Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
  • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
• • 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
  • G03C7/36—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

• magenta couplers for example, giving dyes having absorption maxima at different wave lengths. This may be for the purpose of securing a broader absorption range or of shifting the maximum of absorption of the final dye to a point which cannot be obtained by other means. In the past this has been accomplished either by coating a physical mixture of two couplers in the same emulsion layer or by coating each coupler in a separate layer, the one layer being superimposed on the other. Both of these methods have serious disadvantages.
• a and D may, for example, be hydrogen, alkyl, aryl or substituted aryl amino or acylamino and B and C may, for example, be hydrogen, alkyl, aryl or substituted aryl groups.
• the pairs of groups AD and BC are chosen in such a way that if AD are the same, then BC are dissimilar and vice versa.
• the compounds of the invention have the above general formula in which at least two of the substituents A, B, C and D are dilferent.
• the unsymmetrical bis-pyrazolone compounds having the above structure are particularly advantageous since during the process of color development in which silver halide is reduced to silver by means of a primary aromatic amino developing agent, the bis-pyrazolones split at the moment of coupling to yield two fragments which react with the developer oxidation product at approximately equivalent rates. This is surprising since the prior art teaches that when symmetrical 4,4 bis-pyrazolones react with color developers, only one of the pyrazolone nuclei reacts with the color developer.
• I can dispense with having to prepare two pyrazolone couplers of high purity and having to weigh these out separately; instead, there can be used a single pure compound in the required quantity.
• the two pyrazolone nuclei obtained from the unsymmetrical bis-pyrazolone compounds appear to produce approximately the same quantity of dye with a given color developing agent and consideration need not be given to differences in reactivity of pyrazolones which are present when the discrete pyrazolone couplers are used.
• Particularly valuable unsymmetrical bis-pyrazolone couplers are those having the above general formula in which R is a methoxy phenyl group especially a p-methoxy phenyl group inasmuch as the reactivity of such couplers is great.
• EXAMPLE H p-phenylenediamine derivatives were examined spectrophotometrically and found to be a mean between the a ⁇ 4((1' benzothiazolyl) 3[(3" tert.amylphen0xy)- images which were obtained from the two components benzamido] 5 pyrazol0nyl) ⁇ 1 phenyl 3 aminocoated separately. The same result was obtained when 4(p-methoxybenzyl)-5-pyrazolone the color development reaction was carried out in solution: the spectrophotometric curve of the resulting dye O H was a mean between the curves of the two dyes obtained 5 from the separate parent components.
• tylphenoxy)phenyl] carbamyI-S-pyrazolone was prepared c c 0. c-NH, by acylation of 4-tert.butylphenoxy aniline with 1(4' S g H l O 1 ll tert.butylphenoxy)phenyl-3-carboxy-5-pyrazolone.
• the desired bis-pyrazolone was prepared as follows:
• aldehydes such as benzaldehyde, p-dimethylamino-, p-chloro-, ochloro-, p-nitro-, p-hydroxy benzaldehydes, syringaldehyde, vanillaldehyde, etc.
• aldehydes such as benzaldehyde, p-dimethylamino-, p-chloro-, ochloro-, p-nitro-, p-hydroxy benzaldehydes, syringaldehyde, vanillaldehyde, etc.
• the coupler compounds of the invention are designed primarily for use in silver halide emulsions and to this end may be incorporated in emulsions by the methods of Mannes et al. U. S. Patents 2,304,939 and 2,304,940, granted December 15, 1942, and Jelley et al. U. S. Patent 2,322,027, granted June 15, 1943.
• the coupler is dissolved in a water-insoluble material such as dimethyl phthalate and the solution is then dispersed in the sensitive emulsion.
• the couplers may be in emulsion layers of gelatin or other waterpermeable colloidal carriers, such as albumin, collodion, organic esters of cellulose, or synthetic resins.
• the emulsion may be supported by transparent medium such as glass, a cellulose ester or synthetic resin or a nontransparent medium such as paper or an opaque cellulose ester.
• the emulsion may be coated as a single layer or as superposed layers on one or both sides of the support.
• the emulsion layers may be differently sensitized, the emulsions containing the couplers of the invention forming magenta images, preferably, but not necessarily, being sensitized primarily to green light.
• a typical color developer for use in developing emulsion layers containing the coupler compounds of the invention is as follows:
• the unsymmetrical bis-pyrazolones of the invention are primarily intended for use in emulsion layers, they can be used in color-developing compositions such as given above.
• the couplers are incorporated into the developer compositions by first dissolving in a solvent such as isopropyl alcohol and this solution is then added to the alkaline developer composition. About 3 grams of coupler are suitable for use in developer compositions such as the above.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Silver Salt Photography Or Processing Solution Therefor (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Priority Applications (4)

Applications Claiming Priority (1)

Publications (1)

Family

ID=22995400

Family Applications (1)

Country Status (4)

Cited By (9)

Citations (4)

• 0
  • BE BE516241D patent/BE516241A/xx unknown
• 1951
  • 1951-12-15 US US261909A patent/US2706683A/en not_active Expired - Lifetime
• 1952
  • 1952-12-15 FR FR1067680D patent/FR1067680A/fr not_active Expired
  • 1952-12-15 GB GB31796/52A patent/GB721520A/en not_active Expired

Patent Citations (4)

Also Published As

Similar Documents