Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
  • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
  • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
  • C07D231/52—Oxygen atom in position 3 and nitrogen atom in position 5, or vice versa
• • 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
  • G03C7/3212—Couplers characterised by a group not in coupling site, e.g. ballast group, as far as the coupling rest is not specific

Definitions

• This invention relates to light-sensitive silver halide emulsions for color photography and more particularly to a photographic silver halide emulsion containing a protective coupler.
• a method of making a coupler water-soluble and incorporating it as a form of an aqueous solution in the emulsion, and a method of making a coupler oil-soluble and incorporating it as a form of an organic solvent solution in the emulsion have occupied important positions.
• the coupler has a higher solubility in an organic solvent in use for dispersing and a higher dispersibility during and after applied to a base as a light-sensitive material.
• a Water-soluble solvent of high boiling point such as butyl phthalate, otolyl phosphate and butyl phosphate.
• A is a coupling component having at least one ketomethylene group, pyrazolone nucleus, phenol nucleus or a nucleus having phenolic hydroxyl group such as naphthol nucleus and n is an integer from 6 to 12.
• A is a coupling component having at least one ketomethylene group, pyrazolone nucleus, phenol nucleus or naphthol nucleus as above and m' is an integer from 2 to 7, n is 14 when m is 3, and from 6 to 14 when m is 2, 4, 5, 6 and 7.
• n is less than 5, the diffusion of the coupler can be observed in the emulsion layer of light sensitive material and when m is 0 or 1, the insuflicient solubility tends to cause a rapid deposition and aggregation during supercooling.
• n 15 or m exceeds 8, the solubility is too low.
• n 14 the solubility may be compared unfavourably with the case of less than this, but the compound can find a practical use in many cases, since the deposition by supercooling is very slow. For example, it is in a very advantageous position particularly when it is adapted for a light-sensitive material which should resist a severe thermal shock or when the coupling A has a property to promote crystallization.
• the compounds 6-9 referred for the comparison are as water, crystallized with the addition of nitromethane and follows: recrystallized from methanol to produce 3 g. of the final 0H product which melted at 64 C.
• the homologue thereof could be synthesized in the OONHCHNHZNHCO (0119156113 same manner as above but, in the case of the intermediate branched acid being oily at room temperature, it was employed as it was for the subsequent step after the step of (6) removing ether.
• Example 1 8 g. of the Compound 1 was dissolved in 20 g. of butyl phthalate with heating, the resulting solution was added to a mixed solution of 10 m1. of 5% saponin aqueous solution and 200 ml. of 5% gelatin aqueous solution, made emulsified and added to 500 g. of an emulsion of iodobromide. A film base coated by the resulting emulsion was dried, exposed, developed by the following developing solution, bleached and fixed.
• Example 2 6 g. of the Compound 2 was dissolved in 20 g. of butyl terephthalate and treated as in Example 1 thereby to obtain a magenta image having the absorption maximum at 545 n.m. The deposition and aggregation of the coupler could not be observed throughout the process and in the color image.
• the Schu value by ASTM at the maximum density was 10.8, while that of the Compound 7 at the same condition was 50.8.
• Example 3 G N,N-diethyl-p-phenylenediamine hydrochloride 2.0 Sodium sulfite 2.0 Sodium carbonate 20.0 Potassium bromide 2.0
• Example 4 10 g. of the Compound 4 was dissolved in a mixed solution of 18 g. of butyl phthalate and 2 g. of o-tolyl phosphate and treated as Example 1 thereby to produce a satisfactory yellow image having the absorption maxi- 6 mum at 442 n.m.
• the Schu value by ASTM at the maximum density was 5.8, while that of the Compound 9 at the same condition was 46.8.
• Example 5 8 g. of the Compound 5 was dissolved in a mixed solution of 15 g. of butyl phosphate and 5 g. of o-tolyl phosphate, dispersed in the similar manner to that described in Example 1 and processed in the developer described in Example 3 thereby to produce a satisfactory yellow image having the absorption maximum at 430 n.m.
• the Schu value by ASTM at the maximum density was 5.7.
• A is a coupling component having at least a member selected from the group consisting of ketomethylene group, pyrazolone nucleus, phenol nucleus, and naphthol nucleus, m is an integer from 2 to 7 and n in an integer from 6 to 14 when m is 2, 4, 5, 6 and 7 and n is 14 when m is 3.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• 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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Cited By (5)

Citations (2)

• 1964
  • 1964-12-09 US US417243A patent/US3418129A/en not_active Expired - Lifetime
  • 1964-12-24 GB GB52485/64A patent/GB1018810A/en not_active Expired
  • 1964-12-24 BE BE657579A patent/BE657579A/xx unknown
  • 1964-12-28 DE DEF44815A patent/DE1285314B/de active Pending

Patent Citations (2)

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