Editing Epoxy (section)

=== Amines ===

Polyfunctional primary amines form an important class of epoxy hardeners. Primary amines undergo an [[addition reaction]] with the epoxide group to form a hydroxyl group and a secondary amine. The secondary amine can further react with an epoxide to form a tertiary amine and an additional hydroxyl group. Kinetic studies have shown the reactivity of the primary amine to be approximately double that of the secondary amine. Use of a difunctional or polyfunctional amine forms a three-dimensional cross-linked network.
Aliphatic, cycloaliphatic and aromatic amines are all employed as epoxy hardeners. Amine type hardeners will alter both the processing properties (viscosity, reactivity) and the final properties (mechanical, temperature and heat resistance) of the cured copolymer network. Thus amine structure is normally selected according to the application. Overall reactivity potential for different hardeners can roughly be ordered; aliphatic amines > cycloaliphatic amines > aromatic amines, though aliphatic amines with steric hindrance near the amino groups may react as slowly as some of the aromatic amines. Slower reactivity allows longer working times for processors. Temperature resistance generally increases in the same order, since aromatic amines form much more rigid structures than aliphatic amines. Aromatic amines were widely used as epoxy resin hardeners, due to the excellent end properties when mixed with a parent resin. Over the past few decades concern about the possible adverse health effects of many aromatic amines has led to increased use of aliphatic or cycloaliphatic amine alternatives. Amines are also blended, adducted and reacted to alter properties and these amine resins are more often used to cure epoxy resins than a pure amine such as TETA. Increasingly, water-based [[polyamine]]s are also used to help reduce the toxicity profile among other reasons.{{citation needed|date=March 2021}}
[[File:N1,N1'-(ethane-1,2-diyl)bis(ethane-1,2-diamine) 200.svg|thumb|150px|Structure of [[Triethylenetetramine|TETA]], a typical hardener. The amine (NH2) groups react with the epoxide groups of the resin during polymerisation.]]