TY - JOUR
T1 - Itaconic Acid as a Comonomer in Betulin-Based Thermosets via Sequential and Bulk Preparation
AU - Lehman-Chong, Alexandra M.
AU - Cox, Casey L.
AU - Kinaci, Emre
AU - Burkert, Sarah E.
AU - Dodge, Megan L.
AU - Rosmarin, Devin M.
AU - Newell, James A.
AU - Soh, Lindsay
AU - Gordon, Melissa B.
AU - Stanzione, Joseph F.
N1 - Publisher Copyright:
© 2023 The Authors. Published by American Chemical Society.
PY - 2023/9/25
Y1 - 2023/9/25
N2 - The inherent chemical functionalities of biobased monomers enable the production of renewably sourced polymers that further advance sustainable manufacturing. Itaconic acid (IA) is a nontoxic, commercially produced biobased monomer that can undergo both UV and thermal curing. Betulin is a biocompatible, structurally complex diol derived from birch tree bark that has been recently studied for materials with diverse applications. Here, betulin, IA, and biobased linear diacids, 1,12-dodecanedioic acid (C12) and 1,18-octadecanedioic acid (C18), were used to prepare thermosets using sequential and bulk curing methods. Thermoplastic polyester precursors were synthesized and formulated into polyester-methacrylate (PM) resins to produce sequential UV-curable thermosets. Bulk-cured polyester thermosets were prepared using a one-pot, solventless melt polycondensation using glycerol as a cross-linker. The structure-property relationships of the thermoplastic polyester precursors, sequentially prepared PM thermosets, and bulk-cured polyester thermosets were evaluated with varying IA content. Both types of thermosets exhibited higher storage moduli, Tgs, and thermal stabilities with greater IA comonomer content. These results demonstrate the viability of using IA as a comonomer to produce betulin-based thermosets each with tunable properties, expanding the scope of their applications and use in polymeric materials.
AB - The inherent chemical functionalities of biobased monomers enable the production of renewably sourced polymers that further advance sustainable manufacturing. Itaconic acid (IA) is a nontoxic, commercially produced biobased monomer that can undergo both UV and thermal curing. Betulin is a biocompatible, structurally complex diol derived from birch tree bark that has been recently studied for materials with diverse applications. Here, betulin, IA, and biobased linear diacids, 1,12-dodecanedioic acid (C12) and 1,18-octadecanedioic acid (C18), were used to prepare thermosets using sequential and bulk curing methods. Thermoplastic polyester precursors were synthesized and formulated into polyester-methacrylate (PM) resins to produce sequential UV-curable thermosets. Bulk-cured polyester thermosets were prepared using a one-pot, solventless melt polycondensation using glycerol as a cross-linker. The structure-property relationships of the thermoplastic polyester precursors, sequentially prepared PM thermosets, and bulk-cured polyester thermosets were evaluated with varying IA content. Both types of thermosets exhibited higher storage moduli, Tgs, and thermal stabilities with greater IA comonomer content. These results demonstrate the viability of using IA as a comonomer to produce betulin-based thermosets each with tunable properties, expanding the scope of their applications and use in polymeric materials.
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U2 - 10.1021/acssuschemeng.3c04178
DO - 10.1021/acssuschemeng.3c04178
M3 - Article
AN - SCOPUS:85173010620
SN - 2168-0485
VL - 11
SP - 14216
EP - 14225
JO - ACS Sustainable Chemistry and Engineering
JF - ACS Sustainable Chemistry and Engineering
IS - 38
ER -