GB1130323A - Process for preparing lactam polymers - Google Patents
Process for preparing lactam polymersInfo
- Publication number
- GB1130323A GB1130323A GB86966A GB86966A GB1130323A GB 1130323 A GB1130323 A GB 1130323A GB 86966 A GB86966 A GB 86966A GB 86966 A GB86966 A GB 86966A GB 1130323 A GB1130323 A GB 1130323A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- dimethyl
- lactams
- azetidinone
- catalyst
- 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 abstract 6
- 238000004519 manufacturing process Methods 0.000 title 1
- 229920000642 polymer Polymers 0.000 title 1
- 239000003054 catalyst Substances 0.000 abstract 6
- 239000007788 liquid Substances 0.000 abstract 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 239000000243 solution Substances 0.000 abstract 3
- 125000001424 substituent group Chemical group 0.000 abstract 3
- 239000006185 dispersion Substances 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 239000003999 initiator Substances 0.000 abstract 2
- 239000000178 monomer Substances 0.000 abstract 2
- -1 oxalyl pyrrolidone Chemical compound 0.000 abstract 2
- WBULCZWMWLOUQW-UHFFFAOYSA-N 10-methylundecylbenzene Chemical compound CC(C)CCCCCCCCCC1=CC=CC=C1 WBULCZWMWLOUQW-UHFFFAOYSA-N 0.000 abstract 1
- DCAKVVTXKWWUGN-UHFFFAOYSA-N 3,3-dimethylazetidin-2-one Chemical compound CC1(C)CNC1=O DCAKVVTXKWWUGN-UHFFFAOYSA-N 0.000 abstract 1
- IGWGXZKGWFYOHE-UHFFFAOYSA-N 4,4-dimethylazetidin-2-one Chemical compound CC1(C)CC(=O)N1 IGWGXZKGWFYOHE-UHFFFAOYSA-N 0.000 abstract 1
- ZEWHMWFASYXCAO-UHFFFAOYSA-N 4-ethenylazetidin-2-one Chemical compound C=CC1CC(=O)N1 ZEWHMWFASYXCAO-UHFFFAOYSA-N 0.000 abstract 1
- XMSFNEZQRPOHAR-UHFFFAOYSA-N 4-methylazetidin-2-one Chemical compound CC1CC(=O)N1 XMSFNEZQRPOHAR-UHFFFAOYSA-N 0.000 abstract 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 abstract 1
- 229920002367 Polyisobutene Polymers 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000000084 colloidal system Substances 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 abstract 1
- 239000003350 kerosene Substances 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract 1
- 230000001681 protective effect Effects 0.000 abstract 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 abstract 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 abstract 1
- 229940124530 sulfonamide Drugs 0.000 abstract 1
- 239000002562 thickening agent Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
- C08G69/22—Beta-lactams
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
1,130,323. Poly-#-lactams. FARBWERKE HOECHST A.G. 7 Jan., 1966 [7 Jan., 1965], No. 869/66. Heading C3R. Poly-#-lactams are produced by adding the lactam dropwise to a solution or dispersion of a basic catalyst in an inert liquid. Suitable lactams are those which are unsubstituted in the N-position but may contain up to 4 substituents on the α- and #-carbon atoms, these substituents containing up to a total of 12 aliphatic carbon atoms or 1 aromatic group and up to 9 aliphatic carbon atoms. A divalent substituent may be present giving rise to a ring in the molecule. Specified lactams include 4-methyl azetidinone, 4-vinyl azetidinone, 3,3-dimethyl azetidinone and 4,4-dimethyl azetidinone. Basic catalysts specified include the potassium salt of α-pyrrolidone. Solvents or dispersing media for the catalyst specified include dimethyl sulphoxide, tetramethylene sulphone, phosphoric acid tris(dimethyl amide), dimethyl formamide and N-methyl pyrrolidone. An initiator may be added to the catalyst before or simultaneously with the addition of monomer. Initiators specified include oxalyl pyrrolidone. A chain terminator, e.g. water, may also be added. The rate of lactam addition may equal the rate of consumption and the polymerization temperature may be between -15‹ and + 120‹ C. In a particular embodiment of the invention the catalyst solution or dispersion is emulsified with a liquid with which it is only partially miscible. This liquid may, however, be completely miscible with the lactam. Suitable liquids are C 5-24 aliphatic or cycloaliphatic hydrocarbons, e.g. kerosene (b.p. 160-180‹ C.), aliphatic ethers having 1-3 ether oxygen atoms and 4-24 carbon atoms, e.g. isopropyl ether, araliphatic ethers having 1-3 ether oxygen atoms, 6-24 aliphatic carbon atoms and 1-3 phenyl radicals or araliphatic hydrocarbons having 1-3 phenyl radicals and 3-24 aliphatic carbon atoms, e.g. isododecyl benzene. The emulsion may be formed with the aid of an emulsifier, e.g. a sulphonamide of an ethylenepropylene copolymer of repeating unit a thickener or a protective colloid. In Examples (2-4) a small quantity of monomer is mixed with the catalyst before the solution is emulsified. In Example (2) polyisobutylene is present.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0044889 | 1965-01-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1130323A true GB1130323A (en) | 1968-10-16 |
Family
ID=7100250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB86966A Expired GB1130323A (en) | 1965-01-07 | 1966-01-07 | Process for preparing lactam polymers |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE674838A (en) |
| DE (1) | DE1570529A1 (en) |
| FR (1) | FR1463301A (en) |
| GB (1) | GB1130323A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116515102A (en) * | 2022-01-21 | 2023-08-01 | 苏州万维生命科学技术有限公司 | Star-shaped beta-antibacterial glycopeptide, and preparation method and application thereof |
-
1965
- 1965-01-07 DE DE19651570529 patent/DE1570529A1/en active Pending
-
1966
- 1966-01-07 FR FR45205A patent/FR1463301A/en not_active Expired
- 1966-01-07 BE BE674838D patent/BE674838A/xx unknown
- 1966-01-07 GB GB86966A patent/GB1130323A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116515102A (en) * | 2022-01-21 | 2023-08-01 | 苏州万维生命科学技术有限公司 | Star-shaped beta-antibacterial glycopeptide, and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| BE674838A (en) | 1966-07-07 |
| DE1570529A1 (en) | 1970-03-05 |
| FR1463301A (en) | 1966-12-23 |
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