Effect of Acetylation on Stability to Retrogradation of Starch Extracted from Wild Polynesian Arrowroot (Tacca leontopetaloides (L.) Kuntze) for Utilization as Adhesive on Paper
Starch was isolated from T. leontopetaloides tubers, chemically modified by acetylation with varying amounts of acetic anhydride. Monolayer of the ten acetylated and control starch powders was exposed on roof top for five weeks and pastes of both exposed and unexposed (control) samples were prepared with distilled water (1？:？3 w/w). The effects of acetylation, degree of substitution (DS), and exposure to sunlight were investigated to evaluate the retrogradation tendency of the adhesive pastes from changes in syneresis, tack strength, optical clarity, viscosity, gelation time, and drying time. The results obtained showed that all the adhesive properties studied were affected by both DS and exposure to sunlight. While tack strength, viscosity, and drying time were found to increase with increase in DS, syneresis, optical clarity, and gelation time were found to decrease with increase in DS. Increase in tack strength and reduction in syneresis imply that the acetylation treatment has made T. leontopetaloides starch more suitable for use in remoistenable adhesive applications. The reduction in syneresis, optical clarity, and gelation time with increase in DS was attributed to the strengthening of the bonds between the amylose and amylopectin molecules, preventing water leaching out of the starch granules. 1. Introduction Adhesive is a natural or synthetic substance that, when applied to surfaces of materials, binds them and the joint resist separation. Natural bioadhesives are obtained from vegetable matter, starch, plant exudates, and resins or from animals, for example, casein [1–5]. Advantages of adhesives over other binding techniques include ability to bind different materials together, efficient distribution of stress across the bonded joint, cost effectiveness, easy process mechanization, improvement in aesthetics design, and design flexibility [6–9]. Starch, , is a complex carbohydrate occurring in the form of minute granules in seeds, fruits, tubers, roots, and stem pith of plants, consisting of two polymers, amylose and amylopectin, and the molar ratio of which is about 20–30% and 80–70%, respectively [10–13]. Amylose is a linear polysaccharide composed of mostly linear chains with 500–20,000 α- -D-glucose units, as can be seen in Figure 1 [14, 15]. Figure 1: Amylose molecule (adapted from Ward et al. [ 19]). Depending on the botanic source, amylose can form an extended shape (hydrodynamic radius 7–22？nm) but generally tends to wind up into a rather stiff left-handed single helix or form even stiffer parallel left-handed double helical junction
References
[1]
J. Zalucha, “The chemistry and structure of adhesives,” in Rieldel’s Handbook of Industrial Chemistry, J. A. Kent, Ed., pp. 239–247, S.K. Jain Publishers, New Delhi, India, 9th edition, 1997.
[2]
S. Ebnesajjad, Handbook of Adhesives and Surface Preparation: Technology, Applications and Manufacturing, Elsevier, Amsterdam, The Netherlands, 2010.
[3]
K. L. Mittal and A. Pizzi, Handbook of Adhesive Technology, Marcel Dekker, New York, NY, USA, 2nd edition, 2003.
[4]
H. Wiese, “Characterization of aqueous polymer dispersions,” in Polymer Dispersions and Their Industrial Applications, D. Urban and K. Takamura, Eds., pp. 41–73, Wiley-VCH, Weinheim, Germany, 2002.
[5]
J. Comyn, “What are adhesives and sealants and how do they work?” in Adhesive Bonding: Science, Technology and Applications, D. Adams, Ed., pp. 23–51, CRC Press, Boca Raton, Fla, USA, 2005.
[6]
Y. Y. Huang, W. Zhou, K. J. Hsia et al., “Stamp collapse in soft lithography,” Langmuir, vol. 21, no. 17, pp. 8058–8068, 2005.
[7]
N. Maeda, N. Chen, M. Tirrell, and J. N. Israelachvili, “Adhesion and friction mechanisms of polymer-on-polymer surfaces,” Science, vol. 297, no. 5580, pp. 379–382, 2002.
[8]
B. K. Sharma, Industrial Chemistry, Krishna Prakashan Media (P) Limited, Meerut, India, 2011.
[9]
J. Custódio, J. Broughton, and H. Cruz, “A review of factors influencing the durability of structural bonded timber joints,” International Journal of Adhesion and Adhesives, vol. 29, no. 2, pp. 173–185, 2009.
[10]
S. H. Yoo and J. L. Jane, “Structural and physical characteristics of waxy and other wheat starches,” Carbohydrate Polymers, vol. 49, no. 3, pp. 297–305, 2002.
[11]
L. A. Bello-Pérez, E. Agama-Acevedo, S. G. Sáyago-Ayerdi, E. Moreno-Damian, and J. D. C. Figueroa, “Some structural, physicochemical and functional studies of banana starches Isolated from two varieties growing in Guerrero, México,” Starch/St？rke, vol. 52, no. 2-3, pp. 68–73, 2000.
[12]
L. Jayakody, R. Hoover, Q. Liu, and E. Donner, “Studies on tuber starches. II. Molecular structure, composition and physicochemical properties of yam (Dioscorea sp.) starches grown in Sri Lanka,” Carbohydrate Polymers, vol. 69, no. 1, pp. 148–163, 2007.
[13]
J. E. McMurry, Organic Chemistry, Brooks/Cole Cengage Learning, Belmont, Calif, USA, 2012.
[14]
M. Li, P. Liu, W. Zou et al., “Extrusion processing and characterization of edible starch films with different amylose contents,” Journal of Food Engineering, vol. 106, no. 1, pp. 95–101, 2011.
[15]
M. Thuwall, A. Boldizar, and M. Rigdahl, “Extrusion processing of high amylose potato starch materials,” Carbohydrate Polymers, vol. 65, no. 4, pp. 441–446, 2006.
[16]
Y. Tian, Y. Li, X. Xu et al., “A novel size-exclusion high performance liquid chromatography (SE-HPLC) method for measuring degree of amylose retrogradation in rice starch,” Food Chemistry, vol. 118, no. 2, pp. 445–448, 2010.
[17]
K. Kohyama, J. Matsuki, T. Yasui, and T. Sasaki, “A differential thermal analysis of the gelatinization and retrogradation of wheat starches with different amylopectin chain lengths,” Carbohydrate Polymers, vol. 58, no. 1, pp. 71–77, 2004.
[18]
R. N. Waduge, R. Hoover, T. Vasanthan, J. Gao, and J. Li, “Effect of annealing on the structure and physicochemical properties of barley starches of varying amylose content,” Food Research International, vol. 39, no. 1, pp. 59–77, 2006.
[19]
R. M. Ward, Q. Gao, H. de Bruyn, R. G. Gilbert, and M. A. Fitzgerald, “Improved methods for the structural analysis of the amylose-rich fraction from rice flour,” Biomacromolecules, vol. 7, no. 3, pp. 866–876, 2006.
[20]
M. Tako and S. Hizukuri, “Rheological properties of wheat (Halberd) amylopectin,” Starch/St？rke, vol. 55, no. 8, pp. 345–349, 2003.
[21]
M. Tako, I. Shiroma, and S. Uechi, “Rheological properties of wheat amylopectin,” Science Buletin of Faculty of Agriculture, University of Ryukyus, vol. 51, pp. 139–143, 2004.
[22]
D. Plackett, H. Anturi, M. Hedenqvist et al., “Physical properties and morphology of films prepared from microfibrillated cellulose and microfibrillated cellulose in combination with amylopectin,” Journal of Applied Polymer Science, vol. 117, no. 6, pp. 3601–3609, 2010.
[23]
D. R. Askeland and P. P. Pradeep, The Science and Engineering of Materials, Thomson Engineering, Boston, Mass, USA, 5th edition, 2005.
[24]
C. Hall, Polymer Materials: An Introduction for Technologists and Scientists, Macmillan Educational, Hampshire, UK, 2008.
[25]
J. Delville, C. Joly, P. Dole, and C. Bliard, “Influence of photocrosslinking on the retrogradation of wheat starch based films,” Carbohydrate Polymers, vol. 53, no. 4, pp. 373–381, 2003.
[26]
M. A. Ottenhof, S. E. Hill, and I. A. Farhat, “Comparative study of the retrogradation of intermediate water content waxy maize, wheat, and potato starches,” Journal of Agricultural and Food Chemistry, vol. 53, no. 3, pp. 631–638, 2005.
[27]
A. L. M. Smits, P. H. Kruiskamp, J. J. G. van Soest, and J. F. G. Vliegenthart, “The influence of various small plasticisers and malto-oligosaccharides on the retrogradation of (partly) gelatinised starch,” Carbohydrate Polymers, vol. 51, no. 4, pp. 417–424, 2003.
[28]
A. A. Karim, M. H. Norziah, and C. C. Seow, “Methods for the study of starch retrogradation,” Food Chemistry, vol. 71, no. 1, pp. 9–36, 2000.
[29]
Y. Tian, Y. Li, X. Xu, and Z. Jin, “Starch retrogradation studied by thermogravimetric analysis (TGA),” Carbohydrate Polymers, vol. 84, no. 3, pp. 1165–1168, 2011.
[30]
M. Tako and S. Hizukuri, “Retrogradation mechanism of rice starch,” Cereal Chemistry, vol. 77, no. 4, pp. 473–477, 2000.
[31]
Q. Liu and D. B. Thompson, “Effects of moisture content and different gelatinization heating temperatures on retrogradation of waxy-type maize starches,” Carbohydrate Research, vol. 314, no. 3-4, pp. 221–235, 1998.
[32]
X. Lian, S. Zhao, Q. Liu, and X. Zhang, “A photographic approach to the possible mechanism of retrogradation of sweet potato starch,” International Journal of Biological Macromolecules, vol. 48, no. 1, pp. 125–128, 2011.
[33]
S. Charoenrein, O. Tatirat, and J. Muadklay, “Use of centrifugation-filtration for determination of syneresis in freeze-thaw starch gels,” Carbohydrate Polymers, vol. 73, no. 1, pp. 143–147, 2008.
[34]
S. Charoenrein, O. Tatirat, K. Rengsutthi, and M. Thongngam, “Effect of konjac glucomannan on syneresis, textural properties and the microstructure of frozen rice starch gels,” Carbohydrate Polymers, vol. 83, no. 1, pp. 291–296, 2011.
[35]
G. Wu, C. van Alsenoy, H. J. Geise et al., “Acetic anhydride in the gas phase, studied by electron diffraction and infrared spectroscopy, supplemented with ab initio calculations of geometries and force fields,” Journal of Physical Chemistry A, vol. 104, no. 7, pp. 1576–1587, 2000.
[36]
A. Deb, I. Malvade, P. Biswas, and J. Schroeder, “An experimental and analytical study of the mechanical behaviour of adhesively bonded joints for variable extension rates and temperatures,” International Journal of Adhesion and Adhesives, vol. 28, no. 1-2, pp. 1–15, 2008.
[37]
C. E. Carraher Jr., Introduction to Polymer Chemistry, CRC Press, Boca Raton, Fla, USA, 2nd edition, 2010.
[38]
E. Johansson, L. Lundstr？m, M. Norgren, and L. W？gberg, “Adsorption behavior and adhesive properties of biopolyelectrolyte multilayers formed from cationic and anionic starch,” Biomacromolecules, vol. 10, no. 7, pp. 1768–1776, 2009.
[39]
H. R. Allock, Introduction to Materials Chemistry, John Wiley & Sons, Singapore, 2008.
[40]
L. S. Collado, R. C. Mabesa, and H. Corke, “Genetic variation in the physical properties of sweet potato starch,” Journal of Agricultural and Food Chemistry, vol. 47, no. 10, pp. 4195–4201, 1999.
[41]
D. R. Lu, C. M. Xiao, and S. J. Xu, “Starch-basedcompletely biodegradable polymer materials,” Express Polymer Letters, vol. 3, no. 6, pp. 366–375, 2009.
[42]
X. Y. Song, G. Q. He, H. Ruan, and Q. H. Chen, “Preparation and properties of octenyl succinic anhydride modified early Indica rice starch,” Starch/St？rke, vol. 58, no. 2, pp. 109–117, 2006.
[43]
S. Saartratra, C. Puttanlekb, V. Rungsardthong, and D. Uttapap, “Paste and gel properties of low-substituted acetylated canna starches,” Carbohydrate Polymers, vol. 61, no. 2, pp. 211–221, 2005.
[44]
S. J. Gao and K. Nishinari, “Effect of degree of acetylation on gelation of konjac glucomannan,” Biomacromolecules, vol. 5, no. 1, pp. 175–185, 2004.
[45]
Y. Xu, V. Miladinov, and M. A. Hanna, “Synthesis and characterization of starch acetates with high substitution,” Cereal Chemistry, vol. 81, no. 6, pp. 735–740, 2004.
[46]
S. Richardson and L. Gorton, “Characterisation of the substituent distribution in starch and cellulose derivatives,” Analytica Chimica Acta, vol. 497, no. 1-2, pp. 27–65, 2003.
[47]
R. N. Waduge, R. Hoover, T. Vasanthan, J. Gao, and J. Li, “Effect of annealing on the structure and physicochemical properties of barley starches of varying amylose content,” Food Research International, vol. 39, no. 1, pp. 59–77, 2006.
[48]
K. M. Chung, T. W. Moon, and J. K. Chun, “Influence of annealing on gel properties of Mung bean starch,” Cereal Chemistry, vol. 77, no. 5, pp. 567–571, 2000.
[49]
R. F. Tester and S. J. J. Debon, “Annealing of starch—a review,” International Journal of Biological Macromolecules, vol. 27, no. 1, pp. 1–12, 2000.
[50]
C. Pukkahuta and S. Varavinit, “Structural transformation of sago starch by heat-moisture and osmotic-pressure treatment,” Starch/St？rke, vol. 59, no. 12, pp. 624–631, 2007.
[51]
R. V. Manek, O. O. Kunle, M. O. Emeje et al., “Physical, thermal and sorption profile of starch obtained from Tacca leontopetaloides,” Starch/St？rke, vol. 57, no. 2, pp. 55–61, 2005.
[52]
C. S. Hwang, A. Shemorry, and A. Varshavsky, “N-terminal acetylation of cellular proteins creates specific degradation signals,” Science, vol. 327, no. 5968, pp. 973–977, 2010.
[53]
A. Y. Utkin, L. Y. Bogel'fer, and A. L. Chimishkyan, “Reversible reactions in the acidolysis of methyoxyacetic acid by acetic anhydride,” Russian Journal of Physical Chemistry, vol. 65, pp. 1049–1059, 1991.
[54]
J. J. Shatynski and D. Hanesian, “Adiabatic kinetic studies of the cytidine/acetic anhydride reaction by utilizing temperature versus time data,” Industrial and Engineering Chemistry Research, vol. 32, no. 4, pp. 594–599, 1993.
[55]
Z. G. Luo and Y. C. Shi, “Preparation of acetylated waxy, normal, and high-amylose maize starches with intermediate degrees of substitution in aqueous solution and their properties,” Journal of Agriculture and Food Chemistry, vol. 60, no. 37, pp. 9468–9475, 2012.
[56]
F. Han, C. Gao, M. Liu, F. Huang, and B. Zhang, “Synthesis, optimization and characterization of acetylated corn starch with the high degree of substitution,” International Journal of Biological Macromolecules, vol. 59, pp. 372–376, 2013.
[57]
S. I. Ofoefule, A. C. Osuji, and O. Okorie, “Effects of physical and chemical modifications on the disintegrant and dissolution properties of Tacca involucrata starch,” Bio-Research, vol. 2, no. 1, pp. 97–102, 2004.
[58]
S. Ahemen and A. O. Raji, “Development and performance evaluation of a motorized rasping machine for Tacca involucrata starch production,” Journal of Agricultural Engineering and Technology, vol. 16, no. 1, pp. 52–63, 2008.
[59]
A. B. Adebiyi, M. O. Omojola, A. T. Orishadipe, M. O. Afolayan, and D. Olalekan, “Tacca starch citrate—a potential pharmaceutical excipient,” Archives of Applied Science Research, vol. 3, no. 6, pp. 114–121, 2011.
[60]
M. Arbonnier, Trees, Shrubs and Lianas of West African Dry Zones, CIRAD, Margraf Publishers, Paris, France, 2004.
[61]
O. O. Kunle, Y. E. Ibrahim, M. O. Emeje, S. Shaba, and Y. Kunle, “Extraction, physicochemical and compaction properties of tacca starch—a potential pharmaceutical excipient,” Starch/St？rke, vol. 55, no. 7, pp. 319–325, 2003.
[62]
U. J. Ukpabi, E. Ukenye, and A. O. Olojede, “Raw materials potentials of Nigerian wild Polynesian arrowroot (Tacca leontopetaloides) tubers and starch,” Journal of Food Technology, vol. 7, no. 4, pp. 135–138, 2009.
[63]
A. Rudin, Elements of Polymer Science and Engineering, Elsevier, Singapore, 2nd edition, 2006.
[64]
C. M. Stafford, B. D. Vogt, C. Harrison, D. Julthongpiput, and R. Huang, “Elastic moduli of ultrathin amorphous polymer films,” Macromolecules, vol. 39, no. 15, pp. 5095–5099, 2006.
[65]
J. E. Braddy, N. D. Jerspersen, and A. Hyslop, Chemistry, John Wiley & Sons, Singapore, 6th edition, 2012.
[66]
L. A. Bello-Pérez, E. Agama-Acevedo, S. G. Sáyago-Ayerdi, E. Moreno-Damian, and J. D. C. Figueroa, “Some structural, physicochemical and functional studies of banana starches isolated from two varieties growing in Guerrero, México,” Starch/St？rke, vol. 52, no. 2-3, pp. 68–73, 2000.
[67]
L. Brown and T. Holme, Chemistry for Engineering Students, Brooks/Cole, Cengage Learning, Belmont, Calif, USA, 2nd edition, 2011.
[68]
Anonymous, “Standard test method for peel resistance of adhesives,” in Annual Book of ASTM Standards, (ASTM D1876), pp. 189–197, American Society for Testing and Materials, Philadelphia, Pa, USA, 2009.
[69]
M. G. D. Baumann and A. H. Conner, “Carbohydrate polymers as adhesives,” in Handbook of Adhesive Technology, A. Pizzi and K. L. Mittal, Eds., pp. 375–379, Marcel Dekker, New York, NY, USA, 2nd edition, 2003.
[70]
Anonymous, “Standard test method for viscosity of adhesives,” in Annual Book of ASTM Standards, (ASTM D1084), pp. 549–557, American Society for Testing and Materials, Philadelphia, Pa, USA, 2006.
