DE1046311B - Process for the production of polycarbonates - Google Patents
Process for the production of polycarbonatesInfo
- Publication number
- DE1046311B DE1046311B DEF19984A DEF0019984A DE1046311B DE 1046311 B DE1046311 B DE 1046311B DE F19984 A DEF19984 A DE F19984A DE F0019984 A DEF0019984 A DE F0019984A DE 1046311 B DE1046311 B DE 1046311B
- Authority
- DE
- Germany
- Prior art keywords
- weight
- parts
- polycarbonates
- triethylamine
- dioxy compounds
- 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.)
- Pending
Links
- 229920000515 polycarbonate Polymers 0.000 title claims description 12
- 239000004417 polycarbonate Substances 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 241000790917 Dioxys <bee> Species 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 150000003512 tertiary amines Chemical class 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 4
- 239000012670 alkaline solution Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000010695 polyglycol Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 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
- 230000035484 reaction time Effects 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-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
- KBLAMUYRMZPYLS-UHFFFAOYSA-N 2,3-bis(2-methylpropyl)naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 KBLAMUYRMZPYLS-UHFFFAOYSA-N 0.000 description 1
- PNXAPWZUZUZMDA-UHFFFAOYSA-N 2,3-bis(2-methylpropyl)naphthalene-1-sulfonic acid;sodium Chemical compound [Na].C1=CC=C2C(S(O)(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PNXAPWZUZUZMDA-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-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
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- XMSGXJCDVYZSEJ-UHFFFAOYSA-N C(C)N(CC)CC.C1CO1 Chemical compound C(C)N(CC)CC.C1CO1 XMSGXJCDVYZSEJ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- SLABEOONBHLKSD-UHFFFAOYSA-N O=S1(=O)C(C=C2)=CC=C2OOC2=CC=C1C=C2 Chemical compound O=S1(=O)C(C=C2)=CC=C2OOC2=CC=C1C=C2 SLABEOONBHLKSD-UHFFFAOYSA-N 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000004651 carbonic acid esters Chemical class 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- CIXSDMKDSYXUMJ-UHFFFAOYSA-N n,n-diethylcyclohexanamine Chemical compound CCN(CC)C1CCCCC1 CIXSDMKDSYXUMJ-UHFFFAOYSA-N 0.000 description 1
- WAHWCUPSBZVYPH-UHFFFAOYSA-N n,n-diethylethanamine;sodium Chemical compound [Na].CCN(CC)CC WAHWCUPSBZVYPH-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/22—General preparatory processes using carbonyl halides
- C08G64/24—General preparatory processes using carbonyl halides and phenols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/02—Preparation of esters of carbonic or haloformic acids from phosgene or haloformates
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)
Description
Verfahren zur Herstellung von Polycarbonaten Es ist bekannt, Polycarbonate durch Umsetzung von aromatischen oder aliphatischen Dioxyverbindungen mit Phosgen oder mit Bis-chlorkohlensäureestern solcher Dioxyverbindungen herzustellen. Technisch besonders wertvolle, hochmolekulare Polycarbonate erhält man z. B. durch Umsetzung von Di-monooxyaryl-alkanen, gegebenenfalls im Gemisch Feit anderen Dio_xyverbindungen, oder von Di-monooxyaryl-sulfonen, wiederum gegebenenfalls im Gemisch mit anderen Dioxyverbindungen, oder von Gemischen aus solchen oder anderen aromatischen Dioxyverbindungen und aliphatischen oder/und cycloaliphatischen Dioxyverbindungen mit Derivaten der Kohlensäure, wie hohlensäurediestern, Bis-chlorkohlensäureestern von Dioxyverbindungen und Phosgen, nach den Verfahren gemäß der Patentanmeldungen F 13040 IVb/39c, F 17166 IVb/39c, F 17168 IVh/39c, F 17528 IVb/ 39e, F 19123 IVb/39c.Process for the Production of Polycarbonates It is known to produce polycarbonates by reacting aromatic or aliphatic dioxy compounds with phosgene or with bis-chlorocarbonic acid esters of such dioxy compounds. Technically particularly valuable, high molecular weight polycarbonates are obtained, for. B. by reacting di-monooxyaryl-alkanes, optionally in a mixture of other Dio_xyverbindungen, or di-monooxyaryl-sulfones, again optionally in a mixture with other dioxy compounds, or mixtures of such or other aromatic dioxy compounds and aliphatic and / or cycloaliphatic dioxy compounds with derivatives of carbonic acid, such as hollow diesters, bis-chlorocarbonic acid esters of dioxy compounds and phosgene, according to the process according to patent applications F 13040 IVb / 39c, F 17166 IVb / 39c, F 17168 IVh / 39c, F 17528 IVb / 39e, F 19123 IVb / 39c.
Die Umsetzung der erwähnten Dioxyverbindungen mit Phosgen oder mit Bis-chlorkohlensäureestern von Dioxyverbindungen in wäßrig-alkalischer Lösung oder Suspension" gegebenenfalls in Gegenwart indifferenter Lösungsmittel, wird durch ZuLatz geringer Men gen quarternärer Ammoniumverbindungen in Form der freien Basen oder als. Salze gefördert nach dem Verfahren gemäß Gegenstand des Patentes 959497. The reaction of the dioxy compounds mentioned with phosgene or with bis-chlorocarbonic acid esters of dioxy compounds in aqueous-alkaline solution or suspension "optionally in the presence of inert solvents, is promoted by adding small amounts of quaternary ammonium compounds in the form of the free bases or as salts according to the method according to Subject of patent 959497.
Es wurde nun gefunden, daß man bei der Herstellung von Polycarbonaten unter Verwendung von Bischlorkohlensäureestern von Dioxyverbindungen oder von Phosgen und insbesondere bei der Herstellung hochmolekularer Polycarbonate nach den zuletzt genannten Verfahren auch dann nur relativ kurze Reaktionszeiten benötigt, wenn man dem Reaktionsgemisch geringe Mengen von tertiären Aminen allein oder in Verbindung mit oberflächenaktiven Stoffen zusetzt, insbesondere, wenn man in Gegenwart inerter organischer Lösungsmittel arbeitet. Die Verwendung der tertiären Amine, gegebenenfalls in Verbindung mit oberflächenaktiven Substanzen, führt zu besser reproduzierbaren Ergebnissen als die Verwendung der quarternären Ammoniumverbindungen.It has now been found that in the production of polycarbonates using bishopric carbonic acid esters of dioxy compounds or of phosgene and especially in the production of high molecular weight polycarbonates after the last mentioned method only requires relatively short reaction times if one the reaction mixture small amounts of tertiary amines alone or in combination with surfactants added, especially if you are in the presence of inert organic solvent works. The use of the tertiary amines, if appropriate in connection with surface-active substances, leads to more reproducible Results than the use of the quaternary ammonium compounds.
Tertiäre Amine, die erfindungsgemäß zugesetzt werden können, sind z. B. Trimethylamin, Triäthylamin, Tripropylamin, N,N-Dimethylcyclohexylamin, N,N-Diäthylcyclohexylamin, N,N-Dimethylanilin, N,N-Diäthylanilin, Pyridin, Picolin, Chinolin oder deren Salze.Tertiary amines that can be added according to the invention are z. B. trimethylamine, triethylamine, tripropylamine, N, N-dimethylcyclohexylamine, N, N-diethylcyclohexylamine, N, N-dimethylaniline, N, N-diethylaniline, pyridine, picoline, quinoline or their salts.
Der Zusatz der tertiären Amine beschleunigt die Kondensation zu den Polycarbonaten derart, daß meist schon in i/2 bis 2i/2 Stunden gegebenenfalls hochmolekulare Polycarbonate erhalten werden können. Hierzu genügen im allgemeinen Mengen von 0,05 bis 1 Gewichtsprozent, bezogen auf die eingesetzte Menge der Dioxyverbindungen. Die Amine können vor oder während der Umsetzung dem Reaktionsgemisch zugesetzt werden.The addition of the tertiary amines accelerates the condensation to the Polycarbonates in such a way that usually in ½ to 2½ hours, if necessary, high molecular weight Polycarbonates can be obtained. For this purpose, amounts of 0.05 are generally sufficient up to 1 percent by weight, based on the amount of dioxy compounds used. The amines can be added to the reaction mixture before or during the reaction.
Oberflächenaktive Stoffe, die erfindungsgemäß weiterhin dem Reaktionsgemisch zugesetzt werden können, sind ionogene Netzmittel, wie Fettsäuren oder deren Salze, saure Schwefelsäureester von Fettalkoholen oder deren Salze, aliphatische oder aromatische Sulfonsäuren oder deren Salze, Säureamide aus aliphatischen Carbonsäuren mit Alkylaminosulfonsäuren oder deren Salze, quarternäre Ammoniumverbindungen, und nicht ionogene oberflächenaktive Substanzen, wie Polyglykoläther oder deren Ester mit Fettsäuren und Alkylarylpolyglykoläther.Surface-active substances, according to the invention, continue to be added to the reaction mixture can be added are ionic wetting agents, such as fatty acids or their salts, acidic sulfuric acid esters of fatty alcohols or their salts, aliphatic or aromatic Sulphonic acids or their salts, acid amides from aliphatic carboxylic acids with alkylaminosulphonic acids or their salts, quaternary ammonium compounds, and non-ionic surface-active Substances such as polyglycol ethers or their esters with fatty acids and alkylaryl polyglycol ethers.
Der gleichzeitige Zusatz dieser Stoffe vermag die Reaktionsgeschwindigkeit noch weiter zu erhöhen. Im allgemeinen genügen 0,5 bis 5 Gewichtsprozent der oberflächenaktiven Stoffe, bezogen auf die eingesetzte Menge der Dioxyverbindungen. Auch diese Stoffe können dem Reaktionsgemisch vor oder während der Kondensation zugesetzt werden. In der dem Beispiel 1 folgenden Tabelle sind Reaktionszeiten aufgeführt, die bei Verwendung verschiedener Amine und oberflächenaktiver Stoffe gemessen wurden.The simultaneous addition of these substances can increase the rate of the reaction to increase even further. In general, 0.5 to 5 percent by weight of the surfactant is sufficient Substances, based on the amount of dioxy compounds used. These substances too can be added to the reaction mixture before or during the condensation. In the table which follows Example 1, reaction times are listed which are at Use of various amines and surfactants were measured.
Beispiel 1 In ein Gemisch aus 137,6 Gewichtsteilen 2,2-(4,4'-Dioxydiphenyl)-propan,
69 Gewichtsteilen Natriumhydroxyd, 700 Gewichtsteilen Wasser und 330 Gewichtsteilen
Methylenchlorid werden unter Rühren bei 25° C in 2 Stunden 71,6 Gewichtsteile Phosgen
gasförmig eingeleitet. Dann werden die in der folgenden Tabelle angegebenen Mengen
tertiärer Amine bzw. Netzmittel zugegeben. Die Zeit in Minuten gibt an, wann das
Polycarbonat nach Zugabe der angegebenen Stoffe seine Endviskosität erreicht hat.
Beispiel 3 In ein Gemisch aus 68,8 Gewichtsteilen 2,2-(4,4'-Dioxydiphenyl)Propan (0,5 Mol), 56,2 Gewichtsteilen 4,4'-Dioxydiphenyl (0,5 Mol), 330 Gewichtsteilen Methylenchlorid, 700 Gewichtsteilen Wasser und 69 Gewichtsteilen Natriumhydroxyd werden unter Rühren bei 25° C in 2 Stunden 71,6 Gewichtsteile Phosgen eingeleitet. Dann werden 0,24 Gewichtsteile Triäthylamin und 2 Gewichtsteile diisobutylnaphthalinsulfosaures Natrium zugegeben. Bei weiterem Rühren bei Zimmertemperatur erreicht die Methylenchloridlösung des gebildeten Polycarbonats schon nach 15 Minuten ihre Endviskosität.Example 3 In a mixture of 68.8 parts by weight of 2,2- (4,4'-dioxydiphenyl) propane (0.5 mole), 56.2 parts by weight of 4,4'-dioxydiphenyl (0.5 mole), 330 parts by weight Methylene chloride, 700 parts by weight of water and 69 parts by weight of sodium hydroxide 71.6 parts by weight of phosgene are passed in with stirring at 25 ° C. in 2 hours. Then 0.24 parts by weight of triethylamine and 2 parts by weight of diisobutylnaphthalenesulfonic acid Sodium added. With further stirring at room temperature, the methylene chloride solution reaches of the polycarbonate formed reaches its final viscosity after just 15 minutes.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF19984A DE1046311B (en) | 1956-04-06 | 1956-04-06 | Process for the production of polycarbonates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF19984A DE1046311B (en) | 1956-04-06 | 1956-04-06 | Process for the production of polycarbonates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1046311B true DE1046311B (en) | 1958-12-11 |
Family
ID=7089516
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF19984A Pending DE1046311B (en) | 1956-04-06 | 1956-04-06 | Process for the production of polycarbonates |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1046311B (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1141789B (en) * | 1960-04-21 | 1962-12-27 | Gevaert Photo-Producten N. V., Mortsel, Antwerpen (Belgien) | Process for the production of high molecular weight polycarbonates. |
| US3110698A (en) * | 1959-03-12 | 1963-11-12 | Eastman Kodak Co | Polyesters of carbonyldichlorides and process for polymerization and dope making |
| DE1162079B (en) * | 1960-03-16 | 1964-01-30 | Gevaert Photo Producten N V Mortsel Antwerpen (Belgien) | Process for the production of thermoplastic high molecular weight polycarbonates. |
| DE1163544B (en) | 1960-03-16 | 1964-02-20 | Gevaert Photo Prod Nv | Process for the production of thermoplastic high molecular weight polycarbonates |
| US3207777A (en) * | 1961-11-02 | 1965-09-21 | Electro Chimie Metal | Polycarbonates of polyhydroxy-perchlorobiphenyls |
| DE1210853B (en) | 1961-05-25 | 1966-02-17 | Bayer Ag | Process for the production of carbonic acid esters or carboxylic acid esters or their anhydrides |
| EP0000753A1 (en) * | 1977-08-09 | 1979-02-21 | Bayer Ag | Process for the preparation of polycarbonates and the polycarbonates obtained |
-
1956
- 1956-04-06 DE DEF19984A patent/DE1046311B/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3110698A (en) * | 1959-03-12 | 1963-11-12 | Eastman Kodak Co | Polyesters of carbonyldichlorides and process for polymerization and dope making |
| DE1162079B (en) * | 1960-03-16 | 1964-01-30 | Gevaert Photo Producten N V Mortsel Antwerpen (Belgien) | Process for the production of thermoplastic high molecular weight polycarbonates. |
| DE1163544B (en) | 1960-03-16 | 1964-02-20 | Gevaert Photo Prod Nv | Process for the production of thermoplastic high molecular weight polycarbonates |
| DE1141789B (en) * | 1960-04-21 | 1962-12-27 | Gevaert Photo-Producten N. V., Mortsel, Antwerpen (Belgien) | Process for the production of high molecular weight polycarbonates. |
| DE1210853B (en) | 1961-05-25 | 1966-02-17 | Bayer Ag | Process for the production of carbonic acid esters or carboxylic acid esters or their anhydrides |
| US3207777A (en) * | 1961-11-02 | 1965-09-21 | Electro Chimie Metal | Polycarbonates of polyhydroxy-perchlorobiphenyls |
| EP0000753A1 (en) * | 1977-08-09 | 1979-02-21 | Bayer Ag | Process for the preparation of polycarbonates and the polycarbonates obtained |
| US4346210A (en) | 1977-08-09 | 1982-08-24 | Bayer Aktiengesellschaft | Process for the preparation of polycarbonates catalyzed by cyclic aza compounds |
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