TWI841567B - 聚碳酸酯系樹脂及其製造方法、以及聚碳酸酯系樹脂組合物 - Google Patents
聚碳酸酯系樹脂及其製造方法、以及聚碳酸酯系樹脂組合物 Download PDFInfo
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- TWI841567B TWI841567B TW108119083A TW108119083A TWI841567B TW I841567 B TWI841567 B TW I841567B TW 108119083 A TW108119083 A TW 108119083A TW 108119083 A TW108119083 A TW 108119083A TW I841567 B TWI841567 B TW I841567B
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- polycarbonate resin
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- polycarbonate
- carbon atoms
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- 229920005668 polycarbonate resin Polymers 0.000 title claims abstract description 167
- 239000004431 polycarbonate resin Substances 0.000 title claims abstract description 167
- 238000004519 manufacturing process Methods 0.000 title claims description 28
- 239000000203 mixture Substances 0.000 title claims description 21
- 150000001412 amines Chemical class 0.000 claims abstract description 32
- -1 polytetrafluoroethylene Polymers 0.000 claims description 46
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- 239000004417 polycarbonate Substances 0.000 claims description 41
- 239000006085 branching agent Substances 0.000 claims description 39
- 229920000515 polycarbonate Polymers 0.000 claims description 37
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 29
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 239000003960 organic solvent Substances 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 239000003054 catalyst Substances 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 15
- 239000003963 antioxidant agent Substances 0.000 claims description 14
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 14
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 230000003078 antioxidant effect Effects 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical group OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims description 11
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 11
- 239000003063 flame retardant Substances 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 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 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- BRPSWMCDEYMRPE-UHFFFAOYSA-N 4-[1,1-bis(4-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=C(O)C=C1 BRPSWMCDEYMRPE-UHFFFAOYSA-N 0.000 claims description 8
- 239000002685 polymerization catalyst Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 150000003512 tertiary amines Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 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 28
- 239000007864 aqueous solution Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 15
- 229910052783 alkali metal Inorganic materials 0.000 description 13
- 238000000465 moulding Methods 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 229920001296 polysiloxane Polymers 0.000 description 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 10
- 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 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
- 150000001340 alkali metals Chemical class 0.000 description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 150000002989 phenols Chemical class 0.000 description 7
- 229910052700 potassium Inorganic materials 0.000 description 7
- 239000011591 potassium Substances 0.000 description 7
- 239000003513 alkali Substances 0.000 description 6
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 230000003068 static effect Effects 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 238000004898 kneading Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 150000003568 thioethers Chemical class 0.000 description 5
- PTFIPECGHSYQNR-UHFFFAOYSA-N 3-Pentadecylphenol Chemical compound CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 238000000748 compression moulding Methods 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 238000001746 injection moulding Methods 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 229910001961 silver nitrate Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- RQCACQIALULDSK-UHFFFAOYSA-N 4-(4-hydroxyphenyl)sulfinylphenol Chemical compound C1=CC(O)=CC=C1S(=O)C1=CC=C(O)C=C1 RQCACQIALULDSK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229910052792 caesium Inorganic materials 0.000 description 3
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000002485 combustion reaction Methods 0.000 description 3
- 150000001924 cycloalkanes Chemical class 0.000 description 3
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical compound [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 3
- 230000000670 limiting effect Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000002530 phenolic antioxidant Substances 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 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 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- 150000003462 sulfoxides Chemical class 0.000 description 3
- QZHDEAJFRJCDMF-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F QZHDEAJFRJCDMF-UHFFFAOYSA-M 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 2
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- VCSYXZQBBCIQCJ-UHFFFAOYSA-N 2-phenyl-4-propan-2-ylphenol Chemical compound CC(C)C1=CC=C(O)C(C=2C=CC=CC=2)=C1 VCSYXZQBBCIQCJ-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical class C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 2
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical class C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 2
- ODJUOZPKKHIEOZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 ODJUOZPKKHIEOZ-UHFFFAOYSA-N 0.000 description 2
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 2
- FUQKDGZVPBENHV-UHFFFAOYSA-N 4-[bis(3,5-dibromo-4-hydroxyphenyl)methyl]-2,6-dibromophenol Chemical compound C1=C(Br)C(O)=C(Br)C=C1C(C=1C=C(Br)C(O)=C(Br)C=1)C1=CC(Br)=C(O)C(Br)=C1 FUQKDGZVPBENHV-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- CGRTZESQZZGAAU-UHFFFAOYSA-N [2-[3-[1-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]-2-methylpropan-2-yl]-2,4,8,10-tetraoxaspiro[5.5]undecan-9-yl]-2-methylpropyl] 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCC(=O)OCC(C)(C)C2OCC3(CO2)COC(OC3)C(C)(C)COC(=O)CCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 CGRTZESQZZGAAU-UHFFFAOYSA-N 0.000 description 2
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052785 arsenic Inorganic materials 0.000 description 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 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
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- NJDNXYGOVLYJHP-UHFFFAOYSA-L disodium;2-(3-oxido-6-oxoxanthen-9-yl)benzoate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=CC(=O)C=C2OC2=CC([O-])=CC=C21 NJDNXYGOVLYJHP-UHFFFAOYSA-L 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 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
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229920002863 poly(1,4-phenylene oxide) polymer Polymers 0.000 description 2
- 238000004445 quantitative analysis Methods 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
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- 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 1
- PXLCSHVXTZAPBB-UHFFFAOYSA-N [4-(2-amino-3-hydroxypropyl)phenyl]boronic acid Chemical compound OCC(N)CC1=CC=C(B(O)O)C=C1 PXLCSHVXTZAPBB-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- JNRDSUISOREMIW-UHFFFAOYSA-M [Na+].OS(=O)(=O)c1ccccc1.Cc1ccc(cc1)S([O-])(=O)=O Chemical compound [Na+].OS(=O)(=O)c1ccccc1.Cc1ccc(cc1)S([O-])(=O)=O JNRDSUISOREMIW-UHFFFAOYSA-M 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000005370 alkoxysilyl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-UHFFFAOYSA-M 0.000 description 1
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 230000002457 bidirectional effect Effects 0.000 description 1
- 238000000071 blow moulding Methods 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- ZWRWUGGYDBHANL-UHFFFAOYSA-N butyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCC)OC1=CC=CC=C1 ZWRWUGGYDBHANL-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- RNLRCBMCGGCMJK-UHFFFAOYSA-L calcium;3-(3-sulfonatophenyl)benzenesulfonate Chemical compound [Ca+2].[O-]S(=O)(=O)C1=CC=CC(C=2C=C(C=CC=2)S([O-])(=O)=O)=C1 RNLRCBMCGGCMJK-UHFFFAOYSA-L 0.000 description 1
- SDHLBAKWSYRYHX-UHFFFAOYSA-N calcium;4-methoxynaphthalene-1-sulfonic acid Chemical compound [Ca].C1=CC=C2C(OC)=CC=C(S(O)(=O)=O)C2=C1 SDHLBAKWSYRYHX-UHFFFAOYSA-N 0.000 description 1
- MJAWRLQUGPGXEM-UHFFFAOYSA-L calcium;thiophene-2,5-disulfonate Chemical compound [Ca+2].[O-]S(=O)(=O)C1=CC=C(S([O-])(=O)=O)S1 MJAWRLQUGPGXEM-UHFFFAOYSA-L 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- VGNIIAPVRLMILS-UHFFFAOYSA-M cesium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [Cs+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F VGNIIAPVRLMILS-UHFFFAOYSA-M 0.000 description 1
- FAXNSSHWASVXKY-UHFFFAOYSA-M cesium;trifluoromethanesulfonate Chemical compound [Cs+].[O-]S(=O)(=O)C(F)(F)F FAXNSSHWASVXKY-UHFFFAOYSA-M 0.000 description 1
- NHYCGSASNAIGLD-UHFFFAOYSA-N chlorine monoxide Inorganic materials Cl[O] NHYCGSASNAIGLD-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical class OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- GLOQRSIADGSLRX-UHFFFAOYSA-N decyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCCCC)OC1=CC=CC=C1 GLOQRSIADGSLRX-UHFFFAOYSA-N 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- NMAKPIATXQEXBT-UHFFFAOYSA-N didecyl phenyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OC1=CC=CC=C1 NMAKPIATXQEXBT-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- MKZVQIIAAIPNGH-UHFFFAOYSA-N dioctyl phenyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OC1=CC=CC=C1 MKZVQIIAAIPNGH-UHFFFAOYSA-N 0.000 description 1
- KCXKCSAUAYYDLG-UHFFFAOYSA-L dipotassium;naphthalene-2,6-disulfonate Chemical compound [K+].[K+].C1=C(S([O-])(=O)=O)C=CC2=CC(S(=O)(=O)[O-])=CC=C21 KCXKCSAUAYYDLG-UHFFFAOYSA-L 0.000 description 1
- LRUDDHYVRFQYCN-UHFFFAOYSA-L dipotassium;terephthalate Chemical compound [K+].[K+].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 LRUDDHYVRFQYCN-UHFFFAOYSA-L 0.000 description 1
- ZLTIJLROZQLDAC-UHFFFAOYSA-L dipotassium;thiophene-2,5-disulfonate Chemical compound [K+].[K+].[O-]S(=O)(=O)C1=CC=C(S([O-])(=O)=O)S1 ZLTIJLROZQLDAC-UHFFFAOYSA-L 0.000 description 1
- BFCMKCZVPUQSPN-UHFFFAOYSA-L disodium;thiophene-2,5-disulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC=C(S([O-])(=O)=O)S1 BFCMKCZVPUQSPN-UHFFFAOYSA-L 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- FEDFHMISXKDOJI-UHFFFAOYSA-M lithium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F FEDFHMISXKDOJI-UHFFFAOYSA-M 0.000 description 1
- HYGFDDCMWQPLSR-UHFFFAOYSA-M lithium;1,1,2,2,3,3,4,4,5,5,6,6,7,7,7-pentadecafluoroheptane-1-sulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F HYGFDDCMWQPLSR-UHFFFAOYSA-M 0.000 description 1
- MCVFFRWZNYZUIJ-UHFFFAOYSA-M lithium;trifluoromethanesulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(F)F MCVFFRWZNYZUIJ-UHFFFAOYSA-M 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- KYWBVOVSUISYPN-UHFFFAOYSA-L magnesium;benzenesulfonate Chemical compound [Mg+2].[O-]S(=O)(=O)C1=CC=CC=C1.[O-]S(=O)(=O)C1=CC=CC=C1 KYWBVOVSUISYPN-UHFFFAOYSA-L 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- AXRSHKZFNKUGQB-UHFFFAOYSA-N octyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCC)OC1=CC=CC=C1 AXRSHKZFNKUGQB-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- SMIZARYCGYRDGF-UHFFFAOYSA-N phenyl dipropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC1=CC=CC=C1 SMIZARYCGYRDGF-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 125000002444 phloroglucinyl group Chemical group [H]OC1=C([H])C(O[H])=C(*)C(O[H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- RSCGQEBKFSGWJT-UHFFFAOYSA-M potassium;1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane-1-sulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RSCGQEBKFSGWJT-UHFFFAOYSA-M 0.000 description 1
- WFRUBUQWJYMMRQ-UHFFFAOYSA-M potassium;1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F WFRUBUQWJYMMRQ-UHFFFAOYSA-M 0.000 description 1
- GLGXXYFYZWQGEL-UHFFFAOYSA-M potassium;trifluoromethanesulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)F GLGXXYFYZWQGEL-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229940077386 sodium benzenesulfonate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HSHFKGVNYJYBCJ-UHFFFAOYSA-M sodium;1,1,2,2,2-pentafluoroethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(F)(F)C(F)(F)F HSHFKGVNYJYBCJ-UHFFFAOYSA-M 0.000 description 1
- QBJDFZSOZNDVDE-UHFFFAOYSA-M sodium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F QBJDFZSOZNDVDE-UHFFFAOYSA-M 0.000 description 1
- ZQOXGRIKWKXDIJ-UHFFFAOYSA-M sodium;1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZQOXGRIKWKXDIJ-UHFFFAOYSA-M 0.000 description 1
- REVGHZFBRYPAOO-UHFFFAOYSA-M sodium;1-benzothiophene-2-sulfonate Chemical compound [Na+].C1=CC=C2SC(S(=O)(=O)[O-])=CC2=C1 REVGHZFBRYPAOO-UHFFFAOYSA-M 0.000 description 1
- DVFFDTYHFQEBLC-UHFFFAOYSA-M sodium;anthracene-1-sulfonate Chemical compound [Na+].C1=CC=C2C=C3C(S(=O)(=O)[O-])=CC=CC3=CC2=C1 DVFFDTYHFQEBLC-UHFFFAOYSA-M 0.000 description 1
- MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 0.000 description 1
- GRONZTPUWOOUFQ-UHFFFAOYSA-M sodium;methanol;hydroxide Chemical compound [OH-].[Na+].OC GRONZTPUWOOUFQ-UHFFFAOYSA-M 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- FUAAEMCCEGHVCH-UHFFFAOYSA-L strontium;benzenesulfonate Chemical compound [Sr+2].[O-]S(=O)(=O)C1=CC=CC=C1.[O-]S(=O)(=O)C1=CC=CC=C1 FUAAEMCCEGHVCH-UHFFFAOYSA-L 0.000 description 1
- 150000008054 sulfonate salts Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- QOQNJVLFFRMJTQ-UHFFFAOYSA-N trioctyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OCCCCCCCC QOQNJVLFFRMJTQ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/045—Aromatic polycarbonates containing aliphatic unsaturation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
- C08G64/08—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen
- C08G64/081—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
- C08G64/08—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen
- C08G64/10—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen containing halogens
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
- C08G64/08—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen
- C08G64/12—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
- C08G64/14—Aromatic polycarbonates not containing aliphatic unsaturation containing a chain-terminating or -crosslinking agent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Abstract
本發明係一種聚碳酸酯系樹脂,其中胺末端相對於全部末端基之比率為1.0莫耳%以上。
Description
本發明係關於一種聚碳酸酯系樹脂及其製造方法、以及聚碳酸酯系樹脂組合物。
聚碳酸酯系樹脂之耐熱性、耐衝擊性及透明性等物性優異,而作為工程塑膠廣泛用於OA(Office Automation,辦公自動化)設備領域、電氣-電子領域、機械零件及汽車領域等各種領域。尤其是經阻燃化之聚碳酸酯系樹脂可較佳地用作電腦、筆記型或平板型電腦、各種移動終端、印表機及影印機等OA-資訊設備等之零件。
作為聚碳酸酯系樹脂之阻燃性之等級,使用UL(Underwriters Laboratories,保險商實驗室)標準(美國保險商實驗室標準)94。聚碳酸酯系樹脂與丙烯酸系樹脂、苯乙烯樹脂等具有透明性之樹脂之阻燃性相比具有優異之阻燃特性,但為了獲得UL標準所規定之較高之阻燃特性,需要防止燃燒時樹脂之滴落(drop)(專利文獻1)。
為了提高聚碳酸酯系樹脂之阻燃性,進行了如下嘗試:對聚碳酸酯系樹脂添加作為抗滴落劑之聚四氟乙烯、添加以有機鹼金屬鹽化合物及有機鹼土金屬鹽化合物為代表之有機金屬鹽化合物有用之阻燃劑、及/或使聚碳酸酯系樹脂具有支鏈結構等(專利文獻2及3)。
先前技術文獻
專利文獻
專利文獻1:日本專利特開2000-169696號公報
專利文獻2:日本專利特開2006-143949號公報
專利文獻3:日本專利第3129374號公報
[發明所欲解決之問題]
就防止滴落之觀點而言,添加聚四氟乙烯之方法有效,但現今阻燃性之要求等級進一步提高,而尋求用以賦予阻燃性之進一步方法。因此,本發明之目的在於提供一種阻燃性進一步得到改良之聚碳酸酯系樹脂。
[解決問題之技術手段]
本發明者等發現,具有特定量之胺末端之聚碳酸酯系樹脂具有更優異之阻燃性。即,本發明係關於下述[1]~[16]。
[1]一種聚碳酸酯系樹脂,其中胺末端相對於全部末端基之比率為1.0莫耳%以上。
[2]如[1]記載之聚碳酸酯系樹脂,其中上述胺末端相對於全部末端基之比率為20.0莫耳%以下。
[3]如[1]或[2]記載之聚碳酸酯系樹脂,其具有下述通式(II)所表示之重複單元。
[化1]
[式中,R1
及R2
分別獨立地表示鹵素原子、碳數1~6之烷基或碳數1~6之烷氧基;X表示單鍵、碳數1~8之伸烷基、碳數2~8之亞烷基、碳數5~15之伸環烷基、碳數5~15之亞環烷基、-S-、-SO-、-SO2
-、-O-或-CO-;a及b分別獨立地表示0~4之整數]
[4]如[1]~[3]中任一項記載之聚碳酸酯系樹脂,其中上述聚碳酸酯系樹脂包含支鏈狀聚碳酸酯系樹脂(A-1)10~100質量份、及除上述支鏈狀聚碳酸酯系樹脂(A-1)以外之芳香族聚碳酸酯系樹脂(A-2)90~0質量份。
[5]如[4]記載之聚碳酸酯系樹脂,其中上述支鏈狀聚碳酸酯系樹脂(A-1)具有下述通式(I)所表示之支鏈結構,且分支率為0.3莫耳%以上3.0莫耳%以下。
[化2]
[式中,R表示氫原子或碳數1~5之烷基,R21
~R26
分別獨立地表示氫原子、碳數1~5之烷基或鹵素原子;PC表示聚碳酸酯部分,f、g及h表示整數]
[6]如[5]記載之聚碳酸酯系樹脂,其中上述通式(I)所表示之支鏈結構為源自1,1,1-三(4-羥基苯基)乙烷之結構。
[7]如[1]~[6]中任一項記載之聚碳酸酯系樹脂,其黏度平均分子量為17,000以上28,000以下。
[8]一種聚碳酸酯系樹脂之製造方法,其具有使二元酚與光氣於有機溶劑中反應而製造聚碳酸酯低聚物之步驟(1)、及使上述聚碳酸酯低聚物、二元酚及末端封端劑反應而製造聚碳酸酯系樹脂之步驟(2),且使用相對於步驟(1)中所獲得之聚碳酸酯低聚物之氯甲酸酯基,以莫耳比計為0.002以上0.030以下之胺系觸媒作為聚合觸媒。
[9]如[8]記載之聚碳酸酯系樹脂之製造方法,其中於上述步驟(1)及/或步驟(2)中加入分支劑。
[10]如[9]記載之聚碳酸酯系樹脂之製造方法,其中上述分支劑具有下述通式(III)之結構。
[化3]
[式中,R表示氫原子或碳數1~5之烷基,R21
~R26
分別獨立地表示氫原子、碳數1~5之烷基或鹵素原子]
[11]如[9]或[10]記載之聚碳酸酯系樹脂之製造方法,其中於上述步驟(2)中進而加入上述分支劑。
[12]如[10]或[11]記載之聚碳酸酯系樹脂之製造方法,其中加入相對於上述步驟(1)及步驟(2)中所加入之二元酚、分支劑及末端封端劑之總莫耳數為0.3莫耳%以上3.0莫耳%以下之上述通式(III)所表示之上述分支劑。
[13]如[10]~[12]中任一項記載之聚碳酸酯系樹脂之製造方法,其中上述通式(III)所表示之分支劑為1,1,1-三(4-羥基苯基)乙烷。
[14]如[8]~[13]中任一項記載之聚碳酸酯系樹脂之製造方法,其中上述胺系觸媒為三級胺或其鹽。
[15]如[8]~[14]中任一項記載之聚碳酸酯系樹脂之製造方法,其中上述胺系觸媒為三乙胺。
[16]一種聚碳酸酯系樹脂組合物,其包含如[1]~[7]中任一項記載之聚碳酸酯系樹脂(A)、及選自由阻燃劑(B)、聚有機矽氧烷(C)、聚四氟乙烯(D)及抗氧化劑(E)所組成之群中之至少1種。
[發明之效果]
根據本發明,能夠獲得具有優異之阻燃性之聚碳酸酯系樹脂。
以下,分別對本發明之聚碳酸酯系樹脂及其製造方法、聚碳酸酯系樹脂組合物詳細地進行說明。於本說明書中,視為較佳之界定可任意地採用,較佳者彼此之組合可謂更佳。於本說明書中,「XX~YY」之記載意指「XX以上YY以下」。
<聚碳酸酯系樹脂>
作為本發明之第一態樣,對聚碳酸酯系樹脂進行詳細說明。
本發明之聚碳酸酯系樹脂需要胺末端相對於全部末端基之比率為1.0莫耳%以上。只要滿足該要件,聚碳酸酯系樹脂可為芳香族聚碳酸酯系樹脂及/或脂肪族聚碳酸酯系樹脂之任一者,就耐衝擊性、耐熱性及阻燃性等觀點而言,較佳為芳香族聚碳酸酯系樹脂。作為芳香族聚碳酸酯系樹脂,通常可使用藉由二元酚與碳酸酯前驅物之反應所製造之芳香族聚碳酸酯系樹脂。
聚碳酸酯系樹脂較佳為具有下述通式(II)所表示之重複單元。
[化4]
[式中,R1
及R2
分別獨立地表示鹵素原子、碳數1~6之烷基或碳數1~6之烷氧基;X表示單鍵、碳數1~8之伸烷基、碳數2~8之亞烷基、碳數5~15之伸環烷基、碳數5~15之亞環烷基、-S-、-SO-、-SO2
-、-O-或-CO-;a及b分別獨立地表示0~4之整數]
上述通式(II)中,作為R1
及R2
分別獨立表示之鹵素原子,可列舉氟原子、氯原子、溴原子、及碘原子。
作為R1
及R2
分別獨立表示之烷基,可列舉甲基、乙基、正丙基、異丙基、各種丁基(「各種」係表示包括直鏈狀及所有支鏈狀者;以下,說明書中相同)、各種戊基、及各種己基。作為R1
及R2
分別獨立表示之烷氧基,可列舉具有上述烷基作為烷基部位者。
作為X表示之伸烷基,例如可列舉亞甲基、伸乙基、三亞甲基、四亞甲基、六亞甲基等,較佳為碳數1~5之伸烷基。作為X表示之亞烷基,可列舉亞乙基、亞異丙基等。作為X表示之伸環烷基,可列舉環戊烷二基或環己烷二基、環辛烷二基等,較佳為碳數5~10之伸環烷基。作為X表示之亞環烷基,例如可列舉亞環己基、3,5,5-三甲基亞環己基、2-亞金剛烷基等,較佳為碳數5~10之亞環烷基,更佳為碳數5~8之亞環烷基。
a及b分別獨立地表示0~4之整數,較佳為0~2,更佳為0或1。
其中,較佳為a及b為0且X為單鍵或碳數1~8之伸烷基者;或a及b為0且X為碳數3之伸烷基、尤其是亞異丙基者。
所謂本發明之聚碳酸酯系樹脂「具有胺末端」,意指具有胺結構作為聚碳酸酯結構之一部分末端。若具體地列舉一例,則意指具有以下結構。聚碳酸酯系樹脂例如具有源自下文所述之末端封端劑之式(i)之結構,「具有胺末端」意指具有式(ii)所表示之胺末端結構作為一部分末端。胺末端之存在及其量可藉由核磁共振(NMR)測定進行確認及算出。關於更多詳情,於實施例中進行記載。
[化5]
[式中,R11
及R12
分別獨立地表示經取代或未經取代之碳數1~6之烷基、經取代或未經取代之碳數5~8之環烷基、或經取代或未經取代之碳數6~12之芳基]
作為R11
及R12
所表示之碳數1~6之烷基,例如可列舉甲基、乙基、丁基、丙基等,作為碳數5~8之環烷基,可列舉環己基,作為碳數6~12之芳基,可列舉苯基。其中,特別是R11
及R12
兩者均為乙基之胺末端尤佳。
如上所述,本發明之聚碳酸酯系樹脂需要包含相對於全部末端基為1.0莫耳%以上之上述胺末端。若胺末端量未達1.0莫耳%,則阻燃性較差。
本發明之聚碳酸酯系樹脂中之胺末端相對於全部末端基之量較佳為2.0莫耳%以上,更佳為3.0莫耳%以上,進而較佳為4.0莫耳%以上;且
較佳為20.0莫耳%以下,更佳為10.0莫耳%以下,進而更佳為7.0莫耳%以下,尤佳為5.0莫耳%以下。只要胺末端之量範圍為20.0莫耳%以下,則可獲得良好之阻燃性。
本發明之聚碳酸酯系樹脂較佳為具有17,000以上28,000以下之黏度平均分子量(Mv)。上述黏度平均分子量可使用分子量調節劑(末端封端劑)等、或藉由反應條件進行調整。藉由將黏度平均分子量設為上述範圍,可製成阻燃性更優異之聚碳酸酯系樹脂。
黏度平均分子量(Mv)更佳為19,000以上,進而較佳為20,000以上。關於其上限值,就成形性之觀點而言,更佳為27,500以下,進而較佳為26,000以下,進而更佳為25,500以下,尤佳為22,500以下。
上述黏度平均分子量(Mv)係測定20℃下之二氯甲烷溶液之極限黏度[η]並根據下述Schnell之式所算出之值。
[數1]
進一步具體而言,本發明之聚碳酸酯系樹脂更佳為包含支鏈狀聚碳酸酯系樹脂(A-1)10~100質量份及除上述支鏈狀聚碳酸酯系樹脂(A-1)以外之芳香族聚碳酸酯系樹脂(A-2)90~0質量份。支鏈狀聚碳酸酯系樹脂(A-1)更佳為30~100質量份,進而較佳為40~100質量份,芳香族聚碳酸酯系樹脂(A-2)更佳為70~0質量份,進而較佳為60~0質量份。藉由以上述範圍之量包含支鏈狀聚碳酸酯系樹脂(A-1),能夠進一步提高聚碳酸酯系樹脂之阻燃性。
<支鏈狀聚碳酸酯系樹脂(A-1)>
支鏈狀聚碳酸酯系樹脂(A-1)只要為支鏈狀之聚碳酸酯系樹脂,則並無特別限定,例如可列舉具有上述通式(II)所表示之重複單元且具有下述通式(I)所表示之支鏈結構者。
[化6]
[式中,R表示氫原子或碳數1~5之烷基,R21
~R26
分別獨立地表示氫原子、碳數1~5之烷基或鹵素原子;PC表示聚碳酸酯部分,f、g及h表示整數]
式(I)中PC所表示之聚碳酸酯部分具有上述通式(II)所表示之重複單元,作為具體例,表示下述式(IV)所表示之源自雙酚A之重複單元。關於獲得支鏈狀聚碳酸酯系樹脂(A-1)時所使用之分支劑或原料二元酚,於下文進行敍述。
[化7]
支鏈狀聚碳酸酯系樹脂(A-1)較佳為具有上述通式(I)所表示之支鏈結構,且分支率為0.3莫耳%以上3.0莫耳%以下。藉由使支鏈狀聚碳酸酯系樹脂(A-1)之分支率率成為上述範圍,能夠更為提高本發明之聚碳酸酯系樹脂之阻燃性。於本說明書中,「分支率」意指源自分支劑之結構單元之莫耳數相對於支鏈聚碳酸酯系樹脂(A-1)之製造所使用之源自二元酚之結構單元、源自分支劑之結構單元及末端單元之總莫耳數(源自分支劑之結構單元之莫耳數/(源自二元酚之結構單元+源自分支劑之結構單元+末端單元)之總莫耳數×100(以mol%表示))。分支率可藉由1
H-NMR測定進行實測。
於聚碳酸酯系樹脂之製造時,藉由加入相對於作為支鏈狀聚碳酸酯系樹脂(A-1)之原料之二元酚、分支劑及末端封端劑之總莫耳數為0.3莫耳%以上3.0莫耳%以下之下述分支劑,能夠獲得具有上述範圍之分支率之支鏈狀聚碳酸酯系樹脂。
就獲得更優異之阻燃性之觀點而言,支鏈狀聚碳酸酯系樹脂(A-1)之分支率更佳為0.5莫耳%以上,進而較佳為1.0莫耳%以上,進而更佳為1.2莫耳%以上,進而更佳為1.4莫耳%以上,尤佳為1.5莫耳%以上。就獲得更良好之物性之觀點而言,支鏈狀聚碳酸酯系樹脂(A-1)之分支率更佳為2.5莫耳%以下,進而較佳為2.3莫耳%以下,進而更佳為2.0莫耳%以下。支鏈核結構可源自單獨之分支劑,亦可源自2種以上分支劑。其中,進而較佳為上述通式(I)所表示之支鏈結構具有作為源自1,1,1-三(4-羥基苯基)乙烷之結構之支鏈結構。
<芳香族聚碳酸酯系樹脂(A-2)>
芳香族聚碳酸酯系樹脂(A-2)係除上述支鏈狀聚碳酸酯系樹脂(A-1)以外之非支鏈狀聚碳酸酯系樹脂,如上所述,較佳為具有通式(II)所表示之重複單元。
[化8]
[式中,R1
、R2
、X、a及b如上所述]
其中,較佳為a及b為0且X為單鍵或碳數1~8之伸烷基者;或者a及b為0且X為亞烷基、尤其是亞異丙基者。再者,作為芳香族聚碳酸酯系樹脂(A-2),亦可包含複數種聚碳酸酯嵌段。
於作為芳香族聚碳酸酯系樹脂(A-2)包含複數種聚碳酸酯嵌段之情形時,就透明性之觀點而言,較佳為a及b為0且X為亞異丙基者較佳為90質量%以上,更佳為90.9質量%以上,進而較佳為93.3質量%以上,尤佳為95質量%以上,最佳為100質量%。
<聚碳酸酯系樹脂之製造方法>
繼而,作為本發明之第二態樣,對聚碳酸酯系樹脂之製造方法進行詳細說明。
本發明之聚碳酸酯系樹脂具有使二元酚與光氣於有機溶劑中反應而製造聚碳酸酯低聚物之步驟(1);及使上述聚碳酸酯低聚物、二元酚及末端封端劑反應而製造聚碳酸酯系樹脂之步驟(2),且使用相對於步驟(1)中所獲得之聚碳酸酯低聚物之氯甲酸酯基以莫耳比計為0.002以上0.030以下之胺系觸媒作為聚合觸媒。
作為有機溶劑,可列舉能夠溶解聚碳酸酯系樹脂之溶劑。具體而言,可列舉二氯甲烷(methylene chloride)、二氯乙烷、三氯乙烷、四氯乙烷、五氯乙烷、六氯乙烷、二氯乙烯、氯苯、二氯苯等鹵化烴溶劑,尤佳為二氯甲烷。
<步驟(1)>
於本步驟中,使二元酚與光氣於有機溶劑中反應,製造具有氯甲酸酯基之聚碳酸酯低聚物。
作為二元酚,較佳為使用下述通式(iii)所表示之化合物。
[化9]
式中,R1
、R2
、a、b及X如上所述。
作為上述通式(iii)所表示之二元酚,例如可列舉:2,2-雙(4-羥基苯基)丙烷[雙酚A]、雙(4-羥基苯基)甲烷、1,1-雙(4-羥基苯基)乙烷、2,2-雙(4-羥基-3,5-二甲基苯基)丙烷等雙(羥基苯基)烷烴系、4,4'-二羥基聯苯、雙(4-羥基苯基)環烷烴、雙(4-羥基苯基)氧化物、雙(4-羥基苯基)硫醚、雙(4-羥基苯基)碸、雙(4-羥基苯基)亞碸、雙(4-羥基苯基)酮等。該等二元酚可單獨使用1種,亦可將2種以上混合使用。
該等之中,較佳為雙(羥基苯基)烷烴系二元酚,更佳為雙酚A。於使用雙酚A作為二元酚之情形時,成為上述通式(II)中X為亞異丙基且a=b=0之聚碳酸酯系樹脂。
作為除雙酚A以外之二元酚,例如可列舉:雙(羥基芳基)烷烴類、雙(羥基芳基)環烷烴類、二羥基芳基醚類、二羥基二芳基硫醚類、二羥基二芳基亞碸類、二羥基二芳基碸類、二羥基聯苯類、二羥基二芳基茀類、二羥基二芳基金剛烷類等。該等二元酚可單獨使用1種,亦可將2種以上混合使用。
作為雙(羥基芳基)烷烴類,例如可列舉:雙(4-羥基苯基)甲烷、1,1-雙(4-羥基苯基)乙烷、2,2-雙(4-羥基苯基)丁烷、2,2-雙(4-羥基苯基)辛烷、雙(4-羥基苯基)苯基甲烷、雙(4-羥基苯基)二苯基甲烷、2,2-雙(4-羥基-3-甲基苯基)丙烷、雙(4-羥基苯基)萘基甲烷、1,1-雙(4-羥基-3-第三丁基苯基)丙烷、2,2-雙(4-羥基-3-溴苯基)丙烷、2,2-雙(4-羥基-3,5-二甲基苯基)丙烷、2,2-雙(4-羥基-3-氯苯基)丙烷、2,2-雙(4-羥基-3,5-二氯苯基)丙烷、2,2-雙(4-羥基-3,5-二溴苯基)丙烷等。
作為雙(羥基芳基)環烷烴類,例如可列舉:1,1-雙(4-羥基苯基)環戊烷、1,1-雙(4-羥基苯基)環己烷、1,1-雙(4-羥基苯基)-3,5,5-三甲基環己烷、2,2-雙(4-羥基苯基)降𦯉烷、1,1-雙(4-羥基苯基)環十二烷等。作為二羥基芳基醚類,例如可列舉4,4'-二羥基二苯基醚、4,4'-二羥基-3,3'-二甲基苯基醚等。
作為二羥基二芳基硫醚類,例如可列舉4,4'-二羥基二苯基硫醚、4,4'-二羥基-3,3'-二甲基二苯基硫醚等。作為二羥基二芳基亞碸類,例如可列舉4,4'-二羥基二苯基亞碸、4,4'-二羥基-3,3'-二甲基二苯基亞碸等。作為二羥基二芳基碸類,例如可列舉4,4'-二羥基二苯基碸、4,4'-二羥基-3,3'-二甲基二苯基碸等。
作為二羥基聯苯類,例如可列舉4,4'-二羥基聯苯等。作為二羥基二芳基茀類,例如可列舉9,9-雙(4-羥基苯基)茀、9,9-雙(4-羥基-3-甲基苯基)茀等。作為二羥基二芳基金剛烷類,例如可列舉1,3-雙(4-羥基苯基)金剛烷、2,2-雙(4-羥基苯基)金剛烷、1,3-雙(4-羥基苯基)-5,7-二甲基金剛烷等。
作為除上述以外之二元酚,例如可列舉4,4'-[1,3-伸苯基雙(1-甲基亞乙基)]雙酚、10,10-雙(4-羥基苯基)-9-蒽酮、1,5-雙(4-羥基苯基硫)-2,3-二氧雜戊烷等。
光氣通常為使用活性碳作為觸媒並以相對於1莫耳之氯、一氧化碳為1.01~1.3莫耳之比例使氯及一氧化碳反應而獲得之化合物。於使用之光氣中,於以碳醯氯(phosgene gas)之形式使用之情形時,可使用包含1~30體積%左右之未反應之一氧化碳之碳醯氯。又,亦可使用液化狀態之光氣。
於步驟(1)中製造聚碳酸酯低聚物時,將二元酚之鹼水溶液、光氣、有機溶劑導入至反應器內並使該等進行反應。關於有機溶劑之使用量,較理想為以有機溶劑相與水相之體積比成為5/1~1/7、較佳為2/1~1/4之方式進行選定。於反應器內,由於藉由光氣使二元酚之末端基進行氯甲酸酯化之反應、或藉由鹼使光氣分解之反應會引起發熱,而反應產物之溫度會變高。因此,較佳為以反應產物之溫度成為0~50℃、較佳為5~40℃之方式進行冷卻。關於光氣之使用量,較佳為以相對於二元酚1莫耳成為過量之1.1~1.5莫耳之方式使用光氣。反應後所獲得之反應液係分離成水相與有機相,而獲得包含聚碳酸酯低聚物之有機相。所獲得之聚碳酸酯低聚物之重量平均分子量通常為5,000以下,聚合度通常為20聚體以下,較佳為2~10聚體。
於上述聚碳酸酯低聚物之製造時,為了促進反應,亦可使用後續之步驟(2)中所使用之胺系聚合觸媒。亦可使用作為聚碳酸酯之分子量調節劑來使用之末端封端劑。作為末端封端劑所使用之化合物,例如可列舉:苯酚、對甲酚、對第三丁基苯酚、對第三辛基苯酚、對異丙苯基苯酚、3-十五烷基苯酚、溴苯酚、三溴苯酚、壬基苯酚等一元酚。該等之中,就經濟性、取得之容易性等方面而言,較佳為對第三丁基苯酚、對異丙苯基苯酚及苯酚。又,能夠大幅提昇藉由使用3-十五烷基苯酚所獲得之聚碳酸酯之流動性。
製造聚碳酸酯低聚物時所使用之反應器較佳為靜止型混合器,即靜態混合器(static mixer)。靜止型混合器較佳為於內部具備具有使流體分開、轉換、反轉之作用之元件的管狀反應器。藉由於靜止型混合器之後進而使用具有攪拌機之槽型攪拌槽,可促進低聚物化,故而較佳為組合使用此種反應器。
藉由步驟(1)可獲得包含具有氯甲酸酯基之聚碳酸酯低聚物之反應混合液。反應混合液係藉由使用靜置分離等分離方法而分離成包含聚碳酸酯低聚物之有機相與水相,包含聚碳酸酯低聚物之有機相係於下文所述之步驟(2)中使用。
<步驟(2)>
於步驟(2)中,使步驟(1)中所獲得之聚碳酸酯低聚物、及二元酚與末端封端劑進行反應而製造聚碳酸酯系樹脂。
步驟(2)中,使聚碳酸酯低聚物與二元酚進行縮聚反應,而將分子量調整至目標之分子量範圍。進行縮聚反應直至所獲得之聚碳酸酯系樹脂之黏度平均分子量成為上述範圍內。
具體而言,將步驟(1)中所分離之包含聚碳酸酯低聚物之有機溶劑相、根據所需所使用之末端封端劑、根據所需所使用之聚合觸媒、有機溶劑、鹼水溶液、及二元酚之鹼水溶液進行混合,於通常0~50℃、較佳為20~40℃之範圍之溫度下進行界面縮聚。
作為本步驟中所使用之鹼水溶液之鹼、有機溶劑、末端封端劑,可列舉與上述步驟(1)中所說明者相同者。步驟(2)中之有機溶劑之使用量通常以有機相與水相之體積比成為較佳為7/1~1/1、更佳為5/1~2/1之方式進行選擇。
關於步驟(2)中所使用之反應器,根據反應器之處理能力,僅利用1座反應器便可完成反應,可視需要使用後續之第2基之反應器、進而第3基之反應器等複數個反應器。作為該等反應器,可使用攪拌槽、多段塔型攪拌槽、無攪拌槽、靜態混合器、管路混合機(line mixer)、孔口混合機、及/或配管等。
所獲得之反應液由於具有包含聚碳酸酯系樹脂之有機溶劑相及包含未反應之二元酚之水相,故而進行油水分離。作為分離裝置,可列舉靜置分離槽或離心分離機。針對所分離之包含聚碳酸酯系樹脂之有機溶劑相依序進行鹼洗淨、酸洗淨及純水洗淨,獲得精製過之包含聚碳酸酯系樹脂之有機溶劑相。將精製過之包含聚碳酸酯系樹脂之有機溶劑相視需要進行濃縮,繼而進行捏合機處理或溫水造粒等,藉此可獲得聚碳酸酯系樹脂之粉體。由於在所獲得之聚碳酸酯系樹脂之粉體中殘留有有機溶劑,故而藉由進行加熱處理等乾燥處理,可獲得去除了有機溶劑之聚碳酸酯系樹脂粉體。所獲得之聚碳酸酯系樹脂粉體可使用造粒機等進行顆粒化而製成各種成形體。
<分支劑>
藉由加入任意之分支劑,可製造支鏈聚碳酸酯系樹脂(A-1)。藉由不加入分支劑,可製造芳香族聚碳酸酯系樹脂(A-2)。分支劑於上述步驟(1)及/或(2)中均可加入。於在步驟(1)中加入時,與二元酚及光氣一併加入而進行反應。雖根據所使用之分支劑而不同,但由於下文所述之通式(III)所表示之分支劑可溶解於鹼水溶液中,故而較理想為溶解於鹼水溶液中而導入。又,難以溶解於鹼水溶液中之分支劑較理想為溶解於二氯甲烷等有機溶劑中而導入。
分支劑可於步驟(1)或步驟(2)之任一步驟、或步驟(1)及(2)之兩個步驟中加入。亦可於步驟(2)中進而加入分支劑。關於分支劑之添加量,以於步驟(1)及步驟(2)中所加入之分支劑之合計量計,較佳為相對於作為原料之二元酚、分支劑及末端封端劑之總莫耳數,最終加入0.3莫耳%以上3.0莫耳%以下。藉由設為上述添加量,能夠獲得具有上述較佳之分支率之支鏈聚碳酸酯系樹脂(A-1)。關於上述分支劑相對於二元酚、分支劑及末端封端劑之總莫耳數之添加量,就獲得更優異之阻燃性之觀點而言,更佳為0.5莫耳%以上,進而較佳為1.0莫耳%以上,進而更佳為1.2莫耳%以上,進而更佳為1.4莫耳%以上,尤佳為1.5莫耳%以上,就獲得更良好之物性之觀點而言,更佳為2.5莫耳%以下,進而較佳為2.3莫耳%以下,進而更佳為2.0莫耳%以下。藉由將分支劑之添加量設為上述範圍內,能夠獲得更優異之阻燃性。
具體而言,於製造上述通式(I)所表示之支鏈聚碳酸酯系樹脂時,使用下述通式(III)所表示之分支劑。
[化10]
[式中,R表示氫原子或碳數1~5之烷基,R21
~R26
分別獨立地表示氫原子、碳數1~5之烷基或鹵素原子]
針對上述通式(III)所表示之分支劑進一步詳細說明。
R所表示之碳數1~5之烷基例如為甲基、乙基、正丙基、正丁基或正戊基等。作為R21
~R26
所表示之碳數1~5之烷基,例如可列舉甲基、乙基、正丙基、正丁基、正戊基等,作為鹵素原子,例如可列舉氯原子、溴原子、氟原子等。
關於通式(III)所表示之分支劑,更具體而言,為1,1,1-三(4-羥基苯基)甲烷;1,1,1-三(4-羥基苯基)乙烷;1,1,1-三(4-羥基苯基)丙烷;1,1,1-三(2-甲基-4-羥基苯基)甲烷;1,1,1-三(2-甲基-4-羥基苯基)乙烷;1,1,1-三(3-甲基-4-羥基苯基)甲烷;1,1,1-三(3-甲基-4-羥基苯基)乙烷;1,1,1-三(3,5-二甲基-4-羥基苯基)甲烷;1,1,1-三(3,5-二甲基-4-羥基苯基)乙烷;1,1,1-三(3-氯-4-羥基苯基)甲烷;1,1,1-三(3-氯-4-羥基苯基)乙烷;1,1,1-三(3,5-二氯-4-羥基苯基)甲烷;1,1,1-三(3,5-二氯-4-羥基苯基)乙烷;1,1,1-三(3-溴-4-羥基苯基)甲烷;1,1,1-三(3-溴-4-羥基苯基)乙烷;1,1,1-三(3,5-二溴-4-羥基苯基)甲烷;1,1,1-三(3,5-二溴-4-羥基苯基)乙烷、4,4'-[1-[4-[1-(4-羥基苯基)-1-甲基乙基]苯基]亞乙基]雙酚;α,α',α''-三(4-羥基苯基)-1,3,5-三異丙基苯;1-[α-甲基-α-(4'-羥基苯基)乙基]-4-[α',α'-雙(4''-羥基苯基)乙基]苯;間苯三酚、偏苯三甲酸、靛紅雙(鄰甲酚)等具有3個以上官能基之化合物等。上述中,就取得性、反應性及經濟性之觀點而言,較佳為使用1,1,1-三(4-羥基苯基)乙烷(以下,有時亦略記為THPE)。
<聚合觸媒>
聚合觸媒於上述步驟(1)及步驟(2)中均可使用,於本發明中係使用胺系觸媒。
作為胺系觸媒,可使用三級胺或其鹽、或四級銨鹽。作為三級胺,例如可列舉三乙胺、三丁基胺、N,N-二甲基環己胺、吡啶、二甲基苯胺等,又,作為三級胺鹽,可列舉該等三級胺之鹽酸鹽、溴酸鹽等。作為四級銨鹽,例如可列舉:氯化三甲基苄基銨、氯化三乙基苄基銨、氯化三丁基苄基銨、氯化三辛基甲基銨、氯化四丁基銨、溴化四丁基銨等。作為胺系觸媒,較佳為三級胺,尤佳為三乙胺。該等觸媒若為液體狀態者,則可直接、或溶解於有機溶劑或水中而導入。又,固體狀態者可溶解於有機溶劑或水中而導入。
於在步驟(2)中使用聚合觸媒之情形時,相對於步驟(1)中所獲得之聚碳酸酯低聚物之氯甲酸酯基,以莫耳比計為0.002以上0.030以下。若於步驟(2)中加入之聚合觸媒之量處於上述範圍內,則能夠提高所獲得之聚碳酸酯系樹脂之阻燃性。上述添加量為遠高於通常之觸媒添加量之量,但本發明者等人發現:藉由將步驟(2)中之聚合觸媒量設為上述範圍,能夠提昇所獲得之聚碳酸酯系樹脂之阻燃性。
關於步驟(2)中所加入之聚合觸媒之量,相對於聚碳酸酯低聚物之氯甲酸酯基,以莫耳比計更佳為0.004以上,進而較佳為0.006以上,進而更佳為0.010以上,進而更佳為0.015以上,更佳為0.025以下,進而較佳為0.020以下。
<聚碳酸酯系樹脂組合物>
根據本發明之第三態樣,能夠獲得包含聚碳酸酯系樹脂(A)、及選自由阻燃劑(B)、聚有機矽氧烷(C)、聚四氟乙烯(D)及抗氧化劑(E)所組成之群中之至少1種之聚碳酸酯系樹脂組合物。
作為聚碳酸酯系樹脂(A),使用於本發明之第一態樣及第二態樣中詳細說明之聚碳酸酯系樹脂。
<阻燃劑(B)>
為了進一步提昇阻燃性,於本發明之聚碳酸酯系樹脂組合物中可調配阻燃劑。
阻燃劑並無特別限定,可使用公知者,具體而言,可列舉有機鹼金屬鹽及有機鹼土金屬鹽。該等可單獨使用1種或可將2種以上組合使用。作為阻燃劑(B),較佳為有機鹼金屬鹽及有機鹼土金屬鹽之任1種。
作為上述鹼金屬或鹼土金屬(以下,有時將兩者合併記載為「鹼(土類)金屬」)之有機磺酸鹽,可列舉全氟烷烴磺酸與鹼金屬或鹼土金屬之金屬鹽之類之氟取代烷基磺酸之金屬鹽、以及芳香族磺酸與鹼金屬或鹼土金屬之金屬鹽等。
作為鹼金屬,可列舉鋰、鈉、鉀、銣及銫。作為鹼土金屬,可列舉鈹、鎂、鈣、鍶及鋇。更佳為鹼金屬。
該等鹼金屬之中,就阻燃性及熱穩定性之觀點而言,較佳為鉀及鈉,尤佳為鉀。亦可將鉀鹽與其他包含鹼金屬之磺酸鹼金屬鹽併用。
作為全氟烷烴磺酸鹼金屬鹽之具體例,例如可列舉全氟丁烷磺酸鉀、三氟甲烷磺酸鉀、全氟己烷磺酸鉀、全氟辛烷磺酸鉀、五氟乙烷磺酸鈉、全氟丁烷磺酸鈉、全氟辛烷磺酸鈉、三氟甲烷磺酸鋰、全氟丁烷磺酸鋰、全氟庚烷磺酸鋰、三氟甲烷磺酸銫、全氟丁烷磺酸銫、全氟辛烷磺酸銫、全氟己烷磺酸銫、全氟丁烷磺酸銣及全氟己烷磺酸銣等,該等可使用1種或將2種以上併用而使用。
全氟烷基之碳數較佳為1~18,更佳為1~10,進而較佳為1~8。
該等之中,尤佳為全氟丁烷磺酸鉀。
作為芳香族磺酸鹼(土類)金屬鹽之具體例,例如可列舉:二苯硫醚-4,4'-二磺酸二鈉、二苯硫醚-4,4'-二磺酸二鉀、間苯二甲酸5-磺酸鉀、間苯二甲酸5-磺酸鈉、聚乙烯對苯二甲酸聚磺酸多鈉、1-甲氧基萘-4-磺酸鈣、4-十二烷基苯基醚二磺酸二鈉、聚(2,6-二甲基苯醚)聚磺酸多鈉、聚(1,3-苯醚)聚磺酸多鈉、聚(1,4-苯醚)聚磺酸多鈉、聚(2,6-二苯基苯醚)聚磺酸多鉀、聚(2-氟-6-丁基苯醚)聚磺酸鋰、苯磺酸鉀、苯磺酸鈉、對甲苯磺酸鈉、苯磺酸鍶、苯磺酸鎂、對苯二磺酸二鉀、萘-2,6-二磺酸二鉀、聯苯基-3,3'-二磺酸鈣、二苯基碸-3-磺酸鈉、二苯基碸-3-磺酸鉀、二苯基碸-3,3'-二磺酸二鉀、二苯基碸-3,4'-二磺酸二鉀、α,α,α-三氟苯乙酮-4-磺酸鈉、二苯甲酮-3,3'-二磺酸二鉀、噻吩-2,5-二磺酸二鈉、噻吩-2,5-二磺酸二鉀、噻吩-2,5-二磺酸鈣、苯并噻吩磺酸鈉、二苯基亞碸-4-磺酸鉀、萘磺酸鈉之福馬林縮合物、及蒽磺酸鈉之福馬林縮合物等。
該等芳香族磺酸鹼(土類)金屬鹽中,尤佳為鈉鹽及鉀鹽。
關於本發明之聚碳酸酯系樹脂組合物中之阻燃劑(B)之含量,相對於聚碳酸酯系樹脂(A)100質量份,較佳為0.001~1質量份,更佳為0.01~0.1質量份,進而較佳為0.02~0.08質量份。只要為0.001質量份以上,則可獲得充分之阻燃性,只要為1質量份以下,則可抑制模具之污染。
<聚有機矽氧烷(C)>
本發明之聚碳酸酯系樹脂組合物亦可含有聚有機矽氧烷(C)。聚有機矽氧烷(C)就維持成形品之機械強度或穩定性、耐熱性等特性之方面而言較佳。
作為聚有機矽氧烷(C),並無特別限定,例如可列舉烷基氫聚矽氧、烷氧基聚矽氧等。作為烷基氫聚矽氧,例如可列舉甲基氫聚矽氧、乙基氫聚矽氧等,作為烷氧基聚矽氧,例如可列舉甲氧基聚矽氧、乙氧基聚矽氧等。
其中,尤佳為可使用烷氧基聚矽氧作為聚有機矽氧烷(C)。烷氧基聚矽氧具體而言係包含烷氧基直接或經由二價烴基鍵結至矽原子之烷氧基矽烷基的聚矽氧化合物。例如可列舉直鏈狀、環狀、網狀及於一部分具有支鏈之直鏈狀聚有機矽氧烷,尤佳為直鏈狀聚有機矽氧烷。更具體而言,較佳為具有相對於聚矽氧主鏈經由亞甲基鏈與烷氧基鍵結之分子結構之聚有機矽氧烷。
作為聚有機矽氧烷(C),例如可較佳地使用市售之Dow Corning Toray(股)製造之SH1107、SR2402、BY16-160、BY16-161、BY16-160E、BY16-161E、信越化學工業(股)製造之KR511等。
關於本發明之聚碳酸酯系樹脂組合物中之聚有機矽氧烷(C)之含量,相對於聚碳酸酯系樹脂(A)100質量份,較佳為0.05~0.30質量份,更佳為0.05~0.20質量份,進而較佳為0.07~0.15質量份。只要為0.05質量份以上,則不易引起聚碳酸酯系樹脂之劣化,可抑制樹脂之分子量之降低,只要為0.30質量份以下,則經濟性之平衡良好,並且於成形體表面不會產生銀紋等,能夠良好地保持成形品之外觀。
<聚四氟乙烯(D)>
為了提昇抗滴落效果或阻燃性,可於本發明之聚碳酸酯系樹脂組合物中調配聚四氟乙烯(D)。
作為聚四氟乙烯(D),並無特別限定,可使用公知者,較佳為水性分散型之聚四氟乙烯、經丙烯酸被覆之聚四氟乙烯。藉由使用水性分散型或經丙烯酸被覆之聚四氟乙烯,能夠抑制外觀不良。例如若使用固定量之粉體之聚四氟乙烯,則有引起凝集而生成凝集體從而導致有損成形品之外觀之虞。
關於本發明之聚碳酸酯系樹脂組合物中之聚四氟乙烯(D)之含量,相對於聚碳酸酯系樹脂(A)成分100質量份,較佳為0質量份以上0.5質量份以下,更佳為0質量份以上0.3質量份以下。只要為上述範圍內,則能夠進一步抑制聚四氟乙烯之凝集體之生成。
<抗氧化劑(E)>
本發明之聚碳酸酯系樹脂組合物可視需要包含抗氧化劑。作為抗氧化劑,可使用公知者,較佳為可使用酚系抗氧化劑及磷系抗氧化劑。抗氧化劑可單獨使用1種,亦可將2種以上組合使用。
作為酚系抗氧化劑,例如可列舉:三乙二醇-雙[3-(3-第三丁基-5-甲基-4-羥基苯基)丙酸酯]、1,6-己二醇-雙[3-(3,5-二-第三丁基-4-羥基苯基)丙酸酯]、季戊四醇-四[3-(3,5-二-第三丁基-4-羥基苯基)丙酸酯]、3-(3,5-二-第三丁基-4-羥基苯基)丙酸十八烷基酯、1,3,5-三甲基-2,4,6-三(3,5-二-第三丁基-4-羥基苄基)苯、N,N-六亞甲基雙(3,5-二-第三丁基-4-羥基-氫肉桂醯胺)、3,5-二-第三丁基-4-羥基-苄基膦酸二乙酯、三(3,5-二-第三丁基-4-羥基苄基)異氰尿酸酯、3,9-雙[1,1-二甲基-2-[β-(3-第三丁基-4-羥基-5-甲基苯基)丙醯氧基]乙基]-2,4,8,10-四氧雜螺(5,5)十一烷等。
具體而言,作為酚系抗氧化劑,可列舉Irganox 1010(BASF公司製造,商標)、Irganox 1076(BASF公司製造,商標)、Irganox 1330(BASF公司製造,商標)、Irganox 3114(BASF公司製造,商標)、Irganox 3125(BASF公司製造,商標)、BHT(武田藥品工業(股)製造,商標)、Cyanox 1790(Cyanamid公司製造,商標)及Sumilizer GA-80(住友化學(股)製造,商標)等市售品。
作為磷系抗氧化劑,例如可列舉:亞磷酸三苯酯、亞磷酸三(壬基苯基)酯、亞磷酸三(2,4-二-第三丁基苯基)酯、亞磷酸十三烷酯、亞磷酸三辛酯、亞磷酸三(十八烷基)酯、亞磷酸二癸基單苯基酯、亞磷酸二辛基單苯基酯、亞磷酸二異丙基單苯基酯、亞磷酸單丁基二苯基酯、亞磷酸單癸基二苯基酯、亞磷酸單辛基二苯基酯、雙(2,6-二-第三丁基-4-甲基苯基)季戊四醇二亞磷酸酯、2,2-亞甲基雙(4,6-二-第三丁基苯基)辛基亞磷酸酯、雙(壬基苯基)季戊四醇二亞磷酸酯、雙(2,4-二-第三丁基苯基)季戊四醇二亞磷酸酯、二硬脂基季戊四醇二亞磷酸酯等。
具體而言,作為磷系抗氧化劑,可列舉Irgafos 168(BASF公司製造,商標)、Irgafos 12(BASF公司製造,商標)、Irgafos 38(BASF公司製造,商標)、ADKSTAB 329K(ADEKA(股)製造,商標)、ADKSTAB PEP-36(ADEKA(股)製造,商標)、ADKSTAB PEP-8(ADEKA(股)製造,商標)、Irgafos P-EPQ(Clariant公司製造,商標)、Weston 618(GE公司製造,商標)、Weston 619G(GE公司製造,商標)及Weston 624(GE公司製造,商標)等市售品。
關於聚碳酸酯系樹脂組合物中之抗氧化劑(E)之含量,相對於聚碳酸酯系樹脂(A)100質量份,較佳為0.01~0.5質量份,更佳為0.01~0.2質量份。若含量處於上述範圍內,則能夠維持成形步驟等中之熱穩定性、成形品之長期熱穩定性,而不易引起分子量降低,故而較佳。
本發明之聚碳酸酯系樹脂組合物較佳為具有17,000以上28,000以下之黏度平均分子量(Mv)。上述黏度平均分子量可藉由各成分之調配條件進行調整。藉由將黏度平均分子量設為上述範圍,能夠製成成形性優異且阻燃性更優異之聚碳酸酯系樹脂。
黏度平均分子量(Mv)更佳為19,000以上,進而較佳為20,000以上。關於其上限值,就成形性之觀點而言,更佳為27,500以下,進而較佳為26,000以下,進而更佳為25,500以下,尤佳為22,500以下。
關於上述黏度平均分子量(Mv),如上所述,係對20℃下之二氯甲烷溶液之極限黏度[η]進行測定並根據Schnell之式所算出之值。「組合物之黏度平均分子量」可藉由於黏度測定時進行通常之處理(組合物於處理溶液中之溶解及不溶物之去除等)而進行測定。
<成形品>
包含本發明之聚碳酸酯系樹脂組合物之成形品可將調配上述各成分並進行混練而得者進行成形而獲得。
作為混練方法,並無特別限制,例如可列舉使用帶式混合機、亨舍爾混合機、班布里混合機、轉鼓、單螺桿擠出機、雙螺桿擠出機、雙向捏合機、多螺桿擠出機等之方法。又,混練時之加熱溫度係於通常240~330℃、較佳為250~320℃之範圍內進行選擇。
作為成形方法,可使用先前公知之各種成形方法,例如可列舉:射出成形法、射出壓縮成形法、擠出成形法、吹塑成形法、加壓成形法、真空成形法及發泡成形法等。
除聚碳酸酯系樹脂以外之含有成分亦可預先與聚碳酸酯系樹脂或其他熱塑性樹脂進行熔融混練、即以母料之形式進行添加。
或較佳為使聚碳酸酯系樹脂組合物顆粒化而進行射出成形,可使用普通之射出成形法或射出壓縮成形法、以及氣體輔助成形法等特殊成形法,而可製造各種成形品。
於將本發明之成形體用作外觀構件之情形時,較佳為使用熱循環成形法、高溫模具、隔熱模具等提昇外觀之成形技術。
為了獲得大型薄壁之射出成形品,較佳為使用射出壓縮成形或高壓或者超高壓之射出成形,於成形具有部分之薄壁部之成形品時,亦可使用部分壓縮成形等。
[實施例]
藉由實施例進一步具體地說明本發明,但本發明不受該等實施例任何限定。各例之特性值、評價結果係按照以下而求出。
<黏度平均分子量>
黏度平均分子量(Mv)係使用烏氏黏度計對20℃下之二氯甲烷溶液之黏度進行測定,藉此求出極限黏度[η],並利用以下式(Schnell式)算出。
[數2]
<氯甲酸酯基濃度(CF值)之測定>
以氯離子濃度基準計,以JIS K 8203-1994為參考,使用氧化-還原滴定、硝酸銀滴定來進行測定。
使用全移液管採取聚碳酸酯低聚物溶液10 mL至200 mL三角燒瓶中。使用二氯甲烷20 mL於全移液管中進行洗淨,將該洗淨液亦加入至上述三角燒瓶中。於該三角燒瓶中加入NaOH-MeOH溶液(使氫氧化鈉36 g溶解於純水39 mL中而製備48質量%NaOH水溶液,將該水溶液加入至500 mL之甲醇中並使之溶解而成者)約10 mL並攪拌3分鐘,進行氯甲酸酯基之水解。進而加入脫離子水10 mL,確認為於三角燒瓶中無析出物之狀態。
一面攪拌三角燒瓶之內容物一面緩慢地加入1 mol/L硝酸水溶液(純正化學股份有限公司製造,體積分析用當量濃度液),且一面使用通用pH值試紙進行pH值之確認一面將pH值中和調整至6~7。於三角燒瓶中加入3滴螢光素鈉溶液(使螢光素鈉(關東化學股份有限公司製造)0.1 g溶解於乙醇20 mL中而製備),確認到黃色之顯色後,一面攪拌三角燒瓶之內容物一面藉由滴定管滴加1 mol/L硝酸銀水溶液(體積分析用,和光純藥工業股份有限公司製造,f=1.001),並記錄三角燒瓶之內容物自黃色變成粉紅色時之滴加量。藉由以下計算式求出氯甲酸酯基濃度(CF)。
CF=1 mol/L硝酸銀滴加量(mL)×f×1/10
(上述式中,為f=1.001(硝酸銀水溶液之係數))
<胺末端量之定量方法>
使1,1,1-三(4-羥基苯基)乙烷(THPE)共聚而成之對第三丁基苯酚(PTBP)末端聚碳酸酯之全部末端中之胺末端分率之定量方法
NMR裝置:JEOL RESONANCE(股)製造 ECA-500
探針:TH5 與5NMR試樣管對應
觀測範圍:-5~15 ppm
觀測中心:5 ppm
脈衝重複時間:9秒
脈衝寬度:45°
累計次數:256次
NMR試樣管:5
樣品量:30~40 mg
溶劑:氘化氯仿
測定溫度:室溫
A:於δ6.6~6.8附近所觀測到之BPA-OH末端部之OH基鄰位氫之積分值
B:於δ3.3~3.5附近所觀測到之胺末端部之亞甲基之積分值
C:於δ1.2~1.4附近所觀測到之對第三丁基苯基部之丁基之積分值
a=A/2
b=B/4
c=C/9
T=a+b+c
胺末端分率(mol%)=b/T×100
製造例1
(1)聚碳酸酯低聚物合成步驟
於5.6質量%氫氧化鈉水溶液中,加入相對於之後溶解之雙酚A(以下,有時簡記為BPA)為2,000質量 ppm之二硫亞磺酸鈉,以雙酚A濃度成為13.5質量%之方式使雙酚A溶解於其中,而製備雙酚A之氫氧化鈉水溶液。
使雙酚A之氫氧化鈉水溶液以40 L/hr、二氯甲烷以20 L/hr及光氣以4.0 kg/hr連續地通入內徑6 mm、管長30 m之管型反應器。管型反應器具有套管部分,將冷卻水通入套管而使反應液之溫度保持於40℃以下。
將流出管型反應器之反應液連續地導入至具備後掠翼之內容積40 L之附檔板之槽型反應器中,進而將雙酚A之氫氧化鈉水溶液以1.4 L/hr、25質量%氫氧化鈉水溶液以0.03 L/hr、水以8 L/hr、及1質量%三乙胺(以下,有時簡記為TEA)水溶液以0.32 L/hr添加至其中而進行反應。
連續地抽出自槽型反應器溢出之反應液並進行靜置,藉此將水相分離去除,而採取二氯甲烷相。所獲得之聚碳酸酯低聚物濃度為236 g/L,氯甲酸酯基濃度為0.72 mol/L。再者,上述二氯甲烷相中未包含TEA。
(2)聚碳酸酯之聚合步驟
於具備隔板、槳型攪拌葉之50 L槽型反應器中投入低聚物溶液20.0 L、二氯甲烷3.6 L、及TEA 4.0 mL(相對於氯甲酸酯基量為0.002 mol/mol)。向其中添加THPE之氫氧化鈉水溶液(使THPE 110.2 g溶解於使氫氧化鈉115 g溶解於水1.7 L中而得之水溶液中)作為分支劑,並實施20分鐘聚合反應。
繼而,於二氯甲烷1.0 L中添加溶解有對第三丁基苯酚(PTBP)168.6 g之溶液及BPA之氫氧化鈉水溶液(使氫氧化鈉749 g溶解於水11.0 L中,並使二硫亞磺酸鈉2.9 g、BPA 1445 g溶解而成者),實施40分鐘聚合反應。
加入二氯甲烷12 L以進行稀釋,其後,分離成包含聚碳酸酯系樹脂之有機相與包含過量之BPA及氫氧化鈉之水相,將有機相單離。將所獲得之聚碳酸酯系樹脂之二氯甲烷溶液依序利用相對於該溶液為15體積%之0.03 mol/L・氫氧化鈉水溶液及0.2 mol/L鹽酸進行洗淨,繼而,利用純水反覆進行洗淨直至洗淨後之水相中之導電率成為0.05 μS/m以下。將藉由洗淨所獲得之聚碳酸酯系樹脂之二氯甲烷溶液進行濃縮並粉碎,將所獲得之薄片(flake)於減壓下以100℃進行乾燥,獲得聚碳酸酯系樹脂PC1。
製造例2
於製造例1之步驟(2)中,將TEA量變更為12.0 mL(相對於氯甲酸酯基量為0.006 mol/mol),將THPE量變更為127.9 g,將PTBP量變更為205.7 g,除此以外,以與製造例1相同之方式獲得聚碳酸酯系樹脂PC2。
製造例3
於製造例1之步驟(2)中,將TEA量變更為40.0 mL(相對於氯甲酸酯基量為0.020 mol/mol),將PTBP量變更為195.8 g,除此以外,以與製造例1相同之方式獲得聚碳酸酯系樹脂PC3。
製造例4
於製造例1之步驟(2)中,將THPE量變更為165.4 g,將PTBP量變更為228.3 g,除此以外,以與製造例1相同之方式獲得聚碳酸酯系樹脂PC4。
製造例5
於製造例1之步驟(2)中,將TEA量變更為20.0 mL(相對於氯甲酸酯基量為0.010 mol/mol),將THPE量變更為166.0 g,將PTBP量變更為253.6 g,除此以外,以與製造例1相同之方式獲得聚碳酸酯系樹脂PC5。
製造例6
於製造例1之步驟(2)中,將TEA量變更為40.0 mL(相對於氯甲酸酯基量為0.020 mol/mol),將THPE量變更為166.0 g,將PTBP量變更為247.6 g,除此以外,以與製造例1相同之方式獲得聚碳酸酯系樹脂PC6。
關於各製造例中所獲得之聚碳酸酯系樹脂PC1~PC6,彙總於表1及表2中。針對PC1~PC6測定黏度平均分子量(Mv)。將黏度平均分子量合併記載於表1及表2。
[表1]
[表2]
<阻燃劑(B)>
九氟丁烷磺酸鉀鹽[Mitsubishi Materials(股)製造,商品名「Eftop KFBS」]
<聚有機矽氧烷(C)>
反應性聚矽氧化合物[信越化學工業(股)製造,商品名「KR511」:含有苯基、甲氧基及乙烯基,折射率=1.518]
<抗氧化劑(E)>
抗氧化劑:「IRGAFOS 168(商品名)」[亞磷酸三(2,4-二-第三丁基苯基)酯,BASF JAPAN股份有限公司製造]
實施例1~4,比較例1~2
將上述製造步驟中所獲得之PC1~PC6之任一聚碳酸酯系樹脂(A)、以及其他各成分以表3及表4所示之調配比例進行混合,供給至排氣式雙軸擠出機(TANABE PLASTICS MACHINERY(股)製造,VS40-28),以螺桿轉速100 rpm、噴出量10 kg/hr、設定溫度280℃進行熔融混練,獲得評價用顆粒物樣品。
[評價試驗]
使上述所獲得之顆粒物於120℃下乾燥8小時,其後,使用射出成形機(東芝機械(股)製造,EC75PNII,螺桿徑36 mm)以料缸溫度290℃、模具溫度90℃進行射出成形,獲得厚度0.8 mm之試片(長度125 mm,寬度13 mm)。於製作該試片時,樹脂係自模具之長軸方向上之對向之兩端(相當於試片之寬)開始填充。使用該試片並依據保險商實驗室-對象(Underwriters Laboratories subject)94(UL94)燃燒試驗進行垂直燃燒試驗,分類為V-0、V-1及V-2來進行評價。分類為V-0者係表示阻燃性優異。
[表3]
[表4]
[產業上之可利用性]
根據本發明,能夠於無損聚碳酸酯系樹脂所具有之優異物性之情況下獲得樹脂本身之耐滴落性得到改良之聚碳酸酯系樹脂。
Claims (15)
- 如請求項1或2之聚碳酸酯系樹脂,其中上述聚碳酸酯系樹脂包含支鏈狀聚碳酸酯系樹脂(A-1)10~100質量份、及除上述支鏈狀聚碳酸酯系樹脂(A-1)以外之芳香族聚碳酸酯系樹脂(A-2)90~0質量份。
- 如請求項4之聚碳酸酯系樹脂,其中上述通式(I)所表示之支鏈結構為源自1,1,1-三(4-羥基苯基)乙烷之結構。
- 如請求項1或2之聚碳酸酯系樹脂,其黏度平均分子量為17,000以上28,000以下。
- 如請求項7之聚碳酸酯系樹脂之製造方法,其中於上述步驟(1)及/或步驟(2)加入分支劑。
- 如請求項8或9之聚碳酸酯系樹脂之製造方法,其中於上述步驟(2)中 進而加入上述分支劑。
- 如請求項9之聚碳酸酯系樹脂之製造方法,其中加入相對於上述步驟(1)及步驟(2)中所加入之二元酚、分支劑及末端封端劑之總莫耳數為0.3莫耳%以上3.0莫耳%以下之上述通式(III)所表示之上述分支劑。
- 如請求項9之聚碳酸酯系樹脂之製造方法,其中上述通式(III)所表示之分支劑為1,1,1-三(4-羥基苯基)乙烷。
- 如請求項7至9中任一項之聚碳酸酯系樹脂之製造方法,其中上述胺系觸媒為三級胺或其鹽。
- 如請求項7至9中任一項之聚碳酸酯系樹脂之製造方法,其中上述胺系觸媒為三乙胺。
- 一種聚碳酸酯系樹脂組合物,其包含如請求項1至6中任一項之聚碳酸酯系樹脂(A)、及選自由阻燃劑(B)、聚有機矽氧烷(C)、聚四氟乙烯(D)及抗氧化劑(E)所組成之群中之至少1種。
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US4973664A (en) * | 1989-07-20 | 1990-11-27 | General Electric Company | Method for preparing polycarbonates of controlled molecular weight from bischloroformates |
US5367044A (en) * | 1990-10-12 | 1994-11-22 | General Electric Company | Blow molded article molded from a composition comprising a randomly branched aromatic polymer |
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