EP0135901A2 - Matériel pour l'enregistrement thermosensible - Google Patents
Matériel pour l'enregistrement thermosensible Download PDFInfo
- Publication number
- EP0135901A2 EP0135901A2 EP84111015A EP84111015A EP0135901A2 EP 0135901 A2 EP0135901 A2 EP 0135901A2 EP 84111015 A EP84111015 A EP 84111015A EP 84111015 A EP84111015 A EP 84111015A EP 0135901 A2 EP0135901 A2 EP 0135901A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- heat
- color developing
- sensitive recording
- developing agent
- nitrobenzoic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000463 material Substances 0.000 title claims abstract description 20
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 47
- 229910052751 metal Inorganic materials 0.000 claims abstract description 38
- 239000002184 metal Substances 0.000 claims abstract description 38
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000006185 dispersion Substances 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 23
- -1 sensitizers Substances 0.000 claims description 20
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 16
- 239000011248 coating agent Substances 0.000 claims description 15
- 238000000576 coating method Methods 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 8
- 239000011230 binding agent Substances 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 239000000945 filler Substances 0.000 claims description 6
- LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 claims description 4
- 239000008199 coating composition Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 239000011575 calcium Substances 0.000 claims description 3
- 238000000227 grinding Methods 0.000 claims description 3
- 239000000314 lubricant Substances 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 49
- 239000000975 dye Substances 0.000 description 38
- 229920002451 polyvinyl alcohol Polymers 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 239000004372 Polyvinyl alcohol Substances 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 11
- 239000003086 colorant Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 5
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 5
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 4
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000010419 fine particle Substances 0.000 description 3
- TZPGGFYKIOBMCN-UHFFFAOYSA-N 3-chloro-4-nitrobenzoic acid Chemical class OC(=O)C1=CC=C([N+]([O-])=O)C(Cl)=C1 TZPGGFYKIOBMCN-UHFFFAOYSA-N 0.000 description 2
- XDTTUTIFWDAMIX-UHFFFAOYSA-N 3-methyl-4-nitrobenzoic acid Chemical class CC1=CC(C(O)=O)=CC=C1[N+]([O-])=O XDTTUTIFWDAMIX-UHFFFAOYSA-N 0.000 description 2
- AFPHTEQTJZKQAQ-UHFFFAOYSA-N 3-nitrobenzoic acid Chemical class OC(=O)C1=CC=CC([N+]([O-])=O)=C1 AFPHTEQTJZKQAQ-UHFFFAOYSA-N 0.000 description 2
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000013256 coordination polymer Substances 0.000 description 2
- JJXVDRYFBGDXOU-UHFFFAOYSA-N dimethyl 4-hydroxybenzene-1,2-dicarboxylate Chemical compound COC(=O)C1=CC=C(O)C=C1C(=O)OC JJXVDRYFBGDXOU-UHFFFAOYSA-N 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- XIKIUQUXDNHBFR-UHFFFAOYSA-N monobenzyl phthalate Chemical compound OC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 XIKIUQUXDNHBFR-UHFFFAOYSA-N 0.000 description 2
- 150000005338 nitrobenzoic acids Chemical class 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 150000003751 zinc Chemical class 0.000 description 2
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 2
- MKWJZTFMDWSRIH-UHFFFAOYSA-N (4-fluoro-3-nitrophenyl)methanol Chemical class OCC1=CC=C(F)C([N+]([O-])=O)=C1 MKWJZTFMDWSRIH-UHFFFAOYSA-N 0.000 description 1
- UEXAQQULOLUJRX-UHFFFAOYSA-N 1-N,1-N-dibutyl-2-chloro-3-N-fluoro-4-methylbenzene-1,3-diamine Chemical compound C(CCC)N(C=1C(=C(NF)C(=CC=1)C)Cl)CCCC UEXAQQULOLUJRX-UHFFFAOYSA-N 0.000 description 1
- YPQAFWHSMWWPLX-UHFFFAOYSA-N 1975-50-4 Chemical class CC1=C(C(O)=O)C=CC=C1[N+]([O-])=O YPQAFWHSMWWPLX-UHFFFAOYSA-N 0.000 description 1
- RYHQDYUGPBZCFQ-UHFFFAOYSA-N 2'-anilino-3'-methyl-6'-piperidin-1-ylspiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound CC1=CC=2OC3=CC(N4CCCCC4)=CC=C3C3(C4=CC=CC=C4C(=O)O3)C=2C=C1NC1=CC=CC=C1 RYHQDYUGPBZCFQ-UHFFFAOYSA-N 0.000 description 1
- SOMMOMFRWWYPHK-UHFFFAOYSA-N 2-(4-ethylphenoxy)carbonylbenzoic acid Chemical compound C1=CC(CC)=CC=C1OC(=O)C1=CC=CC=C1C(O)=O SOMMOMFRWWYPHK-UHFFFAOYSA-N 0.000 description 1
- GOVBKFNXUNXORO-UHFFFAOYSA-N 2-(4-methylphenoxy)carbonylbenzoic acid Chemical compound C1=CC(C)=CC=C1OC(=O)C1=CC=CC=C1C(O)=O GOVBKFNXUNXORO-UHFFFAOYSA-N 0.000 description 1
- VQCAQTNPROLAJK-UHFFFAOYSA-N 2-benzoyl-3-nitrobenzoic acid Chemical class OC(=O)C1=CC=CC([N+]([O-])=O)=C1C(=O)C1=CC=CC=C1 VQCAQTNPROLAJK-UHFFFAOYSA-N 0.000 description 1
- YZDQOKBFBUAJPD-UHFFFAOYSA-N 2-benzoyl-4-nitrobenzoic acid Chemical class OC(=O)C1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 YZDQOKBFBUAJPD-UHFFFAOYSA-N 0.000 description 1
- MXOGJBKTZBIWOT-UHFFFAOYSA-N 2-phenoxycarbonylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OC1=CC=CC=C1 MXOGJBKTZBIWOT-UHFFFAOYSA-N 0.000 description 1
- VYWYYJYRVSBHJQ-UHFFFAOYSA-N 3,5-dinitrobenzoic acid Chemical class OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 VYWYYJYRVSBHJQ-UHFFFAOYSA-N 0.000 description 1
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 1
- YLQAJBKACBLUCM-UHFFFAOYSA-N 3-chloro-5-nitrobenzoic acid Chemical class OC(=O)C1=CC(Cl)=CC([N+]([O-])=O)=C1 YLQAJBKACBLUCM-UHFFFAOYSA-N 0.000 description 1
- XAPRFOJQNGFJSZ-UHFFFAOYSA-N 3-methyl-5-nitrobenzoic acid Chemical class CC1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 XAPRFOJQNGFJSZ-UHFFFAOYSA-N 0.000 description 1
- XHQYAMKBTLODDV-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)heptan-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)(CCCCC)C1=CC=C(O)C=C1 XHQYAMKBTLODDV-UHFFFAOYSA-N 0.000 description 1
- HJSPWKGEPDZNLK-UHFFFAOYSA-N 4-benzylphenol Chemical compound C1=CC(O)=CC=C1CC1=CC=CC=C1 HJSPWKGEPDZNLK-UHFFFAOYSA-N 0.000 description 1
- MSOMKPVOBYNJIP-UHFFFAOYSA-N 4-chloro-3-n,3-n-diethyl-1-n-fluoro-6-methylbenzene-1,3-diamine Chemical compound CCN(CC)C1=CC(NF)=C(C)C=C1Cl MSOMKPVOBYNJIP-UHFFFAOYSA-N 0.000 description 1
- 229940073735 4-hydroxy acetophenone Drugs 0.000 description 1
- BBEWSMNRCUXQRF-UHFFFAOYSA-N 4-methyl-3-nitrobenzoic acid Chemical class CC1=CC=C(C(O)=O)C=C1[N+]([O-])=O BBEWSMNRCUXQRF-UHFFFAOYSA-N 0.000 description 1
- WHTXLZQPQJAELS-UHFFFAOYSA-N 4-tert-butyl-3,5-dinitrobenzoic acid Chemical class CC(C)(C)C1=C([N+]([O-])=O)C=C(C(O)=O)C=C1[N+]([O-])=O WHTXLZQPQJAELS-UHFFFAOYSA-N 0.000 description 1
- QIHHYQWNYKOHEV-UHFFFAOYSA-N 4-tert-butyl-3-nitrobenzoic acid Chemical class CC(C)(C)C1=CC=C(C(O)=O)C=C1[N+]([O-])=O QIHHYQWNYKOHEV-UHFFFAOYSA-N 0.000 description 1
- SYCDPZQKLVQBKY-UHFFFAOYSA-N 4-tert-butyl-4-(1-tert-butyl-4-hydroxy-6-methylcyclohexa-2,4-dien-1-yl)sulfanyl-3-methylcyclohexa-1,5-dien-1-ol Chemical compound CC1C=C(O)C=CC1(C(C)(C)C)SC1(C(C)(C)C)C(C)C=C(O)C=C1 SYCDPZQKLVQBKY-UHFFFAOYSA-N 0.000 description 1
- OIIAWEYLHHHZJC-UHFFFAOYSA-N 5-[4-(diethylamino)-2-ethoxyphenyl]-5-(1-ethyl-2-methylindol-3-yl)furo[3,4-b]pyridin-7-one Chemical compound CCOC1=CC(N(CC)CC)=CC=C1C1(C=2C3=CC=CC=C3N(CC)C=2C)C2=CC=CN=C2C(=O)O1 OIIAWEYLHHHZJC-UHFFFAOYSA-N 0.000 description 1
- MWTMXYXPZGPRJQ-UHFFFAOYSA-N 5-hydroxy-2-phenylmethoxycarbonylbenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1C(=O)OCC1=CC=CC=C1 MWTMXYXPZGPRJQ-UHFFFAOYSA-N 0.000 description 1
- DFXQXFGFOLXAPO-UHFFFAOYSA-N 96-99-1 Chemical class OC(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 DFXQXFGFOLXAPO-UHFFFAOYSA-N 0.000 description 1
- QAYNSPOKTRVZRC-UHFFFAOYSA-N 99-60-5 Chemical class OC(=O)C1=CC=C([N+]([O-])=O)C=C1Cl QAYNSPOKTRVZRC-UHFFFAOYSA-N 0.000 description 1
- MOZDKDIOPSPTBH-UHFFFAOYSA-N Benzyl parahydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)OCC1=CC=CC=C1 MOZDKDIOPSPTBH-UHFFFAOYSA-N 0.000 description 1
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 1
- 101100282617 Bovine herpesvirus 1.1 (strain Cooper) gC gene Proteins 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- XPJVKCRENWUEJH-UHFFFAOYSA-N Isobutylparaben Chemical compound CC(C)COC(=O)C1=CC=C(O)C=C1 XPJVKCRENWUEJH-UHFFFAOYSA-N 0.000 description 1
- CMHMMKSPYOOVGI-UHFFFAOYSA-N Isopropylparaben Chemical compound CC(C)OC(=O)C1=CC=C(O)C=C1 CMHMMKSPYOOVGI-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- IUGQFMIATSVYLK-UHFFFAOYSA-N benzyl 2-(4-hydroxyphenyl)acetate Chemical compound C1=CC(O)=CC=C1CC(=O)OCC1=CC=CC=C1 IUGQFMIATSVYLK-UHFFFAOYSA-N 0.000 description 1
- BPLKDVGMXNZCQO-UHFFFAOYSA-N benzyl 4-phenylmethoxybenzoate Chemical compound C=1C=C(OCC=2C=CC=CC=2)C=CC=1C(=O)OCC1=CC=CC=C1 BPLKDVGMXNZCQO-UHFFFAOYSA-N 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- LKWSCLZNBWZMTI-UHFFFAOYSA-N dibenzyl 4-hydroxybenzene-1,2-dicarboxylate Chemical compound C=1C=CC=CC=1COC(=O)C1=CC(O)=CC=C1C(=O)OCC1=CC=CC=C1 LKWSCLZNBWZMTI-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- GRQJKRYSORWWTI-UHFFFAOYSA-N dipropan-2-yl 4-hydroxybenzene-1,2-dicarboxylate Chemical compound CC(C)OC(=O)C1=CC=C(O)C=C1C(=O)OC(C)C GRQJKRYSORWWTI-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- PMDKYLLIOLFQPO-UHFFFAOYSA-N monocyclohexyl phthalate Chemical compound OC(=O)C1=CC=CC=C1C(=O)OC1CCCCC1 PMDKYLLIOLFQPO-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 238000001454 recorded image Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
- B41M5/323—Organic colour formers, e.g. leuco dyes
- B41M5/327—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
- B41M5/333—Colour developing components therefor, e.g. acidic compounds
- B41M5/3333—Non-macromolecular compounds
- B41M5/3335—Compounds containing phenolic or carboxylic acid groups or metal salts thereof
Definitions
- the invention relates to a heat-sensitive recording sheet in which the color image and the whiteness of the background are surprisingly well stabilized against the adverse effects of hair oil, fat, oil, etc.
- a heat-sensitive recording sheet using a heat color reaction between a basic colorless or lightly colored chromogenic dye and an organic color developing agent such as a phenolic substance or an organic acid is disclosed in Japanese Patent Publication No.
- a heat-sensitive recording sheet is generally prepared by placing on the surface of the support,
- a coating paint which by grinding and dispersing a colorless ohromogeneous dye and a color developing material, phenolic substances, into fine particles, by mixing the dispersions obtained and by adding a binder, filler, sensitizer, lubricant and other auxiliaries was obtained.
- the oily materials are the color-forming layer consisting of a basic colorless chromogenic dye of fine particles and an organic color developing agent of fine particles, or the color-forming reaction product which is made of a basic colorless chromogenic Dye and an organic color developing agent is formed, partially dissolve or destabilize.
- the heat-sensitive recording sheets in which 4-hydroxybenzoic acid ester or 4-hydroxyphthalic acid diester are used are superior in the above fundamental qualities, but in terms of stability to oily materials, they are superior to the previous heat-sensitive recording sheets in which Bisphenol compounds can be used as color developing agents.
- the invention has for its object to provide a heat-sensitive recording sheet in which the recording image is very stable against the action of oily materials.
- color developing agents other than the metal salts of nitrobenzoic acid used in the present invention, but the effects of this invention are significant when monophenolic 4-hydroxyphenyl compounds and / or phthalic acid monoesters are used as the color developing agent.
- Examples of monophenolic 4-hydroxyphenyl compounds are 4-hydroxybenzoic acid esters, for example 4-hydroxybenzoic acid propyl ester, 4-hydroxybenzoic acid isopropyl ester, 4-hydroxybenzoic acid butyl ester, 4-hydroxybenzoic acid isobutyl ester, 4-hydroxybenzoic acid methyl benzyl ester, 4 4-hydroxyphthalic diesters such as dimethyl 4-hydroxyphthalate, diisopropyl 4-hydroxyphthalate, dibenzyl 4-hydroxyphthalate, di-4-hydroxyphthalate, etc .; 4-hydroxyacetophenone; p-phenylphenol; Benzyl 4-hydroxyphenylacetate; p-benzylphenol; 4-hydroxyphenyl-4'-n-sulfone, 4-hydroxyphenyl- 4'-n-butyloxyphenylsulfone, 4-hydroxyphenyl-4'-n-hexyloxyphenylsulfone, 4-hydroxyphenyl-4'-n-octyloxyphenylsul
- phthalic acid monoesters are phthalic acid monophenyl ester, phthalic acid monobenzyl ester, phthalic acid monocyclohexyl ester, phthalic acid monomethylphenyl ester, phthalic acid monoethylphenyl ester, phthalic acid monoalkylbenzyl esters, phthalic acid monohalobenzyl esters, phthalic acid monoalkoxybenzyl esters and the like.
- Such color developing agents are superior in terms of the quality required in principle, but have a disadvantage that they are inferior to the bisphenol compounds which have hitherto been used in terms of stability to oily materials.
- bisphenol compounds examples include 4,4'-isopropylidenediphenol (bisphenol A); 4,4 '- (1-methyl-n-hexylidene) diphenol; 4,4'-cyclohexylidenediphenol; 4,4'-thiobis (4-tertiary-butyl-3-methylphenol) and the like.
- bisphenol A 4,4'-isopropylidenediphenol
- 4,4'-cyclohexylidenediphenol 4,4'-thiobis (4-tertiary-butyl-3-methylphenol) and the like.
- Colorless or slightly colored chromogenic dyes useful in the present invention are many, and they are not particularly limited.
- the following dyes from the black color developing fluoran dyes give a heat-sensitive recording sheet with a little low image density: 3-diethylamino-6-methyl- (para-chloroanilino) fluorane, 3-diethylamino-7- (ortho-chloroanilino) fluorane, 3- (N-ethyl-P-to-luidino) -6-methyl-7-anilinofluorane, 3-dibutylamino-6-methyl- (ortho-chloroanilino) fluorane, 3- (N-ethyl-isoamyl) -6-methyl - anilinofluoran etc.
- thermochromic phenomenon in which the color image is extinguished immediately or slowly. Therefore, these dyes cannot be used in heat-sensitive recording sheets.
- thermochromism phenomenon etallsalzderivate by use of the invention M of nitrobenzoic acid is eliminated, thereby making it possible to use the above basic colorless dyes.
- the nitrobenzoic acid together with at least one substance from the group consisting of crystal violet lactone, fluorene-leuk o dyestuff and azaphthalide leuco dye is a superior stability to oily materials.
- Fluorene-leuco dyes of the general formulas (III) or (IV) are particularly superior among the above basic colorless or slightly colored chromogenic dyes.
- the metal salts of nitrobenzoic acid according to the invention are very advantageous as organic color developing agents. They are characterized by the fact that they absorb the ultraviolet rays more strongly than other organic color developing agents and have a superior stability towards oily materials.
- Typical examples of metal salt derivatives according to the invention of nitrobenzoic acid of the general formulas. (I) or (II) are metal salts of 4-nitrobenzoic acid, 3-nitrobenzoic acid, 3,4-dinitrobenzoic acid, 4-nitro-3-methylbenzoic acid, 4-nitro-5 -methylbenzoic acid, 3,5-dinitrobenzoic acid, 2-benzoyl-4-nitrobenzoic acid, 2-benzoyl-3-nitrobenzoic acid, 4-t-butyl-3-nitrobenzoic acid, 4-t-butyl-3,5-dinitrobenzoic acid, 3-nitro -4-methylbenzoic acid, 3-nitro-5-methylbenzoic acid, 3-nitro-2-methylbenzoic acid, 4-nitro-5-chlorobenzoic acid, 4-nitro-2-chlorobenzoic acid, 4-nitro-5-chlorobenzoic acid, 3-nitro-4 -chlorobenzoic acid, 3-nitro-5-chlorobenzoic acid, etc., the metal salts of 3-nitrobenzoic
- Suitable metals are polyvalent metals, such as zinc, calcium, magnesium, aluminum, barium and lead, preferably zinc, calcium and magnesium.
- radicals R 1 , R 2 , R 3 , R 4 in the general formulas I and II represent a halogen atom, it is preferably a chlorine or bromine atom. If the above radicals R 1-4 represent an alkyl radical, then this is preferably an H 3 C, H 5 C 2 -, H 7 C 3 -, iso-H 7 C 3 , tert.-H 9 C 4 or H 11 C 5 group.
- the metal salts of nitrobenzoic acids can be used individually or in a mixture.
- the above-mentioned organic color developing agent, the above-mentioned organic colorless chromogenic dye and the metal salt derivative of the nitrobenzoic acid are ground to a particle size of several microns or smaller by means of a grinding device such as a ball mill, grinder, sand grinder, etc. or by means of a suitable emulsifying machine.
- additives are added, depending on the intended use, in order to produce the coating composition.
- the additives which can be used according to the invention are, for example, the following: binders, such as polyvinyl alcohol, are more modified Polyvinyl alcohol, hydroxyethyl cellulose, methyl cellulose, starch, styrene-maleic anhydride copolymers, vinyl acetate-maleic anhydride copolymers, styrene-butadiene copolymers, etc .; inorganic or organic fillers such as kaolin, baked kaolin, diatomaceous earth, talc, titanium dioxide,
- the desired heat-sensitive sheet is obtained by applying this coating color on paper or on various films.
- the amount of the metal salt derivatives of nitrobenzoic acid according to the invention and the type and the amount of the other constituents which are determined depending on the desired effect and suitability for recording purposes are not particularly limited.
- a metal salt derivative of nitrobenzoic acid and another color developing agent are used in combination, it is generally advantageous to use 1 to 8 parts by weight of the metal salt derivative of nitrobenzoic acid, 3 to 10 parts by weight of the other organic color developing agent and 1 to 20 parts by weight of filler , based on 1 part by weight of the basic colorless or slightly colored chromogenic dye, and 10 to 25 parts by weight of binder, based on the total solids content.
- the metal salt derivative of nitrobenzoic acid when using the metal salt derivative of nitrobenzoic acid as an organic color developing agent, it is generally advantageous to use 1 to 8 parts by weight of the metal salt derivative of nitrobenzoic acid and 1 to 20 parts by weight of filler, based on 1 part by weight of the basic colorless or slightly colored to use chromogenic dye, and to use 10 to 25 parts by weight of binder, based on the total solids content.
- a non-recorded material is left to stand at 60 ° C and 45% relative humidity for 24 hours and then measured with a Macbeth sealing knife.
- the examples according to the invention in which the zinc salt derivative of a nitrobenzoic acid is used, have a high residual image density even when contaminated with oil.
- Another solution B using the same amount of 4-hydroxyphthalic acid monobenzyl ester instead of the 4-hydroxybenzoic acid benzyl ester in solution B (color developing agent dispersion) of Example 1, was prepared and with calcium carbonate dispersion and solutions A and C in the weight ratio of the table 3 mixed.
- a recording image is obtained with a metal salt derivative of nitrobenzoic acid as a color developing agent in combination with crystal violet lactone, fluorene leuco dye or azaphthalide leuco dye, which is very stable to the action of oily materials.
- Reflectance of ultraviolet light The heat sensitive recording sheets were printed with a bar cord printer at a pulse width of 4.0 milliseconds and an applied voltage of 30 volts.
- the reflectance of the recorded image was measured with a spectrophotometer (at a wavelength of 800 nm).
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Color Printing (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP169269/83 | 1983-09-16 | ||
| JP58169269A JPS6061289A (ja) | 1983-09-16 | 1983-09-16 | 感熱記録紙 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0135901A2 true EP0135901A2 (fr) | 1985-04-03 |
| EP0135901A3 EP0135901A3 (en) | 1986-05-14 |
| EP0135901B1 EP0135901B1 (fr) | 1988-11-30 |
Family
ID=15883370
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP84111015A Expired EP0135901B1 (fr) | 1983-09-16 | 1984-09-14 | Matériel pour l'enregistrement thermosensible |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4591888A (fr) |
| EP (1) | EP0135901B1 (fr) |
| JP (1) | JPS6061289A (fr) |
| DE (1) | DE3475387D1 (fr) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0171810A3 (en) * | 1984-08-15 | 1986-10-29 | Jujo Paper Co., Ltd. | Heat-sensitive recording sheet |
| EP0249885A3 (en) * | 1986-06-17 | 1989-08-30 | Kanzaki Paper Manufacturing Company Limited | Heat-sensitive recording material |
| EP0251209A3 (en) * | 1986-06-25 | 1989-09-06 | Jujo Paper Co., Ltd. | Heat-sensitive registration material |
| EP0319283A3 (en) * | 1987-12-04 | 1990-08-16 | Appleton Papers Inc. | Thermally responsive record material |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4658276A (en) * | 1985-06-22 | 1987-04-14 | Kanzaki Paper Manufacturing Co., Ltd. | Phthalide derivatives and recording system utilizing the same |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1330984A (en) * | 1970-09-28 | 1973-09-19 | Fuji Photo Film Co Ltd | Colour-developer compositions |
| CA1009841A (en) * | 1971-06-16 | 1977-05-10 | Shinichi Oda | Sensitized record sheet material and process for making the same |
| JPS5318921B2 (fr) * | 1972-07-28 | 1978-06-17 | ||
| US4147830A (en) * | 1976-01-28 | 1979-04-03 | Fuji Photo Film Co., Ltd. | Recording sheet |
| JPS5538826A (en) * | 1978-09-11 | 1980-03-18 | Fuji Photo Film Co Ltd | Color-developing ink |
-
1983
- 1983-09-16 JP JP58169269A patent/JPS6061289A/ja active Granted
-
1984
- 1984-09-14 DE DE8484111015T patent/DE3475387D1/de not_active Expired
- 1984-09-14 EP EP84111015A patent/EP0135901B1/fr not_active Expired
- 1984-09-14 US US06/650,793 patent/US4591888A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0171810A3 (en) * | 1984-08-15 | 1986-10-29 | Jujo Paper Co., Ltd. | Heat-sensitive recording sheet |
| EP0249885A3 (en) * | 1986-06-17 | 1989-08-30 | Kanzaki Paper Manufacturing Company Limited | Heat-sensitive recording material |
| EP0251209A3 (en) * | 1986-06-25 | 1989-09-06 | Jujo Paper Co., Ltd. | Heat-sensitive registration material |
| EP0319283A3 (en) * | 1987-12-04 | 1990-08-16 | Appleton Papers Inc. | Thermally responsive record material |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0135901B1 (fr) | 1988-11-30 |
| DE3475387D1 (en) | 1989-01-05 |
| JPH0239994B2 (fr) | 1990-09-07 |
| JPS6061289A (ja) | 1985-04-09 |
| US4591888A (en) | 1986-05-27 |
| EP0135901A3 (en) | 1986-05-14 |
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