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

Definitions

• the present invention relates to a light-sensitive silver halide color photographic material containing cyan coupler which has appreciable solubility in a water-immiscible high boiling solvent (hereinafter known as coupler solvent), said cyan coupler falling within the class of so-called colored couplers which provide auto-masking mechanism for the lightsensitive silver halide color photographic material so as to compensate for the deficient color reproductivity' of said material.
• coupler solvent water-immiscible high boiling solvent
• cyan couplers used as color former in color photography are compounds of l-naphthol-Z-carboxylic acid or aminophenol type. Where these coupler compounds are intended for use in photographic emulsions, a long chain alkyl group or a dialkylphenoxy group should preferably be introduced as a diffusion-preventing group into their molecule so that diffusion of the couplers from photographic layers can be prevented.
• cyan couplers those which-have an arylazo group at their 4-position have been known as colored couplers provided with auto-masking mechanism so as to compensate for deficiencies in color reproduction of color photographic materials concerned. See US. Pat. Nos. 2,449,966 and 2,455,169.
• a coupler of the l-hydroxy-4-ary1azo- Z-naphthoamide or naphthoanilide type having the formula wherein X is hydrogen or alkyl, Y is a mononuclear aryl or aralkyl radical and R is a mononuclear aryl radical (cf. U.S. Pat. No.
• X is hydrogen
• Y is a mononuclear aryl radical substituted in a position ortho to the amido group with either halogen, alkoxy or mononuclear 'aryloxy radical and R is a mononuclear aryl radical
• colored cyan couplers of the 4-ary1azo-substituted l-hydroxy-2-naphthoamide type generally are not so good in solubility in coupler solvents, and this has been appreciated as a great disadvantage in the production of lightsensitive color photographic materials.
• almost all of these couplers have an aryl group at the 2-position of their naphthol nucleus.
• the introduction of an aryl groupat the 2- position of the naphthol nucleus causes a decrease in solubility of said couplers in coupler solvents, wherebythe couplers become difficult to be prepared in dispersion and tend to cause undesired crystallization in photographic-emulsions. Accordingly, many attempts have been made to improvetheir solubility, but they are not successful.
• the above compounds have good solubility in coupler solvents and have good dispersibility in photographic emulsions. Further, the photographic emulsions containing the above coupler compounds have high relative speed and are excellent in color shade of the resulting color image andin photographic properties, eg fog, etc. Density and spectral characteristics of the colored cyan coupler which may remain unreacted are not changed through the overall process of color development, while said coupler can provide an image having sufficient color density. Thus, a light-sensitive color photographic material having said coupler incorporated therein has good color reproductivity and is quite satisfactory in photographic properties.
• couplers usable in the invention are notlimited only to these.
• the couplers represented by the aforesaid structural formulas can be synthesized.
• Physical properties of the exemplified couplers synthesized in the above mariner are set forth in the table 353 .2 g. of benzenesulfonyl chloride. Subsequently, 94.1 g. of below.
• This reaction liquid was subjected to "filtration to recover a precipitate, whichwas then washed with 20 0 ml. of hot 80 percent acetic acid.'To the filtrate was addedZ-A lof water, and a deposited crystal was recovered by filtration,
• This reaction liquid was charged into-a solution comprising 2 l of concentrated hydrochloric-acid and 2 kg. of ice, and the deposited red precipitatewas recovered by filtration, water-washed, driedand then recrystallized from propyl alcohol, whereby a crystal was obtained.
• the thus obtained crystal was washed with methyl alcohol and then dried to obtain 1 g. of 1-hydroxy-4-('2-carbophenoxyphenylazo)-N- dodecyl-Z-naphthamide, yield about 85 percent, m.p. 164
• the colored cyan couplers employed in the present invention are longer in time ofinitiation of crystallization than other colored cyan couplers of this kind, and hence are markedly high in solubility for coupler solvents.
• the coupler is dissolved in a waterimmiscible high boiling solvent having a boiling point of above 180 C., such as dibutyl phthalate, tricresyl phosphate, dibutyl laurate or the like, either singly or, if necessary, in admixture with such low boiling solvent as ethyl acetate, butyl acetate, butyl propionate or the like.
• a waterimmiscible high boiling solvent having a boiling point of above 180 C.
• such as dibutyl phthalate, tricresyl phosphate, dibutyl laurate or the like either singly or, if necessary, in admixture with such low boiling solvent as ethyl acetate, butyl acetate, butyl propionate or the like.
• the solution is mixed with an aqueous gelatine solution containing a surface active agent, is emulsified by means of a high speed rotary mixer or a colloid mill, is directly added to a silver halide photographic emulsion, and is then coated onto a suitable support such as film base, or the like, followed by drying, whereby a light-sensitive color photographic material can be obtained.
• the amount of the coupler employed is desirably within the range of l0-l00 g. per mole of silver halide, but is optionally variable according to the purpose of application, without being limited to said range.
• the coupler of the present invention is further enhanced in solubility and comes to be quite easily dispersible in the silver halide photographic en'iulsion.
• Light-sensitive silver halide color photographic materials obtained in the above manner do not suffer from crystallization of couplers and are excellent in transparency. When these materials are subjected, after exposure, to ordinary developing treatment, the resulting dye images have desirable spectral absorption characteristics, good transparency and excellent photographic properties.
• EXAMPLE 1 One part of the coupler of exemplification (2) was dissolved in 5 parts of D.B.P. with stirring at 80 C. and was added to 100 parts of a 10 percent aqueous gelatine solution kept at 60 C., and the mixed solution was further charged with 2 parts of a 10 percent aqueous sodium alkylbenzenesulfonate solution. Subsequently, the liquid was stirred at about 65 C. for 5 minutes by use of a high speed rotary mixer. This operation was repeated five times at intervals of 1 minute to prepare a coupler dispersion. 13.5 parts of the thus prepared coupler dispersion was added at 35 C.
• control coupler (C) 1 part of a control coupler of the structural formula (C) shown below was dissolved in 10 parts of D.B.P. and was treated in the same manner as above to prepare a coupler dispersion. In this case, it is necessary that the temperature at which the coupler is dissolved in the coupler solvent should be strictly maintained at above C. and the temperature of the aqueous gelatine solution at the time of stirring should be strictly maintained at above 70 C. The thus prepared coupler emulsion was treated in the same manner as above to obtain a red light-sensitive color photographic material.
• the materials were further treated with a bleaching solution and a fixing solution of the compositions shown below to remove undeveloped silver halide and byproduced reduced silver.
• a mixture comprising 1 part of the control coupler of the structural formula (C) and 3 parts of l-hydroxy-N-[8-(2,4-ditert-amylphenoxy)-butyl]-2-naphthamide was dissolved in 10 parts of butyl phthalate and was treated in the same manner as above to prepare a coupler dispersion.
• the temperature at which the coupler is dissolved in the coupler solvent should be strictly maintained at above 80 C. and the temperature of the aqueous gelatine solution at the time of stirring should be strictly maintained at above 70 C.
• Example 2 in the same manner as in Example 1, the thus obtained two kinds of color photographic materials were subjected to exposure, color development, bleaching and fixing to simultaneously obtain cyan colored negative images and red and reddish orange positive images.
• the film using the coupler (2) was good in transparency, whereas the film using the control coupler (C) was opaque and was extremely hazy, and the difference between the two materials was greater than in the case of Example 1.
• EXAMPLE 4 The coupler of exemplification (9) was treated in the same manner as in Example 1 toprepare a red light-sensitive photographic material. This material was treated in the same manner as in Example 1 to obtain simultaneously a cyan colored negative image and a red color positive image. This film was excellent in transparency and the red positive image had a sufficiently red color. Further, the film was satisfactory in photographic speed.
• a light-sensitive silver halide color photographic material characterized by containing a compound represented by the formula wherein is an integer in the range of 0-4, y is 0 or 1, R is phenyl radical, alkyl or alkenyl radical having four to 15 carbon atoms in either straight or branched chain, alkyl-substituted phenylradical, alkyl-substituted phenoxyphenyl radical, alkylsuccinimide radical or alkoxycarbonylaklyl radical, and R is an aryl or aralkyl radical which may be substituted with at least one member selected from the group consisting of halogen, lower alkyl or lower alkoxy.
• a light-sensitive silver halide color photographic emulsion which contains as cyan color coupler a compound of the formula

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• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Silver Salt Photography Or Processing Solution Therefor (AREA)

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Citations (3)

• 1969
  • 1969-12-13 DE DE1962574A patent/DE1962574C3/de not_active Expired
  • 1969-12-19 US US886779A patent/US3658545A/en not_active Expired - Lifetime
  • 1969-12-22 GB GB62479/69A patent/GB1286688A/en not_active Expired

Patent Citations (3)

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