Sustainable High‐Temperature Phthalonitrile Resins Derived from Resveratrol and Dihydroresveratrol

Abstract

The renewable triphenols, resveratrol and dihydroresveratrol, were used in the preparation of two new phthalonitrile resins (PN), each containing three phthalonitrile groups. These are the first reported PN resins generated from a renewable feedstock. These amorphous PN resins were characterized thoroughly by DSC, NMR spectroscopy and rheometry. The monomers exhibited excellent rheometric viscosities suitable for resin transfer molding and resin infusion molding. After complete cure, the PN polymers exhibited thermal stability to above 500 8C and no glass transition temperature (T g ). As a result of the highly cross-linked nature of the network, these materials exhibited a low water uptake of 1 AE 0.2 % and dielectric constant values of approximately 3.0. These results suggest that resveratrol-derived PN resins are excellent candidates for use in maritime environments and aerospace applications.[a] Dr.

Oligomeric phthalonitriles and tetrakis(phenylethynyl)benzene blends with improved processing and thermal properties

“…According to the DSC thermograms of resins after postcuring, which exhibit no transitions, all samples are fully cross‐linked using this procedure. In addition, no glass transitions are observed after posturing, which is consistent with previous studies of PN resins …”

Sustainable, fire‐resistant phthalonitrile‐based glass fiber composites

“…Phthalonitrile (PN) monomer 1 was synthesized from a previously published procedure and dry mixed with 2.7 wt % bis[4‐(3‐aminophenoxy)phenyl]sulfone ( m ‐BAPS) to form the PN formulation used in preparation of the composite panels. The PN‐glass fabric prepreg was prepared by a solution impregnation process using monomer 1 suspended in acetone and painted onto the fibers.…”

“…The natural product resveratrol ( trans ‐3,5,4′‐trihydroxystilbene), in contrast, is a renewable feedstock and a less toxic alternative to the use of bisphenols in traditional PN systems. We recently highlighted the synthesis and properties of a resveratrol‐based PN resin 1 and the cured polymers . Resveratrol has many potential human health benefits and is found in foods such as grapes or peanuts and is commercially isolated from Japanese Knotwood.…”

Synthesis of cardanol‐based phthalonitrile monomer and its copolymerization with phenol–aniline‐based benzoxazine

“…Regardless of PN properties, they are also prepared as traditional high performance polymers from petroleum‐based materials. The bio‐based PN is successfully synthesized from the resveratrol, dihydroresveratrol, eugenol, and guaiacol via nucleophilic displacement reaction between 4‐nitrophthalonitrile and the bio‐based phenolic compounds . The bio‐based PN monomers showed low melt viscosity and wider processing windows suitable for the composites fabrication.…”