Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
  • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
  • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
• • 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
  • C07D231/18—One oxygen or sulfur atom
  • C07D231/20—One oxygen atom attached in position 3 or 5
  • C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
  • C07D231/26—1-Phenyl-3-methyl-5- pyrazolones, unsubstituted or substituted on the phenyl ring
• • 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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
  • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
  • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
  • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
• • 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

• This invention relates *pler compounds for color photography and more Patented Mar. 24,1953
• pyrazolone couplers in processes of color development in which the oxidation product of a primary aromatic amino developing agent couples with the pyrazolone to producea is well known in the art.
• the pyrazolone couplers are generally used to produce the magenta is affected by a single developer. solution freeof couplercompounds. In such processes'it is hecessary that the pyr'azolone coupler in the magenta layer react with the developing agent at the same speed as do the couplers in the other layers.
• the resulting dye image should i 15 Claims. (Cl. 95-6) such as alloxan hydrate, or triketohydrindene hydrate.
• coupler compounds have exlceptionally good solubility in coupler solvents customarily used for dispersin the compounds in gelatino-silver halide emulsion layers.
• the principal "Object of my invention is to provide pyrazolone couplers of good stability and solubility from which stable "dyef'ima'ges may be obtained by means of color development.
• the couplers contemplated by my invention are obtained by condensation of either one or two mols'of a pyrazolone witha compound, as for example, xanthydrol, or a gem-diol compound dye image in situ with a developed silver image i carbon atom which is-a part of a conjugated sys- Alloxan' hydrate and triketohydrindene hyidrate are typical gem-diol compounds.
• a compound as for example, xanthydrol
• g The compounds fall under the following gerreral :formula:
• the couplers of my invention are obtained by condensation of a pyrazolone coupler havingja reactive methylene group in the ll-position with compoundsof' the above class.
• Monomolecular 'or bisrpyrazolonecouplers are obtained depending upon the reaction conditions and the proportions of the reactants used.
• a monomolecular coupler can be obtained from alloxan hydrate by reacting it with approximately an equal mpl glllarl; rcpprnon of 1 apyrazol'one whereas two niols of pyr'azolone' are used to pro Jerusalem the bis-compound.
• the following compounds are illustrative of those which may be used according to my invention:-
• reaction mixture is poured mtofz oo cc. ma and suflicierit sodium hydroxide added to make neutral to litmus.
• the white solid is collected by suction filtration and recrystallized from 1,4-
• the white crystalline powder had an M. P. of 220-222 0.
• Example 2. (2',4',6" tMChZOTDphBM/D- A mixture of 6.72 g. (.01 mole) 1-(2',-4',6'-
• Example 4 -4,4 -aZZoman-bis-1 (p-tertbutyZphe- -alloxan monohydrate in 25 cc. pyridine is refluxed for 2 hours. After cooling somewhat, the -mixture is-poured into 200 cc. water and neutralized to litmus with acetic acid. The precipitate is collected and extracted with 200 cc. boiling ethyl alcohol. The alcohol extract is evaporated to crystallization; The yield of brownish crystals melting at 164166is 2.5 g., which is 42.1 per cent of the theoretical quantity, 5.94 g.
• the compound No. '7 the above list may be prepared in a similar mannerbylreacting triketohydrindene hydrate in place of alloxanwith the pyrazolone in approximately equal molecular proportions.
• the'same dye is Monomolecular .and bis-pyrazolone; coupler .cdrnpounds similar in structur'e. tothe compounds I of my invention have previously been suggested pler compounds.
• the couplers of the invention are especially suitable for use in sensitive silver halide emulsion layers for use in processes such as those described in Fischer U. S. l,055,l55,- Mannes and. Godowsky, U. S. 2,304,940 and Jelley and Vittum, U. S. 2,322,027. Their usefulness in such processes is apparent, particularly since the couplers have little tendency to wander in emulsion layers.
• the couplers can be incorporated in the emulsion layers especially as described in the latter patent.
• any color-forming developer containing a primary amino group may be used.
• the pamino phenols and their substitutionproducts may also be used where the amino group is unsubstituted.
• My development process may be employed for the production of colored photographic images in layers of gelatin or other water-permeable colloidalcarriers, such as albumen, collodion, organic esters of cellulose or synthetic resins.
• the carrier may be supported by a transparent medium such as glass, a cellulose ester or synthetic resin or a non-transparent reflecting medium such as paper or an opaque cellulose ester.
• the emulsion may be coated as a single layer on the support or as superposed layers on one or both sides of the support. The superposed layers may be, difierentially sensitized to form natural color images.
• a photographic emulsion layer comprising a carrier, silver halide and as a color-forming development component, the condensation product of a pyrazolone having a reactive methylene group in the 4-position and a compound containing the following group:
• X is a member of the group consisting of H and OH and Z represents the atoms noes..- sary to complete a cyclic ring free of substituents reactive with said methylene group, the condensation taking place at said methylene group and at a hydroxyl group of said compound.
• a photographic emulsion layer comprising a carrier, silver halide and as a color-forming development component, the condensation product of a, pyrazolone having a reactive methylene group in the 4-position and a compound containing the following group:
• Z represents the atoms necessary to complete a cyclic ring free of substituents reactive with said methylene group, the condensation taking place at said methylene group and at a hydroxyl group of said compound.
• a photographic emulsion layer comprising a carrier, silver halide and as a color-forming deof a 3 -acylaminopyrazolone having a reactive methylene group in the 4-position and triketohydrindene hydrate, the condensation taking place at said methylene group and at a hydroxyl group of said hydrate.
• a photographic emulsion layer comprising a carrier, silver halide and pea color forming development component, the condensation prodnot of a pyrazolone having a reactive methylene group in the 4-position and alloxan hydrate,-the condensation taking place at said methylene roup and at a hydroxyl group of alloxan.
• a photographic emulsion layer comprising a carrier, silver halide and as a color-forming development component, the reaction product of a 3-acylamino pyrazolone having a reactive methylene group in the 4-position and alloxan hydrate,
• a photographic emulsion layer comprising a carrier, silver halide and as a color-forming development component, the condensation product of a pyrazolone having a reactive methylene group in the 4-position and a compound containing the following group:
• Z represents the atoms necessary to complete a heterocyclic ring free of substituents reactive with said methylene group, the condensation taking place at said methylene group and at a hydroxyl group of said compound.
• a photographic emulsion layer comprising a carrier, silver halide and as a color-forming development component, the condensation product of a pyrazolone having a reactive methylene group in the 4-position and xanthydrol, the condensation taking place at said methylene group and at the hydroxyl group of xanthydrol.
• a photographic emulsion layer comprising a carrier, silver halide and as a color-forming development component, the condensation product of one molecule of a pyrazolone having a reactive methylene group in the 4-position and one molecule of a compound containing the following group:
• condensation product of two molecules of a pyrazolone having a reactive methylene group in the 4-position and one molecule of a compound containing the following group:
• Z represents the atoms necessary to complete a cyclic ring free of substituents reactive with said methylene group, the condensation taking place at said methylene group and the hydroxyl groups of said compound.
• a photographic emulsion layer comprising a carrier, silver halide and as a color-forming development component, the condensation product of one molecule of a pyrazolone having a reactive methylene group in the 4-positlon and one molecule of xanthydrol, the condensation taking place at said methylene group and at the hydroxyl group of xanthydrol.
• a photographic emulsion layer comprising a carrier, silver halide and as a, color-formin development component, the condensation product of two molecules of a pyrazolone having a reactive methylene group in the 4-position and one molecule of alloxan hydrate, the condensation taking place at said methylene group and at the hydroxy groups of said hydrate.
• a photographic emulsion layer comprising a carrier, silver halide and as a color-forming development component, the condensation product of two molecules of a pyrazolone having a reactive methylene group in the 4-position and one molecule of triketohydrindene hydrate, the condensation taking place at said methylene group and at the hydroxy groups of said hydrate.
• a photographic emulsion layer comprising a. carrier, silver halide and as a color-forming development component, the condensation product of a pyrazolone having a reactive methylene group in the 4-position and a compound selected from the class consisting of xanthydrol, alloxan hydrate and triketohydrindene hydrate, the condensation taking place at said reactive methylene group and at a hydroxyl group of a compound of said class.
• X is a member of the group consisting of H and OH and Z represents the atoms necessary to complete a cyclic ring free of substituents reactive with said methylene group, the condensation taking place at said methylene group and at a hydroxyl group of said compound.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Plural Heterocyclic Compounds (AREA)
• Indole Compounds (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Priority Applications (4)

Applications Claiming Priority (1)

Publications (1)

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ID=22270197

Family Applications (1)

Country Status (4)

Cited By (4)

Citations (5)

• 0
  • BE BE496132D patent/BE496132A/xx unknown
• 1949
  • 1949-06-11 US US98629A patent/US2632702A/en not_active Expired - Lifetime
• 1950
  • 1950-06-10 FR FR1066012D patent/FR1066012A/fr not_active Expired
  • 1950-06-12 GB GB14556/50A patent/GB680489A/en not_active Expired

Patent Citations (5)

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