JP4685018B2 - アニオン重合ジイニシエーターおよびその調製方法 - Google Patents
アニオン重合ジイニシエーターおよびその調製方法 Download PDFInfo
- Publication number
- JP4685018B2 JP4685018B2 JP2006528104A JP2006528104A JP4685018B2 JP 4685018 B2 JP4685018 B2 JP 4685018B2 JP 2006528104 A JP2006528104 A JP 2006528104A JP 2006528104 A JP2006528104 A JP 2006528104A JP 4685018 B2 JP4685018 B2 JP 4685018B2
- Authority
- JP
- Japan
- Prior art keywords
- diinitiator
- compound
- diisopropenylbenzene
- ethylene
- present
- 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
- 238000010539 anionic addition polymerization reaction Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 54
- -1 diisopropenylbenzene compound Chemical class 0.000 claims description 44
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 20
- 239000005977 Ethylene Substances 0.000 claims description 20
- 150000002900 organolithium compounds Chemical class 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 229920006318 anionic polymer Polymers 0.000 claims description 4
- 125000002029 aromatic hydrocarbon group Chemical class 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 17
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 15
- 238000006116 polymerization reaction Methods 0.000 description 15
- 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 12
- 229910052744 lithium Inorganic materials 0.000 description 12
- 239000003999 initiator Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 239000000178 monomer Substances 0.000 description 11
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 10
- 229920001400 block copolymer Polymers 0.000 description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 238000010791 quenching Methods 0.000 description 6
- 239000005062 Polybutadiene Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 229920002857 polybutadiene Polymers 0.000 description 5
- 230000000171 quenching effect Effects 0.000 description 5
- IBVPVTPPYGGAEL-UHFFFAOYSA-N 1,3-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC(C(C)=C)=C1 IBVPVTPPYGGAEL-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical compound [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 2
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- ISJYRTKOQVJTRP-UHFFFAOYSA-N 1,2,3,5-tetraethyl-4,6-bis(prop-1-en-2-yl)benzene Chemical compound CCC1=C(CC)C(C(C)=C)=C(CC)C(C(C)=C)=C1CC ISJYRTKOQVJTRP-UHFFFAOYSA-N 0.000 description 1
- 238000011925 1,2-addition Methods 0.000 description 1
- IOQSSIPMPIYMDF-UHFFFAOYSA-N 1,3-diethoxypropane Chemical compound CCOCCCOCC IOQSSIPMPIYMDF-UHFFFAOYSA-N 0.000 description 1
- ZENYUPUKNXGVDY-UHFFFAOYSA-N 1,4-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=C(C(C)=C)C=C1 ZENYUPUKNXGVDY-UHFFFAOYSA-N 0.000 description 1
- BVUFUXGQLRJYDA-UHFFFAOYSA-N 1-(3-methylcyclopentyl)-3,5-bis(prop-1-en-2-yl)benzene Chemical compound C1C(C)CCC1C1=CC(C(C)=C)=CC(C(C)=C)=C1 BVUFUXGQLRJYDA-UHFFFAOYSA-N 0.000 description 1
- OEVVKKAVYQFQNV-UHFFFAOYSA-N 1-ethenyl-2,4-dimethylbenzene Chemical compound CC1=CC=C(C=C)C(C)=C1 OEVVKKAVYQFQNV-UHFFFAOYSA-N 0.000 description 1
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- VCNONMCQKBPBCY-UHFFFAOYSA-N 1-ethyl-3,5-bis(prop-1-en-2-yl)benzene Chemical compound CCC1=CC(C(C)=C)=CC(C(C)=C)=C1 VCNONMCQKBPBCY-UHFFFAOYSA-N 0.000 description 1
- WAEOXIOXMKNFLQ-UHFFFAOYSA-N 1-methyl-4-prop-2-enylbenzene Chemical group CC1=CC=C(CC=C)C=C1 WAEOXIOXMKNFLQ-UHFFFAOYSA-N 0.000 description 1
- ZMYIIHDQURVDRB-UHFFFAOYSA-N 1-phenylethenylbenzene Chemical group C=1C=CC=CC=1C(=C)C1=CC=CC=C1 ZMYIIHDQURVDRB-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- IRZJWDIVVZUDKM-UHFFFAOYSA-N 2-cyclopentyl-3-methyl-1,4-bis(prop-1-en-2-yl)-5-propylbenzene Chemical compound CC1=C(C(C)=C)C(CCC)=CC(C(C)=C)=C1C1CCCC1 IRZJWDIVVZUDKM-UHFFFAOYSA-N 0.000 description 1
- WBJWXIQDBDZMAW-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(O)=CC=C21 WBJWXIQDBDZMAW-UHFFFAOYSA-N 0.000 description 1
- BPERVJJFOOSUPU-UHFFFAOYSA-N 2-methyl-1,4-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=C(C(C)=C)C(C)=C1 BPERVJJFOOSUPU-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- UXWXHEVHZVXRQU-UHFFFAOYSA-N 4-(2-cyclobutylethyl)-1,2-bis(prop-1-en-2-yl)benzene Chemical compound C1=C(C(C)=C)C(C(=C)C)=CC=C1CCC1CCC1 UXWXHEVHZVXRQU-UHFFFAOYSA-N 0.000 description 1
- UEAFNORNMPYBAU-UHFFFAOYSA-N 4-methyl-1,2-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=C(C)C=C1C(C)=C UEAFNORNMPYBAU-UHFFFAOYSA-N 0.000 description 1
- ZYWUIIGAFQRAGK-UHFFFAOYSA-N 5-hexyl-2-methyl-1,3-bis(prop-1-en-2-yl)benzene Chemical compound CCCCCCC1=CC(C(C)=C)=C(C)C(C(C)=C)=C1 ZYWUIIGAFQRAGK-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical class CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 1
- HWDGACUYPXSDAV-UHFFFAOYSA-N CCC(C)CC(C)(C)c1cccc(C(C)(C)CC(C)CC)c1 Chemical compound CCC(C)CC(C)(C)c1cccc(C(C)(C)CC(C)CC)c1 HWDGACUYPXSDAV-UHFFFAOYSA-N 0.000 description 1
- GPCKFIWBUTWTDH-UHFFFAOYSA-N CCC(CC)(N)N Chemical compound CCC(CC)(N)N GPCKFIWBUTWTDH-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- NTYDXFVCCCPXRG-UHFFFAOYSA-N [Li]C(C)(C)CC(C)(C)C Chemical compound [Li]C(C)(C)CC(C)(C)C NTYDXFVCCCPXRG-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- PYHXGXCGESYPCW-UHFFFAOYSA-N alpha-phenylbenzeneacetic acid Natural products C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- VXTQKJXIZHSXBY-UHFFFAOYSA-N butan-2-yl 2-methylprop-2-enoate Chemical compound CCC(C)OC(=O)C(C)=C VXTQKJXIZHSXBY-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@](C)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- GTBGXKPAKVYEKJ-UHFFFAOYSA-N decyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C(C)=C GTBGXKPAKVYEKJ-UHFFFAOYSA-N 0.000 description 1
- 229920000359 diblock copolymer Polymers 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 230000001902 propagating effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 230000000717 retained effect Effects 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
- 150000004760 silicates Chemical class 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920006132 styrene block copolymer Polymers 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/02—Lithium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
- C08F297/04—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 polymerising vinyl aromatic monomers and conjugated dienes
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/46—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides selected from alkali metals
- C08F4/48—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides selected from alkali metals selected from lithium, rubidium, caesium or francium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Polymerization Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
Description
RLi
(式中、Rは、1〜20個の炭素原子を有する、脂肪族、脂環式、芳香族またはアルキル置換芳香族炭化水素基である)を有する有機リチウム化合物である。典型的な有機リチウム化合物は、イソプロピルリチウム、s−ブチルリチウム、t−オクチルリチウム、t−ブチルリチウム等である。s−ブチルリチウムおよびt−ブチルリチウムは、本発明での使用にとって好ましい。有機リチウム化合物の混合物も本発明方法で使用することができる。
以下の実施例は、本発明を例示するために与えられる。実施例は本発明の範囲を限定しようとするものではなく、その様に解釈されるべきものではない。量は、別段の指示がなければ、重量部または重量%である。
Claims (4)
- ジイソプロペニルベンゼン化合物対有機リチウム化合物のモル比が0.4:1〜0.6:1であり、ジエチルエーテル対有機リチウム化合物のモル比が0.1:1〜2:1であり、エチレン対有機リチウム化合物のモル比が1:1〜10:1となるように、ジイソプロペニルベンゼン化合物、エチレン、および有機リチウム化合物をジエチルエーテル、および溶剤中で、0℃以上55℃未満の範囲内の温度で反応させることにより調製されるアニオン重合ジイニシエーター。
- ジイソプロペニルベンゼン化合物対有機リチウム化合物のモル比が0.4:1〜0.6:1であり、ジエチルエーテル対有機リチウム化合物のモル比が0.1:1〜2:1であり、エチレン対有機リチウム化合物のモル比が1:1〜10:1となるように、ジイソプロペニルベンゼン化合物、エチレン、および有機リチウム化合物をジエチルエーテル、および溶剤中で、0℃以上55℃未満の範囲内の温度で反応させることを含むアニオン重合ジイニシエーターの調製方法。
- 請求項1または2に記載のジイニシエーターの存在下で共役非環式ジエン又はアクリル化合物を重合して得られたアニオンポリマー。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US50567003P | 2003-09-24 | 2003-09-24 | |
PCT/US2004/030890 WO2005030816A1 (en) | 2003-09-24 | 2004-09-22 | Anionic polymerization diinitiator and process for preparing same |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2007506841A JP2007506841A (ja) | 2007-03-22 |
JP4685018B2 true JP4685018B2 (ja) | 2011-05-18 |
Family
ID=34393053
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006528104A Expired - Fee Related JP4685018B2 (ja) | 2003-09-24 | 2004-09-22 | アニオン重合ジイニシエーターおよびその調製方法 |
Country Status (8)
Country | Link |
---|---|
US (2) | US7285596B2 (ja) |
EP (1) | EP1709090B1 (ja) |
JP (1) | JP4685018B2 (ja) |
KR (1) | KR100788111B1 (ja) |
CN (2) | CN100422225C (ja) |
ES (1) | ES2576631T3 (ja) |
TW (1) | TWI314562B (ja) |
WO (1) | WO2005030816A1 (ja) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100422225C (zh) * | 2003-09-24 | 2008-10-01 | 克拉通聚合物研究有限公司 | 阴离子聚合双引发剂和其制备方法 |
KR101044070B1 (ko) * | 2008-09-23 | 2011-06-27 | 주식회사 엘지화학 | 이관능성 유기 리튬 개시제 및 이를 이용하여 생산되는 공역디엔계 공중합체 및 이들의 제조방법 |
JP5602000B2 (ja) * | 2010-12-15 | 2014-10-08 | 旭化成ケミカルズ株式会社 | 粘接着剤用共重合体、その製造方法及び粘接着剤用組成物 |
KR101800496B1 (ko) * | 2014-06-16 | 2017-11-22 | 주식회사 엘지화학 | 변성 공액 디엔계 중합체, 이를 포함하는 변성 고무 조성물 및 변성 공액 디엔계 중합체의 제조방법 |
KR101775761B1 (ko) * | 2014-07-30 | 2017-09-19 | 주식회사 엘지화학 | 변성 공액 디엔계 중합체, 이를 포함하는 변성 고무 조성물 및 변성 공액 디엔계 중합체의 제조방법 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07304810A (ja) * | 1994-05-09 | 1995-11-21 | Shell Internatl Res Maatschappij Bv | 工業的に用いうる二官能性陰イオン重合開始剤の製造方法およびその使用 |
JPH0848709A (ja) * | 1994-06-27 | 1996-02-20 | Shell Internatl Res Maatschappij Bv | 工業的に適用可能な二官能価アニオン重合イニシエーターの製造方法及び該イニシエーターの使用 |
JP2001064328A (ja) * | 1999-09-01 | 2001-03-13 | Kuraray Co Ltd | α,ω−ジリチオポリマーまたはそれから誘導されるポリマーの製造方法 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3734973A (en) * | 1971-11-04 | 1973-05-22 | Phillips Petroleum Co | Multifunctional polymerization initiators from diisopropenylbenzene |
US5166277A (en) * | 1991-10-31 | 1992-11-24 | Shell Oil Company | Hydrogenation of unsaturation in low molecular weight diene polymers |
US5393843A (en) * | 1992-08-31 | 1995-02-28 | Shell Oil Company | Butadiene polymers having terminal functional groups |
US6043316A (en) * | 1996-11-13 | 2000-03-28 | Shell Oil Company | Crosslinkable hydroxy terminated polydiene polymer coating compositions for use on substrates and a process for preparing them |
US6462143B1 (en) * | 1998-02-03 | 2002-10-08 | Kraton Polymers Us Llc | Gel-free process for making functionalized anionically polymerized polymers |
US6242537B1 (en) * | 1998-03-30 | 2001-06-05 | Shell Oil Company | Gel-free process for making hydrogenated functionalized anionically polymerized polymers |
US6242538B1 (en) * | 1998-06-04 | 2001-06-05 | Shell Oil Company | Process for making hydrogenated gel-free functionalized anionically polymerized polymers |
US6613858B1 (en) * | 1998-08-31 | 2003-09-02 | Asahi Kasei Kabushiki Kaisha | Solution of dilithium polymerization initiator |
US6217798B1 (en) * | 1998-10-09 | 2001-04-17 | Shell Oil Company | Method for synthesis of a dilithium diisopropenylbenzene-based diinitiator |
US6455651B1 (en) * | 1999-04-23 | 2002-09-24 | Kraton Polymers U.S. Llc | Uniform initiation of anionic polymerization using organo-substituted alkali metal initiators |
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 |
US20020198343A1 (en) * | 2000-03-14 | 2002-12-26 | Willis Carl Lesley | Uniform initiation of anionic polymerization using organo-substituted alkali metal initiators |
CN100422225C (zh) * | 2003-09-24 | 2008-10-01 | 克拉通聚合物研究有限公司 | 阴离子聚合双引发剂和其制备方法 |
-
2004
- 2004-09-22 CN CNB200480031038XA patent/CN100422225C/zh not_active Expired - Fee Related
- 2004-09-22 US US10/947,011 patent/US7285596B2/en active Active
- 2004-09-22 JP JP2006528104A patent/JP4685018B2/ja not_active Expired - Fee Related
- 2004-09-22 CN CN200810145932XA patent/CN101402693B/zh not_active Expired - Fee Related
- 2004-09-22 EP EP04784675.3A patent/EP1709090B1/en not_active Not-in-force
- 2004-09-22 ES ES04784675.3T patent/ES2576631T3/es active Active
- 2004-09-22 WO PCT/US2004/030890 patent/WO2005030816A1/en active Application Filing
- 2004-09-22 KR KR1020067007713A patent/KR100788111B1/ko active IP Right Grant
- 2004-09-24 TW TW093129112A patent/TWI314562B/zh not_active IP Right Cessation
-
2007
- 2007-10-22 US US11/876,596 patent/US7550537B2/en not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07304810A (ja) * | 1994-05-09 | 1995-11-21 | Shell Internatl Res Maatschappij Bv | 工業的に用いうる二官能性陰イオン重合開始剤の製造方法およびその使用 |
JPH0848709A (ja) * | 1994-06-27 | 1996-02-20 | Shell Internatl Res Maatschappij Bv | 工業的に適用可能な二官能価アニオン重合イニシエーターの製造方法及び該イニシエーターの使用 |
JP2001064328A (ja) * | 1999-09-01 | 2001-03-13 | Kuraray Co Ltd | α,ω−ジリチオポリマーまたはそれから誘導されるポリマーの製造方法 |
Also Published As
Publication number | Publication date |
---|---|
JP2007506841A (ja) | 2007-03-22 |
EP1709090B1 (en) | 2016-03-23 |
US20080111256A1 (en) | 2008-05-15 |
TWI314562B (en) | 2009-09-11 |
US20050101741A1 (en) | 2005-05-12 |
WO2005030816A1 (en) | 2005-04-07 |
CN1871265A (zh) | 2006-11-29 |
KR20060080232A (ko) | 2006-07-07 |
CN101402693B (zh) | 2011-11-30 |
ES2576631T3 (es) | 2016-07-08 |
CN101402693A (zh) | 2009-04-08 |
EP1709090A1 (en) | 2006-10-11 |
US7550537B2 (en) | 2009-06-23 |
US7285596B2 (en) | 2007-10-23 |
TW200524965A (en) | 2005-08-01 |
KR100788111B1 (ko) | 2007-12-21 |
CN100422225C (zh) | 2008-10-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN107406474B (zh) | 包含聚烯烃-聚苯乙烯嵌段共聚物的有机锌化合物及其制备方法 | |
US6391981B1 (en) | Increased throughput in the manufacture of anionic polymers by reduction in polymer cement viscosity through the addition of metal alkyls | |
KR101768293B1 (ko) | 신규 음이온 중합 개시제 및 이를 이용한 공역디엔계 공중합체의 제조방법 | |
US4182818A (en) | Polyfunctional lithium containing initiator | |
Yu et al. | Efficiency of the sec-butyllithium/m-diisopropenylbenzene diadduct as an anionic polymerization initiator in apolar solvents | |
US7550537B2 (en) | Organo-dilithium compound and process for preparing the same | |
MXPA04009240A (es) | Composicion iniciadora y proceso para polimerizacion anionica. | |
KR20160064724A (ko) | 신규 음이온 중합 개시제 및 이를 이용한 공역디엔계 공중합체의 제조방법 | |
JPH0770264A (ja) | ブロック共重合体の製造方法 | |
JPS5837321B2 (ja) | アニオン重合方法 | |
KR20210068516A (ko) | 적어도 하나의 폴리(알파-메틸스티렌) 블록을 포함하는 열가소성 엘라스토머의 합성 방법 | |
JPS6112712A (ja) | ブロツクコポリマ−及びその製造方法 | |
US6300441B1 (en) | Method for the production of an initiator composition for retarded anionic polymerization | |
CN101932542A (zh) | 碱金属-硅胶(m-sg)材料在其用于阴离子聚合的溶剂和单体干燥与纯化中的用途 | |
JPH04246408A (ja) | 二官能性リビングポリマーの製法及びテレキーリックポリマー及びブロックコポリマーの製法 | |
KR100649780B1 (ko) | 디리튬 개시제의 제조방법, 및 이의 용도 | |
US9487629B2 (en) | Method for preparing a statistical copolymer based on diene monomers and cyclic carbosilane monomers | |
JPH03134008A (ja) | 星形に分枝したコポリマー、その水素化生成物およびリビングポリマー用のカプリング剤 | |
JP2008063300A (ja) | カチオン錯体、これを含有してなる重合触媒、この重合触媒を用いる重合方法及び重合体 | |
GB2516233A (en) | Microstructure modification of polydienes using polar modifiers | |
WO2020016783A2 (en) | Methods of synthesizing polymers | |
CN117186325A (zh) | 一类基于共轭烯烃聚合物的多官能大分子引发剂制备星形聚合物的方法 | |
MX2012000550A (es) | Metodo de obtencion de polidienos en presencia de liquidos ionicos. | |
JP2000072808A (ja) | ジリチウム開始剤の製造方法 | |
CN106589170A (zh) | 一种复合引发剂和阴离子聚合方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20090113 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20090210 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20090501 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20090513 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20090806 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20090915 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20091214 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20091215 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20091221 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20100914 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20101216 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20101224 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20110125 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20110209 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140218 Year of fee payment: 3 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 4685018 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |