In the study of polymerization behavior of 1,3-dioxolane derivatives, 2-phenyl-7-ethoxy-8-cyano-1,3,6-trioxaspiro[4,5]dec-7-ene(PEC-1,3,6-TOSDE) was prepared and its polymerization behavior was investigated.
PEC-1,3,6-TOSDE was prepared from 2-phenyl-4-methylene-1,3-dioxolane and ethyl α-cyano acrylate by the Diels-Alder reaction. PEC-1,3,6-TOSDE was readily polymerized by various cationic initiators in high conversion and the obtained polymers had linear chain structure resulting from double ring-opening and the structure was confirmed by NMR and IR. PEC-1,3,6-TOSDE decomposed around 300℃ as determined by TGA and exhibited a glass transition at 90℃. Volume change during the polymerization of PEC-1,3,6-TOSDE was also investigated. PEC-1,3,6-TOSDE showed small volume shrinkge during the polymerization under various conditions except the polymerization with $WCl_6$ at 0℃. In this case 4.6% of volume expansion was observed.
