CA2627253C - Brominated butadiene/vinyl aromatic copolymers, blends of such copolymers with a vinyl aromatic polymer, and polymeric foams formed from such blends - Google Patents
Brominated butadiene/vinyl aromatic copolymers, blends of such copolymers with a vinyl aromatic polymer, and polymeric foams formed from such blends Download PDFInfo
- Publication number
- CA2627253C CA2627253C CA2627253A CA2627253A CA2627253C CA 2627253 C CA2627253 C CA 2627253C CA 2627253 A CA2627253 A CA 2627253A CA 2627253 A CA2627253 A CA 2627253A CA 2627253 C CA2627253 C CA 2627253C
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- Canada
- Prior art keywords
- copolymer
- weight
- brominated
- butadiene
- percent
- 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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- 229920001577 copolymer Polymers 0.000 title claims abstract description 148
- 239000000203 mixture Substances 0.000 title claims abstract description 68
- 229920000642 polymer Polymers 0.000 title claims description 76
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title claims description 63
- 239000006260 foam Substances 0.000 title claims description 59
- 229920002554 vinyl polymer Polymers 0.000 title claims description 58
- 239000000654 additive Substances 0.000 claims abstract description 26
- 239000003063 flame retardant Substances 0.000 claims abstract description 22
- 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 20
- 230000000996 additive effect Effects 0.000 claims abstract description 14
- 229920001400 block copolymer Polymers 0.000 claims abstract description 11
- 229920000578 graft copolymer Polymers 0.000 claims abstract description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 71
- 238000005893 bromination reaction Methods 0.000 claims description 64
- 230000031709 bromination Effects 0.000 claims description 62
- 229910052794 bromium Inorganic materials 0.000 claims description 57
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 55
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 51
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 50
- 238000000034 method Methods 0.000 claims description 48
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 30
- 239000011324 bead Substances 0.000 claims description 27
- 239000000178 monomer Substances 0.000 claims description 26
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 25
- 230000008569 process Effects 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 22
- 239000004793 Polystyrene Substances 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 21
- 229920002223 polystyrene Polymers 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 19
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical class CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 claims description 18
- 239000004088 foaming agent Substances 0.000 claims description 17
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical group Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 16
- 238000002411 thermogravimetry Methods 0.000 claims description 15
- 230000004580 weight loss Effects 0.000 claims description 15
- -1 4-methylstryrene Chemical compound 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 229920002959 polymer blend Polymers 0.000 claims description 10
- 150000003440 styrenes Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229920005604 random copolymer Polymers 0.000 claims description 6
- 230000000979 retarding effect Effects 0.000 claims description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 claims description 5
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 5
- 229920000428 triblock copolymer Polymers 0.000 claims description 5
- WGGLDBIZIQMEGH-UHFFFAOYSA-N 1-bromo-4-ethenylbenzene Chemical compound BrC1=CC=C(C=C)C=C1 WGGLDBIZIQMEGH-UHFFFAOYSA-N 0.000 claims description 3
- OEVVKKAVYQFQNV-UHFFFAOYSA-N 1-ethenyl-2,4-dimethylbenzene Chemical compound CC1=CC=C(C=C)C(C)=C1 OEVVKKAVYQFQNV-UHFFFAOYSA-N 0.000 claims description 3
- 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
- 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 3
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 3
- 239000003086 colorant Substances 0.000 claims description 3
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 229920000359 diblock copolymer Polymers 0.000 claims description 2
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 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
- 229920003251 poly(α-methylstyrene) Polymers 0.000 claims description 2
- 239000003017 thermal stabilizer Substances 0.000 claims description 2
- SSZOCHFYWWVSAI-UHFFFAOYSA-N 1-bromo-2-ethenylbenzene Chemical compound BrC1=CC=CC=C1C=C SSZOCHFYWWVSAI-UHFFFAOYSA-N 0.000 claims 2
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 claims 2
- 230000001413 cellular effect Effects 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- CTHJQRHPNQEPAB-UHFFFAOYSA-N 2-methoxyethenylbenzene Chemical compound COC=CC1=CC=CC=C1 CTHJQRHPNQEPAB-UHFFFAOYSA-N 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 1
- SFBTTWXNCQVIEC-UHFFFAOYSA-N o-Vinylanisole Chemical compound COC1=CC=CC=C1C=C SFBTTWXNCQVIEC-UHFFFAOYSA-N 0.000 claims 1
- 229920003048 styrene butadiene rubber Polymers 0.000 abstract description 24
- 238000002360 preparation method Methods 0.000 abstract description 17
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical class C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 abstract description 14
- 229920002857 polybutadiene Polymers 0.000 description 45
- 239000000243 solution Substances 0.000 description 45
- 239000005062 Polybutadiene Substances 0.000 description 36
- 238000012360 testing method Methods 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 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 23
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000006116 polymerization reaction Methods 0.000 description 19
- 239000011347 resin Substances 0.000 description 18
- 229920005989 resin Polymers 0.000 description 18
- 229920006132 styrene block copolymer Polymers 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 14
- 238000002156 mixing Methods 0.000 description 14
- IYSTUUQQVNNJDN-UHFFFAOYSA-N 2-[4-(4,5-diphenyl-1H-imidazol-2-yl)phenyl]-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C1(=CC=CC=C1)C=1N=C(NC=1C1=CC=CC=C1)C1=CC=C(C=C1)C=1NC=2C(=C3C=CC=NC3=C3N=CC=CC=23)N=1 IYSTUUQQVNNJDN-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 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
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000008188 pellet 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
- 229920001519 homopolymer Polymers 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000003381 stabilizer Substances 0.000 description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 8
- 239000002174 Styrene-butadiene Substances 0.000 description 8
- 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
- 125000001246 bromo group Chemical group Br* 0.000 description 8
- 239000000499 gel Substances 0.000 description 8
- 239000003999 initiator Substances 0.000 description 8
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 8
- 229910002092 carbon dioxide Inorganic materials 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000003607 modifier Substances 0.000 description 7
- 239000011541 reaction mixture Substances 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
- 238000005481 NMR spectroscopy Methods 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
- 239000012141 concentrate Substances 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- 230000002411 adverse Effects 0.000 description 5
- 150000001649 bromium compounds Chemical group 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000005187 foaming Methods 0.000 description 4
- 239000001282 iso-butane Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229920006248 expandable polystyrene Polymers 0.000 description 3
- 239000004795 extruded polystyrene foam Substances 0.000 description 3
- 210000000497 foam cell Anatomy 0.000 description 3
- 230000000977 initiatory effect Effects 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
- 239000002798 polar solvent Substances 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
- 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
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-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
- 239000002879 Lewis base Substances 0.000 description 2
- 239000004698 Polyethylene Substances 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
- 239000002585 base Substances 0.000 description 2
- 230000033228 biological regulation 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
- 210000004027 cell Anatomy 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
- 239000006185 dispersion Substances 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 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
- 230000006872 improvement Effects 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 150000007527 lewis bases Chemical class 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000003947 neutron activation analysis Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000002952 polymeric resin Substances 0.000 description 2
- 229920006327 polystyrene foam Polymers 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000007347 radical substitution reaction Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 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
- PRXNKYBFWAWBNZ-UHFFFAOYSA-N trimethylphenylammonium tribromide Chemical compound Br[Br-]Br.C[N+](C)(C)C1=CC=CC=C1 PRXNKYBFWAWBNZ-UHFFFAOYSA-N 0.000 description 2
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing 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
- HTCRKQHJUYBQTK-UHFFFAOYSA-N 2-ethylhexyl 2-methylbutan-2-yloxy carbonate Chemical compound CCCCC(CC)COC(=O)OOC(C)(C)CC HTCRKQHJUYBQTK-UHFFFAOYSA-N 0.000 description 1
- MGTZNGICWXYDPR-ZJWHSJSFSA-N 3-[[(2r)-2-[[(2s)-2-(azepane-1-carbonylamino)-4-methylpentanoyl]amino]-3-(1h-indol-3-yl)propanoyl]amino]butanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)NC(C)CC(O)=O)C(=O)N1CCCCCC1 MGTZNGICWXYDPR-ZJWHSJSFSA-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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241001133184 Colletotrichum agaves Species 0.000 description 1
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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
-
- 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 (2)
| Publication Number | Publication Date |
|---|---|
| CA2627253A1 CA2627253A1 (en) | 2007-05-24 |
| CA2627253C true CA2627253C (en) | 2013-11-19 |
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| Application Number | Title | Priority Date | Filing Date |
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| CA2627253A Active CA2627253C (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 |
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| DE (1) | DE602006011944D1 (enExample) |
| ES (1) | ES2336951T3 (enExample) |
| HR (1) | HRP20080206A2 (enExample) |
| NO (1) | NO20081960L (enExample) |
| RU (1) | RU2414479C2 (enExample) |
| WO (1) | WO2007058736A1 (enExample) |
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| EP2054445B1 (en) * | 2006-08-16 | 2014-06-18 | Dow Global Technologies LLC | Process for brominating butadiene/vinyl aromatic copolymers |
| US8114943B2 (en) * | 2006-08-16 | 2012-02-14 | Dow Global Technologies Llc | Process for brominating butadiene/vinyl aromatic copolymers |
| CN101848942B (zh) | 2007-11-07 | 2012-04-18 | 陶氏环球技术公司 | 从溶液中回收溴化丁二烯聚合物的部分溶剂汽提法 |
| CN101959901B (zh) * | 2008-03-06 | 2013-05-08 | 陶氏环球技术公司 | 通过添加水或特定的溶剂溴化丁二烯共聚物的方法 |
| US8304492B2 (en) | 2008-04-07 | 2012-11-06 | Dow Global Technologies Llc | Process for brominating butadiene/vinyl aromatic copolymers |
| CN102015774B (zh) * | 2008-05-01 | 2013-01-02 | 陶氏环球技术公司 | 用于溴化丁二烯共聚物的两步法 |
| US9732178B1 (en) | 2008-07-24 | 2017-08-15 | Bridgestone Corporation | Block copolymers including high vinyl segments |
| WO2010017134A1 (en) * | 2008-08-05 | 2010-02-11 | Dow Global Technologies Inc. | Solvent transfer process for organic polymers |
| EP2315795B1 (en) * | 2008-08-18 | 2012-09-19 | Dow Global Technologies LLC | Process for forming and devolatilizing brominated polybutadiene polymer particles |
| US8372921B2 (en) * | 2008-08-22 | 2013-02-12 | Dow Global Technologies Llc | Process for brominating unsaturated organic compounds using a quaternary phosphonium tribromide as the brominating agent |
| RU2506289C2 (ru) | 2008-10-31 | 2014-02-10 | ДАУ ГЛОБАЛ ТЕКНОЛОДЖИЗ ЭлЭлСи | Экструдированные полимерные пены, содержащие сложные эфиры сахара и бромированной жирной кислоты, в качествe добавки, ингибирующей воспламенение |
| CN102257050B (zh) * | 2008-12-18 | 2013-09-04 | 陶氏环球技术有限责任公司 | 含有在脂族上结合的溴的阻燃剂聚合物用的稳定剂 |
| EP2379605B1 (en) | 2008-12-19 | 2014-03-12 | Dow Global Technologies LLC | Process for brominating butadiene polymers using ester solvent mixtures |
| EP2414403B1 (en) | 2009-03-31 | 2014-04-30 | Dow Global Technologies LLC | Process for brominating unsaturated organic compounds with removal of quaternary ammonium or quaternary phosphonium monochlorides |
| CN102471397B (zh) * | 2009-06-30 | 2013-11-06 | 陶氏环球技术有限责任公司 | 溴化并环氧化的阻燃剂 |
| DE102009059781A1 (de) | 2009-12-18 | 2011-06-22 | Basf Se, 67063 | Flammgeschützte Polymerschaumstoffe |
| RU2012137686A (ru) | 2010-02-05 | 2014-03-10 | Басф Се | Огнезащитное средство |
| US8691896B2 (en) | 2010-02-05 | 2014-04-08 | Basf Se | Halogen-free, phosphorus-containing flame-retardant polymer foams |
| EP2531552A2 (de) | 2010-02-05 | 2012-12-12 | Basf Se | Halogenfreie, phosphorhaltige flammgeschützte polymerschaumstoffe |
| WO2011113795A2 (de) | 2010-03-17 | 2011-09-22 | Basf Se | Flammgeschützter verbundschaumstoff |
| US9115312B2 (en) | 2010-04-01 | 2015-08-25 | Basf Se | Flame retardant |
| EP2553008B1 (de) | 2010-04-01 | 2016-08-24 | Basf Se | Flammschutzmittel |
| EP2580250B1 (en) * | 2010-06-14 | 2021-10-27 | DDP Specialty Electronic Materials US, LLC | Process for brominating butadiene polymers |
| EP2601254A1 (de) | 2010-08-05 | 2013-06-12 | Basf Se | Halogenhaltige polymermischungen |
| JP5894188B2 (ja) * | 2010-12-17 | 2016-03-23 | ダウ グローバル テクノロジーズ エルエルシー | ポリスチレン溶融押出し法 |
| ES2535972T3 (es) * | 2011-06-08 | 2015-05-19 | Italmatch Chemicals S.P.A. | Espumas de poliestireno extruidas de combustión lenta |
| EP2718367A1 (en) * | 2011-07-14 | 2014-04-16 | Dow Global Technologies LLC | Impact-modified styrenic polymers containing brominated vinyl aromatic-butadiene copolymer |
| RU2014105432A (ru) * | 2011-07-14 | 2015-08-20 | ДАУ ГЛОБАЛ ТЕКНОЛОДЖИЗ ЭлЭлСи | Пленки для селективного переноса газов, содержащие бромированные стирол-бутадиеновые сополимеры |
| 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 |
| CN108997740A (zh) * | 2011-12-19 | 2018-12-14 | 陶氏环球技术有限责任公司 | 含溴化聚合阻燃剂的热固性聚氨酯泡沫 |
| WO2013092322A2 (de) | 2011-12-21 | 2013-06-27 | Basf Se | Verfahren zur herstellung von expandierbaren, graphit- und flammschutzmittelhaltigen styrolpolymerisaten |
| 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 |
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- 2006-10-23 BR BRPI0619699-3A patent/BRPI0619699A2/pt not_active Application Discontinuation
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- 2006-10-23 KR KR1020087011118A patent/KR20080066787A/ko not_active Withdrawn
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| NO20081960L (no) | 2008-08-11 |
| DE602006011944D1 (de) | 2010-03-11 |
| RU2008123837A (ru) | 2009-12-27 |
| HRP20080206A2 (hr) | 2008-08-31 |
| ATE455796T1 (de) | 2010-02-15 |
| BRPI0619699A2 (pt) | 2011-10-11 |
| CN101305022B (zh) | 2012-06-20 |
| WO2007058736A1 (en) | 2007-05-24 |
| EP1957544B1 (en) | 2010-01-20 |
| US7851558B2 (en) | 2010-12-14 |
| JP2009516019A (ja) | 2009-04-16 |
| CA2627253A1 (en) | 2007-05-24 |
| CN101305022A (zh) | 2008-11-12 |
| US20080287559A1 (en) | 2008-11-20 |
| KR20080066787A (ko) | 2008-07-16 |
| EP1957544A1 (en) | 2008-08-20 |
| JP5302001B2 (ja) | 2013-10-02 |
| ES2336951T3 (es) | 2010-04-19 |
| RU2414479C2 (ru) | 2011-03-20 |
| AU2006315878A1 (en) | 2007-05-24 |
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