Phosphonium phenoxide catalysts for promoting reacting of epoxides with phenols and/or carboxylic acids
AssigneeThe Dow Chemical Company
InventorsGeorge A. Doorakian, James L. Bertram
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Abstract
Certain tetrahydrocarbyl phosphonium phenoxide salts are described herein which are novel compounds and/or novel catalysts for promoting the reaction between vicinal epoxides and phenols and/or carboxylic acids or anhydrides. These catalysts are particularly useful in preparing high molecular weight epoxy resins by the advancement reaction of diglycidyl ether of bisphenol A with bisphenol A.
Claims21
A precatalyzed epoxy resin comprising (a) an epoxy resin bearing an average of more than one vicinal epoxy group per molecule and (b) a catalytic amount of a compound represented by the formula ##STR11## or a complex of the compound represented by Formula I with one or more equivalents of (1) an aromatic carbocyclic hydroxyl compound, H.sub.m X, or (2) a tetrahydrocarbyl phosphonium hydroxide salt, wherein
- (1) R.sub.1 -R.sub.4 each independently is hydrocarbyl or inertly-substituted hydrocarbyl;
- (2) X is the conjugate base or the diconjugate base of an aromatic carbocyclic nuclear hydroxylbearing compound;
- and
- (3) m is the valence of the anion X.
A precatalyzed polyhydric phenol comprising (a) a polyhydric phenol represented by the formula ##STR12## wherein, (1) each R independently is hydrogen, halogen, hydrocarbyl, inertly-substituted hydrocarbyl or hydrocarbyloxy;
- and (2) Y is a single covalent bond, oxygen, sulfur, --CO--, --SO--, --SO.sub.2 -- or lower alkylene or alkylidene of from 1 to 6 carbon atoms, inclusive;
- and (b) a catalytic amount of a compound corresponding to the formula ##STR13## or a complex of the compound represented by Formula I with one or more equivalents of (1) an aromatic carbocyclic hydroxyl compound, H.sub.m X, or (2) a tetrahydrocarbyl phosphonium hydroxide salt, wherein
- (1) R.sub.1 -R.sub.4 each independently is a hydrocarbyl or inertly-substituted hydrocarbyl;
- (2) X is a conjugate base of an aromatic carbocyclic nuclear hydroxyl-bearing compound;
- and
- (3) m is the valence of the anion X.
In the process of reacting, at an elevated temperature, (a) an epoxy resin bearing an average of more than one vicinal group per molecule with (b) a polyhydric phenol or carboxylic acid or anhydride, the improvement comprising conducting the reaction in the presence of a catalytic amount of the compound represented by the formula ##STR14## or a complex of the compound represented by Formula I with one or more equivalents of (1) an aromatic carbocyclic hydroxyl compound, H.sub.m X, or (2) a tetrahydrocarbyl phosphonium hydroxide salt, wherein
- (1) R.sub.1 -R.sub.4 each independently is a hydrocarbyl or inertly-substituted hydrocarbyl;
- (2) X is a conjugate base of an aromatic carbocyclic nuclear hydroxyl-bearing compound;
- and
- (3) m is the valence of the anion X.
In a process of reacting (a) an epoxy-containing material with (b) a phenol or carboxylic acid or anhydride, the improvement comprising conducting the reaction in the presence of a catalytic amount of the compound represented by the formula ##STR15## or a complex of this compound with one or more equivalents of (1) an aromatic carbocyclic hydroxyl compound, H.sub.m X, or (2) a tetrahydrocarbyl phosphonium hydroxide salt, wherein
- (1) R.sub.1 -R.sub.4 each independently is a hydrocarbyl or inertly-substituted hydrocarbyl;
- (2) X is a conjugate base of an aromatic carbocyclic nuclear hydroxyl-bearing compound;
- and
- (3) m is the valence of the anion X.
A process for preparing an ultra-high molecular weight resin whose backbone is substantially linear and consists essentially of oxyaryleneoxy(1,3-(2-hydroxy)alkylene) units comprising reacting substantially equivalent quantities of a polyhydric phenol and polyepoxide in an organic diluent in the presence of a catalytic amount of a compound represented by the formula ##STR16## or a complex of the compound represented by Formula I with one or more equivalents of (1) a phenol, H.sub.m X, or (2) a tetrahydrocarbyl phosphonium hydroxide salt, wherein
- (1) R.sub.1 -R.sub.4 each independently is a hydrocarbyl or inertly-substituted hydrocarbyl;
- (2) X is a phenoxide anion, said anion being a conjugate base of a polyhydric phenol bearing from 2 to 6 nuclear hydroxyl groups and having from about 12 to about 30 carbon atoms;
- and
- (3) m is the valence of the anion X.
A precatalyzed polyhydric phenol comprising (a) an advancement reaction product of a polyhydric phenol and a polyepoxide, said advancement reaction product bearing more than one phenolic hydroxyl group;
- and (b) a catalytic amount of a compound corresponding to the formula ##STR20## or a complex of the compound represented by Formula I with one or more equivalents of (1) an aromatic carbocyclic hydroxyl compound, H.sub.m X, or (2) a tetrahydrocarbyl phosphonium hydroxide salt, wherein
- (1) R.sub.1 -R.sub.4 each independently is a hydrocarbyl or inertly-substituted hydrocarbyl;
- (2) X is a conjugate base of an aromatic carbocyclic nuclear hydroxyl-bearing compound;
- and
- (3) m is the valence of the anion X.
Dependencies are inferred from the claim text.