US2698241A - Photographic elements and process of preparing the same - Google Patents

Photographic elements and process of preparing the same Download PDF

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Publication number
US2698241A
US2698241A US292387A US29238752A US2698241A US 2698241 A US2698241 A US 2698241A US 292387 A US292387 A US 292387A US 29238752 A US29238752 A US 29238752A US 2698241 A US2698241 A US 2698241A
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Prior art keywords
weight
polyester
diisocyanate
film
acid
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US292387A
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English (en)
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Saner William Russell
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EIDP Inc
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EI Du Pont de Nemours and Co
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Priority to BE520491D priority Critical patent/BE520491A/xx
Priority to IT491646D priority patent/IT491646A/it
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Priority to US292387A priority patent/US2698241A/en
Priority to GB14298/53A priority patent/GB732607A/en
Priority to FR1088197D priority patent/FR1088197A/fr
Priority to DEP9899A priority patent/DE941764C/de
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Publication of US2698241A publication Critical patent/US2698241A/en
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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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/0427—Coating with only one layer of a composition containing a polymer binder
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/043—Improving the adhesiveness of the coatings per se, e.g. forming primers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/056—Forming hydrophilic coatings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
    • C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2475/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers

Definitions

  • This invention is concerned withphotographic iilms Which have a unique substratum.
  • 'More particularly 'it is concerned with photographicfilms which have a hydrophobic film base, a substratumcomposed ofa mixture ple andeffective and provide firmv anchorage ofa colloid .silver halide emulsion to a hydrophobic film'base both While under wet and dry conditions.
  • stilllfurther-object is to provide such anchorage when the'base'is composed of a polyethylene terephthalate.
  • a colloid silver'halide emulsion layer can be firmly anchored to a hydrophobic orientable polyester film'base by'first applying to the sur- :face or surfaces of thefilmbasea solution oframixture of (1) a polyester of a glycol and terephthalic acid which has amolecular weight in excess of 5,000 and is soluble to the extent of atleast /2 by weight in trichlorethylene and (2) anorganic polyisocyanate or an organic -polyisothiocyanate including diisocyanate dimers.
  • Com- ponent (2) may be presentin anamount constituting from 1% to 50% by weight of the solid materials-pres- 'ent in the coating solution.
  • the mixture of the polyester and polyisocyflnate or polyisothiocyanate can be applied to the'orienta'blepoiyester base from about /z% to 25% or'moreby'weight solution in a'suitable non-reactive solvent such as chlorinated hydrocarbon.
  • a'suitable non-reactive solvent such as chlorinated hydrocarbon.
  • the solvents should be'volatile and preferred solvents are, methylene chloride, t'riChlorethylene, carbon tetrachloride, etc.
  • the water-permeablecolloid may be gelatin, polyvinyl alcohol, a partiallyhydrolyzeldj p0lyvinyl acetace or chloracetate, apolyvinyl. acetalor a-cellulose derivative, all of hydrophilic character.
  • Polyesters suitable for use'in the mixturesofthessnblayer that have a substantial solubility in trichlorethylene can be made by condensing a mixture of (-1-) a -poly- 'methylene glycol havingfrom 2 to l0 methylen'e groups and (2) a polyethyleneglycol containing" from'l to 5 'oxyethylene radicals with terephthalic't acid oran acid r chloride oracid bromide thereof, ora diester thereof with an alkanol of 1 to 6 carbon :atoms.
  • Thexmol-percent of polyethylene glycol in the polymethylenezglycol/polyethylene glycol mixture may vary from 20% to 100%, with a preferred range of -25 'to 75%.
  • Suitable.polyesters are those.obtainable by condensing a polymethylene glycolLliavin'gLZ; to"10 methylene groups with a mixture of (1-) .tereph'thalic acid or'an acid 'chloride'or acidibromide' thereof, or a diester thereof withan' alkanol of'1'to6 carbon' fatoms and (2) a saturated aliphatic *dicarboxylic'acidof 4 to 16 carbon atoms or an acid chloride or anacidbromide 2,698,241 Patented Dec. 28,1954
  • Preferred aliphatic :dicarboxylic"acid compounds are adipic,'sebaciciacid and azelaic acid' and :their .acid .chlorides and bromides, and their dimethyl and diethyl esters.
  • the polyesterificationreactioncan takeplacein the same manner described in:the preceding paragraph.
  • polyesters :andpolymethylene glycol should be in excess and'the terephthalic acid compound should constitute at least 25% of the total acid compound, and the aliphaticdicarboxylic acid compound may'cons'titute from 10% to 75% of the total acid compound.
  • the aliphaticdicarboxylic acid compound may'cons'titute from 10% to 75% of the total acid compound.
  • 'In addition to these two compounds'there may alsobe' present from 1% to 25% of another dicar'boxylic acid compound which is capable offorming a polyester by a condensation reaction.
  • bibenzoic acid, phthalic acid, isophthalic acid and their dimethyl and 'diethyl esters are bibenzoic acid, phthalic acid, isophthalic acid and their dimethyl and 'diethyl esters.
  • Fig. 2 is a schematic cross-sectional view of another type of .film element of-the invention.
  • the'film element is like that described in' Fig. '1 except that a sublayer 3 composed of a water-permea- .blecolloid, e. g., gelatin is interposed between the'layer 2-and silver halide emulsion layer 3.
  • a sublayer 3 composed of a water-permea- .blecolloid, e. g., gelatin is interposed between the'layer 2-and silver halide emulsion layer 3.
  • anyofthe conventional coating methods can be used for applying the layer of the mixture of the solvent-soluble polyester and the poiyisocyanate or polyisothiocyanate to the surface of the film support, e. g.,.coating from a hop- -per,. skim coating where the surface ofthe filnrpa sses un'der azrollerand contactswiththe'surface of the liquid, coating with applicator or transfer rolls, spray coating, etc.
  • "'Do'ctorblades, air doctor blades, etc. can be used to remove excess'liquid. After the sublayerhas been applied to one or both surfaces of the sheet of film th'e sublayer is dried by heating it to a temperature of 50 C. or less to C. or more. A current of air can be passed over the coated surface during this'drying operation.
  • Example I A polyester was preparedbyheating dimethyl terephthalate with a stoichiometrical excess of diethylene glycol .at.170.220 C,. in the presence of- 003% byweight oflitharge based on-the-dimethyl terephthalate untilevolut-ion.of methanol ceased. The temperature wasthen increased to 250 to 280 C., and the pressure reduced to 0.1 to 0.5 mm. of mercury. Diethylene glycol was evolved as polymerization proceeded. The resulting polyester, after cooling to room temperature, was clear, soft and flexible and had an intrinsic viscosity of 0.64 in a 40/60 by volume phenol-tetrachloroethane mixture.
  • the film was washed in water for 10 minutes and found to have good wet anchorage.
  • Example II A photographic film was prepared, exposed and processed as in Example 1, except that a polyester prepared by reacting dimethyl terephthalate and adipic acid in equal molar quantities with ethylene glycol, was substituted for the polyester of Example 1.
  • Example III A photographic film was prepared, exposed and processed as in Example I, except that a polyester prepared by reacting dimethyl terephthalate and sebacic acid in equal molar quantities with ethylene glycol was substituted for the polyester of Example I.
  • the wet and dry anchorages were similar.
  • Example V A photographic film was prepared, exposed and processed as in Example I, except that a polyester prepared by reacting dimethyl terephthalate, dimethyl bibenzoate, and azelaic acid (40/20/40 mole percent) with ethylene glycol was substituted for the polyester of Example I.
  • the wet and dry anchorages were similar.
  • Example VI A photographic film was prepared, exposed and processed as in Example I, except that a polyester, prepared by reacting dimethyl terephthalate, dimethyl isophthalate and sebacic acid (50/25/25 mole percent) with ethylene glycol, was substituted for the polyester of Example I.
  • Example VII The entire procedure of Example II was repeated, except that the film base was not biaxially stretched. The wet and dry anchorages were good.
  • Example VIII Example II was repeated except that no gelatin sublayer was applied to the base, the gelatino-silver halide layer being applied to the base directly.
  • the wet and dry anchorages were adequate but not quite as good as in Example I.
  • Example IX Example II was repeated except that toluene-2,4-diisocyanate was substituted for methylene bis (4-phenylisocyanate) and similar anchorage results were obtained.
  • Example X Example II was repeated except that the dimer of toluene-2,4-diisocyanate was substituted for methylene bis (4-phenylisocyanate) and similar anchorage results were obtained.
  • Example XI A 4% solution in methylene chloride of the polyester of Example II, containing 25% methylene bis (4-phenylisocyanate), based on the polyester, was applied to biaxially stretched polyethylene terephthalate film. After drying, a layer of meta-(benzoylacetamido)-benzaldehyde-sodium-o-sulfobenzaldehyde polyvinyl mixed acetal described in McQueen U. S. Patent 2,513,190 having the following composition was applied:
  • the film was dried at 50 C. and heated at C. for two minutes and coated with a polyvinyl acetal color former silver halide dispersion 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 U. S. Patent 2,513,190. After drying at 75 F. the emulsion was found to have good adherence to the film base. It was exposed and processed in the following solutions:
  • Suitable diisocyanate dimers are described in Kirkpatrick and Willett, U. S. application Ser. No. 261,922, filed December 15, 1951. These compounds are more reactive when the coated film is heated to an elevated temperature, e. g., 150 C.
  • 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.
  • colloid silver-halide emulsions there may be coated onto the layer of isocyanate compound various other colloid silver halide emulsion layers and water-permeable colloid sublayers free from light-sensitive silver-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-acetates, hydrolyzed interpolymers of vinyl acetate with unsaturated compounds, for example, maleic anhydride, acrylic acid esters, etc.
  • colloids of the last mentioned types are disclosed in United States Patents 2,276,322, 2,276,323 and 2,397,866.
  • Still other 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.
  • three diiferentially sensitized colloid silver halide emulsion layers containing color formers or using colloid color formers as the binding agent for the silver halide grains can be used. These layers should be so arranged and sensitized that they record light of a difierent color of the visible spectrum.
  • the color formers thus can be selected to yield yellow, blue-green (cyan) and magenta quinoneimine, azomethine, etc., dyes in the appropriate layers as is common in the art and described in Jennings 2,397,864 and other patents. Filter dyes may be present in one or more of the above color former layers or in a separate 6 stratum, e.
  • aiyellow filter dye is used in a stratum above the two lightesensitive layers most .distantfrom the camera side 'of the filmt-
  • An advantage of this-invention is that itFprOVidesa-simple and economical methodof subbing film base; Another advantage is that the films have; good and adequatean: chorage between thefilm base and a colloid silver halide emulsion layer. This advantage is of special importance with regard to films having a polyethylene terephthalate base. A further advantage is that the anchorage is equally good' whether the mixture is applied to-oriented or nom oriented. film. Still' other advantages 'will be 'apparent from the above.
  • a photographic element comprising a hydrophobic orientable polyester film base bearing on at least one surface a substratum composed of a mixture of 99 to 50 parts by weight of a polyester of a glycol and terephthalic acid which has a molecular weight in excess of 5,000 and is soluble to the extent of at least /2% by weight in trichlorethylene and 1 to 50 parts by Weight of an organic compound taken from the group consisting of organic polyisocyanates and organic polyisothiocyanates and having a water-permeable colloid layer in contact with said substratum.
  • a photographic film comprising a hydrophobic orientable polyester film base bearing on at least one surface a substratum composed of a mixture of 99 to 50 parts by weight of a polyester of a glycol and terephthalic acid which has a molecular weight in excess of 5,000 and is soluble to the extent of at least /2% by weight in trichlorethylene and 1 to 50 parts by weight of an organic compound taken from the group consisting of organic polyisocyanates and organic polyisothiocyanates, having a water-permeable colloid layer on said substratum and having a water-permeable colloid silver halide emulsion layer on said latter layer.
  • a photographic film comprising a polyethylene terephthalate film base bearing on at least one surface a substratum composed of a mixture of 99 to 50 parts by weight of a polyester of a glycol and terephthalic acid which has a molecular weight in excess of 5,000 and is soluble to the extent of at least /2% by weight in trichlorethylene and 1 to 50 parts by weight of an organic compound taken from the group consisting of organic polyisocyanates and organic polyisothiocyanates and having a water-permeable colloid layer in contact with said substratum.
  • diisocyanate is methylene bis(4-phenylisocyanate).
  • a photographic element comprising a hydrophobic orientable polyester film base bearing on at least one surface a substratum composed of a mixture of 99 .to 50 parts by weight of a polyester of a glycol and terephthalic acid which has a molecular weight in excess of 5,000 and is soluble to the extent of at least /2% by Weight in trichlorethylene and 1 to 50 parts by weight of an organic compound taken from the group consisting of organic polyisocyanates and organic polyisothiocyanates and having a gelatin silver halide emulsion layer in contact with said substratum.
  • a photographic film comprising a polyethylene terephthalate film base bearing on one surface a substratum composed of a mixture of 99 to 50 parts by weight of a polyester of a glycol and terephthalic acid which has a molecular weight in excess of 5,000 and is soluble to the extent of at least /z% by weight in trichlorethylene and 1 to 50 parts by weight of an organic compound taken from the group consisting of organic polyisocyanates and organic polyisothiocyanates, a gelatin layer on said substratum and a gelatino silver halide emulsion layer on said gelatin layer.
  • a process which comprises applying to at least one surface of a hydrophobic orientable polyester film base, a film-forming mixture in a solvent containing 99 to 50 parts by weight of a polyester of a glycol and terephthalic acid which has a molecular weight in excess of 5,000 and is soluble to the extent of at least /2% by weight in trichlorethylene and 1 to 50 parts by Weight of an organic compound taken from the group consisting of organic polyisocyanates and organic polyisothiocyanates, drying the resulting layer and coating thereon a Water-permeable colloid layer.

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  • Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Laminated Bodies (AREA)
  • Paints Or Removers (AREA)
US292387A 1952-06-07 1952-06-07 Photographic elements and process of preparing the same Expired - Lifetime US2698241A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
BE520491D BE520491A (hr) 1952-06-07
IT491646D IT491646A (hr) 1952-06-07
US292387A US2698241A (en) 1952-06-07 1952-06-07 Photographic elements and process of preparing the same
GB14298/53A GB732607A (en) 1952-06-07 1953-05-21 Film bases and photographic elements and process of preparing the same
FR1088197D FR1088197A (fr) 1952-06-07 1953-06-05 éléments photographiques et leur procédé de fabrication
DEP9899A DE941764C (de) 1952-06-07 1953-06-07 Photographische Filme und Verfahren zu ihrer Herstellung

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US292387A US2698241A (en) 1952-06-07 1952-06-07 Photographic elements and process of preparing the same

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BE (1) BE520491A (hr)
DE (1) DE941764C (hr)
FR (1) FR1088197A (hr)
GB (1) GB732607A (hr)
IT (1) IT491646A (hr)

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2897099A (en) * 1955-08-31 1959-07-28 Ganahl Carl De Methyl cellulose coated polyester tape
US2911321A (en) * 1955-02-19 1959-11-03 Kalle & Co Ag Polyterephthalic acid ester laminated foils
US2943936A (en) * 1956-12-13 1960-07-05 Keuffel & Esser Co Cartographic material
US3007901A (en) * 1953-11-12 1961-11-07 Eastman Kodak Co Resinous mixed alkyl ester and carboxy ester lactones and preparation process therefor
US3023101A (en) * 1955-04-14 1962-02-27 Agfa Ag Photographic film
US3025163A (en) * 1957-03-29 1962-03-13 Agfa Ag Photographic element having polycarbonate sub-layer
US3038880A (en) * 1959-07-17 1962-06-12 Eastman Kodak Co Block copolymers of polycarbonates from 2-phenyl-bisphenol a and 4, 4'-bis(hydroxyphenyl)-methyl-dihalophenylmethanes and the latter compounds per se
US3038879A (en) * 1959-07-17 1962-06-12 Eastman Kodak Co Block copolycarbonates from tetrachlorobisphenol a and 4, 4'-bis(hydroxyphenyl)-naphthyl methanes
US3106545A (en) * 1959-07-17 1963-10-08 Eastman Kodak Co Block copolymers of polycarbonates from bisphenol a and 4, 4'-bis (hydroxyphenyl)-monohalophenylmethanes or methyl substituted derivatives thereof, the latter compounds per se and homopolymers thereof
US3106546A (en) * 1959-07-17 1963-10-08 Eastman Kodak Co Block copolymers of polycarbonates from bisphenol a and 4, 4'-bis (hydroxyphenyl) naphthylmethanes, the latter compounds per se and homopolymers thereof
US3106544A (en) * 1959-07-17 1963-10-08 Eastman Kodak Co Block copolycarbonates from bisphenol a and 4, 4'-bis (hydroxyphenyl) methyl dihalophenyl methanes
US3123492A (en) * 1962-02-28 1964-03-03 Maffet
US3128264A (en) * 1959-07-17 1964-04-07 Eastman Kodak Co Block copolycarbonates of bisphenol a and 4,4'-bis(hydroxyphenyl) diphenyl methane
US3158494A (en) * 1962-08-21 1964-11-24 Minnesota Mining & Mfg Coated polymeric thermoplastic sheet material
US3178287A (en) * 1960-05-23 1965-04-13 Minnesota Mining & Mfg Thin photographically sensitive film element
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
US3212920A (en) * 1960-09-20 1965-10-19 Du Pont Delustering of glossy surfaces by the use of a non-particle containing coating composition
US3393087A (en) * 1955-04-22 1968-07-16 Monsanto Co Plastic vessel coated with epoxy resin containing lacquer
US3617352A (en) * 1966-02-02 1971-11-02 Takeo Shima Process, agent and article relating to improved adhesion between a shaped article of a crystalline polyester and rubber
US3775114A (en) * 1968-07-15 1973-11-27 Itek Corp Photosensitive silver halide layers and process
US3835780A (en) * 1968-07-15 1974-09-17 Itek Corp Process of printing by driography
US3839038A (en) * 1970-06-12 1974-10-01 Itek Corp Photosensitive silver halide layers and process
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
FR2389158A1 (fr) * 1977-04-27 1978-11-24 Du Pont Composition pour faire adherer une emulsion photographique a un support pelliculaire de polyester
US4584262A (en) * 1982-05-27 1986-04-22 E. I. Du Pont De Nemours And Company Process of making post-stretch polyester terpolymer resin subs for polyester supports for photographic elements
US4617468A (en) * 1983-02-24 1986-10-14 Fuji Photo Film Co., Ltd. Stimulable phosphor sheet with hydrophilic surface

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE611224A (hr) * 1961-12-07
GB1088906A (en) * 1964-12-09 1967-10-25 Bexford Ltd Synthetic film materials
US4167593A (en) 1976-06-04 1979-09-11 Ciba-Geigy Ag Method of subbing a polyester base

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
US2282827A (en) * 1939-11-13 1942-05-12 Du Pont Resinous product and method of making
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
US2625531A (en) * 1950-09-29 1953-01-13 Wingfoot Corp Isocyanate modified polymers
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
US2216736A (en) * 1938-09-27 1940-10-08 Du Pont Photographic film
US2282827A (en) * 1939-11-13 1942-05-12 Du Pont Resinous product and method of making
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
US2627088A (en) * 1950-03-22 1953-02-03 Du Pont Preparation of oriented coated films
US2625531A (en) * 1950-09-29 1953-01-13 Wingfoot Corp Isocyanate modified polymers

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3007901A (en) * 1953-11-12 1961-11-07 Eastman Kodak Co Resinous mixed alkyl ester and carboxy ester lactones and preparation process therefor
US2911321A (en) * 1955-02-19 1959-11-03 Kalle & Co Ag Polyterephthalic acid ester laminated foils
US3023101A (en) * 1955-04-14 1962-02-27 Agfa Ag Photographic film
US3393087A (en) * 1955-04-22 1968-07-16 Monsanto Co Plastic vessel coated with epoxy resin containing lacquer
US2897099A (en) * 1955-08-31 1959-07-28 Ganahl Carl De Methyl cellulose coated polyester tape
US2943936A (en) * 1956-12-13 1960-07-05 Keuffel & Esser Co Cartographic material
US3025163A (en) * 1957-03-29 1962-03-13 Agfa Ag Photographic element having polycarbonate sub-layer
US3128264A (en) * 1959-07-17 1964-04-07 Eastman Kodak Co Block copolycarbonates of bisphenol a and 4,4'-bis(hydroxyphenyl) diphenyl methane
US3106546A (en) * 1959-07-17 1963-10-08 Eastman Kodak Co Block copolymers of polycarbonates from bisphenol a and 4, 4'-bis (hydroxyphenyl) naphthylmethanes, the latter compounds per se and homopolymers thereof
US3106544A (en) * 1959-07-17 1963-10-08 Eastman Kodak Co Block copolycarbonates from bisphenol a and 4, 4'-bis (hydroxyphenyl) methyl dihalophenyl methanes
US3038880A (en) * 1959-07-17 1962-06-12 Eastman Kodak Co Block copolymers of polycarbonates from 2-phenyl-bisphenol a and 4, 4'-bis(hydroxyphenyl)-methyl-dihalophenylmethanes and the latter compounds per se
US3038879A (en) * 1959-07-17 1962-06-12 Eastman Kodak Co Block copolycarbonates from tetrachlorobisphenol a and 4, 4'-bis(hydroxyphenyl)-naphthyl methanes
US3106545A (en) * 1959-07-17 1963-10-08 Eastman Kodak Co Block copolymers of polycarbonates from bisphenol a and 4, 4'-bis (hydroxyphenyl)-monohalophenylmethanes or methyl substituted derivatives thereof, the latter compounds per se and homopolymers thereof
US3178287A (en) * 1960-05-23 1965-04-13 Minnesota Mining & Mfg Thin photographically sensitive film element
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
US3212920A (en) * 1960-09-20 1965-10-19 Du Pont Delustering of glossy surfaces by the use of a non-particle containing coating composition
US3123492A (en) * 1962-02-28 1964-03-03 Maffet
US3158494A (en) * 1962-08-21 1964-11-24 Minnesota Mining & Mfg Coated polymeric thermoplastic sheet material
US3617352A (en) * 1966-02-02 1971-11-02 Takeo Shima Process, agent and article relating to improved adhesion between a shaped article of a crystalline polyester and rubber
US3775114A (en) * 1968-07-15 1973-11-27 Itek Corp Photosensitive silver halide layers and process
US3835780A (en) * 1968-07-15 1974-09-17 Itek Corp Process of printing by driography
US3839038A (en) * 1970-06-12 1974-10-01 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
FR2389158A1 (fr) * 1977-04-27 1978-11-24 Du Pont Composition pour faire adherer une emulsion photographique a un support pelliculaire de polyester
US4584262A (en) * 1982-05-27 1986-04-22 E. I. Du Pont De Nemours And Company Process of making post-stretch polyester terpolymer resin subs for polyester supports for photographic elements
US4617468A (en) * 1983-02-24 1986-10-14 Fuji Photo Film Co., Ltd. Stimulable phosphor sheet with hydrophilic surface

Also Published As

Publication number Publication date
FR1088197A (fr) 1955-03-03
GB732607A (en) 1955-06-29
BE520491A (hr)
DE941764C (de) 1956-04-19
IT491646A (hr)

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