JP2014520929A - 臭素化ビニル芳香族−ブタジエンコポリマーを含有する耐衝撃性改良スチレン系ポリマー - Google Patents
臭素化ビニル芳香族−ブタジエンコポリマーを含有する耐衝撃性改良スチレン系ポリマー Download PDFInfo
- Publication number
- JP2014520929A JP2014520929A JP2014520200A JP2014520200A JP2014520929A JP 2014520929 A JP2014520929 A JP 2014520929A JP 2014520200 A JP2014520200 A JP 2014520200A JP 2014520200 A JP2014520200 A JP 2014520200A JP 2014520929 A JP2014520929 A JP 2014520929A
- Authority
- JP
- Japan
- Prior art keywords
- impact
- brominated
- polymer resin
- styrenic polymer
- copolymer
- 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.)
- Pending
Links
- 229920001577 copolymer Polymers 0.000 title claims abstract description 83
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title claims abstract description 37
- 229920000642 polymer Polymers 0.000 title claims description 37
- 239000000203 mixture Substances 0.000 claims abstract description 50
- 239000003063 flame retardant Substances 0.000 claims abstract description 26
- 229920005669 high impact polystyrene Polymers 0.000 claims abstract description 19
- 239000004797 high-impact polystyrene Substances 0.000 claims abstract description 19
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims abstract description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 43
- 229910052794 bromium Inorganic materials 0.000 claims description 43
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 43
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 39
- 239000002952 polymeric resin Substances 0.000 claims description 30
- 229920003002 synthetic resin Polymers 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims 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 description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 16
- 238000010128 melt processing Methods 0.000 claims description 11
- 239000004793 Polystyrene Substances 0.000 claims description 10
- 229920002223 polystyrene Polymers 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000005227 gel permeation chromatography Methods 0.000 claims description 7
- 230000004580 weight loss Effects 0.000 claims description 7
- 238000004949 mass spectrometry Methods 0.000 claims description 6
- 238000005562 fading Methods 0.000 claims description 5
- 239000000049 pigment Substances 0.000 claims description 5
- 239000003381 stabilizer Substances 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 3
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 238000000465 moulding Methods 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims 2
- 238000012360 testing method Methods 0.000 abstract description 14
- 229920005990 polystyrene resin Polymers 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 19
- 229920002554 vinyl polymer Polymers 0.000 description 19
- -1 aromatic brominated flame retardant Chemical class 0.000 description 18
- 238000005893 bromination reaction Methods 0.000 description 17
- 230000031709 bromination Effects 0.000 description 16
- 229920005989 resin Polymers 0.000 description 14
- 239000011347 resin Substances 0.000 description 14
- 239000004593 Epoxy Chemical class 0.000 description 13
- 229920001971 elastomer Polymers 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000005060 rubber Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000004594 Masterbatch (MB) Substances 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- 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 8
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 8
- 150000003384 small molecules Chemical class 0.000 description 8
- 238000002156 mixing Methods 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 229920003048 styrene butadiene rubber Polymers 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 125000001246 bromo group Chemical group Br* 0.000 description 5
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical group CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 5
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical class C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 5
- 230000000379 polymerizing effect Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- 239000008188 pellet Substances 0.000 description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 229920000428 triblock copolymer Polymers 0.000 description 4
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 3
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000002485 combustion reaction Methods 0.000 description 3
- 229930003836 cresol Natural products 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 239000012760 heat stabilizer Substances 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 125000000746 allylic group Chemical group 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 231100000693 bioaccumulation Toxicity 0.000 description 2
- XZKRXPZXQLARHH-UHFFFAOYSA-N buta-1,3-dienylbenzene Chemical group C=CC=CC1=CC=CC=C1 XZKRXPZXQLARHH-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 150000002118 epoxides Chemical group 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002605 large molecules Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 239000004597 plastic additive Substances 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- BKKVYNMMVYEBGR-UHFFFAOYSA-N (2,3,4,5,6-pentabromophenyl) prop-2-enoate Chemical compound BrC1=C(Br)C(Br)=C(OC(=O)C=C)C(Br)=C1Br BKKVYNMMVYEBGR-UHFFFAOYSA-N 0.000 description 1
- YUAPUIKGYCAHGM-UHFFFAOYSA-N 1,2-dibromo-3-(2,3-dibromopropoxy)propane Chemical compound BrCC(Br)COCC(Br)CBr YUAPUIKGYCAHGM-UHFFFAOYSA-N 0.000 description 1
- DGZQEAKNZXNTNL-UHFFFAOYSA-N 1-bromo-4-butan-2-ylbenzene Chemical class CCC(C)C1=CC=C(Br)C=C1 DGZQEAKNZXNTNL-UHFFFAOYSA-N 0.000 description 1
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- WBWXVCMXGYSMQA-UHFFFAOYSA-N 3,9-bis[2,4-bis(2-phenylpropan-2-yl)phenoxy]-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C=1C=C(OP2OCC3(CO2)COP(OC=2C(=CC(=CC=2)C(C)(C)C=2C=CC=CC=2)C(C)(C)C=2C=CC=CC=2)OC3)C(C(C)(C)C=2C=CC=CC=2)=CC=1C(C)(C)C1=CC=CC=C1 WBWXVCMXGYSMQA-UHFFFAOYSA-N 0.000 description 1
- PZRWFKGUFWPFID-UHFFFAOYSA-N 3,9-dioctadecoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCCCCCCCCCCCC)OCC21COP(OCCCCCCCCCCCCCCCCCC)OC2 PZRWFKGUFWPFID-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- XQMVBICWFFHDNN-UHFFFAOYSA-N 5-amino-4-chloro-2-phenylpyridazin-3-one;(2-ethoxy-3,3-dimethyl-2h-1-benzofuran-5-yl) methanesulfonate Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1.C1=C(OS(C)(=O)=O)C=C2C(C)(C)C(OCC)OC2=C1 XQMVBICWFFHDNN-UHFFFAOYSA-N 0.000 description 1
- GEIYZNFNTVEVJJ-KQYNXXCUSA-N 9-[(2r,3r,4s,5r)-5-(dihydroxyphosphinothioyloxymethyl)-3,4-dihydroxyoxolan-2-yl]-3h-purin-6-one Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(O)=S)O[C@H]1N1C(NC=NC2=O)=C2N=C1 GEIYZNFNTVEVJJ-KQYNXXCUSA-N 0.000 description 1
- 229920003319 Araldite® Polymers 0.000 description 1
- SGXVTRUKGXCZQB-UHFFFAOYSA-N Br[Br-]Br.CC[N+](CC)(CC)CC Chemical compound Br[Br-]Br.CC[N+](CC)(CC)CC SGXVTRUKGXCZQB-UHFFFAOYSA-N 0.000 description 1
- GRPDMURFAUPTFZ-UHFFFAOYSA-N C=CCCC(CC1C=CCC1)I Chemical compound C=CCCC(CC1C=CCC1)I GRPDMURFAUPTFZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 229910000410 antimony oxide Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- AGXUVMPSUKZYDT-UHFFFAOYSA-L barium(2+);octadecanoate Chemical compound [Ba+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O AGXUVMPSUKZYDT-UHFFFAOYSA-L 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- WHHGLZMJPXIBIX-UHFFFAOYSA-N decabromodiphenyl ether Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br WHHGLZMJPXIBIX-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 1
- 229920000359 diblock copolymer Polymers 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 229960001545 hydrotalcite Drugs 0.000 description 1
- 229910001701 hydrotalcite Inorganic materials 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000012667 polymer degradation Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920006327 polystyrene foam Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000012783 reinforcing fiber Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 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
- 238000007614 solvation Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- JEJAMASKDTUEBZ-UHFFFAOYSA-N tris(1,1,3-tribromo-2,2-dimethylpropyl) phosphate Chemical compound BrCC(C)(C)C(Br)(Br)OP(=O)(OC(Br)(Br)C(C)(C)CBr)OC(Br)(Br)C(C)(C)CBr JEJAMASKDTUEBZ-UHFFFAOYSA-N 0.000 description 1
- NSBGJRFJIJFMGW-UHFFFAOYSA-N trisodium;stiborate Chemical compound [Na+].[Na+].[Na+].[O-][Sb]([O-])([O-])=O NSBGJRFJIJFMGW-UHFFFAOYSA-N 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L55/00—Compositions of homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C08L23/00 - C08L53/00
- C08L55/02—ABS [Acrylonitrile-Butadiene-Styrene] polymers
-
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/04—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to rubbers
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)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161507633P | 2011-07-14 | 2011-07-14 | |
| US61/507,633 | 2011-07-14 | ||
| US201261638546P | 2012-04-26 | 2012-04-26 | |
| US61/638,546 | 2012-04-26 | ||
| PCT/US2012/044296 WO2013009469A1 (en) | 2011-07-14 | 2012-06-27 | Impact-modified styrenic polymers containing brominated vinyl aromatic-butadiene copolymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2014520929A true JP2014520929A (ja) | 2014-08-25 |
| JP2014520929A5 JP2014520929A5 (enExample) | 2015-08-13 |
Family
ID=46579313
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014520200A Pending JP2014520929A (ja) | 2011-07-14 | 2012-06-27 | 臭素化ビニル芳香族−ブタジエンコポリマーを含有する耐衝撃性改良スチレン系ポリマー |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20140187692A1 (enExample) |
| EP (1) | EP2718367A1 (enExample) |
| JP (1) | JP2014520929A (enExample) |
| CN (1) | CN103649211A (enExample) |
| CA (1) | CA2841547A1 (enExample) |
| WO (1) | WO2013009469A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014198807A (ja) * | 2013-03-15 | 2014-10-23 | 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 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6091305B2 (ja) * | 2013-04-16 | 2017-03-08 | 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 |
| EP3063216B1 (en) | 2013-10-30 | 2017-03-22 | Dow Global Technologies LLC | Foamed styrenic polymers containing a brominated styrene-butadiene copolymer and having enhanced cell size homogeneity |
| JP5950056B2 (ja) | 2013-11-14 | 2016-07-13 | 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 |
| CN104072708A (zh) * | 2014-07-03 | 2014-10-01 | 青岛方达化工有限公司 | 一种共聚物类阻燃剂及其制备方法 |
| CN109804004B (zh) | 2016-10-10 | 2022-12-09 | 道达尔研究技术弗吕公司 | 改进的能膨胀的乙烯基芳族聚合物 |
| CN114341256A (zh) | 2019-09-04 | 2022-04-12 | 道达尔能源一技术比利时公司 | 具有改进的阻燃性的可膨胀乙烯基芳族聚合物 |
| US11939445B2 (en) | 2020-12-01 | 2024-03-26 | Ddp Specialty Electronic Materials Us, Llc | Flame retardant masterbatch composition for foams containing a pH moderator |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000500182A (ja) * | 1995-11-14 | 2000-01-11 | ザ ダウ ケミカル カンパニー | 難燃性ゴム変性ポリマー組成物 |
| JP2005272646A (ja) * | 2004-02-26 | 2005-10-06 | Dai Ichi Kogyo Seiyaku Co Ltd | 難燃性スチレン系樹脂組成物 |
| JP2009516019A (ja) * | 2005-11-12 | 2009-04-16 | ダウ グローバル テクノロジーズ インコーポレイティド | 臭素化ブタジエン・ビニル芳香族炭化水素共重合体、その共重合体とビニル芳香族炭化水素重合体との配合物、およびその配合物から形成された重合体発泡体 |
| WO2011073141A1 (de) * | 2009-12-18 | 2011-06-23 | Basf Se | Flammgeschützte polymerschaumstoffe |
| JP2014527096A (ja) * | 2011-07-14 | 2014-10-09 | ダウ グローバル テクノロジーズ エルエルシー | 臭素化スチレン−ブタジエンコポリマーを含有する選択的気体透過性フィルム |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD137308A3 (de) * | 1969-09-24 | 1979-08-29 | Paul Herte | Verfahren zur herstellung von bromierten ungesaettigten niedermolekularen polymeren |
| DE2047618A1 (de) * | 1969-09-29 | 1971-04-01 | Cities Service Co | Feuerhemmendes kautschukverstarktes Harz |
| US3767527A (en) | 1971-10-07 | 1973-10-23 | Mobil Oil Corp | Method for producing hydrocarbon-utilizing yeasts |
| US4279808A (en) * | 1980-02-14 | 1981-07-21 | Ethyl Corporation | Polybromostyrene resin |
| US4578416A (en) * | 1982-08-31 | 1986-03-25 | Mobil Oil Corporation | Flame retardant high impact poly paramethylstyrene compositions |
| US5180780A (en) | 1989-01-12 | 1993-01-19 | Idemitsu Petrochemical Company Limited | Rubber-modified styrene-based copolymer |
| US5194491A (en) | 1989-05-30 | 1993-03-16 | Mitsubishi Monsanto Chemical Company | Process for producing rubber-modified styrene resin, and resin composition |
| GB8918157D0 (en) | 1989-08-09 | 1989-09-20 | Dow Benelux | A process for the preparation of rubber-reinforced monovinylidene aromatic polymers |
| DE10358798A1 (de) * | 2003-12-12 | 2005-07-14 | Basf Ag | Expandierbare Styrolpolymergranulate |
| 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 |
| 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 |
| DE102006056629A1 (de) | 2006-11-30 | 2008-06-05 | Bayerische Motoren Werke Ag | Verfahren zur Geschwindigkeits- und/oder Abstandsregelung bei Kraftfahrzeugen |
| 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 |
| RU2528677C2 (ru) | 2008-12-18 | 2014-09-20 | ДАУ ГЛОБАЛ ТЕКНОЛОДЖИЗ ЭлЭлСи | Стабилизаторы для полимеров, содержащих бром алифатического присоединения |
| WO2010099020A2 (en) * | 2009-02-26 | 2010-09-02 | Icl-Ip America Inc. | Styrenic polymer composition |
| 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 |
| CN101875745B (zh) * | 2010-03-30 | 2013-07-03 | 金发科技股份有限公司 | 含有抑烟剂的阻燃苯乙烯类聚合物复合物及其制备方法 |
-
2012
- 2012-06-27 CN CN201280034609.XA patent/CN103649211A/zh active Pending
- 2012-06-27 CA CA2841547A patent/CA2841547A1/en not_active Abandoned
- 2012-06-27 WO PCT/US2012/044296 patent/WO2013009469A1/en not_active Ceased
- 2012-06-27 JP JP2014520200A patent/JP2014520929A/ja active Pending
- 2012-06-27 EP EP12738661.3A patent/EP2718367A1/en not_active Withdrawn
- 2012-06-27 US US14/127,204 patent/US20140187692A1/en not_active Abandoned
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000500182A (ja) * | 1995-11-14 | 2000-01-11 | ザ ダウ ケミカル カンパニー | 難燃性ゴム変性ポリマー組成物 |
| JP2005272646A (ja) * | 2004-02-26 | 2005-10-06 | Dai Ichi Kogyo Seiyaku Co Ltd | 難燃性スチレン系樹脂組成物 |
| JP2009516019A (ja) * | 2005-11-12 | 2009-04-16 | ダウ グローバル テクノロジーズ インコーポレイティド | 臭素化ブタジエン・ビニル芳香族炭化水素共重合体、その共重合体とビニル芳香族炭化水素重合体との配合物、およびその配合物から形成された重合体発泡体 |
| WO2011073141A1 (de) * | 2009-12-18 | 2011-06-23 | Basf Se | Flammgeschützte polymerschaumstoffe |
| JP2014527096A (ja) * | 2011-07-14 | 2014-10-09 | ダウ グローバル テクノロジーズ エルエルシー | 臭素化スチレン−ブタジエンコポリマーを含有する選択的気体透過性フィルム |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014198807A (ja) * | 2013-03-15 | 2014-10-23 | 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20140187692A1 (en) | 2014-07-03 |
| CA2841547A1 (en) | 2013-01-17 |
| CN103649211A (zh) | 2014-03-19 |
| EP2718367A1 (en) | 2014-04-16 |
| WO2013009469A1 (en) | 2013-01-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2014520929A (ja) | 臭素化ビニル芳香族−ブタジエンコポリマーを含有する耐衝撃性改良スチレン系ポリマー | |
| CA2747386C (en) | Stabilizers for flame retardant polymers containing aliphatically-bound bromine | |
| Levchik et al. | New developments in flame retardancy of styrene thermoplastics and foams | |
| JP4755399B2 (ja) | 難燃性スチレン系樹脂組成物 | |
| KR102318927B1 (ko) | 우수한 난연성을 부여하는 복합난연제 및 이를 포함하는 난연 수지 조성물 | |
| JP2014520929A5 (enExample) | ||
| JP2013518957A (ja) | 五酸化アンチモンを含む芳香族ビニルポリマーをベースにした耐火組成物 | |
| JP2005145988A (ja) | 難燃性スチレン系樹脂組成物 | |
| JP6353948B1 (ja) | 熱可塑性樹脂組成物 | |
| KR101731679B1 (ko) | 방향족 비닐-염화비닐 공중합체 및 이를 포함하는 열가소성 수지 조성물 | |
| KR101847249B1 (ko) | 난연성 열가소성 수지 조성물 및 이를 포함하는 성형품 | |
| KR101981471B1 (ko) | 열가소성 수지 조성물 및 이를 포함하는 성형품 | |
| KR101769185B1 (ko) | 열가소성 수지 조성물 | |
| JP3397768B2 (ja) | 難燃性スチレン系樹脂組成物 | |
| JP5570920B2 (ja) | ゴム変性ポリスチレン系難燃樹脂組成物 | |
| JP2002210734A (ja) | スチレン系樹脂ペレットの製造方法 | |
| JP2000309700A (ja) | ポリフェニレンエーテル系樹脂組成物の製造方法 | |
| JPS5853947A (ja) | 射出成形用ポリフエニレンエ−テル組成物およびその製造方法 | |
| JPH11209600A (ja) | ポリフェニレンエーテル系難燃樹脂組成物 | |
| JPS6013834A (ja) | 難燃性樹脂組成物 | |
| JPH0762100B2 (ja) | 難燃性熱可塑性樹脂組成物 | |
| JP2002212367A (ja) | 難燃性樹脂組成物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20150626 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20150626 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20160107 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20160112 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20160830 |