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Article

Biodegradable and Biocompatible Thermoplastic Poly(Ester-Urethane)s Based on Poly(ε-Caprolactone) and Novel 1,3-Propanediol Bis(4-Isocyanatobenzoate) Diisocyanate: Synthesis and Characterization

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Institute of Polymer Science and Technology (CSIC), Juan de la Cierva, 3, 28006 Madrid, Spain
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Universidad Nacional de Educación a Distancia (UNED), Facultad de Ciencias, C/Bravo Murillo, 38, 28015 Madrid, Spain
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Instituto Politécnico Nacional, Escuela Superior de Ingeniería Química e Industrias Extractivas, UPALM-Zacatenco, Col Lindavista, Mexico City 07738, Mexico
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Universidad de Guanajuato, Departamento de Química, Noria Alta s/n, Guanajuato 36050, Mexico
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Biomedical Research Networking Center in the Subject Area of Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Avenida Monforte de Lemons 3–5, 28029 Madrid, Spain
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Authors to whom correspondence should be addressed.
Academic Editor: Andreea-Teodora Iacob
Polymers 2022, 14(7), 1288; https://doi.org/10.3390/polym14071288
Received: 25 February 2022 / Revised: 17 March 2022 / Accepted: 18 March 2022 / Published: 23 March 2022
(This article belongs to the Special Issue Biomedical Applications of Polymeric Materials)
A series of non-toxic biodegradable and biocompatible polyurethanes bearing p-aminobenzoate moieties are presented. The introduction of this attractive motif was carried out by the synthesis of a novel isocyanate. These biodegradable polymers were chemically and physically characterized by several techniques and methods including bioassay and water uptake measurements. The molecular weight of the soft segment (poly-ε-caprolactone, PCL) and hard segment crystallinity dictated the mechanical behavior and water uptake. The behavior of short PCL-based polyurethanes was elastomeric, whilst increasing the molecular weight of the soft segment led to plastic polyurethanes. Water uptake was hindered for long PCL due to the crystallization of the soft segment within the polyurethane matrix. Furthermore, two different types of chain extender, hydrolyzable and non-hydrolyzable, were also evaluated: polyurethanes based on hydrolyzable chain extenders reached higher molecular weights, thus leading to a better performance than their unhydrolyzable counterparts. The good cell adhesion and cytotoxicity results demonstrated the cell viability of human osteoblasts on the surfaces of these non-toxic biodegradable polyurethanes. View Full-Text
Keywords: biodegradability; biocompatibility; thermoplastic polyurethane; non-toxic polyurethane; hydrolyzable chain extender biodegradability; biocompatibility; thermoplastic polyurethane; non-toxic polyurethane; hydrolyzable chain extender
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MDPI and ACS Style

Rubio Hernández-Sampelayo, A.; Navarro, R.; González-García, D.M.; García-Fernández, L.; Ramírez-Jiménez, R.A.; Aguilar, M.R.; Marcos-Fernández, Á. Biodegradable and Biocompatible Thermoplastic Poly(Ester-Urethane)s Based on Poly(ε-Caprolactone) and Novel 1,3-Propanediol Bis(4-Isocyanatobenzoate) Diisocyanate: Synthesis and Characterization. Polymers 2022, 14, 1288. https://doi.org/10.3390/polym14071288

AMA Style

Rubio Hernández-Sampelayo A, Navarro R, González-García DM, García-Fernández L, Ramírez-Jiménez RA, Aguilar MR, Marcos-Fernández Á. Biodegradable and Biocompatible Thermoplastic Poly(Ester-Urethane)s Based on Poly(ε-Caprolactone) and Novel 1,3-Propanediol Bis(4-Isocyanatobenzoate) Diisocyanate: Synthesis and Characterization. Polymers. 2022; 14(7):1288. https://doi.org/10.3390/polym14071288

Chicago/Turabian Style

Rubio Hernández-Sampelayo, Alejandra, Rodrigo Navarro, Dulce M. González-García, Luis García-Fernández, Rosa A. Ramírez-Jiménez, María R. Aguilar, and Ángel Marcos-Fernández. 2022. "Biodegradable and Biocompatible Thermoplastic Poly(Ester-Urethane)s Based on Poly(ε-Caprolactone) and Novel 1,3-Propanediol Bis(4-Isocyanatobenzoate) Diisocyanate: Synthesis and Characterization" Polymers 14, no. 7: 1288. https://doi.org/10.3390/polym14071288

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