CA2768987A1 - Multifunctional chain shuttling agents - Google Patents
Multifunctional chain shuttling agents Download PDFInfo
- Publication number
- CA2768987A1 CA2768987A1 CA2768987A CA2768987A CA2768987A1 CA 2768987 A1 CA2768987 A1 CA 2768987A1 CA 2768987 A CA2768987 A CA 2768987A CA 2768987 A CA2768987 A CA 2768987A CA 2768987 A1 CA2768987 A1 CA 2768987A1
- Authority
- CA
- Canada
- Prior art keywords
- chain shuttling
- olefin
- independently
- polyolefin
- integer
- 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
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 157
- 229920000098 polyolefin Polymers 0.000 claims abstract description 131
- 238000000034 method Methods 0.000 claims abstract description 105
- 239000000203 mixture Substances 0.000 claims abstract description 87
- 230000008569 process Effects 0.000 claims abstract description 75
- 239000003054 catalyst Substances 0.000 claims abstract description 70
- 150000001336 alkenes Chemical class 0.000 claims description 257
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 233
- -1 polyfluoro Chemical group 0.000 claims description 85
- 239000002685 polymerization catalyst Substances 0.000 claims description 75
- 238000006116 polymerization reaction Methods 0.000 claims description 70
- 125000002947 alkylene group Chemical group 0.000 claims description 55
- 230000003647 oxidation Effects 0.000 claims description 55
- 238000007254 oxidation reaction Methods 0.000 claims description 55
- 239000000178 monomer Substances 0.000 claims description 52
- 239000000047 product Substances 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 48
- 229910052751 metal Inorganic materials 0.000 claims description 47
- 239000002184 metal Substances 0.000 claims description 47
- 125000006659 (C1-C20) hydrocarbyl group Chemical group 0.000 claims description 44
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 125000004450 alkenylene group Chemical group 0.000 claims description 31
- 125000000524 functional group Chemical group 0.000 claims description 31
- 230000000977 initiatory effect Effects 0.000 claims description 26
- 238000009826 distribution Methods 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 20
- 125000005647 linker group Chemical group 0.000 claims description 19
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 150000001768 cations Chemical class 0.000 claims description 14
- 230000000737 periodic effect Effects 0.000 claims description 13
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 12
- 125000000743 hydrocarbylene group Chemical group 0.000 claims description 12
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 11
- 239000000376 reactant Substances 0.000 claims description 11
- 230000003197 catalytic effect Effects 0.000 claims description 10
- 239000004615 ingredient Substances 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 229910021482 group 13 metal Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 230000000379 polymerizing effect Effects 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000002524 organometallic group Chemical group 0.000 claims description 5
- 125000004437 phosphorous atom Chemical class 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 4
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical compound C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910000096 monohydride Inorganic materials 0.000 claims description 3
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims description 2
- SCESWTHQFQXGMV-UHFFFAOYSA-N ethenylphosphane Chemical compound PC=C SCESWTHQFQXGMV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical class N* 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 76
- 229920000642 polymer Polymers 0.000 description 68
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 58
- 239000005977 Ethylene Substances 0.000 description 58
- 229920001400 block copolymer Polymers 0.000 description 58
- 239000000243 solution Substances 0.000 description 53
- 239000004711 α-olefin Substances 0.000 description 50
- 150000003254 radicals Chemical class 0.000 description 41
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 32
- 238000003756 stirring Methods 0.000 description 30
- 239000002904 solvent Substances 0.000 description 28
- 229910052782 aluminium Inorganic materials 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
- 238000010348 incorporation Methods 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000004721 Polyphenylene oxide Substances 0.000 description 19
- 235000010210 aluminium Nutrition 0.000 description 19
- 229920000728 polyester Polymers 0.000 description 18
- 229920000570 polyether Polymers 0.000 description 18
- 229920001228 polyisocyanate Polymers 0.000 description 18
- 239000005056 polyisocyanate Substances 0.000 description 18
- 229920001577 copolymer Polymers 0.000 description 17
- 229930195733 hydrocarbon Natural products 0.000 description 17
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 16
- 239000003446 ligand Substances 0.000 description 16
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 16
- 239000004952 Polyamide Substances 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 15
- 229920000359 diblock copolymer Polymers 0.000 description 15
- 239000000543 intermediate Substances 0.000 description 15
- 229920002647 polyamide Polymers 0.000 description 15
- 239000000523 sample Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 13
- 239000004215 Carbon black (E152) Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 238000012546 transfer Methods 0.000 description 13
- 239000011521 glass Substances 0.000 description 12
- 150000002430 hydrocarbons Chemical class 0.000 description 12
- 229920006030 multiblock copolymer Polymers 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 11
- 239000007789 gas Substances 0.000 description 11
- 239000011701 zinc Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000007792 addition Methods 0.000 description 10
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 10
- 238000000113 differential scanning calorimetry Methods 0.000 description 10
- 230000005714 functional activity Effects 0.000 description 10
- 229920001519 homopolymer Polymers 0.000 description 10
- 238000010550 living polymerization reaction Methods 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000012528 membrane Substances 0.000 description 10
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 229920000573 polyethylene Polymers 0.000 description 9
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 9
- 238000000926 separation method Methods 0.000 description 9
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000004810 polytetrafluoroethylene Substances 0.000 description 8
- 239000004698 Polyethylene Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- UIZVMOZAXAMASY-UHFFFAOYSA-N hex-5-en-1-ol Chemical compound OCCCCC=C UIZVMOZAXAMASY-UHFFFAOYSA-N 0.000 description 7
- 238000004806 packaging method and process Methods 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 description 6
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 6
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 6
- 230000003213 activating effect Effects 0.000 description 6
- 125000002015 acyclic group Chemical group 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 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 6
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 6
- 229910052796 boron Inorganic materials 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 description 6
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 239000002841 Lewis acid Substances 0.000 description 5
- 229920001244 Poly(D,L-lactide) Polymers 0.000 description 5
- 238000012644 addition polymerization Methods 0.000 description 5
- 238000012653 anionic ring-opening polymerization Methods 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- WYURNTSHIVDZCO-SVYQBANQSA-N deuterated tetrahydrofuran Substances [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 5
- 150000001993 dienes Chemical class 0.000 description 5
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 150000007517 lewis acids Chemical class 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
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- 238000002360 preparation method Methods 0.000 description 5
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- 238000003786 synthesis reaction Methods 0.000 description 5
- 229920006250 telechelic polymer Polymers 0.000 description 5
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 4
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
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- 239000007983 Tris buffer Substances 0.000 description 4
- 125000005234 alkyl aluminium group Chemical group 0.000 description 4
- 239000000010 aprotic solvent Substances 0.000 description 4
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- 238000013461 design Methods 0.000 description 4
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- 239000003999 initiator Substances 0.000 description 4
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
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- SOEVKJXMZBAALG-UHFFFAOYSA-N octylalumane Chemical compound CCCCCCCC[AlH2] SOEVKJXMZBAALG-UHFFFAOYSA-N 0.000 description 4
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 description 3
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 101150041968 CDC13 gene Proteins 0.000 description 3
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- 101100378708 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) AIR2 gene Proteins 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 description 3
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
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- 239000011575 calcium Substances 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
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- 239000012986 chain transfer agent Substances 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
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- 125000002993 cycloalkylene group Chemical group 0.000 description 3
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052735 hafnium Inorganic materials 0.000 description 3
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
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- 150000002596 lactones Chemical class 0.000 description 3
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- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 3
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- QXALIERKYGCHHA-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl)borane Chemical compound BC1=C(F)C(F)=C(F)C(F)=C1F QXALIERKYGCHHA-UHFFFAOYSA-N 0.000 description 2
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
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- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
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- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- PJLHTVIBELQURV-UHFFFAOYSA-N 1-pentadecene Chemical compound CCCCCCCCCCCCCC=C PJLHTVIBELQURV-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- AQZWEFBJYQSQEH-UHFFFAOYSA-N 2-methyloxaluminane Chemical compound C[Al]1CCCCO1 AQZWEFBJYQSQEH-UHFFFAOYSA-N 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
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- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012900 molecular simulation Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KDFFXYVOTKKBDI-UHFFFAOYSA-N n-ethylnaphthalen-1-amine Chemical compound C1=CC=C2C(NCC)=CC=CC2=C1 KDFFXYVOTKKBDI-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- VFLWKHBYVIUAMP-UHFFFAOYSA-N n-methyl-n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCCCC VFLWKHBYVIUAMP-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001181 organosilyl group Chemical class [SiH3]* 0.000 description 1
- 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000006709 oxidative esterification reaction Methods 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 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 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 239000004038 photonic crystal Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920006124 polyolefin elastomer Polymers 0.000 description 1
- 229920005629 polypropylene homopolymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical compound OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000002760 rocket fuel Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 150000004819 silanols Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- SCABQASLNUQUKD-UHFFFAOYSA-N silylium Chemical class [SiH3+] SCABQASLNUQUKD-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical group [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 description 1
- FGWRMMTYIZKYMA-UHFFFAOYSA-N tert-butyl-hydroxy-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)O FGWRMMTYIZKYMA-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- WYXIGTJNYDDFFH-UHFFFAOYSA-Q triazanium;borate Chemical compound [NH4+].[NH4+].[NH4+].[O-]B([O-])[O-] WYXIGTJNYDDFFH-UHFFFAOYSA-Q 0.000 description 1
- RGGPNXQUMRMPRA-UHFFFAOYSA-N triethylgallium Chemical compound CC[Ga](CC)CC RGGPNXQUMRMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 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
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- 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
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M50/00—Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
- H01M50/40—Separators; Membranes; Diaphragms; Spacing elements inside cells
- H01M50/409—Separators, membranes or diaphragms characterised by the material
- H01M50/411—Organic material
- H01M50/414—Synthetic resins, e.g. thermoplastics or thermosetting resins
- H01M50/417—Polyolefins
-
- 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
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/14—Monomers containing five or more carbon atoms
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
- H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/42—Methods or arrangements for servicing or maintenance of secondary cells or secondary half-cells
- H01M10/4235—Safety or regulating additives or arrangements in electrodes, separators or electrolyte
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Electrochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
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| US22942509P | 2009-07-29 | 2009-07-29 | |
| US61/229,425 | 2009-07-29 | ||
| PCT/US2010/043483 WO2011014533A1 (en) | 2009-07-29 | 2010-07-28 | Multifunctional chain shuttling agents |
Publications (1)
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| CA2768987A1 true CA2768987A1 (en) | 2011-02-03 |
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| CA2768987A Abandoned CA2768987A1 (en) | 2009-07-29 | 2010-07-28 | Multifunctional chain shuttling agents |
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| EP (1) | EP2459597B1 (enExample) |
| JP (1) | JP5744868B2 (enExample) |
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| CN (1) | CN102471393B (enExample) |
| BR (1) | BR112012001942B1 (enExample) |
| CA (1) | CA2768987A1 (enExample) |
| SG (1) | SG177774A1 (enExample) |
| WO (1) | WO2011014533A1 (enExample) |
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| JP5675609B2 (ja) * | 2009-07-01 | 2015-02-25 | 三井化学株式会社 | 有機金属化合物およびその製造方法 |
| DE102011088910A1 (de) * | 2011-12-16 | 2013-06-20 | Robert Bosch Gmbh | Lithium-Schwefel-Zellen-Separator mit Polysulfidsperrschicht |
| PT3063155T (pt) * | 2013-10-28 | 2017-12-11 | Akzo Nobel Chemicals Int Bv | Processo para preparar aluminoxanos por hidrólise de alquilalumínio com álcoois alílicos |
| CN103855351A (zh) * | 2014-03-11 | 2014-06-11 | 东莞新能源科技有限公司 | 锂离子电池、所使用的隔离膜及隔离膜的制备方法 |
| WO2016077455A1 (en) * | 2014-11-11 | 2016-05-19 | Cornell University | Isotactic polyethers and bimetallic catalysts, methods of making same, and uses thereof |
| FR3029920B1 (fr) * | 2014-12-12 | 2016-12-09 | Univ Claude Bernard Lyon | Polyolefine fonctionnelle ou telechelique, ses derives, et son procede de preparation |
| EP3034546B1 (en) * | 2014-12-17 | 2019-10-16 | SABIC Global Technologies B.V. | A process for the preparation of a block copolymer comprising a first polyolefin block and a second polymer block |
| EP3034545B1 (en) | 2014-12-17 | 2020-11-04 | SABIC Global Technologies B.V. | A process for the preparation of a graft copolymer comprising a polyolefin main chain and one or a multiple polymer side chains and the products obtained therefrom |
| EP3034544B1 (en) * | 2014-12-17 | 2019-10-16 | SABIC Global Technologies B.V. | A process for the preparation of a graft copolymer comprising a polyolefin main chain and one or a multiple polymer side chains |
| EP3034547B1 (en) | 2014-12-17 | 2019-10-09 | SABIC Global Technologies B.V. | A process for the preparation of a block copolymer comprising a first polyolefin block and a second polymer block |
| EP3037437A1 (en) | 2014-12-23 | 2016-06-29 | SABIC Global Technologies B.V. | Process for the preparation of a polyolefin having one or multiple end-functionalized branches. |
| EP3037438A1 (en) | 2014-12-23 | 2016-06-29 | SABIC Global Technologies B.V. | Process for the preparation of a branched polyolefin |
| JP6791871B2 (ja) | 2015-03-26 | 2020-11-25 | ダウ グローバル テクノロジーズ エルエルシー | 鎖シャトリング剤の添加方法 |
| US10618988B2 (en) | 2015-08-31 | 2020-04-14 | Exxonmobil Chemical Patents Inc. | Branched propylene polymers produced via use of vinyl transfer agents and processes for production thereof |
| EP3344385A4 (en) | 2015-08-31 | 2019-08-14 | ExxonMobil Chemical Patents Inc. | ALUMINUM ALKYLE WITH HANGING OLEFINS ON SOUND |
| KR102081523B1 (ko) * | 2015-08-31 | 2020-02-25 | 엑손모빌 케미칼 패턴츠 인코포레이티드 | 비닐 이동제의 사용을 통해 제조된 중합체 |
| WO2017039995A1 (en) * | 2015-08-31 | 2017-03-09 | Exxonmobil Chemical Patents Inc. | Aluminum alkyls with pendant olefins for polyolefin reactions |
| US9982067B2 (en) | 2015-09-24 | 2018-05-29 | Exxonmobil Chemical Patents Inc. | Polymerization process using pyridyldiamido compounds supported on organoaluminum treated layered silicate supports |
| BR112018005199B1 (pt) * | 2015-09-30 | 2020-12-15 | Dow Global Technologies Llc | Processo para a preparação de uma composição, composição e processo para polimerização de pelo menos um monômero polimerizável por adição para formar uma composição de polímero |
| FR3044663B1 (fr) * | 2015-12-08 | 2017-12-29 | Michelin & Cie | Copolymere monofonctionnel ou telechelique de 1,3-butadiene et d'ethylene. |
| FR3044664B1 (fr) * | 2015-12-08 | 2017-12-29 | Michelin & Cie | Copolymere monofonctionnel ou telechelique de 1,3-diene et d'ethylene ou d'alpha-monoolefine. |
| WO2017097568A1 (en) * | 2015-12-09 | 2017-06-15 | Sabic Global Technologies B.V. | Process for the preparation of polyolefin-based graft copolymers comprising a first long chain branched polyolefin block and one or multiple polymer side chains |
| US10787545B2 (en) | 2015-12-09 | 2020-09-29 | Sabic Global Technologies B.V. | Process for the preparation of polyolefin-based graft copolymers comprising a first functionalized short chain branched polyolefin block and one or multiple polymer side chains |
| WO2017097569A1 (en) * | 2015-12-09 | 2017-06-15 | Sabic Global Technologies B.V. | Process for the preparation of polyolefin-based graft copolymers comprising a first functionalized short chain branched polyolefin block and one or multiple polymer side chains |
| WO2017097570A1 (en) * | 2015-12-09 | 2017-06-15 | Sabic Global Technologies B.V. | Process for the preparation of polyolefin-based graft copolymers comprising a first long chain branched polyolefin block and one or multiple polymer side chains |
| US10562987B2 (en) | 2016-06-30 | 2020-02-18 | Exxonmobil Chemical Patents Inc. | Polymers produced via use of quinolinyldiamido transition metal complexes and vinyl transfer agents |
| JP7123040B2 (ja) * | 2016-09-30 | 2022-08-22 | ダウ グローバル テクノロジーズ エルエルシー | 連鎖シャトリングに有用な多頭または二頭組成物の調製方法 |
| JP7029448B2 (ja) | 2016-09-30 | 2022-03-03 | ダウ グローバル テクノロジーズ エルエルシー | チェーンシャトリングに有用な封鎖されたマルチまたはデュアルヘッド組成物、およびそれを調製するプロセス |
| JP7096236B2 (ja) * | 2016-09-30 | 2022-07-05 | ダウ グローバル テクノロジーズ エルエルシー | チェーンシャトリングに有用なマルチヘッドまたはデュアルヘッド組成物、およびそれを調製するプロセス |
| US10626200B2 (en) | 2017-02-28 | 2020-04-21 | Exxonmobil Chemical Patents Inc. | Branched EPDM polymers produced via use of vinyl transfer agents and processes for production thereof |
| US10676551B2 (en) | 2017-03-01 | 2020-06-09 | Exxonmobil Chemical Patents Inc. | Branched ethylene copolymers produced via use of vinyl transfer agents and processes for production thereof |
| US11492450B2 (en) | 2017-12-29 | 2022-11-08 | Dow Global Technologies Llc | Dual-headed organoaluminum compositions |
| SG11202005532YA (en) * | 2017-12-29 | 2020-07-29 | Dow Global Technologies Llc | Capped dual-headed organoaluminum compositions |
| CN109467660B (zh) * | 2018-10-06 | 2021-03-02 | 天津大学 | 利用链穿梭方法合成聚(乙烯-r-降冰片烯/乙烯)多嵌段共聚物 |
| US10711016B1 (en) | 2019-05-01 | 2020-07-14 | The Goodyear Tire & Rubber Company | Functionalized aluminum reagents |
| US10703837B1 (en) | 2019-05-01 | 2020-07-07 | The Goodyear Tire & Rubber Company | Method of making a functionalized elastomer, elastomer, rubber composition and tire |
| US10968239B2 (en) | 2019-05-01 | 2021-04-06 | The Goodyear Tire & Rubber Company | Functionalized aluminum reagents |
| US11352455B2 (en) | 2019-05-01 | 2022-06-07 | The Goodyear Tire & Rubber Company | Method of making a functionalized elastomer, elastomer, rubber composition and tire |
| WO2022204732A1 (en) * | 2021-03-26 | 2022-09-29 | Cornell University | Ultrathin polymer films as protective coatings for battery electrodes |
Family Cites Families (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5153157A (en) | 1987-01-30 | 1992-10-06 | Exxon Chemical Patents Inc. | Catalyst system of enhanced productivity |
| US7163907B1 (en) | 1987-01-30 | 2007-01-16 | Exxonmobil Chemical Patents Inc. | Aluminum-free monocyclopentadienyl metallocene catalysts for olefin polymerization |
| US4981605A (en) | 1987-06-08 | 1991-01-01 | Mitsui Petrochemical Industries, Ltd. | Liquid modified ethylenic random copolymer and its uses |
| IT1226097B (it) | 1988-07-07 | 1990-12-10 | Ausimont Spa | Polimeri monofunzionali delle olefine e copolimeri a blocchi da essi ottenuti. |
| US5064802A (en) | 1989-09-14 | 1991-11-12 | The Dow Chemical Company | Metal complex compounds |
| JP2545006B2 (ja) | 1990-07-03 | 1996-10-16 | ザ ダウ ケミカル カンパニー | 付加重合触媒 |
| US5247023A (en) | 1991-06-06 | 1993-09-21 | The Pennsylvania Research Corporation | Hydrocarbon polymers containing borane groups at chain ends or in polymer backbone |
| US5721185A (en) | 1991-06-24 | 1998-02-24 | The Dow Chemical Company | Homogeneous olefin polymerization catalyst by abstraction with lewis acids |
| US5296433A (en) | 1992-04-14 | 1994-03-22 | Minnesota Mining And Manufacturing Company | Tris(pentafluorophenyl)borane complexes and catalysts derived therefrom |
| US5350723A (en) | 1992-05-15 | 1994-09-27 | The Dow Chemical Company | Process for preparation of monocyclopentadienyl metal complex compounds and method of use |
| US5470993A (en) | 1993-06-24 | 1995-11-28 | The Dow Chemical Company | Titanium(II) or zirconium(II) complexes and addition polymerization catalysts therefrom |
| US5372682A (en) | 1993-06-24 | 1994-12-13 | The Dow Chemical Company | Electrochemical preparation of addition polymerization catalysts |
| US5625087A (en) | 1994-09-12 | 1997-04-29 | The Dow Chemical Company | Silylium cationic polymerization activators for metallocene complexes |
| JP3719727B2 (ja) * | 1994-10-13 | 2005-11-24 | 三井化学株式会社 | 末端に官能基を有するポリオレフィンの製造方法 |
| CA2245839C (en) | 1996-03-27 | 2005-06-14 | The Dow Chemical Company | Highly soluble olefin polymerization catalyst activator |
| US5883204A (en) | 1996-03-27 | 1999-03-16 | The Dow Chemical Company | Solution polymerization process with dispersed catalyst activator |
| ES2224266T3 (es) | 1996-08-08 | 2005-03-01 | Dow Global Technologies Inc. | Copmplejos metalicos que contienen ciclopentadienilo sustituido en la posicion 3 con un heteroatomo y procedimiento de polimerizacion de olefinas. |
| US6015868A (en) | 1996-10-03 | 2000-01-18 | The Dow Chemical Company | Substituted indenyl containing metal complexes and olefin polymerization process |
| US5783512A (en) | 1996-12-18 | 1998-07-21 | The Dow Chemical Company | Catalyst component dispersion comprising an ionic compound and solid addition polymerization catalysts containing the same |
| US5965756A (en) | 1996-12-19 | 1999-10-12 | The Dow Chemical Company | Fused ring substituted indenyl metal complexes and polymerization process |
| ATE213250T1 (de) | 1996-12-19 | 2002-02-15 | Dow Chemical Co | Metallkomplexe enthaltend in position 3 arylsubstituierte indenylderivate, und polymerisationsverfahren |
| EP1007998A1 (en) | 1997-02-11 | 2000-06-14 | Massachusetts Institute Of Technology | Polymeric photonic band gap materials |
| US6103657A (en) | 1997-07-02 | 2000-08-15 | Union Carbide Chemicals & Plastics Technology Corporation | Catalyst for the production of olefin polymers |
| US6150297A (en) | 1997-09-15 | 2000-11-21 | The Dow Chemical Company | Cyclopentaphenanthrenyl metal complexes and polymerization process |
| US6696379B1 (en) | 1997-09-19 | 2004-02-24 | The Dow Chemical Company | Supported modified alumoxane catalyst activator |
| KR100371398B1 (ko) | 1998-12-08 | 2003-05-12 | 주식회사 엘지화학 | 폴리올레핀블렌드로제조된통기성필름과그의제조방법및2차전지의격리막 |
| EP1161774A2 (en) | 1999-02-19 | 2001-12-12 | Amtek Research International LLC | Electrically conductive, freestanding microporous polymer sheet |
| AU3764600A (en) | 1999-05-13 | 2000-12-05 | Dow Chemical Company, The | Di- and tri-heteroatom substituted indenyl metal complexes |
| JP3940546B2 (ja) * | 1999-06-07 | 2007-07-04 | 株式会社東芝 | パターン形成方法およびパターン形成材料 |
| WO2001042315A1 (en) | 1999-12-10 | 2001-06-14 | Dow Global Technologies Inc. | Substituted group 4 metal complexes, catalysts and olefin polymerization process |
| US6825295B2 (en) | 1999-12-10 | 2004-11-30 | Dow Global Technologies Inc. | Alkaryl-substituted group 4 metal complexes, catalysts and olefin polymerization process |
| AU2001236687A1 (en) | 2000-02-04 | 2001-08-14 | Amtek Research International Llc | Freestanding microporous separator including a gel-forming polymer |
| US6372379B1 (en) | 2000-02-25 | 2002-04-16 | Abbas M. Samii | Microporous membrane battery separator for silver zinc batteries |
| US6749961B1 (en) | 2000-04-10 | 2004-06-15 | Celgard Inc. | Shutdown battery separator made with a blend of polymer and oligomer |
| CA2411712C (en) | 2000-06-30 | 2011-01-25 | Dow Global Technologies Inc. | Polycyclic, fused ring compounds, metal complexes and polymerization process |
| EP1334139A2 (en) | 2000-11-07 | 2003-08-13 | Symyx Technologies, Inc. | Substituted pyridyl amine ligands, complexes and catalysts therefrom. processes for producing polyolefins therewith |
| ES2240735T3 (es) | 2001-05-14 | 2005-10-16 | Dow Global Technologies Inc. | Complejos metalicos ciclopentadienilo 3-aril-sustituido y procedimiento de polimerizacion. |
| EP1264847A1 (fr) | 2001-06-06 | 2002-12-11 | SOLVAY POLYOLEFINS EUROPE - BELGIUM (Société Anonyme) | Procédé pour la polymérisation des alpha-oléfines |
| US6960635B2 (en) | 2001-11-06 | 2005-11-01 | Dow Global Technologies Inc. | Isotactic propylene copolymers, their preparation and use |
| US6919467B2 (en) | 2001-12-18 | 2005-07-19 | Univation Technologies, Llc | Imino-amide catalyst compositions for the polymerization of olefins |
| ATE403684T1 (de) | 2002-03-14 | 2008-08-15 | Dow Global Technologies Inc | Metallkomplexe mit substituierten indenylliganden und polymerisationsverfahren |
| AU2003216477A1 (en) | 2002-03-14 | 2003-09-29 | Dow Global Technologies Inc. | Polycyclic, fused heteroring compounds, metal complexes and polymerization process |
| ATE492552T1 (de) | 2002-04-24 | 2011-01-15 | Symyx Solutions Inc | Verbrückte bi-aromatische liganden, komplexe, katalysatoren, verfahren zur polymerisierung und entstehende polymere |
| WO2003100954A2 (en) | 2002-05-24 | 2003-12-04 | Amtek Research International Llc | Microporous, mixed polymer phase membrane |
| DE60308885T2 (de) | 2002-09-12 | 2007-04-12 | Dow Global Technologies, Inc., Midland | Herstellung von metallkomplexen |
| KR100643106B1 (ko) | 2003-03-24 | 2006-11-13 | 아사히 가세이 케미칼즈 가부시키가이샤 | 폴리에틸렌 미다공막 |
| US6953764B2 (en) | 2003-05-02 | 2005-10-11 | Dow Global Technologies Inc. | High activity olefin polymerization catalyst and process |
| CN101044643B (zh) * | 2003-06-06 | 2012-05-16 | 阿姆泰克研究国际公司 | 含有活性功能基团的电池隔离板 |
| JP2005105147A (ja) | 2003-09-30 | 2005-04-21 | National Institute Of Advanced Industrial & Technology | ランダム共重合体及びその製造方法 |
| RU2386646C2 (ru) | 2004-01-22 | 2010-04-20 | Дау Глобал Текнолоджиз Инк. | Функционализированные эластомерные композиции |
| US7608668B2 (en) | 2004-03-17 | 2009-10-27 | Dow Global Technologies Inc. | Ethylene/α-olefins block interpolymers |
| CA2557870A1 (en) * | 2004-03-17 | 2005-09-29 | Dow Global Technologies Inc. | Catalyst composition comprising shuttling agent for higher olefin multi-block copolymer formation |
| CN1976965B (zh) | 2004-03-17 | 2012-10-10 | 陶氏环球技术有限责任公司 | 用于形成乙烯多嵌段共聚物的包含梭移剂的催化剂组合物 |
| US7355089B2 (en) | 2004-03-17 | 2008-04-08 | Dow Global Technologies Inc. | Compositions of ethylene/α-olefin multi-block interpolymer for elastic films and laminates |
| MXPA06010485A (es) * | 2004-03-17 | 2006-12-19 | Dow Global Technologies Inc | Composicion catalizadora que comprende agente de enlace para la formacion de copolimeros de etileno. |
| JP4439323B2 (ja) | 2004-04-26 | 2010-03-24 | 独立行政法人産業技術総合研究所 | 極性基含有共重合体及びその製造方法 |
| AU2006227475A1 (en) * | 2005-03-17 | 2006-09-28 | Dow Global Technologies Inc. | Functionalized ethylene/alpha-olefin interpolymer compositions |
| EP2894176B1 (en) | 2005-03-17 | 2022-06-01 | Dow Global Technologies LLC | Catalyst composition comprising shuttling agent for regio-irregular multi-block copolymer formation |
| CA2622720A1 (en) * | 2005-09-15 | 2007-03-29 | Dow Global Technologies Inc. | Catalytic olefin block copolymers via polymerizable shuttling agent |
| RU2008114500A (ru) | 2005-09-15 | 2009-10-20 | Дау Глобал Текнолоджиз Инк. (Us) | Блок-сополимеры каталитической полимеризации олефинов с контролируемым распределением последовательности блоков |
| WO2007035493A2 (en) | 2005-09-15 | 2007-03-29 | Dow Global Technologies Inc. | Control of polymer architecture and molecular weight distribution via multi-centered shuttling agent |
| WO2008027283A2 (en) | 2006-08-25 | 2008-03-06 | Dow Global Technologies Inc. | Production of meta-block copolymers by polymer segment interchange |
| EP2170604B1 (en) | 2007-07-13 | 2019-05-15 | Dow Global Technologies LLC | Ethylene/alpha-olefin interpolymers having low crystallinity hard blocks |
| JP6184048B2 (ja) | 2008-01-30 | 2017-08-23 | ダウ グローバル テクノロジーズ エルエルシー | エチレン／α−オレフィンブロック共重合体 |
| EP2238187B1 (en) | 2008-01-30 | 2017-05-10 | Dow Global Technologies LLC | Ethylene/alpha -olefin block interpolymers |
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- 2010-07-28 US US12/845,023 patent/US8324416B2/en active Active
- 2010-07-28 SG SG2012006136A patent/SG177774A1/en unknown
- 2010-07-28 CN CN2010800335518A patent/CN102471393B/zh active Active
- 2010-07-28 CA CA2768987A patent/CA2768987A1/en not_active Abandoned
- 2010-07-28 KR KR1020127005240A patent/KR101621703B1/ko active Active
- 2010-07-28 EP EP10739443.9A patent/EP2459597B1/en active Active
- 2010-07-28 WO PCT/US2010/043483 patent/WO2011014533A1/en not_active Ceased
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|---|---|
| WO2011014533A1 (en) | 2011-02-03 |
| EP2459597A1 (en) | 2012-06-06 |
| US20130072707A1 (en) | 2013-03-21 |
| CN102471393A (zh) | 2012-05-23 |
| US20110028657A1 (en) | 2011-02-03 |
| BR112012001942A2 (pt) | 2016-03-15 |
| SG177774A1 (en) | 2012-03-29 |
| JP5744868B2 (ja) | 2015-07-08 |
| US8324416B2 (en) | 2012-12-04 |
| US20130085247A1 (en) | 2013-04-04 |
| KR20120065340A (ko) | 2012-06-20 |
| BR112012001942B1 (pt) | 2019-10-22 |
| JP2013501093A (ja) | 2013-01-10 |
| US8765877B2 (en) | 2014-07-01 |
| CN102471393B (zh) | 2013-12-04 |
| US8772523B2 (en) | 2014-07-08 |
| US20130072639A1 (en) | 2013-03-21 |
| US8716166B2 (en) | 2014-05-06 |
| US8765886B2 (en) | 2014-07-01 |
| US20130072640A1 (en) | 2013-03-21 |
| EP2459597B1 (en) | 2013-10-23 |
| US20130072377A1 (en) | 2013-03-21 |
| KR101621703B1 (ko) | 2016-05-17 |
| US8759453B2 (en) | 2014-06-24 |
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