Benzyl β-malolactonate: Synthesis, copolymerization and design of novel biodegradable macromolecular surfactants

Olivier Coulembier, Jessica Ghisdal, Philippe Degée, Philippe Dubois

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Abstract

Racemic [R,S] benzyl β-malolactonate monomer (MLABz) was synthesized according to the well-established "aspartic acid" route and purified to such an extend that it allowed the controlled synthesis of poly([R,S] β-malic acid)-b-poly((D,L)-lactide) diblock copolymers by a versatile three-step pathway combining anionic and coordination-insertion ROP of MLABz and lactide monomers, respectively. For the sake of comparison, amphiphilic poly([R,S] β-malic acid)-b-poly(ε-caprolactone) diblock copolymers of identical composition were synthesized as well. The associating behavior of monodisperse diblock copolymers consisting of water-soluble poly(β-malic acid) block and hydrophobic polylactide or poly(ε-caprolactone) block was studied in aqueous solution. Accordingly, both types of copolymers were dissolved directly in water and (dynamic) surface tension measurements were carried out. It came out that poly(β-malic acid)-b-poly((D,L)-lactide) amphiphilic diblock copolymers showed tensioactive properties with a lower critical micellar concentration, a higher efficiency of adsorption and a better monomer coefficient diffusion compared to corresponding poly(β-malic acid)-b-poly(ε-caprolactone) diblock copolymers of comparative composition.

Original languageEnglish
Pages (from-to)57-70
Number of pages14
JournalARKIVOC
Volume2007
Issue number10
Publication statusPublished - 1 Jan 2007
Externally publishedYes

Keywords

  • Amphiphilic copolymer
  • Lactide
  • Surface tension
  • Surfactant biodegradablility
  • [R,S]benzyl β-malolactonate

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