Incorporating isosorbide as the chain extender improves mechanical properties of linear biodegradable polyurethanes as potential bone regeneration materials

Ma, Yufei; Liu, Juan; Luo, Min; Xing, Juan; Wu, Jicang; Pan, Haobo; Ruan, Changshun; Luo, Yanfeng

doi:10.1039/c6ra28826j

Cited by 20 publications

(20 citation statements)

References 33 publications

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“…1,4:3,6-dianhydrohexitol is one of the few inexpensive difunctional monomers available from renewable resources derived from biomass such as wheat, sugar, and corn [ 5 ]. Isosorbide is a stereoisomer of 1,4:3,6-dianhydrohexitol, and, due to its accessible and affordable polymer synthesis, it is the most favored candidate for renewable monomers used in addressing environmental issues [ 6 ]. Its unique molecular structure and chirality enhance the glass transition temperature and transparency of the resulting polymers [ 7 ].…”

Section: Introductionmentioning

confidence: 99%

Fabrication of Two Polyester Nanofiber Types Containing the Biobased Monomer Isosorbide: Poly (Ethylene Glycol 1,4-Cyclohexane Dimethylene Isosorbide Terephthalate) and Poly (1,4-Cyclohexane Dimethylene Isosorbide Terephthalate)

et al. 2018

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The thermal and mechanical properties of two types of polyester nanofiber, poly (1,4-cyclohexanedimethylene isosorbide terephthalate) (PICT) copolymers and the terpolyester of isosorbide, ethylene glycol, 1,4-cyclohexane dimethanol, and terephthalic acid (PEICT), were investigated. This is the first attempt to fabricate PICT nanofiber via the electrospinning method; comparison with PEICT nanofiber could give greater understanding of eco-friendly nanofibers containing biomass monomers. The nanofibers fabricated from each polymer show similar smooth and thin-and-long morphologies. On the other hand, the polymers exhibited significantly different mechanical and thermal properties; in particular, a higher tensile strength was observed for PICT nanofiber mat than for that of PEICT. We hypothesized that PICT has more trans-configuration than PEICT, resulting in enhancement of its tensile strength, and demonstrated this by Fourier transform infrared spectroscopy. In addition, PICT nanofibers showed clear crystallization behavior upon increased temperature, while PEICT nanofibers showed completely amorphous structure. Both nanofibers have better tensile properties and thermal stability than the typical polyester polymer, implying that they can be utilized in various industrial applications.

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Section: Introductionmentioning

confidence: 99%

Fabrication of Two Polyester Nanofiber Types Containing the Biobased Monomer Isosorbide: Poly (Ethylene Glycol 1,4-Cyclohexane Dimethylene Isosorbide Terephthalate) and Poly (1,4-Cyclohexane Dimethylene Isosorbide Terephthalate)

et al. 2018

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“…The molecules containing hydroxyl groups are usually employed as coinitiator to initiate the ring‐opening polymerization of lactide and regulate the molecular weight of PLA as well . Since the surfaces of the HA particles contain the reactive hydroxyl groups, they could be used as the coinitiator of lactide to produce PDLLA‐grafted HA, as shown in Figure .…”

Section: Resultsmentioning

confidence: 99%

The reactivity of surface modification of hydroxyapatite particles depends on their shape

Wang

Yang

et al. 2019

Polymer Composites

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The effect of hydroxyapatite (HA) particle shape on the reactivity of HA surfaces was investigated by selecting the rod‐shaped (r‐HA) and spherical HA particles (s‐HA) to coinitiate the ring‐opening polymerization of d,l‐lactide (DLLA) used stannous octoate (Sn(Oct)2) as the catalyst, respectively. It was found that both s‐HA and r‐HA could be grafted with PDLLA and the reactivity of s‐HA was higher than that of r‐HA according to the results from FTIR, NMR, TGA and BET method. The potential mechanism was that the shape of HA particles determined the crystal faces exposed to participate in graft reaction clarified by performing X‐ray diffraction detections and Materials Studio analysis. The primary crystal faces were (211) and (112) for s‐HA yet (002) and (300) for r‐HA. These findings suggested that the shape of HA particles might influence their reactivity, which might provide a new way to improve the graft ratio of polymers so as to prepare HA/polymer composites with strong interfacial strength by selecting or designing the shape of the HA particles.

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“…Linear polyurethanes with poly( dl ‐lactic acid) macrodiol as soft segments (PDLLA‐PUs) have been widely studied as tissue engineering scaffolds and shape memory implants due to their excellent shape memory effects, processibility, biodegradability, and biocompatibility . PDLLA‐PUs are generally prepared in organic solvent through the reactions of macrodiol with diisocyanate and then with a chain extender.…”

Section: Introductionmentioning

confidence: 99%

“…PDLLA‐PUs are generally prepared in organic solvent through the reactions of macrodiol with diisocyanate and then with a chain extender. To form a PDLLA‐PU with a high molecular weight and linear structure without branching or crosslinking, carefully controlling the reaction conditions, such as temperature, formulations, solvent or agitation, is essentially required . Otherwise, unexpected crosslinking or branching may take place, which may further complicate the compositions, degradation, and other biofunctional properties of the obtained polyurethanes.…”

Section: Introductionmentioning

confidence: 99%

Facile Preparation of Linear Polyurethane from UPy‐Capped Poly(dl‐Lactic Acid) Macrodiol

Ren

Chen

et al. 2018

Macro Materials & Eng

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Linear polyurethanes based on poly(dl‐lactic acid) (PDLLA) macrodiol are promising materials in tissue engineering, yet their synthesis requires rigorous control on various parameters. A facile way to prepare linear polyurethanes by capping the PDLLA macrodiol (M n = 4536) with 2‐ureido‐4[1H]‐pyrimidone (UPy) is reported. The obtained low‐molecular‐weight UPy‐capped polyurethane can form flexible, stretchable, and hydrophobic supramolecular films due to the strong and unidirectional quadruple hydrogen bonding of UPy dimers. Tensile tests, shape recovery, and self‐healing observations indicate that, compared with conventional PDLLA macrodiol‐based linear polyurethane (M n = 48840 and PDI = 1.8), the UPy‐capped polyurethane films have comparable mechanical properties (tensile modulus: 900 ± 38 MPa; ultimate strength: 9.6 ± 0.8 MPa) yet significantly better shape memory and self‐healing properties. These results suggest that the UPy‐capped polyurethane might become an alternative for conventional linear polyurethane as a new biomedical material.

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Incorporating isosorbide as the chain extender improves mechanical properties of linear biodegradable polyurethanes as potential bone regeneration materials

Abstract: Novel linear biodegradable polyurethanes based on poly (d,l-lactic acid) as soft segments and isosorbide as chain extender were exhibited with high molecular weight and appropriate mechanical performances, promising as the scaffold materials for bone regeneration.

Cited by 20 publications

References 33 publications

Fabrication of Two Polyester Nanofiber Types Containing the Biobased Monomer Isosorbide: Poly (Ethylene Glycol 1,4-Cyclohexane Dimethylene Isosorbide Terephthalate) and Poly (1,4-Cyclohexane Dimethylene Isosorbide Terephthalate)

Fabrication of Two Polyester Nanofiber Types Containing the Biobased Monomer Isosorbide: Poly (Ethylene Glycol 1,4-Cyclohexane Dimethylene Isosorbide Terephthalate) and Poly (1,4-Cyclohexane Dimethylene Isosorbide Terephthalate)

The reactivity of surface modification of hydroxyapatite particles depends on their shape

Facile Preparation of Linear Polyurethane from UPy‐Capped Poly(dl‐Lactic Acid) Macrodiol

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