US2453661A - Colored couplers - Google Patents

Colored couplers Download PDF

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Publication number
US2453661A
US2453661A US533930A US53393044A US2453661A US 2453661 A US2453661 A US 2453661A US 533930 A US533930 A US 533930A US 53393044 A US53393044 A US 53393044A US 2453661 A US2453661 A US 2453661A
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US
United States
Prior art keywords
coupler
compound
developing
group
colored
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US533930A
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English (en)
Inventor
Dudley B Glass
Weissberger Arnold
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eastman Kodak Co
Original Assignee
Eastman Kodak Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to US533930A priority Critical patent/US2453661A/en
Priority to FR950285D priority patent/FR950285A/fr
Priority to NL134793A priority patent/NL71531C/nl
Priority to BE476359A priority patent/BE476359A/fr
Priority to CH280512D priority patent/CH280512A/fr
Priority to CH282409D priority patent/CH282409A/fr
Application granted granted Critical
Publication of US2453661A publication Critical patent/US2453661A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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

Definitions

  • This invention relates to color photography and particularly to coupler compounds for use in photographic processes.
  • Color-forming compounds which react with the development product of aromatic amino develop- .ing agents to form colored images upon photographic development are well known. Generally, these color-forming compounds or 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 colcred image. When the coupler is used in the developing solution, it may be colored without detriment to the final image, and some colored couplers are known, such as paraphenylazoacetoacetanilide which was disclosed in 5Mannes and Godowsky Patent 2,108,602.
  • the new couplers are, in themselves, more or less strongly colored, and during the coupling reaction, the chromophore system in the coupler is broken up with the result that the original color of the coupler is destroyed and a new dye is formed.
  • the coupler color is destroyed, and a new color is formed by the coupling reaction, at those points where development occurs. There is formed in this way a dye image of one color on a background of another color.
  • an object of the present invention to provide a colored coupler whose chromophore system is destroyed on coupling.
  • a further object is to provide a novel radical-replacement type of chemical reaction.
  • a still further object is to provide color couplers suitable for color correction processes of color phtography.
  • H j' R. is an alkyl, aryl or a heterocyclic group
  • R is a substituted or unsubstituted aromatic or heterocycllc radical.
  • the structure may be that of a hydrazone or some other tautomeric form or a mixture of these as indicated" by the following structures:
  • the compounds When incorporated in the emulsion layer, the compounds may be added directly to the silver halide emulsion as the sodium or other Water-soluble salt, or they may be incorporated in a coupler solvent as described in Mannes and Godowsky U. S. Patent 2,304,940 or Jelley and Vittum U. S. Patent 2,322,027.
  • the compounds employed according to our invention may be produced by any suitable method, such as by reaction of the reactive methylene compound with the appropriate diazonium compound.
  • compound No. 2 was prepared as follows;
  • Our compounds are particularly useful in a process such as that of Hanson U. S. application Serial No. 538,910 filed May 33, 1944, now Patent No. 2,449,966, September 21, 1948.
  • the Hanson process involves a color correction method in which a colored coupler is incorporated in the photographic emulsion layer prior to exposure and upon development is converted into a colored image where the layer was exposed.
  • the coupler remaining in the unexposed portions of the layer retains its original color, and by suitable choice of the color of the originalcoupler and the color of the final dye image, a masking or correction effect can be obtained.
  • the primary aromatic amino developing agents are generally suitable including the phenylenedia mines and the aminophenols;
  • the alkyl phenylenediamines may be substituted in the amino group as well as in the ring.
  • Suitable compounds are diethyl paraphenylenediamine, monomethyl paraphenylene-diamine, dimethyl paraphenylenediamine and paraaminophenol. These compounds are usually employed in the salt form, such as the hydrochloride or the sulphate, which are more stable than the free amines. All of these compounds have a primary amino group which enables the oxidation product of the developer to couple with the color-forming compounds to form dye images.
  • the following developing solution is suitable for developing gelatino silver halide layers containing colored couplers according to our invention.
  • OHN NR where X and Y are negative groups selected from the class consisting of COR, -COOR,
  • R. is selected from the class consisting of alkyl, aryl, and heterocyclic groups and R is selected from the class consisting of aromatic and heterocyclic radicals and said coupler compound contains no other reactive CH group, and at the place of the silver image formed by the development, splittingsaid coupler compound at the azo linkage and coupling said coupler compound where the splitting occurs, with the development product of the primary aromatic amino developing agent.
  • ⁇ CH-N N-R'
  • X and Y are negative groups selected from the class consisting of -COR, --COOR,
  • -COCOR, -COCOOR, -CONI]IR., -C6H4NO2 and CN R is selected from the class consisting of alkyl, aryl, and heterocyclic groups and R is an aromatic radical of the benzene series and said coupler compound contains no other reactive CH group, and at the place of the silver image formed by the development, splitting said coupler compound at the azo linkage and coupling said coupler compound where the splitting occurs, with the development product of the primary aromatic amino developing agent.
  • X and Y are negative groups selected from the class consisting of COR, -COOR,
  • R is selected from the class consisting of alkyl, aryl and heterocyclic and R is selected from the class consisting of aromatic and heterocyclic radicals and said coupler compound contains no other reactive CH group, exposing said layer and developing it with a primary aromatic amino developing agent, thereby splitting off the --N:N-R 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, leaving said coupler compound intact in the re gions of said layer undeveloped by said. developing agent.
  • X and Y are negative groups selected from the class consisting of COR, COOR, COCOR, COCOOR, CONHR, 'CsI-I4NO2 and CN
  • B is selected from the class consisting of alkyl, aryl and heterocyclic and R is an aromatic radical of the benzene series
  • X and Y are negative groups selected from the class consisting of COR, COOR,
  • R is selected from the class consisting of alkyl, aryl and heterocyclic groups and R is selected from the class consisting of aromatic and heterocyclic radicals, and said coupler compound contains no other reactive CH group.
  • X and Y are negative groups selected from the class consisting of --COR, -COOR,
  • R is selected from the class consisting of alkyl, aryl and heterocyclic groups and R is an aromatic radical of the benzene series, and said coupler compound contains no other reactive CH group.
  • COCOR,--COCOOR, --CONHR, CsH4NO-z and CN and R is selected from the class consisting of alkyl, aryl and heterocyclic groups, and said coupler compound contains no other reactive CI-I group.
  • R is a carboxylic acid acyl group and R is an aryl group
  • said coupler compound contains no other reactive CH group and at the place of the silver image formed by the development, splitting said coupler compound at the azo linkage and coupling said coupler compound where the splitting occurs, with the development product of the primary aromatic amino developing agent.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US533930A 1944-05-03 1944-05-03 Colored couplers Expired - Lifetime US2453661A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US533930A US2453661A (en) 1944-05-03 1944-05-03 Colored couplers
FR950285D FR950285A (fr) 1944-05-03 1946-08-29 Coupleurs colorés
NL134793A NL71531C (uk) 1944-05-03 1947-09-13
BE476359A BE476359A (uk) 1944-05-03 1947-09-27
CH280512D CH280512A (fr) 1944-05-03 1947-12-22 Procédé pour l'obtention d'une image colorée exempte d'argent métallique, et image obtenue par ce procédé.
CH282409D CH282409A (fr) 1944-05-03 1947-12-22 Matériel photosensible pour la photographie en couleurs.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US533930A US2453661A (en) 1944-05-03 1944-05-03 Colored couplers

Publications (1)

Publication Number Publication Date
US2453661A true US2453661A (en) 1948-11-09

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Family Applications (1)

Application Number Title Priority Date Filing Date
US533930A Expired - Lifetime US2453661A (en) 1944-05-03 1944-05-03 Colored couplers

Country Status (5)

Country Link
US (1) US2453661A (uk)
BE (1) BE476359A (uk)
CH (2) CH280512A (uk)
FR (1) FR950285A (uk)
NL (1) NL71531C (uk)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2515691A (en) * 1946-08-21 1950-07-18 Gevaert Photo Prod Nv Azo dyestuffs as photographic coupling components
US2531004A (en) * 1947-11-26 1950-11-21 Gen Aniline & Film Corp Acetonitriles as azo components in diazotypes
US2533185A (en) * 1947-10-22 1950-12-05 Gen Aniline & Film Corp Alkyl malonamates as azo coupling components in diazotype layers
US2537001A (en) * 1947-08-06 1951-01-02 Gen Aniline & Film Corp Diazotype layers having cyan acetyl amides as azo components
US2543691A (en) * 1946-06-07 1951-02-27 Gen Aniline & Film Corp Azo dyes as silver halide photographic developing agents
US2584349A (en) * 1944-11-10 1952-02-05 Gen Aniline & Film Corp Color forming development with an aromatic primary amino developer and alpha-[4-sulfophenylazo]-aceto-acet-2-4-dichloroanilide
US2774668A (en) * 1953-05-28 1956-12-18 Polaroid Corp Process and product for forming color images from complete dyes
US2874146A (en) * 1955-06-29 1959-02-17 Ici Ltd Polymeric compositions
US3148062A (en) * 1959-04-06 1964-09-08 Eastman Kodak Co Photographic elements and processes using splittable couplers
US3227550A (en) * 1962-09-07 1966-01-04 Eastman Kodak Co Photographic color reproduction process and element
US3227554A (en) * 1959-04-06 1966-01-04 Eastman Kodak Co Photographic elements and processes utilizing mercaptan-forming couplers
US5100760A (en) * 1986-02-24 1992-03-31 Fuji Photo Film Co., Ltd. Light-sensitive material containing silver halide, reducing agent and polymerizable compound
US20080015342A1 (en) * 2004-12-27 2008-01-17 Enrico Traverso Aromatic-Aliphatic Azo Derivatives Particularly As Markers For Petroleum Products, Method For Synthesizing Them, Use Thereof And Derived Compositions

Citations (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB503752A (en) * 1936-07-07 1939-04-11 Kodak Ltd Process of colour photography
GB503824A (en) * 1936-07-07 1939-04-11 Kodak Ltd Process of colour photography
US2220123A (en) * 1938-10-01 1940-11-05 Bela Gaspar Color photographic process
US2220065A (en) * 1938-10-29 1940-11-05 Du Pont Aminophenols and their preparation
US2227981A (en) * 1937-10-22 1941-01-07 Eastman Kodak Co Method of preparation of natural color pictures
US2263012A (en) * 1937-12-23 1941-11-18 Eastman Kodak Co Process for making natural color photographs
US2271230A (en) * 1939-09-07 1942-01-27 Eastman Kodak Co Sulphonamides of dyes
US2295009A (en) * 1940-03-12 1942-09-08 Eastman Kodak Co Photographic color forming compound
US2295008A (en) * 1940-03-12 1942-09-08 Eastman Kodak Co Photographic color forming compound
US2296306A (en) * 1938-10-26 1942-09-22 Eastman Kodak Co Nondiffusing metallic salt coupler compound
US2299641A (en) * 1939-12-26 1942-10-20 Du Pont Processes of color photography and compositions and elements therefor
US2301861A (en) * 1939-11-10 1942-11-10 Du Pont Ketone-amine compounds
US2304820A (en) * 1939-10-24 1942-12-15 Du Pont Substituted monoamides of aliphatic dibasic acids
US2310943A (en) * 1938-10-05 1943-02-16 Du Pont Polyvinyl acetals
US2328802A (en) * 1942-05-02 1943-09-07 Wingfoot Corp New process
US2336215A (en) * 1941-03-15 1943-12-07 Eastman Kodak Co Isoalkylidene aminophenol

Patent Citations (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB503824A (en) * 1936-07-07 1939-04-11 Kodak Ltd Process of colour photography
GB503752A (en) * 1936-07-07 1939-04-11 Kodak Ltd Process of colour photography
US2227981A (en) * 1937-10-22 1941-01-07 Eastman Kodak Co Method of preparation of natural color pictures
US2263012A (en) * 1937-12-23 1941-11-18 Eastman Kodak Co Process for making natural color photographs
US2220123A (en) * 1938-10-01 1940-11-05 Bela Gaspar Color photographic process
US2310943A (en) * 1938-10-05 1943-02-16 Du Pont Polyvinyl acetals
US2296306A (en) * 1938-10-26 1942-09-22 Eastman Kodak Co Nondiffusing metallic salt coupler compound
US2220065A (en) * 1938-10-29 1940-11-05 Du Pont Aminophenols and their preparation
US2271230A (en) * 1939-09-07 1942-01-27 Eastman Kodak Co Sulphonamides of dyes
US2304820A (en) * 1939-10-24 1942-12-15 Du Pont Substituted monoamides of aliphatic dibasic acids
US2301861A (en) * 1939-11-10 1942-11-10 Du Pont Ketone-amine compounds
US2299641A (en) * 1939-12-26 1942-10-20 Du Pont Processes of color photography and compositions and elements therefor
US2295008A (en) * 1940-03-12 1942-09-08 Eastman Kodak Co Photographic color forming compound
US2295009A (en) * 1940-03-12 1942-09-08 Eastman Kodak Co Photographic color forming compound
US2336215A (en) * 1941-03-15 1943-12-07 Eastman Kodak Co Isoalkylidene aminophenol
US2328802A (en) * 1942-05-02 1943-09-07 Wingfoot Corp New process

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2584349A (en) * 1944-11-10 1952-02-05 Gen Aniline & Film Corp Color forming development with an aromatic primary amino developer and alpha-[4-sulfophenylazo]-aceto-acet-2-4-dichloroanilide
US2543691A (en) * 1946-06-07 1951-02-27 Gen Aniline & Film Corp Azo dyes as silver halide photographic developing agents
US2515691A (en) * 1946-08-21 1950-07-18 Gevaert Photo Prod Nv Azo dyestuffs as photographic coupling components
US2537001A (en) * 1947-08-06 1951-01-02 Gen Aniline & Film Corp Diazotype layers having cyan acetyl amides as azo components
US2533185A (en) * 1947-10-22 1950-12-05 Gen Aniline & Film Corp Alkyl malonamates as azo coupling components in diazotype layers
US2531004A (en) * 1947-11-26 1950-11-21 Gen Aniline & Film Corp Acetonitriles as azo components in diazotypes
US2774668A (en) * 1953-05-28 1956-12-18 Polaroid Corp Process and product for forming color images from complete dyes
US2874146A (en) * 1955-06-29 1959-02-17 Ici Ltd Polymeric compositions
US3148062A (en) * 1959-04-06 1964-09-08 Eastman Kodak Co Photographic elements and processes using splittable couplers
US3227554A (en) * 1959-04-06 1966-01-04 Eastman Kodak Co Photographic elements and processes utilizing mercaptan-forming couplers
US3227550A (en) * 1962-09-07 1966-01-04 Eastman Kodak Co Photographic color reproduction process and element
US5100760A (en) * 1986-02-24 1992-03-31 Fuji Photo Film Co., Ltd. Light-sensitive material containing silver halide, reducing agent and polymerizable compound
US20080015342A1 (en) * 2004-12-27 2008-01-17 Enrico Traverso Aromatic-Aliphatic Azo Derivatives Particularly As Markers For Petroleum Products, Method For Synthesizing Them, Use Thereof And Derived Compositions
US7956170B2 (en) * 2004-12-27 2011-06-07 Enrico Traverso Aromatic-aliphatic azo derivatives particularly as markers for petroleum products, method for synthesizing them, use thereof and derived compositions

Also Published As

Publication number Publication date
CH282409A (fr) 1952-04-30
CH280512A (fr) 1952-01-31
FR950285A (fr) 1949-09-22
NL71531C (uk) 1952-12-16
BE476359A (uk) 1947-10-31

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