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

Abstract

In 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 (T g ) 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 T g 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 T g 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).

From the synthesis and characterization of methacrylated fatty acid based precursors to shape memory polymers

“…The resulting adducts of the reaction of GMA and fatty acids will be mostly monomers, which will have a vinyl group, a hydroxyl group and an alkenyl double bond if the starting fatty acid is unsaturated . This type of reaction–addition synthesis has been used to produce vegetable oil based polyols with high hydroxyl equivalent weight, methacrylated fatty acid monomers to be used as diluent in vinyl ester based polymers, triglyceride based thermosetting resins and as one of the components for emulsion paints to improve the emulsion film property . Moreover, this synthesis route can also be applied to modify saturated fatty acids like lauric one, with the additional advantage of adding to it terminal unsaturations that can be further polymerized by free radical polymerization, for example.…”

Replacement of styrene with acrylated epoxidized soybean oil in an unsaturated polyester resin from propylene glycol and maleic anhydride

“…Methacrylates from reactions of glycidyl methacrylate and various fatty acids have been investigated as styrene replacements in vinyl ester resins. However, the complete replacement of styrene was found to result in high resin viscosity and inferior mechanical properties of the cured resins …”

The use of acrylated fatty acid methyl esters as styrene replacements in triglyceride‐based thermosetting polymers

“…Researchers have been working in recent years on the replacement of styrene in vinyl ester and unsaturated polyesters resins [26][27][28]. Methacrylated fatty acids (MFA) were prepared by reacting different types of fatty acid with glycidyl methacylate.…”