US2698242A - R saner - Google Patents

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US2698242A
US2698242A US29257352A US2698242A US 2698242 A US2698242 A US 2698242A US 29257352 A US29257352 A US 29257352A US 2698242 A US2698242 A US 2698242A
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water
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diisocyanate
colloid
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Priority to FR1083568D priority patent/FR1083568A/fr
Priority to DEP9915A priority patent/DE941765C/de
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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
    • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/91—Photosensitive materials characterised by the base or auxiliary layers characterised by subbing layers or subbing means
    • G03C1/93—Macromolecular substances therefor

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  • ./-Organic polyisocyanale or polyisolhiocyanale L/ Walerpermeable colloid and silver halide v Hydrophobic film base e.g., cellulose derivative, polyester, etc.
  • Water-permeable colloid and silver halide Water-permeable colloid, e.g., gelatin Organic polyisocyanale or polyisolhiocyanale Hydrophobic film base, e.g., cellulose derivative, polyesler,elc.
  • Water-permeable colloid and silver halide Water-permeable colloid e.g., gelatin Organic polyisocyanale or palyisolhiocyanale Vinylidene chloride-acrylic esler-ilacanic acid copolymer Polyethylene lerephlhalale INVENTOR WILLIAM RUSSELL SANER ATTORNEY United States Patent PHOTOGRAPHIC ELEMENTS AND PREPARATION THEREOF William Russell Saner, Plainfield, N. 1., assignor to E. I. du Pont de Nemours and Company, Wilmington, DeL, a corporation of Delaware Application June 9, 1952, Serial No. 292,573 12 Claims. (Cl.
  • This invention relates to photographic film elements and to their preparation. More particularly it relates to a process of improving the anchorage between a hydrophobic film base and a colloid silver halide layer. Still more particularly it relates to a process for improving the anchorage between (1) a photographic film base consisting of an oriented polyester film bearing on at least one surface, a substratum coating composed of a copolymer of vinylidene chloride, an acrylic ester and itaconic acid, and (2) a water-permeable colliod layer, and to the resulting photographic film.
  • Photographic manufacturers are continuously trying to obtain improvements in the anchorage of photographic emulsions to hydrophobic film bases. With the advent of synthetic polymer films the conventional procedures are not always satisfactory.
  • the preparation of photographic films by coating an orientable highly polymeric ester of a dicarboxylic acid and a dihydric alcohol, e. g., a polyethylene terephthalate with an aqueous dispersion of a copolymer of vinylidene chloride, an acrylic acid ester and itaconic acid, then biaxially orienting the coated base and subsequently applying a water-permeable colloid layer is described in Alles and Saner, U. S. app. Ser. No. 151,274, filed March 22, 1950, now U. S.
  • Patent 2,627,088 It has been found that if such copolymer coated polyester film bases are not coated within a short time after the layer of copolymer has dried, the degree of adherence between the base and a subsequently applied waterpermeable colloid layer progressively decreases with the length of time. This is true even when a water-permeable colloid sublayer is applied to the copolymer layer.
  • the present invention is not limited to the use of poyester film bases which are provided with a vinylidene chloride-acrylic ester-itaconic acid copolymer layer, although that constitutes the preferred embodiment, as the anchorage between water-permeable colloid silver halide emulsion layers and other types of film base can be improved in like manner by applying a layer of an organic polyisocyanate or polyisothiocyanate before applying a water-permeable colloid layer and/or waterpermeable colloid silver halide emulsion layer.
  • the film base or support may consist of a hydrophobic cellulose derivative, e.
  • An object of this invention is to provide a new process for anchoring colloid silver halide emulsion layers to hydrophobic film supports. Another object of this invention is to provide a process for improving the adherence between photographic film base having a film support composed of an oriented polyester and a substratum coating composed of a copolymer of vinylidene chloride. an acrylic ester and itaconic acid and a water-permeable colloid silver halide emulsion. Yet another object is to 2,698,242 Patented Dec. 28, 1954 "ice provide such a process which can be practiced with the usual equipment of a photographic film manufacturer. A further object is to provide such a process which is economical and utilizes available chemicals. A still further object is to provide photographic elements of the above type which have a novel anchoring substratum. Still other objects will be apparent from the following description of the invention.
  • the process of this invention in its broader aspects consists in coating a hydrophobic film base with a thin layer of an organic polyisocyanate or polyisothiocyanate and then applying a layer of a water-permeable colloid and/or a Water-permeable silver halide emulsion layer.
  • the organic polyisocyanate or polyisothiocyanate can be applied from a solution in a suitable organic solvent, preferably a volatile solvent which does not have any significant solvent action on the film base, which solution is essentially free from water or anhydrous and which does not react with the isocyanate compound. After drying an aqueous solution of a water-permeable colloid, e.
  • gelatin may be applied and then an aqueous dispersion of light-sensitive silver halides in an aqueous solution of a water-permeable colloid, e. g., gelatin is applied to the dry light-insensitive colloid substratum.
  • aqueous dispersion of silver halides can be directly applied to the polyisocyanate or polyisothiocyanate layer.
  • the colloid layer is then heated, e. g., from 50 C. to C.
  • an orientable hydrophobic film composed of a polyester of a dicarboxylic acid and a dihydric alcohol of the type described in Carothers U. S. P. 2,071,250 and particularly the high-melting difiicultly soluble, usually microcrystalline, cold-drawing linear, highly polymerized esters of terephthalic acid and glycols of the series HO(CH2)1OH, where n is an integer with the range of 2 to 10, described in Whinfield et al. U. S. P.
  • Fig. 1 is a schematic cross-sectional view of one type of film element of this invention.
  • Fig. 2 is a schematic cross-sectional view of another type of film element of this invention.
  • Fig. 3 is a schematic cross-sectional view and yet another type of film element of this invention.
  • a hydrophobic film base which may be composed of a cellulose derivative, polyester, etc. as described above, is provided with a layer 2 composed of an organic polyisocyanate or polyisothiocyanate which in turn is provided with a layer 3 composed essentially of water permeable colloid and silver halide.
  • the film element is like that described in Fig. 1 except that a layer 3 composed of a waterperrneable colloid, e. g., gelatin is interposed between the layer of polyisocyanate or polyisothiocyanate and the water-permeable colloid silver halide emulsion layer.
  • a layer 3 composed of a waterperrneable colloid, e. g., gelatin is interposed between the layer of polyisocyanate or polyisothiocyanate and the water-permeable colloid silver halide emulsion layer.
  • the film element of Fig. 3 consists of a hydrophobic polyethylene terephthalate film base 1' which is provided with a layer of 2 composed of a vinylidene chlorideacrylic ester-itaconic acid copolymer, which in turn is coated with layer 2 composed of an organic polyisocyanate or polyisothiocyanate.
  • layer 2 composed of an organic polyisocyanate or polyisothiocyanate.
  • the latter layer in turn supports water-permeable colloid silver halide emulsion layer 3.
  • the useful acrylic esters which may housed in the copolymers are the alkyl esters of acrylic and methacrylic acids having from 1 to 18 carbon atoms in the alkyl group (e. g., methyl methacrylate, ethyl methacrylate, butyl methacrylate, octyl methacrylate, n-dodecyl methacrylate, n-octadecyl methacrylate), methyl acrylate, ethyl acrylate and propyl acrylate; vinyl chloride, acrylonitrile and methacrylonitrile.
  • alkyl esters of acrylic and methacrylic acids having from 1 to 18 carbon atoms in the alkyl group (e. g., methyl methacrylate, ethyl methacrylate, butyl methacrylate, octyl methacrylate, n-dodecyl methacrylate, n-octadecy
  • the monomers may be copolymerized by various methods.
  • the copolymerization may be conducted in aqueous dispersion containing a catalyst and activator, e. g., ammonium persulfate and meta sodium bisulfite, and an emulsifying and/or dispersing agent.
  • a catalyst and activator e. g., ammonium persulfate and meta sodium bisulfite
  • an emulsifying and/or dispersing agent e.g., ammonium persulfate and meta sodium bisulfite
  • an emulsifying and/or dispersing agent e.g., ammonium persulfate and meta sodium bisulfite
  • an emulsifying and/or dispersing agent e.g., ammonium persulfate and meta sodium bisulfite
  • an emulsifying and/or dispersing agent e.g., ammonium persulfate and meta sodium bisulfite
  • mercaptans such as ethyl mercaptan, lauryl mercaptan, tertiary dodecyl mercaptan, etc., which are effective in reducing cross-linking in the copolymer.
  • the mercaptans should be used in concentrations of 0.1% to 5.0% by weight, based on the weight of polymerizable monomers present in the charge.
  • the layer of polyisocyanate and polyisothiocyanate and water-permeable colloid and/or water-permeable colloid silver halide dispersions are applied as described above and dried.
  • Example I Asample of polyethylene terephthalate film, having a melting point above 200 C., and an intrinsic viscosity of approximately 0.50 in a mixture of 2,4,6-trichlorophenol and phenol (70: 100 parts by weight), was coated with an aqueous dispersion of a vinylidene chloride-acrylic esteritaconic acid'copolymer of the type described in Alles and Saner U. S. Patent No. 2,627,088. After drying at 50 C., the film was stretched biaxially about 3 times its original dimensions, and coated with a 1% solution of methylene bis (4-phenylisocyanate) in methylene chloride.
  • Example 11 The entire procedure of Example I was repeated except that toluene-2,4-diisocyanate was substituted for the diisocyanate of that example. The results were similar.
  • Example III The entire procedure pf Example I was repeated except that the dimer of toluene 2,4-diisocyanate was substituted for the diisocyanate of that example. The results were similar.
  • Example IV A sample of polyethylene terephthalate film, having a melting point above 200 C., and an intrinsic viscosity of approximately 0.50 in a mixture of 2,4,6-trichlorophenol and phenol (70:100 parts by weight) was coated with an aqueous dispersion of a vinylidene chloride copolymer of the type described in U. S. Patent 2,627,088. After drying at 50 C., the film was stretched biaxially (3 times the original dimensions in both directions) and treated with a 1% solution of methylene bis[4-phenylisocyanate] in methylene chloride.
  • Example 'V A sample of polyethylene terephthalate film base having-a melting point above 200 C., and an intrinsic viscoslty of 'approximately 0.50 infa mix'tur'e of 2,4,6-trichlorophenpl and phenol (70:100 parts by weight), was treate w t 1.11%, fs lu 10 et 'y e -D 'y lso'cyan'ate) "in methylene chloride, 'dried a't'50 'C., h'eated at 100 C. for 2 minutes and coated with a gelatinosilver halide emulsion. After exposing, developing, washing, fixing and washing in the manner described in Example I, the adhesion both wet and dry, was satisfactory.
  • Example VI A sample of polyethylene terephthalate film of the type described in Example V was treated as in Example V, except that the film had been biaxially stretched before the solution of methylene bis (4-phenylisocyanate) was applied. The results, after coating with a gelatino-silver halide emulsion, and processing as described in Example I, were similar.
  • Example VII A sample of biaxially stretched polyethylene terephthalate of the type described in Example V was treated with a solution of methylene bis (4-phenyl-isocyanate) as described in Example V. After drying, a gelatin dispersion of the following composition was applied over the diisocyanate layer:
  • Example VIII fobenzaldehyde-polyvinyl mixed acetal 1.5 Boric acid 1.9 Diisopropanolamin'e 1.3 Acetone 40.0 Ethyl alcohol (95%) 55.3
  • the film thus treated was heated for 2 minutes at 100 C. and coated with a polyvinyl acetal color-former-silver halide emulsion containing 1.5% by weight of silver iodobromide comprised of approximately 1.3% silver iodide and 98.7% silver bromide, dispersed in the polymeric color former (3.8% by weight of the total emulsion) described in Martin U. S. Patent 2,513,190. After drying, the emulsion was found to have good adherence to the film base. It was exposed and processed in the following solutions:
  • Example IX Example VII was repeated except that toluene 2,4-di
  • Example VII was repeated except that hexamethylene diisocyanate was substituted for the methylene bis (4- phenylisocyanate) of that example.
  • Example XI Example VII was repeated except that the dimer of toluene-2,4-diisocyanate was substituted for the methylene bis (4-phenylisocyanate) of that example. Similar results were obtained.
  • the diisocyanate or diisothiocyanate layer is very thin and the remaining layers have their conventional thicknesses.
  • the thicknesses of the various layers may be as set forth in aforesaid Patent No. 2,627,088.
  • Exemplary compounds include polymethylene diisocyanates and diisothiocyanates such as ethylene diisocyanate, trimethylene diisocyanate, do-' decamethylene diisocyanate, hexamethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, and the corresponding diisothiocyanates; alkylene diisocyanates and diisothiocyanates such as propylene 1,2- diisocyanate, 2,3-dimethyltetramethylene diisocyanate and diisothiocyanate, butylene-1,2-diisocyanate, butylene-1,3- diisothiocyanate, and butylene-l,3-diisocyanate; alkylidene diisocyanates and diisothiocyanates such as ethylidene diisocyanate (CH3CH(NCO)2) and heptylidene diisothiocyanate (CH3(CH
  • the preferred diisocyanates, diisothiocyanates and mixed isocyanate-isothiocyanates have the general formula ZCNRNCZ in which R is a divalent hydrocarbon radical and Z is a chalcogen of atomic weight less than 33.
  • Suitable diisocyanate dimers are described in Kirkpatrick and Willett, N. S. app. Ser. No. 261,922, filed December 15, 1951.
  • solvents or mixtures of solvents for the cyanate compounds which have a slight solvent action on the particular film base and do not react with polyisocyanates or polyisothiocyanates.
  • solvents include hydrocarbons, ethers, esters, and chlorinated hydrocarbons.
  • the polyisocyanate or polyisothiocyanate can constitute from 0.10% to 10% and preferably 0.25% to 4.0% by weight of the solution.
  • solvents are benzene, toluene, xylene hexane, heptane, dioxane, methylene chloride, chloroform,,trichlorethylene, tetrachlor'ethane, carbon tetrachloride, methyl acetate, ethyl acetate andmixtures of'two or more ofsuchs'o'lvents.
  • the heating period may vary considerably depending: on the particular temperature, colloid layer, colloid silver halide layer, etc.
  • a practical period is from /2 minute tov 15minutes.
  • colloid silver-halide emulsions In place of the specific colloid silver-halide emulsions described in the foregoing examples there may becoated onto the layer of isocyanate compound various other colloid silver halide emulsion layers and water-permeable colloid sublayers free from light-sensitivesilver-halides.
  • additional colloids which can be anchored in accordance with the invention. are polyvinyl alcohols and water-soluble polyvinyl alcohol derivatives in general, e. g., partially hydrolyzed polyvinyl acetates, and mixed polyvinyl-chloride-acetatcs, hydrolyzed interpolymers of vinyl acetate with unsaturated compounds, for example, maleic anhydride, acrylic acid esters, etc.
  • colloids include hydrophilic partially substituted polyvinyl esters and acetals and the low substituted cellulose esters of saturated aliphatic monocarboxylic acids of 2 to 4 carbon atoms and low substituted cellulose ethers, e. g., methyl-cellulose, ethyl-cellulose, etc.
  • Additional natural colloids include casein, albumin, gum arabic, agar agar, polyglycuronic acid, etc., which are also anchored to supports by these new substrata.
  • the invention can be used in the preparation of all types of photographic film elements including black and white and color films for motion picture and still photography, portrait film, document recording film, lithographic film, medical, dental and industrial X-ray .film, soundrecording film, films of the type described in Frankenburger et al. U. S. 2,180,409, stripping films'of the type described in Jennings U. S. Patent 2,462,503, etc.
  • An advantage of the invention is that it provides a simple and economical manner for improving the anchorage of water-permeable colloid silver halide emulsion layers to hydrophobic film bases. Another advantage is that the invention can be practiced with the conventional equipment of a photographic film manufacture. The invention enables one to obtain good anchorage between formaldehyde hardened gelatinosilver halide emulsions and a hydrophobic film base. A further advantage is that the invention enables one to obtain adequate anchorage to a hydrophobic film base that has been aged. The invention is particularly advantageous with the copolymer coated polyester film bases described above. Still other advantages will be apparent from the above description of the invention.
  • a process which comprises coating an essentially anhydrous organic solvent solution containing an organic isocyanate compound taken from the group consisting of polyisocyanates and polyisothiocyanates onto a hydrophobic film base, drying the resulting layer, applying an aqueous solution containing a water-permeable colloid to the layer of isocyanate compound and drying the film element at a temperature from-50 (3.10
  • a process which comprises coating an essentially anhydrous organic solvent solution containing an organ c" polyisocyanate onto a hydrophobic film base, drying the resulting layer, applying an aqueous solution-containing a water-permeable colloid to the layer of polyisocyanate and heating the resulting element to a temperature from 50 C. to 150 C.
  • a process which comprises coating an essentially anhydrous organic; solven olu io con aining: an. rcmatie'diisocyanate. onto a hydrophobic film base, drying the r lt n v y r apply ng. n aqueo s. so ut on. @01 taining a. w t r-p rme b e coll i to; he ay r at dii o cyanate, and heating the resulting element; to. a tempera: ture from 50 C. to. 150 C.
  • a process which comprises coating an essentially anhydrous organic solvent solution containing an aromatic diisothiocyanate onto a hydrophobic film base, drying e. resulting laye pp y ng aque us olu n containing a water-permeable. Colloid to the layer of diisothiocyanate and heating the resulting element to a temperature from 50 C. to 150 C.
  • a process which comprises coating an essentially anhydrous volatile organic solvent solution containing an aromatic diisocyanate onto a hydrophobic film base;
  • a process which comprises coating an essentially anhydrous volatile organic solvent solution containing an aromatic diisocyana'te onto a hydrophobic film base, consisting of a polyethylene terephthalate film bearing a coating of a vinylidene chloride-acrylic ester-itaconi'c acid copolymer substratum, drying the resulting layer, coating an aqueous solution of gelatin onto the diisocyanate layer, drying the gelatin layer, applying a gelatino-silver-halide emulsion layer to said gelatin layer and heating the resulting element to a temperature from 50 C. to 100 C., fora period of /2 to 15 minutes.
  • a photographic film element comprising a hydrophobic film base, bearing in order on one surface a stratum composed of an organic isocyanate compound taken from the group consisting of polyisocyanates and pol isothiocyanates and at least one water-permeable col oid layer.
  • a photographic element comprising a hydrophobic film base, bearing in order on one surface a stratum composed of an isocyanate compound taken from the group consisting of polyisocyanates and polyisothiocyanates, a. tayer of gelatin and a gelatino-silver-halideemulsion ayer.
  • said film base is composed of a' polyethylene terephthalate film having a substratum composed of a vin'ylidenechloride-acrylic ester.-itaconic acid copolymer.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Laminated Bodies (AREA)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)
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US29257352 1952-06-09 1952-06-09 R saner Expired - Lifetime US2698242A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
BE520417D BE520417A (fr) 1952-06-09
US29257352 US2698242A (en) 1952-06-09 1952-06-09 R saner
GB13951/53A GB726736A (en) 1952-06-09 1953-05-18 Photographic film bases and elements
FR1083568D FR1083568A (fr) 1952-06-09 1953-05-28 Procédé de préparation d'éléments de pellicules photographiques et produits en résultant
DEP9915A DE941765C (de) 1952-06-09 1953-06-10 Photographischer Film und Verfahren zu seiner Herstellung

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GB (1) GB726736A (fr)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2805173A (en) * 1956-06-11 1957-09-03 Ici Ltd Photographic film base and process for the manufacture thereof
US2943936A (en) * 1956-12-13 1960-07-05 Keuffel & Esser Co Cartographic material
US3005728A (en) * 1956-10-19 1961-10-24 Tee Pak Inc Cellulosic laminates
US3030223A (en) * 1959-02-02 1962-04-17 Minnesota Mining & Mfg Bonding structure for laminates
US3043695A (en) * 1959-02-27 1962-07-10 Du Pont Photographic films
US3052543A (en) * 1958-12-05 1962-09-04 Du Pont Photographic film base and film
US3090716A (en) * 1958-09-12 1963-05-21 Gates Rubber Co Adhesive treatment and article of manufacture
US3117046A (en) * 1959-09-30 1964-01-07 Agfa Ag Process for joining a polycarbonate resin sheet to a cellulose ester sheet
US3196035A (en) * 1960-07-16 1965-07-20 Fuji Tsushinki Seizo Kk Method of bonding an epoxy coating to a polyisocyanate treated polyester fiber base
US3277032A (en) * 1958-11-03 1966-10-04 Eastman Kodak Co Blends of cellulose triacetate with methyl acrylate polymer
US3393087A (en) * 1955-04-22 1968-07-16 Monsanto Co Plastic vessel coated with epoxy resin containing lacquer
US3502475A (en) * 1967-07-13 1970-03-24 Du Pont Highly adherent coated films and method of producing same
US3775114A (en) * 1968-07-15 1973-11-27 Itek Corp Photosensitive silver halide layers and process
USB354008I5 (fr) * 1973-04-24 1975-01-28
US3885080A (en) * 1971-11-03 1975-05-20 Ilford Ltd Cellulosic film base assembly
US3885966A (en) * 1970-06-12 1975-05-27 Itek Corp Photosensitive silver halide layers and process

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2216736A (en) * 1938-09-27 1940-10-08 Du Pont Photographic film
US2287827A (en) * 1938-07-30 1942-06-30 Standard Oil Co California Pipe coating coupler
US2333917A (en) * 1941-07-15 1943-11-09 Du Pont Coated fabric
US2430479A (en) * 1941-07-23 1947-11-11 Du Pont Bonding of laminates by means of isocyanates
US2491023A (en) * 1945-09-12 1949-12-13 Du Pont Photographic film elements
US2627088A (en) * 1950-03-22 1953-02-03 Du Pont Preparation of oriented coated films

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2287827A (en) * 1938-07-30 1942-06-30 Standard Oil Co California Pipe coating coupler
US2216736A (en) * 1938-09-27 1940-10-08 Du Pont Photographic film
US2333917A (en) * 1941-07-15 1943-11-09 Du Pont Coated fabric
US2430479A (en) * 1941-07-23 1947-11-11 Du Pont Bonding of laminates by means of isocyanates
US2491023A (en) * 1945-09-12 1949-12-13 Du Pont Photographic film elements
US2627088A (en) * 1950-03-22 1953-02-03 Du Pont Preparation of oriented coated films

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3393087A (en) * 1955-04-22 1968-07-16 Monsanto Co Plastic vessel coated with epoxy resin containing lacquer
US2805173A (en) * 1956-06-11 1957-09-03 Ici Ltd Photographic film base and process for the manufacture thereof
US3005728A (en) * 1956-10-19 1961-10-24 Tee Pak Inc Cellulosic laminates
US2943936A (en) * 1956-12-13 1960-07-05 Keuffel & Esser Co Cartographic material
US3090716A (en) * 1958-09-12 1963-05-21 Gates Rubber Co Adhesive treatment and article of manufacture
US3277032A (en) * 1958-11-03 1966-10-04 Eastman Kodak Co Blends of cellulose triacetate with methyl acrylate polymer
US3052543A (en) * 1958-12-05 1962-09-04 Du Pont Photographic film base and film
US3030223A (en) * 1959-02-02 1962-04-17 Minnesota Mining & Mfg Bonding structure for laminates
US3043695A (en) * 1959-02-27 1962-07-10 Du Pont Photographic films
US3117046A (en) * 1959-09-30 1964-01-07 Agfa Ag Process for joining a polycarbonate resin sheet to a cellulose ester sheet
US3196035A (en) * 1960-07-16 1965-07-20 Fuji Tsushinki Seizo Kk Method of bonding an epoxy coating to a polyisocyanate treated polyester fiber base
US3502475A (en) * 1967-07-13 1970-03-24 Du Pont Highly adherent coated films and method of producing same
US3775114A (en) * 1968-07-15 1973-11-27 Itek Corp Photosensitive silver halide layers and process
US3885966A (en) * 1970-06-12 1975-05-27 Itek Corp Photosensitive silver halide layers and process
US3885080A (en) * 1971-11-03 1975-05-20 Ilford Ltd Cellulosic film base assembly
USB354008I5 (fr) * 1973-04-24 1975-01-28
US3925081A (en) * 1973-04-24 1975-12-09 Polaroid Corp Photographic products containing anti-reflection layer
US4066814A (en) * 1973-04-24 1978-01-03 Polaroid Corporation Transparent supports for photographic products

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GB726736A (en) 1955-03-23
DE941765C (de) 1956-04-19
FR1083568A (fr) 1955-01-11

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