Abstract
Branched polyesters based on the polyethylene terephthalate were synthesized by incorporating isophthalic acid (IPA) and trimellitic anhydride (TMA). TMA has the branching agent role. During the esterification step, only terephthalic acid, IPA, and ethylene glycol were reacted and TMA was added at the beginning of the polycondensation step. Reaction progress was studied using water production and mixing torque increase during esterification and polycondensation steps, respectively. Polycondensation time increases with IPA and decreases with TMA. Fourier transform infrared spectroscopy spectrum shows the production of polyester. Randomness and sequence length were studied using 13CNMR. Results reveal that randomness increases with TMA. Crystallinity and morphology of samples were studied using differential scanning microscopy (DSC). DSC thermograms show that samples turn to an amorphous structure by adding IPA and TMA with decreasing glass transition temperature, Tg. X-ray diffraction spectra approve changing nature similar to DSC results. Dynamic light scattering results present that with an increase in TMA, some size-increasing particles were detected. The rheological behavior of samples was studied using RMS. By adding TMA, the elastic behavior of samples changes to viscous behaviors.
Similar content being viewed by others
Data availability
On request, it will be handed.
References
Gupta VB, Bashir Z (2002) Handbook of Thermoplastic Polyesters: Homopolymers, Copolymers. Wiley-VCH Verlag GmbH, Weinheim, Blends and Composites
Scheirs J, Long TE (2005) Modern polyesters: chemistry and technology of polyesters and copolyesters. John Wiley & Sons, West Sussex
Fei B (2018) High-performance fibers for textiles. In: Miao M, Xin J (eds) Engineering of High-Performance Textiles, 1st edn. Woodhead Publishing, pp 27–58
Korivi NS (2015) Preparation, characterization, and applications of poly (ethylene terephthalate) nanocomposites. In: Mittal V (ed) Manufacturing of Nanocomposites with Engineering Plastics, 1st edn. Woodhead Publishing, pp 167–98
Zekriardehani S, Joshi AS, Jabarin SA, Gidley DW, Coleman MR (2018) Effect of dimethyl terephthalate and dimethyl isophthalate on the free volume and barrier properties of poly (ethylene terephthalate)(PET): amorphous PET. Macromolecules 51(2):456–467. https://doi.org/10.1021/acs.macromol.7b02230
Liu RYF, Hu YS, Hibbs MR, Collard DM, Schiraldi DA, Hiltner A, Baer E (2005) Improving oxygen barrier properties of poly (ethylene terephthalate) by incorporating isophthalate. I. Effect of orientation. J Appl Polymer Sci 98(4):1615–1628. https://doi.org/10.1002/app.22213
Hu YS, Hiltner A, Baer E (2005) Improving oxygen barrier properties of poly (ethylene terephthalate) by incorporating isophthalate. II. Effect of crystallization. J Appl Polymer Sci 98(4):1629–1642. https://doi.org/10.1002/app.22214
Jayakannan M, Ramakrishnan S (1999) Effect of branching on the crystallization kinetics of poly (ethylene terephthalate). J Appl Polym Sci 74(1):59–66. https://doi.org/10.1002/(SICI)1097-4628(19991003)74:1%3c59::AID-APP6%3e3.0.CO;2-0
Verhoyen O, Dupret F, Legras R (1998) Isothermal and non-isothermal crystallization kinetics of polyethylene terephthalate: mathematical modeling and experimental measurement. Polym Eng Sci 38(9):1594–1610
Karayannidis GP, Sideridou ID, Zamboulis DN, Bikiaris DN, Sakalis AJ (2000) Thermal behavior and tensile properties of poly (ethylene terephthalate-co-ethylene isophthalate). J Appl Polymer Sci 78(1):200–207. https://doi.org/10.1002/1097-4628(20001003)78:1%3c200::AID-APP240%3e3.0.CO;2-R
Gaonkar AA, Murudkar VV, Deshpande VD (2020) Comparison of crystallization kinetics of polyethylene terephthalate (PET) and reorganized PET. Thermochimica Acta 683:178472
Yu J, Li B, Lee S, Ree M (1999) Relationship between physical properties and chemical structures of poly (ethylene terephthalate-co-ethylene isophthalate). J Appl Polym Sci 73(7):1191–1195. https://doi.org/10.1002/(SICI)1097-4628(19990815)73:7%3c1191::AID-APP12%3e3.0.CO;2-S
Ubach J, de Ilarduya AM, Quintana R, Alla A, Rudé E, Muñoz-Guerra S (2010) Poly (ethylene terephthalate-co-isophthalate) copolyesters obtained from ethylene terephthalate and isophthalate oligomers. J Appl Polym Sci 115(3):1823–1830. https://doi.org/10.1002/app.31308
Manaresi P, Munari A, Pilati F, Alfonso GC, Russo S, Sartirana ML (1986) Synthesis and characterization of highly-branched poly (ethylene terephthalate). Polymer 27(6):955–960. https://doi.org/10.1016/0032-3861(86)90311-3
Hudson N, MacDonald WA, Neilson A, Richards RW, Sherrington DC (2000) Synthesis and characterization of nonlinear PETs produced via a balance of branching and end-capping. Macromolecules 33(25):9255–9261. https://doi.org/10.1021/ma000656c
Qiu T, Tang L, Fu Z, Tuo X, Li Y, Liu D, Yang W (2004) Modification of end-groups of aliphatic hyperbranched polyester. Polym Adv Technol 15(1–2):65–69. https://doi.org/10.1002/pat.432
Ma S, Qian J, Zhuang Q, Li X, Kou W, Peng S (2018) Synthesis and application of water-soluble hyperbranched polyester modified by trimellitic anhydride. J Macromol Sci Part A 55(5):414–421. https://doi.org/10.1080/10601325.2018.1453261
Chen MH, Lai CC, Chen HL, Lin CH, Hsiao HT, Liu LC, Chen CM (2019) Preparation of long-chain branched polyethylene terephthalates (PETs), and crystallization behaviors, thermal characteristics, and hydrolysis resistance of their biaxially stretching films. J Phys Chem Solids 1(129):354–367. https://doi.org/10.1016/j.jpcs.2019.01.031
Zhang D, Jia D, Chen S (2009) Synthesis and characterization of low viscosity aromatic hyperbranched poly (trimellitic anhydride ethylene glycol) ester epoxy resin. Macromol Chem Phys 210(13–14):1159–1166. https://doi.org/10.1002/macp.200900230
Zhang D, Chen Y, Jia D (2009) Toughness and reinforcement of diglycidyl ether of bisphenol-A by hyperbranched poly (trimellitic anhydride-butanediol glycol) ester epoxy resin. Polym Compos 30(7):918–925. https://doi.org/10.1002/pc.20633
Lamberti G, Peters GWM, Titomanlio G (2007) Crystallinity and linear rheological properties of polymers. Int Polym Proc 22(3):303–310. https://doi.org/10.3139/217.2006
Suneel DMA, Buzza A, Groves DJ, McLeish TCB, Parker D, Keeney AJ, Feast WJ (2002) Rheology and molecular weight distribution of hyperbranched polymers. Macromolecules 35(25):9605–9612. https://doi.org/10.1021/ma020820r
Kil SB, Augros Y, Leterrier Y, Månson JAE, Christel A, Borer C (2003) Rheological properties of hyperbranched polymer/poly (ethylene terephthalate) reactive blends. Polym Eng Sci 43(2):329–343. https://doi.org/10.1002/pen.10028
Kruse M, Wagner MH (2017) Rheological and molecular characterization of long-chain branched poly (ethylene terephthalate). Rheol Acta 56(11):887–904. https://doi.org/10.1007/s00397-017-1043-y
Zhang F, Kang H, Bai Y, Jiang B, Huang Y, Liu L (2016) Catalytic property of poly (ethylene terephthalate-co-isophthalate) synthesized with a novel Sb/Al bimetallic compound catalyst. RSC Adv 6(72):67677–67684. https://doi.org/10.1039/C6RA09055A
Charles J, Ramkumaar GR (2009) FTIR and thermal studies on polyethylene terephthalate and acrylonitrile butadiene styrene. Asian J Chem 21(6):4389–4398
Mayouf I, Guessoum M, Fuensanta M, Martìnez JMM (2020) Appraisal of ε-Caprolactam and Trimellitic Anhydride Potential as Novel Chain Extenders for Poly(lactic acid). Polymer Eng Sci 60(5):944–955. https://doi.org/10.1002/pen.25350
De Luca E, Richards RW (2003) Molecular characterization of a hyperbranched polyester. I. Dilute solution properties. J Polymer Sci Part B: Polymer Phys 41(12):1339–1351. https://doi.org/10.1002/polb.10463
de Ilarduya AM, Kint DPR, Muñoz-Guerra S (2000) Sequence analysis of poly (ethylene terephthalate-co-isophthalate) copolymers by 13CNMR. Macromolecules 33(12):4596–4598. https://doi.org/10.1021/ma991882t
Lbbett RN (1993) NMR spectroscopy of polymers. Blackie Academic & Professional
Johnson JE (1959) X-ray diffraction studies of the crystallinity in polyethylene terephthalate. J Appl Polym Sci 2(5):205–209. https://doi.org/10.1002/app.1959.070020514
Aoyama S, Ismail I, Park YT, Yoshida Y, Macosko CW, Ougizawa T (2018) Polyethylene terephthalate/trimellitic anhydride modified graphene nanocomposites. ACS Appl Nano Mater 1(11):6301–6311. https://doi.org/10.1021/acsanm.8b01525
Kharchenko SB, Kannan RM (2003) Role of architecture on the conformation, rheology, and orientation behavior of linear, star, and hyperbranched polymer melts. 2. Linear viscoelasticity and flow birefringence. Macromolecules 36(2):407–415. https://doi.org/10.1021/ma025649y
Funding
Not applicable.
Author information
Authors and Affiliations
Contributions
All authors have enough contribution in this work.
Corresponding author
Ethics declarations
Conflict of interest
Author declares that there is no conflict of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Mohammadi Avarzman, A., Rafizadeh, M. & Afshar Taromi, F. Branched polyester based on the polyethylene tere/iso phthalate and trimellitic anhydride as branching agent. Polym. Bull. 79, 6099–6121 (2022). https://doi.org/10.1007/s00289-021-03802-x
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00289-021-03802-x