JP2008506829A - 新規難燃性ポリスチレン - Google Patents
新規難燃性ポリスチレン Download PDFInfo
- Publication number
- JP2008506829A JP2008506829A JP2007522118A JP2007522118A JP2008506829A JP 2008506829 A JP2008506829 A JP 2008506829A JP 2007522118 A JP2007522118 A JP 2007522118A JP 2007522118 A JP2007522118 A JP 2007522118A JP 2008506829 A JP2008506829 A JP 2008506829A
- Authority
- JP
- Japan
- Prior art keywords
- flame retardant
- styrenic polymer
- formula
- polymer
- phosphorus compound
- 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
- 239000003063 flame retardant Substances 0.000 title claims abstract description 70
- 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 59
- 239000004793 Polystyrene Substances 0.000 title claims description 39
- 229920002223 polystyrene Polymers 0.000 title claims description 32
- 239000000203 mixture Substances 0.000 claims abstract description 93
- 229920000642 polymer Polymers 0.000 claims abstract description 55
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 21
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 38
- -1 phosphate ester compound Chemical class 0.000 claims description 38
- 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 32
- 239000000654 additive Substances 0.000 claims description 28
- 239000006260 foam Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 23
- 239000011574 phosphorus Substances 0.000 claims description 23
- 229910052698 phosphorus Inorganic materials 0.000 claims description 23
- 239000004794 expanded polystyrene Substances 0.000 claims description 21
- HGTUJZTUQFXBIH-UHFFFAOYSA-N (2,3-dimethyl-3-phenylbutan-2-yl)benzene Chemical compound C=1C=CC=CC=1C(C)(C)C(C)(C)C1=CC=CC=C1 HGTUJZTUQFXBIH-UHFFFAOYSA-N 0.000 claims description 20
- 239000004594 Masterbatch (MB) Substances 0.000 claims description 17
- 229910019142 PO4 Inorganic materials 0.000 claims description 15
- 239000010452 phosphate Substances 0.000 claims description 14
- 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 14
- 230000000996 additive effect Effects 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 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 8
- 150000003018 phosphorus compounds Chemical class 0.000 claims description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
- 238000001125 extrusion Methods 0.000 claims description 7
- 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 6
- 238000001746 injection moulding Methods 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 5
- 239000004593 Epoxy Substances 0.000 claims description 5
- 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 4
- 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
- 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
- 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
- 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 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
- 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
- 229920006248 expandable polystyrene Polymers 0.000 claims description 3
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims 6
- YUAPUIKGYCAHGM-UHFFFAOYSA-N 1,2-dibromo-3-(2,3-dibromopropoxy)propane Chemical compound BrCC(Br)COCC(Br)CBr YUAPUIKGYCAHGM-UHFFFAOYSA-N 0.000 claims 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 claims 3
- QEJPOEGPNIVDMK-UHFFFAOYSA-N 3-bromo-2,2-bis(bromomethyl)propan-1-ol Chemical compound OCC(CBr)(CBr)CBr QEJPOEGPNIVDMK-UHFFFAOYSA-N 0.000 claims 3
- BHYQWBKCXBXPKM-UHFFFAOYSA-N tris[3-bromo-2,2-bis(bromomethyl)propyl] phosphate Chemical compound BrCC(CBr)(CBr)COP(=O)(OCC(CBr)(CBr)CBr)OCC(CBr)(CBr)CBr BHYQWBKCXBXPKM-UHFFFAOYSA-N 0.000 claims 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 2
- 239000000523 sample Substances 0.000 description 22
- 238000009472 formulation Methods 0.000 description 21
- 238000012360 testing method Methods 0.000 description 17
- 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 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 12
- 235000021317 phosphate Nutrition 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 238000012545 processing Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 125000004970 halomethyl group Polymers 0.000 description 7
- 125000001246 bromo group Chemical group Br* 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 238000013329 compounding Methods 0.000 description 5
- 238000007906 compression Methods 0.000 description 5
- 230000006835 compression Effects 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 229920006327 polystyrene foam Polymers 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- 239000000460 chlorine Substances 0.000 description 4
- 238000009413 insulation Methods 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 125000005340 bisphosphate group Chemical group 0.000 description 3
- 125000005997 bromomethyl group Chemical group 0.000 description 3
- 238000000748 compression moulding Methods 0.000 description 3
- 239000004795 extruded polystyrene foam Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 229920005990 polystyrene resin Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 229920000426 Microplastic Polymers 0.000 description 2
- 239000006057 Non-nutritive feed additive Substances 0.000 description 2
- 229920001890 Novodur Polymers 0.000 description 2
- 150000007824 aliphatic compounds Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 230000000979 retarding effect Effects 0.000 description 2
- 238000010561 standard procedure Methods 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
- 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
- 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 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
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000004604 Blowing Agent Substances 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
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- PTMMCIFMVIXHBD-UHFFFAOYSA-N [4-(4-hydroxyphenyl)phenyl] phenyl hydrogen phosphate Chemical compound C1=CC(O)=CC=C1C(C=C1)=CC=C1OP(O)(=O)OC1=CC=CC=C1 PTMMCIFMVIXHBD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives 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
- 239000012141 concentrate Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 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
- 238000006731 degradation reaction Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000009969 flowable effect Effects 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
- 239000012760 heat stabilizer Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000007788 liquid Substances 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
- 239000003607 modifier Substances 0.000 description 1
- 239000002667 nucleating agent Substances 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate 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
- 238000003825 pressing Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000009966 trimming Methods 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2325/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Derivatives of such polymers
- C08J2325/02—Homopolymers or copolymers of hydrocarbons
- C08J2325/04—Homopolymers or copolymers of styrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL16310004 | 2004-07-19 | ||
| PCT/IL2005/000767 WO2006013554A1 (en) | 2004-07-19 | 2005-07-19 | Novel flame-retardant polystyrenes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008506829A true JP2008506829A (ja) | 2008-03-06 |
| JP2008506829A5 JP2008506829A5 (enExample) | 2008-06-05 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007522118A Pending JP2008506829A (ja) | 2004-07-19 | 2005-07-19 | 新規難燃性ポリスチレン |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7585912B2 (enExample) |
| EP (1) | EP1786853B1 (enExample) |
| JP (1) | JP2008506829A (enExample) |
| KR (1) | KR20070050442A (enExample) |
| CN (1) | CN1989188B (enExample) |
| AT (1) | ATE428745T1 (enExample) |
| DE (1) | DE602005013975D1 (enExample) |
| ES (1) | ES2326036T3 (enExample) |
| IL (1) | IL180428A (enExample) |
| PL (1) | PL1786853T3 (enExample) |
| WO (1) | WO2006013554A1 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012515249A (ja) * | 2009-01-15 | 2012-07-05 | 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 |
| JP2014208730A (ja) * | 2013-04-16 | 2014-11-06 | 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 |
| JP2016508146A (ja) * | 2013-01-06 | 2016-03-17 | ブロミン・コンパウンズ・リミテツド | 臭素含有芳香族化合物の調製およびその難燃剤としての利用 |
| JP2017528546A (ja) * | 2014-07-08 | 2017-09-28 | ブローミン コンパウンズ リミテッド | 臭素含有重合体の調製およびその難燃剤としての応用 |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006008738A1 (en) * | 2004-07-19 | 2006-01-26 | Bromine Compounds Ltd. | Synthesis of aromatic polyhalogenated halomethyl compounds |
| 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 |
| IL188983A (en) | 2008-01-23 | 2014-01-30 | Bromine Compounds Ltd | Delay in combustion in fabrics |
| GB2435479A (en) * | 2006-02-23 | 2007-08-29 | Bromine Compounds Ltd | Formulations comprising pentabromobenzylbromide and their use as flame retardants |
| US20080221239A1 (en) * | 2007-03-07 | 2008-09-11 | Falloon Stephen B | Flame retardant composition for use in styrenics |
| JP2011503335A (ja) * | 2007-11-20 | 2011-01-27 | アクゾ ノーベル ナムローゼ フェンノートシャップ | スチレン系（コ）ポリマーの調製方法 |
| 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 |
| 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 |
| CN106715516B (zh) | 2014-07-08 | 2019-04-19 | 溴化合物有限公司 | 用作阻燃剂的含溴聚合物的制备 |
| CN109312108A (zh) | 2016-05-11 | 2019-02-05 | 欧文斯科宁知识产权资产有限公司 | 包含低水平溴化阻燃剂的聚合物泡沫及其制备方法 |
| 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS493942A (enExample) * | 1972-04-24 | 1974-01-14 | ||
| 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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|---|---|---|---|---|
| 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 (enExample) * | 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 |
| 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 |
| DK0533742T3 (da) * | 1990-06-14 | 1997-08-18 | Dow Chemical Co | Brandsikre alkenylaromatiske skum |
| 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 |
| EP1112308A1 (en) | 1998-08-28 | 2001-07-04 | The Dow Chemical Company | 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 |
-
2005
- 2005-07-19 US US11/632,891 patent/US7585912B2/en not_active Expired - Fee Related
- 2005-07-19 DE DE602005013975T patent/DE602005013975D1/de not_active Expired - Lifetime
- 2005-07-19 EP EP05761339A patent/EP1786853B1/en not_active Expired - Lifetime
- 2005-07-19 KR KR1020077003810A patent/KR20070050442A/ko not_active Ceased
- 2005-07-19 PL PL05761339T patent/PL1786853T3/pl unknown
- 2005-07-19 JP JP2007522118A patent/JP2008506829A/ja active Pending
- 2005-07-19 AT AT05761339T patent/ATE428745T1/de active
- 2005-07-19 WO PCT/IL2005/000767 patent/WO2006013554A1/en not_active Ceased
- 2005-07-19 ES ES05761339T patent/ES2326036T3/es not_active Expired - Lifetime
- 2005-07-19 CN CN2005800242620A patent/CN1989188B/zh not_active Expired - Fee Related
-
2006
- 2006-12-28 IL IL180428A patent/IL180428A/en not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS493942A (enExample) * | 1972-04-24 | 1974-01-14 | ||
| 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 |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012515249A (ja) * | 2009-01-15 | 2012-07-05 | 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 |
| JP2016508146A (ja) * | 2013-01-06 | 2016-03-17 | ブロミン・コンパウンズ・リミテツド | 臭素含有芳香族化合物の調製およびその難燃剤としての利用 |
| US9988332B2 (en) | 2013-01-06 | 2018-06-05 | Bromine Compounds Ltd. | Preparation of bromine-containing aromatic compounds and their application as flame retardants |
| JP2014208730A (ja) * | 2013-04-16 | 2014-11-06 | 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 |
| JP2017528546A (ja) * | 2014-07-08 | 2017-09-28 | ブローミン コンパウンズ リミテッド | 臭素含有重合体の調製およびその難燃剤としての応用 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1989188A (zh) | 2007-06-27 |
| KR20070050442A (ko) | 2007-05-15 |
| IL180428A (en) | 2011-10-31 |
| CN1989188B (zh) | 2010-05-12 |
| EP1786853A1 (en) | 2007-05-23 |
| US20070257241A1 (en) | 2007-11-08 |
| ATE428745T1 (de) | 2009-05-15 |
| EP1786853B1 (en) | 2009-04-15 |
| PL1786853T3 (pl) | 2009-09-30 |
| DE602005013975D1 (de) | 2009-05-28 |
| IL180428A0 (en) | 2007-06-03 |
| WO2006013554A1 (en) | 2006-02-09 |
| US7585912B2 (en) | 2009-09-08 |
| ES2326036T3 (es) | 2009-09-29 |
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