CA1177194A - Reactive organic diluent in polyol resin film-forming compositions - Google Patents
Reactive organic diluent in polyol resin film-forming compositionsInfo
- Publication number
- CA1177194A CA1177194A CA000379755A CA379755A CA1177194A CA 1177194 A CA1177194 A CA 1177194A CA 000379755 A CA000379755 A CA 000379755A CA 379755 A CA379755 A CA 379755A CA 1177194 A CA1177194 A CA 1177194A
- Authority
- CA
- Canada
- Prior art keywords
- composition
- polyol
- acid
- hydroxyl
- functional material
- 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
Links
- 229920005862 polyol Polymers 0.000 title claims abstract description 86
- 150000003077 polyols Chemical class 0.000 title claims abstract description 69
- 239000003085 diluting agent Substances 0.000 title claims abstract description 43
- 239000000203 mixture Substances 0.000 title claims description 63
- 229920005989 resin Polymers 0.000 title claims description 35
- 239000011347 resin Substances 0.000 title claims description 35
- -1 glycidyl ester Chemical class 0.000 claims abstract description 72
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 34
- 239000008199 coating composition Substances 0.000 claims abstract description 26
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims description 28
- 239000000463 material Substances 0.000 claims description 23
- 239000012948 isocyanate Substances 0.000 claims description 13
- 229920005906 polyester polyol Polymers 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 150000002513 isocyanates Chemical class 0.000 claims description 9
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 claims description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 8
- 229920003180 amino resin Polymers 0.000 claims description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 150000002430 hydrocarbons Chemical group 0.000 claims description 6
- 229920000570 polyether Polymers 0.000 claims description 6
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 claims description 5
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical group OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 5
- 229940114072 12-hydroxystearic acid Drugs 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 4
- 229920002396 Polyurea Polymers 0.000 claims description 4
- 239000001361 adipic acid Substances 0.000 claims description 4
- 235000011037 adipic acid Nutrition 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 229920002647 polyamide Polymers 0.000 claims description 4
- 239000004814 polyurethane Substances 0.000 claims description 4
- 229920002635 polyurethane Polymers 0.000 claims description 4
- SZCWBURCISJFEZ-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) 3-hydroxy-2,2-dimethylpropanoate Chemical compound OCC(C)(C)COC(=O)C(C)(C)CO SZCWBURCISJFEZ-UHFFFAOYSA-N 0.000 claims description 3
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 claims description 3
- 229920001568 phenolic resin Polymers 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 23
- 239000002904 solvent Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 150000007513 acids Chemical class 0.000 description 12
- 239000000178 monomer Substances 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 10
- 239000010408 film Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- 239000004925 Acrylic resin Substances 0.000 description 8
- 229920000178 Acrylic resin Polymers 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 125000005442 diisocyanate group Chemical group 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- 229940072282 cardura Drugs 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 description 6
- 125000003700 epoxy group Chemical group 0.000 description 6
- 150000002334 glycols Chemical class 0.000 description 6
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- 239000005056 polyisocyanate Substances 0.000 description 5
- 229920001228 polyisocyanate Polymers 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 150000004072 triols Chemical class 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 150000001414 amino alcohols Chemical class 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 4
- WIHMDCQAEONXND-UHFFFAOYSA-M butyl-hydroxy-oxotin Chemical compound CCCC[Sn](O)=O WIHMDCQAEONXND-UHFFFAOYSA-M 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 150000002596 lactones Chemical class 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- 239000008204 material by function Substances 0.000 description 4
- 229940063559 methacrylic acid Drugs 0.000 description 4
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- RJSZFSOFYVMDIC-UHFFFAOYSA-N tert-butyl n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OC(C)(C)C RJSZFSOFYVMDIC-UHFFFAOYSA-N 0.000 description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 229920006397 acrylic thermoplastic Polymers 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 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 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- 229940063557 methacrylate Drugs 0.000 description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 3
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 2
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 2
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 235000019256 formaldehyde Nutrition 0.000 description 2
- 229960004279 formaldehyde Drugs 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 150000002688 maleic acid derivatives Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
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- 150000002825 nitriles Chemical class 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- JKXONPYJVWEAEL-UHFFFAOYSA-N oxiran-2-ylmethyl acetate Chemical compound CC(=O)OCC1CO1 JKXONPYJVWEAEL-UHFFFAOYSA-N 0.000 description 1
- XRQKARZTFMEBBY-UHFFFAOYSA-N oxiran-2-ylmethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1CO1 XRQKARZTFMEBBY-UHFFFAOYSA-N 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical class C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- QNAJAJLBHMMOJB-UHFFFAOYSA-N oxiran-2-ylmethyl propanoate Chemical compound CCC(=O)OCC1CO1 QNAJAJLBHMMOJB-UHFFFAOYSA-N 0.000 description 1
- NRZWYNLTFLDQQX-UHFFFAOYSA-N p-tert-Amylphenol Chemical compound CCC(C)(C)C1=CC=C(O)C=C1 NRZWYNLTFLDQQX-UHFFFAOYSA-N 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- 150000002976 peresters Chemical group 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000003334 potential effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- QROGIFZRVHSFLM-UHFFFAOYSA-N prop-1-enylbenzene Chemical compound CC=CC1=CC=CC=C1 QROGIFZRVHSFLM-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical compound OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 150000003336 secondary aromatic amines Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940044603 styrene Drugs 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/163,354 US4314918A (en) | 1980-06-26 | 1980-06-26 | Coating compositions containing organic alcoholic reactive diluents |
| US163,354 | 1980-06-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1177194A true CA1177194A (en) | 1984-10-30 |
Family
ID=22589661
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000379755A Expired CA1177194A (en) | 1980-06-26 | 1981-06-15 | Reactive organic diluent in polyol resin film-forming compositions |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4314918A (enExample) |
| AU (1) | AU527370B2 (enExample) |
| BR (1) | BR8103991A (enExample) |
| CA (1) | CA1177194A (enExample) |
| DE (1) | DE3124784C2 (enExample) |
| ES (1) | ES503358A0 (enExample) |
| FR (1) | FR2485556A1 (enExample) |
| GB (1) | GB2078766B (enExample) |
| IT (1) | IT1137256B (enExample) |
| ZA (1) | ZA814058B (enExample) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4465815A (en) * | 1981-12-28 | 1984-08-14 | Ford Motor Company | Polyhydroxy oligomers for high solids coatings II |
| US4424334A (en) | 1981-12-28 | 1984-01-03 | Ford Motor Company | High solids urethane coatings from new tetrahydroxy oligomers |
| US4403093A (en) * | 1982-09-28 | 1983-09-06 | Ppg Industries, Inc. | Polyesters |
| US4515835A (en) * | 1982-12-23 | 1985-05-07 | Rohm And Haas Company | High solids thermosetting coating compositions, cured coatings, coated articles, and processes |
| US4533534A (en) * | 1983-07-05 | 1985-08-06 | Ford Motor Company | Thermosetting coating composition useful as primer and chip resistant primer II |
| US4533684A (en) * | 1983-07-05 | 1985-08-06 | Ford Motor Company | Thermosetting coating composition useful as chip resistant primer II |
| US4609717A (en) * | 1985-04-03 | 1986-09-02 | Ppg Industries, Inc. | High solids coating compositions based on long chain diols |
| US5039759A (en) * | 1985-08-01 | 1991-08-13 | Technology Corporation United Carbide Chemicals And Plastics | Water borne high solids coating compositions |
| US5158808A (en) * | 1985-08-01 | 1992-10-27 | Union Carbide Chemicals & Plastics Technology Corporation | Method of coating with a water borne composition |
| US4789706A (en) * | 1986-04-21 | 1988-12-06 | Nl Chemicals, Inc. | Narrow molecular weight polyester oligomers and method of preparation |
| US4743655A (en) * | 1986-04-21 | 1988-05-10 | Nl Chemicals, Inc. | Narrow molecular weight polyester oligomers and method of preparation |
| US4988766A (en) * | 1987-05-13 | 1991-01-29 | Ppg Industries, Inc. | Polymers prepared by polymerizing alpha, beta-ethylenically unsaturated acids and epoxy compounds and crosslinked products therefrom |
| US4912187A (en) * | 1988-01-29 | 1990-03-27 | Questra Chemicals Corp. | Solid ester products of sterically hindered polyhydroxymonocarboxylic acids |
| US4978741A (en) * | 1988-01-29 | 1990-12-18 | Questra Chemicals Corp. | Method for preparing essentially haze-free isophthalic acid- and polymethylolalkanoic acid-containing resins |
| US5300363A (en) * | 1989-04-20 | 1994-04-05 | A-Line Products Corporation | Aqueous coating composition |
| US5227198A (en) * | 1989-04-20 | 1993-07-13 | A-Line Products Corporation | Aqueous coating composition and method of use |
| US5756566A (en) * | 1989-04-20 | 1998-05-26 | A-Line Products Corp. | Aqueous coating composition |
| JP2793878B2 (ja) * | 1990-03-20 | 1998-09-03 | 関西ペイント株式会社 | 熱硬化性樹脂組成物 |
| GB9006577D0 (en) * | 1990-03-23 | 1990-05-23 | Shell Int Research | Thermosetting polyol resins and coating compositions based upon such resins |
| US5066688A (en) * | 1991-04-10 | 1991-11-19 | E. I. Du Pont De Nemours And Company | Cathodic electrodeposition coatings containing a reactive additive |
| KR0167002B1 (ko) * | 1994-12-27 | 1999-03-20 | 김충세 | 폴리우레탄 수분산 수지의 제조방법과 이에 따른 수지가 함유된 도료 조성물 |
| US6117931A (en) * | 1996-07-01 | 2000-09-12 | Basf Corporation | Curable coating compositions having improved effect pigment orientation and a method of using the same |
| US6069203A (en) * | 1997-09-29 | 2000-05-30 | Shell Oil Company | High solids coating compositions |
| US6610817B2 (en) * | 2000-12-18 | 2003-08-26 | Basf Corporation | Coating composition containing alcoholic reactive diluents |
| JP4824877B2 (ja) * | 2001-08-21 | 2011-11-30 | 関西ペイント株式会社 | 水酸基含有樹脂およびその製造方法 |
| DE10152294A1 (de) | 2001-10-26 | 2003-05-08 | Solutia Austria Gmbh Werndorf | Hochmolekulare Polyurethan-Dispersionen |
| AT500555B1 (de) * | 2003-06-13 | 2009-11-15 | Cytec Surface Specialties At | Selbstvernetzende wässrige polyurethandispersionen |
| US7838076B2 (en) * | 2004-09-09 | 2010-11-23 | Kansai Paint Co., Ltd. | Thermosetting aqueous paint composition |
| US8197905B2 (en) * | 2005-10-05 | 2012-06-12 | E I Du Pont De Nemours And Company | Method of applying high solids coating composition to multilayer coating |
| US7842756B2 (en) * | 2005-11-23 | 2010-11-30 | Ppg Industries Ohio, Inc. | Copolymer with hydrolyzable groups by reacting glycidyl ester and/or ether, polyol and hydrolyzable group-containing compound |
| US7425594B2 (en) * | 2005-11-23 | 2008-09-16 | Ppg Industries Ohio, Inc. | Copolymer of glycidyl ester and/or ether with polyol |
| US20090191407A1 (en) * | 2008-01-18 | 2009-07-30 | Lewarchik Ronald J | Coatings providing low surface emissivity |
| US8193293B2 (en) * | 2008-03-17 | 2012-06-05 | Ppg Industries Ohio, Inc. | Low temperature curable coating compositions and related methods |
| US7871704B2 (en) * | 2008-09-02 | 2011-01-18 | Ppg Industries Ohio, Inc. | Multi-cure compositions comprising polythiol |
| EP2316868A1 (en) | 2009-10-27 | 2011-05-04 | Cytec Surface Specialties Austria GmbH | Aqueously Dispersible Polyurethane |
| EP2690117A1 (en) | 2012-07-24 | 2014-01-29 | ALLNEX AUSTRIA GmbH | Aqueously Dispersible Polyurethane |
| EP3118234A1 (en) | 2015-07-15 | 2017-01-18 | ALLNEX AUSTRIA GmbH | Coating compositions |
| BE1026321B1 (nl) * | 2018-05-29 | 2020-01-13 | Orineo Bvba | Hardingsmiddel voor het uitharden van een hars |
| CN116987438B (zh) * | 2023-08-22 | 2024-03-29 | 广东波特新材料有限公司 | 一种改进型双组份聚氨酯涂料 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB130697A (en) * | 1918-03-18 | 1919-08-14 | James Gordon Gray | Improvements in Gyroscopic Apparatus. |
| GB1317969A (en) | 1970-11-12 | 1973-05-23 | Shell Int Research | Process for the preparation of polyester resin |
| US3994851A (en) * | 1972-10-26 | 1976-11-30 | Ppg Industries, Inc. | High solids polyester coating composition |
| US3883454A (en) * | 1972-10-31 | 1975-05-13 | Bayer Ag | Binders for environmentally harmless laquer systems |
| US3954715A (en) * | 1973-03-05 | 1976-05-04 | E. I. Du Pont De Nemours And Company | Coating compositions containing diesters of dibasic acids and glycidyl esters and aminoplast resins |
| US3954899A (en) * | 1973-04-02 | 1976-05-04 | Ppg Industries, Inc. | Extensible coatings |
| CA1056545A (en) * | 1973-04-18 | 1979-06-12 | Bernd-Ulrich Kaiser | Environmentally harmless stoving lacquer systems based on alkyd resins containing condensed monohydric alcohols |
| US3962369A (en) * | 1973-05-16 | 1976-06-08 | Ppg Industries, Inc. | Sealer-primer for elastomeric coatings |
| US3928420A (en) * | 1973-06-12 | 1975-12-23 | Du Pont | Mixed esters of polybasic saturated acids, glycols and glycidyl esters |
| US3919351A (en) * | 1973-08-29 | 1975-11-11 | Ppg Industries Inc | Composition useful in making extensible films |
| US3975457A (en) * | 1973-09-21 | 1976-08-17 | Ppg Industries, Inc. | Thermoplastic extensible coating compositions |
| AT331941B (de) * | 1973-10-22 | 1976-08-25 | Erz & Stahl Ges M B H | Losungsmittel fur lacke |
| ZA747610B (en) * | 1973-12-11 | 1976-07-28 | Dulux Australia Ltd | Novel coating compositions |
| ZA744070B (en) * | 1974-06-25 | 1976-05-26 | Prolux Paint Mfg Pty | Film forming compositions and their preparation |
| GB1509418A (en) * | 1974-06-25 | 1978-05-04 | Prolux Paint Mfg Pty | Coating compositions |
| DE2507985C2 (de) * | 1975-02-25 | 1982-05-06 | Deutsche Texaco Ag, 2000 Hamburg | Verfahren zur Herstellung von niedrigviskosen, fettsäuremodifizierten Polyestern für lösungsmittelarme Einbrennlacksysteme |
| US4028309A (en) * | 1975-03-12 | 1977-06-07 | E. I. Du Pont De Nemours And Company | Coating compositions containing esters of dibasic acids, glycols and glycidyl esters, and polyisocyanates |
| AU493100B1 (en) | 1975-05-15 | 1977-11-17 | Dulux Australia Ltd | Autoxidisable composition and process |
| US4107113A (en) * | 1975-05-15 | 1978-08-15 | Dulux Australia Ltd. | Autoxidisable composition |
-
1980
- 1980-06-26 US US06/163,354 patent/US4314918A/en not_active Expired - Lifetime
-
1981
- 1981-06-15 CA CA000379755A patent/CA1177194A/en not_active Expired
- 1981-06-16 ZA ZA814058A patent/ZA814058B/xx unknown
- 1981-06-24 AU AU72124/81A patent/AU527370B2/en not_active Ceased
- 1981-06-24 DE DE3124784A patent/DE3124784C2/de not_active Expired
- 1981-06-25 BR BR8103991A patent/BR8103991A/pt unknown
- 1981-06-25 GB GB8119651A patent/GB2078766B/en not_active Expired
- 1981-06-25 IT IT22550/81A patent/IT1137256B/it active
- 1981-06-25 ES ES503358A patent/ES503358A0/es active Granted
- 1981-06-25 FR FR8112524A patent/FR2485556A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3124784C2 (de) | 1986-06-26 |
| FR2485556A1 (fr) | 1981-12-31 |
| GB2078766A (en) | 1982-01-13 |
| AU527370B2 (en) | 1983-03-03 |
| US4314918A (en) | 1982-02-09 |
| ZA814058B (en) | 1983-01-26 |
| ES8305398A1 (es) | 1983-04-01 |
| BR8103991A (pt) | 1982-03-09 |
| IT8122550A0 (it) | 1981-06-25 |
| FR2485556B1 (enExample) | 1984-06-29 |
| DE3124784A1 (de) | 1982-04-01 |
| AU7212481A (en) | 1982-01-07 |
| GB2078766B (en) | 1985-02-20 |
| ES503358A0 (es) | 1983-04-01 |
| IT1137256B (it) | 1986-09-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |