Preparation and Characterization of Highly Bio‐Based Epoxy Amine Thermosets Derived from Lignocellulosics

Abstract

The development of chemicals from renewable sources as replacements for current toxic and unsustainable petrochemicals is an area of expanding study and interest. Phenolic epoxies derived from lignin, an underutilized resource generated as waste by the pulp and paper industry, and furanyl–amine epoxy curing agents derived from cellulosic biomass, are already proven independently to yield thermosetting resins possessing adequate thermal and thermomechanical properties. In this work, the union of the aforementioned technologies is examined to determine the properties and characteristics of such highly bio‐derived epoxy and amine thermosets. Resins with bio‐derived carbon content greater than 97% are synthesized and characterized via Fourier transform infrared (FTIR) spectroscopy, thermogravimetric analysis (TGA), and dynamic mechanical analysis (DMA). Lignin‐derived epoxy resins are found to be compatible with a cellulose‐derived furanyl diamine curing agent to produce thermosetting resins with good thermomechanical and thermogravimetric properties, rivaling the levels of properties exhibited by similar commercial petroleum‐derived systems, indicating viability for replacing petroleum‐based polymers in high‐temperature applications.

Biobased epoxy resin derived from eugenol with excellent integrated performance and high renewable carbon content

“…Generally, the former is calculated according to the typical rubber state theory (Eqn ), and the latter is measured with the PALS technique and then calculated based on the well‐established Tau–Eldrup model (Eqns ) where E′ is the storage modulus of the thermosetting resin in the rubbery plateau region, R is the universal constant and T is the temperature at which the storage modulus reaches a minimum where τ 3 and I 3 are the positronium lifetime and intensity in the void, respectively; r is the radius of a pore cavity, r 0 = r + Δr, Δr is empirically determined to be 0.166 nm; f app is the free volume fraction.…”

Bright Side of Lignin Depolymerization: Toward New Platform Chemicals

“…The methoxy groups improved the modulus of cured resins; however, a lower T g (100–124 vs 131–149 °C) was found ( Table 4 , entry 5). Subsequently, the diglycidyl ethers of gastrodigenin, vanillyl alcohol, bisguaiacol, and hydroquinone were employed by Mauck et al 395 to be reacted with the cellulose-derived 5,5-methylenedifurfurylamine as curing agent and obtain epoxy amine thermosets ( Table 4 , entry 6). These new highly bioderived thermosetting epoxy and amine resins were characterized by good thermogravimetric and thermomechanical properties comparable with a commercial BPA-epoxy resin demonstrating the possibility of its replacement.…”

Preparation of Renewable Epoxy-Amine Resins With Tunable Thermo-Mechanical Properties, Wettability and Degradation Abilities From Lignocellulose- and Plant Oils-Derived Components

“…Indeed, the aromatic moieties present in these bio-based chemicals confer rigidity to the resulting polymers (Wang et al, 2017; Feghali et al, 2018). For example, there have been many reports on epoxy resins from eugenol (Wan et al, 2016), vanillin (Fache et al, 2015a,b; Hernandez et al, 2016; Mauck et al, 2017; Nicastro et al, 2018; Savonnet et al, 2018; Zhao et al, 2018), ferulic and sinapic acids (Maiorana et al, 2016; Janvier et al, 2017; Ménard et al, 2017), guaiacols (Maiorana et al, 2015), and creosol (Meylemans et al, 2011) with promising performances capable of competing with current DGEBA-based materials. However, few researchers have considered the potential toxicity of these BPA substitutes, especially endocrine disruption, which remains a crucial health issue for both plastic sector workers and consumers (Jiang et al, 2018).…”