DE2035733C3 - Verfahren zur anionischen Polymerisation von Lactamen und Katalysatorlösungen hierfür - Google Patents
Verfahren zur anionischen Polymerisation von Lactamen und Katalysatorlösungen hierfürInfo
- Publication number
- DE2035733C3 DE2035733C3 DE2035733A DE2035733A DE2035733C3 DE 2035733 C3 DE2035733 C3 DE 2035733C3 DE 2035733 A DE2035733 A DE 2035733A DE 2035733 A DE2035733 A DE 2035733A DE 2035733 C3 DE2035733 C3 DE 2035733C3
- Authority
- DE
- Germany
- Prior art keywords
- lactams
- solutions
- room temperature
- pyrrolidone
- caprolactam
- 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
- 150000003951 lactams Chemical class 0.000 title claims description 42
- 239000003054 catalyst Substances 0.000 title claims description 27
- 238000010539 anionic addition polymerization reaction Methods 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 7
- 239000000203 mixture Substances 0.000 claims description 17
- 239000007788 liquid Substances 0.000 claims description 11
- 239000003513 alkali Substances 0.000 claims description 10
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 10
- 239000012190 activator Substances 0.000 claims description 6
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000004952 Polyamide Substances 0.000 description 10
- 229920002647 polyamide Polymers 0.000 description 10
- 229910052783 alkali metal Inorganic materials 0.000 description 9
- 150000001340 alkali metals Chemical class 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- 239000000155 melt Substances 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 150000001447 alkali salts Chemical class 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 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 2
- -1 carboxylic acid chlorides Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- YDLSUFFXJYEVHW-UHFFFAOYSA-N azonan-2-one Chemical compound O=C1CCCCCCCN1 YDLSUFFXJYEVHW-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002561 ketenes Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- MOMGDEWWZBKDDR-UHFFFAOYSA-M sodium;3,4,5,6-tetrahydro-2h-azepin-7-olate Chemical compound [Na+].O=C1CCCCC[N-]1 MOMGDEWWZBKDDR-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
- C08G69/14—Lactams
- C08G69/16—Preparatory processes
- C08G69/18—Anionic polymerisation
- C08G69/20—Anionic polymerisation characterised by the catalysts used
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2035733A DE2035733C3 (de) | 1970-07-18 | 1970-07-18 | Verfahren zur anionischen Polymerisation von Lactamen und Katalysatorlösungen hierfür |
| DK352771AA DK129801B (da) | 1970-07-18 | 1971-07-16 | Fremgangsmåde til anionisk polymerisation af lactamer. |
| US00163413A US3793258A (en) | 1970-07-18 | 1971-07-16 | Process for the anionic polymerization of lactams |
| GB3352471A GB1352409A (en) | 1970-07-18 | 1971-07-16 | Process for the anionic polymerisation of lactams |
| FR7126224A FR2099459B1 (enExample) | 1970-07-18 | 1971-07-16 | |
| BE770139A BE770139A (fr) | 1970-07-18 | 1971-07-16 | Procede pour la polymerisation anionique de lactames |
| NLAANVRAGE7109862,A NL172751C (nl) | 1970-07-18 | 1971-07-16 | Werkwijze voor de bereiding van polyamiden, alsmede gevormd voortbrengsel, dat geheel of gedeeltelijk daaruit bestaat. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2035733A DE2035733C3 (de) | 1970-07-18 | 1970-07-18 | Verfahren zur anionischen Polymerisation von Lactamen und Katalysatorlösungen hierfür |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2035733A1 DE2035733A1 (de) | 1972-01-27 |
| DE2035733B2 DE2035733B2 (de) | 1981-02-26 |
| DE2035733C3 true DE2035733C3 (de) | 1982-03-25 |
Family
ID=5777176
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2035733A Expired DE2035733C3 (de) | 1970-07-18 | 1970-07-18 | Verfahren zur anionischen Polymerisation von Lactamen und Katalysatorlösungen hierfür |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3793258A (enExample) |
| BE (1) | BE770139A (enExample) |
| DE (1) | DE2035733C3 (enExample) |
| DK (1) | DK129801B (enExample) |
| FR (1) | FR2099459B1 (enExample) |
| GB (1) | GB1352409A (enExample) |
| NL (1) | NL172751C (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2230732C3 (de) * | 1972-06-23 | 1982-03-25 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Polyamiden durch die Polymerisation von Lactamen und Katalysatorlösungen hierfür |
| US4264503A (en) * | 1975-06-20 | 1981-04-28 | Chevron Research Company | Polymerization process using a sodium carboxylactamate catalyst |
| US4098774A (en) * | 1976-05-19 | 1978-07-04 | Chevron Research Company | Quaternary ammonium catalyst system for the polymerization of 2-pyrrolidone |
| CH631188A5 (de) * | 1977-10-14 | 1982-07-30 | Harwe Ag | Katalysator fuer die polymerisation von lactammonomeren und verfahren zu dessen herstellung. |
| NL7902966A (nl) * | 1979-04-14 | 1980-10-16 | Stamicarbon | Werkwijze voor het polymeriseren van pyrrolidon. |
| DE19603305C2 (de) * | 1996-01-25 | 1999-07-22 | Inventa Ag | Flüssiges Mehrkomponentensystem zur Durchführung der anionischen Lactampolymerisation |
| DE19603303C2 (de) * | 1996-01-25 | 1999-07-22 | Inventa Ag | Kontinuierliches Verfahren zur aktivierten anionischen Lactampolymerisation |
| DE19602683C1 (de) * | 1996-01-25 | 1997-09-18 | Inventa Ag | Flüssigsystem zur Durchführung der anionischen Lactampolymerisation |
| DE102008000259A1 (de) | 2008-02-08 | 2009-08-13 | Rhein Chemie Rheinau Gmbh | Verfahren zur Herstellung von Lactamaten durch Dünnschichtverdampfung |
| KR102262531B1 (ko) | 2017-11-28 | 2021-06-08 | 한화솔루션 주식회사 | 아마이드계-분자량조절제를 포함하는 폴리아마이드 제조방법 및 이에 의해 제조된 폴리아마이드 |
| EP4071198A4 (en) * | 2019-12-06 | 2024-01-03 | Hanwha Solutions Corporation | METHOD FOR PRODUCING A POLYAMIDE BY ANIONIC POLYMERIZATION AND POLYAMIDE THUS PREPARED |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2727017A (en) * | 1954-03-05 | 1955-12-13 | Olin Mathieson | Polymerization of caprolactam |
| GB863859A (en) * | 1956-07-23 | 1961-03-29 | Monsanto Chemicals | Polymerisation of lactams |
| DE1221446B (de) * | 1960-05-21 | 1966-07-21 | Basf Ag | Verfahren zum Herstellen lagerfaehiger Katalysatorloesungen aus Alkalilactam in Lactam |
| BE630860A (enExample) * | 1962-04-11 | |||
| NL122981C (enExample) * | 1964-02-28 | |||
| CH452893A (de) * | 1964-04-03 | 1968-03-15 | Bayer Ag | Verfahren zum Herstellen von Polyamiden |
-
1970
- 1970-07-18 DE DE2035733A patent/DE2035733C3/de not_active Expired
-
1971
- 1971-07-16 FR FR7126224A patent/FR2099459B1/fr not_active Expired
- 1971-07-16 BE BE770139A patent/BE770139A/xx unknown
- 1971-07-16 NL NLAANVRAGE7109862,A patent/NL172751C/xx not_active IP Right Cessation
- 1971-07-16 US US00163413A patent/US3793258A/en not_active Expired - Lifetime
- 1971-07-16 GB GB3352471A patent/GB1352409A/en not_active Expired
- 1971-07-16 DK DK352771AA patent/DK129801B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL172751C (nl) | 1983-10-17 |
| NL7109862A (enExample) | 1972-01-20 |
| FR2099459A1 (enExample) | 1972-03-17 |
| FR2099459B1 (enExample) | 1975-10-10 |
| US3793258A (en) | 1974-02-19 |
| DK129801B (da) | 1974-11-18 |
| DE2035733B2 (de) | 1981-02-26 |
| DK129801C (enExample) | 1975-04-28 |
| BE770139A (fr) | 1971-12-01 |
| DE2035733A1 (de) | 1972-01-27 |
| GB1352409A (en) | 1974-05-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |