JP2009516019A5 - - Google Patents
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- JP2009516019A5 JP2009516019A5 JP2008540035A JP2008540035A JP2009516019A5 JP 2009516019 A5 JP2009516019 A5 JP 2009516019A5 JP 2008540035 A JP2008540035 A JP 2008540035A JP 2008540035 A JP2008540035 A JP 2008540035A JP 2009516019 A5 JP2009516019 A5 JP 2009516019A5
- Authority
- JP
- Japan
- Prior art keywords
- copolymer
- mass
- brominated
- butadiene
- content
- 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
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- 229920001577 copolymer Polymers 0.000 claims description 69
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 33
- 230000031709 bromination Effects 0.000 claims description 28
- 238000005893 bromination reaction Methods 0.000 claims description 28
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 18
- 229920000642 polymer Polymers 0.000 claims description 14
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical class CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 claims description 13
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- -1 vinyl aromatic hydrocarbon Chemical class 0.000 claims description 11
- 229920002554 vinyl polymer Polymers 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 239000000178 monomer Substances 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 230000004580 weight loss Effects 0.000 claims description 7
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 6
- 239000003063 flame retardant Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical group Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
- 238000002411 thermogravimetry Methods 0.000 claims description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 claims description 3
- 229920001400 block copolymer Polymers 0.000 claims description 3
- JQRYUMGHOUYJFW-UHFFFAOYSA-N pyridine;trihydrobromide Chemical compound [Br-].[Br-].[Br-].C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1 JQRYUMGHOUYJFW-UHFFFAOYSA-N 0.000 claims description 3
- 239000004793 Polystyrene Substances 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 229920005604 random copolymer Polymers 0.000 claims description 2
- 229920002959 polymer blend Polymers 0.000 claims 8
- 239000000203 mixture Chemical class 0.000 claims 5
- 239000002904 solvent Substances 0.000 claims 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 150000003440 styrenes Chemical class 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- SSZOCHFYWWVSAI-UHFFFAOYSA-N 1-bromo-2-ethenylbenzene Chemical compound BrC1=CC=CC=C1C=C SSZOCHFYWWVSAI-UHFFFAOYSA-N 0.000 claims 2
- WGGLDBIZIQMEGH-UHFFFAOYSA-N 1-bromo-4-ethenylbenzene Chemical compound BrC1=CC=C(C=C)C=C1 WGGLDBIZIQMEGH-UHFFFAOYSA-N 0.000 claims 2
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 claims 2
- VKVLTUQLNXVANB-UHFFFAOYSA-N 1-ethenyl-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1C=C VKVLTUQLNXVANB-UHFFFAOYSA-N 0.000 claims 2
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 claims 2
- YFZHODLXYNDBSM-UHFFFAOYSA-N 1-ethenyl-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(C=C)C=C1 YFZHODLXYNDBSM-UHFFFAOYSA-N 0.000 claims 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 2
- 230000000996 additive effect Effects 0.000 claims 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 239000006260 foam Substances 0.000 claims 2
- SFBTTWXNCQVIEC-UHFFFAOYSA-N o-Vinylanisole Chemical compound COC1=CC=CC=C1C=C SFBTTWXNCQVIEC-UHFFFAOYSA-N 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- BTOVVHWKPVSLBI-UHFFFAOYSA-N 2-methylprop-1-enylbenzene Chemical compound CC(C)=CC1=CC=CC=C1 BTOVVHWKPVSLBI-UHFFFAOYSA-N 0.000 claims 1
- CVEPFOUZABPRMK-UHFFFAOYSA-N 2-methylprop-2-enoic acid;styrene Chemical compound CC(=C)C(O)=O.C=CC1=CC=CC=C1 CVEPFOUZABPRMK-UHFFFAOYSA-N 0.000 claims 1
- TXQHJLUVWZNSLH-UHFFFAOYSA-N 5-ethenyl-2,5-dimethylcyclohexa-1,3-diene Chemical compound CC1(C=C)CC=C(C=C1)C TXQHJLUVWZNSLH-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 239000003963 antioxidant agent Substances 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 claims 1
- 239000011324 bead Substances 0.000 claims 1
- 230000001413 cellular effect Effects 0.000 claims 1
- 238000004581 coalescence Methods 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 229920000359 diblock copolymer Polymers 0.000 claims 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 claims 1
- 239000004088 foaming agent Substances 0.000 claims 1
- 229920000578 graft copolymer Polymers 0.000 claims 1
- 239000012760 heat stabilizer Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000002667 nucleating agent Substances 0.000 claims 1
- 229920003251 poly(α-methylstyrene) Polymers 0.000 claims 1
- 239000002516 radical scavenger Substances 0.000 claims 1
- 229920000428 triblock copolymer Polymers 0.000 claims 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 claims 1
- 239000002174 Styrene-butadiene Substances 0.000 description 9
- 229920003048 styrene butadiene rubber Polymers 0.000 description 9
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- DEIGXXQKDWULML-UHFFFAOYSA-N 1,2,5,6,9,10-hexabromocyclododecane Chemical compound BrC1CCC(Br)C(Br)CCC(Br)C(Br)CCC1Br DEIGXXQKDWULML-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001649 bromium compounds 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
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73536105P | 2005-11-12 | 2005-11-12 | |
| US60/735,361 | 2005-11-12 | ||
| PCT/US2006/041295 WO2007058736A1 (en) | 2005-11-12 | 2006-10-23 | Brominated butadiene/vinyl aromatic copolymers, blends of such copolymers with a vinyl aromatic polymer, and polymeric foams formed from such blends |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009516019A JP2009516019A (ja) | 2009-04-16 |
| JP2009516019A5 true JP2009516019A5 (https=) | 2009-12-10 |
| JP5302001B2 JP5302001B2 (ja) | 2013-10-02 |
Family
ID=37836853
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008540035A Active JP5302001B2 (ja) | 2005-11-12 | 2006-10-23 | 臭素化ブタジエン・ビニル芳香族炭化水素共重合体、その共重合体とビニル芳香族炭化水素重合体との配合物、およびその配合物から形成された重合体発泡体 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7851558B2 (https=) |
| EP (1) | EP1957544B1 (https=) |
| JP (1) | JP5302001B2 (https=) |
| KR (1) | KR20080066787A (https=) |
| CN (1) | CN101305022B (https=) |
| AT (1) | ATE455796T1 (https=) |
| AU (1) | AU2006315878A1 (https=) |
| BR (1) | BRPI0619699A2 (https=) |
| CA (1) | CA2627253C (https=) |
| DE (1) | DE602006011944D1 (https=) |
| ES (1) | ES2336951T3 (https=) |
| HR (1) | HRP20080206A2 (https=) |
| NO (1) | NO20081960L (https=) |
| RU (1) | RU2414479C2 (https=) |
| WO (1) | WO2007058736A1 (https=) |
Families Citing this family (112)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| ATE534670T1 (de) | 2007-11-07 | 2011-12-15 | Dow Global Technologies Llc | Verfahren zum partiellen lösungsmittelstrippen zur gewinnung von bromierten butadienpolymeren aus lösung |
| 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 |
| US9732178B1 (en) | 2008-07-24 | 2017-08-15 | Bridgestone Corporation | Block copolymers including high vinyl segments |
| 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 |
| JP5628810B2 (ja) * | 2008-08-18 | 2014-11-19 | ダウ グローバル テクノロジーズ エルエルシー | 臭素化ポリブタジエンポリマー粒子の形成及び脱揮方法 |
| 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 |
| EP2387578B1 (en) | 2008-10-31 | 2014-06-11 | Dow Global Technologies LLC | Extruded polymer foams containing esters of a sugar and a brominated fatty acid as a flame retardant additive |
| US20110240906A1 (en) * | 2008-12-18 | 2011-10-06 | Kram Shari L | Stabilizers for polymers containing aliphatically-bound bromine |
| EP2379605B1 (en) * | 2008-12-19 | 2014-03-12 | Dow Global Technologies LLC | Process for brominating butadiene polymers using ester solvent mixtures |
| WO2010114637A1 (en) | 2009-03-31 | 2010-10-07 | Dow Global Technologies Inc. | Process for brominating unsaturated organic compounds with removal of quaternary ammonium or quaternary phosphonium monochlorides |
| EP2448975B8 (en) * | 2009-06-30 | 2021-09-29 | DDP Specialty Electronic Materials US, LLC | Brominated and epoxidized flame retardants |
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| EP2580250B1 (en) * | 2010-06-14 | 2021-10-27 | DDP Specialty Electronic Materials US, LLC | Process for brominating butadiene polymers |
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| JP2014527096A (ja) * | 2011-07-14 | 2014-10-09 | 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する選択的気体透過性フィルム |
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| KR102209565B1 (ko) | 2013-11-14 | 2021-02-01 | 가부시키가이샤 가네카 | 스티렌계 수지 압출 발포체 및 그의 제조 방법 |
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2006
- 2006-10-23 BR BRPI0619699-3A patent/BRPI0619699A2/pt not_active Application Discontinuation
- 2006-10-23 CA CA2627253A patent/CA2627253C/en active Active
- 2006-10-23 US US12/091,346 patent/US7851558B2/en active Active
- 2006-10-23 JP JP2008540035A patent/JP5302001B2/ja active Active
- 2006-10-23 WO PCT/US2006/041295 patent/WO2007058736A1/en not_active Ceased
- 2006-10-23 AU AU2006315878A patent/AU2006315878A1/en not_active Abandoned
- 2006-10-23 CN CN2006800422261A patent/CN101305022B/zh active Active
- 2006-10-23 EP EP06836467A patent/EP1957544B1/en active Active
- 2006-10-23 DE DE602006011944T patent/DE602006011944D1/de active Active
- 2006-10-23 ES ES06836467T patent/ES2336951T3/es active Active
- 2006-10-23 KR KR1020087011118A patent/KR20080066787A/ko not_active Withdrawn
- 2006-10-23 AT AT06836467T patent/ATE455796T1/de not_active IP Right Cessation
- 2006-10-23 HR HR20080206A patent/HRP20080206A2/xx not_active Application Discontinuation
- 2006-10-23 RU RU2008123837/04A patent/RU2414479C2/ru active
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2008
- 2008-04-25 NO NO20081960A patent/NO20081960L/no not_active Application Discontinuation
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