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Ring‐Opening Polymerization of a New Diester Cyclic Dimer of Mandelic and Glycolic Acid: An Efficient Synthesis Method for Derivatives of Amorphous Polyglycolide with High T g
Author(s) -
Nakajima Hajime,
Loos Katja,
Ishizu Shinobu,
Kimura Yoshiharu
Publication year - 2018
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.201700865
Subject(s) - glycolic acid , polymer chemistry , ring opening polymerization , polyester , polymerization , materials science , mandelic acid , amorphous solid , glass transition , dimer , lactide , polymer , chemistry , lactic acid , organic chemistry , composite material , genetics , bacteria , biology
In this study, poly(mandelate‐ co‐ glycolate) (PMG), a modified polyglycolide (PGL), is prepared by ring‐opening polymerization (ROP) of L‐3‐phenyl‐1,4‐dioxane‐2,5‐dione (PDD); the cyclic dimer of biobased mandelic acid and glycolic acid. The resulting polymer shows an increased glass transition temperature ( T g ) due to the incorporation of phenyl groups in the chain. High molecular weight PMG is obtained by bulk ROP at 150 °C, and it exhibits a glassy amorphous state with enhanced thermal properties such as a T g being 35 °C higher than conventional PGL. PDD is also copolymerized with glycolide (GL) and lactide (LA), resulting in poly(mandelate‐ co‐ glycolate/glycolate) ((P(MG/GL)) with GL and poly(mandelate‐ co‐ glycolate/lactide) ((P(MG/LA)) with LA. The thermal properties of P(MG/GL) and P(MG/LA) are found to be distinctly different from PMG and conventional PGL and polylactide, and they are tunable with a changing molar ratio of PDD, GL, and LA. Therefore, PDD opens an elegant way to control and tailor the properties of biobased polyesters.