CA2841547A1 - Impact-modified styrenic polymers containing brominated vinyl aromatic-butadiene copolymer - Google Patents
Impact-modified styrenic polymers containing brominated vinyl aromatic-butadiene copolymer Download PDFInfo
- Publication number
- CA2841547A1 CA2841547A1 CA2841547A CA2841547A CA2841547A1 CA 2841547 A1 CA2841547 A1 CA 2841547A1 CA 2841547 A CA2841547 A CA 2841547A CA 2841547 A CA2841547 A CA 2841547A CA 2841547 A1 CA2841547 A1 CA 2841547A1
- Authority
- CA
- Canada
- Prior art keywords
- impact
- brominated
- polymer resin
- modified styrenic
- styrenic polymer
- 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.)
- Abandoned
Links
- 229920001577 copolymer Polymers 0.000 title claims abstract description 71
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title claims abstract description 36
- 229920000642 polymer Polymers 0.000 title description 33
- 239000000203 mixture Substances 0.000 claims abstract description 50
- 239000003063 flame retardant Substances 0.000 claims abstract description 17
- 229920005669 high impact polystyrene Polymers 0.000 claims abstract description 15
- 239000004797 high-impact polystyrene Substances 0.000 claims abstract description 15
- 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 12
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims abstract description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 42
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 42
- 229910052794 bromium Inorganic materials 0.000 claims description 40
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 27
- 239000002952 polymeric resin Substances 0.000 claims description 26
- 229920003002 synthetic resin Polymers 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 22
- 239000004793 Polystyrene Substances 0.000 claims description 9
- 238000010128 melt processing Methods 0.000 claims description 9
- 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
- 229920002223 polystyrene Polymers 0.000 claims description 9
- 230000004580 weight loss Effects 0.000 claims description 9
- 238000005227 gel permeation chromatography Methods 0.000 claims description 6
- 238000005562 fading Methods 0.000 claims description 5
- 239000000049 pigment Substances 0.000 claims description 5
- 238000002411 thermogravimetry Methods 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
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 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
- 239000000155 melt Substances 0.000 claims description 2
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 claims 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims 1
- 238000012360 testing method Methods 0.000 abstract description 16
- 229920005990 polystyrene resin Polymers 0.000 abstract 1
- -1 poly(pentabromophenyl acrylate) Polymers 0.000 description 21
- 229920002554 vinyl polymer Polymers 0.000 description 20
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 16
- 238000005893 bromination reaction Methods 0.000 description 13
- 229920005989 resin Polymers 0.000 description 13
- 239000011347 resin Substances 0.000 description 13
- 239000004593 Epoxy Chemical class 0.000 description 12
- 230000031709 bromination Effects 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- 229920001971 elastomer Polymers 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 239000005060 rubber Substances 0.000 description 10
- 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
- 150000003384 small molecules Chemical class 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- 239000004594 Masterbatch (MB) Substances 0.000 description 6
- 230000001413 cellular effect Effects 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical class C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 5
- 229920003048 styrene butadiene rubber Polymers 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical group CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 4
- 238000011068 loading method Methods 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 description 4
- 239000000243 solution 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
- 239000000126 substance Substances 0.000 description 4
- 229920000428 triblock copolymer Polymers 0.000 description 4
- 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
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- 239000003017 thermal stabilizer Substances 0.000 description 3
- 239000003039 volatile agent 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
- 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 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- 230000009471 action Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000000217 alkyl 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
- 230000008901 benefit Effects 0.000 description 2
- 231100000693 bioaccumulation Toxicity 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 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
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 150000002118 epoxides Chemical group 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 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 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 150000002605 large molecules Chemical class 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000009467 reduction Effects 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
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- RGASRBUYZODJTG-UHFFFAOYSA-N 1,1-bis(2,4-ditert-butylphenyl)-2,2-bis(hydroxymethyl)propane-1,3-diol dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.C(C)(C)(C)C1=C(C=CC(=C1)C(C)(C)C)C(O)(C(CO)(CO)CO)C1=C(C=C(C=C1)C(C)(C)C)C(C)(C)C RGASRBUYZODJTG-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
- 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
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
- SPIUEOWNLJQKJK-UHFFFAOYSA-J 2-sulfanylacetate tin(4+) Chemical class [Sn+4].[O-]C(=O)CS.[O-]C(=O)CS.[O-]C(=O)CS.[O-]C(=O)CS SPIUEOWNLJQKJK-UHFFFAOYSA-J 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
- 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
- 229930185605 Bisphenol Natural products 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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- XAQKFOUWWAKVCH-UHFFFAOYSA-N OP(O)OP(O)O.C(C)(C)(C1=CC=CC=C1)C1=C(C=CC(=C1)C(C)(C)C1=CC=CC=C1)C(O)C(CO)(CO)CO Chemical compound OP(O)OP(O)O.C(C)(C)(C1=CC=CC=C1)C1=C(C=CC(=C1)C(C)(C)C1=CC=CC=C1)C(O)C(CO)(CO)CO XAQKFOUWWAKVCH-UHFFFAOYSA-N 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
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
- GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000000746 allylic 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
- 238000004458 analytical method Methods 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
- 229920001400 block copolymer Polymers 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
- 238000005266 casting Methods 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940127204 compound 29 Drugs 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000002537 cosmetic Substances 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
- 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
- 239000013536 elastomeric material Substances 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
- 229960001545 hydrotalcite Drugs 0.000 description 1
- 229910001701 hydrotalcite Inorganic materials 0.000 description 1
- 238000007654 immersion Methods 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
- 239000007788 liquid Substances 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
- 238000004519 manufacturing process 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
- 229910052757 nitrogen Inorganic materials 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 group [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004597 plastic additive Substances 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
- 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
- 238000003672 processing method Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000012783 reinforcing fiber Substances 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium 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
- 238000010186 staining Methods 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
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 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
- 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
- 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
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 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
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 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 (1)
| Publication Number | Publication Date |
|---|---|
| CA2841547A1 true CA2841547A1 (en) | 2013-01-17 |
Family
ID=46579313
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2841547A Abandoned CA2841547A1 (en) | 2011-07-14 | 2012-06-27 | Impact-modified styrenic polymers containing brominated vinyl aromatic-butadiene copolymer |
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) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6113576B2 (ja) * | 2013-03-15 | 2017-04-12 | 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 |
| 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 |
| US10093781B2 (en) | 2013-10-30 | 2018-10-09 | Dow Global Technologies Llc | Foamed styrenic polymers containing a brominated styrene-butadiene copolymer and having enhanced cell size homogeneity |
| EP3070118B1 (en) | 2013-11-14 | 2020-02-26 | Kaneka Corporation | Extruded styrenic resin foam and method for manufacturing same |
| 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 |
| EP3523361A1 (en) | 2016-10-10 | 2019-08-14 | Total Research & Technology Feluy | Improved expandable vinyl aromatic polymers |
| EP3680287B1 (en) * | 2019-01-09 | 2025-10-01 | Trinseo Europe GmbH | Extremely low odor styrenic polymer composition |
| US20220298320A1 (en) | 2019-09-04 | 2022-09-22 | Totalenergies One Tech Belgium | Expandable Vinyl Aromatic Polymers with Improved Flame Retardancy |
| CA3200054A1 (en) | 2020-12-01 | 2022-06-09 | Wenyi Huang | Flame retardant masterbatch composition for foams containing a ph moderator |
Family Cites Families (22)
| 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 |
| US6372831B1 (en) * | 1995-11-14 | 2002-04-16 | The Dow Chemical Company | Flame resistant rubber modified polymer compositions |
| DE10358798A1 (de) * | 2003-12-12 | 2005-07-14 | Basf Ag | Expandierbare Styrolpolymergranulate |
| JP4755399B2 (ja) * | 2004-02-26 | 2011-08-24 | 第一工業製薬株式会社 | 難燃性スチレン系樹脂組成物 |
| HRP20080206A2 (hr) * | 2005-11-12 | 2008-08-31 | Dow Global Technologies Inc. | Bromirani butadien/vinil aromatski kopolimeri, smjese takvih kopolimera s vinil aromatskim polimerom i polimerne pjene formirane od takvih smjesa |
| EP2054446B1 (en) | 2006-08-16 | 2019-07-24 | Dow Global Technologies LLC | Process for brominating butadiene/vinyl aromatic copolymers |
| US8202945B2 (en) * | 2006-08-16 | 2012-06-19 | Dow Global Technologies Llc | Process for brominating butadieneninyl aromatic copolymers |
| DE102006056629A1 (de) | 2006-11-30 | 2008-06-05 | Bayerische Motoren Werke Ag | Verfahren zur Geschwindigkeits- und/oder Abstandsregelung bei Kraftfahrzeugen |
| JP5508397B2 (ja) | 2008-05-01 | 2014-05-28 | ダウ グローバル テクノロジーズ エルエルシー | ブタジエン共重合体を臭素化する２段階方法 |
| 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 |
| 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 |
| DE102009059781A1 (de) * | 2009-12-18 | 2011-06-22 | Basf Se, 67063 | Flammgeschützte Polymerschaumstoffe |
| 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 |
| CN103649191B (zh) * | 2011-07-14 | 2016-05-18 | 陶氏环球技术有限责任公司 | 包含溴化苯乙烯-丁二烯共聚物的选择性气体运输薄膜 |
-
2012
- 2012-06-27 EP EP12738661.3A patent/EP2718367A1/en not_active Withdrawn
- 2012-06-27 WO PCT/US2012/044296 patent/WO2013009469A1/en not_active Ceased
- 2012-06-27 CA CA2841547A patent/CA2841547A1/en not_active Abandoned
- 2012-06-27 JP JP2014520200A patent/JP2014520929A/ja active Pending
- 2012-06-27 US US14/127,204 patent/US20140187692A1/en not_active Abandoned
- 2012-06-27 CN CN201280034609.XA patent/CN103649211A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP2718367A1 (en) | 2014-04-16 |
| CN103649211A (zh) | 2014-03-19 |
| US20140187692A1 (en) | 2014-07-03 |
| JP2014520929A (ja) | 2014-08-25 |
| WO2013009469A1 (en) | 2013-01-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2013009469A1 (en) | Impact-modified styrenic polymers containing brominated vinyl aromatic-butadiene copolymer | |
| CA2747386C (en) | Stabilizers for flame retardant polymers containing aliphatically-bound bromine | |
| Levchik et al. | New developments in flame retardancy of styrene thermoplastics and foams | |
| EP2410016B1 (en) | Brominated polymers as flame retardant additives and polymer systems containing same | |
| JP4755399B2 (ja) | 難燃性スチレン系樹脂組成物 | |
| CN105189628A (zh) | 阻燃性发泡苯乙烯系树脂组合物 | |
| EP3140346B1 (en) | Environmental friendly flame retardant moulding compositions based on thermoplastic impact modified styrenic polymers | |
| HUE032417T2 (en) | Self-extinguishing polymer composition | |
| 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 | |
| JP6353948B1 (ja) | 熱可塑性樹脂組成物 | |
| JP6836246B2 (ja) | 熱可塑性衝撃改良スチレン系ポリマーをベースとした、環境にやさしい難燃性組成物および成形材料 | |
| JP3397768B2 (ja) | 難燃性スチレン系樹脂組成物 | |
| KR101769185B1 (ko) | 열가소성 수지 조성물 | |
| JPH08208939A (ja) | 滴下性を有する自己消炎性ポリスチレン系難燃樹脂組成物 | |
| JP5570920B2 (ja) | ゴム変性ポリスチレン系難燃樹脂組成物 | |
| KR20160052194A (ko) | 방향족 비닐-염화비닐 공중합체 및 이를 포함하는 열가소성 수지 조성물 | |
| JPH0762100B2 (ja) | 難燃性熱可塑性樹脂組成物 | |
| JP2002210734A (ja) | スチレン系樹脂ペレットの製造方法 | |
| JPS6236063B2 (enExample) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20170627 |