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FUTA Journal of Research in Sciences ISSN: 2315 – 8239 (Print); E-ISSN: 2489 - 0413 FUTA Journal of Research in Sciences, Vol

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FUTA Journal of Research in Sciences ISSN: 2315 – 8239 (Print); E-ISSN: 2489 - 0413 FUTA Journal of Research in Sciences, Vol Fjrs.futa.edu.ng FUTA Journal of Research in Sciences ISSN: 2315 – 8239 (Print); E-ISSN: 2489 - 0413 FUTA Journal of Research in Sciences, Vol. 15(2), October, 2019: 201-211 SYNTHESIS AND CHARACTERIZATION OF NOVEL PLUKENETIA CONOPHORA SEED OIL- STYRENE-DIVINYLBENZENE THERMOSETTING COPOLYMER I.O. AROGUNDADE *, B.M. BABALOLA, S. O. AFOLABI, H. O. ADUBIARO and C. O. AKINTAYO Industrial Chemistry Department, Federal University Oye, Oye Ekiti, Ekiti State, Nigeria. *Corresponding author: [email protected] ABSTRACT Vegetable oils are perfect alternatives for petrochemicals. During this study the cationic copolymerization of conjugated and unconjugated Plukenetia conophora E. seed oil with styrene and divinylbenzene was carried out in the presence of boron triflouride etherate as catalyst. Polymers starting from soft rubbers to strong and rigid plastic were formed in quantitative yield. Nuclear magnetic resonance spectroscopy (1HNMR) was employed in monitoring the functionalization process. The polymers were soxhlet-extracted using methylene chloride as refluxing solvents and also the extracts were studied using 1HNMR in order to understand the microstructure of the materials. About 71 – 96 wt% of insoluble substances were retained after extraction of bulk polymers. Result of spectroscopic analysis indicated that all the aromatic monomers were incorporated within the cross-linked polymer networks. Thermogravimetric analysis (TGA) indicated that these copolymers were thermally stable below 150oC. The maximum temperature (Tmax) of the TGA derivative curves of polymers prepared from unconjugated Plukenetia conophora (320oC) and conjugated Plukenetia conophora (330oC) which was determined as a corresponding derivative weight loss curve only varied slightly. The tensile mechanical properties of the conjugated Plukenetia conophora polymer showed a significant decrease in the tensile modulus (єt) from 304.25Mpa to 240.40Mpa and yield stress (бb) from 6.85Mpa to 2.52Mpa. There was a rise in the elongation at break (єb) from 2.77Mpa to (20.26Mpa) showing the impact of conjugation on the polymer which resulted in an increased ductility of the resulting polymer compared to polymers prepared from the unconjugated Plukenetia conophora. This result revealed that both Plukenetia conophora and its conjugated derivative are good candidate for preparation of thermosetting polymers which may find application in industries and serve as alternative to polymers made from fossil fuel. Keywords: Plukenetia conophora, styrene, divinylbenzene, conjugation, copolymerization INTRODUCTION triglyceride make it easy to attach appropriate functional groups through chemical modification. The application of vegetable oil as raw material for The availability, sustainability, versatility in monomers and polymers is of great interest to structure and properties and comparative low cost scientists as it can be used in partial or total of plant oil give it the advantage of serving as a replacement for petrochemical products. Vegetable potential alternative to petroleum products (Meier oil in this regard has served variety of objectives et al., 2007; de and Meier, 2011). The change from from environmental challenges to reduction in the fossil feed stock to renewable resources can use of fossil fuels, reduced volume of waste and considerably contribute to a sustainable reduction in ozone layer depletion. The presence of development in the future. reactive groups (double bond, hydroxyl etc.) in 201 Arogundade et al., FUTA J. Res. Sci., Vol. 15 (2), October, 2019: 201 - 211 Furthermore, the environmental friendliness of edible and usually eaten up with rice. The leaves products obtained from plant oils are primarily are also used historically for curing headache and derived from the fact that chemists take advantage also the contemporary fresh leaves are used for of the synthetic potential of nature by slightly curing snakebites (Zhou et al., 2018). The oil is fast modifying the triglyceride, thereby retaining the drying and has been employed in the formulation naturally occurring chemical structure, which of wood varnish, stand oil, vulcanized oil for rubber makes the derived compounds biocompatible and and leather substitute (Awodoyin et al., 2000; biodegradable (Bornscheuer, 2006). Some oils like Jiofack et al., 2013). sunflower, linseed, soybean, and rubber seed have The seed yields 48-60% oil with a flavor been employed in the preparation of different resembling linseed oil. The oil has been reported to polymers from alkyds (Akintayo and Bayer 2002), be extremely unsaturated and consist of linolenic polyesteramides, (Lam et al., 2004) , polyepoxides (70.1%), oleic (11.7%), stearic (0.6%) and palmitic ( John et al., 2002), or polyurethanes (Ahmad et al., (0.8%) acids (Akintayo and Bayer, 2002). It is 2003 ; Alam et al., 2004). Due to the quest for therefore a very high unsaturated oil with high environmental sustainability, there have been an content of linolenic acid compared to soybean oil increasing demand for replacing petroleum derived that has been popularly studied for lubricating raw materials with renewable materials in the substance applications (Akintayo and Bayer, production of polymers by scientists. (Belgacem 2002). The very high saponification and iodine and Gandini, 2011). values of Plukenetia conophora (PKCO) recommends its utilisation in alkyd resin, shoe The African walnut, Plukentia conophora polish, and shampoo production (Akintayo and (Tetracarpidium conophorum) called ‘‘Awusa’’, Bayer, 2002). Edem et al. (2009) have reported ‘‘Asala’’ in Yoruba, ‘‘Ukpa’’ in Igbo, Nigeria and proximate analysis of the seed to be crude fat ‘‘Kaso’’,‘‘ Ngak’’ in Cameroon is one of the top (6.21%), moisture content (48.70%), crude protein non-timber yielding plant species in the tropical (35.22%), crude fibre (3.34%), ash content (2.03%) lowland rainforest of southwestern Nigeria (Amusa and carbohydrate content (53.2%). Considering the and Jimoh, 2012). It is a perennial plant belonging percentage of the crude fat, it is very low which to the family Euphorbiaceae in the order may be due to the condition for the proximate. Malpighiales. It is widely cultivated for its nuts, Okpero (2001) reported on the methods of which are cooked and consumed as snack. The seed processing the Plukenetia conophora nuts. can be grounded into a powder and used with flour Moreover, PKCO which consists of 98.0% in baking cakes. It is contained in a pod which may unsaturated fatty acids made up of mainly 70.1% of be one shelled nut (single), two shelled nut linolenic acid, has been reported to belong to the (double) and three shelled nut, the nut is whitish drying oil group and might be a substitute for upon cracking from the shell. There is always a linseed oil (Akintayo and Bayer, 2002). It was bitter taste upon drinking water immediately after reported that Adenopus breviflorus and Plukenetia eating the nuts. This might be attributed to the conophora possess high oil content, indicating that presence of chemical substances like alkaloids processing of its oil for industrial or edible (Oke, 1995; Ayodele, 2003). purposes would be economical. Plukenetia The leaves of Walnut are used for the treatment of conophora has low moisture content which implies infectious disease and also the presence of good shelf life characteristics (Akintayo and Bayer, tocopherol within the leaf supports its use in 2002). With the increased interest in the southern Nigeria ethno drugs as a male fertility exploitation of less-common seed oils, several agent (Ajaiyeoba and Fadare, 2006). The leaves are studies have been carried out on Plukenetia 202 Arogundade et al., FUTA J. Res. Sci., Vol. 15 (2), October, 2019: 201 - 211 conophora and based on the Nigerian government refined by agitating with 18 M NaOH (1:30 g/g of initiative to promote industrialization following its alkali: oil) for 15 min. The resultant mixture was natural resources, this research focuses on the heated to 75-80 0C to break the soap stock and the synthesis of polymers from both modified and neutral oil separated by centrifugation. unmodified PKCO through cationic copolymerization with styrene and divinylbenzene Isomerization of Plukenetia conophora oil initiated by boron triflouride etherate as catalyst. To 30.8 g (100 mmol) of PKCO in 200 ml ethanol MATERIALS AND METHODS were added 71.5 mg (5mol %) of [RhCl (C8H14)2]2, Materials 120.5 mg (20mol %) of (P – CH3C6H4)3P, and Walnut seeds were obtained from Erekesan market, 180.5 mg (40 mol %) of SnCl2.2H2O. The system Ado Ekiti, Nigeria. Chlorobis(cyclooctene) was flushed with nitrogen gas while stirring was o rhodium(I) [RhCl (C8H14)2]2, ethanol (C2H5OH), carried out for 24h at 60 C. The solvent was Tin(II) chloride dihydrate (SnCl2.2H2O), Tris(o- removed over rotary evaporator and the product tolyl) phosphine (P – CH3C6H4)3P, pH paper, purified by chromatography on a silica gel column boron triflouride etherate (BF3E), styrene (C8H8), to obtain the conjugated Plukenetia conophora oil divinyl benzene (C10H10), toluene (C6H5CH3), (CPKCO) (Andjelkovic et al., 2006). tetramethyl ammonium hydroxide (C4H13NO), Cationic copolymerization hydrogen peroxide(H2O2), magnesium sulphate Varying amount of the styrene and divinylbenzene (MgSO4), sodium bicarbonate (NaHCO3), and (DVB) were added to the desired amount of methylene chloride (CH Cl), were all purchased 3 Plukenetia conophora seed oil in a flask with a from Sigma-Aldrich and used as received. magnetic stirring bar followed by the addition
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