CA2999864A1 - Metal carbene olefin metathesis catalysts - Google Patents
Metal carbene olefin metathesis catalysts Download PDFInfo
- Publication number
- CA2999864A1 CA2999864A1 CA2999864A CA2999864A CA2999864A1 CA 2999864 A1 CA2999864 A1 CA 2999864A1 CA 2999864 A CA2999864 A CA 2999864A CA 2999864 A CA2999864 A CA 2999864A CA 2999864 A1 CA2999864 A1 CA 2999864A1
- Authority
- CA
- Canada
- Prior art keywords
- substituted
- trans
- phenyl
- alkyl
- 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.)
- Abandoned
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 187
- 238000005865 alkene metathesis reaction Methods 0.000 title claims abstract description 113
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 110
- 239000002184 metal Substances 0.000 title claims abstract description 110
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 title claims abstract description 107
- -1 olefin compounds Chemical class 0.000 claims abstract description 273
- 239000000203 mixture Substances 0.000 claims abstract description 81
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 52
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 194
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 178
- 125000005842 heteroatom Chemical group 0.000 claims description 145
- 239000001257 hydrogen Substances 0.000 claims description 101
- 229910052739 hydrogen Inorganic materials 0.000 claims description 101
- 125000001424 substituent group Chemical group 0.000 claims description 96
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 claims description 62
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 58
- 125000000524 functional group Chemical group 0.000 claims description 57
- 239000011342 resin composition Substances 0.000 claims description 56
- 239000003446 ligand Substances 0.000 claims description 47
- 150000004820 halides Chemical class 0.000 claims description 46
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 35
- 125000005538 phosphinite group Chemical group 0.000 claims description 30
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 23
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 14
- 125000003518 norbornenyl group Chemical class C12(C=CC(CC1)C2)* 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 10
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
- 229920002554 vinyl polymer Chemical group 0.000 claims description 8
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 2
- 125000006735 (C1-C20) heteroalkyl group Chemical group 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 29
- 238000000034 method Methods 0.000 abstract description 24
- 238000005649 metathesis reaction Methods 0.000 abstract description 21
- 229920000642 polymer Polymers 0.000 abstract description 21
- 238000004519 manufacturing process Methods 0.000 abstract description 18
- 150000001336 alkenes Chemical class 0.000 abstract description 10
- 238000002360 preparation method Methods 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 239000012847 fine chemical Substances 0.000 abstract description 2
- 239000003317 industrial substance Substances 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 description 130
- 125000000217 alkyl group Chemical group 0.000 description 109
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 88
- 239000007787 solid Substances 0.000 description 75
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 70
- 238000006243 chemical reaction Methods 0.000 description 70
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 56
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 56
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 51
- 125000004432 carbon atom Chemical group C* 0.000 description 44
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 239000002904 solvent Substances 0.000 description 41
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 125000000743 hydrocarbylene group Chemical group 0.000 description 36
- 125000004122 cyclic group Chemical group 0.000 description 34
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 33
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 33
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 32
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 32
- 239000000243 solution Substances 0.000 description 32
- 229910052757 nitrogen Inorganic materials 0.000 description 31
- 229920006395 saturated elastomer Polymers 0.000 description 31
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
- 239000011521 glass Substances 0.000 description 29
- 125000004404 heteroalkyl group Chemical group 0.000 description 29
- 235000010290 biphenyl Nutrition 0.000 description 28
- 239000004305 biphenyl Substances 0.000 description 28
- 125000003545 alkoxy group Chemical group 0.000 description 27
- 238000003756 stirring Methods 0.000 description 27
- 125000003342 alkenyl group Chemical group 0.000 description 26
- 238000005481 NMR spectroscopy Methods 0.000 description 25
- 239000000047 product Substances 0.000 description 25
- 125000002723 alicyclic group Chemical group 0.000 description 24
- 229910052799 carbon Inorganic materials 0.000 description 24
- 239000000839 emulsion Substances 0.000 description 24
- LMZLQYYLELWCCW-UHFFFAOYSA-N dimethoxy(phenyl)phosphane Chemical compound COP(OC)C1=CC=CC=C1 LMZLQYYLELWCCW-UHFFFAOYSA-N 0.000 description 23
- ADLVDYMTBOSDFE-UHFFFAOYSA-N 5-chloro-6-nitroisoindole-1,3-dione Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC2=C1C(=O)NC2=O ADLVDYMTBOSDFE-UHFFFAOYSA-N 0.000 description 22
- 125000000304 alkynyl group Chemical group 0.000 description 22
- 239000004593 Epoxy Substances 0.000 description 21
- 239000002318 adhesion promoter Substances 0.000 description 21
- 239000000463 material Substances 0.000 description 21
- 238000004513 sizing Methods 0.000 description 21
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 20
- 239000004744 fabric Substances 0.000 description 20
- 239000003921 oil Substances 0.000 description 19
- 101150041968 CDC13 gene Proteins 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 235000019198 oils Nutrition 0.000 description 18
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 18
- 125000005647 linker group Chemical group 0.000 description 17
- 239000000178 monomer Substances 0.000 description 17
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 16
- 239000007788 liquid Substances 0.000 description 16
- 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 15
- 125000002619 bicyclic group Chemical group 0.000 description 15
- 239000000654 additive Substances 0.000 description 14
- 229920005989 resin Polymers 0.000 description 14
- 239000011347 resin Substances 0.000 description 14
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 14
- 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 14
- 238000004679 31P NMR spectroscopy Methods 0.000 description 13
- 125000002877 alkyl aryl group Chemical group 0.000 description 13
- 125000003710 aryl alkyl group Chemical group 0.000 description 13
- 229910052707 ruthenium Inorganic materials 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- 239000000741 silica gel Substances 0.000 description 13
- 229960001866 silicon dioxide Drugs 0.000 description 13
- 229920002633 Kraton (polymer) Polymers 0.000 description 12
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 12
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
- 229920000049 Carbon (fiber) Polymers 0.000 description 11
- 239000000499 gel Substances 0.000 description 11
- 239000000314 lubricant Substances 0.000 description 11
- 230000002829 reductive effect Effects 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 10
- 125000003367 polycyclic group Chemical group 0.000 description 10
- 230000002787 reinforcement Effects 0.000 description 10
- 239000013638 trimer Substances 0.000 description 10
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000003963 antioxidant agent Substances 0.000 description 9
- 125000004429 atom Chemical group 0.000 description 9
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 9
- 239000002131 composite material Substances 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 9
- 239000002002 slurry Substances 0.000 description 9
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 8
- 229920001971 elastomer Polymers 0.000 description 8
- 239000003365 glass fiber Substances 0.000 description 8
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 8
- 238000000465 moulding Methods 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- 239000004760 aramid Substances 0.000 description 7
- 125000004104 aryloxy group Chemical group 0.000 description 7
- 239000004917 carbon fiber Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 125000005442 diisocyanate group Chemical group 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 239000000835 fiber Substances 0.000 description 7
- 125000001841 imino group Chemical group [H]N=* 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- 125000002950 monocyclic group Chemical group 0.000 description 7
- 229910052698 phosphorus Inorganic materials 0.000 description 7
- 229920000098 polyolefin Polymers 0.000 description 7
- 239000012779 reinforcing material Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000004609 Impact Modifier Substances 0.000 description 6
- 239000005062 Polybutadiene Substances 0.000 description 6
- 239000004698 Polyethylene Substances 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 238000005266 casting Methods 0.000 description 6
- 239000000919 ceramic Substances 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 230000000670 limiting effect Effects 0.000 description 6
- 239000003607 modifier Substances 0.000 description 6
- 229920002857 polybutadiene Polymers 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 239000006228 supernatant Substances 0.000 description 6
- 229910052723 transition metal Inorganic materials 0.000 description 6
- 150000003624 transition metals Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- OJOWICOBYCXEKR-APPZFPTMSA-N (1S,4R)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound CC=C1C[C@@H]2C[C@@H]1C=C2 OJOWICOBYCXEKR-APPZFPTMSA-N 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 5
- 238000011068 loading method Methods 0.000 description 5
- 239000004005 microsphere Substances 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
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- 229920000573 polyethylene Polymers 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 229920005996 polystyrene-poly(ethylene-butylene)-polystyrene Polymers 0.000 description 5
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- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Natural products C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 5
- 125000006686 (C1-C24) alkyl group Chemical group 0.000 description 4
- YXRKNIZYMIXSAD-UHFFFAOYSA-N 1,6-diisocyanatohexane Chemical compound O=C=NCCCCCCN=C=O.O=C=NCCCCCCN=C=O.O=C=NCCCCCCN=C=O YXRKNIZYMIXSAD-UHFFFAOYSA-N 0.000 description 4
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 4
- 239000004971 Cross linker Substances 0.000 description 4
- 229920002943 EPDM rubber Polymers 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000008186 active pharmaceutical agent Substances 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 150000008064 anhydrides Chemical group 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 125000005577 anthracene group Chemical group 0.000 description 4
- 229920003235 aromatic polyamide Polymers 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000013058 crude material Substances 0.000 description 4
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 239000000806 elastomer Substances 0.000 description 4
- 125000001033 ether group Chemical group 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- OAADXJFIBNEPLY-UHFFFAOYSA-N methoxy(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(OC)C1=CC=CC=C1 OAADXJFIBNEPLY-UHFFFAOYSA-N 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 239000004810 polytetrafluoroethylene Substances 0.000 description 4
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- 229920002635 polyurethane Polymers 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 238000007142 ring opening reaction Methods 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
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- 150000004756 silanes Chemical class 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 4
- 150000003568 thioethers Chemical class 0.000 description 4
- 238000001721 transfer moulding Methods 0.000 description 4
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 4
- 238000003828 vacuum filtration Methods 0.000 description 4
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 3
- 241000191291 Abies alba Species 0.000 description 3
- 235000004507 Abies alba Nutrition 0.000 description 3
- 101100275770 Caenorhabditis elegans cri-3 gene Proteins 0.000 description 3
- 102100029579 Diphosphoinositol polyphosphate phosphohydrolase 1 Human genes 0.000 description 3
- IIGAAOXXRKTFAM-UHFFFAOYSA-N N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C Chemical compound N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C IIGAAOXXRKTFAM-UHFFFAOYSA-N 0.000 description 3
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 3
- 229920002582 Polyethylene Glycol 600 Polymers 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 125000003158 alcohol group Chemical group 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
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- AOQUKZYKYIPBFR-UHFFFAOYSA-N trihydroxy-nonyl-phenyl-$l^{5}-phosphane Chemical compound CCCCCCCCCP(O)(O)(O)C1=CC=CC=C1 AOQUKZYKYIPBFR-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
- 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
- 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
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Classifications
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
-
- 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
- C08G61/08—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 of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
- B01J2231/54—Metathesis reactions, e.g. olefin metathesis
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/821—Ruthenium
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
- C08G2261/332—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms
- C08G2261/3324—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms derived from norbornene
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
- C08G2261/332—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms
- C08G2261/3325—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms derived from other polycyclic systems
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/40—Polymerisation processes
- C08G2261/41—Organometallic coupling reactions
- C08G2261/418—Ring opening metathesis polymerisation [ROMP]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Catalysts (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562222989P | 2015-09-24 | 2015-09-24 | |
| US62/222,989 | 2015-09-24 | ||
| PCT/US2016/053288 WO2017053690A1 (en) | 2015-09-24 | 2016-09-23 | Metal carbene olefin metathesis catalysts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2999864A1 true CA2999864A1 (en) | 2017-03-30 |
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ID=58387388
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2999864A Abandoned CA2999864A1 (en) | 2015-09-24 | 2016-09-23 | Metal carbene olefin metathesis catalysts |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US10501488B2 (OSRAM) |
| EP (1) | EP3353187B1 (OSRAM) |
| JP (2) | JP7013370B2 (OSRAM) |
| KR (1) | KR20180059489A (OSRAM) |
| CN (2) | CN108779134B (OSRAM) |
| BR (1) | BR112018005823A2 (OSRAM) |
| CA (1) | CA2999864A1 (OSRAM) |
| MX (1) | MX2018003639A (OSRAM) |
| PL (1) | PL3353187T3 (OSRAM) |
| WO (1) | WO2017053690A1 (OSRAM) |
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| CN108779134B (zh) * | 2015-09-24 | 2023-10-03 | 优美科股份公司及两合公司 | 金属卡宾烯烃易位催化剂 |
| KR102670566B1 (ko) * | 2019-01-18 | 2024-05-31 | 광주과학기술원 | 루테늄 착화합물, 이의 제조를 위한 리간드 및 이의 용도 |
| WO2020214399A2 (en) * | 2019-03-28 | 2020-10-22 | University Of Florida Research Foundation, Inc. | High temperature bulk metathesis polymerization |
| CN115819724A (zh) * | 2022-12-27 | 2023-03-21 | 上海中化科技有限公司 | 环氧-环烯烃树脂组合物、热固性树脂材料及其制备方法 |
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| US4899005A (en) | 1987-11-19 | 1990-02-06 | The B. F. Goodrich Company | Method for preparing cycloolefin copolymers with improved heat stability |
| US5204427A (en) | 1989-11-01 | 1993-04-20 | Nippon Zeon Co., Ltd. | Method of making ring-opened polynorbornene polymers using pot life extending agents |
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-
2016
- 2016-09-23 CN CN201680055546.4A patent/CN108779134B/zh active Active
- 2016-09-23 EP EP16849676.8A patent/EP3353187B1/en active Active
- 2016-09-23 CN CN202110611820.4A patent/CN113307830A/zh active Pending
- 2016-09-23 BR BR112018005823A patent/BR112018005823A2/pt not_active Application Discontinuation
- 2016-09-23 MX MX2018003639A patent/MX2018003639A/es unknown
- 2016-09-23 JP JP2018515840A patent/JP7013370B2/ja active Active
- 2016-09-23 WO PCT/US2016/053288 patent/WO2017053690A1/en not_active Ceased
- 2016-09-23 CA CA2999864A patent/CA2999864A1/en not_active Abandoned
- 2016-09-23 PL PL16849676T patent/PL3353187T3/pl unknown
- 2016-09-23 US US15/762,918 patent/US10501488B2/en active Active
- 2016-09-23 KR KR1020187011391A patent/KR20180059489A/ko not_active Withdrawn
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2021
- 2021-11-05 JP JP2021181172A patent/JP2022010098A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| MX2018003639A (es) | 2019-04-25 |
| CN108779134B (zh) | 2023-10-03 |
| CN108779134A (zh) | 2018-11-09 |
| CN113307830A (zh) | 2021-08-27 |
| BR112018005823A2 (pt) | 2018-10-16 |
| EP3353187A4 (en) | 2019-05-01 |
| EP3353187B1 (en) | 2021-07-21 |
| JP2018537546A (ja) | 2018-12-20 |
| US20180265532A1 (en) | 2018-09-20 |
| US10501488B2 (en) | 2019-12-10 |
| JP7013370B2 (ja) | 2022-01-31 |
| KR20180059489A (ko) | 2018-06-04 |
| JP2022010098A (ja) | 2022-01-14 |
| EP3353187A1 (en) | 2018-08-01 |
| PL3353187T3 (pl) | 2021-11-22 |
| WO2017053690A1 (en) | 2017-03-30 |
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