JP2007521326A5 - - Google Patents
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- JP2007521326A5 JP2007521326A5 JP2006538555A JP2006538555A JP2007521326A5 JP 2007521326 A5 JP2007521326 A5 JP 2007521326A5 JP 2006538555 A JP2006538555 A JP 2006538555A JP 2006538555 A JP2006538555 A JP 2006538555A JP 2007521326 A5 JP2007521326 A5 JP 2007521326A5
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- JP
- Japan
- Prior art keywords
- branched
- linear
- wca
- substituted
- mecn
- Prior art date
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- -1 carboxylate anion Chemical class 0.000 claims description 20
- 150000001450 anions Chemical class 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 10
- 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 9
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 150000004645 aluminates Chemical class 0.000 claims description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 230000007935 neutral effect Effects 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 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 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000002879 Lewis base Substances 0.000 claims description 3
- 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 3
- 150000007527 lewis bases Chemical group 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 150000003949 imides Chemical class 0.000 claims description 2
- 239000003999 initiator Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 41
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 14
- 150000002941 palladium compounds Chemical class 0.000 claims 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 12
- 229910052763 palladium Inorganic materials 0.000 claims 7
- 239000012876 carrier material Substances 0.000 claims 6
- 239000007788 liquid Substances 0.000 claims 6
- 229910052698 phosphorus Inorganic materials 0.000 claims 6
- 238000000034 method Methods 0.000 claims 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 239000003446 ligand Substances 0.000 claims 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 239000011574 phosphorus Substances 0.000 claims 3
- 125000005592 polycycloalkyl group Polymers 0.000 claims 3
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 2
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 2
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 claims 2
- BKCIQPUIDHPJSI-UHFFFAOYSA-N 2,3,4,5-tetramethylpyridine Chemical compound CC1=CN=C(C)C(C)=C1C BKCIQPUIDHPJSI-UHFFFAOYSA-N 0.000 claims 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- FINHMKGKINIASC-UHFFFAOYSA-N Tetramethylpyrazine Chemical compound CC1=NC(C)=C(C)N=C1C FINHMKGKINIASC-UHFFFAOYSA-N 0.000 claims 2
- 229910052782 aluminium Chemical group 0.000 claims 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 2
- 229910052796 boron Inorganic materials 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 229910052805 deuterium Inorganic materials 0.000 claims 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims 2
- 230000000737 periodic effect Effects 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- 125000006755 (C2-C20) alkyl group Chemical group 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- AVVOZVZKWKNBTK-UHFFFAOYSA-N 1-adamantyl(dicyclohexyl)phosphane Chemical compound C1CCCCC1P(C12CC3CC(CC(C3)C1)C2)C1CCCCC1 AVVOZVZKWKNBTK-UHFFFAOYSA-N 0.000 claims 1
- FALDXOCRXXUAHJ-UHFFFAOYSA-N 1-isocyano-2,3-dimethylbenzene Chemical compound CC1=CC=CC([N+]#[C-])=C1C FALDXOCRXXUAHJ-UHFFFAOYSA-N 0.000 claims 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- ALICXZWFCYTZBM-UHFFFAOYSA-N C1CCCCC1[As](C(C)(C)C)C1CCCCC1 Chemical compound C1CCCCC1[As](C(C)(C)C)C1CCCCC1 ALICXZWFCYTZBM-UHFFFAOYSA-N 0.000 claims 1
- QMIJUBUWAWJFCA-UHFFFAOYSA-N CC(C)(C)[As](C(C)(C)C)C1CCCCC1 Chemical compound CC(C)(C)[As](C(C)(C)C)C1CCCCC1 QMIJUBUWAWJFCA-UHFFFAOYSA-N 0.000 claims 1
- YNXPAZRJQZRPQA-UHFFFAOYSA-N CC(C)[As](C(C)(C)C)C(C)(C)C Chemical compound CC(C)[As](C(C)(C)C)C(C)(C)C YNXPAZRJQZRPQA-UHFFFAOYSA-N 0.000 claims 1
- NCAZFNKNPRDPHZ-UHFFFAOYSA-N FC(F)C(F)(F)F.FC(F)(F)S(=O)(=O)NS(=O)=O Chemical compound FC(F)C(F)(F)F.FC(F)(F)S(=O)(=O)NS(=O)=O NCAZFNKNPRDPHZ-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- FQFZASRJFRAEIH-UHFFFAOYSA-N adamantane-1-carbonitrile Chemical compound C1C(C2)CC3CC2CC1(C#N)C3 FQFZASRJFRAEIH-UHFFFAOYSA-N 0.000 claims 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000129 anionic group Chemical group 0.000 claims 1
- 229910052785 arsenic Inorganic materials 0.000 claims 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims 1
- 239000012965 benzophenone Substances 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- XLTOFYXJTSGAAW-UHFFFAOYSA-N bis(1-adamantyl)-cyclohexylphosphane Chemical compound C1CCCCC1P(C12CC3CC(CC(C3)C1)C2)C1(C2)CC(C3)CC2CC3C1 XLTOFYXJTSGAAW-UHFFFAOYSA-N 0.000 claims 1
- 238000012662 bulk polymerization Methods 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000007942 carboxylates Chemical group 0.000 claims 1
- 239000013522 chelant Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- HFFHNJKBAYQARL-UHFFFAOYSA-N ditert-butyl(cyclohexyl)phosphane Chemical compound CC(C)(C)P(C(C)(C)C)C1CCCCC1 HFFHNJKBAYQARL-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims 1
- 125000000262 haloalkenyl group Chemical group 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 238000004377 microelectronic Methods 0.000 claims 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 230000005693 optoelectronics Effects 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- JAMNHZBIQDNHMM-UHFFFAOYSA-N pivalonitrile Chemical compound CC(C)(C)C#N JAMNHZBIQDNHMM-UHFFFAOYSA-N 0.000 claims 1
- 229910052696 pnictogen Inorganic materials 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- FAGLEPBREOXSAC-UHFFFAOYSA-N tert-butyl isocyanide Chemical compound CC(C)(C)[N+]#[C-] FAGLEPBREOXSAC-UHFFFAOYSA-N 0.000 claims 1
- MQYZHXLHUNLBQH-UHFFFAOYSA-N tert-butyl(dicyclohexyl)phosphane Chemical compound C1CCCCC1P(C(C)(C)C)C1CCCCC1 MQYZHXLHUNLBQH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- BTBCWVARCVKLST-UHFFFAOYSA-N tri(propan-2-yl)arsane Chemical compound CC(C)[As](C(C)C)C(C)C BTBCWVARCVKLST-UHFFFAOYSA-N 0.000 claims 1
- 125000005389 trialkylsiloxy group Chemical group 0.000 claims 1
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 1
- 125000005106 triarylsilyl group Chemical group 0.000 claims 1
- PMZLFYBZWYRRAZ-UHFFFAOYSA-N tricyclohexylarsane Chemical compound C1CCCCC1[As](C1CCCCC1)C1CCCCC1 PMZLFYBZWYRRAZ-UHFFFAOYSA-N 0.000 claims 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 claims 1
- INUKEARJELAONK-UHFFFAOYSA-N tricyclopentylarsane Chemical compound C1CCCC1[As](C1CCCC1)C1CCCC1 INUKEARJELAONK-UHFFFAOYSA-N 0.000 claims 1
- DHWBYAACHDUFAT-UHFFFAOYSA-N tricyclopentylphosphane Chemical compound C1CCCC1P(C1CCCC1)C1CCCC1 DHWBYAACHDUFAT-UHFFFAOYSA-N 0.000 claims 1
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 claims 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 claims 1
- SJHCUXCOGGKFAI-UHFFFAOYSA-N tripropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC(C)C SJHCUXCOGGKFAI-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 150000001768 cations Chemical class 0.000 description 7
- 229910052723 transition metal Inorganic materials 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910013385 LiN(SO2C2F5)2 Inorganic materials 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 229910018286 SbF 6 Inorganic materials 0.000 description 1
- MEJXJZMCNYJBDB-UHFFFAOYSA-N [Li].FC(F)C(F)(F)F.FC(F)(F)S(=O)(=O)NS(=O)=O Chemical compound [Li].FC(F)C(F)(F)F.FC(F)(F)S(=O)(=O)NS(=O)=O MEJXJZMCNYJBDB-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000005626 carbonium group Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- ACFSQHQYDZIPRL-UHFFFAOYSA-N lithium;bis(1,1,2,2,2-pentafluoroethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)C(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)C(F)(F)F ACFSQHQYDZIPRL-UHFFFAOYSA-N 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- ACCDBHBOYZJSDT-UHFFFAOYSA-N n-(4-bromophenyl)-2-fluoroacetamide Chemical compound FCC(=O)NC1=CC=C(Br)C=C1 ACCDBHBOYZJSDT-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 150000003624 transition metals Chemical class 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
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51605403P | 2003-10-31 | 2003-10-31 | |
| US10/976,350 US20050187398A1 (en) | 2003-10-31 | 2004-10-28 | Single component cationic palladium proinitiators for the latent polymerization of cycloolefins |
| PCT/US2004/037983 WO2005042147A2 (en) | 2003-10-31 | 2004-10-29 | Single component cationic palladium proinitiators for the latent polymerization of cycloolefins |
Publications (2)
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| JP2007521326A JP2007521326A (ja) | 2007-08-02 |
| JP2007521326A5 true JP2007521326A5 (enExample) | 2007-12-20 |
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| US (1) | US20050187398A1 (enExample) |
| EP (1) | EP1680218A2 (enExample) |
| JP (1) | JP2007521326A (enExample) |
| KR (1) | KR20060127396A (enExample) |
| TW (1) | TW200535158A (enExample) |
| WO (1) | WO2005042147A2 (enExample) |
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| KR20070116610A (ko) | 2005-02-22 | 2007-12-10 | 프로메러스, 엘엘씨 | 노르보르넨-타입 폴리머, 이들의 조성물 및 그러한조성물을 사용하는 리소그라피 프로세스 |
| 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 |
| AU2007254464B2 (en) * | 2006-02-21 | 2013-02-21 | 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 |
| CN101535852B (zh) | 2006-11-16 | 2011-01-26 | 住友电木株式会社 | 光导波路及光导波路结构体 |
| 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 |
| 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 |
| US20240002586A1 (en) | 2020-12-02 | 2024-01-04 | 3M Innovative Properties Company | Curable compositions, composite foam, method of making the same, and article including the same |
| 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 |
| EP4612126A1 (en) | 2022-10-31 | 2025-09-10 | 3M Innovative Properties Company | Compositions including a mixture of isomers of itaconimide norbornene and citraconimide norbornene |
| WO2024100476A1 (en) | 2022-11-07 | 2024-05-16 | 3M Innovative Properties Company | Curable and cured thermosetting compositions |
Family Cites Families (6)
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|---|---|---|---|---|
| JP3476819B2 (ja) * | 1992-06-23 | 2003-12-10 | ザ・ダウ・ケミカル・カンパニー | テトラキスフルオロフェニル硼酸塩の製造方法 |
| 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 |
| EP1034196B1 (en) * | 1998-10-05 | 2005-01-12 | Promerus LLC | Catalyst and methods for polymerizing cycloolefins |
| DE69925939T2 (de) * | 1998-12-09 | 2006-05-04 | Sumitomo Bakelite Co. Ltd. | Additionspolymerisation in einer form unter benutzung von polymeren des norbornentyps mit gruppe-3-metallkomplexen |
| 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 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
- 2004-10-29 JP JP2006538555A patent/JP2007521326A/ja active Pending
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