JPS6215573B2 - - Google Patents
Info
- Publication number
- JPS6215573B2 JPS6215573B2 JP52134171A JP13417177A JPS6215573B2 JP S6215573 B2 JPS6215573 B2 JP S6215573B2 JP 52134171 A JP52134171 A JP 52134171A JP 13417177 A JP13417177 A JP 13417177A JP S6215573 B2 JPS6215573 B2 JP S6215573B2
- Authority
- JP
- Japan
- Prior art keywords
- polyester
- bis
- polyol
- carbonate
- aryl
- 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
- 229920000728 polyester Polymers 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 32
- 229920005906 polyester polyol Polymers 0.000 claims description 20
- -1 hydroxyaryl compound Chemical class 0.000 claims description 18
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 14
- 150000002009 diols Chemical class 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 150000005846 sugar alcohols Polymers 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 238000005809 transesterification reaction Methods 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 150000002596 lactones Chemical class 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 150000007860 aryl ester derivatives Chemical class 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 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 20
- 229920000515 polycarbonate Polymers 0.000 description 19
- 239000004417 polycarbonate Substances 0.000 description 19
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 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
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000001361 adipic acid Substances 0.000 description 5
- 235000011037 adipic acid Nutrition 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 4
- 229920001400 block copolymer Polymers 0.000 description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 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 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000004455 differential thermal analysis Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- ZYPNBSUWRMDKPK-UHFFFAOYSA-N (2,3-dichlorophenyl) hydrogen carbonate Chemical compound OC(=O)OC1=CC=CC(Cl)=C1Cl ZYPNBSUWRMDKPK-UHFFFAOYSA-N 0.000 description 1
- SLYBYYOFYNYTAY-UHFFFAOYSA-N (2-chloro-3-phenylphenyl) hydrogen carbonate Chemical compound OC(=O)OC1=CC=CC(C=2C=CC=CC=2)=C1Cl SLYBYYOFYNYTAY-UHFFFAOYSA-N 0.000 description 1
- ZGSHFDSKHTZINF-UHFFFAOYSA-N (2-methyl-6-phenylphenyl) hydrogen carbonate Chemical compound CC1=CC=CC(C=2C=CC=CC=2)=C1OC(O)=O ZGSHFDSKHTZINF-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-LURJTMIESA-N (2s)-hexane-1,2,6-triol Chemical compound OCCCC[C@H](O)CO ZWVMLYRJXORSEP-LURJTMIESA-N 0.000 description 1
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-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
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
- KNDQHSIWLOJIGP-UHFFFAOYSA-N 826-62-0 Chemical compound C1C2C3C(=O)OC(=O)C3C1C=C2 KNDQHSIWLOJIGP-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- JOZSCPCCPRBYNA-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol;[4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1.OCC1(CO)CCCCC1 JOZSCPCCPRBYNA-UHFFFAOYSA-N 0.000 description 1
- PZKZDBBWDMPJKN-UHFFFAOYSA-N [4-chloro-2-(4-methylphenyl)phenyl] hydrogen carbonate Chemical compound C1=CC(C)=CC=C1C1=CC(Cl)=CC=C1OC(O)=O PZKZDBBWDMPJKN-UHFFFAOYSA-N 0.000 description 1
- LJCTUEPREAVQFG-UHFFFAOYSA-N [4-methyl-3-(2-methylphenyl)phenyl] hydrogen carbonate Chemical compound CC1=CC=CC=C1C1=CC(OC(O)=O)=CC=C1C LJCTUEPREAVQFG-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- IHQIYIBQSPHBNT-UHFFFAOYSA-N bis[4-[2-(4-hydroxyphenyl)propan-2-yl]phenyl] carbonate Chemical compound C=1C=C(OC(=O)OC=2C=CC(=CC=2)C(C)(C)C=2C=CC(O)=CC=2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IHQIYIBQSPHBNT-UHFFFAOYSA-N 0.000 description 1
- 229920000402 bisphenol A polycarbonate polymer Polymers 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- VKONPUDBRVKQLM-UHFFFAOYSA-N cyclohexane-1,4-diol Chemical compound OC1CCC(O)CC1 VKONPUDBRVKQLM-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- OASFYFTVWALXTH-UHFFFAOYSA-L disodium;diphenoxide Chemical compound [Na+].[Na+].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OASFYFTVWALXTH-UHFFFAOYSA-L 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012774 insulation material Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229940113165 trimethylolpropane Drugs 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/64—Polyesters containing both carboxylic ester groups and carbonate groups
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/91—Polymers modified by chemical after-treatment
- C08G63/914—Polymers modified by chemical after-treatment derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/916—Dicarboxylic acids and dihydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762651639 DE2651639A1 (de) | 1976-11-12 | 1976-11-12 | Verfahren zur herstellung von kohlensaeureestern von polyesterpolyolen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5361690A JPS5361690A (en) | 1978-06-02 |
| JPS6215573B2 true JPS6215573B2 (en, 2012) | 1987-04-08 |
Family
ID=5993008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13417177A Granted JPS5361690A (en) | 1976-11-12 | 1977-11-10 | Manufacture of carbonate of polyesterrpolyol and new type carbonate obtained |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4191705A (en, 2012) |
| JP (1) | JPS5361690A (en, 2012) |
| DE (1) | DE2651639A1 (en, 2012) |
| FR (1) | FR2370765A1 (en, 2012) |
| GB (1) | GB1558018A (en, 2012) |
| IT (1) | IT1109439B (en, 2012) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2726376A1 (de) * | 1977-06-10 | 1978-12-21 | Bayer Ag | Verfahren zur herstellung von kohlensaeure-bis-diphenolestern von polyesterdiolen und ihre verwendung zur herstellung von hochmolekularen, segmentierten, thermoplastisch verarbeitbaren polyester- polycarbonaten |
| US4297455A (en) * | 1977-03-22 | 1981-10-27 | Bayer Aktiengesellschaft | Process for the preparation of carbonic acid aryl esters of polyester-diols lengthened via carbonate groups and their use for the preparation of polyester-diol bis-diphenol carbonates and polyester/polycarbonates |
| DE2732718A1 (de) * | 1977-07-20 | 1979-02-15 | Bayer Ag | Carbonatgruppen enthaltende polyester |
| DE2837526A1 (de) * | 1978-08-28 | 1980-03-20 | Bayer Ag | Verfahren zur herstellung von polymeren mit diphenolcarbonat-endgruppen |
| DE2930787A1 (de) * | 1979-07-28 | 1981-02-12 | Bayer Ag | Vernetzbare polycarbonat-elastomere, ein verfahren zu ihrer herstellung und ihre verwendung fuer medizinische verpackungen nach erfolgter vernetzung |
| DE3120594A1 (de) * | 1981-05-23 | 1982-12-16 | Bayer Ag, 5090 Leverkusen | Neue copolyestercarbonate und deren abmischung mit bekannten polycarbonaten zu thermoplastischen formmassen |
| DE3316851A1 (de) | 1983-05-07 | 1984-11-08 | Bayer Ag, 5090 Leverkusen | Polymerisierbare dentalmassen und hieraus hergestellte dentalformkoerper |
| US4686273A (en) * | 1985-07-01 | 1987-08-11 | The Dow Chemical Company | Process for preparing modified poly(alkylene carbonate) polyahls |
| US4816529A (en) * | 1985-11-18 | 1989-03-28 | The Dow Chemical Company | Novel ester-modified poly(alkylene carbonate) polyahls and polyurethanes therefrom |
| US4795810A (en) * | 1985-11-18 | 1989-01-03 | The Dow Chemical Company | Modified poly(alkylene carbonate) polyahls |
| US4686274A (en) * | 1985-12-16 | 1987-08-11 | The Dow Chemical Company | Process for preparing modified poly(alkylene carbonate) polyahls |
| US4948862A (en) * | 1985-12-16 | 1990-08-14 | The Dow Chemical Company | Modified poly(alkylene carbonate) polyahls |
| US5084528A (en) * | 1985-12-16 | 1992-01-28 | The Dow Chemical Company | Novel ester-modified poly(alkylene carbonate) polyahls |
| US4689353A (en) * | 1986-02-21 | 1987-08-25 | The Dow Chemical Company | Hydroxy and amino-functional polyahls containing carbonate, urethane and/or urea moieties |
| US4861909A (en) * | 1986-04-11 | 1989-08-29 | The Dow Chemical Company | Isocyanate-modified poly(alkylene carbonate) polyahls |
| US4879357A (en) * | 1986-10-02 | 1989-11-07 | The Dow Chemical Company | Novel poly(alkylene carbonate) polyahls having more than one pendant acid group |
| US4956424A (en) * | 1986-10-02 | 1990-09-11 | The Dow Chemical Company | Novel poly (alkylene carbonate) polyahls having more than one pendant acid group |
| US4959499A (en) * | 1986-11-04 | 1990-09-25 | The Dow Chemical Company | Liquid polymers containing urethane and urea moieties and hydroxyl and/or amino end groups and a process for the preparation thereof |
| DE4137842A1 (de) * | 1991-11-16 | 1993-05-19 | Zimmer Ag | Verfahren zur kontinuierlichen polykondensation von terephthalsaeure und 1,4-bis-(hydroxymethyl)-cyclohexan |
| DE4137841C2 (de) * | 1991-11-16 | 2003-08-28 | Zimmer Ag | Diskontinuierliches Verfahren zur Polykondensation von Terephthalsäure und 1,4-Bis-(hydroxymethyl)-cyclohexan |
| JP4928394B2 (ja) * | 2007-09-19 | 2012-05-09 | 株式会社オートネットワーク技術研究所 | コネクタ |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3161615A (en) * | 1957-02-05 | 1964-12-15 | Gen Electric | Resinous copolymeric polycarbonate of a mixture of dihydric phenols |
| IT595468A (en, 2012) * | 1957-08-22 | |||
| BE570530A (en, 2012) * | 1957-08-22 | |||
| US3030331A (en) * | 1957-08-22 | 1962-04-17 | Gen Electric | Process for preparing copolyesters comprising reacting a carbonyl halide with a dicarboxylic acid and a dihydroxy compound in the presence of a tertiary amine |
| GB898775A (en) | 1958-01-13 | 1962-06-14 | Bexford Ltd | Improvements in or relating to polymeric materials |
| US3030335A (en) * | 1959-01-02 | 1962-04-17 | Gen Electric | Aromatic polycarbonate reaction products |
| BE593044A (en, 2012) | 1959-07-17 | |||
| GB954500A (en) | 1960-07-05 | 1964-04-08 | Bx Plastics Ltd | Process for the manufacture of linear co-polycondensation products |
| US3207814A (en) * | 1961-01-03 | 1965-09-21 | Gen Electric | Carbonate-polyester copolymer resinous compositions |
| US3290409A (en) * | 1962-03-08 | 1966-12-06 | Gen Electric | Preparation of polycarbonate resins |
| US3287442A (en) * | 1962-10-18 | 1966-11-22 | Eastman Kodak Co | Polycarbonate elastomers |
| DE1301552B (de) * | 1963-06-19 | 1969-08-21 | Teijin Ltd | Verfahren zur Herstellung von linearen Polyestern |
| FR1401635A (fr) * | 1964-06-19 | 1965-06-04 | Teijin Ltd | Procédé de préparation de polyesters essentiellement linéaires |
| GB1139413A (en) * | 1965-02-03 | 1969-01-08 | Ici Fibres Ltd | Polyester/polycarbonate block copolymers |
| US3449467A (en) * | 1965-06-03 | 1969-06-10 | Union Carbide Corp | Hydroxyl terminated polyester oligomers |
| US3461187A (en) * | 1965-12-02 | 1969-08-12 | Gen Electric | Graft copolymers of polycarbonate on an addition polymer backbone |
| DE1493757A1 (de) * | 1965-12-29 | 1969-01-30 | Bayer Ag | Verfahren zur Herstellung von gemischten Kohlensaeureestern |
| DE1593864A1 (de) * | 1967-03-25 | 1971-02-25 | Bayer Ag | Verfahren zur Herstellung von Hydrazincarbonsaeureestern |
| DE1643978C3 (de) | 1967-07-12 | 1975-05-07 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Neopentylglykol-carbonsäure-kohlensäure-Mischestern |
| US3843708A (en) * | 1969-01-17 | 1974-10-22 | Union Carbide Corp | Extended polylactone diol compositions |
| US3641200A (en) * | 1969-01-17 | 1972-02-08 | Union Carbide Corp | Block copolycarbonates containing polylactone blocks and dihydric phenol polycarbonate blocks |
| DE1964998C3 (de) * | 1969-12-24 | 1979-02-15 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Polyurethanelastomeren |
| JPS495630B1 (en, 2012) * | 1970-03-19 | 1974-02-08 | ||
| DE2217470A1 (de) * | 1971-04-13 | 1972-11-02 | Denki Onkyo Co. Ltd., Tokio | Block-Copolymerisate |
| GB1440311A (en) * | 1972-07-06 | 1976-06-23 | Ici Ltd | Polyester film |
| GB1422676A (en) | 1972-11-29 | 1976-01-28 | Gen Electric | Production of polyesters |
| FR2235965A1 (en) | 1973-06-15 | 1975-01-31 | Ugine Kuhlmann | Sequenced polycarbonate-polycaprolactone copolymers - prepd. from oligomers with reactive end gps |
| DE2726417A1 (de) * | 1977-06-11 | 1978-12-21 | Bayer Ag | Verfahren zur herstellung von kohlensaeure-bis-diphenolestern von ueber carbonat-gruppen-verlaengerten polyesterdiolen und ihre verwendung zur herstellung von hochmolekularen, segmentierten, thermoplastisch verarbeitbaren polyester- polycarbonaten |
| DE2712435A1 (de) * | 1977-03-22 | 1978-09-28 | Bayer Ag | Verfahren zur herstellung von kohlensaeurearylestern von ueber carbonat- gruppen-verlaengerten polyesterdiolen |
| US4105633A (en) * | 1977-05-11 | 1978-08-08 | The Dow Chemical Company | Alternating copolyestercarbonate resins |
-
1976
- 1976-11-12 DE DE19762651639 patent/DE2651639A1/de not_active Ceased
-
1977
- 1977-10-25 US US05/845,174 patent/US4191705A/en not_active Expired - Lifetime
- 1977-11-09 GB GB46636/77A patent/GB1558018A/en not_active Expired
- 1977-11-10 IT IT51761/77A patent/IT1109439B/it active
- 1977-11-10 JP JP13417177A patent/JPS5361690A/ja active Granted
- 1977-11-10 FR FR7734012A patent/FR2370765A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2370765A1 (fr) | 1978-06-09 |
| GB1558018A (en) | 1979-12-19 |
| US4191705A (en) | 1980-03-04 |
| FR2370765B1 (en, 2012) | 1983-10-07 |
| IT1109439B (it) | 1985-12-16 |
| DE2651639A1 (de) | 1978-05-24 |
| JPS5361690A (en) | 1978-06-02 |
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