Abstract
The synthesis of an alkyd resin through an enzymatic alcoholysis provided by Novozym 435 was analyzed in this study. The alcoholyses were performed in different enzyme concentrations (2.63, 4.00, 6.00, 8.00, and 9.36%, based on oil’s mass), oil/glycerin ratios (1.68, 2.50, 3.50, 4.50, and 5.18 oil mol/glycerin mol), at temperatures (33.18, 40.00, 50.00, 60.00, and 66.82 °C) to determine the best reaction conditions for obtaining the highest percentage of monoacylglycerides and diacylglycerides [glycerin/vegetal oil ratio of 1:3.5 (mol/mol), at temperature of 56.73 °C, and 9.36% enzyme concentration based on oil’s mass (w/w)]. It was verified that 2 h was the ideal reaction time. Under the best alcoholysis condition, the alkyd resin was produced using phthalic anhydride and the product presented similar characteristics as the current resin produced by a chemical catalyst in the industrial process (final viscosity = Y2, solid content = 44.00%, and IA ≤ 12). 1H NMR and FTIR analyses confirmed the formation of an alkyd resin as they showed the presence of characteristic signals of the final product. The re-usability of the enzyme was investigated, and significant results were observed in the reaction after five cycles (by activity reduction of 6%) showing the viability of applying enzymatic steps in industrial procedures to produce resins in the future, once the application of enzymes also reduced the level of toxicity in the processes.
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References
Assanvo EF, Gogoi P, Dolui SK, Baruah SD (2015) Synthesis, characterization, and performance characteristics of alkyd resins based on Ricinodendron heudelotii oil and their blending with epoxy resins. Ind Crops Prod 65:293–302
Huang Q, Liu C, Chen S, Bai G, An Q, Cao J, Zheng S, Liang Y, **ang B (2015) Effects of formulation on set-to-touch time of waterborne alkyd resin by uniform design. Prog Org Coat 87:189–196
Otabor GO, Ifijen IH, Mohammed FU, Aigbodion AI, Ikhuoria EU (2019) Alkyd resin from rubber seed oil/linseed oil blend: a comparative study of the physiochemical properties. Heliyon 5:16–21
Salata RR, Pellegrene B, Soucek MD (2019) Synthesis and properties of a high solids triethoxysilane-modified alkyd coatings. Prog Org Coat 133:340–349
John G, Nagarajan S, Vemula PK, Julian R, Silverman JR, Pillai CKS (2019) Natural monomers: a mine for functional and sustainable materials—occurrence, chemical modification and polymerization. Prog Polym Sci 92:158–209
Nosal H, Nowicki J, Warzała M, Nowakowska-Bogdan E, Zarebska M (2015) Synthesis and characterization of alkyd resins based on Camelina sativa oil and polyglycerol. Prog Org Coat 86:59–70
Rämänen P, Maunu SL (2014) Structure of tall oil fatty acid-based alkyd resins and alkyd–acrylic copolymers studied by NMR spectroscopy. Prog Org Coat 77:361–368
Bora MM, Deka R, Ahmed N, Kakati DK (2014) Karanja (Millettia pinnata (L.) Panigrahi) seed oil as a renewable raw material for the synthesis of alkyd resin. Ind Crops Prod 61:106–114
Patil DM, Phalak GA, Mhaske ST (2018) Design and synthesis of bio-based epoxidized alkyd resin for anticorrosive coating application. Iran Polym J 27:709–719
Hofland A (2012) Alkyd resins: from down and out to alive and kicking. Prog Org Coat 73:274–282
Salata R, Pellegrene B, Soucek M (2019) Migration of fluorinated alkyd and fluorinated tung oil additives for partially self-stratifying coatings. Prog Org Coat 133:406–417
De Silva U, Amarasinghe ADUS, Premachandra BAJK, Prashantha B (2012) Effect of karawila (Momordica charantia) seed oil on synthesizing the alkyd resins based on soya bean (Glycine max) oil. Prog Org Coat 74:228–232
Vallejo PP, López BL, Murillo EA (2015) Hyperbranched phenolic-alkyd resins with high solid content. Prog Org Coat 87:213–221
Ezeh IE, Umoren SA, Essien EE, Udoh AP (2015) Studies on the utilization of Hura crepitans L. seed oil in the preparation of alkyd resins. Ind Crops Prod 36:94–99
Firestone D (2011) Official methods and recommended practices of the American Oil Chemist’s Society, 6th edn, 2nd Printing. American Oil Chemist's Society—AOCS, Champaign
Lerin LA, Loss RA, Remonatto D, Zenevicz MC, Balen M, OenningNetto V, Ninow JL, Trentin CM, Oliveira JV, De Oliveira D (2014) A review on lipase-catalyzed reactions in ultrasound-assisted systems. Bioprocess Biosyst Eng 37:2381–2394
Oh Y, Park S, Yoo E, Jo S, Hong J, Kim HJ, Kim KJ, Oh KK, Lee SH (2019) Dihydrogen-bonding deep eutectic solvents as reaction media for lipase-catalyzed transesterification. Biochem Eng J 142:34–40
Aarthy M, Saravanan P, Gowthaman MK, Rose C, Kamini NR (2014) Enzymatic transesterification for production of biodiesel using yeast lipases: an overview. Chem Eng Res Des 92:1591–1601
Uyama H (2007) Enzymatic polymerization. Future Dir Biocatal 10:205–249
Blanco SFMM, Santos JS, Feltes MMC, Dors G, Licodiedoff S, Lerin LA, De Oliveira D, Ninow JL, Furigo A Jr (2015) Optimization of diacylglycerol production by glycerolysis of fish oil catalyzed by lipozyme TL IM with Tween 65. Bioprocess Biosyst Eng 38:2379–2388
Patton TC (1962) Alkyd resin technology—formulating techniques and applied calculation. Interscience manual, 8ª. Wiley Interscience, New York
American Society for Testing and Materials—ASTM (1992) Paints, related coatings, and aromatics. ASTM Book of Standards, Section 6, Philadelphia, USA
Poorabdollah M, Beheshty MH (2013) Effect of resin composition on curing kinetic of nanoclay-reinforced unsaturated polyester resins. Iran Polym J 22:385–398
Silverstein RM, Webster FX, Kiemle DJ, Bryce DL (2014) Spectrometric identification of organic compounds, 8thª edn. Wiley, New York
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The authors would like to thank BASF SA for allowing the use of its laboratories and facilities for the development of part of the work, Fundação Educacional Inaciana Padre Sabóia de Medeiros (Centro Universitário FEI) for supporting this research, and Dr. Nivaldo Boralle for the NMR measurements.
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de Carvalho, R.K.C., Ortega, F.d. & Morandim-Giannetti, A.d. Alkyd resin synthesis by enzymatic alcoholysis. Iran Polym J 28, 747–757 (2019). https://doi.org/10.1007/s13726-019-00738-y
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DOI: https://doi.org/10.1007/s13726-019-00738-y