Synthesis and characterization of biodegradable acrylated polyurethane based on poly(ε-caprolactone) and 1,6-hexamethylene diisocyanate

Alishiri, M.; Shojaei, Akbar; Abdekhodaie, Mohammad J.; Yeganeh, Hamid

doi:10.1016/j.msec.2014.05.056

Cited by 47 publications

(52 citation statements)

References 49 publications

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“…and Table , the glass transition temperatures, measured in the second heating by DSC ( T g,DSC ), ranged between −1.2°C and 29.5°C for PTMG‐based SMPUs and between −2.1°C and 10.9°C for PEG‐based SMPUs. These T g,DSC values can be assigned to the amorphous structure of polyol because of the lack of crystalline structure in SMPUs, as reported in literature . Moreover, it is observed that the T g,DSC values increase with increasing hard segment (higher n ).…”

Section: Resultssupporting

confidence: 78%

Influence of the soft segment nature on the thermomechanical behavior of shape memory polyurethanes

Sáenz-Pérez

Laza

García-Barrasa³

et al. 2017

Polymer Engineering & Sci

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Shape‐memory polyurethanes (SMPUs) represent a highly interesting class of materials due to their applications in different sectors such as biomedical, textile, and aerospace. Moreover, it is possible to synthesize a variety of polyurethanes with different molecular architectures just choosing properly the chemical structure of their components. In this work, it is described the influence of the soft segment on the thermomechanical properties and shape memory behavior of shape memory polyurethanes. The synthesis, based on two‐step polymerization, was prepared by two different soft segments: poly(oxytetramethylene) glycol (PTMG) or poly(ethylene glycol) (PEG). Depending on the molecular architecture achieved, the materials present different properties that were studied by thermogravimetric analysis (TGA), differential scanning calorimetry (DSC) and dynamic mechanical analysis (DMA). Furthermore, the shape memory response of thermally activated SMPUs is determined qualitative and quantitatively by visually monitoring the shape recovery process and by thermomechanical analysis (TMA), respectively. All developed compositions have shown good shape memory behavior, with recovery ratios higher than 99.8%. POLYM. ENG. SCI., 58:238–244, 2018. © 2017 Society of Plastics Engineers

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Section: Resultssupporting

confidence: 78%

Influence of the soft segment nature on the thermomechanical behavior of shape memory polyurethanes

Sáenz-Pérez

Laza

García-Barrasa³

et al. 2017

Polymer Engineering & Sci

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“…1b), the signal of -OH on ADO disappeared, and that of -NH on ABPU was observed at 7.15 ppm, 30 meanwhile, the signals located at 1.50, 3.05, and 4.05 ppm were attributed to protons of AD, decoyl, and butyl, respectively. [31][32][33] Furthermore, molecular weight of ABPUs was determined by GPC, and the M n ranges from 34 200 to 66 700. These results conrm that AD-containing polyurethanes were successfully synthesized.…”

Section: Synthesis and Characterization Of Abpusmentioning

confidence: 99%

Shape memory materials based on adamantane-containing polyurethanes

Zou

Chen

2018

RSC Adv.

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In this contribution, a series of adamantane (AD)-containing polyurethanes were prepared from 1,3-adamantanediol, 1,4-butanediol and hexamethylene diisocyanate, and the influences of AD on the shape memory behavior of polyurethanes were systematically studied. Due to large steric hindrance, AD was able to disrupt the regular arrangement of polyurethane chains and contributed to forming an amorphous domain. It was found that moderate AD-containing polyurethanes had good mechanical properties and broad glass transition, and shape memory tests confirmed these polyurethanes possessed a shape fixation rate of 98% and shape recovery rate of 91% during a dual-shape memory procedure. Furthermore, they also exhibited a triple-shape memory effect. This work demonstrated a facile and feasible way to prepare polyurethane-based shape memory materials by using adamantane as a functional unit.

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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%

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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Synthesis and characterization of biodegradable acrylated polyurethane based on poly(ε-caprolactone) and 1,6-hexamethylene diisocyanate

Cited by 47 publications

References 49 publications

Influence of the soft segment nature on the thermomechanical behavior of shape memory polyurethanes

Influence of the soft segment nature on the thermomechanical behavior of shape memory polyurethanes

Shape memory materials based on adamantane-containing polyurethanes

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

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