The most common epoxy resins are based on reacting epichlorohydrin (ECH) with bisphenol A, resulting in a different chemical substance known as bisphenol A diglycidyl ether (commonly known as BADGE or DGEBA). Bisphenol A-based resins are the most widely commercialised resins but also other bisphenols are analogously reacted with epichlorohydrin, for example Bisphenol F.
In this two-stage reaction, epichlorohydrin is first added to bisphenol A (bis(3-chloro-2-hydroxy-propoxy)bisphenol A is formed), then a bisepoxide is formed in a condensation reaction with a stoichiometric amount of sodium hydroxide. The chlorine atom is released as sodium chloride (NaCl) and the hydrogen atom as water.
Higher molecular weight diglycidyl ethers (n ≥ 1) are formed by the reaction of the bisphenol A diglycidyl ether formed with further bisphenol A, this is called prepolymerization:
Synthesis of bisphenol-A-diglycidyl ether with a high molar mass
A product comprising a few repeat units (n = 1 to 2) is a viscous, clear liquid; this is called a liquid epoxy resin. A product comprising more repeating units (n = 2 to 30) is at room temperature a colourless solid, which is correspondingly referred to as solid epoxy resin.
Instead of bisphenol A, other bisphenols (especially bisphenol F) or brominated bisphenols (e. g. tetrabromobisphenol A) can be used for the said epoxidation and prepolymerisation. Bisphenol F may undergo epoxy resin formation in a similar fashion to bisphenol A. These resins typically have lower viscosity and a higher mean epoxy content per gram than bisphenol A resins, which (once cured) gives them increased chemical resistance.
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