EP0011051B1 - Matériel d'enregistrement photographique en couleurs, procédé pour sa stabilisation et préparation d'images photographiques en couleurs - Google Patents
Matériel d'enregistrement photographique en couleurs, procédé pour sa stabilisation et préparation d'images photographiques en couleurs Download PDFInfo
- Publication number
- EP0011051B1 EP0011051B1 EP79810141A EP79810141A EP0011051B1 EP 0011051 B1 EP0011051 B1 EP 0011051B1 EP 79810141 A EP79810141 A EP 79810141A EP 79810141 A EP79810141 A EP 79810141A EP 0011051 B1 EP0011051 B1 EP 0011051B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- carbon atoms
- alkyl
- recording material
- light
- hydrogen
- 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
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- 239000000463 material Substances 0.000 title claims description 37
- 238000000034 method Methods 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 230000006641 stabilisation Effects 0.000 title 1
- -1 piperidine compound Chemical class 0.000 claims description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
- 239000010410 layer Substances 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 27
- 239000000839 emulsion Substances 0.000 claims description 27
- 239000004611 light stabiliser Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 229910052709 silver Inorganic materials 0.000 claims description 16
- 239000004332 silver Substances 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 239000006096 absorbing agent Substances 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 238000011161 development Methods 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 239000011241 protective layer Substances 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 230000009931 harmful effect Effects 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 239000011229 interlayer Substances 0.000 claims 2
- SLYRGJDSFOCAAI-UHFFFAOYSA-N 1,3-thiazolidin-2-one Chemical compound O=C1NCCS1 SLYRGJDSFOCAAI-UHFFFAOYSA-N 0.000 claims 1
- 230000003019 stabilising effect Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
- 108010010803 Gelatin Proteins 0.000 description 11
- 229920000159 gelatin Polymers 0.000 description 11
- 239000008273 gelatin Substances 0.000 description 11
- 235000019322 gelatine Nutrition 0.000 description 11
- 235000011852 gelatine desserts Nutrition 0.000 description 11
- 150000002431 hydrogen Chemical group 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 238000002604 ultrasonography Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 238000005452 bending Methods 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
- 238000001035 drying Methods 0.000 description 3
- 238000005562 fading Methods 0.000 description 3
- 239000004848 polyfunctional curative Substances 0.000 description 3
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- ZEUDGVUWMXAXEF-UHFFFAOYSA-L bromo(chloro)silver Chemical compound Cl[Ag]Br ZEUDGVUWMXAXEF-UHFFFAOYSA-L 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 125000006289 hydroxybenzyl group Chemical group 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000003053 piperidines Chemical class 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 0 CCc(cc(CCC(*)C(OC(C)[C@](C)**)=O)cc1C)c1O Chemical compound CCc(cc(CCC(*)C(OC(C)[C@](C)**)=O)cc1C)c1O 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 230000006181 N-acylation Effects 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 229910021612 Silver iodide Inorganic materials 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- RUTWCOZYFYYRSL-UHFFFAOYSA-N benzyl(hydroxy)carbamodithioic acid Chemical class SC(=S)N(O)CC1=CC=CC=C1 RUTWCOZYFYYRSL-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- OIPQUBBCOVJSNS-UHFFFAOYSA-L bromo(iodo)silver Chemical compound Br[Ag]I OIPQUBBCOVJSNS-UHFFFAOYSA-L 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical class NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical compound ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 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
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000001043 yellow dye 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
- 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
- G03C7/392—Additives
- G03C7/39208—Organic compounds
- G03C7/3924—Heterocyclic
- G03C7/39244—Heterocyclic the nucleus containing only nitrogen as hetero atoms
- G03C7/39248—Heterocyclic the nucleus containing only nitrogen as hetero atoms one nitrogen atom
Definitions
- the present invention relates to a color photographic recording material which contains at least one light stabilizer in at least one light-sensitive silver halide emulsion layer and / or in at least one of the customary auxiliary layers.
- Phenols or lX- naphthols are usually used as cyan couplers, pyrazolones as purple couplers and acylacetylamides as yellow couplers.
- the dyes formed after development are accordingly indophenols, indamines or azomethines.
- the ultraviolet absorbers In order to achieve adequate light protection, however, relatively large amounts of the ultraviolet absorbers must be used, which generally has the consequence that the thickness of the photographic layers into which the ultraviolet absorbers are incorporated must be increased. Such a measure is highly undesirable for the photographic properties of the material.
- the ultraviolet absorbers also do not provide effective protection against fading of color images by visible light.
- Another disadvantage of using relatively large amounts of ultraviolet absorbers is that large amounts of solvent are required in order to achieve the desired fine distribution of these compounds in the aqueous binder emulsions. If concentrated solutions of the ultraviolet absorbers are used, there is a risk that they will become uncontrolled during incorporation into the binder emulsions. H. do not deposit in the desired fine distribution and so uniform protection against ultraviolet radiation cannot be achieved.
- the present invention therefore provides a color photographic recording material comprising at least p nt sexual a piperidine compound as light stabilizer in at least one photosensitive silver halide emulsion layer, an intermediate layer and / or a protective layer, characterized in that the piperidine compound of formula corresponds, in which R 1 is hydrogen or alkyl having 1 to 4 carbon atoms, R 2 is alkyl or hydroxyalkyl each having 1 to 12 carbon atoms, alkenyl or alkynyl having 3 or 4 carbon atoms, benzyl or R 6 C0-, in which R 6 is hydrogen, alkyl phenyl or phenylethyl substituted by 1 to 12 carbon atoms, alkenyl having 2 or 3 carbon atoms, chloromethyl, cyclohexyl, benzyl or optionally substituted by two alkyl groups each having 1 to 4 carbon atoms and a hydroxyl group, R 3 is hydrogen or methyl, R 4 and R 5 each are alkyl having 1 to
- the light stabilizers can also be used in combination with conventional ultraviolet absorbers.
- the present invention furthermore relates to a process for stabilizing color photographic recording materials by incorporating at least one light stabilizer of the formula (1), if appropriate in combination with an ultraviolet absorber, into at least one light-sensitive and / or auxiliary layer of the material, a process for the preparation of the harmful action light-stabilized color photographic images by imagewise exposure and color development of said recording materials and the color photographic images thus obtained.
- R 1 is alkyl with 1 to 4 carbon atoms, such as. As methyl, ethyl, n-propyl or n-butyl. Ethyl and especially methyl are preferred.
- R 2 is alkyl having 1 to 12 carbon atoms
- primary alkyl groups such as those mentioned above generally come, furthermore, for. B. n-amyl, n-hexyl, n-octyl, n-nonyl, n-decyl or n-dodecyl in question.
- the analogous radicals apply to the meaning of hydroxyalkyl.
- R 2 in the meaning alkenyl or alkynyl with 3 or 4 carbons can, for. As allyl, methallyl or propargyl.
- R 2 are alkyl or hydroxyalkyl each having 1 to 4 carbon atoms, alkenyl or alkynyl having 3 or 4 carbon atoms, benzyl and also acyl, where formyl, acetyl, propionyl, acrylyl, methacrylyl, crotonyl, benzoyl or benzylcarbonyl can be mentioned.
- the substituent Y as an optionally present substituent on the central carbon atom in the compounds of the formula (1) can be hydrogen, straight-chain or branched alkyl having 1 to 12 carbon atoms, such as, for. B. methyl, ethyl, propyl, iso-propyl, butyl, n-amyl, n-hexyl, n- and iso-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl or dodecyl and the corresponding Isomers.
- R 7 may be hydrogen, methyl, ethyl or a radical of the formula (1a).
- R 8 is methyl or ethyl, furthermore phenyl or benzyl; Y is also cyan, benzyl or a radical of the formula (1b).
- the substituents in the radicals of the formulas (1a) and (1b) have the meanings given.
- the substituent Rg in the formula (1 b) has the meaning hydrogen, methyl or ethyl.
- Color photographic recording materials which have at least one compound of the formula as light stabilizers are preferred contain, wherein R 10 is methyl, ethyl, benzyl, acetyl, acrylyl, methacrylyl, crotonyl, allyl or propargyl.
- the compounds of the formulas (1) to (31) are known compounds which, for. B. are described in DE-OS 2 456 364, 2 647 452, 2 654 058 and 2 656 769.
- the compounds can be prepared by various methods, generally requiring several reaction steps.
- Starting materials for the first reaction stage are e.g. B. the malonic acid, or one of its reactive derivatives, such as the dialkyl esters, and 4-hydroxy- or 4-aminopiperidines, where the substituents (R 2 ) on the nitrogen atom of the piperidine ring may already be present in the molecule or in a later N.
- -Alkyl ists- or N-acylation step can be introduced into the molecule by conventional methods.
- Suitable alkylating or acylating agents are, for example, alkyl halides, alkenyl halides, propargyl chloride, benzyl chloride or carboxylic acid chlorides, which are preferably reacted with the piperidine derivative in the presence of molar amounts of a base.
- Hydroxyalkyl residues are introduced into the molecule by reaction with epoxides, for example ethylene oxide or propylene oxide.
- the hydroxybenzyl group can be introduced by reaction with an alkyl-substituted hydroxybenzyldithiocarbamate of the formula HO-benzyl-S-CS-N (R ") 2 , where R" denotes an alkyl group with 1 to 5 carbon atoms or both groups R "together with the nitrogen one Such morpholine, pyrrolidine or piperidine ring .
- Such dithiocarbamates can be obtained by reacting a phenol with formaldehyde, carbon disulfide and a secondary amine.
- substituent Y is present in the compounds of the formulas (1) and (2), it can be introduced into the molecule by the known methods of C-alkylation of activated methylene compounds.
- the compounds of the formulas (1) and (2) are hardly soluble in water, and they are therefore in a low-boiling organic solvent, such as methaloacetate, ethyl acetate, carbon tetrachloride, chloroform, methanol, ethanol, n-butanol, dioxane, acetone or benzene, a high-boiling organic solvent, such as tricresyl phosphate, dimethylformamide, dimethyl sulfoxide, di-n-butyl phthalate or ethyl-N-diphenylcarbamate, or a solvent mixture of the above-mentioned low-boiling and high-boiling organic solvents, the resulting solution becomes a protective colloid solution, such as, in particular, an aqueous gelatin solution , given and dispersed by means of a colloid mill, a homogenizer or by using ultrasound.
- a protective colloid solution such as, in particular, an
- the dispersions thus obtained are then used to produce the layers of color photographic recording materials (for example film, paper or silver color bleaching materials).
- These layers can e.g. B. Intermediate or protective layers, but especially photosensitive (blue and red sensitive) silver halide emulsion layers, in which the cyan (cyan), magenta (magenta) and yellow dyes are formed during the development of the exposed recording material from the corresponding color couplers .
- ultraviolet absorbers are also used, they are located in the same layers, but preferably in the intermediate or protective layers.
- Any cyan, magenta and yellow couplers that are used to form the dyes mentioned and thus the color images can be used.
- the silver halide emulsions preferably contain gelatin as a binder, optionally in a mixture with other high-molecular natural or synthetic compounds.
- the silver halide emulsions can, for example, be silver bromide, silver chloride or silver iodide emulsions or also those emulsions which contain a mixture of silver halides, such as, for. B. silver bromide-iodide or silver chloride bromide emulsions.
- the emulsions can be chemically sensitized, they can also be conventional organic stabilizers and antifoggants and also conventional plasticizers, such as. B. glycerin.
- the emulsions can also be hardened with the hardeners customary for gelatin.
- the emulsions may also contain conventional pouring aids.
- the emulsions can be applied to conventional supports for photographic recording material.
- the customary developer baths can be used to develop the color photographic recording material. These usually contain a developer substance of the p-phenylenediamine type, a development retardant such as potassium bromide, an antioxidant such as sodium sulfite, and a base, e.g. B. an alkali hydroxide or alkali carbonate.
- the developing baths may also contain a conventional antifoggant and complexing agent.
- the ultraviolet absorber can be present together with the light stabilizer in one layer or in an adjacent layer.
- the weight ratio between a conventional ultraviolet absorber and the light stabilizer of the formula (1) is approximately (5-10): 1, the molar ratio approximately (10-20): 1.
- Examples of ultraviolet absorbers are e.g. B. Compounds of the benzophenone, acrylonitrile, thiazolidine, benzotriazole, oxazole, thiazole and imidazole type.
- the color images obtained with the recording material according to the invention by exposure and development show a clearly improved light fastness to visible and ultraviolet light.
- the compounds of formula (1) are practically colorless, so that there is no discoloration of the images; in addition, they are well compatible with the usual photographic additives present in the individual layers; Because of their good effectiveness, their use amount can be reduced and their precipitation or crystallization can be avoided if they are incorporated as an organic solution in the aqueous binder emulsions used for the production of photographic layers.
- the individual processing steps necessary for the production of the color images after the exposure of the photographic recording material are not adversely affected by the light stabilizers. Furthermore, the so-called pressure fog formation that frequently occurs with blue-sensitive emulsions can be largely suppressed.
- 0.4 ml of 1.5% aqueous gelatin solution and 4.0 ml of water are mixed together, adjusted to a pH of 6.5 and poured at 40 ° C. onto a 13 x 18 cm format glass plate. After the layer has solidified at 10 ° C., the plate is dried in a drying cabinet with ambient air at room temperature.
- a strip of the coated glass plate cut to a format of 4.0 cm x 6.5 cm is exposed to 500 lux for 6 seconds under a step wedge and then processed at 32.8 ° C ( ⁇ 0.3 ° C) as follows:
- the developer bath has the following composition:
- a conventional bath is used as a bleach-fixing bath, e.g. B. has the following composition.
- the step wedge obtained in this way is irradiated in an Atlas device (lamp 2500 W) with 10,000 Langley units each with and without an ultraviolet filter (Kodak filter 2C).
- a step wedge produced in an analog manner, which contains no additive, and further step wedges which were produced using the compounds of the formulas (104) and (107) to (110) are used for comparison.
- the data show the good protection of the photographic material against the harmful influence of light, which can be achieved when using the light stabilizers used according to the invention.
- the effects are significantly improved compared to those that can be achieved with known light stabilizers already used in photographic materials.
- Good results are also obtained with the compounds of the formulas (4), (6), (8) to (22) and (24) to (31).
- a strip of the coated glass plate cut to a format of 4.0 cm ⁇ 6.5 cm is exposed under a step wedge at 500 lux for 6 seconds and then at 32.8 ° C. ( ⁇ 0.3 ° C) processed as described in Example 1.
- a clear, sharp, blue-green colored step wedge is obtained with an absorption maximum at 653 nm and a maximum density of 1.10.
- step wedge and step wedges produced analogously, which were produced using the compounds (105) to (110), are exposed and measured as described in Example 1. Table 2 contains the results.
- 3,510- 3 mol of the yellow coupler of the formula (DE-OS 2716204) are dissolved in 10 ml of ethyl acetate and mixed with 1.5 g of tricresyl phosphate.
- This solution is emulsified in 100 ml of 4% gelatin solution, which contains 0.3 g of an alkyl aryl sulfonate emulsifier, using an ultrasound device.
- the ethyl acetate is then distilled off.
- a light-sensitive silver chloride bromide dispersion average particle size of the silver halide crystals about 1 ⁇ m which was chemically sensitized in the usual way is then mixed in at about 40 ° C.
- ⁇ D min so-called pressure veil.
- the increase in the minimum density compared to the blank is a measure of the bending stress.
- Gelatin solutions are prepared as in Example 1, but the light stabilizers of the formulas (23) (according to the invention) and (105) and (106) (comparison) and the yellow coupler of the formula are used or the formula (DE-OS 2 757 380).
- the light stabilizers and the yellow couplers are used in a molar ratio of 1: 1.
- Example 1 The production of the coated glass plates, the exposure and photographic processing and the light fastness test are carried out as in Example 1.
- the light fastness test is carried out with an irradiation of 15,000 Langley units.
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Hydrogenated Pyridines (AREA)
Claims (8)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH11396/78 | 1978-11-06 | ||
CH1139678 | 1978-11-06 |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0011051A2 EP0011051A2 (fr) | 1980-05-14 |
EP0011051A3 EP0011051A3 (en) | 1980-05-28 |
EP0011051B1 true EP0011051B1 (fr) | 1982-09-15 |
Family
ID=4373117
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP79810141A Expired EP0011051B1 (fr) | 1978-11-06 | 1979-10-31 | Matériel d'enregistrement photographique en couleurs, procédé pour sa stabilisation et préparation d'images photographiques en couleurs |
Country Status (5)
Country | Link |
---|---|
US (1) | US4268593A (fr) |
EP (1) | EP0011051B1 (fr) |
JP (1) | JPS5565954A (fr) |
CA (1) | CA1145605A (fr) |
DE (1) | DE2963689D1 (fr) |
Families Citing this family (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS58102231A (ja) * | 1981-12-14 | 1983-06-17 | Fuji Photo Film Co Ltd | カラ−写真感光材料 |
DE3275592D1 (en) * | 1981-12-17 | 1987-04-09 | Ciba Geigy Ag | Colour-photographic recording material |
EP0103540A1 (fr) * | 1982-08-18 | 1984-03-21 | Ciba-Geigy Ag | Matériel d'enregistrement photographique en couleurs |
EP0104146B1 (fr) * | 1982-09-21 | 1986-07-30 | Ciba-Geigy Ag | Matériau d'enregistrement photographique couleur |
DE3375431D1 (en) * | 1982-11-18 | 1988-02-25 | Ciba Geigy Ag | Colour-photographic recording material |
DE3375432D1 (en) * | 1982-11-26 | 1988-02-25 | Ciba Geigy Ag | Colour-photographic recording material |
DE3375230D1 (en) * | 1982-12-03 | 1988-02-11 | Ciba Geigy Ag | Colour-photographic recording material |
EP0111448B1 (fr) * | 1982-12-08 | 1988-01-13 | Ciba-Geigy Ag | Matériel d'enregistrement photographique couleur |
DE3377596D1 (en) * | 1982-12-16 | 1988-09-08 | Ciba Geigy Ag | Colour-photographic recording material |
DE3373720D1 (en) * | 1982-12-16 | 1987-10-22 | Ciba Geigy Ag | Colour-photographic recording material |
DE3375231D1 (en) * | 1982-12-16 | 1988-02-11 | Ciba Geigy Ag | Colour-photographic recording material |
JPS59124340A (ja) * | 1982-12-30 | 1984-07-18 | Konishiroku Photo Ind Co Ltd | ハロゲン化銀写真感光材料 |
JPS60222853A (ja) * | 1984-04-20 | 1985-11-07 | Konishiroku Photo Ind Co Ltd | ハロゲン化銀写真感光材料 |
EP0203746B2 (fr) * | 1985-05-11 | 1994-08-24 | Konica Corporation | Matériau photographique à l'halogénure d'argent sensible à la lumière |
US4728599A (en) * | 1985-12-02 | 1988-03-01 | Eastman Kodak Company | Sterically hindered phenolic ester photographic coupler dispersion addenda and photographic elements employing same |
EP0256537B1 (fr) | 1986-08-15 | 1992-12-30 | Fuji Photo Film Co., Ltd. | Epreuve couleur et méthode pour sa production |
EP0382285B1 (fr) * | 1989-02-08 | 1994-10-26 | Agfa-Gevaert N.V. | Matériau de toner en particules |
US5449777A (en) * | 1993-07-08 | 1995-09-12 | Ciba-Geigy Corporation | Phenolic s-triazines |
JP3584119B2 (ja) | 1996-04-05 | 2004-11-04 | 富士写真フイルム株式会社 | ハロゲン化銀カラー写真感光材料 |
US7090969B1 (en) | 2005-03-15 | 2006-08-15 | Eastman Kodak Company | Coupler and image dye light-stabilizing systems |
WO2008076101A1 (fr) * | 2006-12-18 | 2008-06-26 | 3M Innovative Properties Company | Composition de résine (méth)acrylique et films fabriqués à partir de cette composition |
JP4988383B2 (ja) * | 2007-03-02 | 2012-08-01 | スリーエム イノベイティブ プロパティズ カンパニー | (メタ)アクリル系着色フィルム、マーキングフィルム、レセプターシート、及びその製造方法 |
JP5307378B2 (ja) * | 2007-10-26 | 2013-10-02 | スリーエム イノベイティブ プロパティズ カンパニー | (メタ)アクリル系フィルムおよびこれを用いたマーキングフィルム |
JP2009270062A (ja) | 2008-05-09 | 2009-11-19 | Fujifilm Corp | 紫外線吸収剤組成物 |
CN112010800B (zh) * | 2020-09-08 | 2021-11-16 | 宿迁联盛科技股份有限公司 | 一种含受阻酚的受阻胺光稳定剂及其制备方法和应用 |
CN112010799B (zh) * | 2020-09-08 | 2022-03-25 | 宿迁联盛科技股份有限公司 | 一种受阻胺光稳定剂中间体及其制备方法和应用 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2596926A (en) * | 1949-12-16 | 1952-05-13 | Gen Aniline & Film Corp | Preparation of azine dye images |
US3183219A (en) * | 1963-10-29 | 1965-05-11 | Polaroid Corp | 2-benzoyl-5-methoxyphenyl acrylate and polymers thereof |
JPS4920973B1 (fr) * | 1970-05-28 | 1974-05-29 | ||
CH601232A5 (fr) * | 1975-12-08 | 1978-06-30 | Ciba Geigy Ag |
-
1979
- 1979-10-31 DE DE7979810141T patent/DE2963689D1/de not_active Expired
- 1979-10-31 EP EP79810141A patent/EP0011051B1/fr not_active Expired
- 1979-11-02 CA CA000339028A patent/CA1145605A/fr not_active Expired
- 1979-11-05 US US06/091,275 patent/US4268593A/en not_active Expired - Lifetime
- 1979-11-06 JP JP14288279A patent/JPS5565954A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS5565954A (en) | 1980-05-17 |
EP0011051A2 (fr) | 1980-05-14 |
US4268593A (en) | 1981-05-19 |
JPS5720617B2 (fr) | 1982-04-30 |
DE2963689D1 (en) | 1982-11-04 |
EP0011051A3 (en) | 1980-05-28 |
CA1145605A (fr) | 1983-05-03 |
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