US2930693A - Photographic materials containing n-substituted phthalimide compounds - Google Patents

Photographic materials containing n-substituted phthalimide compounds Download PDF

Info

Publication number
US2930693A
US2930693A US619137A US61913756A US2930693A US 2930693 A US2930693 A US 2930693A US 619137 A US619137 A US 619137A US 61913756 A US61913756 A US 61913756A US 2930693 A US2930693 A US 2930693A
Authority
US
United States
Prior art keywords
photographic materials
substituted
materials containing
substituted phthalimide
layers
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US619137A
Other languages
English (en)
Inventor
Ganguin Karl Otto
Ramsay David William Crichton
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from GB3117955A external-priority patent/GB803783A/en
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Application granted granted Critical
Publication of US2930693A publication Critical patent/US2930693A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00Photosensitive materials
    • G03C1/005Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/42Developers or their precursors
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/407Development processes or agents therefor
    • G03C7/413Developers
    • G03C7/4136Developers p-Phenylenediamine or derivatives thereof

Definitions

  • This invention relates to photographic materials and more particularly to light-sensitive photographic materials containing developers.
  • the photographic materials are passed through a tank containing the developer insolution.
  • the concentration of the developer falls so that the processing conditions vary and it is eventually necessary to add new developer to the tank.
  • the developer solution has to ditluse through the upper layers of the photographic materials before it can reach the lower layers so that an' even development of the various layers cannot'be achieved.
  • correct development of the bottom layer can only be obtained by having a high concentration of developer in the developer solution, but under these conditions there is a tendency forthe top layer to be over-developed.
  • a light sensitive gelatino-silver halide emulsion layer which contains a substituted phthalimide of the formula R1 C i 1 RI ⁇ C O J wherein R and R are substituted or unsubstituted alkyl radicals or R and R may be joined together or each or both joined to the benzene ring to form with the nitrogen atom a heterocyclic ring, X is hydrogen, an alkyl, substituted alkyl, alkyloxy, substituted alkyloxy, amino or substituted amino radical, and Y is a solubilising group, and wherein the benzene nuclei may carry substituents.
  • the solubilising group may be for example a carboxylic or sulphonic acid group or a salt of one of these, for example an alkali metal or ammonium salt.
  • the substitutedphthalimidea may- :be made-iby.1-.-heating.-.
  • R R and X have the meaning given above and thephenyl nucleus may carry further.substituents,,with1: phthalic anhydride or a substituted phthalic anhydrideg.. and, where both the amine and; phthalicranhydride-are groups, further treatingthe free from water solubilising product to introduce a water solubilisinggroupr
  • the gelatinosilver halideiemulsion nlayer also contains a ,colour coupler.
  • the emulsions vused .for forming -the-layers ofounirb; vention may be made by simply.,mixing;an- .aqueousisolu tion or dispersion of the substituted phthalim de with a normal gelatino-silver halide emulsiqn prepared in thre known manner and if desiredadding one. onmore sen-1:
  • halide emulsion layer containing a substituted phthalimide as hereinbefore-- defined forms a further feature of our invention.
  • Photographic materials containing the light-sensitive emulsion layers of our invention may be exposed to light in the normal way and then developed with an alkaline solution containing hydroxylamine or hydrazine and this process of development forms a further feature of our invention. If desired other adjuvants for example sodium sulphite and potassium bromide may be added to the developer solution. The material may then be fixed and, when the emulsion layer contains a colour coupler, the developed silver may be bleached.
  • Example parts of a gelatin-silver iodo-bromide emulsion containing 7.25% of gelatine, 3.35% of silver bromide and 0.05 of silver iodide are stirred and there are added 3 parts of a 0.05% solution in methanol of bis (3 ethyl 5 phenyl benzoxazole 2-) 9-ethy1trimethineyanine iodide (the iodide of the green sensitising dyestuit Rl340 described in B.I.O.S. Final Report No. 1355, page 86).
  • the mixture is stirred at 40 C.
  • the paper is washed and then transferred to a stop bath of the following composition:
  • the paper is washed and the developed silver is bleached and fixed in a solution of the following composition:
  • the paper is finally washed and dried.
  • a light sensitive gelatino-silver halide emulsion which contains a substituted phthalimide of the formula:
  • R and R are alkyl radicals
  • X is selected from the group consisting of alkyl, alkoxy and amino
  • Y is a solubilising group selected from the class consisting of sulphonic and carboxylic acid groups.
  • a light sensitive gelatino-silver halide emulsion ac cording to claim 1 which contains, in addition to the substituted phthalimide as defined in claim 1, a colour coupler capable of coupling with the oxidation product of a primary aromatic amino developer to form a dye.
  • a photographic material comprising a plurality of layers coated on a support, at least one of said layers being a light sensitive gelatino-silver halide emulsion layer which contains a substituted phthalimide of the formula:
  • R and R are alkyl radicals
  • X is selected from the group consisting of alkyl, alkoxy and amino
  • Y is a solubilising group selected from the class consisting of sulphonic and carboxylic acid groups, and which further contains a colour coupler capable of coupling with the oxidation product of a primary aromatic amino developer to form a dye.
  • a 'colour photographic process which comprises imagewise exposing to light a light sensitive gelatino-silver halide emulsion which contains a substituted phthalimide of the formula:
  • R and R are allcyl radicals
  • X is selected from the group consisting of alltyl, alkoxy and amino
  • Y is a solubilising group selected from the class consisting of sulphonic and carboxylic acid groups, and subsequently developing with an alkaline solution of a member of the class consisting of hydroxylamine and hydrazine.

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US619137A 1955-11-01 1956-10-30 Photographic materials containing n-substituted phthalimide compounds Expired - Lifetime US2930693A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB3117955A GB803783A (en) 1955-11-01 1955-11-01 Photographic materials
GB2930693X 1956-10-19

Publications (1)

Publication Number Publication Date
US2930693A true US2930693A (en) 1960-03-29

Family

ID=32396010

Family Applications (1)

Application Number Title Priority Date Filing Date
US619137A Expired - Lifetime US2930693A (en) 1955-11-01 1956-10-30 Photographic materials containing n-substituted phthalimide compounds

Country Status (4)

Country Link
US (1) US2930693A (fr)
BE (1) BE552264A (fr)
DE (1) DE1019560B (fr)
FR (1) FR1159499A (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1167650B (de) * 1960-08-22 1964-04-09 Polaroid Corp Mehrschichtiges, fuer Mehrfarben-Diffusionsverfahren geeignetes photographisches Material mit Entwicklersubstanzen in der Emulsionsschicht
US3161512A (en) * 1959-12-23 1964-12-15 Ilford Ltd Colour couplers and their production and use in colour photography
US4157915A (en) * 1977-05-02 1979-06-12 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material containing development precursor

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2137785A (en) * 1936-10-09 1938-11-22 Truecolour Film Ltd Color photography and cinematography
US2478400A (en) * 1945-08-17 1949-08-09 Eastman Kodak Co Silver halide photographic emulsion with developer and color coupler dispersed therein
US2706157A (en) * 1951-07-21 1955-04-12 Grant Photo Products Inc Processing photographic paper and film

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2137785A (en) * 1936-10-09 1938-11-22 Truecolour Film Ltd Color photography and cinematography
US2478400A (en) * 1945-08-17 1949-08-09 Eastman Kodak Co Silver halide photographic emulsion with developer and color coupler dispersed therein
US2706157A (en) * 1951-07-21 1955-04-12 Grant Photo Products Inc Processing photographic paper and film

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3161512A (en) * 1959-12-23 1964-12-15 Ilford Ltd Colour couplers and their production and use in colour photography
DE1167650B (de) * 1960-08-22 1964-04-09 Polaroid Corp Mehrschichtiges, fuer Mehrfarben-Diffusionsverfahren geeignetes photographisches Material mit Entwicklersubstanzen in der Emulsionsschicht
US4157915A (en) * 1977-05-02 1979-06-12 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material containing development precursor

Also Published As

Publication number Publication date
FR1159499A (fr) 1958-06-27
BE552264A (fr)
DE1019560B (de) 1957-11-14

Similar Documents

Publication Publication Date Title
US2367531A (en) Acylaminophenol photographic couplers
US2353754A (en) Color photography using metallic salt coupler compounds
JPH0152742B2 (fr)
US4009035A (en) Process for forming cyan dye photographic images
JPS6186750A (ja) 写真記録材料
US2453661A (en) Colored couplers
US2933391A (en) Photographic emulsions containing 5-pyrazolone coupler compounds
US2706684A (en) 1-hydroxy-2-naphthamide colored couplers
US2364675A (en) Color forming compounds containing sulphonamide groups
US3488193A (en) Silver halide emulsions containing naphthol color couplers
US2976146A (en) Novel cyan-forming couplers
US2455170A (en) Colored couplers
US3700454A (en) Light-sensitive silver halide color photographic material containing couplers and coupler solvents
US2435173A (en) Acetyl n-heterocyclic couplers for color photography
US2930693A (en) Photographic materials containing n-substituted phthalimide compounds
US2271229A (en) Fog inhibitor for photographic developers
US2350138A (en) Nondiffusing acylacetyl sulphonamide coupler
JPS59146050A (ja) ハロゲン化銀カラ−写真感光材料
US2186736A (en) Coupling compounds for color forming development
US3850638A (en) Benzimidazole nucleating agents
US2295008A (en) Photographic color forming compound
US2411951A (en) 4,4'-bis (pyrazolone) couplers for color photography
US2728660A (en) Salicylic acid ester and amide photographic coupler compounds
JPS6396656A (ja) 色再現性にすぐれたハロゲン化銀写真感光材料
US2350812A (en) Diketopyrimidine coupler