Epoxy

12/06/2024, 21:12 Epoxy - Wikipedia
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 A syringe of "5-minute" epoxy glue,
containing separate compartments
group is an oxirane.
for the epoxy resin and the hardener
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
Structure of the epoxide group, a
with favorable mechanical properties and high thermal and
reactive functional group present in
chemical resistance. Epoxy has a wide range of applications, all epoxy resins
including metal coatings, composites,[2] 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[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 from compounds 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. In 1946, Sylvan Greenlee, working for the
Devoe & Raynolds Company (now part of Hexion Inc.[11]), patented resin derived from bisphenol-
A and epichlorohydrin.[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-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.
https://en.wikipedia.org/wiki/Epoxy 1/21
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.
Coupling reaction of a hydroxy
The other production route for epoxy resins is the conversion of group with epichlorohydrin, followed
aliphatic or cycloaliphatic alkenes with peracids:[13][14] In by dehydrohalogenation
contrast to glycidyl-based epoxy resins, this production of such
epoxy monomers does not require an acidic hydrogen atom but
an aliphatic double bond.
Synthesis of an epoxide by use of a
The epoxide group is also sometimes referred to as an oxirane peracid
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
ether
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:
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 Structure of bisphenol-A diglycidyl
the molecular weight achieved. This route of synthesis is known ether epoxy resin: n denotes the
as the "taffy" process. The usual route to higher molecular number of polymerized subunits and
weight epoxy resins is to start with liquid epoxy resin (LER) is typically in the range from 0 to 25
and add a calculated amount of 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 General structure of epoxyphenol
high crosslink 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
Structural formula of 3,4-
(once cured) good weather resistance, low dielectric constants
Epoxycyclohexylmethyl-3’,4’-
epoxycyclohexane carboxylate and high Tg. However, aliphatic epoxy resins polymerize very
slowly at room temperature, so higher 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]
The induced stresses 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
Structure of a cured epoxy glue. The
produces the qualities of the substance such as resistance,
triamine hardener is shown in red,
durability, versatility, and adhesion. In principle, any molecule the resin in black. The resin's
containing a reactive hydrogen may react with the epoxide epoxide groups have reacted with
groups of the epoxy resin. Common classes of hardeners for the hardener and are not present
epoxy resins include amines, acids, acid anhydrides, phenols, anymore. The material is highly
alcohols and thiols. Relative reactivity (lowest first) is crosslinked and contains many OH
groups, which confer adhesive
approximately in the order: phenol < anhydride < aromatic
properties
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
network with incomplete polymerisation, and thus reduced mechanical, chemical and heat
resistance. Cure temperature should typically attain the glass transition temperature (Tg) of the
fully cured network in order to achieve maximum properties. Temperature is sometimes increased
in a step-wise fashion to control the rate of curing and prevent excessive heat build-up from the
exothermic reaction.
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. The most widely used accelerator is 2,4,6-
Tris(dimethylaminomethyl)phenol.[31][32]
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
Epoxy resins may be thermally cured with anhydrides to create polymers Structure of TETA, a
with significant property retention at elevated temperatures for extended typical hardener. The
periods of time. Reaction and subsequent crosslinking occur only after amine (NH2) groups
react with the epoxide
opening of the anhydride ring, e.g. by secondary hydroxyl groups in the
groups of the resin
epoxy resin. Homopolymerization may also occur between epoxide and
during polymerisation.
hydroxyl groups. 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.[33]
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.[34]
The applications include coatings, adhesives[35][36] 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.[37]
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.[38]
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.[39]
Rubber toughening is a key technology used for toughening.[40][41]
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.[42] Epoxy coatings have also been used in drinking water
applications.[43] Epoxy coatings find much use to protect mild and other steels due to their
excellent protective properties.[44]
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) [45] and later in 1986 (high-intensity light aging).[46]
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.[47] 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.[48]
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
Special epoxy is strong enough to
strength bonds are required. Epoxy adhesives can be developed
withstand the forces between a
to suit almost any application. They can be used as adhesives
surfboard fin and the fin mount. This
for wood, metal, glass, stone, and some plastics. They can be epoxy is waterproof and capable of
made flexible or rigid, transparent or opaque/colored, fast curing underwater. The blue-
setting or slow setting. Epoxy adhesives are better in heat and coloured epoxy on the left is still
chemical resistance than other common adhesives. In general, undergoing curing
epoxy adhesives cured with heat will be more heat- and chemical-resistant than those cured at
room temperature. The strength of epoxy adhesives is degraded at temperatures above 350 °F
(177 °C).[49]
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.[50] 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.[51]
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 An epoxy encapsulated hybrid
circuit board—an "FR-4 board"—is a sandwich of layers of glass circuit on a printed circuit board.
cloth bonded into a composite by an epoxy resin. 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
The dark lump of epoxy in the
dispensing. 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.[52] 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.[53]
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.[54] 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.[55]
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.[56]
Biology
Water-soluble epoxies such as Durcupan[57][58] are commonly used for embedding electron
microscope samples in plastic so they may be sectioned (sliced thin) with a microtome and then
imaged.[59]
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.[60] It is also used in jewelry, as a doming resin for
decorations and labels, and in decoupage type applications for art, countertops, and tables.[61] 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[62]
and into various other design styles, including industrial, rustic, and even eclectic. It has been used
and studied for art and historic structure preservation.[63][64][65]
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 [51] 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.[66][67][68][69] Waterborne epoxy paints have been
around since the 1970s and research is ongoing.[70] 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.[71] Other work is ongoing to produce epoxy
and epoxy based coatings from recycled raw materials including PET bottles.[72] Monomers for
epoxy resins can be derived from several different biomass sources.[73]
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.[74] 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.[75] 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.[76] Safe disposal also needs considering but usually involves deliberate curing to produce
solid rather than liquid waste.[77]
See also
Pollution
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dcat.org/issn/0039-3630). JSTOR 1506076 (https://www.jstor.org/stable/1506076).
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1971. ISSN 0044-9466 (https://www.worldcat.org/issn/0044-9466). JSTOR 27670051 (https://w
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External links
Epoxy Resin Systems (https://www.cdph.ca.gov/Programs/CCDPHP/DEODC/OHB/HESIS/CD
PH%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
Massingill, J. L.; Bauer, R. S. (2000-01-01). "Epoxy Resins" (https://www.sciencedirect.com/sci
ence/article/pii/B9780080434179500234). In Craver, Clara D.; Carraher, Charles E. (eds.).
Applied Polymer Science: 21st Century. Oxford: Pergamon. pp. 393–424. doi:10.1016/b978-
008043417-9/50023-4 (https://doi.org/10.1016%2Fb978-008043417-9%2F50023-4).
ISBN 978-0-08-043417-9. Retrieved 2023-12-20.
Paul F. Bruins, ed. (1968). Epoxy resin technology (https://www.worldcat.org/oclc/182890).
New York: Interscience Publishers. 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: Noyes Publications.
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/ami
nes/#:~:text=The%20amine%20functional%20group%20contains,by%20a%20carbon-containin
g%20substituent.&text=Amine%20groups%20bonded%20to%20an,are%20known%20as%20a
romatic%20amines.). courses.lumenlearning.com. Retrieved 2021-07-22.
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12/06/2024, 21:12 Epoxy - Wikipedia

Reaction of polyepoxides with themselves or with

Di- and polyols lead to glycidyl ethers. Dicarboxylic acids such

In this two-stage reaction, epichlorohydrin is first added to

A product comprising a few repeat units (n = 1 to 2) is a

Increasing the ratio of bisphenol A to epichlorohydrin during

and add a calculated amount of bisphenol A and then a catalyst

Cycloaliphatic epoxides contain one or more aliphatic rings in

reaction and in some cases produces sufficient heat to cause

Curing may be achieved by reacting an epoxy with itself

While some epoxy resin/ hardener combinations will cure at

Paints and coatings

Industrial tooling and composites

Wind turbine technology composites

Electrical systems and electronics

Flexible epoxy resins are used for potting transformers and

Petroleum & petrochemical

Consumer and marine applications

Renewable, recycled, waterborne and biobased epoxy

OCLC 311631322 (https://www.worldcat.org/oclc/311631322).

Retrieved from "https://en.wikipedia.org/w/index.php?title=Epoxy&oldid=1227559192"

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