EP0021108A1 - Procédé d'allongement de la chaîne moléculaire de la gélatine par durcissement partiel, et composition à base de gélatine et matériau photographique contenant une gélatine ainsi obtenue - Google Patents

Procédé d'allongement de la chaîne moléculaire de la gélatine par durcissement partiel, et composition à base de gélatine et matériau photographique contenant une gélatine ainsi obtenue Download PDF

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Publication number
EP0021108A1
EP0021108A1 EP80103012A EP80103012A EP0021108A1 EP 0021108 A1 EP0021108 A1 EP 0021108A1 EP 80103012 A EP80103012 A EP 80103012A EP 80103012 A EP80103012 A EP 80103012A EP 0021108 A1 EP0021108 A1 EP 0021108A1
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EP
European Patent Office
Prior art keywords
gelatin
oder
alkyl
mit
layer
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Granted
Application number
EP80103012A
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German (de)
English (en)
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EP0021108B1 (fr
Inventor
Heinrich Dr. Jung
Ulrich Dr. Biskup
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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 EP0021108A1 publication Critical patent/EP0021108A1/fr
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Publication of EP0021108B1 publication Critical patent/EP0021108B1/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
    • G03C1/04—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with macromolecular additives; with layer-forming substances
    • G03C1/047—Proteins, e.g. gelatine derivatives; Hydrolysis or extraction products of proteins
    • 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
    • G03C1/30—Hardeners

Definitions

  • the invention relates to a method for chain extension of gelatin by partial hardening using an instant hardening agent.
  • the curing agent is either added to the casting solutions or introduced into the finished layers by subsequent application of a curing agent solution.
  • the invention has for its object to develop a gelatin, in particular a gelatin suitable for the production of photographic layers, which has an improved solidification behavior and which can be used as a binder without the casting defects caused by blowing, without disturbing sedimentation phenomena and without wrinkling, even if high pouring speeds are used.
  • the object is achieved according to the invention by a method for chain extension of gelatin by partial hardening, which is characterized in that a gelatin solution which contains at least 5% by weight of gelatin, 0.011 to 10 minutes at 30 to 90 ° C with 0.001 is contacted to 0.01 moles per 100 g of dry gelatin of a curing agent which is able to activate the carboxyl groups of the gelatin and which has a 20 / um thick dry gelatine layer, when this is covered with an aqueous solution of the curing agent so that 0.01 up to 0.03 mol hardening agent per 100 g dry gelatin and the pH of the moist gelatin layer is 5-7, at a good temperature of 20 ° C after 3 to 6 minutes converted into a boil-proof, no longer post-curing gelatin layer.
  • Photographic layer dressings produced with the aid of the gelatin of the invention are distinguished by a reduced lateral swelling of the individual layers, as a result of which the formation of wrinkles is suppressed. These effects are based on a chain extension of the gelatin.
  • the chain extension is achieved by homogeneously mixing a gelatin solution that is as concentrated as possible with a suitable hardening agent.
  • the mixing must take place in a time that is short compared to the reaction time of the curing agent used.
  • the amount of hardening agent is chosen so that the resulting reaction product is still soluble or can be brought back into solution after solidification. For gelatins with high Bloom values, hardener quantities of 0.6% based on the gelatin are sufficient.
  • the preferred embodiment of the method of the invention is to process aqueous gelatin solutions and to keep the concentration of the gelatin higher than 5% by weight, preferably higher than 10% by weight. Excellent results are achieved with concentrations of 10 to 30% by weight.
  • the amount of hardening agent used should advantageously be chosen so large that just no or just an insoluble gelatin reaction product is obtained. In general, good results will be obtained with 0.01 to 0.001 mol and in particular 0.008 to 0.002 mol hardener per 100 g gelatin or, in other words, with 3 to 0.3% by weight, preferably 2.4 to 0.6% by weight of the hardening agent, based on the dry weight of the gelatin.
  • the optimal amount of hardener depends on the type of gelatin (molecular weight) and the chemical nature of the hardener. It can easily be determined by simple experiments.
  • the treatment time of the gelatin with the hardening agent is in the range of about 0.01 seconds to 10 minutes, depending on the temperature and the hardener used. In the work area of interest for practice, good results are achieved with reaction times of 5 to 200 seconds and preferably 7 to 100 seconds.
  • the treatment temperature is 30 to 90 ° C and preferably 30 to 60 ° C.
  • the chain extension reaction can be accelerated by vigorous stirring of the reaction solution.
  • Treatment of the gelatin according to the invention can advantageously be carried out in the presence of surface active compounds such as e.g. Na dodecyl sulfate can be carried out. Suitable amounts of such surface-active compounds are 1-6% by weight, based on gelatin.
  • the resulting product can be diluted to the desired concentration directly in a suitable mixing unit.
  • Particularly suitable as starting material for the production of the gelatins are gelatin qualities which meet the usual requirements in the production of photographic layers.
  • the gelatins produced therefrom in the manner according to the invention differ very advantageously from the corresponding starting products with regard to the rate of solidification and the viscosity of the casting solutions produced therefrom and in the lateral swelling of dried layers.
  • low-quality starting products can also be used to obtain gelatins with significantly improved solidification behavior and increased viscosity in the manner described.
  • the carboxyl group activating compounds are hardening agents which do not directly attack the amino groups of the gelatin, but rather react with the carboxyl groups of the gelatin to form reactive intermediates of the activated ester or anhydride type, the activated intermediates forming isopeptide bonds with the amino groups of the gelatin with crosslinking continue to react.
  • the hardening agents used according to the invention are so-called instant hardening agents, which are hardening agents activating the carboxyl groups of the gelatin. It is characteristic of these instant hardening agents that photographic gelatin layers treated with them are boil-proof and do not cure further after they have left the casting machine after casting and drying.
  • the hardening agent used in this case is an immediate hardening agent.
  • post-curing if:
  • the curing agent used is then not an instant curing agent in the sense of the invention.
  • Helicated form is understood to mean a partial plasma conversion of the gelatin molecules during cooling. Helication is important for gel formation.
  • the desired intermolecular (intercaternary) bonds are obtained, which are predominantly formed by linear chain extension into one Increase the molecular weight without impairing the triple helix formation tendency, whereby triple helix formation is understood to mean the partial transition from statistical balls into ordered helical regions which consist of three molecules.
  • gelatin derivatives With a higher gelation rate and with an increased viscosity of aqueous solutions prepared therefrom and less lateral swelling of layers cast therefrom are obtained.
  • Figure 1 shows the gel chromatograms of three bone gelatins compared to a gelatin treated by the method of the invention.
  • microgel a very high molecular weight fraction occurs in the exclusion volume, which is referred to below as microgel. This proportion is 3 to 4.5% for the starting products, due to the chain extension it increases to over 20% (curve G4).
  • the gelatins obtained by the process of the invention have a microgel content of up to 40%.
  • a more precise analysis of the microgel was carried out by viscometric measurements on solutions, namely before and after a double centrifugation.
  • the ratio g of the viscosity numbers of the samples to a linear calibration sample was determined.
  • the deviation of the number g from the value 1 is a measure of the deviation of the sample from the linear structure.
  • a relatively linear chain extension has therefore preferably taken place.
  • the fast acting curing agents suitable for the process of the invention are known as such. Details regarding their manufacture and properties can be found in the following publications. Carbamoylonium compounds from British Patent 1,383,630 and carbamoyloxypyridinium compounds from Belgian Patent 825,726. Carbodiimide hardeners are described in American Patent Specifications 2,938,892, 3,098,693 and the work of E. Schmidt, F. Hitzler and E. Lahde in Ber. 71, 1933 (1938) or by G. Amiard and R. Heynes in Bull.Soc.Chim. France 1360 (1956) and in Belgian patent 830 866. Details of suitable dihydroquinoline compounds can be found in British Patent 1,452,669. Isoxazolium salts and bis-isoxazoles are e.g. in U.S. Patent Nos. 3,316,095, 3,321,313, 3,543,292 and 3,681,372, or British Patent 1,030,882.
  • the chain extended gelatins of the invention are excellently suitable as binders for building photographic layers. They can be used both unmixed and in a mixture with the gelatin customary for photographic purposes, the mixing ratio being practically unlimited and being readily adaptable to the particular application.
  • photographic gelatin is to be understood as gelatins, such as those found in Ullmann's Encyclopedia of Industrial Chemistry, 3rd edition, 13th volume, pages 620 and 621, in the essay by HW Wood. I.Phot.Sci.9,151 (1961), in the work of WS Wittenberg, Photo-Technik und Boat, 11 (1960), 279 or the work of RJCroome, FGClegg "Photographic Gelatin", Focal Press London-New York 1965 will.
  • photographic layers layers are to be understood in the present context in general, find the photographic under materials use, such as light-sensitive silver Halo g enidemul- sion layers, protective layers, filter layers, antihalation layers, backing layers or, more generally, photographic auxiliary layers.
  • the gelatins of the invention have proven themselves for the production of the gelatin layers used for the various black and white and color photographic processes, such as negative, positive and diffusion transfer processes or printing processes.
  • the gelatins of the invention have proven to be particularly advantageous for the production of photographic layer dressings intended for carrying out color photographic processes, e.g. those which contain emulsion layers with color couplers or emulsion layers which are intended for treatment with solutions which contain color couplers.
  • the emulsion layers can contain any known silver halides as light-sensitive components, such as silver chloride, silver iodide, silver bromide, silver iodobromide, silver chlorobromide, silver chlorobiodobromide and the like.
  • the emulsions can be chemically sensitized by noble metal compounds, e.g. by compounds of ruthenium, rhodium, palladium, iridium, platinum, gold and the like, such as ammonium chloropalladate, potassium chloroplatinate, potassium chloropalladite, or potassium chloroaurate. They can also contain special sensitizers for sulfur compounds, tin (II) salts, polyamines or polyalkylene oxide compounds.
  • the emulsions can e.g. be optically sensitized with cyanine dyes, merocyanine dyes and mixed cyanine dyes.
  • the emulsions can be a wide variety of water-soluble or emulsified water-insoluble couplers, colorless couplers, colored couplers, stabilizers, such as mercury compounds, triazole compounds, azainden compounds, benzothiazolium compounds or zinc compounds, wetting agents, such as dihydroxyalkanes, agents which improve film formation properties, for example those used in the emulsion polymerization or alkylacrylation of alkylacrylation alkyl methacrylate / acrylic or Methacrylklamischpolymeren obtained water-dispersible particulate high polymers, styrene / maleic acid copolymers or styrene / Maleinklareanhydridraumalkylester copolymers, coating aids such as Polyäthylenglykollaurylreliher and contain various other photographic additives.
  • wetting agents such as dihydroxyalkanes
  • colloidal albumin In addition to the modified gelatin, colloidal albumin, agar, gum arabic, dextrans, alginic acid, cellulose derivatives, e.g. up to an acetyl content of 19 to 26% hydrolyzed cellulose acetate, polyacrylamides, imidated polyacrylamides, zein, vinyl alcohol polymers with urethane / carboxylic acid groups or cyanoacetyl groups, such as vinyl alcohol / vinyl cyanoacetate mixed polymers, polyvinyl alcohols, polyvinylpyrrolidones, hydrolyzed or polymerized polymers, such as proteins, hydrolysed polymers, such as proteins, hydrolysed polymers, such as vinylated polymers, such as proteins, hydrolysed polymers, such as proteins, hydrolysed polymers, such as vinylated polymers, such as proteins, hydrolysed polymers, such as vinylates, or hydrolyzed polymers, such as proteins, such as vinylates acylated proteins with monomers having vinyl groups can be
  • the photographic layers made using the gelatins of the invention can be cured in a conventional manner, e.g. with hardening agents as described in the journal "Research Disclosure", Industrial Opportunities Ltd. Homewell, Harant, Hampshire, England, Dec. 1978, page 26 under (X). It is found that the gelatins of the invention require around 30% less hardener than conventional gelatins.
  • the gelatins of the invention can advantageously be used not only in the photographic field.
  • the characteristic properties achieved by the chain extension also make the gelatin extremely suitable for use in cosmetic articles, for the production of gelatin capsules or gelatin membranes and for use in the food field.
  • An inferior gelatin (last removal of a bone gelatin) was pretreated as in Example 7 and tested for solidification speed and gel strength.
  • the shear modulus which the 5% by weight aqueous gelatin achieves after a very long time is stated as the gel strength.
  • This value G oo is determined by extrapolation to t ⁇ oo. It is proportional to the Bloom value.
  • the bloom value is determined by first cooling a 6.66% strength by weight aqueous gelatin solution in a bloom glass at 10 ° C. for 16 hours. For the measurement, a stamp with a diameter of 12.7 mm is pressed 4 mm deep into the gel. The weight in grams that is necessary to impress this stamp is called the Bloom value.
  • the rate of solidification of a last withdrawal of an alkaline ashed bone gelatin is increased by the factor 4.6 by the pretreatment according to the invention.
  • the thrust module G oo is increased by a factor of 2.3.
  • a comparison with the solidification times t o of a high-quality gelatin (D) shows that with the sample (C) according to the invention, which starts from a gelatin of inferior quality, a solidification rate was achieved which is comparable to that of a high-quality gelatin.
  • An inferior gelatin (last peel of a skin gelatin) was pretreated as in Example 8 and characterized in terms of solidification rate and gel strength.
  • the rate of solidification of a last withdrawal of an alkaline ashed skin gelatin is increased by a factor of 14 by the pretreatment according to the invention.
  • the thrust module G oo is increased by a factor of 6.
  • the swelling factor is the ratio of the thicknesses of a layer in the swollen and air-dry state. It is measured on layers that adhere to a base. The swelling takes place in dest. Water for 5 min at 20 ° C.
  • Sample I Untreated comparative gelatin from Example 8.
  • Sample II Chain-extended gelatin from Example 8.
  • the example shows that the gelatin II pretreated according to the invention has very low A values on cold drying and is almost independent of the hardening.
  • the A value of the uncured gelatin II is already lower than that of the cured gelatin I and is reduced relatively little by the curing.
  • the low A values achieved by the pre-crosslinking have the effect that the tendency of semi-finished goods to reticulate is reduced or avoided as the material continues to build up.
  • Samples were cast from 5% casting solutions using a skin gelatin and a gelatin produced therefrom according to Example 4 (Verbdg. II / 15).
  • the wet application was 100 .mu.m, the casting speed 70 m / min.
  • the solidification took place at 15 ° C for 16 to 0 seconds, then was at 19 0 C good temperature with an air speed of 26 m / sec. dried and the casting quality assessed with regard to blowing.
  • the result is shown in the following table.
  • an aqueous solution of the curing agent of the formula is applied to the layer 8 applied in an amount of 0.6 g of curing agent per m 2 and the material then dried.
  • the preparation of the material is repeated with the difference that in the gelatin layers 1 to 8 the gelatin is replaced by the chain-extended gelatin of example 1.
  • a photographic material is obtained which is in no way inferior in quality to the material produced using conventional photographic gelatin and which is superior to the conventional material in terms of its production, owing to the advantageous solidification properties and higher viscosity of the chain-extended gelatin.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
EP80103012A 1979-06-13 1980-05-30 Procédé d'allongement de la chaîne moléculaire de la gélatine par durcissement partiel, et composition à base de gélatine et matériau photographique contenant une gélatine ainsi obtenue Expired EP0021108B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19792924035 DE2924035A1 (de) 1979-06-13 1979-06-13 Verfahren zur kettenverlaengerung von gelatine durch partielle haertung
DE2924035 1979-06-13

Publications (2)

Publication Number Publication Date
EP0021108A1 true EP0021108A1 (fr) 1981-01-07
EP0021108B1 EP0021108B1 (fr) 1983-02-09

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EP80103012A Expired EP0021108B1 (fr) 1979-06-13 1980-05-30 Procédé d'allongement de la chaîne moléculaire de la gélatine par durcissement partiel, et composition à base de gélatine et matériau photographique contenant une gélatine ainsi obtenue

Country Status (5)

Country Link
US (1) US4421847A (fr)
EP (1) EP0021108B1 (fr)
JP (1) JPS562324A (fr)
CA (1) CA1155440A (fr)
DE (2) DE2924035A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0247482A3 (en) * 1986-05-28 1988-08-03 Miles Laboratories, Inc. Hardened reagent coatings, and processes for the preparation thereof
EP0286913A3 (en) * 1987-04-11 1989-03-08 Agfa-Gevaert Ag Colour-photographic recording material
EP0267523A3 (en) * 1986-11-14 1989-03-15 Agfa-Gevaert Ag Colour-photographic silver halide material
EP0267522A3 (en) * 1986-11-12 1989-04-26 Agfa-Gevaert Ag Photographic recording material
WO1991014968A1 (fr) * 1990-03-22 1991-10-03 Eastman Kodak Company Controle du voile du a l'effet de la pression avec des particules de latex polymere souple a greffe de gelatine et a greffe de gelatine cementee

Families Citing this family (19)

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Publication number Priority date Publication date Assignee Title
US4530905A (en) * 1984-10-25 1985-07-23 The Dow Chemical Company Crosslinked gelatin foams
JPS60237445A (ja) * 1984-05-10 1985-11-26 Fuji Photo Film Co Ltd ハロゲン化銀カラ−写真感光材料
JPS60258545A (ja) * 1984-05-10 1985-12-20 Fuji Photo Film Co Ltd ハロゲン化銀カラ−写真感光材料
US4751173A (en) * 1985-12-27 1988-06-14 Fuji Photo Film Co., Ltd. Process for hardening gelatin
DE3608998A1 (de) * 1986-03-18 1987-10-01 Agfa Gevaert Ag Fotografisches aufzeichnungsmaterial
JPS62291565A (ja) * 1986-05-28 1987-12-18 マイルス・ラボラトリ−ズ・インコ−ポレ−テッド 硬化試薬マトリックス被膜及びその製造方法
US4804715A (en) * 1986-08-26 1989-02-14 Cook Paint And Varnish Company Cyanoacetic ester system
DE3629388A1 (de) * 1986-08-29 1988-03-03 Agfa Gevaert Ag Verfahren zur haertung proteinartige bindemittel enthaltender schichten
JPH0687124B2 (ja) * 1987-02-26 1994-11-02 アグフアーゲヴエルト・アクチエンゲゼルシヤフト 写真記録材料
US4877724A (en) * 1987-03-05 1989-10-31 Eastman Kodak Company Method and composition for hardening gelatin
JP2565548B2 (ja) * 1987-09-18 1996-12-18 イーストマン コダック カンパニー カルバモイルオニウム化合物を用いてポリマー粒子に化合物を結合させる方法
US5219992A (en) * 1990-06-18 1993-06-15 Eastman Kodak Company Modification of gelatin
US5155166A (en) * 1990-06-18 1992-10-13 Eastman Kodak Company Use of 1-(1-pyrrolidinylcarbonyl)pyridinium salts to attach compounds to carboxylated particles and a kit containing same
US5187259A (en) * 1990-11-14 1993-02-16 Eastman Kodak Company Chain extended gelatin
US5378598A (en) * 1992-12-21 1995-01-03 Eastman Kodak Company Use of acid processed ossein gelatin and chain-extened acid processed ossein gelatin as peptizers in the preparation of photographic emulsions
US5318889A (en) * 1992-12-21 1994-06-07 Eastman Kodak Company Use of chain-extended acid processed ossein gelatin in the preparation of photographic elements
US5948857A (en) * 1998-06-04 1999-09-07 Eastman Kodak Company Gelatin-modified polyurethane
JP4275836B2 (ja) 2000-02-24 2009-06-10 富士フイルム株式会社 水可溶性鎖延長ゼラチンの製造方法、それにより製造されたゼラチン、及び該ゼラチンを含むハロゲン化銀写真感光材料
WO2010115159A1 (fr) 2009-04-03 2010-10-07 Meridian Research And Development, Inc. Nanoparticules de métal

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US2652345A (en) * 1952-04-29 1953-09-15 Eastman Kodak Co Method of setting protein containing coatings with ammonium
US2996405A (en) * 1956-07-05 1961-08-15 Eastman Kodak Co Method of quick-setting proteincontaining coatings
GB963772A (en) * 1961-06-05 1964-07-15 Swift & Co Method for improving the flocculating properties of proteinaceous materials
US3171831A (en) * 1961-02-14 1965-03-02 Schwarz Biores Inc Thiolation of proteins by reaction with homocysteine thiolactone in the presence of tertiary amine
FR2021444A1 (fr) * 1968-10-24 1970-07-24 Eastman Kodak Co
FR2173009A1 (fr) * 1972-02-25 1973-10-05 Ciba Geigy Ag
DE2439551A1 (de) * 1974-08-17 1976-02-26 Agfa Gevaert Ag Verfahren zur haertung photographischer schichten
DE2602150A1 (de) * 1975-02-10 1976-08-19 Agfa Gevaert Ag Verfahren zum haerten von photographischen proteinhaltigen schichten
DE2545755A1 (de) * 1975-10-11 1977-04-21 Agfa Gevaert Ag Verfahren zur haertung photographischer schichten

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US3100704A (en) * 1958-07-24 1963-08-13 Gen Aniline & Film Corp Photographic materials containing carbodhmides
US3103437A (en) * 1959-04-10 1963-09-10 Hardening
US3619236A (en) * 1968-11-25 1971-11-09 Eastman Kodak Co Method for coating layers of gelatin and a carboxyl-containing polymer on a support
DE2417779A1 (de) * 1974-04-11 1975-10-30 Agfa Gevaert Ag Verfahren zur haertung photographischer schichten
DE2625026A1 (de) * 1976-06-03 1977-12-22 Agfa Gevaert Ag Verfahren zur haertung photographischer gelatinehaltiger schichten

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2652345A (en) * 1952-04-29 1953-09-15 Eastman Kodak Co Method of setting protein containing coatings with ammonium
US2996405A (en) * 1956-07-05 1961-08-15 Eastman Kodak Co Method of quick-setting proteincontaining coatings
US3171831A (en) * 1961-02-14 1965-03-02 Schwarz Biores Inc Thiolation of proteins by reaction with homocysteine thiolactone in the presence of tertiary amine
GB963772A (en) * 1961-06-05 1964-07-15 Swift & Co Method for improving the flocculating properties of proteinaceous materials
FR2021444A1 (fr) * 1968-10-24 1970-07-24 Eastman Kodak Co
FR2173009A1 (fr) * 1972-02-25 1973-10-05 Ciba Geigy Ag
DE2439551A1 (de) * 1974-08-17 1976-02-26 Agfa Gevaert Ag Verfahren zur haertung photographischer schichten
DE2602150A1 (de) * 1975-02-10 1976-08-19 Agfa Gevaert Ag Verfahren zum haerten von photographischen proteinhaltigen schichten
DE2545755A1 (de) * 1975-10-11 1977-04-21 Agfa Gevaert Ag Verfahren zur haertung photographischer schichten

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0247482A3 (en) * 1986-05-28 1988-08-03 Miles Laboratories, Inc. Hardened reagent coatings, and processes for the preparation thereof
EP0267522A3 (en) * 1986-11-12 1989-04-26 Agfa-Gevaert Ag Photographic recording material
EP0267523A3 (en) * 1986-11-14 1989-03-15 Agfa-Gevaert Ag Colour-photographic silver halide material
EP0286913A3 (en) * 1987-04-11 1989-03-08 Agfa-Gevaert Ag Colour-photographic recording material
WO1991014968A1 (fr) * 1990-03-22 1991-10-03 Eastman Kodak Company Controle du voile du a l'effet de la pression avec des particules de latex polymere souple a greffe de gelatine et a greffe de gelatine cementee

Also Published As

Publication number Publication date
US4421847A (en) 1983-12-20
DE2924035A1 (de) 1981-01-08
CA1155440A (fr) 1983-10-18
DE3061882D1 (en) 1983-03-17
JPS562324A (en) 1981-01-12
EP0021108B1 (fr) 1983-02-09

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