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Synthesis and characterization of poly(linoleic-g-ε-caprolactone) graft copolymers via “click” reaction and ring-opening polymerization

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Abstract

Linoleic acid modified with auto-oxidation, hydroxylation, bromination and azidation was used to synthesis graft copolymers using ω-alkyne-terminated poly(ε-caprolactone) (alk-PCLs) via “click” reaction. In the first step, the polymeric linoleic acid (PLina) as macroinitiator was obtained by the autoxidation of linoleic acid. Hydroxylation of the PLina was then carried out using diethanolamine to produce hydroxylated polymeric linoleic acid (PLina-OH). The PLina-OH was chemically modified with 2-bromopropionyl bromide to obtain bromo-functionalized polymeric linoleic acid (PLina-Br). This macroinitiator was then modified with sodium azide, resulting in azide polymeric linoleic acid (PLina-N3). In a parallel process, ω-alkyne-terminated poly(ε-caprolactone) (alk-PCLs) were prepared via ROP of the ε-caprolactone monomer in the presence of propiolic acid, 3-butyn-1-ol, 5-hexynoic acid, and propargyl alcohol as the precursors and tin(II) 2-ethyl hexanoate (Sn(Oct)2) as the catalyst. These preliminary steps involved the synthesis of azide and alkyne compounds capable of being linked together via the alkyne-azide cycloaddition reaction catalyzed by copper (Cu(I)), which led to poly(linoleic acid)-g-poly(ε-caprolactone) (PLina-g-PCL). The obtained polymers were characterized by proton nuclear magnetic resonance (1H NMR), Fourier-transform infrared (FTIR), differential scanning calorimetry (DSC), thermal gravimetric analysis (TGA) and elemental analysis.

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JCSC-D-21-00100

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Acknowledgements

This study was funded by the Düzce University Research Fund (Grant Number: 2016.07.06.487, 2019.07.06.1021).

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  1. Department of Chemistry, Düzce University, 81620, Düzce, Turkey

    Sema Alli

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Alli, S. Synthesis and characterization of poly(linoleic-g-ε-caprolactone) graft copolymers via “click” reaction and ring-opening polymerization. J Chem Sci 133, 74 (2021). https://doi.org/10.1007/s12039-021-01923-4

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  • DOI: https://doi.org/10.1007/s12039-021-01923-4

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