Low dielectric thermoset. IV. Synthesis and properties of a dipentene‐containing cyanate ester and its copolymerization with bisphenol A dicyanate ester

Abstract

AbstractA 2,6‐dimethylphenol‐dipentene dicyanate ester (DPCY) was synthesized from the reaction of 2,6‐dimethylphenol‐dipentene adduct and cyanogen bromide. The proposed structure was confirmed by Fourier transform infrared (FTIR), elemental analysis, mass, and nuclear magnetic resonance (NMR) spectra. DPCY was then cured by itself or cured with bisphenol A dicyanate ester (BADCY). Thermal properties of cured epoxy resins were studied using differential scanning calorimetry (DSC), dynamic mechanical analysis (DMA), dielectric analysis (DEA), and thermogravimetric analysis (TGA). These data are compared with those of BADCY. The cured DPCY exhibits a lower dielectric constant (2.61 at 1 MHz), dissipation factor (29.3 mU at 1 MHz), thermal stability (5% degradation temperature and char yield are 429 °C and 17.64%, respectively), glass transition temperature (246 °C by TMA and 258 °C by DMA), coefficient of thermal expansion (33.6 ppm before Tg and 134.1 ppm after Tg), and moisture absorption (0.95% at 48 h) than those of BADCY, but higher moduli (5.12 GPa at 150 °C and 4.60 GPa at 150 °C) than those of the bisphenol A system. The properties of cured cocyanate esters lie between cured BADCY and DPCY, except for moduli. Moduli of some cocyanate esters are even higher than those of cured BADCY and DPCY. A positive deviation from the Fox equation was observed for cocyanate esters. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 3986–3995, 2004