EP0569074A1 - Verfahren zur Herstellung einer wässrigen Dispersion von festen Teilchen einer photographisch verwendbaren Verbindung - Google Patents

Verfahren zur Herstellung einer wässrigen Dispersion von festen Teilchen einer photographisch verwendbaren Verbindung Download PDF

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Publication number
EP0569074A1
EP0569074A1 EP93201135A EP93201135A EP0569074A1 EP 0569074 A1 EP0569074 A1 EP 0569074A1 EP 93201135 A EP93201135 A EP 93201135A EP 93201135 A EP93201135 A EP 93201135A EP 0569074 A1 EP0569074 A1 EP 0569074A1
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EP
European Patent Office
Prior art keywords
compound
silica
dispersion
solution
precipitation
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.)
Granted
Application number
EP93201135A
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English (en)
French (fr)
Other versions
EP0569074B1 (de
Inventor
Hubert C/O Agfa-Gevaert N.V. Vandenabeele
Hendrik c/o Agfa-Gevaert N.V. Lambrecht
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Agfa Gevaert NV
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Agfa Gevaert NV
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Publication of EP0569074A1 publication Critical patent/EP0569074A1/de
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Classifications

    • 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
    • G03C7/388—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor
    • 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
    • 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
    • G03C5/16—X-ray, infrared, or ultraviolet ray processes
    • G03C5/17—X-ray, infrared, or ultraviolet ray processes using screens to intensify X-ray images

Definitions

  • One general suitable dispersion method consists of ball-milling the compound in gelatinous medium. It is also possible to disperse an organic solution of the compound in an aqueous gelatinous medium followed by removal of the solvent e.g. by evaporation under vacuum.
  • fine silica dispersions of dyes can be prepared for incorporation in at least one of the layers of a photographic material e.g. as filter, screening or antihalation dye, thereby showing an increased efficiency of light absorption, requiring a reduced coating amount of a dye and showing a high decolouration speed in the processing of said photographic material, making it particularly suitable for rapid processing applications.
  • a photographic material e.g. as filter, screening or antihalation dye
  • Silica is well-known as suitable hydrophilic binder for replacing gelatin in hydrophilic layers and more particularly in silver-halide emulsion layers. As has been disclosed in EP Application No 91.202082/3 an increased amount of silica sol used as a protective colloid in the preparation of silver halide emulsions results in an acceptable physical stability of the emulsion after coating.
  • silica and/or dispersing agent(s) may be divided partially between the reaction vessel and the solution(s) to be added to said vessel.
  • pH-stat it is possible to measure the pH value in the vessel continuously with a glass electrode and to derive the rate of addition of the acidic aqueous solution therefrom electronically so that it is possible to conduct this acidifying step in perfectly controlled conditions.
  • This preferably constant value should be low enough to get a quantitative flocculate of the compound e.g. dye, a pH value lower than 6.0 being recommended and a value of about 3.0 being particularly preferred.
  • the rate of addition of the alkaline solution strongly depends on the concentration of the alkaline solution, of the stirring rate and of the constant pH value to be maintained in the reaction vessel. The rate of addition of the alkaline solution to the reaction vessel and/or the stirring rate in the vessel may be increased during the precipitation procedure.
  • the pH precipitation value can be chosen beforehand. It is clear that the preferred rate of addition of the aqueous alkaline solution also depends on the pH value of the aqueous alkaline solution of the compound or compounds and on the stirring rate in the vessel. Amounts of silica present in the reaction vessel with relation to the amount of compound may vary from weight ratios of 5/1 to 1/5.
  • the ultrafiltration technique is preferred: in about half an hour it is possible to get a stable silica dispersion concentrated to about 6% and even to about 10% by weight for the compound although these higher values are not recommended as the viscosity may rise and as afterwards a dilution may become necessary before addition to coating compositions.
  • aqueous-insoluble compounds as e.g. colour couplers without an ionizable soluble group are dissolved in a minimum amount of an organic solvent and added to an aqueous alkaline solution.
  • the solution is slowly added, simultaneously with a neutralizing acidic solution to a reaction vessel containing a stirred aqueous dispersion of silica particles wherein preferably a suitable dispersing agent is present.
  • These additions are preferably performed under partially or fully controlled stirring conditions of temperature, concentration, sequence of addition, and rates of addition. It should be recommended to perform this precipitation in the presence of at least one polymer and/or surfactant present in the reaction vessel to get a finely dispersed compound in a stable colloidal medium.
  • Said dispersing agent may be chosen from the classes of chemical compounds known as partially ionizable polymers and surfactants and may act as a synergetically working co-stabilizer. Any combination may be used to optimize the stabilization of the silica particle dispersion of the organic compound obtained.
  • the preparation procedure described hereinbefore may be applied to prepare fine, stable and homogeneous silica dispersions for all organic compounds that are normally used in dissolved or finely divided state in the coated layers of photographic materials as e.g. spectrally sensitizing or desensitizing dyes, stabilizers, developers or developer accelerators, coupler compounds as DIR-couplers, coloured mask couplers and couplers, being coloured or uncoloured after coupling reactions with oxidised developer compounds as those used in colour photographic materials, coupler precursors etc.
  • heterocyclic nitrogen-containing compounds such as benzothiazolium salts, nitroimidazoles, nitrobenzimidazoles, chlorobenzimidazoles, bromobenzimidazoles, mercaptothiazoles, mercaptobenzothiazoles, mercaptobenzimidazoles, mercaptothiadiazoles, aminotriazoles, benzotriazoles (preferably 5-methyl-benzotriazole), nitrobenzotriazoles, mercaptotetrazoles, in particular 1-phenyl-5-mercapto-tetrazole, mercaptopyrimidines, mercaptotriazines, benzothiazoline-2-thione.
  • benzothiazolium salts such as benzothiazolium salts, nitroimidazoles, nitrobenzimidazoles, chlorobenzimidazoles, bromobenzimidazoles, mercaptothiazoles, mercaptobenzothiazoles, mercaptobenzimidazoles
  • silica dispersions in hydrophilic layers are e.g. developing agents as dihydroxy benzene or derivatives, phenidones and the like, whether or not in combination with other organic compounds used in developers as e.g. stabilizers as benztriazole and/or indazole or benzimidazole derivatives.
  • Such an absorber dye can e.g. be present in one or more filter layers between silver halide emulsion layers that are coated at opposite sides of a transparent film support of a duplitized X-ray recording material in order to improve image sharpness.
  • the imagewise exposure of said recording material proceeds in a cassette between a pair of X-ray intensifying screens that each are held in contact with an adjacent silver halide emulsion layer.
  • SILICA B The dispersion called SILICA B was made in the presence of an amphoteric surfactant corresponding to the formula given hereinafter (surfactant 1). During the preparation of said dispersion the procedure was followed as for SILICA A except for the further presence of surfactant 1 in the reaction vessel. Nanosizer measurements gave an average particle diameter of 320 nm.
  • a silica dispersion was made from dye 2, the formula of which is given hereinafter, in a vessel containing aqueous silica sol 'Kieselsol 500' (product of Bayer AG) by the addition of an alkaline solution of dye 2 the pH value of which was adjusted at 11.5 at a constant rate of addition and the simultaneous addition of a citric acid solution at a constant pH value of 3.0.
  • the dispersion called SILICA C had an average particle diameter of 175 nm.
  • Said dyes being coated on both sides of a polyethylene terephthalate film support in an anti cross-over layer were overcoated with an emulsion and a protective layer, the silver halide emulsion being spectrally unsensitized.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Colloid Chemistry (AREA)
EP19930201135 1992-05-04 1993-04-20 Verfahren zur Herstellung einer wässrigen Dispersion von festen Teilchen einer photographisch verwendbaren Verbindung Expired - Lifetime EP0569074B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP92201228 1992-05-04
EP92201228 1992-05-04

Publications (2)

Publication Number Publication Date
EP0569074A1 true EP0569074A1 (de) 1993-11-10
EP0569074B1 EP0569074B1 (de) 1998-10-14

Family

ID=8210585

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19930201135 Expired - Lifetime EP0569074B1 (de) 1992-05-04 1993-04-20 Verfahren zur Herstellung einer wässrigen Dispersion von festen Teilchen einer photographisch verwendbaren Verbindung

Country Status (3)

Country Link
EP (1) EP0569074B1 (de)
JP (1) JP3222266B2 (de)
DE (1) DE69321514T2 (de)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0704749A1 (de) * 1994-09-27 1996-04-03 Agfa-Gevaert N.V. Verfahren zur Herstellung von lichtempfindlichen Silberhalogenidemulsionen und Dispersionen von photographisch verwendbaren Verbindungen
EP0720046A2 (de) * 1994-12-29 1996-07-03 Eastman Kodak Company Verfahren zur Pufferung von konzentrierten wässerigen Aufschlämmungen
EP0790526A1 (de) 1996-02-19 1997-08-20 Agfa-Gevaert N.V. System von Film und Schirm zur Herstellung radiographischen Bildes
US5994041A (en) * 1985-04-06 1999-11-30 Eastman Kodak Company Process for buffering concentrated aqueous slurries

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2835711B2 (ja) * 1995-07-24 1998-12-14 アグファ・ゲヴェルト・ナームロゼ・ベンノートチャップ 写真材料の親水性層の被覆溶液にすぐ使用できる写真的に有用な化合物の分散体の製造方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5079134A (en) * 1989-06-01 1992-01-07 Fuji Photo Film Co., Ltd. X-ray photographic material

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5079134A (en) * 1989-06-01 1992-01-07 Fuji Photo Film Co., Ltd. X-ray photographic material

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5994041A (en) * 1985-04-06 1999-11-30 Eastman Kodak Company Process for buffering concentrated aqueous slurries
EP0704749A1 (de) * 1994-09-27 1996-04-03 Agfa-Gevaert N.V. Verfahren zur Herstellung von lichtempfindlichen Silberhalogenidemulsionen und Dispersionen von photographisch verwendbaren Verbindungen
US5627019A (en) * 1994-09-27 1997-05-06 Agfa-Gevaert, N.V. Method of preparing light-sensitive silver halide emulsions and dispersions of photographically useful compounds
EP0720046A2 (de) * 1994-12-29 1996-07-03 Eastman Kodak Company Verfahren zur Pufferung von konzentrierten wässerigen Aufschlämmungen
EP0720046A3 (de) * 1994-12-29 1996-07-24 Eastman Kodak Co
US5609998A (en) * 1994-12-29 1997-03-11 Eastman Kodak Company Process for dispersing concentrated aqueous slurries
US5750321A (en) * 1994-12-29 1998-05-12 Eastman Kodak Company Process for buffering concentrated aqueous slurries
EP0790526A1 (de) 1996-02-19 1997-08-20 Agfa-Gevaert N.V. System von Film und Schirm zur Herstellung radiographischen Bildes

Also Published As

Publication number Publication date
DE69321514D1 (de) 1998-11-19
JPH06194763A (ja) 1994-07-15
DE69321514T2 (de) 1999-05-27
EP0569074B1 (de) 1998-10-14
JP3222266B2 (ja) 2001-10-22

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