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
  • G03C7/346—Phenolic couplers

Definitions

• R is a hydrogen atom or a lower alkyl group; R is an aliphatic hydrocarbon residue having 8 to '18 carbon atoms; 11 is zero or 1; and m is zero or 1.
• This invention relates to a light-sensitive color photographic material. More particularly, the invention is concerned with a color photographic material containing a blue image-forming novel coupler belonging to the socalled protect type coupler, i.e. a Water-insoluble or difficultly water-soluble coupler to be used by dissolving the same in a diflicultly water-miscible high boiling solvent and dispersing the resulting solution in a photographic emulsion.
• the novel coupler is represented by the general formula,
• R is a hydrogen atom or a lower alkyl group
• R is an aliphatic hydrocarbon residue having 8 to 18 carbon atoms
• m is zero or 1
• n is zero or 1. 7
• the coupler of the present invention is quite useful as a protect type coupler, and has greatly overcome the drawbacks of known couplers. Accordingly, the light-sesitive color photographic material according to the present invention, which has been incorporated with the said coupler, is excellent in spectral absorption characteristic and can give a high densitv color 15 image excellent in transparency.
• the coupler used in the present invention is synthesized, for example, in the following manner:
• a long chain alkyl bromide and catechol are condensed with each other in dimethylformamide in the presence of potassium bicarbonate to form a catechol monoalkyl ether, which is then condensed with a halogenated fatty acid to obtain a long chain alkoxyphenoxy fatty acid.
• This acid is treated with phosphorus pentachloride to form an acid chloride, which is then condensed with a phenol derivative having an amino group in the o-position to synthesize the desired coupler.
• couplers represented by the general formula are set forth below, but couplers usable in the present invention are not limited only to these.
• catechol monododecyl ether B.P. 203-205 C./ 4 mm. Hg
• catechol monooctyl ether B.P. l183 C./4 mm. Hg
• catechol decyl ether B.P. 192-195 C./4 mm. Hg
• catechol tetradecyl ether B.P. 220-225 C./4 mm. Hg
• catechol octadecyl ether B.P. 230-235" C./3 mm. Hg.
• Tables 1 and 2 show the fact that the couplers used in the present invention have a low melting point and have excellent solubility in a high boiling solvent as compared with known couplers.
• the exemplified coupler (4) and know couplers were individually treated in the same manner as in Example 2 mentioned later, and the resulting color images were subjected to heat resistance test (at 77 C. for 2 days) and light resistance test (irradiation with an arc-lamp for 32 hours) to obtain such results as set forth in Table 3, in which the heat and light resistance values are residual color ratios at a density of 1.0.
• the couplers used in the present invention are not only low in melting point but also excellent in solubility in high boiling solvents and particularly high in durability of resulting color images as compared with known couplers, and hence are extremely useful as protect type couplers.
• the couplers used in the present invention into a light-sensitive color photographic material, there may be adopted any of the known procedures.
• the couplers are dissolved either singly or in combination of 2 or more in a high boiling solvent (B.P. 175 C. or more) such as tricrcsyl phosphate or dibutyl phthalate, or a low boiling solvent such as butyl acetate or butyl propionate, or a mixture of said solvents.
• a high boiling solvent such as tricrcsyl phosphate or dibutyl phthalate, or a low boiling solvent such as butyl acetate or butyl propionate, or a mixture of said solvents.
• This solution is mixed with an aqueous gelatin solutioucontaining a surface active agent and then emulsified by means of a high speed rotary mixer or a colloid mill.
• the emulsified liquid is added directly to a silver halide photographic emulsion, which is then coated on a support such as a glass plate, synthetic resin sheet, film ing aids, etc.
• a support such as a glass plate, synthetic resin sheet, film ing aids, etc.
• the emulsion may contain a known carbocyanine or merocyanine dye as an optical sensitizer therefor.
• the thus obtained light-sensitive color photographic material is exposed to radioactive rays such as a-rays or S-rays, visible rays or infrared rays, developed with a 5 developer containing a p-phenylenediamine type developing agents as an active ingredient, and then bleached, desilvered and fixed to obtain a-high density color.
• radioactive rays such as a-rays or S-rays, visible rays or infrared rays
• a 5 developer containing a p-phenylenediamine type developing agents as an active ingredient
• a color photographic material using the coupler of the present inventionrnay be incorporated with an UV- absorber of the benzophenorie t'ype (e.-g. 2-hydroxy-4- dodecyloxybenzophenone) or the triazole type [c.g. 2(2'- hydroxy-3,5'-di-tcrt-butylphenyl) benzotriazole], whereby the resulting image can further be increased in durabilityl base, baryta paper or laminated paper, followed by dryethyl N B methanesulfonamidoethyl y ing, to prepare a light-sensitive color photographiiunaie-w rial.
• an UV- absorber of the benzophenorie t'ype e.-g. 2-hydroxy-4- dodecyloxybenzophenone
• the triazole type c.g. 2(2'- hydroxy-3,5'-di-tcrt-butylphenyl) be
• the above-mentioned emulsified liquid is once set, finely cut, freed from the low boiling solvent by water-washing or the like means and added to a photo- .ra a acaail heaelinthyl.eliehytlmxr hxl.aparhenyla enediamine, N ethyl N hydroxyethyl 2 methyl-pphenylenediamine and N,N diethyl 2 methyl-p-phenylenediamine.
• the developer may contain a developgraphic emulsion, which is then coated on a support such mam-Controlling agent, -8- citralinic acid, in addition to as mentioned above, followed by drying, to prepare a lightsensitive color photographic material.
• a developgraphic emulsion which is then coated on a support such mam-Controlling agent, -8- citralinic acid, in addition to as mentioned above, followed by drying, to prepare a lightsensitive color photographic material.
• T The above-mentioned procedures are illustrative and are not limitative.
• the coupler may be incorporated into 2 or more different emulsion layers of a multi-layered color photo- 65 graphic material.
• the photographic emulsion used in the present invention may be prepared by use of various silver halides such as silver chloride, silver iodobromide or silver chlorobromide,
• the emulsion may have been incorporated with any of ordinary photographic additives such as, for example, anti-foggants, stabilizers,
• the material was subjected to ordinary stopping, film-hardening and water-washing treatments, and then subjected to second exposure by use of a white Water to make 1,000 ml.
• a light-sensitive silver halide color photographic material characterized by containing as a coupler a comlight. Subsequently, the thus treated material was depound f h general f la,
• a mixture comprising 10 g. of the exemplified coupler (4) and ml. of dibutyl phthalate was heated to 50 C. to form a solution.
• This solution was mixed with 5 ml. of a 10% aqueous Alkanol B solution and 200 ml. of a 5% aqueous gelatin solution, and the resulting mixture was subjected several times to a colloid mill to form a dispersion.
• This dispersion was added to 500 g. of a gelatin silver chlorobromide emulsion, which was then coated on a baryta paper and dried to prepare a light-sensitive material.
• N-ethyl-N-B methanesulfonamidoethyl-3-methyl- N ethyl N p-methanesulfonamidoethyl-3-methyl- Water to make 1,000 mil.
• the developed material was then dipped for 2 to 4 minutes in a stopping-fixing bath of the following composition:
• R is a hydrogen atom or a lower alkyl group; R is an aliphatic hydrocarbon residue having 8 to 18 carbon atoms; n is zero or 1; and m is zero or 1.

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• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Silver Salt Photography Or Processing Solution Therefor (AREA)
• Heat Sensitive Colour Forming Recording (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Applications Claiming Priority (1)

Publications (1)

Family

ID=12582035

Family Applications (1)

Country Status (3)

Cited By (2)

• 1970
  • 1970-05-14 JP JP45040491A patent/JPS4916056B1/ja active Pending
• 1971
  • 1971-05-13 US US00143240A patent/US3737318A/en not_active Expired - Lifetime
  • 1971-05-14 GB GB05019/71A patent/GB1298305A/en not_active Expired

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