US2322001A - Method of producing dye images - Google Patents

Method of producing dye images Download PDF

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Publication number
US2322001A
US2322001A US360622A US36062240A US2322001A US 2322001 A US2322001 A US 2322001A US 360622 A US360622 A US 360622A US 36062240 A US36062240 A US 36062240A US 2322001 A US2322001 A US 2322001A
Authority
US
United States
Prior art keywords
dye
image
silver
acid
layer
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
US360622A
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English (en)
Inventor
Ehrenfried George
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 US360622A priority Critical patent/US2322001A/en
Priority to GB812/41A priority patent/GB546704A/en
Priority to GB10577/41A priority patent/GB551501A/en
Priority to US446054A priority patent/US2326055A/en
Application granted granted Critical
Publication of US2322001A publication Critical patent/US2322001A/en
Priority to FR919792D priority patent/FR919792A/fr
Priority to FR54933D priority patent/FR54933E/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/28Silver dye bleach processes; Materials therefor; Preparing or processing such materials

Definitions

  • This invention relates to a method for producing colored photographic images and particularly to a method of forming colored images in image in which a dyed gelatin layer containing a silver image is treated with a solution of a strong reducing agent such as sodium hydrosulilte or stannous chloride.
  • the reducing bleach bath destroys the dye in the layer selectively in the region of the silver image, giving'a positive dye image from a. negative silver image.
  • the destruction of a dye to form a photographic image in this process appears to depend upon the catalytic action of the silver image which results in the destruction of thedye in that portion of the film when treated with a suitable reducing bleach bath.
  • the silver salt image may be produced, for example, by rehalogenizing a developed and fixed'silver image.
  • an objeetto provide a novel method of forming a colored photographic image in a photographic layer.
  • A-iurther object is to provide a novel method for destroying a dye uniformly dispersed in a photographic layer under the influence of a silver salt image.
  • the photographic element treated according to my invention may comprise a single emulsion of poly-azo dyes as disclosed in Christensen U. S.
  • the three emulsion layers preferably contain dyes coupling with 2 mols of R-salt.
  • the red sensitive layer may be colored blue-green with one of the following dyes.
  • Example 1 Pontamine Fast Green 581. (Du Pont)
  • Example 2. A blue dye of less suitable color, bfit of satisfactory bleaching properties, made by tetrazotizing 4,4"-diamino-2,2'-dimethyl, 5,5'-dimethoxy triphenylmethane and coupling it with two mols of chromotropic acid.
  • the green-sensitive magenta with one of the following dyes, some of which are described in Seymour, Young, and
  • Example 4. Monosol Carmine LS (Color Index Example 5.-A dye made by tetrazotizing 4,4 diamino-Zi,3'-dimethoxy diphenyl methane and Example 6. The dye made by tetrazotizing 1 mol of 4,4'-diamino triphenyl methane and coupling with 2 mols of N-lauroyl H-acid.
  • Example 7 The dyes made by tetrazotizing 1 1 mol of 4,4'-diamino-3,3', 6,6'.-tetramethyl triphenyl methane and coupling-with 2 mols of N-he'ptoyl H-acicl or one of the following compounds:
  • Example Z --N(naphthalene B sulfonyl) H- acid.
  • Example 1%.Thfi dye made by tetrazotlzing 4,4'-diam.ino 2,2-dimetl1yl-5,5-dimethoxy trl phenylmethane and coupling with .2 mols of 1-naphthol-8-para-tolyl sulionatedfi-disulionlc acid.
  • Example i The dye made by tetrazotizing Pool-amine l'liaao Yellow 2G1 and coupling with layer may be colored Example 19.--The dye made by tetrazotizing 4A-cliamino3,3-dimethyl-d' -"nethoxy triphenylmethane-3"-sulfonic acid and coupling with 2 mols of haphthionic acid.
  • Example 20 The dye made by diaaotizing 2- naphthyla1nine-4, li-disulfonlc acid, coupling with meta-toluidine and treating the product with phosgene.
  • Example 21 The dye made by tetrazotizing benzicline and coupling with 2 mols of phenol p-sulfonlc acid.
  • Example 22 The dye made by tetrazotizing d,e'-diarnino stilbene disulionic acid, coupling with 2 mols of phenol and forming the di-npropyl ether of the product.
  • Example 23 The dye made by tetrazotizing e-,ddiarnino stilbene disulfonic acid, coupling with 2 mole of phenol and forming the dibutyl ether of the product.
  • Example 2 The dye made by tetrazotizing i,'diamino stilbene .disulfonic acid, coupling with 2 mole of 2,6-dimethyl phenol and forming the di-n-propyl ether of the product.
  • the layers need not be colored complementary to their sensitivity, however, but may be colored alternatively with a dye that transmits the color for which the layer is mainly sensitive.
  • This film is exposed in a camera or under a suitable color positive or negative.
  • it may be exposed to a natural color transparency by a single exposure to tungsten light through suitable correcting filters or by three simultaneous or successive exposures to light transmitted by red, green and blue filters in a suitable ratio of times or intensities. It is then developed in an ordinary black and white developer, washed,
  • the silver image is then reconverted to a sliver halide such as silver chloride and the dyes are bleached by treatment in a sodium stannite or sodium hydrosulfite bleach bath. This reduces the silver halide image to metallic silver, and during the same operation, destroys the dye in the region of the silver image so formed.
  • the film is then again washed and the silver image is reconverted to silver halide in the same solution previously used for this purpose or in any other suitable bath.
  • the film is then fixed in hypo to remove the silver halide and is washed and dried leaving pure dye images in the layers,
  • the element is again washed and may then be hardened in a 1 to 20 formalin solution, although this hardening step may be omitted if the emulsions have been suitably hardened before coatmg.
  • the silver images produced by the development are bleached to silver chloride by treatment for about ten minutes in the following solution:
  • baths of the following composition may be used:
  • Pontamine Fast Green 58L for example, a 2% solution of sodium hydrosulfite can be used to bleach the dyes in the presence of the silver chloride image.
  • a photographic element containing the dyes reierred to above may be processed according to the method of the present invention to form coloreduccessfully bleached by these aflected the dye in the remaining claims.
  • the method -'of forming a colored image in a photographic layer containing a bleachable azo dye uniformly dispersed therein and a rehalogenized silver image, which comprises bleaching the dye in the region of said image with a sodium hydrosulflte bleach bath.
  • the method of forming a colored image in a photographic layer containing a bleachable azo dye and unexposed silver halide uniformly dispersed therein which comprises exposing and developing said layer, removing the silver halide without aiiecting the silver image formed by development, reconverting the silver image to silver halide. and bleaching the dye in the presence of said image with a stannit oi alkali-metal to form a colorless dye compound and leave unafiected the dye in the remaining portions of the layer.
  • the method of forming a colored image in a photographic layer containing a bleachable aao dye and unexposed silver halide uniformly dispersed therein which comprises exposing and developing said layer, removing the undeveloped silver halide without aflecting the silver image formed by development, reconverting the silver image'to silver halide, and bleaching the dye in an alkaline, reducing bleach bath comprising an alkali metal salt of an acid selected from the group consisting oi stannous acid and hydrosulfurous acid and free of silver halide developing agent in the presence of said image to form a colorless dye compound and leave unaffected the dye in the remaining portions of the layer.

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Indole Compounds (AREA)
US360622A 1940-10-10 1940-10-10 Method of producing dye images Expired - Lifetime US2322001A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US360622A US2322001A (en) 1940-10-10 1940-10-10 Method of producing dye images
GB812/41A GB546704A (en) 1940-10-10 1941-01-21 Improvements in the production of coloured photographic images
GB10577/41A GB551501A (en) 1940-10-10 1941-08-19 Improvements in multi-layer colour photography
US446054A US2326055A (en) 1940-10-10 1942-06-06 Dye bleaching process
FR919792D FR919792A (fr) 1940-10-10 1945-08-02 Procédé pour l'obtention d'images photographiques colorées
FR54933D FR54933E (fr) 1940-10-10 1946-08-23 Procédé pour l'obtention d'images photographiques colorées

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US360622A US2322001A (en) 1940-10-10 1940-10-10 Method of producing dye images
GB10577/41A GB551501A (en) 1940-10-10 1941-08-19 Improvements in multi-layer colour photography

Publications (1)

Publication Number Publication Date
US2322001A true US2322001A (en) 1943-06-15

Family

ID=26247618

Family Applications (2)

Application Number Title Priority Date Filing Date
US360622A Expired - Lifetime US2322001A (en) 1940-10-10 1940-10-10 Method of producing dye images
US446054A Expired - Lifetime US2326055A (en) 1940-10-10 1942-06-06 Dye bleaching process

Family Applications After (1)

Application Number Title Priority Date Filing Date
US446054A Expired - Lifetime US2326055A (en) 1940-10-10 1942-06-06 Dye bleaching process

Country Status (3)

Country Link
US (2) US2322001A (fr)
FR (2) FR919792A (fr)
GB (2) GB546704A (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2434272A (en) * 1944-05-03 1948-01-13 Eastman Kodak Co Color photography with azosubstituted couplers
US2688542A (en) * 1949-02-09 1954-09-07 Bela Gaspar Material and process for the production of color photographic images
US3716362A (en) * 1969-07-30 1973-02-13 Ciba Geigy Ag Process for the removal of metallic silver from photographic material
DE2651920A1 (de) * 1975-11-17 1977-05-26 Du Pont Photographisches verfahren
US4029509A (en) * 1975-11-17 1977-06-14 E. I. Du Pont De Nemours And Company Positive process using a low coating weight silver halide
US4304847A (en) * 1978-11-13 1981-12-08 Fuji Photo Film Co., Ltd. Color image forming dye bleach process

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE23357E (en) * 1939-08-28 1951-04-17 Processes for producing same
US2418624A (en) * 1943-03-02 1947-04-08 Eastman Kodak Co Azo dyes for color photography
GB711233A (en) * 1951-08-16 1954-06-30 Geigy Ag J R Improvements in or relating to colour photography
NL227619A (fr) * 1957-05-09
US3061433A (en) * 1958-08-04 1962-10-30 Ilford Ltd Process and solution for bleaching photographic images
BE622239A (fr) * 1961-09-08

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2434272A (en) * 1944-05-03 1948-01-13 Eastman Kodak Co Color photography with azosubstituted couplers
US2688542A (en) * 1949-02-09 1954-09-07 Bela Gaspar Material and process for the production of color photographic images
US3716362A (en) * 1969-07-30 1973-02-13 Ciba Geigy Ag Process for the removal of metallic silver from photographic material
DE2651920A1 (de) * 1975-11-17 1977-05-26 Du Pont Photographisches verfahren
US4029509A (en) * 1975-11-17 1977-06-14 E. I. Du Pont De Nemours And Company Positive process using a low coating weight silver halide
US4047956A (en) * 1975-11-17 1977-09-13 E. I. Du Pont De Nemours And Company Low coating weight silver halide element and process
US4304847A (en) * 1978-11-13 1981-12-08 Fuji Photo Film Co., Ltd. Color image forming dye bleach process

Also Published As

Publication number Publication date
FR54933E (fr) 1951-04-30
US2326055A (en) 1943-08-03
GB546704A (en) 1942-07-27
GB551501A (en) 1943-02-25
FR919792A (fr) 1947-03-18

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