Synthesis and characterization of novel vinylester prepolymers from cardanol

Abstract

A novel thermosetting vinylester (VE) resin was prepared form cardanol, coming from cashew nut shell liquid (CNSL), a renewable resource and waste of the cashew industry. A VE cardanol-based prepolymer was synthesized by reacting commercial cardanol diepoxy and methacrylic acid. The VE cardanol-based prepolymer was polymerized by free radical polymerization to yield a thermoset resin with different monomers used as reactive diluents such as styrene (ST), isobornyl methacrylate (IBOMA), dibutyl itaconate (DBI), butanediol dimethacrylate (BDDMA), and hexanediol dimethacrylate (HDDMA). The resulting VE resin was characterized by TGA, DSC, and DMA analyses and compared to diglycidyl ether of bisphenol A (DGEBA)-based VE resin. Cardanol-based VE resins exhibit interesting mechanical and thermal properties for composite materials. The T g value is 86°C with 40% by mass of ST and 116°C with 40% by mass of IBOMA. Around 70°C of T g are lost compared to DGEBA-based VE resin, whereas with an oil-based VE resin the loss of T g value is around 150°C.Practical application: The acrylated cardanol-based monomer described in this contribution, that is, acrylated cardanol from CNSL, provided new biobased aromatic building blocks for further free radical polymerizations with various reactive diluents. The obtained VE materials are partially biobased and may be used as binders in composite applications. nut shell liquid; DBI, dibutyl itaconate; DGEBA, diglycidyl ether of bisphenol A; DMA, dynamic mechanical analyses; HDDMA, hexanediol dimethacrylate; IBOMA, isobornyl methacrylate; ST, styrene; TGA, thermogravimetric analysis; VE, vinylester 928Eur.

Bio-based reactive diluents as sustainable replacements for styrene in MAESO resin

“…The rst degradation (250-340 C) showed a weight loss of approximately 30%. This was caused by the loss of isobornyl fragment by ester scission, 39 which was in agreement with the fact that the MAESO-IM and MAESO-IA resin contained 35% of IM and IA. The second degradation (340-500 C) was attributed to the random scission of the MAESO-IM and MAESO-IA structure.…”

A chemical platform approach on cardanol oil: from the synthesis of building blocks to polymer synthesis

“…Moreover, we synthesized new building blocks from cardanol 1 in one or two step synthesis by various reactions (Jaillet et al, 2015), such as thiol-ene coupling, allylation, epoxidation, carbonation or acrylation (Scheme 1). These reactions lead to di-and polyepoxide monomers 2, 3 (Jaillet et al, 2013), mono-or di-(meth)acrylic monomers 4 (Jaillet et al, 2014(Jaillet et al, , 2016 and carbonate 5 by carbonation reaction (Besse et al, 2013), primary amines 6, 7 . All these building blocks were used for the synthesis of various polymers such as polyurethanes (PUs), non-isocyanate polyurethanes (NIPUs), vinyl esters and epoxy networks (Darroman et al, , 2016.…”

“…The cardanol-based VE prepolymer (CMAVE) and the DGEBA-based VE prepolymer (BMAVE) were prepared as described earlier (Jaillet et al, 2014). Then, they were diluted in styrene (ST) or isobornyl methacrylate (IBOMA) reactive diluents (ratio prepolymer/reactive diluent 60/40) and cured 12 h at 120…”

New aromatic amine based on cardanol giving new biobased epoxy networks with cardanol

“…The synthesis of the thiol-ene product is proceeded in two step: first the allylation of the phenol then the thiol-ene reaction with cysteamine hydrochloride. The formulation of epoxy-amine resins with epoxidized cardanol, previously characterized by our team [27,28], and the two amine based on cardanol were thermally and mechanically characterized. This work is the first to our knowledge to present a synthesis of TEC on cardanol and its use in a formulation in epoxy resin.…”