Synthesis and Characterization of Supramolecular Elastomers from
Polyacids Composed of Vegetable Oils
Ehsan Zeimaran
1, a
, Sobhan Bahraeian
1, b
, Taravat Ghanbari
1, c
,
Sara Pourshahrestani
2, d
and Hussin Mohd Nor
1, e
1
Department of Polymer Engineering, Faculty of Chemical Engineering,
Universiti Teknologi Malaysia, 81310 Skudai, Johor, Malaysia
2
Department of Organic Chemistry, Faculty of Chemical Engineering,
University of Esfahan, Esfahan, Iran
a
Zehsan3@live.utm.my,
b
sobhan.bahraeian@gmail.com,
c
gtaravat2@live.utm.my
d
spourshahrestani@yahoo.com,
e
hussin@fkkksa.utm.my
Keywords: supramolecular elastomer, polycondensation, vegetable oil, epoxidized oil, polyacid
Abstract. Supramolecular elastomers were synthesized using vegetable oil materials namely palm
acid oil (PAO) and sunflower oil (SFO). The oils were first epoxidized using formic acid and
hydrogen peroxide. The epoxidized oils and adipic acid were then reacted to make polyacids,
mainly triacid. Finally, diethylenetriamine (DETA) was added to polyacid to yield fatty amide and a
polycondensation with urea performed to achieve the desired elastomers. The synthesized materials
were characterized by using Fourier Transform Infrared (FTIR), Nuclear Magnetic Resonance
(NMR) and Thermogravimetric Analyzer (TGA) in order to determine structure, type of bonding
and thermal stability. The spectrums revealed that the synthesized fatty amides are contained amide
groups that correctly formed from reaction of amine groups of DETA and acid functionality of
polyacids. Moreover, the resulted structures showed the formation of multiple hydrogen-bonding in
the elastomers. TGA thermograms clearly indicated good thermal stability of the elastomers to 500
°C.
Introduction
In two last decades, supramolecular polymers have been attracted attention due to reversible
property of the bonds and high directionality. Supramolecular polymers composed of small
molecules associating by non-covalent interactions such as hydrogen bonding, hydrophobic forces,
metal coordination, π–π interactions, and van der Waals forces in which multifunctional molecules
with an average functionality more than two are capable of making directional supramolecular
networks. Among them, hydrogen bonding was achieved special attention owing to their synthetic
accessibility, directionality and thermal reversibility. Further, Thermal reversibility of hydrogen
bonding led to facile controlling of strength of interaction and thermal responsive of system.
Hydrogen bondings by high directionality are appropriate for supramolecular polymers.
Furthermore, more stability will achieved by enhancing the number of hydrogen bondings [1]. The
polymer networks with self-complementary quadruple hydrogen bonding array was easily
synthesized by 2-ureido-4-pyrimidone (UPy) [2]. Further, from reaction of a low molecular weight
polyols with three groups of UPy, reversible polymer networks were achieved which were similar
to covalent polymer networks without the need for additional stabilization by phase separation. The
cross-links are reversible and the polymer networks have same tensile properties as conventional
cross-link elastomers. Supramolecular polymers that are made from hydrogen bonding are an
alternative route to improve thermoplastic elastomers when they are easier to process and repair or
reuse [1,3.4]. Recently, [3] applied supramolecular concept to prepare a new self-healing elastomer
in which an oligomer of dimer fatty acid and diethylenetriamine (DETA) was reacted with urea.
This elastomer can withstand a large deformation and the torn parts can be easily healed by keeping
them together.
This research aimed to production of supramolecular elastomer from polyacids of vegetable oils.
For this purpose polycondensation technique was used.
Advanced Materials Research Vol. 747 (2013) pp 505-508
Online available since 2013/Aug/30 at www.scientific.net
© (2013) Trans Tech Publications, Switzerland
doi:10.4028/www.scientific.net/AMR.747.505
All rights reserved. No part of contents of this paper may be reproduced or transmitted in any form or by any means without the written permission of TTP,
www.ttp.net. (ID: 161.139.220.106, Universiti Teknologi Malaysia UTM, Johor Bahru, Johor, Malaysia-17/09/13,14:58:46)