DE1570533C3 - Verfahren zum Herstellen von Polycarbonaten - Google Patents
Verfahren zum Herstellen von PolycarbonatenInfo
- Publication number
- DE1570533C3 DE1570533C3 DE19651570533 DE1570533A DE1570533C3 DE 1570533 C3 DE1570533 C3 DE 1570533C3 DE 19651570533 DE19651570533 DE 19651570533 DE 1570533 A DE1570533 A DE 1570533A DE 1570533 C3 DE1570533 C3 DE 1570533C3
- Authority
- DE
- Germany
- Prior art keywords
- weight
- parts
- polycarbonates
- phosgene
- methylene chloride
- 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
- 229920000515 polycarbonate Polymers 0.000 title claims description 29
- 239000004417 polycarbonate Substances 0.000 title claims description 29
- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 19
- 229930185605 Bisphenol Natural products 0.000 claims description 12
- 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 claims description 11
- 239000000155 melt Substances 0.000 claims description 11
- 150000002989 phenols Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 238000010406 interfacial reaction Methods 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 235000011121 sodium hydroxide Nutrition 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- WUQYBSRMWWRFQH-UHFFFAOYSA-N 2-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC=C1O WUQYBSRMWWRFQH-UHFFFAOYSA-N 0.000 description 14
- 239000012153 distilled water Substances 0.000 description 14
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 13
- 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 description 13
- 239000012299 nitrogen atmosphere Substances 0.000 description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 230000008018 melting Effects 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 238000000149 argon plasma sintering Methods 0.000 description 5
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical class CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 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 3
- -1 p-tert-butylphenol Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- 239000004416 thermosoftening plastic Substances 0.000 description 3
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical class CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 2
- RQTDWDATSAVLOR-UHFFFAOYSA-N 4-[3,5-bis(4-hydroxyphenyl)phenyl]phenol Chemical compound C1=CC(O)=CC=C1C1=CC(C=2C=CC(O)=CC=2)=CC(C=2C=CC(O)=CC=2)=C1 RQTDWDATSAVLOR-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-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
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000008187 granular material Substances 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
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical class CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 1
- BRPSWMCDEYMRPE-UHFFFAOYSA-N 4-[1,1-bis(4-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=C(O)C=C1 BRPSWMCDEYMRPE-UHFFFAOYSA-N 0.000 description 1
- CIEGINNQDIULCT-UHFFFAOYSA-N 4-[4,6-bis(4-hydroxyphenyl)-4,6-dimethylheptan-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)CC(C)(C=1C=CC(O)=CC=1)CC(C)(C)C1=CC=C(O)C=C1 CIEGINNQDIULCT-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 244000198134 Agave sisalana Species 0.000 description 1
- AZXKCFRHEOPVBA-UHFFFAOYSA-N C(CC)O.CC=1C=CC=C(C1)C Chemical compound C(CC)O.CC=1C=CC=C(C1)C AZXKCFRHEOPVBA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 239000006085 branching agent Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000006866 deterioration Effects 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
- 239000000975 dye Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical class CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000010626 work up procedure Methods 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
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
- C08G64/14—Aromatic polycarbonates not containing aliphatic unsaturation containing a chain-terminating or -crosslinking agent
-
- 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
- C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
- C08G64/1608—Aliphatic-aromatic or araliphatic polycarbonates saturated
- C08G64/1616—Aliphatic-aromatic or araliphatic polycarbonates saturated containing a chain-terminating or -crosslinking agent
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0044973 | 1965-01-15 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1570533A1 DE1570533A1 (de) | 1970-01-29 |
| DE1570533B2 DE1570533B2 (de) | 1974-10-17 |
| DE1570533C3 true DE1570533C3 (de) | 1975-05-28 |
Family
ID=7100285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651570533 Expired DE1570533C3 (de) | 1965-01-15 | 1965-01-15 | Verfahren zum Herstellen von Polycarbonaten |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE675110A (enExample) |
| DE (1) | DE1570533C3 (enExample) |
| FR (1) | FR1464376A (enExample) |
| GB (1) | GB1079821A (enExample) |
| NL (1) | NL148337B (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4174359A (en) * | 1977-09-06 | 1979-11-13 | Mobay Chemical Corporation | Flame retardant polycarbonate polyblends |
| DE3017419A1 (de) * | 1980-05-07 | 1981-11-12 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung aromatischer polycarbonate |
| EP0103231B1 (de) | 1982-09-10 | 1988-09-28 | Bayer Ag | Flammwidrige Polymermischungen |
| CA1289290C (en) | 1985-04-11 | 1991-09-17 | John V. Bailey | Stabilized polycarbonates |
| DE68928766T2 (de) * | 1988-09-22 | 1999-03-25 | Ge Plastics Japan Ltd., Tokio/Tokyo | Verfahren zur Herstellung von Polycarbonaten |
| DE4013112A1 (de) * | 1990-04-25 | 1991-11-07 | Bayer Ag | Stabilisierte thermoplastische formmassen |
| DE4013113A1 (de) * | 1990-04-25 | 1991-10-31 | Bayer Ag | Stabilisierte thermoplastische formmassen |
| EP0496258B1 (en) * | 1991-01-24 | 2001-06-20 | Idemitsu Petrochemical Co., Ltd. | Polymer composition containing a branched polycarbonate |
| US5314949A (en) * | 1991-01-24 | 1994-05-24 | Idemitsu Petrochemical Co., Ltd. | Polycarbonate resin composition |
| JP2878854B2 (ja) * | 1991-01-24 | 1999-04-05 | 出光石油化学株式会社 | ポリカーボネート樹脂組成物 |
| US6437083B1 (en) | 2001-12-06 | 2002-08-20 | General Electric Company | Process for preparing branched aromatic polycarbonates |
| JP5023151B2 (ja) | 2006-09-06 | 2012-09-12 | ソルヴェイ アドバンスド ポリマーズ リミテッド ライアビリティ カンパニー | 新規な芳香族ポリカーボネート組成物 |
| US20090043053A1 (en) | 2007-08-07 | 2009-02-12 | Rudiger Gorny | Aircraft window |
| US7754793B2 (en) | 2007-08-07 | 2010-07-13 | Bayer Materialscience Llc | Flame resistant polycarbonate composition |
| US20120319031A1 (en) | 2011-06-15 | 2012-12-20 | Thermal Solution Resources, Llc | Thermally conductive thermoplastic compositions |
| EP2724113B1 (en) | 2011-06-21 | 2018-04-25 | Covestro LLC | Polycarbonate laminate for close-proximity blast events |
| US9417038B2 (en) | 2012-08-29 | 2016-08-16 | Covestro Llc | Energy absorber for high-performance blast barrier system |
| KR20150127082A (ko) | 2013-03-13 | 2015-11-16 | 바이엘 머티리얼싸이언스 엘엘씨 | 증진된 광택 수준을 갖는 중합체 및 중합체 블렌드 |
| US20150090411A1 (en) | 2013-09-30 | 2015-04-02 | Bayer Materialscience Llc | Polycarbonate laminate window covers for rapid deployment providing protection from forced-entry and ballistics |
| JP6581587B2 (ja) | 2013-12-18 | 2019-09-25 | コベストロ・エルエルシー | 耐弾丸構造用防護パネル |
| EP3140487A1 (en) | 2014-05-06 | 2017-03-15 | Covestro LLC | Polycarbonate based rapid deployment cover system |
| CA2973507A1 (en) | 2015-02-09 | 2016-08-18 | Covestro Llc | Lightweight blast-mitigating polycarbonate-based laminate system |
| JP2018528306A (ja) | 2015-09-09 | 2018-09-27 | ソルベイ スペシャルティ ポリマーズ ユーエスエー， エルエルシー | ポリアリールエーテルケトンおよびポリカーボネートポリマーを含むポリマー組成物ならびにそれから得ることができる成形品 |
| EP3251827B1 (en) | 2016-05-30 | 2021-07-28 | Covestro Deutschland AG | Combined carbon- and glass-fiber reinforced thermoplastic polyurethane and polyamide composites and its manufacturing |
| US20190194940A1 (en) | 2016-08-19 | 2019-06-27 | Plaskolite Massachusetts, Llc | Ultrathin polycarbonate panels for security isolation cells |
| WO2020076579A1 (en) | 2018-10-09 | 2020-04-16 | Covestro Llc | Insert-molded electronic modules using thermally conductive polycarbonate and molded interlocking features |
-
1965
- 1965-01-15 DE DE19651570533 patent/DE1570533C3/de not_active Expired
-
1966
- 1966-01-14 BE BE675110D patent/BE675110A/xx not_active IP Right Cessation
- 1966-01-14 GB GB188166A patent/GB1079821A/en not_active Expired
- 1966-01-14 NL NL6600516A patent/NL148337B/xx not_active IP Right Cessation
- 1966-01-15 FR FR46044A patent/FR1464376A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL148337B (nl) | 1976-01-15 |
| NL6600516A (enExample) | 1966-07-18 |
| GB1079821A (en) | 1967-08-16 |
| DE1570533B2 (de) | 1974-10-17 |
| DE1570533A1 (de) | 1970-01-29 |
| BE675110A (enExample) | 1966-07-14 |
| FR1464376A (fr) | 1966-12-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |