JP3378582B2 - 改善された特性の組合せを示すブロックコポリマー - Google Patents
改善された特性の組合せを示すブロックコポリマーInfo
- Publication number
- JP3378582B2 JP3378582B2 JP51423095A JP51423095A JP3378582B2 JP 3378582 B2 JP3378582 B2 JP 3378582B2 JP 51423095 A JP51423095 A JP 51423095A JP 51423095 A JP51423095 A JP 51423095A JP 3378582 B2 JP3378582 B2 JP 3378582B2
- Authority
- JP
- Japan
- Prior art keywords
- styrene
- poly
- block
- weight
- butadiene
- 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 - Lifetime
Links
- 229920001400 block copolymer Polymers 0.000 title claims description 51
- 230000001747 exhibiting effect Effects 0.000 title description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 56
- 239000000203 mixture Substances 0.000 claims description 53
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 52
- 229920002223 polystyrene Polymers 0.000 claims description 36
- 229920000428 triblock copolymer Polymers 0.000 claims description 34
- 229920000359 diblock copolymer Polymers 0.000 claims description 25
- 238000006116 polymerization reaction Methods 0.000 claims description 17
- 239000000178 monomer Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 239000003999 initiator Substances 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 10
- 125000001979 organolithium group Chemical group 0.000 claims description 9
- 230000000379 polymerizing effect Effects 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- VPBZZPOGZPKYKX-UHFFFAOYSA-N 1,2-diethoxypropane Chemical compound CCOCC(C)OCC VPBZZPOGZPKYKX-UHFFFAOYSA-N 0.000 claims description 5
- 229920003247 engineering thermoplastic Polymers 0.000 claims description 5
- 238000009826 distribution Methods 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 claims description 3
- HQSLKNLISLWZQH-UHFFFAOYSA-N 1-(2-propoxyethoxy)propane Chemical compound CCCOCCOCCC HQSLKNLISLWZQH-UHFFFAOYSA-N 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 claims description 3
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 claims description 2
- 239000004606 Fillers/Extenders Substances 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 239000003921 oil Substances 0.000 claims description 2
- 150000001993 dienes Chemical class 0.000 description 11
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 10
- 229920006132 styrene block copolymer Polymers 0.000 description 9
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 8
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 8
- 239000004793 Polystyrene Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000005227 gel permeation chromatography Methods 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 238000005299 abrasion Methods 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 5
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical group [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- FGQLGYBGTRHODR-UHFFFAOYSA-N 2,2-diethoxypropane Chemical compound CCOC(C)(C)OCC FGQLGYBGTRHODR-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- -1 alkali metal salts Chemical class 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
- 230000000977 initiatory effect Effects 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000004831 Hot glue Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000011088 calibration curve Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
- QRLSTWVLSWCGBT-UHFFFAOYSA-N 4-((4,6-bis(octylthio)-1,3,5-triazin-2-yl)amino)-2,6-di-tert-butylphenol Chemical compound CCCCCCCCSC1=NC(SCCCCCCCC)=NC(NC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=N1 QRLSTWVLSWCGBT-UHFFFAOYSA-N 0.000 description 2
- ZYBZLPTXDDWJFH-UHFFFAOYSA-N CCC(C)CC(C)([Li])C1=CC=CC(C([Li])(C)CC(C)CC)=C1 Chemical compound CCC(C)CC(C)([Li])C1=CC=CC(C([Li])(C)CC(C)CC)=C1 ZYBZLPTXDDWJFH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000010426 asphalt Substances 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical group CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- RGASRBUYZODJTG-UHFFFAOYSA-N 1,1-bis(2,4-ditert-butylphenyl)-2,2-bis(hydroxymethyl)propane-1,3-diol dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.C(C)(C)(C)C1=C(C=CC(=C1)C(C)(C)C)C(O)(C(CO)(CO)CO)C1=C(C=C(C=C1)C(C)(C)C)C(C)(C)C RGASRBUYZODJTG-UHFFFAOYSA-N 0.000 description 1
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- IUGPRERXXKWPFI-UHFFFAOYSA-N 1,2-di(propan-2-yloxy)propane Chemical compound CC(C)OCC(C)OC(C)C IUGPRERXXKWPFI-UHFFFAOYSA-N 0.000 description 1
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-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
- MGZCLRWCEUBEGO-UHFFFAOYSA-N 2-(2-propan-2-yloxyethoxy)propane Chemical compound CC(C)OCCOC(C)C MGZCLRWCEUBEGO-UHFFFAOYSA-N 0.000 description 1
- JHOOWURXQGAXHL-UHFFFAOYSA-N 2-[2-(2-propan-2-yloxyethoxy)ethoxy]propane Chemical compound CC(C)OCCOCCOC(C)C JHOOWURXQGAXHL-UHFFFAOYSA-N 0.000 description 1
- KWGJJEBPCVMBIG-UHFFFAOYSA-N 2-methyl-2-[2-[(2-methylpropan-2-yl)oxy]ethoxy]propane Chemical compound CC(C)(C)OCCOC(C)(C)C KWGJJEBPCVMBIG-UHFFFAOYSA-N 0.000 description 1
- FITVQUMLGWRKKG-UHFFFAOYSA-N 2-methyl-2-propoxypropane Chemical compound CCCOC(C)(C)C FITVQUMLGWRKKG-UHFFFAOYSA-N 0.000 description 1
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
- AIBRSVLEQRWAEG-UHFFFAOYSA-N 3,9-bis(2,4-ditert-butylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP1OCC2(COP(OC=3C(=CC(=CC=3)C(C)(C)C)C(C)(C)C)OC2)CO1 AIBRSVLEQRWAEG-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- APMOEFCWQRJOPS-UHFFFAOYSA-N 5-ethenyl-1,5-dimethylcyclohexa-1,3-diene Chemical compound CC1=CC=CC(C)(C=C)C1 APMOEFCWQRJOPS-UHFFFAOYSA-N 0.000 description 1
- SXRLRTAOSJEJCG-UHFFFAOYSA-N C=1C=CC=CC=1C(C=1C=CC=CC=1)([Li])CCC([Li])(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)([Li])CCC([Li])(C=1C=CC=CC=1)C1=CC=CC=C1 SXRLRTAOSJEJCG-UHFFFAOYSA-N 0.000 description 1
- GSGXSPUPTHLEIQ-UHFFFAOYSA-N CC(CC(C1=CC=CC=C1)([Li])[Li])CC Chemical compound CC(CC(C1=CC=CC=C1)([Li])[Li])CC GSGXSPUPTHLEIQ-UHFFFAOYSA-N 0.000 description 1
- ZSVBMZPGHCNSNF-UHFFFAOYSA-N CCC(C)CC([Li])C1=CC=CC(C([Li])CC(C)CC)=C1 Chemical compound CCC(C)CC([Li])C1=CC=CC(C([Li])CC(C)CC)=C1 ZSVBMZPGHCNSNF-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- IORUEKDKNHHQAL-UHFFFAOYSA-N [2-tert-butyl-6-[(3-tert-butyl-2-hydroxy-5-methylphenyl)methyl]-4-methylphenyl] prop-2-enoate Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)OC(=O)C=C)=C1O IORUEKDKNHHQAL-UHFFFAOYSA-N 0.000 description 1
- 230000001594 aberrant effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical group CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
- 239000012285 osmium tetroxide Substances 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000003313 weakening effect Effects 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
- 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
- C08F297/06—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 coordination type
- C08F297/08—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 coordination type polymerising mono-olefins
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP93203244 | 1993-11-18 | ||
| AT93203244.4 | 1993-11-18 | ||
| PCT/EP1994/003849 WO1995014049A1 (en) | 1993-11-18 | 1994-11-16 | Block copolymers having improved combinations of properties |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH09506123A JPH09506123A (ja) | 1997-06-17 |
| JP3378582B2 true JP3378582B2 (ja) | 2003-02-17 |
Family
ID=8214176
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51423095A Expired - Lifetime JP3378582B2 (ja) | 1993-11-18 | 1994-11-16 | 改善された特性の組合せを示すブロックコポリマー |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5693718A (en, 2012) |
| EP (1) | EP0729482B1 (en, 2012) |
| JP (1) | JP3378582B2 (en, 2012) |
| KR (1) | KR100360173B1 (en, 2012) |
| CN (1) | CN1070872C (en, 2012) |
| BR (1) | BR9408075A (en, 2012) |
| DE (1) | DE69406014T2 (en, 2012) |
| ES (1) | ES2107295T3 (en, 2012) |
| RU (1) | RU2162093C2 (en, 2012) |
| TW (1) | TW283152B (en, 2012) |
| WO (1) | WO1995014049A1 (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3936547A1 (en) | 2020-07-09 | 2022-01-12 | Asahi Kasei Kabushiki Kaisha | Hydrogenated block copolymer, elastomer composition comprising hydrogenated block copolymer, seal member comprising elastomer composition, plug body and medical plug |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5750623A (en) * | 1996-05-20 | 1998-05-12 | The Dow Chemical Co. | Hot-melt adhesives for disposable items and articles made therefrom |
| TW446733B (en) * | 1998-03-05 | 2001-07-21 | Japan Elastomer Co Ltd | Block copolymer composition for modifying asphalt and asphalt composition comprising the same |
| US6362282B1 (en) * | 2000-09-29 | 2002-03-26 | Firestone Polymers, Llc | Polymers with high vinyl end segments |
| US6359075B1 (en) * | 2001-01-09 | 2002-03-19 | Bridgestone/Firestone, Inc. | Means of producing high diblock content thermoplastic elastomers via chain transfer |
| US6417270B1 (en) * | 2001-01-09 | 2002-07-09 | Firestone Polymers, Llc | Means of producing high diblock content thermoplastic elastomers with functional termination |
| US20040077789A1 (en) * | 2002-01-10 | 2004-04-22 | Keiichi Toda | Block copolymer |
| US7517932B2 (en) * | 2003-03-24 | 2009-04-14 | Kraton Polymers U.S. Llc | Poly(styrene-butadiene-styrene)polymers having a high vinyl content in the butadiene block and hot melt adhesive composition comprising said polymers |
| WO2005030821A1 (en) * | 2003-09-24 | 2005-04-07 | Kraton Polymers Research B.V. | Conjugated diene polymers and copolymer blocks having high vinyl content prepared using mixed microstructure control agents and process for preparing same |
| US20050137295A1 (en) * | 2003-12-17 | 2005-06-23 | Kraton Polymers U.S. Llc | Bituminous compositions modified by non-blocking elastomers |
| WO2005087867A1 (en) * | 2004-03-05 | 2005-09-22 | Gls Corporation | Block copolymer compositions for overmolding any nylon |
| US7241540B2 (en) * | 2004-04-27 | 2007-07-10 | Kraton Polymers U.S. Llc | Photocurable compositions and flexographic printing plates comprising the same |
| US7560503B2 (en) * | 2004-06-03 | 2009-07-14 | Kraton Polymers U.S. Llc | Gels from high molecular weight block copolymers |
| US7048979B2 (en) * | 2004-06-03 | 2006-05-23 | Kraton Polymers U.S. Llc | Articles prepared from high molecular weight/low coupled block copolymers |
| DE102004059783A1 (de) * | 2004-12-10 | 2006-06-14 | Basf Ag | Transparente Mischungen linearer Styrol-Butadien-Blockcopolymerer |
| US7585916B2 (en) * | 2006-03-24 | 2009-09-08 | Kraton Polymers Us Llc | Block copolymer compositions |
| US7858693B2 (en) * | 2006-03-24 | 2010-12-28 | Kratonpolymers U.S. Llc | Unhydrogenated block copolymer compositions |
| US7592390B2 (en) * | 2006-03-24 | 2009-09-22 | Kraton Polymers U.S. Llc | Hydrogenated block copolymer compositions |
| US7582702B2 (en) * | 2006-03-24 | 2009-09-01 | Kraton Polymers U.S. Llc | Block copolymer compositons |
| EP1847557A1 (en) * | 2006-04-21 | 2007-10-24 | Kraton Polymers Research B.V. | High molecular weight coupled block copolymer compositions |
| KR20100009799A (ko) * | 2008-07-21 | 2010-01-29 | 주식회사 엘지화학 | 아스팔트 개질제 조성물 및 이를 함유하는 아스팔트 조성물 |
| CN102453305B (zh) * | 2010-10-28 | 2013-07-03 | 中国石油化工股份有限公司 | 单乙烯基芳烃和共轭二烯烃嵌段共聚物组合物、其制备方法及其应用 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5089550A (en) | 1986-09-05 | 1992-02-18 | Shell Internationale Research Maatschappij B.V. | Block copolymer composition |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU401153A1 (ru) * | 1970-08-10 | 1974-09-25 | В. П. Шаталов, Л. А. Григорьева, А. Е. Кистерева , В. Д. Алехин | Способ получения термостойких термоэластопластов |
| JPS4945309B2 (en, 2012) * | 1971-08-31 | 1974-12-03 | ||
| NL7113482A (en, 2012) * | 1971-10-01 | 1973-04-03 | ||
| US4163764A (en) * | 1977-06-23 | 1979-08-07 | Phillips Petroleum Company | Coupled block copolymers with improved tack for adhesives |
| US4260694A (en) * | 1979-11-29 | 1981-04-07 | Mobil Oil Corporation | p-Methylstyrene diene block copolymers |
| US4704435A (en) * | 1986-03-24 | 1987-11-03 | Phillips Petroleum Company | Craze-resistant polymodal linear block copolymers with resinous terminal blocks |
| US4704434A (en) * | 1986-03-24 | 1987-11-03 | Phillips Petroleum Company | Craze-resistant polymodal linear block copolymers with terminal tapered blocks |
| BE1001592A3 (fr) * | 1988-04-27 | 1989-12-12 | Fina Research | Procede de preparation de copolymeres sequences. |
| US5171800A (en) * | 1989-06-28 | 1992-12-15 | Basf Aktiengesellschaft | Anionic polymerization with bifunctional initiators |
| US5405903A (en) * | 1993-03-30 | 1995-04-11 | Shell Oil Company | Process for the preparation of a block copolymer blend |
-
1994
- 1994-11-15 TW TW083110566A patent/TW283152B/zh not_active IP Right Cessation
- 1994-11-16 KR KR1019960702621A patent/KR100360173B1/ko not_active Expired - Lifetime
- 1994-11-16 DE DE69406014T patent/DE69406014T2/de not_active Expired - Fee Related
- 1994-11-16 RU RU96113057/04A patent/RU2162093C2/ru not_active IP Right Cessation
- 1994-11-16 JP JP51423095A patent/JP3378582B2/ja not_active Expired - Lifetime
- 1994-11-16 BR BR9408075A patent/BR9408075A/pt not_active IP Right Cessation
- 1994-11-16 CN CN94194205A patent/CN1070872C/zh not_active Expired - Lifetime
- 1994-11-16 ES ES95901406T patent/ES2107295T3/es not_active Expired - Lifetime
- 1994-11-16 WO PCT/EP1994/003849 patent/WO1995014049A1/en active IP Right Grant
- 1994-11-16 EP EP95901406A patent/EP0729482B1/en not_active Expired - Lifetime
-
1995
- 1995-11-06 US US08/553,947 patent/US5693718A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5089550A (en) | 1986-09-05 | 1992-02-18 | Shell Internationale Research Maatschappij B.V. | Block copolymer composition |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3936547A1 (en) | 2020-07-09 | 2022-01-12 | Asahi Kasei Kabushiki Kaisha | Hydrogenated block copolymer, elastomer composition comprising hydrogenated block copolymer, seal member comprising elastomer composition, plug body and medical plug |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2107295T3 (es) | 1997-11-16 |
| US5693718A (en) | 1997-12-02 |
| EP0729482B1 (en) | 1997-10-01 |
| EP0729482A1 (en) | 1996-09-04 |
| KR100360173B1 (ko) | 2003-01-24 |
| CN1070872C (zh) | 2001-09-12 |
| DE69406014D1 (de) | 1997-11-06 |
| KR960705863A (ko) | 1996-11-08 |
| DE69406014T2 (de) | 1998-02-12 |
| WO1995014049A1 (en) | 1995-05-26 |
| RU2162093C2 (ru) | 2001-01-20 |
| BR9408075A (pt) | 1996-10-29 |
| JPH09506123A (ja) | 1997-06-17 |
| TW283152B (en, 2012) | 1996-08-11 |
| CN1135226A (zh) | 1996-11-06 |
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