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Article

Crosslinking of Electrospun Fibres from Unsaturated Polyesters by Bis-Triazolinediones (TAD)

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Department of Chemical Engineering and Food Engineering, Federal University of Santa Catarina (UFSC), Florianópolis, SC 88040-900, Brazil
2
Department of Chemistry, Royal College of Surgeons in Ireland, 123 St. Stephens Green, Dublin 2, Ireland
*
Author to whom correspondence should be addressed.
Current Addresses: Viviane Chiaradia: Department of Chemistry, University of Birmingham, Birmingham, United Kingdom B15 2TT. Saltuk B. Hanay: Faculty of Engineering and Natural Sciences, Sabanci University, Tuzla, 34956, Istanbul, Turkey. Scott D. Kimmins: Instituto de Química, Pontificia Universidad Católica de Valparaíso, Avda. Universidad 330, Curauma, Placilla, Valparaíso Casilla, 4059, Valparaíso, Chile.
Polymers 2019, 11(11), 1808; https://doi.org/10.3390/polym11111808
Received: 3 October 2019 / Revised: 25 October 2019 / Accepted: 29 October 2019 / Published: 4 November 2019
Crosslinking of an unsaturated aliphatic polyester poly(globalide) (PGl) by bistriazolinediones (bisTADs) is reported. First, a monofunctional model compound, phenyl–TAD (PTAD), was tested for PGl functionalisation. 1H-NMR showed that PTAD–ene reaction was highly efficient with conversions up to 97%. Subsequently, hexamethylene bisTAD (HM–bisTAD) and methylene diphenyl bisTAD (MDP–bisTAD) were used to crosslink electrospun PGl fibres via one- and two-step approaches. In the one-step approach, PGl fibres were collected in a bisTAD solution for in situ crosslinking, which resulted in incomplete crosslinking. In the two-step approach, a light crosslinking of fibres was first achieved in a PGl non-solvent. Subsequent incubation in a fibre swelling bisTAD solution resulted in fully amorphous crosslinked fibres. SEM analysis revealed that the fibres’ morphology was uncompromised by the crosslinking. A significant increase of tensile strength from 0.3 ± 0.08 MPa to 2.7 ± 0.8 MPa and 3.9 ± 0.5 MPa was observed when PGI fibres were crosslinked by HM–bisTAD and MDP–bisTAD, respectively. The reported methodology allows the design of electrospun fibres from biocompatible polyesters and the modulation of their mechanical and thermal properties. It also opens future opportunities for drug delivery applications by selected drug loading. View Full-Text
Keywords: aliphatic polyesters; electrospinning; triazolinediones; fibres aliphatic polyesters; electrospinning; triazolinediones; fibres
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MDPI and ACS Style

Chiaradia, V.; Hanay, S.B.; Kimmins, S.D.; Oliveira, D.d.; Araújo, P.H.H.; Sayer, C.; Heise, A. Crosslinking of Electrospun Fibres from Unsaturated Polyesters by Bis-Triazolinediones (TAD). Polymers 2019, 11, 1808. https://doi.org/10.3390/polym11111808

AMA Style

Chiaradia V, Hanay SB, Kimmins SD, Oliveira Dd, Araújo PHH, Sayer C, Heise A. Crosslinking of Electrospun Fibres from Unsaturated Polyesters by Bis-Triazolinediones (TAD). Polymers. 2019; 11(11):1808. https://doi.org/10.3390/polym11111808

Chicago/Turabian Style

Chiaradia, Viviane, Saltuk B. Hanay, Scott D. Kimmins, Débora d. Oliveira, Pedro H.H. Araújo, Claudia Sayer, and Andreas Heise. 2019. "Crosslinking of Electrospun Fibres from Unsaturated Polyesters by Bis-Triazolinediones (TAD)" Polymers 11, no. 11: 1808. https://doi.org/10.3390/polym11111808

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