Increasing demand for safe, convenient,
and affordable packaging
has prompted tremendous growth in single-use plastics, with attendant
increases in carbon dioxide emissions and environmental waste. This
study presents a family of engineering polyesters featuring biobased
naphthalate rigid segments. The proposed polyesters can serve as an
eco-friendly substitute for existing packaging materials, such as
poly(ethylene terephthalate) (PET). Bio-PET analogs using 2,7-naphthalate-based
rigid segments of dimethyl 1,2,3,4-tetrahydronaphthalene-2,7-dicarboxylate
(THN) or dimethyl 2,7-naphthalene dicarboxylate (2,7-N) were synthesized
via transesterification with ethylene glycol to the bis-hydroxy ester
followed by polycondensation. The proposed bionaphthalate polyesters
provide unique performance advantages. In experiments, the glass transition
temperature of poly(ethylene THN) was comparable to that of PET (T
g = 67.7 °C), and the glass transition
temperature of poly(ethylene 2,7-N) was far higher (T
g = 121.8 °C). The thermal stability of poly(ethylene
2,7-N) far exceeded that of PET, as evidenced by its char yield of
33.4 wt % at 1000 °C. Moreover, the poly(ethylene 2,7-N) also
produced 30% less acetaldehyde under typical processing temperatures
at 250–300 °C. Finally, the oxygen permeability values
of these naphthalate-based polymers were less than P
O2
= 0.0034 barrer, which represents a 3-fold
improvement over PET (0.0108 barrer). Overall, biobased naphthalate
rigid segment polyesters are promising candidates for sustainable
packaging materials, particularly those requiring high gas barrier
performance.