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.[1] The IUPAC name for an epoxide group is an oxirane. A syringe of "5-minute" epoxy glue,
containing separate compartments
Epoxy resins may be reacted (cross-linked) either with themselves for the epoxy resin and the hardener
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,[2] use in electronics, electrical components (e.g. for Structure of the epoxide group, a
chips on board ), LEDs, high-tension electrical insulators, reactive functional group present in
paintbrush manufacturing, fiber-reinforced plastic materials, and all epoxy resins
adhesives for structural[3] and other purposes.[4][5]

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 when not fully
cured.[6][7][8]

History
Condensation of epoxides and amines was first reported and patented by Paul Schlack of Germany in
1934.[9] Claims of discovery of bisphenol-A-based epoxy resins include Pierre Castan[10] 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. Ciba's epoxy business was spun off as Vantico in the late 1990s, which was
subsequently sold in 2003 and became the Advanced Materials business unit of Huntsman Corporation of
the United States. In 1946, Sylvan Greenlee, working for the Devoe & Raynolds Company, patented resin
derived from bisphenol-A and epichlorohydrin.[11] Devoe & Raynolds, which was active in the early days
of the epoxy resin industry, was sold to Shell Chemical; the division involved in this work was eventually
sold, and via a series of other corporate transactions is now part of Hexion Inc.[12]

Chemistry
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-
Coupling reaction of a hydroxy group
based epoxy resins. The hydroxy group may be derived from
with epichlorohydrin, followed by
aliphatic diols, polyols (polyether polyols), phenolic compounds or
dehydrohalogenation
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:[13][14] In contrast
to glycidyl-based epoxy resins, this production of such epoxy Synthesis of an epoxide by use of a
monomers does not require an acidic hydrogen atom but an peracid
aliphatic double bond.

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

Bisphenol-based

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
Synthesis of bisphenol A diglycidyl formed), then a bisepoxide is formed in a condensation reaction
ether 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:

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. Synthesis of bisphenol-A-diglycidyl
ether with a high molar mass
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.
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
Structure of bisphenol-A diglycidyl
achieved. This route of synthesis is known as the "taffy" process.
ether epoxy resin: n denotes the
The usual route to higher molecular weight epoxy resins is to start
number of polymerized subunits and
with liquid epoxy resin (LER) and add a calculated amount of is typically in the range from 0 to 25
bisphenol A and then a catalyst is added and the reaction heated to
circa 160 °C (320 °F). This process is known as
"advancement".[15] 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.

Epoxy resins are polymeric or semi-polymeric materials or an oligomer, 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 then require melting to enable processing.

An important criterion for epoxy resins is the Epoxy value which is connected to the epoxide group content.
This is expressed as the "epoxide equivalent weight", which is the ratio between the molecular weight of the
Rorar and the number of epoxide groups. This parameter is used to calculate the mass of co-reactant
(hardener) to use when curing epoxy resins. Epoxies are typically cured with stoichiometric or near-
stoichiometric quantities of hardener to achieve the best physical properties.

Novolaks

Novolaks are produced by reacting phenol with methanal

(formaldehyde). The reaction of epichlorohydrin and novolaks
produces novolaks with glycidyl residues, such as epoxyphenol
novolak (EPN) or epoxycresol novolak (ECN). These highly
viscous to solid resins typically carry 2 to 6 epoxy groups per
molecule. By curing, highly cross-linked polymers with high
temperature and chemical resistance but low mechanical flexibility
are formed due to the high functionality, and hence high crosslink
General structure of epoxyphenol
density of these resins.[13] novolak with n usually in the range
from 0 to 4. The compound is
present in the form of various
Aliphatic
constitutional isomers.

There are two common types of aliphatic epoxy resins: those

obtained by epoxidation of double bonds (cycloaliphatic epoxides
and epoxidized vegetable oils) and those formed by reaction with epichlorohydrin (glycidyl ethers and
esters).
 Cycloaliphatic epoxides contain one or more aliphatic rings in the
molecule on which the oxirane ring is contained (e.g. 3,4-
epoxycyclohexylmethyl-3',4'-epoxycyclohexane carboxylate). They
are produced by the reaction of a cyclic alkene with a peracid (see
above).[16] Cycloaliphatic epoxides are characterised by their
aliphatic structure, high oxirane content and the absence of chlorine,
which results in low viscosity and (once cured) good weather
Structural formula of 3,4- resistance, low dielectric constants and high Tg . However, aliphatic
Epoxycyclohexylmethyl-3’,4’- epoxy resins polymerize very slowly at room temperature, so higher
epoxycyclohexane carboxylate temperatures and suitable accelerators are usually required. Because
aliphatic epoxies have a lower electron density than aromatics,
cycloaliphatic epoxies react less readily with nucleophiles than
bisphenol A-based epoxy resins (which have aromatic ether groups). This means that conventional
nucleophilic hardeners such as amines are hardly suitable for crosslinking. Cycloaliphatic epoxides are
therefore usually homopolymerized thermally or UV-initiated in an electrophilic or cationic reaction. Due to
the low dielectric constants and the absence of chlorine, cycloaliphatic epoxides are often used to
encapsulate electronic systems, such as microchips or LEDs. They are also used for radiation-cured paints
and varnishes. Due to their high price, however, their use has so far been limited to such applications.[13]

Epoxidized vegetable oils are formed by epoxidation of unsaturated fatty acids by reaction with peracids. In
this case, the peracids can also be formed in situ by reacting carboxylic acids with hydrogen peroxide.
Compared with LERs (liquid epoxy resins) they have very low viscosities. If, however, they are used in
larger proportions as reactive diluents, this often leads to reduced chemical and thermal resistance and to
poorer mechanical properties of the cured epoxides. Large scale epoxidized vegetable oils such as
epoxidized soy and lens oils are used to a large extent as secondary plasticizers and cost stabilizers for
PVC.[13]

Aliphatic glycidyl epoxy resins of low molar mass (mono-, bi- or polyfunctional) are formed by the reaction
of epichlorohydrin with aliphatic alcohols or polyols (glycidyl ethers are formed) or with aliphatic
carboxylic acids (glycidyl esters are formed). The reaction is carried out in the presence of a base such as
sodium hydroxide, analogous to the formation of bisphenol A-diglycidyl ether. Also aliphatic glycidyl
epoxy resins usually have a low viscosity compared to aromatic epoxy resins. They are therefore added to
other epoxy resins as reactive diluents or as adhesion promoters. Epoxy resins made of (long-chain) polyols
are also added to improve tensile strength and impact strength.

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
lower 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. As aromaticity is not present in these
materials as it is in Bisphenol A and F resins, the UV stability is considerably improved.

Halogenated

Halogenated epoxy resins are admixed for special properties, in particular brominated and fluorinated epoxy
resins are used.[13]

Brominated bisphenol A is used when flame retardant properties are required, such as in some electrical
applications (e.g. printed circuit boards). The tetrabrominated bisphenol A (TBBPA, 2,2-bis(3,5-
dibromophenyl)propane) or its diglycidyl ether, 2,2-bis[3,5-dibromo-4-(2,3-epoxypropoxy)phenyl]propane,
can be added to the epoxy formulation. The formulation may then be reacted in the same way as pure
bisphenol A. Some (non-crosslinked) epoxy resins with very high molar mass are added to engineering
thermoplastics, again to achieve flame retardant properties.

Fluorinated epoxy resins have been investigated for some high performance applications, such as the
fluorinated diglycidether 5-heptafluoropropyl-1,3-bis[2-(2,3-epoxypropoxy)hexafluoro-2-propyl]benzene.
As it has a low surface tension, it is added as a wetting agent (surfactant) for contact with glass fibres. Its
reactivity to hardeners is comparable to that of bisphenol A. When cured, the epoxy resin leads to a
thermosetting plastic with high chemical resistance and low water absorption. However, the commercial use
of fluorinated epoxy resins is limited by their high cost and low Tg .

Diluents

Epoxy resins diluents are typically formed by glycidylation of aliphatic alcohols or polyols and also
aromatic alcohols.[17][18] The resulting materials may be monofunctional (e.g. dodecanol glycidyl ether),
difunctional (1,4-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.[19] They are rarely used alone, but are rather employed to modify (reduce)
the viscosity of other epoxy resins.[20] This has led to the term ‘modified epoxy resin’ to denote those
containing viscosity-lowering reactive diluents.[21] The use of the diluent does effect mechanical properties
and microstructure of epoxy resins.[22] Mechanical properties of epoxy resins are generally not improved by
use of diluents.[23] Biobased epoxy diluents are also available.[24]

Glycidylamine

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)-methane (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.

Curing
There are several dozen chemicals that can be used to cure epoxy, including amines, imidazoles, anhydrides
and photosensitive chemicals.[25] The study of epoxy curing is usually carried out by using Differential
scanning calorimetry.[26]

In general, uncured epoxy resins have only poor mechanical, chemical and heat resistance properties.[27]
However, good properties are obtained by reacting the linear epoxy resin with suitable curatives to form
three-dimensional cross-linked thermoset structures. This process is commonly referred to as curing or
gelation process.[28] Curing of epoxy resins is an exothermic reaction and in some cases produces sufficient
heat to cause thermal degradation if not controlled.[29] Curing does induce residual stress in epoxy systems
which have been studied.[30] They may be alleviated with flexibilisers.

Curing may be achieved by reacting an epoxy with itself (homopolymerisation) or by forming a copolymer
with polyfunctional curatives or hardeners. This curing is what produces the qualities of the substance such
as resistance, durability, versatility, and adhesion. In principle, any molecule containing a reactive hydrogen
may react with the epoxide groups of the epoxy resin. Common classes of hardeners for epoxy resins
include amines, acids, acid anhydrides, phenols, alcohols and thiols.
Relative reactivity (lowest first) is approximately in the order:
phenol < anhydride < aromatic amine < cycloaliphatic amine <
aliphatic amine < thiol.

While some epoxy resin/ hardener combinations will cure at

ambient temperature, many require heat, with temperatures up to
150 °C (302 °F) being common, and up to 200 °C (392 °F) for
some specialist systems. Insufficient heat during cure will result in a Structure of a cured epoxy glue. The
network with incomplete polymerisation, and thus reduced triamine hardener is shown in red,
mechanical, chemical and heat resistance. Cure temperature should the resin in black. The resin's
typically attain the glass transition temperature (Tg ) of the fully epoxide groups have reacted with the
cured network in order to achieve maximum properties. hardener and are not present
Temperature is sometimes increased in a step-wise fashion to anymore. The material is highly
control the rate of curing and prevent excessive heat build-up from crosslinked and contains many OH
the exothermic reaction. groups, which confer adhesive
properties
Hardeners which show only low or limited reactivity at ambient
temperature, but which react with epoxy resins at elevated
temperature are referred to as latent hardeners. When using latent hardeners, the epoxy resin and hardener
may be mixed and stored for some time prior to use, which is advantageous for many industrial processes.
Very latent hardeners enable one-component (1K) products to be produced, whereby the resin and hardener
are supplied pre-mixed to the end user and only require heat to initiate curing. One-component products
generally have shorter shelf-lives than standard 2-component systems, and products may require cooled
storage and transport.

The epoxy curing reaction may be accelerated by addition of small quantities of accelerators. Tertiary
amines, carboxylic acids and alcohols (especially phenols) are effective accelerators. Bisphenol A is a
highly effective and widely used accelerator, but is now increasingly replaced due to health concerns with
this substance.

Homopolymerisation

Epoxy resin may be reacted with itself in the presence of an anionic catalyst (a Lewis base such as tertiary
amines or imidazoles) or a cationic catalyst (a Lewis acid such as a boron trifluoride complex) to form a
cured network. This process is known as catalytic homopolymerisation. The resulting network contains
only ether bridges, and exhibits high thermal and chemical resistance, but is brittle and often requires
elevated temperature for the curing process, so finds only niche applications industrially. Epoxy
homopolymerisation is often used when there is a requirement for UV curing, since cationic UV catalysts
may be employed (e.g. for UV coatings).

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 polyamines are also used to help reduce the toxicity profile among other
reasons.

Anhydrides
Structure of TETA, a
Epoxy resins may be thermally cured with anhydrides to create polymers with
typical hardener. The
significant property retention at elevated temperatures for extended periods of
amine (NH2) groups
time. Reaction and subsequent crosslinking occur only after opening of the
react with the epoxide
anhydride ring, e.g. by secondary hydroxyl groups in the epoxy resin.
groups of the resin
Homopolymerization may also occur between epoxide and hydroxyl groups. during polymerisation.
The high latency of anhydride hardeners makes them suitable for processing
systems which require addition of mineral fillers prior to curing, e.g. for high
voltage electrical insulators. Cure speed may be improved by matching anhydrides with suitable
accelerators. For dianhydrides, and to a lesser extent, monoanhydrides, non-stoichiometric, empirical
determinations are often used to optimize dosing levels. In some cases, blends of dianhydrides and
monoanhydrides can improve metering and mixing with liquid epoxy resins.[31]

Phenols

Polyphenols, such as bisphenol A or novolacs can react with epoxy resins at elevated temperatures (130–
180 °C, 266–356 °F), normally in the presence of a catalyst. The resulting material has ether linkages and
displays higher chemical and oxidation resistance than typically obtained by curing with amines or
anhydrides. Since many novolacs are solids, this class of hardeners is often employed for powder coatings.

Thiols

Also known as mercaptans, thiols contain a sulfur which reacts very readily with the epoxide group, even at
ambient or sub-ambient temperatures. While the resulting network does not typically display high
temperature or chemical resistance, the high reactivity of the thiol group makes it useful for applications
where heated curing is not possible, or very fast cure is required e.g. for domestic DIY adhesives and
chemical rock bolt anchors. Thiols have a characteristic odour, which can be detected in many two-
component household adhesives.

Applications
The applications for epoxy-based materials are extensive and they are considered very versatile.[32] The
applications include coatings, adhesives[33][34] and composite materials such as those using carbon fiber
and fiberglass reinforcements (although polyester, vinyl ester, and other thermosetting resins are also used
for glass-reinforced plastic). The chemistry of epoxies and the range of commercially available variations
allows cure polymers to be produced with a very broad range of properties. They have been extensively
used with concrete and cementitious systems.[35] In general, epoxies are known for their excellent adhesion,
chemical and heat resistance, good-to-excellent mechanical properties and very good electrical insulating
properties. Many properties of epoxies can be modified (for example silver-filled epoxies with good
electrical conductivity are available, although epoxies are typically electrically insulating). Variations
offering high thermal insulation, or thermal conductivity combined with high electrical resistance for
electronics applications, are available.[36]

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 or final properties, or to
reduce cost. Use of blending, additives and fillers is often referred to as formulating.

All quantities of mix generate their own heat because the reaction is exothermic. Large quantities will
generate more heat and thus greatly increase the rate of the reaction and so reduce working time (pot-life).
So it is good practice to mix smaller amounts which can be used quickly to avoid waste and to be safer.
There are various methods of toughening them, as they can be brittle.[37] Rubber toughening is a key
technology used for toughening.[38][39]

Paints and coatings

Two part epoxy coatings were developed for heavy duty service on metal substrates and use less energy
than heat-cured powder coatings. These systems provide a tough, protective coating with excellent
hardness. One part epoxy coatings are formulated as an emulsion in water, and can be cleaned up without
solvents.

Epoxy coatings are often used in industrial and automotive applications since they are more heat resistant
than latex-based and alkyd-based paints. Epoxy paints tend to deteriorate, known as "chalking out", due to
UV exposure.[40] Epoxy coatings have also been used in drinking water applications.[41] Epoxy coatings
find much use to protect mild and other steels due to their excellent protective properties.[42]

Change in color, known as yellowing, is a common phenomenon for epoxy materials and is often of
concern in art and conservation applications. Epoxy resins yellow with time, even when not exposed to UV
radiation. Significant advances in understanding yellowing of epoxies were achieved by Down first in 1984
(natural dark aging) [43] and later in 1986 (high-intensity light aging).[44] Down investigated various room-
temperature-cure epoxy resin adhesives suitable for use in glass conservation, testing their tendency to
yellow. A fundamental molecular understanding of epoxy yellowing was achieved, when Krauklis and
Echtermeyer discovered the mechanistic origin of yellowing in a commonly used amine epoxy resin,
published in 2018.[45] They found that the molecular reason for epoxy yellowing was a thermo-oxidative
evolution of carbonyl groups in the polymeric carbon–carbon backbone via a nucleophilic radical attack.

Polyester epoxies are used as powder coatings for washers, driers and other "white goods". Fusion Bonded
Epoxy Powder Coatings (FBE) are extensively used for corrosion protection of steel pipes and fittings used
in the oil and gas industry, potable water transmission pipelines (steel), and concrete reinforcing rebar.
Epoxy coatings are also widely used as primers to improve the adhesion of automotive and marine paints
especially on metal surfaces where corrosion (rusting) resistance is important. Metal cans and containers are
often coated with epoxy to prevent rusting, especially for foods like tomatoes that are acidic. Epoxy resins
are also used for decorative flooring applications such as terrazzo flooring, chip flooring, and colored
aggregate flooring.

Epoxies have been modified in a variety of ways, including reacting with fatty acids derived from oils to
yield epoxy esters, which were cured the same way as alkyds. Typical ones were L8 (80% linseed) and D4
(40% dehydrated castor oil). These were often reacted with styrene to make styrenated epoxy esters, used as
primers. Curing with phenolics to make drum linings, curing esters with amine resins and pre-curing
epoxies with amino resins to make resistant top coats. Organic chains maybe used to hydrophobically
modify epoxy resins and change their properties. The effect of chain length of the modifiers has been
studied.[46]

Adhesives

Epoxy adhesives are a major part of the class of adhesives called

"structural adhesives" or "engineering adhesives" (that includes
polyurethane, acrylic, cyanoacrylate, and other chemistries.) These
high-performance adhesives are used in the construction of aircraft,
automobiles, bicycles, boats, golf clubs, skis, snowboards, and
other applications where high strength bonds are required. Epoxy
adhesives can be developed to suit almost any application. They Special epoxy is strong enough to
can be used as adhesives for wood, metal, glass, stone, and some withstand the forces between a
plastics. They can be made flexible or rigid, transparent or surfboard fin and the fin mount. This
opaque/colored, fast setting or slow setting. Epoxy adhesives are epoxy is waterproof and capable of
curing underwater. The blue-coloured
better in heat and chemical resistance than other common adhesives.
epoxy on the left is still undergoing
In general, epoxy adhesives cured with heat will be more heat- and
curing
chemical-resistant than those cured at room temperature. The
strength of epoxy adhesives is degraded at temperatures above
350 °F (177 °C).[47]

Some epoxies are cured by exposure to ultraviolet light. Such epoxies are commonly used in optics, fiber
optics, and optoelectronics.

Industrial tooling and composites

Epoxy systems are used in industrial tooling applications to produce molds, master models, laminates,
castings, fixtures, and other industrial production aids. This "plastic tooling" replaces metal, wood and other
traditional materials, and generally improves the efficiency and either lowers the overall cost or shortens the
lead-time for many industrial processes. Epoxies are also used in producing fiber-reinforced or composite
parts. They are more expensive than polyester resins and vinyl ester resins, but usually produce stronger and
more temperature-resistant thermoset polymer matrix composite parts. Machine bedding to overcome
vibrations is a use in the form of epoxy granite.

Wind turbine technology composites

Epoxy resins are used as bonding matrix along with glass or carbon fiber fabrics to produce composites
with very high strength to weight characteristics, allowing longer and more efficient rotor blades to be
produced.[48] In addition, for offshore and onshore wind energy installations, epoxy resins are used as
protective coatings on steel towers, base struts and concrete foundations. Aliphatic polyurethane top coats
are applied on top to ensure full UV protection, prolong operational lifetimes and lowering maintenance
costs. Electric generators, connected via the drivetrain with the rotor blades, convert mechanical wind
energy to usable electric energy, and rely on epoxies electrical insulation and high thermal resistance
properties. The same applies to transformers, bushings, spacers, and composites cables connecting the
windmills to the grid. In Europe, wind energy components account for the largest segment of epoxy
applications, about 27% of the market.[49]

Electrical systems and electronics

Epoxy resin formulations are important in the electronics industry,

and are employed in motors, generators, transformers, switchgear,
bushings, insulators, printed wiring boards (PWB), and
semiconductor encapsulants. Epoxy resins are excellent electrical
insulators and protect electrical components from short circuiting,
dust and moisture. In the electronics industry epoxy resins are the
primary resin used in overmolding integrated circuits, transistors
and hybrid circuits, and making printed circuit boards. The largest
volume type of circuit board—an "FR-4 board"—is a sandwich of
An epoxy encapsulated hybrid circuit
layers of glass cloth bonded into a composite by an epoxy resin.
on a printed circuit board.
Epoxy resins are used to bond copper foil to circuit board
substrates, and are a component of the solder mask on many circuit
boards.

Flexible epoxy resins are used for potting transformers and

inductors. By using vacuum impregnation on uncured epoxy,
winding-to-winding, winding-to-core, and winding-to-insulator air
voids are eliminated. The cured epoxy is an electrical insulator and
a much better conductor of heat than air. Transformer and inductor
hot spots are greatly reduced, giving the component a stable and
longer life than unpotted product.
The interior of a pocket calculator.
Epoxy resins are applied using the technology of resin dispensing.
The dark lump of epoxy in the center
covers the processor chip
Petroleum & petrochemical

Epoxies can be used to plug selective layers in a reservoir which are producing excessive brine. The
technique is named "water shut-off treatment".[28]

Consumer and marine applications

Epoxies are sold in hardware stores, typically as a pack containing separate resin and hardener, which must
be mixed immediately before use. They are also sold in boat shops as repair resins for marine applications.
Epoxies typically are not used in the outer layer of a boat because they deteriorate by exposure to UV light.
They are often used during boat repair and assembly, and then over-coated with conventional or two-part
polyurethane paint or marine-varnishes that provide UV protection.

There are two main areas of marine use. Because of the better mechanical properties relative to the more
common polyester resins, epoxies are used for commercial manufacture of components where a high
strength/weight ratio is required. The second area is that their strength, gap filling properties and excellent
adhesion to many materials including timber have created a boom in amateur building projects including
aircraft and boats.
Normal gelcoat formulated for use with polyester resins and vinylester resins does not adhere to epoxy
surfaces, though epoxy adheres very well if applied to polyester resin surfaces. "Flocoat" that is normally
used to coat the interior of polyester fibreglass yachts is also compatible with epoxies.

Epoxy materials tend to harden somewhat more gradually, while polyester materials tend to harden quickly,
particularly if a lot of catalyst is used.[50] The chemical reactions in both cases are exothermic.

While it is common to associate polyester resins and epoxy resins, their properties are sufficiently different
that they are properly treated as distinct materials. Polyester resins are typically low strength unless used
with a reinforcing material like glass fibre, are relatively brittle unless reinforced, and have low adhesion.
Epoxies, by contrast, are inherently strong, somewhat flexible and have excellent adhesion. However,
polyester resins are much cheaper.

Epoxy resins typically require a precise mix of two components which form a third chemical to get the
stated properties. Depending on the properties required, the ratio may be anything from 1:1 or over 10:1,
but in usually they must be mixed exactly. The final product is then a precise thermoset plastic. Until they
are mixed the two elements are relatively inert, although the 'hardeners' tend to be more chemically active
and should be protected from the atmosphere and moisture. The rate of the reaction can be changed by
using different hardeners, which may change the nature of the final product, or by controlling the
temperature.

By contrast, polyester resins are usually made available in a 'promoted' form, such that the progress of
previously-mixed resins from liquid to solid is already underway, albeit very slowly. The only variable
available to the user is to change the rate of this process using a catalyst, often Methyl-Ethyl-Ketone-
Peroxide (MEKP), which is very toxic. The presence of the catalyst in the final product actually detracts
from the desirable properties, so that small amounts of catalyst are preferable, so long as the hardening
proceeds at an acceptable pace. The rate of cure of polyesters can therefore be controlled by the amount and
type of catalyst as well as by the temperature.

As adhesives, epoxies bond in three ways: a) Mechanically, because the bonding surfaces are roughened; b)
by proximity, because the cured resins are physically so close to the bonding surfaces that they are hard to
separate; c) ionically, because the epoxy resins form ionic bonds at an atomic level with the bonding
surfaces. This last is substantially the strongest of the three.[51] By contrast, polyester resins can only bond
using the first two of these, which greatly reduces their utility as adhesives and in marine repair.

Construction applications

Epoxies have been researched and used for construction for a few decades.[52] Although they increase cost
of mortars and concrete when used as an additive, they enhance properties. Research is ongoing to
investigate the use of epoxies and other recycled plastics in mortars to enhance properties and recycle waste.
Densifying plastic materials such as PET and plastic bags and then using them to partially replace aggregate
and depolymerizing PET to use as a polymeric binder in addition to epoxy to enhance concrete are actively
being studied.[53]

Aerospace applications
In the aerospace industry, epoxy is used as a structural matrix material which is then reinforced by fiber.
Typical fiber reinforcements include glass, carbon, Kevlar, and boron. Epoxies are also used as a structural
glue. Materials like wood, and others that are 'low-tech' are glued with epoxy resin. Epoxies generally out-
perform most other resin types in terms of mechanical properties and resistance to environmental
degradation.[54]

Biology

Water-soluble epoxies such as Durcupan[55][56] are commonly used for embedding electron microscope
samples in plastic so they may be sectioned (sliced thin) with a microtome and then imaged.[57]

Art

Epoxy resin, mixed with pigment, may be used as a painting medium, by pouring layers on top of each
other to form a complete picture.[58] It is also used in jewelry, as a doming resin for decorations and labels,
and in decoupage type applications for art, countertops, and tables.[59] Its seamless and glossy finish, along
with its ability to be molded into various shapes, makes epoxy resin a favored choice for creating minimalist
and statement pieces in modern furniture design[60] and into various other design styles, including
industrial, rustic, and even eclectic. It has been used and studied for art and historic structure
preservation.[61][62][63]

Production
The global epoxy resin market was valued at approximately $8 billion in 2016. The epoxy resin market is
dominated by the Asia-Pacific region, which contributes 55.2% of the total market share. China is the major
producer and consumer globally, consuming almost 35% of the global resin production. The global market
is made up of approximately 50–100 manufacturers of basic or commodity epoxy resins and hardeners. In
Europe, about 323,000 tonnes of epoxy resin were manufactured in 2017 generating some €1,055 million
in sales. Germany [49] is the largest market for epoxy resins in Europe, followed by Italy, France, the UK,
Spain, the Netherlands and Austria.

These commodity epoxy manufacturers mentioned above typically do not sell epoxy resins in a form usable
to smaller end users, so there is another group of companies that purchases epoxy raw materials from the
major producers and then compounds (blends, modifies, or otherwise customizes) epoxy systems from these
raw materials. These companies are known as "formulators". The majority of the epoxy systems sold are
produced by these formulators and they comprise over 60% of the dollar value of the epoxy market. There
are hundreds of ways that these formulators can modify epoxies—by adding mineral fillers (talc, silica,
alumina, etc.), by adding flexibilizers, viscosity reducers, colorants, thickeners, accelerators, adhesion
promoters, etc. These modifications are made to reduce costs, to improve performance, and to improve
processing convenience. As a result, a typical formulator sells dozens or even thousands of formulations—
each tailored to the requirements of a particular application or market.

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).

Renewable, recycled, waterborne and biobased epoxy

As there is a general trend to renewable and "green" sources and greater use of biobased materials, research
is ongoing in the epoxy arena too.[64][65][66][67] Waterborne epoxy paints have been around since the
1970s and research is ongoing.[68] There is also movement to use waste as well as recycled raw materials
where possible. Waste granite filings are produced in the mining industry. Research is being done on
innovative solutions such as using waste granite powders in epoxy resins and designing binders for coatings
based on this.[69] Other work is ongoing to produce epoxy and epoxy based coatings from recycled raw
materials including PET bottles.[70]

Health risks
Liquid epoxy resins in their uncured state are mostly classed as irritant to the eyes and skin, as well as toxic
to aquatic organisms.[71] Solid epoxy resins are generally safer than liquid epoxy resins, and many are
classified non-hazardous materials. One particular risk associated with epoxy resins is sensitization. The risk
has been shown to be more pronounced in epoxy resins containing low molecular weight epoxy
diluents.[72] Exposure to epoxy resins can, over time, induce an allergic reaction. Sensitization generally
occurs due to repeated exposure (e.g. through poor working hygiene or lack of protective equipment) over a
long period of time. Allergic reaction sometimes occurs at a time which is delayed several days from the
exposure. Allergic reaction is often visible in the form of dermatitis, particularly in areas where the exposure
has been highest (commonly hands and forearms). Epoxy use is a main source of occupational asthma
among users of plastics.[73] Safe disposal also needs considering but usually involves deliberate curing to
produce solid rather than liquid waste.[74]

See also
Pollution

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External links
Epoxy Resin Systems (https://www.cdph.ca.gov/Programs/CCDPHP/DEODC/OHB/HESIS/
 CDPH%20Document%20Library/epoxy.pdf) (California Department of Public Health) Link
Updated 31 August 2021
The chemistry of epoxide (http://pslc.ws/macrog/epoxy.htm)
Methods of staining epoxy resin (https://profypainter.com/can-you-paint-on-resin)

Further reading
Epoxy resin technology (https://www.worldcat.org/oclc/182890). Paul F. Bruins, Polytechnic
Institute of Brooklyn. New York: Interscience Publishers. 1968. ISBN 0-470-11390-1.
OCLC 182890 (https://www.worldcat.org/oclc/182890).
Flick, Ernest W. (1993). Epoxy resins, curing agents, compounds, and modifiers : an
industrial guide (https://www.worldcat.org/oclc/915134542). Park Ridge, NJ. ISBN 978-0-
8155-1708-5. OCLC 915134542 (https://www.worldcat.org/oclc/915134542).
Lee, Henry (1967). Handbook of epoxy resins (https://www.worldcat.org/oclc/311631322).
Kris Neville ([2nd, expanded work] ed.). New York: McGraw-Hill. ISBN 0-07-036997-6.
OCLC 311631322 (https://www.worldcat.org/oclc/311631322).
"Amines | Introduction to Chemistry" (https://courses.lumenlearning.com/introchem/chapter/a
mines/#:~:text=The%20amine%20functional%20group%20contains,by%20a%20carbon-con
taining%20substituent.&text=Amine%20groups%20bonded%20to%20an,are%20known%20
as%20aromatic%20amines.). courses.lumenlearning.com. Retrieved 2021-07-22.

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