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US2455169A - Colored couplers - Google Patents

Colored couplers Download PDF

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Publication number
US2455169A
US2455169A US533931A US53393144A US2455169A US 2455169 A US2455169 A US 2455169A US 533931 A US533931 A US 533931A US 53393144 A US53393144 A US 53393144A US 2455169 A US2455169 A US 2455169A
Authority
US
United States
Prior art keywords
coupler
developing
layer
colored
compound
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
US533931A
Other languages
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
Priority to NL71530D priority Critical patent/NL71530C/xx
Priority to BE476360D priority patent/BE476360A/xx
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to US533931A priority patent/US2455169A/en
Priority to FR950286D priority patent/FR950286A/fr
Priority to CH282410D priority patent/CH282410A/fr
Priority to CH280513D priority patent/CH280513A/fr
Priority to ES0181502A priority patent/ES181502A1/es
Application granted granted Critical
Publication of US2455169A publication Critical patent/US2455169A/en
Priority to DEE2173A priority patent/DE902582C/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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

  • 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 or couplers are colorless or substantially colorless. This lack of color is usually desirable where the coupler is to be incorporatedin the emulsion layer and the unused coupler remains after formation of the colored image. When the coupler is used in the developing solution, it ma be colored without detriment to the final image, and some colored couplers are known, such as paraphenylazo acetoacetanilide which wasdisclosed in Mannes an Godowsky Patent 2,108,602.
  • the new couplers are, in themselves, more or less strongly colored, and during the coupling reacfurther substituted.
  • the aromatic or heterotion 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 corwhere R is an aromatic or heterocyclic radical, especially an aromatic radical of the benzene series. Either the phenol nucleus or the aromatic or heterocyclic radical may contain other substltuents.
  • the phenol radical may have a fused-on benzene ring which may be cyclic radical (R in the general formula) may contain substituents; such as alkyl, carboxylic acid, hydroxyl, sulfonic acid, sulfonamide, alkylamine, acylamine or alkoxy.
  • the photographic developing solution-or in the emulsion layer according to their intended use and diffusion characteristics.
  • Nos. 4, 5, 6-,. and .8 are suitable for use in the'emulsion layer.
  • the compounds When. incorporated in the emulsion layer, the compounds may be added directly to their silver halide emulsion as the sodium or other water-soluble salt or they may be incorporated in a coupler solvent as. de
  • diazotized solution was added to a solution of 144 g. (01 mole) of a-naphthol in 160 cc. of water which contained g. (0.5 mole) of sodium hydroxide. Ice was added in order to keep the temperature below 5 C. After standing for two hours .at.5 0., the alkaline solution was acidified mine and-para-aminophenol.
  • TheI-Ianson process involves a color correction methodin which a colored coupler is incorporated in the photographic emulsion layer prior to exposureand upon development is converted into 'a colored imagewhere the layer was exposed.
  • the coupler remaining in the unexposed portions of the layer retains its original color, and by suitable choice of thecolor of the original coupler and the color of the. final dye image, a masking or correction efiect. can be. obtained.
  • 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 are diethylparaphenylenediamine, monomethyl'paraphenylenediamine, dimethyl paraphenylenedia- These compounds are. usually employed in the salt form, such as the hydrochloride or the sulphate whichare more stable than the free amines. All of' these compounds have a primary amino group which en- ;ables-the oxidation product of' the developer to couplewith'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.
  • R is selected from the class consisting of aromatic and heterocyclic radicals
  • R is a naphthalene nucleus, said nucleus having the azo group and the hydroxyl para to each other, and R is selected from the class consisting of aromatic and heterocyclic radicals
  • said coupler compound contains no reactive phenolic hydroxyl group other than that to which the azo group is attached, exposing said layer and developing it with a primary aromatic amino developing agent, thereby splitting off 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, leaving said coupler compound intact in the regions of said layer undeveloped by said developing agent.
  • X is selected from the class consisting of hydrogen, hydroxyl, sulfonic acid, sulfonamido, dialkylamino, and acetylamino groups
  • said coupler compound contains no reactive phenolic hydroxyl group other than that to which the azo group is attached, exposing said layer and developing it with a primary aromatic amino developing agent, thereby splitting off 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, leaving said coupler compound intact in the regions of said layer undeveloped by said developing agent.
  • R is selected from class consisting of aromatic and heterocyclic radicals

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US533931A 1944-05-03 1944-05-03 Colored couplers Expired - Lifetime US2455169A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
NL71530D NL71530C (hu) 1944-05-03
BE476360D BE476360A (hu) 1944-05-03
US533931A US2455169A (en) 1944-05-03 1944-05-03 Colored couplers
FR950286D FR950286A (fr) 1944-05-03 1946-08-29 Nouveaux coupleurs colorés
CH282410D CH282410A (fr) 1944-05-03 1947-12-23 Matériel photosensible pour la photographie en couleurs.
CH280513D CH280513A (fr) 1944-05-03 1947-12-23 Procédé pour l'obtention d'une image colorée exempte d'argent métallique, et image obtenue par ce procédé.
ES0181502A ES181502A1 (es) 1944-05-03 1947-12-31 UN PROCEDIMIENTO DE OBTENCIoN DE UNA IMAGEN COLORADA EN UNA CAPA DE EMULSIoN A LOS HALOGENUROS DE PLATA.
DEE2173A DE902582C (de) 1944-05-03 1950-09-22 Verfahren zum Entwickeln eines Farbbildes in einer Silberhalogenid-Emulsionsschicht

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US533931A US2455169A (en) 1944-05-03 1944-05-03 Colored couplers

Publications (1)

Publication Number Publication Date
US2455169A true US2455169A (en) 1948-11-30

Family

ID=24128024

Family Applications (1)

Application Number Title Priority Date Filing Date
US533931A Expired - Lifetime US2455169A (en) 1944-05-03 1944-05-03 Colored couplers

Country Status (7)

Country Link
US (1) US2455169A (hu)
BE (1) BE476360A (hu)
CH (2) CH280513A (hu)
DE (1) DE902582C (hu)
ES (1) ES181502A1 (hu)
FR (1) FR950286A (hu)
NL (1) NL71530C (hu)

Cited By (20)

* 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
US2521908A (en) * 1947-03-13 1950-09-12 Eastman Kodak Co 1-hydroxy-2-naphthamide colored couplers
US2725292A (en) * 1952-05-15 1955-11-29 Eastman Kodak Co Colored couplers containing solubilizing groups
US2725291A (en) * 1952-05-01 1955-11-29 Eastman Kodak Co Azo dye couplers having two coupling nuclei
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
US3625919A (en) * 1967-02-10 1971-12-07 Hiroyoshi Kamogawa Process for the preparation of diazotized vinylphenol polymers having phototropic properties
US3647468A (en) * 1967-05-15 1972-03-07 Ferrania Spa Photographic silver halide elements having magenta-colored coupler dyes
US3977825A (en) * 1973-06-22 1976-08-31 L'oreal Indoanilines in keratinic fiber dye cmpositions
US4007747A (en) * 1973-12-12 1977-02-15 Societe Anonyme Dite: L'oreal N-monosubstituted indoanilines as dyestuffs for keratinic fibers
US4379819A (en) * 1980-04-30 1983-04-12 Ciba-Geigy Ag Color-photographic recording material for the silver dye bleach process
US4777120A (en) * 1987-05-18 1988-10-11 Eastman Kodak Company Photographic element and process comprising a masking coupler
US4871655A (en) * 1987-01-16 1989-10-03 Konica Corporation Light-sensitive silver halide color photographic material containing multi-functional dye
US5100760A (en) * 1986-02-24 1992-03-31 Fuji Photo Film Co., Ltd. Light-sensitive material containing silver halide, reducing agent and polymerizable compound
EP0695968A2 (en) 1994-08-01 1996-02-07 Eastman Kodak Company Viscosity reduction in a photographic melt
EP0779544A1 (en) 1995-12-11 1997-06-18 Eastman Kodak Company Photographic element containing an improved pyrazolotriazole coupler
EP1914594A2 (en) 2004-01-30 2008-04-23 FUJIFILM Corporation Silver halide color photographic light-sensitive material and color image-forming method
WO2013032827A1 (en) 2011-08-31 2013-03-07 Eastman Kodak Company Motion picture films to provide archival images
CN114933818A (zh) * 2022-06-28 2022-08-23 绍兴文理学院 一种吲哚啉分散染料及其制备方法

Citations (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1102028A (en) * 1913-01-27 1914-06-30 Rudolf Fischer Process of making colored photographs.
US2092425A (en) * 1934-12-15 1937-09-07 Soc Of Chemical Ind Nu-anthraquinonyl amino-benzene arsonic acid and process of making the same
US2107941A (en) * 1938-02-08 Fast brown leather dyesttjffs and a
US2108602A (en) * 1935-03-21 1938-02-15 Eastman Kodak Co Photographic color-forming compounds
US2135366A (en) * 1938-11-01 Naphthazarine intermediate-aro
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
US2182814A (en) * 1938-12-12 1939-12-12 Du Pont Film Mfg Corp Photographic film
US2189817A (en) * 1939-03-13 1940-02-13 Du Pont Film Mfg Corp Color-forming photographic composition, element, and process
US2220123A (en) * 1938-10-01 1940-11-05 Bela Gaspar Color photographic process
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
US2297732A (en) * 1940-05-15 1942-10-06 Du Pont Photographic color process involving the formation of azo dye images
US2299641A (en) * 1939-12-26 1942-10-20 Du Pont Processes of color photography and compositions and elements therefor
US2304820A (en) * 1939-10-24 1942-12-15 Du Pont Substituted monoamides of aliphatic dibasic acids
US2308023A (en) * 1938-10-26 1943-01-12 Eastman Kodak Co Colored photographic image
US2322006A (en) * 1939-12-29 1943-06-15 Eastman Kodak Co Photographic filter and antihalation layer
US2330291A (en) * 1939-10-24 1943-09-28 Du Pont Dye intermediate
US2367531A (en) * 1942-06-12 1945-01-16 Eastman Kodak Co Acylaminophenol photographic couplers

Patent Citations (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2107941A (en) * 1938-02-08 Fast brown leather dyesttjffs and a
US2135366A (en) * 1938-11-01 Naphthazarine intermediate-aro
US1102028A (en) * 1913-01-27 1914-06-30 Rudolf Fischer Process of making colored photographs.
US2092425A (en) * 1934-12-15 1937-09-07 Soc Of Chemical Ind Nu-anthraquinonyl amino-benzene arsonic acid and process of making the same
US2108602A (en) * 1935-03-21 1938-02-15 Eastman Kodak Co Photographic color-forming compounds
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
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
US2308023A (en) * 1938-10-26 1943-01-12 Eastman Kodak Co Colored photographic image
US2182814A (en) * 1938-12-12 1939-12-12 Du Pont Film Mfg Corp Photographic film
US2189817A (en) * 1939-03-13 1940-02-13 Du Pont Film Mfg Corp Color-forming photographic composition, element, and process
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
US2330291A (en) * 1939-10-24 1943-09-28 Du Pont Dye intermediate
US2299641A (en) * 1939-12-26 1942-10-20 Du Pont Processes of color photography and compositions and elements therefor
US2322006A (en) * 1939-12-29 1943-06-15 Eastman Kodak Co Photographic filter and antihalation layer
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
US2297732A (en) * 1940-05-15 1942-10-06 Du Pont Photographic color process involving the formation of azo dye images
US2367531A (en) * 1942-06-12 1945-01-16 Eastman Kodak Co Acylaminophenol photographic couplers

Cited By (21)

* 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
US2521908A (en) * 1947-03-13 1950-09-12 Eastman Kodak Co 1-hydroxy-2-naphthamide colored couplers
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
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
US3625919A (en) * 1967-02-10 1971-12-07 Hiroyoshi Kamogawa Process for the preparation of diazotized vinylphenol polymers having phototropic properties
US3647468A (en) * 1967-05-15 1972-03-07 Ferrania Spa Photographic silver halide elements having magenta-colored coupler dyes
US3977825A (en) * 1973-06-22 1976-08-31 L'oreal Indoanilines in keratinic fiber dye cmpositions
US4007747A (en) * 1973-12-12 1977-02-15 Societe Anonyme Dite: L'oreal N-monosubstituted indoanilines as dyestuffs for keratinic fibers
US4379819A (en) * 1980-04-30 1983-04-12 Ciba-Geigy Ag Color-photographic recording material for the silver dye bleach process
US5100760A (en) * 1986-02-24 1992-03-31 Fuji Photo Film Co., Ltd. Light-sensitive material containing silver halide, reducing agent and polymerizable compound
US4871655A (en) * 1987-01-16 1989-10-03 Konica Corporation Light-sensitive silver halide color photographic material containing multi-functional dye
US4777120A (en) * 1987-05-18 1988-10-11 Eastman Kodak Company Photographic element and process comprising a masking coupler
EP0695968A2 (en) 1994-08-01 1996-02-07 Eastman Kodak Company Viscosity reduction in a photographic melt
EP0779544A1 (en) 1995-12-11 1997-06-18 Eastman Kodak Company Photographic element containing an improved pyrazolotriazole coupler
EP1914594A2 (en) 2004-01-30 2008-04-23 FUJIFILM Corporation Silver halide color photographic light-sensitive material and color image-forming method
WO2013032827A1 (en) 2011-08-31 2013-03-07 Eastman Kodak Company Motion picture films to provide archival images
CN114933818A (zh) * 2022-06-28 2022-08-23 绍兴文理学院 一种吲哚啉分散染料及其制备方法
CN114933818B (zh) * 2022-06-28 2024-01-16 绍兴文理学院 一种吲哚啉分散染料及其制备方法

Also Published As

Publication number Publication date
ES181502A1 (es) 1948-04-16
BE476360A (hu)
DE902582C (de) 1954-01-25
CH280513A (fr) 1952-01-31
CH282410A (fr) 1952-04-30
NL71530C (hu)
FR950286A (fr) 1949-09-22

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