DE1944417A1 - Verfahren zur Herstellung von Formkoerpern durch kontinuierliche Polymerisation von Laktamen - Google Patents
Verfahren zur Herstellung von Formkoerpern durch kontinuierliche Polymerisation von LaktamenInfo
- Publication number
- DE1944417A1 DE1944417A1 DE19691944417 DE1944417A DE1944417A1 DE 1944417 A1 DE1944417 A1 DE 1944417A1 DE 19691944417 DE19691944417 DE 19691944417 DE 1944417 A DE1944417 A DE 1944417A DE 1944417 A1 DE1944417 A1 DE 1944417A1
- Authority
- DE
- Germany
- Prior art keywords
- polymerization
- zone
- polylactam
- melting point
- reaction zone
- 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
- 238000006116 polymerization reaction Methods 0.000 title claims description 131
- 238000000034 method Methods 0.000 title claims description 74
- 230000008569 process Effects 0.000 title claims description 41
- 150000003951 lactams Chemical class 0.000 title claims description 34
- 238000004519 manufacturing process Methods 0.000 title description 23
- 238000006243 chemical reaction Methods 0.000 claims description 69
- 238000002844 melting Methods 0.000 claims description 65
- 230000008018 melting Effects 0.000 claims description 65
- 239000000203 mixture Substances 0.000 claims description 32
- 239000003999 initiator Substances 0.000 claims description 30
- 238000006073 displacement reaction Methods 0.000 claims description 17
- 239000012632 extractable Substances 0.000 claims description 15
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 10
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims description 7
- 238000011161 development Methods 0.000 claims description 7
- 239000000945 filler Substances 0.000 claims description 7
- 229920002292 Nylon 6 Polymers 0.000 claims description 4
- 239000011952 anionic catalyst Substances 0.000 claims description 3
- 238000005496 tempering Methods 0.000 claims description 2
- 239000007822 coupling agent Substances 0.000 claims 1
- 239000000463 material Substances 0.000 description 67
- 239000000047 product Substances 0.000 description 42
- 230000000379 polymerizing effect Effects 0.000 description 40
- 239000000178 monomer Substances 0.000 description 37
- 229920000642 polymer Polymers 0.000 description 36
- 239000007787 solid Substances 0.000 description 32
- 239000007788 liquid Substances 0.000 description 28
- 239000003054 catalyst Substances 0.000 description 26
- 238000001125 extrusion Methods 0.000 description 21
- 235000012438 extruded product Nutrition 0.000 description 15
- 238000002156 mixing Methods 0.000 description 15
- -1 N-acyllactams Chemical class 0.000 description 14
- 239000012141 concentrate Substances 0.000 description 12
- 238000002425 crystallisation Methods 0.000 description 11
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- DVPHDWQFZRBFND-DMHDVGBCSA-N 1-o-[2-[(3ar,5r,6s,6ar)-2,2-dimethyl-6-prop-2-enoyloxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-[4-[(2s,3r)-1-butan-2-ylsulfanyl-2-(2-chlorophenyl)-4-oxoazetidin-3-yl]oxy-4-oxobutanoyl]oxyethyl] 4-o-[(2s,3r)-1-butan-2-ylsulfanyl-2-(2-chloropheny Chemical group C1([C@H]2[C@H](C(N2SC(C)CC)=O)OC(=O)CCC(=O)OC(COC(=O)CCC(=O)O[C@@H]2[C@@H](N(C2=O)SC(C)CC)C=2C(=CC=CC=2)Cl)[C@@H]2[C@@H]([C@H]3OC(C)(C)O[C@H]3O2)OC(=O)C=C)=CC=CC=C1Cl DVPHDWQFZRBFND-DMHDVGBCSA-N 0.000 description 6
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 2
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- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 229920006125 amorphous polymer Polymers 0.000 description 2
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
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- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
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- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
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- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
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- 150000004679 hydroxides Chemical class 0.000 description 2
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- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N meta-toluidine Natural products CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N ortho-methyl aniline Natural products CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
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- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
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- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 1
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- LTIKIBFTASQKMM-UHFFFAOYSA-N 1-[bis(4-isocyanatophenyl)methyl]-4-isocyanatobenzene Chemical compound C1=CC(N=C=O)=CC=C1C(C=1C=CC(=CC=1)N=C=O)C1=CC=C(N=C=O)C=C1 LTIKIBFTASQKMM-UHFFFAOYSA-N 0.000 description 1
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- PGKVHYTTXBKQQT-UHFFFAOYSA-N 1-isocyanato-4-[2-(4-isocyanatophenyl)propan-2-yl]benzene Chemical compound C=1C=C(N=C=O)C=CC=1C(C)(C)C1=CC=C(N=C=O)C=C1 PGKVHYTTXBKQQT-UHFFFAOYSA-N 0.000 description 1
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- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
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- GELMWIVBBPAMIO-UHFFFAOYSA-N 2-methylbutan-2-amine Chemical compound CCC(C)(C)N GELMWIVBBPAMIO-UHFFFAOYSA-N 0.000 description 1
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- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
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- AHCDZZIXAMDCBJ-UHFFFAOYSA-N CCC[Na] Chemical compound CCC[Na] AHCDZZIXAMDCBJ-UHFFFAOYSA-N 0.000 description 1
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- PKMBLJNMKINMSK-UHFFFAOYSA-N magnesium;azanide Chemical compound [NH2-].[NH2-].[Mg+2] PKMBLJNMKINMSK-UHFFFAOYSA-N 0.000 description 1
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- WNTBDUYEISRPNS-UHFFFAOYSA-N n-butyl-2-ethylhexan-1-amine Chemical compound CCCCNCC(CC)CCCC WNTBDUYEISRPNS-UHFFFAOYSA-N 0.000 description 1
- AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 1
- IOXXVNYDGIXMIP-UHFFFAOYSA-N n-methylprop-2-en-1-amine Chemical compound CNCC=C IOXXVNYDGIXMIP-UHFFFAOYSA-N 0.000 description 1
- KFMINNMMWXMERW-UHFFFAOYSA-N n-prop-1-enylbutan-1-amine Chemical compound CCCCNC=CC KFMINNMMWXMERW-UHFFFAOYSA-N 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical class ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 238000010944 pre-mature reactiony Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000001373 regressive effect Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical class O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910001415 sodium ion Inorganic materials 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
- 239000011343 solid material Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000013526 supercooled liquid Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 208000006379 syphilis Diseases 0.000 description 1
- 230000028016 temperature homeostasis Effects 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 125000003441 thioacyl group Chemical group 0.000 description 1
- FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000005406 washing 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
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75686768A | 1968-09-03 | 1968-09-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1944417A1 true DE1944417A1 (de) | 1970-03-12 |
Family
ID=25045399
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691944417 Pending DE1944417A1 (de) | 1968-09-03 | 1969-09-02 | Verfahren zur Herstellung von Formkoerpern durch kontinuierliche Polymerisation von Laktamen |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE738356A (enrdf_load_stackoverflow) |
| DE (1) | DE1944417A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2020523A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1289349A (enrdf_load_stackoverflow) |
| NL (1) | NL6913448A (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6441109B1 (en) | 1999-12-30 | 2002-08-27 | Basf Corporation | Continuous polymerization and direct fiber spinning and apparatus for accomplishing same |
| FR2993887B1 (fr) | 2012-07-27 | 2014-12-19 | Setup Performance | Procede de preparation de polyamide par extrusion reactive et extrudeuse adaptee pour la mise en oeuvre d'un tel procede |
| CN115869891A (zh) * | 2021-09-27 | 2023-03-31 | 成都肆零壹科技有限公司 | 一种酰胺聚合的连续流反应系统及方法 |
-
1969
- 1969-09-02 GB GB1289349D patent/GB1289349A/en not_active Expired
- 1969-09-02 DE DE19691944417 patent/DE1944417A1/de active Pending
- 1969-09-02 FR FR6929957A patent/FR2020523A1/fr not_active Withdrawn
- 1969-09-03 BE BE738356D patent/BE738356A/xx unknown
- 1969-09-03 NL NL6913448A patent/NL6913448A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1289349A (enrdf_load_stackoverflow) | 1972-09-13 |
| NL6913448A (enrdf_load_stackoverflow) | 1970-03-05 |
| BE738356A (enrdf_load_stackoverflow) | 1970-03-03 |
| FR2020523A1 (enrdf_load_stackoverflow) | 1970-07-17 |
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