Polylactide thermosets using a bis(cyclic diester) crosslinker

[Display omitted] •A novel bis(cyclic diester) crosslinker with flexible linker was synthesized.•Two model monofunctional comonomers and their relative reactivities were studied.•Multi-arm prepolymers gave access to polylactide-based thermosets.•The thermosets had a reduced Young’s modulus and tensi...

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Bibliographic Details
Published in:European polymer journal 2019-11, Vol.120, p.109192, Article 109192
Main Authors: Kuroishi, Paula K., Delle Chiaie, Kayla R., Dove, Andrew P.
Format: Article
Language:English
Subjects:
Aliphatic compounds
Biodegradability
Biomedical materials
Crosslinked polylactide
Crosslinking
Mechanical properties
Modulus of elasticity
Molecular chains
Molecular weight
Polylactic acid
Polymerization
Ring opening polymerization
Ring-opening polymerisation
Studies
Tensile strength
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Summary:[Display omitted] •A novel bis(cyclic diester) crosslinker with flexible linker was synthesized.•Two model monofunctional comonomers and their relative reactivities were studied.•Multi-arm prepolymers gave access to polylactide-based thermosets.•The thermosets had a reduced Young’s modulus and tensile strength compared to poly(l-lactide).•The thermosets presented high elongation at break (up to 268% elongation). Features such as the renewability and biodegradability of polylactide (PLA) have resulted in numerous applications in biomedical and commodity polymers. However, the brittle nature of PLA hinders its wider implementation; consequently, investigations have focused on improving its mechanical properties. This work describes the preparation of PLA thermosets that are crosslinked with a novel bis(cyclic diester) containing an aliphatic chain, as a strategy to modify the mechanical properties. Kinetic studies with monofunctional model monomers showed reactivities comparable to lactide (LA) in the presence of 1,1,3,3-tetramethylguanidine as the catalyst, which additionally provided good control over the ring-opening polymerisation. Despite the low Young’s modulus and tensile strength, the crosslinked materials prepared with the bis(cyclic diester) demonstrated high ductility when compared to high molecular weight PLLA, a property that was attributed to the presence of a flexible chain in the crosslinker.
ISSN:0014-3057
1873-1945
DOI:10.1016/j.eurpolymj.2019.08.019