Bio‐resourced eugenol derived phthalonitrile resin for high temperature composite

Abstract

Eugenol (EG) is an abundant renewable compound that has been widely used in the synthesis of bio‐based thermosetting resin, but there are few reports on the phthalonitrile (PN) resin derived from EG. In this study, a new kind of bio‐based PN resin (MEG‐PN) derived from EG derivative was successfully synthesized. PN is a traditional class of high‐performance thermosets with poor processability for its ultra‐high melting point and curing temperature. The MEG‐PN resin possesses excellent processability: its melting temperature is much lower (77°C), and it can be cured at a moderate temperature (281°C) in the absence of curing agents. The cured MEG‐PN resin exhibited great heat resistance according to its 5% weight loss temperature at 448°C and its char yield percentage as high as 75.6% at 800°C under nitrogen. The properties of the carbon‐fiber reinforced MEG‐PN composite were comparable to those of petroleum‐based PN resins: the glass transition temperature was around 397°C; the flexural strength and modulus were as high as 756 MPa and 119 GPa, respectively. Overall, a bio‐based PN thermoset with great comprehensive performance was synthesized possessing the potential in the application of advanced composite.

Self-Curing Phthalonitrile Resin with Disulfide Bond as the Curing Group

“…The progressively enhanced absorption at 1508 cm −1 was attributed to the increased triazine content. 47,48 The increased contents of isoindoline 49 and phthalocyanine 15−22 resulted in the gradually increasing absorption at 1093 and 1011 cm −1 , respectively, as shown in Figure 2c,d. In fact, the UV−vis spectra of precured DPBPN (200 °C for 5 min) showed characteristic absorptions of phthalocyanine at 669 and 701 nm (Figure S5), 27 which further demonstrated the formation of phthalocyanine during the curing process.…”

Characteristics and Application of Eugenol in the Production of Epoxy and Thermosetting Resin Composites: A Review

“…Ning et al used eugenol (EG) and hydroxymethylated eugenol (MEG) as a bio-component for the synthesis of phthalonitrile resin (PN) [ 83 ]. Bio-based resin (MEG-PN) has been used in the production of fourteen-layer carbon fabric reinforced laminates.…”

Vanillin- and Isovanillin-Based Phthalonitrile Resins Containing Spirocycle Acetal Structures

“…The reports have proven that the performance of biobased thermosets is comparable to that of its petroleum-based counterparts and shows promising potential in applications. − Due to the lack of biobased phenolic compounds, the preparation of biobased PN resins is not easy and is receiving increasing attention. , Zhang et al prepared phthalocyanine resin from anethole derived from vegetable oil, which has a high T g ( T g > 450 °C), a low thermal expansion coefficient, and a high char yield . The preparation of thermosetting epoxy and phthalocyanine resins with excellent performance uses eugenol as a raw material. ,− Peng et al obtained a type of l -tyrosine-based phthalonitrile with a biomass content of 61%, and the PN resin not only shows higher T g and outstanding thermal stability but also has an autocatalytic performance . Liu et al synthesized a lignin-based phthalonitrile monomer (BPN) with a biomass content of 54%; compared with petroleum-based bisphenol A-based phthalonitrile, the cured BPN has better thermal stability and a comparable T g (400 °C) …”