Novel copolyesters containing naphthalene structure. I. From bis(hydroxyalkyl)naphthalate and bis[4-(2-hydroxyethoxy)aryl] compounds

Abstract

Copolyesters containing naphthalene structure were synthesized from bis(hydroxyethyl)naphthalate (BHEN) or bis(hydroxybutyl)naphthalate (BHBN) and various aralkyloxy diols. The starting bis[4-(2-hydroxyethoxy)aryl] compounds were derived from a nucleophilic substitution of various bisphenols with ethylene carbonate in the presence of KI. Copolyesters having intrinsic viscosities of 0.45-0.60 dL/g were obtained by the melt polycondensation in the presence of metallic catalysts. The effect of reaction temperature and time on the formation of copolyesters were investigated to obtain an optimum condition for copolyesters manufacturing. Most copolyesters have better solubilities than polyethylene naphthalate (PEN) or polybutylene naphthalate (PBN) in aprotic solvents, such as N-methyl-2-pyrrolidone or m-cresol. The thermal properties of the copolyesters were investigated by the differential scanning calorimetry (DSC) and thermal gravimetric analysis (TGA). Glass transition temperatures (T g ) of copolyesters result from BHEN were in the range of 90-141°C, and 10% weight loss in nitrogen were all above 460°C. Another series of copolyesters result from BHBN have T g in the range of 75-135°C, and 10% weight loss in nitrogen of over 420°C.