporated in'the. emulsion layer and the unused coupler remains after'formation of the colored image.
  • the coupler is used in the developing'solution,it may be colored without detriment to the final image" and certain colored couplers have been used in this way.
  • I T N- B especially ⁇ a'mononuclear aryl radical such as phenyl or substituted phenyl, a mononuclear aryloxyphenyl radical such as p-tertiary-butylphenoiryphenyl, p-tert.-amylphenoxyphenyl, 2,4-
  • d-iamylnhenoxyphenyl or phenoxypnenyl or an active po'sitionof the coupler issubstituted with an azo group --and this .group is split offi or removed by the oxidized developer when thea'zosubstituted coupler is treated with the-oxidized developer either in aqueous solution or in the photographic emulsion layer.
  • the coupler may be converted to a difierently colored compound and the azo .group readily -removed;trom it by means oi :reaction wi-th the oxidized deasarpoa OOl lehydroxy-l-phenylazo-N-isoamyl-2maphthanilide 1-hydroxy-4- (2 metl1oxy-4-nitrophenylazo -N-is0amyl- 2-naphthanilide 3 C H3 00 Ha 1-hydroxy-4- [Z-methoxyl- (o-methoxyphenylazo) phenylazo] -N-isoamyl2-naphthanilide Our compounds may be incorporated either in the developing solution or in the emulsion layer according to their intended use and diffusion characteristics.
  • the Hanson process involves a color correction method in which a color coupler is incorporated in the photographic emulsion layer prior to exposure and upon development is con.- verted to a colored image where theJayer is eX-- posed.
  • the coupler remaining in the: unexposedportions of the layer retains itsv original color and by suitable choiceof the colorofthe original coupler and the color of the final dye image, a masking or correction effect can be obtained.
  • the compounds employed according to our invention may be prepared by any suitable method such as by reaction of the naphthamide with the appropriate diazonium compound.
  • compound No. 1 was prepared as follows:
  • l hydroxy 4' (p-tert. butylphenoxy) -2- naphthanilide was prepared by the condensation of equi-molecular quantities of phenyl l-hydroxy-2-naphthoate and p-(p-tert-butylphenoxy-) -aniline at 200 for one hour.
  • the product was purified by recrystallizationfrom a mixture of benzene and ligroin.
  • the p (p-tert.-butylphenoxy) aniline was prepared by alkali condensation of hot p-nitro chlorobenzene and p-tert-butylphenol followed by catalytic reduction of the nitro compound in the presence of Raney nickel.
  • Coupler Diazonium salt o-methoxybenz-ene diazonlum chloride.
  • diazonium chloride 4' 1-hydroxy-4-(p-tert.-butylphe- Z-meth o xylenitronoxy) -2-naphthanilide.
  • benzene diazonium f chloride 5.----- l-hydroxy-4'- (p-tert.-butylpl1e- 2-n1ethoxy4-pl1enylnoxy) -2-naphtlianilide. azobenzene diazonium chloride.
  • Compound No. 6 was: prepared as follows:
  • the ,4- (p-tert-.-amylphenoxy-)aniline was preparedby the condensation of hot p-nitrochlorobenzene and p-terteamylphenol in alkali to yield 4 (p tert. amylphenoxy)nitrobenzene.
  • 1-- hydroxy--(o met-hoxyphenylazo)-4'-(ptert. amylphenoxy)-2-naphthanilide (6) was prepared by adding an equivalent solution of 1.05 mols of omethoxybenzene diazonium chloride to 1 mol of 1hydroxy-4-(p-tert.-amy1phenoxy)-2- naphthanilide in 8 liters of pyridine ethanol (1:1) solution at 5 C. The product was isolated by pouring the mixture into an excess of hydrochloric acid. The pure dye was obtained by crystallization from dioxane or acetic acid.
  • Compound No. 8 was prepared in the following manner:
  • the final compound was prepared by the simple treatment of 1 hydroxy-N- ⁇ i-[2-(2,4-diamylphenoxy) 5-(3,5-dichlorosulfonylbenzamido) benzamido] phenethyl ⁇ 2-naphthamide with benzene diazonium chloride.
  • Compound 9 was prepared by the condensation in ether of two equivalents of N-methylaniline with 1 equivalent of l-hydroxy-Z-naphthoyl chloride to produce l-hydroxy-N-methyl- 2-naphthanilide.
  • the final compound was prepared by treating this intermediate with o-carbethoXy-benzene diazonium chloride.
  • Compound 10 was prepared by the condensation in ether of 2 equivalents of N-isoamylaniline with 1 equivalent of 1-hydroxy-2-naphthoyl chloride to produce l-hydroxy-N-isoamyl-Z- naphthanilide. This intermediate was treated with benzene diazonium chloride to produce the final compound.
  • the primary aromatic amino developing agents are generally suitable including the phenylenediamines and aminophenols.
  • the alkyl phenylenediamines may be substituted in the amino group as well as in the ring.
  • Suitable compounds Grams 2-amino-5-diethyl-amino toluene HCl 2 Sodium sulphite 2 Sodium carbonate Potassium bromide 2 Water .to V1 liter.
  • X is selected from the class consisting of hydrogen and alkyl radicals
  • Y is selected from the class consisting of mononuclear aryl radicals and aralkyl radicals
  • R is a mononuclear aryl radical
  • X is selected from the class consisting of hydrogen and alkyl radicals
  • Y is selected'from the class consisting of mononuclear aryl radicals and aralkyl radicals and R is a mononuclear aryl radical
  • Y is a mononuclear aryl-oxyphenyl radical and R is a mononuclear aryl radical
  • X is selected from the class consisting of hydrogen and alkyl radicals
  • Y is selected from the class consisting of mononuclear aryl radicals, aralkyl radicals and R is a mononuclear aryl radical.
  • O ONH-Y N NR Where Y and R are mononuclear aryl radicals.

Description

Patented Sept. 12, 1950 COUPLERS Dndley-EHGrlass, Paul W. Vitturn, and Arnold Weissherger, {Roche-aster, N. 1 'assignors to Eastman Kodak Company; "Rochester, NI'YJ a corporation cf New Jersey N 0 Drawing. Application March 13, 1947,
' Serial No. 734,548
10 Claims.
.1 This invention relates to color photography and particularly to color couplers for use in photographic processes.
Color-forming compounds which react with the development product of aromatic amino developing agents to form colored images "upon photographic development'are well known. Generally, these color-forming-compounds of couplers are colorless or substantially colorless. This lack of color is usually desirable where the coupler is to be incorporated in'the. emulsion layer and the unused coupler remains after'formation of the colored image. When the coupler is used in the developing'solution,it may be colored without detriment to the final image" and certain colored couplers have been used in this way.
In our prior application Serial No. 533931, filed May 3, 1944, now PatentNo. 2,455,169, of which the present application is a continuationin-part, we have described couplers having the general formula in which R is a benzene or naphthalene nucleus which has the=azo group in a position para to the hydroxyl group and R an aromatic or heterocyclic radical. 'These -couplers are in them selves more or less strongly colorecLand during the coupling reaction, the chromophore system in the coupler is destroyed or split off with the.
result that the-original color of the coupler is destroyed and a new dye is formed upon coupling. Thus on developing an emulsion layer containing one of these colored couplers, the coupler color is destroyed-and a new color is formed by the coupling reaction :at thosepoints where development occurs. There-is formed in-thisway a dye image of one color on, 'abaclz gro-und of another color.
We have now found a class of colored couplers to orange-red in color and yield cyan or bluegreen dyes by reaction with the oxidizedd'eveloD- ing agent.
The'couplers'yvhich we proposeto use according to the present invention have thefollowinfg general formula: p
I T N- B especially \a'mononuclear aryl radical such as phenyl or substituted phenyl, a mononuclear aryloxyphenyl radical such as p-tertiary-butylphenoiryphenyl, p-tert.-amylphenoxyphenyl, 2,4-
d-iamylnhenoxyphenyl or phenoxypnenyl or an active po'sitionof the coupler, issubstituted with an azo group --and this .group is split offi or removed by the oxidized developer when thea'zosubstituted coupler is treated with the-oxidized developer either in aqueous solution or in the photographic emulsion layer. Thus the coupler may be converted to a difierently colored compound and the azo .group readily -removed;trom it by means oi :reaction wi-th the oxidized deasarpoa OOl lehydroxy-l-phenylazo-N-isoamyl-2maphthanilide 1-hydroxy-4- (2 metl1oxy-4-nitrophenylazo -N-is0amyl- 2-naphthanilide 3 C H3 00 Ha 1-hydroxy-4- [Z-methoxyl- (o-methoxyphenylazo) phenylazo] -N-isoamyl2-naphthanilide Our compounds may be incorporated either in the developing solution or in the emulsion layer according to their intended use and diffusion characteristics. Generally, they will be used in one of the emulsion layers of a multi-layer coating in order to secure the masking effects described in Hanson U. S. application Serial No. 533,910, filed May 3, 1944, now Patent. No. 2,449,966. The Hanson process involves a color correction method in which a color coupler is incorporated in the photographic emulsion layer prior to exposure and upon development is con.- verted to a colored image where theJayer is eX-- posed. The coupler remaining in the: unexposedportions of the layer retains itsv original color and by suitable choiceof the colorofthe original coupler and the color of the final dye image, a masking or correction effect can be obtained.
The compounds employed according to our invention may be prepared by any suitable method such as by reaction of the naphthamide with the appropriate diazonium compound. For example, compound No. 1 was prepared as follows:
1. l hydroxy 4' (p-tert. butylphenoxy) -2- naphthanilide was prepared by the condensation of equi-molecular quantities of phenyl l-hydroxy-2-naphthoate and p-(p-tert-butylphenoxy-) -aniline at 200 for one hour. The product was purified by recrystallizationfrom a mixture of benzene and ligroin.
The p (p-tert.-butylphenoxy) aniline was prepared by alkali condensation of hot p-nitro chlorobenzene and p-tert-butylphenol followed by catalytic reduction of the nitro compound in the presence of Raney nickel.
1 hydroxyl-phenylazo-' (p-tert.-butylphenoXy)-2-naphtl'1anilide (1) was prepared by adding an aqueous solution of 1.05 moles ofrben-.- zene diazonium chloride to one mole of l-hydroxy 4 (p-tert.-butylphenoxy) 2 naphthanilide dissolved in eight liters of pyridineethanol (1-1) solution at- 5 C'. The product is isolated by pouring the mixturev into an excess 6 Q ofzdilute hyd'rochloric.acid. The pure.adye.:is..ob tained by crystallization from. dioxane or acetic acid.
Compounds 2 to v5. wereprepared. in the same mannerascompound l using the following couplers and diazonium salts.
Coupler Diazonium salt o-methoxybenz-ene diazonlum chloride. p aoetamldobenzene noxy) 2 naphthanilide. diazonium chloride. 4' 1-hydroxy-4-(p-tert.-butylphe- Z-meth o xylenitronoxy) -2-naphthanilide. benzene diazonium f chloride. 5.----- l-hydroxy-4'- (p-tert.-butylpl1e- 2-n1ethoxy4-pl1enylnoxy) -2-naphtlianilide. azobenzene diazonium chloride.
Compound No. 6 was: prepared as follows:
6. lg-hydroxy l (p-tert-.-amylphenoxy)- 2+naphthanilidewas, prepared: by the condensation at-room temperature: of on equivalent of 1+hydroxy-2-naphthoyl chloride with two equivalents of 4- ('p' tert. amylphenoxy) aniline in ether. The amine hydrochloride was removed by filtration and the filtratewas concentrated toacrude product which was recrystallized from amixture of ligroin and benzene.
The ,4- (p-tert-.-amylphenoxy-)aniline was preparedby the condensation of hot p-nitrochlorobenzene and p-terteamylphenol in alkali to yield 4 (p tert. amylphenoxy)nitrobenzene. The nitro compound was reduced catalytically in' the presence of Raney nickel to- 4-(=p-tert.-amylphenoxy) aniline.
1-- hydroxy--(o met-hoxyphenylazo)-4'-(ptert. amylphenoxy)-2-naphthanilide (6) was prepared by adding an equivalent solution of 1.05 mols of omethoxybenzene diazonium chloride to 1 mol of 1hydroxy-4-(p-tert.-amy1phenoxy)-2- naphthanilide in 8 liters of pyridine ethanol (1:1) solution at 5 C. The product was isolated by pouring the mixture into an excess of hydrochloric acid. The pure dye was obtained by crystallization from dioxane or acetic acid.
Compound No. '7 was prepared as follows:
1 hydroxy-J-(2,4-diamylphenoxy) -2-naphthanilide was prepared in a manner similar to 1 hydroxy-4 -(p-tert.-butylphenoxy) -2-naphthanilide, which was used in the preparation of compound No. 1, by using p (2,4 diamylphenoxy aniline instead of p (p-tert-butylphenoxy) aniline.
1- hydroxy-4- (p-br-omophenylazo) -4- (2,4-diamylphenoxy) 2 naphthanilide was prepared by treating l-hydroxy-4- (ZA-diamylphenoxy) Z-naphthanilid'e with p-bromobenzene diazonium chloride.
Compound No. 8 was prepared in the following manner:
8. l hydroXy-N {4-['2-(2A-diamylphenoxy)- 5- 3.5-dichloro-sulfamylbenzamido) benzarnidol phen'ethyl}-2-naphthamide was prepared by the following steps:
(a) Phenyl l-hydroxy-Z-naphthoate was condensed at for one-half hour with an equimolecular quantity of p-nitrophenethylamine yielding 1 hydroXy-N-(p-nitrophenethyl) 2- naphthamide.
(b) The nitro compound was reduced catalytically in the presence of Raney nickel to the amine.
(c) 1.- hydroxy -.N (p-ami'nophenethyll-Z- naphthamide. was condensed in acetic acid and sodium acetate at room temperature with an equimolecular quantity of 2 (2,4 diamylphenoxy) --nitrobenzoyl chloride.
(d) l-hydroxy-N-{4-[2- (2,4-diamylphenox'y) 5 aminobe'nzamido]phenethy1}-2-naphthamide was prepared by the catalytic reduction in the presence of Raney nickel of the nitro compound obtained in step (c).
(e) 1 hydroxy N {4.- [2 (2,4 diamylphenoxy) 5 (3,5-dichlorosulfonybenzamido)- benzamido]phenethyl}-2-naphthamide was prepared by th condensation of an equimolecular quantity of 3,5-dichlorosul fonyl benzoyl chloride and the amine of step (d) in dioxane and qinoline.
The final compound was prepared by the simple treatment of 1 hydroxy-N-{ i-[2-(2,4-diamylphenoxy) 5-(3,5-dichlorosulfonylbenzamido) benzamido] phenethyl}2-naphthamide with benzene diazonium chloride.
Compound 9 was prepared by the condensation in ether of two equivalents of N-methylaniline with 1 equivalent of l-hydroxy-Z-naphthoyl chloride to produce l-hydroxy-N-methyl- 2-naphthanilide. The final compound was prepared by treating this intermediate with o-carbethoXy-benzene diazonium chloride.
Compound 10 Was prepared by the condensation in ether of 2 equivalents of N-isoamylaniline with 1 equivalent of 1-hydroxy-2-naphthoyl chloride to produce l-hydroxy-N-isoamyl-Z- naphthanilide. This intermediate was treated with benzene diazonium chloride to produce the final compound.
Compounds 11 and 12 were prepared similarly to compound 10 by treating l-hydroxy-N-isoamyl-Z-naphthanilide with the appropriate diazonium salt as follows:
Coupler Diazonium salt Z-meth oxyA-nitrobenzene diazonium chloride.
Z-rnethoxyi- (o-methoxyphenyl-azo) benzene diazonium chloride.
l-hydroxy-N-isoamyl-Z-naphthanilide.
l-hydroxy-N-isoamyl-2-naphthanilide.
Various photographic developing agents can be employed with the couplers of our invention.
The primary aromatic amino developing agents are generally suitable including the phenylenediamines and aminophenols. The alkyl phenylenediamines may be substituted in the amino group as well as in the ring. Suitable compounds Grams 2-amino-5-diethyl-amino toluene HCl 2 Sodium sulphite 2 Sodium carbonate Potassium bromide 2 Water .to V1 liter.
It will be understood that the examples and,
where X is selected from the class consisting of hydrogen and alkyl radicals, Y is selected from the class consisting of mononuclear aryl radicals and aralkyl radicals and R is a mononuclear aryl radical.
2. The method of developing a colored image in a silver halide emulsion layer which comprises incorporating in said layer' a coupler compound having the formula:
Where X is selected from the class consisting of hydrogen and alkyl radicals, Y is selected'from the class consisting of mononuclear aryl radicals and aralkyl radicals and R is a mononuclear aryl radical, exposing said layer and developing it with a primary aromatic amino developing agent, thereby splitting oil the N='NR, group in said coupler compound and coupling said compound at the point of splitting with the oxidation prodnot of the primary aromatic amino developing agent to form a dye image.
3. The method of developing a colored image in a silver halide emulsion layer which comprises incorporating in said layer a coupler compound having the formula:
where Y is a mononuclear aryl-oxyphenyl radical and R is a mononuclear aryl radical, exposing said layer and developing it with a primary aromatic amino developing agent, thereby splitting oi'i the N=NR group in said coupler compound and coupling said compound at the point of splitting with the oxidation product of the primary aromatic amino developing agent to form a dye image.
4. The method of developing a colored image n a silver halide emulsion layer which comprises incorporating in said layer a coupler compound having the formula:
I CH
exposing said layer and developing it with a primary aromatic amino developing agent, thereby splitting 01f the group in said coupler compound and coupling said compound at the point of splitting with the oxidation product of the primary aromatic amino developing agent to form a dye image.
5. The method of developing a colored image in a silver halide emulsion layer which comprises incorporating in said layer a coupler compound having the formula:
C ON
exposing said layer and developing it with a primary aromatic amino developing agent, thereby splitting 01f the group in said coupler compound and coupling said compound at the point of splitting with the oxidation product of the primary aromatic amino developing agent to form a, dye image.
6. A gelatino silver halide emulsion layer containing a coupler compound having the formula:
N=NR
where X is selected from the class consisting of hydrogen and alkyl radicals, Y is selected from the class consisting of mononuclear aryl radicals, aralkyl radicals and R is a mononuclear aryl radical.
7. A gelatino silver halide emulsion layer containing a coupler compound having the formula:
O ONH-Y N=NR Where Y and R are mononuclear aryl radicals.
a 8. A gelatino silver halide emulsion layer containing a coupler compound having the formula:
O ONH-Y where Y is a mononuclear aryloxyphenyl radical and R is a mononuclear aryl radical.
9. A gelatino silver halide emulsion layer containing a coupler compound having the formula:
O OK CH3 1 O N=N 10. A gelatino silver halide emulsion layer containing a, coupler compound having the formula:
C O N- 5 DUDLEY B. GLASS.
PAUL W. VITTUM. ARNOLD WEISSBERGER.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS

Claims (1)

1. THE METHOD OF DEVELOPING A COLORED IMAGE IN A SILVER HALIDE EMULSION LAYER WHICH COMPRISES EXPOSING SAID EMULSION LAYER AND DEVELOPING IT WITH A PRIMARY AROMATIC AMINO DEVELOPING AGENT IN THE PRESENCE OF A COUPLER COMPOUND HAVING THE FORMULA:
US734548A 1945-08-30 1947-03-13 1-hydroxy-2-naphthamide colored couplers Expired - Lifetime US2521908A (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
BE480525D BE480525A (en) 1947-03-13
BE476362D BE476362A (en) 1947-03-13
US613456A US2428054A (en) 1945-08-30 1945-08-30 Photographic color correction using colored couplers
FR950288D FR950288A (en) 1947-03-13 1946-08-29 Improvements in color photography
US734548A US2521908A (en) 1947-03-13 1947-03-13 1-hydroxy-2-naphthamide colored couplers
GB18258/47A GB627814A (en) 1947-03-13 1947-07-10 Improvements in colour photographic development and colour-forming developers
FR950228D FR950228A (en) 1947-03-13 1947-07-28 Method and furnace for heating steel parts
CH283456D CH283456A (en) 1947-03-13 1947-12-23 Process for obtaining a colored image free from metallic silver and image obtained by this process.
CH285169D CH285169A (en) 1947-03-13 1947-12-23 Photosensitive material for color photography.
FR980372D FR980372A (en) 1947-03-13 1948-02-16 Colored couplers of the 1-hydroxy-2-naphthamide series
ES0183158A ES183158A1 (en) 1947-03-13 1948-04-06 A CHROMOGEN DEVELOPMENT PROCEDURE FOR COLOR PHOTOGRAPHY

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BE (2) BE476362A (en)
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GB (1) GB627814A (en)

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US2706684A (en) * 1952-11-28 1955-04-19 Eastman Kodak Co 1-hydroxy-2-naphthamide colored couplers
US3034892A (en) * 1958-10-27 1962-05-15 Eastman Kodak Co Magenta-colored cyan-forming couplers
US3077402A (en) * 1954-12-06 1963-02-12 Polaroid Corp Photographic color processes, products, and compositions
US3227550A (en) * 1962-09-07 1966-01-04 Eastman Kodak Co Photographic color reproduction process and element
US3459552A (en) * 1965-02-03 1969-08-05 Fuji Photo Film Co Ltd Silver halide emulsions containing magenta-colored cyan couplers
US3658545A (en) * 1968-12-20 1972-04-25 Konishiroku Photo Ind Light-sensitive silver halide color photographic material containing cyan couplers
EP0112162A2 (en) 1982-12-13 1984-06-27 Konica Corporation Light-sensitive silver halide photographic material
EP0124795A2 (en) 1983-04-11 1984-11-14 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion
EP0147854A2 (en) 1983-12-29 1985-07-10 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive 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
EP0209118A2 (en) 1985-07-17 1987-01-21 Konica Corporation Silver halide photographic material
EP0228914A2 (en) 1985-12-28 1987-07-15 Konica Corporation Method of processing lightsensitive silver halide color photographic material
US5178993A (en) * 1990-03-01 1993-01-12 Fuji Photo Film Co., Ltd. Method for processing silver halide color photographic material
US5256772A (en) * 1990-11-14 1993-10-26 Toyo Ink Manufacturing Co., Ltd. Monoazo lake pigment and uses thereof
US5286287A (en) * 1990-10-11 1994-02-15 Toyo Ink Manufacturing Co., Ltd. Monoazo lake pigment suitable for use in printing ink and process for the production thereof
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
EP0711804A2 (en) 1994-11-14 1996-05-15 Ciba-Geigy Ag Latent light stabilizers

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US2725291A (en) * 1952-05-01 1955-11-29 Eastman Kodak Co Azo dye couplers having two coupling nuclei
US2725292A (en) * 1952-05-15 1955-11-29 Eastman Kodak Co Colored couplers containing solubilizing groups
US3418121A (en) * 1964-11-11 1968-12-24 Fuji Photo Film Co Ltd Photographic developer composition containing 2-(o-propionamido-beta-phenylethyl) - 1 - hydroxynaphthamide as a color former

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Cited By (18)

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Publication number Priority date Publication date Assignee Title
US2706684A (en) * 1952-11-28 1955-04-19 Eastman Kodak Co 1-hydroxy-2-naphthamide colored couplers
US3077402A (en) * 1954-12-06 1963-02-12 Polaroid Corp Photographic color processes, products, and compositions
US3034892A (en) * 1958-10-27 1962-05-15 Eastman Kodak Co Magenta-colored cyan-forming couplers
US3227550A (en) * 1962-09-07 1966-01-04 Eastman Kodak Co Photographic color reproduction process and element
US3459552A (en) * 1965-02-03 1969-08-05 Fuji Photo Film Co Ltd Silver halide emulsions containing magenta-colored cyan couplers
US3658545A (en) * 1968-12-20 1972-04-25 Konishiroku Photo Ind Light-sensitive silver halide color photographic material containing cyan couplers
EP0112162A2 (en) 1982-12-13 1984-06-27 Konica Corporation Light-sensitive silver halide photographic material
EP0124795A2 (en) 1983-04-11 1984-11-14 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion
EP0147854A2 (en) 1983-12-29 1985-07-10 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive 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
EP0209118A2 (en) 1985-07-17 1987-01-21 Konica Corporation Silver halide photographic material
EP0228914A2 (en) 1985-12-28 1987-07-15 Konica Corporation Method of processing lightsensitive silver halide color photographic 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
US5178993A (en) * 1990-03-01 1993-01-12 Fuji Photo Film Co., Ltd. Method for processing silver halide color photographic material
US5286287A (en) * 1990-10-11 1994-02-15 Toyo Ink Manufacturing Co., Ltd. Monoazo lake pigment suitable for use in printing ink and process for the production thereof
US5256772A (en) * 1990-11-14 1993-10-26 Toyo Ink Manufacturing Co., Ltd. Monoazo lake pigment and uses thereof
EP0711804A2 (en) 1994-11-14 1996-05-15 Ciba-Geigy Ag Latent light stabilizers

Also Published As

Publication number Publication date
BE476362A (en)
FR950228A (en) 1949-09-21
FR980372A (en) 1951-05-11
BE480525A (en)
GB627814A (en) 1949-08-16
CH283456A (en) 1952-06-15
ES183158A1 (en) 1948-06-01
FR950288A (en) 1949-09-22
CH285169A (en) 1952-08-31

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