DE1570530A1 - Verfahren zur Herstellung von Copolymerisaten von ss-Lactamen - Google Patents
Verfahren zur Herstellung von Copolymerisaten von ss-LactamenInfo
- Publication number
- DE1570530A1 DE1570530A1 DE19651570530 DE1570530A DE1570530A1 DE 1570530 A1 DE1570530 A1 DE 1570530A1 DE 19651570530 DE19651570530 DE 19651570530 DE 1570530 A DE1570530 A DE 1570530A DE 1570530 A1 DE1570530 A1 DE 1570530A1
- Authority
- DE
- Germany
- Prior art keywords
- solution
- catalyst
- dispersion
- emulsified
- solvent
- 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
- 238000000034 method Methods 0.000 title claims description 23
- 229920001577 copolymer Polymers 0.000 title claims description 11
- 150000003952 β-lactams Chemical class 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 2
- 239000002904 solvent Substances 0.000 claims description 26
- 239000003054 catalyst Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 17
- 239000000178 monomer Substances 0.000 claims description 12
- 239000006185 dispersion Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 238000009826 distribution Methods 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
- 150000003951 lactams Chemical class 0.000 description 18
- 238000006116 polymerization reaction Methods 0.000 description 16
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 14
- IGWGXZKGWFYOHE-UHFFFAOYSA-N 4,4-dimethylazetidin-2-one Chemical compound CC1(C)CC(=O)N1 IGWGXZKGWFYOHE-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- GDNULDIPPDQVRH-UHFFFAOYSA-N potassium;pyrrolidin-2-one Chemical compound [K].O=C1CCCN1 GDNULDIPPDQVRH-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- XMSFNEZQRPOHAR-UHFFFAOYSA-N 4-methylazetidin-2-one Chemical compound CC1CC(=O)N1 XMSFNEZQRPOHAR-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 4
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 239000008385 outer phase Substances 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 230000001804 emulsifying effect Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HUCDNALJLARZTQ-UHFFFAOYSA-N 3,4-dimethylazetidin-2-one Chemical compound CC1NC(=O)C1C HUCDNALJLARZTQ-UHFFFAOYSA-N 0.000 description 2
- ZEWHMWFASYXCAO-UHFFFAOYSA-N 4-ethenylazetidin-2-one Chemical compound C=CC1CC(=O)N1 ZEWHMWFASYXCAO-UHFFFAOYSA-N 0.000 description 2
- BODONWZDNUQEBV-UHFFFAOYSA-N 4-methyl-4-propylazetidin-2-one Chemical compound CCCC1(C)CC(=O)N1 BODONWZDNUQEBV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000008384 inner phase Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- -1 polycyclic lactams Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- ADTJRKBVIPQVNP-UHFFFAOYSA-N 1-(4-chlorophenyl)azetidin-2-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)CC1 ADTJRKBVIPQVNP-UHFFFAOYSA-N 0.000 description 1
- ROKSAUSPJGWCSM-UHFFFAOYSA-N 2-(7,7-dimethyl-4-bicyclo[3.1.1]hept-3-enyl)ethanol Chemical compound C1C2C(C)(C)C1CC=C2CCO ROKSAUSPJGWCSM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- OLFOOXKLYNDRGR-UHFFFAOYSA-N 4-methyl-4-(phenoxymethyl)azetidin-2-one Chemical compound O(C1=CC=CC=C1)CC1(CC(N1)=O)C OLFOOXKLYNDRGR-UHFFFAOYSA-N 0.000 description 1
- UMECPVGLNIYFEO-UHFFFAOYSA-N 4-propan-2-ylazetidin-2-one Chemical compound CC(C)C1CC(=O)N1 UMECPVGLNIYFEO-UHFFFAOYSA-N 0.000 description 1
- 101100096533 Drosophila melanogaster SelD gene Proteins 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
- 229920002367 Polyisobutene Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000012693 lactam polymerization Methods 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- KSMWLICLECSXMI-UHFFFAOYSA-N sodium;benzene Chemical compound [Na+].C1=CC=[C-]C=C1 KSMWLICLECSXMI-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000012982 x-ray structure analysis 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
- C08G69/22—Beta-lactams
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Catalysts (AREA)
- Polyamides (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0044890 | 1965-01-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1570530A1 true DE1570530A1 (de) | 1970-01-29 |
Family
ID=7100251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651570530 Pending DE1570530A1 (de) | 1965-01-07 | 1965-01-07 | Verfahren zur Herstellung von Copolymerisaten von ss-Lactamen |
Country Status (4)
-
1965
- 1965-01-07 DE DE19651570530 patent/DE1570530A1/de active Pending
-
1966
- 1966-01-07 FR FR45206A patent/FR1464333A/fr not_active Expired
- 1966-01-07 BE BE674845D patent/BE674845A/xx unknown
- 1966-01-07 GB GB96066A patent/GB1106351A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1464333A (fr) | 1966-12-30 |
| GB1106351A (en) | 1968-03-13 |
| BE674845A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-07-07 |
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