DE69733136T2 - Bromiertes polystyrol mit verbesserter thermischer stabilität und farbstabilität und verfahren zur herstellung davon - Google Patents
Bromiertes polystyrol mit verbesserter thermischer stabilität und farbstabilität und verfahren zur herstellung davon Download PDFInfo
- Publication number
- DE69733136T2 DE69733136T2 DE69733136T DE69733136T DE69733136T2 DE 69733136 T2 DE69733136 T2 DE 69733136T2 DE 69733136 T DE69733136 T DE 69733136T DE 69733136 T DE69733136 T DE 69733136T DE 69733136 T2 DE69733136 T2 DE 69733136T2
- Authority
- DE
- Germany
- Prior art keywords
- polystyrene
- bromination
- brominated
- color
- solution
- 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.)
- Revoked
Links
- 229920002223 polystyrene Polymers 0.000 title claims abstract description 126
- 239000004793 Polystyrene Substances 0.000 title claims abstract description 123
- 238000000034 method Methods 0.000 title claims abstract description 64
- 238000004519 manufacturing process Methods 0.000 title description 12
- 230000031709 bromination Effects 0.000 claims abstract description 42
- 238000005893 bromination reaction Methods 0.000 claims abstract description 42
- 239000000654 additive Substances 0.000 claims abstract description 35
- 230000008569 process Effects 0.000 claims abstract description 34
- 239000003054 catalyst Substances 0.000 claims abstract description 29
- 230000026030 halogenation Effects 0.000 claims abstract description 28
- 238000005658 halogenation reaction Methods 0.000 claims abstract description 28
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 27
- 150000002367 halogens Chemical class 0.000 claims abstract description 27
- 230000000996 additive effect Effects 0.000 claims abstract description 25
- 239000002904 solvent Substances 0.000 claims abstract description 24
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 239000000376 reactant Substances 0.000 claims abstract description 14
- 230000001629 suppression Effects 0.000 claims abstract description 10
- 238000004132 cross linking Methods 0.000 claims abstract description 6
- 150000008282 halocarbons Chemical class 0.000 claims abstract description 5
- 229910001507 metal halide Inorganic materials 0.000 claims abstract description 5
- 150000005309 metal halides Chemical class 0.000 claims abstract description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 14
- 230000000694 effects Effects 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 4
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 4
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 3
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims description 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 claims description 2
- -1 alkali metal bisulfite Chemical class 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 230000006698 induction Effects 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 238000010791 quenching Methods 0.000 claims 1
- 230000000171 quenching effect Effects 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 54
- 239000000047 product Substances 0.000 description 33
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 27
- 238000007792 addition Methods 0.000 description 26
- 239000000243 solution Substances 0.000 description 24
- 239000000523 sample Substances 0.000 description 14
- 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 description 13
- 238000002474 experimental method Methods 0.000 description 13
- 239000000178 monomer Substances 0.000 description 13
- 238000012545 processing Methods 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- 239000003063 flame retardant Substances 0.000 description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000008901 benefit Effects 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229920001169 thermoplastic Polymers 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- 239000007789 gas Substances 0.000 description 6
- 239000004416 thermosoftening plastic Substances 0.000 description 6
- 229920003247 engineering thermoplastic Polymers 0.000 description 5
- 210000003244 etp Anatomy 0.000 description 5
- JVPKLOPETWVKQD-UHFFFAOYSA-N 1,2,2-tribromoethenylbenzene Chemical compound BrC(Br)=C(Br)C1=CC=CC=C1 JVPKLOPETWVKQD-UHFFFAOYSA-N 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- 239000012815 thermoplastic material Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229910014265 BrCl Inorganic materials 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- CYLVUSZHVURAOY-UHFFFAOYSA-N 2,2-dibromoethenylbenzene Chemical compound BrC(Br)=CC1=CC=CC=C1 CYLVUSZHVURAOY-UHFFFAOYSA-N 0.000 description 2
- 101710134784 Agnoprotein Proteins 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920002449 FKM Polymers 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- JCIMPKROVFAHTN-UHFFFAOYSA-N (2-bromo-2-chloroethenyl)benzene Chemical compound ClC(Br)=CC1=CC=CC=C1 JCIMPKROVFAHTN-UHFFFAOYSA-N 0.000 description 1
- CISIJYCKDJSTMX-UHFFFAOYSA-N 2,2-dichloroethenylbenzene Chemical compound ClC(Cl)=CC1=CC=CC=C1 CISIJYCKDJSTMX-UHFFFAOYSA-N 0.000 description 1
- 238000003547 Friedel-Crafts alkylation reaction Methods 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 206010040007 Sense of oppression Diseases 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- YMOONIIMQBGTDU-VOTSOKGWSA-N [(e)-2-bromoethenyl]benzene Chemical compound Br\C=C\C1=CC=CC=C1 YMOONIIMQBGTDU-VOTSOKGWSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000005998 bromoethyl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 229940082150 encore Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000009474 immediate action Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000009304 pastoral farming Methods 0.000 description 1
- 229920001596 poly (chlorostyrenes) Polymers 0.000 description 1
- 229920000314 poly p-methyl styrene Polymers 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000012430 stability testing Methods 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000001291 vacuum drying Methods 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/18—Introducing halogen atoms or halogen-containing groups
- C08F8/20—Halogenation
- C08F8/22—Halogenation by reaction with free halogens
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US661350 | 1996-06-14 | ||
| US08/661,350 US5637650A (en) | 1996-06-14 | 1996-06-14 | Brominated polysytrene having improved thermal stability and color and process for the preparation thereof |
| PCT/US1997/009598 WO1997047663A1 (en) | 1996-06-14 | 1997-05-30 | Brominated polystyrene having improved thermal stability and color and process for the preparation thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69733136D1 DE69733136D1 (de) | 2005-06-02 |
| DE69733136T2 true DE69733136T2 (de) | 2006-03-02 |
Family
ID=24653227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69733136T Revoked DE69733136T2 (de) | 1996-06-14 | 1997-05-30 | Bromiertes polystyrol mit verbesserter thermischer stabilität und farbstabilität und verfahren zur herstellung davon |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US5637650A (enExample) |
| EP (1) | EP0906345B1 (enExample) |
| JP (2) | JP2000512328A (enExample) |
| AT (1) | ATE294191T1 (enExample) |
| AU (1) | AU3154597A (enExample) |
| CA (1) | CA2256530C (enExample) |
| DE (1) | DE69733136T2 (enExample) |
| GB (1) | GB2329897B (enExample) |
| WO (1) | WO1997047663A1 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5882551A (en) * | 1995-04-06 | 1999-03-16 | Ferro Corporation | Brominated syndiotactic polystyrene and the use thereof |
| US6518368B2 (en) | 1996-06-14 | 2003-02-11 | Albemarle Corporation | Brominated polystyrene having improved thermal stability and color and process for the preparation thereof |
| US5637650A (en) | 1996-06-14 | 1997-06-10 | Ferro Corporation | Brominated polysytrene having improved thermal stability and color and process for the preparation thereof |
| US6521714B2 (en) | 1996-09-26 | 2003-02-18 | Albemarle Corporation | Brominated polystyrenic resins |
| CA2265642C (en) * | 1996-09-26 | 2006-03-14 | Albemarle Corporation | Process for brominated styrenic polymers |
| US6133381A (en) * | 1996-09-26 | 2000-10-17 | Albelmarle Corporation | Brominated polystyrenic flame retardants |
| US6235831B1 (en) | 1996-09-26 | 2001-05-22 | Albemarle Corporation | Polymer compositions containing brominated polystyrenic resins |
| US6326439B1 (en) | 1996-09-26 | 2001-12-04 | Albemarle Corporation | Process for brominating polystyrenic resins |
| US6232408B1 (en) | 1996-09-26 | 2001-05-15 | Albemarle Corporation | Brominated polstyrenic resins |
| US6232393B1 (en) | 1996-09-26 | 2001-05-15 | Albemarle Corporation | Polymers flame retarded with brominated polystyrenic resins |
| US6235844B1 (en) | 1996-09-26 | 2001-05-22 | Albemarle Corporation | Brominated polystyrenic resins |
| US6221614B1 (en) * | 1997-02-21 | 2001-04-24 | The Regents Of The University Of California | Removal of prions from blood, plasma and other liquids |
| US6146555A (en) * | 1998-01-19 | 2000-11-14 | Ferro Corporation | Brominated copolymer flame retardant additives having improved color characteristics and related method |
| US6313252B1 (en) | 1999-02-04 | 2001-11-06 | The Dow Chemical Company | Functionalized ethylene/vinyl or vinylidene aromatic interpolymers |
| CA2566982C (en) * | 2004-05-20 | 2012-02-21 | Albemarle Corporation | Pelletized brominated anionic styrenic polymers and their preparation and use |
| CN101155639A (zh) * | 2005-03-31 | 2008-04-02 | 雅宝公司 | 改进的具有催化剂回收的聚合物卤化方法 |
| BRPI0614223A2 (pt) * | 2005-06-30 | 2011-03-15 | Albemarle Corp | polìmeros estirênicos bromados e suas preparações |
| KR101353883B1 (ko) * | 2005-12-21 | 2014-02-18 | 알베마를 코포레이션 | 브롬화 음이온성 스티렌계 중합체 및 이의 제조 |
| ES2534767T3 (es) | 2006-07-20 | 2015-04-28 | Albemarle Corporation | Tecnología del proceso de recuperación de polímeros estirénicos bromados a partir de mezclas de reacción en las cuales se forman y/o convierten estas mezclas en pellets o en gránulos o pastillas |
| WO2008066970A1 (en) * | 2006-11-28 | 2008-06-05 | Albemarle Corporation | Converting brominated anionic styrenic polymer into harder and larger form for storage, shipment, and use |
| SG184732A1 (en) * | 2007-06-07 | 2012-10-30 | Albemarle Corp | Low molecular weight brominated polymers and their use in thermoplastic formulations |
| PL2288628T3 (pl) | 2008-06-06 | 2019-06-28 | Albemarle Corporation | Bromowane polimery o niskim ciężarze cząsteczkowym, sposoby ich wytwarzania i ich zastosowanie w formulacjach termoplastycznych |
| US8993684B2 (en) | 2008-06-06 | 2015-03-31 | Albemarle Corporation | Low molecular weight brominated polymers, processes for their manufacture and their use in thermoplastic formulations |
| WO2010065462A2 (en) * | 2008-12-02 | 2010-06-10 | Albemarle Corporation | Toluene and styrene derived telomer distributions and brominated flame retardants produced therefrom |
| WO2010065464A1 (en) * | 2008-12-02 | 2010-06-10 | Albemarle Corporation | Bromination of telomer mixtures derived from toluene and styrene |
| JP2012510562A (ja) | 2008-12-02 | 2012-05-10 | アルベマール・コーポレーシヨン | 分岐および星型分岐スチレンの重合体、短鎖重合体、ならびに付加物、それらの合成、それらの臭素化、およびそれらの使用 |
| JO3423B1 (ar) * | 2008-12-02 | 2019-10-20 | Albemarle Corp | مؤخرات لهب معالجة بالبروم و مواد مشتقه منها |
| JO3059B1 (ar) | 2009-05-01 | 2017-03-15 | Albemarle Corp | معالجة بالبروم لتراكيب بوليمرات عطرية ذات وزن جزيئي منخفض |
| CN102439080A (zh) | 2009-05-01 | 2012-05-02 | 阿尔比马尔公司 | 粒状低分子量溴化芳族聚合物组合物 |
| JP5848556B2 (ja) * | 2011-09-08 | 2016-01-27 | 三菱エンジニアリングプラスチックス株式会社 | ポリエステル樹脂組成物及び成形体 |
| JP5848555B2 (ja) * | 2011-09-08 | 2016-01-27 | 三菱エンジニアリングプラスチックス株式会社 | ポリエステル樹脂組成物及び成形体 |
| US11021425B2 (en) | 2018-10-12 | 2021-06-01 | International Business Machines Corporation | Polybrominated diphenyl-based flame retardant compounds |
| CN119529143B (zh) * | 2025-01-23 | 2025-04-08 | 山东东信新材料科技股份有限公司 | 一种溴化聚苯乙烯的制备方法 |
Family Cites Families (72)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1890772A (en) | 1930-01-28 | 1932-12-13 | Du Pont | Chlorination of meta styrene |
| US2199026A (en) | 1937-04-01 | 1940-04-30 | Du Pont | Chlorinated aromatic resins |
| US2823201A (en) | 1952-03-10 | 1958-02-11 | Dow Chemical Co | Halogenated polymers of nuclear methylated aromatic hydrocarbons, their quaternary ammonium salts and method of making the same |
| US3009906A (en) | 1957-05-09 | 1961-11-21 | Dow Chemical Co | Halogenation of solid resinous polymers of alkenylaromatic compounds with gaseous halogens |
| US3050476A (en) | 1958-12-08 | 1962-08-21 | Koppers Co Inc | Method of making a self extinguishing expandable polymer of styrene by bromination |
| US3039977A (en) | 1959-12-03 | 1962-06-19 | Koppers Co Inc | Method of producing self-extinguishing foamable polystyrene by brominating foamable polystyrene in aqueous suspension |
| US3132045A (en) | 1961-10-26 | 1964-05-05 | Dow Chemical Co | Method of impregnating film materials with ammonium bromide |
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-
1996
- 1996-06-14 US US08/661,350 patent/US5637650A/en not_active Expired - Lifetime
-
1997
- 1997-02-07 US US08/796,277 patent/US5726252A/en not_active Ceased
- 1997-05-30 EP EP97926887A patent/EP0906345B1/en not_active Revoked
- 1997-05-30 WO PCT/US1997/009598 patent/WO1997047663A1/en not_active Ceased
- 1997-05-30 AT AT97926887T patent/ATE294191T1/de not_active IP Right Cessation
- 1997-05-30 CA CA002256530A patent/CA2256530C/en not_active Expired - Fee Related
- 1997-05-30 AU AU31545/97A patent/AU3154597A/en not_active Abandoned
- 1997-05-30 JP JP10501668A patent/JP2000512328A/ja active Pending
- 1997-05-30 GB GB9827416A patent/GB2329897B/en not_active Expired - Fee Related
- 1997-05-30 DE DE69733136T patent/DE69733136T2/de not_active Revoked
-
1999
- 1999-07-19 US US09/356,734 patent/USRE37902E1/en not_active Expired - Lifetime
-
2008
- 2008-02-12 JP JP2008030178A patent/JP2008133484A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| USRE37902E1 (en) | 2002-11-05 |
| EP0906345A1 (en) | 1999-04-07 |
| ATE294191T1 (de) | 2005-05-15 |
| WO1997047663A1 (en) | 1997-12-18 |
| AU3154597A (en) | 1998-01-07 |
| CA2256530A1 (en) | 1997-12-18 |
| JP2000512328A (ja) | 2000-09-19 |
| JP2008133484A (ja) | 2008-06-12 |
| CA2256530C (en) | 2006-09-12 |
| GB2329897B (en) | 2001-01-10 |
| EP0906345B1 (en) | 2005-04-27 |
| US5637650A (en) | 1997-06-10 |
| US5726252A (en) | 1998-03-10 |
| GB9827416D0 (en) | 1999-02-03 |
| GB2329897A (en) | 1999-04-07 |
| DE69733136D1 (de) | 2005-06-02 |
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| 8363 | Opposition against the patent | ||
| 8331 | Complete revocation |