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

• This invention relates to a light-sensitive rolor photographic material containing a cyan coupler usable in the form of a solution in an organic solvent, said cyan coupler falling within the class of so-called colored cyan couplers which provide auto-masking mechanism for the light-sensitive color photographic material so as to compensate for the deficient color reproductivity of said material.
• cyan couplers to be used as color formers in light-sensitive color photographic materials are compounds of the l-naphthol-Z-carboxylic acid or aminophenol type. Further, these couplers have been incorporated with a diffusion-preventing group such as a long chain alkyl group or a dialkylphenoxy group so that when they are used in photographic emulsions, diffusion or exudation thereof from photographic layers can be prevented.
• a diffusion-preventing group such as a long chain alkyl group or a dialkylphenoxy group
• cyan couplers those having an arylazo group at their 4position 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 United States Pats. 2,449,966 and 2,455,169). Particularly, a coupler having the formula on @Ocomuo 119mm.
• x is an integer of -4, y is 0-1, R is phenyl, C -C alkyl, alkyl-substituted phenyl, or alkyl-substituted phenoxyphenyl, and R is straight or branched C -C alkyl, (cf. United States Pat. 3,034,892), and a coupler having the formula United States Patent 0 ice CONHRa wherein R is branched alkyl of C or more, and R, is lower alkyl (cf. Japanese patent publication No. 11,- 304/1967), have been well known as good couplers.
• coupler solvent water-immiscible high boiling solvent
• the abovementioned compound is not only so excellent in solubility in the coupler solvent as to easily form a dispersion thereof but also has good dispersibility in a photographic emulsion, so that it is possible to obtain a reddish orange, red light-sensitive color photographic material having good transparency. Further, a photographic emulsion containing the above-mentioned compound has high relative speed and is excellent in color shade of the resulting image and in photographic properties, e.g. fog, etc. Moreover, the density and spectral characteristic of the colored cyan coupler which may remain unreacted are not changed throughout the overall process of color development, thereby providing an image sufficient in color density.
• the light-sensitive color photographic materials of the present invention which have been incorporated with the aforesaid compounds are prominent in color reproductivity and have excellent photographic properties.
• the couplers employed in the present invention can be prepared according to extremely simple synthesis procedures using easily obtainable inexpensive starting materials, as will be described in the synthesis examples set forth later.
• couplers employed in the present invention include those of the cis and trans types, and typical examples of the couplers represented by the aforesaid general formula are as shown below, but couplers usable in the present invention are not limited to these.
• Couplers of exemplification (1) 3 hr. and 30 min.
• Coupler of exemplification (5) 4 hr. and 30 min.
• the coupler of exemplification (4) which is similar in structure to the control couplers is far more excellent in solubility than the control couplers. Accordingly, light-sensitive color photographic materials incorporated with these couplers employed in the present invention do not suffer from deposition of the couplers during the production step and during the storage thereof and are not deteriorated in photographic properties due to deposition of the couplers.
• couplers The production of light-sensitive color photographic materials by use of these couplers may be carried out according to the prior art process.
• the coupler is dissolved in dibutyl phthalate, tricresyl phosphate, dibutyl lauramide or the like water-immiscible high boiling solvent having a boiling point of about 180 C., either singly or in admixture with ethyl acetate, butyl acetate, butyl propionate or the like low boiling solvent.
• 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 a film base or the like, followed by drying, whereby a light-sensitive color photographic material can be obtained.
• the amount of the coupled employed is desirably within the range of -100 g. per mole of the silver halide, but is optionally variable according to the purpose of application without being limited to said range.
• the coupler according to the present invention is further enhanced in solubility and the resulting photographic material is improved in photographic properties.
• Emulsions usable in the present invention include various silver salts such as silver chloride, silver iodide, silver chlorobromide, etc., and may contain chemical sensitizers such as, for example, sulfur sensitizers and reduction sensitizers, and noble metal salts. Further, they may contain common photographic additives such as, for example, fog inhibitors, stabilizers, contamination-preventing agents, coating aids, etc. They can further be incorporated with carbocyanine dyes and merocyanine dyes known as optical sensitizers for emulsions.
• Light-sensitive color photographic materials of the present invention which are obtained in the above manner do not suffer from crystallization of couplers and are excellent in transparency. When these materials are exposed to light and are then subjected to ordinary color development, the resulting dye images exhibit desirable spectral absorption characteristics and provide excellent photographic properties.
• EXAMPLE 1 1.2 parts of the coupler of exemplification (4) was dissolved in 10 parts of tricresyl phosphate with stirring at C. and was added to parts of a 10% aqueous gelatine solution kept at 60 C., and the mixed solution was charged with 2 parts of a 10% 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 5 times at intervals of 1 minute to prepare a coupler dispersion. 13 parts of the thus prepared dispersion was added at 35 C.
• N,N-diethyl-p-aminoaniline sulfate 2.0 g.
• Sodium sulfite 2.0 g.
• Sodium carbonate (monohydrate) 50.0 g.
• Hydroxylarnine hydrochloride 1.5 g.
• Potassium bromide 1.0 g. Water to make 1,000 ml. (pH 10.8 $0.1).
• the material was bleached and fixed by use of a bleaching solution and a fixing solution of the compositions shown below to remove undeveloped silver halide and by-produced reduced silver.
• Red prussiate 100 g.
• Potassium bromide 20 g.
• Water to make 1,000 ml.
• control coupled (A) 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 maintained at above 80 C. and the temperature of the aqueous gelatine solution at the time of dispersion should be maintained at above 70 C.
• the thus prepared coupler dispersion was treated in the same manner as above to obtain a red light-sensitive color photographic material. This material was exposed to red light through an optical wedge and was then subjected to color development, bleaching and fixing to obtain a cyan colored negative image and a reddish orange positive image containing unreacted residual coupler which were hazy and somewhat opaque.
• EXAMPLE 2 The coupler of exemplification (1) was treated in the same manner as in Example 1 to prepare a red lightsensitive color photographic material. This material was exposed to red light and was treated in the same manner as in Example 1, whereby a cyan colored negative image and a reddish orange positive image were simultaneously obtained. This film was markedly excellent in transparency.
• EXAMPLE 4 The coupler of exemplification (5) was treated in the same manner as in Example 1 to prepare a red lightsensitive color photographic material. This material was exposed to red light and was treated in the same manner as in Example 1, whereby a cyan colored negative image and a reddish orange positive image were simultaneously obtained. This film was markedly excellent in transparency.
• EXAMPLE 5 The coupler of exemplification (7) was treated in the same manner as in Example 1 to prepare a red lightsensitive material. This material was exposed to red light and was treated in the same manner as in Example 1, whereby a cyan colored negative image and a reddish orange positive image were simultaneously obtained. This film was markedly excellent in transparency.
• EXAMPLE 6 A mixture comprising 1 part of the coupler of exemplification (4) and 3 parts of 2-(N-octadecenylcarbamoy1) l-naphthol was dissolved in 5 parts of di-n-butyl phthalate with stirring at 80 C. and was added to 100 parts of a 10% aqueous gelatine solution kept at 60 C., and the mixed solution was further charged with 2 parts of a 10% aqueous sodium alkylbenzenesulfonate solution. Subsequently, the liquid was stirred and dispersed at about 65 C. for 5 minutes by use of a high speed rotary mixer. This operation was repeated 5 times at intervals of 1 minute to prepare a coupler dispersion.
• the film using the coupler of exemplification (4) was markedly excellent in transparency, whereas the film using the control coupler (A) was hazy and somewhat opaque.
• a light-sensitive silver halide color photographic material characterized by containing a. coupler represented by the general formula i COR 3.

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

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Publications (1)

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ID=11826946

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Cited By (4)

Families Citing this family (1)

• 1969
  • 1969-02-24 JP JP44013216A patent/JPS4817888B1/ja active Pending
• 1970
  • 1970-02-18 US US12476A patent/US3667956A/en not_active Expired - Lifetime
  • 1970-02-23 GB GB8662/70A patent/GB1271202A/en not_active Expired

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