Res Chem Intermed

DOI 10.1007/s11164-015-2141-z

Synthesis and characterization of Luffa cylindrica

fatty acids-based alkyd resins

Emmanuel E. Essien1 • Saviour A. Umoren1 •

Edidiong E. Effiong1

Received: 9 May 2015 / Accepted: 18 June 2015

 Springer Science+Business Media Dordrecht 2015

Abstract The work reports on preparation of three grades of alkyd resins using a
two-stage alcoholysis-polyesterification method. Phthalic anhydride, glycerol and
Luffa cylindrica seed oil were used in the formulation of the alkyds. The oil was
extracted with n-hexane and 30.30 % was obtained. The fatty acids and physico-
chemical analyses of L. cylindrica seed oil revealed 77.78 % unsaturated fatty acids
with linoleic acid (50.25 %), oleic acid (27.30 %), palmitic acid (13.40 %), and
stearic acid (6.38 %) being the most abundant; and iodine value, 153 mg I2/g
respectively. Properties of the alkyds having oil content of 40 % (I), 50 % (II) and
60 % (III) were evaluated. The acid value was observed to decrease as the reaction
progressed. FTIR spectra of the alkyds revealed ester linkages and olefenic
hydrogen stretch at 1737.92–1734.06 and 3064.99–3007.12 cm-1 respectively.
Evaluation of prepared alkyds by determination of acid values, iodine values, sol-
ubility in xylene, toluene and acetone; resistance of dry film to acid, alkali and
water; scratch and gouge film hardness and drying time revealed that L. cylindrica
seed oil is a potential raw material for the coatings industry.

Keywords Luffa cylindrica
Seed oil
Linoleic acid
Oleic acid
Alkyd resin

Introduction

Alkyd resins belong to an important family of resins which are as old as the modern
paint and coating industry. These resins are polyesters that contain mono and poly-
functional acids and alcohols. The coatings made of long-oil alkyd resins deliver
properties such as ability to be air-dryable and good interactions with polar

& Saviour A. Umoren

saviourumoren@yahoo.com
1
Department of Chemistry, Faculty of Science, University of Uyo, Uyo, Nigeria

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substrates such as wood and steel. In addition, the coatings containing alkyd resins
have a relatively lower cost. The coatings of conventional alkyd resins with any oil
content or acid value are solvent based and usually diluted in an organic solvent
such as toluene, xylene and different oil cuts or a mixture of these solvents [1].
The paint industry envisages a future expansion in view of development in
Automobile Industry, utility in Nuclear Power Station, development in Corrosion
Resistant Coatings, expansion in housing activity and other industry uses. The
demand of alkyd resin being an ingredient in Paint, Varnish and Printing ink
industry would be linked with the Paint industry [2]. Therefore, there are many
significant efforts that have been made to increase alkyd resin production. Many
researchers have also attempted to search different sources for alkyd resin
preparation [1–5]. The oils that are mostly employed for alkyd resin synthesis are
linseed oil, soybean oil, dehydrated castor oil, fish oil and tall oil [2].
Luffa cylindrica (Linn) M. Roem (Fig. 1), (family: Cucurbitaceae) is a climber
with slender, slightly hairy, furrowed stem. The fruit is the loofah or vegetable
sponge which is the hard fibro-vascular network found within the ripe fruit. The
interior of the immature fruit has a resemblance of cucumber, but develops into a
network of fibre surrounding large number of flat blackish seeds about 1 cm long.
They are merely seen as weeds since neither the fruits nor seeds are consumed. The
kernel contains between 45 and 51 % oil, which is composed of mainly oleic and
linoleic acids [6]. The colour of the seed oil is reported by different researchers as
being green, brown and dark red [7, 8]. Melon (Colocynthis vulgaris Shrad, the
edible member of the Cucurbitaceae) seed oil has been utilized in the formulation of
alkyd resins [9, 10].
As a practical step towards exploiting this abundant resource which hitherto is
considered as a weed and the seeds having no commercial value, this study
investigates the utilization of a non-conventional seed oil of L. cylindrica in the
synthesis of alkyd resins.

Materials and methods

Materials

Analytical grade phthalic anhydride, calcium carbonate and glycerol from BDH
were used in the preparation of the alkyds without further purification while the
reference alkyd was a commercial medium oil alkyd purchased from Aba Industrial
Layout, Nigeria. The mature fruits of L. cylindrica were harvested from the wild in
November, 2012 at Abak Local Government Area of Akwa Ibom State, Nigeria.
The sample was authenticated by a taxonomist, Dr. (Mrs.) M. E. Bassey of the
Department of Botany and Ecological Studies, University of Uyo where a voucher
specimen was deposited. Luffa cylindrica seeds were hand-picked after loosening
the intervening tissues, sun-dried and pulverized in the laboratory. The ground seed
(556.6 g) was macerated in n-hexane for 72 h and fixed oils obtained by distillation.
The oil samples were placed in the oven at 50 C for 48 h to ensure that all traces of
the solvent evaporated.

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Fig. 1 Luffa cylindrica a plant

with fruit b dry fruit and c dry
seed

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 E. E. Essien et al.

Fatty acids composition analysis

The fatty acids composition of the oil was evaluated by Gas Liquid Chromatography
of fatty acid methyl esters (FAMEs) prepared by boron trifluoride-catalyzed trans-
esterification [11, 12]. FAMEs were analyzed on a HP 6890 Powered with HP
ChemStation Rev. A09.01 (1206) software and equipped with a hydrogen flame
ionization detector (FID). Separation was performed using a fused capillary column
(HPINNOWax, 30 m 9 0.25 mm 9 0.25 lm) as stationary phase. The oven
temperature was programmed as follows: initial temperature at 60 C, first ramping
at 12 C/min for 20 min; second ramping at 15 C/min for 3 min, and maintained
for 8 min. The injector and detector temperatures were 250 and 320 C respectively.
The carrier gas was nitrogen and a split ratio of 20:1 was used. The FAMEs were
identified by comparing their retention times to those of a standard mixture of fatty
acids and the peak areas were integrated.

Physicochemical properties

The physicochemical properties of the seed oil: refractive index, iodine value,
saponification value, free fatty acids/acid value and peroxide value were determined
according to the methods described in [12].

Preparation of alkyd resins

The oil sample was measured into a three-necked reaction flask and heated to a
temperature between 220 and 240 C with constant stirring. A calculated amount of
glycerol and calcium (II) oxide (0.5 %) based on oil length was added (Table 1)
while maintaining the temperature at 240 C until alcoholysis reaction was
completed [10]. The completion of alcoholysis was monitored by removing aliquots
(two drops) of the reaction mixture from the reaction flask after every 5 min and
testing for its solubility in four drops of methanol. A complete dissolution of the
aliquot in methanol to give a clear solution indicated the completion of alcoholysis
reaction. The reaction mixture was allowed to cool to 180 C, when a measured
quantity of polybasic acid followed by xylene (5 % by weight of the total
ingredients charged) were added (Table 1), and the temperature raised quickly to
about 230 C. The temperature was maintained between 230 and 250 C throughout

Table 1 Formulations for the

Sample LC-SOA LC-MOA LC-LOA
different alkyd resins
Composition (g)
Oil 30.00 36.50 45.00
Phthalic anhydride 29.70 25.54 19.83
Glycerol 15.30 10.96 10.17
LC-SOA = L. cylindrica short
oil alkyd; LC-MOA = L. CaO 0.04 0.02 0.02
cylindrica medium oil alkyd; Total 75.04 73.02 75.02
LC-LOA = L. cylindrica long Oil length (%) 40 50 60
oil alkyd

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the duration of the reaction. The extent of polycondensation reaction was monitored
by removing the aliquots (2.0 g) of the reaction mixture at 30 min intervals and
dissolving it in a neutralized mixture of toluene/ethanol (1:1 ratio). The resulting
mixture was titrated with standard KOH (0.1 M) solution using phenolphthalein as
indicator. The reaction was quenched by allowing it to cool when the acid value was
about 10 mg KOH/g.

Evaluation of alkyd resins

The alkyd resins were tested for various performance properties such as solubility,
hardness and chemical resistance using the methods specified by ASTM D1639-90
and ASTM D1647-89 [13–15]. The resins were also tested for drying performance
using the touch method specified in ASTM standard (ASTM D1640-69). Each resin
(3.0 g) was dissolved in acetone, toluene and xylene (5 ml) with intermittent stirring.
The drying time of the alkyd resins were studied at indoor and outdoor temperatures
using various substrates—wood and mild steel panels with cobalt drier. Each alkyd
resin (6.5 g) was mixed with cobalt dryer (0.32 g) and toluene (4 g) in a 100 ml
beaker. The sample mixtures were applied on the surfaces of wood and mild steel
panels and monitored periodically for set-to-touch, surface dry and dry through time.
The sharpened edges of a set of different grades of pencils were used to press slowly
along the surface with force. The hardness was expressed in terms of the designation of
the hardest pencil that failed to scratch the film to give a continuous mark [10].
Infrared spectroscopic analysis was also performed on the prepared and
commercial alkyds. The FTIR spectra were recorded with a Shimadzu FTIR
spectrophotometer (100 series).

Results and discussion

Physicochemical properties of L. cylindrica seed oil

The result of the physiochemical properties of L. cylindrica seed oil is presented in

Table 2. The seed oil was liquid at room temperature with percentage yield of

Table 2 Physicochemical
Property Value
properties of L. cylindrica seed
oil
% yield 30.30
Colour Greenish brown
Refractive index (25 C) 1.46
State (28 C) Liquid
Acid value (mg KOH/g) 4.77
Iodine value (g I2/100 g) 153.0
Saponification value (mg KOH/g) 202.00
Peroxide value (meq O2/kg) 5.00
% Free fatty acids 2.4

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30.3 %. The oil yield is in close range with some cucurbits: musk melon (29.4 %),
bitter gourd (34.8 %), red pepper (26.3 %) and snake gourd (31.8 %) reported by
Vibhute [16]. Analysis of L. siceraria, L. breviflorus and L. cylindrica seed oil by
Essien et al. [17], gave percentage oil yield within the range 22–29. The relatively
low oil yield in this study compared to the reported yield by Burkill [6] may be
attributed to the harvest period, environmental factors, method of processing and
extraction technique, etc.
The iodine value of L. cylindrica (153 g I2/100 g) in this study is slightly higher
than some cucurbits: musk melon (111.3 g I2/100 g), bitter gourd (128.8 g I2/
100 g), rough cocklebur (133.4 g I2/100 g), red pepper (136.4 g I2/100 g) and
snake gourd (124.7 g I2/100 g) [16]. Some seed oils iodine values: rubber
(136.2 g I2/100 g), melon (112.9 g I2/100 g), soybean (128.4 g I2/100 g) and
jojoba (95 g I2/100 g), investigated as possible alternatives for conventional oils
used in the synthesis of alkyd resins have been reported in the literature [18–22].
The high iodine value is desirous for the synthesis of oil-modified alkyd resin. The
relatively low acid value (4.77 mg KOH/g), percentage free fatty acids (2.4 %) and
peroxide value (5.0 meq O2/kg) are advantageous to the production of alkyd resin
by reducing corrosion on coated materials. The level of acidity of oil used in alkyd
resins synthesis also determines the quantity of excess polyol required to neutralize
the acid for the polycondensation reaction [10]. Thus, the relatively low value of
acid index of L. cylindrica oil further suggest their preference for use in alkyd resin
synthesis and other industrial applications.

Fatty acids composition of L. cylindrica seed oil

The fatty acid profile of L. cylindrica seed oil is tabulated in Table 3. The result
reveals the presence of four major fatty acids: palmitic (13.4 %), stearic (6.38 %),

Table 3 Fatty acid composition

Fatty acids Value (%)
of L. cylindrica oil
Myristic acid (C14:0) 0.17
Palmitic acid (C16:0) 13.40
Palmitoleic acid (C16:1) 0.11
Stearic acid (C18:0) 6.38
Oleic acid (C18:1) 27.30
Linoleic acid (C18: 2) 50.25
Linolenic acid (C18:3) 0.12
Arachidonic acid (C 20:0) 0.02
Behenic acid (C22:0) 2.20
Lignoceric acid (C24:0) 0.05
Total saturated acids 22.22
Total unsaturated acids 77.78
Monounsaturated acids 27.41
Polyunsaturated acids 50.37

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oleic (27.3 %) and linoleic (50.25 %) acids. The studied seed oil has higher
percentage of unsaturated fatty acids (77.78 %) than saturated 22.2 %. The result
follows the trend (linoleic acid [ oleic acid [ palmitic acid) of fatty acids
composition of some legume seeds as described by Olaofe et al. [23]. The result
also indicates that L. cylindrica seed oil could be employed in the synthesis of alkyd
resin having sufficient unsaturated fatty acids that could enhance air drying property
[24].

Changes in acid value during synthesis

The fall in acid values during the polyesterification stage of alkyd resin synthesis
was determined at suitable intervals. The decrease in acid value is distinct for the
short, medium and long oils alkyds. Thus the rate of decrease in acid value can be
said to depend on the amount of oil used in the formulation. The change in acid
value from the plots (Fig. 2) was more rapid at the early stage than in the later.
Similar observation has been reported in the literature [25, 26]. The rapid initial
changes are attributed to the different reactivities of primary and secondary
hydroxyl groups of the glycerol; primary hydroxyl group reacts faster with the
carboxyl group of the phthalic anhydride than the secondary. It is also considered to
be due to the incorporation of almost all the reactants in the polymer chain at the
initial stage of the reaction, property of a step growth polymerization [26]. Also,
high amount of water was absorbed by the calcium oxide used at the early stages of
the reaction and then decreased as the reaction progressed. This can be attributed to

Fig. 2 Changes in acid value with reaction time

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the high initial esterification rate. Generally, the rate of polyesterification decreases
towards the end of the reaction as the concentration of the free acids decreases [20].

FTIR spectra of the alkyd resins

The infrared spectra of the short, medium and long oil alkyds and the commercial
sample are shown in Figs. 3, 4, 5 and 6, respectively. All the samples had absorption
bands at 1737.9–1734.0 cm-1 suggesting a phthalate type of ester group present. It
also suggests a carbonyl stretch of an ester. Similar (C=O) bands have also been
observed elsewhere for carbonyl esters of alkyd resins [2, 3, 15, 27]. A broad band peak
between 3491.2 and 3300.3 cm-1 in the spectra, results from free OH group; also
reported by Ezeh et al. [3], Chawla [28] and Dhoke et al. [29]. Carbon–oxygen stretch
at 1278.85–1274.99 cm-1 in all the samples suggests an ester group [30]. Also, all
samples exhibited absorption bands at 989.52–704.04 cm-1 and this could indicate a
monosubstituted aromatic ring. The spectra also show C–H vibrations 2926.11 cm-1
(LC-SOA), 3007.12, 2926.11 cm-1 (LC-MOA), 3009.05, 2926.11 cm-1 (LC-LOA)
and 3064, 2924.18 cm-1 (COA), indicative of C=C–H bond in the alkyd structures;
similar interpretation of spectra is also reported by Hlaing and Oo [2]. The similarity in
stretching frequencies of implicated functional groups of the prepared alkyd resins and
the commercial alkyd suggest successful conversion of the seed oil to alkyd resins.

Physicochemical properties of the alkyd resins

Some physicochemical properties of the synthesized light yellow alkyd resins and
commercial standard are presented in Table 4. The acid value ranged from 4.9 to

Fig. 3 Infrared spectrum of L. cylindrica short oil alkyd

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Synthesis and characterization of Luffa cylindrica fatty…

Fig. 4 Infrared spectrum of L. cylindrica medium oil alkyd

Fig. 5 Infrared spectrum of L. cylindrica long oil alkyd

7.1 mg KOH/g; iodine value (21.07–47.71 g I2/100 g); and non-volatile matter
(52.9–98.9 %). The acid values of all the prepared alkyds fall below 15 mg KOH/g.
The low acid value of the alkyds is necessary to reduce corrosion on substrates

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Fig. 6 Infrared spectrum of commercial alkyd resin

Table 4 Physiochemical properties of the prepared alkyd resins

Alkyds Colour Acid value Iodine value % Non-volatile
(mg KOH/g) (g I2/100 g) organic matter (%)

LC-SOA Light yellow 7.10 21.07 98.9

LC-MOA Light yellow 6.10 22.59 95.0
LC-LOA Light yellow 4.90 37.31 99.0
COA Light yellow 7.28 47.71 52.9

LC-SOA = L. cylindrica short oil alkyd; LC-MOA = L. cylindrica medium oil alkyd; LC-LOA = L.
cylindrica long oil alkyd; COA = commercial alkyd

Table 5 Performance properties of alkyd resins

Solubility Chemical resistance

Alkyd Toluene Acetone Xylene Distilled 0.1 M NaOH 0.1 M H2SO4 5 % NaCl
water

LC-SOA s s s n b n n
LC-MOA s s s n b n n
LC-LOA s s s n r n n
COA s s s n n n n

s = soluble; b = blistering of film; r = removal of film; n = no effect on film; LC-SOA = L. cylindrica

short oil alkyd; LC-MOA = L. cylindrica medium oil alkyd; LC-LOA = L. cylindrica long oil alkyd;
COA = commercial alkyd

coated with substances formulated with the finished alkyds [31]. The non-volatile
organic matter of the prepared alkyd resins was high compared to the commercial
sample. The iodine values of the prepared alkyd resins increase with increase in oil

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Table 6 Drying properties on wooden substrate

Alkyd In-door (26–28 C ± 2 C) Out-door (28–31 C ± 2 C)

Set-to-touch Surface dry Dry through Set-to-touch Surface dry Dry through
(min) (h) (h) (min) (h) (h)

LC-SOA 35 3.0 8.0 25 2.0 4.5

LC-MOA 40 4.0 8.5 30 2.5 5.5
LC-LOA 55 4.5 9.5 40 3.5 6.5
COA 40 3.5 8.5 30 3.0 5.0

LC-SOA = L. cylindrica short oil alkyd; LC-MOA = L. cylindrica medium oil alkyd; LC-LOA = L.
cylindrica long oil alkyd; COA = commercial alkyd

Table 7 Drying properties on metallic substrate

Alkyd In-door (26–28 C ± 2 C) Out-door (28–31 C ± 2 C)

Set-to-touch Surface dry Dry through Set-to-touch Surface dry Dry through
(min) (h) (h) (min) (h) (h)

LC-SOA 50 5.0 9.5 35 3.0 8.0

LC-MOA 60 5.5 10.5 40 3.5 8.5
LC-LOA 60 6.5 11.0 55 4.5 9.5
COA 50 5.5 10.0 40 3.5 9.5

LC-SOA = L. cylindrica short oil alkyd; LC-MOA = L. cylindrica medium oil alkyd; LC-LOA = L.
cylindrica long oil alkyd; COA = commercial alkyd

length. The trend is attributed to the increase in oil content and by implication the
level of unsaturation in the fatty acid chain [10].

Performance properties of the alkyd resins

The results of the solubility and chemical resistance tests for the alkyd resins and the
commercial standard are shown in Table 5. All the alkyd resins were soluble in the
three solvent media: acetone, toluene and xylene within 5 min. It was also observed
that the short oil alkyds took a longer time (5 min) to dissolve than the medium oil
alkyd (4 min), while the long oil alkyd dissolved within a minute. The rate of
dissolution of the alkyd resins was observed to decrease with increased viscosity.
Short oil alkyds are known to have higher viscosity due to higher extent of
polymerization, which necessitates swelling before dissolution [32]. The alkyd films
showed resistance to distilled water, aqueous sodium chloride and dilute H2SO4
solutions. However, the prepared alkyd samples showed poor resistance to sodium
hydroxides solution (alkali medium). This tendency is likely due to the basic
hydrolysis of the ester linkages in the alkyd resins [33].
The drying properties of the prepared alkyd resins on wooden and metallic
substrates are presented in Tables 6 and 7 respectively. The drying time is

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Table 8 Pencil hardness of

Alkyd Hardness
alkyds
Scratch Gouge
LC-SOA = L. cylindrica short
LC-SOA 3H 5H
oil alkyd; LC-MOA = L.
cylindrica medium oil alkyd; LC-MOA 2H 4H
LC-LOA = L. cylindrica long LC-LOA H H
oil alkyd; COA = commercial COA 4H 6H
alkyd

comparable with other oil-modified alkyd resins [10]. Generally, the set-to-touch,
surface dry and dry-through time for the alkyds increased with oil length. This could
be linked to the degree of cross-linkage, which is highest for the short oil alkyd and
reduces towards the long oil when subjected to same manufacturing conditions [5].
The differences observed on the drying performances of the alkyds indoor and
outdoor are evidences to the fact that sunlight, temperature and volume of oxygen,
influence the drying properties of alkyd resins [10]. The nature of substrate also
affects the drying performance of alkyd resins. According to Yadav et al. [34], the
presence of some polar functional groups (OH, COOH and COO-) on wood surface
similar to those on the alkyd resin, helps to enhance adhesion and by implication
improve the dry-through property of the alkyd resin.
Table 8 shows both scratch and gouge hardness of the prepared alkyd samples.
Both scratch and gouge hardness were observed to increase with decrease in oil
length. This shows that hardness is influenced by the drying time of the resins; the
faster the drying, the harder the film [10].

Conclusions

This study reveals that the underutilized and non-conventional vegetable oil from L.
cylindrica is a potential raw material for the coating industry. Some properties of the
synthesized alkyd resins compared well with the commercial standard. Hence, L.
cylindrica seed oil is suitable for the formulation of alkyd resins. It may be blended
with fast drying resins to impart gloss, flexibility and to reduce cost. Chemical
modification by co-polymerization with styrene, for example, may also be required;
since it is known that polystyrene is very resistant to the action of alkalis both in
alcoholic and non-aqueous media. This may lead to products that could meet up
with a wide range of applications.

Acknowledgments We appreciate the assistance of Dr. I. O. Isaac (Department of Chemistry, Akwa

Ibom State University, Mkpat Enin, Nigeria) in the preparation of the alkyds and Dr. N. O. Eddy
(Department of Chemistry, Akwa Ibom State University, Mkpat Enin, Nigeria) and Prof. Idara Akpabio
(Department of Physics, University of Uyo, Nigeria) in the infra red spectral analysis.

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