CA2539560A1 - Romp with fluorinated groups - Google Patents

Info

Publication number

CA2539560A1

CA2539560A1 CA002539560A CA2539560A CA2539560A1 CA 2539560 A1 CA2539560 A1 CA 2539560A1 CA 002539560 A CA002539560 A CA 002539560A CA 2539560 A CA2539560 A CA 2539560A CA 2539560 A1 CA2539560 A1 CA 2539560A1

Authority

CA

Canada

Prior art keywords

compound

formula

butyl

independently

bis

Prior art date

2003-09-25

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

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 239000000203 mixture Substances 0.000 claims abstract description 82
• 239000003054 catalyst Substances 0.000 claims abstract description 32
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 26
• 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 25
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 24
• 238000005649 metathesis reaction Methods 0.000 claims abstract description 16
• 239000011368 organic material Substances 0.000 claims abstract description 16
• HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims abstract description 11
• 229910052762 osmium Inorganic materials 0.000 claims abstract description 10
• SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims abstract description 10
• 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 claims abstract description 9
• 150000001875 compounds Chemical class 0.000 claims description 167
• -1 trifluoroethyl allyl ether Chemical compound 0.000 claims description 68
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 27
• 239000003921 oil Substances 0.000 claims description 23
• 150000001925 cycloalkenes Chemical class 0.000 claims description 18
• 239000000654 additive Substances 0.000 claims description 17
• 229910052731 fluorine Inorganic materials 0.000 claims description 17
• 239000003446 ligand Substances 0.000 claims 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 claims description 15
• JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 15
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 14
• 239000011737 fluorine Substances 0.000 claims description 14
• ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 13
• 239000000178 monomer Substances 0.000 claims description 13
• 229920001059 synthetic polymer Polymers 0.000 claims description 12
• 125000003118 aryl group Chemical group 0.000 claims description 10
• 239000012986 chain transfer agent Substances 0.000 claims description 10
• 239000003795 chemical substances by application Substances 0.000 claims description 9
• 238000000034 method Methods 0.000 claims description 8
• LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 6
• 230000007935 neutral effect Effects 0.000 claims description 6
• SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 claims description 6
• 239000003381 stabilizer Substances 0.000 claims description 6
• RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 5
• XIVPVSIDXBTZLM-UHFFFAOYSA-N prop-2-enyl 2,2,2-trifluoroacetate Chemical compound FC(F)(F)C(=O)OCC=C XIVPVSIDXBTZLM-UHFFFAOYSA-N 0.000 claims description 5
• ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims description 4
• 125000000129 anionic group Chemical group 0.000 claims description 4
• MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims description 4
• HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 4
• RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 claims description 3
• 125000005110 aryl thio group Chemical group 0.000 claims description 3
• 230000015556 catabolic process Effects 0.000 claims description 3
• URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 claims description 3
• 239000004913 cyclooctene Substances 0.000 claims description 3
• 238000006731 degradation reaction Methods 0.000 claims description 3
• 239000004611 light stabiliser Substances 0.000 claims description 3
• 230000008569 process Effects 0.000 claims description 3
• 238000012545 processing Methods 0.000 claims description 3
• GWYPDXLJACEENP-UHFFFAOYSA-N 1,3-cycloheptadiene Chemical compound C1CC=CC=CC1 GWYPDXLJACEENP-UHFFFAOYSA-N 0.000 claims description 2
• CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-UHFFFAOYSA-N 0.000 claims description 2
• ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 claims description 2
• OOXWYYGXTJLWHA-UHFFFAOYSA-N cyclopropene Chemical compound C1C=C1 OOXWYYGXTJLWHA-UHFFFAOYSA-N 0.000 claims description 2
• 230000001590 oxidative effect Effects 0.000 claims description 2
• 239000002530 phenolic antioxidant Substances 0.000 claims description 2
• 238000009740 moulding (composite fabrication) Methods 0.000 claims 1
• 238000006243 chemical reaction Methods 0.000 abstract description 6
• 238000004519 manufacturing process Methods 0.000 abstract description 2
• 235000013350 formula milk Nutrition 0.000 description 143
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 84
• 238000002360 preparation method Methods 0.000 description 60
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 47
• 229920001577 copolymer Polymers 0.000 description 47
• 239000011541 reaction mixture Substances 0.000 description 40
• 239000000243 solution Substances 0.000 description 39
• 229920000642 polymer Polymers 0.000 description 36
• 239000002904 solvent Substances 0.000 description 25
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 23
• 238000001704 evaporation Methods 0.000 description 20
• 230000008020 evaporation Effects 0.000 description 20
• 235000019198 oils Nutrition 0.000 description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
• 229920005989 resin Polymers 0.000 description 15
• 239000011347 resin Substances 0.000 description 15
• 125000003963 dichloro group Chemical group Cl* 0.000 description 14
• DHWBYAACHDUFAT-UHFFFAOYSA-N tricyclopentylphosphane Chemical compound C1CCCC1P(C1CCCC1)C1CCCC1 DHWBYAACHDUFAT-UHFFFAOYSA-N 0.000 description 14
• 238000005481 NMR spectroscopy Methods 0.000 description 13
• 150000002148 esters Chemical class 0.000 description 13
• 229910052757 nitrogen Inorganic materials 0.000 description 13
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 11
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 11
• 239000005977 Ethylene Substances 0.000 description 11
• 239000004952 Polyamide Substances 0.000 description 11
• 239000004743 Polypropylene Substances 0.000 description 11
• RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 11
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
• BJFLSHMHTPAZHO-UHFFFAOYSA-N benzotriazole Chemical compound [CH]1C=CC=C2N=NN=C21 BJFLSHMHTPAZHO-UHFFFAOYSA-N 0.000 description 10
• 239000012964 benzotriazole Substances 0.000 description 10
• 229910052736 halogen Inorganic materials 0.000 description 10
• 150000002367 halogens Chemical class 0.000 description 10
• 229920002554 vinyl polymer Polymers 0.000 description 10
• LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 9
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
• NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 9
• 238000000465 moulding Methods 0.000 description 9
• 229920002647 polyamide Polymers 0.000 description 9
• KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 8
• 239000005062 Polybutadiene Substances 0.000 description 8
• 150000001412 amines Chemical class 0.000 description 8
• FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 8
• KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
• 239000012230 colorless oil Substances 0.000 description 8
• 150000001993 dienes Chemical class 0.000 description 8
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
• 239000000835 fiber Substances 0.000 description 8
• 229920001684 low density polyethylene Polymers 0.000 description 8
• 239000004702 low-density polyethylene Substances 0.000 description 8
• 239000000463 material Substances 0.000 description 8
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
• 229920002857 polybutadiene Polymers 0.000 description 8
• 239000007983 Tris buffer Substances 0.000 description 7
• 229910052799 carbon Inorganic materials 0.000 description 7
• 229910052751 metal Inorganic materials 0.000 description 7
• 239000002184 metal Substances 0.000 description 7
• 229920006324 polyoxymethylene Polymers 0.000 description 7
• 229920001155 polypropylene Polymers 0.000 description 7
• 125000001424 substituent group Chemical group 0.000 description 7
• 229910019142 PO4 Inorganic materials 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
• 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
• 125000000217 alkyl group Chemical group 0.000 description 6
• DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
• 239000010408 film Substances 0.000 description 6
• 239000004700 high-density polyethylene Substances 0.000 description 6
• TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 6
• 229920000728 polyester Polymers 0.000 description 6
• 229920000098 polyolefin Polymers 0.000 description 6
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
• 239000004721 Polyphenylene oxide Substances 0.000 description 5
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
• 239000002253 acid Substances 0.000 description 5
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
• BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 5
• 150000008064 anhydrides Chemical class 0.000 description 5
• 238000004821 distillation Methods 0.000 description 5
• 239000011521 glass Substances 0.000 description 5
• 229920001903 high density polyethylene Polymers 0.000 description 5
• 229920001519 homopolymer Polymers 0.000 description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
• WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
• 235000021317 phosphate Nutrition 0.000 description 5
• 150000003013 phosphoric acid derivatives Chemical class 0.000 description 5
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• 239000007787 solid Substances 0.000 description 5
• 150000005846 sugar alcohols Polymers 0.000 description 5
• 238000012360 testing method Methods 0.000 description 5
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
• DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
• BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 4
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• ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 4
• CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
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• OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 4
• 229920000877 Melamine resin Polymers 0.000 description 4
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
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• ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
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• 150000002170 ethers Chemical class 0.000 description 4
• 239000007789 gas Substances 0.000 description 4
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• 238000009413 insulation Methods 0.000 description 4
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• RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 3
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• 239000011248 coating agent Substances 0.000 description 3
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• 239000004744 fabric Substances 0.000 description 3
• 238000001914 filtration Methods 0.000 description 3
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• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
• 229920000554 ionomer Polymers 0.000 description 3
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• FDAKZQLBIFPGSV-UHFFFAOYSA-N n-butyl-2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CCCCNC1CC(C)(C)NC(C)(C)C1 FDAKZQLBIFPGSV-UHFFFAOYSA-N 0.000 description 3
• OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
• 238000012856 packing Methods 0.000 description 3
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• 150000003003 phosphines Chemical class 0.000 description 3
• 229920001281 polyalkylene Polymers 0.000 description 3
• 229920001707 polybutylene terephthalate Polymers 0.000 description 3
• 229920000515 polycarbonate Polymers 0.000 description 3
• 125000003367 polycyclic group Chemical group 0.000 description 3
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• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
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