JPS6330341B2 - - Google Patents
Info
- Publication number
- JPS6330341B2 JPS6330341B2 JP54017041A JP1704179A JPS6330341B2 JP S6330341 B2 JPS6330341 B2 JP S6330341B2 JP 54017041 A JP54017041 A JP 54017041A JP 1704179 A JP1704179 A JP 1704179A JP S6330341 B2 JPS6330341 B2 JP S6330341B2
- Authority
- JP
- Japan
- Prior art keywords
- aromatic polyester
- polyester polycarbonate
- resin composition
- bis
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 229920000515 polycarbonate Polymers 0.000 claims description 23
- 239000004417 polycarbonate Substances 0.000 claims description 23
- 229920000728 polyester Polymers 0.000 claims description 23
- 229920001283 Polyalkylene terephthalate Polymers 0.000 claims description 11
- KKEYFWRCBNTPAC-UHFFFAOYSA-N terephthalic acid group Chemical group C(C1=CC=C(C(=O)O)C=C1)(=O)O KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 9
- 150000001875 compounds Chemical group 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- 239000011342 resin composition Substances 0.000 claims description 6
- 230000009477 glass transition Effects 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 12
- 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 11
- -1 hydroxy-3,5-dichlorophenyl Chemical group 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- 229920001707 polybutylene terephthalate Polymers 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000012695 Interfacial polymerization Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical group OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- WGMBWDBRVAKMOO-UHFFFAOYSA-L disodium;4-[2-(4-oxidophenyl)propan-2-yl]phenolate Chemical compound [Na+].[Na+].C=1C=C([O-])C=CC=1C(C)(C)C1=CC=C([O-])C=C1 WGMBWDBRVAKMOO-UHFFFAOYSA-L 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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 1
- POSQGFWJUAQFMQ-UHFFFAOYSA-N 2,5-dibromobenzene-1,4-dicarbonyl chloride Chemical compound ClC(=O)C1=CC(Br)=C(C(Cl)=O)C=C1Br POSQGFWJUAQFMQ-UHFFFAOYSA-N 0.000 description 1
- IQNTUYCIRRCRDY-UHFFFAOYSA-N 2,5-dichlorobenzene-1,4-dicarbonyl chloride Chemical compound ClC(=O)C1=CC(Cl)=C(C(Cl)=O)C=C1Cl IQNTUYCIRRCRDY-UHFFFAOYSA-N 0.000 description 1
- KOVOSORRBURNCU-UHFFFAOYSA-N 2,5-dimethylbenzene-1,4-dicarbonyl chloride Chemical compound CC1=CC(C(Cl)=O)=C(C)C=C1C(Cl)=O KOVOSORRBURNCU-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- RVHUMFJSCJBNGS-UHFFFAOYSA-N 2-[2,6-dibromo-4-[2-[3,5-dibromo-4-(2-hydroxyethoxy)phenyl]propan-2-yl]phenoxy]ethanol Chemical compound C=1C(Br)=C(OCCO)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(OCCO)C(Br)=C1 RVHUMFJSCJBNGS-UHFFFAOYSA-N 0.000 description 1
- MSWAXXJAPIGEGZ-UHFFFAOYSA-N 2-chlorobenzene-1,4-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C(Cl)=C1 MSWAXXJAPIGEGZ-UHFFFAOYSA-N 0.000 description 1
- NTNUPCREDHXJEL-UHFFFAOYSA-N 2-methylbenzene-1,4-dicarbonyl chloride Chemical compound CC1=CC(C(Cl)=O)=CC=C1C(Cl)=O NTNUPCREDHXJEL-UHFFFAOYSA-N 0.000 description 1
- KTMNDTPAJZKQPF-UHFFFAOYSA-N 2-tert-butyl-4-[1-(3-tert-butyl-4-hydroxyphenyl)propyl]phenol Chemical compound C=1C=C(O)C(C(C)(C)C)=CC=1C(CC)C1=CC=C(O)C(C(C)(C)C)=C1 KTMNDTPAJZKQPF-UHFFFAOYSA-N 0.000 description 1
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 1
- CKNCVRMXCLUOJI-UHFFFAOYSA-N 3,3'-dibromobisphenol A Chemical compound C=1C=C(O)C(Br)=CC=1C(C)(C)C1=CC=C(O)C(Br)=C1 CKNCVRMXCLUOJI-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RSSGMIIGVQRGDS-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)-phenylmethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C1=CC=CC=C1 RSSGMIIGVQRGDS-UHFFFAOYSA-N 0.000 description 1
- OVVCSFQRAXVPGT-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)cyclopentyl]phenol Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCC1 OVVCSFQRAXVPGT-UHFFFAOYSA-N 0.000 description 1
- QHJPJZROUNGTRJ-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)octan-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)(CCCCCC)C1=CC=C(O)C=C1 QHJPJZROUNGTRJ-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- UUAGPGQUHZVJBQ-UHFFFAOYSA-N Bisphenol A bis(2-hydroxyethyl)ether Chemical compound C=1C=C(OCCO)C=CC=1C(C)(C)C1=CC=C(OCCO)C=C1 UUAGPGQUHZVJBQ-UHFFFAOYSA-N 0.000 description 1
- HTVITOHKHWFJKO-UHFFFAOYSA-N Bisphenol B Chemical compound C=1C=C(O)C=CC=1C(C)(CC)C1=CC=C(O)C=C1 HTVITOHKHWFJKO-UHFFFAOYSA-N 0.000 description 1
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- XMUZQOKACOLCSS-UHFFFAOYSA-N [2-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=CC=C1CO XMUZQOKACOLCSS-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229920003232 aliphatic polyester Polymers 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 229940043430 calcium compound Drugs 0.000 description 1
- 150000001674 calcium compounds Chemical class 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 229920005680 ethylene-methyl methacrylate copolymer Polymers 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- NZZGQZMNFCTNAM-UHFFFAOYSA-N naphthalene-2,6-dicarbonyl chloride Chemical compound C1=C(C(Cl)=O)C=CC2=CC(C(=O)Cl)=CC=C21 NZZGQZMNFCTNAM-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920005606 polypropylene copolymer Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000012254 powdered material Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Description
本発明は機械的および化学的性質のすぐれた樹
脂組成物に関するものである。詳しくは、成形
性、耐衝撃性および耐溶剤性が改善された芳香族
ポリエステルポリカーボネート樹脂組成物に関す
るものである。
芳香族ポリエステルポリカーボネートは、同一
分子内にエステル結合とカーボネート結合を有す
る線状の樹脂であり、例えば、2,2−ビス(4
−ヒドロキシフエニル)プロパン(ビスフエノー
ルA)、テルフタロイルクロリドおよびホスゲン
を反応させることによつて製造され、すぐれた機
械的性質、耐候性、耐薬品性および透明性を有す
るものであることが知られている。(特開昭52−
158992)
しかしながら、このような芳香族ポリエステル
ポリカーボネートは軟化温度が高く溶融粘度も高
いため、成形性が悪い欠点がある。例えば、射出
成形によつて成形品を製造する場合、高い成形温
度、金型温度および射出圧力を必要とするが、高
い温度を採用することはポリマーの熱劣化の原因
となり、高い射出圧力を採用することは製品の歪
の原因となる等の不都合があり、しかもコスト高
となるので、その成形性の改善が望まれていた。
本発明者らは、上記した芳香族ポリエステルポ
リカーボネートの欠点を改良すべく鋭意研究の結
果、芳香族ポリエステルポリカーボネートに芳香
族ポリエステル樹脂を配合するときは、その成形
性を大巾に改善することができるのみならず、耐
衝撃性および耐溶剤性も向上させ得ることを知得
して本発明を完成した。
すなわち本発明は、成形性、耐衝撃性および耐
溶剤性の改善された工業的価値の大きい芳香族ポ
リエステルポリカーボネートを提供することを目
的とするものであり、その要旨とするところは、
一般式
(式中、Xは2価の基を示し、芳香核は置換基
を有していてもよい。)
で表わされる構造単位と、一般式
(式中、Xおよび芳香核は上と同一意義を有す
る。)
で表わされる構造単位とからなり、かつジヒドロ
キシジアリール化合物残基:テレフタル酸残基:
カーボネート結合のモル比が1:0.33〜0.75:
0.67〜0.25である芳香族ポリエステルポリカーボ
ネート100重量部に、ポリアルキレンテレフタレ
ート1〜150重量部を配合してなる樹脂組成物で
ある。
以下、本発明を詳細に説明する。
本発明で使用する芳香族ポリエステルポリカー
ボネートは、例えば、一般式
(式中、Xは、
The present invention relates to a resin composition with excellent mechanical and chemical properties. Specifically, the present invention relates to an aromatic polyester polycarbonate resin composition with improved moldability, impact resistance, and solvent resistance. Aromatic polyester polycarbonate is a linear resin having an ester bond and a carbonate bond in the same molecule, for example, 2,2-bis(4
-Hydroxyphenyl)propane (bisphenol A), terphthaloyl chloride and phosgene, and has excellent mechanical properties, weather resistance, chemical resistance and transparency. Are known. (Unexamined Japanese Patent Publication No. 52-
158992) However, such aromatic polyester polycarbonates have a high softening temperature and high melt viscosity, so they have the disadvantage of poor moldability. For example, when manufacturing molded products by injection molding, high molding temperature, mold temperature, and injection pressure are required, but high temperatures cause thermal deterioration of the polymer, so high injection pressure is necessary. Since doing so has disadvantages such as causing distortion of the product and also increases costs, it has been desired to improve the moldability. As a result of intensive research to improve the above-mentioned drawbacks of aromatic polyester polycarbonate, the present inventors found that when aromatic polyester resin is blended with aromatic polyester polycarbonate, its moldability can be greatly improved. The present invention was completed based on the knowledge that not only impact resistance and solvent resistance can also be improved. That is, an object of the present invention is to provide an aromatic polyester polycarbonate having improved moldability, impact resistance, and solvent resistance and having great industrial value, and its gist is as follows:
general formula (In the formula, X represents a divalent group, and the aromatic nucleus may have a substituent.) A structural unit represented by the following and the general formula (In the formula, X and the aromatic nucleus have the same meanings as above.) Consisting of a structural unit represented by: dihydroxydiaryl compound residue: terephthalic acid residue:
The molar ratio of carbonate bonds is 1:0.33-0.75:
This resin composition is prepared by blending 1 to 150 parts by weight of polyalkylene terephthalate to 100 parts by weight of aromatic polyester polycarbonate having a molecular weight of 0.67 to 0.25. The present invention will be explained in detail below. The aromatic polyester polycarbonate used in the present invention has, for example, the general formula (In the formula, X is
【式】−O−,−S
−,−SO−または−SO2−などの2価の基、R
は、水素原子または1価の炭化水素基、R′は、
2価の炭化水素基を示し芳香核はハロゲン原子ま
たは1価の炭化水素基を有していてもよい。)
で表わされる、ジヒドロキシジアリール化合物
と、テレフタロイルクロリドとを、塩化メチレン
のような有機溶媒およびピリジンのような酸結合
剤の存在下で反応させ、次いでこの反応混合物に
ホスゲンを導入して重縮合させる溶液重合法(特
開昭52−128992)、あるいは、前示一般式〔〕
で表わされるジヒドロキシジアリール化合物のア
ルカリ性水溶液とテレフタロイルクロリドの有機
溶媒溶液とを反応させ、次いでこの反応混合物に
ホスゲンを導入して末端がクロロホーメート基の
オリゴマーとし、このオリゴマーの有機溶媒に前
示一般式〔〕で表わされるジヒドロキシジアリ
ール化合物のアルカリ性水溶液を加えて重縮合さ
せる界面重合法などによつて製造することができ
る。
工業的には、回収損失が大きく臭気の強いピリ
ジンを使用する必要がない点で、界面重合法が有
利である。
ジヒドロキシジアリール化合物、テレフタロイ
ルクロリド類およびホスゲンの使用量は、得られ
る芳香族ポリエステルポリカーボネート中のジヒ
ドロキシジアリール化合物残基:テレフタル酸残
基:カーボネート結合のモル比が1:0.33〜
0.75:0.67〜0.25、好ましくは1:0.33〜0.49:
0.67〜0.51となるよう適宜選択される。テレフタ
ル酸残基のモル比がこれより少ないとガラス転移
点の改善の点で不満足であり、逆にカーボネート
結合のモル比が少なすぎるとポリカーボネートが
本来有する性質が損なわれる。ただし、この組成
モル比は赤外線スペクトル分析により−COO−
基1740cm-1および−OCOO−基1770cm-1のピーク
比より求めた値である。
前示一般式〔〕で表わされるジヒドロキシジ
アリール化合物の具体例としては、ビス(4−ヒ
ドロキシフエニル)メタン、1,1−ビス(4−
ヒドロキシフエニル)エタン、2,2−ビス(4
−ヒドロキシフエニル)プロパン、2,2−ビス
(4−ヒドロキシフエニル)ブタン、2,2−ビ
ス(4−ヒドロキシフエニル)オクタン、ビス
(4−ヒドロキシフエニル)フエニルメタン、2,
2−ビス(4−ヒドロキシ−3−メチルフエニ
ル)プロパン、1,1−ビス(4−ヒドロキシ−
3−第3ブチルフエニル)プロパン、2,2−ビ
ス(4−ヒドロキシ−3−ブロモフエニル)プロ
パン、2,2−ビス(4−ヒドロキシ−3,5−
ジブロモフエニル)プロパン、2,2−ビス(4
−ヒドロキシ−3,5−ジクロロフエニル)プロ
パンのようなビス(ヒドロキシアリール)アルカ
ン類、1,1−ビス(4−ヒドロキシフエニル)
シクロペンタン、1,1−ビス(4−ヒドロキシ
フエニル)シクロヘキサンのようなビス(ヒドロ
キシアリール)シクロアルカン類、4,4′−ジヒ
ドロキシジフエニルエーテル、4,4−ジヒドロ
キシ−3,3′−ジメチルジフエニルエーテル、の
ようなジヒドロキシジアリールエーテル類、4,
4′−ジヒドロキシジフエニルスルフイド、1,
4′−ジヒドロキシ−3,3′−ジメチルジフエニル
スルフイドのようなジヒドロキシジアリールスル
フイド類、4,4′−ジヒドロキシジフエニルスル
ホキシド、4,4′−ジヒドロキシ−3,3′−ジメ
チルジフエニルスルホキシドのようなジヒドロキ
シジアリールスルホキシド類、4,4′−ジヒドロ
キシジフエニルスルホン、4,4′−ジヒドロキシ
−3,3′−ジメチルジフエニルスルホンのような
ジヒドロキシジアリールスルホン類等があげられ
る。
テレフタロイルクロリド類としては、テレフタ
ロイルクロリドの他に、その核にハロゲン原子、
アルキル基を有するテレフタロイルクロリド、例
えば2,5−ジクロルテレフタロイルクロリド、
2,5−ジブロムテレフタロイルクロリド、クロ
ルテレフタロイルクロリド、メチルテレフタロイ
ルクロリド、2,5−ジメチルテレフタロイルク
ロリドなどがあげられる。また、少量の他の二塩
基酸のクロリド、例えば20%未満のイソフタロイ
ルクロリド、2,6−ナフタリンジカルボン酸ジ
クロリド、4,4′−ベンゾフエノンジカルボン酸
ジクロリドなどを混合して用いてもよい。
このようにして製造された本発明の芳香族ポリ
エステルポリカーボネートは、0.6g/dl塩化メ
チレン溶液を用い20℃で測定したηspから、式
ηsp/C=〔η〕+0.427〔η〕2C
により算出した固有粘度〔η〕が、0.4〜1.5、好
ましくは0.43〜1.1であることが望ましい。〔η〕
があまりに大きいと成形性が悪く、逆にあまりに
小さいと機械的性質が十分でない。
また、上記芳香族ポリエステルポリカーボネー
トのガラス転移点(Tg)は、通常160〜190℃、
好ましくは170〜185℃である。さらに、該芳香族
ポリエステルポリカーボネートは、末端カルボキ
シル基が10μ当量/g樹脂以下であることが好ま
しい。
本発明で使用するポリアルキレンテレフタレー
トは、テレフタル酸またはそのジアルキルエステ
ルと、脂肪族グリコール類とを主成分として重縮
合反応を行つて得られる重合体または共重合体で
あり、代表的なものとしては、ポリエチレンテレ
フタレート、ポリブチレンテレフタレートなどが
あげられる。
上記脂肪族グリコール類としては、エチレング
リコール、プロピレングリコール、テトラメチレ
ングリコール、ヘキサメチレングリコールなどが
あげられるが、これら脂肪族グリコール類と共に
少量の他のジオール類または多価アルコール類、
例えば脂肪族グリコール類に対して20重量%以下
のシクロヘキサンジオール、シクロヘキサンジメ
タノール、キシリレングリコール、2,2−ビス
(4−ヒドロキシフエニル)プロパン、2,2−
ビス(4−ヒドロキシ−3,5−ジブロモフエニ
ル)プロパン、2,2−ビス(4−ヒドロキシエ
トキシフエニル)プロパン、2,2−ビス(4−
ヒドロキシエトキシ−3,5−ジブロモフエニ
ル)プロパン、グリセリン、ペンタエリスリトー
ルなどを混合して用いてもよい。
また、テレフタル酸またはそのジアルキルエス
テルと共に少量の他の二塩基酸、多塩基酸または
そのアルキルエステル、例えばテレフタル酸また
はそのジアルキルエステルに対して20重量%以下
のフタル酸、イソフタル酸、ナフタリンジカルボ
ン酸、ジフエニルジカルボン酸、アジピン酸、セ
バシン酸、トリメシン酸、トリメリツト酸、それ
らのアルキルエステルなどを混合して用いてもよ
い。
本発明で用いるポリアルキレンテレフタレート
は、固有粘度(テトラクロルエタン:フエノール
の1:1重量混合溶媒を用い、樹脂1g/100ml
溶媒の溶液について30℃で測定)が0.4〜1.5、好
ましくは0.6〜1.2程度のものを用いるのがよい。
ポリアルキレンテレフタレートの配合量は、芳
香族ポリエステルポリカーボネート100重量部に
対し、1〜150重量部、好ましくは5〜100重量部
である。ポリアルキレンテレフタレートの量があ
まりに少いと、本発明の効果が期待できなくな
る。逆にあまりに多いと、成形性は改良されるけ
れども、耐衝撃性その他の機械的性質が低下する
ようになるので好ましくない。
芳香族ポリエステルポリカーボネートとポリア
ルキレンテレフタレートとを配合する方法として
は、公知の種々の方法を採用することができ、例
えば、両者の粒状物または粉状物をブレンダーや
ミキサーを用いてドライブレンドする方法、両者
を押出機などを用いて溶融混合する方法、両者の
溶液を混合した混合物から溶媒を蒸発させるか、
または沈澱析出させる方法、あるいは芳香族ポリ
エステルポリカーボネート製造の任意の段階でポ
リアルキレンテレフタレートを添加する方法など
を採用することができる。
本発明の組成物には、その性質を損なわない範
囲において他種の樹脂、例えば、ポリカプロラク
トンのような脂肪族ポリエステル樹脂、ポリリエ
チレン、ポリプロピレン、エチレン−酢酸ビニル
共重合体のようなポリオレフイン系樹脂、ポリメ
チルメタアクリレート、エチレン−メチルメタア
クリレート共重合体、ポリメタアクリル酸のよう
なポリアクリレート系樹脂、ポリアセタール樹脂
などを配合してもよい。また、リン酸、亜リン
酸、それらのエステル、またはそれらの金属塩の
ような安定剤、ガラス繊維、炭素繊維のような補
強剤、シリカ、アルミナ、シリカーアルミナ、シ
リカーマグネシア、カルシウム化合物のような充
填剤、その他可塑性、滑剤、紫外線吸収剤、難燃
剤、染顔料などの添加剤を加えることもできる。
本発明の組成物は、芳香族ポリエステルポリカ
ーボネートが本来有するすぐれた性質を損なうこ
となく、成形性、耐衝撃性および耐溶剤性が改善
されており、射出成形、押出成形その他の熱成形
による加工が容易であるから、エンジニアリング
プラスチツクとして広範囲の用途に使用すること
ができ、工業的価値が大きい。
以下、実施例によつて本発明を具体的に説明す
るが、本発明はその要旨をこえない限り以下の実
施例に限定されるものではない。
なお、実施例中〓部〓は重量部を示し、引張強
度、曲げ強度およびアイゾツド衝撃強度は、それ
ぞれASTM D638、ASTM D790およびASTM
D256に基いて測定した値である。
また、耐溶剤性は、巾1/2″、厚さ1/8″、長さ
5″の試験片に50Kg/cm3の曲げ応力を加えて室温の
トルエンまたは酢酸ブチルにそれぞれ5分間浸漬
した後、クラツクまたはクレーズの発生の有無を
肉眼判定した。後記表中〇はクラツクまたはクレ
ーズの発生がなかつたこと、×はクレーズの発生
が認められたことを示す。
芳香族ポリエステルポリカーボネートの製造例
テレフタロイルクロリドの3%塩化メチレン溶
液、ビスフエノールAを5%水酸化ナトリウム水
溶液に溶解して調製したビスフエノールAナトリ
ウム塩13%の水溶液および2%トリエチルアミン
水溶液を、それぞれ44.2Kg/hr、15.9Kg/hrおよ
び0.2Kg/hrの流量で、内径30mm、長さ1.5mのガ
ラス球充填塔に供給し、該塔の供給口から0.75m
の位置からホスゲン0.75Kg/hrを吹込んで反応を
行い、エステル結合を有し、末端にクロロホーメ
ート基を有するオリゴマーを製造した。
反応混合物を分液して得た上記オリゴマーの塩
化メチレン溶液44.0Kg/hr、上記と同じビスフエ
ノールAナトリウム塩の13%水溶液17.6Kg/hr、
25%水酸化ナトリウム水溶液1.1Kg/hr、2%ト
リエチルアミンの水溶液0.67Kg/hrおよびp−タ
−シヤリーブチルフエノール27g/hrを、撹拌槽
に供給し、平均滞留時間が2時間となるようにし
て重縮合反応を行つた。
反応混合物を分液して得たポリマーの塩化メチ
レン溶液を、水、塩酸水溶液、次いで水で洗浄し
た後、塩化メチレンを蒸気させて、〔η〕が0.75
でビスフエノールA残基:テレフタル酸残基:カ
ーボネート結合のモル比が1:0.46:0.54の芳香
族ポリエステルポリカーボネートを得た。
実施例1〜5および比較例1.2
上記製造例により製造した芳香族ポリエステル
ポリカーボネートの粉末100部に対し下記表1に
示す量のポリアルキレンテレフタレートを混合し
て押出機を用いて300℃で溶融混合し、押出して
ペレツト化した。
これらのペレツトを、射出成形機(日精樹脂(株)
製TS−100型)およびASTMで規定する試験片
成形用金型を用いて射出成形した。その際の成形
温度、金型温度および射出圧力は下記表1に示す
値が必要であつた。
かくして得られた試験片の機械的性質および熱
変形温度は下記表2に示す通りであつた。
なお、比較のためポリアルキレンテレフタレー
トを配合しなかつた場合、および多量に用いた場
合の結果を併記する。[Formula] Divalent group such as -O-, -S -, -SO- or -SO 2 -, R
is a hydrogen atom or a monovalent hydrocarbon group, R′ is
It represents a divalent hydrocarbon group, and the aromatic nucleus may have a halogen atom or a monovalent hydrocarbon group. ) and terephthaloyl chloride are reacted in the presence of an organic solvent such as methylene chloride and an acid binder such as pyridine, and then phosgene is introduced into the reaction mixture to Condensation solution polymerization method (JP-A-52-128992) or the general formula shown above []
An alkaline aqueous solution of a dihydroxydiaryl compound represented by the formula is reacted with a solution of terephthaloyl chloride in an organic solvent, and then phosgene is introduced into the reaction mixture to form an oligomer with a chloroformate group at the end. It can be produced by an interfacial polymerization method in which an alkaline aqueous solution of a dihydroxydiaryl compound represented by the general formula [] is added and polycondensed. Industrially, the interfacial polymerization method is advantageous in that it is not necessary to use pyridine, which has a large recovery loss and a strong odor. The amounts of the dihydroxydiaryl compound, terephthaloyl chloride, and phosgene to be used are such that the molar ratio of dihydroxydiaryl compound residue: terephthalic acid residue: carbonate bond in the resulting aromatic polyester polycarbonate is 1:0.33 or more.
0.75:0.67-0.25, preferably 1:0.33-0.49:
It is appropriately selected to be 0.67 to 0.51. If the molar ratio of terephthalic acid residues is less than this, the improvement in the glass transition point is unsatisfactory, and on the other hand, if the molar ratio of carbonate bonds is too small, the inherent properties of polycarbonate will be impaired. However, this composition molar ratio was determined by infrared spectrum analysis as −COO−
This value was determined from the peak ratio of the group 1740 cm -1 and the -OCOO- group 1770 cm -1 . Specific examples of the dihydroxydiaryl compound represented by the general formula [] include bis(4-hydroxyphenyl)methane, 1,1-bis(4-
hydroxyphenyl)ethane, 2,2-bis(4
-hydroxyphenyl)propane, 2,2-bis(4-hydroxyphenyl)butane, 2,2-bis(4-hydroxyphenyl)octane, bis(4-hydroxyphenyl)phenylmethane, 2,
2-bis(4-hydroxy-3-methylphenyl)propane, 1,1-bis(4-hydroxy-
3-tert-butylphenyl)propane, 2,2-bis(4-hydroxy-3-bromophenyl)propane, 2,2-bis(4-hydroxy-3,5-
dibromophenyl)propane, 2,2-bis(4
-bis(hydroxyaryl)alkanes such as hydroxy-3,5-dichlorophenyl)propane, 1,1-bis(4-hydroxyphenyl)
Cyclopentane, bis(hydroxyaryl)cycloalkanes such as 1,1-bis(4-hydroxyphenyl)cyclohexane, 4,4'-dihydroxydiphenyl ether, 4,4-dihydroxy-3,3'-dimethyl Dihydroxy diaryl ethers such as diphenyl ether, 4.
4'-dihydroxydiphenyl sulfide, 1,
Dihydroxydiaryl sulfides such as 4'-dihydroxy-3,3'-dimethyldiphenyl sulfide, 4,4'-dihydroxydiphenyl sulfoxide, 4,4'-dihydroxy-3,3'-dimethyl diphenyl sulfide; Examples include dihydroxydiarylsulfoxides such as enyl sulfoxide, dihydroxydiarylsulfones such as 4,4'-dihydroxydiphenylsulfone, and 4,4'-dihydroxy-3,3'-dimethyldiphenylsulfone. In addition to terephthaloyl chloride, terephthaloyl chloride has a halogen atom in its nucleus,
Terephthaloyl chloride having an alkyl group, such as 2,5-dichloroterephthaloyl chloride,
Examples include 2,5-dibromterephthaloyl chloride, chlorterephthaloyl chloride, methylterephthaloyl chloride, and 2,5-dimethylterephthaloyl chloride. In addition, a small amount of other dibasic acid chloride, such as less than 20% of isophthaloyl chloride, 2,6-naphthalene dicarboxylic acid dichloride, 4,4'-benzophenone dicarboxylic acid dichloride, etc., may be mixed and used. good. The aromatic polyester polycarbonate of the present invention produced in this manner has the formula η sp /C=[η]+0.427[η] 2 from η sp measured at 20°C using a 0.6 g/dl methylene chloride solution. It is desirable that the intrinsic viscosity [η] calculated by C is 0.4 to 1.5, preferably 0.43 to 1.1. [η]
If it is too large, the moldability will be poor, and if it is too small, the mechanical properties will be insufficient. In addition, the glass transition point (Tg) of the above aromatic polyester polycarbonate is usually 160 to 190°C,
Preferably it is 170-185°C. Furthermore, it is preferable that the aromatic polyester polycarbonate has a terminal carboxyl group of 10 μ equivalent/g resin or less. The polyalkylene terephthalate used in the present invention is a polymer or copolymer obtained by performing a polycondensation reaction mainly consisting of terephthalic acid or its dialkyl ester and aliphatic glycols. , polyethylene terephthalate, polybutylene terephthalate, etc. Examples of the aliphatic glycols include ethylene glycol, propylene glycol, tetramethylene glycol, hexamethylene glycol, etc. Along with these aliphatic glycols, small amounts of other diols or polyhydric alcohols,
For example, cyclohexanediol, cyclohexanedimethanol, xylylene glycol, 2,2-bis(4-hydroxyphenyl)propane, 2,2-
Bis(4-hydroxy-3,5-dibromophenyl)propane, 2,2-bis(4-hydroxyethoxyphenyl)propane, 2,2-bis(4-
Hydroxyethoxy-3,5-dibromophenyl)propane, glycerin, pentaerythritol, etc. may be used in combination. In addition, together with terephthalic acid or its dialkyl ester, a small amount of other dibasic acid, polybasic acid or its alkyl ester, such as phthalic acid, isophthalic acid, naphthalene dicarboxylic acid, not more than 20% by weight relative to terephthalic acid or its dialkyl ester, Diphenyldicarboxylic acid, adipic acid, sebacic acid, trimesic acid, trimellitic acid, alkyl esters thereof, and the like may be used in combination. The polyalkylene terephthalate used in the present invention has an inherent viscosity (resin 1g/100ml using a 1:1 weight mixed solvent of tetrachloroethane:phenol).
It is preferable to use a solvent having a value of 0.4 to 1.5 (measured at 30°C for a solvent solution), preferably 0.6 to 1.2. The blending amount of polyalkylene terephthalate is 1 to 150 parts by weight, preferably 5 to 100 parts by weight, based on 100 parts by weight of the aromatic polyester polycarbonate. If the amount of polyalkylene terephthalate is too small, the effects of the present invention cannot be expected. On the other hand, if the amount is too large, moldability is improved, but impact resistance and other mechanical properties are deteriorated, which is not preferable. Various known methods can be used to blend the aromatic polyester polycarbonate and polyalkylene terephthalate, such as dry blending the granular or powdered materials of the two using a blender or mixer; A method of melt-mixing both using an extruder etc., a method of evaporating the solvent from a mixture of both solutions,
Alternatively, a method of precipitation or a method of adding polyalkylene terephthalate at any stage of the production of aromatic polyester polycarbonate can be adopted. The composition of the present invention may include other resins, such as aliphatic polyester resins such as polycaprolactone, polyolefin resins such as polyethylene, polypropylene, and ethylene-vinyl acetate copolymers, to the extent that their properties are not impaired. , polymethyl methacrylate, ethylene-methyl methacrylate copolymer, polyacrylate resin such as polymethacrylic acid, polyacetal resin, etc. may be blended. Also stabilizers such as phosphoric acid, phosphorous acid, their esters or their metal salts, reinforcing agents such as glass fiber, carbon fiber, silica, alumina, silica-alumina, silica-magnesia, calcium compounds. Other additives such as fillers, plasticizers, lubricants, ultraviolet absorbers, flame retardants, dyes and pigments can also be added. The composition of the present invention has improved moldability, impact resistance, and solvent resistance without impairing the excellent properties inherent to aromatic polyester polycarbonate, and can be processed by injection molding, extrusion molding, and other thermoforming methods. Since it is easy to use, it can be used in a wide range of applications as an engineering plastic, and has great industrial value. EXAMPLES The present invention will be specifically explained below with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist thereof. In the examples, parts indicate parts by weight, and tensile strength, bending strength, and Izod impact strength are based on ASTM D638, ASTM D790, and ASTM D790, respectively.
This is a value measured based on D256. In addition, the solvent resistance is 1/2" in width, 1/8" in thickness, and 1/8" in length.
After applying a bending stress of 50 Kg/cm 3 to a 5" test piece and immersing it in toluene or butyl acetate at room temperature for 5 minutes, the presence or absence of cracks or crazes was determined visually. In the table below, ○ indicates cracks or crazes. No generation of craze was observed, and × indicates the occurrence of craze. Production example of aromatic polyester polycarbonate A 3% methylene chloride solution of terephthaloyl chloride and bisphenol A were dissolved in a 5% aqueous sodium hydroxide solution. A 13% aqueous solution of bisphenol A sodium salt and a 2% aqueous triethylamine solution prepared as above were filled into a glass bulb with an inner diameter of 30 mm and a length of 1.5 m at flow rates of 44.2 Kg/hr, 15.9 Kg/hr, and 0.2 Kg/hr, respectively. Supply to the tower, 0.75m from the supply port of the tower
A reaction was carried out by blowing 0.75 Kg/hr of phosgene from the position, and an oligomer having an ester bond and a chloroformate group at the end was produced. A methylene chloride solution of the above oligomer obtained by separating the reaction mixture 44.0 Kg/hr, a 13% aqueous solution of the same bisphenol A sodium salt as above 17.6 Kg/hr,
1.1 kg/hr of 25% aqueous sodium hydroxide solution, 0.67 kg/hr of 2% aqueous triethylamine solution, and 27 g/hr of p-tert-butylphenol were supplied to a stirring tank so that the average residence time was 2 hours. A polycondensation reaction was carried out. The methylene chloride solution of the polymer obtained by separating the reaction mixture was washed with water, an aqueous hydrochloric acid solution, and then water, and then the methylene chloride was vaporized until [η] was 0.75.
An aromatic polyester polycarbonate having a bisphenol A residue: terephthalic acid residue: carbonate bond molar ratio of 1:0.46:0.54 was obtained. Examples 1 to 5 and Comparative Example 1.2 100 parts of the aromatic polyester polycarbonate powder produced in the above production example was mixed with polyalkylene terephthalate in the amount shown in Table 1 below, and melt-mixed at 300°C using an extruder. and extruded into pellets. These pellets are processed into an injection molding machine (Nissei Plastics Co., Ltd.).
TS-100 model) and a test piece mold specified by ASTM. The molding temperature, mold temperature and injection pressure at that time required the values shown in Table 1 below. The mechanical properties and heat distortion temperature of the test piece thus obtained were as shown in Table 2 below. For comparison, the results obtained when polyalkylene terephthalate was not blended and when a large amount of polyalkylene terephthalate was used are also shown.
【表】【table】
【表】
ただし上表中、PBTは固有粘度1.10のポリブ
チレンテレフタレート(三菱化成工業(株)製、ノバ
ドウール5010)、PETは固有粘度0.66のポリエチ
レンテレフタレート(三菱化成工業(株)製、ノバペ
ツト1065B)である。[Table] In the above table, PBT is polybutylene terephthalate with an intrinsic viscosity of 1.10 (manufactured by Mitsubishi Chemical Industries, Ltd., Novad Wool 5010), and PET is polyethylene terephthalate with an intrinsic viscosity of 0.66 (manufactured by Mitsubishi Chemical Industries, Ltd., Novapet 1065B). It is.
Claims (1)
を有していてもよい。) で表わされる構造単位と、一般式 (式中、Xおよび芳香核は上記と同一意義を有
する。) で表わされる構造単位とからなり、かつジヒドロ
キシジアリール化合物残基:テレフタル酸残基:
カーボネート結合のモル比が1:0.33〜0.75:
0.67〜0.25である芳香族ポリエステルポリカーボ
ネート100重量部に、ポリアルキレンテレフタレ
ート1〜150重量部を配合してなる138℃以上の熱
変形温度をもち、成形性、耐衝撃性および耐溶剤
性に優れた樹脂組成物。 2 芳香族ポリエステルポリカーボネートの固有
粘度が0.4〜1.5である特許請求の範囲第1項記載
の樹脂組成物。 3 芳香族ポリエステルポリカーボネートのガラ
ス転移点が、160〜190℃である特許請求の範囲第
1項記載の樹脂組成物。 4 芳香族ポリエステルポリカーボネートの末端
カルボキシル基が10μ当量/g樹脂以下である特
許請求の範囲第1項記載の樹脂組成物。[Claims] 1. General formula (In the formula, X represents a divalent group, and the aromatic nucleus may have a substituent.) A structural unit represented by the following and the general formula (In the formula, X and the aromatic nucleus have the same meanings as above.) Consisting of a structural unit represented by: dihydroxydiaryl compound residue: terephthalic acid residue:
The molar ratio of carbonate bonds is 1:0.33-0.75:
100 parts by weight of aromatic polyester polycarbonate having a molecular weight of 0.67 to 0.25, mixed with 1 to 150 parts by weight of polyalkylene terephthalate, has a heat distortion temperature of 138°C or higher, and has excellent moldability, impact resistance, and solvent resistance. Resin composition. 2. The resin composition according to claim 1, wherein the aromatic polyester polycarbonate has an intrinsic viscosity of 0.4 to 1.5. 3. The resin composition according to claim 1, wherein the aromatic polyester polycarbonate has a glass transition point of 160 to 190°C. 4. The resin composition according to claim 1, wherein the aromatic polyester polycarbonate has a terminal carboxyl group of 10 μ equivalent/g resin or less.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1704179A JPS55110153A (en) | 1979-02-16 | 1979-02-16 | Resin composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1704179A JPS55110153A (en) | 1979-02-16 | 1979-02-16 | Resin composition |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS55110153A JPS55110153A (en) | 1980-08-25 |
JPS6330341B2 true JPS6330341B2 (en) | 1988-06-17 |
Family
ID=11932906
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP1704179A Granted JPS55110153A (en) | 1979-02-16 | 1979-02-16 | Resin composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS55110153A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018040745A1 (en) * | 2016-08-29 | 2018-03-08 | 江苏扬农化工集团有限公司 | Method for synthesizing terephthaloyl chloride through continuous flow in micro-channel reactor |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS55131049A (en) * | 1979-04-02 | 1980-10-11 | Sumitomo Chem Co Ltd | Novel thermoplastic resin composition |
US4461877A (en) * | 1981-05-01 | 1984-07-24 | General Electric Company | Polycarbonate/poly(ethylene terephthalate) resin solutions |
CA1177593A (en) * | 1981-05-01 | 1984-11-06 | Daniel W. Fox | Polycarbonate/poly(ethylene terephthalate) resin solutions |
US4645804A (en) * | 1981-05-01 | 1987-02-24 | General Electric Company | Polycarbonate/imide hetero group condensation polymer blends |
US4652617A (en) * | 1981-05-01 | 1987-03-24 | General Electric Company | Polycarbonate/ester hetero group condensation polymer blends |
EP0137230A3 (en) * | 1983-08-30 | 1986-09-03 | General Electric Company | Thermoplastic molding compositions |
WO1985002622A1 (en) * | 1983-12-14 | 1985-06-20 | General Electric Company | Color stabilized compositions of polycarbonate-polyester compositions and method of stabilization |
DE3570244D1 (en) * | 1984-02-10 | 1989-06-22 | Gen Electric | Use of a polymer blend for producing medical devices with improved resistance to yellowing under ionizing radiation |
EP0244480A1 (en) * | 1985-10-24 | 1987-11-11 | Culler Scientific Systems Corporation | Integrated, multicomputer data processing system |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4854160A (en) * | 1971-11-09 | 1973-07-30 | ||
JPS52128992A (en) * | 1976-04-02 | 1977-10-28 | Allied Chem | Melt processing copolymer of bisphenol aatelephthalateecarbonate and preparation thereof |
-
1979
- 1979-02-16 JP JP1704179A patent/JPS55110153A/en active Granted
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4854160A (en) * | 1971-11-09 | 1973-07-30 | ||
JPS52128992A (en) * | 1976-04-02 | 1977-10-28 | Allied Chem | Melt processing copolymer of bisphenol aatelephthalateecarbonate and preparation thereof |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018040745A1 (en) * | 2016-08-29 | 2018-03-08 | 江苏扬农化工集团有限公司 | Method for synthesizing terephthaloyl chloride through continuous flow in micro-channel reactor |
US10689321B2 (en) | 2016-08-29 | 2020-06-23 | Jiangsu Yangnong Chemical Group Co., Ltd | Method for synthesizing paraphthaloyl chloride through continuous flow in microchannel reactor |
Also Published As
Publication number | Publication date |
---|---|
JPS55110153A (en) | 1980-08-25 |
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