Novel biobased epoxy compounds: epoxidized sucrose esters of fatty acids

Abstract

Novel biobased high functionality epoxy resins were synthesized by the epoxidation of sucrose ester resins of vegetable oil fatty acids (SEFA). A series of sucrose esters of fatty acids were epoxidized by peracetic acid generated in situ from hydrogen peroxide and acetic acid in the presence of an ion exchange resin catalyst to produce the epoxidized sucrose esters of fatty acids (ESEFA). The conversion of double bonds to epoxides was greater than 99%. The products were characterized by matrix-assisted laser desorption and ionization time-of-flight (MALDI-TOF) mass spectrometry, Fourier-transform infrared (FTIR) spectroscopy, and nuclear magnetic resonance (NMR) spectroscopy. The physical properties were characterized using bulk viscosity, intrinsic viscosity, and density measurements. The thermal properties were characterized by differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). Since sucrose esters consist of a sucrose core fully substituted with eight vegetable oil fatty acids, both SEFAs and ESEFAs possess well-defined compact macromolecular structures. As novel biobased epoxy compounds, ESEFAs possess high epoxy functionality (8-15 per molecule), high density, and a compact molecular structure. Thus, ESEFAs are very promising in a number of uses from the formation of biobased thermosets by crosslinking of the epoxy groups, to further derivatization by reaction of the epoxy groups.

Impact of Structure and Functionality of Core Polyol in Highly Functional Biobased Epoxy Resins

“…[17] The use of sucrose esters has been further expanded beyond their use as alkyds by epoxidation. [18] Epoxidized sucrose esters (ESEs) have been used as resins for cationic UV-curable coatings. [19] The epoxy-anhydride curing of ESEs has been studied, and the performance of ESE-based thermosets has been shown to be exceptional in comparison with epoxidized soybean oil (ESO).…”

Vegetable oil-derived epoxy monomers and polymer blends: A comparative study with review

“…Esters of saturated FAs may only behave as plasticizers [38]. Novel epoxy compounds such as epoxidized sucrose esters of fatty acids have been synthesized and crosslinked to prepare polyester thermosets [30,39]. High modulus polymer was achieved due to the well-defined compact macromolecular structures and high oxirane functionality.…”

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2011–2012

“…linked O-GalNAc at Thr 11 residue TOF Synthesis, functional and structural characterization (Ahn et al, 2011a) Epoxidized fatty acid esters of sucrose TOF (CHCA) conditions (Pan et al, 2011b) Fluoro-sugar-terminated oligosaccharides TOF For investigating sequence specificity of carbohydrate polymerase (Brown et al, 2012a) Galacto-oligosaccharides R-TOF (DHB + NaI)…”