Citation: Jia-Xing Wang, Yan-Bin Huang, Wan-Tai Yang. Photo-grafting Poly(acrylic acid) onto Poly(lactic acid) Chains in Solution[J]. Chinese Journal of Polymer Science, ;2020, 38(2): 137-142. doi: 10.1007/s10118-019-2308-y shu

Photo-grafting Poly(acrylic acid) onto Poly(lactic acid) Chains in Solution

Department of Chemical Engineering, Tsinghua University, Beijing 100084, China

Corresponding author: Yan-Bin Huang, yanbin@tsinghua.edu.cn
Received Date: 12 May 2019
Revised Date: 23 May 2019
Available Online: 12 September 2019

Poly(lactic acid) (PLA) is one of the most important bio-plastics, and chemical modification of the already-polymerized poly(lactic acid) chains may enable optimization of its material properties and expand its application areas. In this study, we demonstrated that poly(lactic acid) can be readily dissolved in acrylic acid at room temperature, and acrylic acid can be graft-polymerized onto poly(lactic acid) chains in solution with the help of photoinitiator benzophenone under 254 nm ultraviolet (UV) irradiation. Similar photo-grafting polymerization of acrylic acid (PAA) has only been studied before in the surface modification of polymer films. The graft ratio could be controlled by various reaction parameters, including irradiation time, benzophenone content, and monomer/polymer ratios. This photo-grafting reaction resulted in high graft ratio (graft ratio PAA/PLA up to 180%) without formation of homopolymers of acrylic acid. When the PAA/PLA graft ratio was higher than 100%, the resulting PLA-g-PAA polymer was found dispersible in water. The pros and cons of the photo-grafting reaction were also discussed.
- Photo-grafting,
- Polymer modification,
- Poly(acrylic acid),
- Poly(lactic acid)
1. [1]
  Di Lorenzo, M. L.; Androsch R. (eds.) Synthesis, structure and properties of poly(lactic acid). Springer, Switzerland, 2018, p. 1.
2. [2]
  Aurus, R.; Lim, L.; Selke, S. E. M.; Tsuji, H. (eds.) Poly(lactic acid): synthesis, structures, properties, processing, and applications. Wiley, Canada, 2010, p. 141.
3. [3]
  Krishnan, S.; Pandey, P.; Mohanty, S.; Nayak, S. K. Toughening of poly(lactic acid): an overview of research progress. Polym. Plastic. Tech. Eng. 2016, 55, 1623−1652. doi: 10.1080/03602559.2015.1098698
4. [4]
  Ramot, Y.; Haim-Zada, M.; Domb, A. J.; Nyska, A. Biocompatibility and safety of PLA and its copolymers. Adv. Drug Deliver. Rev. 2016, 107, 153−159. doi: 10.1016/j.addr.2016.03.012
5. [5]
  Tyler, B.; Gullotti, D.; Mangraviti, A.; Utsuki, T.; Brem, H. Poly(lactic acid) (PLA) controlled delivery carriers for biomedical applications. Adv. Drug Deliver. Rev. 2016, 107, 163−168. doi: 10.1016/j.addr.2016.06.018
6. [6]
  Rasal, R. M.; Janorkar, A. V.; Hirt, D. E. Poly(lactic acid) modifications. Prog. Polym. Sci. 2010, 35, 338−356. doi: 10.1016/j.progpolymsci.2009.12.003
7. [7]
  Critechfield, F. E.; Koleske, J. V. US Patent 3, 760, 034, 1973.
8. [8]
  Wu, C. Improving polylactide/starch biocomposites by grafting polylactide with acrylic acid—characterization and biodegradability assessment. Macromol. Biosci. 2005, 5, 352−361. doi: 10.1002/(ISSN)1616-5195
9. [9]
  Dorman, G.; Nakamura, H.; Pulsipher, A.; Prestwich, G. D. The life of pi star: exploring the exciting and forbidden worlds of the benzophenone photophore. Chem. Rev. 2016, 116, 15284−15398. doi: 10.1021/acs.chemrev.6b00342
10. [10]
  Yang, W. T.; Ranby, B. Bulk surface photografting process and its applications. I. Reactions and kinetics. J. Appl. Polym. Sci. 1996, 62, 533−543. doi: 10.1002/(ISSN)1097-4628
11. [11]
  Li, Y.; DeSimone, J. M.; Poon, C.; Samulski, E. T. Photoinduced graft polymerization of styrene onto polypropylene substrates. J. Appl. Polym. Sci. 1997, 64, 883−889. doi: 10.1002/(ISSN)1097-4628
12. [12]
  Ranby, B.; Yang, W. T. Tretinnikov, V. Tokarev, V.; Xu, Y. H. Lamination of polymer films by bulk surface photografting process and properties. Chinese J. Polym. Sci. 2001, 19, 123−127.
13. [13]
  Yang, W. T.; Ranby, B. Bulk surface photografting process and its applications. II. Principal factors affecting surface photografting. J. Appl. Polym. Sci. 1996, 62, 545−555. doi: 10.1002/(ISSN)1097-4628
14. [14]
  Ma, H.; Davis, R. H.; Bowman, C. N. A novel sequential photoinduced living graft polymerization. Macromolecules 2000, 33, 331−335. doi: 10.1021/ma990821s
15. [15]
  Janorkar, A. V.; Metters, A. T.; Hirt, D. E. Modification of poly(lactic acid) films: enhanced wettability from surface-confined photografting and increased degradation rate due to an artifact of the photografting process. Macromolecules 2004, 37, 9151−9159. doi: 10.1021/ma049056u
16. [16]
  Ikada, E. Photo- and bio-degradable polyesters, photodegradation behaviours of aliphatic polyesters. J. Photopolym. Sci. Tech. 1997, 10, 265−269. doi: 10.2494/photopolymer.10.265
17. [17]
  Tsuji, H.; Echizen, Y.; Nishimura, Y. Photodegradation of biodegradable polyesters: a comprehensive study on poly(L-lactide) and poly(ε-caprolactone). Polym. Degrad. Stab. 2006, 91, 1128−1137. doi: 10.1016/j.polymdegradstab.2005.07.007
18. [18]
  Li, L.; Raghupathi, K.; Song, C.; Prasad, P.; Thayumanavan, S. Self-assembly of random copolymers. Chem. Commun. 2014, 50, 13417−13432. doi: 10.1039/C4CC03688C
19. [19]
  Zhou, Y.; Liu, B.; Wang, X. Self-assembly of homopolymers through strong dipole-dipole interaction in their aqueous solutions. Polymer 2016, 97, 1−10. doi: 10.1016/j.polymer.2016.05.011
20. [20]
  Choucair, A.; Lavigueur, C.; Eisenberg, A. Polystyrene-b-poly(acrylic acid) vesicle size control using solution properties and hydrophilic block length. Langmuir 2004, 20, 3894−3900. doi: 10.1021/la035924p
21. [21]
  McNeill, I. C.; Sadeghi, S. M. T. Thermal-stability and degradation mechanisms of poly(acrylic acid) and its salts. I. Poly(acrylic acid). Polym. Degrad. Stab. 1990, 29, 233. doi: 10.1016/0141-3910(90)90034-5
22. [22]
  Chen, L.; Hu, K.; Sun, S.; Jiang, H.; Huang, D.; Zhang, K.; Pan, L.; Li, Y. Toughening poly(lactic acid) with imidazolium-based elastomeric ionomers. Chinese J. Polym. Sci. 2018, 36, 1342−1352. doi: 10.1007/s10118-018-2143-6
23. [23]
  Zhang, J.; Jia, J.; Kim, J. P.; Shen, H.; Yang, F.; Zhang, Q.; Xu, M.; Bi, W.; Wang, X.; Yang, J.; Wu, D. Ionic colloidal molding as a biomimetic scaffolding strategy for uniform bone tissue regeneration. Adv. Mater. 2017, 29, 1605546−1605554. doi: 10.1002/adma.v29.17
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