Monitoring the structure–reactivity relationship in epoxidized perilla and safflower oil thermosetting resins

For the first time, the effect of reactant structure, stoichiometry and heating rate on the reactivity of epoxidized perilla oil (EPLO) and epoxidized safflower oil (ESFO) with dicarboxylic acids (DCAs) was studied using in situ FT-IR. The epoxy content in the monomer structure was found to affect the copolymerization system’s reactivity, with epoxidized linseed oil (ELO) considered as a reference. In this study we discuss also the influence of the DCA structure on the copolymerization reactivity. Two aromatic diacids, dithiodibenzoic acid (DTBA) and diphenic acid (DPA), were studied and compared in the copolymerization of the 3 EVOs, in the presence of imidazole (IM) initiator. The kinetics of these reactions were followed by in situ FT-IR. The corresponding activation energies were calculated via different kinetic models. These data highlight the higher reactivity of the EPLO monomer and the DTBA hardener.

[1]  A. Graillot,et al.  Chemical Reactivity and the Influence of Initiators on the Epoxidized Vegetable Oil/Dicarboxylic Acid System , 2020 .

[2]  N. Sbirrazzuoli,et al.  Biomass derived epoxy systems: From reactivity to final properties , 2019 .

[3]  Xinxin Yang,et al.  Bio-based thermosetting epoxy foams from epoxidized soybean oil and rosin with enhanced properties , 2019, Industrial Crops and Products.

[4]  A. Somwangthanaroj,et al.  Synthesis, Thermal Properties and Curing Kinetics of Hyperbranched BPA/PEG Epoxy Resin , 2019, Polymers.

[5]  Kerstin Thiele,et al.  Bio-Based Epoxy Resins Based on Linseed Oil Cured with Naturally Occurring Acids , 2019, Polymers.

[6]  L. Avérous,et al.  A fully bio-based polyimine vitrimer derived from fructose , 2019, Green Chemistry.

[7]  Yongjun Zhang,et al.  Rapid Stress Relaxation and Moderate Temperature of Malleability Enabled by the Synergy of Disulfide Metathesis and Carboxylate Transesterification in Epoxy Vitrimers. , 2019, ACS macro letters.

[8]  Jianfeng Fan,et al.  A robust and stretchable cross-linked rubber network with recyclable and self-healable capabilities based on dynamic covalent bonds , 2019, Journal of Materials Chemistry A.

[9]  Pedro Miguel Moreira,et al.  A Review of Recent Research on Bio-Based Epoxy Systems for Engineering Applications and Potentialities in the Aviation Sector , 2018, Aerospace.

[10]  S. Caillol,et al.  Vanillin-derived amines for bio-based thermosets , 2018 .

[11]  A. Björklund,et al.  Innovative Chemical Process for Recycling Thermosets Cured with Recyclamines® by Converting Bio-Epoxy Composites in Reusable Thermoplastic—An LCA Study , 2018, Materials.

[12]  S. Mohanty,et al.  Recent Development of Biobased Epoxy Resins: A Review , 2018 .

[13]  M. Misra,et al.  Green Approaches To Engineer Tough Biobased Epoxies: A Review , 2017 .

[14]  Mitsuhiro Shibata,et al.  Fully biobased epoxy resin systems composed of a vanillin-derived epoxy resin and renewable phenolic hardeners , 2017 .

[15]  Zuming Hu,et al.  Bio-based epoxy vitrimers: Reprocessibility, controllable shape memory, and degradability , 2017 .

[16]  Smita Mohanty,et al.  Biobased epoxy blends from epoxidized castor oil: Effect on mechanical, thermal, and morphological properties , 2017, Macromolecular Research.

[17]  A. R. D. Luzuriaga,et al.  Epoxy resin with exchangeable disulfide crosslinks to obtain reprocessable, repairable and recyclable fiber-reinforced thermoset composites , 2016 .

[18]  X. Sun,et al.  Network from Dihydrocoumarin via Solvent-Free Metal-Mediated Pathway: A Potential Structure for Substantial Toughness Improvement of Epoxidized Plant Oil Materials , 2016 .

[19]  N. Guigo,et al.  Copolymerization as a Strategy to Combine Epoxidized Linseed Oil and Furfuryl Alcohol: The Design of a Fully Bio-Based Thermoset. , 2015, ChemSusChem.

[20]  N. Guigo,et al.  Inside Cover: Copolymerization as a Strategy to Combine Epoxidized Linseed Oil and Furfuryl Alcohol: The Design of a Fully Bio‐Based Thermoset (ChemSusChem 24/2015) , 2015 .

[21]  Avtar S. Matharu,et al.  New insights into the curing of epoxidized linseed oil with dicarboxylic acids , 2015 .

[22]  J. Robin,et al.  Plant oil-based epoxy resins from fatty diamines and epoxidized vegetable oil , 2015 .

[23]  Damien Montarnal,et al.  Reprocessing and Recycling of Highly Cross-Linked Ion-Conducting Networks through Transalkylation Exchanges of C-N Bonds. , 2015, Journal of the American Chemical Society.

[24]  Jorge F. J. Coelho,et al.  The quest for sustainable polyesters – insights into the future , 2014 .

[25]  Yong J. Yuan,et al.  Room-Temperature Self-Healable and Remoldable Cross-linked Polymer Based on the Dynamic Exchange of Disulfide Bonds , 2014 .

[26]  Wei Zhang,et al.  Reprocessing and recycling of thermosetting polymers based on bond exchange reactions , 2014 .

[27]  V. Pettarin,et al.  Self-healable polymer networks based on the cross-linking of epoxidised soybean oil by an aqueous citric acid solution , 2013 .

[28]  H. Otsuka,et al.  Insertion Metathesis Depolymerization of Aromatic Disulfide-containing Dynamic Covalent Polymers under Weak Intensity Photoirradiation , 2013 .

[29]  S. Caillol,et al.  New biobased carboxylic acid hardeners for epoxy resins , 2013 .

[30]  Z. Ahmad,et al.  Relationships of cure kinetics and processing for epoxidized soybean oil bio-thermoset , 2013 .

[31]  C. Zhao,et al.  Effect of Curing Agent and Temperature on the Rheological Behavior of Epoxy Resin Systems , 2012, Molecules.

[32]  R. Balart,et al.  Properties of Biobased Epoxy Resins from Epoxidized Soybean Oil (ESBO) Cured with Maleic Anhydride (MA) , 2012 .

[33]  Ludwik Leibler,et al.  Making insoluble polymer networks malleable via olefin metathesis. , 2012, Journal of the American Chemical Society.

[34]  I. Blanco,et al.  Effects of novel reactive toughening agent on thermal stability of epoxy resin , 2012, Journal of Thermal Analysis and Calorimetry.

[35]  Ludwik Leibler,et al.  Silica-Like Malleable Materials from Permanent Organic Networks , 2011, Science.

[36]  J. Espinoza-Perez,et al.  Comparison of curing agents for epoxidized vegetable oils applied to composites , 2011 .

[37]  Wen Shyang Chow,et al.  Curing Characteristics and Thermal Properties of Epoxidized Soybean Oil Based Thermosetting Resin , 2011 .

[38]  Michael A. R. Meier,et al.  Plant oils: The perfect renewable resource for polymer science?! , 2011 .

[39]  B Kollbe Ahn,et al.  Thermally stable, transparent, pressure-sensitive adhesives from epoxidized and dihydroxyl soybean oil. , 2011, Biomacromolecules.

[40]  Bert Klumperman,et al.  Self-Healing Materials Based on Disulfide Links , 2011 .

[41]  Krzysztof Matyjaszewski,et al.  Repeatable photoinduced self-healing of covalently cross-linked polymers through reshuffling of trithiocarbonate units. , 2011, Angewandte Chemie.

[42]  Jonathan Seppala,et al.  A healable supramolecular polymer blend based on aromatic pi-pi stacking and hydrogen-bonding interactions. , 2010, Journal of the American Chemical Society.

[43]  Y. Shin,et al.  A comparison of some imidazoles in the curing of epoxy resin , 2010 .

[44]  W. Chow,et al.  Thermal properties of anhydride-cured bio-based epoxy blends , 2010 .

[45]  F. Tournilhac,et al.  Epoxy‐based networks combining chemical and supramolecular hydrogen‐bonding crosslinks , 2010 .

[46]  M. Xian,et al.  Synthesis of biobased epoxy and curing agents using rosin and the study of cure reactions , 2008 .

[47]  Ulrich S Schubert,et al.  Plant oil renewable resources as green alternatives in polymer science. , 2007, Chemical Society reviews.

[48]  Jean-Joseph Max,et al.  Infrared Spectroscopy of Aqueous Carboxylic Acids: Comparison between Different Acids and Their Salts , 2004 .

[49]  Jun-gang Gao,et al.  Curing kinetics and thermal property characterization of a bisphenol-S epoxy resin and DDS system , 2000 .

[50]  C. Fringant,et al.  Polymer networks derived from curing of epoxidised linseed oil: influence of different catalysts and anhydride hardeners , 2000 .

[51]  L. Matějka,et al.  Network formation involving epoxide and carboxyl groups , 1982 .

[52]  Ling Zhao,et al.  Curing kinetics of bio‐based epoxy resin based on epoxidized soybean oil and green curing agent , 2017 .

[53]  A. Kandelbauer,et al.  Synthesis and Characterization of a Bio‐Based Resin from Linseed Oil , 2012 .

[54]  V. Cádiz,et al.  Vegetable oils as platform chemicals for polymer synthesis , 2011 .

[55]  H. Hiller.  In: Ullmann''''s Encyclopedia of Industrial Chemistry , 1989 .