Synthesis and Photoinitiated Crosslinking of Active Poly(lactic acid) Materials

Abstract

Acrylate-terminated poly(lactic acid) (DPLA) was synthesized by polycondensation, using lactic acid, polyalcohol and acrylic acid as the raw materials. The prepolymer products in each process were characterized by FT-IR, ¹H-NMR, GPC and DSC. DPLAs were then formulated with reactive diluent and diphenyl ketone as photoinitiator and photopolymerized into film(FPLA). Thermal stability and degradation properties of the UV curing PLA film were studied. The results showed that the structures of prepolymer and the performances of the film could be adjusted by changing the types and content of the branching agent polyalcohol. After crosslinking modification, the degradation rate of FPLA was reduced and FPLA had better thermal stability than the pure PLA.

Keywords

photoactivity / PLA / UV curing / biodegradable

References

[1] Fortunati E, Armentano I, Iannoni A, et al. Development and Thermal Behaviour of Ternary PLA Matrix Composites[J]. Polym. Degrad. Stab., 2010, 95(11): 2200-2206.

[2] Vieira A C, Marques A T, Guedes R M, et al. Material Model Proposal for Biodegradable Materials[J]. Procedia Engineering, 2011, 10(7): 1597-1602.

[3] Vroman I, Tighzert L. Biodegradable Polymers[J]. Materials, 2009, 2(2): 307-344.

[4] Garlotta D A. Literature Review of Poly(Lactic Acid)[J]. J. Polym. Environ., 2001, 9(2): 63-84.

[5] Lim L T, Auras R, Rubino M. Processing Technologies for Poly(Lactic Acid)[J]. Prog. Polym. Sci., 2008, 33(8): 820-852.

[6] Singh S, Ray S S. Polylactide Based Nanostructured Biomaterials and Their Applications[J]. J. Nanosci. Nanotechnol., 2007, 7(8): 2596-2615.

[7] Chen Y, Lin J, Wan Y Q, et al. Preparation and Blood Compatibility of Electrospun PLA/Curcumin Composite Membranes[J]. Fiber. Polym., 2012, 13(10): 1254-1258.

[8] Lin L H, Liu H J, Yu N K. Morphology and Thermal Properties of Poly(L-Lactic Acid)/Organoclay Nanocomposites[J]. J. Appl. Polym. Sci., 2007, 106(1): 260-265.

[9] Auras R, Harte B, Swlke S. An Overview of Polylactides as Packaging Materials[J]. Macromol. Biosci., 2004, 4(9): 835-864.

[10] Li H, Wang C H, Yue J, et al. Living Ring-Opening Polymerization of Lactides Catalyzed by Guanidinium Acetate[J]. Polym. Sci.: Polym. Chem., 2004, 42(15): 3775-3781.

[11] Takasu A, Narukawa Y, Hirabayashi T J. Direct Dehydration Polycondensation of Lactic Acid Catalyzed by Water-Stable Lewis Acids[J]. Polym. Sci., Part A: Polym. Chem., 2006, 44(18): 5247-5253.

[12] Chen G X, Kim H S K E S, et al. Synthesis of High-Molecular-Weight Poly(L-Lactic Acid)Through the Direct Condensation Polymerization of L-Lactic Acid in Bulk State[J]. Eur. Polym. J., 2006, 42(2): 468-472.

[13] Hakala R A, Korhonen H, Seppälä J V. Hydrolysis Behaviour of Crosslinked Poly(Ester Anhydride) Networks Prepared from Functionalised Poly(e-Caprolactone) Precursors[J]. React. Funct. Polym., 2013, 73(1): 11-17.

[14] Koo G H, Jang J h. Preparation of Melting-Free Poly(Lactic Acid) by Amorphous and Crystal Crosslinking under UV Irradiation[J]. J. Appl. Polym. Sci., 2013, 127(6): 4515-4523.

[15] Quyhh T M, Mitomo H, Nagasawa N, et al. Properties of Crosslinked Polylactides (PLLA & PDLA) by Radiation and Its Biodegradability[J]. Eur. Polym. J., 2007, 43(5): 1779-1785.

[16] Xu C G, Luo X G, Zhou X R. Research on Crosslinking of Polylactide Using Low Concentration of Dicumyl Peroxide[J]. Mater. Sci. Forum, 2009, 620-622: 189-192.

[17] Yang S L, Wu Z H, Yang W. Thermal and Mechanical Properties of Chemically Crosslinked Polylactide (PLA)[J]. Polym. Test, 2008, 27(8): 957-963.

[18] Chang S K, Zeng C, Li J b. Synthesis of Polylactide-Based Thermoset Resin and Its Curing Kinetics[J]. Polym. Int., 2012, 61(10): 1492-1502.

[19] Ali M A, Ooi T L, Salmiah A, et al. New Polyester Acrylate Resins from Palm Oil for Wood Coating Application[J]. J. Appl. Polym. Sci., 2001, 79(12): 2156-2163.

[20] Raquez J M, Deléglise M, Lacrampe M F, et al. Thermosetting (Bio) Materials Derived from Renewable Resources: A Critical Review[J]. Progress in Polymer Science, 2010, 35(4): 487-509.

[21] Bajpai M, Shukla V, Singh D K, et al. A Study of the Film Properties of Pigmented UV-Curable Epoxidised Soybean Oil[J]. Resin Technol., 2004, 33(3): 160-164.

[22] Bunker S P, Wool R P. Synthesis and Characterization of Monomers and Polymers for Adhesives from Methyl Oleate[J]. J. Polym. Sci.: Polym. Chem., 2002, 40(4): 451-458.

[23] Bunker S, Staller C, Willenbacher N, et al. Miniemulsion Polymerization of Acrylated Methyl Oleate for Pressure Sensitive Adhesives[J]. Int. J. Adhes. Adhes., 2003, 23(1): 29-38.

[24] Miller K R, Soucek M D. Photopolymerization of Biocompatible Films Containing Poly(Lactic Acid)[J]. Eur. Polym. J., 2012, 48(12): 2107-2116.

[25] Akessona D, Skrifvars M, Lv S C. Preparation of Nanocomposites from Bio-Based Thermoset Resins by UV-Curing [J]. Prog. Org. Coat., 2010, 67(3): 281-286.

[26] Zhao X P, Wu T, Lin Q, et al. Synthesis and Characterization of Optical Active PLA Degradable Materials[J]. Mater. Sci. Forum, 2015, 815: 464-469.

[27] Signori F, Coltelli M B, Bronco S. Thermal Degradation of Poly(Lactic Acid) (PLA) and Poly(Butylene Adipate-Co-Terephthalate) (PBAT) and Their Blends upon Melt Processing[J]. Polym. Degrad. Stabil., 2009, 94(1): 74-82.