July 2010, Volume 1, No.

1
International Journal of Chemical and Environmental Engineering

Cation Exchange Properties of a Terpolymer:

Synthesis and Characterization

M. Riswan Ahamed1, R. Azarudeen1, M. Karunakaran2, T. Karikalan1, R. Manikandan1, A. Burkanudeen1*

1
PG & Research Department of Chemistry, Jamal Mohamed College (Autonomous) Tiruchirappalli – 620 020, Tamil
Nadu, India
2
Department of Science and Humanities, P.A. College of Engineering and Technology, Pollachi – 642 001, Tamil Nadu,
India
*Corresponding author: a_deen@rediffmail.com

Abstract
4-hydroxybenzoic acid - thiourea - formaldehyde (4-HBTUF) terpolymer has been prepared by polycondensation technique in 2:3:5
mole ratio using 2M H2SO4 as a catalyst was proved to be a selective chelation ion-exchange for certain metals. The characterization
and the structural elucidation of the prepared terpolymer were confirmed by elemental analysis, FTIR and 1H-NMR spectral studies.
The morphological feature of the 4-HBTUF tepolymer was established by scanning electron microscopy (SEM). The gel permeation
chromatography (GPC) was used to determine the average molecular weight of the terpolymer resin. The cation-exchange properties
of the terpolymer were determined by batch equilibrium method. The method involves ion-exchange behavior of the terpolymer with
specific cations like Cd2+, Mg2+, Fe3+, Cu2+, and UO22+ in various electrolytes, wide pH ranges and different time intervals. The results
of the ion-exchange studies reveal that the 4-HBTUF terpolymer was found to be an excellent cation-exchanger for selective metal
ions. Hence the resin can be used to recover metal ions from waste solutions and used for the purpose of purification of waste water
and for the removal of iron from boiler water. The ion-exchange capacity of the terpolymer has also been compared with the other
commercial resins.
Keywords: Terpolymer, FTIR, Morphology, Gel Permeation Chromatography, Chelation Ion-exchange Study.

1. Introduction
Over the past few decades, significant research work
has been done on enhancing the properties of new
synthesized ion-exchange terpolymers for the treatment of
waste water and pollution control. Ion-exchange may be
defined as the reversible exchange of ions between the
substrate and surrounding medium. The removal of heavy
metal ions from industrial wastewater has been given
much attention in the last decade, as the heavy metals
released into the environment pose potential threat,
because of their tendency to accumulate in living
organisms. The necessity to reduce the amount of heavy
metal ions pollution in wastewater streams has led to an
increasing interest in ion-exchange terpolymers [1-6].
Therefore, attempt has been made to synthesize
terpolymer and to evaluate the ion-exchange properties.
Various combinations of thiourea based terpolymers like
8-hydroxyquinoline-5-sulfonic acid – thiourea -
formaldehyde, ortho-nitro phenol – thiourea –
paraformaldehyde and anthranilic acid – thiourea -
paraformaldehyde have been synthesized by condensation
polymerization and reported for their chelation ion-
exchange properties toward selective metal ions [7-9].
Ion-exchange terpolymer derived from 2, 2-
dihydroxybiphenyl-urea-formaldehyde has been reported
as an effective ion-exchanger against certain transition
metal ions [10]. The chelating behavior of the synthesized
resin was studied using metal ions Ni(II), Cu(II), Zn(II),
Cd(II) and Pb(II) and the sorption capacities of the resin
follows the order Pb(II)<Zn(II)<Cd(II)<Cu(II)<Ni(II)
[11]. Cation-exchange behavior of a reported terpolymer
show higher selectivity for Cu (II), Zn (II) and Co (II) as
compared to Ni (II), Pb (II) and Cd (II) metal ions [12]. p-
Cresol and oxamide with formaldehyde terpolymer was a
selective chelating ion-exchange resin for Fe3+, Cu2+,
Ni2+, Co2+, Zn2+, Cd2+ and Pb2+ ions [13].
Ion-exchange technique can be used to remove traces
of ionic impurities from water/process liquors and gives
out a product of ultra pure quality in a simple efficient
and techno-economically viable manner. Hence, the
present article describes the preparation, characterization
and ion-exchange properties of 4-hydroxybenzoic acid
and thiourea with formaldehyde terpolymer.
2. Experimental
2.1 Chemicals and Reagents
4-hydroxybenzoic acid (SRL, Mumbai) and thiourea
 Cation Exchange Properties of a Terpolymer: Synthesis and Characterization
(Merck, India) were purified by rectified spirit.
Formaldehyde (37%), metal nitrates of chosen metals
(AR grade, Merck) was used as received. All the other
chemicals, solvents and the indicators were of analytical
grade procured from Qualigens fine chemicals, Mumbai,
India. Standardized Na2EDTA was used as a titrant for all
the complex metric titrations. Double distilled water was
used for all the experiments.
2.2 Terpolymerization
The terpolymer resin was synthesized by the
condensation reaction of 4-hydroxybenzoic acid (0.2
mol), thiourea (0.3 mol) and formaldehyde (0.5 mol)
using 2M H2SO4 as the reaction medium and refluxed
with occasional shaking at 140 ± 2 °C for 4 h [8-13]. The
reaction mixture was then cooled, poured into crushed ice
with constant stirring and left.
OH
S taken in a pre-cleaned glass bottles and each of the
+ H2N C +
NH2
COOH
4-Hydroxybenzoic acid Thiourea
2M H 2SO4 140 ± 2°C
4h
OH
H2 H2
C NH C NH C
S
COOH
4-HBTUF Terpolymer
Scheme 1. Reaction route of 4-HBTUF terpolymer
Overnight. The dark brown coloured resin separated
out was washed with warm water and methanol. It was
then filtered off to remove the unreacted monomers.
Finally, the terpolymer was air dried. The dried sample
was then dissolved in 8% NaOH and regenerated using
1:1(v/v) HCl/water. It was filtered off and cured in an air
oven at 75 °C for 24 h. The yield of the terpolymer was
found to be 83% and the reaction route is shown in
Scheme 1.
2.3 Spectral analysis
The FTIR spectrum of the synthesized terpolymer
had been scanned in KBr pellets on a Bruker (Model
Tensor 27) spectrophotometer to identify the linkages and
the functional groups. The proton NMR spectrum of the
terpolymer was recorded in DMSO-d6 solvent using
Bruker 400 MHz.
2.4 Surface analysis and GPC
The average molecular weight of the 4-HBTUF
terpolymer was determined by gel permeation
chromatography in Shimadzu using DMSO column. The
surface analysis of the 4-HBTUF terpolymer was
examined by scanning electron microscope Hitachi
(Model S-3000H).
2.5 Ion-exchange characteristics
The cation-exchange properties of 4-HBTUF
terpolymer were studied by batch equilibrium method.
The finely ground terpolymer was used to determine the
metal ion uptake capacity of the metal ions like Cd2+,
Mg2+, Fe3+, Cu2+, and UO22+ in the form of their aqueous
metal nitrate solutions. Metal ion binding capacity for the
terpolymer was studied in various electrolytes with
different concentrations, pH ranges and time intervals.
2.6 Effect of metal ion uptake in different electrolytes with
variation in concentrations
The prepared 4-HBTUF terpolymer (25 mg) was
CH 2O
electrolytes (25 mL) such as NaCl, NaNO3, NaClO4, and
Na2SO4 in different concentrations viz. 0.1, 0.5 and 1.0 M.
The pH of the suspension was adjusted to the required
value either by adding 0.1 M HCl or 0.1 M NaOH. This
Formaldehyde suspension was mechanically stirred for 24 h at 25 °C for
the swelling of the terpolymer. To this suspension 2 ml of
0.1 M of specific metal ion solution was added and
vigorously stirred for 24 h at 25 °C. It was then filtered
OH off and washed with distilled water. The filtrate and the
washings were collected and then the amount of metal ion
n was estimated by titrating against standard Na2EDTA
solution. A blank experiment was also performed
following the same procedure without the polymer
sample. The amount of metal ions taken up by the
polymer in the presence of a given electrolyte can be
COOH
calculated from the difference between the actual titre
value and that of from the blank. The chelating
mechanism of the terpolymer resin is as follows.
(Res.A-)B+ + C+ (solution) ↔ (Res.A-)C+ + B+ (solution) (1)
where, Res., A-, B+, and C+ represents the polymeric
resin, the anion attached to the polymeric framework, the
active or mobile cation, and the metal ion respectively.
2.7 Effect of the distribution of metal ions at various pH
The distribution of each one of the metal ions at various
pH ranging from 3 to 5.5 between the polymer phase and
the aqueous phase were determined in the presence of 1
M NaNO3 at 25 ºC. The distribution ratio KD, may be
defined as
Weight (in mg) of metal ions taken
up by 1 g of the resin sample
KD = --------------------------------------------- (2)
Weight (in mg) of metal ions
present in 1 mL of the solution
2.8 Effect of rate of metal ion uptake
8
 Cation Exchange Properties of a Terpolymer: Synthesis and Characterization

A series of experiments were carried out to may be assigned due to the ν C-N stretching vibration.
determine the amount of metal ion adsorbed by the The tetra substitution in the benzene ring is established by
terpolymer at specific time intervals. 25 mg of the the presence of the medium bands at 1022 and 758 cm-1
polymer sample was mechanically stirred with 25 mL of 1 are assumed ν (C-H) bending vibrations [14-17].
M NaNO3 to allow the polymer to swell. The pH of the Table 2.Elemental analysis of 4-HBTUF Terpolymer
suspension was adjusted to the required value by adding
either 0.1 M HCl or 0.1 M NaOH. It is assumed that Analysis (%)
under the given experimental conditions the state of Sample Calculated (Found)
equilibrium is established within 24 h at 25 ºC. The rate name C H N S
of metal ion uptake is expressed as the percentage of the
metal ion uptake after a specific time related to that of the
state of equilibrium. It is given as, 4-HBTUF 55..43 4.86 6.81 7.79
terpolymer (55.21) (4.21) (6.34) (7.41)
Amount of metal ion adsorbed
Metal ion uptake = -------------------------------------- ×100 (3)
Amount of metal ion adsorbed
at equilibrium

3. Result and discussion

The 4-hydroxybenzoic acid and thiourea with
formaldehyde (4-HBTUF) terpolymer was soluble in
solvents like N,N-dimethylformamide (DMF),
tetrahydrofuran (THF), dimethylsulphoxide (DMSO), and
aqueous sodium and potassium hydroxide solutions.
3.1Physicochemical and Elemental Analysis
The physicochemical parameters such as moisture
content, solid percentage, void volume fraction, true
density and sodium exchange capacity of the 4-HBTUF
terpolymer are shown in Table I. The results of the
elemental analysis of the terpolymer are presented in Fig.1 FTIR spectrum of 4-HBTUF terpolymer
Table 2. Based on the analytical data, the empirical 1
formula of the terpolymer is found to be C19H20N2O6S H NMR spectrum of 4-HBTUF terpolymer is
which is in good agreement with the calculated values of depicted in Fig. 2 and the spectral data are presented in
C, H, N and S. Table 4. The NMR spectrum reveals that the signal
around 3.3 δ is due to the methylene proton of the Ar-
3.2 Spectral Studies CH2-N linkage. The multiple signals observed in the
The recorded FTIR spectrum of the 4-HBTUF range of 6.9 – 7.5 δ indicate the presence of aromatic
terpolymer is shown in Fig. 1 and the important IR bands protons. The signal displayed at 8.4 δ may be due to the
along with their assignments appeared in the spectrum is carboxylic proton of Ar-COOH group. The signal in the
presented in Table 3. The spectrum shows a strong band region of 8.7 δ is assigned to the –OH of Ar-OH group.
at 3479 cm-1 due to the ν (O-H) stretching of Ar-OH An intense signal appeared in the region of 5.5 δ is
group. The band appeared at 2640 cm-1 is due to aromatic assigned to the –NH protons of in the terpolymer [18].
ν (C-H) stretching group. The weak band at 2872 cm-1 is
Table. 3 FTIR Spectral data of 4-HBTUF Terpolymer
due to the ν (C-H) stretching of methylene group. The
band at 1672 cm-1 may be assigned to ν (C=O) stretching Frequency (cm-1)
Vibrational mode
of ketonic group of acid. The band appeared at 3376 cm-1 Reported Observed
-OH of Ar-OH group 3500-3200 3479.8
is due to ν NH-stretching vibrations. Methylene(-CH2) 3000-2850 2872.8
Table 1.Physicochemical characteristics of 4-HBTUF Terpolymer stretching
>C=O stretching 1690-1620 1672.1
Properties Value (SD) (carboxylic ketone)
Moisture (%) 10.4 ± 0.25 1,2,3,5-substituted 1200-700 1022.0 & 758.1
Solid (%) 89.6 ± 0.25 benzene ring
True density (dry resin) g/cm3 1.498 ± 0.05 (C-N) stretching 1100-1200 1116.1
Void volume fraction 0.765 ± 0.025 Aromatic ring stretching 2700-3000 2640.6
Sodium exchange capacity ( mmol/g dry 6.78 ± 0.40 (C-H)
resin) NH bridge 3500-3200 3376.3
The band appeared at 1299 cm-1 and 916 cm-1 may be C=S stretching & - 1299.1 & 916.6
bending
due to ν C=S stretching and bending vibration
respectively. The band clearly appeared around 1116 cm-1

9
 Cation Exchange Properties of a Terpolymer: Synthesis and Characterization

Table 4. 1H NMR Spectral data of 4-HBTUF Terpolymer

Assigned protons Expected Observed

chemical shift chemical shift
(δ) ppm (δ) ppm

Aromatic proton (Ar-H) 6.2-8.5 6.9-7.5

Protons of NH bridge 5.5-6.0 5.5

Ar-COOH group 8.0-12.0 8.4

Phenolic (Ar-OH) 7.5-12.0 8.7

1
Fig.2 H NMR spectrum of 4-HBTUF terpolymer Ar-CH2- moiety 1.5-2.5 1.8
3.3 Surface analysis and molecular weight measurements
Ar-CH2-N moiety 3.0-3.5 3.3
The average molecular weight of the 4-HBTUF
terpolymer is determined by gel permeation
chromatography. The number average molecular weight
( Mn ) and weight average molecular weights ( Mw ) are 3.5 Effect of metal ion uptake in different electrolytes with
5575 and 5764 respectively. The polydispersity index variation in concentrations
( Mw / Mn ) is found to be 1.033. The average molecular The chelation ion-exchange property of the 4-HBTUF
weight ( Mz ) of the terpolymer is 5943. The polydisperstiy terpolymer was measured by batch equilibrium method
involving Cd2+, Mg2+, Fe3+, Cu2+, and UO22+ metal ions in
( Mz / Mn ) is 1.066. The data obtained from molecular
various electrolytes viz. NaCl, NaNO3, NaClO4, and
weight measurements are presented in Table 5.
Na2SO4 in different concentrations such as 0.1, 0.5, and
3.4 Morphological studies 1.0 M. The results are presented in Table 6.
The typical microphotograph at 6000× magnification Table 6. Effect of metal ion uptake by 4-HBTUF Terpolymer
from SEM of 4-HBTUF is shown in Fig. 3. The SEM
image shows the surface feature of the sample. The
Weight of metal ion uptake in presence of
photograph clearly shows that the terpolymer has deep Electrolyte electrolytes
shallow pits with more amorphous character and less concentrations (mg)
Metal
close packed surface. Further, it is interesting to note that (mol.L-1)
ions
the high porosity and less close packed nature of the NaCl NaNO3 NaClO4 Na2SO4
terpolymer provide enough space for the metal ions of
specific size to be accommodated in the pores. Hence, 0.1 5.3 6.2 4.9 6.3
these kinds of polymers can act as effective ion- Fe3+
0.5 5.7 6.5 5.1 5.9
exchangers. 1.0 5.9 6.9 5.4 5.2

Table. 5 GPC for molecular weight measurements

0.1 2.9 4.3 2.4 3.2
2+ 0.5 3.1 4.8 2.7 2.9
Polydispersity Polydispersity Cd
Compound 1.0 3.4 5.1 3.0 2.8
Mn Mw Mz Mw / Mn Mz / Mn

0.1 4.7 5.4 4.4 6.1

0.5 4.8 5.8 4.1 5.3
4-HBTUF 5575 5764 5943 1.033 1.066 Cu2+
terpolymer 1.0 5.0 6.1 3.8 5.1

0.1 3.8 4.9 3.1 4.7

0.5 4.2 5.2 3.5 4.1
UO22+ 1.0 4.6 5.7 3.7 3.6

0.1 1.8 2.9 1.5 2.2

Mg2+ 0.5 2.0 3.3 1.7 1.7
1.0 2.4 3.7 1.9 1.4

M2+(NO3)2 = 0.1 M; volume = 2 mL; volume of electrolyte = 25 mL;

weight of resin = 25 mg; time = 24 h; temperature = 25 ºC.

From the data it is observed that the amount of metal

Fig.3 SEM photograph of 4-HBTUF terpolymer ion taken up by the terpolymer depends on the nature and
concentrations of the electrolytes. The increase in the
10
 Cation Exchange Properties of a Terpolymer: Synthesis and Characterization

metal ion uptake with the increase in concentration may
be explained on the basis of the stability constants of the
complexes. From the results, it is observed that the
amount of metal ion taken up by the terpolymer increases
with the increasing concentration of Cl-, NO3-, and ClO4-
and decreases with the increasing concentration of SO42-
ion. This may be due to the sulphate ion forming strong
chelates with metal ions, while other anions form weak
chelates. The amount of uptake of Fe3+ and Cu2+ ions by
the terpolymer is comparatively higher than that of the
other metal ions such as UO22+, Cd2+, and Mg2+ [19]. This
may be due to the Fe3+ and Cu2+ ions form weak chelates
with the anions of the electrolytes compared to the other
metal ions.
Further, the polymer is amorphous in nature and has
porosity in its structure; hence they can accommodate
metal ions of specific size, easily into its cavities. The
metal binding property of the 4-HBTUF terpolymer is
found to be higher than that of the other polymeric resins
reported earlier [13].
3.6 Effect of distribution of metal ions at various pH
The distribution of each one of the metal ions such as
Cd2+, Mg2+, Fe3+, Cu2+, and UO22+ between polymer phase
and the aqueous phase was determined at 25 °C in the
presence of 1 M NaNO3 at various pH ranging from 3 to
5.5. The study was restricted up to maximum pH of 5.5,
due to the precipitation of metal ions at higher pH. The
formations of metal hydroxide also interfere with the ion-
exchange process. The amount of the metal ion which
remained in the aqueous phase was estimated. If the
original metal ion concentration is known, the metal ion
adsorbed by the resin can be calculated. The effect of pH
on the amount of metal ions reveals that the uptake of
metal ions by the terpolymer at equilibrium increases with
increasing pH (Table 7). It is perceived that the
equilibrium state is attained in 24 h at 25 ºC under the
given conditions.
Table 7.Effect of distribution ratios (KD), as a function of pH by 4-
HBTUF Terpolymer
Distribution ratio (KD) of the metal ions
Metal pH of the medium
ions
3 3.5 4 4.5 5 5.5
It is also observed that the terpolymer takes up Fe3+
ions more effectively than other ions under study at all pH
values. Among the other ions taken up for the study, Cu2+
and UO22+ shows selective uptake of the metal ions under
moderate pH values. Further, Cd2+ and Mg2+ ions have
lower distribution ratio over the pH ranges from 3 to 5.5.
This can be explained as the weak stabilization energy of
the metal chelates formed from these ions. In the present
investigation it is observed that the order of the
distribution ratio of the metal ions are Fe3+ > Cu2+ > UO22+
> Cd2+ > Mg2+ for the pH ranges from 3 to 5.5. The values
of the distribution ratio and the order at different pH
depend on the nature of the polymeric resin and its
structure.
3.7 Effect of rate of metal ion uptake
The rate refers to the change in the concentration of
the metal ions in the aqueous solution, which is in contact
with the terpolymer. Perusal of the Table 8 reveals that
the time taken for the uptake of the different metal ions at
a given stage depends on the nature of the metal ion and
its ionic size. The rate of metal ion uptake follows the
order Fe3+ > Cu2+ > UO22+ > Cd2+ > Mg2+ for the 4-
HBTUF terpolymer.
3.8 Comparative study for resin
The ion-exchange capacity of the terpolymer resin
was compared with the commercially available resins.
The metal ion uptake capacity for the 4-HBTUF resin was
found to be 5.58 mmol/g for Fe3+ ion. Futher the ion-
exchange capacity of the terpolymer is comparable to the
commercially available ion-exchange resins for the other
metal ions also under study. This shows that the PUF
resin has higher uptake capacity for the ion-exchange
process than commercial phenolic and polystyrene ion-
exchange resins (Table 9).
Table 8 Effect of rate of metal ion uptake by 4-HBTUF
Terpolymer
Equilibrium attainment (%)
Metal Time (h)
ions
1 2 3 4 5 6 7
Fe3+ 58 67 73 86 97 - -

Fe3+ 143.2 231.23 332.15 454.24 523.64 591.43

1 Cu2+ 44 56 69 76 88 95 -

Cu2+ 106.9 165.74 276.21 345.86 467.86 511.54

8 UO22+ 35 47 58 64 79 87 94

UO22+ 97.34 143.49 258.34 332.52 453.76 489.65

Cd2+ 26 38 45 59 71 84 92

Cd2+ 75.36 136.21 221.87 321.76 399.79 434.45

Mg2+ 14 30 38 48 65 73 90

M2+(NO3)2 = 0.1 M; volume = 2 mL; NaNO3 = 1 M; volume = 25 mL;

Mg2+ 71.35 113.45 211.65 301.66 335.67 397.27
weight of resin = 25 mg; temperature = 25 ºC.

M2+(NO3)2 = 0.1 M; volume = 2 mL; NaNO3 = 1 M; volume = 25 mL;

weight of resin = 25 mg; time = 24 h; temperature = 25 ºC.

11
 Cation Exchange Properties of a Terpolymer: Synthesis and Characterization

Table 9.Comparative study of the various Ion exchange resins

Ion-Exchange [5] O. Szabadka, E. Varga, and L. Nagy, “Determination of

Trade Name Polymer Matrix capacity protonation and metal complex stability constants for a chelating
(mmol/g) monomer and its immobilized in polymer resin,” Talanta., vol.
Amberlite IR-120 Polystryrene 5.0-5.2 59, pp. 1081–1088, 2003.

Duolite C-3 Phenolic 2.8-3.0 [6] Q. Rong-jun, J. Chun-nuan, S. Yan-zhi, L. Zhong-fang, C. Guo-
xiang, and S. Ren-feng, “Syntheses and adsorption properties of
Amberlite IRC-50 Methacrylic 9.5
phenol-formaldehyde-type chelating resins bearing the functional
Duolite ES-63 Polystryrene 6.6 group of tartaric acid,” Chinese J. Polym. Sci., vol. 22(5), pp.
469–475, 2004.
Dowex – 1 Polystryrene 3.5
Amberlite IRA-45 Polystryrene 5.6 [7] V.D. Mane, N.J. Wahane, and W.B. Gurnule, “Copolymer resin.
VII. 8-hydroxyquinoline-5-sulfonic acid–thiourea–formaldehyde
Dowex – 3 Polystryrene 5.8
copolymer resins and their ion-exchange properties,” J. Appl.
4-HBTUF Resin Phenolic 5.58 Polym. Sci., vol. 111, pp. 3039–3049, 2009.

[8] A. Burkanudeen, and M. Karunakaran, “Chelation ion-exchange

4. Conclusion
A terpolymer (4-HBTUF) was prepared from 4-
hydroxybenzoic acid and thiourea with formaldehyde in
sulphuric acid medium by condensation polymerization
technique. From the elemental analysis, FTIR, and NMR
spectral studies the proposed structure of the terpolymer
was confirmed. In the ion-exchange studies, the resin was
highly selective for Fe3+ > Cu2+ > UO22+ > Cd2+ > Mg2+
ions which may be due to the presence of S and N atoms.
The sulfur atom plays the key role in binding the metal
ions and nitrogen helps in chelation. The highly
amorphous nature of the 4-HBTUF terpolymer confirmed
by SEM studies further proves that the terpolymer can act
as an effective ion-exchanger. The exchange capacity of
the chosen metal ions is comparable to the commercial resins.
ACKNOWLEDGMENT
The authors thank the Management & Principal of
Jamal Mohamed College, Tiruchirappalli, Tamil Nadu
and Dr. D. Jeyakumar, Scientist, Central Electrochemical
Research Institute, Karaikudi, Tamil Nadu for their
support and encouragement.
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