US2449919A - 3-methylsulfonamido-4-amino dimethyl aniline photographic developer - Google Patents

3-methylsulfonamido-4-amino dimethyl aniline photographic developer Download PDF

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Publication number
US2449919A
US2449919A US759302A US75930247A US2449919A US 2449919 A US2449919 A US 2449919A US 759302 A US759302 A US 759302A US 75930247 A US75930247 A US 75930247A US 2449919 A US2449919 A US 2449919A
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Prior art keywords
methylsulfonamido
photographic
amino
dimethyl aniline
photographic developer
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US759302A
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Weissberger Arnold
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to US759302A priority Critical patent/US2449919A/en
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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
    • G03C7/4136—Developers p-Phenylenediamine or derivatives thereof

Definitions

  • This invention relates to photographic de- CH velopers and more particularly to photographic developers for color photography.
  • Developing agents of the p-phenylene diamine type having a lower fatty acid acyl amino group such as an acetylamino group on the phenylene ring are described in Hanson U. S. Patent 2,350,109, granted May 30, 1944. While these developing agents are suitable for producing colored images by coupling with color-forming compounds, they are of rather low solubility in the developing solution.
  • a further object is to provide developing agents of the p-phenylene diamine type which are of suflicient solubility in the developing solution to enable the production of dye images upon color development, having the required density.
  • Developing agents which may be used according to my invention are 3-methy1sulfonam1do-4- amino-dimethylaniline, 3-methylsulfonamido-4- 'amino-diethylaniline, etc.
  • a typical compound, 3 methylsulfonamido-4-amino-dimethylaniline has the following structure:
  • the corresponding diethyl compound may be prepared by treating the diethylaminonitroso compound in a similar manner.
  • the developers of my invention may be used in conjunction with any well-known coupler compounds such as those described in Fischer U. 8. Patent 1,102,028, granted June 30, 1914, Mannes and Godowsky U. 8. Patent 2,108,602, granted February 15, 1938, or Mannes,
  • the developers of my invention produce magneta to red dyes with phenolic hydroxyl coupiers, such as 2,4-dichloro-a-naphthol. These dyes are of the azine class.
  • the following example illustrates a developing solution which may be used according to my invention 3 methylsulfonamido 4-amino-dimethylaniline "grams" 1 Sodium suliite do 0.5 Sodium carbonate do 20 Potassium bromide do 1 Water to 1 liter (1:) Coupler (2,4-dichloro-a-naphtho1) --do 2 Sodium hydroxide (10% solution) cc 10 For use, b is added to a.
  • the developing agents described in the present application may be used to form photographic images by development of exposed silver halide contained in the usual gelatin carrier or in carriers such as coll-odion, water-permeable cellulose ester or water-permeable synthetic resins.
  • a developing solution for producing a colored photographic image comprising 3-methylsulfonamido-4-amino-dimethyl aniline and a compound which couples with the development of said developing agent to form a colored image upon photographic development.

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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 Sept. 21 1948 2,449,919 I v3-METHYLsunrolvniun'io-4-AMmo m 'ME'mYn'ANmmn PHOTOGRAPHIC DEVELOPER Arnold Weissberger, Rochester, N. -Y.,,assignor to vj.
Eastman Kodak Company, Rochester, N.; Y.,. a 1
corporation of New Jersey No Drawing. Application July 5, 194
Serial No. 759,302 2 Claims. (01. 95-88) 2 This invention relates to photographic de- CH velopers and more particularly to photographic developers for color photography.
It is known that photographic developers of H: on. the p-phenylene diamine type are valuable Oil;- 5 2Hr-' pounds for producing fine grain black-and-w e photographic images and also that these compounds, especially when they contain alkyl sub- N0 NHI stituents on one of the nitrogen atoms are useful m as developers in producing colored photographic The troso compound (7 ms) was susimages.
Developing agents of the p-phenylene diamine type having a lower fatty acid acyl amino group such as an acetylamino group on the phenylene ring are described in Hanson U. S. Patent 2,350,109, granted May 30, 1944. While these developing agents are suitable for producing colored images by coupling with color-forming compounds, they are of rather low solubility in the developing solution.
It is therefore an object of the present invention to provide a new class of photographic developing agents of the p-phenylene diamine type. A further object is to provide developing agents of the p-phenylene diamine type which are of suflicient solubility in the developing solution to enable the production of dye images upon color development, having the required density.
These objects are accomplished by the present invention by the use as developing agents of 3 methylsulfonamido i-amino-dialkylaniline compounds.
Developing agents which may be used according to my invention are 3-methy1sulfonam1do-4- amino-dimethylaniline, 3-methylsulfonamido-4- 'amino-diethylaniline, etc. A typical compound, 3 methylsulfonamido-4-amino-dimethylaniline has the following structure:
C HI
NHSOlC HI This compound was prepared by reduction of the nitroso compound according to the following reaction:
pended in alcohol and reduced with Raney nickel catalyst and hydrogen at room temperature. The filtered solution was treated with 2.8 grams of sulfuric acid in 2 cc. of water, stirred and cooled in ice. The crystalline sulfate was filtered from the deep purple solution, washed with alcohol, ether and dried. The yield was 5.5 grains (69%). It was a grayish powder, readily soluble in water.
The corresponding diethyl compound may be prepared by treating the diethylaminonitroso compound in a similar manner.
When used for the formation of colored photographic images, the developers of my invention may be used in conjunction with any well-known coupler compounds such as those described in Fischer U. 8. Patent 1,102,028, granted June 30, 1914, Mannes and Godowsky U. 8. Patent 2,108,602, granted February 15, 1938, or Mannes,
'Godowsky and Peterson U. S. Patent 2,115,394,
granted April 26, 1938, and 2,126,337, granted August 9, 1938.v
The developers of my invention produce magneta to red dyes with phenolic hydroxyl coupiers, such as 2,4-dichloro-a-naphthol. These dyes are of the azine class.
The following example illustrates a developing solution which may be used according to my invention 3 methylsulfonamido 4-amino-dimethylaniline "grams" 1 Sodium suliite do 0.5 Sodium carbonate do 20 Potassium bromide do 1 Water to 1 liter (1:) Coupler (2,4-dichloro-a-naphtho1) --do 2 Sodium hydroxide (10% solution) cc 10 For use, b is added to a.
The developing agents described in the present application may be used to form photographic images by development of exposed silver halide contained in the usual gelatin carrier or in carriers such as coll-odion, water-permeable cellulose ester or water-permeable synthetic resins. My developing agents may be used with photographic films containing the coupler in the emulsion layer as described in Mannes and Godowsky 'U.:.'"S .1Patent 2,304;94 0, granted December=15, .,1*942,1or .Jelley andWittum-KLUJ S." Batent 2,322,027, granted June 15, 1943.
It will be understood that the examples in-- 1. A photographic developing *solution com prising as the developing agent ii-methylsulfonamido-4-amino-dimethy1 aniline.
Tile of "this patent:
2. A developing solution for producing a colored photographic image comprising 3-methylsulfonamido-4-amino-dimethyl aniline and a compound which couples with the development of said developing agent to form a colored image upon photographic development.
ARNOLD WEISSBERGER.
REFERENCES CITED The followingi'referencesare of record in the UNITED STATES PATENTS
US759302A 1947-07-05 1947-07-05 3-methylsulfonamido-4-amino dimethyl aniline photographic developer Expired - Lifetime US2449919A (en)

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2527379A (en) * 1948-07-15 1950-10-24 Gen Aniline & Film Corp Silver halide developers for the production of azine dyestuff images
US2537460A (en) * 1948-07-15 1951-01-09 Gen Aniline & Film Corp Production of azine dye images by means of a developer containing two n-substituted-diamino-meta-nilic acids
US2592364A (en) * 1947-05-23 1952-04-08 Eastman Kodak Co p-phenylenediamine developer containing alkylacylamidoethyl or alkylacylamidoethoxyring substituents
US2592363A (en) * 1947-05-23 1952-04-08 Eastman Kodak Co P-phenylenediamine developer containing nu-alkylacetamido ethyl substituent
US2594917A (en) * 1949-12-16 1952-04-29 Gen Aniline & Film Corp Suppression of proximity development with azine color developers
EP0364845A2 (en) * 1988-10-20 1990-04-25 Agfa-Gevaert AG Photographic-reversal process
EP0370351A2 (en) * 1988-11-24 1990-05-30 Agfa-Gevaert AG Photographic reversal process
EP0370348A1 (en) * 1988-11-24 1990-05-30 Agfa-Gevaert AG Photographic-reversal method
EP0433812A1 (en) * 1989-12-21 1991-06-26 Agfa-Gevaert AG Method for colour developing

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2163166A (en) * 1936-05-27 1939-06-20 Agfa Ansco Corp Photographic developer
US2350109A (en) * 1941-09-11 1944-05-30 Eastman Kodak Co Photographic developers containing acylamino groups
US2414491A (en) * 1945-01-27 1947-01-21 Gen Aniline & Film Corp Photographic developer

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2163166A (en) * 1936-05-27 1939-06-20 Agfa Ansco Corp Photographic developer
US2350109A (en) * 1941-09-11 1944-05-30 Eastman Kodak Co Photographic developers containing acylamino groups
US2414491A (en) * 1945-01-27 1947-01-21 Gen Aniline & Film Corp Photographic developer

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2592364A (en) * 1947-05-23 1952-04-08 Eastman Kodak Co p-phenylenediamine developer containing alkylacylamidoethyl or alkylacylamidoethoxyring substituents
US2592363A (en) * 1947-05-23 1952-04-08 Eastman Kodak Co P-phenylenediamine developer containing nu-alkylacetamido ethyl substituent
US2527379A (en) * 1948-07-15 1950-10-24 Gen Aniline & Film Corp Silver halide developers for the production of azine dyestuff images
US2537460A (en) * 1948-07-15 1951-01-09 Gen Aniline & Film Corp Production of azine dye images by means of a developer containing two n-substituted-diamino-meta-nilic acids
US2594917A (en) * 1949-12-16 1952-04-29 Gen Aniline & Film Corp Suppression of proximity development with azine color developers
EP0364845A2 (en) * 1988-10-20 1990-04-25 Agfa-Gevaert AG Photographic-reversal process
EP0364845A3 (en) * 1988-10-20 1991-09-25 Agfa-Gevaert AG Photographic-reversal process
EP0370351A2 (en) * 1988-11-24 1990-05-30 Agfa-Gevaert AG Photographic reversal process
EP0370348A1 (en) * 1988-11-24 1990-05-30 Agfa-Gevaert AG Photographic-reversal method
EP0370351A3 (en) * 1988-11-24 1991-09-18 Agfa-Gevaert AG Photographic reversal process
EP0433812A1 (en) * 1989-12-21 1991-06-26 Agfa-Gevaert AG Method for colour developing

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