DE2237003C2 - Verfahren zur Herstellung von Polyamiden durch aktivierte anionische Polymerisation von Lactamen oder Lactamgemischen - Google Patents
Verfahren zur Herstellung von Polyamiden durch aktivierte anionische Polymerisation von Lactamen oder LactamgemischenInfo
- Publication number
- DE2237003C2 DE2237003C2 DE19722237003 DE2237003A DE2237003C2 DE 2237003 C2 DE2237003 C2 DE 2237003C2 DE 19722237003 DE19722237003 DE 19722237003 DE 2237003 A DE2237003 A DE 2237003A DE 2237003 C2 DE2237003 C2 DE 2237003C2
- Authority
- DE
- Germany
- Prior art keywords
- mol
- polymerization
- caprolactam
- lactams
- polyamides
- 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
- 239000004952 Polyamide Substances 0.000 title claims description 13
- 229920002647 polyamide Polymers 0.000 title claims description 13
- 150000003951 lactams Chemical class 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 10
- 239000000203 mixture Substances 0.000 title claims description 10
- 125000000129 anionic group Chemical group 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000010539 anionic addition polymerization reaction Methods 0.000 title claims description 4
- 239000012190 activator Substances 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 3
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 32
- 238000006116 polymerization reaction Methods 0.000 description 17
- 229920000642 polymer Polymers 0.000 description 12
- 159000000000 sodium salts Chemical class 0.000 description 10
- -1 p-diethylaminophenyl Chemical group 0.000 description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 3
- 229920002292 Nylon 6 Polymers 0.000 description 3
- 229960002319 barbital Drugs 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 238000012693 lactam polymerization Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 150000007656 barbituric acids Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000000711 cancerogenic effect Effects 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 231100000315 carcinogenic Toxicity 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 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 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 150000003585 thioureas Chemical class 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical compound O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000002561 ketenes Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical class ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 238000004383 yellowing 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
- 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS547971A CS156780B1 (Direct) | 1971-07-27 | 1971-07-27 | |
| CS548071A CS156174B1 (Direct) | 1971-07-27 | 1971-07-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2237003A1 DE2237003A1 (de) | 1973-02-15 |
| DE2237003C2 true DE2237003C2 (de) | 1982-04-22 |
Family
ID=25746177
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722237003 Expired DE2237003C2 (de) | 1971-07-27 | 1972-07-27 | Verfahren zur Herstellung von Polyamiden durch aktivierte anionische Polymerisation von Lactamen oder Lactamgemischen |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS4934594A (Direct) |
| CA (1) | CA997099A (Direct) |
| CH (1) | CH572501A5 (Direct) |
| DD (1) | DD97433A1 (Direct) |
| DE (1) | DE2237003C2 (Direct) |
| EG (1) | EG11277A (Direct) |
| FR (1) | FR2147248B1 (Direct) |
| GB (1) | GB1360899A (Direct) |
| HU (1) | HU165502B (Direct) |
| IT (1) | IT963407B (Direct) |
| NL (1) | NL7210307A (Direct) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS511277B2 (Direct) * | 1972-02-03 | 1976-01-16 | ||
| EP3305829A1 (de) * | 2016-10-07 | 2018-04-11 | LANXESS Deutschland GmbH | Polymerisierbare zusammensetzung |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3017391A (en) * | 1956-12-13 | 1962-01-16 | Monsanto Chemicals | Preparation of polycaprolactam using n-acyl activators |
| US3017392A (en) * | 1956-12-13 | 1962-01-16 | Monsanto Chemicals | Polymerization of higher lactams |
| US3138575A (en) * | 1961-09-15 | 1964-06-23 | Du Pont | Process for the anionic polymerization of omega-lactams with poly (fluoromethylene)sulfide as activator |
| BE638901A (Direct) * | 1961-10-20 | |||
| DE1520593A1 (de) * | 1963-02-27 | 1970-01-22 | Polymer Corp | Verfahren zur Regelung des viskosen Bereiches bei Polymerisationen von Lactamen |
| DE1595617A1 (de) * | 1966-04-05 | 1970-04-30 | Bayer Ag | Verfahren zur ionischen Polymerisation von Lactamen |
| CH499565A (de) * | 1968-10-09 | 1970-11-30 | Inventa Ag | Verfahren zur Regulierung der Polymerisationsgeschwindigkeit der anionischen Polymerisation von Lactamen |
| JPS511277B2 (Direct) * | 1972-02-03 | 1976-01-16 |
-
1972
- 1972-07-12 GB GB3263472A patent/GB1360899A/en not_active Expired
- 1972-07-20 CH CH1086872A patent/CH572501A5/xx not_active IP Right Cessation
- 1972-07-25 EG EG30972A patent/EG11277A/xx active
- 1972-07-26 CA CA148,030A patent/CA997099A/en not_active Expired
- 1972-07-26 NL NL7210307A patent/NL7210307A/xx not_active Application Discontinuation
- 1972-07-26 DD DD16469772A patent/DD97433A1/xx unknown
- 1972-07-26 IT IT2747072A patent/IT963407B/it active
- 1972-07-26 JP JP7426472A patent/JPS4934594A/ja active Pending
- 1972-07-27 FR FR7227044A patent/FR2147248B1/fr not_active Expired
- 1972-07-27 HU HUCE000890 patent/HU165502B/hu not_active IP Right Cessation
- 1972-07-27 DE DE19722237003 patent/DE2237003C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA997099A (en) | 1976-09-14 |
| FR2147248B1 (Direct) | 1977-08-26 |
| FR2147248A1 (Direct) | 1973-03-09 |
| CH572501A5 (Direct) | 1976-02-13 |
| HU165502B (Direct) | 1974-09-28 |
| EG11277A (en) | 1977-01-31 |
| JPS4934594A (Direct) | 1974-03-30 |
| NL7210307A (Direct) | 1973-01-30 |
| IT963407B (it) | 1974-01-10 |
| DD97433A1 (Direct) | 1973-05-14 |
| DE2237003A1 (de) | 1973-02-15 |
| GB1360899A (en) | 1974-07-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| D2 | Grant after examination |