TY - JOUR
T1 - Benzyl β-malolactonate
T2 - Synthesis, copolymerization and design of novel biodegradable macromolecular surfactants
AU - Coulembier, Olivier
AU - Ghisdal, Jessica
AU - Degée, Philippe
AU - Dubois, Philippe
PY - 2007/1/1
Y1 - 2007/1/1
N2 - 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.
AB - 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.
KW - Amphiphilic copolymer
KW - Lactide
KW - Surface tension
KW - Surfactant biodegradablility
KW - [R,S]benzyl β-malolactonate
UR - http://www.scopus.com/inward/record.url?scp=33846250887&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:33846250887
SN - 1551-7012
VL - 2007
SP - 57
EP - 70
JO - ARKIVOC
JF - ARKIVOC
IS - 10
ER -