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
  • G03C7/333—Coloured coupling substances, e.g. for the correction of the coloured image
  • G03C7/3335—Coloured coupling substances, e.g. for the correction of the coloured image containing an azo chromophore
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B29/00—Monoazo dyes prepared by diazotising and coupling
  • C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
  • C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
  • C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series

Definitions

• red cyan coupler has advantageous properties with respect to suitable absorption dyes, efficient emulsifiability and excellent reactivity.
• the invention relates to a color photographic material with improved color reproduction which contains red cyan couplers for the production of so-called builtin masks, preferably in an emulsified form.
• the image dye is formed in the exposed and developed areas while in the unexposed areas the color of the colored coupler used is preserved.
• the gradation of unwanted side densities obtained in the course of processing is compensated by an equal but opposite gradation of the masking dye so that the density in the unwanted region of the spectrum is uniform regardless of the conditions of exposure.
• the yellow and magenta side densities measured behind color filters after processing are constant and independent of the conditions of exposure.
• the azo masking couplers mentioned above may either be emulsified in the photographic layers or introduced in the form of aqueous alkaline solutions. It is frequently observed that the coupling activity of hydrophobic emulsified couplers is less than that of hydrophilic couplers dissolved in an aqueous alkaline solvent. If, however, attempts are made to render such couplers envisaged for the emulsification process more hydrophilic by introducing suitable substituents, difficulties arise in the emulsification process. This causes the choice of substituents to be severely restricted. The choice is still further reduced by the necessity of keeping the dyes used within a suitable absorption range for masking the cyan side densities.
• red azo masking couplers which are sufficiently hydrophobic to ensure that they can be efficiently emulsified but are sufficiently hydrophilic to enable the coupling reaction in the layer to take place sufficiently rapidly; furthermore, the absorption maximum should be situated so that the side densities of the cyan partial image are masked as completely as possible.
• a Rf, R or R represent hydrogen or alkyl with up to 18 carbon atoms, these groups being either the same or different, at least one of these groups being an alkyl radical with preferably 12 to 18 carbon atoms which renders the compound resistant to diffusion;
• R represents alkyl with four to seven carbon atoms, or cycloalkyl such as cyclohexyl which may contain other substituents, e.g. alkyl preferably with up to five carbon atoms, especially methyl.
• reaction mixture is adjusted to pH 7 with glacial acetic acid and the slimy precipitate formed is taken up in methylene chloride which is then dried with sodium sulfate and the residue is concentrated by evaporation.
• the product is purified by recrystallizing from ethyl acetate.
• the new red azo masking couplers are superior to the corresponding known couplers in many of their properties. They are red to magenta in color, having an absorption maximum between 450 and 510 nm. This absorption range satisfies the requirement that both the blue and the green absorption range of the cyan coupling dyes formed should be effectively masked.
• Another advantage of the couplers is that due to the combination of esters of aliphatic alcohols which have a medium number of carbon atoms with a sulfonamide group in the'same molecule the couplers are especially advantageous in three of their properties: Suitable absorption of dyes, efficient emulsifiability and excellent reactivity.
• the masking couplers to be used according to the invention may be used either alone of preferably together with colorless cyan couplers in color photographic silver halide emulsions, especially in'layers which are sensitized to red light.
• the masking couplers are preferably incorporated in an emulsified form with the silver halide emulsion.
• the compound is dissolved in known manner in suitable organic solvents, e.g. in esters of aliphatic carboxylic acids, especially in ethyl acetate, and this solution a is emulsified in the silver halide emulsion which is ready for casting.
• suitable organic solvents e.g. in esters of aliphatic carboxylic acids, especially in ethyl acetate
• crystalloids that is to say high boiling solvents, e.g. tricresyl phosphate or dibutylphthalate
• the new substances are used together with colorless cyan couplers, the substances may be added to the light sensitive silver halide emulsions either successively or together from a common solution.
• the method of addition to the emulsion is not critical. and the most suitable method can easily be determined by simple tests.
• the required dye emulsions may be prepared, for example, as follows:
• a fatty alcohol sulfonate per 100 g of gelatin solution is added as emulsifier to a 7.5 percent solution of a photographic gelatin.
• the required quantity of dye is then dissolved in 3 to 5 times its quantity of ethyl acetate and this solution is run into a gelatin solution heated to 50 C, using a Kotthoff stirrer.
• the emulsification time is 5 to 15 minutes, depending on the quantity. Any ethyl acetate still present is removed under vacuum.
• the emulsion is then ready for use. If necessary, 10 to 100 percent of an oil forming substance such as dibutylphthalate, the amount being preferably based on the quantity of dye per kg:
• the light sensitive emulsions may contain silver chloride, silver bromide or mixtures thereof, or with a small iodide content of up to mols percent.
• the binders used may be the usual hydrophilic binders such as proteins, especially gelatin, polyvinyl alcohol, polyvinyl pyrrolidone, cellulose derivatives such as carboxymethylcellulose or derivatives of alginic acid.
• the emulsions may also contain the usual derivatives, e.g. optical or chemical sensitizers, stabilizers, hardeners, and plasticizers.
• Any color forming developers which contain a primary amino group may be used for development. It is preferred to use those of the paraphenylenediamine series, e.g. N,N-diethyl-para-phenylenediamine, 2- amino-5-diethylaminotoluene-N-butyl-N-w-sulfobutylparaphenylenediamine, 2-amino-5-(N-ethyl-N-B- methanesulfonamidoethylamino)toluene, and 2- amino-S-N-ethyl-N-hydroxyethylaminotoluene.
• paraphenylenediamine series e.g. N,N-diethyl-para-phenylenediamine, 2- amino-5-diethylaminotoluene-N-butyl-N-w-sulfobutylparaphenylenediamine, 2-amino-5-(N-ethy
• EXAMPLE 1 3.2 g of the red masking coupler 6 in that table of formulae are dissolved in ml of ethyl acetate and then emulsified in 250 g of a 7.5 percent gelatin solution.
• the emulsion is mixed with 100 g of silver bromide gelatin emulsion (50 g of silver in the form of silver halide per kg) with stirring and diluted with 1 200 ml of water.
• To this emulsion mixture are added 15 ml of a 10 percent aqueous saponin solution and 5 ml of a 0.5 percent aqueous chrome acetate solution and the emulsion is then cast on. a layer support of cellulose triacetate. Thickness of layer 5 After drying, the film is exposed behind a grey step wedge and developed for 6 minutes in a developer of the following composition:
• EXAMPLE 2 2.5 g of the cyan coupler of the following formula are added in the form of a gelatin dispersion together with 0.25 g of dibutylphthalate, as oil forming agent, to 100 g of a red-sensitized silver bromide gelatin emulsion which contains 70 g of silver in the form of silver halide aiin 1.7 g of masking coupler 3, also dispersed in gelatin, are then added.
• R R and R represents alkyl and one of R R or R,-, is an alkyl radical with 12 to l8 carbon atoms.
• a material as claimed in claim 3 in which 10 to percent, based on the quantity of dye used, of dibutylphthalate is added to the dye solution before emulsification.
• a material as claimed in claim 1 containing in the silver halide emulsion layer in addition colorless cyan coupler selected from the group consisting of cyan couplers of the phenol or naphthol series.

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• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Silver Salt Photography Or Processing Solution Therefor (AREA)

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Citations (4)

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• 1971
  • 1971-05-07 DE DE2122570A patent/DE2122570C3/de not_active Expired
• 1972
  • 1972-05-04 US US00250300A patent/US3844795A/en not_active Expired - Lifetime
  • 1972-05-04 GB GB2074572A patent/GB1356176A/en not_active Expired
  • 1972-05-04 BE BE782997A patent/BE782997A/xx unknown
  • 1972-05-05 CA CA141,359A patent/CA998281A/en not_active Expired
  • 1972-05-05 FR FR7216208A patent/FR2137576B1/fr not_active Expired
  • 1972-05-05 IT IT50060/72A patent/IT958571B/it active
  • 1972-05-05 CH CH667372A patent/CH565396A5/xx not_active IP Right Cessation

Patent Citations (4)

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