US2691588A - Photographic developers containing 8-hydroxyquinolines - Google Patents

Photographic developers containing 8-hydroxyquinolines Download PDF

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Publication number
US2691588A
US2691588A US276676A US27667652A US2691588A US 2691588 A US2691588 A US 2691588A US 276676 A US276676 A US 276676A US 27667652 A US27667652 A US 27667652A US 2691588 A US2691588 A US 2691588A
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United States
Prior art keywords
hydroxyquinoline
sulfonic acid
hydroxyquinolines
photographic
photographic developers
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Expired - Lifetime
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US276676A
Inventor
Richard W Henn
John I Crabtree
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to US276676A priority Critical patent/US2691588A/en
Priority to GB7057/53A priority patent/GB720812A/en
Priority to FR1072957D priority patent/FR1072957A/en
Application granted granted Critical
Publication of US2691588A publication Critical patent/US2691588A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • 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
    • G03C7/407—Development processes or agents therefor
    • G03C7/413—Developers

Definitions

  • the developing solutions which we propose to use contain a silver or equivalent material such as potassium bisulfite, and an 8-hydroxyquinoline.
  • 8-hydroxyquinolines which may 'be used for this purpose are 8-hydroXyquinoline-5-sulfonic acid, 7- chloro-8-hydroxyquinoline-5-sulfonic acid, 7- bromo-8-hydroxyquinoline-5-sulfonic acid and S-methyl 8 hydroxyquinoline sulfonic acid.
  • the developing solution is an alkaline solution ten alkaline;material such as ghydroxide- 'or sodium tsimay-alsobe present.
  • v I The :following examples illustrate developer formulas constituted; according to our (invention.
  • Example III Grams Hydroquinone 2.5 on 5.0 Sodium sulfite 100.0 0 Sodium metaborate 20.0 Ethylenediamine tetracetic acid 5.0 8-hydroxyquinoline-sulfat 1.0 Water to 1 liter.
  • the B-hydroxyquinolines developer in amounts varying from of two parts of without the 8-hydroxyquinoline-5-sulfonic acid decreased the aeration life to a vided air bubbles 8-hydroxyquinoline-5-sulfonic acid was aeration life was restored to its normal of 24 A similar effect was observed in of Example IH.
  • the color developer of Example I shows espe- 3.
  • a photographic developing solution having cially good aeration life and is used for developreduced tendency to oxidation caused by heavy ing an emulsion containing color couplers, for exmetals and capable of forming a colored image ample, for developingafilm such as that described upon development of an exposed silver halide in Jelley and Vittum U. S. Patent 2,322,027.
  • the S-hydroxyquinolines of prising an aqueous solution of sodium carbonate our invention may be incorporated in the emul- 2-amino-fi-diethylaminotoluene, sodium sulfite sion, overcoat, backing layer or interlayer of a and approximately 0.25 gram per liter of soluim. tion of B-hydroxyquinoline-S-sulfonic acid. It will be understood that the examples and 4.
  • a photographic developer having reduced modifications included herein are illustrative only tendency to oxidation caused by heavy metals, and that our invention is to be taken as limited comprising an alkaline solution of a silver halide only by the scope of the appended claims.
  • a photographic developing solution having class consisting oi 8-hydroxyquinoline, S-hyreduced tendency to oxidation caused by heavy droxyquinoline-fi-sulfonic acid and 8-hydroxymetals and capable of forming a colored image quinoline-S-sulfonic acid substituted withamemupon development of an exposed silver halide ber of the class consisting of halogen and alkyl.
  • emulsion in the presence of a color coupler comprising an alkaline solution of a primary am- References Cited in the file of this Patent matic paradiamino developing agent, an alkali UNITED STATES PATENTS metal sulfite, and S-hydroxyquinoline-E-sulfonic acid. Number Name Date 2.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)

Description

Patented Oct. 12 1954 irnoxrojoaarnro'nsvrnornns ,.CONTAIN1NG I T'8-HYDR0XYQU'IN0LINES rRichard .':Hcnn.;and John pany, Rochester, N. Y.
Jersey 'I. Qrabtrce, R h- ;-,;assignors to Eastman Kodak iQoma corporation of New Nomrawing. Application March =14, 1952, [Serial No. 2763376 4 Claims. j9588) This invention relates -.to,photography and parcularly to photographic developers having re- .duced tendency to oxidation caused by heavy metals. i p I} "Fog in photographic emulsions is produced 1n several ways, one
.ofthe developer'when the emulsion is exposed to the air while wet with U type which is known as'aerialfog OCGUIS'ChlBflY developer. Fog of this or are otherwise unsatisfactory.
It is therefore an tion to provide photographic developers which accomplished by incorporating in the developing solution an 8-hydroxyquinoline especially an B-hydroxyquinoline-S-sulfonic acid.
The developing solutions which we propose to use contain a silver or equivalent material such as potassium bisulfite, and an 8-hydroxyquinoline. Among the 8-hydroxyquinolines which may 'be used for this purpose are 8-hydroXyquinoline-5-sulfonic acid, 7- chloro-8-hydroxyquinoline-5-sulfonic acid, 7- bromo-8-hydroxyquinoline-5-sulfonic acid and S-methyl 8 hydroxyquinoline sulfonic acid. The developing solution is an alkaline solution ten alkaline;material such as ghydroxide- 'or sodium tsimay-alsobe present. v I The :following examples illustrate developer formulas constituted; according to our (invention.
Example! 2-amino-fi-diethylaminotoluene monohydrochloride 3.0 Sodium carbonate (mono) 20.0 Potassium bromide 2.0
8-hydroxyquinoline-5-sulfonic acid 0.25 Water to 1 liter.
Example I! Grams Elon 5.0 Sodium sulfite 100.0 Sodium carbonate 2.5 Ethylenediamine sulfate 12.0 8-hydroxyquinoline-5-sulfonic acid 0.25 Water to 1 liter.
Example III Grams Hydroquinone 2.5 on 5.0 Sodium sulfite 100.0 0 Sodium metaborate 20.0 Ethylenediamine tetracetic acid 5.0 8-hydroxyquinoline-sulfat 1.0 Water to 1 liter.
The B-hydroxyquinolines developer in amounts varying from of two parts of without the 8-hydroxyquinoline-5-sulfonic acid decreased the aeration life to a vided air bubbles 8-hydroxyquinoline-5-sulfonic acid was aeration life was restored to its normal of 24 A similar effect was observed in of Example IH.
The color developer of Example I shows espe- 3. A photographic developing solution having cially good aeration life and is used for developreduced tendency to oxidation caused by heavy ing an emulsion containing color couplers, for exmetals and capable of forming a colored image ample, for developingafilm such as that described upon development of an exposed silver halide in Jelley and Vittum U. S. Patent 2,322,027. emulsion in the presence of a color coupler, com- In certain cases, the S-hydroxyquinolines of prising an aqueous solution of sodium carbonate, our invention may be incorporated in the emul- 2-amino-fi-diethylaminotoluene, sodium sulfite sion, overcoat, backing layer or interlayer of a and approximately 0.25 gram per liter of soluim. tion of B-hydroxyquinoline-S-sulfonic acid. It will be understood that the examples and 4. A photographic developer having reduced modifications included herein are illustrative only tendency to oxidation caused by heavy metals, and that our invention is to be taken as limited comprising an alkaline solution of a silver halide only by the scope of the appended claims. developing agent, an alkali metal sulfite, an ali- What we claim is: phatic amine, and. a compound selected from the 1. A photographic developing solution having class consisting oi 8-hydroxyquinoline, S-hyreduced tendency to oxidation caused by heavy droxyquinoline-fi-sulfonic acid and 8-hydroxymetals and capable of forming a colored image quinoline-S-sulfonic acid substituted withamemupon development of an exposed silver halide ber of the class consisting of halogen and alkyl. emulsion in the presence of a color coupler, comprising an alkaline solution of a primary am- References Cited in the file of this Patent matic paradiamino developing agent, an alkali UNITED STATES PATENTS metal sulfite, and S-hydroxyquinoline-E-sulfonic acid. Number Name Date 2. A photographic developing solution having gg fig Ulnch et 53 195;?! reduced ndency to oxidation caused by heavy as i g 2, :2 metals and capable of forming a colored image 235243241 i i g- 950 upon development of an exposed silver halide 2544649 g'fi g s i 1951 emulswn m the pr nce of a color coupler, com- 2,596,978 Burtner H May 20 1952 prising an alkaline solution of 2amino-5-diethylaminotoluene, sodium sulfite, and 8hydroxyquinoline-5-sulionic acid.

Claims (1)

  1. 4. A PHOTOGRAPHIC DEVELOPER HAVING REDUCED TENDENCY TO OXIDIZATION CAUSED BY HEAVY METALS, COMPRISING AN ALKALINE SOLUTION OF A SILVER HALIDE DEVELOPING AGENT, AN ALKALI METAL SULFITE, AN ALIPHATIC AMINE, AND A COMPOUND SELECTED FROM THE CLASS CONSISTING OF 8-HYDROXYQUINOLINE, 8-HYDROXYQUINOLINE-5-SULFONIC ACID AND 8-HYDROXYQUINOLINE-5-SULFONIC ACID SUBSTITUTED WITH A MEMBER OF THE CLASS CONSISTING OF HALOGEN AND ALKYL.
US276676A 1952-03-14 1952-03-14 Photographic developers containing 8-hydroxyquinolines Expired - Lifetime US2691588A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US276676A US2691588A (en) 1952-03-14 1952-03-14 Photographic developers containing 8-hydroxyquinolines
GB7057/53A GB720812A (en) 1952-03-14 1953-03-13 Improvements in photographic developers
FR1072957D FR1072957A (en) 1952-03-14 1953-03-13 Process for developing photographic images and new products for its implementation

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US2691588A true US2691588A (en) 1954-10-12

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FR (1) FR1072957A (en)
GB (1) GB720812A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3193386A (en) * 1961-11-29 1965-07-06 Du Pont Silver halide emulsions and elements containing antifoggants
US3335004A (en) * 1963-12-09 1967-08-08 Eastman Kodak Co Method for stabilization processing of color emulsions
US3386825A (en) * 1957-07-02 1968-06-04 Polaroid Corp Photographic product containing zinc
US4520099A (en) * 1982-09-02 1985-05-28 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive materials

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2168181A (en) * 1936-06-25 1939-08-01 Agfa Ansco Corp Photographic treating bath
US2268419A (en) * 1938-10-28 1941-12-30 Us Rubber Co Antiager
US2381863A (en) * 1943-05-01 1945-08-14 Monsanto Chemicals Method of fungusproofing textiles
US2524741A (en) * 1946-01-10 1950-10-03 Gen Aniline & Film Corp Magenta phenazonium dyestuff images from 6-substituted-8-hydroxyquinoline couplers
US2544649A (en) * 1949-01-14 1951-03-13 Frederick C Bersworth Caustic alkali composition of matter and its use as a polyvalent metal precipitationinhibitor
US2596978A (en) * 1947-09-17 1952-05-20 Searle & Co 8-hydroxy-1, 2, 3, 4-tetrahydroquinoline as a silver halide developer

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2168181A (en) * 1936-06-25 1939-08-01 Agfa Ansco Corp Photographic treating bath
US2268419A (en) * 1938-10-28 1941-12-30 Us Rubber Co Antiager
US2381863A (en) * 1943-05-01 1945-08-14 Monsanto Chemicals Method of fungusproofing textiles
US2524741A (en) * 1946-01-10 1950-10-03 Gen Aniline & Film Corp Magenta phenazonium dyestuff images from 6-substituted-8-hydroxyquinoline couplers
US2596978A (en) * 1947-09-17 1952-05-20 Searle & Co 8-hydroxy-1, 2, 3, 4-tetrahydroquinoline as a silver halide developer
US2544649A (en) * 1949-01-14 1951-03-13 Frederick C Bersworth Caustic alkali composition of matter and its use as a polyvalent metal precipitationinhibitor

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3386825A (en) * 1957-07-02 1968-06-04 Polaroid Corp Photographic product containing zinc
US3193386A (en) * 1961-11-29 1965-07-06 Du Pont Silver halide emulsions and elements containing antifoggants
US3335004A (en) * 1963-12-09 1967-08-08 Eastman Kodak Co Method for stabilization processing of color emulsions
US4520099A (en) * 1982-09-02 1985-05-28 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive materials

Also Published As

Publication number Publication date
GB720812A (en) 1954-12-29
FR1072957A (en) 1954-09-17

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