WO1995017445B1 - Process to react epoxide-containing compounds and aliphatic alcohols - Google Patents
Process to react epoxide-containing compounds and aliphatic alcoholsInfo
- Publication number
- WO1995017445B1 WO1995017445B1 PCT/US1994/013427 US9413427W WO9517445B1 WO 1995017445 B1 WO1995017445 B1 WO 1995017445B1 US 9413427 W US9413427 W US 9413427W WO 9517445 B1 WO9517445 B1 WO 9517445B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- moieties
- containing compound
- previous
- epoxide
- aliphatic hydroxyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract 12
- 238000000034 method Methods 0.000 title claims 12
- 150000002118 epoxides Chemical class 0.000 title claims 6
- -1 aliphatic alcohols Chemical class 0.000 title 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 6
- 125000001931 aliphatic group Chemical group 0.000 claims abstract 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-N Trifluoromethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000003054 catalyst Substances 0.000 claims abstract 4
- 125000003700 epoxy group Chemical group 0.000 claims abstract 2
- 229920005989 resin Polymers 0.000 claims abstract 2
- 239000011347 resin Substances 0.000 claims abstract 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 3
- 125000004432 carbon atoms Chemical group C* 0.000 claims 2
- 239000004593 Epoxy Substances 0.000 claims 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N Glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 230000003197 catalytic Effects 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 125000005496 phosphonium group Chemical group 0.000 claims 1
- 229920000647 polyepoxide Polymers 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims 1
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
- BZLZKLMROPIZSR-UHFFFAOYSA-N triphenylsilicon Chemical group C1=CC=CC=C1[Si](C=1C=CC=CC=1)C1=CC=CC=C1 BZLZKLMROPIZSR-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract 1
Abstract
A reaction between: (1) a compound that contains one or more epoxide moieties per molecule, and (2) a compound that contains one or more primary aliphatic hydroxyl groups per molecule; is catalyzed by: (3) trifluoromethanesulfonic acid or a derivative therof and run at a temperature of no more than 130 °C. The catalyst preferably catalyzes reaction at the primary aliphatic hydroxyl group, so that the resulting resin does not gel. It can be optionally used at relatively moderate temperatures without solvents.
Claims
1. A process to react:
(1) an epoxide-containing compound that contains one or more epoxide moieties per molecule, and
(2) an aliphatic hydroxyl-containing compound that contains one or more aliphatic hydroxyl groups per molecule, characterized in that:
(a) the aliphatic hydroxyl groups in component (2) are bonded to a primary carbon atom;
(b) the reaction is carried out in the presence of a catalytic amount of trifluoromethanesulfonic acid or a derivative thereof which is not a metal trifluorosulfonate salt; and
(c) the reaction is carried out at a temperature of no more than 130°C.
2. A process as described in Claim 1 wherein the equivalent ratio of aliphatic hydroxyl-containing compound to epoxide-containing compound is from 40:60 to 60:40.
3. A process as described in Claim 1 wherein the equivalent ratio of aliphatic hydroxyl-containing compound to epoxide-containing compound is from 1 :99 to 40:60.
4. A process as described in any of the previous Claims wherein the catalyst contains trifluoromethylsulfonate moieties and any of the following counter-moieties: hydrogen atoms, silyl moieties, ammonium moieties, phosphonium moieties, sulfonium moieties, cations.
5. A process as described in any of the previous claims wherein the catalyst is trifluoromethanesulfonic acid; an alkylsiiyi trifiuoromethanesuifonate; or a polymer or resin that contains trifluoromethanesulfonic acid moieties or alkylsiiyi trifiuoromethanesuifonate moieties or both.
6. A process as described in any of the previous claims wherein the catalyst contains an organosilyl moiety.
7. A process as described in any of the previous claims, wherein the organosilyl moiety is any of: a trialkylsilyl moiety, a triphenyl silyl moiety, a dialkylphenyl moiety, or a hydrodialkylsilyl moiety, wherein each alkyl group contains 1 to 6 carbon atoms.
8. A process as described in any of the previous claims wherein the temperature of the reaction is 20°C to 110°C.
9. A process as described in any of the previous claims wherein the epoxide- containing compound is any of: a glycidyl acryiate, a glycidyl methacrylate, an alkylene oxide or an epihalohydrin.
10. A process as described in any of Claims 1-8 wherein the epoxide-containing compound is a polyepoxide having an epoxy equivalent weight of 100 to 1000.
11. A process as described in any of the previous claims wherein 75 to 100 percent of all hydroxyl groups in the aliphatic hydroxyl-containing compound are primary aliphatic hydroxyl groups.
-15-
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019960703280A KR960706519A (en) | 1993-12-21 | 1994-11-17 | Process to react epoxide-containing compounds and aliphatic alcohols |
| JP7517418A JPH09507254A (en) | 1993-12-21 | 1994-11-17 | Method for reacting epoxide-containing compound with aliphatic alcohol |
| EP95903575A EP0736052B1 (en) | 1993-12-21 | 1994-11-17 | Process to react epoxide-containing compounds and aliphatic alcohols |
| DE69420047T DE69420047T2 (en) | 1993-12-21 | 1994-11-17 | METHOD FOR REACTION OF COMPOUNDS CONTAINING EPOXY GROUPS WITH ALIPHATIC ALCOHOLS |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17105493A | 1993-12-21 | 1993-12-21 | |
| US08/171,054 | 1993-12-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1995017445A1 WO1995017445A1 (en) | 1995-06-29 |
| WO1995017445B1 true WO1995017445B1 (en) | 1995-07-20 |
Family
ID=22622311
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1994/013427 WO1995017445A1 (en) | 1993-12-21 | 1994-11-17 | Process to react epoxide-containing compounds and aliphatic alcohols |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5728796A (en) |
| EP (1) | EP0736052B1 (en) |
| JP (1) | JPH09507254A (en) |
| KR (1) | KR960706519A (en) |
| CN (1) | CN1138338A (en) |
| CA (1) | CA2177174A1 (en) |
| DE (1) | DE69420047T2 (en) |
| TW (1) | TW349964B (en) |
| WO (1) | WO1995017445A1 (en) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4446877A1 (en) * | 1994-12-27 | 1996-07-04 | Henkel Kgaa | Process for ring opening of epoxides |
| ATE255610T1 (en) * | 1998-10-22 | 2003-12-15 | Vantico Ag | CURABLE EPOXY RESIN COMPOSITIONS |
| EP1301553A2 (en) * | 2000-07-11 | 2003-04-16 | Vantico AG | High functional polymers |
| GB0200505D0 (en) * | 2002-01-10 | 2002-02-27 | Vantico Ag | Highly functional polymers |
| CA2602013A1 (en) * | 2005-03-24 | 2006-09-28 | Goldschmidt Gmbh | Low surface tension surfactants based on ether alcohol and their use |
| MX2009012951A (en) * | 2007-06-05 | 2010-03-03 | Akzo Nobel Paints Llc | Radiation curable coating composition derived from epoxidized vegetable oils. |
| EP2161295A1 (en) | 2008-09-05 | 2010-03-10 | Basf Se | Highly functional polyetherols, method for their manufacture and application thereof |
| EP2090606A1 (en) * | 2008-02-15 | 2009-08-19 | Basf Se | Highly functional polyetherols, method for their manufacture and application thereof |
| WO2009101141A1 (en) * | 2008-02-15 | 2009-08-20 | Basf Se | Highly functional polyetherols and the production and use thereof |
| RU2539981C2 (en) | 2009-03-05 | 2015-01-27 | Акцо Нобель Коатингс Интернэшнл Б.В. | Grafted acryl copolymers of oil polyols with hydroxyl functional groups |
| EP2576670A4 (en) | 2010-05-31 | 2013-12-18 | Basf Se | Mechanically stabilized polyazoles |
| PL3878912T3 (en) | 2011-02-07 | 2023-06-26 | Swimc Llc | Coating compositions for containers and other articles and methods of coating |
| WO2013017417A1 (en) | 2011-07-29 | 2013-02-07 | Basf Se | Polymer flame retardant |
| ES2599253T3 (en) | 2011-12-21 | 2017-01-31 | Akzo Nobel Coatings International B.V. | Solvent based coating compositions |
| CN103998019A (en) * | 2011-12-21 | 2014-08-20 | 阿克佐诺贝尔化学国际公司 | Functional oil polyol acrylic graft copolymers and their use in personal care applications |
| US9260625B2 (en) | 2011-12-21 | 2016-02-16 | Akzo Nobel Coatings International B.V. | Water-based coating compositions |
| AU2013299578A1 (en) | 2012-08-09 | 2015-02-19 | Valspar Sourcing, Inc. | Compositions for containers and other articles and methods of using same |
| CN104640909B (en) | 2012-09-20 | 2018-11-13 | 巴斯夫欧洲公司 | Hyperbranched phosphate |
| CN106536624B (en) | 2014-04-14 | 2019-11-19 | 宣伟投资管理有限公司 | Preparation is used for the method for the composition of container and other products and the method using the composition |
| CN115894890A (en) * | 2022-12-05 | 2023-04-04 | 华南理工大学 | Selective functionalized modification method of primary alcohol compound |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2536069A1 (en) * | 1982-11-17 | 1984-05-18 | Bp Chimie Sa | PROCESS FOR THE PREPARATION OF ADDITION PRODUCTS OF EPOXIDES AND HYDROXYL COMPOUNDS |
| AU571499B2 (en) * | 1983-04-01 | 1988-04-21 | Dow Chemical Company, The | Preparing epoxy resins |
| US4707535A (en) * | 1983-10-27 | 1987-11-17 | Union Carbide Corporation | Low viscosity adducts of a poly(active hydrogen) organic compound and polyepoxide |
| US5134239A (en) * | 1984-07-17 | 1992-07-28 | The Dow Chemical Company | Latent catalysts for epoxy-phenolic reactions |
| US5169473A (en) * | 1990-05-21 | 1992-12-08 | The Dow Chemical Company | Latent catalysts, epoxy compositions incorporating same, and coating, impregnating and bonding methods employing the compositions |
| GB9027448D0 (en) * | 1990-12-18 | 1991-02-06 | Ciba Geigy Ag | Production of glycidyl compounds |
| GB9027406D0 (en) * | 1990-12-18 | 1991-02-06 | Ciba Geigy Ag | Production of compounds |
| GB9102421D0 (en) * | 1991-02-05 | 1991-03-20 | Shell Int Research | Modified epoxy resins having a narrow molecular weight distribution |
| US5117010A (en) * | 1991-08-15 | 1992-05-26 | Ciba-Geigy Corporation | Process for the preparation of addition products of epoxides and alcohols |
| GB9125116D0 (en) * | 1991-11-23 | 1992-01-22 | Ciba Geigy Ag | Chemical process |
| GB9200566D0 (en) * | 1992-01-11 | 1992-03-11 | Ciba Geigy | Compounds |
| TW224108B (en) * | 1992-05-06 | 1994-05-21 | Ciba Geigy |
-
1994
- 1994-11-17 JP JP7517418A patent/JPH09507254A/en active Pending
- 1994-11-17 CA CA002177174A patent/CA2177174A1/en not_active Abandoned
- 1994-11-17 CN CN94194563A patent/CN1138338A/en active Pending
- 1994-11-17 EP EP95903575A patent/EP0736052B1/en not_active Expired - Lifetime
- 1994-11-17 WO PCT/US1994/013427 patent/WO1995017445A1/en active IP Right Grant
- 1994-11-17 KR KR1019960703280A patent/KR960706519A/en not_active Application Discontinuation
- 1994-11-17 DE DE69420047T patent/DE69420047T2/en not_active Expired - Fee Related
- 1994-12-20 TW TW083111957A patent/TW349964B/en active
-
1996
- 1996-05-31 US US08/652,580 patent/US5728796A/en not_active Expired - Fee Related
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