JPS6367488B2 - - Google Patents
Info
- Publication number
- JPS6367488B2 JPS6367488B2 JP56013883A JP1388381A JPS6367488B2 JP S6367488 B2 JPS6367488 B2 JP S6367488B2 JP 56013883 A JP56013883 A JP 56013883A JP 1388381 A JP1388381 A JP 1388381A JP S6367488 B2 JPS6367488 B2 JP S6367488B2
- Authority
- JP
- Japan
- Prior art keywords
- tetrahydrofuran
- molecular weight
- reaction
- anhydride
- weight
- 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 52
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 26
- 238000006116 polymerization reaction Methods 0.000 claims description 14
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 claims description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 9
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 claims description 9
- 229920000909 polytetrahydrofuran Polymers 0.000 claims description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 150000002500 ions Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical group OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 claims description 2
- OBCUTHMOOONNBS-UHFFFAOYSA-N phosphorus pentafluoride Chemical compound FP(F)(F)(F)F OBCUTHMOOONNBS-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000003460 sulfonic acids Chemical class 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000000047 product Substances 0.000 description 13
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 125000004185 ester group Chemical group 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 229920000557 Nafion® Polymers 0.000 description 2
- 229910018286 SbF 6 Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000006276 transfer reaction Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MBAKFIZHTUAVJN-UHFFFAOYSA-I hexafluoroantimony(1-);hydron Chemical compound F.F[Sb](F)(F)(F)F MBAKFIZHTUAVJN-UHFFFAOYSA-I 0.000 description 1
- 239000011346 highly viscous material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- -1 perfluorinated aliphatic sulfonic acids Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011345 viscous material 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
- 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
- C08G65/04—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 only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/16—Cyclic ethers having four or more ring atoms
- C08G65/20—Tetrahydrofuran
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polyethers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803004328 DE3004328A1 (de) | 1980-02-06 | 1980-02-06 | Polytetrahydrofurane mit acrylat- oder methacrylatendgruppen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56125428A JPS56125428A (en) | 1981-10-01 |
| JPS6367488B2 true JPS6367488B2 (OSRAM) | 1988-12-26 |
Family
ID=6093901
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1388381A Granted JPS56125428A (en) | 1980-02-06 | 1981-02-03 | Manufacture of polytetrahydrofuran |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4412063A (OSRAM) |
| EP (1) | EP0033883B1 (OSRAM) |
| JP (1) | JPS56125428A (OSRAM) |
| DE (2) | DE3004328A1 (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3211635A1 (de) * | 1982-03-30 | 1983-10-06 | Bayer Ag | Verfahren zur herstellung von polyetrahydrofuranen mit esterendgruppen |
| DE10101387A1 (de) | 2001-01-13 | 2002-07-18 | Merck Patent Gmbh | Polyester mit Methacrylatendgruppen |
| CN103865055B (zh) * | 2014-03-19 | 2016-03-23 | 上海应用技术学院 | 一种大分子疏水性单体聚四氢呋喃二丙烯酸酯及其制备方法 |
| WO2018177729A1 (en) | 2017-03-28 | 2018-10-04 | Arkema France | Compositions useful for forming soft touch coatings |
| US20230235199A1 (en) * | 2020-08-27 | 2023-07-27 | 3M Innovative Properties Company | Polymers derived from a poly(tetrahydrofuran)(meth)acrylate macromer, adhesive compositions, and articles |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH533654A (de) * | 1966-03-11 | 1973-02-15 | Minnesota Mining & Mfg | Verfahren zur Herstellung von Polyäthern und deren Verwendung |
| US3660532A (en) * | 1970-01-30 | 1972-05-02 | Firestone Tire & Rubber Co | Castable elastomers and their manufacture |
| JPS5232677B2 (OSRAM) * | 1972-12-29 | 1977-08-23 | ||
| DE2445961C2 (de) * | 1974-09-26 | 1983-12-01 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Polymerisation von Tetrahydrofuran |
| US4163115A (en) * | 1976-03-31 | 1979-07-31 | E. I. Du Pont De Nemours And Company | Preparation of esters of poly-(tetramethylene ether) glycol |
| DE2760272C2 (de) * | 1976-03-31 | 1987-04-16 | E.I. Du Pont De Nemours And Co., Wilmington, Del. | Verfahren zur Herstellung von Poly-(tetramethylenether)-glykol durch Alkoholyse eines Ester-Endgruppen aufweisenden Poly-(tetramethylenether)-glykols |
| US4127513A (en) * | 1977-11-09 | 1978-11-28 | E. I. Du Pont De Nemours And Company | Method for preparing polyether glycols |
| US4189566A (en) * | 1978-01-14 | 1980-02-19 | Basf Aktiengesellschaft | Polymerization of tetrahydrofuran |
| DE2827510A1 (de) * | 1978-06-22 | 1980-01-17 | Du Pont | Verfahren zur herstellung von esterendgruppen aufweisenden copolyaetherglykolen |
-
1980
- 1980-02-06 DE DE19803004328 patent/DE3004328A1/de not_active Withdrawn
-
1981
- 1981-01-26 EP EP81100536A patent/EP0033883B1/de not_active Expired
- 1981-01-26 DE DE8181100536T patent/DE3161058D1/de not_active Expired
- 1981-02-03 JP JP1388381A patent/JPS56125428A/ja active Granted
-
1982
- 1982-04-02 US US06/364,986 patent/US4412063A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE3161058D1 (en) | 1983-11-10 |
| JPS56125428A (en) | 1981-10-01 |
| US4412063A (en) | 1983-10-25 |
| DE3004328A1 (de) | 1981-08-13 |
| EP0033883A1 (de) | 1981-08-19 |
| EP0033883B1 (de) | 1983-10-05 |
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