NL8002431A - Werkwijze ter bereiding van copolyester-carbonaten. - Google Patents
Werkwijze ter bereiding van copolyester-carbonaten. Download PDFInfo
- Publication number
- NL8002431A NL8002431A NL8002431A NL8002431A NL8002431A NL 8002431 A NL8002431 A NL 8002431A NL 8002431 A NL8002431 A NL 8002431A NL 8002431 A NL8002431 A NL 8002431A NL 8002431 A NL8002431 A NL 8002431A
- Authority
- NL
- Netherlands
- Prior art keywords
- acid
- carbonate
- process according
- copolyester
- dichloride
- Prior art date
Links
- 229920001634 Copolyester Polymers 0.000 title claims description 29
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 27
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 18
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 14
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 7
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000002243 precursor Substances 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 claims description 4
- 229940106691 bisphenol a Drugs 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- ROFMCPHQNWGXGE-SFHVURJKSA-N (3s)-n-[2-[2-(dimethylamino)ethoxy]-4-(1h-pyrazol-4-yl)phenyl]-6-methoxy-3,4-dihydro-2h-chromene-3-carboxamide Chemical compound O=C([C@@H]1COC2=CC=C(C=C2C1)OC)NC(C(=C1)OCCN(C)C)=CC=C1C=1C=NNC=1 ROFMCPHQNWGXGE-SFHVURJKSA-N 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000002989 phenols Chemical class 0.000 description 7
- -1 resorcinoins Chemical class 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 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 4
- UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-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
- 150000007513 acids Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229920006026 co-polymeric resin Polymers 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 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
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-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
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000005205 dihydroxybenzenes Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 150000004675 formic acid derivatives Chemical class 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000005067 haloformyl group Chemical group 0.000 description 2
- ZHQLTKAVLJKSKR-UHFFFAOYSA-N homophthalic acid Chemical compound OC(=O)CC1=CC=CC=C1C(O)=O ZHQLTKAVLJKSKR-UHFFFAOYSA-N 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
- 239000000463 material Substances 0.000 description 2
- YDSWCNNOKPMOTP-UHFFFAOYSA-N mellitic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O YDSWCNNOKPMOTP-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 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
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-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
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 2
- GJHVEONIFIJEIH-UHFFFAOYSA-N (2-chloronaphthalen-1-yl) (2-chlorophenyl) carbonate Chemical compound ClC1=CC=CC=C1OC(=O)OC1=C(Cl)C=CC2=CC=CC=C12 GJHVEONIFIJEIH-UHFFFAOYSA-N 0.000 description 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- AEQDJSLRWYMAQI-UHFFFAOYSA-N 2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline Chemical compound C1CN2CC(C(=C(OC)C=C3)OC)=C3CC2C2=C1C=C(OC)C(OC)=C2 AEQDJSLRWYMAQI-UHFFFAOYSA-N 0.000 description 1
- AYNPIRVEWMUJDE-UHFFFAOYSA-N 2,5-dichlorohydroquinone Chemical compound OC1=CC(Cl)=C(O)C=C1Cl AYNPIRVEWMUJDE-UHFFFAOYSA-N 0.000 description 1
- ZKZKMLKTQUCSNX-UHFFFAOYSA-N 2,6-dibromo-4-(3,5-dibromo-4-hydroxyphenyl)sulfinylphenol Chemical compound C1=C(Br)C(O)=C(Br)C=C1S(=O)C1=CC(Br)=C(O)C(Br)=C1 ZKZKMLKTQUCSNX-UHFFFAOYSA-N 0.000 description 1
- TXYQFJWVHVYIHB-UHFFFAOYSA-N 2,6-dichloro-4-(3,5-dichloro-4-hydroxyphenoxy)phenol Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1OC1=CC(Cl)=C(O)C(Cl)=C1 TXYQFJWVHVYIHB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-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
- MLDIQALUMKMHCC-UHFFFAOYSA-N 4,4-Bis(4-hydroxyphenyl)heptane Chemical compound C=1C=C(O)C=CC=1C(CCC)(CCC)C1=CC=C(O)C=C1 MLDIQALUMKMHCC-UHFFFAOYSA-N 0.000 description 1
- KXYDGGNWZUHESZ-UHFFFAOYSA-N 4-(2,2,4-trimethyl-3h-chromen-4-yl)phenol Chemical compound C12=CC=CC=C2OC(C)(C)CC1(C)C1=CC=C(O)C=C1 KXYDGGNWZUHESZ-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
- KSYGTCNPCHQRKM-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KSYGTCNPCHQRKM-UHFFFAOYSA-N 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-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
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000012695 Interfacial polymerization Methods 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920002732 Polyanhydride Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940107816 ammonium iodide Drugs 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- CJPIDIRJSIUWRJ-UHFFFAOYSA-N benzene-1,2,4-tricarbonyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C(C(Cl)=O)=C1 CJPIDIRJSIUWRJ-UHFFFAOYSA-N 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- VCYAMSXIIWQHKV-UHFFFAOYSA-N bis(2,3,4-tribromophenyl) carbonate Chemical compound BrC1=C(Br)C(Br)=CC=C1OC(=O)OC1=CC=C(Br)C(Br)=C1Br VCYAMSXIIWQHKV-UHFFFAOYSA-N 0.000 description 1
- DSEORJACOQDMQX-UHFFFAOYSA-N bis(2,3,4-trichlorophenyl) carbonate Chemical compound ClC1=C(Cl)C(Cl)=CC=C1OC(=O)OC1=CC=C(Cl)C(Cl)=C1Cl DSEORJACOQDMQX-UHFFFAOYSA-N 0.000 description 1
- LUQQDEDMRRRWGN-UHFFFAOYSA-N bis(2-bromophenyl) carbonate Chemical compound BrC1=CC=CC=C1OC(=O)OC1=CC=CC=C1Br LUQQDEDMRRRWGN-UHFFFAOYSA-N 0.000 description 1
- SJWFGMZZMOUDTF-UHFFFAOYSA-N bis(2-chloronaphthalen-1-yl) carbonate Chemical compound C1=CC=C2C(OC(=O)OC3=C4C=CC=CC4=CC=C3Cl)=C(Cl)C=CC2=C1 SJWFGMZZMOUDTF-UHFFFAOYSA-N 0.000 description 1
- MUCRFDZUHPMASM-UHFFFAOYSA-N bis(2-chlorophenyl) carbonate Chemical compound ClC1=CC=CC=C1OC(=O)OC1=CC=CC=C1Cl MUCRFDZUHPMASM-UHFFFAOYSA-N 0.000 description 1
- POZGCGJFBOZPCM-UHFFFAOYSA-N bis(2-methylphenyl) carbonate Chemical compound CC1=CC=CC=C1OC(=O)OC1=CC=CC=C1C POZGCGJFBOZPCM-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 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
- IKWKJIWDLVYZIY-UHFFFAOYSA-M butyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCC)C1=CC=CC=C1 IKWKJIWDLVYZIY-UHFFFAOYSA-M 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004653 carbonic acids Chemical class 0.000 description 1
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- OREAFAJWWJHCOT-UHFFFAOYSA-N dimethylmalonic acid Chemical compound OC(=O)C(C)(C)C(O)=O OREAFAJWWJHCOT-UHFFFAOYSA-N 0.000 description 1
- ZQUZPFYNEARCQO-UHFFFAOYSA-N dinaphthalen-1-yl carbonate Chemical compound C1=CC=C2C(OC(OC=3C4=CC=CC=C4C=CC=3)=O)=CC=CC2=C1 ZQUZPFYNEARCQO-UHFFFAOYSA-N 0.000 description 1
- GWZCCUDJHOGOSO-UHFFFAOYSA-N diphenic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1C(O)=O GWZCCUDJHOGOSO-UHFFFAOYSA-N 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 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
- NNYHMCFMPHPHOQ-UHFFFAOYSA-N mellitic anhydride Chemical compound O=C1OC(=O)C2=C1C(C(OC1=O)=O)=C1C1=C2C(=O)OC1=O NNYHMCFMPHPHOQ-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000008379 phenol ethers Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000004023 quaternary phosphonium compounds Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000176 sodium gluconate Substances 0.000 description 1
- 229940005574 sodium gluconate Drugs 0.000 description 1
- 235000012207 sodium gluconate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- 229920006344 thermoplastic copolyester Polymers 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
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- HNJXPTMEWIVQQM-UHFFFAOYSA-M triethyl(hexadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](CC)(CC)CC HNJXPTMEWIVQQM-UHFFFAOYSA-M 0.000 description 1
- NJMOHBDCGXJLNJ-UHFFFAOYSA-N trimellitic anhydride chloride Chemical compound ClC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 NJMOHBDCGXJLNJ-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-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
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3339079 | 1979-04-26 | ||
| US06/033,390 US4238596A (en) | 1979-04-26 | 1979-04-26 | Process for obtaining copolyester-carbonates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8002431A true NL8002431A (nl) | 1980-10-28 |
Family
ID=21870145
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8002431A NL8002431A (nl) | 1979-04-26 | 1980-04-25 | Werkwijze ter bereiding van copolyester-carbonaten. |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4238596A (enExample) |
| JP (1) | JPS56822A (enExample) |
| AU (1) | AU5771280A (enExample) |
| CA (1) | CA1140298A (enExample) |
| DE (1) | DE3016019A1 (enExample) |
| FR (1) | FR2455058A1 (enExample) |
| GB (1) | GB2047723B (enExample) |
| IT (1) | IT1141321B (enExample) |
| NL (1) | NL8002431A (enExample) |
Families Citing this family (67)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4360656A (en) * | 1977-05-11 | 1982-11-23 | The Dow Chemical Co. | Alternating copolyestercarbonate resins |
| US4330662A (en) * | 1980-10-27 | 1982-05-18 | The Dow Chemical Company | Ordered copolyestercarbonate resins |
| US4358569A (en) * | 1980-12-31 | 1982-11-09 | General Electric Company | Blends of copolyester-carbonate with polysulfone |
| EP0069157A1 (en) * | 1981-07-02 | 1983-01-12 | The Dow Chemical Company | Alternating copolyestercarbonate resins |
| JPS5864127U (ja) * | 1981-10-22 | 1983-04-30 | セイコ−京葉工業株式会社 | 圧電振動子ウエハ |
| US4386196A (en) * | 1982-04-02 | 1983-05-31 | Allied Corporation | Interfacial process for producing poly(ester-carbonate) containing phenolphthalein |
| US4469850A (en) * | 1982-11-05 | 1984-09-04 | General Electric Company | Compositions |
| US4499257A (en) * | 1983-04-18 | 1985-02-12 | Union Carbide Corporation | Poly(ester-carbonate)s |
| DE3346945A1 (de) * | 1983-12-24 | 1985-07-04 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von aromatischen polyestercarbonaten |
| US4506065A (en) * | 1984-01-03 | 1985-03-19 | General Electric Company | Copolyestercarbonates |
| DE3535663A1 (de) * | 1985-10-05 | 1987-04-09 | Bayer Ag | Aromatische polyestercarbonate, verfahren zu ihrer herstellung und ihre verwendung zur herstellung von formkoerpern, folien und ueberzuegen |
| US4788275A (en) * | 1986-12-23 | 1988-11-29 | General Electric Company | Aromatic copolyester carbonate endcapped with chromanyl I compound |
| US4902737A (en) * | 1986-12-23 | 1990-02-20 | General Electric Company | Resin blends exhibiting improved impact properties |
| US5037889A (en) * | 1986-12-23 | 1991-08-06 | General Electric Company | Resin blends exhibiting improved impact properties |
| US4774315A (en) * | 1986-12-23 | 1988-09-27 | General Electric Company | Copoly isophthalate carbonate end-capped with paracumylphenol |
| US5070177A (en) * | 1988-11-04 | 1991-12-03 | General Electric Company | Ultraviolet radiation resistant polyphthalatecarbonate resin |
| US4918149A (en) * | 1988-11-04 | 1990-04-17 | General Electric Company | Polyphthalatecarbonate/polycarbonate resin blends |
| CA2030616A1 (en) | 1989-12-22 | 1991-06-23 | Luca P. Fontana | Composition |
| US4983706A (en) * | 1990-01-30 | 1991-01-08 | General Electric Company | Interfacial process comprising reacting a dihydric phenol, a carbonate precursor and an aliphatic alpha omega dicarboxylic salt |
| US5015720A (en) * | 1990-06-08 | 1991-05-14 | General Electric Company | Method for preparing polycarbonates containing aliphatic ester groups |
| US5274068A (en) * | 1992-04-23 | 1993-12-28 | General Electric Company | Catalytic, interfacial, pH controlled preparation of polyester polycarbonate |
| EP0681037B1 (en) * | 1994-05-03 | 1997-09-24 | General Electric Company | Process for the manufacture of a metallized article |
| US5494997A (en) | 1994-08-01 | 1996-02-27 | General Electric Company | Preparation of by the bischloroformate process of soft segment polycarbonate |
| US5614599A (en) * | 1994-10-31 | 1997-03-25 | The Dow Chemical Company | Stilbene-based polyester and polycarbonate compositions |
| US6288203B1 (en) * | 1995-11-27 | 2001-09-11 | Idemitsu Petrochemical Co., Ltd. | Processes for the production of polycarbonate |
| JPH11106635A (ja) * | 1997-09-30 | 1999-04-20 | Ge Plastics Japan Ltd | ポリカーボネート樹脂組成物およびその成形品 |
| WO2000026274A1 (en) | 1998-10-29 | 2000-05-11 | General Electric Company | Weatherable block copolyestercarbonates and blends containing them |
| ES2251233T3 (es) | 1998-10-29 | 2006-04-16 | General Electric Company | Copoliestercarbonatos de bloque resistentes a la interperie, procedimientos para su preparacion y mezclas que los contienen. |
| US6096853A (en) * | 1998-12-21 | 2000-08-01 | General Electric Company | Synthesis of phenolic monomers containing imide or diimide moieties and high heat carbonate polymers prepared therefrom |
| US6689474B2 (en) | 1999-05-18 | 2004-02-10 | General Electric Company | Thermally stable polymers, method of preparation, and articles made therefrom |
| US6306507B1 (en) | 1999-05-18 | 2001-10-23 | General Electric Company | Thermally stable polymers, method of preparation, and articles made therefrom |
| US7169859B2 (en) * | 1999-05-18 | 2007-01-30 | General Electric Company | Weatherable, thermostable polymers having improved flow composition |
| US7790292B2 (en) * | 1999-05-18 | 2010-09-07 | Sabic Innovative Plastics Ip B.V. | Polysiloxane copolymers, thermoplastic composition, and articles formed therefrom |
| US7605221B2 (en) * | 1999-05-18 | 2009-10-20 | Sabic Innovative Plastics Ip B.V. | Weatherable, thermostable polymers having improved flow composition |
| US6861482B2 (en) | 1999-05-18 | 2005-03-01 | General Electric Company | Weatherable, thermostable polymers having improved flow composition |
| US6664366B2 (en) | 1999-05-18 | 2003-12-16 | General Electric Company | Thermally stable polymers, method of preparation, and articles made therefrom |
| US6333394B1 (en) | 1999-08-09 | 2001-12-25 | General Electric Company | Copolycarbonate preparation by solid state polymerization |
| US6265527B1 (en) | 1999-11-01 | 2001-07-24 | General Electric Company | Method for making polyester carbonates |
| US6232429B1 (en) | 1999-11-01 | 2001-05-15 | General Electric Company | Method for making polyester carbonates |
| US6346597B1 (en) | 1999-12-27 | 2002-02-12 | General Electric Company | Method for making polyester carbonates |
| US6255438B1 (en) | 2000-07-20 | 2001-07-03 | General Electric Company | Phenolic compounds, polymers derived therefrom, and method |
| JP2002194073A (ja) | 2000-12-26 | 2002-07-10 | Ge Plastics Japan Ltd | 新規なポリカーボネート系樹脂および該ポリカーボネート系樹脂の製造方法 |
| US6538065B1 (en) | 2001-07-26 | 2003-03-25 | General Electric Company | Method for preparing copolyestercarbonates and articles therefrom |
| EP1316419A3 (en) * | 2001-11-30 | 2004-01-28 | General Electric Company | Weatherable multilayer articles and method for their preparation |
| US8057903B2 (en) * | 2001-11-30 | 2011-11-15 | Sabic Innovative Plastics Ip B.V. | Multilayer articles comprising resorcinol arylate polyester and method for making thereof |
| US7318958B2 (en) * | 2001-11-30 | 2008-01-15 | General Electric Company | Weatherable multilayer articles and method for their preparation |
| US6790573B2 (en) | 2002-01-25 | 2004-09-14 | Xerox Corporation | Multilayered imaging member having a copolyester-polycarbonate adhesive layer |
| WO2003070806A1 (en) * | 2002-02-21 | 2003-08-28 | Stichting Dutch Polymer Institute | Copolymer containing one or more amide segments |
| US6812320B2 (en) | 2002-03-25 | 2004-11-02 | General Electric Company | Method for copolyestercarbonate synthesis |
| US7514147B2 (en) * | 2003-01-14 | 2009-04-07 | Sabic Innovative Plastics Ip B.V. | Formable thermoplastic multi-layer laminate, a formed multi-layer laminate, an article, and a method of making an article |
| JP2006522696A (ja) * | 2003-02-21 | 2006-10-05 | ゼネラル・エレクトリック・カンパニイ | 耐候性多層物品及びその製造方法 |
| US7270882B2 (en) * | 2003-02-21 | 2007-09-18 | General Electric Company | Weatherable multilayer articles and method for their preparation |
| US20050158561A1 (en) * | 2004-01-16 | 2005-07-21 | General Electric Company | Weatherable multilayer articles and method for their preparation |
| US7153576B2 (en) * | 2004-01-20 | 2006-12-26 | General Electric Company | Weatherable multilayer article assemblies and method for their preparation |
| US20050228130A1 (en) * | 2004-04-12 | 2005-10-13 | General Electric Company | Thermoplastic composition providing a low gloss, textured surface, and method |
| JP4526865B2 (ja) * | 2004-04-30 | 2010-08-18 | Ｓａｂｉｃイノベーティブプラスチックスジャパン合同会社 | ポリエステル樹脂製光反射体 |
| US7326764B2 (en) * | 2005-05-20 | 2008-02-05 | General Electric Company | Transparent compositions, methods for the preparation thereof, and articles derived therefrom |
| US7323536B2 (en) * | 2005-05-20 | 2008-01-29 | General Electric Company | Transparent compositions, methods for the preparation thereof, and articles derived therefrom |
| US7323535B2 (en) * | 2005-05-20 | 2008-01-29 | General Electric Company | Transparent compositions, methods for the preparation thereof, and articles derived therefrom |
| US7273917B2 (en) | 2005-05-20 | 2007-09-25 | General Electric Company | Transparent compositions, methods for the preparation thereof, and articles derived therefrom |
| KR100645065B1 (ko) * | 2005-06-23 | 2006-11-10 | 삼성전자주식회사 | 핀 전계 효과 트랜지스터와 이를 구비하는 비휘발성 메모리장치 및 그 형성 방법 |
| US20070057400A1 (en) * | 2005-09-09 | 2007-03-15 | General Electric Company | Polycarbonate useful in making solvent cast films |
| US7855241B2 (en) * | 2005-10-18 | 2010-12-21 | Sabic Innovative Plastics Ip B.V. | Method of improving abrasion resistance of plastic article using nanoparticles and article produced thereby |
| US7576140B2 (en) * | 2005-10-18 | 2009-08-18 | Sabic Innovative Plastics Ip B.V. | Method of improving abrasion resistance of plastic article and article produced thereby |
| US7524562B2 (en) * | 2005-10-18 | 2009-04-28 | Sabic Innovative Plastics Ip B.V. | Method of improving abrasion resistance of plastic article using functionalized polymers and article produced thereby |
| US8178208B2 (en) * | 2006-12-01 | 2012-05-15 | Sabic Innovative Plastives IP B.V. | Polyester compositions, methods of manufacture, and uses thereof |
| US20100009207A1 (en) * | 2008-07-10 | 2010-01-14 | Sabic Innovative Plastics Ip B.V. | Formable thermoplastic multi-layer article, a formed multi-layer article, an article, and a method of making an article |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3028364A (en) * | 1957-04-02 | 1962-04-03 | Gevaert Photo Prod Nv | Production of linear aromatic polyesters |
| 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 |
| IT595468A (enExample) * | 1957-08-22 | |||
| US3697481A (en) * | 1971-03-08 | 1972-10-10 | Gen Electric | Chromanyl terminated polycarbonate |
| IT998851B (it) * | 1972-10-30 | 1976-02-20 | Gen Electric | Procedimento per la preparazione di policarbonati aromatici |
| US3989672A (en) * | 1972-10-30 | 1976-11-02 | General Electric Company | Process for preparing aromatic carbonate polymers |
| IT1116721B (it) * | 1976-04-02 | 1986-02-10 | Allied Chem | Copolimero bisfenolo a tereftalato carbonato lavorabili in massa fusa |
| US4156069A (en) * | 1976-04-02 | 1979-05-22 | Allied Chemical Corporation | Bisphenol-A/terephthalate/carbonate melt processable copolymers |
-
1979
- 1979-04-26 US US06/033,390 patent/US4238596A/en not_active Expired - Lifetime
-
1980
- 1980-04-22 GB GB8013185A patent/GB2047723B/en not_active Expired
- 1980-04-23 AU AU57712/80A patent/AU5771280A/en not_active Abandoned
- 1980-04-24 IT IT21617/80A patent/IT1141321B/it active
- 1980-04-24 CA CA000350530A patent/CA1140298A/en not_active Expired
- 1980-04-25 JP JP5438980A patent/JPS56822A/ja active Pending
- 1980-04-25 NL NL8002431A patent/NL8002431A/nl not_active Application Discontinuation
- 1980-04-25 FR FR8009422A patent/FR2455058A1/fr active Granted
- 1980-04-25 DE DE19803016019 patent/DE3016019A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| GB2047723B (en) | 1983-05-25 |
| FR2455058A1 (fr) | 1980-11-21 |
| IT8021617A0 (it) | 1980-04-24 |
| DE3016019A1 (de) | 1980-11-13 |
| CA1140298A (en) | 1983-01-25 |
| IT1141321B (it) | 1986-10-01 |
| JPS56822A (en) | 1981-01-07 |
| FR2455058B1 (enExample) | 1983-09-16 |
| AU5771280A (en) | 1980-10-30 |
| US4238596A (en) | 1980-12-09 |
| GB2047723A (en) | 1980-12-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BV | The patent application has lapsed |