Chapter

Epoxy Adhesives
Chunfu Chen, Bin Li, Masao Kanari and Daoqiang Lu

Abstract

Epoxy adhesives are primarily composed of epoxy resin and curing agent.
Epoxy adhesives are supplied in both one-component package and two-com-
ponent package depending on curing agent used and curing method applied.
Two-component epoxy adhesives are prepared by packing epoxy composition and
curing agent composition separately. They cure soon after mixing the two com-
ponents together. Almost all room temperature cure epoxy adhesives are supplied
in two-component package. One-component epoxy adhesives are prepared and
supplied by mixing all formulated components in advance including epoxy resin
and curing agent. One-component epoxy adhesives usually need cure at elevated
temperature and store at low temperature in a refrigerator or even freezer.
Epoxy adhesives have been widely used as typical reactive adhesives for various
applications ranging from general industry, construction, electronics assembly,
automobile production to aerospace market. Typical room temperature cure
epoxy adhesives, thermal cure epoxy adhesives and UV cure epoxy adhesives are
introduced in detail.

Keywords: epoxy adhesive, one-component, two-component, room temperature cure,

thermal cure, UV cure, latent curing agent

1. Introduction

Epoxy adhesive was first invented in 1936 by Dr. Pierre Castan for dental appli-
cation via curing bisphenol A epoxy resin with phthalic anhydride. Commercial
supply of epoxy adhesives was started in late 1940s in Europe and USA. Various
epoxy adhesives have been developed and commercialized since then and widely
used as typical reactive adhesives for various structural bonding applications
ranging from general industry, construction, electronics assembly, automobile
production to aerospace market [1–11]. Their typical application area and examples
as well as their supply type, curing method are summarized in Table 1. Major global
suppliers for epoxy adhesives are Henkel AG & Co. KGaA, H.B. Fuller Company,
3M, Huntsman Corporation, Sika Corporation, Arkema Corporation, Cemendine
Co., Ltd., Three-Bond Co., ltd., Huitian Adhesive, etc.
Epoxy adhesives show good adhesion on various substrates and are suitable to
bond metals, glass, concrete, ceramics, wood and many plastics. Curing shrinkage
is very low. Cured epoxy resin possesses strong and rigid cross-linked chemical
structure suitable for structural bonding applications. By combination of various
epoxy resins and different curing agents, a number of epoxy adhesives have been
commercialized for different applications. On the other hand, room temperature
and thermal cure epoxy adhesives need relatively long cure time. Most cured
epoxy adhesives are very rigid and are not suitable for bonding flexible substrates.

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Application area Application examples Package type Cure method

Industrial Structural bonding One component; R.T. cure

Two components Thermal cure

Construction Concrete repairing Two components R.T. cure

Anchor bolt fixture

Automotive Structural bonding One component; Thermal cure

Hemming adhesion Two components

Aerospace Metal, honeycomb & composite One component; Thermal cure

bonding, repairing Two components

Electronics Electrically conductive One component; Thermal cure

Display assembly Two components UV cure
Image sensor assembly R.T. cure
Underfills
Medical bonding

Others Sports tools Two components R.T. cure

Consumer applications

Table 1.
Typical applications of epoxy adhesives.

In selection and use of epoxy adhesives, cautions need to be paid on their pot
life, cure condition, cure method, physical properties of un-cure and cured resin as
well as adhesion performance.

2. Epoxy adhesive chemistry

Epoxy adhesives are primarily composed of epoxy resin and curing agent. Filler,
toughener, plasticizer and other additives such as silane coupling agent, deformer
and colorant, etc., can be formulated as needed. Common compositions and their
main role of epoxy adhesives are illustrated in Table 2.
Epoxy resins are mainly synthesized from reaction of active hydrogen in phe-
nols, alcohols, amines and acids with epichorohydrin, abbreviated normally as ECH
at certain well controlled conditions. Epoxy resin can be also prepared by oxidation
of olefin with peroxide as in the case of preparation of cycloaliphatic epoxy resins.
Main commercial epoxy resins, their preparation and key features are shown in
Table 3. Bisphenol A diglycidyl ether, often called as bisphenol A type epoxy resin,
is the first commercialized and still most widely used epoxy resin. Synthesis of
DGEBA is illustrated in Figure 1 [12]. In volume base, it is estimated that over 75%
of epoxy resin used in industry is this type. Figure 2 illustrates chemical structure
and key features of various functional groups for bisphenol A diglycidyl ether [13],
the most common epoxy resin used in epoxy adhesives.
Epoxide group is chemically very active. Epoxy resin can react with active
hydrogen almost equivalently via polyaddition mechanism with polyamines,
mercaptan compounds, phenols and anhydrates to become cross-linked strong
thermoset polymers. Epoxy resin can also polymerize homogeneously via anionic
polymerization mechanism by initiating of Lewis bases such as tertiary amines
or imidazole compounds. It can also polymerize via cationic polymerization
mechanism via initiating of Lewis acid such as Boron trifluoride amine com-
plex or strong acid such as onium salts, iodonium salts. Table 4 lists typical
curing agent, initiator used in epoxy adhesives. By combination of suitable
epoxy resin with curing agent, epoxy adhesive is designed for various substrate
bonding in different applications. It is supplied in both two-component and

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Constituent Ingredient Main role

Primary Epoxy resin, reactive diluent Adhesive base
Curing agent/catalyst, accelerator Curability
Modifying Filler Property modification
Toughener Toughening
Plasticizer Flexibility
Additive Coupling agent Adhesion
Colorant Color

Table 2.
Epoxy adhesive compositions.

Epoxy resin type Preparation from Key features

Glycidyl ether of
Bisphenol A Bisphenol A and ECH Standard epoxy resin
Bisphenol F Bisphenol F and ECH Low viscosity
Novalac Novalac with ECH Multi-functional
Glycidyl ester Carboxylic acids and ECH Mainly for anhydrate cure
Glycidyl amine Amines and ECH Multi-functional
Cycloaliphatic Oxidation of olefin by peroxide Cationic cure

Table 3.
Commercial epoxy resins.

Figure 1.
Synthesis of DGEBA (diglycidyl ether of bisphenol A).

Figure 2.
Chemical structure and key features of DGEBA.

one-component package depending on the curing agent and curing method used.
Two-component epoxy adhesive is prepared by packing epoxy composition and
curing agent composition separately before use. It will cure soon after mixing based
on designed mixing ratio. Almost all room temperature cure epoxy adhesives

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Polymerization mechanism Curing agent, initiator

Polyaddition Polyamines
Modified polyamines
Mercaptans
Phenols
Anhydrates
Dicyandiamide
Anionic Tertiary amines
Imidazole compounds
Cationic Boron trifluoride monoethylamine
Onium salts
Iodonium salts

Table 4.
Epoxy curing agents.

are supplied in two-component package. Epoxy adhesives can be formulated in

one-component package where all components including epoxy resin and curing
agent has been mixed in advance. One-component epoxy adhesives usually use
elevated temperature cure and need to be stored at low temperature conditions in
a refrigerator or even freezer for long shelf life.

3. Room temperature cure epoxy adhesives

Room temperature cure epoxy adhesives are normally prepared and supplied in
two-component package with epoxy resin component parked in one resin part and
curing agent packed as the other hardener part. By mixing these two parts together,
epoxy resin will react with curing agent quickly at room temperature conditions to
become cross-linked strong thermoset structure that can bond adhesion substrates
tightly. By use of different type of curing agents, pot life and cure time can be
designed as needed.

3.1 Fast room temperature cure epoxy adhesives

Mercaptan compounds are usually selected as curing agent for fast room
temperature curable epoxy adhesive because its reaction with epoxy resin is
very fast in the existence of small amount of basic chemicals such as tertiary
amine or imidazole as accelerator. As shown in Figure 3, epoxy resin reacts
with mercaptan group equivalently via polyaddition reaction mechanism [14].
Fixture time can be <30 minutes or even 15 minutes at room temperature. Full
cure time will need 24 hours. Precautions need to be paid on its very short
work life, <10 minutes or even 5 minutes. Commercial fast cure epoxy adhesives
supplied by Henkel AG & Co. KGaA and their typical properties are illustrated
in Table 5 [15].

Figure 3.
Polyaddition reaction of epoxy resin with mercaptan.

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Product LOCTITE EA E-05MR LOCTITE EA E-00NS

Color clear translucent

Viscosity, mPas/25°C 25,000 100,000

Mix ratio 1:1 1:1

Work life, minutes 5 3

Fixture time, minutes 15 10

Room temperature cure time, hours 24 24

Shear strength, psi on steel 3360 1600

Table 5.
Fast room temperature cure epoxy adhesives.

Figure 4.
Polyaddition reaction between epoxy resin and amine.

Product LOCTITE EA E-20HP LOCTITE EA E-120HP

Color Off-White Amber
Viscosity, mPas/25°C 30,000 30,000
Mix ratio 2:1 2:1
Work life, minutes 20 120
Fixture time, minutes 120 >180
Room temperature cure time, hours 24 24
Shear strength, psi on steel 3270 4300

Table 6.
Room temperature cure epoxy adhesives.

3.2 Room temperature cure epoxy adhesives

Aliphatic polyamines are most commonly used curing agents in epoxy resin
technology. A number of modified polyamine type curing agents with adjustment
on curability, handling or other physical properties for easy use have been com-
mercialized in the market by curing agent suppliers. As shown in Figure 4, active
hydrogen of primary and secondary amine reacts equivalently with epoxide via
polyaddition mechanism [16]. Fixture time and work life can be adjusted by com-
bination with suitable curing agent. Table 6 shows commercial room temperature
epoxy adhesives supplied by Henkel AG & Co. KGaA and their properties [17].

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4. Thermal cure epoxy adhesives

Thermal cure epoxy adhesives are prepared and supplied in both one-
component and two-component packages depending mainly on curing agent type
used. Compared to room temperature cure type, thermal cure two-component
epoxy adhesives usually have higher glass transition temperature that is suitable
for high temperature resistance applications. One-component epoxy adhesives do
not need pre-mixing in use and thus can be handled much easily. Many new one-
component epoxy adhesives have been commercialized and become more and more
important in recent years.

4.1 Two-component thermal cure epoxy adhesives

When use cycloaliphatic amine or aromatic amine as curing agent, post

thermal cure process is usually required to achieve full cure as their reactivity,
especially aromatic amines and secondary amine in cycloaliphatic amine, with
epoxide is much lower with compared to aliphatic amines applicable for room
temperature cure. Chemical structure of commonly used cycloaliphatic amine
IPDA (isophorone diamine) and aromatic amine DDM (methylene dianiline) is
shown in Figure 5 [18, 19]. Thermal cure epoxy adhesives have much stronger
and rigid structure and normally possess higher glass transition temperature with
compared to room temperature cure epoxy adhesives mainly based on aliphatic
amines or mercaptans. Two-component thermal cure epoxy adhesives are mainly
used for higher temperature resistance required applications such as automobile
production and aerospace market.

4.2 One-component thermal cure epoxy adhesives

One-component epoxy adhesives do not require pre-mix before use since all
components have been mixed together and there is no concern on insufficient mix-
ing problem as often occurred in two-component use. Pot life of one-component
epoxy adhesives is usually long and one-component adhesives are thus suitable for
automatic dispensing systems. Compared to two-component type, one-component
epoxy adhesives can be handled much easily. On the other hand, one-component
epoxy adhesives usually need cure at higher temperature because of long enough
room temperature stability needed for adhesive preparation and storage. Most
one-component epoxy adhesives require storage condition at lower temperatures
in a refrigerator or even freezer.
Recently one-component thermal cure epoxy adhesives have become more
and more important especially in electronics assembly and automotive produc-
tion where high production efficiency is required. With selection of suitable latent
curing agents, a number of one-component epoxy adhesives have been developed
and commercialized by epoxy adhesive suppliers for various applications. Typical
commercial latent curing agents are summarized in Table 7.

Figure 5.
Chemical structure of IPDA and DDM.

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Latency mechanism Latent curing agent Curing Typical curing

agent state temperature °C

Chemical block and physical DICY Solid ≥150

separation
Dihydrazines ≥120

Physical separation Modified imidazoles Fine powder ≥80

Modified polyamine ≥80

Chemical block Onium salts Solid ≥80

Amine-BF3 complex Liquid ≥130

Table 7.
Typical commercial latent curing agents.

Figure 6.
Chemical structure of DICY.

DICY (dicyandiamide), chemical structure shown in Figure 6 [20], is the oldest

and widely used latent curing agent for epoxy resin technology. It is a solid chemical
with a melting point at 208°C. DICY formulated epoxy composition is very stable,
up to 6 months at room temperature. Latency mechanism is a combination of physi-
cally separation and chemically blocking with epoxide group. DICY cured epoxy
resin shows high adhesion and possesses high glass transition temperature especially
suitable for high performance required applications such as vehicle parts bonding in
automobile production. Cure temperature of DICY alone with epoxy resin normally
needs at least 150°C to achieve full cure. By addition small amount of accelerator
such as modified urea compounds and imidazole compound, cure temperature can
be further lowered to 120°C [21].
In recent years, new type latent curing agents have been developed and com-
mercialized by several curing agent suppliers [22–26]. These latent curing agents are
supplied as fine powder with average particle size well controlled in a few microns or
premix of fine powder latent curing agent in epoxy resin. They are manufactured by
grinding specially synthesized modified polyamine or imidazole solid with a softening
point from 80 to 150°C. Latency mechanism is mainly physically separation between
curing agent and epoxide. Curing temperature has been be lowered to as low as 80°C
and its formulated epoxy composition can be still quite stable at room temperature.
Many one-component epoxy adhesives commercialized recently are based on these
new type latent curing agents because of their lower temperature curability suitable
for use in bonding heat sensitive substrates such as plastics. By combination of small
amount of liquid phenol compound with latent curing agent, it has been found that
cure time of one-component epoxy adhesives can be shortened significantly [27, 28].

5. UV cure epoxy adhesives

Ultra-violet light (UV) curable epoxy adhesives can be cured quickly and have
been very successfully used in several new electronics assembly and general bonding

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Adhesive type UV acrylate UV cationic epoxy Hybrid thermal cure

epoxy

Main compositions Acrylate Epoxy resin Acrylate

Photoinitiator Cationic photoinitiator Photoinitiator

Epoxy resin

Curing agent

Polymerization

UV cure Radical Cationic Radical

Thermal cure N.A. Cationic Polyaddition, anionic

Key features

Oxygen inhibition Yes Yes Partially

Alkali inhibition No Medium No

UV curability High Preferred High

Post thermal cure No need Partially Need

Shadow cure No Low Yes

Cure shrinkage High Good Low

Adhesion Moderate Good

Table 8.
Comparison of UV acrylate, cationic epoxy and hybrid epoxy adhesives.

applications such as image sensor module assembly, display panel and module
assembly where fast production speed and high adhesion performance are required.
Various UV cationic epoxy adhesive and UV acrylate hybrid thermal cure epoxy
adhesives have been commercialized in recent years. As compared in Table 8, UV
cure epoxy adhesives have no oxygen inhibition issue, low curing shrinkage and
show better adhesion with compared to common UV acrylate adhesives.

5.1 UV cationic epoxy adhesives

UV cationic epoxy adhesives are primarily composed of epoxy resin and cationic
photo-initiator [29–31]. Cycloaliphatic type epoxy resins are usually selected for UV
cationic epoxy adhesives because of faster cationic polymerization rate than that
of normal bisphenol A diglycidyl ether type epoxy resin. As illustrated in Figure 7
[32], cationic photoinitiator formulated in UV epoxy adhesives absorbs UV energy to
generate strong acid that will react with epoxy to produce cationic which can initi-
ate homo-polymerization of epoxy resin. Compared to common acrylate based UV
adhesives, UV cationic epoxy adhesives have lower cure shrinkage because of epoxy
structure and have no surface cure issue resulted from oxygen inhibition to free radical
polymerization since they cure via cationic polymerization. On the other hand, UV
cationic epoxy adhesives are not suitable for bonding basic substrates which terminate
cationic polymerization. UV cationic epoxy adhesives will need some longer cure time.
In real use, a post thermal cure of UV cationic epoxy adhesives after the UV radiation
is commonly used for full cure to assure satisfactory adhesion performance.
UV cationic epoxy adhesives have been commercialized and used in optical parts
bonding, camera module sensor packaging and OLED panel assembly applications
[33–37]. The authors have found that adhesion reliability performance of UV cat-
ionic epoxy adhesives can be much improved by combination use of cationic photo
initiator with thermal cationic initiator [38].

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Figure 7.
UV cationic polymerization of epoxy adhesives.

5.2 UV hybrid epoxy adhesives

Most widely used UV cure adhesives are acrylate compositions [39–41].

Acrylate based UV cure adhesives are mainly composed of acrylate monomer,
acrylate oligomer and radical photo-initiator. Acrylate based UV cure adhesives
can be cured instantly, within seconds. Limitations of UV cure acrylate adhesives
are surface cure issue, shadow cure problem, high cure shrinkage and poor humid-
ity reliability. By combination of UV acrylate composition with thermal cure epoxy
composition, UV and thermal cure hybrid epoxy adhesives have been developed
and commercialized for over two decades [42–44]. Acrylate monomer, epoxy
resin, photo-initiator and epoxy curing agent are primarily formulated in the UV
and thermal cure hybrid adhesives. UV hybrid epoxy adhesives combine advan-
tages from both UV acrylate proportion and thermal cure epoxy part. Adhesion
reliability performance could be much improved by introduction of epoxy compo-
sition with compared to normal UV acrylate adhesives. In the meantime, produc-
tion efficiency could be much improved by shortening the fixture time to seconds
via UV radiation with compared to at least dozens of minutes needed for thermal
cure epoxy adhesives. Surface cure issue, shadow cure issue and cure shrinkage
problem of acrylate UV adhesives could also be improved to certain degree because
of lower contents of free radical curable acrylate compositions. In some cases, ther-
mal initiator such as peroxide is also formulated in the hybrid adhesive to assure
curing remained acrylate compositions after UV radiation or those at shadow areas
where UV light cannot reach.
Successful development and industrialization of so called ODF (One Drop Fill)
process for large size LCD (liquid crystal panel) panel production was one important
technology revolution in early 2000s that have made a big impact on our modern
life. Development and commercialization of LCD ODF main sealant, an UV hybrid
epoxy adhesive, played a key role in its mass production success [45–47]. LCD ODF
main sealant is an adhesive material that is used to bond two glass substrates and
seal liquid crystal material between them. It is a UV hybrid epoxy adhesive, typically
composed of acrylate monomer, photo-initiator, partially acrylate epoxy resin and
latent curing agent. Main steps for the adhesive use in this process are: (1) dispensing
LCD main sealant; (2) dropping off liquid crystal materials into each cell;
(3) alignment and assembly; (4) UV cure the sealant; and (5) thermal cure the seal-
ant. The author has invented initiator free UV hybrid thermal cure epoxy adhesives
by combination with bismaleimides that shows much better compatibility with
liquid crystal material and high performance [48–50].

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6. Summary

Epoxy adhesives show very good adhesion to various substrates and are the most
important structural adhesives. Epoxy adhesives can be cured at room temperature
condition, at elevated temperature condition or via UV light radiation mainly
depending on curing agent type formulated. Lots of epoxy adhesives, either sup-
plied in one-component or two-component package, have been commercialized and
widely used for bonding metals, concrete, glass, ceramics, concrete, many plastics,
wood, etc. in various industrial production and applications.

Author details

Chunfu Chen1*, Bin Li2, Masao Kanari1 and Daoqiang Lu2

1 Henkel Technology Center-Asia Pacific, Henkel Japan Ltd., Yokohama, Japan

2 Henkel Adhesive Innovation Center, Henkel (China) Co., Ltd., Shanghai,

PR China

*Address all correspondence to: [email protected]

© 2019 The Author(s). Licensee IntechOpen. This chapter is distributed under the terms
of the Creative Commons Attribution License (http://creativecommons.org/licenses/
by/3.0), which permits unrestricted use, distribution, and reproduction in any medium,
provided the original work is properly cited.

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