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
  • G03C7/34—Couplers containing phenols
  • G03C7/344—Naphtholic couplers

Definitions

• This invention relates to a light-sensitive silver halide colorphotographic emulsion capable of forming a cyan-colored image, which comprises a novel cyan coupler of the formula wherein X is hydrogen atom,thalogen atom or a sulfonic or sulfonate group, Y is (CH -orCH CH(Cl-l and R is an aliphatic hydrocarbon radical of eight to 20 carbon atoms.
• l-hydroxy-Z-naphthoalkyl amide derivatives which, for example, have any one of the following structures:
• a color-photographic material in which the above-mentioned coupler '[l] or [ll] is incorporated has many advantages, e.g. high photographic speed and maximum color density obtained by the usual color development, and good spectral absorption characteristics of cyan-colored images. Further, it is relatively free from staining of unexposed areas. However, the said material is still not entirely satisfactory because the resulting cyan-colored image varies in its density depending on the pH of a developing bath and the time of water-washing during color development. Further, the color image is sensible to light, heat and humidity so that it may be changed or faded out in color during storage. This is a disadvantage when the said material is intended for use as photographic positive.
• the present invention provides a light'sensitive silver halide color-photographic material which does not suffer from the above-mentioned disadvantages.
• the coupler of the above-indicated structural formula which is usable for the present invention is a new compound whose structural characteristic is that a cyan coupler component is connected through a C -alkylene chain by an amide linkage with a diffusion-inhibiting component which includes a water-solubilizing group.
• Such compounds may be prepared by using phenyl-l-hydroxy-Z-naphthoate propylenediamine, long chain alkyl succinic anhydride, etc.
• Typical couplers which are suitably used in the present invention include the following:
• the coupler compounds of the present invention contain three carbon atoms in the alkylene chain linking the cyan coupler component and the diffusion-inhibiting component.
• the conventionally known cyan couplers which are known have at most two carbon atoms in the corresponding alkylene chain, as shown, for example, by the following structuralfonnula
• Such a conventionally known coupler as [lll] is not free from the aforementioned defects.
• a corresponding cyan coupler having a C -alkylene chain is synthesized only by using expensive starting materials.
• Another corresponding coupler having a C -aIkylene chain is difficult to be synthesized.
• N- (3-aminopropyl)-l-hydroxy-4-chloro-2-naphthoamide (intermediate product) melting at 190 C. is obtained.
• the intermediate product is reacted with n-dodecyl succinic anhydride under the same condition as mentioned in the synthesis of compound (1), thereby to yield compound (3) melting at lO4-l06 C.
• This intermediate product (58 g.) is suspended in 500 ml. of acetonitrile and, to this suspension, 35 ml. of chlorosulfonic acid are added in one batch at 20 C. while stirring. The temperature of the suspension rises to 4550 C. and crystals are dissolved therein. After allowing to stand at room temperature, the precipitate formed is filtered off. The filtered precipitate is washed two times with 100 ml. of acetonitrile and dried. The product is then dissolved in a mixture of 300 ml. of N-caustic soda aqueous solution and 300 ml. of methyl alcohol, and the resulting solution is made acidic with acetic acid. The precipitate formed is filtered off and washed with 50 percent methanol and dried. The compound (2) melting at l69-l74 C. is obtained as a white powder.
• the coupler compound thus prepared is dissolved in an aqueous alkali hydroxide or alkali carbonate solution or in an aqueous alcohol solution and then the resulting solution is dispersed in a light-sensitive silver halide color-photographic emulsion, which in turn is coated on an appropriate support, e.g. photographic film base or baryta paper, and then dried, to thereby produce a light-sensitive color-photographic material.
• the coupler content of the silver halide emulsion may vary depending on the type of the emulsion and molecular weight of the coupler, but it should preferably be within the range of from 0.017 moles to 0.l47 moles per mole of the silver halide present.
• any color developer which is commonly used for development of conventional color-photographic materials is usable for the color-photographic material of this invention.
• a light-sensitive color-photographic material which contains a cyan coupler of the present invention has high photographic sensitivity even by usual color development. Further, it has good spectral absorption characteristics for photographic positives because the absorption maximum of the resulting cyan-colored image exists at around 690 mu. Still another advantage is the stability of color image density irrespective of variation in the pH of the treating bath and the time of water-washing during color development. The resulting color image is quite stable against heat, light and humidity and so it can be preserved for a long period of time.
• EXAMPLE 1 In 30 ml. of N-potassium hydroxide solution, 8.0 g. of the coupler compound (3) are dissolved and the solution is diluted with water to ml. The resulting solution is added to 1 kg. of a red-sensitive silver chloride emulsion and the mixture is adjusted to pH 6.7 with an aqueous citric acid solution.
• the resulting emulsion is coated on a baryta paper and dried.
• the light-sensitive material thus prepared is exposed to light and then treated at 20 C. for minutes in a developing bath having the following formulation:
• N-Ethyl-N-hydroxyethyl-p-phenylenediamine sulfate 2.5 g.
• Anhydrous sodium sulfite 2.0 g.
• Hydroxylamine hydrochloride 1.0 g.
• Sodium carbonate (monohydrate) 82.0 g.
• a stopping bath which comprises 10 ml. of glacial acetic acid, 3.0 g. of caustic soda and 1,000 ml. of water
• the light-sensitive material is dipped in an acidic hardening fixing bath for 4 minutes.
• the developed light-sensitive material is washed with water for 10 minutes and subsequently treated at C. for 8 minutes in a bleaching bath having the following formulation:
• Sodium ethylenediamine tetraacetate 40 g. Ferric chloride g. Sodium carbonate (monohydrate) 20 g. Potassium bromide 30 g. Sodium thiosulfate 200 5.
• the bleached product is washed with water for 20 minutes and then dipped in a stabilizing bath for 2 minutes and dried. Cyan colored image having an absorption maximum of 690 mp. is obtained.
• Fading properties of the cyan-colored image obtained from the coupler compound (3) of this invention and the cyan-' colored images obtained from the known couplers [I], [II] and [III] were tested.
• Thecyan-c olored images obtained from the known cyan couplers [I], [II] and [III] by the similar treatment as above were used as controls.
• the fading ratio of the colored images after standing at 50 C. for 7 days under 80 percent of relative humidity and the fading ratio after standing at C. for 4 days in Fade O-meter are shown in the table 1 below.
• the film is reexposed to white light and then treated at 20 C. for 12 minutes with a developing solution of the following formulation:
• the film is washed with water for further 10 minutes and then dipped for 5 minutes in a bath of the following formulation:
• a light-sensitive silver halide color-photographic material containing a cyan coupler having the general formula:
• X is hydrogen atom, halogen atom, or sulfonic or sulfonate group
• Y is(Cl-l -,or CH -CH(CH and R is on an aliphatic hydrocarbon radical of eight to 20 carbon atoms.

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• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Silver Salt Photography Or Processing Solution Therefor (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
• Nitrogen Condensed Heterocyclic Rings (AREA)

Applications Claiming Priority (1)

Publications (1)

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Cited By (2)

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• 1968
  • 1968-03-19 US US714336A patent/US3615605A/en not_active Expired - Lifetime
  • 1968-03-20 DE DE19681768001 patent/DE1768001B1/de active Pending
  • 1968-03-21 FR FR1558147D patent/FR1558147A/fr not_active Expired
  • 1968-03-22 BE BE712616D patent/BE712616A/xx unknown
  • 1968-03-22 GB GB04058/68A patent/GB1210463A/en not_active Expired

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