Synthesis of an aromatic N-heterocycle derived from biomass and its use as a polymer feedstock.
basic_science · Level V
Where this comes from
- Record sourced from PubMed, PMID 31068596.
- Also identified by DOI 10.1038/s41467-019-10178-0 and PMC identifier 6506500.
- Licence recorded as CC BY.
- The licence permits redistribution, so the abstract is shown in full and the full text is available from the publisher.
Abstract
Aromatic N-heterocyclic compounds are very important chemicals, which are currently produced mostly from petroleum. Here we report that a pyridazine-based compound 6-(4-hydroxy-3-methoxyphenyl)pyridazin-3(2H)-one (GSPZ) can be efficiently synthesized by the Friedel-Crafts reaction of guaiacol and succinic anhydride, both of which can be derived from biomass. GSPZ is then treated with bio-based epichlorohydrin to prepare the epoxy resin precursor GSPZ-EP. With 4,4'-diaminodiphenylmethane as curing agent, GSPZ-EP possesses higher glass transition temperature (187 <sup>o</sup>C vs. 173 <sup>o</sup>C) and shows a 140%, 70 and 93% increase in char yield (in N<sub>2</sub>), storage modulus (30 <sup>o</sup>C) and Young's modulus, respectively when compared with a standard petroleum-based bisphenol A epoxy resin. Moreover, the cured GSPZ-EP shows good intrinsic flame retardancy properties and is very close to the V-0 rating of UL-94 test. This work opens the door for production of aromatic N-heterocyclic compounds, which can be derived from biomass and employed to construct high performance polymers.