US3816141A - Fogged, direct positive silver halide emulsion sensitized with an isoindolinone polymethine dye - Google Patents

Fogged, direct positive silver halide emulsion sensitized with an isoindolinone polymethine dye Download PDF

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Publication number
US3816141A
US3816141A US00271152A US27115272A US3816141A US 3816141 A US3816141 A US 3816141A US 00271152 A US00271152 A US 00271152A US 27115272 A US27115272 A US 27115272A US 3816141 A US3816141 A US 3816141A
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Prior art keywords
silver halide
direct positive
fogged
emulsions
isoindolinone
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US00271152A
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English (en)
Inventor
O Riester
H Ohlschlager
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Agfa Gevaert AG
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Agfa Gevaert AG
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/06—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups three >CH- groups, e.g. carbocyanines
    • 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
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/485—Direct positive emulsions
    • G03C1/48515—Direct positive emulsions prefogged
    • G03C1/48523—Direct positive emulsions prefogged characterised by the desensitiser
    • G03C1/4853—Direct positive emulsions prefogged characterised by the desensitiser polymethine dyes

Definitions

  • ABSTRACT Y Light-sensitive photographic direct positive material containing at least one fogged silver halide emulsion layer which layer contains a polymethine sensitizer containing an isoindolinone ring.
  • bromide or iodide perchlorate, sulfate, methylsulfate, p-toluenesulfonate;
  • Q represents the ring members required for completing a 5- or 6-membered heterocyclic ring;
  • the heterocyclic group may contain a condensed benzene or naphthalene ring and additional substituents;
  • the heterocyclic groups may be those commonly found in cyanine chemistry, for example those based on thiazole (e.g., thiazole, 4-methylthiazole, 5- methylthiazole, 4,5-dimethylthiazole, 4- phenylthiazole, S-phenylthiazole or 4,5- diphenylthiazole), benzothiazole (e.g., benzothiazole, 4-chlorobenzothiazole, S-chlorobenzothiazole, 6-chlorobenzothiazole, 7-chlorobenzothiazole, 6- bromobenzothiazole, S-iodobenzothiazole, 6-
  • thiazole e.g., thiazole, 4-methylthiazole,
  • naphtho[l,2-d]thiazole naphtho[ 2, l -d]thiazole, 7-methoxy-naphtho[2, l d]thiazole or 8 methoxynaphtho[l,2-d]thiazole
  • selenazole e.g. 4-methylselenazole or 4- phenylselenazole
  • benzoselenazole e.
  • oxazole 4- methyloxazole, 4-phenyloxazole or 4,5 diphenyloxazole
  • benzoxazole e.g., benzoxazole, 5-chlorobenzoxazole, 6-chlorobenzoxazole, 5,6-dimethylbenzoxazole, S-phenylbenzoxazole, S-hydroxybenzoxazole, S-methoxybenzoxazole, 5- phenylbenzoxazole, S-hydroxybenzoxazole, 5- methoxybenzoxazole, S-ethoxybenzoxazole, 6- dialkylaminobenzoxazole, S-carboxybenzoxazole, 5-sulfobenz0xazole, sulfonamidobenzoxazole or S-carboxyvinylbenzoxazole), naphthoxazole (e.g., naphtho[ l ,2-d1oxazole, naphtho[2, 1 -d]
  • the silver halide of the silver halide emulsions to which the new cyanine dyes may be added may consist of one of the usual silver halides used for preparing photographic silver halide emulsions, i.e., for example silver bromide, silver iodide, silver chloride, silver chlo robromide, silver bromoiodide and silver chlorobrornoiodide.
  • the new cyaninedye's are preferably added to the washed silver halide emulsions and dispersed in them as uniformly as possible.
  • the incorporation of the dyes in the emulsions may be carried out by the usual known methods, for example, the dyes may be added to the emulsions from solutions in suitable solvents.
  • the solvents must, of course, be selected so that they have no adverse effect on the light-sensitive photographic material which is to be produced. Suitable solvents are, for
  • the good sensitizing effect is preserved even in the presence of water-soluble and emulsified color couplers.
  • the emulsion may also contain the usual wetting agents, stabilizers, brightening agents and other additives.
  • EXAMPLE 45 mg of sensitizer 3 in the form of a 1:1000 solution in methanol are added with stirring to 1 kg of a direct positive emulsion which has been prepared by chemical based on the amount of silver, and the mixture is left.
  • the layer is then fixed with an aqueous solution of sodium thiosulfate in the usual manner.
  • a positive image of the test wedge with exceptional whites and an excellent gamma value (gradation) is obtained.
  • the spectral sensitization curve is represented in FIG. 2.
  • FIG. 1 shows for comparison the sensitivity curve obtained without sensitizer.
  • sensitizer 3 When sensitizer 3 is replaced by an equal quantity of compound 8, the sensitization curve of FIG. 3 is obtained, and when an equal quantity of compound 9 is used, the sensitization curve of FIG. 4 is obtained.
  • the sensitization curve of FIG. 5 is obtained when using compound 17 in the same way.
  • Light-sensitive photographic direct positive material containing at least one fogged silver halide emulsion layer which layer contains an isoindolinone polymethine sensitizer of the following formula:
  • R stands for hydrogen or halogen
  • R represents an aliphatic group having up .to 6 carbon atoms, cycloalkyl or aryl;
  • n 0 or 1
  • X represents any anion
  • Q stands for the ring members required for completing a 5- or 6-membered heterocyclic ring based on thiazole, benzothiazole, naphthothiazole, selenazole, benzoselenazole, naphthoselenazole, oxazole, benzoxazole, naphthoxazole, 3,3- dialkylindolenine, Z-pyridine, 4pyridine, 2- quinoline, 4-quinoline, isoquinoline, thiazoline, oxazoline, pyrroline, tetrahydropyridine, thiadiazole, oxadiazole, pyrimidine, triazine, benzothiazine, pyrimidone or thiopyrimidone, which heterocyclic ring may contain a fused benzene or naphthalene rmg'

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Plural Heterocyclic Compounds (AREA)
US00271152A 1971-07-14 1972-07-12 Fogged, direct positive silver halide emulsion sensitized with an isoindolinone polymethine dye Expired - Lifetime US3816141A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2135153A DE2135153A1 (de) 1971-07-14 1971-07-14 Spektral sensibilisierte direktpositiv-emulsion

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US3816141A true US3816141A (en) 1974-06-11

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US (1) US3816141A (show.php)
BE (1) BE785309A (show.php)
DE (1) DE2135153A1 (show.php)
FR (1) FR2145682B1 (show.php)
GB (1) GB1378551A (show.php)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4515955A (en) * 1982-03-08 1985-05-07 Minnesota Mining And Manufacturing Company Isoindoline cationic dyes

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3687675A (en) * 1971-05-03 1972-08-29 Eastman Kodak Co Photographic silver halide emulsions containing a cyanine dye containing at least one 1-cyanoalkyl-2-arylin-dole nucleus
US3687674A (en) * 1969-11-14 1972-08-29 Fuji Photo Film Co Ltd Direct positive fogged silver halide emulsion sensitized with a cyclo-heptatriene cyanine dye

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3687674A (en) * 1969-11-14 1972-08-29 Fuji Photo Film Co Ltd Direct positive fogged silver halide emulsion sensitized with a cyclo-heptatriene cyanine dye
US3687675A (en) * 1971-05-03 1972-08-29 Eastman Kodak Co Photographic silver halide emulsions containing a cyanine dye containing at least one 1-cyanoalkyl-2-arylin-dole nucleus

Also Published As

Publication number Publication date
FR2145682A1 (show.php) 1973-02-23
BE785309A (fr) 1972-12-27
FR2145682B1 (show.php) 1976-10-29
DE2135153A1 (de) 1973-01-25
GB1378551A (en) 1974-12-27

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