JP2018526503A5 - - Google Patents
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- JP2018526503A5 JP2018526503A5 JP2018508194A JP2018508194A JP2018526503A5 JP 2018526503 A5 JP2018526503 A5 JP 2018526503A5 JP 2018508194 A JP2018508194 A JP 2018508194A JP 2018508194 A JP2018508194 A JP 2018508194A JP 2018526503 A5 JP2018526503 A5 JP 2018526503A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- component
- bis
- lithium
- aryl
- 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.)
- Pending
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- 239000000178 monomer Substances 0.000 claims description 94
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 59
- 229910052744 lithium Inorganic materials 0.000 claims description 59
- -1 methoxy, ethoxy Chemical group 0.000 claims description 57
- 239000000203 mixture Substances 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 40
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 claims description 40
- 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 38
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 18
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 16
- 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 15
- HOXINJBQVZWYGZ-UHFFFAOYSA-N fenbutatin oxide Chemical compound C=1C=CC=CC=1C(C)(C)C[Sn](O[Sn](CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C1=CC=CC=C1 HOXINJBQVZWYGZ-UHFFFAOYSA-N 0.000 claims description 15
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 13
- 150000004645 aluminates Chemical class 0.000 claims description 12
- ZTGFJAPGVDKJEB-UHFFFAOYSA-N C(C)(=O)O.C(C)(=O)O.C1(CCCCC1)P(C1CCCCC1)C1CCCCC1.C1(CCCCC1)P(C1CCCCC1)C1CCCCC1 Chemical compound C(C)(=O)O.C(C)(=O)O.C1(CCCCC1)P(C1CCCCC1)C1CCCCC1.C1(CCCCC1)P(C1CCCCC1)C1CCCCC1 ZTGFJAPGVDKJEB-UHFFFAOYSA-N 0.000 claims description 11
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 9
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 239000004305 biphenyl Substances 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- DJHGAFSJWGLOIV-UHFFFAOYSA-K Arsenate3- Chemical compound [O-][As]([O-])([O-])=O DJHGAFSJWGLOIV-UHFFFAOYSA-K 0.000 claims description 6
- 239000007983 Tris buffer Substances 0.000 claims description 6
- 229940000489 arsenate Drugs 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical group [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 claims description 6
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 claims description 6
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-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
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 5
- 230000003213 activating effect Effects 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- ZCBUVBJHVSFIDR-UHFFFAOYSA-N C1(=CC=C(C=C1)CCC1C2C=CC(C1)C2)C1=CC=CC=C1 Chemical compound C1(=CC=C(C=C1)CCC1C2C=CC(C1)C2)C1=CC=CC=C1 ZCBUVBJHVSFIDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000005293 bicycloalkoxy group Chemical group 0.000 claims description 4
- 230000005540 biological transmission Effects 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 claims description 4
- CDJCWEPKSBUOBR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl) dihydrogen phosphate Chemical compound OP(O)(=O)OC1=C(F)C(F)=C(F)C(F)=C1F CDJCWEPKSBUOBR-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 3
- 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 3
- ZNEOOHPDJLKJEE-UHFFFAOYSA-N (3-fluorophenoxy)boronic acid Chemical compound OB(O)OC1=CC=CC(F)=C1 ZNEOOHPDJLKJEE-UHFFFAOYSA-N 0.000 claims description 3
- PHBVXHIVWULVNF-UHFFFAOYSA-N (4-fluorophenoxy)boronic acid Chemical compound OB(O)OC1=CC=C(F)C=C1 PHBVXHIVWULVNF-UHFFFAOYSA-N 0.000 claims description 3
- OGNSDRMLWYNUED-UHFFFAOYSA-N 1-cyclohexyl-4-[4-[4-(4-cyclohexylcyclohexyl)cyclohexyl]cyclohexyl]cyclohexane Chemical group C1CCCCC1C1CCC(C2CCC(CC2)C2CCC(CC2)C2CCC(CC2)C2CCCCC2)CC1 OGNSDRMLWYNUED-UHFFFAOYSA-N 0.000 claims description 3
- GLYQSCZFWIZWEF-UHFFFAOYSA-N 5-bicyclo[2.2.1]hept-2-enylmethoxy-methyl-diphenylsilane Chemical compound C1C(C=C2)CC2C1CO[Si](C)(C=1C=CC=CC=1)C1=CC=CC=C1 GLYQSCZFWIZWEF-UHFFFAOYSA-N 0.000 claims description 3
- KHTIKZLULBHEBR-UHFFFAOYSA-N C(C)(=O)O.C(C)(=O)O.C1(=CC=C(C=C1)P(C1=CC=C(C=C1)C)C1=CC=C(C=C1)C)C.C1(=CC=C(C=C1)P(C1=CC=C(C=C1)C)C1=CC=C(C=C1)C)C Chemical compound C(C)(=O)O.C(C)(=O)O.C1(=CC=C(C=C1)P(C1=CC=C(C=C1)C)C1=CC=C(C=C1)C)C.C1(=CC=C(C=C1)P(C1=CC=C(C=C1)C)C1=CC=C(C=C1)C)C KHTIKZLULBHEBR-UHFFFAOYSA-N 0.000 claims description 3
- XUTKEXDOVRWFEM-UHFFFAOYSA-N C(CC1)CCC1P(C1CCCCC1)C1CCCCC1.C(CC1)CCC1P(C1CCCCC1)C1CCCCC1.Br.Br Chemical compound C(CC1)CCC1P(C1CCCCC1)C1CCCCC1.C(CC1)CCC1P(C1CCCCC1)C1CCCCC1.Br.Br XUTKEXDOVRWFEM-UHFFFAOYSA-N 0.000 claims description 3
- 125000005914 C6-C14 aryloxy group Chemical group 0.000 claims description 3
- XRHIGVKBKVUHBW-UHFFFAOYSA-N CC(C=C1)=CC=C1P(C1=CC=C(C)C=C1)C1=CC=C(C)C=C1.CC(C=C1)=CC=C1P(C1=CC=C(C)C=C1)C1=CC=C(C)C=C1.Cl.Cl Chemical compound CC(C=C1)=CC=C1P(C1=CC=C(C)C=C1)C1=CC=C(C)C=C1.CC(C=C1)=CC=C1P(C1=CC=C(C)C=C1)C1=CC=C(C)C=C1.Cl.Cl XRHIGVKBKVUHBW-UHFFFAOYSA-N 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 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
- IDDVSAPJAKFSQW-UHFFFAOYSA-N [Br-].[Br-].C1(=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C)C1=CC=C(C=C1)C)C.C1(=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C)C1=CC=C(C=C1)C)C Chemical compound [Br-].[Br-].C1(=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C)C1=CC=C(C=C1)C)C.C1(=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C)C1=CC=C(C=C1)C)C IDDVSAPJAKFSQW-UHFFFAOYSA-N 0.000 claims description 3
- AZLJPAXHKBYMPD-UHFFFAOYSA-N [Cl-].[Cl-].C1(CCCCC1)[PH+](C1CCCCC1)C1CCCCC1.C1(CCCCC1)[PH+](C1CCCCC1)C1CCCCC1 Chemical compound [Cl-].[Cl-].C1(CCCCC1)[PH+](C1CCCCC1)C1CCCCC1.C1(CCCCC1)[PH+](C1CCCCC1)C1CCCCC1 AZLJPAXHKBYMPD-UHFFFAOYSA-N 0.000 claims description 3
- 239000012190 activator Substances 0.000 claims description 3
- WXNOJTUTEXAZLD-UHFFFAOYSA-L benzonitrile;dichloropalladium Chemical compound Cl[Pd]Cl.N#CC1=CC=CC=C1.N#CC1=CC=CC=C1 WXNOJTUTEXAZLD-UHFFFAOYSA-L 0.000 claims description 3
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 claims description 3
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical group [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 claims description 3
- MCVFFRWZNYZUIJ-UHFFFAOYSA-M lithium;trifluoromethanesulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(F)F MCVFFRWZNYZUIJ-UHFFFAOYSA-M 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 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 3
- UVBXZOISXNZBLY-UHFFFAOYSA-L palladium(2+);triphenylphosphane;diacetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O.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 UVBXZOISXNZBLY-UHFFFAOYSA-L 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 claims description 3
- KGRJUMGAEQQVFK-UHFFFAOYSA-L platinum(2+);dibromide Chemical compound Br[Pt]Br KGRJUMGAEQQVFK-UHFFFAOYSA-L 0.000 claims description 3
- XAFJSPPHVXDRIE-UHFFFAOYSA-L platinum(2+);triphenylphosphane;dichloride Chemical compound [Cl-].[Cl-].[Pt+2].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 XAFJSPPHVXDRIE-UHFFFAOYSA-L 0.000 claims description 3
- 239000010979 ruby Substances 0.000 claims description 3
- 229910001750 ruby Inorganic materials 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- UEWNEQVNIYYFFF-UHFFFAOYSA-N triphenylphosphanium;dibromide Chemical compound [Br-].[Br-].C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 UEWNEQVNIYYFFF-UHFFFAOYSA-N 0.000 claims description 3
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 claims description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 10
- 229910052763 palladium Inorganic materials 0.000 claims 5
- 230000003796 beauty Effects 0.000 claims 3
- BEHBBKCBARHMJQ-UHFFFAOYSA-N 5-(2-phenylethyl)bicyclo[2.2.1]hept-2-ene Chemical compound C1C(C=C2)CC2C1CCC1=CC=CC=C1 BEHBBKCBARHMJQ-UHFFFAOYSA-N 0.000 claims 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims 2
- VKLJREFHOHZGGJ-UHFFFAOYSA-N 5-(trityloxymethyl)bicyclo[2.2.1]hept-2-ene Chemical compound C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)OCC1C2C=CC(C1)C2 VKLJREFHOHZGGJ-UHFFFAOYSA-N 0.000 claims 1
- VTWPBVSOSWNXAX-UHFFFAOYSA-N 5-decylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCCCCCC)CC1C=C2 VTWPBVSOSWNXAX-UHFFFAOYSA-N 0.000 claims 1
- HAOUSHGZLGWDBP-UHFFFAOYSA-N C12C(CC(C=C1)C2)CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C12C(CC(C=C1)C2)CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 HAOUSHGZLGWDBP-UHFFFAOYSA-N 0.000 claims 1
- MYRCGGWMPWHTOU-UHFFFAOYSA-N C[Si](C)(O[Si](C)(C1=CC=CC=C1)C1=CC=CC=C1)C1CC2CC1C=C2 Chemical compound C[Si](C)(O[Si](C)(C1=CC=CC=C1)C1=CC=CC=C1)C1CC2CC1C=C2 MYRCGGWMPWHTOU-UHFFFAOYSA-N 0.000 claims 1
- SIFPLGJLEHPCOR-UHFFFAOYSA-N C[Si](C)(O[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C1CC2CC1C=C2 Chemical compound C[Si](C)(O[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C1CC2CC1C=C2 SIFPLGJLEHPCOR-UHFFFAOYSA-N 0.000 claims 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- FULSRCPEOUATID-UHFFFAOYSA-N methyl(diphenyl)silane Chemical compound C=1C=CC=CC=1[SiH](C)C1=CC=CC=C1 FULSRCPEOUATID-UHFFFAOYSA-N 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
- 229920003251 poly(α-methylstyrene) Polymers 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 claims 1
- 0 *C1(*)C(*)(*C2(*)C(*)(*)C3C=CC2C3)C2C=CC1C2 Chemical compound *C1(*)C(*)(*C2(*)C(*)(*)C3C=CC2C3)C2C=CC1C2 0.000 description 5
- 238000002834 transmittance Methods 0.000 description 3
- BPORHKUXZCQFSC-UHFFFAOYSA-N C1C2C=CC1CC2c(cc1)ccc1-c1ccc(C2C(C3)C=CC3C2)cc1 Chemical compound C1C2C=CC1CC2c(cc1)ccc1-c1ccc(C2C(C3)C=CC3C2)cc1 BPORHKUXZCQFSC-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562212919P | 2015-09-01 | 2015-09-01 | |
| US62/212,919 | 2015-09-01 | ||
| US201562251206P | 2015-11-05 | 2015-11-05 | |
| US62/251,206 | 2015-11-05 | ||
| PCT/US2016/049822 WO2017040737A1 (en) | 2015-09-01 | 2016-09-01 | Polycycloolefin polymer compositions as optical materials |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2018526503A JP2018526503A (ja) | 2018-09-13 |
| JP2018526503A5 true JP2018526503A5 (https=) | 2019-06-20 |
Family
ID=56943935
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018508194A Pending JP2018526503A (ja) | 2015-09-01 | 2016-09-01 | 光学材料としてのポリシクロオレフィンポリマー組成物 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US9944818B2 (https=) |
| EP (1) | EP3344671B1 (https=) |
| JP (1) | JP2018526503A (https=) |
| KR (1) | KR20180048664A (https=) |
| CN (1) | CN107922549B (https=) |
| TW (1) | TWI675059B (https=) |
| WO (1) | WO2017040737A1 (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018005488A1 (en) * | 2016-06-27 | 2018-01-04 | Momentive Performance Materials Inc. | Flame retardant resin composition |
| TWI723243B (zh) * | 2017-01-06 | 2021-04-01 | 日商住友電木股份有限公司 | 作為光學材料之聚環烯烴聚合物組成物 |
| TWI758525B (zh) * | 2017-08-10 | 2022-03-21 | 日商住友電木股份有限公司 | 作為光學材料之聚環烯烴聚合物組成物 |
| EP3815159A1 (en) * | 2018-06-28 | 2021-05-05 | Merck Patent GmbH | Method for producing an electronic device |
| TWI794520B (zh) | 2018-06-29 | 2023-03-01 | 日商住友電木股份有限公司 | 作為 3d 列印材料之聚環烯烴單體及由能夠產生光酸之化合物活化之催化劑 |
| KR102513170B1 (ko) * | 2018-12-21 | 2023-03-24 | 스미토모 베이클리트 컴퍼니 리미티드 | 폴리사이클로올레핀 모노머 및 가교제에서 유래하는 고충격 강도의 3d 인쇄 재료 |
| TWI834019B (zh) * | 2020-01-09 | 2024-03-01 | 日商住友電木股份有限公司 | 作為3d列印材料之穩定本體聚合型多環烯烴組成物及其製備方法 |
| KR20230095975A (ko) * | 2020-10-30 | 2023-06-29 | 프로메러스, 엘엘씨 | 저장수명이 안정적이고 덩이중합이 가능한 개선된 폴리시클로올레핀 조성물 |
| WO2022118175A1 (en) | 2020-12-02 | 2022-06-09 | 3M Innovative Properties Company | Curable compositions, composite foam, method of making the same, and article including the same |
| TWI895585B (zh) | 2021-02-02 | 2025-09-01 | 日商住友電木股份有限公司 | 作為光學材料之保存期限長期穩定的光活性本體聚合型多環烯烴組成物 |
| US20240279251A1 (en) | 2021-05-14 | 2024-08-22 | 3M Innovative Properties Company | Monomer, Polymerizable Composition, and Polymers Derived Therefrom |
| KR20240052050A (ko) * | 2021-08-31 | 2024-04-22 | 메르크 파텐트 게엠베하 | 조성물 |
| TW202323266A (zh) | 2021-11-29 | 2023-06-16 | 美商普羅梅勒斯有限公司 | 作為光學材料之包含保存期限長期穩定的光活性本體聚合型多環烯烴組成物之雙重ｕｖ阻斷劑 |
| JP2025534788A (ja) | 2022-10-21 | 2025-10-17 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 組成物 |
| CN120152955A (zh) | 2022-10-31 | 2025-06-13 | 3M创新有限公司 | 包含衣康酰亚胺降冰片烯和柠康酰亚胺降冰片烯的异构体混合物的组合物 |
| WO2024100476A1 (en) | 2022-11-07 | 2024-05-16 | 3M Innovative Properties Company | Curable and cured thermosetting compositions |
| TW202442659A (zh) * | 2023-03-15 | 2024-11-01 | 美商普羅梅勒斯有限公司 | 高純度降莰烯矽醚的製備方法 |
| WO2025012183A1 (en) | 2023-07-10 | 2025-01-16 | Merck Patent Gmbh | Composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP1034196B1 (en) * | 1998-10-05 | 2005-01-12 | Promerus LLC | Catalyst and methods for polymerizing cycloolefins |
| WO2000034344A1 (en) * | 1998-12-09 | 2000-06-15 | The B.F.Goodrich Company | In mold addition polymerization of norbornene-type monomers using group 10 metal complexes |
| AU2001280856A1 (en) * | 2000-07-28 | 2002-02-13 | Goodrich Corporation | Polymeric compositions for forming optical waveguides; optical waveguides formed therefrom; and methods for making same |
| CN101308228B (zh) * | 2003-11-21 | 2016-04-06 | 住友电木株式会社 | 光波导及其形成方法 |
| KR101230512B1 (ko) * | 2003-11-21 | 2013-02-18 | 스미토모 베이클리트 컴퍼니 리미티드 | 광-유도 열 현상형 막 및 광도파로 형성 방법 |
| US7329465B2 (en) * | 2004-10-29 | 2008-02-12 | 3M Innovative Properties Company | Optical films incorporating cyclic olefin copolymers |
| JP5153227B2 (ja) | 2007-06-26 | 2013-02-27 | キヤノン株式会社 | 有機発光素子 |
| DE102009013710A1 (de) | 2009-03-20 | 2010-09-23 | Merck Patent Gmbh | Polymere aus Mischungen mit Vinylether-Monomeren |
| KR20130114120A (ko) * | 2010-09-02 | 2013-10-16 | 메르크 파텐트 게엠베하 | 전자 디바이스용 중간층 |
| EP2898551B1 (en) * | 2012-09-21 | 2020-04-22 | Merck Patent GmbH | Organic semiconductor formulations |
| KR101572049B1 (ko) * | 2012-09-25 | 2015-11-26 | 프로메러스, 엘엘씨 | 사이클로올레핀성 중합체를 함유하는 말레이미드 및 그의 용도 |
| WO2014099546A1 (en) * | 2012-12-19 | 2014-06-26 | Promerus, Llc | Process for the preparation of high purity norbornene alkanols and derivatives thereof |
| WO2015038412A2 (en) * | 2013-09-16 | 2015-03-19 | Promerus, Llc | Amine treated maleic anhydride polymers with pendent silyl group, compositions and applications thereof |
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- 2016-09-01 KR KR1020187006051A patent/KR20180048664A/ko not_active Withdrawn
- 2016-09-01 WO PCT/US2016/049822 patent/WO2017040737A1/en not_active Ceased
- 2016-09-01 US US15/253,980 patent/US9944818B2/en active Active
- 2016-09-01 EP EP16767080.1A patent/EP3344671B1/en active Active
- 2016-09-01 CN CN201680050563.9A patent/CN107922549B/zh active Active
- 2016-09-01 JP JP2018508194A patent/JP2018526503A/ja active Pending
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2018
- 2018-03-06 US US15/913,337 patent/US10266720B2/en active Active
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