DE60311103T2 - Auf norbornenester basierendes polymerisat und verfahren zu seiner herstellung - Google Patents
Auf norbornenester basierendes polymerisat und verfahren zu seiner herstellung Download PDFInfo
- Publication number
- DE60311103T2 DE60311103T2 DE60311103T DE60311103T DE60311103T2 DE 60311103 T2 DE60311103 T2 DE 60311103T2 DE 60311103 T DE60311103 T DE 60311103T DE 60311103 T DE60311103 T DE 60311103T DE 60311103 T2 DE60311103 T2 DE 60311103T2
- Authority
- DE
- Germany
- Prior art keywords
- norbornene
- ester
- reaction
- group
- added
- 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
- 238000000034 method Methods 0.000 title claims description 38
- 238000004519 manufacturing process Methods 0.000 title description 14
- 238000006243 chemical reaction Methods 0.000 claims description 243
- 239000000178 monomer Substances 0.000 claims description 205
- 229920001577 copolymer Polymers 0.000 claims description 197
- 229920000642 polymer Polymers 0.000 claims description 180
- -1 norbornene ester Chemical class 0.000 claims description 128
- 239000003054 catalyst Substances 0.000 claims description 122
- 238000002360 preparation method Methods 0.000 claims description 117
- 229920001519 homopolymer Polymers 0.000 claims description 82
- 239000010408 film Substances 0.000 claims description 62
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 54
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 52
- 229930195733 hydrocarbon Chemical group 0.000 claims description 47
- 239000004215 Carbon black (E152) Chemical group 0.000 claims description 46
- 238000006116 polymerization reaction Methods 0.000 claims description 38
- 239000000126 substance Substances 0.000 claims description 34
- 125000004185 ester group Chemical group 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 24
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 21
- 229910052751 metal Inorganic materials 0.000 claims description 21
- 239000002184 metal Substances 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical group 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 19
- 230000035484 reaction time Effects 0.000 claims description 18
- 238000005698 Diels-Alder reaction Methods 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000001188 haloalkyl group Chemical group 0.000 claims description 15
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 15
- 229920002554 vinyl polymer Polymers 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- 230000003287 optical effect Effects 0.000 claims description 13
- 125000000524 functional group Chemical group 0.000 claims description 12
- 239000003446 ligand Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000000129 anionic group Chemical group 0.000 claims description 9
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 9
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 9
- 125000003106 haloaryl group Chemical group 0.000 claims description 9
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 125000001118 alkylidene group Chemical group 0.000 claims description 6
- 150000003623 transition metal compounds Chemical class 0.000 claims description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 150000002848 norbornenes Chemical class 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 239000010703 silicon Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000012788 optical film Substances 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- 125000004996 haloaryloxy group Chemical group 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 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 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 230000001447 compensatory effect Effects 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 289
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 164
- 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 157
- 239000011541 reaction mixture Substances 0.000 description 113
- 239000002244 precipitate Substances 0.000 description 107
- 238000003756 stirring Methods 0.000 description 106
- 239000011521 glass Substances 0.000 description 92
- 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 79
- 239000002253 acid Substances 0.000 description 79
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 79
- 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 77
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 75
- VEEKCIOFMIAGSF-UHFFFAOYSA-N 4-butylbicyclo[2.2.1]hept-2-ene Chemical compound C1CC2C=CC1(CCCC)C2 VEEKCIOFMIAGSF-UHFFFAOYSA-N 0.000 description 74
- 238000001556 precipitation Methods 0.000 description 66
- 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 64
- 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 53
- RMDKEBZUCHXUER-UHFFFAOYSA-N 4-methylbicyclo[2.2.1]hept-2-ene Chemical compound C1CC2C=CC1(C)C2 RMDKEBZUCHXUER-UHFFFAOYSA-N 0.000 description 39
- 239000000047 product Substances 0.000 description 36
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 28
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000758 substrate Substances 0.000 description 17
- 238000005160 1H NMR spectroscopy Methods 0.000 description 16
- 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 16
- 238000004821 distillation Methods 0.000 description 16
- 238000010438 heat treatment Methods 0.000 description 16
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 13
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- TWKVUTXHANJYGH-UHFFFAOYSA-L allyl palladium chloride Chemical class Cl[Pd]CC=C.Cl[Pd]CC=C TWKVUTXHANJYGH-UHFFFAOYSA-L 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 230000009477 glass transition Effects 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- KMRASZKMNHTING-UHFFFAOYSA-N 4-hexylbicyclo[2.2.1]hept-2-ene Chemical compound C1CC2C=CC1(CCCCCC)C2 KMRASZKMNHTING-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 230000037048 polymerization activity Effects 0.000 description 8
- 229910052723 transition metal Inorganic materials 0.000 description 8
- 150000003624 transition metals Chemical class 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 230000001681 protective effect Effects 0.000 description 7
- 230000007704 transition Effects 0.000 description 7
- 238000003775 Density Functional Theory Methods 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 239000004642 Polyimide Substances 0.000 description 6
- 229920001721 polyimide Polymers 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 239000004372 Polyvinyl alcohol Substances 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 229920002451 polyvinyl alcohol Polymers 0.000 description 5
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 description 5
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 4
- 230000001360 synchronised effect Effects 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229910052581 Si3N4 Inorganic materials 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
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- 238000004364 calculation method Methods 0.000 description 3
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
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- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 3
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- 238000000576 coating method Methods 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
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- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- LMJVDYDHTWAXDL-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-4-carboxylic acid Chemical compound C1CC2C=CC1(C(=O)O)C2 LMJVDYDHTWAXDL-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
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- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
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- 239000011630 iodine Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000005076 polymer ester Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000010107 reaction injection moulding Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 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
- 238000012360 testing method Methods 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 230000001052 transient effect Effects 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
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 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
-
- 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
- C08F32/08—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 two condensed rings
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/136—Liquid crystal cells structurally associated with a semi-conducting layer or substrate, e.g. cells forming part of an integrated circuit
- G02F1/1362—Active matrix addressed cells
- G02F1/136227—Through-hole connection of the pixel electrode to the active element through an insulation layer
Landscapes
- 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)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polarising Elements (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR2002040044 | 2002-07-10 | ||
| KR20020040044 | 2002-07-10 | ||
| KR1020030041038A KR100561068B1 (ko) | 2002-07-10 | 2003-06-24 | 노보넨-에스테르계 부가중합체 및 이의 제조방법 |
| KR2003041038 | 2003-06-24 | ||
| PCT/KR2003/001349 WO2004007587A1 (en) | 2002-07-10 | 2003-07-07 | Nobonene-ester based addition polymer and method for preparing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60311103D1 DE60311103D1 (de) | 2007-02-22 |
| DE60311103T2 true DE60311103T2 (de) | 2007-10-25 |
Family
ID=30117538
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60311103T Expired - Lifetime DE60311103T2 (de) | 2002-07-10 | 2003-07-07 | Auf norbornenester basierendes polymerisat und verfahren zu seiner herstellung |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP1521791B1 (enExample) |
| JP (2) | JP4018101B2 (enExample) |
| CN (1) | CN1281653C (enExample) |
| AU (1) | AU2003246159A1 (enExample) |
| DE (1) | DE60311103T2 (enExample) |
| WO (1) | WO2004007587A1 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100827903B1 (ko) | 2004-05-20 | 2008-05-07 | 미츠비시 레이온 가부시키가이샤 | (메트)아크릴산 에스테르, 중합체, 및 레지스트 조성물 |
| JP2006104378A (ja) * | 2004-10-07 | 2006-04-20 | Mitsubishi Rayon Co Ltd | レジスト用単量体およびレジスト用重合体 |
| US20080125556A1 (en) * | 2004-12-22 | 2008-05-29 | Jsr Corporation | Method For Producing Cyclic Olefin Addition Copolymer, Cyclic Olefin Addition Copolymer And Use Thereof |
| JP5017793B2 (ja) * | 2005-04-06 | 2012-09-05 | Ｊｓｒ株式会社 | 環状オレフィン系付加重合体の製造方法 |
| JP2007131704A (ja) * | 2005-11-09 | 2007-05-31 | Fujifilm Corp | 環状オレフィン系重合体、およびそれを用いた光学材料、偏光板および液晶表示装置 |
| JP5034242B2 (ja) * | 2006-01-30 | 2012-09-26 | 日本ゼオン株式会社 | ノルボルネン化合物付加重合体及びそれからなる成形品 |
| JP4876596B2 (ja) * | 2006-01-30 | 2012-02-15 | 日本ゼオン株式会社 | ノルボルネン化合物付加重合体からなるフィルム |
| KR100867855B1 (ko) * | 2006-04-07 | 2008-11-07 | 주식회사 엘지화학 | 고분자 용액 내 잔류 촉매 제거 방법 |
| DE102006027238A1 (de) * | 2006-06-09 | 2007-12-13 | Beiersdorf Ag | Acyclische Merocyanine in kosmetischen Zubereitungen |
| EP2039708A4 (en) * | 2006-07-07 | 2010-02-24 | Jsr Corp | CYCLOOLEFIN ADDITIVE COPOLYMER, PREPARATION METHOD AND COPOLYMER RECEIVED DELAYING FILM |
| KR101414347B1 (ko) | 2006-07-28 | 2014-07-02 | 후지필름 가부시키가이샤 | 노르보르넨계 중합체, 필름, 편광판 및 액정 표시 장치 |
| JP4799320B2 (ja) * | 2006-08-25 | 2011-10-26 | Ｊｘ日鉱日石エネルギー株式会社 | ネガティブａ位相差フィルム及びそれを用いた液晶表示装置 |
| 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 |
| JP5124027B2 (ja) * | 2008-01-18 | 2013-01-23 | エルジー・ケム・リミテッド | 光学フィルム、その製造方法、およびこれを含む液晶表示装置 |
| JP5588626B2 (ja) | 2008-08-04 | 2014-09-10 | 富士フイルム株式会社 | 光学フィルム、偏光板、光学補償フィルム、反射防止フィルムおよび液晶表示装置 |
| KR101079807B1 (ko) | 2008-08-18 | 2011-11-03 | 주식회사 엘지화학 | 노보넨계 단량체, 폴리노보넨 유도체, 이를 포함하는 액정배향막 및 이를 포함하는 액정표시소자 |
| JP4977678B2 (ja) * | 2008-10-23 | 2012-07-18 | Ｊｘ日鉱日石エネルギー株式会社 | 逆分散位相差フィルム及びそれを用いた液晶表示装置 |
| KR101100351B1 (ko) * | 2009-02-13 | 2011-12-30 | 삼성전기주식회사 | 저유전율 및 저손실 특성을 가진 노르보넨계 중합체 및 이를 이용한 절연재 |
| JP4997655B2 (ja) * | 2010-03-03 | 2012-08-08 | 学校法人日本大学 | ノルボルネン系付加重合用パラジウム触媒並びにノルボルネン系付加重合体の製造方法 |
| JP5738097B2 (ja) * | 2010-09-10 | 2015-06-17 | 昭和電工株式会社 | ノルボルネン系重合体の製造方法 |
| US8691915B2 (en) | 2012-04-23 | 2014-04-08 | Sabic Innovative Plastics Ip B.V. | Copolymers and polymer blends having improved refractive indices |
| WO2014099546A1 (en) | 2012-12-19 | 2014-06-26 | Promerus, Llc | Process for the preparation of high purity norbornene alkanols and derivatives thereof |
| RU2523321C1 (ru) * | 2013-05-15 | 2014-07-20 | Открытое акционерное общество "Нефтяная компания "Роснефть" | Материал для проппанта и способ его получения |
| JP6220880B2 (ja) * | 2013-09-06 | 2017-10-25 | 新日鐵住金株式会社 | 鋼管用ねじ継手 |
| KR20150037593A (ko) * | 2013-09-30 | 2015-04-08 | 주식회사 엘지화학 | 기재 필름, 이를 포함하는 적층 구조체 및 디스플레이 소자 |
| CN112625219A (zh) * | 2020-12-18 | 2021-04-09 | 宁波拓烯新材料科技有限公司 | 一种梯形低聚物的合成方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56167640A (en) * | 1980-05-30 | 1981-12-23 | Denki Kagaku Kogyo Kk | Preparation of endo- and exo-5,5-dialkoxycarbonyl-2- norbornene |
| WO1997033198A1 (en) * | 1996-03-07 | 1997-09-12 | The B.F. Goodrich Company | Photoresist compositions comprising polycyclic polymers with acid labile pendant groups |
| WO1998046614A1 (de) * | 1997-04-11 | 1998-10-22 | Ticona Gmbh | Katalysator und verwendung des katalysators für die polymerisation |
| WO1999014635A1 (en) * | 1997-09-12 | 1999-03-25 | The B.F. Goodrich Company | Photoresist compositions comprising polycyclic polymers with acid labile pendant groups |
| EP1034196B1 (en) * | 1998-10-05 | 2005-01-12 | Promerus LLC | Catalyst and methods for polymerizing cycloolefins |
| JP4269119B2 (ja) * | 1999-10-25 | 2009-05-27 | 信越化学工業株式会社 | レジスト材料及びパターン形成方法 |
| KR100332463B1 (ko) * | 1999-12-20 | 2002-04-13 | 박찬구 | 노보난계 저분자 화합물 첨가제를 포함하는 화학증폭형레지스트 조성물 |
| US6403742B2 (en) * | 1999-12-27 | 2002-06-11 | Jsr Corporation | Olefin copolymer having functional group, production process thereof and rubber composition |
| KR100576200B1 (ko) * | 2000-03-06 | 2006-05-03 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 고분자 화합물, 레지스트 재료 및 패턴 형성 방법 |
| US6534586B2 (en) * | 2000-09-20 | 2003-03-18 | Jsr Corporation | Flame-retardant rubber composition and flame-retardant elastomer |
-
2003
- 2003-07-07 WO PCT/KR2003/001349 patent/WO2004007587A1/en not_active Ceased
- 2003-07-07 DE DE60311103T patent/DE60311103T2/de not_active Expired - Lifetime
- 2003-07-07 JP JP2004521250A patent/JP4018101B2/ja not_active Expired - Lifetime
- 2003-07-07 CN CN 03801572 patent/CN1281653C/zh not_active Expired - Lifetime
- 2003-07-07 EP EP03738767A patent/EP1521791B1/en not_active Expired - Lifetime
- 2003-07-07 AU AU2003246159A patent/AU2003246159A1/en not_active Abandoned
-
2007
- 2007-05-02 JP JP2007121886A patent/JP4938544B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP4938544B2 (ja) | 2012-05-23 |
| DE60311103D1 (de) | 2007-02-22 |
| AU2003246159A1 (en) | 2004-02-02 |
| EP1521791B1 (en) | 2007-01-10 |
| JP4018101B2 (ja) | 2007-12-05 |
| EP1521791A4 (en) | 2006-05-31 |
| CN1281653C (zh) | 2006-10-25 |
| EP1521791A1 (en) | 2005-04-13 |
| JP2005527696A (ja) | 2005-09-15 |
| JP2007246914A (ja) | 2007-09-27 |
| CN1592765A (zh) | 2005-03-09 |
| WO2004007587A1 (en) | 2004-01-22 |
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| 8364 | No opposition during term of opposition |