KR20080066787A - 브롬화 부타디엔/비닐 방향족 공중합체, 당해 공중합체와비닐 방향족 중합체와의 블렌드 및 당해 블렌드로부터형성된 중합체성 발포체 - Google Patents
브롬화 부타디엔/비닐 방향족 공중합체, 당해 공중합체와비닐 방향족 중합체와의 블렌드 및 당해 블렌드로부터형성된 중합체성 발포체 Download PDFInfo
- Publication number
- KR20080066787A KR20080066787A KR1020087011118A KR20087011118A KR20080066787A KR 20080066787 A KR20080066787 A KR 20080066787A KR 1020087011118 A KR1020087011118 A KR 1020087011118A KR 20087011118 A KR20087011118 A KR 20087011118A KR 20080066787 A KR20080066787 A KR 20080066787A
- Authority
- KR
- South Korea
- Prior art keywords
- copolymer
- weight
- butadiene
- thermally stable
- brominated
- 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.)
- Withdrawn
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- 229920001577 copolymer Polymers 0.000 title claims abstract description 148
- 239000000203 mixture Substances 0.000 title claims abstract description 67
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title claims abstract description 62
- 229920000642 polymer Polymers 0.000 title claims description 73
- 229920002554 vinyl polymer Polymers 0.000 title claims description 58
- 239000006260 foam Substances 0.000 title claims description 57
- 239000003063 flame retardant Substances 0.000 claims abstract description 32
- 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 29
- 239000000654 additive Substances 0.000 claims abstract description 27
- 230000000996 additive effect Effects 0.000 claims abstract description 15
- 229920001400 block copolymer Polymers 0.000 claims abstract description 10
- 229920000578 graft copolymer Polymers 0.000 claims abstract description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 75
- 238000005893 bromination reaction Methods 0.000 claims description 68
- 230000031709 bromination Effects 0.000 claims description 66
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 62
- 229910052794 bromium Inorganic materials 0.000 claims description 62
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 45
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 44
- 239000000178 monomer Substances 0.000 claims description 28
- 239000011324 bead Substances 0.000 claims description 27
- 239000004793 Polystyrene Substances 0.000 claims description 22
- 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
- 229920002223 polystyrene Polymers 0.000 claims description 21
- 239000003795 chemical substances by application Substances 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
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 20
- 239000004604 Blowing Agent Substances 0.000 claims description 17
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical class CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 claims description 17
- 238000002411 thermogravimetry Methods 0.000 claims description 15
- 230000004580 weight loss Effects 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- -1 hydroxy alcohol Chemical compound 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000001246 bromo group Chemical group Br* 0.000 claims description 10
- 229920002959 polymer blend Polymers 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 6
- 150000003440 styrenes Chemical class 0.000 claims description 6
- 229920005604 random copolymer Polymers 0.000 claims description 5
- 229920000428 triblock copolymer Polymers 0.000 claims description 5
- 238000005160 1H NMR spectroscopy Methods 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
- 239000003086 colorant Substances 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
- 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical group 0.000 claims description 3
- 229920000359 diblock copolymer Polymers 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 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
- 239000012760 heat stabilizer Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000002667 nucleating agent Substances 0.000 claims description 2
- 229920003251 poly(α-methylstyrene) Polymers 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
- 150000002148 esters Chemical class 0.000 claims 2
- SFBTTWXNCQVIEC-UHFFFAOYSA-N o-Vinylanisole Chemical compound COC1=CC=CC=C1C=C SFBTTWXNCQVIEC-UHFFFAOYSA-N 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
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 1
- 230000001413 cellular effect Effects 0.000 claims 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 claims 1
- 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 14
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 229920002857 polybutadiene Polymers 0.000 description 55
- 230000000052 comparative effect Effects 0.000 description 54
- 239000000243 solution Substances 0.000 description 45
- 239000005062 Polybutadiene Substances 0.000 description 37
- 238000012360 testing method Methods 0.000 description 26
- 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 19
- 229920005989 resin Polymers 0.000 description 19
- 239000000047 product Substances 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 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 229920006132 styrene block copolymer Polymers 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000002156 mixing Methods 0.000 description 13
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 11
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000008188 pellet Substances 0.000 description 10
- 239000003381 stabilizer Substances 0.000 description 10
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 9
- GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 description 9
- 239000000499 gel Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 9
- 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
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 8
- 229920001519 homopolymer Polymers 0.000 description 8
- 239000003999 initiator Substances 0.000 description 8
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 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 6
- 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
- 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
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 6
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 6
- 239000003607 modifier Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
- 239000004795 extruded polystyrene foam Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
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- 239000000126 substance Substances 0.000 description 5
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 150000001649 bromium compounds Chemical group 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 230000008859 change Effects 0.000 description 4
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- 230000000694 effects Effects 0.000 description 4
- 230000000977 initiatory effect Effects 0.000 description 4
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- 238000005259 measurement Methods 0.000 description 4
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- 238000001556 precipitation Methods 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 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 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- 229920006248 expandable polystyrene Polymers 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 239000001282 iso-butane Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification 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
- 239000002244 precipitate 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
- 238000007347 radical substitution reaction Methods 0.000 description 3
- 230000002285 radioactive effect Effects 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
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- 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
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 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
- 239000002879 Lewis base Substances 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 241000612182 Rexea solandri Species 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
- 238000004458 analytical method Methods 0.000 description 2
- 238000003556 assay Methods 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
- 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
- 238000007796 conventional method Methods 0.000 description 2
- 238000007334 copolymerization reaction Methods 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
- 238000001035 drying Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000835 fiber 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
- 230000006872 improvement Effects 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 150000007527 lewis bases Chemical class 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
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
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- 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
- 229920001169 thermoplastic Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 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
- 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
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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
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- 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
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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
- 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)
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| US73536105P | 2005-11-12 | 2005-11-12 | |
| US60/735,361 | 2005-11-12 |
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| KR20080066787A true KR20080066787A (ko) | 2008-07-16 |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160086823A (ko) * | 2013-11-14 | 2016-07-20 | 가부시키가이샤 가네카 | 스티렌계 수지 압출 발포체 및 그의 제조 방법 |
| KR20200029129A (ko) * | 2018-09-10 | 2020-03-18 | 에스케이이노베이션 주식회사 | 난연제 및 이를 포함하는 난연성 수지 조성물 |
| WO2022060084A1 (ko) * | 2020-09-18 | 2022-03-24 | 주식회사 엘지화학 | 이소부텐-이소프렌 공중합체의 할로겐화 방법 |
| KR20220037613A (ko) * | 2020-09-18 | 2022-03-25 | 주식회사 엘지화학 | 이소부텐-이소프렌 공중합체의 브롬화 방법 |
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| CN101583631B (zh) * | 2006-08-16 | 2012-08-08 | 陶氏环球技术公司 | 溴化丁二烯/乙烯基芳族共聚物的方法 |
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| EP2207812B1 (en) | 2007-11-07 | 2011-11-23 | Dow Global Technologies LLC | Partial solvent stripping process for recovering brominated butadiene polymers from solution |
| JP2011528380A (ja) * | 2008-03-06 | 2011-11-17 | ダウ グローバル テクノロジーズ エルエルシー | 水又は或る種の溶媒の添加によるブタジエンコポリマーの臭素化方法 |
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| EP2274338B1 (en) * | 2008-05-01 | 2012-12-12 | Dow Global Technologies LLC | Two-step process for brominating butadiene copolymers |
| US9732178B1 (en) | 2008-07-24 | 2017-08-15 | Bridgestone Corporation | Block copolymers including high vinyl segments |
| CN102171257B (zh) * | 2008-08-05 | 2013-02-20 | 陶氏环球技术有限责任公司 | 用于有机聚合物的溶剂转移方法 |
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| 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 |
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| CA2747386C (en) * | 2008-12-18 | 2016-12-06 | Dow Global Technologies Llc | Stabilizers for flame retardant 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 |
| JP5596780B2 (ja) | 2009-03-31 | 2014-09-24 | ダウ グローバル テクノロジーズ エルエルシー | 第四級アンモニウム又は第四級ホスホニウム一塩化物の除去を伴う、不飽和有機化合物の臭素化方法 |
| JP2012532206A (ja) * | 2009-06-30 | 2012-12-13 | ダウ グローバル テクノロジーズ エルエルシー | 臭素化及びエポキシ化難燃剤 |
| DE102009059781A1 (de) | 2009-12-18 | 2011-06-22 | Basf Se, 67063 | Flammgeschützte Polymerschaumstoffe |
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| WO2011113795A2 (de) | 2010-03-17 | 2011-09-22 | Basf Se | Flammgeschützter verbundschaumstoff |
| US9115312B2 (en) | 2010-04-01 | 2015-08-25 | Basf Se | Flame retardant |
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| RU2013109371A (ru) | 2010-08-05 | 2014-09-10 | Басф Се | Галогенсодержащие полимерные смеси |
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| KR20160086823A (ko) * | 2013-11-14 | 2016-07-20 | 가부시키가이샤 가네카 | 스티렌계 수지 압출 발포체 및 그의 제조 방법 |
| KR20200029129A (ko) * | 2018-09-10 | 2020-03-18 | 에스케이이노베이션 주식회사 | 난연제 및 이를 포함하는 난연성 수지 조성물 |
| WO2022060084A1 (ko) * | 2020-09-18 | 2022-03-24 | 주식회사 엘지화학 | 이소부텐-이소프렌 공중합체의 할로겐화 방법 |
| KR20220037613A (ko) * | 2020-09-18 | 2022-03-25 | 주식회사 엘지화학 | 이소부텐-이소프렌 공중합체의 브롬화 방법 |
| US12344699B2 (en) | 2020-09-18 | 2025-07-01 | Lg Chem, Ltd. | Method for halogenating isobutene-isoprene copolymer |
Also Published As
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|---|---|
| ATE455796T1 (de) | 2010-02-15 |
| WO2007058736A1 (en) | 2007-05-24 |
| US20080287559A1 (en) | 2008-11-20 |
| NO20081960L (no) | 2008-08-11 |
| DE602006011944D1 (de) | 2010-03-11 |
| JP2009516019A (ja) | 2009-04-16 |
| HRP20080206A2 (hr) | 2008-08-31 |
| EP1957544B1 (en) | 2010-01-20 |
| US7851558B2 (en) | 2010-12-14 |
| CN101305022A (zh) | 2008-11-12 |
| CA2627253C (en) | 2013-11-19 |
| CA2627253A1 (en) | 2007-05-24 |
| BRPI0619699A2 (pt) | 2011-10-11 |
| AU2006315878A1 (en) | 2007-05-24 |
| JP5302001B2 (ja) | 2013-10-02 |
| RU2414479C2 (ru) | 2011-03-20 |
| RU2008123837A (ru) | 2009-12-27 |
| EP1957544A1 (en) | 2008-08-20 |
| ES2336951T3 (es) | 2010-04-19 |
| CN101305022B (zh) | 2012-06-20 |
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