TWI867226B - 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 - Google Patents
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 Download PDFInfo
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- TWI867226B TWI867226B TW110122991A TW110122991A TWI867226B TW I867226 B TWI867226 B TW I867226B TW 110122991 A TW110122991 A TW 110122991A TW 110122991 A TW110122991 A TW 110122991A TW I867226 B TWI867226 B TW I867226B
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- Prior art keywords
- alkyl
- hept
- borate
- group
- aryl
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- 239000000203 mixture Substances 0.000 title claims abstract description 214
- 230000003287 optical effect Effects 0.000 title abstract description 13
- 150000001412 amines Chemical class 0.000 title abstract description 6
- 239000000463 material Substances 0.000 title description 8
- 229920003050 poly-cycloolefin Polymers 0.000 title 1
- 239000000178 monomer Substances 0.000 claims abstract description 173
- 150000001875 compounds Chemical class 0.000 claims abstract description 118
- 230000005855 radiation Effects 0.000 claims abstract description 34
- 239000003504 photosensitizing agent Substances 0.000 claims abstract description 20
- -1 tetrakis(pentafluorophenyl)borate Chemical compound 0.000 claims description 164
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 126
- 125000000217 alkyl group Chemical group 0.000 claims description 91
- 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 description 72
- 101000692259 Homo sapiens Phosphoprotein associated with glycosphingolipid-enriched microdomains 1 Proteins 0.000 claims description 70
- 102100026066 Phosphoprotein associated with glycosphingolipid-enriched microdomains 1 Human genes 0.000 claims description 70
- 101000987219 Sus scrofa Pregnancy-associated glycoprotein 1 Proteins 0.000 claims description 69
- 229910052763 palladium Inorganic materials 0.000 claims description 61
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 60
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 55
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 53
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 40
- 125000004104 aryloxy group Chemical group 0.000 claims description 35
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 33
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 150000002941 palladium compounds Chemical class 0.000 claims description 27
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 21
- UWKQJZCTQGMHKD-UHFFFAOYSA-N 2,6-di-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=N1 UWKQJZCTQGMHKD-UHFFFAOYSA-N 0.000 claims description 21
- VTWPBVSOSWNXAX-UHFFFAOYSA-N 5-decylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCCCCCC)CC1C=C2 VTWPBVSOSWNXAX-UHFFFAOYSA-N 0.000 claims description 21
- 125000005293 bicycloalkoxy group Chemical group 0.000 claims description 21
- AUFVJZSDSXXFOI-UHFFFAOYSA-N 2.2.2-cryptand Chemical compound C1COCCOCCN2CCOCCOCCN1CCOCCOCC2 AUFVJZSDSXXFOI-UHFFFAOYSA-N 0.000 claims description 19
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 18
- GJFNRSDCSTVPCJ-UHFFFAOYSA-N 1,8-bis(dimethylamino)naphthalene Chemical compound C1=CC(N(C)C)=C2C(N(C)C)=CC=CC2=C1 GJFNRSDCSTVPCJ-UHFFFAOYSA-N 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 16
- YRAJNWYBUCUFBD-UHFFFAOYSA-N 2,2,6,6-tetramethylheptane-3,5-dione Chemical compound CC(C)(C)C(=O)CC(=O)C(C)(C)C YRAJNWYBUCUFBD-UHFFFAOYSA-N 0.000 claims description 16
- NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 15
- RSOILICUEWXSLA-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 RSOILICUEWXSLA-UHFFFAOYSA-N 0.000 claims description 14
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- PGNNHYNYFLXKDZ-UHFFFAOYSA-N 5-phenylbicyclo[2.2.1]hept-2-ene Chemical compound C1=CC2CC1CC2C1=CC=CC=C1 PGNNHYNYFLXKDZ-UHFFFAOYSA-N 0.000 claims description 12
- 150000001336 alkenes Chemical class 0.000 claims description 12
- OSIVCXJNIBEGCL-UHFFFAOYSA-N bis(2,2,6,6-tetramethyl-1-octoxypiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(OCCCCCCCC)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(OCCCCCCCC)C(C)(C)C1 OSIVCXJNIBEGCL-UHFFFAOYSA-N 0.000 claims description 12
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 claims description 12
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 10
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 10
- QAMFBRUWYYMMGJ-UHFFFAOYSA-N hexafluoroacetylacetone Chemical compound FC(F)(F)C(=O)CC(=O)C(F)(F)F QAMFBRUWYYMMGJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000003446 ligand Substances 0.000 claims description 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 8
- 239000007983 Tris buffer Substances 0.000 claims description 8
- 125000002619 bicyclic group Chemical group 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 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 8
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 238000002834 transmittance Methods 0.000 claims description 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 6
- VINIZRWHLWITIZ-UHFFFAOYSA-N 5-hexadecylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCCCCCCCCCCCC)CC1C=C2 VINIZRWHLWITIZ-UHFFFAOYSA-N 0.000 claims description 6
- WMWDGZLDLRCDRG-UHFFFAOYSA-N 5-hexylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCC)CC1C=C2 WMWDGZLDLRCDRG-UHFFFAOYSA-N 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 6
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 claims description 6
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 6
- 125000005000 thioaryl group Chemical group 0.000 claims description 6
- 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 5
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000006529 (C3-C6) alkyl group Chemical group 0.000 claims description 4
- 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 4
- HDLXPNDSLDLJHF-UHFFFAOYSA-N 4,7,13,16,21-pentaoxa-1,10-diazabicyclo[8.8.5]tricosane Chemical compound C1COCCOCCN2CCOCCOCCN1CCOCC2 HDLXPNDSLDLJHF-UHFFFAOYSA-N 0.000 claims description 4
- LVNQVIZBPSRXAN-UHFFFAOYSA-N 4,7,13,18-tetraoxa-1,10-diazabicyclo[8.5.5]icosane Chemical compound C1COCCOCCN2CCOCCN1CCOCC2 LVNQVIZBPSRXAN-UHFFFAOYSA-N 0.000 claims description 4
- GJNKQJAJXSUJBO-UHFFFAOYSA-N 9,10-diethoxyanthracene Chemical compound C1=CC=C2C(OCC)=C(C=CC=C3)C3=C(OCC)C2=C1 GJNKQJAJXSUJBO-UHFFFAOYSA-N 0.000 claims description 4
- JWJMBKSFTTXMLL-UHFFFAOYSA-N 9,10-dimethoxyanthracene Chemical compound C1=CC=C2C(OC)=C(C=CC=C3)C3=C(OC)C2=C1 JWJMBKSFTTXMLL-UHFFFAOYSA-N 0.000 claims description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 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 claims description 4
- 150000003222 pyridines Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 3
- 125000005914 C6-C14 aryloxy group Chemical group 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000005257 alkyl acyl group Chemical group 0.000 claims description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 claims description 3
- DFSWKIGXUOJVAC-UHFFFAOYSA-M (4-phenoxyphenyl)-diphenylsulfanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C=1C=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1OC1=CC=CC=C1 DFSWKIGXUOJVAC-UHFFFAOYSA-M 0.000 claims description 2
- PEALEMBUUUVDRP-UHFFFAOYSA-N 1-[4-(5-bicyclo[2.2.1]hept-2-enyl)butyl]-3,4-dimethylpyrrole-2,5-dione Chemical compound O=C1C(C)=C(C)C(=O)N1CCCCC1C(C=C2)CC2C1 PEALEMBUUUVDRP-UHFFFAOYSA-N 0.000 claims description 2
- GOXVZGOCBRLZOO-UHFFFAOYSA-N 1-n,1-n,8-n,8-n-tetraethylnaphthalene-1,8-diamine Chemical compound C1=CC(N(CC)CC)=C2C(N(CC)CC)=CC=CC2=C1 GOXVZGOCBRLZOO-UHFFFAOYSA-N 0.000 claims description 2
- HVHZEKKZMFRULH-UHFFFAOYSA-N 2,6-ditert-butyl-4-methylpyridine Chemical compound CC1=CC(C(C)(C)C)=NC(C(C)(C)C)=C1 HVHZEKKZMFRULH-UHFFFAOYSA-N 0.000 claims description 2
- WLCVNBXWMQMKGJ-UHFFFAOYSA-N 2-(5-bicyclo[2.2.1]hept-2-enyl)ethyl-trimethoxysilane Chemical compound C1C2C(CC[Si](OC)(OC)OC)CC1C=C2 WLCVNBXWMQMKGJ-UHFFFAOYSA-N 0.000 claims description 2
- GBNPJBBNCBLPQT-UHFFFAOYSA-N 2-(5-bicyclo[2.2.1]hept-2-enylmethoxymethyl)oxirane Chemical compound C1C(C=C2)CC2C1COCC1CO1 GBNPJBBNCBLPQT-UHFFFAOYSA-N 0.000 claims description 2
- DNKWNPPMHHHLPK-UHFFFAOYSA-N 2-[2-(5-bicyclo[2.2.1]hept-2-enyl)ethyl]oxirane Chemical compound C1C(C=C2)CC2C1CCC1CO1 DNKWNPPMHHHLPK-UHFFFAOYSA-N 0.000 claims description 2
- IKQZRBFBKKQBHZ-UHFFFAOYSA-N 2-[4-(2-bicyclo[2.2.1]hept-5-enyl)butoxymethyl]naphthalene Chemical compound C12C(CC(C=C1)C2)CCCCOCC1=CC2=CC=CC=C2C=C1 IKQZRBFBKKQBHZ-UHFFFAOYSA-N 0.000 claims description 2
- FNYHTZZXMGYSDC-UHFFFAOYSA-N 2-[4-(5-bicyclo[2.2.1]hept-2-enyl)butyl]oxirane Chemical compound C1C(C=C2)CC2C1CCCCC1CO1 FNYHTZZXMGYSDC-UHFFFAOYSA-N 0.000 claims description 2
- CTFCLRQTZHMVEE-UHFFFAOYSA-N 2-[6-(5-bicyclo[2.2.1]hept-2-enyl)hexyl]oxirane Chemical compound C1C(C=C2)CC2C1CCCCCCC1CO1 CTFCLRQTZHMVEE-UHFFFAOYSA-N 0.000 claims description 2
- TZBQHBRDKCGZCW-UHFFFAOYSA-N 2-bicyclo[2.2.1]hept-5-enyl 2-(4-phenylphenyl)acetate Chemical compound O=C(CC1=CC=C(C=C1)C1=CC=CC=C1)OC1CC2CC1C=C2 TZBQHBRDKCGZCW-UHFFFAOYSA-N 0.000 claims description 2
- BVHBPGBQMOUTQN-UHFFFAOYSA-N 2-bicyclo[2.2.1]hept-5-enylmethyl 9H-fluoren-9-ylmethyl carbonate Chemical compound O=C(OCC1CC2CC1C=C2)OCC1C2=C(C=CC=C2)C2=C1C=CC=C2 BVHBPGBQMOUTQN-UHFFFAOYSA-N 0.000 claims description 2
- YBLYMWNURUFPMJ-UHFFFAOYSA-N 4-(5-bicyclo[2.2.1]hept-2-enyl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2OC2CC1C1CC2CC1C=C2 YBLYMWNURUFPMJ-UHFFFAOYSA-N 0.000 claims description 2
- JCHDZHTVBMCNRM-UHFFFAOYSA-N 5-(2-chloroethyl)bicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCl)CC1C=C2 JCHDZHTVBMCNRM-UHFFFAOYSA-N 0.000 claims description 2
- MCTHDFQOSYIUTR-UHFFFAOYSA-N 5-(2-phenoxyethyl)bicyclo[2.2.1]hept-2-ene Chemical compound C(CC1CC2CC1C=C2)OC1=CC=CC=C1 MCTHDFQOSYIUTR-UHFFFAOYSA-N 0.000 claims description 2
- SPQKNMZLRIZTOC-UHFFFAOYSA-N 5-(2-phenylethoxy)bicyclo[2.2.1]hept-2-ene Chemical compound C(CC1=CC=CC=C1)OC1C2C=CC(C1)C2 SPQKNMZLRIZTOC-UHFFFAOYSA-N 0.000 claims description 2
- AFDAXUMEBMDDDM-UHFFFAOYSA-N 5-(3-phenylpropyl)bicyclo[2.2.1]hept-2-ene Chemical compound C1C(C=C2)CC2C1CCCC1=CC=CC=C1 AFDAXUMEBMDDDM-UHFFFAOYSA-N 0.000 claims description 2
- UDRXMPPQQMNOIS-UHFFFAOYSA-N 5-(4-phenylbutyl)bicyclo[2.2.1]hept-2-ene Chemical compound C1C(C=C2)CC2C1CCCCC1=CC=CC=C1 UDRXMPPQQMNOIS-UHFFFAOYSA-N 0.000 claims description 2
- OWETXGRKCLKMMD-UHFFFAOYSA-N 5-(phenoxymethyl)bicyclo[2.2.1]hept-2-ene Chemical compound C1C(C=C2)CC2C1COC1=CC=CC=C1 OWETXGRKCLKMMD-UHFFFAOYSA-N 0.000 claims description 2
- ABUDOMSLEKPEEV-UHFFFAOYSA-N 5-(phenylmethoxymethyl)bicyclo[2.2.1]hept-2-ene Chemical compound C1C(C=C2)CC2C1COCC1=CC=CC=C1 ABUDOMSLEKPEEV-UHFFFAOYSA-N 0.000 claims description 2
- JSQDUFHOLSQWEG-UHFFFAOYSA-N 5-[2-(2-phenylphenoxy)ethyl]bicyclo[2.2.1]hept-2-ene Chemical compound C(CC1CC2CC1C=C2)OC1=C(C=CC=C1)C1=CC=CC=C1 JSQDUFHOLSQWEG-UHFFFAOYSA-N 0.000 claims description 2
- BOJLWRGMOWGUDX-UHFFFAOYSA-N 5-[2-(4-phenylphenoxy)ethyl]bicyclo[2.2.1]hept-2-ene Chemical compound C1(=CC=C(C=C1)OCCC1C2C=CC(C1)C2)C1=CC=CC=C1 BOJLWRGMOWGUDX-UHFFFAOYSA-N 0.000 claims description 2
- KRYJNQPFTSNAFW-UHFFFAOYSA-N 5-[2-(4-phenylphenyl)ethoxy]bicyclo[2.2.1]hept-2-ene Chemical compound C1(=CC=C(C=C1)CCOC1C2C=CC(C1)C2)C1=CC=CC=C1 KRYJNQPFTSNAFW-UHFFFAOYSA-N 0.000 claims description 2
- PPOOPTMXXRGDNT-UHFFFAOYSA-N 5-[2-[4-(2,4-dimethylphenyl)phenyl]ethoxy]bicyclo[2.2.1]hept-2-ene Chemical compound CC1=C(C=CC(=C1)C)C1=CC=C(C=C1)CCOC1C2C=CC(C1)C2 PPOOPTMXXRGDNT-UHFFFAOYSA-N 0.000 claims description 2
- UWNCOTJYWUWOHF-UHFFFAOYSA-N 5-[4-(4-phenylphenyl)butyl]bicyclo[2.2.1]hept-2-ene Chemical compound C1C(C=C2)CC2C1CCCCC(C=C1)=CC=C1C1=CC=CC=C1 UWNCOTJYWUWOHF-UHFFFAOYSA-N 0.000 claims description 2
- BDOKDQVOFFMXBX-UHFFFAOYSA-N 5-[4-(5-bicyclo[2.2.1]hept-2-enyl)phenyl]bicyclo[2.2.1]hept-2-ene Chemical compound C1=CC2CC1CC2C(C=C1)=CC=C1C1C(C=C2)CC2C1 BDOKDQVOFFMXBX-UHFFFAOYSA-N 0.000 claims description 2
- HHKDWDAAEFGBAC-UHFFFAOYSA-N 5-bicyclo[2.2.1]hept-2-enyl(triethoxy)silane Chemical compound C1C2C([Si](OCC)(OCC)OCC)CC1C=C2 HHKDWDAAEFGBAC-UHFFFAOYSA-N 0.000 claims description 2
- DZWAQOSWSCOXEW-UHFFFAOYSA-N 5-bicyclo[2.2.1]hept-2-enyl(trimethoxy)silane Chemical compound C1C2C([Si](OC)(OC)OC)CC1C=C2 DZWAQOSWSCOXEW-UHFFFAOYSA-N 0.000 claims description 2
- OUXGYYLEDBRBGE-UHFFFAOYSA-N 5-bicyclo[2.2.1]hept-2-enylmethoxy-dimethyl-phenylsilane Chemical compound C1C(C=C2)CC2C1CO[Si](C)(C)C1=CC=CC=C1 OUXGYYLEDBRBGE-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- PDVFZIUUECEMQX-UHFFFAOYSA-N 5-bicyclo[2.2.1]hept-2-enylmethyl 4-phenylbenzoate Chemical compound C1C(C=C2)CC2C1COC(=O)C(C=C1)=CC=C1C1=CC=CC=C1 PDVFZIUUECEMQX-UHFFFAOYSA-N 0.000 claims description 2
- VVKPRHOUENDOED-UHFFFAOYSA-N 5-dodecylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCCCCCCCC)CC1C=C2 VVKPRHOUENDOED-UHFFFAOYSA-N 0.000 claims description 2
- GOLQZWYZZWIBCA-UHFFFAOYSA-N 5-octylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCCCC)CC1C=C2 GOLQZWYZZWIBCA-UHFFFAOYSA-N 0.000 claims description 2
- VUVMZXSYXNPPEF-UHFFFAOYSA-N 5-phenylmethoxybicyclo[2.2.1]hept-2-ene Chemical compound C1C(C=C2)CC2C1OCC1=CC=CC=C1 VUVMZXSYXNPPEF-UHFFFAOYSA-N 0.000 claims description 2
- BUDHNVQSXHHVLF-UHFFFAOYSA-N 5-tetradecylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCCCCCCCCCC)CC1C=C2 BUDHNVQSXHHVLF-UHFFFAOYSA-N 0.000 claims description 2
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- VTKQLVHDZYRENE-UHFFFAOYSA-N tricyclopentyl phosphite Chemical compound C1CCCC1OP(OC1CCCC1)OC1CCCC1 VTKQLVHDZYRENE-UHFFFAOYSA-N 0.000 description 1
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- SJHCUXCOGGKFAI-UHFFFAOYSA-N tripropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC(C)C SJHCUXCOGGKFAI-UHFFFAOYSA-N 0.000 description 1
- QOPBTFMUVTXWFF-UHFFFAOYSA-N tripropyl phosphite Chemical compound CCCOP(OCCC)OCCC QOPBTFMUVTXWFF-UHFFFAOYSA-N 0.000 description 1
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- NURJXHUITUPBOD-UHFFFAOYSA-N tris(2-methylpropyl) phosphite Chemical compound CC(C)COP(OCC(C)C)OCC(C)C NURJXHUITUPBOD-UHFFFAOYSA-N 0.000 description 1
- DAGQYUCAQQEEJD-UHFFFAOYSA-N tris(2-methylpropyl)phosphane Chemical compound CC(C)CP(CC(C)C)CC(C)C DAGQYUCAQQEEJD-UHFFFAOYSA-N 0.000 description 1
- KJWHEZXBZQXVSA-UHFFFAOYSA-N tris(prop-2-enyl) phosphite Chemical compound C=CCOP(OCC=C)OCC=C KJWHEZXBZQXVSA-UHFFFAOYSA-N 0.000 description 1
- GNFABDZKXNKQKN-UHFFFAOYSA-N tris(prop-2-enyl)phosphane Chemical compound C=CCP(CC=C)CC=C GNFABDZKXNKQKN-UHFFFAOYSA-N 0.000 description 1
- NZIQBDROTUFRHZ-UHFFFAOYSA-N tritert-butyl phosphite Chemical compound CC(C)(C)OP(OC(C)(C)C)OC(C)(C)C NZIQBDROTUFRHZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/14—Monomers containing five or more carbon atoms
-
- 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
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| US11779524B2 (en) | 2020-03-16 | 2023-10-10 | Kabushiki Kaisha Shofu | Photopolymerization initiator comprising an aryliodonium salt for dental photocurable compositions |
| CN115068345A (zh) | 2021-03-12 | 2022-09-20 | 株式会社松风 | 保存稳定性优异的牙科用粘接性组合物 |
| EP4062893A1 (en) | 2021-03-12 | 2022-09-28 | Shofu Inc. | Dental photocurable composition excellent in storage stability |
| WO2023278649A1 (en) * | 2021-06-30 | 2023-01-05 | Promerus, Llc | Stabilized uv active organopalladium compounds as vinyl addition catalysts |
| TW202334314A (zh) * | 2022-02-18 | 2023-09-01 | 美商普羅梅勒斯有限公司 | 乙烯基加成本體聚合及陽離子聚合型組成物用雙觸媒體系 |
| TW202334271A (zh) * | 2022-02-18 | 2023-09-01 | 美商普羅梅勒斯有限公司 | Romp本體聚合及陽離子聚合型組成物用雙觸媒體系 |
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| TW200635968A (en) * | 2004-12-22 | 2006-10-16 | Jsr Corp | Method for producing cyclic olefin addition copolymer, cyclic olefin addition copolymer and use thereof |
| TW201831537A (zh) * | 2017-01-06 | 2018-09-01 | 美商普羅梅勒斯有限公司 | 作為光學材料之聚環烯烴聚合物組成物 |
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| US5112890A (en) * | 1987-09-21 | 1992-05-12 | Ciba-Geigy Corporation | Stabilization of acid catalyzed thermoset resins |
| US6232417B1 (en) * | 1996-03-07 | 2001-05-15 | The B. F. Goodrich Company | Photoresist compositions comprising polycyclic polymers with acid labile pendant groups |
| EP1448617B1 (en) * | 2002-07-10 | 2015-07-01 | LG Chem, Ltd. | Method for preparing norbornene based addition polymer containing ester or acetyl functional group |
| KR100526403B1 (ko) * | 2002-07-10 | 2005-11-08 | 주식회사 엘지화학 | 에스테르기 또는 아세틸기를 포함하는 노보넨계부가중합체의 제조방법 |
| US7718744B2 (en) * | 2002-12-05 | 2010-05-18 | Lg Chem, Ltd. | Method for polymerizing cycloolefin polymer containing polar functional groups and electronic devices employing the polymerized cycloolefins |
| 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 |
| US20050187398A1 (en) * | 2003-10-31 | 2005-08-25 | Andrew Bell | Single component cationic palladium proinitiators for the latent polymerization of cycloolefins |
| JP4075789B2 (ja) * | 2003-12-05 | 2008-04-16 | Ｊｓｒ株式会社 | 環状オレフィン系付加重合体の製造方法 |
| JP4760133B2 (ja) * | 2005-05-23 | 2011-08-31 | 住友ベークライト株式会社 | 光導波路構造体 |
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| PT1979406E (pt) * | 2006-02-01 | 2013-01-28 | Basf Se | Composição estabilizadora para polímeros |
| US7759439B2 (en) * | 2007-03-30 | 2010-07-20 | Promerus Llc | Use of a combination chain transfer and activating agent to control molecular weight and optical density of Pd catalyzed norbornene polymers |
| JP5332883B2 (ja) * | 2009-04-30 | 2013-11-06 | 住友ベークライト株式会社 | 感光性組成物、光導波路、光配線、光電気混載基板、電子機器、および光導波路の形成方法 |
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| US10245562B2 (en) * | 2014-08-15 | 2019-04-02 | Promerus, Llc | Pervaporation membranes derived from polycyclo-olefinic block copolymers |
| CN110366585B (zh) * | 2017-02-24 | 2022-04-29 | 富士胶片株式会社 | 光固化性油墨组合物及图像形成方法 |
| WO2020243381A1 (en) * | 2019-05-31 | 2020-12-03 | Promerus, Llc | Fast photocurable polycycloolefin compositions as optical or 3d printing materials |
| TWI850512B (zh) * | 2019-12-30 | 2024-08-01 | 日商住友電木股份有限公司 | 作為光學材料之uv活性鈀催化多環烯烴聚合物組成物 |
| TWI850509B (zh) * | 2019-12-30 | 2024-08-01 | 日商住友電木股份有限公司 | 催化多環烯烴組成物的uv活性衍生物 |
| TWI848199B (zh) * | 2020-01-02 | 2024-07-11 | 日商住友電木股份有限公司 | 作為光學材料之保存期限延長的本體聚合型多環烯烴組成物 |
| US11760817B2 (en) * | 2020-06-08 | 2023-09-19 | Promerus, Llc | Mass polymerizable polycycloolefin compositions containing soluble photoacid generators |
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| TW200635968A (en) * | 2004-12-22 | 2006-10-16 | Jsr Corp | Method for producing cyclic olefin addition copolymer, cyclic olefin addition copolymer and use thereof |
| TW201831537A (zh) * | 2017-01-06 | 2018-09-01 | 美商普羅梅勒斯有限公司 | 作為光學材料之聚環烯烴聚合物組成物 |
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