Fully biobased epoxy resin systems composed of a vanillin-derived epoxy resin and renewable phenolic hardeners

Abstract A new bio-based epoxy resin (DGEDVCP) was synthesized by the glycidylation of 2,5-bis(4-hydroxy-3-methoxybenzylidene)cyclopentanone (DVCP) prepared by the crossed-aldol condensation of vanillin and cyclopentanone. The thermal and mechanical properties of DGEDVCP resins cured with renewable quercetin (QC) and guaiacol novolac (GCN) in addition to a petroleum-based phenol novolac (PN) were compared with those of bisphenol A diglycidyl ether (DGEBA) resins cured with QC, GCN and PN. Regarding the hardeners used for curing, the higher order of loss modulus (E″) peak temperature of cured products was QC > PN > GCN. The E″ peak temperatures of DGEDVCP/GCN and DGEDVCP/PN cured products were higher than and comparable to those of DGEBA/GCN and DGEBA/PN cured products, respectively. Thermal degradation temperatures of DGEDVCP-based products were slightly lower than those of DGEBA-based products. Char yields at 500 °C for DGEDVCP-based products were much higher than those of DGEBA-based products. The flexural strengths and moduli of the DGEDVCP/QC and DGEDVCP/GCN cured products were comparable to those of DGEBA/QC and DGEBA/GCN cured products, respectively.

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

[2]  Józef Haponiuk,et al.  Potential applications of crude glycerol in polymer technology–Current state and perspectives , 2016 .

[3]  T. Liptaj,et al.  Effect of catalyst and solvent on the furan ring rearrangement to cyclopentanone , 2012 .

[4]  M. Hronec,et al.  Selective transformation of furfural to cyclopentanone , 2012 .

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

[6]  M. Shibata,et al.  Thermal and mechanical properties of sorbitol-based epoxy resin cured with quercetin and the biocomposites with wood flour , 2013 .

[7]  Jin Zhu,et al.  Vanillin-Derived High-Performance Flame Retardant Epoxy Resins: Facile Synthesis and Properties , 2017 .

[8]  M. Wolcott,et al.  Use of eugenol and rosin as feedstocks for biobased epoxy resins and study of curing and performance properties , 2014 .

[9]  Patricia Krawczak,et al.  Thermosetting (bio)materials derived from renewable resources: A critical review , 2010 .

[10]  S. Caillol,et al.  Biobased epoxy thermosets from vanillin-derived oligomers , 2015 .

[11]  J. Galy,et al.  Preparation and properties of bio-based epoxy networks derived from isosorbide diglycidyl ether , 2011 .

[12]  S. Caillol,et al.  Epoxy thermosets from model mixtures of the lignin-to-vanillin process , 2016 .

[13]  G. Knothe,et al.  Synthesis of Epoxidized Cardanol and Its Antioxidative Properties for Vegetable Oils and Biodiesel , 2016 .

[14]  M. Ochi,et al.  Mechanical and dielectric relaxations of epoxide resins containing spiro‐ring structure , 1986 .

[15]  Yanliang Yang,et al.  Conversion of furfural into cyclopentanone over Ni–Cu bimetallic catalysts , 2013 .

[16]  C. Xu,et al.  Curing kinetics and mechanical properties of bio-based epoxy composites comprising lignin-based epoxy resins , 2016 .

[17]  M. Serio,et al.  New Process for Producing Epichlorohydrin via Glycerol Chlorination , 2010 .

[18]  H. Hailes,et al.  Strategies for synthesis of epoxy resins from oleic acid derived from food wastes , 2016 .

[19]  F. Tournilhac,et al.  Control of reactions and network structures of epoxy thermosets , 2016 .

[20]  H. Timmerman,et al.  1,5-Diphenyl-1,4-pentadiene-3-ones and cyclic analogues as antioxidative agents. Synthesis and structure-activity relationship , 1997 .

[21]  Bernard Boutevin,et al.  Biobased thermosetting epoxy: present and future. , 2014, Chemical reviews.

[22]  M. Shibata,et al.  Wood‐derived phenol novolaks and their wood/epoxy biocomposites , 2015 .

[23]  M. Shibata,et al.  Preparation and properties of biocomposites composed of glycerol‐based epoxy resins, tannic acid, and wood flour , 2010 .

[24]  T. Pandita,et al.  Endocrine disrupting chemical, bisphenol-A, induces breast cancer associated gene HOXB9 expression in vitro and in vivo. , 2016, Gene.

[25]  G. Palmese,et al.  Recent advances in bio‐based epoxy resins and bio‐based epoxy curing agents , 2016 .

[26]  S. Caillol,et al.  Vanillin, a key-intermediate of biobased polymers , 2015 .

[27]  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 .

[28]  Joshua M. Sadler,et al.  Synthesis and Characterization of Bio-based Epoxy Resins Derived from Vanillyl Alcohol , 2016 .

[29]  P. Villeneuve,et al.  Synthesis of bio-based epoxy monomers from natural allyl- and vinyl phenols and the estimation of their affinity to the estrogen receptor α by molecular docking , 2016 .

[30]  Joo Ran Kim,et al.  The development and comparison of bio-thermoset plastics from epoxidized plant oils , 2012 .

[31]  Minoo Naebe,et al.  A renewable bio-based epoxy resin with improved mechanical performance that can compete with DGEBA , 2017 .

[32]  T. Koike Progress in development of epoxy resin systems based on wood biomass in Japan , 2012 .

[33]  Tao Zhang,et al.  Synthesis of renewable high-density fuels using cyclopentanone derived from lignocellulose. , 2014, Chemical communications.