US3772021A - Process for the development of silver halide light-sensitive material - Google Patents

Process for the development of silver halide light-sensitive material Download PDF

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Publication number
US3772021A
US3772021A US00079627A US3772021DA US3772021A US 3772021 A US3772021 A US 3772021A US 00079627 A US00079627 A US 00079627A US 3772021D A US3772021D A US 3772021DA US 3772021 A US3772021 A US 3772021A
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US
United States
Prior art keywords
compound
developing
silver halide
development
emulsion
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
US00079627A
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English (en)
Inventor
M Yoneyama
I Shimamura
H Iwano
R Ohi
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.)
Fujifilm Holdings Corp
Original Assignee
Fuji Photo Film Co 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
Application filed by Fuji Photo Film Co Ltd filed Critical Fuji Photo Film Co Ltd
Application granted granted Critical
Publication of US3772021A publication Critical patent/US3772021A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C07D213/20—Quaternary compounds thereof
    • 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
    • C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • G03C1/04—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with macromolecular additives; with layer-forming substances
    • G03C1/043—Polyalkylene oxides; Polyalkylene sulfides; Polyalkylene selenides; Polyalkylene tellurides
    • 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
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/08—Sensitivity-increasing substances
    • 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
    • G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
    • G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
    • G03C5/29—Development processes or agents therefor
    • G03C5/305—Additives other than developers
    • G03C5/3056—Macromolecular additives

Definitions

  • ABSTRACT A process for the development of silver halide photographic materials which comprises developing photographic materials in the presence of a compound of the formula:
  • R is a hydrogen atom, an alkyl group, an alkylphenyl group or (CI-I ),,,OR, R is a hydrogen atom, an alkyl group or m is a positive integer of at least 2, n is O or a positive integer, p is l or 2, X is an anion, and Z is an organic chemical structure necessary for completing a heterocyclic ring together with N, is disclosed.
  • the scope of the present invention also extends to the developed product formed, the developing compounds employed and their process of preparation.
  • R is a hydrogen atom, an alkyl group, an alkylphenyl group or -(CI-I -OR', R being a hydrogen atom, an alkyl group or m being an integer of at least 2, n being or a positive integer, p being 1 or 2, X being an anion, and Z being an organic chemical structure for completing the heterocyclic ring together with N such as pyridinium, imidazolium or quinolinium ring.
  • the compound 2 is obtained after the elimination of the excess pyridine by distillation.
  • Synthesis of Compound 8 l Mole of l-ethoxy-3-chloropropanol-2 synthesized in the manner as in the above example and 1 mole of Z-methylimidazole are dissolved in dioxane and the resulting solution is heated for about hours. The reaction mixture is then washed with ethyl acetate to obtain the Compound 8.
  • the ether parts are collected, dried by anhydrous sodium sulfate and, after removal of ether by distillation, refined to obtain a monoglycidyl ether of a boiling point of l14-5C/2.5 mm Hg and a diglycidyl ether of a boiling point of l23-4C/2.5 mm Hg.
  • One mole of the diglycidyl ether is dissolved in 600 cc of dioxane and gaseous hydrogen chloride is then introduced into the solution with stirring and cooling until hydrogen chloride becomes excessive.
  • the solution is then allowed to stand overnight.
  • the solution is heated on a steam bath for about 1 hour, and nitrogen gas is then introduced to eliminate any excess of hydrogen chloride.
  • reaction product After elimination of dioxane under reduced pressure, the reaction product is refluxed in an excess of hydrous pyridine for 14 hours. During the reflux, the reaction mixture gradually separated to two phases. After removal of the lower layer, pyridine was elirninated from the upper layer. The residue of upper layer is dissolved in a small amount of water and then washed with ether to obtain the Compound 15.
  • the compounds l,3,4,5 and 6 are synthesized by using methanol, propanol, butanol, hexanol and tetradecyl alcohol respectively in the manner as prescribed in the synthesis of the Compound 2.
  • the compounds 7,9,l0 and 1 l are synthesized in the manner as prescribed in the synthesis of the Compound 8 by use of methanol, propanol, butanol and hexanol, respectively.
  • the Compound 13 is synthesized in the similar manner as in the synthesis of the Compound 18 by use of the monoglycidyl ether.
  • the Compounds 14 and 16 are synthesized in the same manner as in the synthesis of the Compound 15.
  • the compounds of the present invention are applicable to the ordinary silver halide photosensitive materials, such as, e.g., black and white positive materials of relatively low sensitivity, black and white negative materials of relatively high sensitivity, X-ray materials and color materials.
  • the known amine compounds and quaternary salt compounds have development accelerating effects and sensitivity increasing effects, they have a drawback of increasing fog.
  • the compounds of the present invention are free from the drawback of increasing fog and moreover considerably accelerate the rate of development and increase the sensitivity.
  • the developing solution in which the compounds of the present invention are used are the ordinary developing solutions which contain at least one of the following compounds, and their known derivatives, as the developing agents: hydroquinone, l-phenyl-3 pyrazolidone, N-methyl-p-aminophenol, N,N-diethylp-phenylenediamine.
  • the developing solutions may contain, in addition to the developing agent, preservatives, such as sodium sulfite, ascorbic acid or hydroxylamine, pH adjusting or bufiering agent, such as sodium sulfate, boric acid, borax, sodium hydroxide, sodium carbonate or trisodium phosphate, development retarders, such as potassium bromide or potassium iodide, or anti-fogging agents, such as 6- nitrobenzimidazole, benzotriazole or 1 mercaptotetrazole.
  • preservatives such as sodium sulfite, ascorbic acid or hydroxylamine
  • pH adjusting or bufiering agent such as sodium sulfate, boric acid, borax, sodium hydroxide, sodium carbonate or trisodium phosphate
  • development retarders such as potassium bromide or potassium iodide
  • anti-fogging agents such as 6- nitrobenzimidazole, benzotriazole or 1 mercaptotetrazole
  • the compounds of the present invention may be effectively incorporated in a developing solution, in a bath preceding the development step andfor in a silver halide emulsion. Satisfactory results are obtainable, in most cases, by use of one of the compounds of the present invention, though, in certain cases, an increased effect may be obtained by a combined use of two or more of the compounds of the present invention.
  • the compound of the present invention is usually used in a concentration of from 0.01 to 20 parts/l and preferably 0.1 to 10 parts/l, depending upon composition of the solution.
  • the compound in a silver halide emulsion, it is preferable to incorporate these compounds in an amount of from 0.01 to 20 parts per mole of silver halide, depending on the composition of the emulsion and/or the method of sensitizing applied to the emulsion.
  • the compound may be added to the emulsion in any stage of the preparation thereof, best results are obtained when it is added to the emulsion between chemical sensitization and coating.
  • the compound may be incorporated in a contiguous layer such as a protective layer instead of incorporating directly in the emulsion layer. In this case, the compound in the contiguous layer migrates immediately or during the later processes including development into the emulsion layer.
  • the silver halide emulsion used in the practice of the present invention includes those containing silver chloride, silver bromide, silver chlorobromide, silver iodide, silver iodobromide or silver chloro-iodobromide.
  • the emulsion may be chemically sensitized by means of an unstable sulfur compound and/or a gold compound.
  • the emulsion may be spectrally sensitized by means of, e.g., a cyanine dye or merocyanine dye.
  • the emulsion may be stabilized by a heterocyclic compound such as, e.g., 4-hydroxy-6-methyl-1,3,3a, 7- tetrazaindene or l-phenyl-5-mercaptotetrazole.
  • the emulsion may be hardened by known hardeners such as formaldehyde or mucochloric acid or may contain a surface active agent as a coating aid.
  • the emulsion may contain a color coupler capable of reacting with an oxidized product of an aromatic primary amine developing agent to form a color image.
  • EXAMPLE 1 A commercially available fine grain positive cine film comprising a fine grain silver chloroiodobromidegelatin emulsion was developed at 20C in a developing solution of the following composition.
  • the developing time could be shortened by addition of a compound of the present invention (Compoundto the developing solution as indicated in the following Table I.
  • a compound of the present invention Compoundto the developing solution as indicated in the following Table I.
  • another test strip which was developed for 8 minutes in the presence of the compounds of the present invention showed an increase in sensitivity as indicated also in the Table 1.
  • the photographic characteristics in the case where a known quaternary ammonium salt compound-l7 was added were also indicated in the Table l.
  • EXAMPLE 2 A commercial high speed film comprising a spectrally sensitized silver iodobromide-gelatin emulsion was developed at C in a developing solution of the following composition.
  • a commercially available fine grain positive cine film comprising a fine grain silver chloroiodobromidegelatin emulsion was developed using the same developing solution as in Example 1 at 20C for 8 minutes. Separately, other pieces of the film were developed in the same manner using the same solution except that a compound of the present invention (Compound 1 to 5) or a Compound 20 which was outside the scope of the present invention had been added for comparison. The results obtained were summarized in the Table-4.
  • An aqueous solution of the Compound 12 or 15 of the present invention was added to a silver iodobromide-gelatin emulsion containing 3.0 mol% of silver iodide (1g per kg-cm.) and coated on a film support and dried.
  • the test films thus obtained were developed at 20C for 8 minutes in the same developing solution as in Example 1.
  • the photographic characteristics obtained were indicated in the Table-6.
  • a process for the development of silver halide photographic materials which comprises developing said photographic materials in the presence of a compound which increases the rate of development and effective sensitivity without increasing fog, said compound being represented by the formula:
  • R is a hydrogen atom, an alkyl group, an alkylphenyl group or -(CH -OR, R is a hydrogen atom, an alkyl group or m is a positive integer of at least 2, n is 0 or a positive integer, with the proviso that when R is a hydrogen atom, n is a positive integer, p is 1 or 2, X is an anion, and Z is an organic chemical structure necessary for completing a heterocyclic ring together with N selected from the group consisting of pyridinium, imidazolium and quinolinium.
  • n is an integer of 0 to 3
  • m is an integer of 2 to 6.
  • said developing solution contains at least one member selected from the group consisting of hydroquinone, l-phenyl-3 -pyrazolidone, N-methyl-p-aminophenol and N,N-diethyl p-phenylenediamine.
  • concentration of developing compound ranges from 0.01 to 20 parts/- mole of silver in said emulsion.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Pyridine Compounds (AREA)
US00079627A 1969-10-09 1970-10-09 Process for the development of silver halide light-sensitive material Expired - Lifetime US3772021A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP44080988A JPS4843136B1 (fr) 1969-10-09 1969-10-09

Publications (1)

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US3772021A true US3772021A (en) 1973-11-13

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Country Status (6)

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US (1) US3772021A (fr)
JP (1) JPS4843136B1 (fr)
BE (1) BE757216A (fr)
DE (1) DE2049754A1 (fr)
FR (1) FR2065165A5 (fr)
GB (1) GB1298965A (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0106306A2 (fr) 1982-10-14 1984-04-25 Fuji Photo Film Co., Ltd. Matériaux photographiques couleur à l'halogénure d'argent
EP0112162A2 (fr) 1982-12-13 1984-06-27 Konica Corporation Matériel photographique photosensible aux halogénures d'argent
EP0147854A2 (fr) 1983-12-29 1985-07-10 Fuji Photo Film Co., Ltd. Matériel photosensible aux hologènures d'argent
EP0209118A2 (fr) 1985-07-17 1987-01-21 Konica Corporation Matériau photographique à l'halogénure d'argent
US6071688A (en) * 1998-07-29 2000-06-06 Eastman Kodak Company Providing additives to a coating composition by vaporization
US7250202B1 (en) 1998-06-18 2007-07-31 Ilford Imaging Ch Gmbh Recording sheets for ink jet printing

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011135673A1 (fr) * 2010-04-27 2011-11-03 荏原ユージライト株式会社 Nouveau composé et son utilisation
JP2012116802A (ja) * 2010-12-02 2012-06-21 Nitto Boseki Co Ltd イオン液体及びその製造方法
US10918624B2 (en) 2019-06-03 2021-02-16 Imam Abdulrahman Bin Faisal University Anti-cancer azole compounds

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2648604A (en) * 1951-12-28 1953-08-11 Gen Aniline & Film Corp Photographic developer containing a pyridinium salt and process of development
US2940851A (en) * 1957-11-27 1960-06-14 Eastman Kodak Co Sensitization of photographic emulsions

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2648604A (en) * 1951-12-28 1953-08-11 Gen Aniline & Film Corp Photographic developer containing a pyridinium salt and process of development
US2940851A (en) * 1957-11-27 1960-06-14 Eastman Kodak Co Sensitization of photographic emulsions

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0106306A2 (fr) 1982-10-14 1984-04-25 Fuji Photo Film Co., Ltd. Matériaux photographiques couleur à l'halogénure d'argent
EP0112162A2 (fr) 1982-12-13 1984-06-27 Konica Corporation Matériel photographique photosensible aux halogénures d'argent
EP0147854A2 (fr) 1983-12-29 1985-07-10 Fuji Photo Film Co., Ltd. Matériel photosensible aux hologènures d'argent
EP0209118A2 (fr) 1985-07-17 1987-01-21 Konica Corporation Matériau photographique à l'halogénure d'argent
US7250202B1 (en) 1998-06-18 2007-07-31 Ilford Imaging Ch Gmbh Recording sheets for ink jet printing
US6071688A (en) * 1998-07-29 2000-06-06 Eastman Kodak Company Providing additives to a coating composition by vaporization

Also Published As

Publication number Publication date
GB1298965A (en) 1972-12-06
DE2049754A1 (de) 1971-04-29
JPS4843136B1 (fr) 1973-12-17
FR2065165A5 (fr) 1971-07-23
BE757216A (fr) 1971-03-16

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