Coordinative polymerization of p-substituted phenyl glycidyl ethers, 1. Effect of electron-donating groups

A series of p-substituted glycidyl phenyl ethers

1 IUPAC nomenclature: 2,3-epoxypropyl phenyl ether.

with electron donor groups was prepared using a multistep synthetic method. These compounds were polymerized using four of the most common aluminium-based coordinative initiators, (C₂H₅)₃Al/H₂O (the Vandenberg catalyst), (C₂H₅)₃Al/CH₃COCH₂COCH₃/H₂O (the Vandenberg chelate catalyst), [(CH₃)₂CHO&]₂Al? O? Zn? O? Al[OCH(CH₃)₂]₂ (the Teyssié catalyst) and [(CH₃)₂CHO]₃AV/ZnCI₂ (the Price catalyst), all with different Lewis acid character. The influence of the electron-donor group on the characteristics and conversion was studied. Generally speaking, both the Vandenberg and the Teyssié catalysts yield mostly an insoluble polymer fraction, whereas the Price catalyst was shown to be the most stereoselective catalyst. Moreover, the Vandenberg chelate catalyst gave the highest molecular weight, the Price catalyst the lowest. Thermal characteristics of polymers were studied by means of differential thermal analysis to obtain glass transition temperatuures, melting temperatures and fusion enthalpies.