KR20060127396A - 시클로올레핀의 잠재성 중합을 위한 단일 성분 양이온성팔라듐 프로개시제 - Google Patents
시클로올레핀의 잠재성 중합을 위한 단일 성분 양이온성팔라듐 프로개시제 Download PDFInfo
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- KR20060127396A KR20060127396A KR1020067010751A KR20067010751A KR20060127396A KR 20060127396 A KR20060127396 A KR 20060127396A KR 1020067010751 A KR1020067010751 A KR 1020067010751A KR 20067010751 A KR20067010751 A KR 20067010751A KR 20060127396 A KR20060127396 A KR 20060127396A
- Authority
- KR
- South Korea
- Prior art keywords
- arsine
- branched
- tri
- butyl
- wca
- 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.)
- Withdrawn
Links
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 title claims abstract description 572
- 229910052763 palladium Inorganic materials 0.000 title claims abstract description 80
- 238000006116 polymerization reaction Methods 0.000 title claims description 52
- 125000002091 cationic group Chemical group 0.000 title description 10
- 150000001925 cycloalkenes Chemical class 0.000 title description 10
- -1 polycyclic olefins Chemical class 0.000 claims abstract description 147
- 239000003446 ligand Substances 0.000 claims abstract description 88
- 239000002879 Lewis base Substances 0.000 claims abstract description 75
- 150000007527 lewis bases Chemical group 0.000 claims abstract description 74
- 239000000203 mixture Substances 0.000 claims abstract description 70
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 150000001450 anions Chemical class 0.000 claims abstract description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
- 150000002941 palladium compounds Chemical class 0.000 claims abstract description 38
- 230000007935 neutral effect Effects 0.000 claims abstract description 31
- 239000001257 hydrogen Substances 0.000 claims abstract description 27
- 125000000129 anionic group Chemical group 0.000 claims abstract description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 233
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 194
- 239000000243 solution Substances 0.000 claims description 150
- 239000000460 chlorine Substances 0.000 claims description 84
- 239000000178 monomer Substances 0.000 claims description 72
- 229910052760 oxygen Inorganic materials 0.000 claims description 68
- 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 66
- 238000000034 method Methods 0.000 claims description 59
- 239000013256 coordination polymer Substances 0.000 claims description 52
- 238000006243 chemical reaction Methods 0.000 claims description 49
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
- 229910052698 phosphorus Inorganic materials 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 32
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 27
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 claims description 24
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 23
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 21
- 125000000217 alkyl group Chemical group 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
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 18
- 229910052797 bismuth Inorganic materials 0.000 claims description 17
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 150000004645 aluminates Chemical class 0.000 claims description 16
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 15
- 150000002431 hydrogen Chemical group 0.000 claims description 15
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 15
- 239000011574 phosphorus Substances 0.000 claims description 15
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
- 229910052805 deuterium Inorganic materials 0.000 claims description 13
- 239000011737 fluorine Substances 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 125000005592 polycycloalkyl group Polymers 0.000 claims description 13
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 claims description 13
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 12
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 12
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 9
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 9
- 239000007983 Tris buffer Substances 0.000 claims description 9
- 229910052785 arsenic Inorganic materials 0.000 claims description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 9
- 150000007942 carboxylates Chemical class 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 8
- FINHMKGKINIASC-UHFFFAOYSA-N Tetramethylpyrazine Chemical compound CC1=NC(C)=C(C)N=C1C FINHMKGKINIASC-UHFFFAOYSA-N 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 229910000072 bismuth hydride Inorganic materials 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 7
- 229910052787 antimony Inorganic materials 0.000 claims description 7
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 claims description 7
- OJJVPGJEBAZOIF-UHFFFAOYSA-N (2,3,4,5-tetrafluorophenoxy)boronic acid Chemical compound OB(O)OC1=CC(F)=C(F)C(F)=C1F OJJVPGJEBAZOIF-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- HFKJQIJFRMRSKM-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenoxy]boronic acid Chemical compound OB(O)OC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 HFKJQIJFRMRSKM-UHFFFAOYSA-N 0.000 claims description 6
- BPBOBPIKWGUSQG-UHFFFAOYSA-N bismuthane Chemical compound [BiH3] BPBOBPIKWGUSQG-UHFFFAOYSA-N 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 claims description 6
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 claims description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- DAFHDCDVTSLGFQ-UHFFFAOYSA-N [3,5-bis(1,1,1,3,3,3-hexafluoro-2-methoxypropan-2-yl)phenoxy]boronic acid Chemical compound COC(C(F)(F)F)(C(F)(F)F)C1=CC(OB(O)O)=CC(C(OC)(C(F)(F)F)C(F)(F)F)=C1 DAFHDCDVTSLGFQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 5
- 229910052782 aluminium Chemical group 0.000 claims description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 125000005447 octyloxy 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])O* 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 230000000737 periodic effect Effects 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- HRFJDIQKZBDQRL-UHFFFAOYSA-N 1-adamantyl(dibutyl)phosphane Chemical compound C1C(C2)CC3CC2CC1(P(CCCC)CCCC)C3 HRFJDIQKZBDQRL-UHFFFAOYSA-N 0.000 claims description 4
- BKCIQPUIDHPJSI-UHFFFAOYSA-N 2,3,4,5-tetramethylpyridine Chemical compound CC1=CN=C(C)C(C)=C1C BKCIQPUIDHPJSI-UHFFFAOYSA-N 0.000 claims description 4
- HJFZAYHYIWGLNL-UHFFFAOYSA-N 2,6-Dimethylpyrazine Chemical compound CC1=CN=CC(C)=N1 HJFZAYHYIWGLNL-UHFFFAOYSA-N 0.000 claims description 4
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 claims description 4
- XTBBSKUFMQJNKJ-UHFFFAOYSA-N C1CCCCC1[Bi](C(C)(C)C)C1CCCCC1 Chemical compound C1CCCCC1[Bi](C(C)(C)C)C1CCCCC1 XTBBSKUFMQJNKJ-UHFFFAOYSA-N 0.000 claims description 4
- BESXVHYNGBLMGC-UHFFFAOYSA-N CC(C)(C)[Sb](C(C)(C)C)C1CCCCC1 Chemical compound CC(C)(C)[Sb](C(C)(C)C)C1CCCCC1 BESXVHYNGBLMGC-UHFFFAOYSA-N 0.000 claims description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 4
- QXTCJLPZCUKMDX-UHFFFAOYSA-N ditert-butyl(propan-2-yl)phosphane Chemical compound CC(C)P(C(C)(C)C)C(C)(C)C QXTCJLPZCUKMDX-UHFFFAOYSA-N 0.000 claims description 4
- VJPHAMJNGICSLT-UHFFFAOYSA-N n-methylcyclohexanecarboxamide Chemical compound CNC(=O)C1CCCCC1 VJPHAMJNGICSLT-UHFFFAOYSA-N 0.000 claims description 4
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 4
- 229910052696 pnictogen Inorganic materials 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- OLSMQSZDUXXYAY-UHFFFAOYSA-N tert-butyl-di(propan-2-yl)phosphane Chemical compound CC(C)P(C(C)C)C(C)(C)C OLSMQSZDUXXYAY-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- QURUUNUACMRPBA-UHFFFAOYSA-N tribenzylbismuthane Chemical compound C=1C=CC=CC=1C[Bi](CC=1C=CC=CC=1)CC1=CC=CC=C1 QURUUNUACMRPBA-UHFFFAOYSA-N 0.000 claims description 4
- IFXORIIYQORRMJ-UHFFFAOYSA-N tribenzylphosphane Chemical compound C=1C=CC=CC=1CP(CC=1C=CC=CC=1)CC1=CC=CC=C1 IFXORIIYQORRMJ-UHFFFAOYSA-N 0.000 claims description 4
- MTWZZHCSSCNQBI-UHFFFAOYSA-N tributylbismuthane Chemical compound CCCC[Bi](CCCC)CCCC MTWZZHCSSCNQBI-UHFFFAOYSA-N 0.000 claims description 4
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 4
- NNNYBMBFHFPUEY-UHFFFAOYSA-N tripropylbismuthane Chemical compound CCC[Bi](CCC)CCC NNNYBMBFHFPUEY-UHFFFAOYSA-N 0.000 claims description 4
- ANEFWEBMQHRDLH-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl) borate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1OB(OC=1C(=C(F)C(F)=C(F)C=1F)F)OC1=C(F)C(F)=C(F)C(F)=C1F ANEFWEBMQHRDLH-UHFFFAOYSA-N 0.000 claims description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 claims description 4
- BOVVZESRDGNHIH-UHFFFAOYSA-N (2,3,5,6-tetrafluoro-4-tripropylsilylphenoxy)boronic acid Chemical compound B(O)(O)OC1=C(C(=C(C(=C1F)F)[Si](CCC)(CCC)CCC)F)F BOVVZESRDGNHIH-UHFFFAOYSA-N 0.000 claims description 3
- QKMJUHHJEKNMBF-UHFFFAOYSA-N CC(C)[Bi](C(C)C)C(C)(C)C Chemical compound CC(C)[Bi](C(C)C)C(C)(C)C QKMJUHHJEKNMBF-UHFFFAOYSA-N 0.000 claims description 3
- GFLVHHVSQGCYHC-UHFFFAOYSA-N [3-(1,1,1,3,3,3-hexafluoro-2-methoxypropan-2-yl)-5-(trifluoromethyl)phenoxy]boronic acid Chemical compound COC(C(F)(F)F)(C(F)(F)F)C1=CC(OB(O)O)=CC(C(F)(F)F)=C1 GFLVHHVSQGCYHC-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 3
- 239000012965 benzophenone Substances 0.000 claims description 3
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- LBZUQWKKMMMVRT-UHFFFAOYSA-N tribenzylarsane Chemical compound C=1C=CC=CC=1C[As](CC=1C=CC=CC=1)CC1=CC=CC=C1 LBZUQWKKMMMVRT-UHFFFAOYSA-N 0.000 claims description 3
- DHWBYAACHDUFAT-UHFFFAOYSA-N tricyclopentylphosphane Chemical compound C1CCCC1P(C1CCCC1)C1CCCC1 DHWBYAACHDUFAT-UHFFFAOYSA-N 0.000 claims description 3
- UPWXXWXICHRHEN-UHFFFAOYSA-N tricyclopropylphosphane Chemical compound C1CC1P(C1CC1)C1CC1 UPWXXWXICHRHEN-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- DWSBPCLAELVSFD-UHFFFAOYSA-N (2-fluorophenoxy)boronic acid Chemical compound OB(O)OC1=CC=CC=C1F DWSBPCLAELVSFD-UHFFFAOYSA-N 0.000 claims description 2
- FWUHUNUOUDQTFG-UHFFFAOYSA-N (3,4,5-trifluorophenoxy)boronic acid Chemical compound OB(O)OC1=CC(F)=C(F)C(F)=C1 FWUHUNUOUDQTFG-UHFFFAOYSA-N 0.000 claims description 2
- GNUFQJQCEBFWDQ-UHFFFAOYSA-N (3,5-difluorophenoxy)boronic acid Chemical compound OB(O)OC1=CC(F)=CC(F)=C1 GNUFQJQCEBFWDQ-UHFFFAOYSA-N 0.000 claims description 2
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- 238000004611 spectroscopical analysis Methods 0.000 description 1
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- 210000003813 thumb Anatomy 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
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- ZRDIWDLIPFZFRO-UHFFFAOYSA-N tricyclohexylbismuthane Chemical compound C1CCCCC1[Bi](C1CCCCC1)C1CCCCC1 ZRDIWDLIPFZFRO-UHFFFAOYSA-N 0.000 description 1
- AVYPTBDUFIEJDP-UHFFFAOYSA-N tricyclohexylstibane Chemical compound C1CCCCC1[Sb](C1CCCCC1)C1CCCCC1 AVYPTBDUFIEJDP-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- VOYMPSZBODLRKS-UHFFFAOYSA-N trimethylsilanylium Chemical compound C[Si+](C)C VOYMPSZBODLRKS-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-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
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000004017 vitrification Methods 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
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Images
Classifications
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- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- 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
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- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| US10/976,350 US20050187398A1 (en) | 2003-10-31 | 2004-10-28 | Single component cationic palladium proinitiators for the latent polymerization of cycloolefins |
| US10/976,350 | 2004-10-28 |
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| KR20060127396A true KR20060127396A (ko) | 2006-12-12 |
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| EP (1) | EP1680218A2 (https=) |
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| KR (1) | KR20060127396A (https=) |
| TW (1) | TW200535158A (https=) |
| WO (1) | WO2005042147A2 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20230020551A (ko) * | 2020-06-24 | 2023-02-10 | 프로메러스, 엘엘씨 | 광학재료로서의 힌더드 아민 안정화 uv 활성 오르가노팔라듐 촉매 폴리시클로올레핀 조성물 |
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| EP2031007B1 (en) | 2005-02-22 | 2011-07-20 | Tokyo Ohka Kogyo Co., Ltd. | Top-coat compositions with norbornene-type polymers and immersion lithographic processes using such compositions |
| 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 |
| JP4826242B2 (ja) * | 2005-12-12 | 2011-11-30 | Jsr株式会社 | 環状オレフィン系付加重合体の製造方法 |
| WO2007136439A2 (en) * | 2006-02-21 | 2007-11-29 | Avrum Belzer | Hyperpolarization methods, systems and compositions |
| US8120168B2 (en) * | 2006-03-21 | 2012-02-21 | Promerus Llc | Methods and materials useful for chip stacking, chip and wafer bonding |
| KR101096300B1 (ko) | 2006-11-16 | 2011-12-20 | 스미토모 베이클리트 컴퍼니 리미티드 | 광도파로 및 광도파로 구조체 |
| JP2009102654A (ja) * | 2009-02-05 | 2009-05-14 | Sumitomo Bakelite Co Ltd | 光導波路構造体 |
| US8541523B2 (en) | 2010-04-05 | 2013-09-24 | Promerus, Llc | Norbornene-type polymers, compositions thereof and lithographic process using such compositions |
| JP2012121956A (ja) * | 2010-12-07 | 2012-06-28 | Sumitomo Bakelite Co Ltd | 付加型ノルボルネン系樹脂、その製造方法、該樹脂を含む樹脂組成物、ならびに該樹脂を含む成形体および該成形体を含む複合部材 |
| US8716421B2 (en) | 2012-06-25 | 2014-05-06 | Promerus, Llc | Norbornene-type formate monomers and polymers and optical waveguides formed therefrom |
| WO2014025735A1 (en) | 2012-08-07 | 2014-02-13 | Promerus, Llc | Cycloalkylnorbornene monomers, polymers derived therefrom and their use in pervaporation |
| CN105283459B (zh) | 2013-05-15 | 2018-01-02 | 广荣化学工业株式会社 | 新型四芳基硼酸盐化合物及其制备方法 |
| RU2626745C2 (ru) * | 2015-07-20 | 2017-07-31 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Иркутский государственный университет" | Способ аддитивной полимеризации норборнена и его производных |
| CN116490538A (zh) | 2020-12-02 | 2023-07-25 | 3M创新有限公司 | 可固化组合物、复合泡沫、制备复合泡沫的方法以及包含复合泡沫的制品 |
| US20240279251A1 (en) | 2021-05-14 | 2024-08-22 | 3M Innovative Properties Company | Monomer, Polymerizable Composition, and Polymers Derived Therefrom |
| TW202348614A (zh) * | 2022-04-05 | 2023-12-16 | 美商普羅梅勒斯有限公司 | 具有改進的成膜特性之乙烯基加成聚合物形成用鈀觸媒 |
| WO2024095078A1 (en) | 2022-10-31 | 2024-05-10 | 3M Innovative Properties Company | Compositions including a mixture of isomers of itaconimide norbornene and citraconimide norbornene |
| CN120152999A (zh) | 2022-11-07 | 2025-06-13 | 3M创新有限公司 | 可固化和固化的热固性组合物 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1028119B1 (en) * | 1992-06-23 | 2004-05-26 | The Dow Chemical Company | Process for producing tetrakisfluorophenylborate |
| US6262200B1 (en) * | 1996-08-19 | 2001-07-17 | Northwestern University | (Polyfluoroaryl)fluoroanions of aluminum, gallium, and indium of enhanced utility, uses thereof, and products based thereon |
| ATE286923T1 (de) * | 1998-10-05 | 2005-01-15 | Promerus Llc | Katalysator und verfahren zur polymerisation von cycloolefinen |
| ID30159A (id) * | 1998-12-09 | 2001-11-08 | Goodrich Co B F | Polimerisasi adisi dalam cetakan dari monomer-monomer tipe-norbene menggunakan kompleksi logam golongan-10 |
| GB2378182A (en) * | 2001-07-31 | 2003-02-05 | Johnson Matthey Plc | Heterocycle-containing phosphines & their use as ligands in palladium catalysed coupling reactions |
| US7674847B2 (en) * | 2003-02-21 | 2010-03-09 | Promerus Llc | Vinyl addition polycyclic olefin polymers prepared with non-olefinic chain transfer agents and uses thereof |
-
2004
- 2004-10-28 US US10/976,350 patent/US20050187398A1/en not_active Abandoned
- 2004-10-29 EP EP04796915A patent/EP1680218A2/en not_active Withdrawn
- 2004-10-29 JP JP2006538555A patent/JP2007521326A/ja active Pending
- 2004-10-29 WO PCT/US2004/037983 patent/WO2005042147A2/en not_active Ceased
- 2004-10-29 KR KR1020067010751A patent/KR20060127396A/ko not_active Withdrawn
- 2004-10-29 TW TW093133204A patent/TW200535158A/zh unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20230020551A (ko) * | 2020-06-24 | 2023-02-10 | 프로메러스, 엘엘씨 | 광학재료로서의 힌더드 아민 안정화 uv 활성 오르가노팔라듐 촉매 폴리시클로올레핀 조성물 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2007521326A (ja) | 2007-08-02 |
| TW200535158A (en) | 2005-11-01 |
| EP1680218A2 (en) | 2006-07-19 |
| US20050187398A1 (en) | 2005-08-25 |
| WO2005042147A2 (en) | 2005-05-12 |
| WO2005042147A3 (en) | 2005-08-04 |
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