Skip to main content
Log in

Melt synthesis and characterization of poly(L-lactic acid) chain linked by multifunctional epoxy compound

  • Published:
Journal of Wuhan University of Technology-Mater. Sci. Ed. Aims and scope Submit manuscript

Abstract

High molecular weight(Mw) poly(L-lactic acid)s(PLLAs) were synthesized using multifunctional epoxy compound(Joncryl-ADR4370) as chain extender. The products were characterized by gel permeation chromatography(GPC) and spectroscopy(1HNMR and FTIR). The results indicated that the Mw of PLLA increased with the increasing of the ratio of epoxy compound and the extending of reaction time. The highest M w of PLLA reached 360 000 g/mol when the ratio of epoxy compound was 1.5 wt%. However, the reactants turned to cross-linking when the ratio of epoxy compound was over 1.5 wt%. Differential scanning calorimetry(DSC) measurements demonstrated that the glass transition(T g) and melting temperatures(T m ) of products increased slightly as the increase of the molecular weight. Analysis of the hydrolytic degradation in vitro showed that the branched PLLA possessed the quicker degradability than that of the linear PLLA.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. A Sodergard, M Stolt. Properties of Lactic Acid Based Polymers and Their Correlation with Composition[J]. Prog. Polym. Sci., 2002, 27: 1 123–1 163

    Article  CAS  Google Scholar 

  2. B Gupta, N Revagade, J Hilborn. Poly (Lactic Acid) Fiber: An Overview[J]. Prog. Polym. Sci., 2007, 32: 455–482

    Article  CAS  Google Scholar 

  3. N D Luong, I S Moon, D Lee, et al. Surface Modification of Poly(L-Lactide) Electrospun Fibers with Nanocrystal Hydroxyapatite for Engineered Scaffold Applications[J]. Materials Science and Engineering C, 2008, 28: 1 242–1 249

    Article  CAS  Google Scholar 

  4. F Yang, R Murugan, S Wang, et al. Electrospinning of Nano/Micro Scale Poly (L-Lactic Acid) Aligned Fibers and Their Potential in Neural Tissue Engineering[J]. Biomaterials, 2005, 26: 2 603–2 610

    CAS  Google Scholar 

  5. X H Liu, Y J Won, P X Ma. Porogen-induced Surface Modification of Nano-fibrous Poly (L-Lactic Acid) Scaffolds for Tissue Engineering[J]. Biomaterials, 2006, 27: 3 980–3 987

    CAS  Google Scholar 

  6. B Jeong, Y K Choi, Y H Bae, et al. New Biodegradable Polymers for Injectable Drug Delivery Systems[J]. Journal of Controlled Release, 1999, 62: 109–114

    Article  CAS  PubMed  Google Scholar 

  7. M S Papkov, K Agashi, A Olaye, et al. Polymer Carriers for Drug Delivery in Tissue Engineering[J]. Advanced Drug Delivery Reviews, 2007, 59: 187–206

    Article  Google Scholar 

  8. Y Q Li, H B You. Polymer Architecture and Drug Delivery[ J]. Pharmaceutical Research, 2006, 23: 1–30

    Article  Google Scholar 

  9. R A Gross, B Kalra. Biodegradable Polymers for the Environment[ J]. Science, 2002, 297: 803–807

    Article  CAS  ADS  PubMed  Google Scholar 

  10. R Hans, Kricheldorf. Syntheses and Application of Polylactides[J]. Chemosphere, 2001, 43: 49–54

    Article  Google Scholar 

  11. R Mehta, V Kumar, H Bhunia, et al. Synthesis of Poly (Lactic Acid): A Review[J]. Journal of Macromolecular Sciencew, Part C: Polymer Reviews, 2005, 45:325–349

    Article  Google Scholar 

  12. S Kaihara, S Matsumura, A G Mikos, et al. Synthesis of Poly(L-Lactide) and Polyglycolide by Ring-opening Polymerization[ J]. Nature Protocols, 2007, 2: 2 767–2 771

    Article  CAS  Google Scholar 

  13. S I Woo, B O Kim, H S Jun, et al. Polymerization of Aqueous Lactic Acid to Prepare High Molecular Weight Poly(Lactic Scid) by Chain-extending with Hexamethylene Diisocyanate[J]. Polymer Bulletin, 1995, 35: 415–421

    Article  CAS  Google Scholar 

  14. J Kylma, J Tuominen, A Helminen, et al. Chain Extending of Lactic Acid Oligomers. Effect of 2, 20-bis (2-Oxazoline) on 1,6-Hexamethylene Diisocyanate Linking Reaction[J]. Polymer, 2001, 42: 3 333–3 343

    Article  CAS  Google Scholar 

  15. J Tuominen, J Kylma, J Seppala. Chain Extending of Lactic Acid Oligomers.2.Increase of Molecular Weight with 1, 6-Hexamethylene Diisocyanate and 2, 2-bis (2-oxazoline)[J]. Polymer, 2002, 43: 3–10

    Article  CAS  Google Scholar 

  16. J Ren, Q F Wang, S Y Gu, et al. Chain-Linked Lactic Acid Polymers by Benzene Diisocyanate[J]. Journal of Applied Polymer Science, 2006, 99: 1 045–1 049

    Article  CAS  Google Scholar 

  17. B H Li, M C Yang. Improvement of Thermal and Mechanical Properties of Poly(L-; Lactic Acid) with 4, 4-Methylene Diphenyl Diisocyanate[J]. Polymers for Advanced Technologies, 2006, 17: 439–443

    Article  CAS  Google Scholar 

  18. M Villalobos, A Awojulu, T Greeley, et al. Oligomeric Chain Extenders for Economic Reprocessing and Recycling of Condensation Plastics[J]. Energy, 2006, 31: 3 227–3 234

    Article  CAS  Google Scholar 

  19. M G McKee, S Unal, G L Wilkes, et al. Branched Polyesters: Recent Advances in Synthesis and Performance[J]. Polym. Sci., 2005, 30: 507–539

    CAS  Google Scholar 

  20. J R Dorgan, H Lehermeier, M Mang. Thermal and Rheological Properties of Commercial-Grade Poly (Lactic Acid)s[J]. Journal of Polymers and the Environment, 2000, 8: 1–9

    Article  Google Scholar 

  21. X C Zhang, U P Wyss, D Pichora, et al. An Investigation of Poly(Lactic Dcid) Degradation[J]. Journal of Bioactive and Compatible Polymers, 1994, 9: 80–100

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yuanliang Wang  (王远亮).

Additional information

Funded by the National Natural Science Foundation of China (No. 30870609), the Natural Science Foundation of Chongqing (Nos.2009BA4025 and CSTC2009BB4382) and the Foundation of Chongqing Municipal Education Commission(No.KJ091415)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Wang, Y., Fu, C., Luo, Y. et al. Melt synthesis and characterization of poly(L-lactic acid) chain linked by multifunctional epoxy compound. J. Wuhan Univ. Technol.-Mat. Sci. Edit. 25, 774–779 (2010). https://doi.org/10.1007/s11595-010-0090-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11595-010-0090-3

Key words

Navigation