US2698241A - Photographic elements and process of preparing the same - Google Patents
Photographic elements and process of preparing the same Download PDFInfo
- 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
- Authority
- US
- United States
- Prior art keywords
- weight
- polyester
- diisocyanate
- film
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title description 6
- 229920000728 polyester Polymers 0.000 claims description 33
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 20
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 19
- 239000005056 polyisocyanate Substances 0.000 claims description 12
- 229920001228 polyisocyanate Polymers 0.000 claims description 12
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 9
- 230000002209 hydrophobic effect Effects 0.000 claims description 9
- 150000002894 organic compounds Chemical class 0.000 claims description 7
- 229920006267 polyester film Polymers 0.000 claims description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- -1 silver halide Chemical class 0.000 description 36
- 239000000084 colloidal system Substances 0.000 description 23
- 229910052709 silver Inorganic materials 0.000 description 20
- 239000004332 silver Substances 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 17
- 239000000839 emulsion Substances 0.000 description 17
- 239000002253 acid Substances 0.000 description 14
- 125000005442 diisocyanate group Chemical group 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 108010010803 Gelatin Proteins 0.000 description 10
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 10
- 229920000159 gelatin Polymers 0.000 description 10
- 239000008273 gelatin Substances 0.000 description 10
- 235000019322 gelatine Nutrition 0.000 description 10
- 235000011852 gelatine desserts Nutrition 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 229920000139 polyethylene terephthalate Polymers 0.000 description 8
- 239000005020 polyethylene terephthalate Substances 0.000 description 8
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Natural products OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 7
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- 238000000576 coating method Methods 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001241 acetals Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
- 235000019345 sodium thiosulphate Nutrition 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 229910021612 Silver iodide Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229910021538 borax Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 229910052798 chalcogen Inorganic materials 0.000 description 2
- 150000001787 chalcogens Chemical class 0.000 description 2
- 238000010622 cold drawing Methods 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- GRLPQNLYRHEGIJ-UHFFFAOYSA-J potassium aluminium sulfate Chemical compound [Al+3].[K+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRLPQNLYRHEGIJ-UHFFFAOYSA-J 0.000 description 2
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 2
- 229940045105 silver iodide Drugs 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 239000004328 sodium tetraborate Substances 0.000 description 2
- 235000010339 sodium tetraborate Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- WOGVOIWHWZWYOZ-UHFFFAOYSA-N 1,1-diisocyanatoethane Chemical compound O=C=NC(C)N=C=O WOGVOIWHWZWYOZ-UHFFFAOYSA-N 0.000 description 1
- VNKVWAHIXVCSTQ-UHFFFAOYSA-N 1,1-diisothiocyanatoheptane Chemical compound CCCCCCC(N=C=S)N=C=S VNKVWAHIXVCSTQ-UHFFFAOYSA-N 0.000 description 1
- MGZPILVOXGOTMY-UHFFFAOYSA-N 1,2,3,4-tetraisocyanatobutane Chemical compound O=C=NCC(N=C=O)C(N=C=O)CN=C=O MGZPILVOXGOTMY-UHFFFAOYSA-N 0.000 description 1
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- VDDIDKWDKHSMKA-UHFFFAOYSA-N 1,2-diisocyanatoethylbenzene Chemical compound O=C=NCC(N=C=O)C1=CC=CC=C1 VDDIDKWDKHSMKA-UHFFFAOYSA-N 0.000 description 1
- PGWNLTOGCUNUFR-UHFFFAOYSA-N 1,3-diisocyanato-5-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(N=C=O)=CC(N=C=O)=C1 PGWNLTOGCUNUFR-UHFFFAOYSA-N 0.000 description 1
- IKYNWXNXXHWHLL-UHFFFAOYSA-N 1,3-diisocyanatopropane Chemical compound O=C=NCCCN=C=O IKYNWXNXXHWHLL-UHFFFAOYSA-N 0.000 description 1
- BOLANQNHTGVOMY-UHFFFAOYSA-N 1,3-diisothiocyanatobenzene Chemical compound S=C=NC1=CC=CC(N=C=S)=C1 BOLANQNHTGVOMY-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 1
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- BEQUUCHROWKGNN-UHFFFAOYSA-N 2-chloro-1,3-diisocyanatopropane Chemical compound O=C=NCC(Cl)CN=C=O BEQUUCHROWKGNN-UHFFFAOYSA-N 0.000 description 1
- YJIGYQKAFCFYNS-UHFFFAOYSA-N 3-isothiocyanatohexane Chemical compound CCCC(CC)N=C=S YJIGYQKAFCFYNS-UHFFFAOYSA-N 0.000 description 1
- XTBFKMDOQMQYPP-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine;hydron;chloride Chemical compound Cl.CCN(CC)C1=CC=C(N)C=C1 XTBFKMDOQMQYPP-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 101100025412 Arabidopsis thaliana XI-A gene Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 229920001756 Polyvinyl chloride acetate Polymers 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
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- 239000001913 cellulose Substances 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004979 cyclopentylene group Chemical group 0.000 description 1
- KIQKWYUGPPFMBV-UHFFFAOYSA-N diisocyanatomethane Chemical compound O=C=NCN=C=O KIQKWYUGPPFMBV-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- VNGOYPQMJFJDLV-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1 VNGOYPQMJFJDLV-UHFFFAOYSA-N 0.000 description 1
- KHAIRHLKBKSNHK-UHFFFAOYSA-L disodium hydrogen sulfite acetate Chemical compound C(C)(=O)O.S(=O)([O-])[O-].[Na+].[Na+] KHAIRHLKBKSNHK-UHFFFAOYSA-L 0.000 description 1
- 238000010981 drying operation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
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- 229960004667 ethyl cellulose Drugs 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- XIRJLSRMAMZTGY-UHFFFAOYSA-N isocyanic acid;isothiocyanic acid Chemical class N=C=O.N=C=S XIRJLSRMAMZTGY-UHFFFAOYSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 229960005222 phenazone Drugs 0.000 description 1
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- 150000004060 quinone imines Chemical class 0.000 description 1
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 1
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- 238000005507 spraying Methods 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
Images
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/76—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.
Landscapes
- 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)
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE520491D BE520491A (hu) | 1952-06-07 | ||
IT491646D IT491646A (hu) | 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 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US292387A US2698241A (en) | 1952-06-07 | 1952-06-07 | Photographic elements and process of preparing the same |
Publications (1)
Publication Number | Publication Date |
---|---|
US2698241A true US2698241A (en) | 1954-12-28 |
Family
ID=23124453
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US292387A Expired - Lifetime US2698241A (en) | 1952-06-07 | 1952-06-07 | Photographic elements and process of preparing the same |
Country Status (6)
Country | Link |
---|---|
US (1) | US2698241A (hu) |
BE (1) | BE520491A (hu) |
DE (1) | DE941764C (hu) |
FR (1) | FR1088197A (hu) |
GB (1) | GB732607A (hu) |
IT (1) | IT491646A (hu) |
Cited By (27)
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 |
US3038879A (en) * | 1959-07-17 | 1962-06-12 | Eastman Kodak Co | Block copolycarbonates from tetrachlorobisphenol a and 4, 4'-bis(hydroxyphenyl)-naphthyl 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 |
US3106544A (en) * | 1959-07-17 | 1963-10-08 | Eastman Kodak Co | Block copolycarbonates from bisphenol a and 4, 4'-bis (hydroxyphenyl) methyl dihalophenyl 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 |
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE611224A (hu) * | 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)
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 |
-
0
- BE BE520491D patent/BE520491A/xx unknown
- IT IT491646D patent/IT491646A/it unknown
-
1952
- 1952-06-07 US US292387A patent/US2698241A/en not_active Expired - Lifetime
-
1953
- 1953-05-21 GB GB14298/53A patent/GB732607A/en not_active Expired
- 1953-06-05 FR FR1088197D patent/FR1088197A/fr not_active Expired
- 1953-06-07 DE DEP9899A patent/DE941764C/de not_active Expired
Patent Citations (6)
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)
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 |
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 |
US3038879A (en) * | 1959-07-17 | 1962-06-12 | Eastman Kodak Co | Block copolycarbonates from tetrachlorobisphenol a and 4, 4'-bis(hydroxyphenyl)-naphthyl 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 |
US3106544A (en) * | 1959-07-17 | 1963-10-08 | Eastman Kodak Co | Block copolycarbonates from bisphenol a and 4, 4'-bis (hydroxyphenyl) methyl dihalophenyl methanes |
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 |
---|---|
DE941764C (de) | 1956-04-19 |
IT491646A (hu) | |
GB732607A (en) | 1955-06-29 |
FR1088197A (fr) | 1955-03-03 |
BE520491A (hu) |
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