The reactions of glycidyl ethers and cyclic carboxylic anhydrides have been studied in detail, and the resins which result from these reactions have found wide acceptability in many fields of application.
In contrast, the reactions of glycidyl esters have escaped investigation almost entirely, although such esters, especially glycidyl acrylate and glycidyl methacrylate, have been used in resin formulations.
The purpose of our work was to prepare a number of members of the series
and to prepare resinous materials by the reaction of these esters with phthalic anhydride and with other cyclic carboxylic anhydrides. It was anticipated that a relationship between the chemical structure of the diglycidyl esters, i.e., the nominal distance between epoxide functions, and the physical properties of the derived resins could be found.
PREPARATION OF REAGENTS AND POLYMERIZATION,
PROCEDURE
Phthdic anhydride. Phthalic anhydride (Eastman Organic Chemicals) $ was dissolved in hot benzene, the solution filtered to remove undissolved o-phthalic acid, and the filtrate cooled to obtain recrystallized o-phthalic anhydride, m.p. 131-131.5OC.
Maleic anhydride. Maleic anhydride (Eastman Organic Chemicals) was distilled at 49 mm. The main cut melted at 52.0-52.5OC.
Hexahydrophthalic anhydride. Hexahydrophthalic anhydride (National Aniline) was distilled at 4 nun. pressure under nitrogen, and the portion boiling at 122OC. was used for subsequent experiments.