Malaysian
Journal of Analytical Sciences Vol 20 No 5 (2016): 1129 - 1137
DOI:
http://dx.doi.org/10.17576/mjas-2016-2005-19
SYNTHESIS OF
BIO-BASED HYDROGEL FROM EPOXIDIZED PALM OIL CATALYZED BY FLUOROANTIMONIC ACID HEXAHYDRATE
(Sintesis Hidrogel Berasaskan Bio Daripada Minyak Sawit Terepoksidasi
Bermangkinkan Asid Fluoroantimonik Heksahidrat)
Wan Nurhayati
Wan Tajulruddin, Abdul Razak Rahmat*, Rohah Abd Majid
Department of Polymer Engineering, Faculty of Chemical
Engineering,
Universiti Teknologi Malaysia, 81310 Skudai, Johor, Malaysia
*Corresponding author: k-razak@cheme.utm.my
Received: 10
June 2015; Accepted: 21 July 2016
Abstract
An epoxidized
palm oil-based hydrogel (HPEPO) was synthesized by using ring opening
polymerization (ROP) in the presence of fluoroantimonic
acid hexahydrate catalyst (HSbF6·6H2O), followed
by chemical hydrolysis catalyzed with sodium hydroxide (NaOH). The structural characterization and thermal property of synthesized hydrogel were studied.
The successful ring opening of EPO was confirmed by disappearing of epoxy functional
group at 833 cm-1 in the Fourier transform infrared (FTIR) spectrum.
The formation of HPEPO was detected at 2500 cm-1 to 3400 cm-1
which represents the O-H stretching of carboxylic acid. Based on nuclear magnetic resonance
(NMR), the disappearance of epoxy ring group at 2.8 – 3.0 ppm has
indicated the completely reacted oxirane ring with the presence of peak at 3.7
ppm corresponded to hydroxyl group. Meanwhile, HPEPO exhibited low thermal
stability by having melting temperature around 45 °C to 60 °C in Differential
scanning calorimetry (DSC) and as showed by the great percentage of weight loss
in thermogravimetric analysis (TGA) curve. However, the formation of char
residue was slow, probably due to the formation of hydrogen linkages in
hydrogel.
Keywords: hydrogel, epoxidized
palm oil, ring opening polymerization, chemical hydrolysis
Abstrak
Hidrogel berasaskan minyak sawit
terepoksidasi (HPEPO) telah disintesis menggunakan polimerisasi pembukaan
cincin (ROP) dengan kehadiran asid fluoroantimonik heksahidrat (HSbF6.6H2O)
sebagai pemangkin, diikuti dengan hidrolisis kimia yang dimangkinkan oleh
natrium hidroksida (NaOH). Pencirian struktur dan sifat termal hidrogel yang
disintesis telah dikaji. Kejayaan pembukaan cincin minyak sawit terepoksidasi
(EPO) telah disahkan melalui kehilangan kumpulan berfungsi epoksi pada 833 cm-1
dalam spektrum Fourier inframerah (FTIR). Pembentukan HPEPO dikesan pada 2500
cm-1 hingga 3400 cm-1 yang mewakili regangan O-H daripada
asid karboksilik. Merujuk kepada resonans magnetik nuklear, kehilangan cincin
epoksi pada 2.8 – 3.0 ppm menunjukkan cincin oksiran
telah bertindakbalas sepenuhnya dengan kewujudan puncak pada 3.7 ppm sepadan
dengan kumpulan hidroksil. Sementara itu, HPEPO telah mempamerkan kestabilan
haba yang rendah dengan mempunyai suhu lebur antara 45 °C to 60 °C daripada kalorimetri pengimbasan pembezaan (DSC) dan seperti yang
ditunjukkan dalam kehilangan peratusan berat yang besar melalui lengkung
analisis Termogravimetri (TGA). Walau bagaimanapun, pembentukan sisa arang
didapati perlahan, berkemungkinan disebabkan oleh pembentukan ikatan hidrogen
dalam hidrogel.
Kata kunci: hidrogel, minyak
sawit terepoksidasi, polimerisasi pembukaan cincin, hidrolisis kimia
References
1. Michael, A. R.
M., Jurgen, O. M. and Ulrich, S. S. (2007). Plant oil renewable resources as
green alternatives in polymer sciences. Chemical Society Reviews, 36: 1788 – 1802.
2. Seniha, G. F.,
Yusuf, Y. A. and Tuncer, E. (2006). Polymer from triglyceride oils. Progress in Polymer Science, 31: 633 –
670.
3. Petrovic, Z. S.,
Zlatanic, A., Lava, C. C. and Sinadinovic-Fiser, S. (2002). Epoxidation of
soybean oil in toluene with peroxy acetic and peroxy formic acids-kinetics and
side reactions. European Journal of Lipid
Science and Technology, 104: 293 – 299.
4. Okieimen, F.E.,
Bakare, O.I., and Okieimen, C.O. (2002). Studies of epoxidation of rubber seed
oil. Industrial Crops and Products,
15: 139 – 144.
5. Milchert, E.
Smagowicz, A. and Lewandowski, G. (2010). Optimization of the reaction
parameters of epoxidation of rapeseed oil with peracetic acid. Journal
Chemical Technology and Biotechnology, 85:1099 – 1107.
6. Vinay, S. and
Kundu, P. P. (2006). Addition polymers from natural oils – A review. Progress in Polymer Science, 31: 983 –
100.
7. Clark, A. J. and
Hoong, S. S. (2013). Copolymers of tetrahydrofuran and epoxidized vegetable
oils: Application to elastomeric polyurethanes. Polymer Chemistry, 5(9): 3238 – 3244.
8. Yahaya, S. M.,
Mohd, A. F. and Mohamed, R. (2013).
Synthesis and characterization of palm oil based polyol. Advance Materials
Research, 812: 275 – 280.
9. Ang, K. P., Lee,
C. S., Cheng, S. F. and Chuah, C. H. (2013). Synthesis of palm-oil based
polyester polyol for polyurethane adhesive production. Journal of Applied Polymer Science, 131: 1 – 8.
10. Hoare, T. R. and
Kohane, D. S. (2008). Hydrogel in drug delivery: progress and challenges. Polymer, 49: 1993 – 2007.
11. Liu, Z. S. and
Erhan, S. Z. (2010). Ring-opening polymerization of epoxidized soybean oil. Journal of Americal Oil Chemical Society,
87: 437 – 444.
12. Denisov, G. S.,
Mavri, J. and Sobczyk, L. (2006). Potential energy shape for the proton motion
in hydrogen bond reflected in Infrared and NMR spectra. The Netherlands :
Springer – Dordrecht.
13. Zhang, L.,
Huang, M., Yu, R., Huang, J., Dong, X., Zhang, R. and Zhu, J. (2014). Bio-based
shape memory polyurethanes (Bio-SMPUs) with short side chains in the soft
segment. Journal
of Materials Chemistry A, 2(29): 11490 – 11498.
14. Rashmi, B.
J. Rusu, D. Prashantha, K. Lacrampe, M. F. and Krawczak, P.
(2013). Development of
bio-based thermoplastic polyurethanes formulations using corn-derived chain
extender for reactive rotational molding. Express
Polymer Letters, 7
(10): 852 – 862.
15. Wang, R. and Schuman, T. P. (2013). Vegetable oil-derived epoxy
monomers and polymer blends: A comparative study with review. Express
Polymer Letters,
7(3) : 272 – 292.
16. Souza, A. G. D., Santos, J. C. O., Conceição, M. M., Silva, M.
C. D. and Prasad, S. (2004). A thermoanalytic and kinetic study of sunflower
oil. Brazilian Journal of Chemical
Engineering, 21: 265 – 273.
17. Vashist, A.,
Shahabuddin, S., Gupta, Y. K. and Ahmad, S. (2013). Polyol induced
interpenetrating networks: chitosan-metylmethacrylate based biocompatible and
pH responsive hydrogels for drug delivery system. Journal of Materials Chemistry B. 1: 168 – 178.