KR101353883B1 - 브롬화 음이온성 스티렌계 중합체 및 이의 제조 - Google Patents
브롬화 음이온성 스티렌계 중합체 및 이의 제조 Download PDFInfo
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- KR101353883B1 KR101353883B1 KR1020087015148A KR20087015148A KR101353883B1 KR 101353883 B1 KR101353883 B1 KR 101353883B1 KR 1020087015148 A KR1020087015148 A KR 1020087015148A KR 20087015148 A KR20087015148 A KR 20087015148A KR 101353883 B1 KR101353883 B1 KR 101353883B1
- Authority
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- South Korea
- Prior art keywords
- polymer
- reaction mixture
- bromine
- feed
- catalyst
- 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.)
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- 229920000642 polymer Polymers 0.000 title claims abstract description 207
- 125000000129 anionic group Chemical group 0.000 title claims abstract description 181
- 238000002360 preparation method Methods 0.000 title description 5
- 239000011541 reaction mixture Substances 0.000 claims abstract description 120
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims abstract description 112
- 238000006243 chemical reaction Methods 0.000 claims abstract description 112
- 239000003054 catalyst Substances 0.000 claims abstract description 92
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 89
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 88
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 86
- 238000005893 bromination reaction Methods 0.000 claims abstract description 68
- -1 aluminum halide Chemical class 0.000 claims abstract description 38
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 28
- 125000003118 aryl group Chemical group 0.000 claims abstract description 25
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 25
- 239000000178 monomer Substances 0.000 claims abstract description 19
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims abstract description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 147
- 239000000243 solution Substances 0.000 claims description 77
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 74
- 238000000034 method Methods 0.000 claims description 61
- 238000010791 quenching Methods 0.000 claims description 57
- 239000002904 solvent Substances 0.000 claims description 51
- 239000004793 Polystyrene Substances 0.000 claims description 44
- 229920002223 polystyrene Polymers 0.000 claims description 44
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 37
- 230000000171 quenching effect Effects 0.000 claims description 32
- 230000008569 process Effects 0.000 claims description 31
- 239000007788 liquid Substances 0.000 claims description 27
- 238000012360 testing method Methods 0.000 claims description 22
- 230000002829 reductive effect Effects 0.000 claims description 18
- 239000002002 slurry Substances 0.000 claims description 18
- 238000010924 continuous production Methods 0.000 claims description 16
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 14
- 125000001246 bromo group Chemical group Br* 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 238000013112 stability test Methods 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 6
- 238000010923 batch production Methods 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 5
- 230000000717 retained effect Effects 0.000 claims description 5
- 239000004615 ingredient Substances 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 230000002730 additional effect Effects 0.000 claims 2
- 150000004820 halides Chemical group 0.000 claims 1
- 239000011259 mixed solution Substances 0.000 claims 1
- 230000031709 bromination Effects 0.000 abstract description 35
- 230000009286 beneficial effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 76
- 239000000047 product Substances 0.000 description 63
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- 239000000523 sample Substances 0.000 description 31
- 229910052757 nitrogen Inorganic materials 0.000 description 23
- 238000002156 mixing Methods 0.000 description 20
- 229920001169 thermoplastic Polymers 0.000 description 17
- 238000004458 analytical method Methods 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 16
- 238000010926 purge Methods 0.000 description 16
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- 239000012535 impurity Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000003063 flame retardant Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000011521 glass Substances 0.000 description 11
- JPOXNPPZZKNXOV-UHFFFAOYSA-N bromochloromethane Chemical compound ClCBr JPOXNPPZZKNXOV-UHFFFAOYSA-N 0.000 description 10
- 230000009849 deactivation Effects 0.000 description 10
- 239000007789 gas Substances 0.000 description 10
- 230000035484 reaction time Effects 0.000 description 10
- 239000004416 thermosoftening plastic Substances 0.000 description 10
- 125000005843 halogen group Chemical group 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 230000010349 pulsation Effects 0.000 description 9
- 230000009467 reduction Effects 0.000 description 9
- 238000005201 scrubbing Methods 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 8
- 235000010265 sodium sulphite Nutrition 0.000 description 8
- 238000010626 work up procedure Methods 0.000 description 8
- FWAJPSIPOULHHH-UHFFFAOYSA-N 1,2,4-tribromobenzene Chemical compound BrC1=CC=C(Br)C(Br)=C1 FWAJPSIPOULHHH-UHFFFAOYSA-N 0.000 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 description 7
- 229920006362 Teflon® Polymers 0.000 description 7
- QCKHVNQHBOGZER-UHFFFAOYSA-N 1,2,4,5-tetrabromobenzene Chemical compound BrC1=CC(Br)=C(Br)C=C1Br QCKHVNQHBOGZER-UHFFFAOYSA-N 0.000 description 6
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 6
- 239000004809 Teflon Substances 0.000 description 6
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 6
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 239000003518 caustics Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 239000012763 reinforcing filler Substances 0.000 description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 238000000149 argon plasma sintering Methods 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 238000012937 correction Methods 0.000 description 4
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 4
- 229920002313 fluoropolymer Polymers 0.000 description 4
- 239000004811 fluoropolymer Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 230000010354 integration Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- 238000002411 thermogravimetry Methods 0.000 description 4
- 101710134784 Agnoprotein Proteins 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920002449 FKM Polymers 0.000 description 3
- 229920001283 Polyalkylene terephthalate Polymers 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 3
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical group Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 238000006900 dealkylation reaction Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 125000000950 dibromo group Chemical group Br* 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000000670 limiting effect Effects 0.000 description 3
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- 229920001778 nylon Polymers 0.000 description 3
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- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- NSBGJRFJIJFMGW-UHFFFAOYSA-N trisodium;stiborate Chemical compound [Na+].[Na+].[Na+].[O-][Sb]([O-])([O-])=O NSBGJRFJIJFMGW-UHFFFAOYSA-N 0.000 description 3
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
- IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000004594 Masterbatch (MB) Substances 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
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- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
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- 238000010539 anionic addition polymerization reaction Methods 0.000 description 2
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- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
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- 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
- 229920001084 poly(chloroprene) Polymers 0.000 description 2
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- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
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- QVLAWKAXOMEXPM-DICFDUPASA-N 1,1,1,2-tetrachloro-2,2-dideuterioethane Chemical group [2H]C([2H])(Cl)C(Cl)(Cl)Cl QVLAWKAXOMEXPM-DICFDUPASA-N 0.000 description 1
- QXSZNDIIPUOQMB-UHFFFAOYSA-N 1,1,2,2-tetrabromoethane Chemical compound BrC(Br)C(Br)Br QXSZNDIIPUOQMB-UHFFFAOYSA-N 0.000 description 1
- QUMDOMSJJIFTCA-UHFFFAOYSA-N 1,1,2-tribromoethane Chemical compound BrCC(Br)Br QUMDOMSJJIFTCA-UHFFFAOYSA-N 0.000 description 1
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- LLVVSBBXENOOQY-UHFFFAOYSA-N 1,2,3,4,5-pentabromobenzene Chemical compound BrC1=CC(Br)=C(Br)C(Br)=C1Br LLVVSBBXENOOQY-UHFFFAOYSA-N 0.000 description 1
- QRFALSDGOMLVIR-UHFFFAOYSA-N 1,2,3,4-tetrabromobenzene Chemical compound BrC1=CC=C(Br)C(Br)=C1Br QRFALSDGOMLVIR-UHFFFAOYSA-N 0.000 description 1
- GMVJKSNPLYBFSO-UHFFFAOYSA-N 1,2,3-tribromobenzene Chemical compound BrC1=CC=CC(Br)=C1Br GMVJKSNPLYBFSO-UHFFFAOYSA-N 0.000 description 1
- XFNJYAKDBJUJAJ-UHFFFAOYSA-N 1,2-dibromopropane Chemical compound CC(Br)CBr XFNJYAKDBJUJAJ-UHFFFAOYSA-N 0.000 description 1
- XAEZQQVZRXSKKJ-UHFFFAOYSA-N 1,3-dibromoimidazolidine-2,4-dione Chemical compound BrN1CC(=O)N(Br)C1=O XAEZQQVZRXSKKJ-UHFFFAOYSA-N 0.000 description 1
- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- LSXKDWGTSHCFPP-UHFFFAOYSA-N 1-bromoheptane Chemical compound CCCCCCCBr LSXKDWGTSHCFPP-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- 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
- LCJNYCWJKAWZKZ-UHFFFAOYSA-N 1-prop-1-en-2-ylnaphthalene Chemical compound C1=CC=C2C(C(=C)C)=CC=CC2=C1 LCJNYCWJKAWZKZ-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
- UPSXAPQYNGXVBF-UHFFFAOYSA-N 2-bromobutane Chemical compound CCC(C)Br UPSXAPQYNGXVBF-UHFFFAOYSA-N 0.000 description 1
- BTOVVHWKPVSLBI-UHFFFAOYSA-N 2-methylprop-1-enylbenzene Chemical compound CC(C)=CC1=CC=CC=C1 BTOVVHWKPVSLBI-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
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- NIUPXOVDDRSEIZ-UHFFFAOYSA-K Br[Al](Br)Br.Cl.Cl Chemical compound Br[Al](Br)Br.Cl.Cl NIUPXOVDDRSEIZ-UHFFFAOYSA-K 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- 229910000975 Carbon steel Inorganic materials 0.000 description 1
- CRLYIUPMCGFJSO-UHFFFAOYSA-K Cl.[Br-].[Al+3].[Br-].[Br-] Chemical compound Cl.[Br-].[Al+3].[Br-].[Br-] CRLYIUPMCGFJSO-UHFFFAOYSA-K 0.000 description 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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- 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
-
- 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
- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
- C08F12/16—Halogens
- C08F12/21—Bromine
-
- 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
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| US7632893B2 (en) * | 2005-06-30 | 2009-12-15 | Albemarle Corporation | Brominated styrenic polymers and their preparation |
| ES2602097T3 (es) | 2005-12-21 | 2017-02-17 | Albemarle Corporation | Polímeros aniónicos estirénicos bromados y su preparación |
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| 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 |
| MX2009013127A (es) | 2007-06-07 | 2010-01-15 | Albemarle Corp | Polimeros bromados de bajo peso molecular y su uso en formulaciones termoplasticas. |
| 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 |
| EP3470441A1 (en) * | 2008-06-06 | 2019-04-17 | Albemarle Corporation | Low molecular weight brominated polymers, processes for their manufacture and their use in thermoplastic formulations |
| JO3423B1 (ar) * | 2008-12-02 | 2019-10-20 | Albemarle Corp | مؤخرات لهب معالجة بالبروم و مواد مشتقه منها |
| US8642821B2 (en) | 2008-12-02 | 2014-02-04 | Albemarle Corporation | Bromination of telomer mixtures derived from toluene and styrene |
| KR20110100216A (ko) | 2008-12-02 | 2011-09-09 | 알베마를 코포레이션 | 분지형 또는 별모양 분지형 스티렌 폴리머, 텔로머, 및 부가물, 그의 합성, 그의 브롬화, 및 그의 용도 |
| CN102224122B (zh) | 2008-12-02 | 2014-09-03 | 雅宝公司 | 甲苯和苯乙烯衍生的调聚物分布物及由其制备的溴化阻燃剂 |
| US8753554B2 (en) | 2009-05-01 | 2014-06-17 | Albemarle Corporation | Pelletized low molecular weight brominated aromatic polymer compositions |
| JO3059B1 (ar) * | 2009-05-01 | 2017-03-15 | Albemarle Corp | معالجة بالبروم لتراكيب بوليمرات عطرية ذات وزن جزيئي منخفض |
| CN101824113B (zh) * | 2010-04-14 | 2011-12-07 | 山东兄弟科技股份有限公司 | 一种可控分子量溴化聚苯乙烯的制备方法 |
| JP6609614B2 (ja) * | 2014-07-08 | 2019-11-20 | ブローミン コンパウンズ リミテッド | 臭素含有重合体の調製およびその難燃剤としての応用 |
| CN107092188A (zh) * | 2017-05-27 | 2017-08-25 | 南京邮电大学 | 一种连续搅拌釜式反应器系统的广义预测控制算法 |
| CN109293854B (zh) * | 2017-07-25 | 2021-01-29 | 中国石油天然气股份有限公司 | 高色度抗冲击聚苯乙烯及其制备方法和制备装置 |
| EP4556625A1 (en) * | 2018-04-09 | 2025-05-21 | Albemarle Corporation | Flame retardants for textile applications |
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| 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 |
| WO2008086362A1 (en) | 2007-01-10 | 2008-07-17 | Albemarle Corporation | Brominated styrenic polymer compositions and processes for producing same |
| TW200838919A (en) | 2007-01-10 | 2008-10-01 | Albemarle Corp | Brominated styrenic polymer compositions and processes for producing same |
-
2006
- 2006-12-19 ES ES06846694.5T patent/ES2602097T3/es active Active
- 2006-12-19 KR KR1020087015148A patent/KR101353883B1/ko active Active
- 2006-12-19 CA CA2629742A patent/CA2629742C/en active Active
- 2006-12-19 CN CN2006800481965A patent/CN101341174B/zh active Active
- 2006-12-19 BR BRPI0620898-3A patent/BRPI0620898A2/pt not_active Application Discontinuation
- 2006-12-19 PL PL06846694T patent/PL1963377T3/pl unknown
- 2006-12-19 WO PCT/US2006/062321 patent/WO2007076369A1/en not_active Ceased
- 2006-12-19 US US11/612,991 patent/US7638583B2/en active Active
- 2006-12-19 EP EP06846694.5A patent/EP1963377B1/en active Active
- 2006-12-19 JP JP2008547734A patent/JP5261190B2/ja active Active
- 2006-12-19 HU HUE06846694A patent/HUE030768T2/en unknown
- 2006-12-20 TW TW095147781A patent/TWI406877B/zh not_active IP Right Cessation
- 2006-12-21 JO JOP/2006/0491A patent/JO3223B1/ar active
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2008
- 2008-06-16 IL IL192217A patent/IL192217A/en active IP Right Grant
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6521714B2 (en) * | 1996-09-26 | 2003-02-18 | Albemarle Corporation | Brominated polystyrenic resins |
Also Published As
| Publication number | Publication date |
|---|---|
| JO3223B1 (ar) | 2018-03-08 |
| KR20080075890A (ko) | 2008-08-19 |
| CN101341174B (zh) | 2011-08-31 |
| US20100087620A1 (en) | 2010-04-08 |
| HUE030768T2 (en) | 2017-05-29 |
| EP1963377B1 (en) | 2016-08-10 |
| US8071688B2 (en) | 2011-12-06 |
| IL192217A (en) | 2015-01-29 |
| IL192217A0 (en) | 2008-12-29 |
| CN101341174A (zh) | 2009-01-07 |
| CA2629742C (en) | 2014-02-18 |
| BRPI0620898A2 (pt) | 2011-11-29 |
| TW200730550A (en) | 2007-08-16 |
| WO2007076369A1 (en) | 2007-07-05 |
| CA2629742A1 (en) | 2007-07-05 |
| JP2009521587A (ja) | 2009-06-04 |
| US20070142566A1 (en) | 2007-06-21 |
| PL1963377T3 (pl) | 2017-05-31 |
| EP1963377A1 (en) | 2008-09-03 |
| JP5261190B2 (ja) | 2013-08-14 |
| US7638583B2 (en) | 2009-12-29 |
| ES2602097T3 (es) | 2017-02-17 |
| TWI406877B (zh) | 2013-09-01 |
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