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An organocatalytic ring-opening polymerization approach to highly alternating copolymers of lactic acid and glycolic acid
| Title: | An organocatalytic ring-opening polymerization approach to highly alternating copolymers of lactic acid and glycolic acid |
| Authors: | Takojima, Kaoru Browse this author | | Makino, Hiroshi Browse this author | | Saito, Tatsuya Browse this author | | Yamamoto, Takuya Browse this author | | Tajima, Kenji Browse this author →KAKEN DB | | Isono, Takuya Browse this author | | Satoh, Toshifumi Browse this author →KAKEN DB |
| Issue Date: | 21-Oct-2020 |
| Publisher: | Royal Society of Chemistry |
| Journal Title: | Polymer chemistry |
| Volume: | 11 |
| Issue: | 39 |
| Start Page: | 6365 |
| End Page: | 6373 |
| Publisher DOI: | 10.1039/d0py01082k |
| Abstract: | The alternating copolymer of lactic acid and glycolic acid (PLGA) is a highly promising next generation biodegradable material for biomedical and pharmaceutical applications due to its uniform degradation behaviors in addition to its ability to form stereocomplexes. However, versatile synthetic methods toward the narrowly dispersed alternating PLGAs with controlled molecular weights and desired end functionalities have been largely unexplored. Herein, we report the organocatalytic regioselective ring-opening polymerization (ROP) of optically active methylglycolides (l- andd-MGs) to produce highly alternating PLGAs. The ROP ofl-MG using a phosphazene base P-2-t-Bu/alcohol system in THF at -78 degrees C achieved the highest regioselectivity (P= 0.95) as well as a good control over the molecular weight (M-n= 6.6-15.6 g mol(-1)), with a relatively narrow dispersity (D= 1.21-1.29). Furthermore, alternating PLGA diol as well as azido-, ethynyl-, and poly(ethylene glycol) monomethyl ether-end-functionalized alternating PLGAs was successfully obtained by employing the corresponding functional alcohol initiators. An enantiomeric 1 : 1 blend of PLGAs prepared froml- andd-MGs formed a stereocomplex with a crystallinity and melting point comparable to the reported data for the stereocomplex from the perfectly alternating PLGAs producedviaa polycondensation approach, which implies the high degree of the alternating sequence of the obtained copolymers. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/82995 |
| Appears in Collections: | 工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 磯野 拓也
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