JP5139981B2 - ポリカーボネート難燃性組成物 - Google Patents

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Publication number

JP5139981B2

JP5139981B2 JP2008526481A JP2008526481A JP5139981B2 JP 5139981 B2 JP5139981 B2 JP 5139981B2 JP 2008526481 A JP2008526481 A JP 2008526481A JP 2008526481 A JP2008526481 A JP 2008526481A JP 5139981 B2 JP5139981 B2 JP 5139981B2

Authority

JP

Japan

Prior art keywords

group

carbon atoms

independently

formula

tert

Prior art date

2005-08-16

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.)

Expired - Fee Related

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• 239000000203 mixture Substances 0.000 title claims abstract description 81
• 239000004417 polycarbonate Substances 0.000 title claims abstract description 73
• 229920000515 polycarbonate Polymers 0.000 title claims abstract description 67
• 239000003063 flame retardant Substances 0.000 title claims abstract description 42
• 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 19
• LVTHXRLARFLXNR-UHFFFAOYSA-M potassium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F LVTHXRLARFLXNR-UHFFFAOYSA-M 0.000 claims abstract description 8
• 125000004432 carbon atom Chemical group C* 0.000 claims description 189
• -1 aromatic carboxylic acids Chemical class 0.000 claims description 183
• 125000000217 alkyl group Chemical group 0.000 claims description 104
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 54
• 150000001875 compounds Chemical class 0.000 claims description 42
• 125000002947 alkylene group Chemical group 0.000 claims description 37
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
• 125000003118 aryl group Chemical group 0.000 claims description 25
• 229910052799 carbon Inorganic materials 0.000 claims description 23
• 229920000307 polymer substrate Polymers 0.000 claims description 23
• 150000003839 salts Chemical class 0.000 claims description 23
• 239000002253 acid Substances 0.000 claims description 22
• 125000003342 alkenyl group Chemical group 0.000 claims description 22
• 125000001153 fluoro group Chemical group F* 0.000 claims description 21
• XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 20
• 229910052731 fluorine Inorganic materials 0.000 claims description 20
• 229910052698 phosphorus Inorganic materials 0.000 claims description 20
• 229910052710 silicon Inorganic materials 0.000 claims description 20
• 239000010703 silicon Substances 0.000 claims description 20
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 17
• 125000001931 aliphatic group Chemical group 0.000 claims description 17
• 239000011574 phosphorus Substances 0.000 claims description 17
• 150000004715 keto acids Chemical class 0.000 claims description 14
• 125000001424 substituent group Chemical group 0.000 claims description 14
• 229940124530 sulfonamide Drugs 0.000 claims description 13
• 150000003456 sulfonamides Chemical class 0.000 claims description 13
• 239000011734 sodium Substances 0.000 claims description 12
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 11
• 229910052708 sodium Inorganic materials 0.000 claims description 11
• 150000003460 sulfonic acids Chemical class 0.000 claims description 9
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
• 125000005843 halogen group Chemical group 0.000 claims description 8
• 125000003277 amino group Chemical group 0.000 claims description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 2
• 239000011737 fluorine Substances 0.000 claims description 2
• 239000000758 substrate Substances 0.000 abstract description 7
• NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 abstract description 4
• KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract description 3
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 47
• 229920001577 copolymer Polymers 0.000 description 47
• 229920000642 polymer Polymers 0.000 description 38
• 239000000654 additive Substances 0.000 description 32
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 19
• 150000001721 carbon Chemical group 0.000 description 18
• 239000004952 Polyamide Substances 0.000 description 17
• 238000000034 method Methods 0.000 description 17
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• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 16
• 239000005977 Ethylene Substances 0.000 description 16
• 150000002148 esters Chemical class 0.000 description 16
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
• IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 14
• 239000003381 stabilizer Substances 0.000 description 14
• 229910052783 alkali metal Inorganic materials 0.000 description 13
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 12
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
• 229910052751 metal Inorganic materials 0.000 description 12
• 239000002184 metal Substances 0.000 description 12
• 229910052757 nitrogen Inorganic materials 0.000 description 12
• 229920000877 Melamine resin Polymers 0.000 description 11
• 239000004743 Polypropylene Substances 0.000 description 11
• 230000000996 additive effect Effects 0.000 description 11
• JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 11
• 229920001155 polypropylene Polymers 0.000 description 11
• 239000003054 catalyst Substances 0.000 description 9
• ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 8
• 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 8
• 150000003863 ammonium salts Chemical class 0.000 description 8
• KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
• ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 8
• 229920001684 low density polyethylene Polymers 0.000 description 8
• 239000004702 low-density polyethylene Substances 0.000 description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
• 229920002857 polybutadiene Polymers 0.000 description 8
• 229920002554 vinyl polymer Polymers 0.000 description 8
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
• 239000005062 Polybutadiene Substances 0.000 description 7
• 239000004698 Polyethylene Substances 0.000 description 7
• XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 7
• 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 7
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 7
• 239000012964 benzotriazole Substances 0.000 description 7
• 150000001993 dienes Chemical class 0.000 description 7
• 239000004700 high-density polyethylene Substances 0.000 description 7
• 229920000573 polyethylene Polymers 0.000 description 7
• 229920006324 polyoxymethylene Polymers 0.000 description 7
• 239000004800 polyvinyl chloride Substances 0.000 description 7
• 229920000915 polyvinyl chloride Polymers 0.000 description 7
• BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• 239000004721 Polyphenylene oxide Substances 0.000 description 6
• 229920000388 Polyphosphate Polymers 0.000 description 6
• KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• 229920001903 high density polyethylene Polymers 0.000 description 6
• 229920001519 homopolymer Polymers 0.000 description 6
• 239000000178 monomer Substances 0.000 description 6
• FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 6
• ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 6
• 235000011007 phosphoric acid Nutrition 0.000 description 6
• 229920001707 polybutylene terephthalate Polymers 0.000 description 6
• 229920000728 polyester Polymers 0.000 description 6
• 239000001205 polyphosphate Substances 0.000 description 6
• 235000011176 polyphosphates Nutrition 0.000 description 6
• 239000000126 substance Substances 0.000 description 6
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
• 239000004114 Ammonium polyphosphate Substances 0.000 description 5
• UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 5
• 239000004433 Thermoplastic polyurethane Substances 0.000 description 5
• 239000007983 Tris buffer Substances 0.000 description 5
• 150000001412 amines Chemical class 0.000 description 5
• 235000019826 ammonium polyphosphate Nutrition 0.000 description 5
• 229920001276 ammonium polyphosphate Polymers 0.000 description 5
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
• FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 5
• 239000003795 chemical substances by application Substances 0.000 description 5
• 125000003709 fluoroalkyl group Chemical group 0.000 description 5
• 239000004611 light stabiliser Substances 0.000 description 5
• TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 5
• WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
• 229920000570 polyether Polymers 0.000 description 5
• 229920000098 polyolefin Polymers 0.000 description 5
• 229920006380 polyphenylene oxide Polymers 0.000 description 5
• 229920001169 thermoplastic Polymers 0.000 description 5
• 229920002803 thermoplastic polyurethane Polymers 0.000 description 5
• KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 5
• HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 4
• DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
• ONTODYXHFBKCDK-UHFFFAOYSA-N 2-(2,4-dimethylphenyl)-1,3,5-triazine Chemical compound CC1=CC(C)=CC=C1C1=NC=NC=N1 ONTODYXHFBKCDK-UHFFFAOYSA-N 0.000 description 4
• OLFNXLXEGXRUOI-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-phenylpropan-2-yl)phenol Chemical compound C=1C(N2N=C3C=CC=CC3=N2)=C(O)C(C(C)(C)C=2C=CC=CC=2)=CC=1C(C)(C)C1=CC=CC=C1 OLFNXLXEGXRUOI-UHFFFAOYSA-N 0.000 description 4
• ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 4
• CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
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• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
• 229930185605 Bisphenol Natural products 0.000 description 4
• 0 C[N+](CC=**)[O-] Chemical compound C[N+](CC=**)[O-] 0.000 description 4
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
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• VJAMBZRWYAAZSN-UHFFFAOYSA-N bis(2,4-dinitrophenyl) carbonate Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC=C1OC(=O)OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O VJAMBZRWYAAZSN-UHFFFAOYSA-N 0.000 description 4
• 150000004649 carbonic acid derivatives Chemical class 0.000 description 4
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
• 239000007859 condensation product Substances 0.000 description 4
• 229920001971 elastomer Polymers 0.000 description 4
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• 229910052736 halogen Inorganic materials 0.000 description 4
• 150000002367 halogens Chemical class 0.000 description 4
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• XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
• 239000000843 powder Substances 0.000 description 4
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• 125000004122 cyclic group Chemical group 0.000 description 3
• GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 3
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• 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 description 1
• 229920001862 ultra low molecular weight polyethylene Polymers 0.000 description 1
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• 239000011709 vitamin E Substances 0.000 description 1
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• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
• 239000002023 wood Substances 0.000 description 1
• 150000003751 zinc Chemical class 0.000 description 1
• 239000011787 zinc oxide Substances 0.000 description 1
• GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
• 239000002446 δ-tocopherol Substances 0.000 description 1