CA2265642C - Process for brominated styrenic polymers - Google Patents
Process for brominated styrenic polymers Download PDFInfo
- Publication number
- CA2265642C CA2265642C CA002265642A CA2265642A CA2265642C CA 2265642 C CA2265642 C CA 2265642C CA 002265642 A CA002265642 A CA 002265642A CA 2265642 A CA2265642 A CA 2265642A CA 2265642 C CA2265642 C CA 2265642C
- Authority
- CA
- Canada
- Prior art keywords
- bromine
- styrenic polymer
- mixture
- polystyrene
- reactor
- 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 - Lifetime
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 62
- 238000000034 method Methods 0.000 title claims description 43
- JPOXNPPZZKNXOV-UHFFFAOYSA-N bromochloromethane Chemical compound ClCBr JPOXNPPZZKNXOV-UHFFFAOYSA-N 0.000 claims abstract description 94
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 40
- 230000031709 bromination Effects 0.000 claims abstract description 27
- 238000005893 bromination reaction Methods 0.000 claims abstract description 27
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 51
- 229910052794 bromium Inorganic materials 0.000 claims description 49
- 239000004793 Polystyrene Substances 0.000 claims description 44
- 229920002223 polystyrene Polymers 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 33
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical group Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 20
- 239000011968 lewis acid catalyst Substances 0.000 claims description 13
- -1 aluminum halide Chemical class 0.000 claims description 11
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 229920001169 thermoplastic Polymers 0.000 claims description 3
- 239000004416 thermosoftening plastic Substances 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 abstract description 35
- 239000007810 chemical reaction solvent Substances 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 46
- 239000000243 solution Substances 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 21
- 238000002156 mixing Methods 0.000 description 17
- 239000000178 monomer Substances 0.000 description 17
- 239000000725 suspension Substances 0.000 description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910052742 iron Inorganic materials 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000011872 intimate mixture Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229910014265 BrCl Inorganic materials 0.000 description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 3
- 229940073584 methylene chloride Drugs 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- AEQDJSLRWYMAQI-UHFFFAOYSA-N 2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline Chemical compound C1CN2CC(C(=C(OC)C=C3)OC)=C3CC2C2=C1C=C(OC)C(OC)=C2 AEQDJSLRWYMAQI-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920003247 engineering thermoplastic Polymers 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000000176 sodium gluconate Substances 0.000 description 2
- 235000012207 sodium gluconate Nutrition 0.000 description 2
- 229940005574 sodium gluconate Drugs 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- XIRPMPKSZHNMST-UHFFFAOYSA-N 1-ethenyl-2-phenylbenzene Chemical group C=CC1=CC=CC=C1C1=CC=CC=C1 XIRPMPKSZHNMST-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- UVHXEHGUEKARKZ-UHFFFAOYSA-N 1-ethenylanthracene Chemical compound C1=CC=C2C=C3C(C=C)=CC=CC3=CC2=C1 UVHXEHGUEKARKZ-UHFFFAOYSA-N 0.000 description 1
- OGMSGZZPTQNTIK-UHFFFAOYSA-N 1-methyl-2-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1C OGMSGZZPTQNTIK-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- BYACHAOCSIPLCM-UHFFFAOYSA-N 2-[2-[bis(2-hydroxyethyl)amino]ethyl-(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(CCO)CCN(CCO)CCO BYACHAOCSIPLCM-UHFFFAOYSA-N 0.000 description 1
- YMOONIIMQBGTDU-UHFFFAOYSA-N 2-bromoethenylbenzene Chemical class BrC=CC1=CC=CC=C1 YMOONIIMQBGTDU-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical class ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 241000590428 Panacea Species 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 229910007932 ZrCl4 Inorganic materials 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Inorganic materials O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- ZYBHSWXEWOPHBJ-UHFFFAOYSA-N potassium;propan-2-ylbenzene Chemical compound [K+].C[C-](C)C1=CC=CC=C1 ZYBHSWXEWOPHBJ-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- YEAUATLBSVJFOY-UHFFFAOYSA-N tetraantimony hexaoxide Chemical compound O1[Sb](O2)O[Sb]3O[Sb]1O[Sb]2O3 YEAUATLBSVJFOY-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 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
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)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72138996A | 1996-09-26 | 1996-09-26 | |
| US721,389 | 1996-09-26 | ||
| US846,156 | 1997-04-25 | ||
| US08/846,156 US5767203A (en) | 1996-09-26 | 1997-04-25 | Process for brominated styrenic polymers |
| PCT/US1997/015622 WO1998013396A1 (en) | 1996-09-26 | 1997-09-05 | Process for brominated styrenic polymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2265642A1 CA2265642A1 (en) | 1998-04-02 |
| CA2265642C true CA2265642C (en) | 2006-03-14 |
Family
ID=27110422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002265642A Expired - Lifetime CA2265642C (en) | 1996-09-26 | 1997-09-05 | Process for brominated styrenic polymers |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US5916978A (enExample) |
| EP (1) | EP0928300B1 (enExample) |
| JP (1) | JP4328388B2 (enExample) |
| CA (1) | CA2265642C (enExample) |
| DE (1) | DE69701997T2 (enExample) |
| IL (1) | IL129113A (enExample) |
| WO (1) | WO1998013396A1 (enExample) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US6232408B1 (en) | 1996-09-26 | 2001-05-15 | Albemarle Corporation | Brominated polstyrenic resins |
| 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 |
| US6232393B1 (en) | 1996-09-26 | 2001-05-15 | Albemarle Corporation | Polymers flame retarded with brominated polystyrenic resins |
| US6521714B2 (en) * | 1996-09-26 | 2003-02-18 | Albemarle Corporation | Brominated polystyrenic resins |
| JP4328388B2 (ja) | 1996-09-26 | 2009-09-09 | アルベマール・コーポレーシヨン | スチレン重合体の臭素化方法 |
| EP1293517B1 (en) * | 1997-05-07 | 2005-12-21 | Albemarle Corporation | Brominated polystyrenic resins |
| EP1115756A1 (en) * | 1998-09-10 | 2001-07-18 | Albemarle Corporation | Improved brominated polystyrenic resins, and their use |
| US6333385B1 (en) | 1999-11-15 | 2001-12-25 | Marquette University | Method to produce flame retardant styrenic polymers and product produced thereby |
| ATE462681T1 (de) * | 2001-12-21 | 2010-04-15 | Chemtura Corp | Verfahren und vorrichtung zur herstellung von decabromdiphenylalkanen |
| US20040072929A1 (en) * | 2002-06-27 | 2004-04-15 | De Schryver Daniel A. | Flame retardant compositions |
| US6657028B1 (en) | 2002-08-01 | 2003-12-02 | Albemarle Corporation | Anionic polymerization process |
| US7666944B2 (en) * | 2004-01-21 | 2010-02-23 | Albemarle Corporation | Flame retarded fibers and filaments and process of production therefor |
| US20050159552A1 (en) * | 2004-01-21 | 2005-07-21 | Reed Jon S. | Flame retarded fibers and filaments and process of production therefor |
| CN100551659C (zh) * | 2004-05-20 | 2009-10-21 | 雅宝公司 | 制成粒状的溴化阴离子苯乙烯系聚合物及其制备和应用 |
| BRPI0614223A2 (pt) * | 2005-06-30 | 2011-03-15 | Albemarle Corp | polìmeros estirênicos bromados e suas preparações |
| US7638583B2 (en) * | 2005-12-21 | 2009-12-29 | Albemarle Corporation | Brominated anionic styrenic polymers and their preparation |
| CN101341175B (zh) * | 2005-12-21 | 2011-03-30 | 雅宝公司 | 溴化的苯乙烯系聚合物或树脂的制备 |
| US8273831B2 (en) | 2006-07-20 | 2012-09-25 | Albemarle Corporation | Process technology for recovering brominated styrenic polymers from reaction mixtures in which they are formed and/or converting such mixtures into pellets or into granules or pastilles |
| TW200817447A (en) | 2006-08-22 | 2008-04-16 | Albemarle Corp | Terminating bromination of styrenic polymer in a bromination reaction mixture |
| CA2669906A1 (en) * | 2006-11-28 | 2008-06-05 | Albemarle Corporation | Converting brominated anionic styrenic polymer into harder and larger form for storage, shipment, and use |
| HUE042388T2 (hu) | 2007-06-07 | 2019-06-28 | Albemarle Corp | Adduktok, adduktok és oligomerek, vagy adduktok, oligomerek és kis molekulatömegû polimerek, és elõállításuk |
| 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 |
| CA2740945C (en) | 2008-06-06 | 2017-07-11 | Albemarle Corporation | Low molecular weight brominated polymers, processes for their manufacture and their use in thermoplastic formulations |
| JP2012510538A (ja) * | 2008-12-02 | 2012-05-10 | アルベマール・コーポレーシヨン | トルエンおよびスチレンに由来するテロマー分布と、それから生成された臭素化難燃剤 |
| TW201030020A (en) * | 2008-12-02 | 2010-08-16 | Albemarle Corp | Branched and star-branched styrene polymers, telomers, and adducts their synthesis, their bromination, and their uses |
| JO3423B1 (ar) * | 2008-12-02 | 2019-10-20 | Albemarle Corp | مؤخرات لهب معالجة بالبروم و مواد مشتقه منها |
| EP2373697A1 (en) * | 2008-12-02 | 2011-10-12 | Albemarle Corporation | Bromination of telomer mixtures derived from toluene and styrene |
| JO3059B1 (ar) | 2009-05-01 | 2017-03-15 | Albemarle Corp | معالجة بالبروم لتراكيب بوليمرات عطرية ذات وزن جزيئي منخفض |
| JP2012525483A (ja) | 2009-05-01 | 2012-10-22 | アルベマール・コーポレーシヨン | ペレット化された低分子量臭素化芳香族ポリマー組成物 |
| WO2022031932A1 (en) * | 2020-08-07 | 2022-02-10 | Albemarle Corporation | Additives for flame retarded polyolefins |
| CN117247482B (zh) * | 2023-11-17 | 2024-02-20 | 山东旭锐新材股份有限公司 | 一种高热稳定性溴化聚苯乙烯合成方法 |
Family Cites Families (67)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1890772A (en) * | 1930-01-28 | 1932-12-13 | Du Pont | Chlorination of meta styrene |
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| NL128916C (enExample) * | 1965-02-18 | 1900-01-01 | ||
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| DE2515473C3 (de) | 1975-04-09 | 1987-01-22 | Basf Ag, 6700 Ludwigshafen | Flammwidrige, lineare Polyester |
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| DE2645711C3 (de) * | 1976-10-09 | 1979-06-07 | Basf Ag, 6700 Ludwigshafen | Halogenhaltige Flammschutzmittel enthaltende Fasern und Fäden aus linearen, thermoplastischen Polyestern |
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| DE2703419B1 (de) * | 1977-01-28 | 1978-02-02 | Basf Ag | Flammwidrig ausgeruestete polyamid- formmassen |
| FR2413409A1 (fr) * | 1978-01-02 | 1979-07-27 | Huels Chemische Werke Ag | Procede pour preparer des polystyrenes resistant a la chaleur, bromes sur le noyau |
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| US4389517A (en) * | 1982-04-02 | 1983-06-21 | The Dow Chemical Company | Hydrogenation of phenylacetylene prior to styrene polymerization |
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| EP0150332A3 (en) * | 1983-12-26 | 1987-08-19 | Mitsubishi Kasei Corporation | Process for producing a chloromethylated polymer |
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| CA1297628C (en) * | 1987-01-28 | 1992-03-17 | David C. Sanders | Aromatic bromination of polystyrene using bromine as the reaction solvent |
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| US4835222A (en) * | 1987-02-19 | 1989-05-30 | The Dow Chemical Company | Alkylation of vinyl aromatic polymer |
| US4832873A (en) * | 1987-10-09 | 1989-05-23 | Great Lakes Chemical Corporation | Process for producing polybrominated higher alkylbenzenes |
| JPH02215807A (ja) * | 1989-02-17 | 1990-08-28 | Nippon Kayaku Co Ltd | 臭素化ポリスチレンの製造方法 |
| NL8901054A (nl) | 1989-04-27 | 1990-11-16 | Gen Electric | Polymeermengsel met polyester, glasvezels, vlamvertragend middel en vulmiddel; daaruit gevormde voorwerpen. |
| US5112898A (en) * | 1989-06-06 | 1992-05-12 | Ferro Corporation | High impact polystyrene containing low molecular weight brominated polystyrene |
| US5112896A (en) * | 1989-06-06 | 1992-05-12 | Ferro Corporation | High-impact polystyrene containing low molecular weight brominated polystyrene |
| US5112897A (en) * | 1989-06-06 | 1992-05-12 | Ferro Corporation | High impact polystyrene containing low molecular weight brominated polystyrene |
| US4975496A (en) * | 1989-08-10 | 1990-12-04 | The Dow Chemical Company | Process for brominating aromatic resins |
| DE69129533T2 (de) | 1990-03-16 | 1998-10-29 | Great Lakes Chemical Corp | Verfahren zur reinigung von bromiertem polystyrol |
| US5194482A (en) * | 1990-08-23 | 1993-03-16 | Ferro Corporation | Flame retardant resin composition containing styrenic polymers |
| US5235000A (en) * | 1990-12-10 | 1993-08-10 | Ethyl Corporation | Preparation, storage, and usage of bromine chloride |
| IL99130A (en) | 1991-08-08 | 1998-04-05 | Bromine Compounds Ltd | Preparation of tribromo (B) bromoethyl (benzene in a high degree of purity) |
| JPH05170809A (ja) * | 1991-12-24 | 1993-07-09 | Tosoh Corp | 塩素化ポリオレフィンの製造法 |
| JP2718851B2 (ja) | 1992-04-07 | 1998-02-25 | 帝人化成株式会社 | ブロモ化スチレンの乳化重合法 |
| US5326837A (en) * | 1992-11-20 | 1994-07-05 | Mobil Oil Corporation | Catalyst systems for syndiospecific polymerization of styrenes |
| JP3359695B2 (ja) | 1993-05-14 | 2002-12-24 | 帝人化成株式会社 | ポリスチレン臭素化反応溶液の精製方法 |
| JP3359698B2 (ja) | 1993-06-15 | 2002-12-24 | 帝人化成株式会社 | 臭素化ポリスチレンの製造方法 |
| US5304618A (en) * | 1993-07-22 | 1994-04-19 | Great Lakes Chemical Corporation | Polymers of brominated styrene |
| JP3471086B2 (ja) * | 1994-08-12 | 2003-11-25 | 帝人化成株式会社 | 臭素化ポリスチレンの製造方法 |
| CN1076366C (zh) | 1995-03-10 | 2001-12-19 | 钟渊化学工业株式会社 | 阻燃性聚对苯二甲酸乙二醇酯类树脂组合物 |
| JPH0977937A (ja) | 1995-09-12 | 1997-03-25 | Idemitsu Petrochem Co Ltd | プリント配線板用プリプレグ及びプリント配線用基板 |
| US5532322B1 (en) * | 1995-09-26 | 1999-12-07 | Manac Inc | Process for preparing brominated polystyrene |
| US5637650A (en) * | 1996-06-14 | 1997-06-10 | Ferro Corporation | Brominated polysytrene having improved thermal stability and color and process for the preparation thereof |
| US5723549A (en) | 1996-06-14 | 1998-03-03 | Ferro Corporation | Process for the preparation of brominated polystyrene having improved color characteristics |
| US5677390A (en) | 1996-09-26 | 1997-10-14 | Albemarle Corporation | Process for brominating polystyrenic resins |
| US5686538A (en) | 1996-09-26 | 1997-11-11 | Albemarle Corporation | Process for brominating polystyrenic resins |
| US5767203A (en) | 1996-09-26 | 1998-06-16 | Albemarle Corporation | Process for brominated styrenic polymers |
| JP4328388B2 (ja) | 1996-09-26 | 2009-09-09 | アルベマール・コーポレーシヨン | スチレン重合体の臭素化方法 |
| JPH10130325A (ja) | 1996-10-31 | 1998-05-19 | Teijin Chem Ltd | ハロゲン化されたスチレン重合物の製法 |
-
1997
- 1997-09-05 JP JP51565898A patent/JP4328388B2/ja not_active Expired - Lifetime
- 1997-09-05 IL IL12911397A patent/IL129113A/en not_active IP Right Cessation
- 1997-09-05 DE DE69701997T patent/DE69701997T2/de not_active Expired - Lifetime
- 1997-09-05 EP EP97940834A patent/EP0928300B1/en not_active Expired - Lifetime
- 1997-09-05 WO PCT/US1997/015622 patent/WO1998013396A1/en not_active Ceased
- 1997-09-05 CA CA002265642A patent/CA2265642C/en not_active Expired - Lifetime
-
1998
- 1998-03-13 US US09/041,632 patent/US5916978A/en not_active Expired - Lifetime
-
1999
- 1999-04-13 US US09/291,428 patent/US6207765B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US6207765B1 (en) | 2001-03-27 |
| IL129113A0 (en) | 2000-02-17 |
| EP0928300B1 (en) | 2000-05-10 |
| IL129113A (en) | 2002-08-14 |
| DE69701997D1 (de) | 2000-06-15 |
| JP4328388B2 (ja) | 2009-09-09 |
| DE69701997T2 (de) | 2000-11-09 |
| JP2001501237A (ja) | 2001-01-30 |
| EP0928300A1 (en) | 1999-07-14 |
| CA2265642A1 (en) | 1998-04-02 |
| US5916978A (en) | 1999-06-29 |
| WO1998013396A1 (en) | 1998-04-02 |
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