JP2013538919A5 - - Google Patents
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- Publication number
- JP2013538919A5 JP2013538919A5 JP2013531640A JP2013531640A JP2013538919A5 JP 2013538919 A5 JP2013538919 A5 JP 2013538919A5 JP 2013531640 A JP2013531640 A JP 2013531640A JP 2013531640 A JP2013531640 A JP 2013531640A JP 2013538919 A5 JP2013538919 A5 JP 2013538919A5
- Authority
- JP
- Japan
- Prior art keywords
- butadiene
- alkane
- brominated
- butadiene polymer
- monohalogenated
- 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
- 238000000034 method Methods 0.000 claims description 28
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 22
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 20
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 239000011877 solvent mixture Substances 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 150000001491 aromatic compounds Chemical class 0.000 claims description 4
- JPOXNPPZZKNXOV-UHFFFAOYSA-N bromochloromethane Chemical compound ClCBr JPOXNPPZZKNXOV-UHFFFAOYSA-N 0.000 claims description 4
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical group BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 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
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 claims description 2
- 229920001400 block copolymer Polymers 0.000 claims description 2
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical group C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 claims description 2
- 229940102396 methyl bromide Drugs 0.000 claims description 2
- PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 claims description 2
- -1 phosphonium tribromide Chemical group 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 238000005893 bromination reaction Methods 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 230000031709 bromination Effects 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
- 239000008346 aqueous phase Substances 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- FACXGONDLDSNOE-UHFFFAOYSA-N buta-1,3-diene;styrene Chemical compound C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 FACXGONDLDSNOE-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000011903 deuterated solvents Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229940030980 inova Drugs 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002244 precipitate Substances 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38826510P | 2010-09-30 | 2010-09-30 | |
| US61/388,265 | 2010-09-30 | ||
| PCT/US2011/052114 WO2012044482A1 (en) | 2010-09-30 | 2011-09-19 | Process for brominating butadiene polymers using mixed solvents |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013538919A JP2013538919A (ja) | 2013-10-17 |
| JP2013538919A5 true JP2013538919A5 (https=) | 2014-11-06 |
| JP5898213B2 JP5898213B2 (ja) | 2016-04-06 |
Family
ID=44736056
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013531640A Active JP5898213B2 (ja) | 2010-09-30 | 2011-09-19 | 混合溶媒を使用するブタジエンポリマーの臭素化方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US9062133B2 (https=) |
| EP (1) | EP2596030B1 (https=) |
| JP (1) | JP5898213B2 (https=) |
| CN (1) | CN103140507B (https=) |
| IL (1) | IL225366A (https=) |
| WO (1) | WO2012044482A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2743445T3 (es) | 2015-01-30 | 2020-02-19 | Dow Global Technologies Llc | Método de producción de polímeros bromados y halohidratados |
| CN115124636A (zh) * | 2022-07-16 | 2022-09-30 | 山东东信阻燃科技有限公司 | 一种高热分解温度溴化sbs的制备方法 |
| CN115010857B (zh) * | 2022-07-25 | 2023-09-29 | 北京工商大学 | 一种高热稳定性溴化丁二烯-苯乙烯共聚物的制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4381374A (en) * | 1981-11-12 | 1983-04-26 | Ppg Industries, Inc. | Halogenation of butadiene polymers in mixed solvents |
| CA2174794C (en) * | 1996-04-23 | 2009-09-22 | Gabor Kaszas | Improved polymer bromination process in solution |
| 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 |
| 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 |
| JP5421356B2 (ja) | 2008-04-07 | 2014-02-19 | 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／ビニル芳香族共重合体を臭素化する方法 |
| WO2009134628A1 (en) | 2008-05-01 | 2009-11-05 | Dow Global Technologies Inc. | Two-step process for brominating butadiene copolymers |
| CN102171257B (zh) | 2008-08-05 | 2013-02-20 | 陶氏环球技术有限责任公司 | 用于有机聚合物的溶剂转移方法 |
| 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 US US13/817,447 patent/US9062133B2/en active Active
- 2011-09-19 WO PCT/US2011/052114 patent/WO2012044482A1/en not_active Ceased
- 2011-09-19 EP EP11764396.5A patent/EP2596030B1/en active Active
- 2011-09-19 JP JP2013531640A patent/JP5898213B2/ja active Active
- 2011-09-19 CN CN201180047573.4A patent/CN103140507B/zh active Active
-
2013
- 2013-03-20 IL IL225366A patent/IL225366A/en active IP Right Grant
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