BRPI0619699A2 - copolìmero bromado termicamente estável, mistura de polìmeros, artigo moldado e processo para preparar um copolìmero bromado - Google Patents
copolìmero bromado termicamente estável, mistura de polìmeros, artigo moldado e processo para preparar um copolìmero bromado Download PDFInfo
- Publication number
- BRPI0619699A2 BRPI0619699A2 BRPI0619699-3A BRPI0619699A BRPI0619699A2 BR PI0619699 A2 BRPI0619699 A2 BR PI0619699A2 BR PI0619699 A BRPI0619699 A BR PI0619699A BR PI0619699 A2 BRPI0619699 A2 BR PI0619699A2
- Authority
- BR
- Brazil
- Prior art keywords
- copolymer
- weight
- butadiene
- styrene
- brominated
- Prior art date
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- 229920001577 copolymer Polymers 0.000 title claims abstract description 152
- 229920002959 polymer blend Polymers 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000000203 mixture Substances 0.000 claims abstract description 57
- 239000003063 flame retardant Substances 0.000 claims abstract description 30
- 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 abstract description 28
- 239000000654 additive Substances 0.000 claims abstract description 25
- 230000000996 additive effect Effects 0.000 claims abstract description 13
- 229920001400 block copolymer Polymers 0.000 claims abstract description 11
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 76
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 74
- 229920000642 polymer Polymers 0.000 claims description 67
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 55
- 229910052794 bromium Inorganic materials 0.000 claims description 55
- 239000006260 foam Substances 0.000 claims description 51
- 229920002554 vinyl polymer Polymers 0.000 claims description 50
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 45
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 44
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 30
- 239000000178 monomer Substances 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 22
- 239000004793 Polystyrene Substances 0.000 claims description 20
- 239000011324 bead Substances 0.000 claims description 20
- 230000031709 bromination Effects 0.000 claims description 20
- 238000005893 bromination reaction Methods 0.000 claims description 20
- 230000008569 process Effects 0.000 claims description 20
- 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 20
- 229920002223 polystyrene Polymers 0.000 claims description 19
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical group Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical class CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 claims description 17
- 239000004088 foaming agent Substances 0.000 claims description 16
- 238000002411 thermogravimetry Methods 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 230000004580 weight loss Effects 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000005481 NMR spectroscopy Methods 0.000 claims description 10
- -1 polyethylene Polymers 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000003440 styrenes Chemical class 0.000 claims description 6
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229920000428 triblock copolymer Polymers 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 4
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- VKVLTUQLNXVANB-UHFFFAOYSA-N 1-ethenyl-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1C=C VKVLTUQLNXVANB-UHFFFAOYSA-N 0.000 claims description 3
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000004698 Polyethylene Substances 0.000 claims description 3
- 229920000359 diblock copolymer Polymers 0.000 claims description 3
- 229920000573 polyethylene Polymers 0.000 claims description 3
- 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 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- BXOUVIIITJXIKB-UHFFFAOYSA-N ethene;styrene Chemical compound C=C.C=CC1=CC=CC=C1 BXOUVIIITJXIKB-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000004611 light stabiliser Substances 0.000 claims description 2
- 239000002667 nucleating agent Substances 0.000 claims description 2
- 229920005604 random copolymer Polymers 0.000 claims description 2
- 238000004611 spectroscopical analysis Methods 0.000 claims description 2
- 239000003017 thermal stabilizer Substances 0.000 claims description 2
- OEVVKKAVYQFQNV-UHFFFAOYSA-N 1-ethenyl-2,4-dimethylbenzene Chemical compound CC1=CC=C(C=C)C(C)=C1 OEVVKKAVYQFQNV-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- SFBTTWXNCQVIEC-UHFFFAOYSA-N o-Vinylanisole Chemical compound COC1=CC=CC=C1C=C SFBTTWXNCQVIEC-UHFFFAOYSA-N 0.000 claims 2
- SSZOCHFYWWVSAI-UHFFFAOYSA-N 1-bromo-2-ethenylbenzene Chemical compound BrC1=CC=CC=C1C=C SSZOCHFYWWVSAI-UHFFFAOYSA-N 0.000 claims 1
- WGGLDBIZIQMEGH-UHFFFAOYSA-N 1-bromo-4-ethenylbenzene Chemical compound BrC1=CC=C(C=C)C=C1 WGGLDBIZIQMEGH-UHFFFAOYSA-N 0.000 claims 1
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- 230000001413 cellular effect Effects 0.000 claims 1
- 125000005395 methacrylic acid group Chemical group 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 17
- 229920003048 styrene butadiene rubber Polymers 0.000 abstract description 16
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical class C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 abstract description 11
- 229920000578 graft copolymer Polymers 0.000 abstract description 2
- 229920002857 polybutadiene Polymers 0.000 description 57
- 239000000243 solution Substances 0.000 description 43
- 239000005062 Polybutadiene Substances 0.000 description 33
- 229920006132 styrene block copolymer Polymers 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000012360 testing method Methods 0.000 description 21
- 238000006116 polymerization reaction Methods 0.000 description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 239000011347 resin Substances 0.000 description 18
- 229920005989 resin Polymers 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 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 16
- 238000002156 mixing Methods 0.000 description 14
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 12
- 239000008188 pellet Substances 0.000 description 12
- 239000011159 matrix material Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- 239000002174 Styrene-butadiene Substances 0.000 description 10
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 10
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000003381 stabilizer Substances 0.000 description 9
- GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 description 8
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 8
- 238000005755 formation reaction Methods 0.000 description 8
- 239000000499 gel Substances 0.000 description 8
- 229920001519 homopolymer Polymers 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 125000001246 bromo group Chemical group Br* 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000001569 carbon dioxide Substances 0.000 description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 6
- 239000003607 modifier Substances 0.000 description 6
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 6
- 229920000638 styrene acrylonitrile Polymers 0.000 description 6
- 230000002411 adverse Effects 0.000 description 5
- 150000001649 bromium compounds Chemical group 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
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- 150000001993 dienes Chemical class 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 229920006248 expandable polystyrene Polymers 0.000 description 4
- 239000004795 extruded polystyrene foam Substances 0.000 description 4
- 230000000977 initiatory effect Effects 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 230000003252 repetitive effect Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 210000000497 foam cell Anatomy 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 239000001282 iso-butane Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 3
- BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 description 3
- 230000002285 radioactive effect Effects 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000011115 styrene butadiene Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- AGXUVMPSUKZYDT-UHFFFAOYSA-L barium(2+);octadecanoate Chemical compound [Ba+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AGXUVMPSUKZYDT-UHFFFAOYSA-L 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
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- 229910052736 halogen Inorganic materials 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
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- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 238000003947 neutron activation analysis Methods 0.000 description 2
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- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 2
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 2
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 2
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- SFLXUZPXEWWQNH-UHFFFAOYSA-K tetrabutylazanium;tribromide Chemical compound [Br-].[Br-].[Br-].CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC SFLXUZPXEWWQNH-UHFFFAOYSA-K 0.000 description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- 229940078499 tricalcium phosphate Drugs 0.000 description 2
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 2
- 235000019731 tricalcium phosphate Nutrition 0.000 description 2
- 238000004846 x-ray emission Methods 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SPPWGCYEYAMHDT-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(C(C)C)C=C1 SPPWGCYEYAMHDT-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
- 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
- 239000004604 Blowing Agent Substances 0.000 description 1
- PKHKSCDFQWKYKA-UHFFFAOYSA-N C=CC1=CC=CC=C1.C=CC=C.C=CC1=CC=CC=C1.C=CC=C.C=CC1=CC=CC=C1 Chemical compound C=CC1=CC=CC=C1.C=CC=C.C=CC1=CC=CC=C1.C=CC=C.C=CC1=CC=CC=C1 PKHKSCDFQWKYKA-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000005065 High vinyl polybutadiene Substances 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910003206 NH4VO3 Inorganic materials 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
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- 229910052792 caesium Inorganic materials 0.000 description 1
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- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
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- 229910052732 germanium Inorganic materials 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
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- 229920002589 poly(vinylethylene) polymer Polymers 0.000 description 1
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- 229920001195 polyisoprene Polymers 0.000 description 1
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- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
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- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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- PRXNKYBFWAWBNZ-UHFFFAOYSA-N trimethylphenylammonium tribromide Chemical compound Br[Br-]Br.C[N+](C)(C)C1=CC=CC=C1 PRXNKYBFWAWBNZ-UHFFFAOYSA-N 0.000 description 1
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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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/12—Incorporating halogen atoms into the molecule
-
- 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
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/10—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated with vinyl-aromatic monomers
-
- 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
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/14—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated containing elements other than carbon and hydrogen
- C08F236/16—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated containing elements other than carbon and hydrogen containing halogen
-
- 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
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/16—Making expandable particles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2325/00—Characterised by the use of homopolymers or 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; Derivatives of such polymers
- C08J2325/02—Homopolymers or copolymers of hydrocarbons
- C08J2325/04—Homopolymers or copolymers of styrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2453/00—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
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 (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0619699A2 true BRPI0619699A2 (pt) | 2011-10-11 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0619699-3A BRPI0619699A2 (pt) | 2005-11-12 | 2006-10-23 | copolìmero bromado termicamente estável, mistura de polìmeros, artigo moldado e processo para preparar um copolìmero bromado |
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 |
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| JP5536452B2 (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 |
| 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 |
| WO2009061600A1 (en) | 2007-11-07 | 2009-05-14 | Dow Global Technologies, Inc. | Partial solvent stripping process for recovering brominated butadiene polymers from solution |
| 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 |
| JP5508397B2 (ja) * | 2008-05-01 | 2014-05-28 | ダウ グローバル テクノロジーズ エルエルシー | ブタジエン共重合体を臭素化する２段階方法 |
| US9732178B1 (en) | 2008-07-24 | 2017-08-15 | Bridgestone Corporation | Block copolymers including high vinyl segments |
| US8481613B2 (en) | 2008-08-05 | 2013-07-09 | Dow Global Technologies Llc | Solvent transfer process for organic polymers |
| 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 |
| EP2318445B1 (en) * | 2008-08-22 | 2012-11-21 | 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 |
| WO2010080285A2 (en) | 2008-12-18 | 2010-07-15 | Dow Global Technologies Inc. | Stabilizers for polymers containing aliphatically-bound bromine |
| US8779066B2 (en) | 2008-12-19 | 2014-07-15 | Dow Global Technologies Llc | Process for brominating butadiene polymers using ester solvent mixtures |
| CN102378769B (zh) | 2009-03-31 | 2013-06-12 | 陶氏环球技术有限责任公司 | 用于溴化不饱和有机化合物并去除单氯化季铵或季*的方法 |
| RU2530021C2 (ru) | 2009-06-30 | 2014-10-10 | ДАУ ГЛОБАЛ ТЕКНОЛОДЖИЗ ЭлЭлСи | Бромированные и эпоксидированные замедлители горения |
| DE102009059781A1 (de) | 2009-12-18 | 2011-06-22 | Basf Se, 67063 | Flammgeschützte Polymerschaumstoffe |
| WO2011095540A2 (de) | 2010-02-05 | 2011-08-11 | Basf Se | Halogenfreie, phosphorhaltige flammgeschützte polymerschaumstoffe |
| EP2531557A1 (de) | 2010-02-05 | 2012-12-12 | Basf Se | Flammschutzmittel |
| US8691896B2 (en) | 2010-02-05 | 2014-04-08 | Basf Se | Halogen-free, phosphorus-containing flame-retardant polymer foams |
| WO2011113795A2 (de) | 2010-03-17 | 2011-09-22 | Basf Se | Flammgeschützter verbundschaumstoff |
| PL2553008T3 (pl) | 2010-04-01 | 2017-02-28 | Basf Se | Środek ogniochronny |
| US9115312B2 (en) | 2010-04-01 | 2015-08-25 | Basf Se | Flame retardant |
| EP2580250B1 (en) * | 2010-06-14 | 2021-10-27 | DDP Specialty Electronic Materials US, LLC | Process for brominating butadiene polymers |
| WO2012016906A1 (de) | 2010-08-05 | 2012-02-09 | Basf Se | Halogenhaltige polymermischungen |
| US9517579B2 (en) * | 2010-12-17 | 2016-12-13 | Dow Global Technologies Llc | Polystyrene melt extrusion process |
| ES2535972T3 (es) | 2011-06-08 | 2015-05-19 | Italmatch Chemicals S.P.A. | Espumas de poliestireno extruidas de combustión lenta |
| WO2013009469A1 (en) * | 2011-07-14 | 2013-01-17 | Dow Global Technologies Llc | Impact-modified styrenic polymers containing brominated vinyl aromatic-butadiene copolymer |
| CN103649191B (zh) * | 2011-07-14 | 2016-05-18 | 陶氏环球技术有限责任公司 | 包含溴化苯乙烯-丁二烯共聚物的选择性气体运输薄膜 |
| WO2013017417A1 (de) | 2011-07-29 | 2013-02-07 | Basf Se | Polymeres flammschutzmittel |
| ITVI20110231A1 (it) | 2011-08-09 | 2013-02-10 | Micaela Lorenzi | Nuova composizione ritardante di fiamma per polistirene |
| ITMI20111982A1 (it) * | 2011-11-02 | 2013-05-03 | Polimeri Europa Spa | Composizioni a base di polimeri vinilaromatici espansibili autoestinguenti |
| JP2013116958A (ja) | 2011-12-02 | 2013-06-13 | Dow Global Technologies Llc | 発泡性スチレン系樹脂組成物及びスチレン系樹脂発泡体の製造方法 |
| RU2014129861A (ru) * | 2011-12-19 | 2016-02-10 | ДАУ ГЛОБАЛ ТЕКНОЛОДЖИЗ ЭлЭлСи | Термоотверждаемый полиуретановый пеноматериал, содержащий бромированный полимерный антипирен |
| CN104011119B (zh) * | 2011-12-21 | 2016-08-24 | 巴斯夫欧洲公司 | 制备包含石墨和阻燃剂的可膨胀苯乙烯聚合物的方法 |
| JP5943730B2 (ja) * | 2012-06-13 | 2016-07-05 | 株式会社ジェイエスピー | ポリスチレン系樹脂押出発泡体の製造方法 |
| WO2014014648A2 (en) | 2012-07-18 | 2014-01-23 | Rohm And Haas Company | Textiles with brominated polymer flame retardant |
| NL2009320C2 (nl) * | 2012-08-14 | 2014-02-18 | Synbra Tech Bv | Deeltjesvormig, expandeerbaar polymeer, werkwijze ter vervaardiging hiervan, alsmede de toepassing. |
| WO2014066089A1 (en) | 2012-10-24 | 2014-05-01 | Dow Global Technologies Llc | Glycerol ester and brominated polymer in styrenic polymer |
| ITMI20121808A1 (it) | 2012-10-24 | 2014-04-25 | Versalis Spa | Composizioni polimeriche concentrate di polimeri e/o copolimeri vinilaromatici |
| EP2945981B1 (en) | 2013-01-18 | 2020-05-06 | BEWiSynbra RAW Oy | Method of producing polystyrene beads containing athermanous particles |
| JP5794406B2 (ja) | 2013-02-14 | 2015-10-14 | 株式会社カネカ | スチレン系樹脂押出発泡体及びそのリサイクル方法 |
| CN105209546B (zh) | 2013-03-20 | 2018-12-28 | 巴斯夫欧洲公司 | 聚氨酯基聚合物组合物 |
| EP2789651A1 (de) | 2013-04-11 | 2014-10-15 | Basf Se | Flammschutzmittelzusammensetzung zur Verwendung in Styrolpolymerschaumstoffen |
| JP6128940B2 (ja) * | 2013-05-09 | 2017-05-17 | 株式会社ジェイエスピー | ポリスチレン系樹脂押出発泡板の製造方法 |
| JP6099495B2 (ja) * | 2013-06-21 | 2017-03-22 | 株式会社ジェイエスピー | 難燃剤溶融混練物及びこれを用いたポリスチレン系樹脂押出発泡体の製造方法 |
| JP6139294B2 (ja) * | 2013-06-24 | 2017-05-31 | 株式会社カネカ | スチレン系樹脂押出発泡体及びその製造方法 |
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| CN101305022B (zh) | 2012-06-20 |
| JP5302001B2 (ja) | 2013-10-02 |
| ES2336951T3 (es) | 2010-04-19 |
| US7851558B2 (en) | 2010-12-14 |
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| CN101305022A (zh) | 2008-11-12 |
| NO20081960L (no) | 2008-08-11 |
| HRP20080206A2 (hr) | 2008-08-31 |
| RU2414479C2 (ru) | 2011-03-20 |
| EP1957544B1 (en) | 2010-01-20 |
| ATE455796T1 (de) | 2010-02-15 |
| RU2008123837A (ru) | 2009-12-27 |
| DE602006011944D1 (de) | 2010-03-11 |
| WO2007058736A1 (en) | 2007-05-24 |
| JP2009516019A (ja) | 2009-04-16 |
| AU2006315878A1 (en) | 2007-05-24 |
| US20080287559A1 (en) | 2008-11-20 |
| KR20080066787A (ko) | 2008-07-16 |
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