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
  • G03C7/38—Couplers containing compounds with active methylene groups in rings
  • G03C7/384—Couplers containing compounds with active methylene groups in rings in pyrazolone rings

Definitions

• R is alkyl, aryl or substituted aryl and R is hydrogen, alkyl, aryl, substituted aryl or a heterocyclic radi cal with the proviso that at least one of R and R contains an aliphatic hydrocarbon radical of 12-20 carbon atoms.
• the invention is concerned with a light-sensitive, color photographic material to yield a magenta color image, which comprises a magenta coupler of the mono-pyrazolone 3,556,799 Patented Jan. 19, 1971 "ice type, wherein a bis-pyrazolone compound of the general formula wherein R is alkyl, non-substituted or substituted aryl, R
• This invention relates to a light-sensitive photographic is hydrogen, alkyl, non-substituted or substituted aryl, or a heterocyclic radical with the proviso that a least one of R and R should contain an aliphatic hydrocarbon radical having 12 to 20 carbon atoms is incorporated in the photographic material. It is a principal object of the present invention to provide a light-sensitive color photographic material which is free from color staining (magenta fog) during and color development.
• magenta couplers which are capable of forming of magenta color image in a light-sensitive, color photographic material.
• a magenta coupler of the mono-pyrazolone type can give a stable color image with good tone quality at high speed.
• a photographic material in which the magenta coupler alone is incorporated is disadvantageous because it suffers from color staining during storage or development.
• a magenta coupler of the mono-pyrazolone type, the pyrazolone ring of which is substituted at the 3-position with a long chain alkyl group is very likely to cause color staining.
• magenta coupler of the monopyrazolone type in combination with an antifoggant (stabilizer) such as 2,4-di-tert. butyl hydroquinone, etc.
• an antifoggant such as 2,4-di-tert. butyl hydroquinone, etc.
• the use of such a stabilizer invariably causes a serious decrease in the sensitivity of high speed photographic emulsion.
• a light-sensitive, color photographic material which contains a magenta coupler of the mono-pyrazolone type which is completely prevented from color staining while retaining all the advantages inherent in said magenta coupler.
• magenta coupler of the present invention Any compound of the pyrazolone type which is heretofore known may be used as the magenta coupler of the present invention.
• useful compounds are the following:
• the required amount of the bis-pyrazolone compound to be added may vary depending on the type of magenta coupler of the mono-pyrazolone type and further on the type of bis-pyrazolone compound used but it usually will be within the range of 150% by weight based on the weight of the magenta coupler.
• Incorporation of the specific compound of the bis-pyrazolone type into a photographic material of the present invention can be made in the manner heretofore known per se in the art. For example, it is possible to add the compound to a light-sensitive, color photographic emulsion containing a magenta coupler of the mono-pyrazolone type at any time just before, during or after the second ripening of the said emulsion.
• the bis-pyrazolone compound as a stabilizer for the magenta coupler is most preferably made at the stage after the second ripening.
• the bis-pyrazolone compound may be added to a starting material for the preparation of the emulsion, for example gelatine. It is desirable to add the bispyrazolone compound in solution dissolved in a suitable solvent, e.g. water, dilute alkali, methanol, ethanol, etc., if the addition is made to an emulsion.
• a suitable solvent e.g. water, dilute alkali, methanol, ethanol, etc.
• the photographic emulsion containing the said bis-pyrazolone compound can be sensitized with a gold, sulfur or other chemical or optical sensitizer.
• a light-sensitive, color photographic emulsion or the like expression used herein is to be understood to mean any conventionally known light-sensitive, color photographic emulsion which contains a magenta coupler of the mono-pyrazolone type.
• a suitable color photographic emulsion will be available with reference to Kagaku- Shashin-Binran (Manual of Photographic Science), vol. I, pp. 455-460 (Maruzen Co., Tokyo, Japan).
• emulsion to which the bis-pyrazolone compound has been added can be applied to a suitable support in the manner heretofore known per se in the art, e.g. coating or pouring.
• suitable supports include films, papers and glass plates.
• films of the types such as cellulose esters, e.g. cellulose triacetate; polyesters obtained by the polycondensation of phthalic, isophthalic or terephthalic acid with a dihydric alcohol, e.g. polyethylene terephthalate, poly[cyc1ohexane-1,4-dimethylol]terephthalate, etc.', and polycarbonates including those obtained by the polycondensation of bisphenyl A with carbonic acid.
• cellulose esters e.g. cellulose triacetate
• polyesters obtained by the polycondensation of phthalic, isophthalic or terephthalic acid with a dihydric alcohol e.g. polyethylene terephthalate, poly[c
• EXAMPLE 1 8 g. of the magenta coupler of the above-indicated Formula 1 and 2 g. of the bis-pyrazolone compound of the above-indicated Formula IX are dissolved in 35 ml. of l N sodium hydroxide. The resulting solution is diluted with 400 ml. of water and then added to 1 kg. of a green light-sensitive, high speed photographic gelatino-silver iodobromide emulsion. Then, the emulsion is adjusted to pH 7.0 and coated on a cellulose acetate film support and dried. The thus obtained film is exposed to green light and treated at 20 C. for 10 minutes with a color developer having the following formulation:
• Example 1 These control samples also are subjected to sensitometric tests.
• photographic speed values are expressed as relative values based on the speed of the control sample (1) which is rated as 100.
• Condition A --For seven days at a temperature of 50 C. under a relative humidity of 20%.
• Condition B For five days at a temperature of 55 C. under a relative humidity of 80%.
• each set of the films are treated by color development in the same manner as before and then tested by sensitometry. The results are set forth in Table 2.
• Color images obtained by using the samples of Example 1 are excellent in tone quality and stability.
• EXAMPLE 2 7 g. of the magenta coupler of the above-indicated Formula 7 and 3 g. of the bis-pyrazolone compound of the above-indicated Formula IV are dissolved in 30 ml. of 1 N sodium hydroxide. The resulting solution is diluted with 500 ml. of water and added to 1 kg. of a green lightsensitive gelatino-silver chlorobromide emulsion, which is then adjusted to pH 6.9 with citric acid and coated on a. cellulose acetate film support. The resulting film is treated in the same manner as in Example 1 to obtain the results given in Table 3.
• control samples are prepared 10 by using in the control sample 3 10 g. of the magenta coupler of the Formula 7 alone and in the contral sample 4 10 g. of the same magneta coupler and 500 mg. of 2,4-di-tert. butyl hydroquinone. These control samples also are tested by sensitometry.
• a light-sensitive, color photographic material which comprises on a support a light-sensitive gelatino-silver halide emulsion layer containing a magenta coupler of the mono-pyrazolone type and a bis-pyrazolone compound of the formula wherein R is alkyl, aryl or carboxyl, sulfo or amido substituted aryl radical and R is hydrogen, alkyl, aryl, carboxyl, sulfo or amido substituted aryl or heterocyclic radical, with the proviso that at least one of said R and R contains an aliphatic hydrocarbon radical having 1220 carbon atoms in an amount sui'ficient to prevent color staining with said magenta coupler.

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

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Cited By (1)

• 1967
  • 1967-09-11 US US666936A patent/US3556799A/en not_active Expired - Lifetime
  • 1967-09-15 DE DE19671597622 patent/DE1597622A1/de active Pending
  • 1967-09-18 BE BE703983D patent/BE703983A/xx unknown
  • 1967-09-19 GB GB42718/67A patent/GB1153029A/en not_active Expired

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