US2455170A - Colored couplers - Google Patents

Colored couplers Download PDF

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Publication number
US2455170A
US2455170A US533932A US53393244A US2455170A US 2455170 A US2455170 A US 2455170A US 533932 A US533932 A US 533932A US 53393244 A US53393244 A US 53393244A US 2455170 A US2455170 A US 2455170A
Authority
US
United States
Prior art keywords
coupler
group
layer
color
developing
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
US533932A
Other languages
English (en)
Inventor
Dudley B Glass
Paul W Vittum
Arnold Weissberger
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 US533932A priority Critical patent/US2455170A/en
Priority to GB18775/44A priority patent/GB598174A/en
Priority to FR950287D priority patent/FR950287A/fr
Priority to NL134794A priority patent/NL71532C/xx
Priority to BE476361A priority patent/BE476361A/fr
Priority to CH282408A priority patent/CH282408A/fr
Priority to CH280207D priority patent/CH280207A/fr
Application granted granted Critical
Publication of US2455170A publication Critical patent/US2455170A/en
Priority to DEE2641A priority patent/DE848154C/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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S56/00—Harvesters
    • Y10S56/12—Brush

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 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 incorporated in the emulsion layer and the unused coupler remains after formation of the colored 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 paraphenylazo acetoacetanilide which was disclosed in Mannes and Godows'ky 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 photography.
  • Z represents the atoms necessary to complete a cyclic structure having adjacent the.
  • the active methylene group may be substituted with an azo group and that this group is removable by the oxidized photographic developer when the azo-subs'tituted coupler is treated with the oxidized developer either in aqueous solution or in the photographic emulsion layer;
  • the'coupler may be converted to a colored compound and the azo group readily removed from itby'means of reaction with the oxidized developing agent. This reaction appears-to proceed as follows:
  • p-I-Iydroxyaniline (5.5 g.; 0.05 mole) was dissolved in a solution of 40 cc. of water and 15 cc. of concentrated hydrochloric acid and di'azotized at C. by the addition of 3 .5 g. (0.05 mole) of sodium nitrite. This solution was added to a solution of 16.1g. (0.05 mole) of 1(p (p-tert.- butylphenoxy) -phenyl) -3-methyl -5- pyrazolone in 200 cc. of water which contained g. of sodium hydroxide. The temperature of the reaction mixphotographic emulsion layer prior to exposure and upon development is converted into a colored image where the layer was exposed. The coupler remaininginthe' unexposed portions of the layer retains 'its'original color; and by suitable choice of the color of the original coupler and the color of the final dye image a masking or correction effect can be obtained.
  • Suitable compounds are diethyl paraphenylenediamine, monomethyl paraphenylenediamine, dimethyl paraphenylenediamine and para-aminophenol. 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 conipounds to form dye images.
  • the following developing solution is suitable for developing gelatino silver halide layers containing-colored couplers according to our invention.
  • oo i ⁇ CH-N NR
  • Z represents the atoms necessary to complete a cyclic structure in which there is adjacent the reactive CI-I group a member selected from the class consisting of -S, -NI-I-, and carbon doubly bound to an atom selected from the class consisting of (l) a carbon atom which is part of a conjugated chain linked to an electro-negatiVe atom, (2) nitrogen and (3) oxygen
  • R is selected from the class consisting of aromatic and heterocyclic radicals
  • X represents the atoms necessary to complete a five-membered ring in which there is adjacent the reactive OH group a member selected from the class consisting of S, NH, and carbon doubly bound to an atom selected from the class consisting of (1) a carbon atom which is part of a conjugated chain linked to an electro-neg-ative atom, (2) nitrogen and (3) oxygen, and R is selected from the class consisting of aromatic and heterocyclic radicals
  • X represents the atoms necessary to complete a pyrazolone ring
  • R is selected from the class consisting of aromatic and heterocyclic radicals
  • R represents a mononuclear aryl radical and R. represents a mononuclear aryl radical, exposing said material and developing it with a developer containing a primary aromatic amino developing agent.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US533932A 1944-05-03 1944-05-03 Colored couplers Expired - Lifetime US2455170A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
US533932A US2455170A (en) 1944-05-03 1944-05-03 Colored couplers
GB18775/44A GB598174A (en) 1944-05-03 1944-10-02 Improvements in and relating to photographic colour forming developers and processesof colour development
FR950287D FR950287A (fr) 1944-05-03 1946-08-29 Perfectionnements aux coupleurs colorés
NL134794A NL71532C (nl) 1944-05-03 1947-09-13 Werkwijze voor fotografische kleurontwikkeling en voor de bereiding van een daarbij te gebruiken fotografische emulsie, en fotografisch element
BE476361A BE476361A (fr) 1944-05-03 1947-09-27 Perfectionnements aux coupleurs colorés
CH282408A CH282408A (fr) 1944-05-03 1947-12-23 Matériel photosensible pour la photographie en couleurs.
CH280207D CH280207A (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.
DEE2641A DE848154C (de) 1944-05-03 1950-10-01 Verfahren zum Entwickeln eines Farbbildes in einer Silber-halogen-Emulsionsschicht, insbesondere einer Gelatine-Silberhalogen-Emulsionsschicht

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US533932A US2455170A (en) 1944-05-03 1944-05-03 Colored couplers
GB18775/44A GB598174A (en) 1944-05-03 1944-10-02 Improvements in and relating to photographic colour forming developers and processesof colour development

Publications (1)

Publication Number Publication Date
US2455170A true US2455170A (en) 1948-11-30

Family

ID=42359001

Family Applications (1)

Application Number Title Priority Date Filing Date
US533932A Expired - Lifetime US2455170A (en) 1944-05-03 1944-05-03 Colored couplers

Country Status (7)

Country Link
US (1) US2455170A (fr)
BE (1) BE476361A (fr)
CH (2) CH282408A (fr)
DE (1) DE848154C (fr)
FR (1) FR950287A (fr)
GB (1) GB598174A (fr)
NL (1) NL71532C (fr)

Cited By (9)

* 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
US2536398A (en) * 1947-10-10 1951-01-02 Gen Aniline & Film Corp Pyrazolone diazotype couplers
US2687957A (en) * 1948-12-08 1954-08-31 Gen Aniline & Film Corp Light-sensitive photographic elements containing azo pyrazolones bleachable in ferricyanide compositions
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
US3227550A (en) * 1962-09-07 1966-01-04 Eastman Kodak Co Photographic color reproduction process and element
US3227551A (en) * 1959-04-06 1966-01-04 Eastman Kodak Co Photographic color reproduction process and element
US3476564A (en) * 1966-05-03 1969-11-04 Ferrania Spa Silver halide emulsion containing an azo-pyrazolone coupler
US3519429A (en) * 1966-05-16 1970-07-07 Eastman Kodak Co Silver halide emulsions containing a stabilizer pyrazolone coupler

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2725292A (en) * 1952-05-15 1955-11-29 Eastman Kodak Co Colored couplers containing solubilizing groups
DE102020004186A1 (de) 2020-03-27 2021-09-30 GKD - Gebr. Kufferath AG. Prozessband mit einem Flächengefüge, Vorrichtung mit umlaufendem Endlosband und Verwendung eines Prozessbandes

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2213986A (en) * 1938-04-08 1940-09-10 Ilford Ltd Production of colored photographic images
US2220123A (en) * 1938-10-01 1940-11-05 Bela Gaspar Color photographic process
US2262055A (en) * 1940-01-25 1941-11-11 Du Pont Film Mfg Corp Method of color photography
US2271230A (en) * 1939-09-07 1942-01-27 Eastman Kodak Co Sulphonamides of dyes
US2308023A (en) * 1938-10-26 1943-01-12 Eastman Kodak Co Colored photographic image
US2310943A (en) * 1938-10-05 1943-02-16 Du Pont Polyvinyl acetals
US2369489A (en) * 1941-09-25 1945-02-13 Eastman Kodak Co Acylated amino pyrazolone couplers
US9334495B2 (en) * 2009-11-25 2016-05-10 Elitechgroup B.V. Minor groove binder (MGB)-oligonucleotide miRNA antagonists

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2213986A (en) * 1938-04-08 1940-09-10 Ilford Ltd Production of colored photographic images
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
US2308023A (en) * 1938-10-26 1943-01-12 Eastman Kodak Co Colored photographic image
US2271230A (en) * 1939-09-07 1942-01-27 Eastman Kodak Co Sulphonamides of dyes
US2262055A (en) * 1940-01-25 1941-11-11 Du Pont Film Mfg Corp Method of color photography
US2369489A (en) * 1941-09-25 1945-02-13 Eastman Kodak Co Acylated amino pyrazolone couplers
US9334495B2 (en) * 2009-11-25 2016-05-10 Elitechgroup B.V. Minor groove binder (MGB)-oligonucleotide miRNA antagonists

Cited By (9)

* 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
US2536398A (en) * 1947-10-10 1951-01-02 Gen Aniline & Film Corp Pyrazolone diazotype couplers
US2687957A (en) * 1948-12-08 1954-08-31 Gen Aniline & Film Corp Light-sensitive photographic elements containing azo pyrazolones bleachable in ferricyanide compositions
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
US3227551A (en) * 1959-04-06 1966-01-04 Eastman Kodak Co Photographic color reproduction process and element
US3227550A (en) * 1962-09-07 1966-01-04 Eastman Kodak Co Photographic color reproduction process and element
US3476564A (en) * 1966-05-03 1969-11-04 Ferrania Spa Silver halide emulsion containing an azo-pyrazolone coupler
US3519429A (en) * 1966-05-16 1970-07-07 Eastman Kodak Co Silver halide emulsions containing a stabilizer pyrazolone coupler

Also Published As

Publication number Publication date
FR950287A (fr) 1949-09-22
DE848154C (de) 1952-09-01
BE476361A (fr) 1947-10-31
GB598174A (en) 1948-02-12
CH280207A (fr) 1952-01-15
CH282408A (fr) 1952-04-30
NL71532C (nl) 1953-01-15

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