DE2020102A1 - Verfahren zur Polymerisation von ss-Lactonen - Google Patents
Verfahren zur Polymerisation von ss-LactonenInfo
- Publication number
- DE2020102A1 DE2020102A1 DE19702020102 DE2020102A DE2020102A1 DE 2020102 A1 DE2020102 A1 DE 2020102A1 DE 19702020102 DE19702020102 DE 19702020102 DE 2020102 A DE2020102 A DE 2020102A DE 2020102 A1 DE2020102 A1 DE 2020102A1
- Authority
- DE
- Germany
- Prior art keywords
- polymerization
- oxide
- lactone
- added
- epoxy
- 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
- 125000003180 beta-lactone group Chemical group 0.000 title claims description 21
- 238000006116 polymerization reaction Methods 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 14
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 14
- 239000004593 Epoxy Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 claims description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 5
- 239000003999 initiator Substances 0.000 claims description 5
- -1 oxyaralkyl Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 1
- 229960000380 propiolactone Drugs 0.000 description 16
- 229920000642 polymer Polymers 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 3
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 2
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 2
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000012986 chain transfer agent Substances 0.000 description 2
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 2
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- GXBYFVGCMPJVJX-UHFFFAOYSA-N Epoxybutene Chemical compound C=CC1CO1 GXBYFVGCMPJVJX-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 239000011952 anionic catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- UCAOGXRUJFKQAP-UHFFFAOYSA-N n,n-dimethyl-5-nitropyridin-2-amine Chemical compound CN(C)C1=CC=C([N+]([O-])=O)C=N1 UCAOGXRUJFKQAP-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2615—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen the other compounds containing carboxylic acid, ester or anhydride groups
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyethers (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3246569 | 1969-04-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2020102A1 true DE2020102A1 (de) | 1970-12-23 |
Family
ID=12359704
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702020102 Pending DE2020102A1 (de) | 1969-04-25 | 1970-04-24 | Verfahren zur Polymerisation von ss-Lactonen |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE2020102A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1295752A (enrdf_load_stackoverflow) |
| NL (1) | NL7005676A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3712578A1 (de) * | 1986-04-15 | 1987-10-29 | Daicel Chem | Poly-(epsilon)-caprolactonharz und verfahren zum verlangsamen der hydrolysegeschwindigkeit fuer dasselbe |
-
1970
- 1970-04-20 NL NL7005676A patent/NL7005676A/xx unknown
- 1970-04-22 GB GB1295752D patent/GB1295752A/en not_active Expired
- 1970-04-24 DE DE19702020102 patent/DE2020102A1/de active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3712578A1 (de) * | 1986-04-15 | 1987-10-29 | Daicel Chem | Poly-(epsilon)-caprolactonharz und verfahren zum verlangsamen der hydrolysegeschwindigkeit fuer dasselbe |
| DE3712578C2 (de) * | 1986-04-15 | 1999-08-12 | Daicel Chem | Poly-epsilon-Caprolactonharz und Verfahren zum Verlangsamen der Hydrolysegeschwindigkeit für dasselbe |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7005676A (enrdf_load_stackoverflow) | 1970-10-27 |
| GB1295752A (enrdf_load_stackoverflow) | 1972-11-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1595484C3 (de) | Verfahren zur Herstellung von Ricinusölpolyglycidyläthem und deren Verwendung zur Herstellung einer härtbaren Masse | |
| EP0164667A1 (de) | Thermoplastische Formmassen auf der Basis von Polyoxymethylen und polymeren Adipatcarbonatmischestern | |
| DE3650211T2 (de) | Polyätherhomo- oder -copolymer, Monomer dafür und Verfahren zu deren Herstellung. | |
| DE2020102A1 (de) | Verfahren zur Polymerisation von ss-Lactonen | |
| DE1180939B (de) | Verfahren zur Herstellung von Copolymerisaten des Trioxans | |
| DE1570365A1 (de) | Verfahren zur Herstellung von neuen Oxymethylencopolymeren | |
| EP0618248B1 (de) | Carbonsäureester- und Kohlensäureestergruppen enthaltendes Polymer und Verfahren zu seiner Herstellung | |
| DE2319359B2 (de) | Preß- und Formmassen mit verbesserter Verarbeitbarkeit | |
| DE1720409A1 (de) | Verfahren zur Herstellung von Polyoxymethylen | |
| DE1495733C (de) | Verfahren zur Herstellung von Oxymethylen Blockcopolymerisaten | |
| DE1234988B (de) | Verfahren zur Herstellung von Copolymerisaten des Trioxans | |
| DE1176862B (de) | Verfahren zur Herstellung von Copolymerisaten des Formaldehyds oder Trioxans | |
| DE1248938B (de) | Verfahren zur Herstellung kristalliner Acetaldehydpolymerisate | |
| DE2112985A1 (de) | Vernetzbares hitzehaertendes Polyesterharz | |
| DE1645681B2 (de) | Verfahren zur herstellung von oxymethylenhomo- oder oxymethylen-copolymerisaten | |
| DE1220607B (de) | Verfahren zur Herstellung von Polymerisaten oder Copolymerisaten des Trioxans | |
| DE1745087B2 (de) | Oxymethylen-mischpolymerisate, deren herstellung und verwendung | |
| DE1233602B (de) | Verfahren zur Herstellung von Copolymerisaten des Trioxans | |
| DE1237781B (de) | Verfahren zum Polymerisieren von N-Sulfonylaziridinen | |
| DE1595033B2 (de) | Verfahren zur polymerisation von 3 4 5 und 6 ringigen cyclischen aethern und deren derivaten | |
| DE1231009B (de) | Verfahren zur Herstellung von Copolymerisaten des Trioxans | |
| DE1201550B (de) | Verfahren zur Herstellung von Polyoxymethylenen | |
| AT261199B (de) | Verfahren zur Herstellung eines festen, kristallinen Polymers aus Äthylen und Propylen | |
| DE1795545A1 (de) | Formbare thermoplastische Oxymethylencopolymere | |
| DE2540206B1 (de) | Polyoxymethylen-Formmassen (II) |