Abstract
Banana starch was modified with B bis(2-hydroxyethyl) terephthalate and its instrumental characterization allowed to propose a chemical structure. In the carbon 6 (C6) of the starch the modification reaction was carried out. The morphology of starch changes due to its chemical modification. The modified starch showed a lower crystallinity and thermal stability, compared to the native starch favoring its film formation. The electrical conductivity of the modified starch films was 2.7 times higher than that for the native starch film. The aqueous hydrolysis of the modified starch films was carried out obtaining a degradation of 77% in a determined time. Modified starch films present different mechanical properties compared to native starch film. These results have high application potential to be used in PET degradation products.
Similar content being viewed by others
References
Ogunsona E, Ojogbo E, Mekonnen T (2018) Advanced material applications of starch and its derivatives. Eur Polym J 108:570–581
Bendoraitiene J, Lekniute KE, Rutkaite R (2018) Biodegradation of cross-linked and cationic starches. Int J Biol Macromol 119:345–351
Tianzhi B, Zhaobin Q (2020) Synthesis, thermal and mechanical properties of fully biobased poly(butylene-co-propylene 2,5-furandicarboxylate) copolyesters with low contents of propylene 2,5-furandicarboxylate units. Polymer 186:122053
Essabti F, Guinault A, Roland S, Régnier G, Ettaqi S, Gervais M (2018) Preparation and characterization of poly(ethylene terephthalate) films coated by chitosan and vermiculite nanoclay. Carbohydr Polym 201:392–401
Yin G, Yang X (2020) Biodegradable polymers: a cure for the planet, but a long way to go. J Polym Res 27:38
Vadim KK, Sergey EP, Nikolay AK (2018) Review of direct chemical and biochemical transformations of starch. Carbohydr Polym 181:460–476
Ayenampudi SB, Rangarajan JM, Ramanathan P (2019) Effect of single and dual-modifications on stability and structural characteristics of foxtail millet starch. Food Chem 271:457–465
Çelik M (2006) Preparation and characterization of starch-g-polymethacrylamide copolymers. J Polym Res 13:427–432
Bhupinder K, Fazilah A, Rajeev B, Alias AK (2012) Progress in starch modification in the last decade. Food Hydrocoll 26:398–404
Nonhlanhla M, Yahya EC, Pradeep K, Lisa CT, Mershen G, Sunaina I, Viness P (2017) A review of the chemical modification techniques of starch. Carbohydr Polym 157:1226–1236
Dai H, Chang PR, Peng F, Jiugao Y, Xiaofei M (2009) N-(2-Hydroxyethyl)formamide as a new plasticizer for thermoplastic starch. J Polym Res 16:529–535
Daisuke H, Yasutaka T, Kazuya Y, Jun-ichi K (2014) Hierarchically self-assembled nanofiber films from amylose-grafted carboxymethyl cellulose. Fibers 2:34–44
Muljana H, Picchioni F, Heeres H, Janssen L (2010) Green starch conversions: Studies on starch acetylation in densified CO2. Carbohydr Polym 82:653–662
Zhang S, Zhang Y, Huang HX, Yan BY, Zhang X, Tang Y (2010) Preparation and properties of starch oxalate half-ester with different degrees of substitution. J Polym Res 17:43–51
Ramírez-Hernández A, Mata-Mata JL, Aparicio-Saguilán A, González-García G, Hernández-Mendoza H, Gutiérrez-Fuentes A, Báez-García E (2016) Chemical modification of banana starch by the in situ polymerization of ε-caprolactone in one step. Starch/starke 69(5–6):1600197
Fares MM, El-faqeeh AS, Osma ME (2003) Graft Copolymerization onto Starch–I. Synthesis and Optimization of Starch Grafted with N-tert-Butylacrylamide Copolymer and its Hydrogels. J Polym Res 10:119–125
Chonthira SC, Schoenlechner R, Sekiguchi K, Berghofer E, Perry K (2014) Effect of extrusion cooking on the physicochemical properties, resistant starch, phenolic content and antioxidant capacities of green banana flour. Food Chem 143:33–39
Mohammadi SR, Khonakdar HA, Ehsani M, Jafari SH, Wagenknecht U, Kretzschmar B (2011) Investigation of thermal behavior and decomposition kinetic of PET/PEN blends and their clay containing nanocomposites. J Polym Res 18:1765–1775
Qiuhui J, Takuya I, Hyuji Y, Dilinazi D, Nattapon L, Shinya S, Fumitake T (2019) The effect of recycling bin design on PET bottle collection performance. Waste Manag 95(2019):32–45
Ghanbari A, Heuzey MC, Carreau PJ, Ton-That MT (2013) A novel approach to control thermal degradation of PET/organoclay nanocomposites and improve clay exfoliation. Polymer 54:1361–1369
Sharma V, Shrivastava P, Agarwal DD (2015) Degradation of PET-bottles to monohydroxyethyl terephthalate (MHT) using ethylene glycol and hydrotalcite. J Polym Res 22:241
Espinoza-García K, Marcos-Fernández A, Navarro R, Ramírez-Hernández A, Baez-García E, Porras-Rangel G (2019) Polymerization of ε-caprolactone with degraded PET for its functionalization. J Polym Res 26:180
Shah TH, Bhatty JI, Gamlen GA, Dollimore D (1984) Aspects of the chemistry of poly(ethylene terephthalate): 5. Polymerization of bis(hydroxyethyl) terephthalate by various metallic catalysts. Polymer 25:1333–1336
Meng-Juan L, Yan-Hong H, An-Qi J, Tian-Shi Y, Ming-Qiao G (2014) Synthesis and characterization of azo dyestuff based on bis(2-hydroxyethyl) terephthalate derived from depolymerized waste poly(ethylene terephthalate) fibers. Chin Chem Lett 25:1550–1554
Güçlü G, Yalçınyuva T, Özgümüş S, Orbay M (2003) Simultaneous glycolysis and hydrolysis of polyethylene terephthalate and characterization of products by differential scanning calorimetry. Polymer 44:7609–7616
Paszun D, Spychaj T (1997) Chemical recycling of poly (ethylene terephthalate). Ind Eng Chem Res 36:1373–1383
Guoxi X, Maixi L, Chen S (2005) Study on depolymerization of waste polyethylene terephthalate into monomer of bis(2-hydroxyethyl terephthalate). Polym Degrad Stabil 87:117–120
Mejjatti AE, Harit T, Riahi A, Khiari R, Bouabdallah I, Malek F (2014) Chemical recycling of poly(ethylene terephthalate). Application to the synthesis of multiblock copolyesters. Express Polym Lett 8:544–553
Achanai B, Duangamol O, Pongsatorn S, Sarinee P, Vorrada L (2018) Synthesis of PET-PLA copolymer from recycle plastic bottle and study of its applications in the electrochromic devices with graphene conductive ink. Mater Today Proc 5:11060–11067
Tong SN, Chen DS, Chen CC, Chung LZ (1983) Unsaturated polyesters based on bis(2-hydroxyethyl)terephthalate. Polym 24:469–472
Wang Y, Zhang Y, Song H, Wang Y, Deng T, Hou X (2019) Zinc-catalyzed ester bond cleavage: Chemical degradation of polyethylene terephthalate. J Clean Prod 208:1469–1475
Viante MF, Zanela TMP, Stoski A, Muniz EC, Almeida CAP (2018) Magnetic microspheres composite from poly(ethylene terephthalate) (PET) waste: Synthesis and characterization. J Clean Prod 198:979–986
Espinoza García K, Navarro R, Ramírez-Hernández A, Marcos-Fernández A (2017) New routes to difunctional macroglycols using ethylene carbonate: Reaction with bis-(2-hydroxyethyl) terephthalate and degradation of poly(ethylene terephthalate). Polym Degrad Stabil 144:195–206
Emadian SM, Turgut TO, Burak D (2017) Biodegradation of bioplastics in natural environments. Waste Manag 59:526–536
Ganesh KA, Anjana K, Hinduja M, Sujitha K, Dharani G (2020) Review on plastic wastes in marine environment – Biodegradation and biotechnological solutions. Mar Pollut Bull 150:110733
Aparicio-Saguilán A, Aguirre-Cruz A, Méndez-Montealvo G, Rodriguez-Ambriz SL, García-Suarez FL, Páramo-Calderón DE, Bello-Pérez LA (2014) The effect of the structure of native banana starch from two varieties on its acid hydrolysis. LWT- Food Sci Technol 58:381–386
Flores-Gorosquieta E, García-Suárez F, Flores-Hiucochea E, Núñez-Santiago M, Gonzáles-Soto R, Bello-Pérez L (2004) Performance starch extraction process of banana fruit (Musa paradisiaca) Pilot plant studies. Acta Cient Venez 55:86–90
Ramírez-Hernández A, Mata-Mata JL, Aparicio-Saguilán A, González-García G, Hernández-Mendoza H, Gutiérrez-Fuentes A, Báez-García E (2016) The effect of ethylene glycol on starch-g-PCL graft copolymer synthesis. Starch/Starke 68:1148–1157
Ramírez-Hernández A, Aparicio‐Saguilán A, Mata‐Mata JL, González‐García G, Hernández‐Mendoza H, Báez‐García E, Conde‐Acevedo J (2017) Clusters of starch‐g‐PCL and their effect on the physicochemical properties of films. Starch-Stärke 70:1700135
Ramírez-Hernández A, Aparicio-Saguilán A, Reynoso-Meza G, Carrillo-Ahumada J (2017) Multi-objective optimization of process conditions in the manufacturing of banana (Musa paradisiaca L.) starch/natural rubber films. Carbohydr Polym 157:1125–1133
Núñez-Santiago MC, Bello-Pérez LA, Tecante A (2004) Swelling-solubility characteristics, granule size distribution and rheological behavior of banana (Musa paradisiaca) starch. Carbohydr Polym 6:65–75
Espinosa SV, Jane J, Bello PL (2009) Physicochemical characteristics of starches from unripe fruits of mango and banana. Starch/Stärke 61:291–299
Šoltýs A, Hronský V, Šmídová N, Olčák D, Ivanič F, Chodák I (2019) Solid-state 1H and 13C NMR of corn starch plasticized with glycerol and urea. Eur Polym J 117:19–27
Wang Y, Min MZ, Mujumdar A (2012) Influence of green banana flour substitution for cassava starch on the nutrition, color, texture and sensory quality in two types of snacks. LWT - Food Sci Technol 4:175–182
Bello-Pérez LA, Agama-Acevedo E, Sáyago-Ayerdi SG, Moreno-Damián E, Figueroa JD (2000) Some structural, physicochemical and functional studies of banana starches isolated from two varieties growing in Guerrero, México. Starch 52:68–73
Faisant N, Gallant DJ, Bouchet B, Champ M (1995) Banana starch breakdown in the human small intestine studied by electron microscopy. Eur J Clin Nutr 49:98–104
Pelissari F, Andrade-Mahecha MM, Amaral SP, Menegalli FC (2013) Comparative study on the properties of flour and starch films of plantain bananas (Musa paradisiaca). Food Hydrocoll 30:681–690
Hizukuri S, Kaneko T, Takeda Y (1983) Measurement of the chain length of amylopectin and its relevance to the origin of crystalline polymorphism of starch granules. Biochim Biophys Acta 760:188–191
Merino D, Mansilla AY, Gutiérrez TJ, Casalongué CA, Alvarez VA (2018) Chitosan coated-phosphorylated starch films: Water interaction, transparency and antibacterial properties. React Funct Polym 131:445–453
Correa AC, Carmona VB, Simão JA, Capparelli-Mattoso LH, Marconcini JM (2017) Biodegradable Blends of Urea Plasticized Thermoplastic Starch (UTPS) and poly(ε-caprolactone) (PCL): Morphological, Rheological, Thermal and Mechanical Properties. Carbohydr Polym 167:177–184
Huang M, Yu J, Ma X (2005) Ethanolamine as a novel plasticizer for thermoplastic starch. Polym Degrad Stabil 90:501–507
Montoya M, Arrieta-Álvaro A, Palencia MS (2018) Synthesis and electrochemical characterization of polypyrrole/sodium p-toluenesulfonate biofilms supported on cassava starch conductive polymers for applications in electrical charge accumulators. Adv J Food Sci Technol 16:142–145
Lavielle L, Nakajima K, Schultz J (1992) Influence of an electric field on polar-group orientation and adhesion at poly(ethylene terephthalate) surfaces. J Appl Polym Sci 46:1045–1050
Gutiérrez TJ, Tapia MS, Pérez E, Famá L (2015) Structural and mechanical properties of edible films made from native and modified cush-cush yam and cassava starch. Food Hydrocoll 45:211–217
Acknowledgements
We are grateful to Concejo Nacional de Ciencia y Tecnología (Conacyt), Instituto de Ciencia y Tecnología de Polímeros (ICTP), Universidad del Papaloapan campus Tuxtepec, Martínez Olguiín Aldo de Jesús, Martha Ferrer Guadalupe and Martha Rocio Valencia Estacio for their assistance on this article.
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
ESM 1
(DOCX 1.80 MB)
Rights and permissions
About this article
Cite this article
Ramírez-Centeno, S., Marcos-Fernández, A., Aparicio-Saguilán, A. et al. Modified starch with bis(2-hydroxyethyl) terephthalate: synthesis, characterization and elaboration of films. J Polym Res 27, 270 (2020). https://doi.org/10.1007/s10965-020-02249-4
Received:
Revised:
Accepted:
Published:
DOI: https://doi.org/10.1007/s10965-020-02249-4