DE1261671B - Verfahren zur anionischen Polymerisation von alpha-Pyrrolidon - Google Patents
Verfahren zur anionischen Polymerisation von alpha-PyrrolidonInfo
- Publication number
- DE1261671B DE1261671B DE1962B0067109 DEB0067109A DE1261671B DE 1261671 B DE1261671 B DE 1261671B DE 1962B0067109 DE1962B0067109 DE 1962B0067109 DE B0067109 A DEB0067109 A DE B0067109A DE 1261671 B DE1261671 B DE 1261671B
- Authority
- DE
- Germany
- Prior art keywords
- pyrrolidone
- polymerization
- parts
- activators
- anionic polymerization
- 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
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 9
- 238000010539 anionic addition polymerization reaction Methods 0.000 title claims description 6
- 239000012190 activator Substances 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 10
- 239000012442 inert solvent Substances 0.000 claims description 3
- 239000002685 polymerization catalyst Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229920001007 Nylon 4 Polymers 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- -1 N-cyanocapryllactam Chemical compound 0.000 description 3
- 150000003951 lactams Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VWCJRVVCWQRZJN-UHFFFAOYSA-N 2-oxoazepane-1-carbonitrile Chemical compound O=C1CCCCCN1C#N VWCJRVVCWQRZJN-UHFFFAOYSA-N 0.000 description 2
- SUVVSXKEWFUHOA-UHFFFAOYSA-N 2-oxopyrrolidine-1-carbonitrile Chemical compound O=C1CCCN1C#N SUVVSXKEWFUHOA-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- CNVYERSDZLTUQK-UHFFFAOYSA-N 2-[(2-oxocyclohexyl)methyl]cyclohexan-1-one Chemical class O=C1CCCCC1CC1C(=O)CCCC1 CNVYERSDZLTUQK-UHFFFAOYSA-N 0.000 description 1
- ZLASRBBEAGFAQM-UHFFFAOYSA-N 2-oxo-azacyclotridecane-1-carbonitrile Chemical compound O=C1CCCCCCCCCCCN1C#N ZLASRBBEAGFAQM-UHFFFAOYSA-N 0.000 description 1
- GOCAXIBFPODMEV-UHFFFAOYSA-N 2-oxo-azacycloundecane-1-carbonitrile Chemical compound C(#N)N1C(CCCCCCCCC1)=O GOCAXIBFPODMEV-UHFFFAOYSA-N 0.000 description 1
- XFRLKSXYOZYITK-UHFFFAOYSA-N 2-oxoazepane-3-carbonitrile Chemical compound O=C1NCCCCC1C#N XFRLKSXYOZYITK-UHFFFAOYSA-N 0.000 description 1
- YHJJFMCSWQKOMK-UHFFFAOYSA-N 2-oxoazocane-1-carbonitrile Chemical compound O=C1CCCCCCN1C#N YHJJFMCSWQKOMK-UHFFFAOYSA-N 0.000 description 1
- DSHBXTLXUSBWIN-UHFFFAOYSA-N 2-oxopiperidine-1-carbonitrile Chemical compound O=C1CCCCN1C#N DSHBXTLXUSBWIN-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000004952 Polyamide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Inorganic materials [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- ZOMBKNNSYQHRCA-UHFFFAOYSA-J calcium sulfate hemihydrate Chemical compound O.[Ca+2].[Ca+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZOMBKNNSYQHRCA-UHFFFAOYSA-J 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000008395 clarifying agent Substances 0.000 description 1
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical class ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000011507 gypsum plaster Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 150000002843 nonmetals Chemical class 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE631857D BE631857A (enrdf_load_stackoverflow) | 1962-05-04 | ||
| DE1962B0067109 DE1261671B (de) | 1962-05-04 | 1962-05-04 | Verfahren zur anionischen Polymerisation von alpha-Pyrrolidon |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1962B0067109 DE1261671B (de) | 1962-05-04 | 1962-05-04 | Verfahren zur anionischen Polymerisation von alpha-Pyrrolidon |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1261671B true DE1261671B (de) | 1968-02-22 |
Family
ID=6975393
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1962B0067109 Pending DE1261671B (de) | 1962-05-04 | 1962-05-04 | Verfahren zur anionischen Polymerisation von alpha-Pyrrolidon |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE631857A (enrdf_load_stackoverflow) |
| DE (1) | DE1261671B (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0047228A3 (en) * | 1980-08-28 | 1982-09-22 | Ciba-Geigy Ag | Mixtures for the preparation of nitrogen-containing addition polymers |
| EP0041048A3 (en) * | 1980-05-23 | 1982-09-22 | Ciba-Geigy Ag | Mixtures for preparing polyadducts containing nitrogen |
| EP2135319A4 (en) * | 2006-07-19 | 2010-04-07 | Lg Chemical Ltd | LACTAM-BASED ADDITIVE FOR ELECTROLYTE AND SECONDARY BATTERY THEREWITH |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE592979A (enrdf_load_stackoverflow) * | 1959-07-14 | |||
| DE1067587B (de) * | 1957-07-20 | 1959-10-22 | Basf Ag | Verfahren zur einstufigen Herstellung von Polyamid-Formkoerpern |
| FR1216331A (fr) * | 1957-10-17 | 1960-04-25 | Procédé pour la polymérisation alcaline rapide du 6-caprolactame |
-
0
- BE BE631857D patent/BE631857A/xx unknown
-
1962
- 1962-05-04 DE DE1962B0067109 patent/DE1261671B/de active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1067587B (de) * | 1957-07-20 | 1959-10-22 | Basf Ag | Verfahren zur einstufigen Herstellung von Polyamid-Formkoerpern |
| FR1216331A (fr) * | 1957-10-17 | 1960-04-25 | Procédé pour la polymérisation alcaline rapide du 6-caprolactame | |
| BE592979A (enrdf_load_stackoverflow) * | 1959-07-14 |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0041048A3 (en) * | 1980-05-23 | 1982-09-22 | Ciba-Geigy Ag | Mixtures for preparing polyadducts containing nitrogen |
| EP0047228A3 (en) * | 1980-08-28 | 1982-09-22 | Ciba-Geigy Ag | Mixtures for the preparation of nitrogen-containing addition polymers |
| EP2135319A4 (en) * | 2006-07-19 | 2010-04-07 | Lg Chemical Ltd | LACTAM-BASED ADDITIVE FOR ELECTROLYTE AND SECONDARY BATTERY THEREWITH |
| US7947398B2 (en) | 2006-07-19 | 2011-05-24 | Lg Chem, Ltd. | Electrode for a secondary battery and secondary battery comprising the same |
Also Published As
| Publication number | Publication date |
|---|---|
| BE631857A (enrdf_load_stackoverflow) |
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