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Epoxy Resin

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Definition

Epoxy Resin is a flexible and usually thermosetting resin made by copolymerization of an epoxide with another compound having two hydroxyl groups and used chiefly in coatings and adhesives - called also epoxy, which is an adhesive, plastic, paint, or other material made from a class of synthetic thermosetting polymers containing epoxide groups.

Overview

1916, in reference to certain chemical compounds, from epi- + first element of oxygen (epoxy- is used as a prefix in chemistry). Resins from them are used as powerful glues. Hence the verb meaning "to bond with epoxy" (1965).

Epoxy resins are low molecular weight pre-polymers or higher molecular weight polymers which normally contain at least two epoxide groups. The epoxide group is also sometimes referred to as a glycidyl or oxirane group.

A wide range of epoxy resins are produced industrially. The raw materials for epoxy resin production are today largely petroleum derived, although some plant derived sources are now becoming commercially available (e.g. plant derived glycerol used to make epichlorohydrin).

Epoxy resins are polymeric or semi-polymeric materials, and as such rarely exist as pure substances, since variable chain length results from the polymerisation reaction used to produce them. High purity grades can be produced for certain applications, e.g. using a distillation purification process. One downside of high purity liquid grades is their tendency to form crystalline solids due to their highly regular structure, which require melting to enable processing.

An important criterion for epoxy resins is the epoxide content. This is commonly expressed as the epoxide number, which is the number of epoxide equivalents in 1 kg of resin (Eq./kg), or as the equivalent weight, which is the weight in grammes of resin containing 1 mole equivalent of epoxide (g/mol). One measure may be simply converted to another:

Equivalent weight (g/mol) = 1000 / epoxide number (Eq./kg)

The equivalent weight or epoxide number is used to calculate the amount of co-reactant (hardener) to use when curing epoxy resins. Epoxies are typically cured with stoichiometric or near-stoichiometric quantities of curative to achieve maximum physical properties.

As with other classes of thermoset polymer materials, blending different grades of epoxy resin, as well as use of additives, plasticizers or fillers is common to achieve the desired processing and/or final properties, or to reduce cost. Use of blending, additives and fillers is often referred to as formulating.

Bisphenol A epoxy resin

Important epoxy resins are produced from combining epichlorohydrin and bisphenol A to give bisphenol A diglycidyl ethers.

Increasing the ratio of bisphenol A to epichlorohydrin during manufacture produces higher molecular weight linear polyethers with glycidyl end groups, which are semi-solid to hard crystalline materials at room temperature depending on the molecular weight achieved. As the molecular weight of the resin increases, the epoxide content reduces and the material behaves more and more like a thermoplastic. Very high molecular weight polycondensates (ca. 30 000 – 70 000 g/mol) form a class known as phenoxy resins and contain virtually no epoxide groups (since the terminal epoxy groups are insignificant compared to the total size of the molecule). These resins do however contain hydroxyl groups throughout the backbone, which may also undergo other cross-linking reactions, e.g. with aminoplasts, phenoplasts and isocyanates.

Bisphenol F epoxy resin

Bisphenol F may also undergo epoxidation in a similar fashion to bisphenol A. Compared to DGEBA, bisphenol F epoxy resins have lower viscosity and a higher mean epoxy content per gramme, which (once cured) gives them increased chemical resistance.

Novolac epoxy resin

Reaction of phenols with formaldehyde and subsequent glycidylation with epichlorohydrin produces epoxidised novolacs, such as epoxy phenol novolacs (EPN) and epoxy cresol novolacs (ECN). These are highly viscous to solid resins with typical mean epoxide functionality of around 2 to 6. The high epoxide functionality of these resins forms a highly crosslinked polymer network displaying high temperature and chemical resistance, but low flexibility.

Aliphatic epoxy resin

Aliphatic epoxy resins are typically formed by glycidylation of aliphatic alcohols or polyols. The resulting resins may be monofunctional (e.g. dodecanol glycidyl ether), difunctional (butanediol diglycidyl ether), or higher functionality (e.g. trimethylolpropane triglycidyl ether). These resins typically display low viscosity at room temperature (10-200 mPa.s) and are often referred to as reactive diluents. They are rarely used alone, but are rather employed to modify (reduce) the viscosity of other epoxy resins. This has led to the term 'modified epoxy resin' to denote those containing viscosity-lowering reactive diluents. A related class is cycloaliphatic epoxy resin, which contains one or more cycloaliphatic rings in the molecule (e.g. 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate). This class also displays low viscosity at room temperature, but offers significantly higher temperature resistance than the aliphatic epoxy diluents. However, reactivity is rather low compared to other classes of epoxy resin, and high temperature curing using suitable accelerators is normally required.

Glycidylamine epoxy resin

Glycidylamine epoxy resins are higher functionality epoxies which are formed when aromatic amines are reacted with epichlorohydrin. Important industrial grades are triglycidyl-p-aminophenol (functionality 3) and N,N',N,N'-tetraglycidyl-bis-(4-aminophenyl)-methan (functionality 4). The resins are low to medium viscosity at room temperature, which makes them easier to process than EPN or ECN resins. This coupled with high reactivity, plus high temperature resistance and mechanical properties of the resulting cured network makes them important materials for aerospace composite applications.






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