US2271229A - Fog inhibitor for photographic developers - Google Patents

Fog inhibitor for photographic developers Download PDF

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Publication number
US2271229A
US2271229A US303878A US30387839A US2271229A US 2271229 A US2271229 A US 2271229A US 303878 A US303878 A US 303878A US 30387839 A US30387839 A US 30387839A US 2271229 A US2271229 A US 2271229A
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US
United States
Prior art keywords
indazole
nitroindazole
developers
fog inhibitor
photographic developers
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
US303878A
Inventor
Willard D Peterson
Ralph M Evans
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 US303878A priority Critical patent/US2271229A/en
Priority to GB2815/40A priority patent/GB541232A/en
Application granted granted Critical
Publication of US2271229A publication Critical patent/US2271229A/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
    • G03C7/407—Development processes or agents therefor
    • G03C7/413—Developers
    • 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
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
    • 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
    • G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
    • G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
    • G03C5/29—Development processes or agents therefor
    • G03C5/305—Additives other than developers

Definitions

  • This invention relates to photographic developers and particularly to fog inhibiting or toning agents for developers.
  • Indazole has the following structural formula:-
  • reaction mixture is always kept slightly alkaline by small additions of 5% alkali, when necessary.
  • the compounds 5-p toluene-sulfonamido-innitrobenzoylamino-indazole are obtained by reduction of 5-nitroindazole and subsequent treatment with the suitable acid chloride.
  • the compound 5 benzoylacetamino-indazole is best prepared by heating 5-amino-indazole with ethyl benzoyl acetate to 165 C.-1'75 C. and distilling off the alcohol generated during the course of the reaction.
  • the compound E-amino-indazole is prepared by simple reduction of 5-nitro-indazole.
  • Example 1 Ablaok and white developer is made as follows:
  • 5-nitroindazole may be prepared as follows: Y 2 parts by weight of 5-nitro-2-amino-toluene dissolved in100 parts of acetic acid are treated at C. with a concentrated aqueous solution containing 0.91 part of sodium nitrite. The re sulting solution is allowed to stand for a day and is then concentrated nearly to dryness.
  • Example 2 A developing solution for forming a colored image by coupler development is made as follows:
  • B is added to A.
  • This developer produces a blue-green dye on development of an exposed silver halide layer.
  • the amountjoi' the indazole derivative used in developers either in black and white or in color developers may vary from about .005 gram to .50 gram per liter or agenhg coupler compound, and 5-nitroindazole.-

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

?atented Jan. 27,, 1942 roe mmarroa non Pno'roermrnrc "DEVELOPERS Willard D. Peterson and Ralph M. Evans, Rochester, N. Y., assignors to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey No Drawing. Application November'10, 1939, Serial No. 303,878
2 Claims.
This invention relates to photographic developers and particularly to fog inhibiting or toning agents for developers.
It is well known that fogging occurs in a photographic film or plate when itis developed at temperatures higher than 70 F. or when developed for unusually long periods of time. It is necessary in most cases to use a relatively weak developer in order to avoid the formation of fog. Soluble bromides, such as potassium bromide, have been used in -the developer to overcome this but they do not permit development with a strong developer for long periods of time at temperatures which may go higher than 70 F. We have discovered that certain derivatives of indazole, for example, 5-nitroindazole and 5- aminoindazole, may be incorporated in the developer to obtain all of these advantages. These compounds may be used either in black and white or in color developers. In some cases they maybe added to the emulsion or to the subbin or backing layers of the film or plate.
Indazole has the following structural formula:-
able are 5-nitroindazole, l-methyl-fi-nitro-indazole, S-amino-indazole, 5-p-.toluene sulfonamido- 5.6 parts by weight of fi-nitro-indazole are suspended in asolutionof 1.5 parts of sodium hydroxide in 40 parts of water. With good stirring, 5.1 parts of dimethyl sulfate are added slowly. The temperature is maintained at 25- 35 C. and the time required for adding the di-v .methyl sulfate is approximately two hours. The
reaction mixture is always kept slightly alkaline by small additions of 5% alkali, when necessary.
The compounds 5-p toluene-sulfonamido-innitrobenzoylamino-indazole are obtained by reduction of 5-nitroindazole and subsequent treatment with the suitable acid chloride. The compound 5 benzoylacetamino-indazole is best prepared by heating 5-amino-indazole with ethyl benzoyl acetate to 165 C.-1'75 C. and distilling off the alcohol generated during the course of the reaction. The compound E-amino-indazole is prepared by simple reduction of 5-nitro-indazole.
The following examples, which are-illustrative only, indicate developing formulae using nitro derivatives of indazole according to our invention.
Example 1 Ablaok and white developer is made as follows:
Monomethyl-paminophenol sulfate grams 1 indazole. 5-benzoylacetamino indazole, and 5-pnitrobenzoylamine indazole. The structural for 'mulas of 5-nitroindazole and 1-methyl-5-nitroindazole, respectively, are as follows:
5-nitroindazole may be prepared as follows: Y 2 parts by weight of 5-nitro-2-amino-toluene dissolved in100 parts of acetic acid are treated at C. with a concentrated aqueous solution containing 0.91 part of sodium nitrite. The re sulting solution is allowed to stand for a day and is then concentrated nearly to dryness. The
' residue is washed well with water to remove the remaining acetic acid. The product is obtained in pure form by recrystallization Irom dilute methyl alcohol, and melts at 2 06-208 C.
1-methy1-5-nitroindazole is prepared as follows:
Hydroquinone' do 5 Sodiums fi do Sodium carb 30 v Potassium bromide; do .5-
5-nitroindazo do .1 Water to liter 1 In this formula the potassium bromide may be entirely omitted since its function is performed by the 5 -nitroindazole. I
Example 2 A developing solution for forming a colored image by coupler development is made as follows:
A. 2-amino-5-diethylaminotoluenehydro- In use, B is added to A. This developer produces a blue-green dye on development of an exposed silver halide layer. The amountjoi' the indazole derivative used in developers either in black and white or in color developers may vary from about .005 gram to .50 gram per liter or agenhg coupler compound, and 5-nitroindazole.-
higher.
ofthe appended claims.
7 2. A color-forming photographic developer We consider as within our invention all equivacomprising a primary aromatic amino developing lents'and modifications coming within the scope agent, a. coupler v I nitroindazole.
. We claim: v v p D. PEI'ERSON.
1. A color-forming photographic developer RALPH M. EVANS.
I comprising a primary aromatic amino geveioping compound, and 1-methyl-5-
US303878A 1939-11-10 1939-11-10 Fog inhibitor for photographic developers Expired - Lifetime US2271229A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US303878A US2271229A (en) 1939-11-10 1939-11-10 Fog inhibitor for photographic developers
GB2815/40A GB541232A (en) 1939-11-10 1940-02-14 Improvements in fog inhibitors for photographic silver salt emulsions

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US303878A US2271229A (en) 1939-11-10 1939-11-10 Fog inhibitor for photographic developers

Publications (1)

Publication Number Publication Date
US2271229A true US2271229A (en) 1942-01-27

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US (1) US2271229A (en)
GB (1) GB541232A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2497917A (en) * 1947-10-17 1950-02-21 Eastman Kodak Co Method of producing direct positive photographs having increased density
US2541472A (en) * 1948-06-29 1951-02-13 Eastman Kodak Co Direct positive emulsion containing desensitizing dye
US2656271A (en) * 1949-10-24 1953-10-20 Keuffel & Esser Co Method of developing aged photosensitive material containing silver halide and a chromate
US2676103A (en) * 1950-03-18 1954-04-20 Fr Corp Process and composition for use in color photography
DE1003581B (en) * 1951-11-14 1957-02-28 Eastman Kodak Co Process for preventing overdevelopment of the top emulsion layer of halogen silver multilayer materials during color development
US4172728A (en) * 1977-12-16 1979-10-30 E. I. Du Pont De Nemours And Company High contrast continuous tone developer and process of use
US4323642A (en) * 1981-03-09 1982-04-06 Eastman Kodak Company Stable photographic developers containing an indazole antifoggant and a lignosulfonate
US4345024A (en) * 1980-04-30 1982-08-17 Fuji Photo Film Co., Ltd. Photographic development inhibitor releasing compound
US5272045A (en) * 1992-11-13 1993-12-21 Sun Chemical Corporation Water soluble antifoggant for powder developer solutions
US5811226A (en) * 1996-03-14 1998-09-22 Eastman Kodak Company Method of processing a silver halide photographic element which reduces fog

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2497917A (en) * 1947-10-17 1950-02-21 Eastman Kodak Co Method of producing direct positive photographs having increased density
US2541472A (en) * 1948-06-29 1951-02-13 Eastman Kodak Co Direct positive emulsion containing desensitizing dye
US2656271A (en) * 1949-10-24 1953-10-20 Keuffel & Esser Co Method of developing aged photosensitive material containing silver halide and a chromate
US2676103A (en) * 1950-03-18 1954-04-20 Fr Corp Process and composition for use in color photography
DE1003581B (en) * 1951-11-14 1957-02-28 Eastman Kodak Co Process for preventing overdevelopment of the top emulsion layer of halogen silver multilayer materials during color development
US4172728A (en) * 1977-12-16 1979-10-30 E. I. Du Pont De Nemours And Company High contrast continuous tone developer and process of use
US4345024A (en) * 1980-04-30 1982-08-17 Fuji Photo Film Co., Ltd. Photographic development inhibitor releasing compound
US4323642A (en) * 1981-03-09 1982-04-06 Eastman Kodak Company Stable photographic developers containing an indazole antifoggant and a lignosulfonate
US5272045A (en) * 1992-11-13 1993-12-21 Sun Chemical Corporation Water soluble antifoggant for powder developer solutions
US5811226A (en) * 1996-03-14 1998-09-22 Eastman Kodak Company Method of processing a silver halide photographic element which reduces fog
US5935771A (en) * 1996-03-14 1999-08-10 Eastman Kodak Company Method of processing a silver halide photographic element which reduces fog

Also Published As

Publication number Publication date
GB541232A (en) 1941-11-19

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