Application of a Palm Oil-Based Alkyd for the Improvement of Polyaniline Properties

Application of a Palm Oil-Based Alkyd for the Improvement of

Polyaniline Properties
Mariam Fadzlina Ramli1, Seng Neon Gan1, Wen Huei Lim2*, and Sook Wai Phang3
1
Department of Chemistry, Faculty of Science, University of Malaya, 50603, Kuala Lumpur
2
Advanced Oleochemical Technology Division (AOTD), Malaysian Palm Oil Board (MPOB), No 6, Persiaran Institusi,
43000 Kajang, Selangor
3
Department of Physical Science, Faculty of Applied Sciences and Computing, Tunku Abdul Rahman University
College, Jalan Genting Kelang, Setapak, 53300, Kuala Lumpur

Summary
This study attempts to produce polyaniline (PAni)/Alkyd films with short curing time, good adhesion on fluoride-
doped tin oxide (FTO) glass and having high conductivity that can be apply in solar cell panel. Both palm
stearin-based alkyd resins and PAni were synthesized via chemical reactions. Chemical structures of the palm
oil-based alkyd and PAni were investigated by proton nuclear magnetic resonance (1H NMR), Fourier Transform
Infrared (FTIR), and Ultraviolet-visible (UV-vis) spectrometers. Palm oil-based alkyds having three different acid
number (AN) (5.66, 14.74, and 17.60 mg KOH/g) were blended with PAni at ratio of 1:0.5, 1:0.75, 1:1 for the
preparation of PAni/Alkyd films via UV curing method. UV-vis spectrometer confirmed the chemical structure
of PAni/Alkyd films. The adhesion of Pani/Alkyd films were tested following ASTM D3359 and conductivity
study of PAni/Alkyd films was carried out using four point probe method. Best result was observed for PAni/
Alkyd at a ratio 1:0.5 with the palm oil-based alkyd having AN value of 5.56 mg KOH/g. The shortest curing
time was 10 minutes, with strong adhesion of PAni/Alkyd films on FTO glass and conductivity of 2.56102 S/
cm. By comparison the conductivity of the pure PAni was 1.31x103 S/cm.

Keywords: Palm stearin; Palm oil-based alkyd; Polyaniline; Adhesion; Conductivity; Solar cell

1. Introduction
Presently, environmental pollution
and shortage of sustainable, safe
and environmental friendly energy
resources become an important
global concern. One of the
sustainable development challenges
is the utilization of renewable
energy resources. Renewable energy
resources refer to the energy that
can be regenerated continuously for
examples sunlight, rain, waves, wind
and geothermal heat. Among the
renewable energy resources available,
solar energy is consider one of the
best that is capable supplying endless
energy for mankind1,2. Solar energy
which obtained from the sun is known
to be efficient in various applications
*Corresponding author: limwen@mpob.gov.my
©
Smithers Information Ltd., 2017
such as in the power plants, seawater
desalination, and various solar battery
powered machineries. There are
various types of solar cells presence
in the market, for examples, dye-
sensitized solar cell (DSSC), organic-
polymer-based photovoltaic solar
cell (OPV), hot carrier solar cell and
others3.
DSSC was developed by O’Regan and
Gratzel in 1991 have raised a great deal
of attention for its benefits such as cost-
effectiveness and high clean energy
conversion process, easy fabrication
process and green environmental
protection4. In a typical DSSC device,
platinum (Pt) is one of the most popular
traditional materials that employed as a
counter electrode (CE) material due to
its excellent redox property and good
chemical stability. However, Pt being
a noble metal is expensive. Therefore,
in order to replace Pt as a CE material,
many functional materials have been
extensively studied, one of which is
the conducting polymers, CPs5.
CPs exhibit semiconducting behaviour
and have an extended π-conjugation
along the polymer chain. They become
electrically conductive during doping
or dedoping process. Among all the
CPs available in the market, polyaniline
PAni is the most promising due to its
high conductivity, good electrocatalytic
(EC) property, unique redox properties
and tunable properties as compared to
other CPs. Besides, the commercial
applications of PAni because of its
facile synthesis, low synthetic cost,
ease availability of raw materials and
good environmental stability6,7.

Polymers & Polymer Composites, Vol. 25, No. 7, 2017 537

 Mariam Fadzlina Ramli, Seng Neon Gan, Wen Huei Lim, and Sook Wai Phang
The role of CE in DSCC is to transfer
electrons flowing from external circuit
and catalyze the reduction of redox
electrolyte. Therefore, PAni that
possesses high conductivity, good
EC property and low cost could be a
better alternative to replace Pt as CE
materials8. Furthermore, the porosity in
the nanostructured of PAni will cause
the electron transfer facile during its
application in DSSC and thus being
an efficient CE9.
In term of solar cell application,
conductivity and contact among
the substrates are two important
properties to be considered for high
performance of solar cell. Conductivity
of the solar cell can be contributed
by the PAni at conductivity range of
(8.6x10-1 – 5.6x101 S/cm)7. Although
the high conductivity of PAni can be
advantageous for high performance
solar cell, PAni is brittle and exhibits
poor contact ability towards the
substrate during solar cell application.
Poor contact ability or adhesion of
material with the substrate can be
related to its surface energy. PAni
can be categorized as a high surface
energy material10. Therefore, when
PAni is coated onto a solid surface, it
will exhibited higher surface energy
than the attractive forces toward
the surface, which result in lower
bond strength11,12. Preliminary study
indicated that contact performance of
PAni on the FTO glass can be improved
in the presence of alkyd compound13.
The palm oil-based alkyd resins which
have vast industrial applications have
exhibited excellent adhesion properties
as the polar groups such as carboxylic
groups (COOH) are very active
promoters of adhesion which attract
strongly to the substrate14-17. As such,
it is foreseen that PAni/Alkyd could be
a good match for solar cell application
in term of conductivity, surface contact
and flexibility properties. In this work,
palm oil-based alkyd was synthesized
through alcoholoysis and esterification
reactions while PAni was synthesized
through chemical oxidation process
538
using dioctyl sodium sulfosuccinate
(AOT) as dopant. Palm oil-based alkyd
resins were blended with PAni in order
to improve the adhesion of films on
the FTO glass. In addition, solar cell
performance will be monitored by
studying the conductivity property of
the new PAni/Alkyd composite.
2. Experimental
2.1 Materials
Glycerine (99.5%) was a kind gift from
Emery Oleochemicals Malaysia Sdn.
Bhd. Refined, bleached, deodorised
palm stearin with iodine value, IV of
38.82, free fatty acid (palmitic acid)
of 0.13% and moisture of 0.03% was
acquired from Southern Edible Oil
Ind. (M) Sdn. Bhd. Phthalic anhydride
(PA) was from DC Chemical Korea,
potassium hydroxide (KOH, 85.0%)
from Systerm, fumaric acid (FA, 99.0%)
and deuterated chloroform, CDCl3
(0.03 volume% TMS, deuteration
degree 99.8%) from Merck were used
as received. Aniline (Ani, 99.5%),
dioctyl sodium sulfosuccinate (AOT,
96.0%), ammonium persulphate (APS,
98.0%) and benzophenone (99.0%)
were acquired from Sigma Aldrich.
Hydrochloric acid (HCl, 37.0%) was
purchased from RCI Labscan Limited
and toluene (99.8%) was purchased
from Bumi-Pharma Sdn. Bhd. FTO
glasses were obtained from AGC
Fabritech Company Incorporation.
2.2 Synthesis of Palm Oil-based
Alkyd
Palm oil-based alkyd was synthesized
by alcoholysis and esterification
reactions. The synthesis began with
the alcoholysis reaction between palm
stearin and glycerine using KOH as the
catalyst. The system was stirred using a
digital overhead stirrer throughout the
cook. The reaction mixture was heated
up to 230 ˚C. The reaction to form
monoglycerides was completed when
the mixture turned transparent in colour,
became brownish-clear, turned clear and
was also confirmed by solubility test
of product in ethanol. The next stage
Polymers & Polymer Composites, Vol. 25, No. 7, 2017
of cooking involved the esterification
of the monoglycerides with diacids.
The esterification reaction was carried
out following fusion method where no
solvent was used during the reaction.
The mixture was allowed to cool down
by itself to around 100 ˚C. Then, PA and
FA were added into the mixture and was
slowly heated up to 220 ˚C. The progress
of the reaction was monitored based
on the acid number (AN) of the palm
oil-based alkyd. Several palm oil-based
alkyds with different AN were isolated
from this synthesis. AN was obtained
following to the standard test method
of AOAC (969.17, 1997).
2.3 Synthesis of PAni
PAni was synthesized via chemical
oxidation method by using Ani as
monomer, AOT as dopant and APS
as oxidant. The synthesis was carried
out at 0 ˚C. Firstly, AOT was dissolved
in HCl solution followed by slow
addition of Ani into the AOT solution
to obtain a homogenized Ani/AOT
mixture. The solution was stirred for
2 hours and then APS was slowly
dropped into the solution in order
to initiate the polymerization. The
polymerization reaction was carried out
for 24 hours. After that, excess amount
of toluene was added to terminate the
polymerization process and PAni was
then extracted into toluene layer by
using separating funnel in order to
separate the unreacted Ani monomer,
AOT and APS in the aqueous phase.
The organic phase was washed with
distilled water to remove water soluble
impurities. Concentration of PAni was
in toluene solution was expressed as
weight percentage (w/w.%).
2.4 Characterizations of Palm
Oil-based Alkyd and PAni
The palm oil-based alkyd was
characterized using 1H NMR (Perkin
Elmer, 270MHz), FTIR (Perkin-Elmer
FTIR RX1) and ultraviolet-visible (UV-
Vis) spectrometer. For 1H NMR analysis,
the sample was dissolved in CDCl3 while
FTIR analysis were carried out by coating
the sample on the sodium chloride (NaCl)
 Application of a Palm Oil-Based Alkyd for the Improvement of Polyaniline Properties

cell. Four scans from 4000 to 400 cm-1
and scanned at resolution of ±4 cm-1 were
performed on the sample in the FTIR
analysis. In addition, UV-Vis analysis
of the sample was carried by using
an UV-Vis spectrometer (Shimadzu,
UV 1650-PC) which scanned in the
wavelength range of 300-900 nm.
PAni was characterized using both
FTIR and UV-Vis spectrometers. FTIR
measurement on PAni thin films were
obtained from a FTIR-ATR spectrometer
(Spectrum 400 Perkin Elmer), scanned
from wavenumber 400 to 4000 cm-1
while UV-Vis measurement for PAni
thin films were carried out using UV-Vis
spectrometer in the wavelength range of
300-900 nm.
2.5 Coatings Preparations
PAni and palm oil-based alkyd were
blended together with several different
ratios of PAni and palm oil-based alkyd.
PAni/Alkyd mixtures were firstly
stirred to homogenise the mixture.
A UV-photoinitiator, benzophenone
was then added to the PAni/Alkyd
mixtures, followed by spin coated
the mixtures onto the FTO glass by
using a spin coater. The films were
then UV-cured using the DYMAX
Ultraviolet Light Source, having
400 W lamp and radiates UV light at
intensity of 225 mW/cm2. The curing
process of PAni/Alkyd films involved
reaction of free radicals generated
from benzophenone with components
carrying C=C in the PAni/Alkyd films.
The thickness of PAni/Alkyd films
were determined by using a micrometer
(Mitsutoyo, Japan).
3. Results and As shown in Figure 3, FTIR spectrum
discussions of the palm oil-based alkyd confirmed
its structure. The strong band at
H NMR, FTIR and UV
1
1740 cm-1 can be attributed to the
Analysis carbonyl group in ester linkages,
while the small peaks at 1580 and
Figure 1 shows the 1H NMR spectrum
1602 cm-1 corresponded to the C=C
of palm oil-based alkyd. The proton
of the aromatic rings in PA. Another
for terminal methyl groups of fatty
important peak of palm oil-based
acids can be depicted by the peak at
alkyd is associated with the broad
around 0.87 ppm, while peaks in the
band of hydroxyl groups present at
range of 1.23 to 1.38 ppm correspond
~3400 cm-1 20,21. The FTIR spectrum of
to protons of CH2 present in the alkyd
PAni as indicated in Figure 4 displays
chain. The peaks appeared at 5.32 to
three important peaks associated
5.37 ppm are due to the protons attached
with a benzenoid peak at 1501 cm-1,
to unsaturated carbon (RCH=CHR)
CH=CH stretching of quinoid peak
and peak at 6.90 ppm corresponded to
at ~1600 cm-1 and NH stretching at
the OOCCH=CHCOO confirmed that
~3200 cm-1. These peaks indicate
FA has been introduced into the alkyd
chain. The proton for the aromatic ring the characteristic peaks of PAni and
is confirmed by the peak at around 7.54 confirmed its chemical structures13.
to 7.74 ppm. A plausible structure of
palm oil-based alkyd compound is The UV-Vis absorption spectra for
shown in Figure 218,19. PAni, palm oil-based alkyd and PAni/
Figure 1. 1H NMR spectrum of palm oil-based alkyd
Figure 2. Plausible structure of palm oil-based alkyd

2.6 Characterization of PAni/

Alkyd Films
PAni/Alkyd films were characterized
using UV-Vis spectrometer in the
wavelength range 300-900 nm. PAni/
Alkyd films were tested for their
adhesion properties using a cross cut
tape test method following ASTM
D3359 and the conductivity of the films
were determined by using a standard
four-probe method (model Loresta GP)
at room temperature.

Polymers & Polymer Composites, Vol. 25, No. 7, 2017 539

 Mariam Fadzlina Ramli, Seng Neon Gan, Wen Huei Lim, and Sook Wai Phang
Alkyd films are shown in Figure 5.
UV-Vis spectrum reveals the chemical
structure and doping level of PAni.
There are three major peaks that can
be attributed to the structure of PAni
which composed of π – π* transition
of benzenoid rings at ~320 nm and the
two peaks at ~440 and ~750 nm which
Figure 3. FTIR spectrum of palm oil-based alkyd
Figure 4. FTIR spectrum of PAni
Figure 5. UV-Vis spectra of PAni, palm oil-based alkyd and PAni/Alkyd films
540
correspond to localized polarons. Peak
at ~750 nm indicates the conductivity
and doping level of PAni where PAni
is in conducting state which exists
as emeraldine salt phase, ES22. The
degree of polymerization for PAni is
considered to be high as it has been
prepared at low temperature (0 ˚C)23.
Polymers & Polymer Composites, Vol. 25, No. 7, 2017
The pattern of the UV-Vis spectrum
for palm oil-based alkyd was found to
exhibit similar trend to the alkyd spectra
as reported by some authors24. From the
UV-Vis spectra, it can be observed that
there is a shift in wavelength at peak
~750 nm (PAni spectrum) to ~815 nm
(PAni/Alkyd spectrum). This suggested
more delocalization of polarons, and
more extended coil-like structure will
be formed through chain rearrangement.
As a result, this would be lowering the
stearic hindrance from PAni and can
interact well with alkyd supposedly
enhances the adhesion property of the
PAni nanocomposite10,25.
3.2 Curing Time and Adhesion
Property
Several ratios (such as 1:0.5, 1:0.75 and
1:1) of PAni/Alkyd mixtures as well as
different AN values of palm oil-based
alkyd were chosen for this study. In this
study, PAni/Alkyd films were prepared
to the thickness of 5.0 μm. Figure 6
shows that PAni/Alkyd film with alkyd
having lowest AN value of 5.66 mg
KOH/g exhibited the shortest curing
time as compared to PAni/Alkyd films
with high AN value. This was due to
the conversion of acid groups during
the esterification reaction of palm
oil-based alkyd. This conversion is
very important because the carboxyl
functionality (F-COO) of diacids, PA
and FA will delay the drying rate. Palm
oil-based alkyd with lowest AN value
will have the highest conversion of acid
groups26-28. Among these three ratios,
1:0.5 of PAni to palm oil-based alkyd
has the fastest curing time.
Adhesion test was carried out on
PAni film on FTO glass and the result
obtained as 0B which indicated poor
adhesion performance. From Table 1,
it was observed that all films mixtures
produced from PAni/Alkyd achieved
good adhesion on FTO glass with
grade of 5B. This indicated that PAni/
Alkyd films with the selected alkyd
having different AN were able to impart
good adhesive property to improve the
adhesion of the films.
 Application of a Palm Oil-Based Alkyd for the Improvement of Polyaniline Properties

3.3 Conductivity Study
The conductivity of PAni film on FTO
glass was determined by using four
point probe method and its conductivity
is 1.31103 S/cm. By comparing the
results in Table 2, the incorporation of
palm oil-based alkyd into PAni films
showed decreasing in conductivity of
the films. Besides, it can be observed
that different AN values of palm
oil-based alkyds could affect the
conductivity of PAni/Alkyd films but
there was no constant pattern of their
conductivity recorded in this study.
Therefore, the focus of the conductivity
study lies more on PAni/Alkyd films
with AN of 5.66 mgKOH/g because it
has the shortest curing time compare to
other AN and at the same time posed
strong adhesion on FTO glass. Table 2
shows that the conductivity of PAni/
Alkyd, AN value of 5.66 mgKOH/g,
decrease with increasing amount of
alkyd.
best ratio for PAni/Alkyd films was
1:0.5 (PAni:Alkyd) with AN of 5.66
mg KOH/g alkyd due to its shortest
curing time, good adhesion and high
conductivity that can offers an excellent
potential application in solar cell panel.
Acknowledgements
The authors wish to acknowledge
Malaysian Palm Oil Board for financial
support for research attachment in
University of Malaya. The authors also
wish to thank for the financial support
by University of Malaya research
grants (PG199-2016A).
Figure 6. Curing time of PAni/Alkyd films with different AN of palm oil-based
alkyd and different PAni/Alkyd ratio
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