July 2010, Volume 1, No.

1
International Journal of Chemical and Environmental Engineering

Metal Sorption Studies of a Novel Terpolymer

Resin
R. Azarudeen1, M. Riswan Ahamed1, P. Arunkumar2, N. Prabu2, D. Jeyakumar2, A. Burkanudeen1*
1
PG &Research Department of Chemistry, Jamal Mohamed College (Autonomous), Tiruchirappalli – 620
020, Tamil Nadu, India
2
Functional Materials Division, Central Electrochemical Research Institute, Karaikudi – 630 006, Tamil
Nadu, India
*Corresponding author: a_deen@rediffmail.com*

Abstract
Novel terpolymer resin involving phthalic acid and urea with formaldehyde (PUF) was synthesized by condensation
polymerization in glacial acetic acid medium and proved to be a selective chelation ion-exchange terpolymer for certain
metals. The resin was characterized by FTIR and 1H NMR spectroscopy. Based on the spectral data, the structure of the
resin was proposed. The average molecular weight of the terpolymer resin was determined by gel permeation
chromatography (GPC). The morphology of the terpolymer was established by scanning electron microscopy (SEM). In
addition, the physicochemical parameters were also determined for the terpolymer resin. A batch equilibrium method
was employed to study the selectivity and sorption capacity of the resin towards certain divalent metal ions such as
Pb2+, Zn2+, Cu2+, Ni2+, Ba2+, Co2+ and Mn2+ in various electrolyte concentrations, wide pH ranges and different
time intervals. Hence the resin can be used to recover certain metal ions from waste solutions and used for the purpose of
purification of waste water and removal of iron from boiler water. The ion-exchange capacity of the metal ions has also
been compared with other commercial resins.

Keywords: Terpolymer, Sorption, Batch Equilibrium, Morphology, Solution Condensation.

1. Introduction
The removal of traces of heavy toxic metal ions
present in industrial waste water, domestic and nuclear
wastes has been given much attention in the last decades,
because of their tendency to accumulate in living
organisms and induces harmful effects to natural
resources. Therefore, an attempt has been made to
synthesize a novel chelating terpolymer and to assess the
ion-exchange characteristics of the terpolymer [1, 2].
Terpolymers were applied in various fields of research as
ion-exchangers, high thermal resistance materials, and
electrical appliances [3, 4]. Ion-exchange is a process of
reversible exchange of ions between the substrate and the
surrounding medium. 2, 4-dihydroxyacetophenone –
biuret – formaldehyde terpolymer resin was synthesized
and its chelating ability for several metal ions was
investigated [5]. Polyacrylonitrile-2-amino-2-thiazoline
resin was synthesized and their sorption behaviors for
ruthenium, rhodium, palladium and iridium metal ions
have been reported [6]. Terpolymer synthesized from o-
nitro phenol and thiourea with paraformaldehyde and its
metal ion uptake capacity for few metal ions were
reported by Burkanudeen et al [7]. Anthranilic acid and
thiourea with paraformaldehyde terpolymer resin was
synthesized and ion-exchange property for few transition
metal ions were reported [8]. Tetracycline sorbed
zirconium tungstophosphate was prepared and it has been
successfully used as a sorbent to remove the La (III) ions
[9]. A chelating terpolymer resin was synthesized using
an eco-friendly technique and reported for its good
binding capacity for specific metal ions such as Zn2+,
Mn2+, Cu2+, Ba2+ and Mg2+ ions [10]. Chelation ion-
exchange behavior of p-cresol and oxamide with
formaldehyde terpolymer was reported for selective metal
ions like Fe (III), Co (II), Zn (II), Pb (II), Cu (II), Ni (II),
and Cd (II). Among the selected metal ions, the
terpolymer was found to have an increased binding
capacity for Cu (II), Fe (III), and Co (II) ions [11].
Polystyrene supported chelating resins containing
heterocyclic groups have been synthesized and it was
reported for its effective adsorption capacity towards
silver, mercury, palladium and gold ions [12]. Recently,
our research group reported a terpolymer resin involving
anthranilic acid and salicylic acid with formaldehyde for
 Metal Sorption Studies of a Novel Terpolymer Resin

COOH
its chelation ion-exchange properties by batch equilibrium NH2
method for Pb2+, Zn2+, Cu2+, Mg2+ and Ba2+ ions [13]. + + CH2 O
In this research article, the synthesis of terpolymer C
H 2N O
involving phthalic acid and urea with formaldehyde is COOH

reported. The synthesized terpolymer was characterized

Phthalic acid Urea Formaldehyde
by spectral studies, SEM and GPC. Batch equilibrium
method was adopted to determine the sorption capacity of
HOAc 160 °C
the terpolymer resin for the selective metal ions like Pb2+,
Zn2+, Cu2+, Ni2+, Ba2+, Co2+ and Mn2+.
HOOC COOH HOOC COOH
2. Materials and Method
2.1 Materials
Phthalic acid (SRL, Mumbai), urea (Merck, India),
H2 H H H2
formaldehyde (37%), metal chlorides and nitrates of C N C N C
chosen metals (AR grade, Merck) were used as received.
O n
All the other chemicals, solvents and the complex metric
titration indicators such as fast sulphon black for copper, PUF Terpolymer Resin

methyl thymol blue for barium, xylenol orange for lead

and cobalt, solo chrome black for zinc and manganese,
and mureoxide for nickel were of the analytic grade
procured from Qualigens, India. Standardized Na2EDTA
was used as a titrant for the complex metric titrations.
2.2 Polymerization of PUF
The PUF terpolymer resin was synthesized by the
solution condensation polymerization of phthalic acid (0.1
mol) and urea (0.1 mol) with formaldehyde (0.2 mol) in
glacial acetic medium at 160 ± 2 °C in an oil bath for 6 h
[5, 11]. The resultant product was then cooled, poured
into crushed ice with constant stirring and left overnight.
The colorless resin obtained was separated and washed
with warm water, ethanol and ether and air dried. The
dried resin was further purified by dissolving in 8%
NaOH and regenerated in 1:1(v/v) HCl/water. The resin
was then filtered off and cured at 80 °C for 36 h in an air
oven. The yield of the terpolymer was found to be 85%.
The dried resin sample was finely grounded and sieved to
obtain uniform particle of 100 mesh size and stored in a
polyethylene container. The reaction sequence for the
synthesis of PUF terpolymer resin is shown in Scheme 1.
2.3 Characterization of the Terpolymer
The physicochemical parameters such as moisture
content, solid percentage, void volume fraction, true
density and sodium exchange capacity were evaluated as
per the earlier procedure [14]. The FTIR spectrum of the
synthesized resin sample had been scanned in KBr pellets
on a Bruker (Model Tensor 27) spectrophotometer. The
1 calculated from the difference between the actual value
H NMR spectrum of the resin was recorded in DMSO-d6
solvent using Bruker 400 MHz. The average molecular
weight of the terpolymer was determined by gel
permeation chromatography Shimadzu using DMSO
column. The surface analysis of the PUF terpolymer resin
was examined by Hitachi (Model S-3000H) scanning
electro microscope.
Scheme 1. Reaction sequence of PUF terpolymer resin
2.4 Ion-Exchange Studies
The ion-exchange properties of PUF terpolymer was
evaluated by batch equilibrium method for specific metal
ions such as Pb2+, Zn2+, Cu2+, Ni2+, Ba2+, Co2+ and Mn2+ in
the form of their aqueous metal nitrate solutions. The ion-
exchange capacity of the terpolymer was studied as a
function of various electrolytes in different
concentrations, pH ranges, and time intervals.
2.5 Evaluation of Metal Ion Uptake in Various
Electrolytes in Different Concentrations
The PUF terpolymer (25 mg) was taken in a pre-
cleaned glass bottles and each of the electrolytes (25 mL)
such as KCl, KNO3, KClO4 and K2SO4 in different
concentrations viz. 0.01, 0.1 and 0.5 M. The pH of the
suspension was adjusted to the required value either by
adding 0.1 M HCl or 0.1 M NaOH and mechanically
stirred for 24 h at 25 °C for swelling of the terpolymer.
Then exactly 0.1 M of the metal ion solution (2 mL) was
added and vigorously stirred for 24 h at room
temperature. The mixture was then filtered off and
washed with distilled water. The filtrate and the washings
were collected and then the amount of metal ion adsorbed
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
and that of from the blank. The mechanism involved in
the chelation of the terpolymer resin is as follows.
(Res.A-)B+ + C+ (solution) ↔ (Res.A-)C+ + B+(solution)
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.

24
 Metal Sorption Studies of a Novel Terpolymer Resin

2.6 Evaluation of the Distribution of Metal Ions at Table I. Phyicochemical Properties of PUF resin
Different pH Properties Value (SD)
The distribution of each of the metal ions at various
pH ranging from 3 to 5.5 between the polymer phase and Moisture (%) 4.1 ± 0.25
the aqueous phase were determined in the presence of 1 Solid (%) 95.9 ± 0.45
M KNO3 at 25 ºC. The distribution ratio KD, may be True density (dry resin) g/cm3 1.47 ± 0.03
defined as Void volume fraction 0.887 ± 0.015
Sodium exchange capacity ( mmol/g 9.19 ± 0.25
KD = Weight (in mg) of metal ions taken up by 1 g of the dry resin)
resin sample / Weight (in mg) of metal ions present in 1
mL of the solution
2.7 Evaluation of Rate of Metal Ion Uptake
The time required for attaining the state of
equilibrium under the experimental conditions was
evaluated by a series of experiments carried out to
determine the amount of metal ion adsorbed by the
terpolymer at specific time intervals. 25 mg of the
polymer sample was mechanically stirred with 25 mL of 1
M KNO3 to allow the polymer to swell. The pH of the
suspension was adjusted to the required value by adding
either 0.1 M HCl or 0.1 M NaOH. It was observed that
under the given experimental conditions the state of
equilibrium established within 24 h at 25 ºC. The rate of
metal ion uptake is expressed as the percentage of the Figure 1. FTIR spectrum of PUF terpolymer resin
metal ion uptake after the specific time related to the state 3.3 1H
NMR Spectral Analysis
of equilibrium. It is given as, The 1H NMR spectrum of the PUF terpolymer is
Metal ion uptake = Amount of metal ion adsorbed / shown in Fig. 2. The signal at 8.85 ppm is assigned to the
Amount of metal ion adsorbed at equilibrium × 100 -OH of Ar-COOH and this downfield shift is due to the
1. Results and Discussion: intermolecular hydrogen bonding [10]. The signals in the
region of 6.5– 7.6 ppm are assigned to all the protons of
3.1 Physicochemical Analysis the aromatic ring [10]. The signals appeared in the region
The PUF terpolymer resin was soluble in solvents of 1.1 to 4.21 ppm is due to the methylene proton of Ar-
like N,N-dimethylformamide (DMF), tetrahydrofuran CH2 bridge [15]. The signal appeared in the region of 6.4
(THF), dimethylsulphoxide (DMSO), aqueous sodium ppm is due to the –NH bridge present in the terpolymer
and potassium hydroxide solutions and insoluble in [18].
alcohol, chloroform and carbon tetrachloride. The
physicochemical parameters such as moisture content, 3.4 Morphology and Molecular Weight Measurements
solid percentage, void volume fraction, true density and The SEM image of the terpolymer at 5000× is shown
sodium exchange capacity of the terpolymer resin are in Fig. 3. The image of the resin was found to be less
shown in Table 1. close packed with high porosity over the surface of the
terpolymer. The micrograph of the resin also shows a
3.2 Infra-Red Spectral Analysis fringed micelle model having deep and shallow voids on
FTIR spectrum of PUF is depicted in Fig. 1. A band the surface of the polymer indicates the presence of
appeared in the region of 3442.7 cm-1 is assigned to the amorphous structure. Presence of voids and cavities of
hydroxyl group of –COOH present in the aromatic ring specific size can adsorb metal ions on their surface. This
which is involved in an intramolecular hydrogen bonding is evident from the higher ion-exchange capacity of the
[15]. A peak appeared at 2807.5 cm-1 is assigned to terpolymer also. The GPC data for the terpolymer is
aromatic ring stretching modes [15]. The 1,2,3,5 tetra presented in Table 2. The average molecular weight of the
substitution of aromatic benzene ring was confirmed by PUF resin is found to be around 2060 by GPC. The
sharp, medium/weak absorption bands appeared between polydispersity index for the resin is 1.016.
1200 cm-1 and 800 cm-1 [16]. The band appeared at
1679.8 cm-1 is due to –C=O stretching vibrations. A weak Table 2.Average molecular weight of PUF resin
band appeared in the region 2901.5 cm-1 is attributed to –
CH2 linkage present in the terpolymer [17]. The band Sample Mn Mw Mz Polydispersity
appeared in the region of 3347.9 cm-1 is assigned to the – ( Mw / Mn )
NH bridge present in the terpolymer resin [18]. PUF Resin 2055 2089 2056 1.016

25
 Metal Sorption Studies of a Novel Terpolymer Resin

Table 3.Evaluation of the uptake of metal ions by PUF resin

Metal Concentration Weight of metal ion uptake in presence
ions of electrolytes of electrolytes (mg)
(mol/L) KCl KNO3 K2SO4 KClO4
Cu2+ 0.01 09.55 10.88 03.47 07.85
0.10 11.25 12.74 02.81 09.22
0.50 13.20 14.09 02.03 10.01
Ni2+ 0.01 07.89 09.14 04.12 06.58
0.10 08.55 10.56 03.67 07.49
0.50 10.01 11.97 03.22 08.69
Zn2+ 0.01 04.69 05.78 01.98 04.82
0.10 05.56 06.59 01.21 05.57
0.50 06.11 07.28 00.83 05.97
Co2+ 0.01 10.45 11.52 04.66 06.34
Figure 2. 1H NMR spectrum of PUF terpolymer resin 0.10 11.88 13.66 03.92 07.85
0.50 13.91 14.88 03.28 08.99
3.5 Evaluation of Metal Ion Uptake in Various Ba2+ 0.01 02.36 03.22 01.12 01.96
Electrolytes at Different Concentrations 0.10 03.05 03.98 00.75 02.33
The chelation ion-exchange property of the PUF 0.50 04.12 04.25 00.34 02.99
Mn2+ 0.01 10.45 11.23 05.69 08.87
terpolymer resin was determined by batch equilibrium 0.10 11.68 12.58 05.01 09.67
method involving Pb2+, Zn2+, Cu2+, Ni2+, Ba2+, Co2+ and 0.50 13.04 14.21 04.88 10.36
Mn2+ ions. The results are presented in Table 3. From the Pb2+ 0.01 02.11 03.05 01.23 02.56
data it is observed that the amount of metal ion uptake for 0.10 02.82 03.66 00.53 02.86
0.50 03.02 03.91 00.33 03.59
a given amount of resin depends on the nature and
concentrations of the electrolyte used for the chelation
studies. From the results, it is observed that the amount of 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
metal ion uptake by the terpolymer resin increases with
the increasing concentration of Cl-, NO3-, and ClO4- ions 3.6 Evaluation of the Distribution of Metal Ions at
and decreases with the increasing concentration of SO42- Different pH
ion. This may be due to the sulphate ion forming strong The distribution of the metal ions such as Pb2+, Zn2+,
chelates with metal ions, while the other anions form Cu2+, Ni2+, Ba2+, Co2+ and Mn2+ between polymer phase
weak chelates. The position of the metal chelate and the aqueous phase were determined at 25 °C in the
equilibrium is less influenced in the presence of Cl-, NO3-, presence of 1 M KNO3 at various pHs ranging from 3 to
and ClO4- ions than that of SO42- ion. The amount of 5.5. The study was restricted up to a maximum pH of 5.5,
uptake of Co2+, Cu2+ and Mn2+ ions by the terpolymer is due to the hydrolysis of metal ion at higher pH. The
higher than that of the other metal ions. This may be due amount of the metal ion which remained in the aqueous
to the Co2+, Cu2+ and Mn2+ ions form weak chelates with phase was estimated. If the original metal ion
the anions of the electrolytes. In addition, the terpolymer concentration is known, the metal ion adsorbed by the
has more porosity in its structure they can accommodate resin can be calculated. The effect of pH on the amount of
metal ions of specific size, easily into its cavities and acts metal ion distributed between the two phases is given in
as a better cation-exchanger. Table 4 which reveals that the amount of uptake of metal
Figure 3. SEM micrograph of PUF resin
ions by the resin at equilibrium increases with increasing
pH. It is assumed that the equilibrium state is attained at
25 ºC under the given conditions in 24 h. It is also
observed that the terpolymer takes up Co2+ and Cu2+ ions
more effectively than the other ions under study at all pH
values. Among the other ions taken up for the study, Zn2+,
Mn2+ and Ni2+ shows selective uptake under moderate pH
values. Further, Pb2+ and Ba2+ ions have lower distribution
over the pH range 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 of the metal ions are Co2+
> Cu2+ > Mn2+ > Ni2+ > Zn2+ > Ba2+ > Pb2+for the pH
ranges from 3 to 5.5. Due to the electrostatic factors and
larger size of its hydrated ion, Ba2+ and Pb2+ ions possess
lower distribution values. The values of the distribution
ratio and the order at different pH depend on the nature of
the terpolymer.

26
 Metal Sorption Studies of a Novel Terpolymer Resin

3.7 Evaluation 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. The metal ion uptake by the polymer
increases with the increase in shaking time. Perusal of the
Table 5 reveals that the time taken for the uptake of the
different metal ions depends on the nature of the resin
under the given conditions. Among the seven metal ions
taken for the study, Co2+ and Cu2+ ion require about 5 h
(shortest time), whereas Mn2+, Zn2+ and Ni2+ require
about 6 h for the establishment of the equilibrium. Ba2+
and Pb2+ ions require 7 h to reach the state of equilibrium.
The rate of the metal ion uptake depends upon the
hydrated ionic radii of the metal ions. Hence, the order of
rate of metal ion uptake is Co2+ > Cu2+ > Mn2+ > Zn2+ >
Ni2+ > Ba2+ > Pb2+ for the PUF resin.
found to be 6.0 mmol/g for Co2+ ion. This shows that the
PUF resin has higher uptake capacity for the ion-
exchange process than commercial phenolic and
polystyrene ion-exchange resins (Table 6) for cobalt ion.
Further the ion-exchange capacity is comparable to the
other metal ion also with the commercial resins.
3.9 Recycling of the resin
The advantage of the PUF chelating resin is their
reusability after the exchange process. The resin, once
used, can be
Table 6 Comparative study with commercial reins
Ion-Exchange
Trade Name Polymer Matrix capacity
(mmol/g)

Table 4. Evaluation of distribution ratio KD, at different pH Amber lite IR-120 Polystryrene 5.0-5.2
Duolite C-3 Phenolic 2.8-3.0
Distribution ratio(KD) of the metal ions Amber lite IRC-50 Meth acrylic 9.5
Metal Duolite ES-63 Polystyrene 6.6
ions pH of the medium Dowex - 1 Polystyrene 3.5
Amberlite IRA-45 Polystyrene 5.6
3 3.5 4 4.5 5 5.5
Dowex – 3 Polystryrene 5.8
Cu2+ 150.22 190.85 280.75 394.45 501.27 610.01 PUF Resin Carboxylic and Urea 6.0
Ni2+ 100.01 140.81 230.23 320.98 410.66 508.93
recovered back to its original form by desorption of the
Zn2+ 91.23 155.28 290.17 380.03 450.82 499.25 chelated metal ions using concentrated nitric acid. The
metal free resin can be reused after repeated washing with
Co2+ 160.41 279.51 394.29 480.33 572.34 630.80 water. The recycling of the purified resin with the
addition of chosen metal ion solution results in the uptake
Ba2+ 70.12 120.63 190.25 250.36 312.27 378.98 of almost the same amount as it was initially adsorbed.
The retention of metal ion uptake capacity, even after few
Mn2+ 130.45 240.96 350.74 430.19 520.37 600.98
cycles of repeated exchanges, suggests that the resin can
Pb2+ 45.66 115.52 208.71 246.11 286.49 320.01 be used as an ion-exchanger.
2. Conclusion
M2+(NO3)2 = 0.1 M; volume = 2 mL; KNO3 = 1 M; volume = 25 mL;
weight of resin = 25 mg; time = 24 h; temperature = 25 ºC PUF terpolymer was synthesized by solution
condensation technique in acid medium. The structure of
Table 5 Evaluation of rate metal ion uptake by PUF resin the resin was confirmed by spectral studies. The
Metal Equilibrium attainment (%) morphology of the resin illustrated the high porosity and
ions Time (h) deep pits on the surface which is an additional evidence
1 2 3 4 5 6 7 for the higher ion-exchange capacity of the terpolymer.
Cu2+ 60 71 79 85 92 - - From the batch equilibrium studies, the resin has good
binding capacity with the selective metal ions and proved
Ni2+ 49 56 64 76 88 94 - as an excellent ion-exchanger.
Zn2+ 48 55 66 78 89 95 - Acknowledgment
Co 2+
61 70 79 88 97 - - The authors thank the Management & Principal
of Jamal Mohamed College (Autonomous),
Ba2+ 21 33 41 52 68 75 83
Tiruchirappalli, Tamil Nadu, India for their support
Mn2+ 46 58 60 71 85 92 - and encouragement.
2+
Pb 16 24 32 42 56 65 80 References
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27
 Metal Sorption Studies of a Novel Terpolymer Resin
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