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

• color photographic material containing a cyan coupler discloses couplers of the formula usable in the form of a solution in an organic solvent, Y
• cyan coupler providing auto-masking mechanism for the light-sensitive color photographic material so as OH to compensate for the deficient color reproductivity of A I said material.
• CONHR' Almost all of the cyan couplers used as color formers in light-sensitive color photographic materials are compounds of the l-naphthol-Z-carboxylic acid or orthoaminophenol type.
• cyan colored couplers having an arylazo group at their 4-position have been utilized as colored couplers provided with autornasking mechanism so as to compensate for deficiencies in color reproductivityofcolor photographic materials concerned.
• the above-mentioned couplers have less of a disadvantage with respect to spectral absorption but are extremely low (about one-half) in emulsion speed as compared with the coupler (I) and inferior in graininess of the resulting color images.
• the protected type colored cyan couplers of Japanese Pat. Publication No. l 1,304/1967 are used for negative sensitive materials. It is therefore desirable that couplers have such properties that they are excellent in solubility in organic solvents, favorable in auto-masking effects (broad in the range of isospecific points of blue and green portions), high in speed and prominent in graininess of the resulting images.
• Couplers having all such properties have, of course, not been provided hitherto, but the coupler (I) has many desirable properties.
• the coupler (I) is actually dissolved in an organic solvent such as tricresyl phosphate or the like and is finely dispersed in an aqueous gelatin solution, the resulting dispersion is somewhat low in stability and the dispersed particles frequently unite with each other when the dispersion is allowed to stand for a long time.
• the COCH of the arylazo group is varied to --COC H -COC H-, or the like, no substantial change is seen in solubility.
• there is a new disadvantage that if said --COCH is varied to COC H the coupler (1) brings about a marked color variation when subjected to ordinary color development and becomes unusable in practice.
• the present invention provides couplers which are free from the above-mentioned disadvantages.
• the present invention is concerned with lightsensitive silver halide color photographic materials characterized by containing a coupler having the formula ( ⁇ OCONH(CHz) 0tC H N II N I COOR wherein n is an integer of l to 4, and R is a lower alkyl group.
• the reaction mixture was charged into 25 liters of water, and the deposited red crystals were recovered by filtration. After washing with water, the crystals were dried and then recrystallized from 55 liters of npropanol to form a red powder.
• This red powder was washed with 300 ml. of methanol and then dried to obtain 750 g. of l-hydroxy-4-(2-carboethoxyphenylazo- N-[ 8-(2,4-di-t-amylphenoxy)-butyl]-2-naphthamide, coupler (l), as a red powder. m.p. 169 170C., yield 92 percent.
• Test Example 1 The couplers used in the present invention and other couplers were compared to each other in solubility for tricresyl phosphate in such a manner that 1 g. of each coupler was dissolved at 80C. in tricresyl phosphate and then allowed to stand at 20C., and the time required for initiation of the crystallization of said coupler was measured to obtain the results as shown below.
• Couplers of the present invention which were of the formula shown below and the known coupler of the same formula, except that R' was different, were tested for solubility in a high boiling solvent to obtain the re- 1 sults set forth in the table below.
• One gram of each coupler was thoroughly dissolved in tricresyl phosphate and the solubility thereof was represented by the minimum amount (cc.) of the tricresyl phosphate in which .the coupler did not deposit at room temperature for more than 24 hours.
• the couplers e mployed in the present invention may be optionally varied in solubility. Moreover, all these 2 couplers are excellent in emulsion property and masking property, and they always give light-sensitive color photographic materials having uniform photographic properties.
• Example 1 minute to prepare a coupler dispersion 13.5 Parts of this dispersion were added with stirring at 35C. to 100 parts of a light-sensitive silver iodobromide emulsion containing a red light-sensitive sensitizing dye, and the resulting mixture was coated on a film support and then dried to obtain a red light-sensitive color photographic material.
• the photographic material was bleached and fixed by use of a bleaching solution and a fixingsolution of the compositions shown below to remove undeveloped silver halide and by-produced reduced silver.
• Example 2 A mixture comprising 1 part of the coupler (3) and 3 parts of l-hydroxy-N-[6-(2.,4-di-t-amylphen0xy)- butyl]-2-naphthamide was dissolved with stirring at C. in 10 parts ofT.C.P., and was added to parts of a 10 percent aqueous gelatin solution kept at 60C., and the mixed solution was charged with 2 parts of a 10 percent aqueous sodium alkylbenzene-sulfonate solution. Subsequently, the liquid was. stirred at about 65C. for 5 minutes by use of a high speed rotary mixer. This procedure was repeated 5 times at intervals of 1 minute to prepare a coupler dispersion.
• This photographic material was exposed to red light through an optical wedge and was color-developed, bleached and fixed in the same manner as in Example 1, whereby a cyan colored negative image and an excellent red positiveimage were obtained simultaneously. Transparency also was quite excellent.
• Example 3 A mixture comprising 0.3 part of the coupler (1), 0.7 part of the coupler (6) and 3 parts of 1-hydroxy-N-[8- (2,4-di-t-amylphenoxy )-butyl ]-2-naphthamide was treated in the same manner as in Example 2 to obtain a red light-sensitive color photographic material. This photographic material was exposed to red light and then treated in the same manner as in Example 2, whereby a cyan colored negative image and an excellent red positive image were obtained simultaneously.
• Example 5 This experiment was conducted to compare the photographic properties of a cyan coupler according to the present invention with three cyan couplers of the prior art having a closely related structure.
• Control coupler D (Coupler lll, U.S. Pat. No.
• coupler (1) is much v at 440 my and 500 mu, as shown below:
• coupler (1) is very preferred for material as claimed in claim 1, wherein said coupler is auto-masking mechanism when it is jointly used with a a compound of the following structure colorless coupler.
• coupler (1) over coupler C results from the on structural difference between the two, in that the azo portion of coupler (I) is of the ester (COOC H5) A comucnmo uwum type whereas that of coupler C is of the ketone @5 -cocn type.
• coupler B In both coupler (l) and the coupler B; the azo portions are of the ester (-COOR) type, which show good 'l spectral characteristics.
• coupler B disadvanl tageously has undesired spectral absorption of masking -COOC2H5 dye, which is due to the inclusion of a branched alkyl group.
• the emulsion test indicates that coupler B has a broad absorption comprising two absorption maxima silver halide col or photographic material as claimed in claim 1, wherein said coupler is a compound of the following structure COOCHa wavel engtb. (m u) This means that coupler B is not appropriate as colored cyan coupler because its maskingaction is too excessive in the short wavelength region.
• coupler (l) and coupler D which have the azo portion of the ester type are equally competent in pho- 0 tographic properties.
• coupler D is detrimentally undesirable because of its having a maximum absorption at a verylong wavelength site, i.e., 720 mp. K/

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

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Cited By (2)

Citations (6)

• 1969
  • 1969-04-14 JP JP44028287A patent/JPS4817889B1/ja active Pending
• 1970
  • 1970-04-13 DE DE19702017625 patent/DE2017625A1/de active Pending
  • 1970-04-14 GB GB07796/70A patent/GB1255111A/en not_active Expired
• 1972
  • 1972-05-23 US US00256010A patent/US3784383A/en not_active Expired - Lifetime

Patent Citations (6)

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