JP2021503021A - ポリカーボネート組成物 - Google Patents
ポリカーボネート組成物 Download PDFInfo
- Publication number
- JP2021503021A JP2021503021A JP2020526361A JP2020526361A JP2021503021A JP 2021503021 A JP2021503021 A JP 2021503021A JP 2020526361 A JP2020526361 A JP 2020526361A JP 2020526361 A JP2020526361 A JP 2020526361A JP 2021503021 A JP2021503021 A JP 2021503021A
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- JP
- Japan
- Prior art keywords
- weight
- alkyl
- tert
- stabilizers
- bis
- Prior art date
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- Ceased
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- 239000000203 mixture Substances 0.000 title claims abstract description 85
- 229920000515 polycarbonate Polymers 0.000 title claims abstract description 67
- 239000004417 polycarbonate Substances 0.000 title claims abstract description 67
- 239000003381 stabilizer Substances 0.000 claims abstract description 79
- 239000000654 additive Substances 0.000 claims abstract description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 28
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims abstract description 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 24
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical class 0.000 claims abstract description 11
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 11
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 7
- 125000003396 thiol group Chemical class [H]S* 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- -1 2,4-di-α-cumylphenyl Chemical group 0.000 claims description 40
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 24
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 16
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 15
- 229910052698 phosphorus Inorganic materials 0.000 claims description 15
- 239000011574 phosphorus Substances 0.000 claims description 15
- 230000000996 additive effect Effects 0.000 claims description 13
- 125000004423 acyloxy group Chemical group 0.000 claims description 11
- 239000002530 phenolic antioxidant Substances 0.000 claims description 11
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 10
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000006096 absorbing agent Substances 0.000 claims description 9
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 8
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 claims description 7
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 7
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- SSIZLKDLDKIHEV-UHFFFAOYSA-N 2,6-dibromophenol Chemical compound OC1=C(Br)C=CC=C1Br SSIZLKDLDKIHEV-UHFFFAOYSA-N 0.000 claims description 5
- YLUZWKKWWSCRSR-UHFFFAOYSA-N 3,9-bis(8-methylnonoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCC(C)C)OCC21COP(OCCCCCCCC(C)C)OC2 YLUZWKKWWSCRSR-UHFFFAOYSA-N 0.000 claims description 5
- PZRWFKGUFWPFID-UHFFFAOYSA-N 3,9-dioctadecoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCCCCCCCCCCCC)OCC21COP(OCCCCCCCCCCCCCCCCCC)OC2 PZRWFKGUFWPFID-UHFFFAOYSA-N 0.000 claims description 5
- DKMAVLSHFTVXRU-UHFFFAOYSA-N CCCCCCCCP(O)(OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C Chemical compound CCCCCCCCP(O)(OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C DKMAVLSHFTVXRU-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 5
- 239000007983 Tris buffer Substances 0.000 claims description 5
- BEIOEBMXPVYLRY-UHFFFAOYSA-N [4-[4-bis(2,4-ditert-butylphenoxy)phosphanylphenyl]phenyl]-bis(2,4-ditert-butylphenoxy)phosphane Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(C=1C=CC(=CC=1)C=1C=CC(=CC=1)P(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C BEIOEBMXPVYLRY-UHFFFAOYSA-N 0.000 claims description 5
- 125000005262 alkoxyamine group Chemical group 0.000 claims description 5
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 5
- ZEFSGHVBJCEKAZ-UHFFFAOYSA-N bis(2,4-ditert-butyl-6-methylphenyl) ethyl phosphite Chemical compound CC=1C=C(C(C)(C)C)C=C(C(C)(C)C)C=1OP(OCC)OC1=C(C)C=C(C(C)(C)C)C=C1C(C)(C)C ZEFSGHVBJCEKAZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000000600 sorbitol Substances 0.000 claims description 5
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 claims description 5
- GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 claims description 4
- SHDUFLICMXOBPA-UHFFFAOYSA-N 3,9-bis(2,4,6-tritert-butylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1OP1OCC2(COP(OC=3C(=CC(=CC=3C(C)(C)C)C(C)(C)C)C(C)(C)C)OC2)CO1 SHDUFLICMXOBPA-UHFFFAOYSA-N 0.000 claims description 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 230000009931 harmful effect Effects 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 claims description 4
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 claims description 4
- MYMKXVFDVQUQLG-UHFFFAOYSA-N 1,3,7,9-tetratert-butyl-11-fluoro-5-methyl-5h-benzo[d][1,3,2]benzodioxaphosphocine Chemical compound CC1C2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2OP(F)OC2=C1C=C(C(C)(C)C)C=C2C(C)(C)C MYMKXVFDVQUQLG-UHFFFAOYSA-N 0.000 claims description 3
- CFTVYNZUEIVNGH-UHFFFAOYSA-N 2,4,8,10-tetratert-butyl-6-(6-methylheptoxy)benzo[d][1,3,2]benzodioxaphosphepine Chemical compound C12=CC(C(C)(C)C)=CC(C(C)(C)C)=C2OP(OCCCCCC(C)C)OC2=C1C=C(C(C)(C)C)C=C2C(C)(C)C CFTVYNZUEIVNGH-UHFFFAOYSA-N 0.000 claims description 3
- SSADPHQCUURWSW-UHFFFAOYSA-N 3,9-bis(2,6-ditert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound CC(C)(C)C1=CC(C)=CC(C(C)(C)C)=C1OP1OCC2(COP(OC=3C(=CC(C)=CC=3C(C)(C)C)C(C)(C)C)OC2)CO1 SSADPHQCUURWSW-UHFFFAOYSA-N 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 230000000087 stabilizing effect Effects 0.000 claims description 3
- IZWGOJSWVITMGN-UHFFFAOYSA-N 2-(diphenylphosphanylmethyl)butanoic acid Chemical compound C=1C=CC=CC=1P(CC(CC)C(O)=O)C1=CC=CC=C1 IZWGOJSWVITMGN-UHFFFAOYSA-N 0.000 claims description 2
- YGRVCNYIEKLRED-UHFFFAOYSA-N 4,4-diphenylbutylphosphane Chemical compound C=1C=CC=CC=1C(CCCP)C1=CC=CC=C1 YGRVCNYIEKLRED-UHFFFAOYSA-N 0.000 claims description 2
- QOPABJOZVXZFJG-UHFFFAOYSA-N 4-diphenylphosphanylphenol Chemical compound C1=CC(O)=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QOPABJOZVXZFJG-UHFFFAOYSA-N 0.000 claims description 2
- PMIAZIGUOOLXDU-UHFFFAOYSA-N CC(C)(C)C(C=C1C(C)(C)C)=CC(C)=C1OP(C)(O)OC1=C(C(C)(C)C)C=C(C(C)(C)C)C=C1C Chemical compound CC(C)(C)C(C=C1C(C)(C)C)=CC(C)=C1OP(C)(O)OC1=C(C(C)(C)C)C=C(C(C)(C)C)C=C1C PMIAZIGUOOLXDU-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- UZCPNEBHTFYJNY-UHFFFAOYSA-N benzyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1CP(C=1C=CC=CC=1)C1=CC=CC=C1 UZCPNEBHTFYJNY-UHFFFAOYSA-N 0.000 claims description 2
- PDDYFPPQDKRJTK-UHFFFAOYSA-N diphenyl(prop-2-enyl)phosphane Chemical compound C=1C=CC=CC=1P(CC=C)C1=CC=CC=C1 PDDYFPPQDKRJTK-UHFFFAOYSA-N 0.000 claims description 2
- QPECWWIZMZHSDR-UHFFFAOYSA-N diphenylphosphanylmethanol Chemical compound C=1C=CC=CC=1P(CO)C1=CC=CC=C1 QPECWWIZMZHSDR-UHFFFAOYSA-N 0.000 claims description 2
- GCDUSCPJMVWSBD-UHFFFAOYSA-N diphenylphosphanylmethyl acetate Chemical compound C=1C=CC=CC=1P(COC(=O)C)C1=CC=CC=C1 GCDUSCPJMVWSBD-UHFFFAOYSA-N 0.000 claims description 2
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- SEXLOAWGADSQPS-UHFFFAOYSA-N octadecyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CCCCCCCCCCCCCCCCCC)C1=CC=CC=C1 SEXLOAWGADSQPS-UHFFFAOYSA-N 0.000 claims description 2
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 2
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 claims description 2
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 claims description 2
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 claims description 2
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 claims description 2
- DMEUUKUNSVFYAA-UHFFFAOYSA-N trinaphthalen-1-ylphosphane Chemical compound C1=CC=C2C(P(C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 DMEUUKUNSVFYAA-UHFFFAOYSA-N 0.000 claims description 2
- IIOSDXGZLBPOHD-UHFFFAOYSA-N tris(2-methoxyphenyl)phosphane Chemical compound COC1=CC=CC=C1P(C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC IIOSDXGZLBPOHD-UHFFFAOYSA-N 0.000 claims description 2
- JNJGSDYMEKOBPD-UHFFFAOYSA-N tris(4-nonylphenyl)phosphane Chemical compound C1=CC(CCCCCCCCC)=CC=C1P(C=1C=CC(CCCCCCCCC)=CC=1)C1=CC=C(CCCCCCCCC)C=C1 JNJGSDYMEKOBPD-UHFFFAOYSA-N 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 abstract description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 9
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 6
- 150000001907 coumarones Chemical class 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000004594 Masterbatch (MB) Substances 0.000 description 5
- AIBRSVLEQRWAEG-UHFFFAOYSA-N 3,9-bis(2,4-ditert-butylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP1OCC2(COP(OC=3C(=CC(=CC=3)C(C)(C)C)C(C)(C)C)OC2)CO1 AIBRSVLEQRWAEG-UHFFFAOYSA-N 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- 238000010276 construction Methods 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 3
- VKLDCBNUFZIAFK-UHFFFAOYSA-N 1,1-bis[2,4-bis(2-phenylpropan-2-yl)phenyl]-2,2-bis(hydroxymethyl)propane-1,3-diol dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.C(C)(C)(C1=CC=CC=C1)C1=C(C=CC(=C1)C(C)(C)C1=CC=CC=C1)C(O)(C(CO)(CO)CO)C1=C(C=C(C=C1)C(C)(C)C1=CC=CC=C1)C(C)(C)C1=CC=CC=C1 VKLDCBNUFZIAFK-UHFFFAOYSA-N 0.000 description 3
- KNJXNSHXJMNRQO-UHFFFAOYSA-N 2,6-dibromophenol Chemical compound BrC1=C(C(=CC=C1)Br)O.BrC1=C(C(=CC=C1)Br)O KNJXNSHXJMNRQO-UHFFFAOYSA-N 0.000 description 3
- IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- 125000006193 alkinyl group Chemical group 0.000 description 3
- 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 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- KLDXJTOLSGUMSJ-UNTFVMJOSA-N (3s,3ar,6s,6ar)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol Chemical compound O[C@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-UNTFVMJOSA-N 0.000 description 2
- VCMZIKKVYXGKCI-UHFFFAOYSA-N 1,1-bis(2,4-ditert-butyl-6-methylphenyl)-2,2-bis(hydroxymethyl)propane-1,3-diol dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.C(C)(C)(C)C1=C(C(=CC(=C1)C(C)(C)C)C)C(O)(C(CO)(CO)CO)C1=C(C=C(C=C1C)C(C)(C)C)C(C)(C)C VCMZIKKVYXGKCI-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- CVSXFBFIOUYODT-UHFFFAOYSA-N 178671-58-4 Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)=C(C#N)C(=O)OCC(COC(=O)C(C#N)=C(C=1C=CC=CC=1)C=1C=CC=CC=1)(COC(=O)C(C#N)=C(C=1C=CC=CC=1)C=1C=CC=CC=1)COC(=O)C(C#N)=C(C=1C=CC=CC=1)C1=CC=CC=C1 CVSXFBFIOUYODT-UHFFFAOYSA-N 0.000 description 2
- LEVFXWNQQSSNAC-UHFFFAOYSA-N 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-hexoxyphenol Chemical compound OC1=CC(OCCCCCC)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 LEVFXWNQQSSNAC-UHFFFAOYSA-N 0.000 description 2
- LVLNPXCISNPHLE-UHFFFAOYSA-N 2-[(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1CC1=CC=CC=C1O LVLNPXCISNPHLE-UHFFFAOYSA-N 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- ZCILGMFPJBRCNO-UHFFFAOYSA-N 4-phenyl-2H-benzotriazol-5-ol Chemical class OC1=CC=C2NN=NC2=C1C1=CC=CC=C1 ZCILGMFPJBRCNO-UHFFFAOYSA-N 0.000 description 2
- 229920001651 Cyanoacrylate Polymers 0.000 description 2
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical class ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- OCWYEMOEOGEQAN-UHFFFAOYSA-N bumetrizole Chemical compound CC(C)(C)C1=CC(C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O OCWYEMOEOGEQAN-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 2
- NZYMWGXNIUZYRC-UHFFFAOYSA-N hexadecyl 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NZYMWGXNIUZYRC-UHFFFAOYSA-N 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
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- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 2
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- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
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- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
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- C08L2666/34—Oxygen-containing compounds, including ammonium and metal salts
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- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
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- Compositions Of Macromolecular Compounds (AREA)
- Building Environments (AREA)
- Plural Heterocyclic Compounds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Abstract
Description
ポリカーボネートと、式Iのベンゾフラノン安定剤からなる群から選択される1つ以上の添加剤と、を含む組成物が開示され、
ポリカーボネートは、縮合によって、ビスフェノールAおよびホスゲンまたはホスゲン類似体、例えばトリクロロメチルクロロホルメート、トリホスゲン、もしくはジフェニルカーボネートから得ることができ、後者の場合は通常、好適なエステル交換触媒、例えば水素化ホウ素、アミン、例えば2−メチルイミダゾール、または第四級アンモニウム塩を添加して得ることができる。ビスフェノールAに加えて、他のビスフェノール成分も使用することができ、ベンゼン核でハロゲン化されているモノマーを使用することも可能である。好適なビスフェノール成分には、例えば、2,2−ビス(4’−ヒドロキシフェニル)プロパン(ビスフェノールA)、2,4’−ジヒドロキシジフェニルメタン、ビス(2−ヒドロキシフェニル)メタン、ビス(4−ヒドロキシフェニル)メタン、ビス−(4−ヒドロキシ−5−プロピルフェニル)メタン、1,1−ビス(4’−ヒドロキシフェニル)エタン、ビス(4−ヒドロキシフェニル)シクロヘキシルメタン、2,2−ビス(4’−ヒドロキシフェニル)−1−フェニルプロパン、2,2−ビス(3’,5’−ジメチル−4’−ヒドロキシフェニル)プロパン、2,2−ビス(3’,5’−ジブロモ−4’−ヒドロキシフェニル)プロパン、2,2−ビス(3’,5’−ジクロロ−4’−ヒドロキシフェニル)プロパン、1,1−ビス(4’−ヒドロキシフェニル)シクロドデカン、1,1−ビス(3’5、’−ジメチル−4’−ヒドロキシフェニル)シクロドデカン、1,1−ビス(4’−ヒドロキシフェニル)−3,3,5−トリメチルシクロヘキサン、1,1−ビス(4’−ヒドロキシフェニル)−3,3,5,5−テトラメチルシクロヘキサン、および1,1−ビス(4’−ヒドロキシフェニル)−3,3,5−トリメチルシクロペンタンが挙げられる。ビスフェノールに加えて、ポリカーボネートは、他のジオール、例えばイソソルビド、イソイジド、およびイソマンニドを含むジアンヒドロヘキシトールから得ることができる。ポリカーボネートは、前述のジオールのうちの1つ以上、ならびにさらなるジオールを使用することができる。ポリカーボネートは、二官能性以上のモノマーの好適な量で分岐されてもよい。
第1の実施形態では、ポリカーボネートと、式Iのベンゾフラノン安定剤からなる群から選択される1つ以上の添加剤と、を含む組成物が開示され、
Claims (23)
- ポリカーボネートと、式Iのベンゾフラノン安定剤からなる群から選択される1つ以上の添加剤と、を含む組成物であって、
R1、R2、R3、R4、およびR5は、それぞれ独立して、水素、ハロゲン、ヒドロキシ、C1−C25アルキル、C2−C25アルケニル、C2−C25アルキニル、C7−C9フェニルアルキル、フェニル、C5−C8シクロアルキル、C1−C18アルコキシ、C1−C8アルキルアミン、ジ(C1−C8アルキル)アミノ、C1−C25アルカノイルオキシ、C1−C25アルカノイルアミノ、C3−C25アルケノイルオキシ、または1〜3個の−O−、−S−、−NH−、もしくは−N(C1−C8アルキル)−によって中断されたC3−C25アルカノイルオキシであり、ここで、C1−C25アルキル、C2−C25アルケニル、C2−C25アルキニル、C7−C9フェニルアルキル、フェニル、C5−C8シクロアルキル、C1−C18アルコキシ、C1−C8アルキルアミン、ジ(C1−C8アルキル)アミノ、C1−C25アルカノイルオキシ、C1−C25アルカノイルアミノ、C3−C25アルケノイルオキシ、および中断されたC3−C25アルケノイルオキシは、非置換であるか、またはハロゲン、ヒドロキシ、チオール、アミノ、C1−C4アルキルアミノ、ジ(C1−C4アルキル)アミノ、およびC1−C4アルキルから選択される1〜3個の基で置換されている、組成物。 - R1およびR2が独立して、水素またはC1−C8アルキルであり、
R3およびR4が独立して、C1−C12アルキルであり、
R5が、C1−C7アルキル、フェニル、C1−C8アルキルフェニル、3,5−ジ(C1−C8アルキル)−4−ヒドロキシフェニル、またはC1−C8アルキル(3,5−ジ(C1−C8アルキル)−4−ヒドロキシフェニル)である、請求項1に記載の組成物。 - R1およびR2が、水素であり、R3およびR4が、C1−C8アルキルである、請求項1または2に記載の組成物。
- R5が、C1−C4アルキル、フェニル、C1−C4アルキルフェニル、3,5−ジ(C1−C4アルキル)−4−ヒドロキシフェニル、またはC1−C4アルキル(3,5−ジ(C1−C4アルキル)−4−ヒドロキシフェニルである、請求項1〜3のいずれか一項に記載の組成物。
- 前記ポリカーボネートの重量に基づいて、約10重量ppm〜約1000重量ppmの前記1つ以上のベンゾフラノン安定剤を含む、請求項1〜5のいずれか一項に記載の組成物。
- 前記ポリカーボネートの重量に基づいて、約0.1重量%〜約7.0重量%の前記1つ以上のベンゾフラノン安定剤を含む、請求項1〜4のいずれか一項に記載の組成物。
- 1つ以上の有機リン安定剤を含む、請求項1〜7のいずれか一項に記載の組成物。
- 有機ホスファイト安定剤、有機ホスホナイト安定剤、および有機ホスフィン安定剤からなる群から選択される1つ以上の有機リン安定剤を含む、請求項1〜8のいずれか一項に記載の組成物。
- トリフェニルホスファイト、ジフェニルアルキルホスファイト、フェニルジアルキルホスファイト、トリス(ノニルフェニル)ホスファイト、トリラウリルホスファイト、トリオクタデシルホスファイト、ジステアリルペンタエリスリトールジホスファイト、トリス(2,4−ジ−tert−ブチルフェニル)ホスファイト、ビス(2,4−ジ−α−クミルフェニル)ペンタエリスルチトールジホスファイト、ジイソデシルペンタエリスリトールジホスファイト、ビス(2,4−ジ−tert−ブチルフェニル)ペンタエリスリトールジホスファイト、ビス(2,6−ジ−tert−ブチル−4−メチルフェニル)ペンタエリスリトールジホスファイト、ビスイソデシルオキシ−ペンタエリスリトールジホスファイト、ビス(2,4−ジ−tert−ブチル−6−メチルフェニル)ペンタエリスリトールジホスファイト、ビス(2,4,6−トリ−tert−ブチルフェニル)ペンタエリスリトールジホスファイト、トリステアリルソルビトールトリホスファイト、テトラキス(2,4−ジ−tert−ブチルフェニル)4,4’−ビフェニレン−ジホスホナイト、6−イソオクチルオキシ−2,4,8,10−テトラ−tert−ブチル−ジベンゾ[d,f][1,3,2]ジオキサホスフェピン、6−フルオロ−2,4,8,10−テトラ−tert−ブチル−12−メチル−ジベンゾ[d,g][1,3,2]ジオキサホスホシン、ビス(2,4−ジ−tert−ブチル−6−メチルフェニル)メチルホスファイト、ビス(2,4−ジ−tert−ブチル−6−メチルフェニル)エチルホスファイト、2,2’,2”−ニトリロ[トリエチルトリス(3,3’5,5’−テトラ−tert−ブチル−1,1’−ビフェニル−2,2’−ジイル)ホスファイト]、ビス(2,4−ジ−t−ブチルフェニル)オクチルホスファイト、ポリ(4,4’−{2,2’−ジメチル−5,5’−ジ−t−ブチルフェニルスルフィド−}オクチルホスファイト)、ポリ(4,4’{−イソプロピリデンジフェノール}−オクチルホスファイト)、ポリ(4,4’−{イソプロピリデンビス[2,6−ジブロモフェノール]}−オクチルホスファイト)、ポリ(4,4’−{2,2’−ジメチル−5,5’−ジ−t−ブチルフェニルスルフィド}−ペンタエリスリチルジホスファイト)、
- 前記ポリカーボネートの重量に基づいて、約10重量ppm〜約1000重量ppmの1つ以上の有機リン安定剤を含む、請求項1〜10のいずれか一項に記載の組成物。
- 前記組成物が、1つ以上のベンゾフラノン安定剤と、1つ以上の有機リン安定剤と、を含み、前記1つ以上のベンゾフラノン安定剤対前記1つ以上の有機リン安定剤の重量/重量比が、約0.05〜約1.0である、請求項1〜11のいずれか一項に記載の組成物。
- 前記組成物が、1つ以上の紫外線吸収剤を含む、請求項1〜12のいずれか一項に記載の組成物。
- 前記組成物が、ヒンダードフェノール系酸化防止剤を本質的に含まない、請求項1〜13のいずれか一項に記載の組成物。
- 請求項1〜14のいずれか一項に記載の組成物を含むフィルム、シート、または成形品。
- 約400nm〜約700nmの波長を有する光に対して透明である、請求項15に記載のフィルム、シート、または成形品。
- 自動車用ヘッドランプカバー、街路灯カバー、太陽エネルギー制御フィルム、照明器具用の反射ハウジング、および光拡散フィルムからなる群から選択される、請求項15または16に記載のフィルム、シート、または成形品。
- 請求項15〜17のいずれか一項に記載のフィルム、シート、または成形品を調製する方法であって、前記組成物を溶融混合することを含む、方法。
- 熱、光、および酸素の有害な影響に対してポリカーボネートを安定化する方法であって、請求項1に記載の式Iのベンゾフラノン安定剤からなる群から選択される1つ以上の添加剤をポリカーボネートに組み込むことを含む、方法。
- 請求項1に記載の式Iの1つ以上のベンゾフラノン安定剤と、
1つ以上の有機リン安定剤と、を含む、添加剤組成物。 - 前記1つ以上のベンゾフラノン安定剤対前記1つ以上の有機リン安定剤の重量/重量比が、約0.05〜約1.0である、請求項20に記載の組成物。
- 前記組成物が、ヒンダードフェノール系酸化防止剤を本質的に含まない、請求項20または21に記載の組成物。
- 前記組成物が、1つ以上の紫外線吸収剤を含む、請求項20〜22のいずれか一項に記載の組成物。
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