WO1995017445B1

WO1995017445B1 - Process to react epoxide-containing compounds and aliphatic alcohols

Info

Publication number: WO1995017445B1
Application number: PCT/US1994/013427
Authority: WO
Filing date: 1994-11-17
Publication date: 1995-07-20

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

[received by the International Bureau on 26 June 1995 (26.06.95); original claims 1 and 4 amended; remaining claims unchanged (1 page)]

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.

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