EP0000753A1 - Procédé de préparation de polycarbonates et polycarbonates obtenus - Google Patents

Procédé de préparation de polycarbonates et polycarbonates obtenus Download PDF

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Publication number
EP0000753A1
EP0000753A1 EP7878100539A EP78100539A EP0000753A1 EP 0000753 A1 EP0000753 A1 EP 0000753A1 EP 7878100539 A EP7878100539 A EP 7878100539A EP 78100539 A EP78100539 A EP 78100539A EP 0000753 A1 EP0000753 A1 EP 0000753A1
Authority
EP
European Patent Office
Prior art keywords
polycarbonates
parts
alkyl
teile
azabicyclo
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.)
Granted
Application number
EP7878100539A
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German (de)
English (en)
Other versions
EP0000753B1 (fr
Inventor
Wolfgang Dr. Alewelt
Dieter Dr. Margotte
Claus Dr. Wulff
Hugo Dr. Vernaleken
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0000753A1 publication Critical patent/EP0000753A1/fr
Application granted granted Critical
Publication of EP0000753B1 publication Critical patent/EP0000753B1/fr
Expired legal-status Critical Current

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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

Definitions

  • the present invention also relates to the polycarbonates obtainable according to the process, which are: characterized by high light transmission and low yellowing tendency even after high temperatures.
  • the color stabilization of aromatic polycarbonates has hitherto preferably been carried out by adding additives, in particular phosphites (cf. DT-AS 1 128 653 (Le 1926), DT - A S 2 140 207, (Le A 1.3 917) and DT- OS 2 255 639 (Le A 14 709)) optionally in combination with other additives such as, for example, with oxetane compounds (DT-OS 2 510 463 (Le A 16 231)).
  • additives in particular phosphites (cf. DT-AS 1 128 653 (Le 1926), DT - A S 2 140 207, (Le A 1.3 917) and DT- OS 2 255 639 (Le A 14 709)
  • additives in particular phosphites (cf. DT-AS 1 128 653 (Le 1926), DT - A S 2 140 207, (Le A 1.3 917) and DT- OS 2 255 639 (Le A 14 709)) optionally
  • the method according to the invention uses a completely different principle in that it serves as catalysts in the production of polycarbonates by the two-phase interfacial polycondensation process (cf. DT-PS 959 497 (Le 1693), DT-PS 1 O46 311 (Le 1 7 4 7) and D T-PS 2 410 716 (Le A 15 514)) cyclic aza compounds.
  • Monocyclic and bicyclic compounds are particularly suitable as cyclic aza compounds, and in this case in turn preferably those of the pyrroliain type, piperidine type and morpholine type.
  • the cyclic aza compounds preferably have between 4 and 20 C atoms, in particular between 5 and 12 C atoms.
  • cyclic aza compounds from 0.01 to 10 mol%, preferably from 0.05) to 5 mol, - and in particular from 0.05 to 2 mol%, based on the mol of diphenols used, of cyclic aza compounds are used.
  • Cyclic aza compounds in the sense of the present invention are those which contain neither a donut bond to an aza nitrogen atom nor a secondary amine group.
  • the cyclic aza compounds must also not contain any substituents which are reactive under the conditions of the phase interface process.
  • the high molecular weight polycarbonates are produced according to the invention by the phase interface process.
  • Diphenols in particular dihydroxydiarylalkanes or -cycloalkanes, for which, in addition to the unsubstituted dihydroxydiarylalkanes or -cycloalkanes, those which are substituted in the o-position to the phenolic hydroxyl groups are also suitable in the aqueous-alkaline phase, and one is used for the Added suitable polycarbonate solvent.
  • phosgene is introduced at a temperature between 0 and 100 ° C and a pH between 9 and 14. The polycondensation takes place after the phosgenation.
  • the addition of the cyclic aza compounds as a catalyst can both before introducing phosgene and after introducing phosgene before polycondensation.
  • the phosgene introduction times are between 1 and 60 minutes, the post-condensation between 2 and 120 minutes.
  • the organic polymer solution is separated off and washed free of electrolytes with water.
  • the polycarbonate can then be isolated by evaporation of the solvent or by precipitation with non-solvents, such as methanol or gasoline.
  • the polycarbonates produced by the process according to the invention can also be branched in a known manner.
  • Suitable diphenols are e.g. B. hydroquinone, resorcinol, 4,4'-dihydroxydiphenyl, bis (hydroxyphenyl) alkanes, such as C 1 -C 8 alkylene or C 2 -C 8 alkylidene bisphenols, bis- '(hydroxyphenyl) cycloalkanes such as for example C5-C6-cycloalkylene or C 5 -C 6 -cycloalkylidene bisphenols, bis (hydroxy - phenyl) sulfides, ethers, ketones, sulfoxides or sulfones.
  • B. hydroquinone, resorcinol, 4,4'-dihydroxydiphenyl bis (hydroxyphenyl) alkanes, such as C 1 -C 8 alkylene or C 2 -C 8 alkylidene bisphenols, bis- '(hydroxyphenyl) cycloalkanes such as for example C5-
  • A ⁇ '-bis (hydroxyphenyl) diisopropylbenzenes and the corresponding ring-alkylated or ring-halogenated compounds.
  • Polycarbonates based on bis- (4-hydroxy-phenyl) propane-2,2 (bisphenol A), bis- (4-hydroxy-3,5-dichlorophenyl) propane-2,2 (tetrachlorobisphenol A) are preferred.
  • the reaction temperature is 72 ° C; the concentration of OH ions in the aqueous reaction phase is 0.08%.
  • the average residence time is 1.4 minutes.
  • the emulsion flowing out of the pump-around reactor is fed with additional sodium hydroxide solution to increase the OH concentration to 0.3 to 0.35%.
  • the oligocarbonate is condensed in a reaction tube as described in DT-OS 1 920 302 or US Pat. No. 3,674,740.
  • the average residence time is 4 minutes; the temperature 83 ° C.
  • the polycarbonate solution is washed free of electrolytes, evaporated and isolated using an evaporation extruder.
  • the polycarbonate has a relative viscosity of 1.30 to 1.31, measured in a 0.5% solution of methylene chloride at 20 ° C. This corresponds approximately to a molecular weight of 34,000.
  • the polycarbonates were processed into test specimens.
  • the test specimens are annealed at 140 ° C in a drying cabinet.
  • the light transmission was measured according to DIN 5033 and DIN 4646 using a spectrophotometer.
  • the drop in light transmission at 420 nm in the course of the heat treatment is a measure of the increasing discoloration of the test specimen.

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)
  • Compositions Of Macromolecular Compounds (AREA)
EP78100539A 1977-08-09 1978-07-28 Procédé de préparation de polycarbonates et polycarbonates obtenus Expired EP0000753B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2735775 1977-08-09
DE19772735775 DE2735775A1 (de) 1977-08-09 1977-08-09 Verfahren zur herstellung von polycarbonaten

Publications (2)

Publication Number Publication Date
EP0000753A1 true EP0000753A1 (fr) 1979-02-21
EP0000753B1 EP0000753B1 (fr) 1980-12-10

Family

ID=6015937

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100539A Expired EP0000753B1 (fr) 1977-08-09 1978-07-28 Procédé de préparation de polycarbonates et polycarbonates obtenus

Country Status (7)

Country Link
US (1) US4346210A (fr)
EP (1) EP0000753B1 (fr)
JP (1) JPS6053049B2 (fr)
BR (1) BR7805075A (fr)
DE (2) DE2735775A1 (fr)
IT (1) IT1106867B (fr)
SU (1) SU1020006A3 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999002579A1 (fr) * 1997-07-05 1999-01-21 Bayer Aktiengesellschaft Procede de production de polycarbonate
WO1999019380A1 (fr) * 1997-10-10 1999-04-22 Bayer Aktiengesellschaft Preparation de dihydroxydiphenyle-copolycarbonates par reesterification par fusion
WO2000023499A1 (fr) * 1998-10-22 2000-04-27 General Electric Company Procede de preparation interfaciale en continu de polycarbonates aromatiques

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4233345A1 (de) * 1992-10-05 1994-04-07 Bayer Ag Verfahren zur Herstellung von Polycarbonaten und von Polyestercarbonaten

Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2991273A (en) 1956-07-07 1961-07-04 Bayer Ag Process for manufacture of vacuum moulded parts of high molecular weight thermoplastic polycarbonates
US2999835A (en) 1959-01-02 1961-09-12 Gen Electric Resinous mixture comprising organo-polysiloxane and polymer of a carbonate of a dihydric phenol, and products containing same
US2999846A (en) 1956-11-30 1961-09-12 Schnell Hermann High molecular weight thermoplastic aromatic sulfoxy polycarbonates
US3014891A (en) 1961-12-26 Resinous compositions
US3028265A (en) 1957-05-06 1962-04-03 Gen Electric Reinforced synthetic enamel coating for electrical conductor
US3148172A (en) 1956-07-19 1964-09-08 Gen Electric Polycarbonates of dihydroxyaryl ethers
US3271368A (en) 1963-05-02 1966-09-06 Borg Warner Sulfonate-thiocarbonate copolymers
US3271367A (en) 1955-03-26 1966-09-06 Bayer Ag Thermoplastic polycarbonates of dihydroxydiarylene sulfones and their preparation
US3280078A (en) 1963-09-26 1966-10-18 Union Carbide Corp Polyethylenically unsaturated polycarbonate polymers
US3674740A (en) 1969-04-22 1972-07-04 Bayer Ag Process of producing polycarbonate
DE2063050A1 (de) 1970-12-22 1972-07-13 Bayer Verseifungsbeständige Polycarbonate
DE2063052A1 (de) 1970-12-22 1972-07-13 Bayer Verseifungsbeständige Polycarbonate
DE2211957A1 (de) 1972-03-11 1973-09-27 Bayer Ag Hochmolekulare, statistische copolycarbonate
DE2211956A1 (de) 1972-03-11 1973-10-25 Bayer Ag Verfahren zur herstellung verseifungsstabiler blockcopolycarbonate

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE959497C (de) 1955-03-27 1957-03-07 Bayer Ag Verfahren zur Herstellung thermoplastischer Kunststoffe
US3275601A (en) * 1956-01-04 1966-09-27 Bayer Ag Manufacture of polycarbonates using tertiary amines, quaternary amines and salts thereof as catalysts
DE1046311B (de) 1956-04-06 1958-12-11 Bayer Ag Verfahren zur Herstellung von Polycarbonaten
US3220975A (en) * 1959-03-19 1965-11-30 Eastman Kodak Co Tri-isoamylamine catalyst in a process for preparing a polycarbonate
NL126830C (fr) 1959-06-27
DE1300274B (de) 1963-05-22 1969-07-31 Hoechst Ag Verfahren zur Herstellung hochmolekularer Polymerisate auf der Basis von Di-[beta-trihalogen-alpha-hydroxyaethoxy]-alkanen
US3527734A (en) 1965-06-07 1970-09-08 Union Carbide Corp Preparation of cylobutanediol polycarbonates by direct phosgenation
US3428600A (en) * 1965-06-18 1969-02-18 Union Carbide Corp Carbonate polymer synthesis
CH554908A (de) * 1971-01-15 1974-10-15 Basf Ag Verfahren zur kontinuierlichen herstellung hochmolekularer, linearer polycarbonate.
DE2140207C3 (de) * 1971-08-11 1975-11-27 Farbenfabriken Bayer Ag, 5090 Leverkusen Stabilisiertes aromatisches PoIycarbonat
US4073769A (en) * 1971-08-11 1978-02-14 Bayer Aktiengesellschaft Esters of phosphorous acid
DE2305144C2 (de) * 1973-02-02 1982-05-06 Basf Ag, 6700 Ludwigshafen Verfahren zur kontinuierlichen Herstellung von Polycarbonaten
DE2410716B2 (de) * 1974-03-06 1977-02-10 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung aromatischer polycarbonate nach der methode der phasengrenzflaechenkondensation
DE2447349A1 (de) 1974-10-04 1976-04-15 Bayer Ag Verfahren zur herstellung von aliphatischen polycarbonaten und aliphatischaromatischen copolycarbonaten
US4025489A (en) * 1975-01-27 1977-05-24 Mobay Chemical Corporation Utilization of bisphenol-A from the alkaline phase generated in the production of polycarbonates
DE2510463C2 (de) 1975-03-11 1986-04-03 Bayer Ag, 5090 Leverkusen Stabilisatormischungen und Verwendung von Stabilisatormischungen zur Stabilisierung von Polycarbonaten

Patent Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3014891A (en) 1961-12-26 Resinous compositions
US3271367A (en) 1955-03-26 1966-09-06 Bayer Ag Thermoplastic polycarbonates of dihydroxydiarylene sulfones and their preparation
US2991273A (en) 1956-07-07 1961-07-04 Bayer Ag Process for manufacture of vacuum moulded parts of high molecular weight thermoplastic polycarbonates
US3148172A (en) 1956-07-19 1964-09-08 Gen Electric Polycarbonates of dihydroxyaryl ethers
US2999846A (en) 1956-11-30 1961-09-12 Schnell Hermann High molecular weight thermoplastic aromatic sulfoxy polycarbonates
US3028265A (en) 1957-05-06 1962-04-03 Gen Electric Reinforced synthetic enamel coating for electrical conductor
US2999835A (en) 1959-01-02 1961-09-12 Gen Electric Resinous mixture comprising organo-polysiloxane and polymer of a carbonate of a dihydric phenol, and products containing same
US3271368A (en) 1963-05-02 1966-09-06 Borg Warner Sulfonate-thiocarbonate copolymers
US3280078A (en) 1963-09-26 1966-10-18 Union Carbide Corp Polyethylenically unsaturated polycarbonate polymers
US3674740A (en) 1969-04-22 1972-07-04 Bayer Ag Process of producing polycarbonate
DE2063050A1 (de) 1970-12-22 1972-07-13 Bayer Verseifungsbeständige Polycarbonate
DE2063052A1 (de) 1970-12-22 1972-07-13 Bayer Verseifungsbeständige Polycarbonate
DE2211957A1 (de) 1972-03-11 1973-09-27 Bayer Ag Hochmolekulare, statistische copolycarbonate
DE2211956A1 (de) 1972-03-11 1973-10-25 Bayer Ag Verfahren zur herstellung verseifungsstabiler blockcopolycarbonate

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999002579A1 (fr) * 1997-07-05 1999-01-21 Bayer Aktiengesellschaft Procede de production de polycarbonate
US6262219B1 (en) * 1997-07-05 2001-07-17 Bayer Aktiengesellschaft Method for producing polycarbonate
WO1999019380A1 (fr) * 1997-10-10 1999-04-22 Bayer Aktiengesellschaft Preparation de dihydroxydiphenyle-copolycarbonates par reesterification par fusion
WO2000023499A1 (fr) * 1998-10-22 2000-04-27 General Electric Company Procede de preparation interfaciale en continu de polycarbonates aromatiques

Also Published As

Publication number Publication date
DE2860295D1 (en) 1981-02-19
JPS6053049B2 (ja) 1985-11-22
EP0000753B1 (fr) 1980-12-10
DE2735775A1 (de) 1979-02-22
BR7805075A (pt) 1979-04-10
IT1106867B (it) 1985-11-18
IT7850631A0 (it) 1978-08-07
US4346210A (en) 1982-08-24
JPS5430293A (en) 1979-03-06
SU1020006A3 (ru) 1983-05-23

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