Synthesis and properties of novel poly(hydroxyurethane) from difunctional alicyclic carbonate and m-xylylenediamine and its possibility as gas barrier materials

摘要

Poly(hydroxyurethane) was synthesized by polyaddition of difunctional alicyclic carbonate (DCHC) and m-xylylenediamine (mXDA), and its oxygen transmittance rate was examined. DCHC was prepared from industrially available difunctional alicyclic epoxide, 3',4'-epoxycyclohexylmethyl 3,4-epoxycyclohexane carboxylate (CEL2021P), by insertion of carbon dioxide using N-methyltetrahydroprimidine as a promoter and tetrabutylammonium bromide as a catalyst. Poly(hydroxyurethane), poly(DCHC-mXDA) (M (n) = 2600, M (w) = 5700 GPC relative to polystyrene standards), was obtained by heating DCHC and mXDA in N,N-dimethylacetamide at 100 A degrees C. The obtained polymer was thermally stable up to 220 A degrees C, and exhibited good processability in film preparation. The oxygen transmission rate of the polymer was found to be 127 cm(3)/m(2) day atm at 5 mu m film thickness laminated with polypropylene films, indicating its relatively high gas barrier property.