Synthesis and characterization of new aliphatic polyesters containing dihydronaphthofuro[3,2-d]furan moiety

Abstract

A dihydronaphthofuro[3,2-d]furan containing diol monomer, viz., 2,13-dihydroxy[7a,14c] dihydro naphtho[2,1-b]naphtho[1′,2′:4,5]furo[3,2-d] furan (DDNF) was synthesized in high yield and purity through the condensation of commercially available 2,7-dihydroxynaphthalene with glyoxal at room temperature. It was used as a new monomer for the synthesis of a series of novel dihydronaphthofuro-containing aliphatic polyesters by interfacial polycondensation method. Optimal conditions for polyesterification were obtained via study of the model compounds. The diol monomer and model compound were fully characterized by infrared, nuclear magnetic resonance (NMR), mass spectroscopies, and elemental analysis. Polyesters derived from DDNF and four aliphatic diacid chlorides had inherent viscosities ranging from 0.36 to 0.51 dL g−1. The chemical structure of the polymers was characterized by Fourier transform infrared, NMR spectroscopies and elemental analysis. The physical properties of the polymers were studied. The glass transition temperature was in the range of 89–118 °C. All the new polymers showed good thermal stability and very good solubility in most organic solvents.