In this study, bifurfural, an inedible
biobased chemical and a
second-generation biomass, was polymerized with several diamines using
an environmentally benign process, and the chemical structures of
the resulting poly(Schiff base)s were analyzed. Because furan rings,
which are only produced from biomass and not from fossil resources,
endow polymers with unique properties that include high rigidity and
expanded π-conjugation, bifurfural, which contains two furan
rings, is of significant interest as a biobased building block.
1
H NMR, IR, and matrix assisted laser desorption ionization-time
of flight mass spectra of the poly(Schiff base)s reveal that they
are composed of mixtures of linear and cyclic structures. The UV–vis
spectroscopy and molecular orbital theory confirm the extended π-conjugation
in the bifurfural/
p
-phenylenediamine poly(Schiff
base) system. Poly(Schiff base)s composed of bifurfural and 1,3-propanediamine,
1,4-butandiamine, 1,5-pentanediamine, and 1,6-hexanediamine were molded
at 120 °C into films that exhibited good strengths and were tough
to bend. These results indicate that bifurfural-based poly(Schiff
base)s are promising biobased materials.