Synthesis, characterisation and antibacterial activity of copolymer (n vinylpyrrolidone – maleic anhydride) with n- diethylethanolamine

IJRET: International Journal of Research in Engineering and Technology eISSN: 2319-1163 | pISSN: 2321-7308
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Volume: 03 Issue: 03 | Mar-2014, Available @ http://www.ijret.org 56
SYNTHESIS, CHARACTERISATION AND ANTIBACTERIAL ACTIVITY
OF COPOLYMER (N-VINYLPYRROLIDONE – MALEIC ANHYDRIDE)
WITH N- DIETHYLETHANOLAMINE
Hemalatha P1
, M K Veeraiah2
, Prasannakumar S3
, Anasuya K V4
1
Lecturer, 2
Prof and Head, Dept of Chemistry,,
Sri Siddhartha Institute of Technology, Tumkur, Karnataka, India
3
Head R&D, Clov Chem. India Private Limited, Harohalli, Bangalore. Karnataka, India.
4
Asst.Prof. Department of Chemistry, Govt First Grade College and PG Centre, Davanagere, Karnataka, India
Abstract
A copolymer of N-vinylpyrrolidone (NVP) with maleic anhydride (MA) is synthesized by radical copolymerization with 2,2-Azo-
bisisobutyronitrile(AIBN) as initiator at 650
C in dioxane solution, under nitrogen atmosphere. The copolymer obtained is
characterized by FTIR and NMR. The copolymer is made to interact with N,N-Diethylaminoethanol (DEAE) in different ratios. The
susceptibility of some Gram - negative bacteria like Klebsiella aerogenes NCIM-2098, Escherichia coli NCIM-5051,
Pseudomonasaeruginosa NCIM2242, Pseudomonas desmolyticum NCIM-2028 and a Gram positive bacteria Staphylococcus aureus
NCIM-5022, to the copolymer and its compound with N,N-Diethylaminoethanol of different compositions in microbiological medium
is studied by Agar well diffusion method. The resulting polymeric antibacterial material is useful in a number of medicines and food
industry.
Keywords: N-vinylpyrrolidone, Maleic anhydride, Copolymerization, N, N-diethylaminoethanol, FTIR, NMR,
Antibacterial activity.
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1. INTRODUCTION
Copolymers with reactive or functional monomers are steadily
gaining importance. Many copolymers with reactive
functional groups are now being synthesized, tested and used
not only for their macromolecular properties, but also for the
properties of functional groups [1]. These functional groups
provide an approach to a subsequent modification of the
polymer for the specific end applications [2]. Nowadays, a
strong demand prevails for ―functional polymer‖ with very
specific properties. Functional groups give a polymer structure
a special character substantially different from the inherent
properties of the basic polymer chain [3].
The antimicrobial property of the polymers plays an important
role for many of its applications. Contamination by
microorganisms is of great concern in several areas such as
medical devices, health care products, water purification
systems, hospital and dental equipments etc. One possible way
to avoid microbial contamination is to develop the polymeric
materials possessing antimicrobial properties [4-10].
Antimicrobial polymers are those, which are capable of killing
pathogenic micro-organisms. These polymeric biocides can
significantly reduce the loss of antimicrobial activity
associated with volatization, photolytic decomposition,
dissolution and permeation migration. Moreover, increased
efficiency, selectivity and handling safety are additional
benefits that are realized [11, 12].
Antimicrobial activity of some linear copolymers, containing
quaternary ammonium and phosphonium salts has been
reported by Kenawy et al. [12, 5, 10]. Patel et al found that
homo and copolymers of N-vinylpyrrolidone (NVP) and 2,4-
dichlorophenyl methacrylate (2,4 DMA) were effective in
inhibiting selective microorganisms [4]. It has been reported
that polymers prepared using 2,4 - DMA showed strong
inhibitory effect towards such tested microorganism as
bacterial strains (S. Aurus, S. Citreus and E.Coli), molds and
yeasts, while poly(VP) has been shown to have relatively
lower antimicrobial activity. Gottenbos et al. reported that
quaternary ammonium silane – coated silicone rubber showed
antimicrobial properties against adhering bacteria, both Gram
– positive and Gram – negative [13]. Ayhan Temiz et al.
studied the antimicrobial behavior of Poly (N-
vinylpyrrolidone - alt-Maleic anhydride) and it’s Poly
(ethyleneimine) macro complexes in aqueous solution and
reported that Gram – positive bacteria affected by the complex
but Gram – negative bacteria are not affected [14].
N-vinylpyrrolidone is a good biocompatible monomer due to
its hydrophilic nature and low toxicity [15-17]. The amide
group of NVP has a high affinity for several small and large

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molecules that are known as good hydrogen-bond acceptors
and has been copolymerized with a variety of monomers [18-
22]. Homo and copolymers of N-vinylpyrrolidone (VP) are of
considerable academic and industrial interest due to their
unique properties, allowing the use of these polymer systems
in lithography as light sensitive thin coatings for printing
plates, for the preparation of separating membranes for ultra
filtration, biocompatible polymers with low toxicity and
carriers of biologically active compounds, sorbents,
coagulants and flocculants [23-27]. Copolymer of 2-
hydroxymethylmethacrylate (HEMA) and N-vinylpyrrolidone
is used in pharmaceutical application, such as, cancer therapy
[28]. Copolymer of NVP and n-butylmetharylate are used for
blood purification therapies [29]. Fullerene (60) C complexed
with Poly (N-vinylpyrrolidone) is used in antiviral activity
[30].
The use of maleic anhydride (MA) copolymers in medicine or
pharmacy was described as antitumor agents, [31-33] drug
carriers, supporters for enzymes or protein modifiers [34-37].
Antitumor functional polymers were synthesized by reaction
of poly (MA-co-VP) with hydroxyl and amino containing
physiologically active compound [38-40]. By the
intermolecular reactions of poly (MA-co-styrene) [43] and
poly(MA-co-methyl methacrylate) [41] with 3,6 – diamino-
10-methylacridiniumchloride (acriflavine as an antiseptic
agent) in DMF and poly[(N-isopropylacrylamide-co-maleic
anhydride)-g-poly(ethylene oxide)] using triethylamine as
catalyst [44], new derivatives of these copolymers with
antimicrobial properties were also synthesized.
In the present work, a copolymer of NVP and MA is
synthesized. It is characterized by FTIR, H1
NMR and C13
NMR. The synthesized copolymer is hydrolyzed. The product
formed is made to react with N-diethylaminoethanol to form a
complex in two different ratios. The complexes formed are
tested for antibacterial activity.
2. EXPERIMENTAL
2.1 Materials
2.1.1 Chemicals
N-vinyl-2-pyrrolidone (NVP) (Sigma-Aldrich) was purified
before use by distillation under moderate vacuum. Maleic
anhydride (MA) (Lobachem) was purified before use by
recrystallisation from anhydrous benzene solution and
sublimation in vacuum. 2,2-Azobisisobutyronitrile (AIBN)
was purified by successive crystallization from chloroform-
methanol mixture. N,N-Diethylaminoethanol was purified by
distillation. The solvents used as copolymerization medium,
for precipitation and extraction were all of analytical grade.
2.1.2 Microbial Strains
Antibacterial activity was screened by Agar well
diffusion method [45] against five bacterial Strains Gram-ve
Klebsiella aerogenes NCIM-2098, Escherichia coli NCIM-
5051, Pseudomonas aeruginosa NCIM2242, Pseudomonas
desmolyticum NCIM-2028 and a Gram +ve bacteria
Staphylococcus aureus NCIM-5022.
2.2 Copolymer Synthesis
The copolymer of N-vinylpyrrolidone with maleic anhydride
was prepared by radical initiated copolymerization in 1,4-
dioxane at 650
C in the presence of AIBN as initiator in three
necked round bottom flask under nitrogen atmosphere using
equimolar monomer mixture. The reaction mixture was
continuously stirred for 48 hours. Copolymer was isolated
from the reaction mixture and purified from 1,4 - dioxane
solution to diethylether (Figure -1). It was precipitated with
acetone. The precipitate was washed well with acetone. The
copolymer was then isolated by centrifugation and dried at
400
C under vacuum to constant weight.
The copolymer (M) prepared was made to react with N, N-
diethylaminoethanol at 400
C in aqueous solution in different
concentrations 1:1(M1), 1:2(M2). The copolymer (M), the
copolymer complexes (M1, M2) were tested for antibacterial
activity.

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Fig 1: Reaction scheme of N-Vinylpyrrolidone and Maleic anhydride, hydrolyzed copolymer and poly(NVP-Co-MA) / DEEA macro
complex
2.3 Copolymer Characterization
Copolymers were characterized by FTIR spectra using
Shimadzu – 1800S spectrometer on KBr pellets in the range of
400-4000 cm-1
. The H1
-NMR and C13
-NMR (Brucker AMX-
400, at Indian Institute of Science, Bangalore) spectra of
copolymer were recorded in methanol as solvent and
tetramethylsilane (TMS) as an internal standard.
2.4 Antimicrobial Activity Test
Nutrient Agar Culture medium plates were prepared and
swabbed using sterile L-shaped glass rod with 100 µl of 24 h
mature broth culture of individual bacterial strains. The wells
were made by using sterile cork borer of 6mm in each petri-
plate. Varied concentrations of given compound
(1000µg/well) were used to assess the activity of the
compounds. The compound dispersed in sterile water acts as a
negative control and the standard antibiotics
Ciprofloxacin (5µg/50µl) (Hi Media, Mumbai, India) acts as
positive control were tested against the bacterial
pathogens. Then the plates were incubated at 37 °C for 24 –
36 hours. The zone inhibition was measured in millimeter for
the every well and also the values were noted. Triplicates were
maintained in every concentration and the average values were
calculated for the ultimate antibacterial activity.
3. RESULTS AND DISCUSSION
3.1 Characterization of Copolymer
3.1.1 Solubility Studies
Solubility of the Copolymer was tested in various polar and
non polar organic solvents. It was soluble in solvents like
tetrahydrofuron, dimethylsulfoxide, dimethylformamide,
dimethylacetamide, isopropylalcohol and methanol. Whereas,
it was insoluble in ethylacetate, chloroform, 1,4-dioxane,
chlorobenzene, toluene, n-hexane, n-heptane, cyclohexane,
carbontetrachloride, diethyl ether and benzene.
3.1.2 Fourier Transform Infrared (FTIR) Spectral
Studies
The structure of copolymer was confirmed by FTIR spectra as
shown in Figure -2.

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Fig 2: FTIR Spectra of prepared NVP – MA Copolymer
The structure of the copolymer is confirmed by FTIR spectra
as shown in Fig-2. Only important peaks are assigned.
NVP 1653.13cm-1
–C=O, 1441.30cm-1
C-N-C,
MA 1991.74cm-1
anhydride ring, 984.25cm-1
cyclic anhydride,
Range 649.99 and 739.61cm-1
C-(CH2)-C of parent chain
3.1.3 Nuclear Magnetic Resonance Spectroscopy (H1
_
NMR):
The structure of copolymer is also confirmed by NMR spectral
studies.
H1_
NMR spectrum of copolymer is as shown in Fig –3.
Fig 3: H1
NMR Spectrum of Copolymer

________________________________________________________________________________________
Ring methyl protons in NVP resonate at 4.9 δ, 2.3 δ and 3.2 δ.
CH2 main chain back bone resonates at 3.5-2.5 δ. Protons of
maleic unhydride resonate at 6.2 δ.
3.1.4 Nuclear Magnetic Resonance Spectroscopy
(C13
_ NMR):
The structure of copolymer was also confirmed by C13_
NMR
spectrum as shown in Fig –4.
Figure 4: C13
NMR Spectrum of Copolymer
Ring methylene carbon of NVP resonates at 49.6 δ, 43.59 δ
and 23.8 δ.
C=O of NVP respnates at 157 δ,
CH2 Main chain back bone resonates at 48.2 and 21.2 δ.
Carbon atoms of maleic unhydride ring resonate at 136.13 δ
3.2 Anti bacterial Properties of Copolymer and its
Compounds:
The antibacterial properties of compounds were evaluated
against four Gram-ve K. aerogenes, E. coli, P. aeruginosa,
and P. desmolyticum and one Gram +ve S.aureus bacterial
strains using agar well diffusion method. In agar well
diffusion method the compounds showed significant
antibacterial activity on all the four Gram-ve bacterial strains.
K. aerogenes, E. coli, P.aeruginosa P. desmolyticum and then
another bacteria Gram +ve S.aureus is inactive. The zone of
inhibition with the concentration 1000 µg per well is as shown
in Fig.5. The data of zone of inhibition is depicted in Table 1.
Table-1: antibacterial activity of (M, M1, M2) on Pathogenic bacterial Strain
Sl.no
Treatment Klebsiella
aerogenes(B1)
(Mean±SE)
Escherichia
coli (B2)
(Mean±SE)
Pseudomonas
aeruginosa(B3)
(Mean±SE)
Staphyloccus
aureus (B4)
(Mean±SE)
Pseudomonas
desmolyticum(B5)
(Mean±SE)
I
Standard
(5µg/50µL)
12.67±0.33** 13.67±0.33** 13.67±0.33** 13.67±0.33** 14.67±0.33**
II M
(100µg/100µL)
1.33±0.33** 1.33±0.33** 2.67±0.33** inactive 2.67±0.33**
III M1
(1000µg/100µL)
2.67±0.33** 2.00±0.00 3.67±0.33** inactive 3.00±0.00
IV M2
(1000µg/100µL)
1.67±0.33** 2.67±0.33** 5.67±0.33** inactive 1.00±0.00

________________________________________________________________________________________
Values are the mean ± SE of clear zone in mm. Symbols
represent statistical significance,
*P < 0.05, **P < 0.01 as compared with the control group.
From this table, it is evident that the Copolymer (NVP – MA)
is showing a better inhibition for the bacteria Pseudomonas
aeruginosa(B3) and Pseudomonas desmolyticum(B5). The
macro complex M1 and M2 are showing a better inhibition
towards Pseudomonas aeruginosa(B3). Among all the
compounds M2 is showing a very good antibacterial property.
Fig 5: Representative photograph showing Antibacterial activity in Agar well diffusion method

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4. CONCLUSIONS
The Copolymer (NVP –MA) was synthesized. Its structure
was confirmed by FTIR, H1_
NMR and C13_
NMR. It was
made to react with DEEA after hydrolysis. The anti bacterial
activity of Copolymer and its macro complex was determined
by agar well diffusion method. It was demonstrated that the
Copolymer and its macro complex have a positive effect in
controlling the growth of the Gram –ve bacteria. Gram +ve
Bacteria were found to be active in the presence of these
compounds. This fact can be explained by the different
responsive behavior of surface layer structures of these two
bacteria. The activity of M2 is more when compared to M and
M1. This may be due to the combination of the functional
groups within the single molecule. This new polymeric
biocide system can be recommended for the biomedical and
food industry application.
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BIOGRAPHIES
Hemalatha P, Obtained her PG degree in
1997 securing IV rank and a gold medal in
Physical Chemistry at Bangalore
University. Served as lecturer in First Grade
College and PU Colleges at Bangalore and
Tumkur. At present working as lecturer at SSIT and pursuing
Ph.D. in VTU, Belgaum, Karnataka, India.
Dr. M K Veeraiah, He was awarded
Doctorate in 1998 from the University of
Mysore. Two of his students are awarded.
He is guiding three research scholars. His
areas of interests are Chemical kinetics,
Polymers and corrosion studies. He has a
credit to his fame in publishing 20 papers both in International
and National journals. He has 39 years of experience in
teaching and 22 years of experience in research and
development.
DR. S Prasanna Kumar, He has been
conferred Doctoral in 2005 from
Kuvempu University. He has 15 years of
Experience in Polymer Synthesis,
Coatings & Adhesives. He has rendered
many number of projects and headed the
R & D sections in leading polymer
companies. He has published 16 papers in national and
international journals.
Anasuya K V, Obtained her PG Degree
from Bangalore University in 1997 with
II rank and two gold medals for securing
highest marks in special subject
Inorganic Chemistry. She has 5 years of
experience and 15 years experience of
teaching chemistry in PU and degree colleges. Presently she is
pursuing her Ph.D. in VTU, Belgaum, Karnataka, India.

Synthesis, characterisation and antibacterial activity of copolymer (n vinylpyrrolidone – maleic anhydride) with n- diethylethanolamine

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Synthesis, characterisation and antibacterial activity of copolymer (n vinylpyrrolidone – maleic anhydride) with n- diethylethanolamine