Synthesis and characterization of naphthoxazine functional poly(-caprolactone)



Baris Kiskan, Yusuf Yagci


A novel naphthoxazine ring-containing poly(e-caprolacton) (PCL) was synthesized and characterized.  For this purpose, first hydroxyl functional naphthoxazine, namely 2-(1H-naphtho[1,2-e][1,3]oxazin-2-yl)-ethanol (N-a-OH) was prepared by the reaction of 2-naphthol, ethanolamine and paraformaldehyde either in bulk or in dioxane as solvent at 110 ºC. Subsequently, N-a-OH was used as the coinitiator for the stannous-2-ethylhexanoate (Sn(Oct)2) catalyzed living ring-opening polymerization of e-caprolactone. The GPC, IR, 1H-NMR, UV, and fluoroscence spectroscopic studies revealed that low-polydispersity PCL with naphthoxazine functionality at the end of the chain was obtained. The resulting PCL macromonomer undergoes thermal curing in the presence of low molar mass benzoxazine (P-a) at various temperatures with the formation of thermosets having PCL segments. 

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