The synthesis of 9–10 Dibromo stearic acid glycidyl methacrylate and its use in vinyl ester resins

Abstract

AbstractIn this study, 9–10 dibromo stearic acid glycidyl methacrylate (Di‐BrSAGMA) was synthesized from oleic acid and used as a replacement for styrene in vinyl ester (bisphenol A type VE (VE 828) and Novalac type VE (VE160)) to introduce fire retardance to these systems and to decrease the volatile organic compound (VOC) emissions caused by styrene. When the Di‐BrSAGMA was used as the comonomer, these resins exhibited too high viscosities, reduced modulus and glass transition temperature (Tg) values compared to those of the styrene based systems. Thus, the Di‐BrSAGMA was used in the presence of styrene in these resins. The viscosities of the resins with various Di‐BrSAGMA contents were determined and the modulus and the Tg values of the resulting polymers were measured via dynamic mechanical analysis (DMA) to determine the ideal formulations for each resin system. Similar analysis was performed, with similar oleic acid glycidyl methacrylate (OAGMA) contents, to determine the effect of the introduction of the bromine groups onto the network. Reactive diluent blends of the fatty acid based monomers with styrene, at styrene contents as low as 15–20 wt % at 35–45 wt % total comonomer content, in VE formulations were shown to have processable viscosities for liquid molding processes, and modulus and Tg values that are comparable to those of the commercial VE‐styrene systems. The effect of the replacement of styrene by the Di‐BrSAGMA monomer on the thermal degradation behavior of the VE 828 and VE 160 networks was also explored by thermal gravimetric analysis (TGA). © 2007 Wiley Periodicals, Inc. J Appl Polym Sci 2007