PREPARATION AND CHARACTERIZATION OF POLYOXETANE RESINS HAVING A PRIMARY AMINO GROUP AT THE SIDE CHAIN-END THROUGH MODERATELY LONG SPACER ARMS

Uncross- and cross-linked polyoxetanes having a pendant hydrophilic pr imary amino group at the terminal of the -CH2O(CH2)(n)- spacers, where n=4 and 6, were prepared. Their prepolymers were obtained by the BF3- initiated cationic ring-opening polymerization of oxetanes having the corresponding pendant phthalimido group at the C-3 position of the oxe tane ring. In this polymerization a bisoxetane or an oxetane having th e hydrophobic pendant was used as a cross-linking agent or a comonomer modifying the degree of hydrophilicity. The pendant phthalimide of th e prepolymers was reduced with hydrazine in ethanol at 40 degrees C to give the pendant amine of the product polymers. The characterization of the phthalimide- and amine-containing polyoxetanes was also perform ed to know their structures and qualities. The analogous oxetane with the phthalimidomethyl pendant at the C-3 position gave a tricyclic pro duct via an intramolecular nucleophilic attack of the phthalimido oxyg en atom on the methylene carbon atom of the oxetane ring.