JPH0440700B2 - - Google Patents
Info
- Publication number
- JPH0440700B2 JPH0440700B2 JP55141886A JP14188680A JPH0440700B2 JP H0440700 B2 JPH0440700 B2 JP H0440700B2 JP 55141886 A JP55141886 A JP 55141886A JP 14188680 A JP14188680 A JP 14188680A JP H0440700 B2 JPH0440700 B2 JP H0440700B2
- Authority
- JP
- Japan
- Prior art keywords
- latex
- monomer
- copolymer
- acid
- aqueous dispersion
- 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
- -1 silver halide Chemical class 0.000 claims description 71
- 239000000178 monomer Substances 0.000 claims description 62
- 229920001577 copolymer Polymers 0.000 claims description 48
- 229910052709 silver Inorganic materials 0.000 claims description 44
- 239000004332 silver Substances 0.000 claims description 44
- 239000000839 emulsion Substances 0.000 claims description 37
- 239000000463 material Substances 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 25
- 239000003792 electrolyte Substances 0.000 claims description 23
- 238000011161 development Methods 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 17
- 239000003112 inhibitor Substances 0.000 claims description 15
- 239000006185 dispersion Substances 0.000 claims description 14
- 239000007844 bleaching agent Substances 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 11
- 230000002860 competitive effect Effects 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 238000012545 processing Methods 0.000 claims description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000010521 absorption reaction Methods 0.000 claims description 5
- 238000003860 storage Methods 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000012190 activator Substances 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 230000003595 spectral effect Effects 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- LOCAIGRSOJUCTB-UHFFFAOYSA-N indazol-3-one Chemical compound C1=CC=C2C(=O)N=NC2=C1 LOCAIGRSOJUCTB-UHFFFAOYSA-N 0.000 claims description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 1
- 239000004816 latex Substances 0.000 description 82
- 229920000126 latex Polymers 0.000 description 82
- 239000000243 solution Substances 0.000 description 37
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 239000002245 particle Substances 0.000 description 29
- 230000002209 hydrophobic effect Effects 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000004519 manufacturing process Methods 0.000 description 22
- 159000000000 sodium salts Chemical class 0.000 description 22
- 238000003756 stirring Methods 0.000 description 15
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 108010010803 Gelatin Proteins 0.000 description 12
- 239000008273 gelatin Substances 0.000 description 12
- 229920000159 gelatin Polymers 0.000 description 12
- 235000019322 gelatine Nutrition 0.000 description 12
- 235000011852 gelatine desserts Nutrition 0.000 description 12
- 230000006870 function Effects 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
- 239000008199 coating composition Substances 0.000 description 10
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 10
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000975 dye Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000084 colloidal system Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 238000007334 copolymerization reaction Methods 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
- 239000004848 polyfunctional curative Substances 0.000 description 5
- 239000003505 polymerization initiator Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 4
- 229960001553 phloroglucinol Drugs 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000005110 aryl thio group Chemical group 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010556 emulsion polymerization method Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 3
- HZVWOTIWSLHAJB-UHFFFAOYSA-N octadecanoic acid prop-2-enamide Chemical compound NC(=O)C=C.CCCCCCCCCCCCCCCCCC(O)=O HZVWOTIWSLHAJB-UHFFFAOYSA-N 0.000 description 3
- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000004149 thio group Chemical group *S* 0.000 description 3
- IFABLCIRROMTAN-MDZDMXLPSA-N (e)-1-chlorooctadec-9-ene Chemical compound CCCCCCCC\C=C\CCCCCCCCCl IFABLCIRROMTAN-MDZDMXLPSA-N 0.000 description 2
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical group O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- YWRMFVZWFSDHFF-UHFFFAOYSA-N 11-(2-methylprop-2-enoylamino)undecanoic acid Chemical compound CC(=C)C(=O)NCCCCCCCCCCC(O)=O YWRMFVZWFSDHFF-UHFFFAOYSA-N 0.000 description 2
- RSNBFOQBVTXHIZ-UHFFFAOYSA-N 11-(2-methylprop-2-enoylamino)undecanoyl chloride Chemical compound CC(=C)C(=O)NCCCCCCCCCCC(Cl)=O RSNBFOQBVTXHIZ-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- SZTBMYHIYNGYIA-UHFFFAOYSA-N 2-chloroacrylic acid Chemical compound OC(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-N 0.000 description 2
- CJAJEZSCULAKCB-UHFFFAOYSA-N 2-sulfohexadecanoic acid Chemical compound CCCCCCCCCCCCCCC(C(O)=O)S(O)(=O)=O CJAJEZSCULAKCB-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241001269524 Dura Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- IFVYHJRLWCUVBB-UHFFFAOYSA-N allyl thiocyanate Chemical compound C=CCSC#N IFVYHJRLWCUVBB-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- ICCKYZGDUAOTHD-UHFFFAOYSA-L disodium;4-[(4-carboxylato-2-cyanobutan-2-yl)diazenyl]-4-cyanopentanoate Chemical compound [Na+].[Na+].[O-]C(=O)CCC(C)(C#N)N=NC(C)(CCC([O-])=O)C#N ICCKYZGDUAOTHD-UHFFFAOYSA-L 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 239000000416 hydrocolloid Substances 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000001617 migratory effect Effects 0.000 description 2
- YYKVDYMYOLDZEZ-UHFFFAOYSA-N n-(4-acetamido-3-hydroxyphenyl)-2-methylprop-2-enamide Chemical compound CC(=O)NC1=CC=C(NC(=O)C(C)=C)C=C1O YYKVDYMYOLDZEZ-UHFFFAOYSA-N 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- GRONZTPUWOOUFQ-UHFFFAOYSA-M sodium;methanol;hydroxide Chemical compound [OH-].[Na+].OC GRONZTPUWOOUFQ-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- MZFGYVZYLMNXGL-UHFFFAOYSA-N undec-10-enoyl chloride Chemical compound ClC(=O)CCCCCCCCC=C MZFGYVZYLMNXGL-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 1
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DSIGYWYKUCPBAF-UHFFFAOYSA-N 1-(prop-2-enoylamino)butane-1-sulfonic acid Chemical compound CCCC(S(O)(=O)=O)NC(=O)C=C DSIGYWYKUCPBAF-UHFFFAOYSA-N 0.000 description 1
- GGZHVNZHFYCSEV-UHFFFAOYSA-N 1-Phenyl-5-mercaptotetrazole Chemical compound SC1=NN=NN1C1=CC=CC=C1 GGZHVNZHFYCSEV-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- LKGFNNSOZPTLSS-UHFFFAOYSA-M 1-benzyl-2-methylpyridin-1-ium;bromide Chemical compound [Br-].CC1=CC=CC=[N+]1CC1=CC=CC=C1 LKGFNNSOZPTLSS-UHFFFAOYSA-M 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical compound CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 1
- OZFIGURLAJSLIR-UHFFFAOYSA-N 1-ethenyl-2h-pyridine Chemical compound C=CN1CC=CC=C1 OZFIGURLAJSLIR-UHFFFAOYSA-N 0.000 description 1
- JPHFEORIGQEXOQ-UHFFFAOYSA-N 1-hydroxy-n-[2-(prop-2-enoylamino)ethyl]naphthalene-2-carboxamide Chemical compound C1=CC=C2C(O)=C(C(=O)NCCNC(=O)C=C)C=CC2=C1 JPHFEORIGQEXOQ-UHFFFAOYSA-N 0.000 description 1
- ZFYKDNCOQBBOST-UHFFFAOYSA-N 1-phenylbut-3-en-1-one Chemical compound C=CCC(=O)C1=CC=CC=C1 ZFYKDNCOQBBOST-UHFFFAOYSA-N 0.000 description 1
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
- GUOSQNAUYHMCRU-UHFFFAOYSA-N 11-Aminoundecanoic acid Chemical compound NCCCCCCCCCCC(O)=O GUOSQNAUYHMCRU-UHFFFAOYSA-N 0.000 description 1
- JAAIPIWKKXCNOC-UHFFFAOYSA-N 1h-tetrazol-1-ium-5-thiolate Chemical compound SC1=NN=NN1 JAAIPIWKKXCNOC-UHFFFAOYSA-N 0.000 description 1
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- IBDVWXAVKPRHCU-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC(=O)C(C)=C IBDVWXAVKPRHCU-UHFFFAOYSA-N 0.000 description 1
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- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003284 rhodium compounds Chemical class 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- OWHUYYOLMQBAHA-UHFFFAOYSA-M sodium octadecanoate prop-2-enamide Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)[O-].[Na+].C(C=C)(=O)N OWHUYYOLMQBAHA-UHFFFAOYSA-M 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- YOECJUSHQJFRQY-UHFFFAOYSA-M sodium;2-(prop-2-enoylamino)hexadecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCCCC(CS([O-])(=O)=O)NC(=O)C=C YOECJUSHQJFRQY-UHFFFAOYSA-M 0.000 description 1
- HSFQBFMEWSTNOW-UHFFFAOYSA-N sodium;carbanide Chemical group [CH3-].[Na+] HSFQBFMEWSTNOW-UHFFFAOYSA-N 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- FYOWZTWVYZOZSI-UHFFFAOYSA-N thiourea dioxide Chemical class NC(=N)S(O)=O FYOWZTWVYZOZSI-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-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
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000005019 zein Substances 0.000 description 1
- 229940093612 zein Drugs 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
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/32—Colour coupling substances
- G03C7/327—Macromolecular coupling substances
- G03C7/3275—Polymers obtained by reactions involving only carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
-
- 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
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/04—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with macromolecular additives; with layer-forming substances
- G03C1/053—Polymers obtained by reactions involving only carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
-
- 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
- Y10S430/132—Anti-ultraviolet fading
-
- 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
- Y10S430/156—Precursor compound
-
- 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
- Y10S430/156—Precursor compound
- Y10S430/158—Development inhibitor releaser, DIR
-
- 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
- Y10S430/156—Precursor compound
- Y10S430/16—Blocked developers
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB7935782 | 1979-10-15 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5681835A JPS5681835A (en) | 1981-07-04 |
JPH0440700B2 true JPH0440700B2 (US06330241-20011211-M00004.png) | 1992-07-03 |
Family
ID=10508530
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP14188680A Granted JPS5681835A (en) | 1979-10-15 | 1980-10-09 | Copolymer latex and photographic silver halide material containing same latex |
Country Status (4)
Country | Link |
---|---|
US (1) | US4340664A (US06330241-20011211-M00004.png) |
EP (1) | EP0027284B1 (US06330241-20011211-M00004.png) |
JP (1) | JPS5681835A (US06330241-20011211-M00004.png) |
DE (1) | DE3064831D1 (US06330241-20011211-M00004.png) |
Families Citing this family (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5842044A (ja) * | 1981-09-07 | 1983-03-11 | Fuji Photo Film Co Ltd | ハロゲン化銀カラ−写真感光材料 |
JPS58111942A (ja) * | 1981-12-25 | 1983-07-04 | Fuji Photo Film Co Ltd | ハロゲン化銀写真感光材料 |
JPS58120252A (ja) * | 1982-01-11 | 1983-07-18 | Fuji Photo Film Co Ltd | ハロゲン化銀カラ−感光材料 |
JPS58178351A (ja) * | 1982-04-14 | 1983-10-19 | Fuji Photo Film Co Ltd | ハロゲン化銀写真感光材料 |
DE3217020A1 (de) * | 1982-05-06 | 1983-11-10 | Agfa-Gevaert Ag, 5090 Leverkusen | Photographisches aufzeichnungsmaterial |
US4490461A (en) * | 1982-07-23 | 1984-12-25 | Ciba-Geigy Ag | Process for the preparation of photographic materials |
JPS5923344A (ja) * | 1982-07-30 | 1984-02-06 | Fuji Photo Film Co Ltd | ハロゲン化銀写真感光材料 |
JPS5936249A (ja) * | 1982-08-24 | 1984-02-28 | Fuji Photo Film Co Ltd | ハロゲン化銀カラ−感光材料 |
JPS5965844A (ja) * | 1982-10-07 | 1984-04-14 | Fuji Photo Film Co Ltd | ハロゲン化銀カラ−写真感光材料 |
JPS5986048A (ja) * | 1982-11-09 | 1984-05-18 | Fuji Photo Film Co Ltd | ハロゲン化銀カラ−写真感光材料 |
JPS59129850A (ja) * | 1983-01-17 | 1984-07-26 | Fuji Photo Film Co Ltd | ハロゲン化銀カラ−写真感光材料 |
EP0185793A1 (en) * | 1984-12-24 | 1986-07-02 | Agfa-Gevaert N.V. | Copolymer latex and photographic silver halide materials containing such latex |
US4557998A (en) * | 1985-01-02 | 1985-12-10 | Eastman Kodak Company | Colorless ligand-releasing monomers and polymers and their use to provide dyes with metal ions |
US4680356A (en) * | 1985-01-02 | 1987-07-14 | Eastman Kodak Company | Colorless ligand-releasing monomers and polymers and their use to provide dyes with metal ions |
DE3627455A1 (de) * | 1985-08-15 | 1987-02-19 | Chevron Res | Acrylamido- und methacrylamido-n-substituierte sulfonsaeuren |
DE3536608C2 (de) * | 1985-10-15 | 1998-01-29 | Agfa Gevaert Ag | Polymere Kuppler und lichtempfindliches fotografisches Silberhalogenidaufzeichnungsmaterial mit derartigen Kupplern |
CA1291031C (en) * | 1985-12-23 | 1991-10-22 | Nikolaas C.J. De Jaeger | Method for the detection of specific binding agents and their correspondingbindable substances |
JPS62178233A (ja) * | 1986-01-31 | 1987-08-05 | Konishiroku Photo Ind Co Ltd | ハロゲン化銀カラ−写真感光材料 |
JPH0673008B2 (ja) * | 1986-09-12 | 1994-09-14 | 富士写真フイルム株式会社 | ハロゲン化銀カラ−写真感光材料 |
DE3882391T2 (de) * | 1987-02-27 | 1993-10-28 | Fuji Photo Film Co Ltd | Farbphotographisches Silberhalogenidmaterial. |
JP2540320B2 (ja) * | 1987-03-25 | 1996-10-02 | 富士写真フイルム株式会社 | ハロゲン化銀写真感光材料 |
JPH07119984B2 (ja) | 1987-04-30 | 1995-12-20 | 富士写真フイルム株式会社 | 写真感光材料 |
US5234807A (en) * | 1991-11-21 | 1993-08-10 | Eastman Kodak Company | Microemulsion polymerization - processes for dispersing photographically useful components |
US5629365A (en) * | 1992-06-23 | 1997-05-13 | Monsanto Company | UV-absorbing polymer latex |
EP0648249A1 (en) * | 1992-06-23 | 1995-04-19 | Monsanto Company | Uv-absorbing polymer latex |
US5385815A (en) * | 1992-07-01 | 1995-01-31 | Eastman Kodak Company | Photographic elements containing loaded ultraviolet absorbing polymer latex |
US5384235A (en) * | 1992-07-01 | 1995-01-24 | Eastman Kodak Company | Photographic elements incorporating polymeric ultraviolet absorbers |
US5372922A (en) * | 1993-12-29 | 1994-12-13 | Eastman Kodak Company | Method of preparing photographic elements incorporating polymeric ultraviolet absorbers |
US5858633A (en) * | 1994-12-21 | 1999-01-12 | Eastman Kodak Company | Photographic elements containing 3-alkyl group substituted 2-hydroxyphenylbenzotriazole UV absorbing polymers |
US5747585A (en) * | 1995-02-17 | 1998-05-05 | Eastman Kodak Company | Process for synthesizing latex polymers from solid monomer particles |
US5766834A (en) * | 1996-05-17 | 1998-06-16 | Eastman Kodak Company | Photographic element containing ultraviolet absorbing polymer |
US6252025B1 (en) | 1998-08-11 | 2001-06-26 | Eastman Kodak Company | Vinyl hyperbranched polymer with photographically useful end groups |
US6589724B1 (en) * | 2001-10-24 | 2003-07-08 | Eastman Kodak Company | Color photographic element containing speed-improving benzotriazole polymer |
US7441886B2 (en) | 2004-02-05 | 2008-10-28 | Hewlett-Packard Development Company, L.P. | Fused ink-jet image with high image quality, air fastness, and light stability |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3926436A (en) * | 1973-02-26 | 1975-12-16 | Marcel Jacob Monbaliu | Silver halide element containing polymeric colour forming couplers |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE596034A (US06330241-20011211-M00004.png) * | 1959-10-12 | |||
US3163625A (en) * | 1960-04-13 | 1964-12-29 | Du Pont | Color-forming monomers and polymers of acrylic acid amides of 3-aminopyrazolone |
NL275031A (US06330241-20011211-M00004.png) * | 1961-03-02 | |||
CH485782A (de) * | 1964-06-23 | 1970-02-15 | Gevaert Photo Prod Nv | Verfahren zur Emulsionspolymerisation |
GB1130581A (en) * | 1965-01-01 | 1968-10-16 | Gevaert Photo Prod Nv | Photographic gelatin compositions containing colour couplers |
DE1770994A1 (de) * | 1967-03-20 | 1972-01-20 | Rohm & Haas | Neue Polymere |
GB1581439A (en) * | 1976-06-15 | 1980-12-17 | Agfa Gevaert | Polymeric coupler latices for use in silver halide photography |
-
1980
- 1980-09-18 EP EP80200879A patent/EP0027284B1/en not_active Expired
- 1980-09-18 DE DE8080200879T patent/DE3064831D1/de not_active Expired
- 1980-09-19 US US06/188,734 patent/US4340664A/en not_active Expired - Lifetime
- 1980-10-09 JP JP14188680A patent/JPS5681835A/ja active Granted
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3926436A (en) * | 1973-02-26 | 1975-12-16 | Marcel Jacob Monbaliu | Silver halide element containing polymeric colour forming couplers |
Also Published As
Publication number | Publication date |
---|---|
US4340664A (en) | 1982-07-20 |
EP0027284B1 (en) | 1983-09-14 |
JPS5681835A (en) | 1981-07-04 |
DE3064831D1 (en) | 1983-10-20 |
EP0027284A1 (en) | 1981-04-22 |
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