JPH0135009B2 - - Google Patents
Info
- Publication number
- JPH0135009B2 JPH0135009B2 JP55083000A JP8300080A JPH0135009B2 JP H0135009 B2 JPH0135009 B2 JP H0135009B2 JP 55083000 A JP55083000 A JP 55083000A JP 8300080 A JP8300080 A JP 8300080A JP H0135009 B2 JPH0135009 B2 JP H0135009B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- mol
- alkyl
- reaction
- linking member
- 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
- -1 diaryl carbonate Chemical compound 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 229920000515 polycarbonate Polymers 0.000 claims description 9
- 239000004417 polycarbonate Substances 0.000 claims description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 238000006068 polycondensation reaction Methods 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000001118 alkylidene group Chemical group 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 4
- 239000012528 membrane Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 229920001169 thermoplastic Polymers 0.000 claims description 4
- 239000004416 thermosoftening plastic Substances 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 230000003197 catalytic effect Effects 0.000 claims 1
- 239000007809 chemical reaction catalyst Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 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 17
- 239000000243 solution Substances 0.000 description 15
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 8
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
- HPUPGAFDTWIMBR-UHFFFAOYSA-N [methyl(phenoxy)phosphoryl]oxybenzene Chemical class C=1C=CC=CC=1OP(=O)(C)OC1=CC=CC=C1 HPUPGAFDTWIMBR-UHFFFAOYSA-N 0.000 description 7
- 238000004455 differential thermal analysis Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 4
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- 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 4
- 239000008187 granular material Substances 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000012086 standard solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 210000002268 wool Anatomy 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
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 2
- IBDMRHDXAQZJAP-UHFFFAOYSA-N dichlorophosphorylbenzene Chemical compound ClP(Cl)(=O)C1=CC=CC=C1 IBDMRHDXAQZJAP-UHFFFAOYSA-N 0.000 description 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 2
- 229940008406 diethyl sulfate Drugs 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000003685 thermal hair damage Effects 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- XJHAKOXOLSWNFR-UHFFFAOYSA-N 2,4-bis(4-hydroxyphenyl)-3-propan-2-ylphenol Chemical compound CC(C)C1=C(C=2C=CC(O)=CC=2)C=CC(O)=C1C1=CC=C(O)C=C1 XJHAKOXOLSWNFR-UHFFFAOYSA-N 0.000 description 1
- MAQOZOILPAMFSW-UHFFFAOYSA-N 2,6-bis[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=C(CC=3C(=CC=C(C)C=3)O)C=C(C)C=2)O)=C1 MAQOZOILPAMFSW-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 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 description 1
- 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 1
- XJGTVJRTDRARGO-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]benzene-1,3-diol Chemical compound C=1C=C(O)C=C(O)C=1C(C)(C)C1=CC=C(O)C=C1 XJGTVJRTDRARGO-UHFFFAOYSA-N 0.000 description 1
- RQTDWDATSAVLOR-UHFFFAOYSA-N 4-[3,5-bis(4-hydroxyphenyl)phenyl]phenol Chemical compound C1=CC(O)=CC=C1C1=CC(C=2C=CC(O)=CC=2)=CC(C=2C=CC(O)=CC=2)=C1 RQTDWDATSAVLOR-UHFFFAOYSA-N 0.000 description 1
- MIJYTDQAOVQRRT-UHFFFAOYSA-N 4-[4,6-bis(4-hydroxyphenyl)-4,6-dimethylhept-2-en-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)=CC(C)(C=1C=CC(O)=CC=1)CC(C)(C)C1=CC=C(O)C=C1 MIJYTDQAOVQRRT-UHFFFAOYSA-N 0.000 description 1
- CIEGINNQDIULCT-UHFFFAOYSA-N 4-[4,6-bis(4-hydroxyphenyl)-4,6-dimethylheptan-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)CC(C)(C=1C=CC(O)=CC=1)CC(C)(C)C1=CC=C(O)C=C1 CIEGINNQDIULCT-UHFFFAOYSA-N 0.000 description 1
- IQNDEQHJTOJHAK-UHFFFAOYSA-N 4-[4-[2-[4,4-bis(4-hydroxyphenyl)cyclohexyl]propan-2-yl]-1-(4-hydroxyphenyl)cyclohexyl]phenol Chemical compound C1CC(C=2C=CC(O)=CC=2)(C=2C=CC(O)=CC=2)CCC1C(C)(C)C(CC1)CCC1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 IQNDEQHJTOJHAK-UHFFFAOYSA-N 0.000 description 1
- LIDWAYDGZUAJEG-UHFFFAOYSA-N 4-[bis(4-hydroxyphenyl)-phenylmethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)(C=1C=CC(O)=CC=1)C1=CC=CC=C1 LIDWAYDGZUAJEG-UHFFFAOYSA-N 0.000 description 1
- ZYUVGYBAPZYKSA-UHFFFAOYSA-N 5-(3-hydroxybutan-2-yl)-4-methylbenzene-1,3-diol Chemical compound CC(O)C(C)C1=CC(O)=CC(O)=C1C ZYUVGYBAPZYKSA-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
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 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
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- LKMDHQMGVTVIRI-UHFFFAOYSA-N [butyl(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(CCCC)OC1=CC=CC=C1 LKMDHQMGVTVIRI-UHFFFAOYSA-N 0.000 description 1
- UHMQAIKRVPHZGY-UHFFFAOYSA-N [ethyl(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(CC)OC1=CC=CC=C1 UHMQAIKRVPHZGY-UHFFFAOYSA-N 0.000 description 1
- HKYWEKLIWPYEOV-UHFFFAOYSA-N [phenoxy(propan-2-yl)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(C(C)C)OC1=CC=CC=C1 HKYWEKLIWPYEOV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- FKPSBYZGRQJIMO-UHFFFAOYSA-M benzyl(triethyl)azanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC1=CC=CC=C1 FKPSBYZGRQJIMO-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- IZJIAOFBVVYSMA-UHFFFAOYSA-N bis(4-methylphenyl) carbonate Chemical compound C1=CC(C)=CC=C1OC(=O)OC1=CC=C(C)C=C1 IZJIAOFBVVYSMA-UHFFFAOYSA-N 0.000 description 1
- 239000006085 branching agent Substances 0.000 description 1
- BWKDLDWUVLGWFC-UHFFFAOYSA-N calcium;azanide Chemical compound [NH2-].[NH2-].[Ca+2] BWKDLDWUVLGWFC-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000002485 combustion 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
- 238000001816 cooling Methods 0.000 description 1
- NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000004193 disodium 5'-ribonucleotide Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 238000007373 indentation Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- XAVQZBGEXVFCJI-UHFFFAOYSA-M lithium;phenoxide Chemical class [Li+].[O-]C1=CC=CC=C1 XAVQZBGEXVFCJI-UHFFFAOYSA-M 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012745 toughening agent Substances 0.000 description 1
- 229960002415 trichloroethylene Drugs 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 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
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
- C08G79/04—Phosphorus linked to oxygen or to oxygen and carbon
-
- 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
- C08G64/083—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen containing phosphorus
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792925208 DE2925208A1 (de) | 1979-06-22 | 1979-06-22 | Verfahren zur herstellung von aromatischen thermoplastischen polyphosphonatocarbonaten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS565823A JPS565823A (en) | 1981-01-21 |
| JPH0135009B2 true JPH0135009B2 (OSRAM) | 1989-07-21 |
Family
ID=6073875
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8300080A Granted JPS565823A (en) | 1979-06-22 | 1980-06-20 | Thermoplastic aromatic polyphosphonate carbonate and its manufacture |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US4322520A (OSRAM) |
| EP (1) | EP0021216B1 (OSRAM) |
| JP (1) | JPS565823A (OSRAM) |
| DE (2) | DE2925208A1 (OSRAM) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2925208A1 (de) * | 1979-06-22 | 1981-01-29 | Bayer Ag | Verfahren zur herstellung von aromatischen thermoplastischen polyphosphonatocarbonaten |
| DE3001863A1 (de) * | 1980-01-19 | 1981-07-23 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von thermoplastischen aromatischen polyphosphonatocarbonaten verbesserter thermischer alterungsbestaendigkeit und deren verwendung |
| DE3111653A1 (de) * | 1981-03-25 | 1982-10-14 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von thermoplastischen, aromatischen polyphosphaten mit geringen anteilen an carbonatstrukturen |
| US4381390A (en) * | 1981-10-15 | 1983-04-26 | Mobay Chemical Corporation | Thermoplastic polyphosphonatophenyl ester carbonate from aryloxycarbonyloxy-benzoic acid aryl ester and preparation thereof |
| US4481350A (en) * | 1982-03-22 | 1984-11-06 | Bayer Aktiengesellschaft | Process for the preparation of thermoplastic aromatic polyphosphonates containing small proportions of carbonate structures and product thereof |
| EP0103227B1 (de) * | 1982-09-10 | 1985-11-27 | Bayer Ag | Verfahren zur Herstellung von Polyphosphaten, nach diesem Verfahren hergestellte Polyphosphate und ihre Verwendung |
| US4444978A (en) * | 1983-07-29 | 1984-04-24 | The Dow Chemical Company | Thermally stable carbonate polymer |
| US4474937A (en) * | 1983-10-03 | 1984-10-02 | The Dow Chemical Company | Phosphorus-modified polyestercarbonate resins |
| US4556698A (en) * | 1984-12-03 | 1985-12-03 | Fmc Corporation | Flame retardant thermoplastic polycarbonate polymers |
| JPS61143573A (ja) * | 1984-12-15 | 1986-07-01 | Nippon Steel Corp | メツキ付着量自動制御方法およびその装置 |
| DE3520296A1 (de) * | 1985-06-07 | 1986-12-11 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von copolyphosphonaten mit hoher zaehigkeit |
| JP2794676B2 (ja) * | 1990-08-24 | 1998-09-10 | 日新製鋼株式会社 | 溶融差厚めっきの付着量制御法 |
| JP2000219745A (ja) * | 1999-02-02 | 2000-08-08 | Johoku Kagaku Kogyo Kk | 難燃性化合物、その製造方法および難燃化有機高分子材料 |
| JP4778601B2 (ja) * | 2000-03-27 | 2011-09-21 | 出光興産株式会社 | 難燃性ポリカーボネート樹脂組成物および成形品 |
| JP5066777B2 (ja) * | 2000-09-22 | 2012-11-07 | 東レ株式会社 | 樹脂および成型体 |
| WO2002024787A1 (fr) * | 2000-09-22 | 2002-03-28 | Toray Industries, Inc. | Composition de resine et articles moules a partir de celle-ci |
| JP3975793B2 (ja) * | 2002-03-20 | 2007-09-12 | 東レ株式会社 | 樹脂およびその成型体 |
| JP2004269844A (ja) * | 2003-02-18 | 2004-09-30 | Toray Ind Inc | 熱可塑性樹脂および成形体 |
| US6861499B2 (en) * | 2003-02-24 | 2005-03-01 | Triton Systems, Inc. | Branched polyphosphonates that exhibit an advantageous combination of properties, and methods related thereto |
| US20040167283A1 (en) * | 2003-02-24 | 2004-08-26 | Michael Vinciguerra | Linear polyphosphonates that exhibit an advantageous combination of properties, and methods related thereto |
| JP2005126575A (ja) * | 2003-10-24 | 2005-05-19 | Toray Ind Inc | 樹脂の製造方法 |
| US7645850B2 (en) * | 2005-08-11 | 2010-01-12 | Frx Polymers, Inc. | Poly(block-phosphonato-ester) and poly(block-phosphonato-carbonate) and methods of making same |
| US7666932B2 (en) * | 2005-10-17 | 2010-02-23 | Frx Polymers, Inc. | Compositions comprising polyphosphonates and additives that exhibit an advantageous combination of properties, and methods related thereto |
| CN101291942B (zh) * | 2005-10-18 | 2012-05-30 | Frx聚合物有限责任公司 | 烷基膦酸二芳基酯及其制备方法 |
| US7838604B2 (en) | 2005-12-01 | 2010-11-23 | Frx Polymers, Inc. | Method for the production of block copolycarbonate/phosphonates and compositions therefrom |
| WO2009018336A2 (en) * | 2007-07-30 | 2009-02-05 | Frx Polymers, Inc. | Insoluble and branched polyphosphonates and methods related thereto |
| DE102008038410A1 (de) | 2007-09-11 | 2009-03-12 | Basf Se | Flammgeschützte Polyester |
| DE102008038411A1 (de) | 2007-09-11 | 2009-03-12 | Basf Se | Flammgeschützte Polyamide |
| WO2009043758A1 (de) | 2007-09-28 | 2009-04-09 | Basf Se | Verfahren zur herstellung flammgeschützter thermoplastischer formmassen |
| US7928259B2 (en) * | 2008-02-12 | 2011-04-19 | Frx Polymers, Inc. | Diaryl alkylphosphonates and methods for preparing same |
| KR20100132537A (ko) * | 2008-04-01 | 2010-12-17 | 바스프 에스이 | 난연성 열가소성 조성물 |
| EP2297240B1 (de) * | 2008-07-07 | 2012-10-24 | Styrolution GmbH | Kautschukmodifizierte flammgeschützte formmassen |
| JP5808253B2 (ja) * | 2009-01-08 | 2015-11-10 | クラリアント・インターナシヨナル・リミテツド | ポリエステル用難燃剤の組み合わせ及びそれにより難燃化されたポリエステル成形組成物 |
| WO2011009877A1 (de) | 2009-07-24 | 2011-01-27 | Basf Se | Flammgeschützte polyamidformmassen |
| WO2011039301A1 (de) | 2009-10-01 | 2011-04-07 | Basf Se | Funktionalisierte expandierbare graphiteinlagerungsverbindungen |
| WO2011039292A1 (de) | 2009-10-01 | 2011-04-07 | Basf Se | Verfahren zur herstellung funktionalisierter expandierbarer graphiteinlagerungsverbindungen |
| US8450407B2 (en) | 2009-10-27 | 2013-05-28 | Basf Se | Heat aging-resistant polyamides with flame retardancy |
| US20110237695A1 (en) | 2010-03-23 | 2011-09-29 | Clariant International Ltd. | Flame Retardant Combinations For Polyester Elastomers And Flame Retarded Extrusion Or Molding Compositions Therefrom |
| KR20130100912A (ko) | 2010-05-05 | 2013-09-12 | 바스프 에스이 | 삽입부 및 플라스틱 재킷류를 포함하는 구성요소 및 그의 제조 방법 |
| WO2012013564A1 (de) | 2010-07-30 | 2012-02-02 | Basf Se | Flammgeschützte formmassen |
| CN105367775B (zh) | 2010-09-16 | 2018-04-13 | Frx 聚合物股份有限公司 | 基于双酚的高分子量无规共聚（膦酸酯碳酸酯） |
| ES2533960T3 (es) | 2010-10-15 | 2015-04-16 | Styrolution Europe Gmbh | Procedimiento para la preparación de masas moldeables termoplásticas ignífugas |
| JP2014503698A (ja) * | 2010-11-17 | 2014-02-13 | エフアールエックス ポリマーズ、インク． | ポリエステル繊維の難燃剤としてのホスホン酸ポリマー、コポリマー、およびそれぞれのオリゴマー |
| WO2012080388A1 (de) | 2010-12-16 | 2012-06-21 | Basf Se | Kautschukmodifizierte flammgeschützte formmassen und deren herstellung |
| WO2014116669A1 (en) | 2013-01-22 | 2014-07-31 | Frx Polymers, Inc. | Phosphorus containing epoxy compounds and compositions therefrom |
| KR102824966B1 (ko) * | 2021-09-30 | 2025-06-24 | 롯데케미칼 주식회사 | 카보네이트 포스포네이트 공중합체 및 이를 포함하는 열가소성 수지 조성물 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2682522A (en) * | 1952-09-10 | 1954-06-29 | Eastman Kodak Co | Process for preparing polymeric organo-phosphonates |
| US3378523A (en) * | 1961-09-14 | 1968-04-16 | Eastman Kodak Co | Bisphenol polyesters containing phosphorus |
| GB1025422A (en) * | 1961-11-30 | 1966-04-06 | Gevaert Photo Prod Nv | Copolyesters and the preparation thereof |
| FR1402407A (fr) * | 1964-07-24 | 1965-06-11 | Nautchno I I Plastitcheskich M | Procédé de préparation de polycarbonates |
| US3597394A (en) * | 1969-10-16 | 1971-08-03 | Mobay Chemical Corp | Branching or crosslinking of polycarbonates |
| US4054552A (en) * | 1970-04-13 | 1977-10-18 | General Electric Company | Thermal oxidatively stable polycarbonate |
| US4223104A (en) * | 1978-08-11 | 1980-09-16 | Stauffer Chemical Company | Copoly (carbonate/phosphonate) compositions |
| DE2925208A1 (de) * | 1979-06-22 | 1981-01-29 | Bayer Ag | Verfahren zur herstellung von aromatischen thermoplastischen polyphosphonatocarbonaten |
| DE3001863A1 (de) * | 1980-01-19 | 1981-07-23 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von thermoplastischen aromatischen polyphosphonatocarbonaten verbesserter thermischer alterungsbestaendigkeit und deren verwendung |
| US4381390A (en) * | 1981-10-15 | 1983-04-26 | Mobay Chemical Corporation | Thermoplastic polyphosphonatophenyl ester carbonate from aryloxycarbonyloxy-benzoic acid aryl ester and preparation thereof |
| US4481350A (en) * | 1982-03-22 | 1984-11-06 | Bayer Aktiengesellschaft | Process for the preparation of thermoplastic aromatic polyphosphonates containing small proportions of carbonate structures and product thereof |
-
1979
- 1979-06-22 DE DE19792925208 patent/DE2925208A1/de not_active Withdrawn
-
1980
- 1980-06-09 EP EP80103194A patent/EP0021216B1/de not_active Expired
- 1980-06-09 DE DE8080103194T patent/DE3066260D1/de not_active Expired
- 1980-06-18 US US06/160,644 patent/US4322520A/en not_active Expired - Lifetime
- 1980-06-20 JP JP8300080A patent/JPS565823A/ja active Granted
-
1985
- 1985-05-20 US US06/735,635 patent/US4762905A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US4322520A (en) | 1982-03-30 |
| EP0021216A1 (de) | 1981-01-07 |
| DE3066260D1 (en) | 1984-03-01 |
| DE2925208A1 (de) | 1981-01-29 |
| EP0021216B1 (de) | 1984-01-25 |
| US4762905A (en) | 1988-08-09 |
| JPS565823A (en) | 1981-01-21 |
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