JP2019534368A - ペンタブロックコポリマー - Google Patents
ペンタブロックコポリマー Download PDFInfo
- Publication number
- JP2019534368A JP2019534368A JP2019527387A JP2019527387A JP2019534368A JP 2019534368 A JP2019534368 A JP 2019534368A JP 2019527387 A JP2019527387 A JP 2019527387A JP 2019527387 A JP2019527387 A JP 2019527387A JP 2019534368 A JP2019534368 A JP 2019534368A
- Authority
- JP
- Japan
- Prior art keywords
- styrene
- polymer
- copolymer
- pentablock
- block
- 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.)
- Granted
Links
- 229920001577 copolymer Polymers 0.000 title claims description 52
- 229920000642 polymer Polymers 0.000 claims abstract description 114
- 239000000178 monomer Substances 0.000 claims description 52
- 239000003999 initiator Substances 0.000 claims description 45
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 44
- 229920001400 block copolymer Polymers 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 29
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 26
- 238000006116 polymerization reaction Methods 0.000 claims description 24
- -1 polybutylene succinate Polymers 0.000 claims description 23
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims description 22
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 21
- 239000000835 fiber Substances 0.000 claims description 20
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 12
- 150000001450 anions Chemical class 0.000 claims description 11
- 239000007822 coupling agent Substances 0.000 claims description 9
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- 150000001993 dienes Chemical class 0.000 claims description 7
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims description 7
- 238000007142 ring opening reaction Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims description 6
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims description 6
- 230000001588 bifunctional effect Effects 0.000 claims description 5
- 150000002118 epoxides Chemical class 0.000 claims description 5
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical group CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 4
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000129 anionic group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000005676 cyclic carbonates Chemical class 0.000 claims description 4
- 150000003951 lactams Chemical class 0.000 claims description 4
- 150000002596 lactones Chemical class 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical group CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 3
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 3
- 150000004292 cyclic ethers Chemical class 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 229920001296 polysiloxane Polymers 0.000 claims description 3
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 claims description 2
- OXHSYXPNALRSME-UHFFFAOYSA-N (4-ethenylphenyl)-trimethylsilane Chemical compound C[Si](C)(C)C1=CC=C(C=C)C=C1 OXHSYXPNALRSME-UHFFFAOYSA-N 0.000 claims description 2
- CORMBJOFDGICKF-UHFFFAOYSA-N 1,3,5-trimethoxy 2-vinyl benzene Chemical group COC1=CC(OC)=C(C=C)C(OC)=C1 CORMBJOFDGICKF-UHFFFAOYSA-N 0.000 claims description 2
- GWYPDXLJACEENP-UHFFFAOYSA-N 1,3-cycloheptadiene Chemical compound C1CC=CC=CC1 GWYPDXLJACEENP-UHFFFAOYSA-N 0.000 claims description 2
- YJCVRMIJBXTMNR-UHFFFAOYSA-N 1,3-dichloro-2-ethenylbenzene Chemical compound ClC1=CC=CC(Cl)=C1C=C YJCVRMIJBXTMNR-UHFFFAOYSA-N 0.000 claims description 2
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical group CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 claims description 2
- WHFHDVDXYKOSKI-UHFFFAOYSA-N 1-ethenyl-4-ethylbenzene Chemical group CCC1=CC=C(C=C)C=C1 WHFHDVDXYKOSKI-UHFFFAOYSA-N 0.000 claims description 2
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 claims description 2
- UVHXEHGUEKARKZ-UHFFFAOYSA-N 1-ethenylanthracene Chemical compound C1=CC=C2C=C3C(C=C)=CC=CC3=CC2=C1 UVHXEHGUEKARKZ-UHFFFAOYSA-N 0.000 claims description 2
- SMSKIVCCLIQXFD-UHFFFAOYSA-N 1-tert-butyl-3-ethenylbenzene Chemical group CC(C)(C)C1=CC=CC(C=C)=C1 SMSKIVCCLIQXFD-UHFFFAOYSA-N 0.000 claims description 2
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 claims description 2
- ADTJCNMCEVKJQM-UHFFFAOYSA-N 2-(2-ethoxyethoxymethyl)oxirane Chemical compound CCOCCOCC1CO1 ADTJCNMCEVKJQM-UHFFFAOYSA-N 0.000 claims description 2
- PDELBHCVXBSVPJ-UHFFFAOYSA-N 2-ethenyl-1,3,5-trimethylbenzene Chemical group CC1=CC(C)=C(C=C)C(C)=C1 PDELBHCVXBSVPJ-UHFFFAOYSA-N 0.000 claims description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical group C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 2
- PMZXJPLGCUVUDN-UHFFFAOYSA-N 4-ethenyl-1,2-dimethylbenzene Chemical group CC1=CC=C(C=C)C=C1C PMZXJPLGCUVUDN-UHFFFAOYSA-N 0.000 claims description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- VJIYRPVGAZXYBD-UHFFFAOYSA-N dibromosilane Chemical compound Br[SiH2]Br VJIYRPVGAZXYBD-UHFFFAOYSA-N 0.000 claims description 2
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 claims description 2
- 150000005690 diesters Chemical class 0.000 claims description 2
- 229920001971 elastomer Polymers 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 2
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 claims 3
- 229920002959 polymer blend Polymers 0.000 claims 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims 2
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 claims 2
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- WGGLDBIZIQMEGH-UHFFFAOYSA-N 1-bromo-4-ethenylbenzene Chemical compound BrC1=CC=C(C=C)C=C1 WGGLDBIZIQMEGH-UHFFFAOYSA-N 0.000 claims 1
- BOVQCIDBZXNFEJ-UHFFFAOYSA-N 1-chloro-3-ethenylbenzene Chemical compound ClC1=CC=CC(C=C)=C1 BOVQCIDBZXNFEJ-UHFFFAOYSA-N 0.000 claims 1
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 claims 1
- JWVTWJNGILGLAT-UHFFFAOYSA-N 1-ethenyl-4-fluorobenzene Chemical compound FC1=CC=C(C=C)C=C1 JWVTWJNGILGLAT-UHFFFAOYSA-N 0.000 claims 1
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 claims 1
- SXXOSRMQLZJZHB-UHFFFAOYSA-N 2-butylhex-1-enylbenzene Chemical group CCCCC(CCCC)=CC1=CC=CC=C1 SXXOSRMQLZJZHB-UHFFFAOYSA-N 0.000 claims 1
- DDBYLRWHHCWVID-UHFFFAOYSA-N 2-ethylbut-1-enylbenzene Chemical group CCC(CC)=CC1=CC=CC=C1 DDBYLRWHHCWVID-UHFFFAOYSA-N 0.000 claims 1
- BTOVVHWKPVSLBI-UHFFFAOYSA-N 2-methylprop-1-enylbenzene Chemical group CC(C)=CC1=CC=CC=C1 BTOVVHWKPVSLBI-UHFFFAOYSA-N 0.000 claims 1
- CEBRPXLXYCFYGU-UHFFFAOYSA-N 3-methylbut-1-enylbenzene Chemical group CC(C)C=CC1=CC=CC=C1 CEBRPXLXYCFYGU-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims 1
- 229920000954 Polyglycolide Polymers 0.000 claims 1
- 229920000331 Polyhydroxybutyrate Polymers 0.000 claims 1
- 238000012648 alternating copolymerization Methods 0.000 claims 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical group CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 claims 1
- XZKRXPZXQLARHH-UHFFFAOYSA-N buta-1,3-dienylbenzene Chemical compound C=CC=CC1=CC=CC=C1 XZKRXPZXQLARHH-UHFFFAOYSA-N 0.000 claims 1
- CJSBUWDGPXGFGA-UHFFFAOYSA-N dimethyl-butadiene Natural products CC(C)=CC=C CJSBUWDGPXGFGA-UHFFFAOYSA-N 0.000 claims 1
- HWXQYUCHSICMAS-UHFFFAOYSA-N octa-3,5-diene Chemical compound CCC=CC=CCC HWXQYUCHSICMAS-UHFFFAOYSA-N 0.000 claims 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims 1
- 239000005015 poly(hydroxybutyrate) Substances 0.000 claims 1
- 229920000218 poly(hydroxyvalerate) Polymers 0.000 claims 1
- 229920001606 poly(lactic acid-co-glycolic acid) Polymers 0.000 claims 1
- 229920002961 polybutylene succinate Polymers 0.000 claims 1
- 239000004631 polybutylene succinate Substances 0.000 claims 1
- 229920001451 polypropylene glycol Polymers 0.000 claims 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical group C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims 1
- 150000003440 styrenes Chemical group 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 57
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 28
- 239000002904 solvent Substances 0.000 description 22
- 239000007787 solid Substances 0.000 description 16
- 238000004458 analytical method Methods 0.000 description 14
- 238000002390 rotary evaporation Methods 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- 239000006185 dispersion Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000012298 atmosphere Substances 0.000 description 10
- 230000008859 change Effects 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 229920000428 triblock copolymer Polymers 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 239000000693 micelle Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 0 CC(*)CCCN=C Chemical compound CC(*)CCCN=C 0.000 description 7
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000010511 deprotection reaction Methods 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
- JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 238000002296 dynamic light scattering Methods 0.000 description 5
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- NPCWHJYLJRDXNV-UHFFFAOYSA-N 2-[ethoxy-[ethoxy(oxiran-2-yl)methoxy]methyl]oxirane Chemical compound C(C)OC(C1CO1)OC(C1CO1)OCC NPCWHJYLJRDXNV-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000004745 nonwoven fabric Substances 0.000 description 4
- 230000001902 propagating effect Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- REKYPYSUBKSCAT-UHFFFAOYSA-N 3-hydroxypentanoic acid Chemical compound CCC(O)CC(O)=O REKYPYSUBKSCAT-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 229920001410 Microfiber Polymers 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 3
- 239000003658 microfiber Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920000346 polystyrene-polyisoprene block-polystyrene Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- KGKAYWMGPDWLQZ-UHFFFAOYSA-N 1,2-bis(bromomethyl)benzene Chemical group BrCC1=CC=CC=C1CBr KGKAYWMGPDWLQZ-UHFFFAOYSA-N 0.000 description 2
- AKXKKSAGNHWXPQ-UHFFFAOYSA-N 1,2-dibromo-3,4-dimethylbenzene Chemical group CC1=CC=C(Br)C(Br)=C1C AKXKKSAGNHWXPQ-UHFFFAOYSA-N 0.000 description 2
- BJZZCHRYTNIBCS-UHFFFAOYSA-N 1,3-bis(2-phenylethenyl)benzene Chemical compound C=1C=CC=CC=1C=CC(C=1)=CC=CC=1C=CC1=CC=CC=C1 BJZZCHRYTNIBCS-UHFFFAOYSA-N 0.000 description 2
- ROGIWVXWXZRRMZ-UHFFFAOYSA-N 2-methylbuta-1,3-diene;styrene Chemical compound CC(=C)C=C.C=CC1=CC=CC=C1 ROGIWVXWXZRRMZ-UHFFFAOYSA-N 0.000 description 2
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 2
- ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 238000000137 annealing Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical group C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 150000001261 hydroxy acids Chemical class 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
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Images
Classifications
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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
- C08F297/02—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type
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Abstract
Description
ΔG≒ΔHm>0
であるブレンドを指す。
のものであり、
R20は、1〜20個の炭素原子、好ましくは1〜12個の炭素原子を有し、任意にカテナリー(鎖内)酸素原子、カルボニル又はカルボキシレートで置換されていてもよい、直鎖又は分岐鎖であり得るアルキレン部分であり、Xは、−O−又はNR1−であり、ここで、R1は、C1〜C4アルキルである。環状ラクトンは、3−ヒドロキシブチレート、4−ヒドロキシブチレート、3−ヒドロキシバレレート、乳酸、3−ヒドロキシプロパノエート、4−ヒドロペンタノエート、3−ヒドロキシペンタノエート、3−ヒドロキシヘキサノエート、3−ヒドロキシヘプタノエート、3−ヒドロキシオクタノエート、ジオキサノン、バレロラクトン、カプロラクトン、及びグリコール酸を含む、ヒドロキシ酸から誘導されると理解される。ラクタムは、対応するアミノ酸から誘導される。ラクチドなどのヒドロキシ酸のダイマーが使用され得る。
Li−R30−Li
(式中、R30は二価炭化水素基である)
によって表される2個のリチウム基を含む有機化合物から選択することができる。R30は、一般に、R30基当たり4〜30個の炭素原子を含有する。有用な二官能性開始剤は、参照により本明細書に組み入れられる、米国特許第7884160号(Wang et al.)及び米国特許第5750055号(Van Der Steen et.al)に記載されている。
MBraun Labmaster SPグローブボックス内で、又はアニオン重合を可能にするように設計された特注ガラス製品内で、ポリマー合成及び試薬精製を行った(例えば、Ndoni,S.;Papadakis,C.M.;Bates,F.S.;Almdal、K.Laboratory−scale Setup for Anionic Polymerization under Inert Atmosphere、Review of Scientific Instruments1995,66(2),1090−1095 DOI:10.1063/1.1146052を参照されたい)。アニオン重合及び試薬操作に標準的な無空気法を使用した。試薬及び対応する供給元を以下の表1に列挙する。
脱気した1,1−ジフェニルエチレンを含有するストラウスフラスコにカニューレで移す前に、1時間超にわたりArでバブリングすることによって、ベンゼンを脱気した。次いで、注射器を介してAr向流下でSec−BuLiを添加したところ、1時間かけて淡黄色から濃いワインレッド色への非常に緩慢な色変化が生じた。一晩撹拌した後、ベンゼンを滴下漏斗に真空移送した。CH2Cl2をCaH2上で乾燥させ、3回の凍結−ポンプ−解凍サイクルで脱気し、受けフラスコに真空移送した。スチレンをCaH2上で一晩撹拌し、3回の凍結−ポンプ−解凍サイクルで脱気し、次いで、乾燥したジブチル−マグネシウムを含むシュレンクボンベに真空移送した。Ar雰囲気中で一晩撹拌した後、スチレンを再び受けフラスコに真空移送して、最終乾燥モノマーを得た。CaH2及びジブチルマグネシウムからの逐次的な真空移動により、上記のようにイソプレンを乾燥させた。rac−ラクチドを酢酸エチルから再結晶させ、高真空下で一晩乾燥させた。
テトラヒドロフラン(Tetrahydrofuran、THF、250ppmのBHTで安定化)を溶媒及び移動相として使用した。既知の濃度の溶液をガラスシンチレーションバイアル内で調製した。目標濃度は約5.0mg/mLであった。溶解を可能にするために、バイアルを少なくとも4時間旋回させた。次いで、0.2μのPTFEシリンジフィルターを用いて溶液を濾過した。GPC条件は以下の通りであった。
Malvern製Zetasizerを使用して、動的光散乱法(Dynamic light scattering、DLS)を実施した。DLS用の溶液を、約4〜5mLのNMP又はDMF中0.1重量%のポリマーで調製し、少なくとも12時間放置して溶解させた。PEOを含有するコポリマー溶液を60℃で少なくとも1時間加熱して、溶液中で結晶ドメインを溶融させ平衡化させた。測定のために、溶液を0.22又は0.45μmのPP注射器フィルターに通して石英キュベットに濾過した。試料をホルダー内で2分間平衡させた後、25℃で測定を行った。測定器ソフトウェアは、測定位置及び減衰器を調整することにより、173°での測定設定を自動で最適化した。分散剤としてNMP又はDMFを用いて、フィッティングを行った。測定相関曲線のキュムラント分析から、強度加重平均流体力学的サイズ(Z−Ave)及び多分散度(PDI)を計算した。全ての試料が単一のピークを示した。ISO/OSISOとISL/LSISLとの比較のグラフ表示については、図2及び3を参照されたい。
Claims (21)
- 式ABCBAのペンタブロックコポリマーであって、式中、
Bは、≧70℃のTgを有しかつ前記コポリマーの30〜80重量%を構成するビニル芳香族ブロックであり、
Cは、≦25℃のTgを有しかつ前記コポリマーの10〜40重量%を構成するゴムブロックであり、
Aは、開環重合から誘導されたブロックであり、B及びCブロックの両方に対して実質的に非相溶性であり、
B+Cは前記コポリマーの70〜95重量%を構成する、ペンタブロックコポリマー。 - Cが前記コポリマーの10〜30重量%を構成する、請求項1に記載のペンタブロックコポリマー。
- Bが、スチレン、α−メチルスチレン、4−メチルスチレン、3−メチルスチレン、4−エチルスチレン、3,4−ジメチルスチレン、2,4,6−トリメチルスチレン、3−tert−ブチル−スチレン、4−tert−ブチルスチレン、4−メトキシスチレン、4−トリメチルシリルスチレン、2,6−ジクロロスチレン、ビニルナフタレン、4−クロロスチレン、3−クロロスチレン、4−フルオロスチレン、4−ブロモスチレン、及びビニルアントラセンから選択される、請求項1に記載のペンタブロックコポリマー。
- Cが、ブタジエン、イソプレン等、並びに1,3−シクロジエンモノマー、例えば、1,3−シクロヘキサジエン、1,3−シクロヘプタジエン、及び1,3−シクロオクタジエン、好ましくは1,3−シクロヘキサジエン、並びにこれらの混合物から選択される、請求項1に記載のペンタブロックコポリマー。
- Cが、−[Si(R10)2−O]−(式中、各R10は、有機基、例えば、アルキル、シクロアルキル又はアリールを表す)の繰り返し単位を有するオルガノポリシロキサンである、請求項1に記載のペンタブロックコポリマー。
- Aが、オキシラン(エポキシド)、環状スルフィド、ラクトン、ラクチド、環状カーボネート、ラクタム及びアジリジンから選択される環状モノマーの開環アニオン重合から誘導されたものである、請求項1に記載のペンタブロックコポリマー。
- 前記Aブロックが、ラクトンの開環重合から誘導された、ポリ(乳酸)、ポリ(グリコール酸)、ポリ(乳酸−co−グリコール酸)、ポリブチレンサクシネート、ポリヒドロキシブチレート、ポリヒドロキシバレレートから選択されるポリエステルを含む、請求項1に記載のペンタブロックコポリマー。
- 前記Aブロックが、環状エーテルの開環重合から誘導された、ポリ(エチレンオキシド)、ポリ(プロピレンオキシド)、ポリ(エトキシエチル−グリシジルエーテル)、及びこれらのコポリマーから選択されるポリエステルである、請求項1に記載のペンタブロックコポリマー。
- Mnが>60kDaである、請求項1に記載のペンタブロックコポリマー。
- Mnが60〜500kDaである、請求項9に記載のペンタブロックコポリマー。
- Bが、スチレン、ビニルピリジン、ビニルトルエン、α−メチルスチレン、メチルスチレン、ジメチルスチレン、エチルスチレン、ジエチルスチレン、t−ブチルスチレン、ジ−n−ブチルスチレン、イソプロピルスチレン、その他のアルキル化スチレン、スチレン類似体、及びスチレン同族体を含むビニル芳香族モノマーから誘導されたものである、請求項1に記載のペンタブロックコポリマー。
- Cが、ブタジエン、イソプレン、エチルブタジエン、フェニルブタジエン、ピペリレン、ペンタジエン、ヘキサジエン、エチルヘキサジエン、及びジメチルブタジエンを含む重合共役ジエンから誘導されたものである、請求項1に記載のペンタブロックコポリマー。
- Aが二酸化炭素とオキシランとの交互共重合から誘導されたものである、請求項1に記載のペンタブロックコポリマー。
- 請求項1に記載のペンタブロックの調製方法であって、a)前記Cブロックモノマーをアニオン重合する工程、b)前記Bブロックモノマーを重合する工程、c)工程a)及びb)における前記ブロックコポリマー形態をカップリング剤によりカップリングし、工程c)のカップリングされた前記ポリマーと開環重合性モノマーとを更に重合する工程を含む、方法。
- 前記カップリング剤が、ジハロゲン化化合物、二酸クロリド、二酸ブロミド、ジクロロ化合物、ジブロモシラン及びジクロロシラン、並びに二官能性化合物:ビス−エポキシド、ビス−アジリジン、ビス−イソシアネート、ビス無水物及びジエステルから選択される、請求項14に記載の方法。
- 請求項1に記載のペンタブロックの調製方法であって、a)官能性アニオン開始剤により前記Cブロックモノマーをアニオン重合する工程、b)前記Bブロックモノマーを重合し、前記官能性アニオン開始剤を脱保護し、工程c)のカップリングされたポリマーと開環重合性モノマーとを更に重合する工程を含む、方法。
- 請求項1に記載のペンタブロックの調製方法であって、a)二官能性アニオン開始剤により前記Cブロックモノマーをアニオン重合する工程、b)前記Bブロックモノマーを重合し、工程b)のBCBコポリマーと開環重合性Aモノマーとを更に重合する工程を含む、方法。
- 請求項1〜13のいずれか一項に記載のペンタブロックコポリマーを含む造形物品。
- フィルム、シート及び繊維を含む、請求項18に記載の造形物品。
- 請求項1〜13のいずれか一項に記載のペンタブロックコポリマーと、A、B、C、BC、BCB、又はABC(コ)ポリマーとを含む、ポリマーブレンド。
- 前記ペンタブロックコポリマーが、前記ポリマーブレンドの>50重量%を構成する、請求項20に記載のポリマーブレンド。
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63117028A (ja) * | 1986-11-05 | 1988-05-21 | Takemoto Oil & Fat Co Ltd | ブロツク共重合体の製造方法 |
JPH0418418A (ja) * | 1989-11-29 | 1992-01-22 | Denki Kagaku Kogyo Kk | 永久帯電防止性樹脂組成物 |
JPH07126359A (ja) * | 1993-11-01 | 1995-05-16 | Daicel Chem Ind Ltd | (ビニル重合体−ポリラクトン)ブロック共重合体 |
JP2003335917A (ja) * | 2002-05-20 | 2003-11-28 | Kuraray Co Ltd | 熱可塑性エラストマー組成物 |
Family Cites Families (41)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL271831A (ja) | 1960-11-29 | |||
US3283042A (en) | 1963-08-23 | 1966-11-01 | Univ California | Method of forming porous membranes |
USRE27145E (en) | 1969-05-20 | 1971-06-22 | Side-chain | |
US4039593A (en) | 1973-05-18 | 1977-08-02 | Lithium Corporation Of America | Preparation of hydroxy-terminated conjugated diene polymers |
US3971373A (en) | 1974-01-21 | 1976-07-27 | Minnesota Mining And Manufacturing Company | Particle-loaded microfiber sheet product and respirators made therefrom |
US4100324A (en) | 1974-03-26 | 1978-07-11 | Kimberly-Clark Corporation | Nonwoven fabric and method of producing same |
US4258144A (en) | 1979-11-21 | 1981-03-24 | Phillips Petroleum Company | Polyphenylene ether blends |
US4429001A (en) | 1982-03-04 | 1984-01-31 | Minnesota Mining And Manufacturing Company | Sheet product containing sorbent particulate material |
IT1194408B (it) | 1983-09-28 | 1988-09-22 | Anic Spa | Processo per la sintesi di copolimeri a blocchi a base di pivalolattone |
JPH0710957B2 (ja) * | 1986-08-21 | 1995-02-08 | 日本油脂株式会社 | 塗装用プライマー組成物 |
US5149576A (en) | 1990-11-26 | 1992-09-22 | Kimberly-Clark Corporation | Multilayer nonwoven laminiferous structure |
US5145727A (en) | 1990-11-26 | 1992-09-08 | Kimberly-Clark Corporation | Multilayer nonwoven composite structure |
US5321148A (en) | 1993-12-30 | 1994-06-14 | Fmc Corporation | Process for preparing functionalized alkyllithium compounds |
US6160054A (en) | 1995-05-08 | 2000-12-12 | Fmc Corporation | Hetero-telechelic polymers and processes for making same |
US6197891B1 (en) | 1994-05-13 | 2001-03-06 | Fmc Corporation | Functionalized chain extended initiators for anionic polymerization |
TW322493B (ja) | 1994-06-27 | 1997-12-11 | Shell Int Research | |
TW346498B (en) * | 1994-10-11 | 1998-12-01 | Shell Int Research | Epoxidized monohydroxylated rubber toughening modifiers for epoxy resins |
US5900464A (en) | 1995-07-25 | 1999-05-04 | Fmc Corporation | Processes for making methacrylate and acrylate polymers |
US6184338B1 (en) | 1997-08-27 | 2001-02-06 | Fmc Corporation | Anionic polymerization initiators containing tertiary amine functionality, their chain extended analogues, and processes for using the same |
US6391981B1 (en) | 1999-04-23 | 2002-05-21 | Kraton Polymers Us Llc | Increased throughput in the manufacture of anionic polymers by reduction in polymer cement viscosity through the addition of metal alkyls |
US7884160B2 (en) | 2005-12-19 | 2011-02-08 | Bridgestone Corporation | Non-spherical nanoparticles made from living triblock polymer chains |
DE102006045282C5 (de) | 2006-09-22 | 2012-11-22 | Helmholtz-Zentrum Geesthacht Zentrum für Material-und Küstenforschung GmbH | Isoporöse Membran und Verfahren zu ihrer Herstellung |
WO2009152349A1 (en) | 2008-06-12 | 2009-12-17 | 3M Innovative Properties Company | Melt blown fine fibers and methods of manufacture |
CA2727701A1 (en) | 2008-06-12 | 2009-12-17 | 3M Innovative Properties Company | Biocompatible hydrophilic compositions |
EP2443185B1 (en) | 2009-06-18 | 2014-06-11 | 3M Innovative Properties Company | Polymer foams |
US9914099B2 (en) | 2010-02-11 | 2018-03-13 | Klaus-Viktor Peinemann | Self-assembled block copolymer membrane |
SG194779A1 (en) | 2011-05-04 | 2013-12-30 | Univ Cornell | Multiblock copolymer films, methods of making same, and uses thereof |
US9861941B2 (en) | 2011-07-12 | 2018-01-09 | Kraton Polymers U.S. Llc | Modified sulfonated block copolymers and the preparation thereof |
DE102012207344A1 (de) | 2012-05-03 | 2013-11-07 | Helmholtz-Zentrum Geesthacht Zentrum für Material- und Küstenforschung GmbH | Membran mit isoporöser trennaktiver Schicht und Verfahren zur Herstellung einer Membran |
DE102012207338A1 (de) | 2012-05-03 | 2013-11-07 | Helmholtz-Zentrum Geesthacht Zentrum für Material- und Küstenforschung GmbH | Membran mit isoporöser trennaktiver Schicht und Verfahren zur Herstellung einer Membran |
EP2695669B1 (de) | 2012-08-09 | 2016-10-12 | Helmholtz-Zentrum Geesthacht Zentrum für Material- und Küstenforschung GmbH | Membran mit isoporöser trennaktiver Schicht und Verfahren zur Herstellung einer Membran |
EP2695668B1 (de) | 2012-08-09 | 2017-10-11 | Helmholtz-Zentrum Geesthacht Zentrum für Material- und Küstenforschung GmbH | Verfahren zum Herstellen einer thermoresponsiven Filtrationsmembran und thermoresponsive Filtrationsmembran |
DE102012221378A1 (de) | 2012-11-22 | 2014-05-22 | Helmholtz-Zentrum Geesthacht Zentrum für Material- und Küstenforschung GmbH | Verfahren zur Herstellung einer integral-asymmetrischen Hohlfaden-Polymermembran, integral-asymmetrische Hohlfaden-Polymermembran, Filtrationsmodul und Verwendung |
EP2969155A4 (en) | 2013-03-11 | 2016-11-23 | Univ Notre Dame Du Lac | MULTIBLOCK COPOLYMERS AND METHOD OF USE THEREOF |
EP3055049A1 (en) | 2013-10-08 | 2016-08-17 | King Abdullah University Of Science And Technology | Polystyrene-b-polyethylene oxide block copolymer membranes, methods of making, and methods of use |
CN103861480B (zh) | 2014-03-21 | 2016-01-06 | 东华大学 | 一种亲水性聚偏氟乙烯平板膜和中空纤维膜的制备方法 |
US9441078B2 (en) | 2014-05-30 | 2016-09-13 | Pall Corporation | Self-assembling polymers—I |
US9592477B2 (en) | 2014-05-30 | 2017-03-14 | Pall Corporation | Membrane comprising self-assembled block copolymer and process for producing the same by hybrid casting (Ib) |
US9592476B2 (en) | 2014-05-30 | 2017-03-14 | Pall Corporation | Membrane comprising self-assembled block copolymer and process for producing the same by hybrid casting (IIb) |
DE102014213027A1 (de) | 2014-07-04 | 2016-01-07 | Helmholtz-Zentrum Geesthacht Zentrum für Material- und Küstenforschung GmbH | Verfahren zur Herstellung einer Membran mit isoporöser trennaktiver Schicht mit einstellbarer Porengröße, Membran, Filtrationsmodul und Verwendung |
EP3544720A4 (en) | 2016-11-22 | 2020-07-01 | 3M Innovative Properties Company | POROUS MEMBRANES COMPRISING PENTA-BLOCK COPOLYMERS AND THEIR MANUFACTURING METHOD |
-
2017
- 2017-11-17 EP EP17817362.1A patent/EP3545023B1/en active Active
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63117028A (ja) * | 1986-11-05 | 1988-05-21 | Takemoto Oil & Fat Co Ltd | ブロツク共重合体の製造方法 |
JPH0418418A (ja) * | 1989-11-29 | 1992-01-22 | Denki Kagaku Kogyo Kk | 永久帯電防止性樹脂組成物 |
JPH07126359A (ja) * | 1993-11-01 | 1995-05-16 | Daicel Chem Ind Ltd | (ビニル重合体−ポリラクトン)ブロック共重合体 |
JP2003335917A (ja) * | 2002-05-20 | 2003-11-28 | Kuraray Co Ltd | 熱可塑性エラストマー組成物 |
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EP3545023B1 (en) | 2020-11-04 |
EP3545023A1 (en) | 2019-10-02 |
CN109983059B (zh) | 2022-05-24 |
JP7204646B2 (ja) | 2023-01-16 |
US20190322788A1 (en) | 2019-10-24 |
US10781279B2 (en) | 2020-09-22 |
CN109983059A (zh) | 2019-07-05 |
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