JP4519654B2 - 極性官能基を含む環状オレフィン重合体の重合方法および環状オレフィン重合体を用いる電子装置 - Google Patents
極性官能基を含む環状オレフィン重合体の重合方法および環状オレフィン重合体を用いる電子装置 Download PDFInfo
- Publication number
- JP4519654B2 JP4519654B2 JP2004556965A JP2004556965A JP4519654B2 JP 4519654 B2 JP4519654 B2 JP 4519654B2 JP 2004556965 A JP2004556965 A JP 2004556965A JP 2004556965 A JP2004556965 A JP 2004556965A JP 4519654 B2 JP4519654 B2 JP 4519654B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- polar functional
- cyclic olefin
- functional group
- 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
Links
- 238000006116 polymerization reaction Methods 0.000 title claims description 95
- 125000000524 functional group Chemical group 0.000 title claims description 91
- 238000000034 method Methods 0.000 title claims description 31
- 229920000089 Cyclic olefin copolymer Polymers 0.000 title description 24
- 239000003054 catalyst Substances 0.000 claims description 135
- 229920000642 polymer Polymers 0.000 claims description 131
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 129
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 114
- 239000000178 monomer Substances 0.000 claims description 104
- 125000004432 carbon atom Chemical group C* 0.000 claims description 86
- -1 norbornene compound Chemical class 0.000 claims description 51
- 238000006243 chemical reaction Methods 0.000 claims description 46
- 238000004519 manufacturing process Methods 0.000 claims description 44
- 229920001577 copolymer Polymers 0.000 claims description 39
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000003342 alkenyl group Chemical group 0.000 claims description 34
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- 125000000304 alkynyl group Chemical group 0.000 claims description 28
- 125000001188 haloalkyl group Chemical group 0.000 claims description 24
- 229910052751 metal Inorganic materials 0.000 claims description 24
- 239000002184 metal Substances 0.000 claims description 24
- 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 claims description 24
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 23
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical group C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- 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 claims description 18
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
- 150000001450 anions Chemical class 0.000 claims description 14
- 239000012041 precatalyst Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 12
- 150000001768 cations Chemical class 0.000 claims description 11
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 238000012644 addition polymerization Methods 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 2
- 239000003426 co-catalyst Substances 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 claims 1
- 238000004581 coalescence Methods 0.000 claims 1
- 229940125898 compound 5 Drugs 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
- 239000002244 precipitate Substances 0.000 description 41
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 36
- 239000010408 film Substances 0.000 description 35
- RMAZRAQKPTXZNL-UHFFFAOYSA-N methyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2C(C(=O)OC)CC1C=C2 RMAZRAQKPTXZNL-UHFFFAOYSA-N 0.000 description 35
- RFIHUFUZAHTZOQ-UHFFFAOYSA-N butyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2C(C(=O)OCCCC)CC1C=C2 RFIHUFUZAHTZOQ-UHFFFAOYSA-N 0.000 description 32
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- 239000002904 solvent Substances 0.000 description 28
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 25
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 25
- 239000011521 glass Substances 0.000 description 22
- 238000003756 stirring Methods 0.000 description 21
- 239000004215 Carbon black (E152) Substances 0.000 description 20
- 239000007795 chemical reaction product Substances 0.000 description 20
- 229930195733 hydrocarbon Natural products 0.000 description 20
- 238000002360 preparation method Methods 0.000 description 20
- 238000001914 filtration Methods 0.000 description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- 125000001183 hydrocarbyl group Chemical group 0.000 description 13
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 10
- 150000002430 hydrocarbons Chemical class 0.000 description 10
- 230000003197 catalytic effect Effects 0.000 description 9
- 230000003287 optical effect Effects 0.000 description 9
- 101150003085 Pdcl gene Proteins 0.000 description 8
- 239000003446 ligand Substances 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 229910052723 transition metal Inorganic materials 0.000 description 8
- 150000003624 transition metals Chemical class 0.000 description 8
- VEEKCIOFMIAGSF-UHFFFAOYSA-N 4-butylbicyclo[2.2.1]hept-2-ene Chemical compound C1CC2C=CC1(CCCC)C2 VEEKCIOFMIAGSF-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 150000002894 organic compounds Chemical class 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 6
- 229910052696 pnictogen Inorganic materials 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- PGKLXLJJGUJWJX-UHFFFAOYSA-N butyl bicyclo[2.2.1]hept-2-ene-4-carboxylate Chemical compound C1CC2C=CC1(C(=O)OCCCC)C2 PGKLXLJJGUJWJX-UHFFFAOYSA-N 0.000 description 5
- 238000007334 copolymerization reaction Methods 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 125000004185 ester group Chemical group 0.000 description 5
- RNWDNEVYZAPIBG-UHFFFAOYSA-N methyl bicyclo[2.2.1]hept-2-ene-4-carboxylate Chemical compound C1CC2C=CC1(C(=O)OC)C2 RNWDNEVYZAPIBG-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- UDMMZSJNHAWYKX-UHFFFAOYSA-N 4-phenylbicyclo[2.2.1]hept-2-ene Chemical compound C1C(C=C2)CCC21C1=CC=CC=C1 UDMMZSJNHAWYKX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000012776 electronic material Substances 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000012788 optical film Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 3
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 239000011593 sulfur Chemical group 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- REBKUVYQFXSVNO-NSCUHMNNSA-N (3E)-1,1-dichloropenta-1,3-diene Chemical compound C\C=C\C=C(Cl)Cl REBKUVYQFXSVNO-NSCUHMNNSA-N 0.000 description 2
- HRVGJQMCNYJEHM-UHFFFAOYSA-N 2-(5-bicyclo[2.2.1]hept-2-enyl)acetic acid Chemical compound C1C2C(CC(=O)O)CC1C=C2 HRVGJQMCNYJEHM-UHFFFAOYSA-N 0.000 description 2
- KMRASZKMNHTING-UHFFFAOYSA-N 4-hexylbicyclo[2.2.1]hept-2-ene Chemical compound C1CC2C=CC1(CCCCCC)C2 KMRASZKMNHTING-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-UHFFFAOYSA-N Dicyclopentadiene Chemical compound C1C2C3CC=CC3C1C=C2 HECLRDQVFMWTQS-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 229910052581 Si3N4 Inorganic materials 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 150000004645 aluminates Chemical class 0.000 description 2
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 2
- FYGUSUBEMUKACF-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-5-carboxylic acid Chemical compound C1C2C(C(=O)O)CC1C=C2 FYGUSUBEMUKACF-UHFFFAOYSA-N 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 229910000085 borane Inorganic materials 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- 150000001721 carbon Chemical class 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000003851 corona treatment Methods 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 229910052732 germanium Inorganic materials 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 239000012968 metallocene catalyst Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 150000002848 norbornenes Chemical class 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- LRMSQVBRUNSOJL-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)F LRMSQVBRUNSOJL-UHFFFAOYSA-N 0.000 description 1
- YPJUNDFVDDCYIH-UHFFFAOYSA-M 2,2,3,3,4,4,4-heptafluorobutanoate Chemical compound [O-]C(=O)C(F)(F)C(F)(F)C(F)(F)F YPJUNDFVDDCYIH-UHFFFAOYSA-M 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229910017008 AsF 6 Inorganic materials 0.000 description 1
- WLQKHRHCTSEXTL-UHFFFAOYSA-N C1C2CCC1C=C2.C1C2CCC1C=C2 Chemical compound C1C2CCC1C=C2.C1C2CCC1C=C2 WLQKHRHCTSEXTL-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910020366 ClO 4 Inorganic materials 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- 241001379910 Ephemera danica Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910018286 SbF 6 Inorganic materials 0.000 description 1
- 238000004639 Schlenk technique Methods 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 239000011954 Ziegler–Natta catalyst Substances 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 125000005626 carbonium group Chemical group 0.000 description 1
- 239000011951 cationic catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003779 heat-resistant material Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- JFNLZVQOOSMTJK-UHFFFAOYSA-N norbornene Chemical compound C1C2CCC1C=C2 JFNLZVQOOSMTJK-UHFFFAOYSA-N 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000636 poly(norbornene) polymer Polymers 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010107 reaction injection moulding Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 125000005353 silylalkyl group Chemical group 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- AIWZOHBYSFSQGV-LNKPDPKZSA-M sodium;(z)-4-oxopent-2-en-2-olate Chemical compound [Na+].C\C([O-])=C\C(C)=O AIWZOHBYSFSQGV-LNKPDPKZSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 125000005389 trialkylsiloxy group Chemical group 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 150000003754 zirconium Chemical class 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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
- 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
- C08F4/70—Iron group metals, platinum group metals or compounds thereof
-
- 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
-
- 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
-
- 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/38—Polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
- C09K2323/03—Viewing layer characterised by chemical composition
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polarising Elements (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2002-0076925A KR100477943B1 (ko) | 2002-12-05 | 2002-12-05 | 극성 작용기를 포함하는 고리형 올레핀 중합 방법 |
| KR10-2003-0086705A KR100515595B1 (ko) | 2003-12-02 | 2003-12-02 | 극성 작용기를 포함하는 고리형 올레핀 중합방법 및고리형 올레핀 중합체를 채용한 전자장치 |
| PCT/KR2003/002634 WO2004050726A1 (en) | 2002-12-05 | 2003-12-03 | Method for polymerizing cycloolefin polymer containing polar functional groups and electronic devices employing the polymerized cycloolefins |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009244740A Division JP2010059428A (ja) | 2002-12-05 | 2009-10-23 | 極性官能基を含む環状オレフィン重合体の重合方法および環状オレフィン重合体を用いる電子装置 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006500468A JP2006500468A (ja) | 2006-01-05 |
| JP2006500468A5 JP2006500468A5 (https=) | 2009-02-26 |
| JP4519654B2 true JP4519654B2 (ja) | 2010-08-04 |
Family
ID=32473817
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004556965A Expired - Lifetime JP4519654B2 (ja) | 2002-12-05 | 2003-12-03 | 極性官能基を含む環状オレフィン重合体の重合方法および環状オレフィン重合体を用いる電子装置 |
| JP2009244740A Pending JP2010059428A (ja) | 2002-12-05 | 2009-10-23 | 極性官能基を含む環状オレフィン重合体の重合方法および環状オレフィン重合体を用いる電子装置 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009244740A Pending JP2010059428A (ja) | 2002-12-05 | 2009-10-23 | 極性官能基を含む環状オレフィン重合体の重合方法および環状オレフィン重合体を用いる電子装置 |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US7718744B2 (https=) |
| EP (1) | EP1468027B1 (https=) |
| JP (2) | JP4519654B2 (https=) |
| AU (1) | AU2003283853A1 (https=) |
| TW (1) | TWI300418B (https=) |
| WO (1) | WO2004050726A1 (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5449649B2 (ja) * | 2004-07-07 | 2014-03-19 | エルジー・ケム・リミテッド | 極性作用基を含む環状オレフィン重合体の製造方法、これにより製造されたオレフィン重合体及びその重合体を含む光学異方性フィルム |
| KR100733923B1 (ko) * | 2004-07-07 | 2007-07-02 | 주식회사 엘지화학 | 극성 작용기를 갖는 고리형 올레핀 중합체 제조용 촉매시스템, 이를 이용한 중합체 제조방법과 이 방법에 의해제조된 올레핀 중합체 및 상기 중합체를 포함하는 광학이방성 필름 |
| WO2006031067A1 (en) | 2004-09-16 | 2006-03-23 | Lg Chem, Ltd. | Catalyst system for polymerizing cyclic olefin having polar functional group, polymerizing method using the catalyst system, olefin polymer produced by the method and optical anisotropic film comprising the olefin polymer |
| US20080125556A1 (en) * | 2004-12-22 | 2008-05-29 | Jsr Corporation | Method For Producing Cyclic Olefin Addition Copolymer, Cyclic Olefin Addition Copolymer And Use Thereof |
| US7964680B2 (en) * | 2006-06-16 | 2011-06-21 | Lg Chem, Ltd. | Method for polymerizing cyclic olefin having polar functional group, olefin polymer produced thereby, optical anisotropic film comprising the same, and catalyst composition for polymerizing the cyclic olefin |
| JP2008031292A (ja) * | 2006-07-28 | 2008-02-14 | Fujifilm Corp | ノルボルネン系重合体フィルム、ならびにそれを用いた位相差フィルム、偏光板および液晶表示装置 |
| JP2008106244A (ja) * | 2006-09-29 | 2008-05-08 | Sumitomo Bakelite Co Ltd | 環状オレフィン系付加共重合体 |
| WO2010047348A1 (ja) * | 2008-10-21 | 2010-04-29 | 日本ゼオン株式会社 | 重合性組成物、樹脂成形体、及び積層体 |
| JP2011084681A (ja) * | 2009-10-19 | 2011-04-28 | Shin-Etsu Chemical Co Ltd | 高気体透過性環状オレフィン付加重合体及びその製造方法 |
| US8541523B2 (en) * | 2010-04-05 | 2013-09-24 | Promerus, Llc | Norbornene-type polymers, compositions thereof and lithographic process using such compositions |
| JP5212659B2 (ja) * | 2010-07-30 | 2013-06-19 | 信越化学工業株式会社 | 高気体透過性環状オレフィン付加重合体の製造方法 |
| KR101746789B1 (ko) | 2014-12-18 | 2017-06-13 | 주식회사 엘지화학 | 고리형 올레핀 화합물의 (공)중합체를 포함하는 수직 배향막 |
| EP3815159A1 (en) * | 2018-06-28 | 2021-05-05 | Merck Patent GmbH | Method for producing an electronic device |
| TWI867226B (zh) * | 2020-06-24 | 2024-12-21 | 日商住友電木股份有限公司 | 作為光學材料之受阻胺穩定型ｕｖ活性有機鈀催化聚環烯烴組成物 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE109224C (https=) | ||||
| US3330815A (en) * | 1964-03-24 | 1967-07-11 | Union Carbide Corp | Novel polynorbornenes, process for production thereof, and products produced therefrom |
| US5179171A (en) * | 1985-05-24 | 1993-01-12 | Mitsui Petrochemical Industries, Ltd. | Random copolymer, and process for production thereof |
| US5011730A (en) * | 1987-08-14 | 1991-04-30 | The B. F. Goodrich Company | Bulk polymerized cycloolefin circuit boards |
| US4831172A (en) * | 1988-03-23 | 1989-05-16 | The Dow Chemical Company | Benzocyclobutene-based organosilane adhesion aids |
| US5516456A (en) * | 1994-02-24 | 1996-05-14 | Japan Synthetic Rubber Co., Ltd. | Liquid crystal display panel |
| US5705503A (en) * | 1995-05-25 | 1998-01-06 | Goodall; Brian Leslie | Addition polymers of polycycloolefins containing functional substituents |
| EP1034196B1 (en) * | 1998-10-05 | 2005-01-12 | Promerus LLC | Catalyst and methods for polymerizing cycloolefins |
| 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 |
| 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 |
-
2003
- 2003-12-03 US US10/502,185 patent/US7718744B2/en not_active Expired - Lifetime
- 2003-12-03 WO PCT/KR2003/002634 patent/WO2004050726A1/en not_active Ceased
- 2003-12-03 AU AU2003283853A patent/AU2003283853A1/en not_active Abandoned
- 2003-12-03 JP JP2004556965A patent/JP4519654B2/ja not_active Expired - Lifetime
- 2003-12-03 EP EP03776048.5A patent/EP1468027B1/en not_active Expired - Lifetime
- 2003-12-04 TW TW092134257A patent/TWI300418B/zh not_active IP Right Cessation
-
2006
- 2006-07-20 US US11/489,848 patent/US7786230B2/en active Active
-
2008
- 2008-11-20 US US12/274,947 patent/US7786231B2/en not_active Expired - Lifetime
-
2009
- 2009-10-23 JP JP2009244740A patent/JP2010059428A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US20070021576A1 (en) | 2007-01-25 |
| TW200424229A (en) | 2004-11-16 |
| JP2010059428A (ja) | 2010-03-18 |
| JP2006500468A (ja) | 2006-01-05 |
| EP1468027B1 (en) | 2014-05-07 |
| AU2003283853A1 (en) | 2004-06-23 |
| WO2004050726A1 (en) | 2004-06-17 |
| US20050085606A1 (en) | 2005-04-21 |
| EP1468027A1 (en) | 2004-10-20 |
| US7718744B2 (en) | 2010-05-18 |
| US7786231B2 (en) | 2010-08-31 |
| US20090092769A1 (en) | 2009-04-09 |
| TWI300418B (en) | 2008-09-01 |
| US7786230B2 (en) | 2010-08-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010059428A (ja) | 極性官能基を含む環状オレフィン重合体の重合方法および環状オレフィン重合体を用いる電子装置 | |
| JP4938544B2 (ja) | ノルボルネン−エステル系付加重合体およびその製造方法 | |
| KR100561068B1 (ko) | 노보넨-에스테르계 부가중합체 및 이의 제조방법 | |
| US8293674B2 (en) | Catalyst system for preparing cyclic olefin addition polymer, cyclic olefin addition polymer prepared by using the catalyst system and method for preparing the same | |
| JP2007246914A5 (https=) | ||
| KR101544562B1 (ko) | 광반응기를 갖는 고리형 올레핀 화합물 및 광반응성 중합체 | |
| JP5449649B2 (ja) | 極性作用基を含む環状オレフィン重合体の製造方法、これにより製造されたオレフィン重合体及びその重合体を含む光学異方性フィルム | |
| KR100733923B1 (ko) | 극성 작용기를 갖는 고리형 올레핀 중합체 제조용 촉매시스템, 이를 이용한 중합체 제조방법과 이 방법에 의해제조된 올레핀 중합체 및 상기 중합체를 포함하는 광학이방성 필름 | |
| KR100515595B1 (ko) | 극성 작용기를 포함하는 고리형 올레핀 중합방법 및고리형 올레핀 중합체를 채용한 전자장치 | |
| KR100477943B1 (ko) | 극성 작용기를 포함하는 고리형 올레핀 중합 방법 | |
| US7964680B2 (en) | Method for polymerizing cyclic olefin having polar functional group, olefin polymer produced thereby, optical anisotropic film comprising the same, and catalyst composition for polymerizing the cyclic olefin | |
| KR100876528B1 (ko) | 극성 작용기를 갖는 고리형 올레핀 중합체 제조용 촉매조성물 | |
| KR100762839B1 (ko) | 극성 작용기를 갖는 고리형 올레핀 중합체 제조용 촉매시스템, 이를 이용한 중합체 제조방법과 이 방법에 의해제조된 올레핀 중합체 및 상기 중합체를 포함하는 광학이방성 필름 | |
| KR100985234B1 (ko) | 극성 작용기를 갖는 고리형 올레핀 중합체의 제조방법, 이방법에 의해 제조된 고리형 올레핀 중합체 및 상기중합체를 포함하는 광학 이방성 필름 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20071116 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20071127 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080227 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20080701 |
|
| RD03 | Notification of appointment of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7423 Effective date: 20080715 |
|
| RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20080808 |
|
| RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20080812 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20081001 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20081008 |
|
| A524 | Written submission of copy of amendment under article 19 pct |
Free format text: JAPANESE INTERMEDIATE CODE: A524 Effective date: 20081104 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20090623 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20091023 |
|
| A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20091030 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20100420 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20100519 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130528 Year of fee payment: 3 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 4519654 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |