EP0049399B1 - Verfahren zur Herstellung von Dispersionen hydrophober Farbkuppler in Wasser sowie deren Verwendung bei der Herstellung lichtempfindlicher Aufzeichnungsmaterialien - Google Patents

Verfahren zur Herstellung von Dispersionen hydrophober Farbkuppler in Wasser sowie deren Verwendung bei der Herstellung lichtempfindlicher Aufzeichnungsmaterialien Download PDF

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Publication number
EP0049399B1
EP0049399B1 EP81107366A EP81107366A EP0049399B1 EP 0049399 B1 EP0049399 B1 EP 0049399B1 EP 81107366 A EP81107366 A EP 81107366A EP 81107366 A EP81107366 A EP 81107366A EP 0049399 B1 EP0049399 B1 EP 0049399B1
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EP
European Patent Office
Prior art keywords
dispersions
acid
water
dispersion
coupler
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
EP81107366A
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German (de)
English (en)
French (fr)
Other versions
EP0049399A3 (en
EP0049399A2 (de
Inventor
Günter Dr. Helling
Helmut Dr. Reiff
Wolfgang Dr. Himmelmann
Günter Dr. Renner
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Agfa Gevaert AG
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Agfa Gevaert AG
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Publication date
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Publication of EP0049399A2 publication Critical patent/EP0049399A2/de
Publication of EP0049399A3 publication Critical patent/EP0049399A3/de
Application granted granted Critical
Publication of EP0049399B1 publication Critical patent/EP0049399B1/de
Expired legal-status Critical Current

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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
    • 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
    • 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
    • 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
    • G03C7/3882—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor characterised by the use of a specific polymer or latex

Definitions

  • the invention relates to a process for the production of dispersions of hydrophobic color couplers with the aid of polyurethanes and the use of such dispersions for the production of light-sensitive recording layers.
  • DE-OS 1812 578 it is known to dissolve color couplers in an emulsion copolymer of styrene / butadiene, acrylonitrile / butadiene or vinyl chloride / vinylidene chloride and to add this solution to a photographic emulsion.
  • DE-OS 2 541 230 relates to a method for loading polymer particles, which are in the form of a polymer latex, with hydrophobic substances by mixing the latex with a solution of the hydrophobic substance in a water-miscible solvent.
  • a photographic material which contains an anionic polyurethane in one or more of its gelatin layers, in which a water-insoluble optical brightener is contained.
  • the amount of the optical brightener which can be introduced into the gelatin layer with the aid of the polyurethane is limited to a maximum of 5% by weight.
  • polyurethanes are described in mixtures of high-boiling and low-boiling solvents for introducing photographic additives into photographic pouring solutions.
  • a disadvantage of the process is the additional loading of the photographic layers thus produced with the high-boiling solvents.
  • the ballast of high-boiling solvents hinders the formation of thin layers, as are required for recordings with high sharpness.
  • the precipitation dispersion process used here according to Angew. Macromol. Chem., 72 (1978), p. 115 ff. Requires considerable amounts of auxiliary solvents if it is to lead to reasonably fine-grain dispersions. This considerably limits the economic usability of the process.
  • the polyurethane latexes known from European patent application 0014921 and loaded with hydrophobic compounds are produced by loading the finished polymer dispersion, the particle size of which is therefore already fixed.
  • a disadvantage of this procedure is that the particles are enlarged by the loading process. This gives dispersions which are coarser than the starting dispersions and which therefore tend to sediment and can cloud the photographic layers.
  • the object of the invention is to develop a method which enables the production of stable, fine-grained dispersions of hydrophobic substances in water with the least possible technical outlay.
  • the invention relates to a process for the preparation of dispersions of hydrophobic substances in water by loading a polyurethane which is ionomeric and contains 4 to 180 milliequivalents per 100 g of ionic groups or groups which can be converted into ionic groups and / or which contains 1 to 20% by weight. % of alkylene oxide units of the formula ⁇ CH 2 ⁇ CH 2 ⁇ O ⁇ built into a polyether chain, by dissolving the polyurethane together with the hydrophobic substance in an organic, water-miscible solvent with a boiling point below 120 ° C.
  • the polyether chain can be contained laterally or in the main chain.
  • the polyurethanes which can be used according to the invention include polyurethanes and e.g. B. polyester polyurethanes, polyether polyurethanes containing 4 to 100 milliequivalents per 100 g of ionic groups or groups which can be converted into ionic groups and / or such polyurethanes which contain 1 to 20% by weight of ethylene oxide units of the formula ⁇ CH incorporated within a polyethylene chain 2 ⁇ CH 2 ⁇ O ⁇ contain, where the polyether chain can be contained laterally or in the main chain.
  • Polyurethanes as used in the invention are known as such and z. B. in Angewandte macromolecular Chemistry, 26 (1972), pages 45 to 106; Angewandte Chemie 82 (1970), pages 53 ff; J. Oil. Col. Chem. Assoc. 53 (1970), page 363. Further descriptions of suitable polyurethanes can be found in DE-OSs 2637690, 2 642 973, 2651 505, 2 651 506, 2 659 617, 2 729 245, 2730514, 2 732 131, 2 734 576 and 2811 148.
  • Ionomeric polyurethanes with anionic groups are preferred.
  • Ionomeric products which are particularly suitable for the process of the invention are described in DE-PS 1 472 746. These ionomeric products are based on polyurethanes, which are obtained from compounds with several reactive hydrogen atoms with a molecular weight of 300 to 10,000, polyisocyanates and, if appropriate, chain extenders with reactive hydrogen atoms. In the production of these polyurethanes or subsequently, isocyanate groups still present in these are reacted with a compound having at least one active hydrogen atom and at least one salt-like group or one capable of salt formation. If compounds with groups capable of salt formation are used, the resulting anionic polyurethanes are then at least partially converted into the salt form in a manner known per se.
  • salt-like group means the following groups: 4 to 180 milliequivalents per 100 g of ionic groups or groups which can be converted into ionic groups are used.
  • the starting components for the preparation of the anionic polyurethanes are, for example, the compounds described below:
  • These compounds are essentially linear and have a molecular weight of about 300 to 10,000, preferably 500 to 4,000.
  • the compounds known per se have terminal hydroxyl and amino groups.
  • Polyhydroxyl compounds such as polyesters, polyacetals, polyethers, polyamides and polyesteramides are preferred. The hydroxyl number of these compounds therefore corresponds to about 370 to 10, in particular 225 to 28.
  • polyethers such.
  • B the polymerization products of ethylene oxide, propylene oxide, tetrahydrofuran, butylene oxide and their mixed or graft polymerization products, and the condensates obtained by condensation of polyhydric alcohols or mixtures thereof and the products obtained by alkoxylation of polyhydric alcohols.
  • polyacetals such.
  • the compounds that can be prepared from hexanediol and formaldehyde are in question.
  • the predominantly linear condensates obtained from polyvalent saturated carboxylic acids and polyvalent saturated alcohols, amino alcohols, diamines and their mixtures are suitable as polyesters, polyester amides and polyamides.
  • Polyhydroxyl compounds already containing urethane or urea groups and also modified natural polyols such as castor oil or carbohydrates can also be used.
  • aromatic and aliphatic diisocyanates are suitable as polyisocyanates such as.
  • the amount of the polyisocyanates is preferably selected so that all groups which are reactive with isocyanate groups react.
  • the reaction is optionally carried out with the use of solvents, low-boiling solvents with a boiling point below 120 ° C., such as, for example, acetone, ethanol, methanol, tert-butanol, methyl ethyl ketone, acetonitrile, tetrahydrofuran, dioxane, which are suitable, if appropriate may contain proportionate water.
  • solvents low-boiling solvents with a boiling point below 120 ° C.
  • Water can optionally be used as a solvent for inorganic bases and compounds with at least one hydrogen reacting with isocyanate groups and at least one salt-like group or one capable of salt formation, without the addition of organic solvents.
  • the predominantly linear, high molecular weight anionic polyurethanes are generally obtained as clear to slightly opalescent solutions in the polar solvents mentioned. Their solids content is about 5 to 50% by weight of ionic polyurethane.
  • a solution adjusted to 30% solids by dilution with acetone has a viscosity of 3,000 mPa ⁇ s.
  • Suitable water-miscible organic solvents for the process of the invention are those which are able to dissolve both the ionomeric polyurethanes and the hydrophobic color couplers.
  • examples of such solvents are acetone, tetrahydrofuran, dioxane, isopropanol, methanol, ethanol, methyl ethyl ketone, acetonitrile.
  • hydrophobic color coupler used for the process of the invention are generally 2 to 200% by weight of hydrophobic color coupler per 100% by weight of polyurethane. Weight ratios of hydrophobic color coupler to polyurethane of 1:20 to 1: 1 are preferred.
  • water is allowed to flow into a solution of the water-insoluble hydrophobic color coupler and of the polyurethane in a water-miscible low-boiling solvent or solvent / water mixture with stirring.
  • the solvent is separated from the resulting dispersion by distillation or by other suitable separation processes such as dialysis or ultrafiltration.
  • the method of the invention is excellently suitable for incorporating color couplers into color photographic recording materials.
  • the silver halide emulsions mixed with the color couplers can advantageously be cast into thin color photographic layers in which the color couplers can react with oxidized color developer compounds, for example consisting of primary aromatic amines, to form dyes.
  • oxidized color developer compounds for example consisting of primary aromatic amines
  • Examples of color couplers which can be incorporated into photographic recording layers by the process of the invention come from the group of ⁇ -dicarbonyl compounds, ⁇ -ketoacetonitriles, 5-pyrazolones, pyrazolobenzimidazoles, indazolones, phenols or naphthols.
  • hydrophobic color couplers are particularly suitable for incorporation into color photographic layers by the process of the invention.
  • the method of the invention enables the production of stable dispersions of hydrophobic substances in water without the simultaneous use of wetting agents and energy-intensive dispersing devices.
  • the dispersions show a surprisingly high sedimentation stability and are therefore outstandingly storable, a property that z. B. in the manufacturing process of recording layers proves to be a valuable advantage.
  • the lightfastness of the image dyes of color photographic recording layers which contain the dispersions prepared by the process according to the invention is significantly improved. Due to the lack of the wetting agent and high-boiling solvent in the dispersions of the invention, it is also possible to keep the binder content of color photographic recording layers low, because the dispersions can also be used without the use of protective colloids, such as. B. gelatin, stable.
  • the process of the invention differs from known processes for the production of aqueous dispersions of hydrophobic substances, in particular in that it advantageously does not start from polymer dispersions but from solutions of the products described above, from which the particles containing the hydrophobic substances are reconstructed.
  • the loaded particles obtained from such solutions are smaller than the particles formed by known processes by loading polymer dispersions.
  • the use of the dispersion prepared by the process of the invention is accordingly associated with a number of advantages: Dispersions can be stored without the risk of sedimentation, they do not cause clouding of the photographic layers and in the photographic layer structure the embedded hydrophobic substances are more accessible due to the large surface area of the particles, chemical reactions.
  • the dispersion is prepared based on the method described in DD-PS 138 831 by stirring a solution of polyurethane and coupler in water and evaporating the solvent. It is a precipitation dispersion.
  • water is metered into a solution of polyurethane and coupler and the solvent is evaporated off. In this case, the dispersion is formed by reversing the phase (see Dispersion 1).
  • the precipitation dispersion process is therefore unsuitable for the production of finely divided dispersions.
  • Polymer 111 and coupler Y 16 were used.
  • the solids content was 20.6% and the particle size was 132 nm.
  • the procedure was as described for dispersion 1. However, the color coupler M 2 was used. The dispersion obtained had a solids content of 23.2%.
  • Example 1 of DE-OS 2 541 274 a latex was produced and loaded with the color coupler Y 6 in the manner described.
  • the weight ratio of color coupler to polymer was 1: 1.
  • the particle sizes were 240 nm and 210 nm, respectively.
  • Dispersions 2, 3 and 4 of DD-PS 138 831 were reworked as dispersions A, B and C with the couplers described by their formulas.
  • the polymer (VI) was a polyaddition product composed of 218.5 g of adipic acid-hexanediol-neopentyl glycol polyester (OH number 63), 55 g of 1,6-hexane diisocyanate and 27.8 g of sodium 1,2-diaminoethane-N-propanesulfonate used.
  • This mixture is stirred at 50 ° C in 100 ml of water with a low-speed laboratory stirrer, the low-boiling organic solvent is removed by vacuum distillation and stabilized by 100 ml of a 5% aqueous gelatin solution.
  • This mixture is stirred at 50 ° C in 100 ml of a 5% aqueous gelatin solution (phthaloyl gelatin).
  • a 5% aqueous gelatin solution phthaloyl gelatin.
  • the gelatin / polymer / coupler phase is flocculated by changing the pH and the low-boiling organic solvent is thus removed.
  • the dispersions produced in the manner described sedimented and the non-sedimented portions had a particle size of about 1 J.Lm. Mixing the dispersions with gelatin produced cloudy layers.
  • Example A was repeated. Instead of coupler Y 5, coupler M 2 was used. The dispersion obtained had a particle size of 28 nm.
  • Example A was repeated. Instead of coupler Y 5, coupler C 1 was used. The dispersion obtained had a particle size of 34 nm.
  • Dispersions 1 to 15 were mixed with samples of a silver halide gelatin emulsion which had been sensitized to blue, green or red in accordance with the color coupler introduced.
  • the silver halide gelatin emulsion used consisted of 75 g of silver bromide iodide (iodide content 3 mol%) and 72 g of gelatin based on 1 kg of emulsion.
  • the emulsions prepared in this way were applied to cellulose triacetate layer supports provided with an adhesive layer and dried.
  • the sensitivity of the color photographic layers which contain dispersions prepared in accordance with the invention is up to 4 DIN higher than that of the comparison layers.
  • the color couplers contained in the samples according to the invention - with only minor deviations - coupled with steeper gamma.
  • the color yields of the couplers incorporated in the manner according to the invention are significantly higher compared to the samples processed in the conventional manner. After incorporation according to the invention, the color couplers prove to be particularly reactive.
  • the data relating to the absorption of the dyes are in no way affected by the use of the dispersions of the invention.
  • Dispersions 1, 2b and 3 and comparative dispersions 8, 9b and 10 were mixed in a silver halide gelatin emulsion of the composition described in Example 1.
  • the ready-to-pour emulsions thus obtained would now be applied to cellulose triacetate substrates provided with adhesive layers.
  • the layer samples were exposed as indicated in Example 1, developed in the manner described below and then checked for their granularity.
  • Two variants were used in the color development. These differed in the approach of the color developer, which had been prepared in one case with citracin acid and in the other case without this acid. It was found that higher color yields were obtained without citracin acid.
  • the quotient Q appearing in Table 2 below results from the difference in color yields when developed with and when developed without citracin acid multiplied by 10 2 .
  • Table 2 shows the outstanding fine-grain nature of samples 1, 2b, 3 according to the invention in comparison with the corresponding comparison samples 8, 9b and 10, respectively.
  • the quotient Q the absolute value of which is proportional to the influence of citracin acid, was also found to be significantly lower in the samples according to the invention. This is related to the already mentioned high reactivity of the color couplers dispersed in the manner according to the invention.
  • the dispersions 1, 2a, 6, 7 and 15 according to the invention and the comparative dispersions 8, 9a, 13 and 14 were mixed in with the silver halide gelatin emulsions which had been sensitized accordingly to the couplers and the emulsions were poured onto a baritized paper base. The samples were then exposed as described in Example 1 and processed in the following baths. Stop bath Bleach-fix bath (pH 7) Processing times 25 ° C
  • a photographic emulsion layer consisting of a silver bromide emulsion, a dispersion prepared according to the invention or a comparison emulsifier, gelatin and a hardening agent was produced and dried on a prepared cellulose triacetate film support. After drying, the layer contained 20% by volume of AgBr and 30% by volume of the dispersion according to the invention or of comparative emulsifier. 36 mm wide strips of this material were 3 days in a climate of 20% r. F. adjusted at 23 ° C. The measurement was made using the drop hammer method in this climate. The test specimens are placed in loops with the emulsion layer on the outside and the energy that leads to the breakage of the film is determined. Around 100 breaking attempts were carried out, at least half of which are said to break.
  • the measured fracture energy values B of the layers which contain the dispersion according to the invention are compared with the fracture energy values obtained with the comparison emulsifiers.
  • the increase in the breaking strength of the layers with the dispersions according to the invention was calculated in% using the following formula.
  • Example A was repeated. Instead of coupler Y 5, coupler M 2 was used. The dispersion obtained had a particle size of 28 nm.
  • Example A was repeated. Instead of coupler Y 5, coupler C 1 was used. The dispersion obtained had a particle size of 34 nm.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
EP81107366A 1980-09-30 1981-09-17 Verfahren zur Herstellung von Dispersionen hydrophober Farbkuppler in Wasser sowie deren Verwendung bei der Herstellung lichtempfindlicher Aufzeichnungsmaterialien Expired EP0049399B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3036846 1980-09-30
DE19803036846 DE3036846A1 (de) 1980-09-30 1980-09-30 Verfahren zur herstellung von dispersionen hydrophober substanzen in wasser

Publications (3)

Publication Number Publication Date
EP0049399A2 EP0049399A2 (de) 1982-04-14
EP0049399A3 EP0049399A3 (en) 1982-11-24
EP0049399B1 true EP0049399B1 (de) 1986-09-10

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EP81107366A Expired EP0049399B1 (de) 1980-09-30 1981-09-17 Verfahren zur Herstellung von Dispersionen hydrophober Farbkuppler in Wasser sowie deren Verwendung bei der Herstellung lichtempfindlicher Aufzeichnungsmaterialien

Country Status (5)

Country Link
US (1) US4388403A (enrdf_load_stackoverflow)
EP (1) EP0049399B1 (enrdf_load_stackoverflow)
JP (1) JPS5787429A (enrdf_load_stackoverflow)
CA (1) CA1163891A (enrdf_load_stackoverflow)
DE (2) DE3036846A1 (enrdf_load_stackoverflow)

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Publication number Priority date Publication date Assignee Title
DE102015008388A1 (de) 2015-06-29 2016-12-29 WAE Marketing GbR (vertr. Gesellsch. Herr Oliver Westerbeek, 51069 Köln) Verwendung einer polymeren Zubereitung zur Beschichtung von Handschuhen

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DE3175302D1 (en) 1986-10-16
US4388403A (en) 1983-06-14
JPS5787429A (en) 1982-05-31
EP0049399A3 (en) 1982-11-24
JPH0315730B2 (enrdf_load_stackoverflow) 1991-03-01
CA1163891A (en) 1984-03-20
DE3036846A1 (de) 1982-05-27
EP0049399A2 (de) 1982-04-14

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