Material Properties

Mechanical Properties
Glass transition temperature (Tg)

120 - 130 C

Tensile strength

85 N/mm

Tensile Modulus

10,500 N/mm

Elongation at break

0.8%

Flexural strength

112 N/mm

Flexural Modulus

10,000 N/mm

Compressive Strength

190 N/mm

Coefficient of linear thermal expansion

34 10-6

Water absorption - 24 hours at 23C

5-10 mg (0.06-0.068%) ISO 62 (1980)

Thermal Properties
Thermal Shock

2000 cycles (90 sec. at 75 C, 90 sec. dwell, 90 sec. at 15C) No effect

Should not be subjected to dry-ice or liquid nitrogen.

Smoke Emission

Low Smoke Emission BS 6853 1999 App. D Clause d.8.4

Result Ao(on) 8.75, Ao(off) 10.41

Flammability

Class 0 as classified by the current Building Regulations

Thermal Decomposition

350 C

Radioactive Decontamination

BS 4247 Part 1 Test

Decontamination factor (geometric mean)

A5598

Deviation factor

1.25

Ease of decontamination classification

Excellent

Chemical Resistance of Epoxy Resin

Colours Available

Epoxy
From Wikipedia, the free encyclopedia

This article is about the thermoset plastic materials. For the chemical group, see epoxide.
[hide]This article has multiple issues. Please help improve it or discuss these issues

This article may contain an excessive amount of intricate detail that may only int
This article may be too technical for most readers to understand.

(February 2013)

A syringe of "5-minute" epoxy, containing separate compartments for each of the two components

Epoxy is the cured end product of epoxy resins, as well as a colloquial name for
the epoxide functional group. Epoxy is also a common name for a type of strong adhesive used for
sticking things together and covering surfaces,[1] typically two resins that need to be mixed together
before use.
Epoxy resins, also known as polyepoxides are a class of reactive prepolymers and polymers which
contain epoxide groups. 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. 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 strong mechanical properties as well as high temperature and chemical resistance. Epoxy
has a wide range of industrial applications, including metal coatings, use in electronic and electrical
components, high tension electrical insulators, fibre-reinforced plastic materials, and
structuraladhesives. Epoxy resin is employed to bind gutta percha in some root canal procedures.[2]
Popular consumer two-part epoxy adhesives for home, shop, and hobby are available in stores
ranging in a wide selection of properties, including slow vs. fast curing time, opaque vs. clear colors,
water-proof vs water-resistant, and flexible vs. rigid. A common misconception is that all epoxies are
waterproof, however many perhaps most are not recommended for long-term submersion (such
as flower vases) nor below the water line. Also, some epoxies bond better than others to different
materials even to different metals.
Contents

[hide]

1 Epoxy chemistry
o

1.1 Bisphenol A epoxy resin

1.2 Bisphenol F epoxy resin

1.3 Novolac epoxy resin

1.4 Aliphatic epoxy resin

1.5 Glycidylamine epoxy resin

2 Curing epoxy resins

o

2.1 Homopolymerisation

2.2 Amines

2.3 Anhydrides

2.4 Phenols

2.5 Thiols

3 History

4 Applications
o

4.1 Paints and coatings

4.2 Adhesives

4.3 Industrial tooling and composites

4.4 Electrical systems and electronics

4.5 Consumer and marine applications

4.6 Aerospace applications

4.7 Biology

4.8 Art

5 Industry

6 Health risks

7 Accidents

8 References

9 External links

Epoxy chemistry[edit]
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 disadvantage 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 characteristic of 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 grams 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)
required when curing epoxy resins. Epoxies are typically cured withstoichiometric or nearstoichiometric quantities of curative to achieve the best physical properties.
As with other classes of thermosetting 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[edit]

The most common and important class of epoxy resins is formed from reacting epichlorohydrin
with bisphenol A to form diglycidyl ethers of bisphenol A. The simplest resin of this class is formed
from reacting two moles of epichlorohydrin with one mole of bisphenol A to form the bisphenol A
diglycidyl ether (commonly abbreviated to DGEBA or BADGE). DGEBA resins are transparent
colourless-to-pale-yellow liquids at room temperature, with viscosity typically in the range of 5-15
Pa.s at 25 C. Industrial grades normally contain some distribution of molecular weight, since pure
DGEBA shows a strong tendency to form a crystalline solid upon storage at ambient temperature.

Structure of bisphenol-A diglycidyl ether epoxy resin: n denotes the number of polymerized subunits and is typically in the
range from 0 to 25

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[edit]

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 gram, which
(once cured) gives them increased chemical resistance.

Novolac epoxy resin[edit]

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. 100% solids hybrid novolac epoxy resin
systems have been developed that contain no solvents and no volatile or organic compounds. These
hybrid novolac epoxies have been documented to withstand up to 98% sulfuric acid.

Aliphatic epoxy resin[edit]

There are two types of aliphatic epoxy resins: glycidyl epoxy resins and cycloaliphatic epoxides.
Glycidyl epoxy resins are typically formed by the reaction of epichlorohydrin with aliphatic alcohols or
polyols to give glycidyl ethers or aliphatic carboxylic acids to give glycidyl esters. [3] This reaction is
normally done in the presence of an alkali, such as sodium hydroxide, to facilitate the
dehydrochlorination of the intermediate chlorohydrin. The resulting resins may be monofunctional
(e.g. dodecanol glycidyl ether), difunctional (diglycidyl ester of hexahydrophthalic acid), or higher
functionality (e.g. trimethylolpropane triglycidyl ether). These resins typically display low viscosity at
room temperature (10-200 mPa.s) and are often used as reactive diluents. As such, they are

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. However, they are also
used without other epoxide ingredients along with anhydride curing agents such as
hexahydrophthalic anhydride to make molded objects such as high voltage insulators. This is in fact
the main use of the diglycidyl esters.
The cycloaliphatic epoxides contain one or more cycloaliphatic rings in the molecule to which the
oxirane ring is fused (e.g. 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate). They are
formed by the reaction of cyclo-olefins with a peracid, such as peracetic acid. [4] This class also
displays low viscosity at room temperature, but offers significantly higher temperature resistance and
correspondingly better electrical properties at high temperatures to cured resins than the glycidyl
aliphatic epoxy resins. Another advantage is the complete absence of chlorine, since no
epichlorohydrin is used in the manufacturing process. This is particularly useful for electronic
applications such as the encapsulation of light emitting diodes. However, room temperature reactivity
is rather low compared to other classes of epoxy resin, and high temperature curing using suitable
accelerators is normally required.

Glycidylamine epoxy resin[edit]

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-4,4-methylenebis benzylamine (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 make them important materials for aerospace composite
applications.

Curing epoxy resins[edit]

In general, uncured epoxy resins have only poor mechanical, chemical and heat resistance
properties. 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. Curing of epoxy resins is an exothermic reaction and in some cases produces
sufficient heat to cause thermal degradation if not controlled.
Curing may be achieved by reacting an epoxy with itself (homopolymerisation) or by forming
a copolymer with polyfunctional curatives or hardeners. 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.
Whilst some epoxy resin/ hardener combinations will cure at ambient temperature, many require
heat, with temperatures up to 150 C being common, and up to 200 C 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.

Homopolymerisation[edit]
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 to effect curing, 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[edit]

Structure of TETA, a typical hardener. The amine (NH2) groups react with the epoxide groups of the resin during
polymerisation.

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. For aliphatic amines both primary and secondary amino hydrogens have
approximately the same reactivity, while for aromatic amines, the reactivity of the secondary amine is
typically 2 to 5 times less than the reactivity of a primary amino hydrogen. [5] Use of a difunctional or
polyfunctional amine along with a difunctional epoxy resin forms a three-dimensional cross-linked
network. Aliphatic, cycloaliphatic and aromatic amines are all employed as epoxy hardeners. Amine
type will alter both the processing properties (viscosity, reactivity) and the final properties
(mechanical, temperature and chemical resistance) of the cured copolymer network. Thus amine

structure is normally selected according to the application. Reactivity is broadly in the order aliphatic
amines > cycloaliphatic amines > aromatic amines. Temperature resistance generally increases in
the same order, since aromatic amines form much more rigid structures than aliphatic amines. Whilst
aromatic amines were once widely used as epoxy resin hardeners due to the excellent end
properties they imparted, health concerns with handling these materials means that they have now
largely been replaced by safer aliphatic or cycloaliphatic alternatives.

Anhydrides[edit]
Epoxy resins may be cured with cyclic anhydrides at elevated temperatures. Reaction occurs only
after opening of the anhydride ring, e.g. by secondary hydroxyl groups in the epoxy resin. A possible
side reaction may also occur between the epoxide and hydroxyl groups, but this may be suppressed
by addition of tertiary amines. The low viscosity and 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.

Phenols[edit]
Polyphenols, such as bisphenol A or novolacs can react with epoxy resins at elevated temperatures
(130-180 C), 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[edit]
Also known as mercaptans, thiols with the (S-H) functional group, contain an electron poor hydrogen
which reacts very readily with the epoxide group, even at ambient or sub-ambient temperatures.
Whilst 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.

History[edit]
The first commercial attempts to prepare resins from epichlorohydrin were made in 1927 in
the United States. Credit for the first synthesis of bisphenol-A-based epoxy resins is shared by Dr.
Pierre Castan of Switzerland and Dr. S.O. Greenlee of the United States in 1936. Dr. 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 and later sold in the late 1990s and
is now the Advanced Materialsbusiness unit of Huntsman Corporation of the United States. Dr.
Greenlee's work was for the firm of Devoe-Reynolds of the United States. Devoe-Reynolds, which
was active in the early days of the epoxy resin industry, was sold to Shell Chemical (now Momentive
Specialty Chemicals, formerly Hexion, Resolution Polymers and others).

Applications[edit]
The shelf life of unmixed two-part epoxies is long. There are many anecdotal reports of epoxies
mislaid for decades and then used successfully.[6] However, one more commonly sees one to two
years published as product specifications.
The applications for epoxy-based materials are extensive and include coatings, adhesives and resin
matrices for composite materials such as those using carbon fiber andfiberglass reinforcements
(although polyester, vinyl ester, and other thermosetting resins are also used for glassreinforced 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. 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. [7]

Paints and coatings[edit]

Two part epoxy coatings were developed for heavy duty service on metal substrates and use less
energy than heat-cured powder coatings. These systems generally use a 4:1 by volume mixing ratio,
and dry quickly providing a tough, protective coating with excellent hardness. Their low volatility and
water cleanup makes them useful for factory cast iron, cast steel, cast aluminium applications and
reduces exposure and flammability issues associated with solvent-borne coatings. They are usually
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 chalk out, due to UV exposure.
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 asterrazzo flooring, chip flooring, and colored aggregate flooring. Epoxy flooring has been
proven to be an environmentally friendly alternate to other types of flooring, reducing the facility's
impact on the environment through less water consumption and less pesticides needed. [8]

Adhesives[edit]

Special epoxy is strong enough to withstand the forces between asurfboard fin and the fin mount. This epoxy is waterproof
and capable ofcuring underwater. The blue-coloured epoxy on the left is still undergoing curing.

Epoxy adhesives are a major part of the class of adhesives called "structural adhesives" or
"engineering adhesives" (that includespolyurethane, 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 can be used as adhesives
for wood, metal, glass, stone, and some plastics. They can be made flexible or
rigid, transparent or opaque/colored, fast setting or slow setting. Epoxy adhesives are better in heat
and chemical resistance than other common adhesives. In general, 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).[9]
Some epoxies are cured by exposure to ultraviolet light. Such epoxies are commonly used
in optics, fiber optics, and optoelectronics.

Industrial tooling and composites[edit]

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
composite parts.

Electrical systems and electronics[edit]

An epoxy encapsulated hybrid circuit on a printed circuit board

The interior of a pocket calculator. The dark lump of epoxy in the center covers the processor chip.

Epoxy resin formulations are important in the electronics industry, and are employed in motors,
generators, transformers, switchgear, bushings, and insulators. 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 boardan "FR-4 board"is a sandwich of layers of glass 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, inductors and LED's. 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 LED industry is an up and coming area in which epoxy resins are playing a big role. The potted
LED's are protected from the environment, while the resin can be either clear to protect the lights
aesthetics, or hazy to offer light diffraction.[10]
Epoxy resins are applied using the technology of resin dispensing.

Consumer and marine applications[edit]

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. The chemical reactions in both cases are exothermic.
Large quantities of mix will generate their own heat and greatly speed the reaction, so it is usual to
mix small amounts which can be used quickly.
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.
Depending on the properties required, the ratio may be anything from 1:1 or over 10:1, but in every
case they must be mixed in exactly the right proportions, and thoroughly to avoid unmixed portions.
The final product is then a precise thermo-setting 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 MethylEthyl-Ketone-Peroxide (MEKP), which is very toxic. The presence of the catalyst in the final product
actually detracts from the desirable properties; just enough catalyst to harden fast enough is
preferable. The rate of cure of polyesters is controlled by the amount and type of catalyst, and 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. By contrast,
polyester resins can only bond using the first two of these, which greatly reduces their utility as
adhesives and in marine repair.

Aerospace applications[edit]
In the aerospace industry, epoxy is used as a structural matrix material which is then reinforced by
fiber.[11] Typical fiber reinforcements include glass, carbon, Kevlar, and boron. Epoxies are also used
as a structural adhesive; wood and other 'low-tech' materials are glued with epoxy resin. In
1968, Apollo 8's capsule reentered Earth's atmosphere, protected by a heat shield of epoxy resins
manufactured by Dow Chemical Company.[12]

Biology[edit]

Cells (black) embedded in epoxy resin (amber) for transmission electron microscopy

Water-soluble epoxies such as Durcupan[13][14] are commonly used for embedding electron
microscope samples in plastic so they may be sectioned (sliced thin) with a microtome and then
imaged.[15]

Art[edit]
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.[16]

Industry[edit]
As of 2006, the epoxy industry amounts to more than US$5 billion in North America and about
US$15 billion worldwide. The Chinese market has been growing rapidly, and accounts for more than
30% of the total worldwide market. It is made up of approximately 50100 manufacturers of basic
or commodity epoxy resins and hardeners.
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 purchase 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 epoxiesby 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 formulationseach
tailored to the requirements of a particular application or market.
Impacted by the global economic slump, the epoxy market size declined to $15.8 billion in 2009,
almost to the level of 2005. In some regional markets it even decreased nearly 20%. The current
epoxy market is experiencing positive growth as the global economy revives. With an annual growth
rate of 3.5 - 4% the epoxy market is expected to reach $17.7 billion by 2012 and $21.35 by 2015.

Higher growth rate is foreseen thereafter due to stronger demands from epoxy composite market
and epoxy adhesive market.[17]

Health risks[edit]
The primary risk associated with epoxy use is often related to the hardener component and not to
the epoxy resin itself. Amine hardeners in particular are generally corrosive, but may also be classed
toxic and/or carcinogenic or mutagenic. Aromatic amines present a particular health hazard (most
are known or suspected carcinogens), but their use is now restricted to specific industrial
applications, and safer aliphatic or cycloaliphatic amines are commonly employed.
Liquid epoxy resins in their uncured state are mostly classed as irritant to the eyes and skin, as well
as toxic to aquatic organisms. 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.[18] Exposure to epoxy resins can, over time, induce an allergic
reaction. Sensitization generally occurs due to repeated exposure (e.g. through poor working
hygiene and/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.
[19]
Bisphenol A, which is used to manufacture a common class of epoxy resins, is a known endocrine
disruptor.

Accidents[edit]
The Big Dig ceiling collapse, which occurred on July 10, 2006, is an accident which was caused by
the use of fast-set epoxy which had a higher rate of creep than standard-set epoxy. The accident
resulted in one fatality and cost $54 million to redesign, repair, and inspect all of the tunnels in the D
Street connector. The cost of the fast-set epoxy used to secure the bolts was $1,287.60.
Epoxy coatings or chemical sealer usually have a slick finish presenting a potential slip and fall
hazard risk, however there are anti skid additives which can help mitigate this and provide increased
traction.[20]

Strength & Stiffness

Two important mechanical properties of any resin system are its tensile strength and stiffness. The two figures below
show results for tests carried out on commercially available polyester, vinylester and epoxy resin systems cured at
20C and 80C.

After a cure period of seven days at room temperature it can be seen that a typical epoxy will have higher properties
than a typical polyester and vinylester for both strength and stiffness. The beneficial effect of a post cure at 80C for
five hours can also be seen.
Also of importance to the composite designer and builder is the amount of shrinkage that occurs in a resin during and
following its cure period. Shrinkage is due to the resin molecules rearranging and re-orientating themselves in the
liquid and semi-gelled phase. Polyester and vinylesters require considerable molecular rearrangement to reach their
cured state and can show shrinkage of up to 8%. The different nature of the epoxy reaction, however, leads to very
little rearrangement and with no volatile by-products being evolved, typical shrinkage of an epoxy is reduced to
around 2%. The absence of shrinkage is, in part, responsible for the improved mechanical properties of epoxies over
polyester, as shrinkage is associated with built-in stresses that can weaken the material. Furthermore, shrinkage
through the thickness of a laminate leads to 'print-through' of the pattern of the reinforcing fibres, a cosmetic defect
that is difficult and expensive to eliminate.

Epoxy plastics general chemical and physical properties

An epoxy resin is defined as a molecule with more than one epoxy group, which can be hardened into a usable
plastic. The epoxy group, which is also called the glycidyl group, has through its characteristic appearance given the
name to epoxy.

Epoxy group
What one sees is an oxygen atom on the outside of the carbon chain. Epi means on the outside of and the second
part of the word comes from oxygen.
There are two spellings, namely epoxi and epoxy. The first comes from the oxygens bond with the carbon chain
being called an oxide. Epoxy resin is manufactured from simple basic chemicals that are readily available.

With the help of chemical formulas, the last stage out is as follows:

Bisphenol A + Epichlorohydrin

Diglycidylether Bisphenol A (DGEBA)

epoxy resin
By varying the relationship between bisphenol A and epichlorohydrin, various molecular weights are obtained for the
completed epoxy resin. The lowest molecular weight an epoxy resin of the DGEBA type can have is 340, but if two
elements together can form different molecular weights when they react, the epoxy resin will contain a mixture of
epoxy molecules of varying lengths. One therefore does not refer to the epoxy resins molecular weight, but rather to
their mean molecular weight.
Epoxy resin with a mean molecular weight of over 700 is called high molecular, and epoxy resin with a mean
molecular weight of under 700 low molecular. Epoxy resins can be allergens, and it is the molecular weight that
determines how great the risk. The higher molecular weight, the lower the probability for allergies.
In the formula for epoxy resin, the letter n is seen after the brace. If n=0, i.e. that which is inside the brace does not
exist, we then have the shortest epoxy molecule with a molecular weight of 340. It has the highest reactivity and thus
also constitutes the greatest allergy risk. If n=1, the molecular weight is 624, for n=2 it is 908, etc.
For each time n increases by 1, the molecular weight increases by 284. In a low molecular epoxy resin with the mean
molecular weight of 380, the distribution is approximately 88% n=0, 10% n=1 and 2% n=2. A pure epoxy resin with
n=2 is not an allergen, but if we look at a commercial epoxy resin with the molecular weight of 1080, the distribution is
approximately 20% n=0, 15% n=1, 15% n=2 and 50% n=3, 4 and 5. This means the even a high molecular epoxy
resin can be an allergen.
A low molecular epoxy resin with a mean molecular weight of 380 is fluid at room temperature, while an epoxy resin
with a mean molecular weight of 1000 is solid at room temperature. The molecular weight determines what the epoxy
resin can be used for.
The low molecular can be handled without solvent additives, which evaporate and are therefore used for casting,
thick coatings, gap-filling glues, etc.
The high molecular epoxy resins must as a rule be dissolved in organic solvents to be manageable, which limits
usage to paints and lacquers.
To convert epoxy resin to epoxy plastic, a reaction with a suitable substance is required. Such a substance in this
context is called a hardener.
Examples of substance groups that function as epoxy hardeners are: amines, amides, acid anhydrides, imidazoles,
boron trifluoride complexes, phenols, mercaptans and metal oxides.

For hardening at room temperature, amines and amides are primarily used, and to a certain extent mercaptans. The
other hardener types generally require temperatures above +150C to react with the epoxy. From this point forward,
only amines and amide hardeners will be further described.
Amines are substances that are closely related to ammonia (NH3). Depending on how many hydrogen atoms that are
replaced by alkyl groups, primary amines NH2-R, secondary amines NH-R1 or tertiary amines N-R2 arise. The total
number of amino groups determines if the amine is a monoamine (NH2-R), a diamine (NH2-R-NH2) or a polyamine
(NH2-R-NH-R-NH-R-NH2).
Furthermore, the amines are divided into aliphatic, i.e. a straight carbon chain, cycloaliphatic with a ring-shaped
carbon chain and finally aromatic where the amino group is bonded to a benzene ring.
As hardener for the epoxy resin, primarily diamines and polyamines are used.
The primary amino group NH2 contains as seen, two hydrogen atoms and one nitrogen atom. It is the hydrogen that
constitutes the reactive part, and the reaction occurs with the oxygen in the epoxy group.
With somewhat simplified chemical formulas, it looks like this:

Primary amine + Epoxy group

gives

Secondary

amino group
In the first reaction phase, one of the amines hydrogen atoms reacts with the epoxy groups oxygen, causing the
formation of a hydroxyl group (OH-) at the same time as the primary amine is reduced to a secondary amine. The
reaction continues:

The secondary amine reacts with yet another epoxy group and the reaction is complete.
An epoxy molecule normally contains two epoxy groups, and one primary diamine has four reactive hydrogen atoms.
A schematic of the epoxy plastic then looks like this:

The epoxy plastic molecule is of course three-dimensional in reality.

Examples of amines that are used as hardeners for epoxy resins

Aliphatic amines

Diethylenetriamine

Triethylenetetramine

Aminoethyl piperazine

Trimethyl hexamethylenediamine

Cycloaliphatic amines

Isophorondiamine

Diamino-dicyclohexylmethane

Aromatic amines

Diaminodiphenylmethane

m-Phenylendiamine

It is very common to pre-react the amines with a certain portion of epoxy resin. The purpose of this is to attain a
hardener that is less fluid than the pure amine and that has a somewhat higher reactivity.
This type of hardener is called amine adducts, and reacts largely in the same way as previously shown.
The next large group of hardeners is the amides, or more correctly expressed, the polyaminoamides. An amide is
formed when a polyamine reacts with a fatty acid.

This generally applies to all polyamides, even nylon. By varying the relationship between fatty acid and amine, one
can decide if the polyamide will be acid-terminated (of the type nylon) or amine-terminated, i.e. which end groups the
polyamide will have. Only amine-terminated polyamides can be used as hardeners for epoxy resin. As fatty acid,

most often used is tall fatty acid, linolic acid or olein. The fatty acids use either monomer (one carboxylic group) or
dimer (two carboxylic groups). As polyamines, diethylenetriamine, triethylenetetramine and tetraethylenepentamine
are used. The hydrogen in the amide group (CONH) is not reactive, but it is rather the hydrogen in the primary amino
groups at the polyamides ends and the secondary amino groups that are derived from the polyamine, which are
reactive with the epoxy resin in the same way as previously described.
Both amine adducts and polyamides can be made water soluble. Such solutions have the capacity to emulsify low
molecular epoxy resin, which in turn provides the possibility to manufacture water soluble epoxy paints.
The reaction between an epoxy resin and a hardener is an irreversible poly-addition, i.e. no by-products are formed,
and the epoxy plastic cannot be decomposed into epoxy resin and hardener. The reaction is exothermic, which
means that heat is released. Depending on the type of hardener one uses, one can achieve very large differences in
reaction speeds. This has significant practical importance when working with epoxy. The time it takes to consume a
mixture of epoxy resin and hardener is called potlife. Depending on the mixtures reactivity, potlife can vary from a
few seconds to several years.
Potlife can be determined in several ways.
One method is to temper the epoxy resin and hardener to +20C. Thereafter an amount of 100 grams is mixed in a
plastic cup. The time for the mixtures temperature to reach +50C is set as the mixtures potlife. For systems with low
reactivity (long potlife), one most often chooses to measure the viscosity or consistency, and measure the time until
the initial viscosity is doubled.
Both of these methods are unusable for aqueous emulsified or aqueous dispersed systems. In this case, one instead
performs a lay-up test and measures the time to gloss reduction.
Most chemical reactions follow Arrhenius law, which states that the reaction speed doubles for each tenth of a
degree the temperature is increased. This means that a reaction is twice as fast at +30C as at +20C.
The larger the amount that is mixed together, the greater the amount of exothermic heat that is created. There is not
enough time for this heat to be dissipated through the mixture vessels surface, so instead it heats the mixture. As the
temperature increases, the reaction speed also increases, which entails that the potlife is shorter, the larger the
amount that is mixed.

Example of potlife for 100 and 500 grams of the same epoxy resin/hardener mixture
Potlife for an epoxy system consequently provides certain information to the user on working time after mixture, but
one must consider the amount of material mixed, and the materials initial temperature. The epoxys hardening time is
defined as the time from the epoxy being applied until the formed epoxy plastic has achieved its final properties
pertaining to strength and chemical resistance.
For epoxy that is applied in thin layers, the exothermic heat will not increase the temperature in the layer to any
significant degree, but instead, the epoxy quickly assumes the temperature of the substrate. The reaction between
the epoxy resin and hardener then goes relatively quick at the beginning because of the large availability of reactive
molecules, and because the mobility of the molecules is high as long as the viscosity is low.
As complete epoxy molecules are formed, the number of reactive molecules is reduced at the same time as the
viscosity increases. The reaction speed gradually slows.
As a rule of thumb, room temperature hardened epoxy needs about 7 days at +20C to attain maximum properties,
but already after 24 hours, one can have attained about 7080% of the final properties.
Arrhenius law naturally applies even if the reaction occurs at a constant temperature. This means that if the substrate
is at +10C, it takes about 14 days to attain final properties.

Example of epoxys hardening process at constant temperature.

Epoxy plastics characteristic basic properties

Currently more than 50 different substances fulfil the definition for an epoxy resin. If one also adds that there are
several hundred different hardeners, it is easy to understand that epoxy plastics properties can be modified to satisfy
the most varied requirements. Nevertheless, certain basic properties are always present.

Adhesion
One of epoxy plastics most characteristic properties is the capacity to adhere to most substrates. The reason for this
is the presence of polar hydroxyl groups, and the ether bonds. The negligible shrinkage also entails that contact
between the epoxy plastic and the substrate is not disturbed by tensions. The epoxy plastics surface tension is most
often under the critical surface energy for most materials. This is one of the requirements for adhesion to be
achieved.

Mechanical strength
No other hard plastic can display as high mechanical strength as correctly formulated epoxy plastic. Again, it is
largely because of the minimal shrinkage that built-in tensions are avoided. The tensile strength can exceed 80 MPa.

Chemical resistance
Thanks to the possibility of varying the epoxy plastics properties, one can make epoxy plastic resistant to most
chemicals. In general, epoxy plastic is very resistant to alkali, which is of importance in surface-treating concrete.

Diffusion density
Epoxy generally has relatively high vapour transmission resistance, but with a special technique, epoxy plastic can be
made open to diffusion. Epoxy that is open to diffusion can be applied on, for example, wet concrete and provide
adhesion higher than the concretes tensile strength.

Water tightness
The epoxy plastics are to be considered as watertight and they are often used to protect against water.

Electrical insulation capacity

Epoxy plastics are excellent electrical insulators. Volume resistivity is normally 1015Ohmcm. This in combination with
high moisture resistance and chemical resistance makes the epoxy suitable for both the manufacture of electronics
components and the embedment of transformers.

Shrinkage
The epoxy plastics have very slight shrinkage during hardening. This is because the epoxy molecule has a rather
small reorientation during the hardening process compared with, for example, polyester and methylmetacrylate.

Heat resistance
When it comes to heat resistance, room temperature hardened epoxy plastic differs very little from heat hardened.
One often specifies heat resistance with HDT (Heat Deflection Temperature) or Tg (Glass transition temperature).
At HDT, the mechanical strength declines quickly. Room temperature hardened epoxy seldom attains HDT above
70C, while heat hardened can reach 250C.

Modifiable
Perhaps the chief property of epoxy is the nearly unlimited capability to modify the final properties of the epoxy plastic
to meet special requirements. It is primarily the hardener that influences the plastics properties, but as presented in
the next chapter, there are many other substances that influence epoxy products.

Stability in light
Epoxy plastics based on aromatic epoxy resins are sensitive to light in the UV range. Direct radiation with ultraviolet
light quickly causes yellowing. Even normal sunlight contains enough ultraviolet radiation for yellowing to occur. Most
resistant are aliphatic epoxy resins with anhydride or amine hardener.

Modification of epoxy resins

Viscosity at 25C of an unmodified low molecular epoxy resin of the DGEBA type, is about 10 Pas, at 20C about 24
Pas and at 15C about 68 Pas.

It is easy to understand that an unmodified epoxy resin cannot always be used outdoors or where the temperature is
low. The first reason for modification is thus viscosity reduction to a suitable working consistency. Several options are
available here.
First, we have non-reactive diluents, which refers to such substances that can be mixed with the epoxy resin but that
do not participate in the reaction between the epoxy and hardener. Included here are the ordinary solvents such as
xylene, toluole, glycol ethers, ketones, lower alcohols, etc.
Other non-reactive diluents include a large number of substances with sufficiently low vapour pressure that they do
not evaporate from the hardened plastic under normal conditions. Examples of these are benzyl alcohol and
coumarone resins. The substances that are not chemically bonded in the epoxy plastic molecule are to be imagined
as deposited between the plastic molecular chains.
In this group are the ordinary solvents that have the strongest influence on viscosity, but which often entail a
dangerous path.
Epoxy resin has very high solvent retention, i.e. the capacity to retain solvents. This means that it will take a long time
before the solvent has evaporated. In a 1 mm thick layer, solvent residue can be detected after several months at
room temperature.
Damage that can arise from solvents is usually blistering, either through high heating or because of osmosis when
moisture occurs in concrete. Another reason to avoid solvents is the shrinkage effect that can result in layers
detaching from weak substrates.
The diluents that under normal conditions do not evaporate affect the epoxy plastics properties in other ways than
viscosity reduction. Positive changes can be flexibility, improved resistance to water and salt solutions because of
hydrophobing, improved reactivity, in part because the mobility of the epoxy and the hardener molecule is better at
lower viscosity, and in part because of the catalytic effect from hydroxyl groups in, for example, benzyl alcohol.
Negative changes are degraded heat resistance and larger thermal expansion.
At higher temperatures, volatility can be substantial with several of these substances. This can result in shrinkage
with cracking and subsequent reduced adhesion. Another aspect that sometimes must be considered is the
compatibility with bitumen. A minority of the non-reactive diluents do not bleed in bitumen.

Furthermore, many diluents in this group are esters that can saponify upon contact with concrete under the influence
of water.

Reactive diluent (thinners)

These substances have, as the name implies, the capacity to react with the epoxy resin or hardener, so that in this
way, bond in the plastic molecule.
The most used types are those that contain one or more epoxy groups. There is a very large group of such
substances that all can give the final plastic different properties.
What characterizes these substances is that they cannot migrate, evaporate or be extracted from the epoxy plastic.
Heat resistance declines somewhat in comparison to unmodified epoxy, but not at all as much as in the case of the
non-reactive diluent. A valuable property of the reactive diluent is that they reduce the surface tension of the epoxy
resin, which in turn can improve wetting capabilities and thus adhesion. Depending on the reactive diluent
composition, both flexibility and chemical resistance can be affected.
Other substances used to modify the epoxy plastics properties are, for example, high molecular isocyanates, which
via the hardener, can react with the epoxy resin. The result is a plastic with rubber-elastic properties, which are
retained down to about -40C.
Such modification changes the epoxy plastics fundamental properties.
Heat resistance and chemical resistance decline with increased elasticity. At the same time, the viscosity increases
because the isocyanates in themselves are very highly viscous. This means that further modification is necessary to
reduce viscosity.
The next group of modification substances is pigments and fillers.
Pigment is used to colour the epoxy material, and the filler to increase the mechanical strength and to reduce costs.
The pigments used are most often metal oxides such as titanium dioxide, iron oxide and chromium oxide.
As a rule, fillers are finely ground minerals and quartz sand. It is important that both pigments and fillers are properly
dispersed in the epoxy binding agent.
In addition to the listed modification substances, there are a number of aids to affect such things as rheology, i.e.
consistency, flow, air bubbles and adhesion.
It is easy to understand that an epoxy product has a relatively complex composition, where the included components
shall interact for the results to be as intended.