Using the glucose derivatives isosorbide
and glucarodilactone along
with a castor oil derivative, 10-undecenoyl chloride, two monomers
were synthesized: glucarodilactone undecenoate (GDLU) and isosorbide
undecenoate (IU). These monomers were polymerized via acyclic diene
metathesis (ADMET) polymerization to yield two homopolymers, P(GDLU)
and P(IU), and two copolymers, P1(GDLU-co-IU) and P2(GDLU-co-IU), of similar number-averaged molecular weight and relative
composition (51 and 61 kDa, Đ = 1.8 and 1.4,
46:54 and 52:48 mol percent). Comparison of the physical properties
and degradation behavior of these polymers revealed divergent characteristics
arising from differences in the nature of the carbohydrate building
blocks. P(IU) is more thermally stable and has a lower glass transition
temperature (T
d = 369 °C, T
g = −10 °C) than P(GDLU) (T
d = 206 °C, T
g = 32 °C) and P1,2(GDLU-co-IU) (T
d = 210 and 203 °C, T
g = 1 and 7 °C). While all of the polymers
were stable in acidic and neutral aqueous conditions, the two analogs
containing GDLU hydrolytically degraded in the presence of base. Tensile
testing of the systems revealed that both homopolymers are brittle
materials while the P(GDLU-co-IU) is more tough.
Notably, P1,2(GDLU-co-IU) was found to be a rubbery material with a low Young’s
modulus (0.020 and 0.002 GPa, respectively), displaying an average
elongation at break of 480 and 640%, and shape memory properties.
Carbohydrates and their derivatives have great potential as building blocks for the development of renewable materials that are cost and performance competitive with conventional petroleum-based materials.
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