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

• colored photographs may be group --CX2 wherein, X represents an-halogen obtained by using a developer which during the 5 atom such as CH3-CO--CHC1zand development forms colored insoluble oxidation products. These products color the gelatine around the silver grains of the silver image.
• color couplers which combine with the oxidation products of the developer with the formation of dyestuifs which precipitate simultaneously with the developed silver grains.
• color couplers have hitherto been used or proposed, such as substituted or unsubstituted phenols and naphthols, nitrophenylacetonitriles and acetamide derivatives, characterized by the presence of an acid-reactive methylene group, isoxazolones, coumarones and pyrazolones.
• color couplers of the new group As typical examples of color couplers of the new group, the following may be mentioned:
• a hot aqueous solution .of cyanoacetylhydrazide is mixed with a hot alcoholic solution of the compound with which the hydrazide is to be condensed.
• condensation takes place immediately and the condensation product precipitates .inthe form of.crystals; ifnot, the solution-.is warmed'forsome time in a water bath.
• the condensation. of. a hydrazide, and especially of cyanoacetylhydrazide ⁇ with various compounds containing a ketone or. an. aldehyde group is.fully described in Berichte 27 (1894) 688, 40 (1907) 712 and 41 (1908)f 643.
• dyestuffs are obtained with an absorption maximumat about 4,800 to 5,500 A.
• the new color couplers maybe added to a developing bath containing a normal quantity of sulphite and on account of this are very stable. They may easily be produced. and isolated, and are, moreover, very stable.
• the new color couplers form dyestuffs practically insoluble in water and photographic baths and arecharacterized by an extreme brightness. or brilliance.
• the absorption curves of these dye-stuffs are generally of marked steepness which in color photography is. of great importance.
• the color yield is generally very high.
• the present invention also comprises:
• New or improved color developers containing besides an aryl amine developer at least one of the above-specified color couplers.
• a photographic material which contains at least in one layer a bright and transparent color image consisting of the condensation product formed during the development from a color coupler as herein described and the oxidation product of an aryl amine developer.
• the aryl amine derivatives which may be used as developers are mono-, diand tri-amino aryl compounds.
• mono-amino developers may be mentioned aminophenols, aminocresols, aminonaphthols and their halogen derivatives.
• the most suitable and at the same time the best developers for use in the present invention are the aryl orthoand para-diamines such as orthoand para-phenylene diamines. These developers may be substituted in one amino group and/or in the nucleus. In this way, several developers may be obtained, as, for instance:
• N-diethyl-paraphenylenediamine N-mono-ethyl-para phenylenediamine N dimethyl-para-phenylenediamine 3 -amino-6-diethyl-aminotoluene
• These developers are usually used in the form of their salts such as hydrochlorides or sulphates.
• color development as used in.this specification is broadly to be understood the formation of a color image by the action of the color couplers. as described above on any oxidizing compounds formed either during development by the action of the silver halide of the latent image on the aryl developers or by the interventionof the silver of the developed image.
• the silver image is treated with an oxidizing. bath before color develop? ment.
• the color couplers may be dissolved in organic solvents, for instance acetone, though it is .'also ,possible to add them directly to the developing baths without using organic solvents.
• the invention is not limited to the use of the color couplers in the photographic developing baths.
• One of the essential ingredients (the color coupler) which forms the dyestuif. during the development may also be added to the photographic emulsion, for instance, by adsorption ,on the silver salts before or after the emulsion is coated.
• the other ingredient of the colorforming baths, especially the aryl amine developer, may afterwards be applied as a bath during the development.
• the invention may be applied for the manufacture of photographic multi-color pictures on plates, paper or film provided with gelatine or any other protective colloid for silver salts.
• the color developing process may be carried out for developing photographic material with one or more light-sensitive layers coated on one or on both sides of the support.
• the silver image formed during development may easily be bleached out, whereby the bleaching bath may not exert any undesirable influence on the color image.
• An aqueous solution of potassium ferricyanide and sodium thiosulphate easily removes the silver without damaging the color image.
• a color-forming developer comprising a primary aromatic amino silver halide developing agent and as color coupler a cyanoacetylhydrazone of the general formula wherein X represents the radical of a compound, which does not contain group capable of coupling with the oxidation product of a primary aromatic amino silver halide developing agent to form a dye image but which is capable of froming a hydrazone by reaction with a hydrazine and selected from the group consisting of aldehydes, ketones, and compounds having two halogen atoms directly linked to the same carbon atom, and n is a positive integer selected from the group consisting of l and 2, the cyanoacetyl group comprising the methylene group which acts as coupling function on color development.
• a color-forming developer comprising a primary aromatic amino silver halide developing agent and as color coupler a cyanoacetylhydrazone of the general formula wherein X represents the radical of a compound which does not contain a group capable of coupling with the oxidation product of a primary aromatic amino silver halide developing agent to form a dye image but which is capable of forming a hydrazone by reacting with a hydrazine and selected from the group consisting of aldehydes, ketones, and compounds having two halogen atoms directly linked to the same carbon atom, the cyano acetyl group comprising the methylene group Which acts as coupling function on color development.
• c I T 3 A color-forming developer comprising a, primary-aromatic amino silver halide developing agent and as' color coupler the cyanoacetylhydrazone of piperonal.
• a color-forming developer comprising a primary aromatic amino silver halide developing agent'and as color coupler the cyanoacetylhydrazone of 5-nitro-7-methylisatin.
• a color-forming developer comprising a primary aromaticamino silver halide developingagent and as color couplerthe cyanoacetylhydrazone of cinnamic aldehyde.
• j I 6 A color-forming developer comprising a primary aromatic amino silver halide developing agent and as color coupler a di-cyanoacetylhydr'azone of the general formula wherein X represent the radical of a comopund which does not contain a group capable of coupling with the oxidation product of a primary aromatic amino silver halide developing agent to form a dye image but which is capable of forming a hydrazone by reacting with a hydrazine and selected from the group consisting of "aldehydes, ketones, diand tetra-halogen compounds, the cyano acetyl group comprising the methylene group which acts as coupling function on color development.
• a photographic emulsion containing silver halide and a color coupler consisting of a cyanoacetylhydrazone of the general formula (CNCH2CONH-N ) "X wherein X represents the radical of a compound, which does not contain a group capable of coupling with the oxidation product of a primary aromatic amino silver halide developing agent to form a dye image but which is capable of forming a hydrazone by reaction with a hydra.- zine and selected from the group consisting of aldehydes, ketones, and compounds having two halogen atoms directly linked to the same carbon atom, and n is a positive integer selected from the group consisting of 1 and 2, the cyanoacetyl group comprising the methylene group which acts as coupling function on color development.
• a photographic emulsion containing silver halide and a color coupler consisting of a cyanoacetylhydrazone of the general formula wherein X represents the radical of a compound which does not contain a group capable of coupling with the oxidation product of a primary aromatic amino silver halide developing agent to form a dye image but which is capable of forming a hydrazone by reacting with a hydrazine and selected from the group consisting of aldehydes, ketones and compounds having two halogen atoms directly linked to the same carbon atom, the cyano acetyl group comprising the methylene group which acts as coupling function on color development.
• a photographic emulsion containing silver halide and a color coupler consisting of a dicyanoacetylhydrazone of the general formula wherein X represents the radical of a compound which does not contain a group capable of coupounds, the cyano acetyl group comprisinglthe methylene group which acts as coupling function on the color development.
• a photographic material having at least one light-sensitive silver halide emulsion layer and containing a color coupler consisting of a cyanoacetylhydrazone of the general, formula wherein X represent the radical of a compound which does not contain a group capable of coupling with the oxidation product of a primary .aromatic amino silver halide developing agent to form a dye image but which is capable of forming a hydrazone by reaction with a hydrazine and selected from the group consisting of aldehydes, ketones, and compounds having two halogen atoms directly linked to. the same carbon atom, and n is a positiveinteger selected from the group consisting of, 1 and 2, the cyanoacetyl group comprising the methylene group which acts as coupling function on color development;
• a process for the manufacture of-a colored photographic image which comprises developing a reducible silver salt image with a vcolor developer comprising a primary aromatic amino silver halide developing agent and a cyanoacetylhydrazone of the general formula wherein X represents the radical of a compound, which does not contain a group capable of coupling with the oxidation product of a primary aromatic amino silver halide developing agent to form a dye image but which is capable of forming a hydrazone by reaction with a hydrazine and selected from the group consisting of aldehydes, ketones, and compounds having two halogen atoms directly linked to the same carbon atom,v and n isa positive integer selected from the group consisting of 1 and 2, the cyanoacetyl group comprising the methylene group which acts as coupling function on color development.

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

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Cited By (4)

Citations (4)

• 1942
  • 1942-03-11 BE BE444782D patent/BE444782A/xx unknown
  • 1942-03-16 FR FR880244D patent/FR880244A/fr not_active Expired
  • 1942-03-17 NL NL105163A patent/NL58029C/xx active
• 1945
  • 1945-12-11 GB GB33443/45A patent/GB615218A/en not_active Expired
• 1947
  • 1947-03-14 US US734854A patent/US2527476A/en not_active Expired - Lifetime

Patent Citations (4)

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