WO2004035636A2 - Polymerized cycloolefins using transition metal catalyst and end products thereof - Google Patents
Polymerized cycloolefins using transition metal catalyst and end products thereof Download PDFInfo
- Publication number
- WO2004035636A2 WO2004035636A2 PCT/US2003/032474 US0332474W WO2004035636A2 WO 2004035636 A2 WO2004035636 A2 WO 2004035636A2 US 0332474 W US0332474 W US 0332474W WO 2004035636 A2 WO2004035636 A2 WO 2004035636A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- branched
- group
- linear
- alkyl
- norbornene
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 147
- 229910052723 transition metal Inorganic materials 0.000 title claims abstract description 57
- 150000003624 transition metals Chemical class 0.000 title claims abstract description 52
- 150000001925 cycloalkenes Chemical class 0.000 title claims abstract description 13
- 239000007795 chemical reaction product Substances 0.000 title description 2
- 229920000642 polymer Polymers 0.000 claims abstract description 203
- 239000003446 ligand Substances 0.000 claims abstract description 124
- 230000003287 optical effect Effects 0.000 claims abstract description 122
- 150000001768 cations Chemical class 0.000 claims abstract description 77
- 150000001450 anions Chemical class 0.000 claims abstract description 56
- 230000007935 neutral effect Effects 0.000 claims abstract description 53
- 125000003367 polycyclic group Chemical group 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims description 367
- -1 alkyl norbornene Chemical compound 0.000 claims description 348
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 243
- 239000000178 monomer Substances 0.000 claims description 200
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 147
- 125000000217 alkyl group Chemical group 0.000 claims description 137
- 229910052763 palladium Inorganic materials 0.000 claims description 109
- 125000003118 aryl group Chemical group 0.000 claims description 106
- VEEKCIOFMIAGSF-UHFFFAOYSA-N 4-butylbicyclo[2.2.1]hept-2-ene Chemical group C1CC2C=CC1(CCCC)C2 VEEKCIOFMIAGSF-UHFFFAOYSA-N 0.000 claims description 86
- 125000004432 carbon atom Chemical group C* 0.000 claims description 83
- 229910052751 metal Inorganic materials 0.000 claims description 66
- 239000002904 solvent Substances 0.000 claims description 65
- 229910052739 hydrogen Inorganic materials 0.000 claims description 63
- 239000001257 hydrogen Substances 0.000 claims description 63
- 239000002184 metal Substances 0.000 claims description 57
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 55
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 55
- 150000003839 salts Chemical class 0.000 claims description 55
- 229910052736 halogen Inorganic materials 0.000 claims description 54
- 150000002367 halogens Chemical class 0.000 claims description 54
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 54
- 125000001188 haloalkyl group Chemical group 0.000 claims description 53
- 239000000460 chlorine Substances 0.000 claims description 51
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 49
- 150000004645 aluminates Chemical class 0.000 claims description 47
- 229910052731 fluorine Inorganic materials 0.000 claims description 46
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
- 125000003545 alkoxy group Chemical group 0.000 claims description 44
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 43
- 239000011737 fluorine Substances 0.000 claims description 43
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 42
- 229920003050 poly-cycloolefin Polymers 0.000 claims description 40
- 239000004065 semiconductor Substances 0.000 claims description 40
- 125000001424 substituent group Chemical group 0.000 claims description 40
- 239000000853 adhesive Substances 0.000 claims description 39
- 230000001070 adhesive effect Effects 0.000 claims description 39
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 37
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 33
- 125000004122 cyclic group Chemical group 0.000 claims description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 28
- 229910052744 lithium Inorganic materials 0.000 claims description 28
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 26
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 24
- 239000000758 substrate Substances 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 239000001301 oxygen Substances 0.000 claims description 23
- 238000001914 filtration Methods 0.000 claims description 22
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 22
- 229910052697 platinum Inorganic materials 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 230000000694 effects Effects 0.000 claims description 19
- 239000010408 film Substances 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
- 238000000576 coating method Methods 0.000 claims description 18
- 229910052759 nickel Chemical group 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 16
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 16
- 230000000379 polymerizing effect Effects 0.000 claims description 16
- 125000004104 aryloxy group Chemical group 0.000 claims description 15
- 239000012788 optical film Substances 0.000 claims description 15
- CBVRSAWYUWTDDH-UHFFFAOYSA-N 4-bicyclo[2.2.1]hept-2-enyl(trimethoxy)silane Chemical group C1CC2C=CC1([Si](OC)(OC)OC)C2 CBVRSAWYUWTDDH-UHFFFAOYSA-N 0.000 claims description 14
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 14
- 230000005693 optoelectronics Effects 0.000 claims description 14
- 229910052710 silicon Chemical group 0.000 claims description 14
- JZEPSDIWGBJOEH-UHFFFAOYSA-N 4-decylbicyclo[2.2.1]hept-2-ene Chemical compound C1CC2C=CC1(CCCCCCCCCC)C2 JZEPSDIWGBJOEH-UHFFFAOYSA-N 0.000 claims description 13
- 239000011248 coating agent Substances 0.000 claims description 13
- 239000005022 packaging material Substances 0.000 claims description 13
- 229910052698 phosphorus Inorganic materials 0.000 claims description 13
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- 239000003990 capacitor Substances 0.000 claims description 12
- 239000008393 encapsulating agent Substances 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 239000012212 insulator Substances 0.000 claims description 12
- 239000011593 sulfur Chemical group 0.000 claims description 12
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 11
- 229910052782 aluminium Chemical group 0.000 claims description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 11
- 229910052796 boron Inorganic materials 0.000 claims description 11
- 238000000746 purification Methods 0.000 claims description 11
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 10
- 125000000746 allylic group Chemical group 0.000 claims description 10
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- 125000000129 anionic group Chemical group 0.000 claims description 9
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical class [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 claims description 9
- 238000001723 curing Methods 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 238000005286 illumination Methods 0.000 claims description 9
- 239000013307 optical fiber Substances 0.000 claims description 9
- 210000001525 retina Anatomy 0.000 claims description 9
- 239000010703 silicon Chemical group 0.000 claims description 9
- OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical class [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 claims description 9
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- 239000011574 phosphorus Substances 0.000 claims description 8
- 150000003222 pyridines Chemical class 0.000 claims description 8
- 150000004292 cyclic ethers Chemical class 0.000 claims description 7
- 125000004342 dicyclopropylmethyl group Chemical group [H]C1([H])C([H])([H])C1([H])C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000000962 organic group Chemical group 0.000 claims description 7
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 7
- 239000011253 protective coating Substances 0.000 claims description 7
- 150000003568 thioethers Chemical class 0.000 claims description 7
- 229910007161 Si(CH3)3 Inorganic materials 0.000 claims description 6
- 229960004132 diethyl ether Drugs 0.000 claims description 6
- 125000003106 haloaryl group Chemical group 0.000 claims description 6
- 239000012939 laminating adhesive Substances 0.000 claims description 6
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 5
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 5
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000002704 decyl 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])C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000000835 fiber Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000004437 phosphorous atom Chemical group 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 claims description 4
- 239000004912 1,5-cyclooctadiene Substances 0.000 claims description 4
- 150000001993 dienes Chemical class 0.000 claims description 4
- 150000001642 boronic acid derivatives Chemical group 0.000 claims description 3
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 150000002903 organophosphorus compounds Chemical class 0.000 claims description 3
- 125000005389 trialkylsiloxy group Chemical group 0.000 claims description 3
- LFMFPKKYRXFHHZ-UHFFFAOYSA-N R24 Chemical group C1=C(Cl)C(C)=CC=C1NC1=NC(N)=C(C=CC=C2)C2=N1 LFMFPKKYRXFHHZ-UHFFFAOYSA-N 0.000 claims description 2
- 229920000636 poly(norbornene) polymer Polymers 0.000 claims description 2
- 125000005369 trialkoxysilyl group Chemical group 0.000 claims description 2
- RGGBKNFGPFEDRC-UHFFFAOYSA-N 4-bicyclo[2.2.1]hept-2-enyl(triethoxy)silane Chemical compound C1CC2C=CC1([Si](OCC)(OCC)OCC)C2 RGGBKNFGPFEDRC-UHFFFAOYSA-N 0.000 claims 13
- KMRASZKMNHTING-UHFFFAOYSA-N 4-hexylbicyclo[2.2.1]hept-2-ene Chemical compound C1CC2C=CC1(CCCCCC)C2 KMRASZKMNHTING-UHFFFAOYSA-N 0.000 claims 13
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 8
- 238000001228 spectrum Methods 0.000 claims 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 claims 2
- 238000001429 visible spectrum Methods 0.000 claims 2
- 229910000074 antimony hydride Inorganic materials 0.000 claims 1
- VIQRCOQXIHFJND-UHFFFAOYSA-N bicyclo[2.2.2]oct-2-ene Chemical compound C1CC2CCC1C=C2 VIQRCOQXIHFJND-UHFFFAOYSA-N 0.000 claims 1
- 238000002329 infrared spectrum Methods 0.000 claims 1
- 229920005567 polycyclic polymer Polymers 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 238000002211 ultraviolet spectrum Methods 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 abstract description 12
- 238000012644 addition polymerization Methods 0.000 abstract description 3
- 150000004696 coordination complex Chemical class 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 811
- 239000000243 solution Substances 0.000 description 220
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 123
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 105
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 102
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
- 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 description 71
- WLTSXAIICPDFKI-FNORWQNLSA-N (E)-3-dodecene Chemical compound CCCCCCCC\C=C\CC WLTSXAIICPDFKI-FNORWQNLSA-N 0.000 description 56
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical class Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 55
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 55
- 238000006243 chemical reaction Methods 0.000 description 53
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 53
- 125000001183 hydrocarbyl group Chemical group 0.000 description 44
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 44
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 42
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 32
- 238000006116 polymerization reaction Methods 0.000 description 31
- 239000007787 solid Substances 0.000 description 31
- 150000002431 hydrogen Chemical class 0.000 description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 28
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 229910052801 chlorine Inorganic materials 0.000 description 22
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 21
- 229910052794 bromium Inorganic materials 0.000 description 21
- 150000003254 radicals Chemical group 0.000 description 21
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 20
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 19
- 125000005394 methallyl group Chemical group 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 238000001035 drying Methods 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 17
- 238000004132 cross linking Methods 0.000 description 16
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 16
- 239000012429 reaction media Substances 0.000 description 16
- YHESWXAODSYVCO-UHFFFAOYSA-N 5-but-1-enylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=CCC)CC1C=C2 YHESWXAODSYVCO-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 229910052716 thallium Inorganic materials 0.000 description 15
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 15
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- 229920001577 copolymer Polymers 0.000 description 14
- 230000008569 process Effects 0.000 description 14
- 229910010199 LiAl Inorganic materials 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 12
- 239000007983 Tris buffer Substances 0.000 description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
- 125000000524 functional group Chemical group 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 229910052709 silver Inorganic materials 0.000 description 12
- 239000004332 silver Substances 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- OTTZHAVKAVGASB-UHFFFAOYSA-N 2-heptene Natural products CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 11
- 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 11
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 11
- 229910052805 deuterium Inorganic materials 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- LJKNRSBEKUSSIE-UHFFFAOYSA-N hept-2-ene Chemical compound [CH2]CCCC=CC LJKNRSBEKUSSIE-UHFFFAOYSA-N 0.000 description 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 description 11
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 11
- 238000004679 31P NMR spectroscopy Methods 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000002841 Lewis acid Substances 0.000 description 10
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 10
- 239000012190 activator Substances 0.000 description 10
- 150000007517 lewis acids Chemical class 0.000 description 10
- 229910052749 magnesium Inorganic materials 0.000 description 10
- 239000011777 magnesium Substances 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 125000001145 hydrido group Chemical group *[H] 0.000 description 9
- 239000003999 initiator Substances 0.000 description 9
- 150000002902 organometallic compounds Chemical class 0.000 description 9
- 239000002002 slurry Substances 0.000 description 9
- DHWBYAACHDUFAT-UHFFFAOYSA-N tricyclopentylphosphane Chemical compound C1CCCC1P(C1CCCC1)C1CCCC1 DHWBYAACHDUFAT-UHFFFAOYSA-N 0.000 description 9
- 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 description 8
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 description 8
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- 238000000434 field desorption mass spectrometry Methods 0.000 description 1
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- AEBDJCUTXUYLDC-UHFFFAOYSA-N methyl 5-methylbicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2C(C(=O)OC)(C)CC1C=C2 AEBDJCUTXUYLDC-UHFFFAOYSA-N 0.000 description 1
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- VRLDDYIKZCBFEZ-UHFFFAOYSA-N trimethoxy(phenyl)phosphanium Chemical compound CO[P+](OC)(OC)C1=CC=CC=C1 VRLDDYIKZCBFEZ-UHFFFAOYSA-N 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-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
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- ZMBHCYHQLYEYDV-UHFFFAOYSA-N trioctylphosphine oxide Chemical compound CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC ZMBHCYHQLYEYDV-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
- HVYVMSPIJIWUNA-UHFFFAOYSA-N triphenylstibine Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 HVYVMSPIJIWUNA-UHFFFAOYSA-N 0.000 description 1
- QOPBTFMUVTXWFF-UHFFFAOYSA-N tripropyl phosphite Chemical compound CCCOP(OCCC)OCCC QOPBTFMUVTXWFF-UHFFFAOYSA-N 0.000 description 1
- KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 0.000 description 1
- POHPFVPVRKJHCR-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)alumane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1[Al](C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F POHPFVPVRKJHCR-UHFFFAOYSA-N 0.000 description 1
- FQLSDFNKTNBQLC-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)phosphane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1P(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F FQLSDFNKTNBQLC-UHFFFAOYSA-N 0.000 description 1
- IDXDWPWXHTXJMZ-UHFFFAOYSA-N tris(2,4,6-trimethylphenyl)phosphane Chemical compound CC1=CC(C)=CC(C)=C1P(C=1C(=CC(C)=CC=1C)C)C1=C(C)C=C(C)C=C1C IDXDWPWXHTXJMZ-UHFFFAOYSA-N 0.000 description 1
- CMLWFCUAXGSMBB-UHFFFAOYSA-N tris(2,6-dimethoxyphenyl)phosphane Chemical compound COC1=CC=CC(OC)=C1P(C=1C(=CC=CC=1OC)OC)C1=C(OC)C=CC=C1OC CMLWFCUAXGSMBB-UHFFFAOYSA-N 0.000 description 1
- LZTKJXHKOLJIHI-UHFFFAOYSA-N tris(2-fluorophenyl)phosphane Chemical compound FC1=CC=CC=C1P(C=1C(=CC=CC=1)F)C1=CC=CC=C1F LZTKJXHKOLJIHI-UHFFFAOYSA-N 0.000 description 1
- IIOSDXGZLBPOHD-UHFFFAOYSA-N tris(2-methoxyphenyl)phosphane Chemical compound COC1=CC=CC=C1P(C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC IIOSDXGZLBPOHD-UHFFFAOYSA-N 0.000 description 1
- 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
- QAPGHLJQIVDTPT-UHFFFAOYSA-N tris(3-chlorophenyl)phosphane Chemical compound ClC1=CC=CC(P(C=2C=C(Cl)C=CC=2)C=2C=C(Cl)C=CC=2)=C1 QAPGHLJQIVDTPT-UHFFFAOYSA-N 0.000 description 1
- CUTRINLXFPIWQB-UHFFFAOYSA-N tris(3-fluorophenyl)phosphane Chemical compound FC1=CC=CC(P(C=2C=C(F)C=CC=2)C=2C=C(F)C=CC=2)=C1 CUTRINLXFPIWQB-UHFFFAOYSA-N 0.000 description 1
- CCXTYQMZVYIQRP-UHFFFAOYSA-N tris(3-methoxyphenyl)phosphane Chemical compound COC1=CC=CC(P(C=2C=C(OC)C=CC=2)C=2C=C(OC)C=CC=2)=C1 CCXTYQMZVYIQRP-UHFFFAOYSA-N 0.000 description 1
- APRCRSUXFGXHEL-UHFFFAOYSA-N tris(3-methoxypropyl)phosphane Chemical compound COCCCP(CCCOC)CCCOC APRCRSUXFGXHEL-UHFFFAOYSA-N 0.000 description 1
- IQKSLJOIKWOGIZ-UHFFFAOYSA-N tris(4-chlorophenyl)phosphane Chemical compound C1=CC(Cl)=CC=C1P(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 IQKSLJOIKWOGIZ-UHFFFAOYSA-N 0.000 description 1
- FEVFLQDDNUQKRY-UHFFFAOYSA-N tris(4-methylphenyl) phosphite Chemical compound C1=CC(C)=CC=C1OP(OC=1C=CC(C)=CC=1)OC1=CC=C(C)C=C1 FEVFLQDDNUQKRY-UHFFFAOYSA-N 0.000 description 1
- MXLDRFIVBLWESA-UHFFFAOYSA-N tris(trifluoromethyl)phosphane Chemical compound FC(F)(F)P(C(F)(F)F)C(F)(F)F MXLDRFIVBLWESA-UHFFFAOYSA-N 0.000 description 1
- OUMZKMRZMVDEOF-UHFFFAOYSA-N tris(trimethylsilyl)phosphane Chemical compound C[Si](C)(C)P([Si](C)(C)C)[Si](C)(C)C OUMZKMRZMVDEOF-UHFFFAOYSA-N 0.000 description 1
- SWPCNGVHIJTPJJ-UHFFFAOYSA-N tris(trimethylsilyl)silanylium Chemical compound C[Si](C)(C)[Si+]([Si](C)(C)C)[Si](C)(C)C SWPCNGVHIJTPJJ-UHFFFAOYSA-N 0.000 description 1
- BPKXQSLAVGBZEM-UHFFFAOYSA-N tris[3,5-bis(trifluoromethyl)phenyl]borane Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(B(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C1 BPKXQSLAVGBZEM-UHFFFAOYSA-N 0.000 description 1
- ITJHLZVYLDBFOJ-UHFFFAOYSA-N tris[3,5-bis(trifluoromethyl)phenyl]phosphane Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(P(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C1 ITJHLZVYLDBFOJ-UHFFFAOYSA-N 0.000 description 1
- RWVACGVJXRKMIZ-UHFFFAOYSA-N tris[4-(trifluoromethyl)phenyl] phosphite Chemical compound C1=CC(C(F)(F)F)=CC=C1OP(OC=1C=CC(=CC=1)C(F)(F)F)OC1=CC=C(C(F)(F)F)C=C1 RWVACGVJXRKMIZ-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
- KUCPTMZJPDVWJL-UHFFFAOYSA-N trithiophen-2-ylphosphane Chemical compound C1=CSC(P(C=2SC=CC=2)C=2SC=CC=2)=C1 KUCPTMZJPDVWJL-UHFFFAOYSA-N 0.000 description 1
- 238000004017 vitrification Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F32/00—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F32/00—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F32/08—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having two condensed rings
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2003287068A AU2003287068A1 (en) | 2002-10-15 | 2003-10-14 | Polymerized cycloolefins using transition metal catalyst and end products thereof |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/271,393 US6903171B2 (en) | 1998-10-05 | 2002-10-15 | Polymerized cycloolefins using transition metal catalyst and end products thereof |
US10/271,393 | 2002-10-15 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2004035636A2 true WO2004035636A2 (en) | 2004-04-29 |
WO2004035636A3 WO2004035636A3 (en) | 2005-01-13 |
Family
ID=32106416
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2003/032474 WO2004035636A2 (en) | 2002-10-15 | 2003-10-14 | Polymerized cycloolefins using transition metal catalyst and end products thereof |
Country Status (3)
Country | Link |
---|---|
US (2) | US6903171B2 (US06903171-20050607-C00043.png) |
AU (1) | AU2003287068A1 (US06903171-20050607-C00043.png) |
WO (1) | WO2004035636A2 (US06903171-20050607-C00043.png) |
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-
2002
- 2002-10-15 US US10/271,393 patent/US6903171B2/en not_active Expired - Lifetime
-
2003
- 2003-06-18 US US10/464,978 patent/US7910674B2/en not_active Expired - Lifetime
- 2003-10-14 AU AU2003287068A patent/AU2003287068A1/en not_active Abandoned
- 2003-10-14 WO PCT/US2003/032474 patent/WO2004035636A2/en not_active Application Discontinuation
Patent Citations (3)
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WO2000020472A1 (en) * | 1998-10-05 | 2000-04-13 | The B.F. Goodrich Company | Catalyst and methods for polymerizing cycloolefins |
WO2002010231A2 (en) * | 2000-07-28 | 2002-02-07 | Goodrich Corporation | Polymeric compositions for forming optical waveguides; optical waveguides formed therefrom; and methods for making same |
EP1195397A1 (en) * | 2000-10-04 | 2002-04-10 | JSR Corporation | Composition of cyclic olefin addition copolymer and cross-linked material |
Non-Patent Citations (1)
Title |
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DATABASE CHEMABS [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 22 May 2002 (2002-05-22) KANAMORI, TARO ET AL: "Heat- and water-resistant transparent cycloolefin polymer compositions containing organosilanes, their manufacture, and their use for optical materials" retrieved from STN Database accession no. 2002:381399 XP002276662 & JP 2002 146145 A2 (JSR LTD., JAPAN) 22 May 2002 (2002-05-22) * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103745257A (zh) * | 2013-12-23 | 2014-04-23 | 温州医科大学眼视光器械有限公司 | 一种基于图像识别的锥细胞密度的计算方法 |
CN103745257B (zh) * | 2013-12-23 | 2016-08-17 | 温州医科大学眼视光器械有限公司 | 一种基于图像识别的锥细胞密度的计算方法 |
Also Published As
Publication number | Publication date |
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AU2003287068A1 (en) | 2004-05-04 |
US7910674B2 (en) | 2011-03-22 |
US20040048994A1 (en) | 2004-03-11 |
AU2003287068A8 (en) | 2004-05-04 |
US6903171B2 (en) | 2005-06-07 |
WO2004035636A3 (en) | 2005-01-13 |
US20030181607A1 (en) | 2003-09-25 |
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