US2434272A - Color photography with azosubstituted couplers - Google Patents

Color photography with azosubstituted couplers Download PDF

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Publication number
US2434272A
US2434272A US533933A US53393344A US2434272A US 2434272 A US2434272 A US 2434272A US 533933 A US533933 A US 533933A US 53393344 A US53393344 A US 53393344A US 2434272 A US2434272 A US 2434272A
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US
United States
Prior art keywords
layer
coupler
colored
couplers
dye
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
US533933A
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English (en)
Inventor
Edwin E Jelley
Paul W Vittum
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 US533933A priority Critical patent/US2434272A/en
Priority to CH287249D priority patent/CH287249A/fr
Application granted granted Critical
Publication of US2434272A publication Critical patent/US2434272A/en
Priority to DEE2645A priority patent/DE837958C/de
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 a method for producing stable dye images in photographic layers.
  • the emulsion layer contains a coupler having the color desired for the final dye image.
  • a coupling developing agent such as diethyl-p-phenylenediamine during which step the coupler color is destroyed at the points where development occurs leaving at these points an azomethine or indoaniline or indophenol dye image in place of the colored coupler originally present.
  • the colored coupler is left intact.
  • the layer is then subjected to a suitable treatment, such as a strong acid bath which destroys and removes the coupled dye without aiTecting the original colored coupler.
  • a suitable treatment such as a strong acid bath which destroys and removes the coupled dye without aiTecting the original colored coupler.
  • the residual silver and silver halide are then removed, leaving a reversed dye image composed of the originally incorporated colored coupler.
  • the colored coupler is incorporated in the silver halide emulsion layer which is generally of the gelatino-silver bromide type, by forming the sodium salt of the coupler and dissolving the solution directly in the emulsion prior to coating or by incorporating the coupler in a solution of a water-insoluble, water-permeable solvent as described in Mannes and Godowsky U. S. Patent 2,304,940 or our prior Patent 2,322,027.
  • the amounts of coupler employed will generally vary between 1.0 gram and 10 grams per liter of wet emulsion.
  • Thelayer containing the coupler is exposed in the usual way and is then developed in any of the usual color developers, such as pphenylenediamine or p-aminophenol.
  • a typical developer formula is as follows:
  • the removal of the silver and residual silver halide may be carried out prior to the acid treatment, or the acid treatment and the fixing may be carried out simultaneously.
  • our process can be adapted to single layer or multi-layer materials.
  • the ma: terial may be arranged in the known manner to give natural-color reversal pictures.
  • the red-sensitive layer containing cyan-col;- ored coupler would be coated on the support followed by the green-sensitive layer containing magenta-colored coupler and the blue-sensitive layer containing yellow-colored coupler.
  • sensitivity maXima which do not correspond with the absorption maxima of the colored couplers.
  • Our process may also be adapted to other known arrangements, such as, those leading to false color pictures.
  • the colored coupler in only a single layer or in less than all of the emulsion layers of the coating.
  • the remaining emulsion layers might contain colorless couplers incorporated directly in the emulsion layer in the usual Way or incorporated in waterpermeable, water-insoluble solvents as described in the Marines and Godowsky U. S. Patent 2,304,949 and in our prior Patent 2,322,027 referred to above.
  • the yellow filter layer normally coated between the top and middle emulsion layers can be dispensed with by use of a blue-sensitive emulsion layer containing a yellow-colored coupler.
  • red light only would reach the bottom red-sensitive layer so that not only would no yellow filter be, required but also the red-green color separation would be improved.
  • the colored coupler having higher stability than the unstable colorless coupler so that the stability of the final dye images could be matched.
  • This advantage is of course due to the higher stability of the azo dyes and is inherent in the colored couplers which we propose to use.
  • the colored couplers containing azo groups may be selected to produce higher fastness to heat and light than can be obtained with the azomethine or indoaniline dyes normally obtained in colordevelopment processes.
  • 'asupp ort of filrn or paper may be coated first with a red-sensitive silver halide emulsion containing a dispersion of a coupler capable of yield- .jing a cyan dye on development, followed by a clear interlayer, a green-sensitive silver halide emulsion containing a dispersion of a, coupler capable of yielding a magenta dye on development, another clear interlayer, and then a, bluesensitive silver halide emulsion containing a dispersion of a yellow-colored coupler capablev of being destroyed on development to yield, an easily removable azomethine dye.
  • An anti-abrasion layer of clear gelatin may be coated as the final layer.
  • the red-sensitive emulsion layer may contain as the cyan coupler o-lauryl phenol incorporated directly in the emulsion or a dispersion of (l) 2-0:-(4'-tert.amylphenoxy )-butyrylamino-l-phenol or (2) 5- (N- (v-phenylpropyl) N-(p-amylbenzoyl) amino) 1' naphthol, in n,- butyl phthalate or tri-orthocresylphosphate age cording to the method of our prior Patent 2,322,027.
  • the cyan coupler o-lauryl phenol incorporated directly in the emulsion or a dispersion of (l) 2-0:-(4'-tert.amylphenoxy )-butyrylamino-l-phenol or (2) 5- (N- (v-phenylpropyl) N-(p-amylbenzoyl) amino) 1' naphthol, in n
  • the green-sensitive emulsion layer may con,- tain a dispersion of (1) 1-phenyl 3;n-pentadecy1 S-pyrazolone, (2) 1-phenyl-3:palrnitylamino-E: pyrazolone, or (3) l-cyanoacetyl-g-tert.amyldiphenyl.
  • a normal color developer that is one containing as the developing agent a primary aromatic washed, treated with an acid bath to remove the azomethine dye from the top emulsion layer, such as the acid loath listed above, treated with ierricyanide to convert the silver to silver ferrocyanide, and finally treated with hypo to remove the silver salts.
  • this bath may contain loading agents to control its penetration.
  • the steps involving the use of the acid bleach bath and the ferricyanide bath can be combined by using a hydrochloric acidquinone bath, such as that described in column 2, lines 17 to 22, of Mannes and Godowsky U. S. Patent 2,113,329.
  • insolubilizing groups may be present in the coupler molecule to render the couplers non-diifusing in the emulsion layer or layers in which they are incorporated. These groups may be so chosen that the fragments of the coupler obtained after development and acid treatment will be small enough to permit easy diffusion and removal from the film.
  • the method of producing a colored image in a photographic silver halide layer which comprises incorporating in said layer a colored coupler having an azo-substituted reactive group selected from the class consisting of methylene and ethanol groups, the azo linkage being directly and forms a dye image in the exposed regions by coupling of the development product of the developer with the residue of the colored coupler, treating said layer with an acid solution to destroy said coupled dye image Without affecting said colored coupler, and removing silver and silver halide from said layer along with the destroyed coupled dye image.
  • the method of producing a colored image in a photographic silver halide layer which comprises incorporating in said layer a colored coupler having an azo-substituted reactive methylene group, the azo linkage being directly linked to said reactive group and to an aryl radical, exposing said layer and developing it with a primary aromatic amino developing agent which simultaneously destroys the azo linkage and forms a dye image in the exposed regions by coupling of the development product of the developer with the residue of the colored coupler, treating said layer with an acid solution to destroy said coupled dye image without afiectin said colored coupler, and removing silver and silver halide from said layer along with the destroyed coupled dye image.
  • the method of producing a colored image in a photographic silver halide layer which comprises incorporating in said layer a colored coupler having an azo-substituted reactive ethanol group, the azo linkage being directly linked to said reactive group and to an aryl radical, exposing said layer and developing it with a primary aromatic amino developing agent which simultaneously destroys the azo linkage and forms a dye image in the exposed regions by coupling of the development product of the developer with the residue of the colored coupler, treating said layer with an acid solution to destroy said coupled dye image without afiecting said colored coupler, and removing silver and silver halide from said layer along with the destroyed coupled dye image.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US533933A 1944-05-03 1944-05-03 Color photography with azosubstituted couplers Expired - Lifetime US2434272A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US533933A US2434272A (en) 1944-05-03 1944-05-03 Color photography with azosubstituted couplers
CH287249D CH287249A (fr) 1944-05-03 1947-12-30 Matériel photosensible pour la photographie en couleurs, destiné à l'obtention d'images à couleurs corrigées.
DEE2645A DE837958C (de) 1944-05-03 1950-10-01 Verfahren zur Herstellung von Azomethin-Farbstoffbildern durch farbgebende Entwicklung

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US533933A US2434272A (en) 1944-05-03 1944-05-03 Color photography with azosubstituted couplers

Publications (1)

Publication Number Publication Date
US2434272A true US2434272A (en) 1948-01-13

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Family Applications (1)

Application Number Title Priority Date Filing Date
US533933A Expired - Lifetime US2434272A (en) 1944-05-03 1944-05-03 Color photography with azosubstituted couplers

Country Status (3)

Country Link
US (1) US2434272A (fr)
CH (1) CH287249A (fr)
DE (1) DE837958C (fr)

Cited By (18)

* 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
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
US2763549A (en) * 1951-11-03 1956-09-18 Eastman Kodak Co False-color or false-sensitized photographic film containing colored couplers
US3028238A (en) * 1957-01-29 1962-04-03 Agfa Ag Color photography
US3053655A (en) * 1950-01-06 1962-09-11 Minnesota Mining & Mfg Photographic material and process
US3087817A (en) * 1956-10-03 1963-04-30 Polaroid Corp Process and product for forming color images from complete dyes
US3227550A (en) * 1962-09-07 1966-01-04 Eastman Kodak Co Photographic color reproduction process and element
EP0112162A2 (fr) 1982-12-13 1984-06-27 Konica Corporation Matériel photographique photosensible aux halogénures d'argent
EP0124795A2 (fr) 1983-04-11 1984-11-14 Fuji Photo Film Co., Ltd. Emulsion photographique aux halogénures d'argent
EP0147854A2 (fr) 1983-12-29 1985-07-10 Fuji Photo Film Co., Ltd. Matériel photosensible aux hologènures d'argent
EP0201033A2 (fr) 1985-04-30 1986-11-12 Konica Corporation Procédé de traitement de matériaux photographiques couleurs à l'halogénure d'argent
EP0202616A2 (fr) 1985-05-16 1986-11-26 Konica Corporation Procédé pour le développement couleur d'un matériau photographique à l'halogénure d'argent sensible à la lumière
EP0204530A2 (fr) 1985-05-31 1986-12-10 Konica Corporation Procédé de formation d'une image directement positive en couleur
EP0228914A2 (fr) 1985-12-28 1987-07-15 Konica Corporation Procédé de traitement d'un matériau photographique couleur à l'halogénure d'argent sensible à la lumière
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
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 (fr) 1994-11-14 1996-05-15 Ciba-Geigy Ag Stabilisateurs à la lumière latents

Citations (13)

* 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
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
US2297732A (en) * 1940-05-15 1942-10-06 Du Pont Photographic color process involving the formation of azo dye images
US2307162A (en) * 1939-06-06 1943-01-05 Gen Aniline & Film Corp Process for the production of color images
US2308023A (en) * 1938-10-26 1943-01-12 Eastman Kodak Co Colored photographic image
US2316782A (en) * 1937-12-09 1943-04-20 Chromogen Inc Process of producing multicolor images
US2320418A (en) * 1935-06-22 1943-06-01 Gen Aniline & Film Corp Color photographs
US2322001A (en) * 1940-10-10 1943-06-15 Eastman Kodak Co Method of producing dye images
US2322084A (en) * 1940-01-11 1943-06-15 Eastman Kodak Co Simultaneous bleaching and fixing bath
US2331326A (en) * 1939-07-22 1943-10-12 Ilford Ltd Production of colored photographic images
US2334495A (en) * 1939-07-22 1943-11-16 Ilford Ltd Color photography
US2342620A (en) * 1942-07-10 1944-02-22 Du Pont Azo-reversal process of color photography

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2320418A (en) * 1935-06-22 1943-06-01 Gen Aniline & Film Corp Color photographs
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
US2316782A (en) * 1937-12-09 1943-04-20 Chromogen Inc Process of producing multicolor images
US2263012A (en) * 1937-12-23 1941-11-18 Eastman Kodak Co Process for making natural color photographs
US2308023A (en) * 1938-10-26 1943-01-12 Eastman Kodak Co Colored photographic image
US2307162A (en) * 1939-06-06 1943-01-05 Gen Aniline & Film Corp Process for the production of color images
US2334495A (en) * 1939-07-22 1943-11-16 Ilford Ltd Color photography
US2331326A (en) * 1939-07-22 1943-10-12 Ilford Ltd Production of colored photographic images
US2322084A (en) * 1940-01-11 1943-06-15 Eastman Kodak Co Simultaneous bleaching and fixing bath
US2297732A (en) * 1940-05-15 1942-10-06 Du Pont Photographic color process involving the formation of azo dye images
US2322001A (en) * 1940-10-10 1943-06-15 Eastman Kodak Co Method of producing dye images
US2342620A (en) * 1942-07-10 1944-02-22 Du Pont Azo-reversal process of color photography

Cited By (18)

* 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
US2515691A (en) * 1946-08-21 1950-07-18 Gevaert Photo Prod Nv Azo dyestuffs as photographic coupling components
US3053655A (en) * 1950-01-06 1962-09-11 Minnesota Mining & Mfg Photographic material and process
US2763549A (en) * 1951-11-03 1956-09-18 Eastman Kodak Co False-color or false-sensitized photographic film containing colored couplers
US3087817A (en) * 1956-10-03 1963-04-30 Polaroid Corp Process and product for forming color images from complete dyes
US3028238A (en) * 1957-01-29 1962-04-03 Agfa Ag Color photography
US3227550A (en) * 1962-09-07 1966-01-04 Eastman Kodak Co Photographic color reproduction process and element
EP0112162A2 (fr) 1982-12-13 1984-06-27 Konica Corporation Matériel photographique photosensible aux halogénures d'argent
EP0124795A2 (fr) 1983-04-11 1984-11-14 Fuji Photo Film Co., Ltd. Emulsion photographique aux halogénures d'argent
EP0147854A2 (fr) 1983-12-29 1985-07-10 Fuji Photo Film Co., Ltd. Matériel photosensible aux hologènures d'argent
EP0201033A2 (fr) 1985-04-30 1986-11-12 Konica Corporation Procédé de traitement de matériaux photographiques couleurs à l'halogénure d'argent
EP0202616A2 (fr) 1985-05-16 1986-11-26 Konica Corporation Procédé pour le développement couleur d'un matériau photographique à l'halogénure d'argent sensible à la lumière
EP0204530A2 (fr) 1985-05-31 1986-12-10 Konica Corporation Procédé de formation d'une image directement positive en couleur
EP0228914A2 (fr) 1985-12-28 1987-07-15 Konica Corporation Procédé de traitement d'un matériau photographique couleur à l'halogénure d'argent sensible à la lumière
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
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
EP0711804A2 (fr) 1994-11-14 1996-05-15 Ciba-Geigy Ag Stabilisateurs à la lumière latents

Also Published As

Publication number Publication date
CH287249A (fr) 1952-11-30
DE837958C (de) 1952-05-05

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