Synthesis of bio-based thermoplastic polyurethane elastomers containing isosorbide and polycarbonate diol and their biocompatible properties

Oh, Seunghoon; Kang, Min-Sil; Knowles, Jonathan C.; Gong, Myoung‐Seon

doi:10.1177/0885328215590054

Cited by 46 publications

(46 citation statements)

References 36 publications

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“…FT-IR spectra of the three types of aligners before and after immersion in coffee were analysed, 38, 39, 40 and the IR peaks of the different groups are shown in Figure 4. FT-IR analysis confirmed that the Invisalign aligners were a PU-based material, 27, 28 the Angelalign aligners and/or retainers were a polycarbonate (PC)-based material, and the Smartee aligners were a PETG-based material.…”

Section: Resultsmentioning

confidence: 99%

Colour stabilities of three types of orthodontic clear aligners exposed to staining agents

et al. 2016

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The aim of this study was to evaluate and compare the colour stabilities of three types of orthodontic clear aligners exposed to staining agents in vitro. Sixty clear orthodontic aligners produced by three manufacturers (Invisalign, Angelalign, and Smartee) were immersed in three staining solutions (coffee, black tea, and red wine) and one control solution (distilled water). After 12-h and 7-day immersions, the aligners were washed in an ultrasonic cleaner and measured with a colourimeter. The colour changes (ΔE*) were calculated on the basis of the Commission Internationale de I'Eclairage L*a*b* colour system (CIE L*a*b*), and the results were then converted into National Bureau of Standards (NBS) units. Fourier transformation infrared (FT-IR) spectroscopy and scanning electron microscopy (SEM) were conducted to observe the molecular and morphologic alterations to the aligner surfaces, respectively. The three types of aligners exhibited slight colour changes after 12 h of staining, with the exception of the Invisalign aligners stained with coffee. The Invisalign aligners exhibited significantly higher ΔE* values (ranging from 0.30 to 27.81) than those of the Angelalign and Smartee aligners (ΔE* values ranging from 0.33 to 1.89 and 0.32 to 1.61, respectively, P<0.05). FT-IR analysis confirmed that the polymer-based structure of aligners did not exhibit significant chemical differences before and after the immersions. The SEM results revealed different surface alterations to the three types of aligner materials after the 7-day staining. The three types of aesthetic orthodontic appliances exhibited colour stability after the 12-h immersion, with the exception of the Invisalign aligners stained by coffee. The Invisalign aligners were more prone than the Angelalign and Smartee aligners to pigmentation. Aligner materials may be improved by considering aesthetic colour stability properties.

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Section: Resultsmentioning

confidence: 99%

Colour stabilities of three types of orthodontic clear aligners exposed to staining agents

et al. 2016

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“…Effect of these soft segments in combination with various chain extenders has been investigated on degradation and physical/mechanical properties of the polyurethanes. Poly(ε‐caprolactone) (PCL) is one the most frequently used soft segment in biodegradable polyurethanes synthesis . However, degradation rate of PCL is rather slow because of its relatively hydrophobic nature and semicrystalline structure .…”

Section: Introductionmentioning

confidence: 99%

“…19 Polyester polyurethanes are known to be susceptible to hydrolytic degradation. 14,19 Poly(ε-caprolactone), 11,[20][21][22] poly(lactic acid), 12,23,24 poly(glycolic acid), poly(R-3-hydroxybutyric acid), 25 and their copolymers 14,[26][27][28][29] are extensively used as soft segments in SPUs. Effect of these soft segments in combination with various chain extenders has been investigated on degradation and physical/ mechanical properties of the polyurethanes.…”

Section: Introductionmentioning

confidence: 99%

“…Poly(ε-caprolactone) (PCL) is one the most frequently used soft segment in biodegradable polyurethanes synthesis. 11,[20][21][22] However, degradation rate of PCL is rather slow because of its relatively hydrophobic nature and semicrystalline structure. 22 On the other hand, biodegradation rate of poly(glycolic acid) is very fast (about 2 weeks) 14 ; therefore, synthesis of glycolideco-caprolactone macrodiols with different glycolide to ε-caprolactone ratios can be considered as an effective strategy to fabricate polyurethanes with tunable biodegradation rate.…”

Section: Introductionmentioning

confidence: 99%

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Polyurethanes with separately tunable biodegradation behavior and mechanical properties for tissue engineering

Moghanizadeh-Ashkezari

Shokrollahi

Zandi

et al. 2017

Polymers for Advanced Techs

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Two series (random and block) poly(glycolide-co-ε-caprolactone) macrodiols with various glycolide to ε-caprolactone ratios (50/50 and 30/70, R-PG50C, R-PG30C, B-PG50C, and B-PG30C) were synthesized. Next, segmented polyurethanes (PUs) were synthesized based on the synthesized macrodiols, 1,6-hexamethylene diisocyanate and 1,4-butanediol (PU-R30, PU-R50, PU-B30, and PU-B50). Effect of glycolide (G) and ε-caprolactone (C) monomers arrangement (random or block) on the PUs properties were investigated via FTIR, 1 H NMR, DSC, TGA, DMA, SEM, and mechanical tests. All PUs illustrated T g (−33°C to −48°C) and T m (102°C to 139°C) corresponding to the soft and the hard segments, respectively. Polymers based on block macrodiols also showed T m related to the soft segments. While PUs underwent a two-step thermal degradation, the PUs based on block macrodiols indicated higher degradation temperature.Dynamic mechanical analysis results evidenced development of a well-defined microphase separated structure in PU-R30. Contact angle (about 70°-80°) and water uptake (around 20% after 24 hours) of the PU films are close to those suitable for tissue engineering materials. The PU based on R-PG30C (PU-R30) exhibited the highest tensile strength (2.87 MPa) followed by PU-B50 and PU-R50. Over a 63-day in vitro degradation study in phosphate buffered saline, the PUs showed variable weight loss (up to 40%) depending on their soft segments composition and arrangement. Also, the PUs showed no cytotoxicity. Thus, these PUs with tunable biodegra- To the best of our knowledge, there are not much reports on systematic synthesis of polyurethanes based on (glycolide-cocaprolactone) macrodiols of different glycolide to caprolactone ratios (as the soft segment), and HDI and butanediol (BD) (as components of the hard segment). Therefore, in this work, PGC macrodiols with different monomer ratios and different comonomers were synthesized and characterized. Then 2 series of SPUs based on these macrodiols and HDI and BD were produced. The effect of macrodiol structure on physicochemical, mechanical properties, and biodegradation rate of the synthesized polymers was investigated. | MATERIALS AND METHODS | MaterialsGlycolide, 1,4-butanediol and tin (II) 2-ethylhexanoate (Sn(Oct)2) were purchased from Sigma_ Aldrich Co, Germany. ε-Caprolactone (>99%), ethylene glycol, 1,6-hexamethylene diisocyanate, 1,2-dichroethane, and n-hexane were obtained from Merck Chemicals, Germany.1,2-Dichroethane and ε-caprolactone were dried prior to use. | Synthesis of PGC macrodiolsRandom and block PGC (R-PGC and B-PGC) macrodiols were synthesized via ring opening polymerization of glycolide and ε-caprolactone initiated by ethylene glycol. In random series, glycolide, ε-caprolactone, ethylene glycol, and the catalyst (stannous octoate)were heated at 130°C under a flow of dry N 2 . After certain time, the reaction mixture was cooled down to room temperature. To remove the catalyst and any residual monomers, the mixture was dissolved in 1.2-dichloroethane, and the copolymer w...

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“…Among different biopolymers, elastomers show high extensibility and recover to their original state when removing the stress. They are made of long polymer chains with excellent degree of flexibility and mobility …”

Section: Introductionmentioning

confidence: 99%

Fabrication, characterization, and biocompatibility assessment of a novel elastomeric nanofibrous scaffold: A potential scaffold for soft tissue engineering

et al. 2017

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With regard to flexibility and strength properties requirements of soft biological tissue, elastomeric materials could be more beneficial in soft tissue engineering applications. The present work investigates the use of an elastic polymer, (polycaprolactone fumarate [PCLF]), for fabricating an electrospun scaffold. PCLF with number-average molecular weight of 13,284 g/mol was synthetized, electrospun PCLF:polycaprolactone (PCL) (70:30) nanofibrous scaffolds were fabricated and a novel strategy (in situ photo-crosslinking along with wet electrospinning) was applied for crosslinking of PCLF in the structure of PCLF:PCL nanofibers was presented. Sol fraction results, Fourier-transform infrared spectroscopy, and mechanical tests confirmed occurrence of crosslinking reaction. Strain at break and Young's modulus of crosslinked PCLF:PCL nanofibers fabricated was found to be 114.5 ± 3.9% and 0.6 ± 0.1 MPa, respectively, and dynamic mechanical analysis results revealed elasticity of nanofibers. MTS assay showed biocompatibility of PCLF:PCL (70:30) nanofibrous scaffolds. Our overall results showed that electrospun PCLF:PCL nanofibrous scaffold could be considered as a candidate for further in vitro and in vivo experiments and its application for engineering of soft tissues subjected to in vivo cyclic mechanical stresses. © 2017 Wiley Periodicals, Inc. J Biomed Mater Res Part B: Appl Biomater, 106B: 2371-2383, 2018.

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Synthesis of bio-based thermoplastic polyurethane elastomers containing isosorbide and polycarbonate diol and their biocompatible properties

Cited by 46 publications

References 36 publications

Colour stabilities of three types of orthodontic clear aligners exposed to staining agents

Colour stabilities of three types of orthodontic clear aligners exposed to staining agents

Polyurethanes with separately tunable biodegradation behavior and mechanical properties for tissue engineering

Fabrication, characterization, and biocompatibility assessment of a novel elastomeric nanofibrous scaffold: A potential scaffold for soft tissue engineering

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