JP3817015B2 - 環状オレフィン系共重合体およびその用途 - Google Patents
環状オレフィン系共重合体およびその用途 Download PDFInfo
- Publication number
- JP3817015B2 JP3817015B2 JP09574997A JP9574997A JP3817015B2 JP 3817015 B2 JP3817015 B2 JP 3817015B2 JP 09574997 A JP09574997 A JP 09574997A JP 9574997 A JP9574997 A JP 9574997A JP 3817015 B2 JP3817015 B2 JP 3817015B2
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- Prior art keywords
- group
- carbon atoms
- cyclic olefin
- atom
- bonded
- 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 - Lifetime
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- 229920000089 Cyclic olefin copolymer Polymers 0.000 title claims description 22
- 239000004713 Cyclic olefin copolymer Substances 0.000 title claims description 22
- -1 cyclic olefin Chemical class 0.000 claims description 87
- 125000004432 carbon atom Chemical group C* 0.000 claims description 66
- 238000006116 polymerization reaction Methods 0.000 claims description 27
- 125000005843 halogen group Chemical group 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 18
- 239000004711 α-olefin Substances 0.000 claims description 16
- 229920002554 vinyl polymer Polymers 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000002950 monocyclic group Chemical group 0.000 claims description 10
- 230000003287 optical effect Effects 0.000 claims description 10
- 125000003367 polycyclic group Chemical group 0.000 claims description 10
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 230000009477 glass transition Effects 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 238000012662 bulk polymerization Methods 0.000 claims description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims description 3
- 239000002002 slurry Substances 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 150000008040 ionic compounds Chemical class 0.000 description 17
- 239000000243 solution Substances 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
- 229920001577 copolymer Polymers 0.000 description 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 10
- 239000005977 Ethylene Substances 0.000 description 10
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- 238000007334 copolymerization reaction Methods 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical compound [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 125000002877 alkyl aryl group Chemical group 0.000 description 6
- 150000001450 anions Chemical group 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 6
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 239000012968 metallocene catalyst Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 150000003623 transition metal compounds Chemical class 0.000 description 6
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 150000002738 metalloids Chemical group 0.000 description 5
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 5
- 229910052726 zirconium Inorganic materials 0.000 description 5
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000001118 alkylidene group Chemical group 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 125000005018 aryl alkenyl group Chemical group 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 150000004678 hydrides Chemical class 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 4
- 238000001746 injection moulding Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 4
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NWBSMOHZFZYBLB-UHFFFAOYSA-L [Cl-].[Cl-].C1=CC2=CC=CC=C2C1[Zr+2](=C(C)C)C1C2=CC=CC=C2C=C1 Chemical compound [Cl-].[Cl-].C1=CC2=CC=CC=C2C1[Zr+2](=C(C)C)C1C2=CC=CC=C2C=C1 NWBSMOHZFZYBLB-UHFFFAOYSA-L 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052735 hafnium Inorganic materials 0.000 description 3
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 3
- 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 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- XBFJAVXCNXDMBH-UHFFFAOYSA-N tetracyclo[6.2.1.1(3,6).0(2,7)]dodec-4-ene Chemical compound C1C(C23)C=CC1C3C1CC2CC1 XBFJAVXCNXDMBH-UHFFFAOYSA-N 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 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 description 3
- 125000003837 (C1-C20) alkyl group Chemical group 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
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- WBGJXNLILNRVBB-UHFFFAOYSA-N BBBBBBCBC Chemical compound BBBBBBCBC WBGJXNLILNRVBB-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- VPAJBWKGGBGQBE-UHFFFAOYSA-L [Cl-].[Cl-].C1=CC2=CC=CC=C2C1[Zr+2](C1C2=CC=CC=C2C=C1)=C(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound [Cl-].[Cl-].C1=CC2=CC=CC=C2C1[Zr+2](C1C2=CC=CC=C2C=C1)=C(C=1C=CC=CC=1)C1=CC=CC=C1 VPAJBWKGGBGQBE-UHFFFAOYSA-L 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910000085 borane Inorganic materials 0.000 description 2
- 229910052800 carbon group element Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 125000005131 dialkylammonium group Chemical group 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-O dimethyl(phenyl)azanium Chemical compound C[NH+](C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-O 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 description 2
- 125000004407 fluoroaryl group Chemical group 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- VAMFXQBUQXONLZ-UHFFFAOYSA-N n-alpha-eicosene Natural products CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- JFNLZVQOOSMTJK-UHFFFAOYSA-N norbornene Chemical class C1C2CCC1C=C2 JFNLZVQOOSMTJK-UHFFFAOYSA-N 0.000 description 2
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000013307 optical fiber Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- ZCBSOTLLNBJIEK-UHFFFAOYSA-N silane titanium Chemical compound [SiH4].[Ti] ZCBSOTLLNBJIEK-UHFFFAOYSA-N 0.000 description 2
- 125000004079 stearyl 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])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 2
- 239000000758 substrate Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 2
- ZOICEQJZAWJHSI-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl)boron Chemical compound [B]C1=C(F)C(F)=C(F)C(F)=C1F ZOICEQJZAWJHSI-UHFFFAOYSA-N 0.000 description 1
- VKMQKNJWQNCEQV-UHFFFAOYSA-N (4-methylphenyl)boron Chemical compound [B]C1=CC=C(C)C=C1 VKMQKNJWQNCEQV-UHFFFAOYSA-N 0.000 description 1
- BNGUZDGWNATSIB-VQHVLOKHSA-N (e)-heptadec-4-ene Chemical class CCCCCCCCCCCC\C=C\CCC BNGUZDGWNATSIB-VQHVLOKHSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
- 229940106006 1-eicosene Drugs 0.000 description 1
- FIKTURVKRGQNQD-UHFFFAOYSA-N 1-eicosene Natural products CCCCCCCCCCCCCCCCCC=CC(O)=O FIKTURVKRGQNQD-UHFFFAOYSA-N 0.000 description 1
- VTPNYMSKBPZSTF-UHFFFAOYSA-N 1-ethenyl-2-ethylbenzene Chemical compound CCC1=CC=CC=C1C=C VTPNYMSKBPZSTF-UHFFFAOYSA-N 0.000 description 1
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- XHUZSRRCICJJCN-UHFFFAOYSA-N 1-ethenyl-3-ethylbenzene Chemical compound CCC1=CC=CC(C=C)=C1 XHUZSRRCICJJCN-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- WHFHDVDXYKOSKI-UHFFFAOYSA-N 1-ethenyl-4-ethylbenzene Chemical compound CCC1=CC=C(C=C)C=C1 WHFHDVDXYKOSKI-UHFFFAOYSA-N 0.000 description 1
- WAUKBOOEPYNAGU-UHFFFAOYSA-N 1-phenylprop-2-enyl acetate Chemical compound CC(=O)OC(C=C)C1=CC=CC=C1 WAUKBOOEPYNAGU-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- ISRGONDNXBCDBM-UHFFFAOYSA-N 2-chlorostyrene Chemical compound ClC1=CC=CC=C1C=C ISRGONDNXBCDBM-UHFFFAOYSA-N 0.000 description 1
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- FZHNODDFDJBMAS-UHFFFAOYSA-N 2-ethoxyethenylbenzene Chemical compound CCOC=CC1=CC=CC=C1 FZHNODDFDJBMAS-UHFFFAOYSA-N 0.000 description 1
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- DHRRIBDTHFBPNG-UHFFFAOYSA-L magnesium dichloride hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Cl-].[Cl-] DHRRIBDTHFBPNG-UHFFFAOYSA-L 0.000 description 1
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- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- AGOOAFIKKUZTEB-UHFFFAOYSA-N tris(3,5-difluorophenyl)borane Chemical compound FC1=CC(F)=CC(B(C=2C=C(F)C=C(F)C=2)C=2C=C(F)C=C(F)C=2)=C1 AGOOAFIKKUZTEB-UHFFFAOYSA-N 0.000 description 1
- YPVVTWIAXFPZLS-UHFFFAOYSA-N tris(4-fluorophenyl)borane Chemical compound C1=CC(F)=CC=C1B(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 YPVVTWIAXFPZLS-UHFFFAOYSA-N 0.000 description 1
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 description 1
- OSMBUUFIZBTSNO-UHFFFAOYSA-N tris[4-(fluoromethyl)phenyl]borane Chemical compound C1=CC(CF)=CC=C1B(C=1C=CC(CF)=CC=1)C1=CC=C(CF)C=C1 OSMBUUFIZBTSNO-UHFFFAOYSA-N 0.000 description 1
- OLFPYUPGPBITMH-UHFFFAOYSA-N tritylium Chemical compound C1=CC=CC=C1[C+](C=1C=CC=CC=1)C1=CC=CC=C1 OLFPYUPGPBITMH-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- C08F277/00—Macromolecular compounds obtained by polymerising monomers on to polymers of carbocyclic or heterocyclic monomers as defined respectively in group C08F32/00 or in group C08F34/00
-
- 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
-
- 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
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/02—Ethene
-
- 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/02—Ethene
-
- 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
- C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F232/02—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings
- C08F232/04—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings having one carbon-to-carbon double bond
-
- 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
- C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F232/08—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having condensed rings
-
- 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
- C08F32/00—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F32/02—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings
- C08F32/04—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings having one carbon-to-carbon double bond
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65912—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an organoaluminium compound
-
- 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
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/943—Polymerization with metallocene catalysts
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Optical Fibers, Optical Fiber Cores, And Optical Fiber Bundles (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP09574997A JP3817015B2 (ja) | 1997-04-14 | 1997-04-14 | 環状オレフィン系共重合体およびその用途 |
| TW087105303A TW370535B (en) | 1997-04-14 | 1998-04-08 | Cycloolefin copolymers |
| CA002234494A CA2234494A1 (en) | 1997-04-14 | 1998-04-09 | Cycloolefin copolymers and uses thereof |
| DE69817432T DE69817432T2 (de) | 1997-04-14 | 1998-04-14 | Cycloolefinpolymere und deren Verwendung |
| US09/059,558 US6063886A (en) | 1997-04-14 | 1998-04-14 | Cycloolefin copolymers and uses thereof |
| KR10-1998-0013344A KR100425791B1 (ko) | 1997-04-14 | 1998-04-14 | 시클로올레핀공중합체및그용도 |
| EP98106741A EP0872506B1 (en) | 1997-04-14 | 1998-04-14 | Cycloolefin copolymers and uses thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP09574997A JP3817015B2 (ja) | 1997-04-14 | 1997-04-14 | 環状オレフィン系共重合体およびその用途 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH10287713A JPH10287713A (ja) | 1998-10-27 |
| JPH10287713A5 JPH10287713A5 (enExample) | 2004-10-07 |
| JP3817015B2 true JP3817015B2 (ja) | 2006-08-30 |
Family
ID=14146156
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP09574997A Expired - Lifetime JP3817015B2 (ja) | 1997-04-14 | 1997-04-14 | 環状オレフィン系共重合体およびその用途 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6063886A (enExample) |
| EP (1) | EP0872506B1 (enExample) |
| JP (1) | JP3817015B2 (enExample) |
| KR (1) | KR100425791B1 (enExample) |
| CA (1) | CA2234494A1 (enExample) |
| DE (1) | DE69817432T2 (enExample) |
| TW (1) | TW370535B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020066529A1 (ja) | 2018-09-27 | 2020-04-02 | 三井化学株式会社 | 環状オレフィン系樹脂組成物、成形体および光学部品 |
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| KR20000048045A (ko) * | 1998-12-11 | 2000-07-25 | 고오사이 아끼오 | 공중합체, 이의 제조 방법 및 이의 성형품 |
| JP2001074915A (ja) * | 1999-06-29 | 2001-03-23 | Mitsui Chemicals Inc | トーリックレンズ |
| WO2001030870A1 (en) * | 1999-10-25 | 2001-05-03 | Idemitsu Petrochemical Co., Ltd. | Olefin copolymer, film, and sheet |
| JP4766359B2 (ja) * | 2000-02-24 | 2011-09-07 | コニカミノルタホールディングス株式会社 | 対物レンズ及び光ピックアップ装置 |
| JP3899511B2 (ja) * | 2001-04-27 | 2007-03-28 | Ｊｓｒ株式会社 | 熱可塑性ノルボルネン系樹脂系光学用フィルム |
| JP4238501B2 (ja) * | 2001-04-27 | 2009-03-18 | Ｊｓｒ株式会社 | 熱可塑性ノルボルネン系樹脂系光学用フィルム |
| TW583191B (en) * | 2001-05-10 | 2004-04-11 | Sumitomo Chemical Co | Phase retarder |
| WO2003020488A1 (de) | 2001-08-30 | 2003-03-13 | Zeptosens Ag | Verfahren zur herstellung von abformkörpern, insbesondere optischen strukturen, und deren verwendung |
| JP4178810B2 (ja) | 2001-12-25 | 2008-11-12 | Ｊｓｒ株式会社 | 熱可塑性ノルボルネン系樹脂系光学用フィルム |
| WO2004016405A1 (en) * | 2002-08-16 | 2004-02-26 | Johnson & Johnson Vision Care, Inc. | Molds for producing contact lenses |
| JP4569396B2 (ja) * | 2004-06-16 | 2010-10-27 | 住友化学株式会社 | 位相差フィルムおよびそれを備えた液晶表示装置 |
| KR20080000568A (ko) * | 2005-03-25 | 2008-01-02 | 니폰 제온 가부시키가이샤 | 노르보넨계 부가 공중합체 및 성형품 |
| JP5119617B2 (ja) * | 2006-07-18 | 2013-01-16 | 住友化学株式会社 | 環状オレフィン系重合体の製造方法 |
| JP2008031319A (ja) * | 2006-07-28 | 2008-02-14 | Fujifilm Corp | ノルボルネン系重合体、フィルム、偏光板および液晶表示装置 |
| CN101889209A (zh) | 2007-10-22 | 2010-11-17 | 贝克顿·迪金森公司 | 评价在含有机基聚硅氧烷的悬浮液中蛋白质聚集的方法和用含蛋白质溶液的有机基聚硅氧烷涂布的医疗制品 |
| KR101137208B1 (ko) * | 2007-12-27 | 2012-04-19 | 주식회사 엘지화학 | 고리형 올레핀 조단량체를 이용한 고리형 올레핀 고분자화합물의 제조방법 |
| EP3536363A1 (en) | 2008-09-22 | 2019-09-11 | Becton, Dickinson and Company | Systems for coating the interior of a container |
| US8802603B2 (en) | 2010-06-17 | 2014-08-12 | Becton, Dickinson And Company | Medical components having coated surfaces exhibiting low friction and low reactivity |
| JP2012220853A (ja) * | 2011-04-12 | 2012-11-12 | Keiwa Inc | メガネ用位相差フィルム、３ｄメガネ用光学シート及び３ｄメガネ |
| DE102015102012B4 (de) | 2015-02-12 | 2024-12-05 | tooz technologies GmbH | Optikelement, Anzeigevorrichtung sowie Verfahren zur Herstellung eines solchen Optikelements |
| ES2797298T3 (es) | 2016-02-10 | 2020-12-01 | Becton Dickinson France | Procedimiento para evaluar la estabilidad de una formulación a base de proteína |
| JP2018145349A (ja) * | 2017-03-08 | 2018-09-20 | 三井化学株式会社 | 光学レンズおよび光学レンズ系 |
| AU2018377771C1 (en) | 2017-11-29 | 2022-12-08 | Mitsui Chemicals, Inc. | Cyclic-olefin-based copolymer, cyclic-olefin-based copolymer composition, molded body, and medical container |
| EP3779521A4 (en) | 2018-03-30 | 2022-01-12 | Mitsui Chemicals, Inc. | OPTICAL LENS |
| JP2020036711A (ja) * | 2018-09-03 | 2020-03-12 | 三井化学株式会社 | 医療用容器および医療用容器用環状オレフィン系共重合体組成物 |
| JP7423332B2 (ja) * | 2019-03-29 | 2024-01-29 | 三井化学株式会社 | 遷移金属化合物、オレフィン重合用触媒、およびオレフィン重合体の製造方法 |
| JP7308644B2 (ja) * | 2019-03-29 | 2023-07-14 | 三井化学株式会社 | オレフィン・環状オレフィン共重合体の製造方法 |
| JP7756719B2 (ja) | 2021-06-28 | 2025-10-20 | 三井化学株式会社 | 環状オレフィン重合体、環状オレフィン重合体組成物および成形体 |
| US20250073123A1 (en) | 2023-08-30 | 2025-03-06 | Becton, Dickinson And Company | Medical Device Comprising Self-Lubricating Rubber Component |
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| US4252421A (en) * | 1978-11-09 | 1981-02-24 | John D. McCarry | Contact lenses with a colored central area |
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| PL276385A1 (en) * | 1987-01-30 | 1989-07-24 | Exxon Chemical Patents Inc | Method for polymerization of olefines,diolefins and acetylene unsaturated compounds |
| US5164469A (en) * | 1987-11-17 | 1992-11-17 | Japan Synthetic Rubber Co., Ltd. | Transparent resin material |
| US5225500A (en) * | 1988-07-15 | 1993-07-06 | Fina Technology, Inc. | Process and catalyst for producing syndiotactic polyolefins |
| US5155080A (en) * | 1988-07-15 | 1992-10-13 | Fina Technology, Inc. | Process and catalyst for producing syndiotactic polyolefins |
| KR930002411B1 (ko) * | 1988-09-14 | 1993-03-30 | 미쓰이세끼유 가가꾸고오교오 가부시끼가이샤 | 벤젠불용성 유기알루미늄 옥시화합물 및 그 제조방법 |
| EP0362814B1 (en) * | 1988-10-06 | 1995-08-16 | Showa Denko Kabushiki Kaisha | Ethylene/polycyclic monomer copolymer, process for preparation thereof, and optical article |
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| DE69026907T2 (de) * | 1989-10-10 | 1996-10-10 | Fina Technology | Metallocenkatalysator mit Lewissäure und Alkylaluminium |
| DE69026679T3 (de) * | 1989-10-30 | 2005-10-06 | Fina Technology, Inc., Houston | Addition von Alkylaluminium zum Verbessern eines Metallocenkatalysators |
| US5387568A (en) * | 1989-10-30 | 1995-02-07 | Fina Technology, Inc. | Preparation of metallocene catalysts for polymerization of olefins |
| JP2545006B2 (ja) * | 1990-07-03 | 1996-10-16 | ザ ダウ ケミカル カンパニー | 付加重合触媒 |
| US5270393A (en) * | 1990-10-24 | 1993-12-14 | Mitsui Petrochemical Industries, Ltd. | Ethylene cycloolefin random copolymer compositions |
| US5494969A (en) * | 1993-01-29 | 1996-02-27 | Mitsui Petrochemical Industries, Ltd. | Cycloolefin polymer composition |
| DE4304311C2 (de) * | 1993-02-12 | 1998-08-06 | Hoechst Ag | Cycloolefin-Copolymere für Extrusions- und Spritzgußartikel und Verfahren zur Herstellung eines Cycloolefin-Copolymers |
| US5434707A (en) * | 1993-09-14 | 1995-07-18 | Polaroid Corporation | Shaped plastic light-polarizing lens and method of making same |
| US5760139A (en) * | 1994-04-18 | 1998-06-02 | Yasuhiro Koike | Graded-refractive-index optical plastic material and method for its production |
| TW312696B (enExample) * | 1994-04-22 | 1997-08-11 | Mitsui Petroleum Chemicals Ind | |
| TW387904B (en) * | 1994-12-28 | 2000-04-21 | Hoechst Ag | Cycloolefin copolymer composition |
| JPH08231652A (ja) * | 1994-12-28 | 1996-09-10 | Mitsui Petrochem Ind Ltd | 環状オレフィン系共重合体組成物 |
| FI105196B (fi) * | 1995-05-08 | 2000-06-30 | Optatech Oy | Amorfiset olefiini-ko/terpolymeerit |
| EP0893245A4 (en) * | 1997-01-21 | 2001-03-07 | Mitsui Chemicals Inc | VULCANIZED MOLDING WITH DECORATIVE COATING, PAINTED THERMOPLASTIC RESIN COMPOSITION AND PAINTED ELASTOMER COMPOSITION |
| JPH10265588A (ja) * | 1997-01-24 | 1998-10-06 | Mitsui Chem Inc | オレフィン系共重合体製収縮フィルム |
-
1997
- 1997-04-14 JP JP09574997A patent/JP3817015B2/ja not_active Expired - Lifetime
-
1998
- 1998-04-08 TW TW087105303A patent/TW370535B/zh not_active IP Right Cessation
- 1998-04-09 CA CA002234494A patent/CA2234494A1/en not_active Abandoned
- 1998-04-14 DE DE69817432T patent/DE69817432T2/de not_active Expired - Lifetime
- 1998-04-14 US US09/059,558 patent/US6063886A/en not_active Expired - Lifetime
- 1998-04-14 EP EP98106741A patent/EP0872506B1/en not_active Expired - Lifetime
- 1998-04-14 KR KR10-1998-0013344A patent/KR100425791B1/ko not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020066529A1 (ja) | 2018-09-27 | 2020-04-02 | 三井化学株式会社 | 環状オレフィン系樹脂組成物、成形体および光学部品 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0872506A1 (en) | 1998-10-21 |
| TW370535B (en) | 1999-09-21 |
| CA2234494A1 (en) | 1998-10-14 |
| EP0872506B1 (en) | 2003-08-27 |
| KR19980081404A (ko) | 1998-11-25 |
| DE69817432T2 (de) | 2004-06-09 |
| DE69817432D1 (de) | 2003-10-02 |
| US6063886A (en) | 2000-05-16 |
| JPH10287713A (ja) | 1998-10-27 |
| KR100425791B1 (ko) | 2004-07-01 |
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Free format text: JAPANESE INTERMEDIATE CODE: R250 |
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| EXPY | Cancellation because of completion of term |