Polymer International Polym Int 49:281±287 (2000)

Toughened epoxy adhesive modified with

acrylate based liquid rubber
D Ratna1 and Ajit K Banthia2*
1
Naval Materials Research Laboratory, Chickloli, Anandanagar PO, Addl Ambernath (E), Thane-421 506, India
2
Materials Science Centre, Kharagpur-721 302, India

Abstract: The adhesive and mechanical properties of epoxy resins modi®ed with carboxyl terminated
poly(2-ethylhexyl acrylate) (CTPEHA) liquid rubber have been investigated as a function of the
concentration of liquid rubber. CTPEHA was synthesized by the bulk polymerization technique.
CTPEHA oligomer was prereacted with the epoxy and the modi®ed epoxy networks were made by
curing with an ambient temperature curing agent. The modi®ed epoxy networks were evaluated with
respect to their adhesive and mechanical properties. The optimum properties were obtained at about
10±15 phr (phr stands for parts per hundred parts of epoxy resin) concentration of modi®er. Fracture
surface analysis by optical microscopy (OM) indicates the presence of two phase microstructures.
# 2000 Society of Chemical Industry

Keywords: epoxy; 2-ethylhexyl acrylate; impact; adhesive; toughened; modi®ed

INTRODUCTION temperature.13 One would imagine that excessive

Epoxy resins have been used as adhesives since the
1950s due to their better wetting ability, low cure
shrinkage, superior mechanical properties and excel-
lent chemical resistance.1±3 However, when cured with
stoichiometric amounts of polyfunctional amines, the
high degree of crosslinking makes epoxy resin a brittle
material having fracture energy about two orders of
magnitude lower than engineering thermoplastics and
three orders lower than metals.4 This weakens the
peeling and impact strength of epoxies and therefore
limits their applications. The use of long chain
hardener, and compatible blendings is reported in
the literature as solutions to this problem,5,6 but these
methods are associated with signi®cant reduction of Tg
and mechanical strength.6 The most successful meth-
od is blending with suitable reactive liquid rubbers.7,8
Initially, the liquid rubber remains compatible with the
epoxy hardener mixture, but with the advancement of
curing reaction it undergoes phase separation at a
certain stage leading to the formation of a two phase
microstructure.8,9 The beauty of this method is that
the improvement of impact and adhesive strength is
achieved without signi®cant deterioration of thermo-
mechanical properties.10,11
A liquid rubber such as carboxyl terminated
copolymer of acrylonitrile and butadiene, ie CTBN
toughened epoxy, often shows outstanding fracture
properties and this technology is exploited in the ®eld
of engineering adhesives.12 However, because the
butadiene component of the elastomers contains
unsaturated bonds, it would appear to be a site for
premature thermal and/or oxidative instability; such
modi®ed resins are not suitable for application at high
crosslinking could take place with time which would
detract from otherwise desirable improvements ac-
complished with these structures. Secondly, there is
some limitation in its use due to the possibility of the
presence of traces of free acrylonitrile which is
carcinogenic.14 Moreover, most of the reported rubber
toughened epoxy formulations suffer from the
problem of heat cure. Heat curing is dif®cult and
impractical for fabrication of certain structures and
requires signi®cant amounts of energy. Ambient
curing saves energy and is advantageous for applica-
tion of surface coating and adhesive onto an intricate
structure. Acrylate based liquid rubber can be a
substitute for butadiene based rubber for toughening
epoxy resin because of its comparatively better oxi-
dative and thermal stability.15 One of the authors has
shown that among acrylate monomers, 2-ethylhexyl
acrylate is an ideal choice for the synthesis of reactive-
group-ended liquid rubber.16
The aim of the present work is to synthesize a low
molecular weight liquid carboxyl terminated poly(2-
ethylhexyl acrylate) (CTPEHA) and examine its effect
on the adhesive properties of epoxy resin. The present
paper discusses the synthesis and characterization of
CTPEHA, development of CTPEHA modi®ed epoxy
networks using an ambient temperature curing agent,
and their evaluation with respect to mechanical and
adhesive strength.
EXPERIMENTAL
Materials
The monomer 2-ethylhexyl acrylate (EHA) (Fluka)

* Correspondence to: Ajit K Banthia, Materials Science Centre, Indian Institute of Technology, Kharagpur-721 302, India
(Received 17 May 1999; revised version received 13 August 1999; accepted 8 November 1999)

# 2000 Society of Chemical Industry. Polym Int 0959±8103/2000/$17.50 281

D Ratna, AK Banthia
was puri®ed by washing twice with sodium hydroxide
solution (5% w/v) to remove the inhibitors and then
repeatedly with distilled water. It was then dried over
anhydrous calcium chloride for 48 h. 4,4'-Azobis(4-
cyanovaleric acid) (ABCVA) (Aldrich) was recrysta-
lized from ethanol before use as a free radical initiator.
Dithiodiglycolic acid (DTDGA) (Aldrich) was used as
a chain transfer agent without further puri®cation.
Triphenyl phosphine (TPP) (SISCO, India) was used
as received. Solvents like toluene, methanol, etc, were
of analytical grade (BDH, India).
Epoxy resin was a liquid diglycidyl ether of bi-
sphenol A type (Ciba Geigy, Araldite LY 556) with an
equivalent weight per epoxide group of 195  5. An
ambient temperature hardener, triethylene tetramine
(Ciba Geigy, HY 951), was used as a curing agent.
Synthesis and characterization of CTPEHA
CTPEHA oligomer was synthesized by bulk polymer-
ization technique, using ABCVA as a free radical
initiator and DTDGA as a chain transfer agent. The
reaction was carried out in a three-necked reaction
¯ask (500 ml) ®tted with a stirrer, thermometer pocket
and gas inlet. Approximately 100 g (0.54 mol) of EHA
monomer was placed in the reaction ¯ask and was
rapidly brought to the desired temperature. After the
system had been well purged with nitrogen gas, 3.0 g of
ABCVA (2 mol%) and 11.3 g of DTDGA (10 mol%)
were added and the reaction was allowed to take place
for 1 h under stirring. The mixture was then diluted
with toluene (200 ml) and immediately quenched to
room temperature and kept overnight. The unreacted
ABCVA and DTDGA were precipitated overnight
and subsequently ®ltered. Unreacted monomer and
the solvents were removed under vacuum on a rotary
evaporator until a constant weight was obtained.
The carboxyl content of CTPEHA was determined
by titration with a methanolic solution of 0.10 N KOH
using phenolphthalein as an indicator.
The viscosity measurement was carried out with a
Haake Rotoviscometer (Haake RVIII) over a shear
rate range of 0±100 sÿ1 at 27 °C using an MV III head
having a clearance of 0.96 mm between the concentric
cylinders of the viscometer.
The molecular weight of CTPEHA was determined
by a Knauer vapor pressure osmometer (VPO) using
toluene as a solvent and benzil as a standard. The
functionality ( f ) of the oligomer was calculated by
multiplying the carboxyl content, expressed in eq gÿ1
with the number average molecular weight. Function-
ality was expressed as eq molÿ1.
Solubility parameters were determined by an itera-
tion method from the three-dimensional solubility
parameters of the solvents in which the polymer is
miscible.17,18
Modification and curing procedure of epoxy using
CTPEHA
CTPEHA (100 pbw) (pbw stands for parts by weight)
was prereacted with epoxy resin (100 pbw) using
282
triphenyl phosphine (1 pbw) as a catalyst. The reac-
tion was carried out at 80 °C under nitrogen atmos-
phere until all carboxyl groups were completely
reacted. The epoxy end-capped poly(2-ethylhexyl
acrylate) oligomer was then diluted with an appro-
priate amount of epoxy resin to obtain various con-
centrations of CTPEHA in the formulations.
All the formulations were analysed for their epoxy
content by standard titration19 with hydrogen bromide
in acetic acid; accordingly, a stoichiometric amount
(26 g for one equivalent of epoxy) of TETA was added
and thoroughly mixed. The mixture was cast into a
te¯on mould and cured at room temperature (RT) for
2 days. Then the samples were post-cured at 80 °C for
2 h.
Characterization of modified networks
Adhesive properties
Adherends
Aluminium alloy (B 51 SWP) containing 0.4% Fe,
0.6% Mn, 1% Si and 0.8% Mg, and hardened teak
wood were used as substrates for measurement of
Al±Al and wood±wood lap shear strength. The
thickness of the substrates was 2 mm for aluminium
and 4 mm for wood. T peel tests were carried out using
0.3 mm thick aluminium adherends.
Treatment of the adherend surfaces
The procedure for the surface treatment of aluminium
adherend included four steps.
(1) The aluminium adherend was thoroughly washed
with acetone; then it was put in a forced air oven in
a vertical position and dried at 60 °C for 2 h.
(2) The acetone-cleaned aluminium adherend was
dipped in fresh distilled chloroform for 24 h and
was then dried in a forced air oven in a vertical
position at 60 °C for 30 min. Any contact with the
surface portion which would adhere should be
avoided.
(3) The chloroform cleaned aluminium adherend was
then dipped in a Na2Cr2O7/H2SO4 solution at
67  2 °C for 30 min. The composition of the
Na2Cr2O7/H2SO4 was Na2Cr2O7:H2SO4:H2O =
1:10:30 by weight. After dipping, the aluminium
adherend was washed with cold water for 3±5 min.
A well treated aluminium adherend should have a
continuous uniform water ®lm attached to the
surface: otherwise the treatment should be re-
peated again until a satisfactory result is obtained.
(4) The water washed aluminium adherend was
®nally dried in a forced air oven in a vertical
position at 60 °C for 1 h. The portion which will
adhere should be in the upper direction; the
specimen thus treated should be used within 12 h.
Hardened teak wood substrates were used without
any surface preparation.
Preparation of test Samples
Using a glass rod, the adhesive formulation was
Polym Int 49:281±287 (2000)

applied evenly to both the surface portions of the
adherends which would adhere; mating was by use of
contact pressure. The coating length was about 1 cm
(0.5 in) longer than the adhering length. The samples
were allowed to cure at room temperature for 2 days
and then post-cured at 80 °C for 2 h.
Measurements
Single lap shear and T peel strength were measured for
the sample before and after post-curing using the
UTM according to ASTM D 1002 and D 1876,
respectively. A crosshead speed of 20 mm minÿ1 was
used for the measurement of lap shear strength and
200 mm minÿ1 was used for measurement of T peel
strength. The lap shear strength is expressed in MPa,
this being calculated by dividing the load required to
break the adhesive bond (in newtons) by the contact
area. The T peel strength is calculated from the
following formula:
G ˆ 2F=w
where F is the force required to separate the joints and
w is the width of the specimen. Five specimens for each
formulation were tested and the average value is
quoted.
Tensile test
Tensile tests were performed on dumb-bell shaped
type IV samples according to ASTM D-638. The
dumb-bell shaped samples were prepared by casting
the liquid resin directly in the te¯on mould. The
samples were allowed to cure for 2 days at room
temperature and then post-cured for 2 h at 80 °C. The
tensile strength and percentage elongation at break
were measured using an Instron Universal Testing
Machine (UTM) (Model 1150) and a Zwick UTM
(Model 1445) ®tted with an extensometer. The cross-
head speed was 10 mm minÿ1 and the gauge length was
45 mm. The tests were carried out at 27  2 °C. The
elongation at break was measured using a non contact
IR extensometer. The results are expressed in MPa,
this being calculated by dividing the load (in newtons)
at break by the cross-sectional area of the dumb-bell
centrepiece. The quoted result is the average of the
results from six dumb-bells.
Flexural test
The ¯exural properties were measured with rectan-
gular samples according to ASTM D-790, using the
same UTM at a crosshead speed of 4 mm minÿ1. The
fracture strength (FS) was determined from the
Table 1. Physicochemical properties of CTPEHA and epoxy
Resin Molecular weight Mn Carboxyl functionality
CTPEHA 3625
LY556 425
a
At 26 °C.
Polym Int 49:281±287 (2000)
Liquid-rubber-modi®ed epoxy adhesive
following formula:
3 9:8
FS ˆ  peak load span   …thickness†2
2 width
…2†
The results are expressed in MPa and are the average
of ®ve samples.
Impact properties
The lzod unnotched impact test was carried out using
an Avery±Dennison impact tester with a striking
velocity of 3.46 m sÿ1. Impact test specimens in all
cases were 125  10  10 mm3. The impact test was
carried out at room temperature and impact energy is
reported in J mÿ1. The quoted result is the average of
the determinations on ten samples which were not
notched.
Fracture surface analysis
An optical microscope was used to analyse the fracture
…1†
surfaces (broken in the impact test) of the toughened
epoxy networks. All the photographs were taken at
600 magni®cation.
RESULTS AND DISCUSSION
Synthesis and characterization of liquid rubber
The physicochemical properties of CTPEHA are
shown in Table 1. The functionality of CTPEHA is
close to the theoretical value of 2, which indicates
essentially its telechelic nature. To evaluate its com-
patibility with the epoxy resin, its solubility parameter
was determined by examining its miscibility in
different solvents. The close proximity of the solubility
parameters indicates its compatibility with the epoxy
in the liquid state.
Prereaction of CTPEHA with epoxy and curing
For effective toughening, the liquid rubber needs to be
chemically bonded to the epoxy matrix.20,21 More-
over, a collection of free liquid rubber molecules at the
metal interface can act as a weak boundary layer in the
adhesive joints leading to substantial decrease in
adhesive joint strength.22,23 For this reason, before
curing the epoxy resin was prereacted with CTPEHA
in the presence of TPP as a catalyst until no carboxyl
group was found by titration. The reaction is basically
a carboxy±epoxy esteri®cation reaction, as proposed
by Romanchick et al. 24
The product was an epoxy end capped poly(2-
ethylhexyl acrylate)±epoxy copolymer which is capable
Viscosity a(Pa s) Solubility parameter (cal cmÿ3)0.5
1.91 27.5 9.79
± 7.4 10.32
283
D Ratna, AK Banthia
Figure 1. Prereaction of CTPEHA with epoxy.
of reacting with the hardener in the same way as epoxy.
A large excess of epoxy resin was used for end-capping
the CTPEHA, which made it possible for each
carboxyl group to react with an unreacted DGEBA
molecule and essentially prevent further polymeriza-
tion. The reaction is illustrated in Fig 1. The modi®ed
sample is liquid and no solidi®cation or gelling was
observed after prereaction. The diluted mixture was
then cured with HY 951. The gel time of unmodi®ed
and modi®ed epoxy with hardener HY 951 at 27 °C
are reported in Table 2. The gel times of the modi®ed
epoxies are longer than that of the unmodi®ed epoxy,
indicating that the epoxy±CTPEHA copolymer
formed by chain extention crosslinks at a slower rate
than the unmodi®ed epoxy.
Evaluation of modified networks
In order to study the effect of CTPEHA modi®cation
on the adhesive properties, various formulations were
made incorporating different levels of CTPEHA. All
the formulations were evaluated with respect to their
lap shear strength for aluminium±aluminium and
wood±wood joints, and T peel strength for alumi-
nium±aluminium joints. The evaluation was carried
out for each sample both before and after post-curing
Table 2. Gel time of prereacted CTPEHA modi-
fied epoxy samples
Epoxy/CTPEHA Gel time at 27 °C (min)
100/0 22
100/5 30
100/10 43
100/15 47
100/20 55
100/30 65
284
Figure 2. Effect of CTPEHA modification on the lap shear strength (Al–Al)
of epoxy resin.
according to the test method described in the
Experimental section.
The lap shear strengths of modi®ed and unmodi®ed
epoxy adhesive formulation for Al±Al joints, measured
both before and after post-curing are illustrated in Fig
2. They initially increased, and reached a maximum
with 10±15 phr of CTPEHA before decreasing.
The maximum lap shear strength was 8.4 MPa for
the sample cured at room temperature and 8.9 MPa
for the post-cured sample. The maximum lap shear
strength is about double the value for unmodi®ed
epoxy. The improvement in adhesive strength has
been reported by many authors using CTBN liquid
rubber as modi®er.25±28 Ramamurty and co-workers29
reported a three-fold increase in lap shear strength
using carboxyl terminated poly(propylene glycol)
adipate as a liquid rubber. The variation of lap shear
strength for wood±wood joints as a function of
CTPEHA concentration is shown in Fig 3. A similar
trend was observed for the lap shear strength of wood±
wood joints and Al±Al joints; however, the lap shear
strength of wood±wood joints was higher, the maxi-
mum value obtained being 11.6 MPa. The higher lap
Figure 3. Effect of CTPEHA modification on the lap shear strength
(wood–wood) of epoxy resin.
Polym Int 49:281±287 (2000)

Figure 4. Effect of CTPEHA modification on T peel strength of epoxy resin.
shear strength of wood±wood joints can be attributed
to the presence of cellulosic ÐOH groups which
increase the interfacial adhesion by hydrogen bonding.
The porosity of the wood surface also increases the
mechanical anchorage and thereby improves adhesive
strength.
The improvement in T peel strength is also achieved
as a result of addition of CTPEHA. T peel strength
increases initially, passes through a maximum and
then decreases with further increase in CTPEHA
concentration (Fig 4). The maximum T peel strength
of 512 J mÿ2 for the post-cured sample is obtained at a
modi®er concentration of 15 phr. The maximum value
of T peel strength for the sample before post-curing is
465 J mÿ2. The improvement in T peel strength due to
addition of rubber is 150% over the unmodi®ed epoxy.
The higher adhesive strength in the case of the post-
cured sample can be attributed to the increase in
crosslinking density resulting from post-curing.6,30
The increase in adhesive strength as a result of
incorporation of CTPEHA can be explained as due
to the toughening effect of the liquid rubber which
prevents or minimizes the catastrophic failure of
structural bonds.
The toughening effect is re¯ected in the increase in
impact strength as a result of the incorporation of
liquid rubber in the adhesive formulation. The effect
of incorporation of CTPEHA on the impact strength
of modi®ed epoxy networks is shown in Fig 5. The
impact energy gradually increases with an increase in
the CTPEHA concentration, attains a maximum and
then again decreases. The maximum impact strength
Table 3. Effect of CTPEHA modification on the mechanical properties of modified epoxy before and after post-curing
CTPEHA (phr) Tensile strength a(MPa) Elongation at break a(%) Flexural strength (MPa) Deformation at break (%)
0 48.3 (52.3)
5 39.7 (47.4)
10 37.8 (45.6)
15 32.6 (43.5)
20 28.6 (36.4)
30 15.7 (30.5)
a
Figures outside parentheses are results of tests carried out before post-curing; ®gures in parentheses are results obtained after curing for 2 days
at room temperature and post-curing at 80 °C for 2 h.
Polym Int 49:281±287 (2000)
Liquid-rubber-modi®ed epoxy adhesive
Figure 5. Effect of CTPEHA modification on impact strength of epoxy
resin.
of 36.2 J mÿ1 was obtained at a CTPEHA concentra-
tion of 10±15 phr; an approximate two-fold increase in
impact strength was achieved. It is well established
that small rubber particles dispersed in an epoxy
matrix increase the impact resistance by cavitation and
shear yielding.31±33 The reduction of impact energy
after an optimum the concentration is due to the
breakdown of the desired particulate morphology.
This will be discussed under optical microscopy (OM)
studies.
Table 3 shows the result of tensile tests carried out
for modi®ed and unmodi®ed epoxy samples before
and after post-curing; it is evident that tensile strength
increases and elongation at break decreases as a result
of post-curing. This can be attributed to the increase in
crosslink density during post-curing.6,30 The high
crosslink density makes the network tighter and more
resistant to yielding. The increase in tensile strength as
a result of post-curing for modi®ed epoxy samples is
more signi®cant in comparison to unmodi®ed epoxy
because the presence of an epoxy±CTPEHA copoly-
mer reduces the curing rate as is evident from the gel
time study (Table 2).
As the concentration of CTPEHA increases, the
tensile strength decreases and the percentage elonga-
tion at break increases slowly. This increase in
¯exibility is due to the presence of rubber particles
(low modulus) in the epoxy matrix. Similar observa-
tions have been reported by many authors34±36 using
CTBN liquid rubber. However, this is in direct
4.0 (4.0) 175.6 3.0
6.5 (5.0) 139.5 3.0
6.0 (5.0) 129.7 5.0
6.0 (5.0) 121.4 5.0
9.5 (7.0) 91.6 5.5
14.0 (10.0) 73.8 7.5
285
D Ratna, AK Banthia

contradiction to the observations made by Achary et

al 11,29 where they have reported increase in tensile
strength as a result of incorporation of CTBN and
carboxyl terminated poly(propylene glycol) adipate
liquid rubber.
A similar trend was observed for ¯exural fracture
strength and deformation (Table 3). A representative
¯exural stress versus deformation curve for pure epoxy
and 10 phr CTPEHA modi®ed epoxy is shown in Fig
6. This indicates higher deformation and lower
strength for modi®ed epoxy. The decrease in ¯exural
strength was also observed by lijima et al 20,37 for epoxy
terminated acrylic rubber modi®ed epoxy.

Optical microscopy analysis

Figure 6. Flexural stress versus strain plot of (a) unmodified epoxy and (b)
10 phr CTPEHA modified epoxy.
To correlate the molecular and morphological par-
ameters with the fracture properties of the toughened
networks, the microstructures of the fracture surfaces
of various CTPEHA modi®ed networks were analysed
by optical microscopy (OM). The micrographs for
unmodi®ed and modi®ed networks are shown in Fig 7.
The fracture surface of the unmodi®ed epoxy is
homogeneous without any dispersed particles,
whereas the fracture surfaces of modi®ed networks

Figure 7. Micrographs of the fracture surfaces of (a) unmodified epoxy, (b) 10 phr modified epoxy (c) 20 phr modified epoxy and (d) 30 phr modified epoxy.

286 Polym Int 49:281±287 (2000)


consists of two distinct phases: globular particles are
dispersed in a continuous epoxy matrix. The number
of particles increases with an increase in the concen-
tration of CTPEHA. The modi®ed epoxy networks
having 10 phr of liquid rubber contain rubber particles
uniformly distributed throughout the matrix. The
aggregation starts at higher concentration. This
explains why the impact and adhesion properties
attain a maximum value at about 10±15 phr and
subsequently decrease.
CONCLUSIONS
CTPEHA was synthesized in the form of liquid rubber
by a bulk polymerization technique. It is compatible
with epoxy resin up to 20 phr concentration at room
temperature. The CTPEHA was incorporated into the
epoxy matrix by a prereact method. No gelling was
observed after prereaction. The modi®ed resin under-
goes curing reaction at a slower rate in comparison to
the pure epoxy. Improvement in impact and adhesive
strength was observed as a result of the incorporation
of CTPEHA into the epoxy matrix. The increase in
adhesive and impact strength depends on the con-
centration of the modi®er; the maximum increase was
obtained at 10±15 phr of modi®er. About two-fold
increase in adhesive and impact strength was achieved
with a moderate loss of tensile and ¯exural strength.
The epoxy±CTPEHA formulation may be a potential
ambient temperature cured structural adhesive.
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