KR20070050442A - 신규한 난연성 폴리스티렌 - Google Patents
신규한 난연성 폴리스티렌 Download PDFInfo
- Publication number
- KR20070050442A KR20070050442A KR1020077003810A KR20077003810A KR20070050442A KR 20070050442 A KR20070050442 A KR 20070050442A KR 1020077003810 A KR1020077003810 A KR 1020077003810A KR 20077003810 A KR20077003810 A KR 20077003810A KR 20070050442 A KR20070050442 A KR 20070050442A
- Authority
- KR
- South Korea
- Prior art keywords
- polymer
- formula
- flame retardant
- compound
- styrene
- 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.)
- Ceased
Links
- 239000003063 flame retardant Substances 0.000 title claims abstract description 73
- 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 title claims abstract description 58
- 239000004793 Polystyrene Substances 0.000 title claims description 51
- 229920002223 polystyrene Polymers 0.000 title claims description 38
- 239000000203 mixture Substances 0.000 claims abstract description 102
- 229920000642 polymer Polymers 0.000 claims abstract description 54
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 28
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 65
- PYOIYKRKAHYOKO-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-(bromomethyl)benzene Chemical compound BrCC1=C(Br)C(Br)=C(Br)C(Br)=C1Br PYOIYKRKAHYOKO-UHFFFAOYSA-N 0.000 claims description 49
- 239000000654 additive Substances 0.000 claims description 30
- 229910052698 phosphorus Inorganic materials 0.000 claims description 27
- -1 phosphorus compound Chemical class 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 26
- 239000011574 phosphorus Substances 0.000 claims description 26
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 claims description 24
- 239000004794 expanded polystyrene Substances 0.000 claims description 22
- HGTUJZTUQFXBIH-UHFFFAOYSA-N (2,3-dimethyl-3-phenylbutan-2-yl)benzene Chemical group C=1C=CC=CC=1C(C)(C)C(C)(C)C1=CC=CC=C1 HGTUJZTUQFXBIH-UHFFFAOYSA-N 0.000 claims description 21
- 238000002347 injection Methods 0.000 claims description 16
- 239000007924 injection Substances 0.000 claims description 16
- 239000004594 Masterbatch (MB) Substances 0.000 claims description 15
- 229910019142 PO4 Inorganic materials 0.000 claims description 14
- 239000010452 phosphate Substances 0.000 claims description 13
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 claims description 11
- 150000003018 phosphorus compounds Chemical class 0.000 claims description 11
- BHYQWBKCXBXPKM-UHFFFAOYSA-N tris[3-bromo-2,2-bis(bromomethyl)propyl] phosphate Chemical group BrCC(CBr)(CBr)COP(=O)(OCC(CBr)(CBr)CBr)OCC(CBr)(CBr)CBr BHYQWBKCXBXPKM-UHFFFAOYSA-N 0.000 claims description 10
- 230000000996 additive effect Effects 0.000 claims description 9
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 8
- UJJSQULCWJOFRO-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-(chloromethyl)benzene Chemical compound ClCC1=C(Br)C(Br)=C(Br)C(Br)=C1Br UJJSQULCWJOFRO-UHFFFAOYSA-N 0.000 claims description 6
- DOWODFHKPUELSK-UHFFFAOYSA-N 1,2,3,4-tetrabromo-5-(bromomethyl)-6-chlorobenzene Chemical compound ClC1=C(Br)C(Br)=C(Br)C(Br)=C1CBr DOWODFHKPUELSK-UHFFFAOYSA-N 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 6
- 238000001125 extrusion Methods 0.000 claims description 6
- JDBYWXRTEWDVGJ-UHFFFAOYSA-N 1,2,4-tribromo-5-(bromomethyl)benzene Chemical compound BrCC1=CC(Br)=C(Br)C=C1Br JDBYWXRTEWDVGJ-UHFFFAOYSA-N 0.000 claims description 5
- OVMQLNVYEPNQJS-UHFFFAOYSA-N 1,2,5-tribromo-3-(bromomethyl)-4,6-dichlorobenzene Chemical compound ClC1=C(Br)C(Cl)=C(CBr)C(Br)=C1Br OVMQLNVYEPNQJS-UHFFFAOYSA-N 0.000 claims description 4
- YUAPUIKGYCAHGM-UHFFFAOYSA-N 1,2-dibromo-3-(2,3-dibromopropoxy)propane Chemical compound BrCC(Br)COCC(Br)CBr YUAPUIKGYCAHGM-UHFFFAOYSA-N 0.000 claims 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 claims description 4
- ODJQKYXPKWQWNK-UHFFFAOYSA-L 3-(2-carboxylatoethylsulfanyl)propanoate Chemical compound [O-]C(=O)CCSCCC([O-])=O ODJQKYXPKWQWNK-UHFFFAOYSA-L 0.000 claims description 4
- QEJPOEGPNIVDMK-UHFFFAOYSA-N 3-bromo-2,2-bis(bromomethyl)propan-1-ol Chemical compound OCC(CBr)(CBr)CBr QEJPOEGPNIVDMK-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 claims description 3
- NODLCKUQQWRUIU-UHFFFAOYSA-N 1-(1-phenylethylsulfonyl)ethylbenzene Chemical compound C=1C=CC=CC=1C(C)S(=O)(=O)C(C)C1=CC=CC=C1 NODLCKUQQWRUIU-UHFFFAOYSA-N 0.000 claims description 3
- PFIQGSKJYVDGCX-UHFFFAOYSA-N 2,5-bis(tribromomethyl)-1,3,4-thiadiazole Chemical compound BrC(Br)(Br)C1=NN=C(C(Br)(Br)Br)S1 PFIQGSKJYVDGCX-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- MJIRQUDRSKNXSM-UHFFFAOYSA-N [1-(1-phenylcyclopentyl)cyclopentyl]benzene Chemical group C1CCCC1(C1(CCCC1)C=1C=CC=CC=1)C1=CC=CC=C1 MJIRQUDRSKNXSM-UHFFFAOYSA-N 0.000 claims description 3
- MWSVUOSVPYCABB-UHFFFAOYSA-N bis(2-bromobutan-2-yl)diazene Chemical compound CCC(C)(Br)N=NC(C)(Br)CC MWSVUOSVPYCABB-UHFFFAOYSA-N 0.000 claims description 3
- FJDFMHRXSYNDIR-UHFFFAOYSA-N bis(2-chlorobutan-2-yl)diazene Chemical compound CCC(C)(Cl)N=NC(C)(Cl)CC FJDFMHRXSYNDIR-UHFFFAOYSA-N 0.000 claims description 3
- ZGXHUGQEDPPKGZ-UHFFFAOYSA-N bis(2-methylbutan-2-yl)diazene Chemical compound CCC(C)(C)N=NC(C)(C)CC ZGXHUGQEDPPKGZ-UHFFFAOYSA-N 0.000 claims description 3
- PZGVVCOOWYSSGB-UHFFFAOYSA-L but-2-enedioate;dioctyltin(2+) Chemical compound CCCCCCCC[Sn]1(CCCCCCCC)OC(=O)C=CC(=O)O1 PZGVVCOOWYSSGB-UHFFFAOYSA-L 0.000 claims description 3
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims 6
- SZGBUFROANKUNE-UHFFFAOYSA-N [1-(1-phenylcyclohexyl)cyclohexyl]benzene Chemical group C1CCCCC1(C1(CCCCC1)C=1C=CC=CC=1)C1=CC=CC=C1 SZGBUFROANKUNE-UHFFFAOYSA-N 0.000 claims 2
- 229940117389 dichlorobenzene Drugs 0.000 claims 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 claims 1
- 238000009472 formulation Methods 0.000 description 37
- 239000006260 foam Substances 0.000 description 23
- 238000012360 testing method Methods 0.000 description 22
- 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 20
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 11
- 235000021317 phosphate Nutrition 0.000 description 10
- 238000012545 processing Methods 0.000 description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 8
- 238000007906 compression Methods 0.000 description 7
- 230000006835 compression Effects 0.000 description 7
- 125000004970 halomethyl group Polymers 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 125000001246 bromo group Chemical group Br* 0.000 description 5
- 238000013329 compounding Methods 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 238000001746 injection moulding Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 229920006248 expandable polystyrene Polymers 0.000 description 4
- 238000005187 foaming Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 229920006327 polystyrene foam Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004604 Blowing Agent Substances 0.000 description 3
- 150000007824 aliphatic compounds Chemical class 0.000 description 3
- 125000005340 bisphosphate group Chemical group 0.000 description 3
- 125000005997 bromomethyl group Chemical group 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000004795 extruded polystyrene foam Substances 0.000 description 3
- 238000009413 insulation Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 239000002667 nucleating agent Substances 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 229920005990 polystyrene resin Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- 230000035882 stress Effects 0.000 description 3
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 2
- 229920000426 Microplastic Polymers 0.000 description 2
- 239000006057 Non-nutritive feed additive Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 229940106691 bisphenol a Drugs 0.000 description 2
- 239000004566 building material Substances 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000000748 compression moulding Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GRKDVZMVHOLESV-UHFFFAOYSA-N (2,3,4,5,6-pentabromophenyl)methyl prop-2-enoate Chemical compound BrC1=C(Br)C(Br)=C(COC(=O)C=C)C(Br)=C1Br GRKDVZMVHOLESV-UHFFFAOYSA-N 0.000 description 1
- WQJUBZMZVKITBU-UHFFFAOYSA-N (3,4-dimethyl-4-phenylhexan-3-yl)benzene Chemical compound C=1C=CC=CC=1C(C)(CC)C(C)(CC)C1=CC=CC=C1 WQJUBZMZVKITBU-UHFFFAOYSA-N 0.000 description 1
- 125000000577 2,6-xylenyl group Chemical group [H]C1=C([H])C(=C(O*)C(=C1[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- KDVYCTOWXSLNNI-UHFFFAOYSA-N 4-t-Butylbenzoic acid Chemical compound CC(C)(C)C1=CC=C(C(O)=O)C=C1 KDVYCTOWXSLNNI-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- 229920001890 Novodur Polymers 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 125000000853 cresyl group Chemical group C1(=CC=C(C=C1)C)* 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
- 238000007872 degassing Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 230000009970 fire resistant effect Effects 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- GZMZJJOMZQVSDC-UHFFFAOYSA-N n-butyl-2,2,6,6-tetramethylpiperidin-4-amine;2,4,6-trichloro-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(Cl)=N1.CCCCNC1CC(C)(C)NC(C)(C)C1 GZMZJJOMZQVSDC-UHFFFAOYSA-N 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000004154 testing of material Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- 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
- C08J9/0014—Use of organic additives
- C08J9/0019—Use of organic additives halogenated
-
- 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
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/20—Compounding polymers with additives, e.g. colouring
- C08J3/22—Compounding polymers with additives, e.g. colouring using masterbatch techniques
- C08J3/226—Compounding polymers with additives, e.g. colouring using masterbatch techniques using a polymer as a carrier
-
- 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
-
- 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
- C08J9/0014—Use of organic additives
- C08J9/0038—Use of organic additives containing phosphorus
-
- 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
-
- 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
- C08K5/02—Halogenated hydrocarbons
- C08K5/03—Halogenated hydrocarbons aromatic, e.g. C6H5-CH2-Cl
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L25/00—Compositions 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; Compositions of derivatives of such polymers
- C08L25/02—Homopolymers or copolymers of hydrocarbons
- C08L25/04—Homopolymers or copolymers of styrene
- C08L25/06—Polystyrene
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- 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
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- 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
- C08J2425/00—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
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- 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
- C08J2425/00—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
- C08J2425/02—Homopolymers or copolymers of hydrocarbons
- C08J2425/04—Homopolymers or copolymers of styrene
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| IL16310004 | 2004-07-19 | ||
| IL163100 | 2004-07-19 |
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| KR20070050442A true KR20070050442A (ko) | 2007-05-15 |
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| US (1) | US7585912B2 (https=) |
| EP (1) | EP1786853B1 (https=) |
| JP (1) | JP2008506829A (https=) |
| KR (1) | KR20070050442A (https=) |
| CN (1) | CN1989188B (https=) |
| AT (1) | ATE428745T1 (https=) |
| DE (1) | DE602005013975D1 (https=) |
| ES (1) | ES2326036T3 (https=) |
| IL (1) | IL180428A (https=) |
| PL (1) | PL1786853T3 (https=) |
| WO (1) | WO2006013554A1 (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1773744B1 (en) * | 2004-07-19 | 2013-01-16 | Bromine Compounds Ltd. | SYNTHESIS OF PENTABROMOBENZYL BROMIDE (PBB-Br) |
| JP4937610B2 (ja) * | 2005-04-12 | 2012-05-23 | 第一工業製薬株式会社 | 難燃性発泡ポリスチレン系樹脂およびその成形体 |
| US7504449B2 (en) | 2006-02-23 | 2009-03-17 | Bromine Compounds Ltd. | Flame retardant compositions |
| IL188983A (en) | 2008-01-23 | 2014-01-30 | Bromine Compounds Ltd | Delay in combustion in fabrics |
| US20080221239A1 (en) * | 2007-03-07 | 2008-09-11 | Falloon Stephen B | Flame retardant composition for use in styrenics |
| KR20100090287A (ko) | 2007-11-20 | 2010-08-13 | 아크조 노벨 엔.브이. | 스티렌계 （코）폴리머의 제조 방법 |
| JP5620406B2 (ja) * | 2009-01-15 | 2014-11-05 | ダウ グローバル テクノロジーズ エルエルシー | 低臭素含有量ポリマーフォーム |
| US20120123007A1 (en) * | 2009-02-26 | 2012-05-17 | Smadar Hini | Styrenic polymer composition |
| CN102786767B (zh) * | 2012-05-15 | 2014-11-26 | 金发科技股份有限公司 | 一种超高流动无卤阻燃abs及其制备方法 |
| US9481621B2 (en) | 2013-01-06 | 2016-11-01 | Bromine Compounds Ltd. | Preparation of bromine-containing aromatic compounds and their application as flame retardants |
| 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 |
| WO2015072514A1 (ja) | 2013-11-14 | 2015-05-21 | 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 |
| WO2016005973A1 (en) * | 2014-07-08 | 2016-01-14 | Bromine Compounds Ltd. | Preparation of bromine-containing polymers and their application as flame retardants |
| EP3166989B1 (en) | 2014-07-08 | 2020-03-25 | Bromine Compounds Ltd. | Preparation of bromine-containing polymers useful as flame retardants |
| MX2018013641A (es) | 2016-05-11 | 2019-04-25 | Owens Corning Intellectual Capital Llc | "espuma polimerica que comprende bajos niveles de retardante de flama brominado y su metodo de elaboracion". |
| CN112852015A (zh) * | 2021-01-11 | 2021-05-28 | 北京工商大学 | 一种高热稳定性的复合溴系阻燃剂及其高效阻燃聚苯乙烯泡沫材料 |
| CN113881152B (zh) * | 2021-09-24 | 2024-03-15 | 江苏金发科技新材料有限公司 | 一种透明阻燃母粒及其制备方法和应用 |
| CN118667229B (zh) * | 2024-07-17 | 2025-03-28 | 华南理工大学 | 一种复合阻燃材料的制备方法 |
Family Cites Families (16)
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|---|---|---|---|---|
| US2676927A (en) * | 1950-09-11 | 1954-04-27 | Dow Chemical Co | Nonflammable cellular resinous bodies and method of making same |
| GB1107283A (en) * | 1966-04-29 | 1968-03-27 | Berk Ltd | Expandable polystyrene compositions and expanded polystyrene formed therefrom |
| DE1794182C3 (de) * | 1968-09-20 | 1976-01-08 | Chemische Werke Huels Ag, 4370 Marl | Schwerentflammbare Formmassen aus Styrolpolymerisaten |
| US3787506A (en) | 1969-11-14 | 1974-01-22 | Dow Chemical Co | Fire retardants for polymers |
| FR2120813A5 (https=) * | 1970-12-31 | 1972-08-18 | Huels Chemische Werke Ag | |
| US3920606A (en) | 1970-12-31 | 1975-11-18 | Huels Chemische Werke Ag | Nonflammable molding compositions of styrene polymers |
| JPS493942A (https=) * | 1972-04-24 | 1974-01-14 | ||
| US4211730A (en) * | 1975-06-21 | 1980-07-08 | Dynamit Nobel Aktiengesellschaft | Acrylate-based polymers and copolymers and their use as flameproofing agents |
| US5204394A (en) | 1988-09-22 | 1993-04-20 | General Electric Company | Polymer mixture having aromatic polycarbonate, styrene I containing copolymer and/or graft polymer and a flame-retardant, articles formed therefrom |
| USRE36188E (en) | 1989-09-20 | 1999-04-06 | General Electric Company | Polymer mixture having aromatic polycarbonate styrene I containing copolymer and/or graft polymer and a flame-retardant, articles formed therefrom |
| DE69124602T2 (de) * | 1990-06-14 | 1997-08-07 | The Dow Chemical Co., Midland, Mich. | Flammbeständige alkenylaromatische schäume |
| US6028156A (en) | 1996-01-16 | 2000-02-22 | Bromine Compounds, Ltd. | Process for the preparation of poly-(halobenzyl acrylate) |
| US5639799A (en) | 1996-10-15 | 1997-06-17 | Albemarle Corporation | Heat stabilized flame retardant styrenic polymer foam compositions |
| AU5900699A (en) * | 1998-08-28 | 2000-03-21 | Dow Chemical Company, The | Fire resistant styrene polymer foams with reduced brominated fire retardant |
| IL147490A0 (en) | 2002-01-06 | 2002-08-14 | Bromine Compounds Ltd | Preparation of phenylphosphate esters of 4,4'-biphenol |
| JP2005248051A (ja) * | 2004-03-05 | 2005-09-15 | Dai Ichi Kogyo Seiyaku Co Ltd | 難燃性発泡スチレン系樹脂組成物 |
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2005
- 2005-07-19 ES ES05761339T patent/ES2326036T3/es not_active Expired - Lifetime
- 2005-07-19 JP JP2007522118A patent/JP2008506829A/ja active Pending
- 2005-07-19 WO PCT/IL2005/000767 patent/WO2006013554A1/en not_active Ceased
- 2005-07-19 DE DE602005013975T patent/DE602005013975D1/de not_active Expired - Lifetime
- 2005-07-19 PL PL05761339T patent/PL1786853T3/pl unknown
- 2005-07-19 EP EP05761339A patent/EP1786853B1/en not_active Expired - Lifetime
- 2005-07-19 US US11/632,891 patent/US7585912B2/en not_active Expired - Fee Related
- 2005-07-19 AT AT05761339T patent/ATE428745T1/de active
- 2005-07-19 CN CN2005800242620A patent/CN1989188B/zh not_active Expired - Fee Related
- 2005-07-19 KR KR1020077003810A patent/KR20070050442A/ko not_active Ceased
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Also Published As
| Publication number | Publication date |
|---|---|
| JP2008506829A (ja) | 2008-03-06 |
| WO2006013554A1 (en) | 2006-02-09 |
| ATE428745T1 (de) | 2009-05-15 |
| IL180428A0 (en) | 2007-06-03 |
| US7585912B2 (en) | 2009-09-08 |
| DE602005013975D1 (de) | 2009-05-28 |
| EP1786853A1 (en) | 2007-05-23 |
| ES2326036T3 (es) | 2009-09-29 |
| US20070257241A1 (en) | 2007-11-08 |
| IL180428A (en) | 2011-10-31 |
| EP1786853B1 (en) | 2009-04-15 |
| CN1989188A (zh) | 2007-06-27 |
| CN1989188B (zh) | 2010-05-12 |
| PL1786853T3 (pl) | 2009-09-30 |
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