Synthesis of poly(lactide-co-glycolide) containing high glycolide contents by ring-opening polymerization as well as their structural characterizations, thermal properties, morphologies, and hydrophilicity
Van Hoang-Khang Phan
Department of Materials Science and Engineering, National Taiwan University of Science and Technology, Taipei, Taiwan
Contribution: Formal analysis (supporting), Methodology (equal), Writing - original draft (supporting)
Search for more papers by this authorYi-Hsin Tai
Department of Materials Science and Engineering, National Taiwan University of Science and Technology, Taipei, Taiwan
Contribution: Formal analysis (supporting), Methodology (supporting)
Search for more papers by this authorCorresponding Author
Tai-Chin Chiang
Global Development Engineering Program, National Taiwan University of Science and Technology, Taipei, Taiwan
Correspondence
Tai-Chin Chiang, Global Development Engineering Program, National Taiwan University of Science and Technology, 43, Section 4, Keelung Road, Taipei 106335, Taiwan.
Email: [email protected]
Chin-Yang Yu, Department of Materials Science and Engineering, National Taiwan University of Science and Technology, 43, Section 4, Keelung Road, Taipei, 106335, Taiwan.
Email: [email protected]
Contribution: Formal analysis (supporting), Methodology (supporting)
Search for more papers by this authorCorresponding Author
Chin-Yang Yu
Department of Materials Science and Engineering, National Taiwan University of Science and Technology, Taipei, Taiwan
Correspondence
Tai-Chin Chiang, Global Development Engineering Program, National Taiwan University of Science and Technology, 43, Section 4, Keelung Road, Taipei 106335, Taiwan.
Email: [email protected]
Chin-Yang Yu, Department of Materials Science and Engineering, National Taiwan University of Science and Technology, 43, Section 4, Keelung Road, Taipei, 106335, Taiwan.
Email: [email protected]
Contribution: Methodology (lead), Supervision (lead), Writing - original draft (lead)
Search for more papers by this authorVan Hoang-Khang Phan
Department of Materials Science and Engineering, National Taiwan University of Science and Technology, Taipei, Taiwan
Contribution: Formal analysis (supporting), Methodology (equal), Writing - original draft (supporting)
Search for more papers by this authorYi-Hsin Tai
Department of Materials Science and Engineering, National Taiwan University of Science and Technology, Taipei, Taiwan
Contribution: Formal analysis (supporting), Methodology (supporting)
Search for more papers by this authorCorresponding Author
Tai-Chin Chiang
Global Development Engineering Program, National Taiwan University of Science and Technology, Taipei, Taiwan
Correspondence
Tai-Chin Chiang, Global Development Engineering Program, National Taiwan University of Science and Technology, 43, Section 4, Keelung Road, Taipei 106335, Taiwan.
Email: [email protected]
Chin-Yang Yu, Department of Materials Science and Engineering, National Taiwan University of Science and Technology, 43, Section 4, Keelung Road, Taipei, 106335, Taiwan.
Email: [email protected]
Contribution: Formal analysis (supporting), Methodology (supporting)
Search for more papers by this authorCorresponding Author
Chin-Yang Yu
Department of Materials Science and Engineering, National Taiwan University of Science and Technology, Taipei, Taiwan
Correspondence
Tai-Chin Chiang, Global Development Engineering Program, National Taiwan University of Science and Technology, 43, Section 4, Keelung Road, Taipei 106335, Taiwan.
Email: [email protected]
Chin-Yang Yu, Department of Materials Science and Engineering, National Taiwan University of Science and Technology, 43, Section 4, Keelung Road, Taipei, 106335, Taiwan.
Email: [email protected]
Contribution: Methodology (lead), Supervision (lead), Writing - original draft (lead)
Search for more papers by this authorFunding information: National Taiwan University of Science and Technology
Abstract
Random copolymers, poly(l-lactide-r-glycolide) are synthesized by one-pot ring-opening polymerization of l-lactide and glycolide in the presence of stannous octoate and 1-dodecanol. Block copolymers, poly(l-lactide-b-glycolide) are synthesized by ring-opening polymerization of l-lactide to generate poly(l-lactide) first and then further ring-opening polymerization of glycolide in the presence of poly(l-lactide) and stannous octoate. The composition ratio of l-lactide and glycolide is determined by the integration of the corresponding signals from 1H NMR spectra, which is consistent with the feeding ratio. Very few hetero-sequences can be observed for block copolymers due to well-defined microstructures. The block copolymers are more thermally stable than that of the random copolymers. The degree of crystallinity of the bock copolymers is relatively high compared to that of the random copolymers. The image of the block copolymers determined by field-emission scanning electron microscopy (FESEM) shows partial aggregate domains containing spherical particles with an average diameter of around 200 nm, which is very different from that of the random copolymers. Block copolymers are more hydrophilic than that of the random copolymers due to the ordered structure and amphiphilic behavior of the block series.
Open Research
DATA AVAILABILITY STATEMENT
Research data are not shared.
Supporting Information
Filename | Description |
---|---|
app53328-sup-0001-Supinfo.docxWord 2007 document , 2.2 MB | Appendix S1: Supporting Information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
REFERENCES
- 1R. Kumar, C. Manna, S. Padha, A. Verma, P. Sharma, A. Dhar, A. Ghosh, P. Bhattacharya, Chemosphere 2022, 298, 134267.
- 2M. Bergmann, F. Collard, J. Fabres, G. W. Gabrielsen, J. F. Provencher, C. M. Rochman, E. V. Sebille, M. B. Tekman, Nat. Rev. Earth Environ. 2022, 3, 323.
- 3C. Çevik, A. E. Kıdeyş, U. N. Tavşanoğlu, G. B. Kankılıç, S. Gündoğdu, Environ. Sci. Pollut. Res. 2022, 29, 26230.
- 4S. Kasavan, S. Yusoff, M. F. R. Fakri, R. Siron, J. Clean. Prod. 2021, 313, 127946.
- 5S. H. Kamarudin, M. Rayung, F. Abu, S. Ahmad, F. Fadil, A. A. Karim, M. N. Norizan, N. Sarifuddin, M. S. Z. M. Desa, L. C. Abdullah, Polymer 2022, 14, 174.
- 6V. Siracusa, P. Rocculi, S. Romani, M. D. Rosa, Trends Food Sci. Technol. 2008, 19, 634.
- 7P. Rai, S. Mehrotra, S. Priya, E. Gnasounou, S. K. Sharma, Bioresour. Technol. 2021, 325, 124739.
- 8A. F. Garcia, B. H. Osorio, R. Y. A. Loredo, H. L. Calambas, C. Caicedo, Carbohydr. Polym. 2022, 293, 119744.
- 9H. S. Ghari, H. Nazockdast, Polymer 2022, 245, 124729.
- 10A. Gamage, A. Liyanapathiranage, A. Manamperi, C. Gunathilake, S. Mani, O. Merah, T. Madhujith, Sustainability. 2022, 14, 6085.
- 11X. Tang, P. Kumar, S. Alavi, K. Sandeep, Crit. Rev. Food Sci. Nutr. 2012, 52, 426.
- 12U. Sonchaeng, F. Iniguez-Franco, R. Auras, S. Selke, M. Rubino, L. T. Lim, Prog. Polym. Sci. 2018, 86, 85.
- 13T. Narancic, F. Cerrone, N. Beagan, K. E. O'Connor, Polymer 2021, 12, 920.
- 14S. Singha, M. S. Hedenqvist, Polymer 2020, 12, 1095.
- 15E. Balla, V. Daniilidis, G. Karlioti, T. Kalamas, M. Stefanidou, N. D. Bikiaris, A. Vlachopoulos, I. Koumentakou, D. N. Bikiaris, Polymer 1822, 2021, 13.
- 16T. P. Haider, C. Völker, J. Kramm, K. Landfester, F. R. Wurm, Angew. Chem. Int. Ed. 2019, 58, 50.
- 17G. X. Wang, D. Huang, J. H. Ji, C. Völker, F. R. Wurm, Adv. Sci. 2021, 8, 2001121.
- 18P. K. Samantaray, A. Little, A. M. Wemyss, E. Iacovidou, C. Wan, ACS Sustain. Chem. Eng. 2021, 9, 9151.
- 19A. Little, A. M. Wemyss, D. M. Haddleton, B. Tan, Z. Sun, Y. Ji, C. Wan, Polymer 2020, 13, 2458.
- 20K. Yamane, H. Sato, Y. Ichikawa, K. Sunagawa, Y. Shigaki, Polym. J. 2014, 46, 769.
- 21K. J. Jem, B. Tan, Adv. Ind. Eng. Polym. Res. 2019, 3, 60.
- 22C. V. Rocha, V. Goncalves, M. C. D. Silva, M. B. Lopez, J. Gallo, Int. J. Mol. Sci. 2022, 23, 2034.
- 23A. Hasan, S. Soliman, F. E. Hajj, Y. T. Tseng, H. C. Yalcin, H. E. Marei, Sci. Rep. 2018, 8, 8187.
- 24E. Snejdrova, J. Loskot, J. Martiska, T. Soukup, L. Prokes, V. Frolov, T. Kucera, J. Drug Deliv. Sci. Technol. 2022, 73, 103435.
- 25M. A. Murcia Valderrama, R. J. van Putten, G. J. M. Gruter, ACS Appl. Polym. Mater. 2020, 2, 2706.
- 26P. K. Samantaray, A. Little, D. Haddleton, T. McNally, B. Tan, Z. Sun, W. Huang, Y. Ji, C. Wan, Green Chem. 2020, 22, 4055.
- 27M. L. Adams, A. Lavasanifar, G. S. Kwon, J. Pharm. Sci. 2003, 92, 1343.
- 28R. M. Stayshich, T. Y. Meyer, J. Am. Chem. Soc. 2010, 132, 10920.
- 29K. Hamad, M. Kaseem, M. Ayyoob, J. H. Joo, F. Deri, Prog. Polym. Sci. 2018, 85, 83.
- 30A. Meduri, T. Fuoco, M. Lamberti, C. Pellecchia, D. Pappalardo, Macromolecules 2014, 47, 534.
- 31P. M. Schäfer, S. Herres-Pawlis, Chem. Plus. Chem. 2020, 85, 1044.
10.1002/cplu.202000252 Google Scholar
- 32O. Dechy-Cabaret, B. Martin-Vaca, D. Bourissou, Chem. Rev. 2004, 104, 6147.
- 33D. Gilding, A. Reed, Polymer 1975, 20, 1459.
- 34P. Dobrzynski, J. Kasperczyk, H. Janeczek, M. Bero, Macromolecules 2001, 34, 5090.
- 35P. Dobrzynski, J. Kasperczyk, H. Janeczek, M. Bero, Polymer 2002, 43, 2595.
- 36N. Wang, X. S. Wu, C. Li, M. F. Feng, J. Biomater. Sci. Polym. Ed. 2000, 11, 301.
- 37C. D. C. Erbetta, R. J. Alves, J. Magalh, R. F. de Souza Freitas, R. G. de Sousa, J. Biomater. Nanobiotechnol. 2012, 3, 18940.
- 38Y. Yu, G. Storti, M. Morbidelli, Ind. Eng. Chem. Res. 2011, 50, 7927.
- 39S.-H. Hyon, K. Jamshidi, Y. Ikada, Biomaterials 1997, 18, 1503.
- 40K. Shinno, M. Miyamoto, Y. Kimura, Y. Hirai, H. Yoshitome, Macromolecules 1997, 30, 6438.
- 41A. Kowalski, A. Duda, S. Penczek, Macromolecules 2000, 33, 7359.
- 42K. Jamshidi, S.-H. Hyon, Y. Ikada, Polymer 1988, 29, 222.
- 43O. F. Solomon, I. Z. Ciuta, J. Appl. Polym. Sci. 1962, 6, 683.
- 44A. K. Richard, O. L. Maryann, T. R. Mahoney, M. S. Lynda, Macromolecules 1987, 20, 2398.
- 45I. G. I. Athanasoulia, M. N. Christoforidis, D. M. Korres, P. A. Tarantili, Pure Appl. Chem. 2017, 89, 125.
- 46E. Altay, Y. J. Jang, X. Q. Kua, M. A. Hillmyer, Biomacromolecules 2021, 22, 2532.
- 47Y. Mai, A. Eisenberg, Chem. Soc. Rev. 2012, 41, 5969.
- 48A. Kozbial, Z. Li, C. Conaway, R. McGinley, S. Dhingra, V. Vahdat, E. Zhou, B. D'Urso, H. T. Liu, L. Li, Langmuir 2014, 30, 8598.