CA1042136A - Polymers of acid anhydride type norbornene derivatives and a method of preparing the same - Google Patents
Polymers of acid anhydride type norbornene derivatives and a method of preparing the sameInfo
- Publication number
- CA1042136A CA1042136A CA209,850A CA209850A CA1042136A CA 1042136 A CA1042136 A CA 1042136A CA 209850 A CA209850 A CA 209850A CA 1042136 A CA1042136 A CA 1042136A
- Authority
- CA
- Canada
- Prior art keywords
- aluminium
- group
- compounds
- tungsten
- molybdenum
- 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
- 229920000642 polymer Polymers 0.000 title claims abstract description 109
- 238000000034 method Methods 0.000 title claims abstract description 49
- 150000008065 acid anhydrides Chemical class 0.000 title claims abstract description 29
- 125000003518 norbornenyl group Chemical class C12(C=CC(CC1)C2)* 0.000 title description 3
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims abstract description 70
- 150000002848 norbornenes Chemical class 0.000 claims abstract description 47
- 239000000203 mixture Substances 0.000 claims abstract description 21
- 229920001577 copolymer Polymers 0.000 claims abstract description 16
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 claims abstract description 15
- 150000001925 cycloalkenes Chemical class 0.000 claims abstract description 9
- -1 monocyclic olefins Chemical class 0.000 claims description 109
- 238000006243 chemical reaction Methods 0.000 claims description 63
- 150000001875 compounds Chemical class 0.000 claims description 61
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 38
- 229910052721 tungsten Inorganic materials 0.000 claims description 38
- 239000010937 tungsten Substances 0.000 claims description 38
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 36
- 229910052750 molybdenum Inorganic materials 0.000 claims description 36
- 239000011733 molybdenum Substances 0.000 claims description 36
- 235000016768 molybdenum Nutrition 0.000 claims description 36
- 230000003197 catalytic effect Effects 0.000 claims description 33
- 239000004411 aluminium Substances 0.000 claims description 25
- 229910052782 aluminium Inorganic materials 0.000 claims description 25
- 235000010210 aluminium Nutrition 0.000 claims description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- MGDOJPNDRJNJBK-UHFFFAOYSA-N ethylaluminum Chemical compound [Al].C[CH2] MGDOJPNDRJNJBK-UHFFFAOYSA-N 0.000 claims description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 17
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 claims description 17
- 150000001399 aluminium compounds Chemical class 0.000 claims description 17
- 229940077746 antacid containing aluminium compound Drugs 0.000 claims description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- 101100058670 Aeromonas hydrophila subsp. hydrophila (strain ATCC 7966 / DSM 30187 / BCRC 13018 / CCUG 14551 / JCM 1027 / KCTC 2358 / NCIMB 9240 / NCTC 8049) bsr gene Proteins 0.000 claims description 13
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 13
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 12
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 150000004820 halides Chemical class 0.000 claims description 11
- 229920001519 homopolymer Polymers 0.000 claims description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 235000019441 ethanol Nutrition 0.000 claims description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 230000001476 alcoholic effect Effects 0.000 claims description 7
- 150000001993 dienes Chemical class 0.000 claims description 7
- 150000002978 peroxides Chemical class 0.000 claims description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 6
- RLAHWVDQYNDAGG-UHFFFAOYSA-N Methanetriol Chemical class OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 claims description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 6
- 150000003949 imides Chemical class 0.000 claims description 6
- 150000002924 oxiranes Chemical class 0.000 claims description 6
- 150000003254 radicals Chemical group 0.000 claims description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 6
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims description 6
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- GICWIDZXWJGTCI-UHFFFAOYSA-I molybdenum pentachloride Chemical compound Cl[Mo](Cl)(Cl)(Cl)Cl GICWIDZXWJGTCI-UHFFFAOYSA-I 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 claims description 4
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 claims description 4
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 claims description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 claims description 4
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 claims description 4
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 claims description 3
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 claims description 3
- WSWMGHRLUYADNA-UHFFFAOYSA-N 7-nitro-1,2,3,4-tetrahydroquinoline Chemical compound C1CCNC2=CC([N+](=O)[O-])=CC=C21 WSWMGHRLUYADNA-UHFFFAOYSA-N 0.000 claims description 3
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 3
- WUVPHCJNAXRVIK-UHFFFAOYSA-I Cl[Mo+3]Cl.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 Chemical compound Cl[Mo+3]Cl.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 WUVPHCJNAXRVIK-UHFFFAOYSA-I 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 3
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 claims description 3
- 239000004914 cyclooctane Substances 0.000 claims description 3
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- DBGPLCIFYUHWKA-UHFFFAOYSA-H hexachloromolybdenum Chemical compound Cl[Mo](Cl)(Cl)(Cl)(Cl)Cl DBGPLCIFYUHWKA-UHFFFAOYSA-H 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- NBJFDNVXVFBQDX-UHFFFAOYSA-I molybdenum pentafluoride Chemical compound F[Mo](F)(F)(F)F NBJFDNVXVFBQDX-UHFFFAOYSA-I 0.000 claims description 3
- BQBYSLAFGRVJME-UHFFFAOYSA-L molybdenum(2+);dichloride Chemical compound Cl[Mo]Cl BQBYSLAFGRVJME-UHFFFAOYSA-L 0.000 claims description 3
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 claims description 3
- QHIRVZBLPRTQQO-UHFFFAOYSA-I pentafluorotungsten Chemical compound F[W](F)(F)(F)F QHIRVZBLPRTQQO-UHFFFAOYSA-I 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 3
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 claims description 3
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 claims description 3
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims description 3
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 claims description 3
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 claims description 3
- NXHILIPIEUBEPD-UHFFFAOYSA-H tungsten hexafluoride Chemical compound F[W](F)(F)(F)(F)F NXHILIPIEUBEPD-UHFFFAOYSA-H 0.000 claims description 3
- WIDQNNDDTXUPAN-UHFFFAOYSA-I tungsten(v) chloride Chemical compound Cl[W](Cl)(Cl)(Cl)Cl WIDQNNDDTXUPAN-UHFFFAOYSA-I 0.000 claims description 3
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 claims description 2
- NGVTXINFTCZHGA-UHFFFAOYSA-N 1,1-dichloro-2,2-dimethoxyethane Chemical compound COC(OC)C(Cl)Cl NGVTXINFTCZHGA-UHFFFAOYSA-N 0.000 claims description 2
- FGGPMAFZNRKKSL-UHFFFAOYSA-N 1-propoxypropane-1,1-diol Chemical compound CCCOC(O)(O)CC FGGPMAFZNRKKSL-UHFFFAOYSA-N 0.000 claims description 2
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 claims description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 2
- KNUFNPDQPWTOTG-UHFFFAOYSA-N 3-methyl-6-oxatetracyclo[9.2.1.02,10.04,8]tetradec-12-ene-5,7-dione Chemical compound C12CC(C(OC3=O)=O)C3C(C)C2C2C=CC1C2 KNUFNPDQPWTOTG-UHFFFAOYSA-N 0.000 claims description 2
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 claims description 2
- QHLVXDNHAIPZFX-UHFFFAOYSA-N 5-(5-bicyclo[2.2.1]hept-2-enyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C2C3CC(C=C3)C2)=C1 QHLVXDNHAIPZFX-UHFFFAOYSA-N 0.000 claims description 2
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 claims description 2
- KOYDEUCOFXFENJ-UHFFFAOYSA-H Cl[W+2](Cl)(Cl)Cl.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 Chemical compound Cl[W+2](Cl)(Cl)Cl.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 KOYDEUCOFXFENJ-UHFFFAOYSA-H 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 2
- BWKCCRPHMILRGD-UHFFFAOYSA-N chloro hypochlorite;tungsten Chemical compound [W].ClOCl BWKCCRPHMILRGD-UHFFFAOYSA-N 0.000 claims description 2
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 claims description 2
- 229940035429 isobutyl alcohol Drugs 0.000 claims description 2
- 150000002846 norbornadienes Chemical class 0.000 claims description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims description 2
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims 7
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims 4
- YOUIDGQAIILFBW-UHFFFAOYSA-J tetrachlorotungsten Chemical compound Cl[W](Cl)(Cl)Cl YOUIDGQAIILFBW-UHFFFAOYSA-J 0.000 claims 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims 2
- MKSYJLRNTDFZCO-UHFFFAOYSA-H [W+6].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 Chemical compound [W+6].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 MKSYJLRNTDFZCO-UHFFFAOYSA-H 0.000 claims 2
- IZMHKHHRLNWLMK-UHFFFAOYSA-M chloridoaluminium Chemical compound Cl[Al] IZMHKHHRLNWLMK-UHFFFAOYSA-M 0.000 claims 2
- 229910000096 monohydride Inorganic materials 0.000 claims 2
- BFXSYWWEMMKKRS-UHFFFAOYSA-I pentabromomolybdenum Chemical compound Br[Mo](Br)(Br)(Br)Br BFXSYWWEMMKKRS-UHFFFAOYSA-I 0.000 claims 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims 2
- GJOKFTHLWOECQN-UHFFFAOYSA-N 4-oxatricyclo[6.2.1.02,7]undec-9-ene-3,6-dione Chemical compound C12C(=O)COC(=O)C2C2C=CC1C2 GJOKFTHLWOECQN-UHFFFAOYSA-N 0.000 claims 1
- FUKYIXXAGHYQRQ-UHFFFAOYSA-N 4a,5,5a,6,9,9a,10,10a-octahydro-4h-benzo[g]isochromene-1,3-dione Chemical compound C1C2CC=CCC2CC2C1CC(=O)OC2=O FUKYIXXAGHYQRQ-UHFFFAOYSA-N 0.000 claims 1
- RQRIHHYFVPLKNY-UHFFFAOYSA-N 5-oxatetracyclo[9.2.1.02,10.03,7]tetradec-12-ene-4,6-dione Chemical compound O=C1OC(=O)C(C23)C1CCC3C1C=CC2C1 RQRIHHYFVPLKNY-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 claims 1
- 125000006267 biphenyl group Chemical group 0.000 claims 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 claims 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 claims 1
- UCAOGXRUJFKQAP-UHFFFAOYSA-N n,n-dimethyl-5-nitropyridin-2-amine Chemical compound CN(C)C1=CC=C([N+]([O-])=O)C=N1 UCAOGXRUJFKQAP-UHFFFAOYSA-N 0.000 claims 1
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- IFKWVQNWZSUEIA-UHFFFAOYSA-N but-1-ene;hex-1-ene Chemical compound CCC=C.CCCCC=C IFKWVQNWZSUEIA-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- LGZKEXCMYAFYIB-UHFFFAOYSA-N butyl bicyclo[2.2.1]hepta-2,5-diene-3-carboxylate Chemical compound C1C2C(C(=O)OCCCC)=CC1C=C2 LGZKEXCMYAFYIB-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- CGEBSWVZXKTWRH-UHFFFAOYSA-N ctk3c7915 Chemical compound C12=CC(C(F)(F)F)=CC=C2C2C=CC1C2 CGEBSWVZXKTWRH-UHFFFAOYSA-N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-UHFFFAOYSA-N 0.000 description 1
- ZOLLIQAKMYWTBR-RYMQXAEESA-N cyclododecatriene Chemical compound C/1C\C=C\CC\C=C/CC\C=C\1 ZOLLIQAKMYWTBR-RYMQXAEESA-N 0.000 description 1
- HYPABJGVBDSCIT-UPHRSURJSA-N cyclododecene Chemical compound C1CCCCC\C=C/CCCC1 HYPABJGVBDSCIT-UPHRSURJSA-N 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- WPFIPEYXJSISPM-UHFFFAOYSA-N decyl bicyclo[2.2.1]hepta-2,5-diene-3-carboxylate Chemical compound C1C2C(C(=O)OCCCCCCCCCC)=CC1C=C2 WPFIPEYXJSISPM-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- VDGBMYHTHINHBJ-UHFFFAOYSA-N diethyl bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate Chemical compound C1C2C(C(=O)OCC)=C(C(=O)OCC)C1C=C2 VDGBMYHTHINHBJ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 229940031098 ethanolamine Drugs 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- QJPCJPRNPRLYDV-UHFFFAOYSA-N ethyl bicyclo[2.2.1]hepta-2,5-diene-3-carboxylate Chemical compound C1C2C(C(=O)OCC)=CC1C=C2 QJPCJPRNPRLYDV-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 1
- QIPIVBBEGFZRPJ-UHFFFAOYSA-N hexyl bicyclo[2.2.1]hepta-2,5-diene-3-carboxylate Chemical compound C1C2C(C(=O)OCCCCCC)=CC1C=C2 QIPIVBBEGFZRPJ-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- LHOWKVRJBYILML-UHFFFAOYSA-N methyl 2-(3-bicyclo[2.2.1]hepta-2,5-dienyl)acetate Chemical compound C1C2C(CC(=O)OC)=CC1C=C2 LHOWKVRJBYILML-UHFFFAOYSA-N 0.000 description 1
- XEVAEAZRZBZNNS-UHFFFAOYSA-N methyl 2-ethylbicyclo[2.2.1]hepta-2,5-diene-3-carboxylate Chemical compound C1C2C(CC)=C(C(=O)OC)C1C=C2 XEVAEAZRZBZNNS-UHFFFAOYSA-N 0.000 description 1
- KQYIZJOKQZGDQC-UHFFFAOYSA-N methyl 2-propylbicyclo[2.2.1]hepta-2,5-diene-3-carboxylate Chemical compound C1C2C(CCC)=C(C(=O)OC)C1C=C2 KQYIZJOKQZGDQC-UHFFFAOYSA-N 0.000 description 1
- WSWOAQSGGIBFBF-UHFFFAOYSA-N methyl tricyclo[6.2.1.02,7]undeca-2(7),3,5,9-tetraene-4-carboxylate Chemical compound C12=CC(C(=O)OC)=CC=C2C2C=CC1C2 WSWOAQSGGIBFBF-UHFFFAOYSA-N 0.000 description 1
- SOOZEQGBHHIHEF-UHFFFAOYSA-N methyltetrahydrophthalic anhydride Chemical compound C1C=CCC2C(=O)OC(=O)C21C SOOZEQGBHHIHEF-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000005078 molybdenum compound Substances 0.000 description 1
- 150000002752 molybdenum compounds Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QWGKQZTTWXHFLZ-UHFFFAOYSA-N octyl bicyclo[2.2.1]hepta-2,5-diene-3-carboxylate Chemical compound C1C2C(C(=O)OCCCCCCCC)=CC1C=C2 QWGKQZTTWXHFLZ-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- PRSMYUQHLOBWJR-UHFFFAOYSA-N pentyl bicyclo[2.2.1]hepta-2,5-diene-3-carboxylate Chemical compound C1C2C(C(=O)OCCCCC)=CC1C=C2 PRSMYUQHLOBWJR-UHFFFAOYSA-N 0.000 description 1
- 238000001782 photodegradation Methods 0.000 description 1
- 125000005543 phthalimide group Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- SDCLEGRGOBBSCY-UHFFFAOYSA-N propan-2-yl bicyclo[2.2.1]hepta-2,5-diene-3-carboxylate Chemical compound C1C2C(C(=O)OC(C)C)=CC1C=C2 SDCLEGRGOBBSCY-UHFFFAOYSA-N 0.000 description 1
- DOXKBUFSLXWEFG-UHFFFAOYSA-N propyl bicyclo[2.2.1]hepta-2,5-diene-3-carboxylate Chemical compound C1C2C(C(=O)OCCC)=CC1C=C2 DOXKBUFSLXWEFG-UHFFFAOYSA-N 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 150000003304 ruthenium compounds Chemical class 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- YGDFZERGENTVHY-UHFFFAOYSA-N tetracyclo[10.2.1.02,11.04,9]pentadeca-2(11),3,5,7,9,13-hexaene-6-carbonitrile Chemical compound C12=CC3=CC(C#N)=CC=C3C=C2C2C=CC1C2 YGDFZERGENTVHY-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
- C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP48106902A JPS5058200A (en, 2012) | 1973-09-25 | 1973-09-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1042136A true CA1042136A (en) | 1978-11-07 |
Family
ID=14445374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA209,850A Expired CA1042136A (en) | 1973-09-25 | 1974-09-24 | Polymers of acid anhydride type norbornene derivatives and a method of preparing the same |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4028482A (en, 2012) |
| JP (1) | JPS5058200A (en, 2012) |
| CA (1) | CA1042136A (en, 2012) |
| DE (1) | DE2445812C2 (en, 2012) |
| FR (1) | FR2244777B1 (en, 2012) |
| GB (1) | GB1487185A (en, 2012) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4329270A (en) * | 1980-09-04 | 1982-05-11 | Eastman Kodak Company | Compositions containing plasticized poly(vinyl chloride) which compositions have improved physical properties |
| US4361666A (en) * | 1982-01-04 | 1982-11-30 | Monsanto Company | Styrenic polymer additive |
| US4360629A (en) * | 1982-01-06 | 1982-11-23 | The B. F. Goodrich Company | Nonsolvent preconcentration of polymeric cycloolefins |
| EP0152371B1 (de) * | 1984-01-31 | 1989-04-26 | Ciba-Geigy Ag | Polymere aus Allyl- oder Methallyl-substituierten bicyclischen ungesättigten Dicarbonsäureanhydriden |
| IN168456B (en, 2012) * | 1985-12-16 | 1991-04-06 | Goodrich Co B F | |
| USRE35717E (en) * | 1986-04-11 | 1998-01-20 | Metton America, Inc. | Cycloolefin copolymerization method, feed composition and product |
| US4945144A (en) * | 1988-07-25 | 1990-07-31 | California Institute Of Technology | Ring opening methathesis polymerization of strained cyclic ethers |
| US4883851A (en) * | 1988-07-25 | 1989-11-28 | California Institute Of Technology | Ring opening metathesis polymerization of strained cyclic ethers |
| US4945141A (en) * | 1988-07-25 | 1990-07-31 | California Institute Of Technology | Ring opening metathesis polymerization of strained cyclic ethers |
| GB8919877D0 (en) * | 1989-09-02 | 1989-10-18 | Ciba Geigy | New polymers |
| US6169152B1 (en) * | 1996-07-05 | 2001-01-02 | Jsr Corporation | Olefin polymerization catalyst comprising transition metal compound containing a cyclic ligand having at least two nitrogen atoms in its main chain skeleton |
| DE60003008T2 (de) * | 1999-03-12 | 2004-04-01 | Sumitomo Bakelite Co. Ltd. | Verfahren zur herstellung von polymeren enthaltend cyclische anhydride als seitengruppen |
| CN1249119C (zh) * | 2000-04-13 | 2006-04-05 | 三井化学株式会社 | 加氢开环易位聚合物及其制造方法 |
| KR20030045770A (ko) * | 2000-07-03 | 2003-06-11 | 바스프 악티엔게젤샤프트 | 개선된 폴리테트라하이드로푸란 제조 방법 및 그를 위한촉매 |
| KR100591007B1 (ko) * | 2004-01-14 | 2006-06-22 | 금호석유화학 주식회사 | 신규한 중합체 및 이를 함유한 화학 증폭형 레지스트 |
| US7879963B2 (en) * | 2007-12-18 | 2011-02-01 | General Electric Company | Composition, article, and associated method |
| CN115605443B (zh) | 2021-03-09 | 2024-12-13 | 法国圣戈班玻璃厂 | 用于玻璃窗制造用设备的用于定位玻璃片材的方法和装置 |
| FR3120626B1 (fr) | 2021-03-09 | 2023-11-24 | Saint Gobain | Dispositif de positionnement de feuilles de verre, installation de fabrication de vitrages comportant un tel dispositif et procédé pour piloter automatiquement le positionnement des feuilles de verre dans une telle installation |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3494897A (en) * | 1963-12-05 | 1970-02-10 | Union Carbide Corp | Ethylene/bicyclo(2.2.1)hept-2-ene copolymers |
| NL135334C (en, 2012) * | 1966-06-29 | |||
| FR1556215A (en, 2012) * | 1967-07-25 | 1969-02-07 | ||
| FR1543497A (fr) * | 1967-08-18 | 1968-10-25 | Charbonnages De France | Polymères dérivés du bicyclo [2, 2, 1] heptène-2 |
| US3859265A (en) * | 1972-06-21 | 1975-01-07 | Ici Ltd | Production of polyalkenmers from monomers of norbornene structure containing polar groups |
| GB1409642A (en) * | 1972-03-31 | 1975-10-08 | Showa Denko Kk | Polymers of cyano-substituted norbornene derivatives and method for prepariang the same |
-
1973
- 1973-09-25 JP JP48106902A patent/JPS5058200A/ja active Pending
-
1974
- 1974-09-19 US US05/507,556 patent/US4028482A/en not_active Expired - Lifetime
- 1974-09-23 GB GB41299/74A patent/GB1487185A/en not_active Expired
- 1974-09-24 CA CA209,850A patent/CA1042136A/en not_active Expired
- 1974-09-25 FR FR7432268A patent/FR2244777B1/fr not_active Expired
- 1974-09-25 DE DE2445812A patent/DE2445812C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2445812A1 (de) | 1975-04-03 |
| GB1487185A (en) | 1977-09-28 |
| US4028482A (en) | 1977-06-07 |
| DE2445812C2 (de) | 1982-04-15 |
| FR2244777A1 (en, 2012) | 1975-04-18 |
| JPS5058200A (en, 2012) | 1975-05-20 |
| FR2244777B1 (en, 2012) | 1977-07-08 |
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