Sustainable and Degradable Epoxy Resins from Trehalose,
Cyclodextrin, and Soybean Oil Yield Tunable Mechanical Performance
and Cell Adhesion
Posted on 2018-10-19 - 20:44
Natural
product feedstocks such as carbohydrates and vegetable
oils offer tremendous potential for creating sustainable cross-linked
epoxy resin thermosets for numerous applications. Herein, we designed
and synthesized trehalose- and β-cyclodextrin-based carboxylic
acid hardeners to cure with epoxidized soybean oil forming predominantly
sustainable epoxy resins. Trehalose (Tr) and β-cyclodextrin
(Cd) were functionalized with heptanoyl chloride (H) and succinic anhydride (S). The resulting
carboxylic acid hardeners were homogeneously formulated and cross-linked
with epoxidized soy bean oil (ESO) at three different
COOH/epoxide ratios. The cured resins were thermally stable up to
300 °C and stable in neutral and acidic aqueous conditions. Yet,
degradation into water-soluble components could be triggered upon
exposure to basic aqueous media. The physical properties of these
materials are tunable based on feedstock composition and identity
of the carbohydrate hardener. The glass transition temperatures (Tg) of the Tr-based
epoxy polymers ranged from −3 to 3 °C, whereas the Cd-based polymers exhibited Tg values of 28–36 °C. The mechanical properties
including tensile strength and Young’s moduli also varied where
the Cd-thermosets offered higher performance due to the
structural rigidity of the cup-like structure. Homogeneous epoxy resin
films of these materials were examined for their ability to promote
cell adhesion and proliferation using neonatal human dermal fibroblast
(HDFn) cells. The results indicated that films composed of the Cd-based epoxy resin with a 50/50 ratio of −COOH/epoxide
promoted cell adhesion and proliferation with density similar to that
of the well-studied control polymer poly(dl-lactide-co-glycolide) (PLG). Interestingly, the Tr-based epoxy films completely prevented cell adhesion and
growth. The starkly different cell adhesion results and favorable
physical characteristics of these predominantly sustainable epoxy
resins support their promise as benign surfaces and scaffolds for
a variety of applications ranging from adhesives and antifouling coatings
to wound healing and tissue engineering.
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Zhang, Quanxuan; Phillips, Haley R.; Purchel, Anatolii; Hexum, Joseph K.; Reineke, Theresa M. (2018). Sustainable and Degradable Epoxy Resins from Trehalose,
Cyclodextrin, and Soybean Oil Yield Tunable Mechanical Performance
and Cell Adhesion. ACS Publications. Collection. https://doi.org/10.1021/acssuschemeng.8b03460
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AUTHORS (5)
QZ
Quanxuan Zhang
HP
Haley R. Phillips
AP
Anatolii Purchel
JH
Joseph K. Hexum
TR
Theresa M. Reineke
KEYWORDS
Degradable Epoxy ResinsSoybean Oil Yield Tunable Mechanical Performancecell adhesionresinvegetable oils offerCOOHepoxidized soybean oilepoxidized soy bean oilglass transition temperaturesPLGCell Adhesion Natural product feedstockspolymercell adhesion resultsTrfilmcarboxylic acid hardenersT g valuesESOβ- cyclodextrin-based carboxylic acid hardeners