Epoxy

Epoxy is the family of basic components or cured end products of epoxy resins. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. The epoxide functional group is also collectively called epoxy. The IUPAC name for an epoxide group is an oxirane.

Epoxy resins may be reacted (cross-linked) either with themselves through catalytic homopolymerisation, or with a wide range of co-reactants including polyfunctional amines, acids (and acid anhydrides), phenols, alcohols and thiols (sometimes called mercaptans). These co-reactants are often referred to as hardeners or curatives, and the cross-linking reaction is commonly referred to as curing.

Reaction of polyepoxides with themselves or with polyfunctional hardeners forms a thermosetting polymer, often with favorable mechanical properties and high thermal and chemical resistance. Epoxy has a wide range of applications, including metal coatings, composites, use in electronics, electrical components (e.g. for chips on board), LEDs, high-tension electrical insulators, paintbrush manufacturing, fiber-reinforced plastic materials, and adhesives for structural and other purposes.

The health risks associated with exposure to epoxy resin compounds include contact dermatitis and allergic reactions, as well as respiratory problems from breathing vapor and sanding dust, especially from compounds not fully cured.

Condensation of epoxides and amines was first reported and patented by Paul Schlack of Germany in 1934. Claims of discovery of bisphenol-A-based epoxy resins include Pierre Castan in 1943. Castan's work was licensed by Ciba, Ltd. of Switzerland, which went on to become one of the three major epoxy resin producers worldwide. In 1946, Sylvan Greenlee, working for the Devoe & Raynolds Company (now part of Hexion Inc.), patented resin derived from bisphenol-A and epichlorohydrin.

Most of the commercially used epoxy monomers are produced by the reaction of a compound with acidic hydroxy groups and epichlorohydrin. First a hydroxy group reacts in a coupling reaction with epichlorohydrin, followed by dehydrohalogenation. Epoxy resins produced from such epoxy monomers are called glycidyl-based epoxy resins. The hydroxy group may be derived from aliphatic diols, polyols (polyether polyols), phenolic compounds or dicarboxylic acids. Phenols can be compounds such as bisphenol A and novolak. Polyols can be compounds such as 1,4-butanediol. Di- and polyols lead to glycidyl ethers. Dicarboxylic acids such as hexahydrophthalic acid are used for diglycide ester resins. Instead of a hydroxy group, also the nitrogen atom of an amine or amide can be reacted with epichlorohydrin.

The other production route for epoxy resins is the conversion of aliphatic or cycloaliphatic alkenes with peracids: In contrast to glycidyl-based epoxy resins, this production of such epoxy monomers does not require an acidic hydrogen atom but an aliphatic double bond.

The epoxide group is also sometimes referred to as an oxirane group.