JPS6141927B2 - - Google Patents
Info
- Publication number
- JPS6141927B2 JPS6141927B2 JP17483884A JP17483884A JPS6141927B2 JP S6141927 B2 JPS6141927 B2 JP S6141927B2 JP 17483884 A JP17483884 A JP 17483884A JP 17483884 A JP17483884 A JP 17483884A JP S6141927 B2 JPS6141927 B2 JP S6141927B2
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- methylstyrene
- styrene
- solution
- weight
- 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
Links
- 229920000642 polymer Polymers 0.000 claims description 109
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 93
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 77
- 239000000178 monomer Substances 0.000 claims description 52
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical group CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 37
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 36
- 238000006116 polymerization reaction Methods 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 22
- 150000001993 dienes Chemical class 0.000 claims description 21
- 229920002554 vinyl polymer Polymers 0.000 claims description 17
- 229920001400 block copolymer Polymers 0.000 claims description 11
- 229920002959 polymer blend Polymers 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 229920005604 random copolymer Polymers 0.000 claims description 7
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical group CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 4
- 230000000977 initiatory effect Effects 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 229920002725 thermoplastic elastomer Polymers 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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 1
- 239000000243 solution Substances 0.000 description 38
- 239000003999 initiator Substances 0.000 description 37
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 229920001577 copolymer Polymers 0.000 description 13
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 11
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical compound [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 11
- 229910052744 lithium Inorganic materials 0.000 description 11
- 229920000428 triblock copolymer Polymers 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000005227 gel permeation chromatography Methods 0.000 description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- 238000007792 addition Methods 0.000 description 7
- 238000007334 copolymerization reaction Methods 0.000 description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- ZAKVZVDDGSFVRG-UHFFFAOYSA-N prop-1-en-2-ylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CC(=C)C1=CC=CC=C1 ZAKVZVDDGSFVRG-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 125000001979 organolithium group Chemical group 0.000 description 5
- 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 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- MDBBOVGSTVJQCA-UHFFFAOYSA-N buta-1,3-diene;prop-1-en-2-ylbenzene;styrene Chemical compound C=CC=C.C=CC1=CC=CC=C1.CC(=C)C1=CC=CC=C1 MDBBOVGSTVJQCA-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- YVWBWDZQFGXBOT-UHFFFAOYSA-N 1,3-bis(1-phenylethenyl)benzene Chemical compound C=1C=CC(C(=C)C=2C=CC=CC=2)=CC=1C(=C)C1=CC=CC=C1 YVWBWDZQFGXBOT-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
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- -1 hydrogen compound Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000005049 silicon tetrachloride Substances 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
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52533683A | 1983-08-22 | 1983-08-22 | |
| US525336 | 1983-08-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6071619A JPS6071619A (ja) | 1985-04-23 |
| JPS6141927B2 true JPS6141927B2 (no) | 1986-09-18 |
Family
ID=24092813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17483884A Granted JPS6071619A (ja) | 1983-08-22 | 1984-08-22 | イソプロペニル芳香族モノマ−とビニル芳香族モノマ−を必須とするコポリマ−ブレンドの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6071619A (no) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013146708A1 (ja) * | 2012-03-27 | 2013-10-03 | 電気化学工業株式会社 | 光学用成形体 |
-
1984
- 1984-08-22 JP JP17483884A patent/JPS6071619A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6071619A (ja) | 1985-04-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4089913A (en) | Process for producing transparent block copolymer resin | |
| JP2633270B2 (ja) | 透明なブロツク共重合体の製造方法 | |
| US4122134A (en) | Method for producing transparent block copolymer resin | |
| US7064164B2 (en) | Transparent styrol-butadiene block copolymer mixtures | |
| EP0413294A2 (en) | Narrow molecular weight distribution block polymers and process therefor | |
| US4427837A (en) | Process for preparation of diene-styrene-α-methylstyrene block polymers and polymers therefrom | |
| US5554696A (en) | Process for the preparation of industrially applicable difunctional anionic polymerization initiators and their use | |
| JP3691149B2 (ja) | ゴム強化ビニル芳香族共重合体の製造方法 | |
| US6462137B2 (en) | Star-block interpolymers and preparation of the same | |
| EP0430014A2 (en) | Tapered block copolymers | |
| US7368504B2 (en) | Method for the production of impact polystyrene | |
| CA2020377A1 (en) | Polymer blends of tapered styrene-butadiene triblock thermoplastic elastomers | |
| US4525532A (en) | Impact resistant α-methylstyrene-styrene copolymer blends | |
| US5756579A (en) | Rubber-reinforced vinyl aromatic (CO) polymer | |
| US5071920A (en) | Tapered block copolymers | |
| US4614768A (en) | Process for preparation of copolymers of isopropenyl aromatic monomer and vinyl aromatic monomer | |
| KR860001032B1 (ko) | 이소프로페닐 방향족 단량체와 비닐 방향족 단량체와의 공중합체의 제조방법 | |
| EP0682041B1 (en) | Process for the preparation of industrially applicable difunctional anionic polymerization initiators and their use | |
| JP2002518562A (ja) | 高い剛性と靭性を有する耐衝撃性ポリスチレン | |
| EP2113002B1 (en) | Method of preparing rubber comprising polymeric compositions and compositions | |
| JPS6141927B2 (no) | ||
| CA1220588A (en) | PROCESS FOR PREPARATION OF DIENE STYRENE .alpha.- METHYLSTYRENE BLOCK POLYMERS AND POLYMERS THEREFROM | |
| US6362282B1 (en) | Polymers with high vinyl end segments | |
| JPH10510567A (ja) | 耐衝撃性に変性されたポリスチレン成形材料の製法 | |
| JP2003532767A (ja) | アニオン重合により形成された耐衝撃性改良ポリスチレン |