EP0046247B1 - Procédé pour la fabrication de dispersions et matériaux photographiques - Google Patents

Procédé pour la fabrication de dispersions et matériaux photographiques Download PDF

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Publication number
EP0046247B1
EP0046247B1 EP81106196A EP81106196A EP0046247B1 EP 0046247 B1 EP0046247 B1 EP 0046247B1 EP 81106196 A EP81106196 A EP 81106196A EP 81106196 A EP81106196 A EP 81106196A EP 0046247 B1 EP0046247 B1 EP 0046247B1
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EP
European Patent Office
Prior art keywords
dispersion
solution
active substance
phase
organic phase
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
Application number
EP81106196A
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German (de)
English (en)
Other versions
EP0046247A1 (fr
Inventor
Hildegard Dr. Schnöring
Karl-Wilhelm Dr. Schranz
Günther Dr. Koepke
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.)
Agfa Gevaert AG
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Agfa Gevaert AG
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Publication of EP0046247A1 publication Critical patent/EP0046247A1/fr
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    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
    • B01F23/00—Mixing according to the phases to be mixed, e.g. dispersing or emulsifying
    • B01F23/40—Mixing liquids with liquids; Emulsifying
    • B01F23/49—Mixing systems, i.e. flow charts or diagrams
    • 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

Definitions

  • the invention relates to a process for the production of dispersions and photographic materials which contain dispersions according to the invention.
  • the invention relates to the production of dispersions of organic, hydrophobic substances in an aqueous phase.
  • dispersions are understood to mean apparently homogeneous systems which contain at least 2 phases in finely divided form and in which the particles of the phases are larger than 1 nm.
  • examples of dispersions are e.g. B. emulsions and suspensions.
  • emulsified is also common in the photographic field.
  • a water-in-oil emulsion can be prepared from the dissolution of a color coupler in a low-boiling solvent by adding water, which emulsion can be converted into an oil by adding more water by phase reversal -can be converted into water emulsion.
  • This oil-in-water emulsion must be stabilized by adding a binder.
  • a disadvantage of the known processes is that it is very difficult to produce highly concentrated Disgate in a binder in a fine phase distribution without the use of low-boiling solvents in one operation.
  • the object of the invention is to find a dispersion process which avoids the disadvantages of the known processes.
  • the invention is based on the object of specifying a dispersion process which, at a high concentration and without the use of low-boiling solvents, ensures a fine distribution of the dispersed compounds in a binder.
  • a process has now been found for producing dispersions from at least one liquid organic phase which contains a hydrophobic, photographically active compound and at least one aqueous phase, in which the two phases are combined with dispersion.
  • the organic phase is initially introduced and the aqueous phase is added to it with dispersion until an oil-in-water emulsion is formed from the water in oil emulsion initially formed by reversing the phase.
  • the phase is reversed, the viscosity exceeds a maximum.
  • the organic phase preferably contains a substance which is essentially immiscible with water at pH 7, in particular a photographically active substance.
  • a preferably high-boiling oil former can be contained in a preferred embodiment.
  • phase inversion method is used e.g. B. in the literature in Ullmann, Encyclopedia of Industrial Chemistry, Vol. 10, page 454 or in Stache, Tensid-Taschenbuch, Hanser-Verlag 1979, page 180 ff.
  • phase reversal method for the production of dispersions with photographically active substances from oil-soluble photographic additives or the melted oil-soluble additive or its pure melt in an aqueous binder solution with active substances is not obvious to the person skilled in the art, because this phase reversal method requires that both phases last longer under high shear must be at temperatures which exceed the higher of the condensing temperatures of both phases. Therefore, on the basis of the generally accepted teaching opinion, the person skilled in the art must assume that the structure of the binders is destroyed under these circumstances by the combined thermal and mechanical stress until the binders become ineffective.
  • the process according to the invention is outstandingly suitable for producing dispersions in an aqueous medium from organic hydrophobic substances which are photographically active.
  • organic hydrophobic substances which are photographically active.
  • hydrophobic couplers of various types (4-equivalent couplers, 2-equivalent couplers, DIR couplers, mask couplers, white couplers, Competitive couplers), dyes or other coloring compounds, e.g. B. for the color diffusion transfer process, UV absorbers, stabilizers and other photographic additives.
  • the aqueous phase preferably contains, to improve the stability of the dispersions, hydrophilic colloidal binders, e.g. B. gelatin.
  • hydrophilic colloidal binders e.g. B. gelatin.
  • the gelatin can also be replaced in whole or in part by other natural, synthetic or semi-synthetic binders, e.g. B. by derivatives of alginic acid or cellulose, by polyvinyl alcohol, polyacrylates, partially saponified polyvinyl acetate or polyvinyl pyrrolidone.
  • the gelatin acts as a dispersing aid, it is not absolutely necessary. So you can also make a fine stock dispersion with z. B. a particle size of 320 nm.
  • the gelatin causes a finer particle size distribution in the aqueous phase.
  • the concentration of organic phase required for phase reversal with gelatin can also be reduced without an increase in the particle size being observed.
  • the gelatin concentration can be used to control the particle size, since a higher gelatin concentration leads to a smaller particle size.
  • the dispersion temperature has little or no influence on the fine distribution. At lower temperatures and thus a higher viscosity of the organic phase, somewhat finer particle size distributions result.
  • the preferred temperature range for the organic phase is 50 to 90 ° C, at dissolving temperatures of 100 to 140 ° C.
  • the aqueous phase is advantageously kept at 50 to 90 ° C.
  • the dispersion takes place at normal pressure, but could also take place under pressure if higher temperatures (e.g. for products with higher liquefaction temperatures) should make this necessary.
  • the average particle size in the dispersions obtained is a function of the residence time, mixing performance and dispersion temperature. In general, the influence of the residence time decreases with higher mixing performance. At higher temperatures, finer dispersions can generally be obtained than at lower temperatures. In principle, any particle sizes can be obtained, particle sizes from 200 to 800 nm, in particular from 300 to 350 nm, are particularly preferred.
  • relatively temperature-sensitive substances can also be dispersed in the dispersing device at high temperatures.
  • a major technical advance of the process according to the invention is that such highly concentrated (up to 70%) dispersions of high fineness can be produced, whereas according to the conventional process, the experience with the various systems, the lower the dispersion fineness, the higher the concentration is disperse phase. Conventionally produced emulsions for the photographic areas therefore hardly have a 20% disperse phase.
  • Another surprising technical advantage is that to achieve the required fineness (usually in the range between 100 to 500 nm), substantially simpler dispersing devices with substantially less energy input are sufficient.
  • oil generator high-boiling solvent such as tricresyl phosphate, dibutyl phthalate
  • oil generator high-boiling solvent such as tricresyl phosphate, dibutyl phthalate
  • the ratio of organic matter (color coupler, UV absorber, etc.) to oil former is not a critical parameter for the success of the process.
  • the oil former high-boiling solvent
  • the oil former is not absolutely necessary, but it is advantageous not to exceed the viscosity of 1,000 mPas at the preferred dispersion temperature. A corresponding setting is possible by adding oil formers.
  • the oil formers are substances which generally boil above 180 ° C. and have good dissolving power for the hydrophobic substance to be dispersed.
  • the esters of glutaric acid, adipic acid, phthalic acid, sebacic acid, succinic acid, maleic acid, fumaric acid, isophthalic acid, terephthalic acid and phosphoric acid or the esters of glycerol, as well as paraffin and fluorinated paraffin are preferably used because these compounds are chemically stable and very easily accessible, very much can be handled easily and have no adverse effect on the light-sensitive materials when the dispersions are used for photographic purposes.
  • oil formers are particularly preferably used as oil formers: tricresyl phosphate, triphenyl phosphate, dibutyl phthalate, di-n-octyl phthalate, di-2-ethylhexyl phthalate, glycerol tributyrate, glycerol tripropionate, dioctyl sebacate. Paraffin and fluorinated paraffin. Examples of the preferred oil formers are given below.
  • the further processing of the binder-containing dispersion can be carried out by conventional methods, for. B. it can be gelled on cooling belts and transferred through a perforated grid into a noodle shape and stored in refrigerated cellars.
  • the high concentration of the photographically active disperse phase requires a corresponding increase in the space / time yield and a reduction in the storage volume and the cooling costs.
  • the highly concentrated dispersate obtained can also be diluted with an aqueous binder-containing solution and / or a silver halide-containing photographic emulsion while maintaining the particle size.
  • these dispersions are in dry emulsions with good storage stability and good solubility and redispersibility, for. B. after the usual drying process for gelatin with a belt drying process, for. B. according to a method as described in US-A-2801 171, can be transferred, especially when the concentration of the hydrophilic binder, based on an aqueous phase, is between 10 and 25%.
  • the economic advantage of drying such highly concentrated and therefore low-water Emulgate is obvious.
  • Fig. 1 shows a useful device with a stirred tank 1, in which a solution of gelatin, water and emulsifier is prepared.
  • a solution of color coupler and oil former is produced at 100 to 140 ° C.
  • This stirred tank 2 also serves as a storage tank and is equipped with a Kotthoff mixing siren 3.
  • the boiler 1 is equipped with a stirrer 4.
  • gelatin, water and emulsifier can be added via the feed lines 5, 6 and 7.
  • oil formers and couplers can be added via the feed lines.
  • the inflow and outflow can be regulated via the valves 10.
  • Particularly fine dispersions are obtained if the phase reversal is moved to the shear zone. This can be done according to FIG. 2.
  • the aqueous phase of water 5, gelatin 6 and emulsifier 7 is prepared in a stirred tank 1 which is equipped with a stirrer 4.
  • the organic phase consisting of oil former 8 and color coupler 9 is placed in a stirred tank 2 equipped with a stirrer 4.
  • a water-in-oil emulsion is prepared by adding the solution from 1 to 2.
  • This water-in-oil emulsion is converted into an oil-in-water emulsion by a dispersing machine 11 by using appropriate shear forces, which is available in a boiler 12 for further use.
  • the dispersions prepared according to the invention are outstandingly suitable for the preparation of light-sensitive photographic materials which contain silver halide.
  • the dispersions can be introduced into such materials in a manner known per se.
  • the dispersions can be introduced both in layers containing silver halide and in layers free of silver halide.
  • the usual silver halide emulsions can be used, which can be prepared by the customary known methods. Gelatin can be used as a binder for the photographic layers, but can be replaced in whole or in part by other binders.
  • stabilizers such as e.g. B. triazole derivatives, thiocarbonic acid derivatives of thiodiazole or azaindenes can be added.
  • the silver halide emulsions can also be sensitized with the usual chemical sensitizers; for optical sensitization, the usual sensitizers, as described for example in the work of S.M. Hamer "The Cyanine Dyes and Related Compounds" (1964), Intersience Publishers John Wiley & Sons.
  • the photographic layers are hardened under conditions which do not adversely affect the image tone, but which allow the layers to be processed quickly even at higher temperatures.
  • Suitable curing agents are, for example, formalin, dialdehydes, divinyl sulfone, triazine derivatives, if appropriate in the presence of tertiary amines, and also instant curing agents such as carbamoylpyridinium compounds or carbodiimides.
  • the usual substrates can be used, e.g. B. polyolefin-laminated underlays, for example polyethylene-coated paper, suitable polyolefins and paper, and also polyester underlays and triacetate-based films.
  • the average droplet size of the dispersion is 350 nm. A 35% dispersion is obtained.
  • the concentrated color coupler dispersion prepared according to Example 1 is blended at 40 ° C. with 520 kg i 25% gelatin solution.
  • the emulsifier formed is dried using methods known per se according to US Pat. No. 2,801,171.
  • the concentrated color coupler dispersion prepared according to Example 1 is mixed with 1,200 kg of a solution of 120 kg of gelatin and 4.8 kg of phenol in 1,075.2 kg of water at 40 ° C. and then converted into a gel form by cooling to 4 ° C. After storage, the gel is dissolved in 2680 kg of a solution of 78 kg of gelatin and 10.8 kg of phenol in 2 591.2 kg of water at 40 ° C. in use.
  • the concentrated color coupler dispersion prepared according to Example 1 is mixed at 40 ° C. with 3,879.5 kg of a solution of 198 kg of gelatin and 12.5 kg of phenol in 3,669 kg of water.
  • the solution can be directly processed further by adding to a photographic silver halide emulsion or by cooling in the gel form and stored until use.
  • FIG. 1 268.1 kg of 10% gelatin solution are prepared according to a known procedure, introduced at 60 ° C. and 9.325 4 kg of emulsifier (75%) of the type of a straight-chain alkylbenzenesulfonate are introduced (aqueous phase).
  • the initial water / oil dispersion produces an oil / water dispersion which is recirculated for 30 minutes using a Knollenberg high-pressure homogenizer at 3,000 l / h at 200 bar.
  • the average particle size is 310 nm. A 14% dispersion is obtained.
  • the concentrated color coupler dispersion prepared according to Example 2 is mixed with the appropriate amount of a silver halide emulsion to form the ready-to-pour photographic emulsion and poured in after the usual additives have been added.
  • the concentrated color coupler dispersion produced according to Example 2 is blended at 40 ° C. with 324 kg of 25% gelatin solution.
  • the resulting emulsifier is dried using methods known per se.
  • the batch is converted into a gel form by cooling to 4 ° C. and stored at 10 ° C. until used.
  • a color coupler melt is made from 350 g coupler of the formula 150 g coupler of the formula and 400 g of tricresyl phosphate at 140 ° C and then cooled to 60 ° C.
  • a solution of 300 g of water and 22.5 g of triisopropylnaphthalenesulfonate at 60 ° C. is added to this solution within 2 minutes.
  • the emulsion is homogenized for 15 minutes with a high pressure homogenizer of the gan pump type at 150 to 200 bar.
  • a 74% dispersion with a particle size of 310 nm is obtained.
  • An organic phase is produced as in example 3a.
  • a solution of 60 g of 250 g of 10% gelatin solution containing 22.5 g of triisopropylnaphthalenesulfonate is added to this solution within 2 minutes.
  • the emulsion is homogenized for 15 minutes with a high pressure homogenizer of the gan pump type at 150-200 bar.
  • a dispersion with a particle size of 270 nm is obtained.
  • a disc stirrer with a diameter of 60 mm and a rotation frequency of 1,000 min -1 is used as the stirrer.
  • a 95 ° C hot mixture of 2.0 kg gelatin solution 10% and 0.07 kg trilsopropylnaphthalene sulfonate with a material flow of 20 kg / h is metered into a heated and stirred open receiver in this kettle by means of a gear metering pump.
  • a finely divided dispersion with an average particle size of 550 nm and a concentration of 14% is formed.
  • 300 g of tricresyl phosphate are heated to 140 ° C. in a second kettle and 300 g of 1- (2 ', 4', 6'-trichlorophenyl) -3- (3 "- ⁇ - [2" ', 4 "' - di -tert.-amylphenoxy] -butyramido) -benzamido-5-pyrazolone; 300 g 1- (2 ', 4', 6'-trichlorophenyl) -3- [2 "-chloro-5" -cetyloxicarbonylamido) -anilino] - 5-pyrazolone stirred in and dissolved.
  • the mixture is cooled to 80 ° C. and the contents of kettle 1 are added to the contents of kettle 2 with stirring and recirculated for 12 minutes using a Manton Gaulin high-pressure homogenizer 3 at 200 to 250 bar.
  • a dispersion with an average particle size of 350 nm and a concentration of 38% is obtained.
  • the emulsified product is then gelled on a cooling belt and stored at + 10 ° C until further processing.
  • the dispersant obtained is added to a silver halide emulsion containing 60 g / l of silver halide in a manner known per se.
  • the dispersion thus obtained is provided with hardening and wetting agents and cast onto a base in a known manner.
  • the material obtained is exposed imagewise and developed in a conventional color developer.
  • the comparison material was processed in the same way as that of the invention.
  • the sensitometric data listed in the table below show that, according to the invention, a higher sensitivity, gradation and maximum density is obtained.
  • Example 6a An organic phase is prepared as in Example 6a. However, 1.884 kg of emulsifier are used with the 12% gelatin solution. The resulting dispersion has a particle size of 475 nm.
  • An organic phase is prepared as in Example 6a. However, a 20% gelatin solution and 1.884 kg emulsifier are used. The resulting dispersion has a particle size of 404 nm.
  • An organic phase is prepared as in Example 6a.
  • a 20% gelatin solution and 1.884 kg emulsifier are used. However, the phase reversal takes place at circumferential speeds of 23 m / s.
  • the resulting dispersion has a particle size of 385 nm.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Colloid Chemistry (AREA)

Claims (10)

1. Procédé de préparation de dispersions à partir d'au moins une phase organique liquide contenant une substance hydrophobe photographiquement active, ainsi que d'au moins une phase aqueuse liquide en chargeant ensemble les phases avec formation d'une dispersion dans un dispositif de dispersion, caractérisé en ce qu'on dépose préalablement la phase organique et on ajoute la phase aqueuse à cette dernière avec formation d'une dispersion jusqu'à ce que, après avoir dépassé un maximum de viscosité, on obtienne une inversion de phases en une dispersion de la phase organique dans la phase aqueuse.
2. Procédé suivant la revendication 1, caractérisé en ce que la phase organique est la masse fondue pure d'une substance photographiquement active, tandis que la dispersion a lieu au-delà de la température de liquéfaction de cette substance photographiquement active.
3. Procédé suivant la revendication 1, caractérisé en ce que la phase organique est la solution d'une substance photographiquement active dans un agent formateur d'huile (solvant à point d'ébullition élevé), tandis que la dispersion a lieu au-delà de la température de liquéfaction de cette solution.
4. Procédé suivant la revendication 1, caractérisé en ce que la phase aqueuse contient des agents liants dissous, tandis que la dispersion a lieu au-delà de la température de liquéfaction de cette solution d'agent liant.
5. Procédé suivant la revendication 1, caractérisé en ce que la phase aqueuse est une solution de gélatine.
6. Procédé suivant les revendications 1 à 5, caractérisé en ce que la dispersion de la phase organique et de la phase aqueuse dans laquelle sont dissous des agents liants, a lieu à une température supérieure aux températures de liquéfaction des deux phases.
7. Procédé suivant la revendication 1, caractérisé en ce que la substance photographiquement active est un copulant chromogène.
8. Procédé suivant la revendication 1, caractérisé en ce que la substance photographiquement active est un agent absorbant les rayons ultraviolets.
9. Procédé suivant la revendication 1, caractérisé en ce que la substance photographiquement active est un agent stabilisant.
- 10. Elément photographique constitué d'un support de couche, d'au moins une couche d'émulsion à l'halogénure d'argent et éventuellement d'autres couches, caractérisé en ce qu'au moins une couche contient une dispersion préparée conformément à la revendication 1.
EP81106196A 1980-08-20 1981-08-07 Procédé pour la fabrication de dispersions et matériaux photographiques Expired EP0046247B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3031404 1980-08-20
DE19803031404 DE3031404A1 (de) 1980-08-20 1980-08-20 Verfahren zur herstellung von dispersionen und fotografische materialien

Publications (2)

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EP0046247A1 EP0046247A1 (fr) 1982-02-24
EP0046247B1 true EP0046247B1 (fr) 1983-09-14

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EP81106196A Expired EP0046247B1 (fr) 1980-08-20 1981-08-07 Procédé pour la fabrication de dispersions et matériaux photographiques

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US (1) US4378425A (fr)
EP (1) EP0046247B1 (fr)
JP (1) JPS5778038A (fr)
DE (2) DE3031404A1 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59203632A (ja) * 1983-05-06 1984-11-17 Fuji Photo Film Co Ltd 乳化方法
JPH0642043B2 (ja) * 1986-04-10 1994-06-01 富士写真フイルム株式会社 固体粒子膜の形成方法
DE3613974C2 (de) * 1986-04-25 1996-01-25 Agfa Gevaert Ag Farbfotografisches Aufzeichnungsmaterial
US5008179A (en) * 1989-11-22 1991-04-16 Eastman Kodak Company Increased activity precipitated photographic materials
US5411715A (en) * 1992-06-09 1995-05-02 Eastman Kodak Company Apparatus for preparing aqueous amorphous particle dispersions of high-melting microcrystalline solids
US5272045A (en) * 1992-11-13 1993-12-21 Sun Chemical Corporation Water soluble antifoggant for powder developer solutions
US5505713A (en) * 1994-04-01 1996-04-09 Minimed Inc. Indwelling catheter with stable enzyme coating
EP0729061B1 (fr) * 1995-02-24 1999-05-06 Fuji Photo Film Co., Ltd. Procédé d'émulsification et de dispersion d'un composé hydrophobe utilisable en photographie
JP2001027795A (ja) * 1999-05-11 2001-01-30 Fuji Photo Film Co Ltd 水不溶性写真有用化合物の水性分散物または溶融物、それらの製造方法、塗布用組成物およびハロゲン化銀写真感光材料

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB636102A (en) * 1940-02-28 1950-04-26 Minnesota Mining & Mfg Improvements in or relating to adhesive dispersions of the oil-in-water type, and processes of preparing the same
BE543744A (fr) * 1954-12-20
GB1272561A (en) * 1968-09-10 1972-05-03 Agfa Gevaert Method of incorporating photographic ingredients into colloid compositions
GB1346426A (en) * 1970-08-13 1974-02-13 Agfa Gevaert Incorporating photographic compounds into hydrophilic colloids
JPS5224412B2 (fr) * 1971-08-25 1977-07-01
DE2410914A1 (de) * 1974-03-07 1975-09-18 Agfa Gevaert Ag Einlagerungsverfahren
JPS55129136A (en) * 1979-03-27 1980-10-06 Fuji Photo Film Co Ltd Emulsifying method

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DE3160876D1 (en) 1983-10-20
JPS5778038A (en) 1982-05-15
EP0046247A1 (fr) 1982-02-24
US4378425A (en) 1983-03-29
DE3031404A1 (de) 1982-04-01

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