Photopolymerizable Synthons from Glycerol Derivatives

Abstract

Photopolymerizable monomers based on monoglycerides were prepared by a convenient two‐step procedure. The first one consists of the synthesis of highly pure monoglycerides by an organocatalyzed solvent‐free route. This process was carried out by condensation of bio‐sourced carboxylic acids (i.e. butyric, decanoic, undecylenic or stearic acids) with glycerol carbonate or glycidol in the presence of a quaternary ammonium salt as a catalyst. The obtained bio‐based monoglycerides were modified in the second step by reaction with acryloyl and methacryloyl chloride leading to a series of new diacrylated and dimethacrylated monomers. The structures of the monoglycerides, diacrylated and dimethacrylated monomers were fully characterized by spectroscopic methods. Photopolymerization investigations monitored by infrared spectroscopy were achieved under ultraviolet radiation in the presence of a photoinitiator. The resulting cross‐linked materials were analyzed by thermal gravimetric analysis, gel content determination and tests of swelling in water, ethanol and methylene chloride. Data relative to the pendulum hardness of these materials are also included.

Efficient microwave‐assisted synthesis of glycerol monodecanoate

“…By contrast with the synthesis pathway based on glycidol, the thermal condensation of glycerol carbonate with fatty acids is not well described in the literature. Previously run classical heating experiments showed that the reaction between glycidol and decanoic acid leads to better yield in shorter time than the reaction starting from glycerol carbonate and decanoic acid .…”

“…In our previous study, conventional heating was performed . The best conditions were as follow: 24 h, 0.5 mol% of TBAI as catalyst and a molar ratio of carboxylic acid/glycerol carbonate of 1/2.…”

“…Its beneficial effect was in particularly reported on the emulsion stability and the storage stability of the mayonnaise . Most recently, in the field of polymer, we showed that α ‐monoglyceride can also serve as a molecule platform for materials applications, describing its modification into photopolymers . For these reasons, we found interesting to improve and optimize the synthesis procedure of 2,3‐dihydroxypropyl decanoate.…”

“…This transfer also strongly exists in the field of polymeric materials where the incorporation of biobased synthons arouses a growing interest worldwide and exhibits convincing and competitive results . In this context and in the course of our ongoing studies on sustainable polymers, we reported the synthesis of photopolymerizable synthons derived from α ‐monoglycerides and leading after UV‐irradiation to bio‐based cross‐linked materials . α ‐Monoglycerides or 1‐monoacylglycerol were obtained by condensation of fatty acids with either glycerol carbonate or glycidol, in a solvent‐free medium, and in the presence of tetrabutylammonium iodide (TBAI) as organocatalyst.…”

Crystal structure of the diglycidyl ether of eugenol

“…Classically, the synthetic approach is based on the functionalization of bio-sourced molecules by the grafting of glycidyl ether groups. In this context and in our ongoing studies on the chemical modification of bio-based building blocks for material applications (Mhanna et al, 2014;Bigot et al, 2016;François et al, 2016), we report herein on the synthesis and crystal structure of the diglycidyl ether of eugenol (DGE-Eu), prepared from eugenol in a three-step synthesis (Qin et al, 2014).…”