CA2446866C - Arborescent thermoplastic elastomers and products therefrom - Google Patents
Arborescent thermoplastic elastomers and products therefrom Download PDFInfo
- Publication number
- CA2446866C CA2446866C CA2446866A CA2446866A CA2446866C CA 2446866 C CA2446866 C CA 2446866C CA 2446866 A CA2446866 A CA 2446866A CA 2446866 A CA2446866 A CA 2446866A CA 2446866 C CA2446866 C CA 2446866C
- Authority
- CA
- Canada
- Prior art keywords
- arborescent
- block copolymer
- process according
- polyisoolefin
- group
- 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
Links
- 229920002725 thermoplastic elastomer Polymers 0.000 title description 29
- 229920001400 block copolymer Polymers 0.000 claims abstract description 124
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 59
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 33
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 33
- 230000009477 glass transition Effects 0.000 claims abstract description 9
- 238000002844 melting Methods 0.000 claims abstract description 7
- 230000008018 melting Effects 0.000 claims abstract description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 84
- 229920002367 Polyisobutene Polymers 0.000 claims description 70
- 238000000034 method Methods 0.000 claims description 69
- 230000008569 process Effects 0.000 claims description 60
- 229920000642 polymer Polymers 0.000 claims description 53
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 36
- 238000006116 polymerization reaction Methods 0.000 claims description 31
- 239000004033 plastic Substances 0.000 claims description 30
- 229920003023 plastic Polymers 0.000 claims description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 24
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 22
- 239000004793 Polystyrene Substances 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 20
- 229920002223 polystyrene Polymers 0.000 claims description 19
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 16
- -1 p-methoxistyrene Chemical compound 0.000 claims description 14
- 230000015572 biosynthetic process Effects 0.000 claims description 12
- 229940050176 methyl chloride Drugs 0.000 claims description 12
- 238000003786 synthesis reaction Methods 0.000 claims description 12
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 239000002841 Lewis acid Substances 0.000 claims description 10
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 239000000178 monomer Substances 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 238000009826 distribution Methods 0.000 claims description 9
- 239000012038 nucleophile Substances 0.000 claims description 9
- UWKQJZCTQGMHKD-UHFFFAOYSA-N 2,6-di-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=N1 UWKQJZCTQGMHKD-UHFFFAOYSA-N 0.000 claims description 8
- 241001120493 Arene Species 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 230000000903 blocking effect Effects 0.000 claims description 7
- 239000012454 non-polar solvent Substances 0.000 claims description 7
- 239000002798 polar solvent Substances 0.000 claims description 7
- 230000000379 polymerizing effect Effects 0.000 claims description 7
- 229920000131 polyvinylidene Polymers 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 239000007943 implant Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 claims description 5
- 229940113088 dimethylacetamide Drugs 0.000 claims description 5
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 238000010538 cationic polymerization reaction Methods 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 230000000977 initiatory effect Effects 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 claims description 3
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 3
- 125000002091 cationic group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims description 3
- 229960003750 ethyl chloride Drugs 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 230000001747 exhibiting effect Effects 0.000 claims description 3
- 229940073584 methylene chloride Drugs 0.000 claims description 3
- 125000000466 oxiranyl group Chemical group 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical group ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims description 3
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- ZVCJBDIMKCDALP-UHFFFAOYSA-N 2,4,4,6,6-pentamethyloct-7-en-2-ol Chemical compound CC(C)(O)CC(C)(C)CC(C)(C)C=C ZVCJBDIMKCDALP-UHFFFAOYSA-N 0.000 claims description 2
- YTOZMAOEVUXFTE-UHFFFAOYSA-N 2,4,4-trimethylhept-6-en-2-ol Chemical compound CC(C)(O)CC(C)(C)CC=C YTOZMAOEVUXFTE-UHFFFAOYSA-N 0.000 claims description 2
- ZETCGVWPFKWYST-UHFFFAOYSA-N 2,4,4-trimethylhex-5-en-2-ol Chemical compound CC(C)(O)CC(C)(C)C=C ZETCGVWPFKWYST-UHFFFAOYSA-N 0.000 claims description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 2
- HVHZEKKZMFRULH-UHFFFAOYSA-N 2,6-ditert-butyl-4-methylpyridine Chemical compound CC1=CC(C(C)(C)C)=NC(C(C)(C)C)=C1 HVHZEKKZMFRULH-UHFFFAOYSA-N 0.000 claims description 2
- HWYDQIOFBPGPDV-UHFFFAOYSA-N 2-(2,2-dimethylpent-4-enyl)-2-methyloxirane Chemical compound C=CCC(C)(C)CC1(C)CO1 HWYDQIOFBPGPDV-UHFFFAOYSA-N 0.000 claims description 2
- OCNSYRGZVKDOOY-UHFFFAOYSA-N 2-(4-ethenylphenyl)-2-methyloxirane Chemical compound C=1C=C(C=C)C=CC=1C1(C)CO1 OCNSYRGZVKDOOY-UHFFFAOYSA-N 0.000 claims description 2
- QLTOZCYMHKUAMK-UHFFFAOYSA-N 2-methyl-2-(2,2,4,4-tetramethylhept-6-enyl)oxirane Chemical compound C=CCC(C)(C)CC(C)(C)CC1(C)CO1 QLTOZCYMHKUAMK-UHFFFAOYSA-N 0.000 claims description 2
- XNZYFQMTNBYBHJ-UHFFFAOYSA-N 2-methyl-2-(2,2,4,4-tetramethylhex-5-enyl)oxirane Chemical compound C=CC(C)(C)CC(C)(C)CC1(C)CO1 XNZYFQMTNBYBHJ-UHFFFAOYSA-N 0.000 claims description 2
- VIRCRRNSHQAMMN-UHFFFAOYSA-N 5-chloro-3,3,5-trimethylhex-1-ene Chemical compound CC(C)(Cl)CC(C)(C)C=C VIRCRRNSHQAMMN-UHFFFAOYSA-N 0.000 claims description 2
- PPJULRHVLHTRER-UHFFFAOYSA-N 6-chloro-4,4,6-trimethylhept-1-ene Chemical compound CC(C)(Cl)CC(C)(C)CC=C PPJULRHVLHTRER-UHFFFAOYSA-N 0.000 claims description 2
- UIBJLZLXTNKJHF-UHFFFAOYSA-N 7-chloro-3,3,5,5,7-pentamethyloct-1-ene Chemical compound CC(C)(Cl)CC(C)(C)CC(C)(C)C=C UIBJLZLXTNKJHF-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WZZJJLCDXMPSOZ-UHFFFAOYSA-N 8-chloro-4,4,6,6,8-pentamethylnon-1-ene Chemical compound CC(C)(Cl)CC(C)(C)CC(C)(C)CC=C WZZJJLCDXMPSOZ-UHFFFAOYSA-N 0.000 claims description 2
- FSFGCYIOMOFJLK-UHFFFAOYSA-N C(C)(C)(C)C1(C=C)CC=C(C=C1)C(C)(C)C Chemical compound C(C)(C)(C)C1(C=C)CC=C(C=C1)C(C)(C)C FSFGCYIOMOFJLK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 12
- 239000003495 polar organic solvent Substances 0.000 claims 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- PLQVCIBHIJNNHD-UHFFFAOYSA-N 2,4,4,6,6-pentamethylnon-8-en-2-ol Chemical compound CC(C)(O)CC(C)(C)CC(C)(C)CC=C PLQVCIBHIJNNHD-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 238000001727 in vivo Methods 0.000 claims 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000003999 initiator Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- 229920001971 elastomer Polymers 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 239000005060 rubber Substances 0.000 description 10
- 238000001542 size-exclusion chromatography Methods 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 238000012512 characterization method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000001788 irregular Effects 0.000 description 4
- 238000005191 phase separation Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 238000010550 living polymerization reaction Methods 0.000 description 3
- 238000000569 multi-angle light scattering Methods 0.000 description 3
- 229920001195 polyisoprene Polymers 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- 238000012552 review Methods 0.000 description 3
- 238000004611 spectroscopical analysis Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- XGBWXISUZXYULS-UHFFFAOYSA-N 2,3-ditert-butylpyridine Chemical compound CC(C)(C)C1=CC=CN=C1C(C)(C)C XGBWXISUZXYULS-UHFFFAOYSA-N 0.000 description 2
- CEBRPXLXYCFYGU-UHFFFAOYSA-N 3-methylbut-1-enylbenzene Chemical compound CC(C)C=CC1=CC=CC=C1 CEBRPXLXYCFYGU-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 239000003791 organic solvent mixture Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000035882 stress Effects 0.000 description 2
- 229920006132 styrene block copolymer Polymers 0.000 description 2
- HIACAHMKXQESOV-UHFFFAOYSA-N 1,2-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC=C1C(C)=C HIACAHMKXQESOV-UHFFFAOYSA-N 0.000 description 1
- RNDNSYIPLPAXAZ-UHFFFAOYSA-N 2-Phenyl-1-propanol Chemical compound OCC(C)C1=CC=CC=C1 RNDNSYIPLPAXAZ-UHFFFAOYSA-N 0.000 description 1
- MRXPNWXSFCODDY-UHFFFAOYSA-N 2-methyl-2-phenyloxirane Chemical compound C=1C=CC=CC=1C1(C)CO1 MRXPNWXSFCODDY-UHFFFAOYSA-N 0.000 description 1
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 239000004831 Hot glue Substances 0.000 description 1
- 241000907903 Shorea Species 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000004630 atomic force microscopy Methods 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- 239000000412 dendrimer Substances 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
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- 238000007336 electrophilic substitution reaction Methods 0.000 description 1
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- 229920000587 hyperbranched polymer Polymers 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000002356 laser light scattering Methods 0.000 description 1
- 238000010551 living anionic polymerization reaction Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 230000004001 molecular interaction Effects 0.000 description 1
- 229920006030 multiblock copolymer Polymers 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000010094 polymer processing Methods 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
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- 238000011084 recovery Methods 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000008027 tertiary esters Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/002—Dendritic macromolecules
- C08G83/005—Hyperbranched macromolecules
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/16—Macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
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- 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
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/002—Dendritic macromolecules
- C08G83/003—Dendrimers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L53/02—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Transplantation (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Inorganic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29350801P | 2001-05-29 | 2001-05-29 | |
| US60/293,508 | 2001-05-29 | ||
| PCT/CA2002/000792 WO2002096967A1 (en) | 2001-05-29 | 2002-05-29 | Arborescent thermoplastic elastomers and products therefrom |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2446866A1 CA2446866A1 (en) | 2002-12-05 |
| CA2446866C true CA2446866C (en) | 2011-05-03 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2446866A Expired - Fee Related CA2446866C (en) | 2001-05-29 | 2002-05-29 | Arborescent thermoplastic elastomers and products therefrom |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6747098B2 (enExample) |
| EP (1) | EP1395622B1 (enExample) |
| JP (1) | JP4231777B2 (enExample) |
| CN (1) | CN100455615C (enExample) |
| AT (1) | ATE527001T1 (enExample) |
| AU (1) | AU2002302269B2 (enExample) |
| CA (1) | CA2446866C (enExample) |
| ES (1) | ES2374719T3 (enExample) |
| WO (1) | WO2002096967A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE10328854A1 (de) * | 2003-06-26 | 2005-01-13 | Basf Ag | Verfahren zur Herstellung von Polyisobutenen |
| CN1305925C (zh) * | 2005-07-07 | 2007-03-21 | 复旦大学 | 一种软硬多嵌段聚合物及其合成方法 |
| WO2007136700A2 (en) * | 2006-05-17 | 2007-11-29 | The University Of Akron | Method of purifying block copolymers |
| US8486135B2 (en) | 2006-06-01 | 2013-07-16 | Abbott Cardiovascular Systems Inc. | Implantable medical devices fabricated from branched polymers |
| KR20090058521A (ko) * | 2006-09-01 | 2009-06-09 | 더 유니버시티 오브 아크론 | 가지형 중합체 및 그 제조 방법 |
| US20080243228A1 (en) | 2007-03-28 | 2008-10-02 | Yunbing Wang | Implantable medical devices fabricated from block copolymers |
| US8262723B2 (en) * | 2007-04-09 | 2012-09-11 | Abbott Cardiovascular Systems Inc. | Implantable medical devices fabricated from polymer blends with star-block copolymers |
| US20080269874A1 (en) | 2007-04-30 | 2008-10-30 | Yunbing Wang | Implantable medical devices fabricated from polymers with radiopaque groups |
| EP2075016A1 (en) * | 2007-11-13 | 2009-07-01 | Abbott Laboratories Vascular Enterprises Limited | Branched polymers in medical devices |
| US20100063211A1 (en) * | 2008-09-11 | 2010-03-11 | Lanxess, Inc. | Arborescent polymers and process for making same |
| US20100059452A1 (en) * | 2008-09-11 | 2010-03-11 | Lanxess, Inc. | Method of purifying block copolymers |
| FR2938543B1 (fr) * | 2008-11-19 | 2010-11-12 | Michelin Soc Tech | Nouveau copolymere a bloc elastomerique, son procede de preparation, son utilisation dans une composition elastomere |
| RU2012148554A (ru) * | 2010-04-16 | 2014-05-27 | Лэнксесс Инк. | Древовидные полимеры, имеющие ядро с высокой температурой стеклования, и способ получения таких полимеров |
| US9079980B2 (en) | 2010-08-31 | 2015-07-14 | The Goodyear Tire & Rubber Company | Copolymers of conjugated triene monomers for improved filler interaction |
| WO2014025986A2 (en) | 2012-08-10 | 2014-02-13 | The University Of Akron | Novel polyisobutylene-based thermoplastic elastomers |
| CN103724508B (zh) * | 2012-10-16 | 2016-03-30 | 中国石油化工股份有限公司 | 一种支化聚合物及其制备方法 |
| WO2014117060A1 (en) * | 2013-01-25 | 2014-07-31 | The University Of Akron | Wound protecting polymers |
| CN104892813B (zh) * | 2014-03-06 | 2017-04-26 | 中国石油化工股份有限公司 | 一种支化聚合物的卤化物及其制备方法 |
| KR20160079323A (ko) * | 2014-12-26 | 2016-07-06 | 한화토탈 주식회사 | 변성 공액디엔계 중합체 및 그를 포함하는 조성물 |
| EP3958050B1 (en) * | 2018-07-16 | 2024-09-11 | Huntsman International LLC | Polymeric ion conductive electrolyte sheet |
| US12157810B1 (en) | 2020-10-20 | 2024-12-03 | Polyballistics LLC | Filled uncured rubber compound for less lethal ammunition and drug-eluting electrospun fiber mat |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4946899A (en) * | 1988-12-16 | 1990-08-07 | The University Of Akron | Thermoplastic elastomers of isobutylene and process of preparation |
| US5260383A (en) * | 1991-04-17 | 1993-11-09 | Polysar Rubber Corporation | Polyisobutylene based block copolymers |
| JPH05310868A (ja) * | 1992-05-11 | 1993-11-22 | Japan Synthetic Rubber Co Ltd | 医療材用組成物 |
| JP3362438B2 (ja) * | 1993-03-30 | 2003-01-07 | 日本ゼオン株式会社 | ブロック共重合体の取得法 |
| US5428111A (en) * | 1993-10-15 | 1995-06-27 | University Of Massachusetts | Living polymerization of olefins to produce copolymer |
| US5395885A (en) * | 1993-12-17 | 1995-03-07 | The University Of Akron | Multi-arm cationic star-polymers |
| US5458796A (en) * | 1994-03-31 | 1995-10-17 | Shell Oil Company | Synthesis of polyisobutylene star-branched polymers via living carbocationic polymerization |
| US5721331A (en) * | 1995-03-08 | 1998-02-24 | Kuraray Co., Ltd. | Isobutylene-based polymer and process of producing the same |
| US5630844A (en) * | 1995-06-07 | 1997-05-20 | Novamed Medical Products Manufacturing, Inc. | Biocompatible hydrophobic laminate with thermoplastic elastomer layer |
| DE19628450A1 (de) * | 1996-07-15 | 1998-01-22 | Bayer Ag | Verfahren zur Herstellung von hochverzweigten Polyisoolefinen |
| US5741331A (en) * | 1996-07-29 | 1998-04-21 | Corvita Corporation | Biostable elastomeric polymers having quaternary carbons |
| US6268446B1 (en) * | 1997-12-04 | 2001-07-31 | The University Of Western Ontario | Initiators for carbocationic polymerization of olefins |
| JP2000038427A (ja) * | 1998-05-20 | 2000-02-08 | Kanegafuchi Chem Ind Co Ltd | 耐熱性医薬・医療用材料およびそれからなる容器、シ―ル性物品 |
| GB0025211D0 (en) | 2000-10-14 | 2000-11-29 | Avecia Bv | Hyperbranched compositions |
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2002
- 2002-05-29 CN CNB028110358A patent/CN100455615C/zh not_active Expired - Fee Related
- 2002-05-29 JP JP2003500146A patent/JP4231777B2/ja not_active Expired - Fee Related
- 2002-05-29 ES ES02729729T patent/ES2374719T3/es not_active Expired - Lifetime
- 2002-05-29 CA CA2446866A patent/CA2446866C/en not_active Expired - Fee Related
- 2002-05-29 WO PCT/CA2002/000792 patent/WO2002096967A1/en not_active Ceased
- 2002-05-29 US US10/156,767 patent/US6747098B2/en not_active Expired - Fee Related
- 2002-05-29 AU AU2002302269A patent/AU2002302269B2/en not_active Ceased
- 2002-05-29 AT AT02729729T patent/ATE527001T1/de active
- 2002-05-29 EP EP02729729A patent/EP1395622B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CN100455615C (zh) | 2009-01-28 |
| ATE527001T1 (de) | 2011-10-15 |
| ES2374719T3 (es) | 2012-02-21 |
| WO2002096967A1 (en) | 2002-12-05 |
| EP1395622B1 (en) | 2011-10-05 |
| CN1604923A (zh) | 2005-04-06 |
| JP2004526857A (ja) | 2004-09-02 |
| AU2002302269B2 (en) | 2007-11-15 |
| EP1395622A1 (en) | 2004-03-10 |
| US6747098B2 (en) | 2004-06-08 |
| US20030065098A1 (en) | 2003-04-03 |
| CA2446866A1 (en) | 2002-12-05 |
| JP4231777B2 (ja) | 2009-03-04 |
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