CA1261529A - Thermosettable polystyrylpyridine prepolymer terminated with ethylenically unsaturated groups and cured products therefrom - Google Patents
Thermosettable polystyrylpyridine prepolymer terminated with ethylenically unsaturated groups and cured products therefromInfo
- Publication number
- CA1261529A CA1261529A CA000502516A CA502516A CA1261529A CA 1261529 A CA1261529 A CA 1261529A CA 000502516 A CA000502516 A CA 000502516A CA 502516 A CA502516 A CA 502516A CA 1261529 A CA1261529 A CA 1261529A
- Authority
- CA
- Canada
- Prior art keywords
- composition
- bis
- imide
- mixture
- aldehyde
- 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
- 239000000203 mixture Substances 0.000 claims abstract description 38
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 21
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 11
- -1 pyridine compound Chemical class 0.000 claims abstract description 11
- 150000003222 pyridines Chemical class 0.000 claims abstract description 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 6
- 238000007334 copolymerization reaction Methods 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 239000000463 material Substances 0.000 claims abstract description 5
- 125000003172 aldehyde group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 229920005989 resin Polymers 0.000 claims description 22
- 239000011347 resin Substances 0.000 claims description 22
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000012779 reinforcing material Substances 0.000 claims description 8
- RUMOYJJNUMEFDD-UHFFFAOYSA-N perillyl aldehyde Chemical compound CC(=C)C1CCC(C=O)=CC1 RUMOYJJNUMEFDD-UHFFFAOYSA-N 0.000 claims description 7
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical group O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 claims description 5
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 claims description 5
- HOPRXXXSABQWAV-UHFFFAOYSA-N 2,3,4-trimethylpyridine Chemical compound CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 claims description 4
- ZAAVUWIYUMVQJG-UHFFFAOYSA-N 2,3,5,6-tetramethylpyridine Chemical compound CC1=CC(C)=C(C)N=C1C ZAAVUWIYUMVQJG-UHFFFAOYSA-N 0.000 claims description 4
- GFYHSKONPJXCDE-UHFFFAOYSA-N 2,3,5-trimethylpyridine Chemical compound CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 claims description 4
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2,5-dimethylpyridine Chemical compound CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 claims description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 4
- 238000006845 Michael addition reaction Methods 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 230000005496 eutectics Effects 0.000 claims description 3
- LFURNOQUNVHWHY-UHFFFAOYSA-N 2,3,4,5,6-pentamethylpyridine Chemical compound CC1=NC(C)=C(C)C(C)=C1C LFURNOQUNVHWHY-UHFFFAOYSA-N 0.000 claims description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 2
- 239000000306 component Substances 0.000 claims 4
- 238000006116 polymerization reaction Methods 0.000 claims 3
- UTBIMNXEDGNJFE-UHFFFAOYSA-N 2,3,6-trimethylpyridine Chemical compound CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 230000009970 fire resistant effect Effects 0.000 abstract description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 18
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 229920002554 vinyl polymer Polymers 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000843 powder Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 230000004580 weight loss Effects 0.000 description 8
- 239000002131 composite material Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 125000006018 1-methyl-ethenyl group Chemical group 0.000 description 6
- VJOWMORERYNYON-UHFFFAOYSA-N 5-ethenyl-2-methylpyridine Chemical compound CC1=CC=C(C=C)C=N1 VJOWMORERYNYON-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 229910002804 graphite Inorganic materials 0.000 description 5
- 239000010439 graphite Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000004570 mortar (masonry) Substances 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000006835 compression Effects 0.000 description 4
- 238000007906 compression Methods 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000002411 thermogravimetry Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- BKCIQPUIDHPJSI-UHFFFAOYSA-N 2,3,4,5-tetramethylpyridine Chemical compound CC1=CN=C(C)C(C)=C1C BKCIQPUIDHPJSI-UHFFFAOYSA-N 0.000 description 2
- QBSVEFGWBSANTE-UHFFFAOYSA-N 2,3,4,6-tetramethylpyridine Chemical compound CC1=CC(C)=C(C)C(C)=N1 QBSVEFGWBSANTE-UHFFFAOYSA-N 0.000 description 2
- MBDOYVRWFFCFHM-UHFFFAOYSA-N 2-hexenal Chemical compound CCCC=CC=O MBDOYVRWFFCFHM-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- SMTDFMMXJHYDDE-UHFFFAOYSA-N 2-prop-1-enylpyridine Chemical compound CC=CC1=CC=CC=N1 SMTDFMMXJHYDDE-UHFFFAOYSA-N 0.000 description 2
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 241000219198 Brassica Species 0.000 description 2
- 235000003351 Brassica cretica Nutrition 0.000 description 2
- 235000003343 Brassica rupestris Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000010460 mustard Nutrition 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 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
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- SATICYYAWWYRAM-UHFFFAOYSA-N (2E,4E)-2,4-heptadienal Natural products CCC=CC=CC=O SATICYYAWWYRAM-UHFFFAOYSA-N 0.000 description 1
- DVVATNQISMINCX-UHFFFAOYSA-N (2E,4E)-octadienal Natural products CCCC=CC=CC=O DVVATNQISMINCX-UHFFFAOYSA-N 0.000 description 1
- ZHHYXNZJDGDGPJ-BSWSSELBSA-N (2e,4e)-nona-2,4-dienal Chemical compound CCCC\C=C\C=C\C=O ZHHYXNZJDGDGPJ-BSWSSELBSA-N 0.000 description 1
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
- DVVATNQISMINCX-YTXTXJHMSA-N (E,E)-2,4-Octadienal Chemical compound CCC\C=C\C=C\C=O DVVATNQISMINCX-YTXTXJHMSA-N 0.000 description 1
- BATOPAZDIZEVQF-MQQKCMAXSA-N (E,E)-2,4-hexadienal Chemical compound C\C=C\C=C\C=O BATOPAZDIZEVQF-MQQKCMAXSA-N 0.000 description 1
- SATICYYAWWYRAM-VNKDHWASSA-N (E,E)-hepta-2,4-dienal Chemical compound CC\C=C\C=C\C=O SATICYYAWWYRAM-VNKDHWASSA-N 0.000 description 1
- AQGZJQNZNONGKY-UHFFFAOYSA-N 1-[4-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=C(N2C(C=CC2=O)=O)C=C1 AQGZJQNZNONGKY-UHFFFAOYSA-N 0.000 description 1
- XOJRVZIYCCJCRD-UHFFFAOYSA-N 1-[4-[4-(2,5-dioxopyrrol-1-yl)phenoxy]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1OC1=CC=C(N2C(C=CC2=O)=O)C=C1 XOJRVZIYCCJCRD-UHFFFAOYSA-N 0.000 description 1
- LIRFWAADGFIXIJ-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)cyclohexyl]methyl]cyclohexyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCC(CC2CCC(CC2)N2C(C=CC2=O)=O)CC1 LIRFWAADGFIXIJ-UHFFFAOYSA-N 0.000 description 1
- PYVHLZLQVWXBDZ-UHFFFAOYSA-N 1-[6-(2,5-dioxopyrrol-1-yl)hexyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCCCCCN1C(=O)C=CC1=O PYVHLZLQVWXBDZ-UHFFFAOYSA-N 0.000 description 1
- ZHHYXNZJDGDGPJ-UHFFFAOYSA-N 2,4-Nonadienal Natural products CCCCC=CC=CC=O ZHHYXNZJDGDGPJ-UHFFFAOYSA-N 0.000 description 1
- IXFAHCCRDSSCPX-UHFFFAOYSA-N 2,5-diethylpyridine Chemical compound CCC1=CC=C(CC)N=C1 IXFAHCCRDSSCPX-UHFFFAOYSA-N 0.000 description 1
- OQLYLAOKFUUBBI-UHFFFAOYSA-N 2,5-dimethylpyridin-3-amine Chemical compound CC1=CN=C(C)C(N)=C1 OQLYLAOKFUUBBI-UHFFFAOYSA-N 0.000 description 1
- MBDOYVRWFFCFHM-SNAWJCMRSA-N 2-Hexenal Natural products CCC\C=C\C=O MBDOYVRWFFCFHM-SNAWJCMRSA-N 0.000 description 1
- OIALIKXMLIAOSN-UHFFFAOYSA-N 2-Propylpyridine Chemical compound CCCC1=CC=CC=N1 OIALIKXMLIAOSN-UHFFFAOYSA-N 0.000 description 1
- QLUUXTUCKOZMEL-UHFFFAOYSA-N 2-ethyl-3,5-dimethylpyridine Chemical compound CCC1=NC=C(C)C=C1C QLUUXTUCKOZMEL-UHFFFAOYSA-N 0.000 description 1
- NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 description 1
- DZLUPKIRNOCKJB-UHFFFAOYSA-N 2-methoxy-n,n-dimethylacetamide Chemical compound COCC(=O)N(C)C DZLUPKIRNOCKJB-UHFFFAOYSA-N 0.000 description 1
- FVMCCWYUWHDLGS-UHFFFAOYSA-N 2-methyl-6-propylpyridine Chemical compound CCCC1=CC=CC(C)=N1 FVMCCWYUWHDLGS-UHFFFAOYSA-N 0.000 description 1
- KGTRKYRJNHRJRF-UHFFFAOYSA-N 3,4-bis(ethenyl)benzaldehyde Chemical compound C=CC1=CC=C(C=O)C=C1C=C KGTRKYRJNHRJRF-UHFFFAOYSA-N 0.000 description 1
- YVZZVKSLYGTCCF-UHFFFAOYSA-N 3,6-dimethyl-2-propylpyridine Chemical compound CCCC1=NC(C)=CC=C1C YVZZVKSLYGTCCF-UHFFFAOYSA-N 0.000 description 1
- TZOLIFFKTHQGGU-UHFFFAOYSA-N 3-chloro-2,5-dimethylpyridine Chemical compound CC1=CN=C(C)C(Cl)=C1 TZOLIFFKTHQGGU-UHFFFAOYSA-N 0.000 description 1
- SRWILAKSARHZPR-UHFFFAOYSA-N 3-chlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1 SRWILAKSARHZPR-UHFFFAOYSA-N 0.000 description 1
- ZXWNFKKVGPYFRR-UHFFFAOYSA-N 3-ethenyl-2-methylpyridine Chemical compound CC1=NC=CC=C1C=C ZXWNFKKVGPYFRR-UHFFFAOYSA-N 0.000 description 1
- KONCGJQKDMQDAA-UHFFFAOYSA-N 3-ethyl-2,5,6-trimethylpyridine Chemical compound CCC1=CC(C)=C(C)N=C1C KONCGJQKDMQDAA-UHFFFAOYSA-N 0.000 description 1
- QTXUVUSRYCXYNP-UHFFFAOYSA-N 4-(4-ethenylphenoxy)benzaldehyde Chemical compound C1=CC(C=C)=CC=C1OC1=CC=C(C=O)C=C1 QTXUVUSRYCXYNP-UHFFFAOYSA-N 0.000 description 1
- PVFRQQZHGFVMSY-UHFFFAOYSA-N 4-(4-ethenylphenyl)benzaldehyde Chemical compound C1=CC(C=C)=CC=C1C1=CC=C(C=O)C=C1 PVFRQQZHGFVMSY-UHFFFAOYSA-N 0.000 description 1
- ICDOLJWVDBMASK-UHFFFAOYSA-N 4-[(4-formylphenyl)methyl]benzaldehyde Chemical compound C1=CC(C=O)=CC=C1CC1=CC=C(C=O)C=C1 ICDOLJWVDBMASK-UHFFFAOYSA-N 0.000 description 1
- QBFNGLBSVFKILI-UHFFFAOYSA-N 4-ethenylbenzaldehyde Chemical compound C=CC1=CC=C(C=O)C=C1 QBFNGLBSVFKILI-UHFFFAOYSA-N 0.000 description 1
- GRTWYYHRIROQRR-UHFFFAOYSA-N 5-bromonaphthalene-1,6-dicarbaldehyde Chemical compound C1=CC=C2C(Br)=C(C=O)C=CC2=C1C=O GRTWYYHRIROQRR-UHFFFAOYSA-N 0.000 description 1
- CNPBSWGRWZKNHJ-UHFFFAOYSA-N 5-ethenylpyrazine-2-carbaldehyde Chemical compound C=CC1=CN=C(C=O)C=N1 CNPBSWGRWZKNHJ-UHFFFAOYSA-N 0.000 description 1
- NFZUUPLZWMTFDR-UHFFFAOYSA-N 6-ethenylpyrazine-2-carbaldehyde Chemical compound C=CC1=CN=CC(C=O)=N1 NFZUUPLZWMTFDR-UHFFFAOYSA-N 0.000 description 1
- KMOBRGIXFVRXDU-UHFFFAOYSA-N 9h-fluorene-2,6-dicarbaldehyde Chemical compound C1=C(C=O)C=C2C3=CC=C(C=O)C=C3CC2=C1 KMOBRGIXFVRXDU-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- 101000952982 Conus striatus Conopressin-S Proteins 0.000 description 1
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 1
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- 229910003873 O—P—O Inorganic materials 0.000 description 1
- 101000916532 Rattus norvegicus Zinc finger and BTB domain-containing protein 38 Proteins 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- AMNPXXIGUOKIPP-UHFFFAOYSA-N [4-(carbamothioylamino)phenyl]thiourea Chemical compound NC(=S)NC1=CC=C(NC(N)=S)C=C1 AMNPXXIGUOKIPP-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920006231 aramid fiber Polymers 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- IZALUMVGBVKPJD-UHFFFAOYSA-N benzene-1,3-dicarbaldehyde Chemical compound O=CC1=CC=CC(C=O)=C1 IZALUMVGBVKPJD-UHFFFAOYSA-N 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
- AJIBZRIAUXVGQJ-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-5-carbaldehyde Chemical compound C1C2C(C=O)CC1C=C2 AJIBZRIAUXVGQJ-UHFFFAOYSA-N 0.000 description 1
- DVZTVIVLAFIUFZ-UHFFFAOYSA-N bicyclo[3.1.0]hex-2-ene-6-carbaldehyde Chemical compound C1C=CC2C(C=O)C21 DVZTVIVLAFIUFZ-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- DCFDVJPDXYGCOK-UHFFFAOYSA-N cyclohex-3-ene-1-carbaldehyde Chemical compound O=CC1CCC=CC1 DCFDVJPDXYGCOK-UHFFFAOYSA-N 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- JDPRWODRPSDQOF-UHFFFAOYSA-N naphthalene-1,2,4,5,7,8-hexacarbaldehyde Chemical compound O=CC1=CC(C=O)=C(C=O)C2=C(C=O)C(C=O)=CC(C=O)=C21 JDPRWODRPSDQOF-UHFFFAOYSA-N 0.000 description 1
- YAELIZGEEWGECG-UHFFFAOYSA-N naphthalene-1,5-dicarbaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1C=O YAELIZGEEWGECG-UHFFFAOYSA-N 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 1
- 230000003534 oscillatory effect Effects 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 239000001301 oxygen Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- FMVACSABYITMQK-UHFFFAOYSA-N phenanthrene-2,6-dicarbaldehyde Chemical compound C1=C(C=O)C=C2C3=CC=C(C=O)C=C3C=CC2=C1 FMVACSABYITMQK-UHFFFAOYSA-N 0.000 description 1
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- HTGODBGFEKUXOL-UHFFFAOYSA-N pyrazine-2,5-dicarbaldehyde Chemical compound O=CC1=CN=C(C=O)C=N1 HTGODBGFEKUXOL-UHFFFAOYSA-N 0.000 description 1
- 229940030966 pyrrole Drugs 0.000 description 1
- PLDCZLLHZFPWRF-UHFFFAOYSA-N quinoline-3,7-dicarbaldehyde Chemical compound C1=C(C=O)C=NC2=CC(C=O)=CC=C21 PLDCZLLHZFPWRF-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- BATOPAZDIZEVQF-UHFFFAOYSA-N sorbic aldehyde Natural products CC=CC=CC=O BATOPAZDIZEVQF-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 238000009966 trimming Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G16/00—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00
- C08G16/02—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/022—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polycondensates with side or terminal unsaturations
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G16/00—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00
- C08G16/02—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes
- C08G16/025—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with heterocyclic organic compounds
- C08G16/0268—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with heterocyclic organic compounds containing nitrogen in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/12—Unsaturated polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
- C08J5/243—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using carbon fibres
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/912—Polymer from nonethylenic monomers only, having pendant unsaturated group
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US726,554 | 1985-04-23 | ||
| US06/726,554 US4575542A (en) | 1985-04-23 | 1985-04-23 | Thermosettable polystyrylpyridine prepolymer terminated with ethylenically unsaturated groups and cured products therefrom |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1261529A true CA1261529A (en) | 1989-09-26 |
Family
ID=24919069
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000502516A Expired CA1261529A (en) | 1985-04-23 | 1986-02-24 | Thermosettable polystyrylpyridine prepolymer terminated with ethylenically unsaturated groups and cured products therefrom |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4575542A (enExample) |
| EP (1) | EP0220204A1 (enExample) |
| JP (2) | JPS62500526A (enExample) |
| KR (1) | KR940003860B1 (enExample) |
| AU (1) | AU570146B2 (enExample) |
| CA (1) | CA1261529A (enExample) |
| WO (1) | WO1986006386A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4736035A (en) * | 1986-04-04 | 1988-04-05 | The Dow Chemical Company | Heterocyclic styryl compounds and resins prepared therefrom |
| DE3622088A1 (de) * | 1986-07-02 | 1988-01-07 | Basf Ag | Flexible bismaleinimide |
| FR2629088B1 (fr) * | 1988-03-24 | 1990-12-14 | Rhone Poulenc Chimie | Polyamide-imides aromatiques fonctionnalises par des groupes maleimido, un procede pour leur preparation et leur emploi pour notamment preparer des polymeres reticules |
| US5210624A (en) * | 1989-09-19 | 1993-05-11 | Fujitsu Limited | Heads-up display |
| US10077606B2 (en) | 2013-03-27 | 2018-09-18 | Halliburton Energy Services, Inc. | Methods of mitigating bituminous material adhesion using nano-particles |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2600698A (en) * | 1948-11-13 | 1952-06-17 | Monsanto Chemicals | Reaction products from an aldehyde, an aminotriazine, and a mono-nheterocyclic compound |
| FR1555564A (fr) * | 1967-07-13 | 1969-01-31 | Rhone Poulenc Sa | Nouvelles résines thermostables dérivées de bis-imides d'acides dicarboxyliques non saturés |
| FR2261296B1 (enExample) * | 1974-02-14 | 1978-09-29 | Onera (Off Nat Aerospatiale) | |
| FR2378052A1 (fr) * | 1977-01-25 | 1978-08-18 | Poudres & Explosifs Ste Nale | Procede de preparation de polystyrylpyridine |
| US4362860A (en) * | 1981-11-02 | 1982-12-07 | Rockwell International Corporation | Addition curing polystyryl pyridine |
| US4471107A (en) * | 1984-01-30 | 1984-09-11 | American Cyanamid Company | Process for the prepartion of vinylpolystyrylpyridine compounds |
| US4515938A (en) * | 1984-03-12 | 1985-05-07 | The Dow Chemical Company | Hydroxystyrylazapolymers |
| US4500690A (en) * | 1984-05-11 | 1985-02-19 | The Dow Chemical Company | Thermosetting polymers from aromatic aldehydes, azines and isopropenyl phenols |
-
1985
- 1985-04-23 US US06/726,554 patent/US4575542A/en not_active Expired - Fee Related
-
1986
- 1986-02-20 WO PCT/US1986/000354 patent/WO1986006386A1/en not_active Ceased
- 1986-02-20 AU AU55459/86A patent/AU570146B2/en not_active Ceased
- 1986-02-20 KR KR1019860700916A patent/KR940003860B1/ko not_active Expired - Lifetime
- 1986-02-20 EP EP86901663A patent/EP0220204A1/en not_active Ceased
- 1986-02-20 JP JP61501409A patent/JPS62500526A/ja active Granted
- 1986-02-24 CA CA000502516A patent/CA1261529A/en not_active Expired
-
1988
- 1988-07-26 JP JP63184776A patent/JPS6454018A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| AU570146B2 (en) | 1988-03-03 |
| US4575542A (en) | 1986-03-11 |
| AU5545986A (en) | 1986-11-18 |
| JPH032444B2 (enExample) | 1991-01-16 |
| JPS6454018A (en) | 1989-03-01 |
| KR870700653A (ko) | 1987-12-30 |
| WO1986006386A1 (en) | 1986-11-06 |
| EP0220204A1 (en) | 1987-05-06 |
| JPS62500526A (ja) | 1987-03-05 |
| KR940003860B1 (ko) | 1994-05-04 |
| JPH0122285B2 (enExample) | 1989-04-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |