DE3028092A1 - Thermoplastische polymermaterialien und ihre herstellung - Google Patents
Thermoplastische polymermaterialien und ihre herstellungInfo
- Publication number
- DE3028092A1 DE3028092A1 DE19803028092 DE3028092A DE3028092A1 DE 3028092 A1 DE3028092 A1 DE 3028092A1 DE 19803028092 DE19803028092 DE 19803028092 DE 3028092 A DE3028092 A DE 3028092A DE 3028092 A1 DE3028092 A1 DE 3028092A1
- Authority
- DE
- Germany
- Prior art keywords
- terephthalate
- bisphenol
- molar ratio
- isophthalate
- copolycarbonate
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 229920001169 thermoplastic Polymers 0.000 title description 5
- 239000002861 polymer material Substances 0.000 title description 4
- 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 86
- 229940106691 bisphenol a Drugs 0.000 claims description 41
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims description 32
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 26
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 claims description 24
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 229920000728 polyester Polymers 0.000 claims description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 12
- 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 11
- 239000012815 thermoplastic material Substances 0.000 claims description 11
- 125000005587 carbonate group Chemical group 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229920001634 Copolyester Polymers 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 claims description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical group OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims description 4
- KHKKBAJAVLCDOE-UHFFFAOYSA-N carbonic acid;phthalic acid Chemical compound OC(O)=O.OC(=O)C1=CC=CC=C1C(O)=O KHKKBAJAVLCDOE-UHFFFAOYSA-N 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000000463 material Substances 0.000 description 25
- 239000000047 product Substances 0.000 description 23
- 230000009477 glass transition Effects 0.000 description 18
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 15
- 238000002474 experimental method Methods 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 10
- 230000035882 stress Effects 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 7
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 230000018109 developmental process Effects 0.000 description 5
- 238000009864 tensile test Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical group OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000000214 vapour pressure osmometry Methods 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 230000002087 whitening effect Effects 0.000 description 3
- 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
- 238000010521 absorption reaction Methods 0.000 description 2
- MGIAHHJRDZCTHG-UHFFFAOYSA-N benzene-1,3-dicarboxylic acid;terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1.OC(=O)C1=CC=CC(C(O)=O)=C1 MGIAHHJRDZCTHG-UHFFFAOYSA-N 0.000 description 2
- 239000004035 construction material Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- 125000006414 CCl Chemical group ClC* 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 102100037709 Desmocollin-3 Human genes 0.000 description 1
- 101000968042 Homo sapiens Desmocollin-2 Proteins 0.000 description 1
- 101000880960 Homo sapiens Desmocollin-3 Proteins 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- LRNRWPYXVVMMLQ-UHFFFAOYSA-N carbonic acid;terephthalic acid Chemical compound OC(O)=O.OC(=O)C1=CC=C(C(O)=O)C=C1 LRNRWPYXVVMMLQ-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 238000007865 diluting Methods 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
- 238000002845 discoloration Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005489 elastic deformation Effects 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 238000000411 transmission spectrum Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 229920006352 transparent thermoplastic Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7925845 | 1979-07-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3028092A1 true DE3028092A1 (de) | 1981-02-19 |
Family
ID=10506743
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803028092 Withdrawn DE3028092A1 (de) | 1979-07-25 | 1980-07-24 | Thermoplastische polymermaterialien und ihre herstellung |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US4355150A (enExample) |
| JP (1) | JPS5620029A (enExample) |
| BE (1) | BE884245A (enExample) |
| DE (1) | DE3028092A1 (enExample) |
| FR (1) | FR2462454A1 (enExample) |
| GB (1) | GB2060664B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2060664B (en) * | 1979-07-25 | 1983-10-26 | Secr Defence | Polyester carbonates |
| US4330662A (en) * | 1980-10-27 | 1982-05-18 | The Dow Chemical Company | Ordered copolyestercarbonate resins |
| US4429083A (en) | 1981-10-05 | 1984-01-31 | Idemitsu Kosan Company Limited | Process for the production of polyesterpolycarbonate |
| US4465820A (en) * | 1983-06-03 | 1984-08-14 | General Electric Company | Copolyestercarbonates |
| US4506065A (en) * | 1984-01-03 | 1985-03-19 | General Electric Company | Copolyestercarbonates |
| US4804700A (en) * | 1985-07-11 | 1989-02-14 | General Electric Company | Resinous compositions |
| 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 |
| US5614599A (en) * | 1994-10-31 | 1997-03-25 | The Dow Chemical Company | Stilbene-based polyester and polycarbonate compositions |
| US20090189321A1 (en) * | 2008-01-29 | 2009-07-30 | Dow Global Technologies Inc. | Thermoplastic composition and use for large parison blow molding applications |
| US8525191B2 (en) * | 2011-04-01 | 2013-09-03 | Sabic Innovative Plastics Ip B.V. | Optoelectronic devices and coatings therefore |
| US10066102B2 (en) | 2013-11-22 | 2018-09-04 | Trinseo Europe Gmbh | Polycarbonate containing compositions |
| KR101890500B1 (ko) | 2013-11-22 | 2018-08-21 | 트린세오 유럽 게엠베하 | 폴리카보네이트 함유 조성물 |
| WO2016042355A1 (en) | 2014-09-15 | 2016-03-24 | Trinseo Europe Gmbh | Flame retardant polycarbonates having high total luminous transmittance |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT595468A (enExample) * | 1957-08-22 | |||
| 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 |
| US4260731A (en) * | 1978-09-11 | 1981-04-07 | Mitsubishi Chemical Industries, Ltd. | Aromatic polyester-polycarbonate |
| GB2060664B (en) * | 1979-07-25 | 1983-10-26 | Secr Defence | Polyester carbonates |
-
1980
- 1980-07-02 GB GB8021608A patent/GB2060664B/en not_active Expired
- 1980-07-09 BE BE0/201348A patent/BE884245A/fr not_active IP Right Cessation
- 1980-07-15 US US06/169,211 patent/US4355150A/en not_active Expired - Lifetime
- 1980-07-18 JP JP9862880A patent/JPS5620029A/ja active Granted
- 1980-07-24 FR FR8016365A patent/FR2462454A1/fr active Granted
- 1980-07-24 DE DE19803028092 patent/DE3028092A1/de not_active Withdrawn
-
1982
- 1982-07-16 US US06/399,128 patent/US4465814A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| FR2462454B1 (enExample) | 1983-06-17 |
| US4355150A (en) | 1982-10-19 |
| JPS6121487B2 (enExample) | 1986-05-27 |
| US4465814A (en) | 1984-08-14 |
| FR2462454A1 (fr) | 1981-02-13 |
| GB2060664A (en) | 1981-05-07 |
| JPS5620029A (en) | 1981-02-25 |
| GB2060664B (en) | 1983-10-26 |
| BE884245A (fr) | 1980-11-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8139 | Disposal/non-payment of the annual fee |