Synthesis methods of poly(lactic acid)

1. Synthesis methods of poly(lactic acid) ผศ.ดร.วราวุฒิ ตั้งพสุธาดล ภาควิชาเคมี คณะวิทยาศาสตร์ จุฬาลงกรณ์มหาวิทยาลัย varawut.t@chula.ac.th

2. Poly(lactic acid) Polylactide Poly(L-lactic acid) Poly-L-lacide Poly(D-lactic acid) Poly-D-lacide Other polyesters: poly(glycolic acid), poly(butylenesuccinate), poly(butyleneadipate terephthalate), poly(ethylene terephthalate) etc. Bioplastics

3. Poly(L-lactic acid) vs Poly(D-lactic acid)

4. Poly(lactic acid) or polylactide or polylactide

6. Mechanism of metal catalyzed esterification

7. Mechanism of metal catalyzed ring-opening polymerization

8. Temperature Vacuum (dehydration process) Catalyst Recommended paper: T. Maharana, B. Mohanty, Y.S. Negi, Progress in Polymer Science 34 (2009) 99–124 Key reaction conditions for making polyesters: (that you can also play with)

9. End-Functionalized PLA-PLA with new properties

10. Crosslinkable PLA By WorapobKitpanitch Program of Petrochemistry and Polymer Science graduated in May 2012

11. Literature review Benzoyl peroxide Park, E.S. et al. Journal of Applied Polymer Science, 2003, 90, 1802-1807.

12. Literature review Irgacure 651 (2,2-dimethoxy-2-phenylacetophenone) UV at365nm Brown, C.D. et al. Journal of Biomaterials Science, Polymer Edition, 2005, 16, 189-201.

13. L-lactic acid was heated to 80 °C under reduced pressurefor 3 h 1.5 mol% 1,4-butanediol and 0.1 mol% TNBT were added The reaction was heated up to 160 °C under reduced pressure for 5 h and then continued at 180 °C for 5 h The resulting polymer was purified by dissolving in chloroform and precipitating in MeOH The white product of PLLA was obtained and dried by vacuum at room temperature I.Synthesis of PLLA-diol Zeng, J.B. et al. Ind. Eng. Chem. Res. 2009, 48, 1706-1711.

14. 1H NMR spectrum of PLLA-diol a b d f e a c b c e d f ppm

15. II.Methacrylated-endcapped PLLA

16. Effect of mole ratios (PLLA:Meth) on the degree of methacrylate substitution on PLLA chain end (reaction time = 24 h, reaction temperature = 80 °C)

17. 1H NMR spectrum of PLLA-MA a b decrease a b ppm

18. Thermal crosslinking The functionalized PLLA was mixed with 10 wt% BPO in chloroform The mixture was poured into a circular mold (3 mm high and 6 mm in diameter) and kept at room temperature for 24 h The mixture was heated at 150 °C for 1 h III.Crosslinking of PLLA (a) (b)

19. Degree of gel content Chloroform immersion 24 h Thermal crosslinking Gel content = 60%

20. Positively-charged PLA By Piyachai Khomein Department of Chemistry, Faculty of Science, CU graduated in May 2012

21. Positively-charged PLA PLA GTMAC Positively-charged PLA • By Piyachai Khomein • Department of Chemistry

22. Positively-charged PLA Hydrophilicity determination of PLA+ films

23. End-Functionalized PLA Lu, D. D.; Yang, L. Q.; Zhou, T. H.; Lei, Z. Q., European Polymer Journal 2008,44 (7), 2140-2145. Kobori, Y.; Iwata, T.; Doi, Y.; Abe, H., Biomacromolecules2004,5 (2), 530-536.

24. End-Functionalized PLA • Ouchi, T.; Kontani, T.; Ohya, Y., Polymer 44 (2003), 3927-3933