Epoxy compounds. VIII. Stereoregular and stereorandom polymerization of phenyl glycidyl ether with tertiary amines,and infrared spectra of poly(phenyl glycidyl ether)

Crystalline and amorphous polymers have been obtained from the polymerization of phenyl glycidyl ether in the presence of tertiary amines. The crystalline fraction is high melting and insoluble at room temperature. The amorphous fractions are soluble at room temperature and their molecular weights are found to be ～950 in benzene at 30°C. The yields of the crystalline fraction and the amorphous paste fraction decreased considerably with increasing the catalyst concentration and reaction temperature above 50°C. The yield of the liquid fraction, however, increased with increasing concentration of the catalyst and the reaction temperature. The x-ray diffraction analysis of the crystalline fraction shows that the fraction has 47–50% crystallinity and that its diffraction pattern is similar to that of poly(phenyl glycidyl ether) obtained by Noshay and Price. The infrared spectra of these fractions have been obtained in the region of 650–4000 cm.^?1. These data are compared with those of polystyrene and poly(styrene oxide) and are used to make an assignment of the normal modes of the poly(phenyl glycidyl ether) molecule. On the basis of analyses of polystyrene and poly(styrene oxide), and a study of the combination bands, it has been possible to make a fairly satisfactory assignment of all of the benzene ring fundamentals of the CH₂, CH, and skeletal modes.