A renewable bio-based epoxy resin with improved mechanical performance that can compete with DGEBA

The aim of this study is to find a suitable substitution for diglycidyl ether bisphenol A (DGEBA) to avoid the devastating side effects of bisphenol A. Vanillin, an aromatic compound, was used as a renewable material to synthesize a bio-based epoxy resin. The structure of the vanillin-based epoxy resin was confirmed by Fourier transform infrared spectroscopy (FT-IR) analysis. The major drawback of bio-based epoxy resins is their poor mechanical properties preventing them from competing with petroleum based epoxy resins such as DGEBA. Herein, a prepared calcium nitrate solution as an inorganic accelerator was used to accelerate the curing reaction of bio-based epoxy resin which reduced curing times as well as improving significantly the mechanical properties e.g., tensile strength, pull-off strength, and Izod impact strength. Differential scanning calorimetry (DSC) analysis was used to investigate the curing process and thermal properties of the vanillin-based epoxy resin with and without inorganic accelerators and also DGEBA without accelerators. The results showed that in the presence of 2 wt% inorganic accelerator, the initial onset curing temperature of vanillin-based epoxy resin was reduced from 60.1 °C to 8.5 °C, while the initial onset curing temperature of DGEBA was 55.8 °C. In addition, tensile strength and Izod impact strength of the vanillin-based epoxy system in the presence of inorganic accelerators increased in comparison to the DGEBA system. Moreover, in order to study the effect of inorganic accelerators on the toughness of the synthesized vanillin-based epoxy resin, fracture surfaces from Izod impact strength tests were observed using scanning electron microscopy (SEM) which confirmed improving mechanical properties.

[1]  D. Achilias,et al.  Cure Kinetics Study of Two Epoxy Systems with Fourier Tranform Infrared Spectroscopy (FTIR) and Differential Scanning Calorimetry (DSC) , 2012 .

[2]  V. B. Gupta,et al.  The temperature‐dependence of some mechanical properties of a cured epoxy resin system , 1985 .

[3]  Bernard Boutevin,et al.  Functionalized green tea tannins as phenolic prepolymers for bio-based epoxy resins , 2014 .

[4]  K. Uhrich,et al.  Ferulic Acid-Based Polymers with Glycol Functionality as a Versatile Platform for Topical Applications. , 2015, Biomacromolecules.

[5]  Bernard Boutevin,et al.  Vanillin, a promising biobased building-block for monomer synthesis , 2014 .

[6]  S. Caillol,et al.  Ferulic acid-based renewable esters and amides-containing epoxy thermosets from wheat bran and beetroot pulp: Chemo-enzymatic synthesis and thermo-mechanical properties characterization , 2017 .

[7]  S. Hsu,et al.  Preparation of epoxy/silica and epoxy/titania hybrid resists via a sol-gel process for nanoimprint lithography , 2010 .

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

[9]  T. Endo,et al.  Efficient accelerating effect of carbonyldiimidazole on epoxy‐dicyandiamide curing system , 2011 .

[10]  M. Milosevic,et al.  Introduction to Spectroscopy , 2012 .

[11]  Yanhua Jiang,et al.  Bio-based epoxy resin from itaconic acid and its thermosets cured with anhydride and comonomers , 2013 .

[12]  M. Naebe,et al.  Fish DNA-modified clays: Towards highly flame retardant polymer nanocomposite with improved interfacial and mechanical performance , 2016, Scientific Reports.

[13]  Jean-Pierre Habas,et al.  A fully biobased epoxy resin from vegetable oils: From the synthesis of the precursors by thiol‐ene reaction to the study of the final material , 2011 .

[14]  F. Haupert,et al.  Toughening effects of titanium dioxide nanoparticles on TiO2/epoxy resin nanocomposites , 2009 .

[15]  C. Sung,et al.  Fluorescence and IR characterization of epoxy cured with aliphatic amines , 2005 .

[16]  S. Caillol,et al.  Multi-functionalization of gallic acid. Synthesis of a novel bio-based epoxy resin , 2013 .

[17]  K. Chandrashekhara,et al.  Curing and mechanical characterization of a soy‐based epoxy resin system , 2004 .

[18]  L. Avérous,et al.  Chemical modification of lignins: Towards biobased polymers , 2014 .

[19]  Shelby A. Flint,et al.  Bisphenol A exposure, effects, and policy: a wildlife perspective. , 2012, Journal of environmental management.

[20]  J. L. Stanford,et al.  Rheological Behavior and Gel-Point Determination for a Model Lewis Acid-Initiated Chain Growth Epoxy Resin , 2001 .

[21]  A. Mirmohseni,et al.  Preparation and characterization of an epoxy nanocomposite toughened by a combination of thermoplastic, layered and particulate nano-fillers , 2010 .

[22]  O. Zabihi Preparation and characterization of toughened composites of epoxy/poly(3,4-ethylenedioxythiophene) nanotube: Thermal, mechanical and electrical properties , 2013 .

[23]  S. Sabagh,et al.  SiAlON nanoparticles effect on the behaviour of epoxy coating , 2012, Iranian Polymer Journal.

[24]  A. Dworak,et al.  Cationic polymerization of glycidol. Polymer structure and polymerization mechanism , 1995 .

[25]  S. Nikafshar,et al.  Increasing toughness and tensile strength of an epoxy–diamine system using an inorganic ultra-accelerator , 2015 .

[26]  A. Rodrigues,et al.  An integrated process to produce vanillin and lignin-based polyurethanes from Kraft lignin , 2009 .

[27]  G. Kabalka,et al.  Sodium percarbonate: A convenient reagent for the dakin reaction , 1992 .

[28]  M. Naebe,et al.  Enhanced thermal stability and lifetime of epoxy nanocomposites using covalently functionalized clay: experimental and modelling , 2015 .

[29]  J. Džunuzović,et al.  Improvement of epoxy resin properties by incorporation of TiO2 nanoparticles surface modified with gallic acid esters , 2014 .

[30]  X. Colom,et al.  STUDY OF THE CURING PROCESS OF AN EPOXY RESIN BY FTIR SPECTROSCOPY , 2000 .

[31]  Xiaoqing Liu Preparation of a bio-based epoxy with comparable properties to those of petroleum-based counterparts , 2012 .

[32]  J. Molina-Aldareguia,et al.  A sustainable, eugenol-derived epoxy resin with high biobased content, modulus, hardness and low flammability: Synthesis, curing kinetics and structure–property relationship , 2016 .

[33]  Juan Baselga,et al.  Applications of FTIR on Epoxy Resins - Identification, Monitoring the Curing Process, Phase Separation and Water Uptake , 2012 .

[34]  Sabu Thomas,et al.  Cure kinetics, morphology and miscibility of modified DGEBA-based epoxy resin – Effects of a liquid rubber inclusion , 2007 .

[35]  Jérôme Lecomte,et al.  Chemo-enzymatic functionalization of gallic and vanillic acids: synthesis of bio-based epoxy resins prepolymers , 2012 .

[36]  Joshua M. Sadler,et al.  Vanillin-based resin for use in composite applications , 2012 .

[37]  Michael Jaffe,et al.  Overview of advances in sugar‐based polymers , 2011 .

[38]  O. Zabihi,et al.  Study on a novel thermoset nanocomposite form DGEBA–cycloaliphatic diamine and metal nanoparticles , 2012, Journal of Thermal Analysis and Calorimetry.

[39]  Carlos A. Grande,et al.  Vanillin production from lignin oxidation in a batch reactor , 2010 .

[40]  J. C. Villar,et al.  Oxidation of hardwood kraft-lignin to phenolic derivatives with oxygen as oxidant , 2001, Wood Science and Technology.

[41]  C. Xu,et al.  Synthesis of lignin-based epoxy resins: optimization of reaction parameters using response surface methodology , 2014 .

[42]  P. Ducrot,et al.  Renewable alternating aliphatic-aromatic poly(ester-urethane)s prepared from ferulic acid and bio-based diols , 2015 .

[43]  M. Naebe,et al.  One-pot synthesis of aminated multi-walled carbon nanotube using thiol-ene click chemistry for improvement of epoxy nanocomposites properties , 2015 .

[44]  Shinn-Gwo Hong,et al.  DSC and FTIR analysis of the curing behaviors of epoxy/DICY/solvent open systems , 1998 .

[45]  O. Zabihi Modeling of phenomenological mechanisms during thermal formation and degradation of an epoxy-based nanocomposite , 2012 .

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

[47]  A. Gupta,et al.  Development of Novel Bio-Based Soybean Oil Epoxy Resins as a Function of Hardener Stoichiometry , 2010 .