Plant oil-based epoxy resins from fatty diamines and epoxidized vegetable oil

Abstract

Herein, the synthesis of vegetable oil-derived diamines by thiol-ene coupling (TEC) using cysteamine hydrochloride is reported. Despite the amine group in cysteamine that is unfavorable to TEC, fatty allylamide (FAl-A) provides an aminated fatty amide (AFA). Due to other diamides, the influence of the fatty structure on the TEC reactivity was demonstrated. The structures were characterized using FTIR and 1 H NMR spectroscopies, and the crosslinking of epoxidized linseed oil (ELO) with AFA was investigated using differential scanning calorimetry (DSC) and dynamic rheometry. The thermomechanical behavior of the plant oil-based thermoset was also characterized and compared toa commercial diamine based ona fatty dimer structure and a branched polyamine prepared from grapeseed oil. Finally, the beneficial effect of oxidation of the epoxy resin on thethermomechanical propertiesis highlighted.

Novel bio-based epoxy-polyurethane materials from modified vegetable oils – synthesis and characterization

“…According to the results of GPC analysis the epoxy fusion product does not contain unreacted epoxidized soybean oil, however there are vestiges of unreacted bisphenol A. Such unreacted residues of unconverted bisphenol A are always observed in case of the synthesis of epoxy resins [14]. It does not contribute any problems, since bisphenol A contains hydroxyl groups and in curing process it reacts with the isocyanate (determination of -OH groups content in the reacting mixture).…”

“…Moreover, application of renewable resources in their synthesis and modification is also of great interest, due to the growing ecological issues as well as economical and societal advantages [8,9]. Vegetable oils, which are biodegradable, renewable, non-toxic, environmentally benign and easily modified [10,11] have already found applications in the technology of epoxies as: additives, flexibilizers [12], and diluents [13], decreasing viscosity of epoxy resins or bio-alternatives for raw petrochemical materials in the process of their synthesis [14,15]. In a respect of functionality of vegetable oils, defined as content of unsaturated bonds and in the same time content of functional groups, which might be introduced in to the molecule, epoxidized derivatives of natural oils can be formally classified as epoxy resins.…”

Preparation and Spectroscopic Characterization of Si‐Coated Vegetable Oils and their Application in In Situ Curing of Hybrid Coatings

“…The modification of renewable materials by phosphorus moieties has been reviewed by David et al, and the applications concern fire retardancy and the corrosion protection of steel. [7,17,18] In addition, sulfur elements through thiol-ene coupling (TEC) remain a versatile tool to modify vegetable oils into polyesters and polyurethanes. [15,16] Amine functional groups have been targeted with the goal of reaching hardeners for bio-based epoxy resins.…”

“…[12][13][14] The insertion of nitrogen elements has also been investigated. [4,17,[19][20][21] The insertion of elements such as silicon and titanium is a very interesting way to modify vegetable oils, since it opens the way to cross-link oils through the sol-gel process. [7,17,18] In addition, sulfur elements through thiol-ene coupling (TEC) remain a versatile tool to modify vegetable oils into polyesters and polyurethanes.…”

Techno‐economic optimization model for “sustainable” insulation material developed for energy efficiency

“…Various ways of modifying unsaturated sites on the fatty acids are utilized to obtain polymers. Polymers with triglyceride are used as strengthening agents in PVC and epoxy resins as well as a main component in various natural resins, composites, and pressure‐sensitive adhesives . The vegetable‐based resins are good alternatives to fossil source‐based resins due to their cost advantage, being derived from renewable resources and other superior properties .…”