An Efficient Thiol-Ene Chemistry for the Preparation of Amphiphilic PHA-Based Graft Copolymers

Authors

  • Gaëlle Le Fer,

    1. Institut de Chimie et des Matériaux Paris-Est (ICMPE), Systèmes Polymères, Complexes, UMR-CNRS 7182, 2–8 rue Henri Dunant, 94320 Thiais, France
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  • Julien Babinot,

    1. Institut de Chimie et des Matériaux Paris-Est (ICMPE), Systèmes Polymères, Complexes, UMR-CNRS 7182, 2–8 rue Henri Dunant, 94320 Thiais, France
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  • Davy-Louis Versace,

    1. Institut de Chimie et des Matériaux Paris-Est (ICMPE), Systèmes Polymères, Complexes, UMR-CNRS 7182, 2–8 rue Henri Dunant, 94320 Thiais, France
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  • Valérie Langlois,

    1. Institut de Chimie et des Matériaux Paris-Est (ICMPE), Systèmes Polymères, Complexes, UMR-CNRS 7182, 2–8 rue Henri Dunant, 94320 Thiais, France
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  • Estelle Renard

    Corresponding author
    1. Institut de Chimie et des Matériaux Paris-Est (ICMPE), Systèmes Polymères, Complexes, UMR-CNRS 7182, 2–8 rue Henri Dunant, 94320 Thiais, France
    • Institut de Chimie et des Matériaux Paris-Est (ICMPE), Systèmes Polymères, Complexes, UMR-CNRS 7182, 2–8 rue Henri Dunant, 94320 Thiais, France.
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Abstract

We present a straightforward method to prepare amphiphilic graft copolymers consisting of hydrophobic poly(3-hydroxyalkanoates) (PHAs) backbone and hydrophilic α-amino-ω-methoxy poly(oxyethylene-co-oxypropylene) (Jeffamine®) units. Poly(3-hydroxyoctanoate)-co-(3-hydroxyundecenoate) (PHOU) was first methanolyzed to obtain the desired molar mass. The amino end groups of Jeffamine were converted into thiol by a reaction with N-acetylhomocysteine thiolactone and subsequently photografted. This “one-pot” functionalization prevents from arduous and time-consuming functionalization of the hydrophilic precursor or tedious modifications of PHAs, thus simplifying the process. The amphiphilic nature of modified PHAs leads to water-soluble copolymers exhibiting thermoresponsive behavior.

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