US2933391A - Photographic emulsions containing 5-pyrazolone coupler compounds - Google Patents

Photographic emulsions containing 5-pyrazolone coupler compounds Download PDF

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Publication number
US2933391A
US2933391A US608210A US60821056A US2933391A US 2933391 A US2933391 A US 2933391A US 608210 A US608210 A US 608210A US 60821056 A US60821056 A US 60821056A US 2933391 A US2933391 A US 2933391A
Authority
US
United States
Prior art keywords
pyrazolone
alkyl
couplers
silver halide
compounds
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
US608210A
Other languages
English (en)
Inventor
Feniak George
Loria Anthony
Warren A Reckhow
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 US608210A priority Critical patent/US2933391A/en
Priority to FR1181999D priority patent/FR1181999A/fr
Priority to GB27988/57A priority patent/GB868937A/en
Application granted granted Critical
Publication of US2933391A publication Critical patent/US2933391A/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
    • G03C7/36—Couplers containing compounds with active methylene groups
    • G03C7/38—Couplers containing compounds with active methylene groups in rings
    • G03C7/384—Couplers containing compounds with active methylene groups in rings in pyrazolone rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
    • C07D231/26—1-Phenyl-3-methyl-5- pyrazolones, unsubstituted or substituted on the phenyl ring

Definitions

  • This invention relates to photography and particularly to compounds which form dyes on coupling with the developing agent to produce colored images.
  • colored photographic images may be formed by using a developer which produces a colored image on development.
  • the colored compound thus formed is deposited adjacent the silver grains of the silver image during development.
  • a colored image may be formed by adding to said developer solution or by incorporating in the silver halide emulsion before or after exposure a compound which couples during development with the oxidation product of the developing agent and which forms a colored compound which is likewise deposited adjacent the silver grains of the silver image during development.
  • a coupling compound or coupler Such a compound which is employed in conjunction with a developing agent for the silver and which couples with the oxidation product of the developing agent during development is referred to herein as a coupling compound or coupler.
  • Couplers such as the 3-alkyl-5-pyrazolone couplers unsubstituted in the 1-position of the pyrazolone nucleus or containing a phenyl group in the 1-position produce with color developing agents magenta dyes having undesirable secondary light absorptions.
  • One object of our invention is to provide a new class of couplers for color photography.
  • a further object is to provide couplers which are stable to light and heat when incorporated into an emulsion layer.
  • a further object is to provide couplers which yield dyes whose secondary light absorptions are at a minimum.
  • the coupler compounds of the invention have the following general formula:
  • N C-R O X II o
  • X is a halogen atom such as chlorine or bromine
  • n is a positive integer at least as great as 2
  • R is an alkyl group of from 11 to 17 carbon atoms.
  • the coupler compounds of the invention are primarily of use in silver halide emulsion layers and can be dispersed in an emulsion layer such as a gelatino-silver halide emulsion layer by means of coupler solvents including cellulose'esters, natural and synthetic resins and "organic crystalloidal materials having a boiling point 'aboveaboutl'76" C., .as described in the Marines et a1.
  • the aromatic amino developing agents used with the coupler compounds of our invention include the mono-, diand tri-amino aryl compounds and their derivatives formed by substitution in the amino group as well as in the ring such as alkyl phenylene diamines and alkyl toluene diamines. These compounds are usually used in the salt form such as the hydrochloride or the sulfate which are more stable than the amines themselves.
  • Suitable compounds are diethyl-p-phenylene diamine hydrochloride, monoethyl-p-phenyleue diamine hydrochloride, dimethyl-p-phenylene diamine hydrochloride, dimethylp-phenylene diamine sulfate and Z-amino-S-diethyl amino toluene sulfate.
  • the p-amino phenols and their substitution products may also be used where the amino group is unsubstitutedL; All of these compounds have an unsubstituted amino group which enables the oxidation Grams 2-amino-5-diethylaminotoluene hydrochloride 32 Sodium sulfite (anhydrous) 2 Sodium carbonate (anhydrous) 20 Potassium bromide 2 Water to 1 liter.
  • the colloid vehicle of the silver halide emulsion containing the couplers of the invention may be gelatin-or other hydrophilic carrier for silver halide such as collodion, organic esters of cellulose or synthetic resins;
  • the support for the emulsion may be a transparent material such as glass, cellulose ester or a non-transparent reflecting material such as paper or an opaque cellulose ester.
  • the emulsion may be coated as a single layer on the support or as superposed layers on one or both'sides of the support.
  • the superposed layers may be differentially sensitized to form natural color photographic images in the Well-known manner. For example, in a multilayer material sensitized to red, green and-*blue light, respectively, our couplers would ordinarily beused in the green-sensitive emulsion layer to form the magenta image.
  • a light-sensitive photographic silver halide emulsion layer containing a member of the class consisting of a 1-(dichlorphenyl-)-3-alkyl-5-pyrazolone and a l-(trichlorophenyl)-3-alkyl-5-pyrazolone, the alkyl radical of which contains from ll-to 17 carbon atoms.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US608210A 1956-09-06 1956-09-06 Photographic emulsions containing 5-pyrazolone coupler compounds Expired - Lifetime US2933391A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US608210A US2933391A (en) 1956-09-06 1956-09-06 Photographic emulsions containing 5-pyrazolone coupler compounds
FR1181999D FR1181999A (fr) 1956-09-06 1957-09-04 Procédé de photographie en couleurs et nouveau produit pour sa mise en oeuvre
GB27988/57A GB868937A (en) 1956-09-06 1957-09-04 Improvements in colour photographic materials

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US608210A US2933391A (en) 1956-09-06 1956-09-06 Photographic emulsions containing 5-pyrazolone coupler compounds

Publications (1)

Publication Number Publication Date
US2933391A true US2933391A (en) 1960-04-19

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Family Applications (1)

Application Number Title Priority Date Filing Date
US608210A Expired - Lifetime US2933391A (en) 1956-09-06 1956-09-06 Photographic emulsions containing 5-pyrazolone coupler compounds

Country Status (3)

Country Link
US (1) US2933391A (fr)
FR (1) FR1181999A (fr)
GB (1) GB868937A (fr)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3079397A (en) * 1959-12-29 1963-02-26 Fiordalisi Fernanda Misani Process for preparation of certain 4, 4-disubstituted pyrazolones
US3311476A (en) * 1962-12-26 1967-03-28 Eastman Kodak Co Two-equivalent couplers for color photography
US3312715A (en) * 1963-06-17 1967-04-04 Ilford Ltd Colour couplers and their production and use in colour photography
US3328419A (en) * 1963-06-17 1967-06-27 Ilford Ltd Colour couplers and their production and use in colour photography
US3369899A (en) * 1963-07-09 1968-02-20 Gevaert Photo Prod Nv Photographic materials containing aroylacetanilide type color couplers
US3393041A (en) * 1963-07-09 1968-07-16 Gevaert Photo Prod Nv Multilayer silver halide elements containing thiazole color couplers for yellow
US3393040A (en) * 1963-07-09 1968-07-16 Gevaert Photo Prod Nv Silver halide photographic elements containing sulfonic acid substituted aroylacetarylide couplers
US4180345A (en) * 1978-06-20 1979-12-25 Routens Jean Paul Saddle support for bicycles and the like
US5270156A (en) * 1991-10-11 1993-12-14 Konica Corporation Silver halide color photographic light sensitive material
EP0782044A1 (fr) 1995-12-27 1997-07-02 Konica Corporation Matériau photographique couleur à l'halogénure d'argent sensible à la lumière
US6410533B1 (en) * 2000-02-10 2002-06-25 Genzyme Corporation Antibacterial compounds

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5280027A (en) * 1975-12-26 1977-07-05 Konishiroku Photo Ind Co Ltd Formation of magenta dye image

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2354552A (en) * 1940-08-08 1944-07-25 Gen Aniline & Film Corp Color photographic image
US2437063A (en) * 1940-08-08 1948-03-02 Gen Aniline & Film Corp Nondiffusing 1-phenyl-5-pyrazolone couplers for color photography
US2600788A (en) * 1949-06-07 1952-06-17 Eastman Kodak Co Halogen-substituted pyrazolone couplers for color photography
US2706683A (en) * 1951-12-15 1955-04-19 Eastman Kodak Co Bis-pyrazolone for color photography

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2354552A (en) * 1940-08-08 1944-07-25 Gen Aniline & Film Corp Color photographic image
US2437063A (en) * 1940-08-08 1948-03-02 Gen Aniline & Film Corp Nondiffusing 1-phenyl-5-pyrazolone couplers for color photography
US2600788A (en) * 1949-06-07 1952-06-17 Eastman Kodak Co Halogen-substituted pyrazolone couplers for color photography
US2706683A (en) * 1951-12-15 1955-04-19 Eastman Kodak Co Bis-pyrazolone for color photography

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3079397A (en) * 1959-12-29 1963-02-26 Fiordalisi Fernanda Misani Process for preparation of certain 4, 4-disubstituted pyrazolones
US3311476A (en) * 1962-12-26 1967-03-28 Eastman Kodak Co Two-equivalent couplers for color photography
US3312715A (en) * 1963-06-17 1967-04-04 Ilford Ltd Colour couplers and their production and use in colour photography
US3328419A (en) * 1963-06-17 1967-06-27 Ilford Ltd Colour couplers and their production and use in colour photography
US3369899A (en) * 1963-07-09 1968-02-20 Gevaert Photo Prod Nv Photographic materials containing aroylacetanilide type color couplers
US3393041A (en) * 1963-07-09 1968-07-16 Gevaert Photo Prod Nv Multilayer silver halide elements containing thiazole color couplers for yellow
US3393040A (en) * 1963-07-09 1968-07-16 Gevaert Photo Prod Nv Silver halide photographic elements containing sulfonic acid substituted aroylacetarylide couplers
US4180345A (en) * 1978-06-20 1979-12-25 Routens Jean Paul Saddle support for bicycles and the like
US5270156A (en) * 1991-10-11 1993-12-14 Konica Corporation Silver halide color photographic light sensitive material
EP0782044A1 (fr) 1995-12-27 1997-07-02 Konica Corporation Matériau photographique couleur à l'halogénure d'argent sensible à la lumière
US6410533B1 (en) * 2000-02-10 2002-06-25 Genzyme Corporation Antibacterial compounds

Also Published As

Publication number Publication date
FR1181999A (fr) 1959-06-19
GB868937A (en) 1961-05-25

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