Synthetic Metals 160 (2010) 1981–1986

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Synthetic Metals
journal homepage: www.elsevier.com/locate/synmet

Synthesis of conductive adhesives based on epoxy resin and polyaniline.DBSA

using the in situ polymerization and physical mixing procedures
Bluma G. Soares a,∗ , Micheli L. Celestino a , Matheus Magioli a , Viviane X. Moreira a , Dipak Khastgir a,b
a
Instituto de Macromoléculas, Universidade Federal do Rio de Janeiro, Centro de Tecnologia, BI. J, Ilha do Fundão, 21945-970 Rio de Janeiro, RJ, Brazil
b
Rubber Technology Centre, Indian Institute of Technology, Kharagpur, India

a r t i c l e i n f o a b s t r a c t

Article history: Electrically conductive adhesives based on epoxy-anhydride system containing polyaniline (PAni) doped
Received 23 July 2009 with dodecylbenzenesulfonic acid (DBSA) have been successfully developed and characterized. The
Received in revised form 18 July 2010 blends were prepared by physical mixing and by in situ polymerization of aniline within epoxy matrix.
Accepted 20 July 2010
The in situ polymerization procedure contributes for the formation of a conducting pathway with lower
Available online 16 August 2010
amount of PAni.DBSA. A conductivity as low as 10−3 S cm−1 with 12 wt% of PAni and excellent adhe-
sion properties were achieved with these systems. The microstructure of the conductive adhesives was
Keywords:
studied by means of scanning electron microscopy (SEM). In the case of blends prepared by in situ poly-
Epoxy
Polyaniline
merization, PAni.DBSA is dispersed within the epoxy matrix in the form of microtubules. Dielectrical
Conductive adhesive properties as a function of frequency and temperature have also indicated a great interaction between
Thermosets polyaniline and epoxy matrix by in situ polymerization procedure.
Dielectric properties © 2010 Elsevier B.V. All rights reserved.

1. Introduction a decrease of the conductivity values because of the deprotona-

Polyaniline (PAni) is considered one of the most promis-
ing intrinsically conducting polymers due to its easy synthesis,
good electrical conductivity and low cost. In addition, it can
be reversibly converted into a conducting or insulating form
through a simple protonation–deprotonation of the polymer. The
use of special organic acids as protonating agents, such as dode-
cylbenzenesulfonic acid (DBSA), camphorsulfonic acid (CSA) and
p-toluenesulfonic acid (TSA) improves the compatibility between
the conducting (protonated) form of PAni and other polymer
matrix [1,2]. Blending polyaniline with epoxy resin constitutes an
interesting approach for developing conductive coatings for elec-
tromagnetic interference shielding [3,4], anti-corrosive protection
[5,6], conducting adhesives [8], etc.
The literature presents some interesting researches on the field
of PAni blends with epoxy resin, which involve the use of PAni
doped with CSA [7,8], DBSA [9–15], TSA [12,16] and chloridric acid
[17,18]. The characteristic of the hardener as well as the prepara-
tion procedure are also critical parameters that govern the electrical
properties of epoxy resin/PAni blends. Aliphatic amines are the
most popular hardener for epoxy resin because they can pro-
mote the curing at room temperature. However, they may cause
∗ Corresponding author. Tel.: +55 21 2562 7207; fax: +55 21 2562 7207.
E-mail address: bluma@ima.ufrj.br (B.G. Soares).
tion of PAni favored by the basic nature of the hardener. Yang et al.
[19] have used oligomer of polyaniline in the emeraldine base form
to blend with epoxy resin, which was cured with aliphatic amine.
The doping process was performed by dipping the cured film in
a solution of TSA. Unfortunately this process is not indicated for
the development of adhesives and coatings. Recently we have used
triethylene tetramine (an aliphatic amine) as a curing system for
epoxy/PAni.DBSA blends [14,15]. By using appropriate proportion
of PAni and amine to keep the stoichiometric ratio with epoxy resin,
it was possible to achieve conductivity values around 10−6 S cm−1 ,
with 10% of PAni.DBSA.
Other curing systems with acidic characteristics have been also
studied in epoxy/PAni blends in order to avoid the deprotonation
of PAni during the curing process. Tsotra et al. [10–12,20–21] have
studied the effect of a BF3 -complex catalytic curing agent on the
electrical properties of epoxy/PAni.DBSA blends. In spite of the
acidic nature of the curing system, the conductivity values achieved
with this curing system were not so high, remaining in the range
of 10−7 S cm−1 with 10% of PAni.DBSA. Anhydride is also a very
common hardener for epoxy resin but the curing process requires
higher temperature than aliphatic amine. Some reports in the liter-
ature deal with the use of anhydride as a curing agent in epoxy/PAni
blends with the purpose of avoiding PAni deprotonation by basic
curing systems. Jia et al. [9,13] have achieved a resistivity value
around 104  cm by using 60% of PAni.DBSA in epoxy systems cured
with anhydride. Yang et al. [22] have used PAni doped with mul-
tiple sulfonic acid in blends with epoxy resin. After curing with

0379-6779/$ – see front matter © 2010 Elsevier B.V. All rights reserved.
doi:10.1016/j.synthmet.2010.07.021
1982 B.G. Soares et al. / Synthetic Metals 160 (2010) 1981–1986
anhydride system, the conductivity of the corresponding network
was in the range of 10−5 S cm−1 . Low percolation threshold in
epoxy/PAni system has been achieved by using polyaniline fibers
or wires in blends cured with 2,4,6-tri(dimethylaminomethyl)
phenol [18] or polyaniline as nanorods [23]. In the last system,
polyaniline played the role of conductive additive and curing
agent.
The method used for the blend preparation may also influence
on the electrical conductivity of the final network because of the
different states of dispersion of PAni inside the epoxy matrix. The
preparation of epoxy resin/PAni-DBSA nanoparticles dispersed in
water and mixed with epoxy-aniline droplets gave rise to materials
with conductivity values in the range of 10−2 S cm−1 with 20% of
PAni [24].
The one step in situ emulsion polymerization of aniline in the
presence of the hosting insulating polymer has been extensively
studied as a good strategy for the development of more homoge-
neous conducting composites. This technique has been employed
to prepare blends of PAni with several thermoplastics [25–27].
Regarding epoxy resin hosting polymers, this technique has not
been well explored. Jeevananda et al. [16] performed the in situ
polymerization of aniline in the presence of epoxy novolac resin,
using p-toluenesulfonic acid as the protonating agent. They found
a conductivity value in the range of 10−1 S cm−1 with 75% of PAni.
Lu et al. [8] used similar approach for developing epoxy resin
with PAni.CSA. After curing with anhydride, this blend prepared
by in situ polymerization displayed a conductivity value around
10−6 S cm−1 .
This article reports a new procedure for preparing high
electrical conducting epoxy/PAni.DBSA blends using the in situ
oxidative polymerization of aniline in an epoxy resin solu-
tion in toluene aiming to develop new conductive adhesives
with good electrical and mechanical properties. The curing
system used in this work was methyl tetrahydrophthalic anhy-
dride, which is expected not to influence on the protonation
of PAni. Dodecylbenzenesulfonic acid was used as the proto-
nating agent and also as the emulsifier in the case of in situ
emulsion polymerization. The in situ polymerization procedure
has the advantage of involving only one simple polymerization
step and also promoting a better dispersion of the conducting
additive.
The effect of physical mixing and in situ polymer-
ization procedure on the properties of epoxy/PAni.DBSA
networks was evaluated by electrical conductivity, dielec-
tric properties and adhesive properties using the lap-shear
procedure.
2. Experimental
2.1. Materials
Aniline (Ani) (analytical grade, Merck) was distilled twice
under vacuum and stored under nitrogen in a refrigerator.
Ammonium peroxydissulfate (APS) (analytical grade, Merck)
and dodecylbenzenensulfonic acid (DBSA) (technical grade, Pro-
Quimica do Brasil) were used without purification. Diglycidyl
ether of bisphenol A (DGEBA)-based ER (DER 331) was pur-
chased by Dow Química (São Paulo, Brasil) and presents the
following characteristics: <Mn > = 380; viscosity = 12,000 cP; epox-
ide equivalent = 192 g/equiv., as determined by acid titration.
The hardener used for the curing process was methyl hex-
ahydrophthalic anhydride (Acros Organics) together with 1% of
2,4,6-tri(dimethylaminomethyl) phenol (Aldrich), as the catalyst
for the curing process.
2.2. Synthesis of PAni.DBSA
Polyaniline doped with DBSA (PAni.DBSA) was prepared by
inverted emulsion polymerization according to the literature
[28,29]. Based on those procedures, 0.22 mol of aniline and 0.22 mol
of DBSA were dissolved into toluene under stirring. The reaction
medium was kept at 0 ◦ C and 100 mL of an aqueous solution con-
taining 2.2 M of APS were slowly added. After 6 h, the medium
was poured into methanol, filtered, washed several times with
methanol and dried under reduced pressure for 72 h.
2.3. Preparation of epoxy resin/PAni.DBSA composite
Two different methods have been employed for the preparation
of ER/PAni.DBSA blends: physical mixing (PM) and in situ polymer-
ization (ISP).
For the physical mixing, different amounts of PAni.DBSA as a
powder were hand-dispersed with epoxy resin in a mortar.
For in situ polymerization method, a fixed amount of ER (8 g) was
dissolved into chloroform. Then, different amounts of Ani (between
0.87 and 18.7 g) and DBSA were added with stirring. The medium
was kept at 0 ◦ C and a 2.2 M aqueous solution of APS was slowly
added. The molar proportion of Ani:DBSA:APS was 1:1:1. The total
polymerization time was 6 h. The polymerization was finished by
pouring the emulsion into a decantation vessel. The emulsion was
washed with water. The organic layer was separated; the solvent
was evaporated and dried under reduced pressure.
The ER/PAni.DBSA blends prepared by both methods were
mixed with the anhydride hardener, which was premixed with 1%
of catalyst. The mixing ratio of the ER to the hardener was kept
constant at 10/9. The mixture was cast into silicon rubber mold
and cured at 80 ◦ C for 5 h, followed by an additional post curing
process at 140 ◦ C for 2 h.
2.4. Characterization
The electrical conductivities of the blends were measured by
using a Keithley 6517A electrometer, a multimeter Minipa ET2907
and a home made four probes device with a medium distance
between the probes of 0.171 ± 0.03 cm. The measurements were
performed on a disk film with a thickness of 0.5 mm.
Dielectric relaxation measurements were made in a dielectric
analyzer DEA (TA Instruments Model 2970) operating with parallel
plate electrodes. The samples (epoxy resin and their blends) used
for this characterization was prepared by casting the epoxy blends
containing the hardener on silicon rubber molds of 2.5 diameter
and around 0.5–1.0 mm thickness. After the curing process (80 ◦ C
for 5 h and 140 ◦ C for 2 h) the samples were put into 0.1 M aqueous
hydroxyl ammonium solution for 48 h in order to deprotonate the
PAni.DBSA component. This treatment was necessary because the
equipment cannot work with conductive samples. The dielectric
constant ε and dielectric loss ε were obtained over the frequency
range from 0.5 to 105 Hz and a temperature range from −130 to
200 ◦ C, under dry nitrogen gas purging. The heating rate was estab-
lished as 3 ◦ C min−1 .
Scanning electron microscopy (SEM) was performed on a Jeol
JSM-5300 microscope operating at 10 kV. The epoxy/PAni.DBSA
composites were cryo-fracturated and the surface fracture was cov-
ered with a thin layer of gold before analysis.
2.5. Mechanical testing
Stress-strain tests were performed on an Instron 4204 testing
machine, according to the ASTM 638-5 method, at a crosshead
speed of 1 mm min−1 .
 B.G. Soares et al. / Synthetic Metals 160 (2010) 1981–1986
Fig. 1. Electrical conductivity of epoxy resin/PAni.DBSA networks as a function of
the PAni content and blend preparation method: (a) Physical mixing and (b) in situ
polymerization procedure.
The adhesive strength measurements were performed in steel
plates of 120 mm × 25 mm and a thickness of 1.8 mm. The surface
of these plates was roughened by using a glass microsphere-blast,
washed with acetone in an ultrasonic bath for 5 min, and then
washed with distilled water. The adhesive formulations were then
applied uniformly to both the surface portions of the adherent
surface of the joints. The coating surface length corresponded to
25 mm. A pressure of approximately 0.5 MPa was applied over the
bonded specimens by using a lever press assembly. The thick-
ness of the adhesives in this lap shear testing corresponded to
0.03 ± 0.005 mm. The adhesive strength was measured in an Instron
4204 testing machine at a cross-head speed of 0.5 mm min−1 ,
according to ASTM D-1002 procedure. All adhesion tests were car-
ried out at room temperature and the values were taken from an
average of at least 10 specimens.
3. Results and discussion
3.1. Electrical conductivity
Fig. 1 compares the effect of PAni.DBSA content on electrical
conductivity of ER/PAni.DBSA networks prepared by the two differ-
ent methods. The percolation curve profile of the blends prepared
by ISP method appears as a sharp insulator–conductor transi-
tion, which occurs at a relatively low amount of PAni inside the
polymer matrix. Differently, a light insulator–conductor transition
can be observed in the percolation curve of the blends prepared
by PM method. The amount of PAni.DBSA in physical mixture
was limited to 30%. Beyond this concentration, the dispersion of
the PAni powder into ER matrix was very difficult. The in situ
formation of PAni.DBSA in the epoxy matrix system resulted in
higher conductivity compared to physically blended composites.
Fig. 2. SEM micrograph of epoxy resin/PAni.DBSA obtained by (a) physical mixing method, (b) “in situ” polymerization. (a) 10 wt% and (b) 7 wt% of Pani.DBSA.
1983
Fig. 3. Dependence of the dielectric loss factor against temperature for the
epoxy/anhydride cured system at different frequencies.
The highest level of conductivity achieved with the ISP system
corresponded to 5.15 × 10−2 S cm−1 in contrast to the highest con-
ductivity value achieved by physical mixing which stayed around
8.85 × 10−4 S cm−1 . These values are also substantially higher than
that reported in the literature for ER/PAni.CSA systems prepared
by in situ polymerization [8]. This also gives us an idea of attain-
ing higher conductivity through addition of PAni doped with DBSA
instead of CSA. In fact by doping with relatively cheaper dopant
DBSA one can increase the processability of Pani which is otherwise
quite difficult to process.
The percolation threshold points of the ER/PAni.DBSA systems
have been found to be in the range of 10 and 2 wt% for the systems
prepared by physical mixing and in situ polymerization methods,
respectively. The lower value found for ER/PAni.DBSA networks
prepared by in situ polymerization suggests the propagation of the
PAni.DBSA chain in a more orientated way, giving rise to an effective
conducting pathway with lower amount of PAni.
3.2. Morphological properties
The orientated PAni.DBSA domains obtained by the in situ
polymerization procedure can be confirmed by SEM microscopy.
Fig. 2 compares these micrographs of ER/PAni.DBSA networks pre-
pared by different procedures. The morphology of the system
prepared by physical mixing is characterized by PAni particles
discretely distributed in the epoxy matrix. The conducting path-
way in this sample containing 10% of PAni.DBSA is not clearly
evident and agrees with the electrical conductivity values around
10−7 S cm−1 . However, in blend prepared by in situ polymerization,
the PAni.DBSA appears in the form of microtubules of relatively
high aspect ratio, interconnected each other just forming evi-
dent conducting pathways. Similar fibrillar morphology has been
1984 B.G. Soares et al. / Synthetic Metals 160 (2010) 1981–1986

reported by Jayanty et al. [30] and may be attributed to a tem-

plate effect exerted by the epoxy resin due to the physical-chemical
interactions through hydrogen bonding between the aniline salt
formed with DBSA and the epoxy matrix. Such interactions pro-
mote an organized assembly of PAni chains leading to these rod-like
morphology. This morphology should be responsible for the higher
conductivity value of this sample (around 10−4 S cm−1 with only
7 wt% of Pani.DBSA).

3.3. Dielectric properties

Dielectric relaxation of epoxy-anhydride cured system is pre-

sented in Fig. 3 in terms of dielectric loss factor (ε ) against
temperature at different frequencies ranging from 102 to 105 Hz.
A relaxation region at higher temperature can be detected through
appearance of broad peak in plots of loss factor. This relaxation peak
may be attributed to the occurrence of glass–rubber transition in
cured epoxy system. This broad peak decreases in height as the fre-
quency is increased and can be well observed only at a frequency
of 104 Hz.
To minimize the ionic conductivity and interfacial polarization
contribution to the relaxation process especially at higher temper-
ature, electric loss modulus M is often plotted to get better picture
of relaxation. It is the imaginary component of complex electric
modulus M* where M* = M + iM and it is calculated from dielectric
constant, ε , and dielectric loss, ε , according to Eq. (1) [31,32]:

 ε 
M =
(ε + ε  )
Fig. 4 compares the dependence of M with temperature
of the epoxy-anhydride cured system with the corresponding
ER/PAni.DBSA (2 wt%) blends prepared by different procedures. We
have been chosen this PAni content For DEA analysis because higher
concentration resulted in dielectric response beyond to the limit
of the equipment detection. These blends have been previously
submitted to a dedoping process, to be detected by the instru-
ment. As observed in this figure, the electrical loss modulus can
give a better picture for the existence of relaxation peaks at high
temperature for these cured epoxy systems. At 102 Hz the relax-
ation peak of epoxy cured with anhydride corresponded to 107 ◦ C.
No relaxation in the temperature range from −100 to +90 ◦ C has
been observed. The electric loss modulus M against temperature
patterns related to the ER/PAni.DBSA blend prepared by physical
mixing are similar to those observed for pure epoxy network. The
transition temperature corresponding to the maximum peak at
102 Hz occurred at 111 ◦ C, which is slightly higher than the neat
epoxy network. Tsotra and Friedrich [10] observed a slight decrease
of the Tg for similar system containing low amount of PAni.DBSA
and cured with a BF3 -complex catalytic curing agent. The Tg results
reported by Tsotra and Friedrich were obtained by differential scan-
ning calorimetry analysis (DSC) using doped samples, whereas our
results were obtained by DEA using dedoped sample. Therefore, the
slightly higher Tg values found in our system prepared by physical
blend may be due to the absence of the DBSA in the sample, which
could act as a plasticizer.
The blend prepared by in situ polymerization and containing
similar amount of polyaniline displayed a significant shift of the
temperature transition towards higher values. At a frequency of
102 Hz, this temperature corresponded to 142 ◦ C. This result is
unusual since almost all literature survey reports a decrease of glass
transition temperature of the epoxy network with the addition of
polyaniline [9–11] including our own work [14]. All these systems
have been prepared by physical blending. Lu et al. [8] also reported
a decrease of the Tg in epoxy polyaniline composites prepared via
in situ polymerization. That system utilized camphorsulfonic acid
as the protonating agent and presented morphology characterized
(1)
Fig. 4. Dependence of the imaginary part of electric modulus, M , against tempera-
ture at different frequencies, for the epoxy/anhydride cured system and their blends
with 2 wt% PAni.DBSA prepared by different procedures.
by the presence of conductive salt cluster regions well dispersed
inside the epoxy matrix. Therefore, the significant increase of the
Tg found in our system prepared by the in situ polymerization may
be related to the peculiar morphology formed by PAni microtubules
of high aspect ratio. This morphology provides a higher interfacial
area that increases the extent of interaction between epoxy matrix
and the conducting filler. Moreover, during the curing process at
high temperature, polyaniline may also act as the curing agent as
claimed by other authors [23,33]. This behavior also contributes for
a better interaction between the phases, which decrease the chain
mobility and increase the Tg.
3.4. Mechanical and adhesion properties
The mechanical properties like tensile strength and elongation
at break for different physically mixed ER/PAni.DBSA blends as well
as for those prepared by the in situ polymerization are compared
in Table 1. It can be seen that the increase in PAni.DBSA con-
centration resulted in a progressively decrease in tensile strength
and elongation at break for both systems. However the physi-
cally mixed system shows much better strength properties than
the corresponding in situ blended ones. This loss in strength with
 B.G. Soares et al. / Synthetic Metals 160 (2010) 1981–1986 1985

Table 1
Tensile properties of ER/PAni.DBSA cured systems as a function of PAni.DBSA content and preparation method.

PAni.DBSA content (wt%) Ultimate tensile strength (MPa) Elongation at break (%)
PM ISP PM ISP

0 53 ± 4 53 ± 4 6.2 ± 0.3 6.2 ± 0.3

2.2 – 42 ± 4 – 5.7 ± 0.5
7 50 ± 2 38 ± 3 5.9 ± 0.1 4.2 ± 0.1
12 43 ± 4 23 ± 1 4.6 ± 0.5 3.3 ± 0.3
18 34 ± 3 14 ± 3 3.3 ± 0.2 2.7 ± 0.5
30 18 ± 4 11 ± 1 2.1 ± 0.3 2.1 ± 0.4
37 – 9 ± 1 – 1.9 ± 0.3

PM, physical mixing procedure; ISP, in situ polymerization procedure.

Table 2
Adhesive strength of epoxy cured with anhydride as a function of the PAni.DBSA content and the blend preparation procedure.

Adhesive Preparation procedure Load required to break (N) Deformation (%) Conductivity (S cm−1 )

ER 1300 ± 72 7.2 ± 0.2 (2.7 ± 0.2) × 10−10

ER/PAni.DBSA (7%) Physical mixing 900 ± 40 6.0 ± 0.1 (2.7 ± 0.2) × 10−8
ER/PAni.DBSA (7%) In situ polymerization 1000 ± 60 6.9 ± 0.5 (6.1 ± 0.6) × 10−4
ER/PAni.DBSA (18%) Physical mixing 780 ± 25 6.2 ± 0.2 (7.0 ± 0.2) × 10−5
ER/PAni.DBSA (18%) In situ polymerization 930 ± 18 5.4 ± 0.2 (1.2 ± 0.2) × 10−2

increased PAni.DBSA concentration is mainly because of two rea-
sons: (1) PAni.DBSA is acting as non-reinforcing filler for epoxy
matrix mainly because of the very brittle nature of polyaniline and
because of significant difference in polarity and crystallinity of two
polymers, and (2) further presence of PAni.DBSA cause some dis-
turbance in the crosslinking formation of epoxy resin. Both factors
are responsible for deterioration of epoxy matrix strength and the
effect is more pronounced in situ blended samples, which presents
better dispersion of PAni.DBSA in the matrix compared to physically
mixed system.
The adhesive properties of these conducting epoxy networks
were evaluated on steel joints, in terms of lap shear strength.
The results are summarized in Table 2. In both systems prepared
by physical mixing and in situ polymerization, the presence of
PAni.DBSA decreases the load required to break and also the elon-
gation at break, as expected since PAni.DBSA introduces some
defects in the bulk network. However, differently to that behav-
ior found for the bulk material, the conductive joints resulted from
ER/PAni.DBSA prepared by in situ polymerization display higher
strength in terms of lap shear force. This behavior may be attributed
to the more homogeneous distribution of polyaniline in the epoxy
matrix. The physical mixing resulted in the formation of PAni.DBSA
agglomerates. Such large nonadhered particles fail catastrophically
during fracture, and hence, cause a diminution of adhesive proper-
ties.
4. Conclusion
Conductive epoxy/PAni.DBSA blends with good adhesive prop-
erties and high conductivity values can be prepared by both
physical mixing as well as in situ polymerization of aniline in
the epoxy matrix, cured with anhydride type system. The in situ
polymerization procedure gives rise to composites with higher con-
ductivity values when compared with physically mixed composites
at the same level of conductive component. The higher conductiv-
ity values for the blends prepared by in situ polymerization were
attributed to the peculiar distribution of the conducting phase in
the epoxy matrix, characterized by the formation of microtubules of
PAni.DBSA during the polymerization in the presence of the epoxy
matrix, which contributes for the formation of conducting path-
ways with lower amount of PAni.DBSA. The preparation procedure
also affects significantly the dielectric properties and the relaxation
profiles. The higher PAni.DBSA–epoxy matrix interaction achieved
by the in situ polymerization procedure resulted in a significant
increase in relaxation temperature of the epoxy matrix. In addi-
tion to the outstanding conductivity, the adhesive properties of
the cured systems prepared by the in situ polymerization were
also superior when compared to the system prepared by physical
mixing. The results achieved in this work confirm that the in situ
polymerization of aniline inside the epoxy system should be a very
good approach for the development of conducting adhesives with
superior electrical and mechanical properties.
Acknowledgements
We are grateful to Conselho Nacional de Desenvolvimento Cien-
tífico e Tecnológico-CNPq, Coordenação de Aperfeiçoamento de
Pessoal de Ensino Superior-CAPES, Fundação de Amparo a Pesquisa
do Estado do Rio de Janeiro-FAPERJ for the financial support, and
Third World Academy of Science (TWAS)-UNESCO for the fellow-
ship to Prof. Dipak Khastgir to visit Brazil
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