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

Definitions

• Yellow colored images are usually obtained by de- Welopment in the presence of compounds which contain an active methylene group, particularly acylacetanilide derivatives.
• a reducible "silver salt image is developed with ;an aromatic aminowdeveloping agent in the presence of a compound according to the formula: i
• the ketodiazine nucleus may be for example 4-pyrirnidone or 4-quinazolone.
• the sodium salt of anthranilic acid is condensed with 0-, mor p-nitrobenzoylchloride.
• the resulting amide is treated with acetic anhydride, thus looses a molecule of water and is converted into a nitrophenylbenzoxazine compound.
• This compound is converted with ammonium hydroxide and pyridine into nitrobenzoylanthranilamide which by boiling in diluted sodium hydroxide is converted into nitrophenylquinazolone.
• the latter is reduced with hydrogen and Raney nickel to the corresponding aminophenyl quinazolone which by condensation with XCH COOC H gives the desired coupler.
• metaand para-nit-robenzoylanthranilic acid obtained according to M. Bogert, R. Gortner and C. Amend, J.A.C.S. 33(1911), 952 may be converted into 2-(mand p-nitrophenyl)benzoxazine according to the same authors.
• the corresponding o-compound may be obtained as follows: o-nitro-benzoylanthranilic acid obtained. according to H. Meyer, Ann. 351 (1907), 273, may be converted into 2-(o-nitrophenyl)benzoxazine according to G. schroeter and O. Eisleb, Ann. 367(1909), 132.
• p-nitrobenzoylanthranilamide .melting at 242 C.
• o-nitro-benzoylanthranilarnide melting at 192 C.
• These anthranilamides may be converted into quinazolones.
• m-nitrobenzoylanthranilamide is refluxed with sodium hydroxide N.
• the reaction mixture is acidified with hydrochloric acid and the precipitate is recrystallized from dimethyl-formamide. Small yellow needles of Z-(m-nitrophenyl)quinazolone, melting above 300 C., are obtained.
• 2-(p-nitrophenyl)-quinazolone is dissolved in a mixtune on? piperidine and Water (equal parts by volume) and reduced in the presence of Raney nickel by hydrogen under a pressure of 30 kg. per sq. cm. and at 75 C. until the theoretical absorption of hydrogen has taken place.
• the reaction mixture is concentrated in vacuum and acidified with acetic acid.
• 2-(m-nitrophenyl)quinazolone is reduced in sodium hydroxide N by hydrogen under a pressure of 3 "kg; per sq. .cm. at 5.0-" C; in the presence .ofRaney nickel.
• the reaction mixture is acidified with hydrochloric acid A precipitate is formed by addition of ammonium hydroxide.
• the resulting 2- (m-aminophenyDquinazolone melts at 251 C.
• 2-(o-nitrophenyl)quinazolone is reduced in dimethylforrnamide in the presence of Raney nickel by hydrogen under a pressure of kg. per sq. cm. at 70 C.
• the resulting 2-(o-aminophenyl)quinazolone melts at 27.5- 227 C.
• couplers may be prepared as follows:
• the said quinazolones are refluxed in dimethylformamide together with an excess of 10-15% of beta-ketcester.
• the resulting beta-keto-anilide precipitates, is washed with methanol and recrystallized from glycolrnet'hyl ether or dimethyl-for-mamide.
• color couplers may arise from adding to the developer a compound which differs from the color coupler only because in the active CH -grou-p one or two hydrogen atoms are replaced by a group capable of splitting off either before development occurs by the action of the alkali in the developing solution or during the color-development.
• aromatic amino compounds which according to our invention are used as developing agents, comprise mono-, diand tri-amino aryl compounds, particularly NzN-dialkyl-para-phenylene diamines and derivatives such as NrN-dialkyl-N'-sulphomethyl-para-phenylene diamines.
• mono-amino developers may be mentioned amino phenols and arnino-cresols and their halogen den'vatives, and also amino-naphthols.
• An exposed photographic film strip coated with a silver halide emulsion layer is developed in a bath of the following composition:
• One of the couplers 1 to' 7 prepared as described above 1 Water to 50 cmfi.
• Solution B is added to'Solution A and water is added to the resulting solution to 1,000 cm.*.
• a yellow image is obtained.
• We claim: 7 1. Process for obtaining a colored photographic image, comprising developing an image consisting of a reducible silver salt with a color forming developer'com tainin-g an N,N-dialkyl-para-pheny1ene diamine as a developing agent, and a quinazolone color coupler selected from the group consisting of 2-(benzoyl-acetamino-phenyl)-4-quinazolone, 2-[m(p-anisoyl-acetamino)-phenyl]- 4 quinazolone, 2 (m-acetyl-acetamino-phenyl) -4-quinazolone, Z-[m-(alpha-furoyl-acetamino)phenyl]-4-quinazolone, and 2-[m-(alpha-thenoyl-acetamino)phenyl]-4- quinazolone.
• Photographic developer containing an N,N-dialkylpara-phenylene diamine as a developing agent, and a quinazolone compound as a color coupler, said quinazolone compound being selected from the group consisting of Z-(benzoyl-acetamiino-phenyl)-4-quinazolone, 2-1[m-' (p-anisoyl-acetamino)phenyl]-4-quinazolone, 2 (m-acetyl-acetamino-phenyl) -4-quinazolone, 2 [m (alpha-furoyl-acetamino)phenyl]-4-quinazolone, and Z-[m-(alphathenoyl-acetamino)-pheny1] -4-quinazolone.
• Process for obtaining a colored photographic image comprising developing an image consisting of a reducible silver salt with a color forming developer containing an N,N-dialkyl-para-phenylene diamine as a developing agent, and 2 (benzoyl-acetamino-phenyl)-4- quinazolone as a color coupler.
• Photographic developer containing an N,N-dialkyl para-pheny-lene diamine as a developing agent, and 2- (benzoyl-acetamino-phenyl) 4-quinazolone as a color coupler.

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• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
• Silver Salt Photography Or Processing Solution Therefor (AREA)

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Cited By (4)

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Citations (2)

• 0
  • BE BE565656D patent/BE565656A/xx unknown
• 1957
  • 1957-03-15 GB GB8588/57A patent/GB856158A/en not_active Expired
• 1958
  • 1958-03-10 US US720013A patent/US2992920A/en not_active Expired - Lifetime
  • 1958-03-14 FR FR1201538D patent/FR1201538A/fr not_active Expired

Patent Citations (2)

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