CA1071231A - Process for the purification of polycarbonates - Google Patents
Process for the purification of polycarbonatesInfo
- Publication number
- CA1071231A CA1071231A CA240,853A CA240853A CA1071231A CA 1071231 A CA1071231 A CA 1071231A CA 240853 A CA240853 A CA 240853A CA 1071231 A CA1071231 A CA 1071231A
- Authority
- CA
- Canada
- Prior art keywords
- set forth
- process set
- water
- acid
- oligocarbonate
- 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
- 238000000034 method Methods 0.000 title claims abstract description 32
- 238000000746 purification Methods 0.000 title claims description 5
- 229920000515 polycarbonate Polymers 0.000 title description 19
- 239000004417 polycarbonate Substances 0.000 title description 19
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 10
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000002009 diols Chemical class 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims abstract description 6
- 238000007872 degassing Methods 0.000 claims abstract description 5
- 239000011261 inert gas Substances 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims abstract description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 6
- 238000011010 flushing procedure Methods 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 239000011260 aqueous acid Substances 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 239000001569 carbon dioxide Substances 0.000 claims description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 3
- 239000012153 distilled water Substances 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 239000001117 sulphuric acid Substances 0.000 claims description 3
- 235000011149 sulphuric acid Nutrition 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 235000011167 hydrochloric acid Nutrition 0.000 claims 1
- 229960000443 hydrochloric acid Drugs 0.000 claims 1
- 235000011007 phosphoric acid Nutrition 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 2
- 238000004383 yellowing Methods 0.000 abstract description 2
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 229920003225 polyurethane elastomer Polymers 0.000 abstract 1
- 238000010926 purge Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229960005419 nitrogen Drugs 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ZWVMLYRJXORSEP-LURJTMIESA-N (2s)-hexane-1,2,6-triol Chemical compound OCCCC[C@H](O)CO ZWVMLYRJXORSEP-LURJTMIESA-N 0.000 description 1
- WYUYEJNGHIOFOC-VVTVMFAVSA-N 2-[(z)-1-(4-methylphenyl)-3-pyrrolidin-1-ylprop-1-enyl]pyridine;hydrochloride Chemical compound Cl.C1=CC(C)=CC=C1C(\C=1N=CC=CC=1)=C\CN1CCCC1 WYUYEJNGHIOFOC-VVTVMFAVSA-N 0.000 description 1
- -1 O - Cl - O Chemical class 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 229910052936 alkali metal sulfate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- CVMNKHMWNZSNLW-UHFFFAOYSA-N hexane-1,6-diol;2-(2-hydroxyethoxy)ethanol Chemical compound OCCOCCO.OCCCCCCO CVMNKHMWNZSNLW-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- HGEVGSTXQGZPCL-UHFFFAOYSA-N nonanedioyl dichloride Chemical compound ClC(=O)CCCCCCCC(Cl)=O HGEVGSTXQGZPCL-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/08—Purification; Separation; Stabilisation
-
- 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
- C08G64/40—Post-polymerisation treatment
- C08G64/406—Purifying; Drying
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyesters Or Polycarbonates (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7440836A FR2294198A1 (fr) | 1974-12-11 | 1974-12-11 | Procede de purification des oligocarbonates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1071231A true CA1071231A (en) | 1980-02-05 |
Family
ID=9146035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA240,853A Expired CA1071231A (en) | 1974-12-11 | 1975-12-01 | Process for the purification of polycarbonates |
Country Status (13)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2373570A1 (fr) | 1976-12-10 | 1978-07-07 | Poudres & Explosifs Ste Nale | Nouveaux polycarbonates aliphatiques triols et leurs applications |
| US4306057A (en) * | 1978-03-27 | 1981-12-15 | General Electric Company | Solvent sweeping of polycarbonates |
| US4498017A (en) * | 1982-12-16 | 1985-02-05 | Parkins William E | Generating power from wind |
| DE3503330A1 (de) * | 1985-02-01 | 1986-08-07 | Herberts Gmbh, 5600 Wuppertal | Verfahren zur verminderung des geruchs von polyesterharzen und deren verwendung |
| EP0302712B1 (en) * | 1987-08-04 | 1996-11-13 | Asahi Kasei Kogyo Kabushiki Kaisha | Novel copolycarbonate |
| US5243093A (en) * | 1990-09-07 | 1993-09-07 | General Electric Company | Process and composition |
| DE4130807A1 (de) * | 1991-09-17 | 1993-03-18 | Wolff Walsrode Ag | Verfahren zur herstellung von polysaccharidcarbonaten |
| US5239106A (en) * | 1992-08-17 | 1993-08-24 | General Electric Company | Method of recovering and purifying diphenylcarbonate from phenolic solutions thereof |
| US5498319A (en) * | 1993-06-29 | 1996-03-12 | General Electric Company | Process for purifying diaryl carbonates |
| DE4420778A1 (de) * | 1994-06-15 | 1995-12-21 | Bayer Ag | Verfahren zur Reinigung von Diphenylcarbonat |
| US5777064A (en) * | 1995-03-22 | 1998-07-07 | Mitsubishi Gas Chemical Company, Inc. | Production method of polycarbonate |
| US7388066B2 (en) * | 2005-09-26 | 2008-06-17 | Bridgestone Sports Co., Ltd. | Golf ball |
| US20070072701A1 (en) * | 2005-09-26 | 2007-03-29 | Bridgestone Sports Co., Ltd. | Golf ball |
| WO2018013886A1 (en) | 2016-07-14 | 2018-01-18 | Lanxess Solutions Us Inc. | Cast urethanes made from low free monomer prepolymer with polycarbonate backbone |
| KR102450692B1 (ko) | 2017-02-28 | 2022-10-06 | 도레이 카부시키가이샤 | 시트상물 |
| WO2018159359A1 (ja) | 2017-02-28 | 2018-09-07 | 三洋化成工業株式会社 | 合成皮革用ポリウレタン樹脂 |
| KR102572560B1 (ko) | 2017-03-29 | 2023-08-30 | 도레이 카부시키가이샤 | 시트상물 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1234900A (fr) * | 1958-10-20 | 1960-10-19 | Columbia Southern Chem Corp | Procédé pour produire des substances synthétiques macromoléculaires, notamment des polycarbonates solides |
| US3213060A (en) * | 1961-09-14 | 1965-10-19 | Eastman Kodak Co | Polycarbonate purification |
| US3470133A (en) * | 1967-09-15 | 1969-09-30 | Ppg Industries Inc | Water washing polyesters of carbonic acid and diphenols |
| US3668181A (en) * | 1970-03-06 | 1972-06-06 | Allied Chem | Purification of polycarbonate resins |
-
1974
- 1974-12-11 FR FR7440836A patent/FR2294198A1/fr active Granted
-
1975
- 1975-11-07 IE IE2428/75A patent/IE42221B1/en unknown
- 1975-11-18 GB GB47471/75A patent/GB1479389A/en not_active Expired
- 1975-12-01 CA CA240,853A patent/CA1071231A/en not_active Expired
- 1975-12-04 US US05/637,760 patent/US4013702A/en not_active Expired - Lifetime
- 1975-12-04 NL NL7514136A patent/NL7514136A/xx not_active Application Discontinuation
- 1975-12-09 LU LU73967A patent/LU73967A1/xx unknown
- 1975-12-09 IT IT70017/75A patent/IT1059854B/it active
- 1975-12-09 DD DD189989A patent/DD124738A5/xx unknown
- 1975-12-10 DK DK558875A patent/DK558875A/da not_active Application Discontinuation
- 1975-12-11 BE BE162657A patent/BE836534A/xx unknown
- 1975-12-11 JP JP50146949A patent/JPS5183692A/ja active Granted
- 1975-12-11 DE DE19752555766 patent/DE2555766A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| IE42221B1 (en) | 1980-07-02 |
| BE836534A (fr) | 1976-06-11 |
| LU73967A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-07-01 |
| FR2294198B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-04-08 |
| NL7514136A (nl) | 1976-06-15 |
| IT1059854B (it) | 1982-06-21 |
| JPS5342359B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-11-10 |
| US4013702A (en) | 1977-03-22 |
| FR2294198A1 (fr) | 1976-07-09 |
| DD124738A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-03-09 |
| AU8688875A (en) | 1977-06-02 |
| JPS5183692A (en) | 1976-07-22 |
| DE2555766A1 (de) | 1976-06-16 |
| IE42221L (en) | 1976-06-11 |
| DK558875A (da) | 1976-06-12 |
| GB1479389A (en) | 1977-07-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |