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New trends in vinyl ester resins

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DOI: 10.1515/revce-2014-0012

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Shipra Jaswal and Bharti Gaur*
New trends in vinyl ester resins
Abstract: Vinyl ester resins (VERs) are high-performance
unsaturated resins derived by the addition reaction of var-
ious epoxide resins with α-β unsaturated carboxylic acids.
These resins have always been classified under unsatu-
rated polyester resins. However, VERs have remarkable
corrosion resistance and superior physical properties as
compared with these conventional polyester resins, which
make VERs a class of their own and hallmark of today’s
resin industries. Hence, there is a need to review the avail-
able literature on this important class of thermosetting
resins separately. In this article, an attempt is made to
review the state of the art of VERs, including synthesis,
characterization, curing, thermal, chemical, oxidative
properties, and applications. The main focus is on the lat-
est developments in this area.
Keywords: corrosion resistance; cross-linking reactions;
mechanical properties; thermosetting resins; vinyl ester
resins.
DOI 10.1515/revce-2014-0012
Received February 20, 2014; accepted July 14, 2014
1 Introduction
Vinyl ester resins (VERs) are widely used thermosetting
resins in solvent storage tanks, sewer pipes, building and
construction, coating, automobile structural parts, swim-
ming pools, and marine composites (Brown and Mathys
1997, Mouritz and Mathys 1999, Varma and Gupta 2000,
Zhang et  al. 2000, Brody and Gillespie 2005) because of
their low cost, excellent chemical and corrosion resist-
ance, outstanding heat performance, favorable mechani-
cal properties, and better processibility. These are the
addition products of epoxy resins and α-β unsaturated
carboxylic acids (Young 1976, Launikitis 1982) and are
structurally similar to unsaturated polyester (UPE) resins
*Corresponding author: Bharti Gaur, Department of Chemistry,
National Institute of Technology, NIT Hamirpur (H.P.) 177005, India,
e-mail: bhartigaur@gmail.com
Shipra Jaswal: Department of Chemistry, National Institute of
Technology, NIT Hamirpur (H.P.) 177005, India
Rev Chem Eng 2014; aop
(Figure 1). Shell Chemical Co. first commercialized these
resins in 1965 under the trade name Epocryl. Dow Chemi-
cal Co. then introduced a similar series of resins under the
name Derakane. VERs are used in place of UPE resins since
the unreacted carbon-carbon double bonds and the ester
group, present in the backbone of UPE resins after curing,
provide sites for hydrolytic attack, oxidation, and halo-
genation, which make the cured UPE resin unsuitable for
aggressive environments (Mallision 1987, Cheremisinoff
and Cheremisinoff 1995, Juska and Puckett 1997), whereas
in VERs, the ester linkages are present only at the terminal
ends of the chains. VERs incorporate the thermal stability
and mechanical strength of the epoxy backbone, and the
presence of double bonds at the chain ends provides it the
ease of cure that is comparable with that in UPE resins.
These resins are costlier than UPE resins but are still widely
used since they have excellent chemical resistance, low
water absorption, as well as low shrinkage during cure as
compared with polyester resins. Moreover, unlike epoxy
resins, vinyl esters (VEs) have controlled cure rate and do
not need any curing agent to form a cured network. Neat
VERs having high viscosity (105 cps) may vary from semi-
solid to solid. Reactive or nonreactive diluents are used to
provide workable viscosity levels and enhanced reactiv-
ity (Varma et  al. 1985, Bhatnagar and Varma 1989, Gaur
and Rai 1992a,b, Choudhary and Varma 1993, Malik et al.
2001) to control the cross-link density and affect strength,
percentage elongation, hardness, chemical resistance,
scratch resistance, and surface finish. The physical and
handling properties of VERs depend on the source of
vinyl termination (methacrylate or acrylate), the amount
and type of co-reactant, and the molecular weight of the
resin backbone. Although acrylate VERs are more suscep-
tible to hydrolysis than methacrylate VERs are, they are
preferred in radiation cure inks and coatings because of
better reactivity (Launikitis 1982). The use of other unsatu-
rated acids such as crotonic and cinnamic acids has also
been reported ( Jackson 1980, Zaske 1998). Although con-
siderable work has been done on VERs, a comprehensive
review dealing with the state of the art of these resins has
not been published. In this paper, an attempt was made to
review the synthesis, characterization, and physicochemi-
cal, thermal, and mechanical properties of VERs.
VERs with wide structural variation can be prepared
by the reaction of different epoxide resins with various
unsaturated acids (Figure 2).
2      S. Jaswal and B. Gaur: Vinyl ester resins
CH3
HO CH2 CH O C C O CH2 C CH2 O C CH CH C
CH3 O O CH3 O O
Unsaturated polyester resin
CH3 CH3
H2C C C O CH2 CH CH2 O C O CH2 CH CH2 O C C CH2
O OH CH3
Figure 1 VER based on BPA epoxy.
Synthesis of VERs is usually catalyzed by tertiary
amines, phosphines, and alkalies or -onium salts (Jackson
1980, Rao et al. 1986, Peter et al. 1991, Boutevin et al. 1993,
Zaske 1998, Aggarwal et al. 1999, Gawdzik and Matynia 2001,
Srivastava et  al. 2002, Pal et  al. 2003) in the temperature
range of 80–110°C and taking reactants in stoichiometric
ratio. Complete esterification of the epoxy resin in practice
is difficult because of gelation of the product before an acid
value below 10 is attained. Therefore, an excess of epoxide
resin is always employed in the esterification reactions
(Sandner and Schreiber 1992, Wheelar 1955). The reaction
is monitored by determining the acid value and by Fourier
transform infra red spectroscopy (FTIR), proton nuclear
magnetic resonance (1H NMR), and Carbon-13 nuclear mag-
netic resonance spectroscopy (13C NMR) performed on the
samples withdrawn at regular intervals (Boutevin et  al.
1993, Aggarwal et  al. 1999, Gawdzik and Matynia 2001,
Malik et al. 2001, Srivastava et al. 2002).
2 Next-generation VERs
VERs in the neat form are highly viscous and, when used
with reactive diluents, show low viscosity during curing,
which leads to wastage of material and results into com-
posite starving of matrix resin in certain applications such
as sheet molding composites (SMCs). Structural modifica-
tions of VERs can be done to get workable viscosity levels
without using reactive diluents. It has been reported by
Oprea et al. (2000) that the reaction of secondary hydroxyl
group of VER with diisocyanate gives a resin with low vis-
cosity. On the contrary, chemical modification of the side
hydroxyl groups by dicarboxylic acid anhydrides produced
half ester acids using pyridine as catalyst, which led to
thickening of resin during cure, as reported by Rao et al.
(1987) and Swisher and Grams (1971). In order to obtain a
product that shows faster cross-linking ability in UV light,
Wang (2003) synthesized siloxane-based epoxy acrylates.
OH
n
CH3
OH O
n
3 Bio-based VERs
Ecofriendly VERs using renewable sources, e.g., cardanol
from cashew nut, can be synthesized to reduce viscosity,
curing time, and concentration of styrene (Sultania et al.
2010). VERs prepared from rosin-acid-based epoxy resin
have been reported, with improved coating abilities of
VERs due to faster drying and better chemical resistance
(Atta et al. 2006). Carbohydrate-derived isosorbide can be
used as core scaffold to synthesize novel and innovative
VERs with extremely low viscosity. These can fulfill the
requirement of high-performance composite resin since
these have higher cross-link density and give a high Tg
value of 245 ± 9°C compared with any other commercially
available VERs. These have the potential to be used as
viscosity modifiers without adversely affecting any other
qualities of the matrix material for high-performance
composite resin (Sadler et  al. 2013). Aliphatic matrix
resins derived from cycloaliphatic VER and glutaric acid
showed reduced UV absorption. These can be used to
obtain coatings and fiber-reinforced composites with
extreme durability to sunlight (Starr et al. 2001). Photo-
stabilization of VER was also reported by synthesized
interpenetrating polymer network modified lignin (Rosu
et al. 2009).
In order to obtain the starting material for the syn-
thesis of VERs from a renewable source, use of mycrene,
which is an oily liquid obtained by cracking on β-pinene of
turpentine, has been reported by Yang et al. (2013). These
mycrene-based VERs have rapid curing (∼50 s) in the pres-
ence of UV light. These resins also show excellent thermal
stability and good shore hardness. Attempts have also been
made by Li et al. (2013) to obtain VE bio-copolymer derived
from dimer fatty acid polymerized with glycidyl meth-
acylate and maleic anhydride modified dimer fatty acid
polymerized with glycidyl methacrylate resin. These were
further copolymerized with styrene and have been shown
to exhibit superior mechanical and thermal properties.
 S. Jaswal and B. Gaur: Vinyl ester resins      3

CH 3 CH 3

CH 2 CH CH 2 O C O CH 2 CH CH 2 O C O CH 2 CH CH 2

O CH 3 OH CH 3 O
n

Diglycidyl Ether of Bisphenol A

CH3 CH3

CH2 CH CH2 O C O CH2 CH CH2 O C O CH2 CH CH2

O CH3 OH CH3 O
n

Diepoxidized Hydrogenated Bisphenol A

O O O
C O CH2

Cycloaliphatic Epoxy
O O
CH 2 CH CH 2 CH 2 CH CH 2
N CH 2 N
CH 2 CH CH 2 CH 2 CH CH 2
O O
Tetraglycidyl Methylene Dianiline

O O
CH 2 CH CH 2 O CH CH 2
CH 2
N S N
CH 2 CH CH2 O CH 2 CH CH2
O O
Tetra Glycidyl Sulphone Dianiline
O
O CH 2 CH CH 2

O O
CH 2 CH CH 2 O CH O CH 2 CH CH2

Tri Glycidyl Triphenylmethane

O O O
O CH 2 CH CH 2 O CH 2 CH CH 2 O CH 2 CH CH 2

CH 2 CH 2

n
Epoxy Novolac

Unsaturated Acids
Acrylic acid: CH2 CH COOH

Methacrylic acid: CH2 CH COOH

CH3
Crotonic acid: CH3 CH CH COOH

Cinnamic acid: CH CH COOH

Figure 2 List of different epoxy resins and unsaturated acids used for VER synthesis.

4 Curing of VERs styrene, divinyl benzene, methyl methacrylate, etc., in

order to reduce its viscosity. These react with the back-
VER is dissolved in a reactive cross-linking monomer such bone polymer in the presence of organic peroxides and
as styrene, vinyl toluene, α-methyl styrene, p-tert-butyl hydroperoxides or azo and diazo compounds as free
4      S. Jaswal and B. Gaur: Vinyl ester resins
radical initiators to form a three-dimensional cross-linked
network. It has been reported that fatty acid monomers
obtained from renewable resources (La Scala et al. 2004a)
and bimodal blends of VE monomers (La Scala et al.
2004b, 2005) can replace styrene as reactive diluent to
reduce emission up to 78% (La Scala et al. 2004c). At low
temperature, promoters such as tertiary amines and salts
of metals like cobalt octoate or naphthenate can be used
to fasten the decomposition of initiators (Saunders 1973).
A mixture of initiators is used when a large temperature
increase is expected (Zaske 1998). Inhibitors like hydro-
quinone, tertiary butyl catechol, and toluhydroquinone
are added in very small amounts (in ppm) to the resin for-
mulations to inhibit premature gelation by consuming free
radicals that occur naturally in the resin. This improves the
shelf life of the resins.
The curing of VER containing styrene as reactive
monomer involves three possible reactive paths: styrene-
VE copolymerization, styrene homopolymerization, and
VE homopolymerization. During the curing process, the
physical state of thermoset resins changes from liquid
to gel and, ultimately, to a glassy solid. It is believed that
the heterogeneity of free radical cross-linking systems
during such reaction is an inherent result of the physi-
cal aspects of the free radical reaction and is explained
through widely accepted microgel theory (Saunders 1973,
Yang and Suspense 1991, Hsu and Lee 1993a,b, Chiu and
Lee 1995, Chen and Yu 1998). The curing of VE/styrene,
like vinyl-divinyl system (Dusek and Spevacek 1980),
shows an induction period due to the presence of inhibi-
tors and cage effect (Ziaee and Palmese 1999), in which
the inhibitor consumes the free radicals and very little
polymerization takes place. In stage I, which is the period
of accelerated propagation, the styrene monomer was
found to react at a slower rate than the VE monomer. The
kinetics of copolymerization is thought to be governed by
the intrinsic reactivity of the styrene and VE double bonds
and not by diffusion. In stage II, the polymerization rate
is dominated by Trommsdorff effect (Dua et  al. 1999).
According to Ganem and Mortaigne (1993), the polymeri-
zation of VE monomer decreases and polymerization of
styrene increases throughout this stage. The reason for
this is attributed to the higher mobility of the styrene mol-
ecule in the entire network, owing to its smaller size. The
VE double bond at the end of stage II becomes immobile
in the network due to its larger size. Toward the end of the
reaction, i.e., during stage III, the VE ceases to react while
the rate of consumption of styrene continues to increase,
which leads to the formation of polystyrene until vitrifi-
cation takes place (Ganem and Mortaigne 1993, Dua et al.
1999). The polystyrene formed cannot be extracted from
the fully cured VE resin as polystyrene chains are either
entangled within the matrix or that each chain is indepen-
dently grafted to the matrix (Ganem et al. 1994).
The cessation of the consumption of the methacrylate
double bond of VE led to the suggestion of biphasic struc-
ture and, subsequently, to the belief in the formation of
microgel with the occurrence of polymerization-induced
phase separation in VE/styrene systems. Atomic force
microscopy photographs of cured VE/styrene system also
endorsed the theory of microgel formation by showing
nodular morphology (Ziaee and Palmese 1999) or closely
packed microgels around 100  nm in diameter (Brill and
Palmese 2000) during the early stages of curing reaction.
Clusters of coral-like microgels with a maximum size of
4 μm were also observed by Li et  al. (2004) using scan-
ning electron microscope on the fractured surface of a
sample cured at 80°C. The density of clusters was found
to decrease when the isothermal curing temperature was
increased to 120°C. It was also observed that after curing,
the biphasic structure disappeared (Li et  al. 2004). Rey
et  al. (2000) investigated the morphological changes
during the course of copolymerization reaction between
tetraethoxylated bisphenol-A (BPA) dimethacrylate and
styrene or divinyl benzene. They reported the formation
of microgels using dynamic light scattering. Aggrega-
tion of microgels of diameter between 19 and 40 nm into
clusters was observed up to the gel point, after which
the macroscopic network is developed. The size of the
cluster was found to be greater for divinyl benzene due to
the large number of pendant double bonds as compared
with styrene. It was also observed that with increasing
cure temperature, the size of the microgels and clusters
became smaller. The two-phase structure of VE matri-
ces, unlike that of UPE resins, was found to be organized
rather than random structured, which gives excellent
hydrolytic stability to VE resins (Mortaigne et  al. 1997).
Various methods employed to study the curing behavior of
VERs are differential scanning calorimetry (DSC) (Chang
1992, Lee and Lee 1994, Cook et al. 1997), infrared (Ganem
and Mortaigne 1993, Brill et  al. 1996, Li et  al. 1999, Brill
and Palmese 2000), gel time studies (Abadie et al. 2002),
dynamic mechanical thermal analysis (DMTA) (Scott et al.
2002a), torsional braid analysis (Stone et  al. 2000), and
thermal scanning rheometry (Martin et al. 2000).
A variety of kinetic models have been used to relate
the rate of the cure reactions of the thermosetting resins
to time, temperature, and the extent of cure. These kinetic
models may be autocatalytic (Lee and Lee 1994, Auad
et al. 1999) or mechanistic (Kamal and Sourour 1973, Rey
et  al. 2000). Of these two models, mechanistic models,
despite giving better prediction and interpretation of the

curing reaction, are not easy to use in the process simu-
lation (Yang and Lee 2001). Autocatalytic models are,
however, generally preferred to mechanistic models since
these are expressed by a relatively simple rate equation
and are developed ignoring the details of how reactive
species take part in the reaction. The autocatalytic model
developed by Kamal and Sourour (1973) is being used by
many workers.
VERs exhibit autoacceleration in the polymerization
rate, which results into a single peak and cessation in
polymerization before the full conversion; i.e., vitrifica-
tion takes place (Mousa and Karger-Kocsis 2000). Many
workers though have observed two overlapping peaks or a
shoulder in isothermal DSC scans (Lem and Han 1984, Lee
and Lee 1994, Cook et al. 1997, Mousa and Karger-Kocsis
2000). Li et al. (1999) and Yang and Lee (2001) suggested
that the first peak was observed due to the copolymeriza-
tion between styrene and VE double bonds, whereas the
second peak was caused by the homopolymerization of
styrene monomers. It has been reported that with increas-
ing styrene content, the overall isothermal rate of curing
of VERs decreased and the shape of DSC isotherm also
changed from one peak to two. It has been reported by Li
et al. (1999) that promoter concentrations and cure tem-
peratures affected the reaction rates but did not change
the copolymerization mechanism between styrene and
VER and therefore did not influence the structure forma-
tion of copolymer. On the contrary, according to Ziaee and
Palmese (1999), the selection of cure temperature does
affect the structure of the VER/styrene network. They
compared the curing behavior of this system at 30°C and
90°C, respectively, by considering the reactivity ratios
of VE and styrene at these two different temperatures. It
has been reported that at 30°C, both active styrene and
VE prefer to react with VE double rather than a styrene
monomer. However at 90°C, an active VE prefers to react
with styrene monomer while active styrene still prefers to
react with VE double bond, thus yielding different struc-
tures at two different cure temperatures.
According to Lem and Han (1984), the first exotherm
peak arises from the cross-linking reaction that starts at
lower temperatures with free radicals generated through
a reversible complex formation between the initiator and
the promoter. However, according to Cook et  al. (1997),
the shoulder or the first smaller peak may be due to short-
term polymerization, attributed to H2O2 (present as impu-
rity in methyl ethyl ketone peroxide) initiation followed
by a broad maximum in the polymerization rate due to
Trommsdorff effect.
An increase in isothermal cure temperature (Lem and
Han 1984, Dhulipala et al. 1993) accelerated the rate of the
S. Jaswal and B. Gaur: Vinyl ester resins      5
reaction. Due to vitrification at low temperature, it was
observed that with an increase in isothermal cure tempera-
ture, there was an increase in heat of cure and a decrease in
residual heat during postcuring and net effect on the total
heat of cure was minimal. As in the dynamic conditions,
the resin cures thoroughly above the glass transition tem-
perature (Tg) and vitrification does not take place; the heat
of cure is found to be more than the total heat of cure under
isothermal conditions. The effect of different reactive dilu-
ents on the curing behavior of VERs has been studied by
many researchers ( Jackson 1980, Varma et al. 1985, Bhat-
nagar and Varma 1989, Gaur and Rai 1992a, Choudhary and
Varma 1993, Malik et  al. 2001). The addition of α-methyl
styrene in VER increased the gel time and suppressed the
peak exotherm (Bhatnagar and Varma 1989). Typical DSC
scans (Gaur and Rai 1992b) for the curing of VERs contain-
ing methyl, ethyl, and butyl acrylates at a program rate of
10°C min-1 are given in Figure  3. Less polar ethyl acrylate
was found to be more reactive to VER as compared with
methyl and butyl acrylate due to large differences in the
polarity of acrylates.
The effect of concentration of styrene on thermome-
chanical properties has also been studied using the DMTA
technique. Glass transition temperature, Tg, can be deter-
mined with significant levels of sensitivity by monitoring
the changes in the storage modulus, E′, loss modulus, E″,
Exothermic
Heat flow
3
1
Endothermic
2
40 60 80 100 120 140 160 180
Temperature (°C)
Figure 3 DSC scans for the curing reaction at 10°C min-1 of VERs
containing 40 wt% of (1) methyl acrylate, (2) ethyl acrylate, and
(3) butyl acrylate.
6      S. Jaswal and B. Gaur: Vinyl ester resins
or the loss tangent, tan δ, as a function of temperature. It
has been reported that the Tg and the temperature of the
tan δ maximum were not significantly affected by styrene
content. The magnitude of the rubbery modulus was found
to increase while the tan δ maximum decreased with the
increased cross-link density (cross-linkable methacrylate
group) (Scott et al. 2002a). The effect of cure temperature
on dynamic mechanical properties has been investigated
by Cook et al. (1997). They found that for the samples cured
at room temperature, two apparent glass transition regions
at approximately 65°C and 115°C were exhibited in the
DMTA trace. In contrast, only one transition was observed
for the “fully” cured sample. The reason for this anoma-
lous behavior was attributed to the additional cure that
occurred on further heating during the DMTA experiment,
which provided sufficient molecular mobility to recom-
mence the curing process, causing a shift in the transi-
tion region and an increase in the modulus. Martin et al.
(2000) determined gel time and vitrification time using the
DMTA technique. According to them, gel time is the time
at which the maximum in tan δ curve appears and corre-
sponds to the difference between the storage and the loss
modulus, i.e., the time at which the resin begins to cross-
link, generating maximum difference between the elastic
and the viscous behavior. The second maximum in tan δ
curve gives the vitrification time (Figure 4). The viscoelas-
tic behavior of the material in this time interval is due to
the increase in either the storage or the loss modulus.
5 Photopolymerization of VERs
VERs are the most common thermosetting resins used for
the fiber-reinforced polymer (FRP) composites that can
1.4
η′′ 400
1.2 η′
tan δ
1.0
η′′ (kPa-s)
0.8
tan δ
0.6
0.4
0.2
0.0
0 20 40 60 80 100 120
Time (min)
Figure 4 Storage modulus (G′), loss modulus (G″), and tan δ vs.
time for the VER from DMTA.
be cured in light using various photoinitiators at room
temperature. It has been reported that photoinitiators
like bis-acylphosphine oxide, its blends with α-hydroxy
ketones, and camphorquionone/amine in the VER/
styrene system were found to provide the fastest curing,
best through-cure of the composites and gel coatings,
high styrene incorporation yields, and good mechanical
properties (Cook 1992, Baikerikar and Scranton 2001, Sitz-
mann et al. 2001, Scott et al. 2002b, 2003a,b), which lead
to significant productivity enhancements. However, rate
of photopolymerization varied with the type of monomer
used as reactive diluents due to the different reactivity of
these monomers.
6 Effect of low-profile additives
To improve fracture resistance and to control volume
shrinkage of VER, they are usually blended or reacted
with different thermoplastics and nonreactive additives
or modifiers such as PVAc, PMMA, and polyurethane-
based low-profile additives (LPAs). The mechanism of
shrinkage control has been studied extensively in the
case of UPE resins. PVAc initially forms soluble or stable
dispersion with UPE resin before cure. During curing at
concentrations higher than the critical value at around 5
wt% PVAc levels, a co-continuous structure is obtained
as PVAc is pushed to the surface of the growing microgel
particle, which reduces the tendency of the resin particles
to coalesce, which leads to the formation of continuous
PVAc phase interpenetrating the cross-linked network
phase (Han and Lem 1983, Bucknall et  al. 1985, 1991a,b,
Suspene et al. 1991, Lucas et al. 1993, Kinkelaar et al. 1994,
Cook et  al. 1998). Although LPAs do not show the same
shrinkage control efficiency in VER as in UPE when cured
80 at low temperatures, they are effective in reducing the
surface defects and internal stresses (Cao and Lee 2003)
due to shrinkage by thermal expansion of thermoplas-
60
tic phase and development of void structure within this
300
phase. Saturated polyester formed from block copolymer
η′ (kPa-s)
40 of dibasic acid and an ethylene oxide/propylene oxide can
200
be used as LPA for the high-temperature SMCs using VER
20 as polymer matrix. The addition of polyester showed good
100
physical properties and zero shrinkage for these compos-
ites (Cook et  al. 1998). It is observed that increased LPA
0 0
concentration, low initial heating rate, and high peak
140 temperature were considered to be the most desirable
conditions for shrinkage control. The curing behavior of
VERs is not affected significantly by the presence of PVAc
or its phase precipitation. Conversely, it has been reported
 S. Jaswal and B. Gaur: Vinyl ester resins      7

elsewhere that the addition of LPA decreased the rate of results in an increase in strength and stiffness than curing
cure and also the final degree of cure of the resin (Han in natural conditions.
and Lem 1984).

8 Rubber toughening of VERs

7 Mechanical properties
VERs are preferred materials for structural composites
due to their excellent mechanical properties and tough-
ness (Table 1) (Cassis and Talbot 1998). The rigidity of the
prepolymer, the type and concentration of reactive dilu-
ents, and the cross-link density are the major contributing
factors to the mechanical strength of the cured VER. It has
been observed that an increase in the cross-link density
results in an increase in the glass transition temperature
and modulus (Scott et al. 2002a) and a decrease in strain-
to-break and impact energy (Cassis and Talbot 1998). The
VERs produced by epoxy novolac with methacrylic acid
provide more unsaturation sites than BPA-based VERs do
and produce greater toughness, resiliency, solvent resist-
ance, and heat resistance due to epoxy backbone of dif-
ferent molecular weights. Dilution with styrene resulted
in a decrease in glass transition temperature (Choudhary
and Varma 1993) and tensile strength and an increase in
the elongation of neat resin casting and glass-fiber-rein-
forced laminates. Cure temperature, cure formulation,
and curing method also affect the mechanical properties
of VERs. Ziaee and Palmese (1999) found that the fracture
toughness of BPA-based VER samples cured at 30°C using
cumyl hydroperoxide as initiator and cobalt naphthen-
ate as promoter and then post cured at 125°C was three
times greater than for the samples cured using the same
formulation at 90°C and post cured at 125°C. Ganglani
et al. (2002) reported that using N,N-dimethyl aniline as
an accelerator during cure lowers the tensile strength,
fracture toughness, and strain-at-break and results in
maximum methacrylate conversion. Benzoyl peroxide
was debated to be a better initiator as compared with
cumyl hydroperoxide. Microwave curing in a shorter time
VERs are limited by their brittleness (Pantano et al. 2002),
especially when good impact behavior is needed. One of
the methods used to increase toughness is the modifica-
tion of the resin with high-molecular-weight reactive liquid
rubbers such as polybutadiene, butadiene acrylonitrile
copolymer, polyepichlorohydrin, and polyacrylates, with
molecular weights in the range of 2000–5000 gmol-1 (Ullett
and Chartoff 1995, Auad et  al. 2001, 2002, 2003). During
cure, the discrete rubber-rich second phase formed in the
matrix improves its fracture toughness provided that this
second phase meets certain criteria relative to size, shape,
volume fraction, dispersion, and adhesion. However, poor
miscibility and poor reactivity of rubber with resin are sig-
nificant problems in achieving a suitable morphology for
toughening. A nonhomogeneous mass is formed that is
undesirable for the composite processing and resin control
during cure. Attempts were made to improve the compat-
ibility of rubber with VER by increasing the temperature,
ultrasonic treatment, and use of surfactants (Dreeman et al.
1999); however, they failed to improve compatibility. The
use of butadiene-acrylonitrile (VTBN)/epoxy-terminated
butadieneacrylonitrile-based rubber modifier without the
use of compatibilizers has been reported. These modifi-
ers, while limiting plasticization of the resin matrix, gave
a system increased fracture toughness and stress intensity
factor (Dreeman et al. 1999, Robinette et al. 2004).
Siebert et  al. (1996) were able to obtain an approxi-
mately 540% increase in stress intensity factor with high
rubber levels, which also led to significant plasticization
of the resin matrix. However, a limited amount of rubber
should be added so that the modulus and the strength
of base resin will not be affected (Achary et  al. 1991,
Ullett and Chartoff 1995, Auad et  al. 2001). Modification

Table 1 Mechanical properties of cured UPE resins and VERs (Malik et al. 2000).

Property   Ortho-  Iso-  BPA  Chlorendic  BPA-based  40 wt% fiber-glass-reinforced

resin resin fumarate VE resin BPA-based VE resin

Tensile strength (MPa)   55  75  40  20  80  160

Tensile modulus (GPa)   3.45  3.38  2.83  3.38  3.5–3.9  11.0
Elongation at break (%)  2.1  3.3  1.4  –  4.0  –
Flexural strength (MPa)   80  130  110  120  140  220
Flexural modulus (GPa)   3.45  3.59  3.38  3.93  3.7  9.0
Heat distortion   80  90  130  140  100  –
temperature (°C)
8      S. Jaswal and B. Gaur: Vinyl ester resins

of low-molecular-weight hydroxy terminated polybuta-
dienes (HTPB) through reaction with diisocyanate gave a
more compatible resin system, which led to improvements
in adhesion and mechanical strength (Achary et al. 1991,
Pham and Burchill 1995). End capping of polybutadiene
with various end groups and the mechanical test results
for the VER toughened with modified polybutadiene are
listed in Tables 2 and 3, respectively (Pham and Burch-
ill 1995), which shows that with increasing length of the
end groups, the ability to provide a tougher cured resin
improves such that the energy to propagate a slow crack
increases 10 times. Addition of only 5% modified rubber
led to a 2- to 3-fold increase in stress intensity factor and
10-fold increase in energy required for fracture in VERs.
Toughening of VER matrix is also reported to be carried
out by blending the resin with core-shell polymer addi-
tive with a polybutadiene core, which is useful for typical
structural commercial materials, e.g., polymer concrete
with increased flexural strength (Burchill et al. 2001). Sat-
urated elastomeric comb copolymers prepared with the
backbone of polyacrylate with a carboxyl group at each
end and pendant chains derived from the macromer of
polycaprolactone in a manner analogous to that of CTBN
have also been reported as reactive modifiers to improve
the toughness or flexibility of thermosetting resins, includ-
ing epoxy resins and VERs (Yu 1996). Due to the absence of
double bonds, these reactive modifiers are preferred to the
conventional CTBN elastomers as these are more resistant
to UV light and thermooxidative degradation and can be
used at elevated temperatures.
9 Thermal, oxidative, and
photostability
VERs containing fillers and reinforcements are com-
monly used in elevated temperature applications,
especially in areas demanding electrical and corrosion
resistance. Although fillers and reinforcements improve
the stability of the composites at high temperatures, the
resin, at some point, begins to dissociate chemically. The
cross-linked resins, irrespective of the composition of VE
or the vinyl monomer, undergo spontaneous decomposi-
tion at temperatures of around 300°C, which is a char-
acteristic of the vinyl polymers. Single-step degradation
has been obtained using a thermogravimetric analyzer
(TGA) for cured VER containing 40 wt% styrene as dilu-
ents (Gaur and Rai 1992a, Agarwal et al. 2002). Two-step
degradation thermogravimetry scan was reported when
a mixture of styrene and methyl methacrylate was used
(Agarwal et  al. 2003). The decomposition behavior of
epoxy novolac-based VER samples of varied acid values
(11–48  mg KOH g-1 solid) containing 40 wt% of styrene
as reactive diluent using TGA (Gaur and Rai 1992a) showed
the cured product with the lowest acid value precur-
sor to be the most thermally stable, with a lifetime of
16.58  years at 400°C. In VE, networks based on BPA
cured in the presence of benzoyl peroxide and exposed
to UV with λ  ≥  300 nm in the presence of oxygen formed
unstable hydroperoxides, which led to the fragmentation
of VE network into highly volatile low-molecular-weight
products (Rosu et al. 2008).
10 Chemical resistance and water
absorption
VERs are used to handle most hot, highly chlorinated,
and acid mixtures even at a high temperature due to the
better chemical and solvent resistance of VERs compared
with other thermoset resins ( Jacob 2003). The excellent
acid base resistance of epoxy-based methacrylated VERs
is due to their low ester content and protection of the ester
linkages by the methyl shield of the methacrylate group.

Table 2 Polybutadiene end capped with various chain ends [Pham and Burchill 1995].

PB1 HTPB end capped with MDI, i.e., bis(4-isocyanatophenyl) methane. Free isocyanate.
(MDI-PB-MDI)
PB2 HTPB end capped with MDI. Excess isocyanate was neutralized with hydroxylpropylmethacrylate (HPM).
(HPM-MDI-PB-MDI-HPM)
PB3 HTPB end capped with MDI. Excess isocyanate was neutralized with triethylene glycol (TG).
(TG-MDI-PB-MDI-TG)
PB4 HTPB end capped with CRM (MDI terminated-terminated polypropylene glycol). Excess of isocyanate was neutralized with methanol (Me).
(Me-CRM-PB-CRM-Me)
PB5 HTPB end capped with MDI. Excess isocyanate was neutralized with TG-MDI-TG.
(TG-MDI-TG-MDI-PB-MDI-TG-MDI-TG)
 S. Jaswal and B. Gaur: Vinyl ester resins      9

Table 3 Mechanical test results for VERs toughened with modified polybutadiene (Pham and Burchill 1995).

Samples   KIci  KIca  GIci  GIca  Ksen  E

Derakane 411-15 (BPA-based VE resin)  0.72  0.63  157  122  1.12  2.82
5 wt% HTPB   1.20  0.65  560  163  1.02  2.24
5 wt% PB1   1.86  0.89  1369  314  1.46  2.08
5 wt% PB2   1.67  0.82  1051  253  1.44  2.32
5 wt% PB3   1.91  0.82  1390  258  1.44  2.36
10 wt% PB3   2.36  2.36  2571  2571  1.63  1.95
5 wt% PB4   2.22  2.22  1948  1948  1.56  2.10
5 wt% PB5   2.04  2.04  1751  1751  1.61  2.13
5 wt% PB3   2.59  2.59  3749  3749  1.75  1.33

The VERs are found to be the most resistant in acidic envi-
ronments and distilled water, with better retention of the
mechanical properties (Lee et  al. 1992, Ghorbel and Val-
entin 1993, Valea et al. 1999, Kumosa et al. 2001). The VER
samples copolymerized with styrene (45 wt%) at room
temperature absorbed less water (0.8 wt%) than did the
samples without styrene. The amount of water absorbed
also increased with the increase in temperature. Karbhari
and Wang (2004) used DMTA to observe that the exposure
of glass-fiber-reinforced VE composites to water initially
caused plasticization, resulting in a decrease in the inten-
sity of the loss tangent (tan δ) peak as well as a decrease
in the glass transition temperature. Subsequent to this,
lower-molecular-weight species gets leached out, result-
ing in an increase in the glass transition temperature and
a change in the loss tangent profile. This phenomenon
could be termed as antiplasticization effect. The response
of these resins to an alkaline solution showed an initial
increase in brittleness due to moisture induced after
curing, followed by the effect of plasticization. Rubber-
modified VER is shown to have property retention similar
to that of standard BPA-based VER except for the lower
solvent resistance to low-molecular-weight solvents such
as ethanol and toluene (Kardenetz et  al. 1985). The cure
schedule also influences the resistance of the resin toward
different solvents. It is observed that the resin samples
that are not subjected to post curing are more easily
attacked by solvents brought in contact with them (Valea
et al. 1998).
11 Applications
11.1 VERs as coatings and adhesives
The use of VERs as coating material has gained increasing
popularity since the 1990s. Nowadays, VERs are being used
as new-generation self-healing coatings. These coatings
have a self-protective ability to smartly resist mechani-
cal and chemical damages caused by external aggressive
environment. VERs containing TiO2 particles have been
reported as a self-healing coating material for aluminum
alloy 5083, which guard the metal surface. In case of abra-
sion to the coating, the aluminum is said to react with BPA,
which is a chemical precursor of VER, and forms a barrier
at the damaged part, where these rutile particles serve as
receptacles for the BPA. This diminishes the damage by
the external hostile conditions on the surface (Stankie-
wicz et al. 2013). Although the same coating was not found
to be effective in inhibiting the corrosion of carbon steel,
a three-layered coating consisting of superabsorbent
polymer mixed with VER sandwiched in between the top
and base layers consisting of pure VER showed better
polarizing resistance (Yabuki and Okumura 2012). Modi-
fication in the base resin by reaction of the secondary
hydroxyl group of triglycidyl ether of m-amino-phenol-
based VERs with isocyanurate to obtain urethane linkages
resulted in a coating that showed superior adhesion to
the steel panels and exhibited good chemical resistance
to various acids, alkalies, water, and organic solvent as
compared with that of triacrylated derivatives (Patel et al.
1999). VER composites with different types of fillers have
also been explored as high-performance coatings. Ehsani
et al. (2013) has reported the use of glass flakes (GFs) as
reinforcement fillers to enhance the physical properties
(i.e., modulus, thermal expansion, thermal and electrical
conductivity, and magnetic recording) of VER composite
used for coating applications. A study of GF-reinforced
polymer composite using DMTA in the temperature range
of 25–180°C showed that in increasing the GF content from
5 parts per hundred resin (phr) to 15 phr, there was an
increase in storage modulus, whereas higher thermal sta-
bility was obtained with 25 phr GF content due to thicker
GF-enriched char layer build up on the surface of the com-
posite. As the filler content was increased from 0 phr to 15
phr, a decrease in reaction enthalpy and glass transition
temperature of the composite system was observed.
10      S. Jaswal and B. Gaur: Vinyl ester resins
VER is a promising class of thermosetting matrices
used as adhesives with high strength and toughness,
enduring service at high temperatures and chemical con-
frontation for structural bonding applications as well as
in repair applications. It has been reported that liquid
crystalline VER synthesized from p-(2,3-epoxypropoxy)-
α-methylstilbene as epoxy monomer showed excellent
adhesive strength for aluminum substrate (Ambrogi et al.
2002). The methacrylate group of the resin acts like Lewis
acid and interacts with aluminum oxide that acts as a
Lewis base, both through the carbon-carbon double bond
and through carbon-oxygen double bond present on the
resin. It is believed that the resin shows adhesion to the
oxide layer immediately before the curing reaction occurs
and thus provides a stable structure after cure.
11.2 VERs as matrix for composite materials
Polymer matrix composites and especially FRPs are
widely utilized in construction applications, including
industrial and agricultural buildings, due to their high
mechanical strength, tailored design through controlled
anisotropy, chemical and thermal stability, acoustical
characteristics, light transmission and translucency,
electromagnetic transparency, electrical nonconduc-
tivity, etc. (Taranu 2009). VERs, which are the leading
candidate among thermosetting polymers, can serve as
matrix material for producing fiber-reinforced compos-
ites, short fiber-reinforced composites, as well as par-
ticulate composites. These thermoset resins are shown to
have very good adhesion to glass fibers, aramid fibers,
as well as carbon fibers. Composites based on VERs are
used in a variety of engineering applications and espe-
cially for wear-sensitive applications. A comparison of
the tribological properties of the composite produced by
using glass fiber and carbon fiber, respectively, showed
that carbon-reinforced VER composites show supe-
rior wear resistance and lower coefficient of friction as
compared with glass-fiber-reinforced VER composites
(Suresha et al. 2010). The influence of aluminum ceramic
particulate on the tribological characteristics of E-glass-
fiber-based VER composites has also been studied by
Chauhan et  al. (2013). The minimization of erosion or
wear performance was also observed in hybrid VER com-
posites consisting of short glass and carbon fiber (1:1)
with different fiber weight fractions (from 20 wt% to
50 wt%) (Kumar et  al. 2012). Ku et  al. (2007) were able
to reduce the shrinkage of the VE composite contain-
ing flyash as particulate filler by curing the composite
sample in the presence of microwave. Microwave curing
not only showed lesser shrinkage but also gave the com-
posite better fracture toughness.
E-glass and Kevlar-49 fiber-reinforced VE laminates
have been reported to be used in ballistic applications
(Panda et  al. 1994). It has also been described that by
optimization of loading of short aramid fibers and exter-
nal variables (standoff resistance, impingement angle,
erodent size, impact velocity, etc.), erosion or wear perfor-
mance enhancement of short aramid-fiber-reinforced VER
composite can be successfully achieved (Kumar et al. 2011)
A comparative study of the chemical and thermal
behavior of two main types of thermosetting polymers,
i.e., polyester resin and VER, showed that the VER cure
reaction proceeded more slowly, because of which it
was able to form a more compact structure; as a result,
the VE/glass fiber composite gave better chemical resist-
ance against seawater (Visco et al. 2011). In order to use
these resins as matrix for preparing composites with high
dielectric strength, hollow glass microballoons were used
as fillers to obtain syntactic foams in order to develop inte-
grated circuit boards having good mechanical strength
(Shunmugasamy et al. 2013).
In the present era, the use of natural fiber reinforce-
ments has also gained substantial attention in composite
technology as a low-cost, lightweight, and environmental-
friendly alternative to other synthetic fibers. The mechani-
cal, chemical, and thermal properties of VER composites
unified with naturally obtained cellulose, cotton, and luffa
cylindrical fibers have also been investigated. Cellulose
fabricated VER composites showed a gradual increase in
water uptake, tensile modulus, and flexural strength with
an increase in cellulose fiber volume fraction in composites
(Alhuthali and Low 2013a). The thermal and mechanical
behaviors of alkali-treated and -untreated cotton-fiber-
reinforced VE composites have also been reported by
Shahedefar and Rezadoust (2013). It was observed that the
use of alkali-treated cotton fiber to reinforce VER improved
the tensile strength and elongation-at-break of composites
by 5% and 25%, respectively, as compared with that of
untreated cotton fiber composites due to increased surface
roughness by the removal of wax and oil from the surface
of the fibers. Attempts have also been made by Siqueira
and Botaro (2013) to replace synthetic fibers by fibrous
mat of Luffa cylindrica ripe fruit as reinforcement and alu-
minum hydroxide as polymer additive to prepare VER com-
posites. These fibers of L. cylindrica were modified with
1,2,4,5-benzenetetracarboxylic dianhydride and NaOH
(mercerization) to increase the interfacial compatibility,
adhesiveness, and wettability between L. cylindrica fibers
and VE matrix. These composites obtained also showed
improved thermal and mechanical properties.

11.3 Nanostructured VER composites
Polymer nanocomposites are polymer matrix composites
in which the reinforcement has at least one of its dimen-
sions in the nanometer range. These composites show
superior mechanical, thermal, electrical, optical, and
other properties at relatively low reinforcement volume
fractions. The transition from microparticles to nano-
particles yields dramatic changes in physical properties.
Nanoscale materials have a large surface area for a given
volume, and many properties (chemical and physical)
are governed by surfaces and surface properties (Luo and
Daniel 2003, Thostenson et al. 2005). The use of organic
or inorganic nanofillers such as carbon nanofibers, cel-
lulose fibers, titanium oxide nanoparticles, etc., has
become ubiquitous in the present-day matrix materials
for developing nanocomposites. Efforts are always being
made in order to develop material with better macro-
scale properties. Jang et  al. (2012) has studied the inter-
facial interactions between the surfaces of oxidized vapor
grown carbon nanofiber (VGCNF) and VE monomer and
reported the formation of 5–10 Å stiffer interphase, which
affected the interfacial adhesive bonding. This bonding
could be increased by increasing the polar interactions
between the matrix and oxidized VGCNFs. Nanocompos-
ites developed by Shahrajabian et  al. (2013) using TiO2
nanoparticles showed excellent mechanical and thermal
properties, which were seen to increase after the compos-
ites were exposed to electron beam. Recycled cellulose
fiber sheet based VE-containing nanoclay filler eco-nano-
composites were developed and were further investigated
for water uptake and mechanical and thermal proper-
ties. Nanoclay addition to the polymer matrix decreased
water uptake and increased thermal stability, mechanical
strength, and fire-resisting properties due to better inter-
facial interactions between fiber and matrix, although it
was observed that the addition made the nanocomposite
brittle (Alhuthali et al. 2012). Chaturvedi et al. (2013) has
described the development of graphene-reinforced VE
nanocomposites. Graphene sheets can be used to resolve
the serious concerns related to the use of carbon nano-
tubes, primarily the cost and limited production. Multi-
walled carbon nanotube unified VER nanostructures can
become an emerging electrically conductive polymeric
system (Yurdakul et  al. 2010). Multiwalled carbon nano-
tube-VE cross-linking nanostructures have also been used
for bipolar plates in proton exchange membrane fuel cells.
This unique system showed significant enhancement in
performance of the fuel cell due to better dispersion of
carbon nanotubes into the matrix, higher mechanical
strength, and superior electrical conductivity. Thostenson
S. Jaswal and B. Gaur: Vinyl ester resins      11
et  al. (2009) has reported that due to the low electrical
percolation threshold of VER as matrix, high aspect ratios
of carbon nanotubes were maintained during nanocom-
posite formation and an electrically conductive network
was formed throughout the laminate, which in turn led to
the utilization of carbon nanotubes as in situ sensors for
detecting deformation and damage in advance naval com-
posite structures.
Halloysite nanotubes (HNTs), which originate from
naturally deposited alumiosilicate [Al2Si2O5 (OH)4.H2O]
and have chemical analogy to kaolin, have been unified
with VERs to reduce water uptake and amplify thermal
and mechanical properties. HNTs have also been found to
be effective in increasing the toughness of the material.
It has also been reported that this nanocomposite attains
good thermal stability and flame retardancy due to the
hollow tubular structure of HNTs as well as the presence
of Fe2O3 as impurity (Alhuthali and Low 2013b). Improved
toughness properties of VER nanocomposites containing
polypropylene mesofibers have been reported by Liang
et al. (2011).
12 Conclusion
VERs either in the pure form or in compounded form
with fillers have use in a wide range of applications. The
growth of VERs has also been boosted because of their
excellent handling characteristics and easy cure. These
are the prime candidates for composites in transporta-
tion and infrastructure applications for construction of
parts of automobiles, polymer concretes, reinforcements
for bridges, etc., due to their excellent thermal perfor-
mance and mechanical properties. Because of their
inherent resistance to chloride attack and long service
life, composites of VERs are adopted by the paper and
pulp industries as well. VERs based on epoxy novolacs
are used for chemical storage tanks, pipes and ducting,
fume extraction system, and gas cleaning units, as these
resins show superior chemical resistance at high tem-
peratures. These have high tensile elongation along
with superior corrosion resistance, which makes them
a promising material for producing lining and coating
with outstanding adhesion to other types of plastics
and conventional materials such as steel and concrete.
VERs also have a variety of applications in optical fiber
coating, topcoats for metal containers, UV curing inks,
as well as printed circuit boards (Radhakrishnan and
Pethrick 1994, Bajpai et  al. 2004, Chattopadhyay et  al.
2005).
12      S. Jaswal and B. Gaur: Vinyl ester resins
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Shipra Jaswal received her bachelor’s degree in 2006 and master’s
degree in 2008 from Himachal Pardesh University, Shimla,
Himachal Pradesh, India. She is currently pursuing her PhD on the
synthesis of hyperbranched vinyl ester resins based on natural
products from the National Institute of Technology, Hamirpur,
Himachal Pradesh, India. She is also working in a project as women
scientist under Women Scientist Scheme-A, approved by Depart-
ment of Science and Technology, New Delhi, India. She has three
publications in national and international conferences.
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Bharti Gaur is an associate professor in the Department of Chemis-
try, National Institute of Technology-Hamirpur, Himachal Pradesh,
India. She received her BSc degree from St. Bedes College Shimla in
1986. She completed her postgraduate studies in organic chemistry
from Sardar Patel University, Anand, Gujarat, India, in 1988. She
obtained her PhD degree from HBTI Kanpur, India, in 1993. She has
worked as a scientist in IIT Delhi for 2 years, where she filed two
patents in the area of energetic binders for solid rocket propellants.
She has taught in a number of undergraduate and postgraduate
institutes before joining NIT Hamirpur as an assistant profes-
sor in 2010. She has more than 25 research papers in national
and international journals and conferences. Her current research
interests include microbial fuel cell, synthesis of proton exchange
membrane for fuel cells, nanocomposites, synthesis of adhesives,
and coatings.