EP0569074A1 - Procédé de préparation d'une dispersion aqueuse de particules solides d'un composé utilisable en photographie - Google Patents
Procédé de préparation d'une dispersion aqueuse de particules solides d'un composé utilisable en photographie Download PDFInfo
- 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
- Authority
- 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
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- 235000019260 propionic acid Nutrition 0.000 description 1
- UGZVCHWAXABBHR-UHFFFAOYSA-O pyridin-1-ium-1-carboxamide Chemical class NC(=O)[N+]1=CC=CC=C1 UGZVCHWAXABBHR-UHFFFAOYSA-O 0.000 description 1
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical class SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000000837 restrainer Substances 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- JJJPTTANZGDADF-UHFFFAOYSA-N thiadiazole-4-thiol Chemical class SC1=CSN=N1 JJJPTTANZGDADF-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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.
Landscapes
- 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)
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 (fr) | 1993-11-10 |
| EP0569074B1 EP0569074B1 (fr) | 1998-10-14 |
Family
ID=8210585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP19930201135 Expired - Lifetime EP0569074B1 (fr) | 1992-05-04 | 1993-04-20 | Procédé de préparation d'une dispersion aqueuse de particules solides d'un composé utilisable en photographie |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0569074B1 (fr) |
| JP (1) | JP3222266B2 (fr) |
| DE (1) | DE69321514T2 (fr) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0704749A1 (fr) * | 1994-09-27 | 1996-04-03 | Agfa-Gevaert N.V. | Procédé de préparation d'émulsions à l'halogénure d'argent sensibles à la lumière et dispersions de composés utiles en photographie |
| EP0720046A2 (fr) * | 1994-12-29 | 1996-07-03 | Eastman Kodak Company | Procédé de tamponnage de boues aqueuses concentrées |
| EP0790526A1 (fr) | 1996-02-19 | 1997-08-20 | Agfa-Gevaert N.V. | Système pellicule-écran formant image radiographique |
| US5994041A (en) * | 1985-04-06 | 1999-11-30 | Eastman Kodak Company | Process for buffering concentrated aqueous slurries |
Families Citing this family (1)
| 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)
| 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 |
-
1993
- 1993-04-20 DE DE1993621514 patent/DE69321514T2/de not_active Expired - Fee Related
- 1993-04-20 EP EP19930201135 patent/EP0569074B1/fr not_active Expired - Lifetime
- 1993-04-30 JP JP12833993A patent/JP3222266B2/ja not_active Expired - Fee Related
Patent Citations (1)
| 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)
| 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 (fr) * | 1994-09-27 | 1996-04-03 | Agfa-Gevaert N.V. | Procédé de préparation d'émulsions à l'halogénure d'argent sensibles à la lumière et dispersions de composés utiles en photographie |
| 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 (fr) * | 1994-12-29 | 1996-07-03 | Eastman Kodak Company | Procédé de tamponnage de boues aqueuses concentrées |
| EP0720046A3 (fr) * | 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 (fr) | 1996-02-19 | 1997-08-20 | Agfa-Gevaert N.V. | Système pellicule-écran formant image radiographique |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3222266B2 (ja) | 2001-10-22 |
| JPH06194763A (ja) | 1994-07-15 |
| DE69321514T2 (de) | 1999-05-27 |
| EP0569074B1 (fr) | 1998-10-14 |
| DE69321514D1 (de) | 1998-11-19 |
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