WO2002046289A1 - Flammwidrige wärmeformbeständige polycarbonat-zusammensetzungen - Google Patents
Flammwidrige wärmeformbeständige polycarbonat-zusammensetzungen Download PDFInfo
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- WO2002046289A1 WO2002046289A1 PCT/EP2001/013712 EP0113712W WO0246289A1 WO 2002046289 A1 WO2002046289 A1 WO 2002046289A1 EP 0113712 W EP0113712 W EP 0113712W WO 0246289 A1 WO0246289 A1 WO 0246289A1
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- 239000000203 mixture Substances 0.000 title claims abstract description 81
- 229920000515 polycarbonate Polymers 0.000 title claims description 20
- 239000004417 polycarbonate Substances 0.000 title claims description 20
- -1 poly(ester) Polymers 0.000 claims abstract description 41
- 125000003118 aryl group Chemical group 0.000 claims abstract description 31
- 239000000178 monomer Substances 0.000 claims abstract description 26
- 229920000642 polymer Polymers 0.000 claims abstract description 26
- 150000003018 phosphorus compounds Chemical class 0.000 claims abstract description 16
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims abstract description 15
- 229920001283 Polyalkylene terephthalate Polymers 0.000 claims abstract description 14
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 14
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 14
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 12
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 11
- 230000009477 glass transition Effects 0.000 claims abstract description 9
- 229920006163 vinyl copolymer Polymers 0.000 claims abstract description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 38
- 229920000578 graft copolymer Polymers 0.000 claims description 30
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 238000000465 moulding Methods 0.000 claims description 19
- 229920001577 copolymer Polymers 0.000 claims description 16
- 229920000728 polyester Polymers 0.000 claims description 15
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 14
- 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 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- 239000011574 phosphorus Substances 0.000 claims description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 9
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical class COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 9
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 8
- 150000001735 carboxylic acids Chemical class 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229920001971 elastomer Polymers 0.000 claims description 5
- 125000002496 methyl group Chemical class [H]C([H])([H])* 0.000 claims description 5
- 239000005060 rubber Substances 0.000 claims description 5
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 4
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical class CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 150000003457 sulfones Chemical class 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 3
- 150000008360 acrylonitriles Chemical class 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- 229920001195 polyisoprene Polymers 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001993 dienes Chemical class 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 150000003440 styrenes Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000000839 emulsion Substances 0.000 description 16
- 239000003063 flame retardant Substances 0.000 description 14
- 239000002245 particle Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 229920000098 polyolefin Polymers 0.000 description 11
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 11
- 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 11
- KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 9
- AUTNMGCKBXKHNV-UHFFFAOYSA-P diazanium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [NH4+].[NH4+].O1B([O-])OB2OB([O-])OB1O2 AUTNMGCKBXKHNV-UHFFFAOYSA-P 0.000 description 8
- 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 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- 229910019142 PO4 Inorganic materials 0.000 description 6
- 229940106691 bisphenol a Drugs 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 235000021317 phosphate Nutrition 0.000 description 6
- 229920002857 polybutadiene Polymers 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical class [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 239000006085 branching agent Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000012779 reinforcing material Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004809 Teflon Substances 0.000 description 3
- 229920006362 Teflon® Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical group OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000006082 mold release agent Substances 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 2
- YIYBRXKMQFDHSM-UHFFFAOYSA-N 2,2'-Dihydroxybenzophenone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1O YIYBRXKMQFDHSM-UHFFFAOYSA-N 0.000 description 2
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 2
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 2
- VXHYVVAUHMGCEX-UHFFFAOYSA-N 2-(2-hydroxyphenoxy)phenol Chemical class OC1=CC=CC=C1OC1=CC=CC=C1O VXHYVVAUHMGCEX-UHFFFAOYSA-N 0.000 description 2
- QUWAJPZDCZDTJS-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfonylphenol Chemical class OC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1O QUWAJPZDCZDTJS-UHFFFAOYSA-N 0.000 description 2
- KYGLCUAXJICESS-UHFFFAOYSA-N 2-[2,3-di(propan-2-yl)phenyl]phenol Chemical class CC(C)C1=CC=CC(C=2C(=CC=CC=2)O)=C1C(C)C KYGLCUAXJICESS-UHFFFAOYSA-N 0.000 description 2
- XBQRPFBBTWXIFI-UHFFFAOYSA-N 2-chloro-4-[2-(3-chloro-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=C(O)C(Cl)=CC=1C(C)(C)C1=CC=C(O)C(Cl)=C1 XBQRPFBBTWXIFI-UHFFFAOYSA-N 0.000 description 2
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 2
- UMPGNGRIGSEMTC-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 UMPGNGRIGSEMTC-UHFFFAOYSA-N 0.000 description 2
- NIRYBKWMEWFDPM-UHFFFAOYSA-N 4-[3-(4-hydroxyphenyl)-3-methylbutyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)CCC1=CC=C(O)C=C1 NIRYBKWMEWFDPM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000004641 Diallyl-phthalate Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- KYPYTERUKNKOLP-UHFFFAOYSA-N Tetrachlorobisphenol A Chemical compound C=1C(Cl)=C(O)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(O)C(Cl)=C1 KYPYTERUKNKOLP-UHFFFAOYSA-N 0.000 description 2
- 229910010413 TiO 2 Inorganic materials 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 2
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 2
- 229910001593 boehmite Inorganic materials 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 125000005587 carbonate group Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000005253 cladding Methods 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 125000000853 cresyl group Chemical group C1(=CC=C(C=C1)C)* 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000010445 mica Substances 0.000 description 2
- 229910052618 mica group Inorganic materials 0.000 description 2
- 150000004712 monophosphates Chemical class 0.000 description 2
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000002667 nucleating agent Substances 0.000 description 2
- 229920002842 oligophosphate Polymers 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- XMNDMAQKWSQVOV-UHFFFAOYSA-N (2-methylphenyl) diphenyl phosphate Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 XMNDMAQKWSQVOV-UHFFFAOYSA-N 0.000 description 1
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- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000019394 potassium persulphate Nutrition 0.000 description 1
- XRVCFZPJAHWYTB-UHFFFAOYSA-N prenderol Chemical compound CCC(CC)(CO)CO XRVCFZPJAHWYTB-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 210000003660 reticulum Anatomy 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
- LIPMRGQQBZJCTM-UHFFFAOYSA-N tris(2-propan-2-ylphenyl) phosphate Chemical compound CC(C)C1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C(C)C)OC1=CC=CC=C1C(C)C LIPMRGQQBZJCTM-UHFFFAOYSA-N 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000002256 xylenyl group Chemical group C1(C(C=CC=C1)C)(C)* 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- 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
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
- C08K5/523—Esters of phosphoric acids, e.g. of H3PO4 with hydroxyaryl compounds
-
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0066—Flame-proofing or flame-retarding additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
Definitions
- the present invention relates to polycarbonate compositions which are flame-retardant with phosphorus compounds and which have excellent mechanical properties
- EP-A 0 640 655 describes film compositions made from aromatic polycarbonate, styrene-containing copolymers and graft polymers which can be flame-retarded with monomeric and / or oligomeric phosphorus compounds. Because of the proportion of monomeric phosphorus compounds, the aforementioned disadvantages can occur.
- EP-A 747 424 describes the use of a combination of phosphate with a molecular weight of approximately 500 to 2,000 and of phosphate with a molecular weight of approximately 2,300 to 11,000 as flame retardants in thermoplastic resins, a number of which is not enumerated by thermoplastic resins
- the present invention relates to compositions comprising
- X represents a mono- or polynuclear aromatic radical having 6 to 30 carbon atoms, Rl, R ⁇ , R ⁇ and R ⁇ independently of one another, optionally halogenated Ci-Cg-alkyl, each optionally by halogen and / or substituted Cs-Cg-cycloalkyl, Cö-C20-aryl or C -C ⁇ aralkyl,
- n depending on one another, 0 or 1, preferably 1,
- composition contains at least 2 phosphorus compounds of the formula (I) in which X or one or more radicals R 1 , R 2 , R 3 and R 4 are different and the sum of the parts by weight of I, II and optionally further additives is 100.
- the present invention preferably relates to compositions comprising
- X represents a mono- or polynuclear aromatic radical having 6 to 30 carbon atoms
- Rl, R ⁇ , R3 and R ⁇ independently of one another, optionally halogenated Cj-Cg-alkyl, each optionally by halogen and / or
- n independently of one another 0 or 1, preferably 1,
- composition contains at least 2 phosphorus compounds of the formula (I) in which X or one or more radicals R 1 , R 2 , R 3 and R 4 are different and the sum of the parts by weight of components A) + B) + C) + D) + E) and, if appropriate, further additives is 100.
- Aromatic polycarbonates and / or aromatic polyester carbonates according to component A which are suitable according to the invention are known from the literature or can be prepared by processes known from the literature (for the preparation of aromatic polycarbonates see, for example, Schnell, “Chemistry and Physics of Polycarbonates”, Interscience Publishers, 1964, and DE-AS 1 495 626, DE-OS 2 232 877, DE-A 2 703 376, DE-A 2 714 544, DE-A 3 000 610, DE-A 3 832 396; for the production of aromatic polyester carbonates, for example DE- A 3 077 934).
- Aromatic polycarbonates are produced e.g. by implementing
- Diphenols with carbonic acid halides preferably phosgene and / or with aromatic dicarboxylic acid dihalides, preferably benzenedicarboxylic acid dihalogenides, according to the phase interface method, optionally using chain terminators, for example monophenols and optionally using trifunctional or more than trifunctional ner branches, for example triphenols or tetrenols.
- Diphenols for the preparation of the aromatic polycarbonates and / or aromatic polyester carbonates are preferably those of the formula (II)
- a 1 is a single bond, -CC-alkylene, C2-C5-alkylidene, Cs-Cg-cycloalkylene, -O-, -SO-, -CO-, -S-, -SO2-, Cß-C ⁇ - Arylene, which may be condensed with further aromatic rings optionally containing heteroatoms, or a radical of the formula
- C 1 -C 4 -alkyl preferably C 1 -C 4 -alkyl, in particular methyl, halogen, preferably chlorine and / or bromine, Cö-CiQ-aryl, preferably phenyl, preferably
- Z carbon and m is an integer from 4 to 7, preferably 4 or 5,
- Preferred diphenols are hydroquinone, resorcinol, 4,4'-dihydroxydiphenyl, bis- (hydroxyphenyl) -C ⁇ -C5-alkanes, bis- (hydroxyphenyl) -C5-C6-cycloalkanes, bis- (hydroxyphenyl) ethers, bis - (hydroxy ⁇ henyl) sulfoxides, bis (hydroxyphenyl) ketones, bis (hydroxyphenyl) sulfones and ⁇ , ⁇ -bis (hydroxyphenyl) diisopropyl benzenes such as their core-brominated and / or core-chlorinated derivatives.
- diphenols are 4,4'-diphenylphenol, bisphenol-A, 2,4-bis (4-hydroxyphenyl) -2-methylbutane, 1,1-bis (4-hydroxyphenyl) cyclohexane, 1,1-bis - (4-hydroxyphenyl) -3,3,5-trimethylcyclohexane, 4,4'-dihydroxydiphenyl sulfide, 4,4'-
- Dihydroxydiphenyl sulfone and their di- and tetrabrominated or chlorinated derivatives such as, for example, 2,2-bis (3-chloro-4-hydroxyphenyl) propane, 2,2-bis (3,5-dichloro-4-hydroxyphenyl) propane or 2,2-bis (3,5-dibromo-4-hydroxyphenyl) propane.
- 2,2-bis (4-hydroxyphenyl) propane (bisphenol-A) is particularly preferred.
- the diphenols can be used individually or as any mixtures.
- the diphenols are known from the literature or can be obtained by processes known from the literature.
- Suitable chain terminators for the production of the thermoplastic, aromatic polycarbonates are, for example, phenol, p-chlorophenol, p-tert-butylphenol or 2,4,6-tribromophenol, but also long-chain alkylphenols, such as 4- (1,3-tetramethylbutyl) -phenol according to DE-OS 2 842 005 or monoalkylphenol or dialkylphenols with a total of 8 to 20 carbon atoms in the alkyl substituents, such as 3,5-di-tert-butylphenol, p-iso-octylphenol, p-tert-octylphenol, p-dodecylphenol and 2- (3,5- Dimethylheptyl) phenol and 4- (3,5-dimethylheptyl) phenol.
- the amount of chain terminators to be used is generally between 0.5 mol% and 10 mol%, based on the molar sum of the diphenols used in each case.
- thermoplastic, aromatic polycarbonates have average weight-average molecular weights (M w , measured, for example, by means of an ultracentrifuge or scattered light measurement) of 10,000 to 200,000, preferably 20,000 to 80,000.
- thermoplastic, aromatic polycarbonates can be branched in a known manner, preferably by incorporating 0.05 to 2.0 mol%, based on the sum of the diphenols used, of compounds having 3 or more functional groups, for example those having see three or more than three phenolic groups.
- copolycarbonates Both homopolycarbonates and copolycarbonates are suitable.
- component A 1 to 25% by weight, preferably 2.5 to 25% by weight (based on the total amount of diphenols to be used), polydiorganosiloxanes with hydroxy-aryloxy end groups can also be used. These are known (see, for example, from US Pat. No. 3,419,634) or can be produced by processes known from the literature.
- the production of polydiorganosiloxane-containing copolycarbonates is e.g. in DE-OS 3 334 782.
- preferred polycarbonates are polystyrene-co-styrene-co-styrene-co-styrene-co-styrene-co-styrene-co-styrene-co-styrene-co-styrene-co-styrene-co-styrene-co-styrene-co-styrene-co-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene
- Aromatic dicarboxylic acid dihalides for the production of aromatic polyester carbonates are preferably the diacid dichlorides of isophthalic acid, tere- phthalic acid, diphenyl ether-4,4'-dicarboxylic acid and naphthalene-2,6-dicarboxylic acid.
- Mixtures of the diacid dichlorides of isophthalic acid and terephthalic acid in a ratio between 1:20 and 20: 1 are particularly preferred.
- a carbonic acid halide preferably phosgene, is additionally used as the bifunctional acid derivative.
- the amount of chain terminators is in each case 0.1 to 10 mol%, based on moles of diphenols in the case of the phenolic chain terminators and on moles of dicarboxylic acid dichlorides in the case of monocarboxylic acid chloride chain terminators.
- the aromatic polyester carbonates can also contain aromatic hydroxycarboxylic acids.
- the aromatic polyester carbonates can be linear or branched in a known manner (see also DE-OS 2 940 024 and DE-OS 3 007 934).
- 3- or polyfunctional carboxylic acid chlorides such as trimesic acid trichloride, cyanuric acid trichloride, 3,3'-4,4'-benzophenonetetracarboxylic acid tetrachloride, 1, 4,5,8-naphthalenetetracarboxylic acid tetrachloride or pyromellitic acid tetrachloride
- branching agents in amounts of 0.01 to 1.0 mol% (based on the dicarboxylic acid dichlorides used) or 3- or polyfunctional phenols, such as phloro- glucin, 4,6-dimethyl-2,4,6-tri- (4-hydroxyphenyl) -hepten-2,4,4-dimethyl-2,4,6-tri- (4-hydroxyphenyl) -heptane, 1, 3,5-tri- (4-hydroxyphenyl) benzene, 1,1,1-tri- (4-hydroxyphenyl) ethane, tri- (4-
- Phenolic branching agents can be introduced with the diphenols, acid chloride branching agents can be introduced together with the acid dichlorides.
- thermoplastic, aromatic polyester carbonates can vary as desired.
- the proportion of carbonate groups is preferably up to 100 mol%, in particular up to 80 mol%, particularly preferably up to 50 mol%, based on the sum of ester groups and carbonate groups.
- Both the ester and the carbonate content of the aromatic polyester carbonates can be present in the form of blocks or randomly distributed in the polycondensate.
- the relative solution viscosity ( ⁇ re l) of the aromatic polyester carbonates is in the range 1.18 to 1.4, preferably 1.22 to 1.3 (measured on solutions of 0.5 g polyester carbonate in 100 ml methylene chloride solution at 25 ° C. ).
- thermoplastic, aromatic polycarbonates and polyester carbonates can be used alone or in any mixture with one another.
- Component B is
- Component B according to the invention is graft polymers. These comprise graft copolymers with rubber-elastic properties which can be obtained from at least 2 of the following monomers: chloroprene, 1,3-butadiene, isoprene, styrene,
- Preferred polymers B are partially crosslinked and have gel contents of more than 20% by weight, preferably more than 40% by weight, in particular more than 60% by weight.
- Preferred graft polymers B comprise graft polymers from:
- Bl2 1 to 50 wt .-% acrylonitrile, methacrylonitrile, methyl methacrylate, maleic anhydride, C j -C ⁇ alkyl or. phenyl-N-substituted maleimides or mixtures of these compounds
- graft polymers B are obtainable by grafting
- ⁇ 10 to 70 preferably 15 to 50, in particular 20 to 40% by weight, based on graft polymate B, of at least one (meth) acrylic ester or 10 to 70, preferably 15 to 50, in particular 20 to 40% by weight of one Mixtures of 10 to 50, preferably 20 to 35% by weight, based on the mixture, acrylonitrile or (meth) -acrylic acid ester and 50 to 90, preferably 65 to 80% by weight, based on the mixture, styrene, as graft B. 1 on
- ⁇ 30 to 90 preferably 50 to 85, in particular 60 to 80% by weight, based on graft polymer B, of a butadiene polymer with at least 50% by weight, based on ⁇ , butadiene residues as the graft base B.2.
- the gel fraction of the graft base ⁇ is generally at least 20% by weight, preferably 40% by weight (measured in toluene), the degree of graft G 0.15 to 0.55 and the average particle diameter d5 Q of the graft polymer B.2 0. 05 to 2 ⁇ m, preferably 0.1 to 0.6 ⁇ m.
- (Meth) -acrylic acid esters ⁇ are esters of acrylic acid or methacrylic acid with monohydric alcohols with 1 to 18 carbon atoms. Methacrylic acid methyl esters, ethyl esters and propyl esters, n-butyl acrylate, t-butyl acrylate and t-butyl methacrylate are particularly preferred.
- the graft base ⁇ can contain up to 50% by weight, based on ⁇ , residues of other ethylenically unsaturated monomers such as styrene, acrylonitrile, esters of acrylic or methacrylic acid with 1 to 4 carbon atoms in the alcohol component (such as methyl acrylate, ethyl acrylate) , Methyl methacrylate, ethyl methacrylate), vinyl ester and / or vinyl ether.
- the preferred graft base ß consists of pure
- the degree of grafting G denotes the weight ratio of grafted graft monomers to the graft base and is dimensionless.
- the average particle size d 50 is the diameter above and below which 50% by weight of the particles lie. It can be determined by means of ultracentrifuge measurement (W. Scholtan, H. Lange, Kolloid, Z. and Z. Polymer 250 (1972), 782-796).
- Particularly preferred polymers B are e.g. also graft polymers
- the acrylate rubbers ⁇ of the polymers B are preferably polymers of acrylic acid alkyl esters, optionally with up to 40% by weight, based on ⁇ , of other polymerizable, ethylenically unsaturated monomers.
- the preferred polymerizable acrylic acid esters include C 1 -C 6 -alkyl esters, for example methyl, ethyl, butyl, n-octyl and 2-ethyl-hexyl esters; Haloalkyl esters, preferably halo-Ci-Cg-alkyl esters, such as chloroethyl acrylate, and mixtures of these monomers.
- Monomers with more than one polymerizable double bond can be copolymerized for crosslinking.
- Preferred examples of crosslinking monomers are esters of unsaturated monocarboxylic acids with 3 to 8 C atoms and unsaturated monohydric alcohols with 3 to 12 C atoms or saturated polyols with 2 to 4
- OH groups and 2 to 20 C atoms e.g. Ethylene glycol dimethacrylate, allyl methacrylate; polyunsaturated heterocyclic compounds, e.g. Trivinyl and triallyl cyanurate; polyfunctional vinyl compounds such as di- and trivinylbenzenes; but also triallyl phosphate and diallyl phthalate.
- Crosslinking monomers are preferably allyl methacrylate, ethylene glycol dimethyl acrylate, diallyl phthalate and heterocyclic compounds which have at least 3 ethylenically unsaturated groups.
- crosslinking monomers are the cyclic monomers triallyl cyanurate, triallyl isocyanurate, trivinyl cyanurate, triacryloylhexahydro-s-triazine and triallylbenzenes.
- the amount of crosslinking monomers is preferably 0.02 to 5% by weight, in particular 0.05 to 2% by weight, based on the graft base ⁇ .
- Preferred “other” polymerizable, ethylenically unsaturated monomers which, in addition to the acrylic acid esters, can optionally be used to prepare the graft base ⁇ , are, for example, acrylonitrile, styrene, ⁇ -methylstyrene, acrylamides, vinyl-Ci-Cg-alkyl ethers, methyl methacrylate, butadiene.
- Preferred acrylate rubbers as Graft base ⁇ are emulsion polymers which have a gel content of at least 60% by weight.
- graft bases according to B.2 are silicone rubbers with graft-active sites, as described in DE-A 3 704 657, DE-A 3 704 655, DE-A 3 631 540 and DE-A 3 631 539.
- the gel content of the graft base B.2 is determined at 25 ° C. in dimethylformamide (M. Hoffmann, H. Krömer, R. Kuhn, Polymeranalytik I and II, Georg Thieme-Verlag, Stuttgart 1977).
- the graft polymers B can be prepared by known processes such as bulk, suspension, emulsion or bulk suspension processes.
- graft polymers B are understood according to the invention to mean those products which are obtained by polyreaction of the
- Graft monomers can be obtained on the graft base.
- the average particle size d5Q is the diameter above and below which 50% by weight of the particles lie. It can be determined by means of ultracentrifuge measurement (W. Scholtan, H. Lange, Kolloid, Z. and Z. Polymer 250 (1972), 782-1796).
- Component C comprises one or more thermoplastic vinyl (co) polymeric C.I. and / or polyalkylene terephthalates C. 2.
- Suitable as vinyl (co) polymers Cl are polymers of at least one monomer from the group of the vinyl aromatics, vinyl cyanides (unsaturated nitriles), (meth) acrylic acid (C 1 -C 8 ) alkyl esters, unsaturated carboxylic acids and derivatives (such as anhydrides and imides) unsaturated carboxylic acids.
- vinyl aromatics vinyl cyanides (unsaturated nitriles)
- (meth) acrylic acid (C 1 -C 8 ) alkyl esters unsaturated carboxylic acids and derivatives (such as anhydrides and imides) unsaturated carboxylic acids.
- Cll 50 to 99 preferably 60 to 80 wt .-% vinyl aromatics and / or core-substituted vinyl aromatics such as styrene, ⁇ -methylstyrene, p-methylstyrene, p-chlorostyrene) and / or methacrylic acid (-C-C 8 ) alkyl esters such as Methyl methacrylate, ethyl methacrylate), and
- Cl2 1 to 50, preferably 20 to 40 wt .-% vinyl cyanides (unsaturated nitriles) such as acrylonitrile and methacrylonitrile and / or (meth) acrylic acid (C] -C 8 ) alkyl esters (such as methyl methacrylate, n-butyl acrylate, t -Butyl acrylate) and or unsaturated carboxylic acids (such as maleic acid) and / or derivatives (such as anhydrides and imides) of unsaturated carboxylic acids (e.g. maleic anhydride and N-phenyl-maleimide).
- unsaturated carboxylic acids such as maleic acid
- derivatives such as anhydrides and imides
- the (co) polymers C.l are resin-like, thermoplastic and rubber-free.
- copolymer of C.I. 1 styrene and C.I. 2 acrylonitrile is particularly preferred.
- the (co) polymers according to Cl are known and can be prepared by radical polymerization, in particular by emulsion, suspension, solution or bulk polymerization.
- the (co) polymers preferably have molecular weights M w (weight average, determined by light scattering or sedimentation) between 15,000 and 200,000.
- the polyalkylene terephthalates of component C.2 are reaction products made from aromatic dicarboxylic acids or their reactive derivatives, such as dimethyl esters or anhydrides, and aliphatic, cycloaliphatic or araliphatic diols and mixtures of these reaction products.
- Preferred polyalkylene terephthalates contain at least 80 mol%, preferably at least 90 mol%, based on the dicarboxylic acid component terephthalic acid residues and at least 80 mol%, preferably at least 90 mol%, based on the diol component ethylene glycol and / or butanediol-1, 4 residues.
- the preferred polyalkylene terephthalates can contain up to 20 mol%, preferably up to 10 mol%, of residues of other aromatic or cycloaliphatic dicarboxylic acids with 8 to 14 C atoms or aliphatic dicarboxylic acids with 4 to 12 C atoms, e.g. Residues of phthalic acid, isophthalic acid, naphthalene-2,6-dicarboxylic acid, 4,4'-diphenyldicarboxylic acid, succinic acid, adipic acid, sebacic acid, azelaic acid, cyclohexane-diacetic acid.
- the preferred polyalkylene terephthalates can contain up to 20 mol%, preferably up to 10 mol%, other aliphatic diols with 3 to 12 carbon atoms or cycloaliphatic diols with 6 to 21 Contain carbon atoms, e.g.
- the polyalkylene terephthalates can be branched by incorporating relatively small amounts of trihydric or tetravalent alcohols or 3- or 4-basic carboxylic acids, for example according to DE-OS 1 900270 and US Pat. No. 3,692,744.
- preferred branching agents are trimesic acid, trimellitic acid, trimethylolethane and -propane and pentaerythritol.
- polyalkylene terephthalates which have been produced solely from terephthalic acid and its reactive derivatives (e.g. its dialkyl esters) and ethylene glycol and / or 1,4-butanediol, and mixtures of these polyalkylene terephthalates.
- Polyalkylene terephthalates contain 1 to 50% by weight, preferably 1 to 30% by weight, polyethylene terephthalate and 50 to 99% by weight, preferably 70 to 99% by weight, polybutylene terephthalate.
- the polyalkylene terephthalates preferably used generally have an intrinsic viscosity of 0.4 to 1.5 dl / g, preferably 0.5 to 1.2 dl / g, measured in phenol / o-dichlorobenzene (1: 1 parts by weight) at 25 ° C. in the Ubbelohde viscometer.
- the polyalkylene terephthalates can be prepared by known methods (see e.g.
- the molding compositions according to the invention contain at least one phosphorus compound of the formula (I-a) as flame retardant
- X 1 represents a mononuclear or polynuclear aromatic radical having 6 to 30 C atoms
- X 2 represents a mononuclear or polynuclear aromatic radical having 6 to 30 carbon atoms
- R *, R2, R3 and R 4 can in turn be independently substituted by halogen and / or alkyl groups, preferably chlorine, bromine and / or C1-C4-alkyl.
- Particularly preferred aryl radicals are cresyl, phenyl, xylenyl, propylphenyl or butylphenyl and the corresponding brominated and chlorinated derivatives thereof.
- Xiund X 2 are each preferably different and stand for a single- or multi-core aromatic radical having 6 to 30 C atoms.
- Preferred residues are derived from diphenols according to formula (II).
- Preferred diphenols are hydroquinone, resorcinol, 4,4'-dihydroxydiphenyl, bis- (hydroxyphenyl) -C ⁇ -C5-alkanes, bis- (hydroxyphenyl) -C5-C6-cycloalkanes, bis- (hydroxyphenyl) ethers, bis - (Hydroxyphenyl) sulfoxides, bis (hydroxyphenyl) ketones, bis (hydroxyphenyl) sulfones and ⁇ , ⁇ -bis (hydroxyphenyl) diisopropyl benzenes such as their core-brominated and / or core-chlorinated derivatives.
- diphenols are 4,4'-diphenylphenol, bisphenol-A, 2,4-bis (4-hydroxyphenyl) -2-methylbutane, 1,1-bis (4-hydroxyphenyl) cyclohexane, 1,1-bis - (4-hydroxyphenyl) -3,3,5-trimethylcyclohexane, 4,4'-dihydroxydiphenyl sulfide, 4,4'-
- Dihydroxydiphenyl sulfone and their di- and tetrabrominated or chlorinated derivatives such as, for example, 2,2-bis (3-chloro-4-hydroxyphenyl) propane, 2,2-bis (3,5-dichloro-4-hydroxyphenyl) propane or 2,2-bis (3,5-dibromo-4-hydroxyphenyl) propane.
- diphenols are bisphenol A, resorcinol, hydroquinone, dihydroxydiphenyl and dihydroxydiphenyl sulfone.
- q 0 compounds such as tributyl phosphate, tris (2-chloroethyl) phosphate, tris (2,3-dibromopropyl) phosphate, triphenyl phosphate, tricresyl phosphate, diphenyl cresyl phosphate, diphenyl octyl phosphate, diphenyl 2-ethyl cresyl phosphate, tri (isopropylphenyl) phosphate, halogen-substituted aryl phosphates, methylphosphonic acid dimethyl ester, methylphosphonic acid diphenyl ester, phenylphosphonic acid diethyl ester, triphenylphosphine oxide or tricresylphosphine oxide.
- the molding compositions according to the invention preferably contain at least one phosphorus compound of the formula (I-c) as flame retardant,
- R 1 , R 2 , R 3 , R 4 , n and q have the abovementioned meanings.
- R 5 is independently -C 4 alkyl and / or halogen, k is 0, 1 or 2, preferably 0, Y is methylene or isopropylidene. Y particularly preferably represents an isopropylidene radical.
- the phosphorus compounds according to component D are generally known compounds of organic chemistry or can be prepared in an analogous manner by known methods (cf., for example, Ullmanns Encyklopadie der Technischen Chemie, vol. 18, pp. 301 ff. 179; Houben-Weyl, methods of Organic Chemistry, vol. 12/1, p. 43; Beistein, vol. 6, p. 177) by using at least 2 different dihydroxy compounds, for example bisphenols, hydroquinone, for the synthesis.
- the fluorinated polyolefins E are high molecular weight and possess glass transition temperatures above -30 ° C, usually above 100 ° C, fluorine contents, preferably of 65 to 76, preferably from 70 to 76 weight .-%, mean particle diameter d 5 o of 0 , 05 to 1,000, preferably 0.08 to 20 ⁇ m.
- the fluorinated polyolefins E have a density of 1.2 to 2.3 g / cm.
- Preferred fluorinated polyolefins E are polytetrafluoroethylene, polyvinylidene fluoride, tetrafluoroethylene (hexafluoropropylene and ethylene / tetrafluoroethylene copolymers.
- the fluorinated polyolefins are known (cf. "Vinyl and Related Polymers" from Schildknecht, John
- ⁇ орcerol ⁇ ⁇ о ⁇ оловки can be prepared by known processes, for example by polymerizing tetrafluoroethylene in an aqueous medium with a free radical-forming catalyst, for example sodium, potassium or ammonium peroxydisulfate at pressures of 7 to 71 kg / cm 2 and at temperatures of 0 to 200 ° C, preferably at temperatures of 20 to 100 ° C. (See U.S. Patent 2,393,967 for more details).
- a free radical-forming catalyst for example sodium, potassium or ammonium peroxydisulfate
- the density of these materials can be between 1.2 and 2.3 g / cm 3 , the average particle size between 0.5 and 1000 ⁇ m.
- Fluorinated polyolefins E preferred according to the invention are tetrafluoroethylene polymers with average particle diameters of 0.05 to 20 ⁇ m, preferably 0.08 to 10 ⁇ m, and a density of 1.2 to 1.9 g / cm 3 and are preferably coagulated Mixture of emulsions of tetrafluoroethylene polymers E with emulsions of graft polymers B used.
- Suitable fluorinated polyolefins E which can be used in powder form are tetrafluoroethylene polymers with average particle diameters of 100 to 1000 ⁇ m and densities of 2.0 g / cm to 2.3 g / cm.
- an aqueous emulsion (latex) of a graft polymer B is first mixed with a finely divided emulsion of a fluorinated polyolefin E;
- Suitable emulsions of fluorinated polyolefins usually have solids contents of 30 to 70% by weight, in particular 50 to 60% by weight, preferably 30 to 35% by weight.
- component B does not include the proportion of the graft polymer for the coagulated mixture of graft polymer and fluorinated polyolefins.
- the equilibrium ratio of graft polymer B to fluorinated polyolefin E in the emulsion mixture is 95: 5 to 60:40.
- the emulsion mixture is coagulated in a known manner, for example by spray drying, freeze drying or coagulation by adding inorganic or organic salts, acids, bases or organic, water-miscible solvents, such as alcohols, ketones, preferably at temperatures from 20 to 150 ° C. , especially from 50 to
- drying can be carried out at 50 to 200 ° C., preferably 70 to 100 ° C.
- Suitable tetrafluoroethylene polymer emulsions are commercially available products and are, for example, from DuPont as Teflon, such as
- compositions according to the invention can be at least one of the usual
- Glass fibers come as inorganic reinforcement materials, if necessary cut or ground, glass beads, glass balls, flake-like reinforcing material, such as kaolin, talc, mica, mica, carbon fibers in question. Cut or ground glass fibers are preferably used as the reinforcing material, preferably with a length of 1 to 10 mm and a diameter of ⁇ 20 ⁇ m in an amount of 1 to 40 parts by weight; the glass fibers are preferably surface-treated.
- compositions according to the invention can moreover comprise at least one polar compound of at least one of the metals of the 1st to 5th main group or of the 1st to 8th secondary group of the periodic table with at least one element selected from the group of oxygen, sulfur, boron, carbon, phosphorus, Contain nitrogen, hydrogen and silicon as finely divided inorganic powder.
- An oxide or hydroxide preferably TiO 2 , SiO 2 , SnO 2 , ZnO, boehmite, ZrO 2 , Al 2 O, iron oxides, their mixtures and doped compounds, particularly preferably boehmite or TiO 2 , are preferred as the polar compound.
- compositions according to the invention can contain one or more further, optionally synergistic flame retardants.
- additional flame retardants from component D are various phosphorus compounds, organic halogen compounds such as decabromobisphenyl ether,
- Tetrabromobisphenol inorganic halogen compounds such as ammonium bromide, nitrogen compounds such as melamine, melamine formaldehyde resins, inorganic hydroxide compounds such as Mg, Al hydroxide, inorganic compounds such as antimony oxides, barium metaborate, hydroxoantimonate, zirconium oxide, zirconium hydroxide, molybdenum oxide, ammonium molybdate and zinc borate, ammonium borate, zinc borate, ammonium borate, zinc borate, ammonium borate, zinc borate, and ammonium borate, zinc borate, zinc borate, and ammonium borate, zinc borate, and ammonium borate, zinc borate, and ammonium borate, zinc borate, and ammonium borate, zinc borate, and ammonium borate, zinc borate, and ammonium borate, zinc borate, and ammonium borate, zinc borate, and ammonium borate, zinc borate, and ammonium bo
- compositions according to the invention containing components A to E and, if appropriate, further known additives such as stabilizers, dyes, pigments elements, lubricants and mold release agents, nucleating agents, nanoparticles as well as antistatic agents and reinforcing materials and flame retardants are produced by mixing the respective components in a known manner and at temperatures of 200 ° C. to 300 ° C. in conventional units such as internal kneaders, extruders and double wave screws melt-compounded and melt-extruded, component E preferably being used in the form of the coagulated mixture already mentioned.
- the individual constituents can be mixed in a known manner both successively and simultaneously, both at about 20 ° C. (room temperature) and at a higher temperature.
- compositions of the present invention can be used for the production of moldings of any kind.
- moldings can be produced by injection molding.
- moldings that can be produced are: Housing parts of all types, eg. B. for household appliances such as juicers, coffee machines, mixers, for office machines such as monitors, printers, copiers or cover plates for the construction sector and parts for the motor vehicle sector. They are also used in the field of electrical engineering because they have very good electrical properties.
- compositions according to the invention can be used, for example, for the production of the following moldings or moldings:
- FR Rail vehicles
- hubcaps housings for electrical equipment containing small transformers, housings for devices for disseminating and transmitting information, housings and linings for medical purposes, massagers and housings therefor, toy vehicles for children, flat wall elements, housings for safety devices, rear spoilers , heat-insulated transport containers, device for keeping or supplying small animals, molded parts for sanitary and bathing equipment, cover grilles for ventilation openings,
- Molded parts for garden and equipment houses, housing for garden tools. Further applications are possible
- telecommunication devices such as telephone devices and faxes, computers, printers, scanners, plotters, monitors, keyboards, typewriters, dictation devices, etc.
- garden tools garden furniture, lawn mower housings, pipes and housings for garden irrigation, garden houses, leaf vacuums, shredders, shredders, sprayers etc.,
- sports / play equipment toy vehicles, seats, pedals, sports equipment, bicycles, table tennis, exercise bikes, golf caddies, snow boards, boat parts, camping items, beach chairs etc.,
- compositions are particularly suitable for the production of molded parts, where particularly high demands are placed on the heat resistance of the plastics used.
- Another form of processing is the production of shaped bodies by deep drawing from previously produced sheets or foils.
- Another object of the present invention is therefore the use of the compositions according to the invention for the production of moldings of any kind, preferably those mentioned above, and the moldings from the compositions according to the invention.
- Component B.2 graft polymer of 84 parts by weight of a copolymer of styrene and acrylonitrile in a ratio of 73:27 to 16 parts by weight of crosslinked polybutadiene rubber, produced by bulk polymerization.
- Tetrafluoroethylene polymer as a coagulated mixture of a SAN graft polymer emulsion according to the above.
- the weight ratio of graft polymer B to tetrafluoroethylene polymer E in the mixture is 90% by weight to 10% by weight.
- the tetrafluoroethylene polymer emulsion has a solids content of 60% by weight, the average particle diameter is between 0.05 and 0.5 ⁇ m.
- the emulsion of the tetrafluoroethylene polymer (Teflon 30 N from DuPont) is mixed with the emulsion of the SAN graft polymer B and stabilized with 1.8% by weight, based on polymer solids, of phenolic antioxidants.
- the mixture is coagulated with an aqueous solution of MgSO4 (Epsom salt) and acetic acid at pH 4 to 5, filtered and washed until practically free of electrolytes, then freed from the main amount of water by centrifugation and then at 100 ° C dried to a powder. This powder can then be compounded with the other components in the units described.
- the components are mixed on a 3-1 kneader.
- the moldings are produced on an Arburg 270 E injection molding machine at 260 ° C.
- the notched impact strength a k is determined in accordance with ISO 180/1 A.
- the fire behavior of the samples was determined according to UL Subj. 94 V measured on rods measuring 127 x 12.7 x 1.6 mm, produced on an injection molding machine at 260 ° C.
- the UL 94 V test is carried out as follows: Substance samples are shaped into rods measuring 127 x 12.7 x 1.6 mm. The rods are mounted vertically so that the underside of the test specimen is 305 mm above a strip of bandaging material. Each test stick is ignited individually by means of two successive ignition processes of 10 s duration, the burning properties after each ignition process are observed and the sample is then evaluated. A Bunsen burner with a 100 mm (3.8 inch) high blue flame of natural gas with a thermal unit of 3.73 x 10 4 kJ / m 3 (1000 BTU per cubic foot) is used to ignite the sample.
- the UL 94 V-O classification includes the properties of materials described below that are tested in accordance with the UL 94 V regulation.
- the molding compounds in this class do not contain any samples that burn longer than 10 s after each exposure to the test flame; they do not show a total flame time of more than 50 s when exposed twice to each sample set; they do not contain any
- Samples that burn completely up to the retaining clip attached to the top of the sample they have no samples which ignite the cotton wool arranged below the sample by burning drops or particles; they also do not contain any samples that glow more than 30 s after the test flame has been removed.
- UL 94 classifications refer to samples that are less flame retardant or less self-extinguishing because they emit flaming drops or particles. These classifications are referred to as UL 94 V-1 and V-2. N.B. means "failed" and is the classification of samples that have an afterburn time of> 30 s.
- MVR is determined according to ISO 1133 A summary of the properties of the molding materials according to the invention is given in Table 1 below:
- compositions and properties (quantity in% by weight)
- the molding compositions according to the invention contain a mixture of two structurally different oligophosphates and are distinguished by a favorable combination of properties of high impact strength, high heat resistance, good processing behavior and improved flame resistance.
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020037007608A KR100794451B1 (ko) | 2000-12-08 | 2001-11-26 | 난연성이고 내열성인 폴리카르보네이트 조성물 |
DE50113952T DE50113952D1 (de) | 2000-12-08 | 2001-11-26 | Flammwidrige wärmeformbeständige polycarbonat-zusammensetzungen |
BRPI0116031-1A BR0116031B1 (pt) | 2000-12-08 | 2001-11-26 | composições de policarbonato resistentes ao fogo e ao calor, seu uso, bem como partes moldadas, pelìculas ou láminas assim obtidas. |
JP2002548017A JP3987433B2 (ja) | 2000-12-08 | 2001-11-26 | 加熱歪み抵抗を有する難燃性ポリカーボネート組成物 |
CA002436697A CA2436697C (en) | 2000-12-08 | 2001-11-26 | Flameproof polycarbonate compositions resistant to thermal deformation |
EP01999605A EP1363973B1 (de) | 2000-12-08 | 2001-11-26 | Flammwidrige wärmeformbeständige polycarbonat-zusammensetzungen |
AU2002216054A AU2002216054A1 (en) | 2000-12-08 | 2001-11-26 | Flameproof polycarbonate compositions resistant to thermal deformation |
MXPA03005117A MXPA03005117A (es) | 2000-12-08 | 2001-11-26 | Composiciones de policarbonato ignifugas, resistentes a deformacion por calor. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10061078.1 | 2000-12-08 | ||
DE10061078A DE10061078A1 (de) | 2000-12-08 | 2000-12-08 | Flammwidrige wärmeformbeständige Polycarbonat-Zusammensetzungen |
Publications (1)
Publication Number | Publication Date |
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WO2002046289A1 true WO2002046289A1 (de) | 2002-06-13 |
Family
ID=7666294
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2001/013712 WO2002046289A1 (de) | 2000-12-08 | 2001-11-26 | Flammwidrige wärmeformbeständige polycarbonat-zusammensetzungen |
Country Status (16)
Country | Link |
---|---|
US (1) | US6713544B2 (de) |
EP (1) | EP1363973B1 (de) |
JP (1) | JP3987433B2 (de) |
KR (1) | KR100794451B1 (de) |
CN (1) | CN1268677C (de) |
AR (1) | AR031643A1 (de) |
AT (1) | ATE394450T1 (de) |
AU (1) | AU2002216054A1 (de) |
BR (1) | BR0116031B1 (de) |
CA (1) | CA2436697C (de) |
DE (2) | DE10061078A1 (de) |
ES (1) | ES2302765T3 (de) |
MX (1) | MXPA03005117A (de) |
RU (1) | RU2003120518A (de) |
TW (1) | TWI248458B (de) |
WO (1) | WO2002046289A1 (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005123824A2 (en) | 2004-06-11 | 2005-12-29 | 3-Form, Inc. | Fire-resistant architectural resin materials |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10036057A1 (de) * | 2000-07-25 | 2002-02-07 | Bayer Ag | Flammwidrige Polycarbonat-Zusammensetzungen |
DE10234419A1 (de) * | 2002-07-29 | 2004-02-12 | Bayer Ag | Flammwidrige Formmassen |
KR100650910B1 (ko) * | 2004-10-13 | 2006-11-27 | 제일모직주식회사 | 난연성 열가소성 수지 조성물 |
FR2924121A1 (fr) * | 2007-11-27 | 2009-05-29 | Total France Sa | Composition bitumineuse elastique reticulee de maniere thermoreversible |
TWI421299B (zh) * | 2010-07-23 | 2014-01-01 | Entire Technology Co Ltd | 阻燃複合材料 |
KR101437140B1 (ko) | 2011-09-21 | 2014-09-02 | 제일모직주식회사 | 폴리카보네이트 및 그 제조방법 |
EP2848640A1 (de) * | 2013-09-13 | 2015-03-18 | LANXESS Deutschland GmbH | Phosphorsäureester-Zubereitungen mit verringerter Hygroskopie |
CN104962059B (zh) * | 2015-06-18 | 2016-11-02 | 金发科技股份有限公司 | 一种聚碳酸酯组合物及其制备方法 |
WO2018149831A1 (de) * | 2017-02-14 | 2018-08-23 | Covestro Deutschland Ag | Verfahren zur herstellung eines gegenstands mittels eines additiven fertigungsverfahrens unter einsatz eines polycarbonat-aufbaumaterials mit verbesserter fliessfähigkeit |
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WO1996011977A1 (en) * | 1994-10-13 | 1996-04-25 | Akzo Nobel N.V. | Polycarbonate-containing polymers flame retarded with oligomeric phosphate esters |
DE19734663A1 (de) * | 1997-08-11 | 1999-02-18 | Bayer Ag | Flammwidrige wärmeformbeständige Polycarbonat-ABS-Formmassen |
EP0936244A2 (de) * | 1998-02-13 | 1999-08-18 | General Electric Company | Flammhemmende Polycarbonatabmischung |
DE19914139A1 (de) * | 1999-03-27 | 2000-09-28 | Bayer Ag | Flammwidrige, schlagzähmodifizierte Polycarbonat-Formmassen |
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WO2000058402A1 (fr) * | 1999-03-26 | 2000-10-05 | Asahi Kasei Kabushiki Kaisha | Composition de resine retardatrice de flamme a base de polycarbonate |
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DE3819081A1 (de) | 1988-06-04 | 1989-12-07 | Bayer Ag | Flammwidrige, schlagzaehe polycarbonat-formmassen |
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 |
DE4328656A1 (de) | 1993-08-26 | 1995-03-02 | Bayer Ag | Flammwidrige, spannungsrißbeständige Polycarbonat-ABS-Formmassen |
TW360681B (en) | 1995-06-07 | 1999-06-11 | Gen Electric | Phosphate flame retardant polymers |
-
2000
- 2000-12-08 DE DE10061078A patent/DE10061078A1/de not_active Withdrawn
-
2001
- 2001-11-26 CA CA002436697A patent/CA2436697C/en not_active Expired - Fee Related
- 2001-11-26 AU AU2002216054A patent/AU2002216054A1/en not_active Abandoned
- 2001-11-26 KR KR1020037007608A patent/KR100794451B1/ko active IP Right Grant
- 2001-11-26 EP EP01999605A patent/EP1363973B1/de not_active Expired - Lifetime
- 2001-11-26 CN CNB018202349A patent/CN1268677C/zh not_active Expired - Fee Related
- 2001-11-26 RU RU2003120518/04A patent/RU2003120518A/ru not_active Application Discontinuation
- 2001-11-26 JP JP2002548017A patent/JP3987433B2/ja not_active Expired - Fee Related
- 2001-11-26 DE DE50113952T patent/DE50113952D1/de not_active Expired - Lifetime
- 2001-11-26 MX MXPA03005117A patent/MXPA03005117A/es active IP Right Grant
- 2001-11-26 ES ES01999605T patent/ES2302765T3/es not_active Expired - Lifetime
- 2001-11-26 WO PCT/EP2001/013712 patent/WO2002046289A1/de active IP Right Grant
- 2001-11-26 AT AT01999605T patent/ATE394450T1/de not_active IP Right Cessation
- 2001-11-26 BR BRPI0116031-1A patent/BR0116031B1/pt not_active IP Right Cessation
- 2001-12-03 US US10/006,517 patent/US6713544B2/en not_active Expired - Lifetime
- 2001-12-07 TW TW090130277A patent/TWI248458B/zh not_active IP Right Cessation
- 2001-12-07 AR ARP010105695A patent/AR031643A1/es unknown
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WO1996011977A1 (en) * | 1994-10-13 | 1996-04-25 | Akzo Nobel N.V. | Polycarbonate-containing polymers flame retarded with oligomeric phosphate esters |
DE19734663A1 (de) * | 1997-08-11 | 1999-02-18 | Bayer Ag | Flammwidrige wärmeformbeständige Polycarbonat-ABS-Formmassen |
US6127465A (en) * | 1997-09-04 | 2000-10-03 | Idemitsu Petrochemical Co., Ltd. | Polycarbonate resin composition |
EP0936244A2 (de) * | 1998-02-13 | 1999-08-18 | General Electric Company | Flammhemmende Polycarbonatabmischung |
WO2000058402A1 (fr) * | 1999-03-26 | 2000-10-05 | Asahi Kasei Kabushiki Kaisha | Composition de resine retardatrice de flamme a base de polycarbonate |
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WO2005123824A2 (en) | 2004-06-11 | 2005-12-29 | 3-Form, Inc. | Fire-resistant architectural resin materials |
EP1763557A4 (de) * | 2004-06-11 | 2010-12-01 | Hunter Douglas Ind Bv | Flammwidrige bauharzmaterialien |
Also Published As
Publication number | Publication date |
---|---|
CA2436697A1 (en) | 2002-06-13 |
KR100794451B1 (ko) | 2008-01-16 |
RU2003120518A (ru) | 2004-12-27 |
JP3987433B2 (ja) | 2007-10-10 |
AU2002216054A1 (en) | 2002-06-18 |
CA2436697C (en) | 2009-09-22 |
KR20030063406A (ko) | 2003-07-28 |
JP2004515589A (ja) | 2004-05-27 |
DE10061078A1 (de) | 2002-06-13 |
CN1268677C (zh) | 2006-08-09 |
BR0116031A (pt) | 2003-10-07 |
ATE394450T1 (de) | 2008-05-15 |
TWI248458B (en) | 2006-02-01 |
ES2302765T3 (es) | 2008-08-01 |
US20020128359A1 (en) | 2002-09-12 |
EP1363973B1 (de) | 2008-05-07 |
US6713544B2 (en) | 2004-03-30 |
MXPA03005117A (es) | 2004-12-06 |
BR0116031B1 (pt) | 2011-04-05 |
EP1363973A1 (de) | 2003-11-26 |
AR031643A1 (es) | 2003-09-24 |
DE50113952D1 (de) | 2008-06-19 |
CN1479764A (zh) | 2004-03-03 |
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