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Synthesis of biobased reactive hydroxyl amines by amination reaction of cardanol-based epoxy monomers

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Abstract Most of the current amines are issued from petrochemical resources and only a few of them are derived from biomass. Hence, there are increasing expectations for bio-based amines, particularly… Click to show full abstract

Abstract Most of the current amines are issued from petrochemical resources and only a few of them are derived from biomass. Hence, there are increasing expectations for bio-based amines, particularly for aromatic ones. We have designed and synthesized new bio-based amines containing aromatic moieties from cardanol, an aromatic non-edible co-product from agri-food industry of cashew nut. We used green amination reaction of epoxy monomers with ammonia under microwave irradiations, from two commercial epoxidized cardanol monomers with different epoxy functions: NC-514 and GX-2551 (Cashew, nutshell liq., polymer with epichlorohydrin). We studied the efficiency of our amination route onto both glycidyl and epoxy functions at the middle of the chain and the reactivity of synthesized amines toward ring opening of epoxy function. The synthesized bio-based amines were further evaluated as curing agents for epoxy resins. The thermo-mechanical properties of final bio-based thermosets synthesized therefrom are almost similar (Tg = 51 °C, Td5% = 332 °C and Tα = 64 °C for T-NC thermoset, Tg = 58 °C, Td5% = 340 °C and Tα = 78 °C for T-GX thermoset). Moreover, another aim of this study was to reduce the viscosity of hardeners compared to DHAVA hardener (400 000 mPa s at 50 °C), which was synthesized in previous work. Lower viscosities were observed in the case of cardanol-based hardener (362 000 and 33 000 mPa s at 50 °C for respectively NC-A and GX-A hardener).

Keywords: amination reaction; amination; bio based; cardanol based; epoxy monomers

Journal Title: European Polymer Journal
Year Published: 2019

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