US3833403A - Process for subbing photographic polyester films - Google Patents
Process for subbing photographic polyester films Download PDFInfo
- Publication number
- US3833403A US3833403A US00363051A US36305173A US3833403A US 3833403 A US3833403 A US 3833403A US 00363051 A US00363051 A US 00363051A US 36305173 A US36305173 A US 36305173A US 3833403 A US3833403 A US 3833403A
- Authority
- US
- United States
- Prior art keywords
- subbing
- film
- photographic
- polyester film
- composition
- 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
- 229920006267 polyester film Polymers 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 18
- -1 ethyleneimino Chemical group 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 abstract description 35
- 229920001577 copolymer Polymers 0.000 abstract description 13
- 239000004816 latex Substances 0.000 abstract description 13
- 229920000126 latex Polymers 0.000 abstract description 13
- 150000001993 dienes Chemical class 0.000 abstract description 7
- 239000000178 monomer Substances 0.000 abstract description 6
- 229920013646 Hycar Polymers 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000839 emulsion Substances 0.000 description 10
- 230000008961 swelling Effects 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 239000002904 solvent Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 229920000139 polyethylene terephthalate Polymers 0.000 description 5
- 239000005020 polyethylene terephthalate Substances 0.000 description 5
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 230000001464 adherent effect Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- MAIFZJHANFOZHK-UHFFFAOYSA-N 3-methylsulfonyloxypropyl methanesulfonate Chemical compound CS(=O)(=O)OCCCOS(C)(=O)=O MAIFZJHANFOZHK-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 208000028659 discharge Diseases 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- LUMLZKVIXLWTCI-NSCUHMNNSA-N (e)-2,3-dichloro-4-oxobut-2-enoic acid Chemical compound OC(=O)C(\Cl)=C(/Cl)C=O LUMLZKVIXLWTCI-NSCUHMNNSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 229920000459 Nitrile rubber Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- 238000003851 corona treatment Methods 0.000 description 2
- 230000001627 detrimental effect Effects 0.000 description 2
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 229940015043 glyoxal Drugs 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- ZAKLKBFCSHJIRI-UHFFFAOYSA-N mucochloric acid Natural products OC1OC(=O)C(Cl)=C1Cl ZAKLKBFCSHJIRI-UHFFFAOYSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- HMDQPBSDHHTRNI-UHFFFAOYSA-N 1-(chloromethyl)-3-ethenylbenzene Chemical compound ClCC1=CC=CC(C=C)=C1 HMDQPBSDHHTRNI-UHFFFAOYSA-N 0.000 description 1
- ZRZHXNCATOYMJH-UHFFFAOYSA-N 1-(chloromethyl)-4-ethenylbenzene Chemical compound ClCC1=CC=C(C=C)C=C1 ZRZHXNCATOYMJH-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- GPOGMJLHWQHEGF-UHFFFAOYSA-N 2-chloroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCl GPOGMJLHWQHEGF-UHFFFAOYSA-N 0.000 description 1
- WHBAYNMEIXUTJV-UHFFFAOYSA-N 2-chloroethyl prop-2-enoate Chemical compound ClCCOC(=O)C=C WHBAYNMEIXUTJV-UHFFFAOYSA-N 0.000 description 1
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 1
- FWWXYLGCHHIKNY-UHFFFAOYSA-N 2-ethoxyethyl prop-2-enoate Chemical compound CCOCCOC(=O)C=C FWWXYLGCHHIKNY-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 1
- ILZXXGLGJZQLTR-UHFFFAOYSA-N 2-phenylethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC=C1 ILZXXGLGJZQLTR-UHFFFAOYSA-N 0.000 description 1
- HPSGLFKWHYAKSF-UHFFFAOYSA-N 2-phenylethyl prop-2-enoate Chemical compound C=CC(=O)OCCC1=CC=CC=C1 HPSGLFKWHYAKSF-UHFFFAOYSA-N 0.000 description 1
- KFNGWPXYNSJXOP-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propane-1-sulfonic acid Chemical compound CC(=C)C(=O)OCCCS(O)(=O)=O KFNGWPXYNSJXOP-UHFFFAOYSA-N 0.000 description 1
- IZUVGRMMRWJVKU-UHFFFAOYSA-N 3-ethoxycarbonylbut-3-enoic acid Chemical compound CCOC(=O)C(=C)CC(O)=O IZUVGRMMRWJVKU-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- IHDBZCJYSHDCKF-UHFFFAOYSA-N 4,6-dichlorotriazine Chemical compound ClC1=CC(Cl)=NN=N1 IHDBZCJYSHDCKF-UHFFFAOYSA-N 0.000 description 1
- FPSPPRZKBUVEJQ-UHFFFAOYSA-N 4,6-dimethoxypyrimidine Chemical compound COC1=CC(OC)=NC=N1 FPSPPRZKBUVEJQ-UHFFFAOYSA-N 0.000 description 1
- ADKSXOTUSDQWFO-UHFFFAOYSA-N 4-chlorobutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCl ADKSXOTUSDQWFO-UHFFFAOYSA-N 0.000 description 1
- MSZCRKZKNKSJNU-UHFFFAOYSA-N 4-chlorobutyl prop-2-enoate Chemical compound ClCCCCOC(=O)C=C MSZCRKZKNKSJNU-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- OIYTYGOUZOARSH-UHFFFAOYSA-N 4-methoxy-2-methylidene-4-oxobutanoic acid Chemical compound COC(=O)CC(=C)C(O)=O OIYTYGOUZOARSH-UHFFFAOYSA-N 0.000 description 1
- NUXLDNTZFXDNBA-UHFFFAOYSA-N 6-bromo-2-methyl-4h-1,4-benzoxazin-3-one Chemical compound C1=C(Br)C=C2NC(=O)C(C)OC2=C1 NUXLDNTZFXDNBA-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 244000186140 Asperula odorata Species 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 229910021555 Chromium Chloride Inorganic materials 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 235000008526 Galium odoratum Nutrition 0.000 description 1
- 229920006385 Geon Polymers 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical class OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 238000007329 Woodward reaction Methods 0.000 description 1
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- JNNKWUPPLJTSSJ-UHFFFAOYSA-N chloromethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCl JNNKWUPPLJTSSJ-UHFFFAOYSA-N 0.000 description 1
- KMKLIOQYUUPLMA-UHFFFAOYSA-N chloromethyl prop-2-enoate Chemical compound ClCOC(=O)C=C KMKLIOQYUUPLMA-UHFFFAOYSA-N 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- XJELOQYISYPGDX-UHFFFAOYSA-N ethenyl 2-chloroacetate Chemical compound ClCC(=O)OC=C XJELOQYISYPGDX-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- UWQBTOIFLYLNRS-UHFFFAOYSA-N ethyl(prop-2-enoyl)carbamic acid Chemical compound CCN(C(O)=O)C(=O)C=C UWQBTOIFLYLNRS-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WARQUFORVQESFF-UHFFFAOYSA-N isocyanatoethene Chemical compound C=CN=C=O WARQUFORVQESFF-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
- 239000000463 material Substances 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- XEHWRFWEMHSVTP-UHFFFAOYSA-N methyl(prop-2-enoyl)carbamic acid Chemical compound OC(=O)N(C)C(=O)C=C XEHWRFWEMHSVTP-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical class C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 description 1
- YMRDXPCIIDUQFY-UHFFFAOYSA-N n-(2-phenylethyl)prop-2-enamide Chemical compound C=CC(=O)NCCC1=CC=CC=C1 YMRDXPCIIDUQFY-UHFFFAOYSA-N 0.000 description 1
- OHLHOLGYGRKZMU-UHFFFAOYSA-N n-benzylprop-2-enamide Chemical compound C=CC(=O)NCC1=CC=CC=C1 OHLHOLGYGRKZMU-UHFFFAOYSA-N 0.000 description 1
- NXFQHRVNIOXGAQ-YCRREMRBSA-N nitrofurantoin Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)NC(=O)C1 NXFQHRVNIOXGAQ-YCRREMRBSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- YHFJPYZZQSBMDZ-UHFFFAOYSA-N phenyl(prop-2-enoyl)carbamic acid Chemical compound C=CC(=O)N(C(=O)O)C1=CC=CC=C1 YHFJPYZZQSBMDZ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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
- G03C1/915—Photosensitive materials characterised by the base or auxiliary layers characterised by subbing layers or subbing means using mechanical or physical means therefor, e.g. corona
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/151—Matting or other surface reflectivity altering material
Definitions
- This invention relates to a process for subbing a photographic polyester film in order to have strong adhesion of a photographic gelatinous composition to the polyester film.
- the invention pertains to a process for subbing a photographic polyester film in order to firmly adhere to the polyester film a photographic gelatinous composition, e.g., a gelatinsilver halide emulsion, a gelatinous composition containing an antihalation agent, or a gelatin backing composition, which comprises subjecting at least one side of the polyester film to electron bombardment, and
- a photographic gelatinous composition e.g., a gelatinsilver halide emulsion, a gelatinous composition containing an antihalation agent, or a gelatin backing composition
- An object of the present invention is to provide a process for subbing a polyester film in which no swelling or solubilizing agent for polyester is substantially used.
- Another object of the invention is to provide a process for subbing a photographic polyester film without injuring the polyester film in flatness, which process makes it possible to firmly adhere a photographic gelatinous composition to the polyester film and does not give any detrimental influence to the photographic properties of said photographic gelatinous composition.
- a process for subbing a polyester film which comprises subjecting at least one side of the polyester film to electron bombardment so that the contact angle thereof with water becomes less than 58, and then applying to the treated surface of the polyester film a subbing composition containing (a) a copolymer latex of a diolefin with other polymerizable ethylenically unsaturated monomer and (b) a compound having two or more of groups selected from ethyleneimino and methylsulfonyloxy groups. If any one of the conditions required in the said subbing proscribed later.
- the polyester film used in the present invention is composed of an aliphatic diol and an aromatic dicarboxylic acid, and a typical example thereof is a polyethylene terephthalate film.
- the copolymer latex used in the present invention is composed of a diolefin and other polymerizable ethylenically unsaturated monomer.
- the diolefin include butadiene, 2-chloroprene, isoprene, neoprene and 2,3-methylbutadiene
- examples of the said other polymerizable ethylenically unsaturated monomer include methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, propyl acrylate, propyl methacrylate, butyl acrylate, butyl methacrylate, chloroethyl acrylate, chloroethyl methacrylate, hydroxyethyl acrylate, hydroxyethyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, 2-ethylhexyl acrylate, glycidy
- N,N-dialkyl acrylamides the alkyl includes, for example, methyl, ethyl, propyl, butyl and amyl, and the two alkyls may be same or different
- copolymer lattice can be easily obtained as commercially available products.
- Typical examples of the obtainable copolymer lattice are Hycar 2570x5, Hycar 1551, Hycar 1561, Hycar 1571, Hycar 1562, Hycar 1577, Nipol 4850, Nipol LX-l l0, Hycar LX-204, Hycar LX-303, Hycar LX-407, Hycar LX- 411, Hycar LX-4l5, Hycar LX-4l6, Hycar 2507 and Hycar 2518 produced by Nippon Geon Co.; Croslene SA-20, Croslene NA-lO, Croslene NS-16, Croslene 2M-30, Croslene NA-ll, Croslene SA-22, Croslene SA-23, Croslene SA-24, Croslene 2M-33, Croslene 2M-33A, Croslene 2M-36, Croslene 2M-38 and Croslene SK-SO produced by Takeda Chemical Industries, Ltd.; Dow
- Binder LF-3 produced by Dainichi Seikako Co.
- NK Binder SM-200R produced by Nakamura Kagaku Co.
- Corporex No. 1001 and Corporex No. 1031 produced by Mitsubishi Gas Kagaku Co.
- Wool Cement 3C and Wool Cement No. CS produced by Kyoritsu Kagaku Sangyo Co.
- Bortex GV produced by Meisei Kagaku Co., and all of these are effectively usable.
- the copolymer latex used in the present invention is preferably one'which contains 25 to 75 percent by weight of a diolefin and about to 30 percent by weight of a polymerizable ethylenically unsaturated monomer containing at least one reactive active or readily reactive) functional group having at the terminals at least one of hydroxyl, formyl, carboxyl, amido, alkoxy, isocyanato and ethyleneimino groups.
- Typical examples of the compound having two or more groups selected from ethyleneimino and methylsulfonyl groups are as follows:
- n is an integer of 1 to NCONH- CH1 CH, NHC ON (3).-- CH; CH,
- n is an integer ol 1 to 10
- n is an integer of 2 to 6
- n is an integer of 2 to 200
- the above-mentioned compound which is the aforesaid component (b), is used in an amount within the range from 0.01 to 100 percent, preferably from about 0.1 to 30 percent, by weight based on the weight of the aforesaid copolymer latex.
- the compound as the component (b) is dissolved in water or an organic solvent or in a mixture of the two, and then added to the aforesaid copolymer latex to prepare a subbing composition.
- the subbing composition is in the form of an aqueous dispersion, in general, but may alternatively be used, depending on the kind of drying means employed, in the form of a dispersion in a mixed solvent comprising water and methanol, ethanol, acetone or the like organic solvent lower in boiling point than water.
- the organic solvent is used in 0.1 to 10 times the amount of waters
- the subbing composition is applied by such means as coating and drying onto the surface of polyester film whose contact angle with water has brought to less than 58 according to electron bombardment.
- the electron bombardment is carried out by use of such corona discharge apparatus or the like that electrons are discharged at a high speed between at least a pair of electrodes in the presence of a gas or under pressure.
- the electron bombardment should be conducted to such an extent that the contact angle of polyester film with water becomes less than 58. If the contact angle is more than the said value, no satisfac-' tory subbing effect can be attained, as is clear from the working examples described later.
- a polyester film is subjected to electron bombardment so that the contact angle thereof with water becomes less than 58", and then a subbing composition containing the aforesaid component (a) (copolymer latex) and the aforesaid component (b) (exemplified compound) is applied according to such means as, for example, coating and drying to the treated side of the polyester film, whereby the subbed polyester film surface becomes highly adherent to a photographic gelatinous composition and sufficiently maintains the excellent adhesion even under severe conditions.
- the subbing composition according to the present invention does not give any detrimental influence to the photographic properties of photographic gelatinous composition and, moreover, does not require the use of swelling or dissolving for polyester to make it possible to overcome various problems derived from the use of said agents.
- the subbing composition used in the present invention may contain various photographic additives in addition to the aforesaid components (a) and (b).
- the subbing composition may be incorporated with such a hardener used to enhance the water resistance of photographic gelatinous composition as, for example, formaldehyde, mucochloric acid, acrolein, glyoxal, divinyl sulfone, vinyl sulfone, dichlorotriazine, hexahydrol ,3,5-triacryloyl-s-triazine, dihydroxybenzene, methylenebis acrylamide, dicarboxylic acid dinitrophenyl ester, dicarboxylic acid dichloromethyl ester, carbodiimide derivative, Woodwards reagent or chromium chloride.
- a hardener used to enhance the water resistance of photographic gelatinous composition as, for example, formaldehyde, mucochloric acid, acrolein, glyoxal
- the subbing composition may be incorporated with a surface active agent, e.g., natural saponin or anionic or nonionic synthetic surface active agent, in order to disperse the copolymer latex, and with a matting agent, e.g., colloidal silica, titanium oxide, zinc oxide, aluminum oxide polymethyl methacrylate or polystyrene beads, or starch powder.
- a surface active agent e.g., natural saponin or anionic or nonionic synthetic surface active agent
- a matting agent e.g., colloidal silica, titanium oxide, zinc oxide, aluminum oxide polymethyl methacrylate or polystyrene beads, or starch powder.
- the subbing composition may be incorporated with dye or pigment for antihalation or for coloration of film base.
- a subbing composition comprising 6 g. of Polylac SL-204 (produced by Mitsui Toatsu Co.), 0.18 g. of hexamethylenebis ethyleneimino ureide (the exemplified compound (1), wherein n
- Dry film adhesion test invention The photographic emulsion layer surface of each sample was scratched with a razor so as to form squares. Subsequently, a cellophane adhesive tape was applied under finger pressure onto the said surface and then quickly stripped off therefrom, and the residual ratio of the photographic emulsion layer on the film base to the adhesion surface area of the tape was repre sented by percentage.
- Wet film adhesion test invention The photographic emulsion layer surface of each sample was scratched with a razor so as to form squares. Subsequently, a cellophane adhesive tape was applied under finger pressure onto the said surface and then quickly stripped off therefrom, and the residual ratio of the photographic emulsion layer on the film base to the adhesion surface area of the tape was repre sented by percentage.
- the photographic emul emulsion layer surface of each sample was scratched with the sharp tip of a gimlet so as to form squares and then rubbed, and the residual ratio of the photographic emulsion layer on the film base was represented by per centage.
- a biaxially stretched polyethylene terephthalate film was pre-treated with a methanol solution containing p-chlorophenol, dried at 80 C. for 2 minutes, and then equally divided into two.
- One film was coated with the above-mentioned subbing composition, and the other film was coated with the same composition as above, except that the trimethylenedimethane sulfonate was not contained.
- These films were individually coated onto the subbed surfaces with the same roentgen emulsion as above, and then dried to prepare samples.
- Example 3 Biaxially stretched polyethylene terephthalate films which had been subjected to corona discharge treatment under the same conditions as in the case of the sample (1) prepared in Example 1, were individually coated onto the surfaces with each of such subbing compositions as shown in Table 3, dried at C. for 1 minute, further coated with an antihalation backing gelatin layer containing an absorption dye, and then dried to prepare samples. These samples were subjected to the same sub layer adhesion tests as in Example l to obtain the results as set forth in Table 3.
- Example 4 A biaxially stretched polyethylene terephthalate film, which had-been subjected to corona discharge treat- .ment under the same conditions as in the case of the Table 3 Sample Subbing composition (made I ccv Dry film Wet film No. by addition of water) adhesion adhesion (I0) Hycur 2570X5 (7 g.)
- a process for subbing a photographic polyester 1.
- a process for subbing photographic polyester film bing composition containing (a) a copolymer latex of as claimed incl aim l, wherein said compound (b) is a diolefin with other polymerizable ethylenically unsatthat whi h at lea t ne methylsulfonyloxy group in adurated monomer and (b) a compound having two or dition to one or more groups selected from more groups selected from ethylenermino and methylthyl i in and methylsulfonyloxy groups. sulfonyloxy groups.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Laminated Bodies (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP47052978A JPS5232568B2 (en(2012)) | 1972-05-30 | 1972-05-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3833403A true US3833403A (en) | 1974-09-03 |
Family
ID=12929974
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00363051A Expired - Lifetime US3833403A (en) | 1972-05-30 | 1973-05-23 | Process for subbing photographic polyester films |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3833403A (en(2012)) |
| JP (1) | JPS5232568B2 (en(2012)) |
| BR (1) | BR7303937D0 (en(2012)) |
| DE (1) | DE2327302C3 (en(2012)) |
| GB (1) | GB1401703A (en(2012)) |
| SU (1) | SU576074A3 (en(2012)) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4168172A (en) * | 1977-11-24 | 1979-09-18 | Fuji Photo Film Co., Ltd. | Method for subbing polyester films |
| US4197129A (en) * | 1973-03-05 | 1980-04-08 | Konishiroku Photo Industry Co., Ltd. | Plastic support having improved adhesivness to material to be bonded thereto |
| US4429039A (en) | 1975-03-31 | 1984-01-31 | Fuji Photo Film Co., Ltd. | Photographic element |
| US4440847A (en) * | 1982-08-20 | 1984-04-03 | Am International, Inc. | Diazo material with waterborne drafting subbing composition of acrylic resin and aziridine and process of using |
| US5425980A (en) * | 1994-02-22 | 1995-06-20 | Eastman Kodak Company | Use of glow discharge treatment to promote adhesion of aqueous coats to substrate |
| EP0736801A3 (en) * | 1995-04-03 | 1997-02-26 | Eastman Kodak Co | Molecular grafting on polyesters pretreated with an energy source to promote the adhesion of layers containing gelatin |
| US5618659A (en) * | 1995-03-01 | 1997-04-08 | Eastman Kodak Company | Photographic element containing a nitrogen glow-discharge treated polyester substrate |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5922217B2 (ja) * | 1973-08-10 | 1984-05-25 | 富士写真フイルム株式会社 | ポリエステルフイルムの下塗法 |
| JPS57486B2 (en(2012)) * | 1973-08-21 | 1982-01-06 | ||
| JPS57487B2 (en(2012)) * | 1974-08-31 | 1982-01-06 | ||
| JPS5858656B2 (ja) * | 1975-04-09 | 1983-12-26 | 富士写真フイルム株式会社 | シヤシンザイリヨウ |
| GB1540067A (en) * | 1975-09-26 | 1979-02-07 | Bexford Ltd | Coated film bases |
| JPS541612A (en) * | 1977-04-27 | 1979-01-08 | Du Pont | Undercoat composition |
| US4220471A (en) * | 1977-10-13 | 1980-09-02 | Mitsubishi Paper Mills, Ltd. | Photographic polypropylene coated paper support with corona discharge treatment and polymeric subbing layer |
| JPS5464572A (en) * | 1977-11-02 | 1979-05-24 | Mitsubishi Paper Mills Ltd | Method of providing hydrophilic material to hydropholic surface |
| JPS5565949A (en) * | 1978-11-13 | 1980-05-17 | Fuji Photo Film Co Ltd | Subbing method for photographic material |
| EP0017717B1 (en) * | 1979-02-16 | 1982-07-07 | EASTMAN KODAK COMPANY (a New Jersey corporation) | Coating composition containing a polyaniline salt semiconductor, a method of preparing said composition and an element with a conductive layer formed from said composition |
| US5968646A (en) * | 1996-01-19 | 1999-10-19 | Eastman Kodak Company | Molecular grafting of hardener/gelatin blends to energetically treated polyesters to promote adhesion of layers |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2964404A (en) * | 1957-07-26 | 1960-12-13 | Eastman Kodak Co | Hardening of gelating with aziridinylsulfonyl compounds |
| US3216825A (en) * | 1961-02-23 | 1965-11-09 | Eastman Kodak Co | Photographic film element comprising butadiene polymeric coatings on polyethylene and other polymeric hydrocarbons |
| US3220842A (en) * | 1961-09-01 | 1965-11-30 | Eastman Kodak Co | Electrically prepared subbing for photo-stencil film on polyethylene terephthalate support |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE633988A (en(2012)) * | 1962-06-25 | |||
| DE1298717B (de) * | 1965-09-09 | 1969-07-03 | Fuji Photo Film Co Ltd | Aufbringen einer Unterschicht auf Polyesterfolien |
| DE1547874A1 (de) * | 1966-03-31 | 1969-12-11 | Fuji Photo Film Co Ltd | Verfahren zum Auflegen einer Unterschicht fuer photographische Filme |
| US3549406A (en) * | 1968-04-26 | 1970-12-22 | Eastman Kodak Co | Process of coating polymer surfaces activated by corona discharge |
| JPS4843122B1 (en(2012)) * | 1969-11-20 | 1973-12-17 |
-
1972
- 1972-05-30 JP JP47052978A patent/JPS5232568B2/ja not_active Expired
-
1973
- 1973-05-23 US US00363051A patent/US3833403A/en not_active Expired - Lifetime
- 1973-05-23 GB GB2469673A patent/GB1401703A/en not_active Expired
- 1973-05-28 BR BR3937/73A patent/BR7303937D0/pt unknown
- 1973-05-29 DE DE2327302A patent/DE2327302C3/de not_active Expired
- 1973-05-29 SU SU7301927357A patent/SU576074A3/ru active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2964404A (en) * | 1957-07-26 | 1960-12-13 | Eastman Kodak Co | Hardening of gelating with aziridinylsulfonyl compounds |
| US3216825A (en) * | 1961-02-23 | 1965-11-09 | Eastman Kodak Co | Photographic film element comprising butadiene polymeric coatings on polyethylene and other polymeric hydrocarbons |
| US3220842A (en) * | 1961-09-01 | 1965-11-30 | Eastman Kodak Co | Electrically prepared subbing for photo-stencil film on polyethylene terephthalate support |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4197129A (en) * | 1973-03-05 | 1980-04-08 | Konishiroku Photo Industry Co., Ltd. | Plastic support having improved adhesivness to material to be bonded thereto |
| US4429039A (en) | 1975-03-31 | 1984-01-31 | Fuji Photo Film Co., Ltd. | Photographic element |
| US4168172A (en) * | 1977-11-24 | 1979-09-18 | Fuji Photo Film Co., Ltd. | Method for subbing polyester films |
| US4440847A (en) * | 1982-08-20 | 1984-04-03 | Am International, Inc. | Diazo material with waterborne drafting subbing composition of acrylic resin and aziridine and process of using |
| US5425980A (en) * | 1994-02-22 | 1995-06-20 | Eastman Kodak Company | Use of glow discharge treatment to promote adhesion of aqueous coats to substrate |
| US5538841A (en) * | 1994-02-22 | 1996-07-23 | Eastman Kodak Company | Use of glow discharge treatment to promote adhesion of aqueous coatings to substrate |
| US5576164A (en) * | 1994-02-22 | 1996-11-19 | Eastman Kodak Company | Photographic element having a polyester substrate with an oxygen modified surface region |
| US5582921A (en) * | 1994-02-22 | 1996-12-10 | Eastman Kodak Company | Use of glow discharge treatment to promote adhesion of aqueous coatings to substrate |
| US5618659A (en) * | 1995-03-01 | 1997-04-08 | Eastman Kodak Company | Photographic element containing a nitrogen glow-discharge treated polyester substrate |
| EP0736801A3 (en) * | 1995-04-03 | 1997-02-26 | Eastman Kodak Co | Molecular grafting on polyesters pretreated with an energy source to promote the adhesion of layers containing gelatin |
| US5700577A (en) * | 1995-04-03 | 1997-12-23 | Eastman Kodak Company | Molecular grafting to energetically treated polyesters to promote adhesion of gelatin-containing layers |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2327302C3 (de) | 1981-09-03 |
| JPS4911118A (en(2012)) | 1974-01-31 |
| DE2327302B2 (de) | 1980-12-04 |
| DE2327302A1 (de) | 1973-12-13 |
| BR7303937D0 (pt) | 1974-08-15 |
| JPS5232568B2 (en(2012)) | 1977-08-23 |
| SU576074A3 (ru) | 1977-10-05 |
| GB1401703A (en) | 1975-07-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: KONICA CORPORATION, JAPAN Free format text: RELEASED BY SECURED PARTY;ASSIGNOR:KONISAIROKU PHOTO INDUSTRY CO., LTD.;REEL/FRAME:005159/0302 Effective date: 19871021 |