US3584391A - Drying ei ement,chemical composition and process - Google Patents

Drying ei ement,chemical composition and process Download PDF

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US3584391A
US3584391A US876179A US3584391DA US3584391A US 3584391 A US3584391 A US 3584391A US 876179 A US876179 A US 876179A US 3584391D A US3584391D A US 3584391DA US 3584391 A US3584391 A US 3584391A
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polymer
drying
organic
photographic
coating
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Robert H Cunningham
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Eastman Kodak Co
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Eastman Kodak Co
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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
    • G03C11/00—Auxiliary processes in photography
    • G03C11/16—Drying
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
    • C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
    • C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02—Polyalkylene oxides

Definitions

  • a liquid permeable, drying element such as a thin coating, containing an organic, polymeric desiccant crosslinked to a polymer, for example cross-linked to a support comprising a polymer, which can be the same as the organic desiccant or different from the organic, polymeric desiccant, rapidly removes diffusible liquid, especially water, from a permeable solid.
  • a drying element, as described, can be used for removing diifusible liquid from layers of a photographic element, such as photographic film.
  • This invention relates to removing diffusible liquids from liquid permeable solid materials containing such liquids. In one of its aspects, it relates to removing diffusible liquid such as water, from a liquid permeable solid material, such as a moist layer of a photographic element. In another of its aspects, it relates to drying a moist colloid coating by intimately contacting the moist coating with a coating containing an organic, polymeric desiccant cross-linked to a polymer, especially a support comprising the polymer.
  • an organic, polymeric desiccant with an aldehyde, such as formaldehyde, to a polymer which may be the organic, polymeric desiccant or a polymer different from said organic desiccant, during coating.
  • an aldehyde such as formaldehyde
  • Drying of photographic elements processed without use of conventional processing baths and where inspection of the processed element as soon as possible is desirable has been especially important.
  • One method which has been advantageous in decreasing the time from exposure to finished product, without the use of conventional processing baths employs a wet or moist, absorbent web containing processing agents, typically a monobath, which is contacted ⁇ m'th the exposed element for a desired length of time.
  • This method and means for carrying out the method are set out, for example, in US. Pat. 3,179,517 of Tregillus et al., issued Apr.
  • a typical drying element described in these applications comprises about 10%, by weight, poly- (ethylene oxide) having an average molecular weight of about 6,000 to about 7,500 with about by weight, of high molecular poly(ethylene oxide) e.g., having an average molecular weight of from about 100,000 to about 5,000,000 or more, on a support.
  • the high molecular weight binder in such a drying element e.g., poly(ethylene oxide) having an average molecular weight of about 100,- 000 to about 5,000,000, is useful in order to prevent contamination of the photographic element being dried by transfer of the lower molecular weight poly(ethylene oxide) to the photographic element.
  • the coating composition employed in preparing such drying elements is high in viscosity, mainly due to the high molecular weights of the components of the compositions. This has caused difiiculty in preparing such coatings.
  • the drying element needed was one which (a) provided means to remove diffusible liquids, such as water, from liquid permeable solid materials, such as moist or Wet photographic elements, in a 3 matter of seconds, (b) could be prepared from coating compositions'of'suitable coating viscosities, (c) could be coated quickly and contain a high percent of solids when coated, and (d) did not provide undesired effects on a photographic element.
  • a ditfusible liquid such as water
  • a liquid permeable solid such as a layer of a photographic element
  • a solid, liquid permeable, drying element comprising (a) an organic, polymeric desiccant cross-linked ;with (b) a cross-linking agent, such as an aldehyde, to (c) an organic polymer which can be the same or different from the described polymeric desiccant.
  • This invention provides processes, means and compositions whereby the diffusible liquid can be removed from the permeable solid, such as a photographic element, in a matter of seconds, leaving a photographic element which can be immediately used in further steps, such as in contact printing.
  • the viscosity of a coating composition from which the described drying element can be prepared is such that greater speed can be used during the coating operation and a higher percentage of solids can be present in the coating composition.
  • the cross-linking reaction of the polymeric desiccant with the cross-linking agent, e.g., formaldehyde allows low viscosity coating compositions, for the preparation of the drying element, of such characteristics that the composition can set or solidify quickly.
  • One embodiment of this invention is a liquid permeable, drying element comprising an organic, polymeric desiccant cross-linked with an aldehyde to an organic polymer, which can be the same as the described desiccant and/or an organic polymer diiferent from the described desiccant.
  • a range of organic, polymeric desiccants can be employed according to the invention. These include any which contain a group which can be cross-linked with a cross-linking agent, such as formaldehyde. These include, for example,
  • Urethane resins (.g) Urethane resins. Compounds of this type are available, for example, from the Dow Chemical Company, Midland, Mich, under the trade name Voranol.
  • a preferred organic, polymeric desiccant of this invention is a so-called modified poly(ethylene oxide) containing acetoacetate end groups.
  • the average molecular weight range of such a polymer is about 900 to about 20,000.
  • the described modified poly(ethylene oxide) can be represented by the formula:
  • polyethylene glycol having an average molecular weight of about 200 to about 20,000, is mixed in about stoichiometric concentrations with diketene under ambient conditions.
  • the alkylene oxide polymer can be reacted with diketene either in an organic solvent such as methanol or ethanol, in an aqueous solvent, such as water, or a mixture of water with ethylene glycol or, preferably, by melting the polyethylene glycol and reacting it with diketene directly in the absence of any solvent. The reaction proceeds spontaneously at about room temperature and pressure.
  • the reaction produces a modified poly(ethylene oxide) some of whose hydroxyl groups have been converted to acetoacetate groups.
  • the reaction can be carried out in the presence of a catalyst, such as an amine, e.g., triethyl amine or diet-hyl amine, or inorganic alkali, e.g., sodium hydroxide.
  • a catalyst such as an amine, e.g., triethyl amine or diet-hyl amine, or inorganic alkali, e.g., sodium hydroxide.
  • modified poly(ethylene oxide) produced by the reaction with diketene has acetoacetate end groups, which are believed to allow cross-linking in the presence of crosslinking agents.
  • the modified poly(ethylene oxide) can cross-link with gelatin, such as gelatin on a gelatin coated support and/ or with the same modified poly(ethylene oxide), and/or with a polymer different from the modified poly(ethyleue oxide) which also has acetoacetate end groups and/ or other groups which can crosslink with the described polymers.
  • cross-linking agents can be employed in the practice of the invention.
  • Especially useful cross-linking agents are aldehydes, e.g., those employed in the photographic art as hardening agents, such as formaldehyde,
  • a range of concentration of cross-linking agent can be employed in the coating compositions from which the described drying element is prepared and/ or in the resulting coating.
  • a suitable concentration will depend on several factors, such as the particular polymers employed, the conditions employed for coating, the support, if any, and the like. Usually the concentration is in excess of a stoichiometric concentration.
  • the polymer to which the described organic, polymeric desiccant is cross-linked can be the same as the organic, polymeric desiccant or different from it, e.g., have a different molecular weight and/or have a different composition.
  • Suitable polymers to which the described organic, polymeric desiccant can be cross-linked include, for example:
  • Gelatino polymers such as a gelatin subbing layer commonly employed on supports in the photographic art
  • the organic polymer II as described can be prepared by dissolving the starting polymer, i.e., poly (vinyl acetal) of 2,4-disulfobenzaldehyde, in an inert solvent, such as dimethyl formamide or dimethyl sulfoxide.
  • an inert solvent such as dimethyl formamide or dimethyl sulfoxide.
  • a solution of diketene in an inert solvent, such as dimethyl formamide or dimethyl sulfoxide is added to the resulting composition at elevated temperature, e.g., about 140 C.
  • the desired polymer containing acetoacetate end groups can be precipitated from the resulting composition by adding the reaction mixture to methanol.
  • a second method of preparing polymer II, or a method for preparing polymer III, or polyvinyl alcohol containing acetoacetate end groups consists of dissolving the starting polymer, e.g., polyvinyl alcohol, poly(vinyl acetal) of 2,4-disulfobenzaldehyde or hydroxyethylcellulose in the case of polymer III, in a solvent, e.g., an aqueous solvent such as water or a mixture of water with ethylene glycol.
  • a solvent e.g., an aqueous solvent such as water or a mixture of water with ethylene glycol.
  • a solution of diketene e.g., an aqueous solution, is added to the resulting composition.
  • the reaction usually proceeds spontaneously under ambient conditions of temperature and pressure, e.g., at about C. to C. at atmospheric pressure, but elevated temperature and pressure can be employed, if desired.
  • the desired product can be separated, such as by precipitation in an organic solvent, e.g., isopropanol.
  • the coating compositions from which the described drying element is prepared is coated on a support, such as a support known to be useful in the photographic art which contains a so-called subbing layer, e.g., of gelatin or other polymer as described.
  • a support such as a support known to be useful in the photographic art which contains a so-called subbing layer, e.g., of gelatin or other polymer as described.
  • one embodiment of the invention is an unsupported web of the socalled modifed poly(ethylene oxide) cross-linked with a cross-linking agent, typically an aldehyde, such as formaldehyde, to a polymer the same as the so-called modified poly(ethylene oxide) and/or different from the modified poly(ethylene oxide), e.g., the described polymers II and/or 111 and/or 1V.
  • Any support if one is employed, can be used for a drying element according to the invention, provided such a support is coated with gelatin or some such material with which the polymeric components containing acetoacetate end groups of the coating can cross-link.
  • a support can be in any suitable shape or form. These include those commonly employed in the photographic art, such as films, including cellulose acetate films, polyester films, such as polyethylene terephthalate films, polyvinyl acetal films, polystyrene films, polycarbonate films, and related materials, paper, e.g., paper supports coated with resinous materials, e.g., coated with polyethylene, polypropylene and/or ethylene-butene copolymers, glass fabrics, metal and the like.
  • Supports in the form of webs and tapes can be used, for example. Supports which act as a reservoir for the diffusible liquid removed are especially suitable. For this reason, absorbent fibrous materials formed from, for example, textiles or glass fibers, paper and/ or similar water absorbent supports can be especially useful.
  • coating compositions and means for applying them can be employed for preparing the coatings of the invention.
  • any composition, coating means or coating process which provides an adherent coating, having the desired thickness, the desired concentrations of components, and the desired liquid removal properties can be employed.
  • Various addenda can be present in and/or on the coating and/or support, if one is employed, according to the invention, especially those known to be beneficial in photographic elements, compositions and processes.
  • a coating composition of the invention from which a drying element can be prepared, comprises (a) a hydrophilic ethylene oxide polymer containing acetoacetata groups, e.g., polymer I, (b) a cross-linking agent as described, especially an aldehyde, e.g., formaldehyde and (c) a solvent.
  • An especially suitable coating composition comprises a mixture of (a) About 60% to about 90%, by weight, of the total composition solvent, comprising about 10% to about 30% by volume, water and about to about 90%, by volume, Water miscible organic solvent, e.g., water miscible alcohol such as methanol,
  • cross-linking agent such as an aldehyde, e.g., formaldehyde.
  • coating compositions as described, are their viscosity before coating.
  • coating compositions before application to a support, if one is employed, have a viscosity of about 50 centipoises to about 15,000 centipoises and preferably, a viscosity of about 75 centipoise to about 200 centipoises.
  • the described polymers in the presence of a suitable cross-linking agent, especially an aldehyde, e.g., formaldehyde, rapidly harden under ambient conditions to form a solid.
  • a suitable cross-linking agent especially an aldehyde, e.g., formaldehyde
  • the support can contain cross-linking agents, such as formaldehyde, e.g., a paper support can contain formaldehyde which aids in adhesion of the coating to the support.
  • the coating operation can be carried out at elevated temperatures, e.g., at above about 30 C., typically about 30 C. to about C.
  • Another embodiment of the invention is in a process for removing a diffusible liquid from a permeable solid containing said liquid by contacting said permeable solid with a solid material which removes said liquid from said permeable solid, the improvement which comprises contacting said permeable solid with a drying element comprising an organic, polymeric desiccant cross-linked to an organic polymer.
  • the permeable solid which is contacted by the described drying element can be a moist photographic element.
  • the drying element of the invention can remove at least about 60%, by weight, of ditfusible liquid, such as Water, in about 1 to about 60 seconds, usually at least 35%, by weight, of water in less than 30 seconds, at
  • any ditfusible liquid can be removed from a permeable solid according to the invention which is more strongly attracted to a drying element of the invention than said permeable solid when the drying element and permeable solid are intimately contacted.
  • Suitable dilfusible liquids include, for example, water, methanol, liquid lower alkyl amines, such as ethyl amine, and lower alkanol amines, such as ethanol amine and propanol amine.
  • the invention can be employed in processing of various moist photographic elements.
  • Such photographic elements can be processed before drying in any suitable process employed for this purpose.
  • Web processing can be employed, described, for instance, in U.S. Pat. 3,179,517 of Tregillus et 211., issued Apr. 20, 1965.
  • one process which is suitable for production of a reversal image consists of the following processing steps and formulas:
  • reversal exposure may be necessary.
  • the reversal of the image may be accomplished chemically by the inclusion of a reversal agent in the color developer (e.g. butyl amine borane, as cited in the composition of the color developer below).
  • a reversal agent e.g. butyl amine borane, as cited in the composition of the color developer below.
  • a drying element and/or process of the ina/ention is useful for rapidly removing diifusible liquid, especially water, from a wide variety of photographic elements containing such liquid. For example, it can be used for removing water from any suitable photographic element in a moist condition.
  • Photographic elements employed in the practice of the invention can contain a layer comprising any of the known water permeable binding materials suitable for photographic purposes. These include, for example, gelatin, colloidal albumin, cellulose derivatives, polymerized vinyl compounds, acrylamide polymers, as well as mixtures of such binding agents. These binding agents can contain water insoluble polymers, such as polymerized ethylenically unsaturated compounds, e.g., water insoluble polymers of acrylates and methacrylates, acrylic acid, sulfoalkyl acrylates or methacrylates and the like.
  • water insoluble polymers such as polymerized ethylenically unsaturated compounds, e.g., water insoluble polymers of acrylates and methacrylates, acrylic acid, sulfoalkyl acrylates or methacrylates and the like.
  • photographic elements which can be dried according to the invention include those which contain conventional addenda such as plasticizers, coating aids,
  • antifoggants such as the azaindenes
  • hardeners such as aldehyde hardeners, e.g., formaldehyde, mucochloric acid, glutaraldehyde bis(sodium bisulfite), maleic dialdehyde, aziridines, dioxane derivatives and oxypolysac charides.
  • Sensitizing dyes useful in sensitizing such emulsions are described, for example, in U.S. Pats. 2,526,632 of Brooker and White, issued Oct. 24, 1950, and 2,503,776 of Sprague, issued April 11, 1950.
  • Spectral sensitizers which can be used are the cyanines, merocyanines, complex (trinuclear) cyanines, complex (trinuclear) merocyanines, styryls, and hemicyanines. Developing agents can also be incorporated into the emulsion if desired or can be contained in a separate contiguous layer.
  • Various silver salts can be used as the sensitive salt, such as silver bromide, silver iodide, silver chloride or mixed silver halides, such as silver chloro- 9 bromide or silver bromoiodide.
  • the silver halides used can be those which form latent images predominantly on the surface of the silver halide grains or those which form latent images inside the silver halide crystals such as described in US. Pat. 2,592,250 of Davey and Knott, issued Apr. 8, 1952.
  • Photographic elements dried in the practice of the invention can also contain speed increasing compounds such as quaternary ammonium compounds, polyethylene glycols or thioethers. Frequently, useful elfects can be obtained by adding the aforementioned speed increasing compounds to photographic developer solution employed for processing instead of, or in addition to, the photographic emulsions.
  • speed increasing compounds such as quaternary ammonium compounds, polyethylene glycols or thioethers.
  • the invention can be used to dry a layer of a photographic element intended for color photography, for example, emulsions containing color-forming couplers or emulsions to be developed by solutions containing couplers or other color-generating materials, emulsions of the mixed-packet type such as described in US. Pat. 2,698,794 of Godowsky, issued Ian. 4, 1955; in silver dye-bleach systems and emulsions of the mixed-grain type such as described in US. Pat. 2,592,243 of Carroll and Hanson, issued Apr. 8, 1952.
  • Photographic emulsions or elements dried in the practice of the invention can be sensitized using any of the well known techniques in emulsion making, for example, by digesting with naturally active gelatin or various sulfur, selenium, tellurium and/or noble metal sensitizers. Combinations of sensitizers can be employed, such as described in U.S. Pat. 3,297,446 of Dunn, issued Jan. 10, 1967, and US. Pat. 3,408,196 of McVeigh, issued Oct. 29, 1968.
  • drying elements and/ or processes of the invention can be employed in the production of layers of liquid permeable solid materials.
  • liquid permeable, drying elements and processes of the invention can be employed in the production of layers of unexposed photographic elements which require removal of water and/or other suitable liquid at some stage.
  • a typical process according to the invention for the production of a layer of a photographic element accordingly comprises applying a hydrophilic colloid coating to a substrate, the resulting coating containing water and/ or other suitable liquid, and subsequently contacting the hydrophilic colloid coating with a liquid permeable, drying element, as described, comprising an organic, polymeric desiccant, to remove a substantial portion of the water and/ or other suitable liquid from the hydrophilic colloid coating.
  • a wide range of coating methods and conditions can be employed for preparing the coatings from which liquids, e.g., water, can be removed according to the invention.
  • coating methods, compositions, and conditions commonly employed in the photographic art can be employed.
  • a typical method for production of a raw photographic emulsion layer comprises applying a coating of a photographic emulsion to a substrate, setting the resulting coating, such as by chilling or fuming with ammonia in the case of gelatino emulsion coatings, and contacting the resulting coating with a liquid permeable, drying element, as described, comprising an organic, polymeric desiccant, such as contacted with a supported or unsupported coating, as described, containing a so-called modified poly- (ethylene oxide), e.g., a so-called modified poly(ethylene oxide) containing acetoacetate groups cross-linked with formaldehyde to a polymer II, III and/or IV and to a gelatin coated support, to remove a substantial portion of the water from the raw photographic emulsion coating.
  • a so-called modified poly- (ethylene oxide) e.g., a so-called modified poly(ethylene oxide) containing acetoacetate groups cross-linked with formaldehyde to a poly
  • the raw photographic emulsion coating can be contacted using essentially the same conditions and time of contact as employed for contacting exposed and processed, wet photographic elements to effect removal of water.
  • a photographic element is typically about 1 second to about 60 seconds, although, if desired, a contact time of 1 minute to several minutes can be employed.
  • the drying element is usually removed from contact with the material dried.
  • any suitable method or means can be employed for contacting the described drying element with the material to be dried.
  • the described drying element e.g., a flexible web coated with gelatin and the described so-called modified poly(ethylene oxide) in the presence of a cross-linking agent, can be rolled in contact with the photographic film on, for instance, a spindle, for about 5 to about 60 seconds.
  • the described drying element can be in any suitable form, such as, in the form of a drum or solid, flat surface or can be a flexible web.
  • EXAMPLE 1 l on and is precipitated in isopropanol. Analysis indicates a polymer containing a mole ratio of alcohol moiety to aceto acetate moiety, i.e., the ratio of x to y, is 129:1.
  • the average molecular weight is about 1000 to about 10,000.
  • EXAMPLE 2 This illustrates preparation of a polymer employed in the practice of the invention as in Example 1.
  • EXAMPLE 3 This illustrates preparation of a polymer as in Example l.
  • EXAMPLE 4 This illustrates preparation of a polymer as in Example 1.
  • EXAMPLE 5 Two liters is prepared of an aqueous solution containing about 8% by weight of the disodium salt of a copolymer having repeating units of the formula:
  • EXAMPLE 6 This illustrates preparation of a so-called modified poly(ethylene oxide) within described Formula I.
  • n is about to about 200.
  • EXAMPLE 8 This illustrates preparation of a drying element according to the invention.
  • the coating contains approximately 6 grams/ft. of a polymer of Formula IV and 9 grams/ft. of the described modified poly(ethylene oxide). The resulting coating is permitted to solidify under atmospheric conditions.
  • EXAMPLE 9 This illustrates drying a moist photographic element according to the invention.
  • the film is a polyethylene terephthalate support containing respectively on the support (a) a red sensitive gelatino silver bromoiodide emulsion containing a cyan dye forming coupler, (b) a clear gelatin layer, (c) a green sensitive gelatino silver bromoiodide emulsion containing a magenta dye forming coupler, (d) a Carey Lea silver layer and (e) a blue sensitive gelatino silver bromoiodide emulsion containing a yellow dye forming coupler.
  • the film is 35 mm. wide and about 25.4 centimeters long. After sensitometric exposure, it is processed in a reversal process as herein described.
  • Drying of the resulting moist film is carried out by pressing the emulsion side of the film in direct contact for varying lengths of time with a drying element as described in Example 7, as set out in Table I.
  • the total percentage of water remaining in the film after direct contact with the drying element is calculated by (a) measuring the thickness of the film (including the support) with a micrometer immediately after processing but before drying and (b) again after drying.
  • the thickness measurement after processing but before drying is taken as a moisture content of TABLE I Relative percent of water Contact time (see): left in emulsion EXAMPLE 10 This illustrates preparation of a drying element according to the invention.
  • a portion of a l-liter aqueous solution containing (a) 37.5 grams of a polymer as described in Example 1, (b) 102.5 grams of a polymer as described in Example 7 and (c) 4.5 grams of formaldehyde is hand-coated on a polyethylene terephthalate film support containing a gelatino subcoat to give an approximate dry coverage of 17 grams solids/ft. (thickness 6 mils), The coating contains approximately 4.25 grams of a polymer as described in Example 1 and 12.75 grams of a polymer as described in Several samples of the drying element prepared as in Example 10 are tested by the procedure described in Example 9. The results are tabulated in Table II.
  • a solid, liquid-permeable, drying element comprising an organic polymeric desiccant cross-linked to an organic polymer.
  • a solid, liquid-permeable, drying element as in claim 1 comprising a hydrophilic ethylene oxide polymer crosslinked with formaldehyde to gelatin.
  • a solid, liquid-permeable, drying element as in claim 1 comprising (a) a support containing thereon (b) gelatin and (c) an organic polymeric desiccant which is (i) a polymer which is acetoacetylated poly(ethylene oxide) which polymer is cross-linked to said gelatin with (ii) formaldehyde.
  • a solid, liquid-permeable, drying element as in claim 1 comprising (a) a support containing thereon (b) gelatin and (c) an organic polymeric desiccant which is (i) a polymer which is the acetal of disodium 2,4-disulfobenzaldehyde and copoly(vinyl alcohol-vinyl acetoacetate) which polymer is cross-linked to said gelatin with (ii) formaldehyde.
  • a solid, liquid-permeable, drying element as in claim 1 comprising (a) a support containing thereon (b) gelatin and (c) an organic polymeric desiccant which is (i) a polymer which is acetoacetylated hydroxy ethyl cellulose which polymer is cross-linked to said gelatin with (ii) formaldehyde.
  • a coating composition comprising (a) a hydrophilic polymer containing acetoacetate groups, (b) an aldehyde and (c) a solvent.
  • a coating composition as in claim 7 comprising an aqueous solution having a viscosity of 75 to 200 centipoises at 20 C.
  • a coating composition as in claim 7 wherein said hydrophilic polymer is the acetal of disodium 2,4-disulfobenzaldehyde and copoly (vinyl alcohol-vinyl acetoacetate).
  • a process as in claim 12 wherein said permeable solid is a photographic element.
  • drying element comprises said organic polymeric desiccant which is acetoacetylated poly(ethylene oxide) cross-linked with an aldehyde to said organic polymer.
  • a process for removing moisture from a moist photographic element which comprises directly contacting said photographic element with a solid liquid permeable drying element comprising an organic polymeric desiccant cross-linked to an organic polymer.
  • organic polymeric desiccant comprises (i) acetoacetylated poly(ethylene oxide) and (ii) the acetal of disodium 2,4-disulfobenzaldehyde and copoly(vinyl alcohol-vinyl acetoacetate) cross-linked with formaldehyde to said gelatin.
  • organic polymeric desiccant comprises (i) acetoacetylated poly(ethy1- ene oxide) and (ii) the acetoacetylated hydroxy ethyl cellulose cross-linked with formaldehyde to said gelatin.
  • a solid organic polymeric desiccant composition comprising (i) an acetoacetylated poly(ethylene oxide) and (ii) the acetal of disodium 2,4-disulfobenzaldehyde and copoly(vinyl alcohol-vinyl acetoacetate) cross-linked with an aldehyde.
  • a solid organic polymeric desiccant composition comprising (i) an acetoacetylated poly-(ethylene oxide) and (ii) acetoacetylated hydroxy ethyl cellulose crosslinked with an aldehyde.

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4154612A (en) * 1975-07-25 1979-05-15 Fuji Photo Film Co., Ltd. Method of making silver halide photographic light-sensitive materials

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US5145997A (en) * 1991-02-12 1992-09-08 Sun Chemical Corporation Poly (alkylene oxide) substituted acetoacetanilides
US10767000B2 (en) 2015-04-10 2020-09-08 Battelle Memorial Institute BPA-free coatings
US10323160B2 (en) 2015-04-10 2019-06-18 Ohio Soybean Council BPA-free coatings

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4154612A (en) * 1975-07-25 1979-05-15 Fuji Photo Film Co., Ltd. Method of making silver halide photographic light-sensitive materials

Also Published As

Publication number Publication date
CA925687A (en) 1973-05-08
BE758216A (fr) 1971-04-01
FR2066650A5 (fr) 1971-08-06
GB1319112A (en) 1973-06-06

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