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

• This invention relates .to a. process for the manufacture of photographic color images by color development in the presence of a color coupler, to photographic developers which contain such color couplers, to photographic material which, contains such color couplers, and to photographic images obtained according to the process referred to.
• a photographic color image by developing a reducible silver salt image in the presence of a color coupler, i. e., a compound which during development couples with the oxidation product of the developing agent and forms a dyestuff that precipitates onto the developed silver grains.
• a color coupler i. e., a compound which during development couples with the oxidation product of the developing agent and forms a dyestuff that precipitates onto the developed silver grains.
• Yellow and magenta color images are'usually obtained by development in the presence of compounds which contain an active methylene group, for instance, compounds wherein the methylene group is connected at one side to a heterocyclic ring and at the other side to another group capable of activating a methylene group, such as, a cyanor a carbonyl group.
• a reducible silver salt image is developed with a primary amino aromatic developing agent in the presence of a compound according to the following formula:
• .fl hesecompounds may be-..obtained; .e therrbv causing anthranilic. acid or a derivative-thereof to react with the imino ether of cyan "acetic" ester, analogously with the method described by A. Finger and L. Schupp in J. Pr. Chem. (2) '74 (1906) 154, or by effecting a ring closure in an anthranilic acid or -amide, wherein the amino developer or to a colloid layer, a light-sensitive group is substituted by R.CO.CH2.CO, R.CO' having the same significance as indicated hereinbefore, in analogy with the method described by Tomisk and Christensen in J. Am. Chem. Soc.
• the presence of the color couplers according to our invention during color development may arise from the adding to the photographic material, or to the developer, a compound which differs from the color coupler only insomuch as in the active CH2- group one or two hydrogen atoms are replaced by a group splitting 01f either before or during the color development.
• the aromatic amino compounds which according to our invention are added to the developer, comprise the mono-, diand triamino aryl compound.
• mono-amino developers may be mentioned amino-phenols and amino-cresols and their halogen derivatives, and also amino naphthols.
• the developers preferred for our purposes are the aromatic orthoand paradiamines, suchas, paraphenylene diamines and their substitution products.
• Example 1 7.95 g. imino ether of cyan acetic acid ethyl ester and 6.85 g. anthranilic acid are refluxed for 5 hours in 30 com. alcohol. After cooling, the precipitate formed is sucked off and recrystallized from ethanol.
• the 2-carbethoxymethyl-4-quinazolone thus obtained corresponds to the following formula:
• a photographic film strip is developed in a bath of the following composition:
• the image is again rinsed for 10 minutes and then fixed for 20 minutes in the following bath:
• Example 2 To 4.4 g. of the compound according to Formula II, dissolved in 100 com. alcohol, 0.6 g. hydrazine dissolved in a minimum of alcohol are added. The mixture is boiled for 1 hour on the water bath and the precipitate formed is recrystallized and washed with ethanol. The product obtained corresponds to the following formula:
• Emmple 3 2.78 g. hydroxylamine hydrochloride and 0.92 g. sodium are dissolved in 50 com. pure alcohol, and 4.6 g. of the compound according to Formula II are added. This mixture is heated for 1 hour on the water bath. After cooling, a precipitate is formed which is washed with. ethanol.
• the hydroxamic acid obtained corresponds to the following formula:
• Example 4 10 g. 4-nitro-anthranilic acid and 12 g. imino ether of cyan acetic acid ethyl ester are melted together at 60 C. for 4 hours on the water bath.
• the product obtained is recrystallized from methanol and corresponds to the following formula:
• Example 5 The compound according to Formula V is dissolved in ethanol and catalytically reduced under 1 to 2 atmosphere pressure with Raney nickel. After evaporation of the alcohol, the amino derivative according ot the following formula:-
• Example 6 To 3.4 g. anthranil amide dissolved in 10 com. chloroform are added 2.1 g. diketene. The mixture isheated until a homogeneous solution is obtained. This solution is left for 24 hours at room temperature whereafter the precipitate formed is sucked off. After recrystallization from ethanol, aceto-acethyl anthranil amide is obtained. Melting point: 142-144 C. 5.5 g. of the product obtained are dissolved in 10 com. aqueous solution of NaOI-I 5%. The solution is heated on the water bath for 40 minutes and neutralized with acetic acid to pH 7. The precipitate formed is sucked ed and recrystallized from dioxane. The compound obtained corresponds to the following formula:
• Example 7 2.05 g. imino ether of para-methyl cyanacetophen m and 1.33- .s.. ant ranilic. arid-are heated together 1 on thenbo-iling waiter bath,f After 2.0- minutes,;the mass melts. but. heating is; continued, for 5 more hours.
• the precipitate formed is recrystallized from glycol-monomethyl ether.
• the product obtained corresponds to the following formula:
• Example 8 3.6 g. imino ether of furoyl acetonitrile and 2.74 g. anthranilic acid are melted together on the boiling water bath and then heated for 3 hours. The oil obtained is shaken with an aqueous solution, of NazCOs and the solution obtained is acidified with acetic acid. The precipitate formed is sucked off.
• the compound obtained corresponds to the following formula:
• Example 9 1.87 g. 2-amino-1-naphtoic acid and 2.40 g. imino ether of cyan acetic acid ethyl ester are heated together for 2 hours at 60 C. on the water bath. The: solid product. formed is. recrystallized from dioxane. Melting, point: 183-185 C. The compound obtained corresponds to the following formula:
• Example 1 0 2.18 g. quinazolonyl acethydrazide according to Formula III and 3.24 g. hexadecyl succinic acid anhydride are refluxed for 3 hours in com. dioxane. After cooling, the precipitate formed is separated by filtration and purified by dissolving in an aqueous solution of NaOI-I 2N and precipitating with an aqueous solution of I-ICl 2N. After recrystallization from dioxane, the melting po nt is lfiaello: c. 'rhmomnound obtained.
• Z is arylene
• --COR is a member selected from the group consisting of an acyl-, an
• ester-. and amide- a hydrazideand a hydroxamic acid group.
• Z is arylene
• --COR is a member selected from the group consisting of an acyl-, an
• ester- an amide-, a hydrazideand a hydroxamic I acid group.
• Photographic developer containing 7 a primary amino aromatic developing agent and a color coupler corresponding to the following formula:
• Photographic developer containing a primary amino aromatic developing agent and a color coupler corresponding to the following formula:
• Photographic developer containing a primary amino aromatic developing agent and a color coupler corresponding to the following formula:
• Light-sensitive photographic material comprising a silver halide emulsion layer and a compound corresponding to the following formula:
• Z is arylene, -CO--R is a hydrazide group.
• Photographic developer containing mary amino aromatic developing agent compound having the following formula:
• Photographic developer containing mary amino aromatic developing agent compound having the following formula:
• Photographic developer containing mary amino aromatic developing agent compound having the following formula:
• Photographic developer containing mary amino aromatic developing agent compound having the following formula:
• Light-sensitive photographic material comprising a silver halide emulsion layer and a compound having the following formula:

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• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Plural Heterocyclic Compounds (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Nitrogen Condensed Heterocyclic Rings (AREA)

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Cited By (9)

Citations (2)

• 0
  • BE BE500139D patent/BE500139A/xx unknown
• 1951
  • 1951-12-12 DE DEG7627A patent/DE893143C/de not_active Expired
  • 1951-12-15 US US261932A patent/US2668112A/en not_active Expired - Lifetime
  • 1951-12-18 FR FR1046512D patent/FR1046512A/fr not_active Expired
  • 1951-12-20 GB GB29852/51A patent/GB689023A/en not_active Expired

Patent Citations (2)

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