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Synthesis and properties of novel biodegradable polyurethanes containing fluorinated aliphatic side chains

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Abstract

This study used 5H–octafluoropentanoylfluoride and 2-amino-2-methyl-1,3-propanediol to synthesize a novel fluoro chain extender 2,2,3,3,4,4,5,5-octafluoro-N-(1,3-dihydroxy-2-methylpropan-2-yl) pentanamide (ODMP). Furthermore, 4,4′-diphenylmethane diisocyanate served as the hard segment, polycaprolactone diol (PCL) served as the soft segment, and ODMP served as the chain extender in the novel synthesized polyurethanes (ODMP/PUs). Gel permeation chromatography revealed that the molecular weight of the ODMP/PUs increased when the ODMP content was increased. 1H and 19F nuclear magnetic resonance and Fourier transform infrared spectroscopy verified that the ODMP chain extenders were successfully synthesized and that the ODMP chain extenders were successfully incorporated into the backbone of the PUs. The interaction between the -NH (hydrogen bond) and CF2 groups in the ODMP/PUs became stronger when the ODMP content was increased. Thermal analysis revealed that the initial decomposition temperature of the ODMP/PUs decreased and the second decomposition temperature increased when the polymers’ ODMP content was increased. Higher ODMP content also resulted in the ODMP/PUs’ higher glass transition and dynamic glass transition temperatures and lower ODMP maximum stress and Young’s modulus, causing a lower elongation at break. ODMP/PUs with higher ODMP content exhibited more protrusions and more rugged surfaces. The chemical resistance of the ODMP/PUs increased when the fluorine content was increased. Scanning electron microscopy revealed that ODMP/PUs with higher PCL content exhibited higher levels of hydrolytic degradation. Finally, in vitro erythrocyte tests revealed that increasing the ODMP chain extender content reduced the average number of erythrocytes adhering to the surface of the PUs.

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Authors and Affiliations

  1. Department of Materials Science and Engineering, National Taiwan University of Science and Technology, Taipei, Taiwan 10607, Republic of China

    Shuenn-Kung Su, Jia-Hao Gu & Cheng-Lung Wu

  2. Department of Materials Science and Engineering, Vanung University, Jongli, Taoyuan, Taiwan 32061, Republic of China

    Hsun-Tsing Lee

  3. Department of Chemical Engineering, Army Academy, Jongli, Taoyuan, Taiwan 32092, Republic of China

    Jiunn-Jer Hwang

  4. Department of Fashion Business Administration, LEE-MING Institute of Technology, No. 22, Sec. 3, Tailin. Rd., New Taipei City, Taiwan 24305, Republic of China

    Maw-Cherng Suen

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  1. Shuenn-Kung Su
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  2. Jia-Hao Gu
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Correspondence to Maw-Cherng Suen.

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Su, SK., Gu, JH., Lee, HT. et al. Synthesis and properties of novel biodegradable polyurethanes containing fluorinated aliphatic side chains. J Polym Res 24, 142 (2017). https://doi.org/10.1007/s10965-017-1301-9

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  • DOI: https://doi.org/10.1007/s10965-017-1301-9

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