JP2013542281A5 - - Google Patents
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- Publication number
- JP2013542281A5 JP2013542281A5 JP2013531641A JP2013531641A JP2013542281A5 JP 2013542281 A5 JP2013542281 A5 JP 2013542281A5 JP 2013531641 A JP2013531641 A JP 2013531641A JP 2013531641 A JP2013531641 A JP 2013531641A JP 2013542281 A5 JP2013542281 A5 JP 2013542281A5
- Authority
- JP
- Japan
- Prior art keywords
- brominated styrene
- butadiene copolymer
- solution
- styrene
- 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.)
- Pending
Links
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical class C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 25
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 150000001555 benzenes Chemical class 0.000 claims description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims description 4
- JPOXNPPZZKNXOV-UHFFFAOYSA-N bromochloromethane Chemical compound ClCBr JPOXNPPZZKNXOV-UHFFFAOYSA-N 0.000 claims description 4
- 238000005187 foaming Methods 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 claims description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 239000002174 Styrene-butadiene Substances 0.000 claims description 2
- 239000012296 anti-solvent Substances 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 claims description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 2
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 claims description 2
- 238000001125 extrusion Methods 0.000 claims description 2
- 125000005496 phosphonium group Chemical group 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 239000011115 styrene butadiene Substances 0.000 claims description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000011903 deuterated solvents Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229940030980 inova Drugs 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38826510P | 2010-09-30 | 2010-09-30 | |
| US61/388,265 | 2010-09-30 | ||
| US201061427194P | 2010-12-26 | 2010-12-26 | |
| US61/427,194 | 2010-12-26 | ||
| PCT/US2011/052116 WO2012044483A1 (en) | 2010-09-30 | 2011-09-19 | Process for recovering brominated styrene-butadiene copolymers from a bromination reaction solution |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013542281A JP2013542281A (ja) | 2013-11-21 |
| JP2013542281A5 true JP2013542281A5 (https=) | 2014-11-06 |
Family
ID=45893500
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013531641A Pending JP2013542281A (ja) | 2010-09-30 | 2011-09-19 | 臭素化反応溶液から臭素化スチレン−ブタジエンコポリマーを回収する方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20130178547A1 (https=) |
| EP (1) | EP2598539A1 (https=) |
| JP (1) | JP2013542281A (https=) |
| CN (1) | CN103140508A (https=) |
| IL (1) | IL225365A0 (https=) |
| WO (1) | WO2012044483A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6113576B2 (ja) * | 2013-03-15 | 2017-04-12 | 株式会社ジェイエスピー | ポリスチレン系樹脂押出発泡体の製造方法 |
| JP6273001B2 (ja) * | 2013-10-30 | 2018-01-31 | ダウ グローバル テクノロジーズ エルエルシー | 臭素化スチレン−ブタジエンコポリマーを含有し、かつ向上したセルサイズ均一性を有する発泡スチレンポリマー |
| CN105849131B (zh) * | 2013-12-29 | 2018-11-09 | 陶氏环球技术有限责任公司 | 从有机溶剂回收溴化的苯乙烯-丁二烯共聚物的方法 |
| ES2743445T3 (es) * | 2015-01-30 | 2020-02-19 | Dow Global Technologies Llc | Método de producción de polímeros bromados y halohidratados |
| US20190263991A1 (en) | 2016-10-10 | 2019-08-29 | Total Research & Technology Feluy | Improved Expandable Vinyl Aromatic Polymers |
| CN109879725A (zh) * | 2019-03-27 | 2019-06-14 | 山东润科化工股份有限公司 | 一种2,3-二溴-1,4-丁烯二醇的合成方法 |
| MX2024005660A (es) * | 2021-11-11 | 2024-07-19 | Polystyvert Inc | Métodos para reciclar material de poliestireno que comprende contaminantes bromados. |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2409910A (en) | 1944-11-29 | 1946-10-22 | Dow Chemical Co | Method of filling containers with resinous foam |
| US2515250A (en) | 1947-11-07 | 1950-07-18 | Dow Chemical Co | Method of making and storing compositions comprising thermoplastic resins and normally gaseous solvents |
| NL84582C (https=) | 1950-06-29 | 1900-01-01 | ||
| US2848428A (en) | 1953-06-01 | 1958-08-19 | Dow Chemical Co | Latent foaming compositions of vinyl aromatic resins and method of making |
| US2928130A (en) | 1955-09-08 | 1960-03-15 | Western Electric Co | Methods for making cellular plastic products |
| GB912888A (https=) | 1959-07-22 | 1900-01-01 | ||
| US3121911A (en) | 1961-03-08 | 1964-02-25 | Monsanto Chemicals | Foamed resin extrusion process and apparatus |
| US3960792A (en) | 1968-07-10 | 1976-06-01 | The Dow Chemical Company | Plastic foam |
| DE2119783B2 (de) | 1971-04-23 | 1974-09-05 | Chemische Werke Huels Ag, 4370 Marl | Überzugsmittel |
| US3815674A (en) | 1971-12-20 | 1974-06-11 | J Duda | Well structure and method for protecting permafrost |
| US3966381A (en) | 1973-11-21 | 1976-06-29 | The Dow Chemical Company | Extrusion of thermoplastic foam |
| NL179914C (nl) | 1975-11-04 | 1986-12-01 | Dow Chemical Co | Werkwijze voor het door extrusie vervaardigen van een schuimvoorwerp uit een thermoplastische alkenyl-aromatische kunsthars. |
| US4146563A (en) | 1977-12-20 | 1979-03-27 | The Dow Chemical Company | Method and apparatus for forming thermoplastic foams |
| DE2907930C2 (de) | 1979-03-01 | 1982-12-16 | Festo-Maschinenfabrik Gottlieb Stoll, 7300 Esslingen | Druckluftbetriebene Handschleifmaschine |
| US4229396A (en) | 1979-03-21 | 1980-10-21 | The Dow Chemical Company | Method of extruding thermoplastic resin foams having enlarged cell-sizes |
| US4454086A (en) | 1982-06-18 | 1984-06-12 | The Dow Chemical Company | Making cross-linked styrene polymer foam |
| US4421866A (en) | 1982-09-29 | 1983-12-20 | The Dow Chemical Company | Method for the preparation of styrene polymer foam |
| US4438224A (en) | 1982-09-29 | 1984-03-20 | The Dow Chemical Company | Method for the preparation of styrene polymer foam and foam prepared thereby |
| US4486550A (en) | 1984-04-24 | 1984-12-04 | The Dow Chemical Company | Styrenic foam and process therefor |
| US4668768A (en) * | 1985-11-25 | 1987-05-26 | General Electric Company | Anti-solvent precipitation process for isolating polymers from solution |
| US4801484A (en) | 1988-01-13 | 1989-01-31 | The Dow Chemical Company | Highly loaded coalesced foam |
| US4824720A (en) | 1988-02-11 | 1989-04-25 | The Dow Chemical Company | Coalesced polyolefin foam having exceptional cushioning properties |
| JPH09309920A (ja) * | 1996-05-21 | 1997-12-02 | Kanegafuchi Chem Ind Co Ltd | 硬化性樹脂及びその製造方法 |
| US6213540B1 (en) | 1997-06-27 | 2001-04-10 | The Dow Chemical Company | Energy absorbing articles of extruded thermoplastic foams |
| FR2806731B1 (fr) * | 2000-03-23 | 2002-06-14 | Solvay | Procede de recyclage d'une matiere plastique |
| KR100590474B1 (ko) * | 2004-01-29 | 2006-06-19 | 주식회사 엘지화학 | 벌크 밀도가 높은 고리형 올레핀 고분자의 제조 방법 및이에 의하여 제조된 고리형 올레핀 고분자 |
| JP2008024794A (ja) * | 2006-07-19 | 2008-02-07 | Mitsui Chemicals Inc | オレフィン系ブロックポリマーを含んでなるポリマーブレンド |
| JP5536451B2 (ja) * | 2006-08-16 | 2014-07-02 | ダウ グローバル テクノロジーズ エルエルシー | ブタジエン／ビニル芳香族コポリマーを臭素化する方法 |
| EP2054446B1 (en) | 2006-08-16 | 2019-07-24 | Dow Global Technologies LLC | Process for brominating butadiene/vinyl aromatic copolymers |
| US8193287B2 (en) * | 2008-03-06 | 2012-06-05 | Dow Global Technologies Llc | Process for brominating butadiene copolymers by the addition of water or certain solvents |
| US8372921B2 (en) * | 2008-08-22 | 2013-02-12 | Dow Global Technologies Llc | Process for brominating unsaturated organic compounds using a quaternary phosphonium tribromide as the brominating agent |
| EP2379605B1 (en) * | 2008-12-19 | 2014-03-12 | Dow Global Technologies LLC | Process for brominating butadiene polymers using ester solvent mixtures |
-
2011
- 2011-09-19 EP EP11764911.1A patent/EP2598539A1/en not_active Withdrawn
- 2011-09-19 WO PCT/US2011/052116 patent/WO2012044483A1/en not_active Ceased
- 2011-09-19 US US13/818,859 patent/US20130178547A1/en not_active Abandoned
- 2011-09-19 JP JP2013531641A patent/JP2013542281A/ja active Pending
- 2011-09-19 CN CN2011800475749A patent/CN103140508A/zh active Pending
-
2013
- 2013-03-20 IL IL225365A patent/IL225365A0/en unknown
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