US3226230A - Light-sensitive emulsions containing non-migratory n-substituted 1-hydroxy-2-naphthamide color couplers - Google Patents

Light-sensitive emulsions containing non-migratory n-substituted 1-hydroxy-2-naphthamide color couplers Download PDF

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US3226230A
US3226230A US65883A US6588360A US3226230A US 3226230 A US3226230 A US 3226230A US 65883 A US65883 A US 65883A US 6588360 A US6588360 A US 6588360A US 3226230 A US3226230 A US 3226230A
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hydroxy
color
light
layer
naphthamide
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Raphael Karel Van Poucke
Eynde Hector Alfons Van Den
Cat Arthur Henri De
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Gevaert Photo Producten NV
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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
    • G03C7/34—Couplers containing phenols
    • G03C7/344—Naphtholic couplers

Definitions

  • a photographic color image by developing a reducible silver salt image in the presence of a color coupler, i.e. a compound which during development couples with the oxidation product of the developing agent and forms a dyestufl on the area where the silver salt is reduced.
  • a color coupler i.e. a compound which during development couples with the oxidation product of the developing agent and forms a dyestufl on the area where the silver salt is reduced.
  • the modern methods of color photography are based upon the subtractive color principle according to which differently sensitized silver halide emulsion layers are superposed, each of them containing a color coupler which produces the subtractive yellow-, cyanand magenta-dyestufl images by development in a solution containing a primary aromatic amine.
  • the new color couplers can be prepared by condensation of a l-hydroxy-Z-naphthoic acid or a derivative thereof with the aromatic amine desired.
  • a sulfonic acid group it is advantageous to bring into the naphthol resp. anilide group before the condensation a sulfofluoride group which after condensation is saponified to the corresponding sulfonic acid, e.g. by application of the method described in Belgian patent specifications 584,152 and 590,934.
  • the color couplers must be incorporated into a photographic silver halide emulsion which in its turn is incorporated into a material having one or more layers.
  • the color couplers can be incorporated into said emulsions by means of the usual colloids such as gelatin, polyvinyl alcohol, collodium or other natural or synthetic colloids such as e.g. those prepared according to the Belgian patent specification 568,153.
  • the silver halide emulsions can be applied to a support consisting of paper, glass, nitrocellulose, cellulose esters such as cellulose triacetate, polyester, polystyrene or an other natural or synthetic resin.
  • This multilayer material is usually composed of the following layers: a support, a red-sensitive emulsion layer having a color coupler for cyan, a green light-sensitive emulsion layer with color coupler for magenta and a blue-light sensitive emulsion layer having a color coupler for yellow. Between the blue-light sensitive and the green-light-sensitive emulsion layer, there is a yellow filter layer which in most cases consists of colloidal silver.
  • the new color couplers into the light-sensitive silver halide emulsion layer itself but they can also be incorporated into an adjacent non-light-sensitive colloid layer or into a non-lightsensitive layer which is separated from the light-sensitive emulsion layer by a water-permeable colloid layer.
  • aromatic amino-compounds can be used as developers for such material: mono-, diand triaminoaryl compounds, more especially N,N-dialkyl-p-phenylene diamine and its derivatives such as N,N-dialkyl-N'- sulphomethylor carboxymethyl p-phenylenediamine.
  • mono-amino-developer aminophenols and aminocresols, or their halogen derivatives and also the aminonaphthols are considered.
  • Example 1 10 parts of N-[(2-cetylmercapto-5-sulfo)phenyl]-1- hydroXy-4-bromo-2-naphthoic acid amide sodium salt are wetted with 40 parts of ethanol. The whole is dissolved by adding 20 parts of water and by heating at 40 C. This solution is diluted with Water up to 200 parts till obtaining a 5% solution. 200 parts of this color coupler solution and 260 parts of Water are added to 500 parts of silver bromo-iodide gelatin emulsion (2% iodide). After adding the usual additives such as hardening agents and wetting agents the emulsion obtained is coated onto a photographic support. After drying, the photographic material is exposed and treated with a developing solution of the following composition:
  • N,N-diethyl-p-phenylenediamine hydrochloride 2.75 Sodium sulphite 2 Potassium carbonate 75 Potassium bromide 0.5 Hydroxylamine hydrochloride 1.2 Sodium hexametaphosphate 1.0
  • This material is rinsed for 30 seconds and fixed in a fixing bath of the following composition:
  • Example 2 10 parts of N (2-cetylmercapto-5-sulfophenyl)-1-hydroxy-4-chloro-2-naphthoic acid amide sodium salt are wetted with 20 parts of ethanol dissolved into 180 parts of water. Now the color coupler solution is incorporated into the emulsion according to Example 1. The material is exposed and treated in the same way as described in Example 1. A cyan image is obtained which shows loW side-absorptions.
  • Example 3 10 parts of N-(o-cetylmercaptophenyl)-1-hydroxy-4- chloro-2-naphthoic acid amide are wetted with 30 parts of ethanol and dissolved in 25 parts of 1 N sodium hydroxide and parts of water. The color coupler solution is brought into the emulsion as described in Example 1. The emulsion is neutralized by 7.5 parts of acetic acid N/2 per 100 parts of color coupler solution.
  • Example 1 After exposure, the material is treated according to Example 1 whereby in the color developing bath 4-amino-N-ethyl- N (,8 methylsulfonamidoethyl)-rn-toluidine sesquisulphate monohydrate is substituted for N,N-diethyl-p-phen.-
  • Example 5 200 cm. of a solution 5% of N-(4-cetylmercapto-5- sulfophenyl) -1-hydroxy-4-sulfo-2-naphthoic acid disodium salt (10 g. of color coupler dissolved in cm. of ethanol and cm. of sodium hydroxide N/ 2 diluted with water to 200 cm?) are added to 500 cm. of a red-sensitized silver bromo-iodide emulsion (2% iodide). After acidification with acidic acid N/ 2 to a pH 6.5, the total volume of the emulsion is brought to 1 1.
  • This emulsion is coated onto a support which alreay is coated with an anti'nalation layer.
  • a gelatin intermediate layer on which is coated a greenlight-sensitive emulsion layer with color coupler for magenta and covered with a yellow filter layer consisting of a thin gelatin layer containing colloidal silver.
  • a blue-light-sensitive emulsion layer with a color coupler for yellow On this filter layer is then coated a blue-light-sensitive emulsion layer with a color coupler for yellow.
  • This layer is coated with an antistress layer.
  • the photographic material obtained is dried, exposed and color developed according to Example 1. In this way an image with a subtractive color reproduction of the original is obtained which has an increased transparency in the green.
  • methyl Cellosolve is a registered trademark for (ethylene glycol monomethyl ether) manufactured by Union Carbide and Carbon, New York, and is used in the foregoing specification.
  • X is selected from the group consisting of a bromine atom and chlorine atom
  • Y represents a member selected from the group consisting of a hydrogen atom, a sulfonic acid group and a sulfonate group
  • R is a hydrocarbon radical having a chain length of about 5-20 carbon atoms and sufficient to render said color coupler resistant to difiusion.
  • Light-sensitive element comprising a red light-sensitive silver halide emulsion layer and a l-hydroxy-Z-naththoic acid anilide color coupler for cyan for said layer, said color coupler being selected from the group consisting of compounds having the formulae:
  • X is selected from the group consisting of a bromine atom and a chlorine atom
  • Y represents a member selected from the group consisting of a hydrogen atom, a sulfonic acid group and a sulfonate group
  • R is a hydrocarbon radical having a chain length of about 5-20 carbon atoms and sufiicient to render said color coupler resistant to diffusion.

Description

United States Patent 3,226,230 LIGHT-SENSITIVE EMULSIONS CONTAINING NON-MIGRATORY N-SUBSTITUTED l-HY- DROXY-Z-NAPHTHAMIDE COLOR COU- PLERS Raphael Karel Van Poucke, Mechlin, and Hector Alfons Van Den Eynde and Arthur Henri De Cat, Mortsel- Antwerp, Belgium, assignors to Gevaert Photo-Producten N.V., Mortsel, Belgium, a Belgian company No Drawing. Filed Oct. 31, 1960, Ser. No. 65,883 Claims priority, application Belgium, Feb. 12, 1960, 39,565, Patent 587,525 2 Claims. (CI. 9655) This invention relates to a process for the manufacture of photographic color images by color development in the presence of a color coupler, to photographic material which contain such color couplers, and to photographic images obtained according to the process referred to.
It is known to obtain a photographic color image by developing a reducible silver salt image in the presence of a color coupler, i.e. a compound which during development couples with the oxidation product of the developing agent and forms a dyestufl on the area where the silver salt is reduced.
The modern methods of color photography are based upon the subtractive color principle according to which differently sensitized silver halide emulsion layers are superposed, each of them containing a color coupler which produces the subtractive yellow-, cyanand magenta-dyestufl images by development in a solution containing a primary aromatic amine.
Different demands are made upon the color couplers according to whether they are designed for negative or for positive material. Thus it is known that l-hydroxy- 2-naphthamide color couplers, giving after the color development clear blue images, are preferably used for the manufacture of positive color materials. On the other hand it is desired to use in the manufacture of negative materials a l-hydroxy-Z-naphthamide color coupler which is developed to a cyan image, the absorption spectrum of which is brought as much as possible to the long wavelengths with side-absorptions as low as possible. But the disadvantage of the bathochromic shifting of the absorption centre is that this eflect is almost always accompanied by an increase of unwanted side absorption viz. in the green and blue part of the spectrum.
To overcome this disadvantage there is a continuous research for cyan color couplers with a bathochromically shifted absorption spectrum whereby the side absorptions are kept as low as possible. In connection herewith we refer to the color couplers which are manufactured according to the British patent specification 831,731.
It is an object of the present invention to provide a photographic material containing a number of new color couplers.
It is another object of the present invention to provide a process to form a cyan dye color image in a lightsensitive silver halide emulsion.
Now it has been found that in the red light-sensitive silver halide emulsion of a photographic material, cyan color images are obtained with increased transparency in the green by incorporating in said emulsion an aromatic N substituted 1-l1ydroxy-2-naphthoic acid amide color coupler corresponding to the following two formulae:
CONH
l X Y and wherein The new color couplers can be prepared by condensation of a l-hydroxy-Z-naphthoic acid or a derivative thereof with the aromatic amine desired. For the preparation of color couplers which contain in the naphthol or the anilide group a sulfonic acid group it is advantageous to bring into the naphthol resp. anilide group before the condensation a sulfofluoride group which after condensation is saponified to the corresponding sulfonic acid, e.g. by application of the method described in Belgian patent specifications 584,152 and 590,934.
Hereinafter follows the preparation of some of these new color couplers.
1. Preparation of N-(o-cetylmercaptophenyl) l hydroxy-4-chloro-2-naphthoic acid amide:
15.42 g. of o-cetyl-mercaptoaniline-hydrochloride (prepared according to Farmaco (Pavia), Ed. pract., Ed. sci. 12, 206-17 (1957)), and 8.08 g. of triethylamine are mixed with cm. of anhydrous benzene whereby a gelatinous precipitate is formed. The reaction mixture is cooled off in ice and 7 g. of o-phenylene chlorophosphite (prepared according to Anschiitz et al., Ber. 76, 1943/ 222) are dropwise added whereby the amount of precipitate increases. After stirring a certain time 8.9 g. of 1-hydroxy-4-chloro'2-naphthoic acid are added and the new mixture is refluxed for 20 min. This condensation is an application of the reaction type described in J. Am. Chem. Soc. 74 (1952), 5304-9. The benzene is removed by steam distillation. On cooling, the reaction mixture, a solid N-(o-cetylmercaptophenyl)-1-hydroxy-4- chloro-Z-naphthoic acid amide is formed in the aqueous layer of the mixture. This product is sucked off and washed with a sodium bicarbonate solution. To purify the product it is recrystallized from isopropanol. Melting point: 83-34 C.
II. Preparation of N (p-cetylmercaptophenyl)-1-hydroxy-4-chloro-2-naphthoic acid amide:
111 g. of p-mercapto-acetanilide (prepared according to J. Org. Chem. 15 (1950) 405) and 203 g. of cetylbromide are dissolved in 825 cm. of methyl Cellosolve. This mixture is refluxed Whilst stirring whereafter 40 g. of potassium hydroxide dissolved in cm. of methyl Cellosolve are dropwise added to the mixture. A potassium bromide precipitate is formed and after the addition of the potassium hydroxide the reaction mixture is still refluxed whilst stirring for 30 min. whereafter 250 cm. of water are added thereto. The formed p-cetylmercaptoacetanilide crystallizes and is recrystallized from a mixture of methanol and methyl Cellosolve. Melting point: 99-100 C.
29.3 g. of the synthetized (p-cetylmercapto-acetanilide) is refluxed for 3 h. in 500 cm. of absolute ethanol with 5 equivalent of dried hydrogen chloride gas. On cooling the mixture, crystals of p-cetylmercapto-anilinehydrochloride are formed. These crystals are recrystal- 3 lized from a mixture of methanol and methyl Cellosolve. Melting point: 130-132 C.
14.75 g. of the hydrochloride and 7.75 g. of triethylamine are mixed with 100 cm? of anhydrous benzene whereby a gelatinous precipitate of treithylamine hydrochloride is formed. The reaction mixture is cooled by means of ice and 6.7 g. of o-phenylenechlorophosphite are dropwise added. The gelatinous precipitate of triethylamine hydrochloride increases and stirring is continued for a little while. Thereupon 8.5 g. of l-hydroxy- 4-chloro-2-naphthoic acid are added to the mixture, the new mixture is refluxed for 20 min., the reaction mixture is poured into hot water, the benzene layer is washed with a saturated sodium bicarbonate solution and hot water and the benzene is evaporated to dryness under vacuum till a precipitate is formed which is composed of N (p-cetylmercaptophenyl)-1-hydroxy-4-chloro-2-naphthoic acid amide. By adding n-hexane, the naphthoic acid amide is completely precipitated. The product is sucked ofi whereafter it is purified by recrystallizing from a mixture of methanol and methyl Cellosolve. Melting point: 110 C.
III. The preparation of N (2 cetylmercapto-5-sulfophenyl)-1-hydroxy-4-chloro-2-naphthoic acid amide sodium salt is described in the Belgian patent specification 590,934 (preparation 6).
IV. The preparation of N (2' cetylmercapto-5-sulfophenyl-1-hydroxy-4-bromo-2-naphthoic acid amide sodium salt is described in the Belgian patent specification 590,934 (preparation 5).
V. The preparation of N-(3'-sulfo-4'cetylmercapto) phenyl-1-hydroxy-4-sulfo-2-naphthoic acid amide disodium salt is described in the Belgian patent specification 590,934 (preparation 8).
To carry out the method according to the present invention, the color couplers must be incorporated into a photographic silver halide emulsion which in its turn is incorporated into a material having one or more layers. The color couplers can be incorporated into said emulsions by means of the usual colloids such as gelatin, polyvinyl alcohol, collodium or other natural or synthetic colloids such as e.g. those prepared according to the Belgian patent specification 568,153. The silver halide emulsions can be applied to a support consisting of paper, glass, nitrocellulose, cellulose esters such as cellulose triacetate, polyester, polystyrene or an other natural or synthetic resin. This multilayer material is usually composed of the following layers: a support, a red-sensitive emulsion layer having a color coupler for cyan, a green light-sensitive emulsion layer with color coupler for magenta and a blue-light sensitive emulsion layer having a color coupler for yellow. Between the blue-light sensitive and the green-light-sensitive emulsion layer, there is a yellow filter layer which in most cases consists of colloidal silver.
It is not only possible to incorporate the new color couplers into the light-sensitive silver halide emulsion layer itself but they can also be incorporated into an adjacent non-light-sensitive colloid layer or into a non-lightsensitive layer which is separated from the light-sensitive emulsion layer by a water-permeable colloid layer.
The following aromatic amino-compounds can be used as developers for such material: mono-, diand triaminoaryl compounds, more especially N,N-dialkyl-p-phenylene diamine and its derivatives such as N,N-dialkyl-N'- sulphomethylor carboxymethyl p-phenylenediamine. As useful mono-amino-developer, aminophenols and aminocresols, or their halogen derivatives and also the aminonaphthols are considered.
The following examples illustrate the present invention without limiting, however, the scope thereof. We draw the attention to the fact that all the amounts mentioned hereafter are parts of weight when no other indication is given.
Example 1 10 parts of N-[(2-cetylmercapto-5-sulfo)phenyl]-1- hydroXy-4-bromo-2-naphthoic acid amide sodium salt are wetted with 40 parts of ethanol. The whole is dissolved by adding 20 parts of water and by heating at 40 C. This solution is diluted with Water up to 200 parts till obtaining a 5% solution. 200 parts of this color coupler solution and 260 parts of Water are added to 500 parts of silver bromo-iodide gelatin emulsion (2% iodide). After adding the usual additives such as hardening agents and wetting agents the emulsion obtained is coated onto a photographic support. After drying, the photographic material is exposed and treated with a developing solution of the following composition:
G. N,N-diethyl-p-phenylenediamine hydrochloride 2.75 Sodium sulphite 2 Potassium carbonate 75 Potassium bromide 0.5 Hydroxylamine hydrochloride 1.2 Sodium hexametaphosphate 1.0
Water to 1000 cm.
This material is rinsed for 30 seconds and fixed in a fixing bath of the following composition:
G. Sodium thiosulphate (dry) 200 Borax 8 Sodium sulphite 25 Potassium alum 15 Boric acid 7.5
Water to 1000 cm.
Now the material is rinsed for 10 min. and bleached in a bath of the following composition:
G. Potassium ferricyanide Potassium bromide 25 Borax 20 Boric acid 5 Water to 1000 cm.
Finally the material is rinsed for 5 min. and fixed in a bath of the following composition:
G. Sodium thiosulphate (dry) Sodium sulphite 10 Sodium carbonate 14 Water to 1000 cm.
As a result of the foregoing treatments, an intense cyan image with low side-absorptions in the green range is obtained.
Example 2 10 parts of N (2-cetylmercapto-5-sulfophenyl)-1-hydroxy-4-chloro-2-naphthoic acid amide sodium salt are wetted with 20 parts of ethanol dissolved into 180 parts of water. Now the color coupler solution is incorporated into the emulsion according to Example 1. The material is exposed and treated in the same way as described in Example 1. A cyan image is obtained which shows loW side-absorptions.
Example 3 10 parts of N-(o-cetylmercaptophenyl)-1-hydroxy-4- chloro-2-naphthoic acid amide are wetted with 30 parts of ethanol and dissolved in 25 parts of 1 N sodium hydroxide and parts of water. The color coupler solution is brought into the emulsion as described in Example 1. The emulsion is neutralized by 7.5 parts of acetic acid N/2 per 100 parts of color coupler solution. After exposure, the material is treated according to Example 1 whereby in the color developing bath 4-amino-N-ethyl- N (,8 methylsulfonamidoethyl)-rn-toluidine sesquisulphate monohydrate is substituted for N,N-diethyl-p-phen.-
ylenediamine hydrochloride. side-absorptions is obtained.
A cyan image with W Example 4 Example 5 200 cm. of a solution 5% of N-(4-cetylmercapto-5- sulfophenyl) -1-hydroxy-4-sulfo-2-naphthoic acid disodium salt (10 g. of color coupler dissolved in cm. of ethanol and cm. of sodium hydroxide N/ 2 diluted with water to 200 cm?) are added to 500 cm. of a red-sensitized silver bromo-iodide emulsion (2% iodide). After acidification with acidic acid N/ 2 to a pH 6.5, the total volume of the emulsion is brought to 1 1. This emulsion is coated onto a support which alreay is coated with an anti'nalation layer. To this emulsion layer is applied a gelatin intermediate layer on which is coated a greenlight-sensitive emulsion layer with color coupler for magenta and covered with a yellow filter layer consisting of a thin gelatin layer containing colloidal silver. On this filter layer is then coated a blue-light-sensitive emulsion layer with a color coupler for yellow. This layer is coated with an antistress layer. The photographic material obtained is dried, exposed and color developed according to Example 1. In this way an image with a subtractive color reproduction of the original is obtained which has an increased transparency in the green.
The term methyl Cellosolve is a registered trademark for (ethylene glycol monomethyl ether) manufactured by Union Carbide and Carbon, New York, and is used in the foregoing specification.
We claim:
1. Process for obtaining a colored photographic image in a red light-sensitive emulsion layer containing a reducible silver salt, comprising exposing said layer and developing same with a primary aromatic amino developing agent in the presence of l-hydroxy-Z-naphthoic acid anilide color coupler for cyan selected from the group consisting of compounds having the formulae:
6 wherein X is selected from the group consisting of a bromine atom and chlorine atom,
Y represents a member selected from the group consisting of a hydrogen atom, a sulfonic acid group and a sulfonate group, and
R is a hydrocarbon radical having a chain length of about 5-20 carbon atoms and sufficient to render said color coupler resistant to difiusion.
2. Light-sensitive element comprising a red light-sensitive silver halide emulsion layer and a l-hydroxy-Z-naththoic acid anilide color coupler for cyan for said layer, said color coupler being selected from the group consisting of compounds having the formulae:
X is selected from the group consisting of a bromine atom and a chlorine atom,
Y represents a member selected from the group consisting of a hydrogen atom, a sulfonic acid group and a sulfonate group, and
R is a hydrocarbon radical having a chain length of about 5-20 carbon atoms and sufiicient to render said color coupler resistant to diffusion.
References Cited by the Examiner UNITED STATES PATENTS 2,474,293 6/ 1949 Weissberger et al 9655 2,979,405 4/1961 De Cat et a1 9655 2,993,791 7/1961 Cole et al. 96--55 3,005,709 10/1961 Coles 9655 3,006,759 10/1961 Loria et al. 96-55 3,013,879 12/1961 De Ramaix et al 9655 FOREIGN PATENTS 550,833 11/1956 Italy. 227,990 11/ 1943 Switzerland.
NORMAN G. TORCHIN, Primary Examiner.
PHILIP E. MANGAN, LOUISE P. QUAST, Examiners.

Claims (1)

1. PROCESS FOR OBTAINING A COLORED PHOTOGRAPHIC IMAGE IN A RED LIGHT-SENSITIVE EMULSION LAYER CONTAINING A REDUCIBLE SILVER SALT, COMPRISING EXPOSING SAID LAYER AND DEVELOPING SAME WITH A PRIMARY AROMATIC AMINO DEVELOPING AGENT IN THE PRESENCE OF 1-HYDROXY-2-NAPHTHOIC ACID ANILIDE COLOR COUPLER FOR CYAN SELECTED FROM THE GROUP CONSISTING OF COMPOUNDS HAVING THE FORMULAE:
US65883A 1960-02-12 1960-10-31 Light-sensitive emulsions containing non-migratory n-substituted 1-hydroxy-2-naphthamide color couplers Expired - Lifetime US3226230A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3542552A (en) * 1966-12-28 1970-11-24 Fuji Photo Film Co Ltd Color developer for color photography
US3622337A (en) * 1968-08-02 1971-11-23 Gaf Corp Cyan color formers for color photography

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH227990A (en) * 1940-07-17 1943-07-31 Ig Farbenindustrie Ag Process for the preparation of color photographic images.
US2474293A (en) * 1947-09-10 1949-06-28 Eastman Kodak Co 1-naphthol-2-carboxylic acid amide couplers for color photography
US2979405A (en) * 1956-06-22 1961-04-11 Gevaert Photo Prod Nv Light-sensitive photographic element containing a 1-hydroxy-2-naphthoic acid anilidecolor coupler
US2993791A (en) * 1957-10-31 1961-07-25 Gen Aniline & Film Corp Color couplers containing long chain alkylaminoisophthalicester groups
US3005709A (en) * 1958-01-13 1961-10-24 Gen Aniline & Film Corp Photographic couplers containing acylamino groups
US3006759A (en) * 1959-08-03 1961-10-31 Eastman Kodak Co Two-equivalent magenta-forming couplers for color photography
US3013879A (en) * 1956-12-31 1961-12-19 Gevaert Photo Prod Nv Production of color photographic images

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH227990A (en) * 1940-07-17 1943-07-31 Ig Farbenindustrie Ag Process for the preparation of color photographic images.
US2474293A (en) * 1947-09-10 1949-06-28 Eastman Kodak Co 1-naphthol-2-carboxylic acid amide couplers for color photography
US2979405A (en) * 1956-06-22 1961-04-11 Gevaert Photo Prod Nv Light-sensitive photographic element containing a 1-hydroxy-2-naphthoic acid anilidecolor coupler
US3013879A (en) * 1956-12-31 1961-12-19 Gevaert Photo Prod Nv Production of color photographic images
US2993791A (en) * 1957-10-31 1961-07-25 Gen Aniline & Film Corp Color couplers containing long chain alkylaminoisophthalicester groups
US3005709A (en) * 1958-01-13 1961-10-24 Gen Aniline & Film Corp Photographic couplers containing acylamino groups
US3006759A (en) * 1959-08-03 1961-10-31 Eastman Kodak Co Two-equivalent magenta-forming couplers for color photography

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3542552A (en) * 1966-12-28 1970-11-24 Fuji Photo Film Co Ltd Color developer for color photography
US3622337A (en) * 1968-08-02 1971-11-23 Gaf Corp Cyan color formers for color photography

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