CA2345798C - Polyolefin graft copolymers made with fluorinated monomers - Google Patents
Polyolefin graft copolymers made with fluorinated monomers Download PDFInfo
- Publication number
- CA2345798C CA2345798C CA002345798A CA2345798A CA2345798C CA 2345798 C CA2345798 C CA 2345798C CA 002345798 A CA002345798 A CA 002345798A CA 2345798 A CA2345798 A CA 2345798A CA 2345798 C CA2345798 C CA 2345798C
- Authority
- CA
- Canada
- Prior art keywords
- olefin
- ethylene
- alpha
- propylene
- copolymer
- 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.)
- Expired - Fee Related
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- 239000000178 monomer Substances 0.000 title claims abstract description 153
- 229920000098 polyolefin Polymers 0.000 title claims abstract description 89
- 229920000578 graft copolymer Polymers 0.000 title claims abstract description 61
- 239000002861 polymer material Substances 0.000 claims abstract description 78
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 77
- 238000000034 method Methods 0.000 claims abstract description 22
- 150000002148 esters Chemical class 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 18
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000011737 fluorine Substances 0.000 claims abstract description 17
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 80
- 239000005977 Ethylene Substances 0.000 claims description 80
- 239000004711 α-olefin Substances 0.000 claims description 74
- -1 unsaturated aliphatic nitrites Chemical class 0.000 claims description 73
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 47
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 46
- 150000001336 alkenes Chemical class 0.000 claims description 41
- 229920001577 copolymer Polymers 0.000 claims description 40
- 229920001384 propylene homopolymer Polymers 0.000 claims description 32
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 27
- 239000011148 porous material Substances 0.000 claims description 21
- 150000001334 alicyclic compounds Chemical class 0.000 claims description 18
- 150000001491 aromatic compounds Chemical class 0.000 claims description 17
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 17
- 230000001590 oxidative effect Effects 0.000 claims description 17
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 16
- 239000008096 xylene Substances 0.000 claims description 16
- 125000001153 fluoro group Chemical group F* 0.000 claims description 15
- 238000010438 heat treatment Methods 0.000 claims description 15
- 229920001897 terpolymer Polymers 0.000 claims description 14
- 239000002245 particle Substances 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 11
- 239000007870 radical polymerization initiator Substances 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 238000001816 cooling Methods 0.000 claims description 9
- 238000000354 decomposition reaction Methods 0.000 claims description 9
- 150000002894 organic compounds Chemical class 0.000 claims description 9
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 8
- 150000001993 dienes Chemical class 0.000 claims description 8
- 229920001519 homopolymer Polymers 0.000 claims description 7
- 229920002397 thermoplastic olefin Polymers 0.000 claims description 6
- 125000003118 aryl group Chemical class 0.000 claims description 5
- 229920005606 polypropylene copolymer Polymers 0.000 claims description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical class 0.000 claims description 4
- 229920001198 elastomeric copolymer Polymers 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229920000092 linear low density polyethylene Polymers 0.000 claims description 2
- 239000004707 linear low-density polyethylene Substances 0.000 claims description 2
- 229920005604 random copolymer Polymers 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 3
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 abstract description 18
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 12
- 239000001301 oxygen Substances 0.000 abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 abstract description 12
- 239000003999 initiator Substances 0.000 abstract description 11
- 150000002978 peroxides Chemical class 0.000 abstract description 7
- 230000004888 barrier function Effects 0.000 abstract description 6
- 150000001451 organic peroxides Chemical class 0.000 abstract description 3
- 238000010559 graft polymerization reaction Methods 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 21
- 239000002033 PVDF binder Substances 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 16
- 239000012298 atmosphere Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 125000005395 methacrylic acid group Chemical group 0.000 description 9
- 229920001155 polypropylene Polymers 0.000 description 9
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 8
- 239000004743 Polypropylene Substances 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 5
- 239000004926 polymethyl methacrylate Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 229940057404 di-(4-tert-butylcyclohexyl)peroxydicarbonate Drugs 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 230000009965 odorless effect Effects 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 235000015096 spirit Nutrition 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 229940063557 methacrylate Drugs 0.000 description 3
- 150000004978 peroxycarbonates Chemical class 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- DFVPUWGVOPDJTC-UHFFFAOYSA-N 2,2,3,4,4,4-hexafluorobutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)C(F)C(F)(F)F DFVPUWGVOPDJTC-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229920002313 fluoropolymer Polymers 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 238000002459 porosimetry Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- HGXJDMCMYLEZMJ-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOOC(=O)C(C)(C)C HGXJDMCMYLEZMJ-UHFFFAOYSA-N 0.000 description 1
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 1
- FMQPBWHSNCRVQJ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C(F)(F)F)C(F)(F)F FMQPBWHSNCRVQJ-UHFFFAOYSA-N 0.000 description 1
- GWYSWOQRJGLJPA-UHFFFAOYSA-N 1,1,2,2-tetrafluoropropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(F)(F)C(C)(F)F GWYSWOQRJGLJPA-UHFFFAOYSA-N 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 1
- STOKTJCBSPVXAK-UHFFFAOYSA-N 1-(4-hydroxy-2-methylpentan-2-yl)peroxyethyl hexanoate Chemical compound CCCCCC(=O)OC(C)OOC(C)(C)CC(C)O STOKTJCBSPVXAK-UHFFFAOYSA-N 0.000 description 1
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical compound CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- VBHXIMACZBQHPX-UHFFFAOYSA-N 2,2,2-trifluoroethyl prop-2-enoate Chemical compound FC(F)(F)COC(=O)C=C VBHXIMACZBQHPX-UHFFFAOYSA-N 0.000 description 1
- JDVGNKIUXZQTFD-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropyl prop-2-enoate Chemical compound FC(F)(F)C(F)(F)COC(=O)C=C JDVGNKIUXZQTFD-UHFFFAOYSA-N 0.000 description 1
- UOKXSSAMUUASQX-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,5-nonafluoropentyl prop-2-enoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)COC(=O)C=C UOKXSSAMUUASQX-UHFFFAOYSA-N 0.000 description 1
- JFDAGRQBXXAVSD-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl prop-2-enoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)COC(=O)C=C JFDAGRQBXXAVSD-UHFFFAOYSA-N 0.000 description 1
- RPHIWWKRMBRETN-UHFFFAOYSA-N 2,2,3,3,4,4-hexafluorobutyl prop-2-enoate Chemical compound FC(F)C(F)(F)C(F)(F)COC(=O)C=C RPHIWWKRMBRETN-UHFFFAOYSA-N 0.000 description 1
- VHJHZYSXJKREEE-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropyl prop-2-enoate Chemical compound FC(F)C(F)(F)COC(=O)C=C VHJHZYSXJKREEE-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- VLSRKCIBHNJFHA-UHFFFAOYSA-N 2-(trifluoromethyl)prop-2-enoic acid Chemical compound OC(=O)C(=C)C(F)(F)F VLSRKCIBHNJFHA-UHFFFAOYSA-N 0.000 description 1
- DJXNLVJQMJNEMN-UHFFFAOYSA-N 2-[difluoro(methoxy)methyl]-1,1,1,2,3,3,3-heptafluoropropane Chemical compound COC(F)(F)C(F)(C(F)(F)F)C(F)(F)F DJXNLVJQMJNEMN-UHFFFAOYSA-N 0.000 description 1
- NGFUZFAPKBLICJ-UHFFFAOYSA-N 2-but-1-enylpyridine Chemical compound CCC=CC1=CC=CC=N1 NGFUZFAPKBLICJ-UHFFFAOYSA-N 0.000 description 1
- VCWDAHMQCOZVQD-UHFFFAOYSA-N 2-chloroprop-1-enylbenzene Chemical compound CC(Cl)=CC1=CC=CC=C1 VCWDAHMQCOZVQD-UHFFFAOYSA-N 0.000 description 1
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- ZACVGCNKGYYQHA-UHFFFAOYSA-N 2-ethylhexoxycarbonyloxy 2-ethylhexyl carbonate Chemical compound CCCCC(CC)COC(=O)OOC(=O)OCC(CC)CCCC ZACVGCNKGYYQHA-UHFFFAOYSA-N 0.000 description 1
- SMTDFMMXJHYDDE-UHFFFAOYSA-N 2-prop-1-enylpyridine Chemical compound CC=CC1=CC=CC=N1 SMTDFMMXJHYDDE-UHFFFAOYSA-N 0.000 description 1
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- FNUBKINEQIEODM-UHFFFAOYSA-N 3,3,4,4,5,5,5-heptafluoropentanal Chemical compound FC(F)(F)C(F)(F)C(F)(F)CC=O FNUBKINEQIEODM-UHFFFAOYSA-N 0.000 description 1
- TYNRPOFACABVSI-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,6-nonafluorohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)F TYNRPOFACABVSI-UHFFFAOYSA-N 0.000 description 1
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- 239000000898 Thymopoietin Substances 0.000 description 1
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- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
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- 238000000071 blow moulding Methods 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000001569 carbon dioxide Substances 0.000 description 1
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- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
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- 239000000945 filler Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
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- 230000001678 irradiating effect Effects 0.000 description 1
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- 125000002950 monocyclic group Chemical group 0.000 description 1
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- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000004663 powder metallurgy Methods 0.000 description 1
- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
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
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
- C08F255/02—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/36—After-treatment
- C08J9/40—Impregnation
- C08J9/405—Impregnation with polymerisable 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
- C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F214/18—Monomers containing fluorine
- C08F214/22—Vinylidene fluoride
-
- 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
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/364,444 | 1999-07-30 | ||
| US09/364,444 US6337373B1 (en) | 1999-07-30 | 1999-07-30 | Polyolefin graft copolymers made with fluorinated monomers |
| PCT/IB2000/001022 WO2001009209A1 (en) | 1999-07-30 | 2000-07-24 | Polyolefin graft copolymers made with fluorinated monomers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2345798A1 CA2345798A1 (en) | 2001-02-08 |
| CA2345798C true CA2345798C (en) | 2007-05-08 |
Family
ID=23434557
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002345798A Expired - Fee Related CA2345798C (en) | 1999-07-30 | 2000-07-24 | Polyolefin graft copolymers made with fluorinated monomers |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US6337373B1 (enExample) |
| EP (1) | EP1127083B1 (enExample) |
| JP (1) | JP4773658B2 (enExample) |
| KR (2) | KR100751608B1 (enExample) |
| CN (1) | CN1237083C (enExample) |
| AR (1) | AR030677A1 (enExample) |
| AT (1) | ATE373028T1 (enExample) |
| AU (1) | AU5702700A (enExample) |
| BR (1) | BR0007068B1 (enExample) |
| CA (1) | CA2345798C (enExample) |
| DE (1) | DE60036364T2 (enExample) |
| MX (1) | MXPA01003248A (enExample) |
| NO (1) | NO20011603L (enExample) |
| TW (1) | TW550272B (enExample) |
| WO (1) | WO2001009209A1 (enExample) |
| ZA (1) | ZA200102500B (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002010234A2 (en) * | 2000-07-28 | 2002-02-07 | E.I. Dupont De Nemours And Company | Grafting of polyolefins |
| EP1449860A4 (en) * | 2001-10-03 | 2005-06-01 | Daikin Ind Ltd | NEW FLUOROPOLYMER, THESE RESISTANT COMPOSITIONS, AND NEW FLUORMONOMERS |
| US6869982B2 (en) * | 2002-11-27 | 2005-03-22 | Basell Poliolefine Italia S.P.A. | Irradiated, oxidized olefin polymer coupling agents |
| US6887940B2 (en) | 2002-11-27 | 2005-05-03 | Basell Poliolefine Italia S.P.A. | Compatibilizing agent for engineering thermoplastic/polyolefin blend |
| US6677395B1 (en) * | 2002-11-27 | 2004-01-13 | Basell Poliolefine Italia S.P.A. | Irradiated, oxidized olefin polymer dispersing agents |
| EP1572763B1 (en) * | 2002-12-20 | 2010-05-26 | ExxonMobil Chemical Patents Inc. | Polymers with new sequence distributions |
| US7425601B2 (en) * | 2002-12-20 | 2008-09-16 | Exxonmobil Chemical Patents Inc. | Polymers with new sequence distributions |
| CA2510860C (en) * | 2002-12-20 | 2012-10-09 | Exxonmobil Chemical Patents Inc. | Polymerization process utilizing hydrofluorocarbons as diluents |
| WO2004058827A1 (en) * | 2002-12-20 | 2004-07-15 | Exxonmobil Chemical Patents Inc. | Polymerization processes |
| US7662892B2 (en) | 2004-06-21 | 2010-02-16 | Exxonmobil Chemical Patents Inc. | Impact copolymers |
| US7981984B2 (en) * | 2004-06-21 | 2011-07-19 | Exxonmobil Chemical Patents Inc. | Polymerization process |
| US7858736B2 (en) * | 2004-06-21 | 2010-12-28 | Exxonmobil Chemical Patents Inc. | Polymer recovery method |
| WO2006009942A1 (en) * | 2004-06-21 | 2006-01-26 | Exxonmobil Chemical Patents Inc. | Polymerization process |
| FR2886767B1 (fr) | 2005-06-02 | 2007-07-27 | Accumulateurs Fixes | Accumulateur alcalin ouvert comportant une membrane microporeuse. |
| US7799882B2 (en) * | 2005-06-20 | 2010-09-21 | Exxonmobil Chemical Patents Inc. | Polymerization process |
| US8163858B2 (en) * | 2006-12-20 | 2012-04-24 | Honeywell International Inc. | Copolymers for barriers |
| US20090112222A1 (en) * | 2007-10-25 | 2009-04-30 | Bausch & Lomb Incorporated | IOL Insertion Apparatus |
| US20090121370A1 (en) * | 2007-10-26 | 2009-05-14 | Bausch & Lomb Incorporated | Molds for Production of Ophthalmic Devices |
| US9234062B2 (en) | 2011-12-14 | 2016-01-12 | Honeywell International Inc. | Process, properties, and applications of graft copolymers |
| JP5799926B2 (ja) * | 2012-09-27 | 2015-10-28 | 旭硝子株式会社 | 含フッ素共重合体の製造方法 |
| BR112017006841A2 (pt) * | 2014-10-06 | 2018-06-19 | Hercules Llc | enxerto de polímero de baixo peso molecular para inibidor de escala. |
| CN108040504B (zh) * | 2015-09-30 | 2022-04-01 | 株式会社吴羽 | 粘合剂组合物、非水电解质二次电池用电极以及非水电解质二次电池 |
| PL3575334T3 (pl) * | 2017-01-27 | 2023-09-25 | Osaka University | Materiał do formowania i sposób wytwarzania, przy jego użyciu, korpusu formowanego z żywicy |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4928902B1 (enExample) * | 1970-08-22 | 1974-07-30 | ||
| US4605704A (en) | 1983-10-12 | 1986-08-12 | Occidental Chemical Corporation | Graft polymers of polymerizable monomers and olefin polymers |
| US4806581A (en) | 1983-10-12 | 1989-02-21 | Occidental Chemical Corporation | Graft polymers of polymerizable monomers and olefin polymers |
| JPS6123616A (ja) * | 1984-07-12 | 1986-02-01 | Showa Denko Kk | 変性オレフイン系重合体の製造方法 |
| US4666991A (en) | 1984-11-05 | 1987-05-19 | Sagami Chemical Research Center | Fluorine-containing graft copolymer and adhesive and composite membrane made thereof |
| CA1298013C (en) * | 1986-11-06 | 1992-03-24 | Martin Vogel | Process for preparing core-shell particle dispersions |
| JP2707597B2 (ja) * | 1988-05-16 | 1998-01-28 | 三井石油化学工業株式会社 | 含フッ素ポリオレフィンの製造方法 |
| US5232600A (en) * | 1989-05-15 | 1993-08-03 | Pall Corporation | Hydrophobic membranes |
| CA2031406C (en) * | 1989-12-21 | 2002-05-28 | Paolo Galli | Graft copolymers of polyolefins and a method of producing same |
| US5140074A (en) | 1990-01-26 | 1992-08-18 | Himont Incorporated | Method of producing olefin polymer graft copolymers |
| US5314959A (en) | 1991-03-06 | 1994-05-24 | Minnesota Mining And Manufacturing Company | Graft copolymers containing fluoroaliphatic groups |
| JP3087379B2 (ja) * | 1991-09-27 | 2000-09-11 | 三菱化学株式会社 | 撥液性の優れた熱可塑性樹脂の製造方法 |
| JPH0586140A (ja) * | 1991-09-27 | 1993-04-06 | Mitsubishi Petrochem Co Ltd | 揆液性の優れた熱可塑性樹脂の製造方法 |
| US5217802A (en) | 1992-03-17 | 1993-06-08 | Millipore Corporation | Hydrophobic polymeric membrane composites |
-
1999
- 1999-07-30 US US09/364,444 patent/US6337373B1/en not_active Expired - Lifetime
-
2000
- 2000-07-24 AU AU57027/00A patent/AU5702700A/en not_active Abandoned
- 2000-07-24 MX MXPA01003248A patent/MXPA01003248A/es active IP Right Grant
- 2000-07-24 AT AT00942338T patent/ATE373028T1/de not_active IP Right Cessation
- 2000-07-24 KR KR1020017004112A patent/KR100751608B1/ko not_active Expired - Fee Related
- 2000-07-24 JP JP2001514013A patent/JP4773658B2/ja not_active Expired - Fee Related
- 2000-07-24 CA CA002345798A patent/CA2345798C/en not_active Expired - Fee Related
- 2000-07-24 EP EP00942338A patent/EP1127083B1/en not_active Expired - Lifetime
- 2000-07-24 DE DE60036364T patent/DE60036364T2/de not_active Expired - Lifetime
- 2000-07-24 CN CNB008020930A patent/CN1237083C/zh not_active Expired - Fee Related
- 2000-07-24 BR BRPI0007068-8A patent/BR0007068B1/pt not_active IP Right Cessation
- 2000-07-24 WO PCT/IB2000/001022 patent/WO2001009209A1/en not_active Ceased
- 2000-07-24 KR KR1020067020213A patent/KR100751609B1/ko not_active Expired - Fee Related
- 2000-07-31 AR ARP000103951A patent/AR030677A1/es unknown
- 2000-08-14 TW TW089116351A patent/TW550272B/zh not_active IP Right Cessation
-
2001
- 2001-03-27 ZA ZA200102500A patent/ZA200102500B/en unknown
- 2001-03-29 NO NO20011603A patent/NO20011603L/no not_active Application Discontinuation
- 2001-09-14 US US09/952,174 patent/US6800694B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP4773658B2 (ja) | 2011-09-14 |
| ZA200102500B (en) | 2002-09-27 |
| JP2003524026A (ja) | 2003-08-12 |
| CN1335863A (zh) | 2002-02-13 |
| EP1127083A1 (en) | 2001-08-29 |
| KR20060116869A (ko) | 2006-11-15 |
| KR100751608B1 (ko) | 2007-08-22 |
| DE60036364D1 (de) | 2007-10-25 |
| KR100751609B1 (ko) | 2007-08-22 |
| TW550272B (en) | 2003-09-01 |
| BR0007068B1 (pt) | 2011-06-14 |
| US6800694B2 (en) | 2004-10-05 |
| MXPA01003248A (es) | 2003-05-15 |
| BR0007068A (pt) | 2001-07-31 |
| AU5702700A (en) | 2001-02-19 |
| NO20011603D0 (no) | 2001-03-29 |
| CA2345798A1 (en) | 2001-02-08 |
| NO20011603L (no) | 2001-05-18 |
| AR030677A1 (es) | 2003-09-03 |
| US6337373B1 (en) | 2002-01-08 |
| WO2001009209A1 (en) | 2001-02-08 |
| ATE373028T1 (de) | 2007-09-15 |
| US20020028884A1 (en) | 2002-03-07 |
| DE60036364T2 (de) | 2008-05-29 |
| EP1127083B1 (en) | 2007-09-12 |
| CN1237083C (zh) | 2006-01-18 |
| KR20010075503A (ko) | 2001-08-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20130724 |