Biorenewable Tough Blends of Polylactide and Acrylated Epoxidized Soybean Oil Compatibilized by a Polylactide Star Polymer

Macromolecules

Volumn 49, Issue 5, 2016, Pages 1605-1615

  Mauck, Sheli C ^a   Wang, Shu ^a   Ding, Wenyue ^a   Rohde, Brian J ^a   Fortune, C Karen ^a   Yang, Guozhen ^a   Ahn, Suk Kyun ^b,c   Robertson, Megan L ^a  

^a UNIVERSITY OF HOUSTON   (United States)

^b OAK RIDGE NATIONAL LABORATORY   (United States)

^c Pusan National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITIVES; CONSUMER PRODUCTS; DROPS; FRACTURE MECHANICS; FRACTURE TOUGHNESS; GLASS TRANSITION; IMPACT STRENGTH; POLYESTERS; POLYMER BLENDS; POLYMERS;

ACRYLATED EPOXIDIZED SOYBEAN OIL; ELEVATED TEMPERATURE; ELONGATION AT BREAK; INTERPARTICLE DISTANCES; MECHANICAL BEHAVIOR; OIL DROPLET SIZE DISTRIBUTION; REACTIVE COMPATIBILIZATION; TUNABLE PROPERTIES;

SOYBEAN OIL;

EID: 84960461920     PISSN: 00249297     EISSN: 15205835     Source Type: Journal    
DOI: 10.1021/acs.macromol.5b02613     Document Type: Article

References (69)

1. Wilbon, P. A.; Chu, F.; Tang, C. Progress in Renewable Polymers from Natural Terpenes, Terpenoids, and Rosin Macromol. Rapid Commun. 2013, 34 (1) 8-37 10.1002/marc.201200513
2. Inkinen, S.; Hakkarainen, M.; Albertsson, A.-C.; Södergård, A. From Lactic Acid to Poly(lactic acid) (PLA): Characterization and Analysis of PLA and Its Precursors Biomacromolecules 2011, 12 (3) 523-532 10.1021/bm101302t
3. Gandini, A. The irruption of polymers from renewable resources on the scene of macromolecular science and technology Green Chem. 2011, 13 (5) 1061-1083 10.1039/c0gc00789g
4. Biermann, U.; Bornscheuer, U.; Meier, M. A. R.; Metzger, J. O.; Schäfer, H. J. Oils and Fats as Renewable Raw Materials in Chemistry Angew. Chem., Int. Ed. 2011, 50 (17) 3854-3871 10.1002/anie.201002767
5. Galia, M.; de Espinosa, L. M.; Ronda, J. C.; Lligadas, G.; Cadiz, V. Vegetable oil-based thermosetting polymers Eur. J. Lipid Sci. Technol. 2010, 112 (1) 87-96 10.1002/ejlt.200900096
6. Sudesh, K.; Iwata, T. Sustainability of biobased and biodegradable plastics Clean: Soil, Air, Water 2008, 36 (5-6) 433-442 10.1002/clen.200700183
7. Meier, M. A. R.; Metzger, J. O.; Schubert, U. S. Plant oil renewable resources as green alternatives in polymer science Chem. Soc. Rev. 2007, 36, 1788-1802 10.1039/b703294c
8. Bhardwaj, R.; Mohanty, A. K. Advances in the properties of polylactides based materials: A review J. Biobased Mater. Bioenergy 2007, 1 (2) 191-209 10.1166/jbmb.2007.023
9. Datta, R.; Henry, M. Lactic acid: recent advances in products, processes and technologies-a review J. Chem. Technol. Biotechnol. 2006, 81 (7) 1119-1129 10.1002/jctb.1486
10. Garlotta, D. A literature review of poly(lactic acid) J. Polym. Environ. 2001, 9 (2) 63-84 10.1023/A:1020200822435
11. Liu, H.; Zhang, J. Research progress in toughening modification of poly(lactic acid) J. Polym. Sci., Part B: Polym. Phys. 2011, 49 (15) 1051-1083 10.1002/polb.22283
12. Rasal, R. M.; Janorkar, A. V.; Hirt, D. E. Poly(lactic acid) modifications Prog. Polym. Sci. 2010, 35 (3) 338-356 10.1016/j.progpolymsci.2009.12.003
13. Anderson, K. S.; Schreck, K. M.; Hillmyer, M. A. Toughening polylactide Polym. Rev. 2008, 48, 85-108 10.1080/15583720701834216
14. Gramlich, W. M. Toughening Polylactide with Phase-Separating Complex Copolymer Architectures Macromol. Chem. Phys. 2015, 216 (2) 145-155 10.1002/macp.201400350
15. Kim, K.-S.; Chin, I.-J.; Yoon, J. S.; Choi, H. J.; Lee, D. C.; Lee, K. H. Crystallization behavior and mechanical properties of poly(ethylene oxide)/poly(L-lactide)/poly(vinyl acetate) blends J. Appl. Polym. Sci. 2001, 82 (14) 3618-3626 10.1002/app.2224.abs
16. Han, J.-J.; Huang, H.-X. Preparation and characterization of biodegradable polylactide/thermoplastic polyurethane elastomer blends J. Appl. Polym. Sci. 2011, 120 (6) 3217-3223 10.1002/app.33338
17. Anderson, K. S.; Lim, S. H.; Hillmyer, M. A. Toughening of polylactide by melt blending with linear low-density polyethylene J. Appl. Polym. Sci. 2003, 89 (14) 3757-3768 10.1002/app.12462
18. Anderson, K. S.; Hillmyer, M. A. The influence of block copolymer microstructure on the toughness of compatibilized polylactide/polyethylene blends Polymer 2004, 45 (26) 8809-8823 10.1016/j.polymer.2004.10.047
19. Broz, M. E.; VanderHart, D. L.; Washburn, N. R. Structure and mechanical properties of poly(d,l-lactic acid)/poly(ε-caprolactone) blends Biomaterials 2003, 24 (23) 4181-4190 10.1016/S0142-9612(03)00314-4
20. Jiang, L.; Wolcott, M. P.; Zhang, J. Study of biodegradable polyactide/poly(butylene adipate-co-terephthalate) blends Biomacromolecules 2006, 7 (1) 199-207 10.1021/bm050581q
21. Pezzin, A. P. T.; Van Ekenstein, G. O. R. A.; Zavaglia, C. A. C.; Ten Brinke, G.; Duek, E. A. R. Poly(para-dioxanone) and poly(L-lactic acid) blends: thermal, mechanical, and morphological properties J. Appl. Polym. Sci. 2003, 88 (12) 2744-2755 10.1002/app.11984
22. Zhang, K.; Mohanty, A. K.; Misra, M. Fully Biodegradable and Biorenewable Ternary Blends from Polylactide, Poly(3-hydroxybutyrate-co-hydroxyvalerate) and Poly(butylene succinate) with Balanced Properties ACS Appl. Mater. Interfaces 2012, 4 (6) 3091-3101 10.1021/am3004522
23. Yoon, J.-S.; Lee, W.-S.; Kim, K.-S.; Chin, I.-J.; Kim, M.-N.; Kim, C. Effect of poly(ethylene glycol)-block-poly(L-lactide) on the poly[(R)-3-hydroxybutyrate]/poly(L-lactide) blends Eur. Polym. J. 2000, 36 (2) 435-442 10.1016/S0014-3057(99)00068-3
24. Ma, X.; Yu, J.; Wang, N. Compatibility characterization of poly(lactic acid)/poly(propylene carbonate) blends J. Polym. Sci., Part B: Polym. Phys. 2006, 44 (1) 94-101 10.1002/polb.20669
25. Liu, T.-Y.; Lin, W.-C.; Yang, M.-C.; Chen, S.-Y. Miscibility, thermal characterization and crystallization of poly(l-lactide) and poly(tetramethylene adipate-co-terephthalate) blend membranes Polymer 2005, 46 (26) 12586-12594 10.1016/j.polymer.2005.10.100
26. Hazer, B. The Properties of PLA/Oxidized Soybean Oil Polymer Blends J. Polym. Environ. 2014, 22 (2) 200-208 10.1007/s10924-014-0645-z
27. Silverajah, V. S. G.; Ibrahim, N. A.; Yunus, W. M. Z. W.; Hassan, H. A.; Woei, C. B. A Comparative Study on the Mechanical, Thermal and Morphological Characterization of Poly(lactic acid)/Epoxidized Palm Oil Blend Int. J. Mol. Sci. 2012, 13 (5) 5878 10.3390/ijms13055878
28. Xu, Y.-Q.; Qu, J.-P. Mechanical and rheological properties of epoxidized soybean oil plasticized poly(lactic acid) J. Appl. Polym. Sci. 2009, 112 (6) 3185-3191 10.1002/app.29797
29. Vijayarajan, S.; Selke, S. E. M.; Matuana, L. M. Continuous Blending Approach in the Manufacture of Epoxidized Soybean-Plasticized Poly(lactic acid) Sheets and Films Macromol. Mater. Eng. 2014, 299 (5) 622-630 10.1002/mame.201300226
30. Ali, F.; Chang, Y. W.; Kang, S. C.; Yoon, J. Y. Thermal, mechanical and rheological properties of poly (lactic acid)/epoxidized soybean oil blends Polym. Bull. 2009, 62 (1) 91-98 10.1007/s00289-008-1012-9
31. Al-Mulla, E. A. J.; Yunus, W. M. Z. W.; Ibrahim, N. A. B.; Ab Rahman, M. Z. Properties of epoxidized palm oil plasticized polytlactic acid J. Mater. Sci. 2010, 45 (7) 1942-1946 10.1007/s10853-009-4185-1
32. Chieng, B. W.; Ibrahim, N. A.; Then, Y. Y.; Loo, Y. Y. Epoxidized Vegetable Oils Plasticized Poly(lactic acid) Biocomposites: Mechanical, Thermal and Morphology Properties Molecules 2014, 19 (10) 16024-16038 10.3390/molecules191016024
33. Fu, C.; Zhang, B.; Ruan, C.; Hu, C.; Fu, Y.; Wang, Y. Improved hydrolytic stability of poly(dl-lactide) with epoxidized soybean oil Polym. Degrad. Stab. 2010, 95 (4) 485-490 10.1016/j.polymdegradstab.2010.01.007
34. Prempeh, N.; Li, J.; Liu, D.; Das, K.; Maiti, S.; Zhang, Y. Plasticizing Effects of Epoxidized Sun Flower Oil on Biodegradable Polylactide Films: A Comparative Study Polym. Sci., Ser. A 2014, 56 (6) 856-863 10.1134/S0965545X14060182
35. Wadhi, M. M.; Weliam, R. Effect of epoxidized sunflower oil on polylactic acid properties Res. Chem. Intermed. 2014, 40 (1) 399-406 10.1007/s11164-012-0971-5
36. Silverajah, V. S. G.; Ibrahim, N. A.; Zainuddin, N.; Yunus, W.; Abu Hassan, H. Mechanical, Thermal and Morphological Properties of Poly(lactic acid)/Epoxidized Palm Olein Blend Molecules 2012, 17 (10) 11729-11747 10.3390/molecules171011729
37. Chang, K. H.; Robertson, M. L.; Hillmyer, M. A. Phase Inversion in Polylactide/Soybean Oil Blends Compatibilized by Poly(isoprene-b-lactide) Block Copolymers ACS Appl. Mater. Interfaces 2009, 1 (10) 2390-2399 10.1021/am900514v
38. Robertson, M. L.; Chang, K. H.; Gramlich, W. M.; Hillmyer, M. A. Toughening of Polylactide with Polymerized Soybean Oil Macromolecules 2010, 43 (4) 1807-1814 10.1021/ma9022795
39. Gramlich, W. M.; Robertson, M. L.; Hillmyer, M. A. Reactive Compatibilization of Poly(L-lactide) and Conjugated Soybean Oil Macromolecules 2010, 43 (5) 2313-2321 10.1021/ma902449x
40. Robertson, M. L.; Paxton, J. M.; Hillmyer, M. A. Tough Blends of Polylactide and Castor Oil ACS Appl. Mater. Interfaces 2011, 3, 3402-3410 10.1021/am2006367
41. Pelletier, H.; Gandini, A. Preparation of acrylated and urethanated triacylglycerols Eur. J. Lipid Sci. Technol. 2006, 108 (5) 411-420 10.1002/ejlt.200501168
42. La Scala, J.; Wool, R. P. The effect of fatty acid composition on the acrylation kinetics of epoxidized triacylglycerols J. Am. Oil Chem. Soc. 2002, 79 (1) 59-63 10.1007/s11746-002-0435-4
43. Campanella, A.; Scala, J. J. L.; Wool, R. P. Fatty acid-based comonomers as styrene replacements in soybean and castor oil-based thermosetting polymers J. Appl. Polym. Sci. 2011, 119 (2) 1000-1010 10.1002/app.32810
44. La Scala, J.; Wool, R. P. Property analysis of triglyceride-based thermosets Polymer 2005, 46 (1) 61-69 10.1016/j.polymer.2004.11.002
45. Bunker, S. P.; Wool, R. P. Synthesis and characterization of monomers and polymers for adhesives from methyl oleate J. Polym. Sci., Part A: Polym. Chem. 2002, 40 (4) 451-458 10.1002/pola.10130
46. Campanella, A.; La Scala, J. J.; Wool, R. P. The Use of Acrylated Fatty Acid Methyl Esters as Styrene Replacements in Triglyceride-based Thermosetting Polymers Polym. Eng. Sci. 2009, 49 (12) 2384-2392 10.1002/pen.21486
47. Huang, S.; Sun, H.; Sun, J.; Li, G.; Chen, X. Biodegradable tough blends of poly(L-lactide) and poly(castor oil)-poly(L-lactide) copolymer Mater. Lett. 2014, 133, 87-90 10.1016/j.matlet.2014.06.133
48. Tsujimoto, T.; Uyama, H. Full Biobased Polymeric Material from Plant Oil and Poly(lactic acid) with a Shape Memory Property ACS Sustainable Chem. Eng. 2014, 2 (8) 2057-2062 10.1021/sc500310s
49. Pratt, R. C.; Lohmeijer, B. G. G.; Long, D. A.; Waymouth, R. M.; Hedrick, J. L. Triazabicyclodecene: A Simple Bifunctional Organocatalyst for Acyl Transfer and Ring-Opening Polymerization of Cyclic Esters J. Am. Chem. Soc. 2006, 128 (14) 4556-4557 10.1021/ja060662+
50. Sveinbjörnsson, B. R.; Miyake, G. M.; El-Batta, A.; Grubbs, R. H. Stereocomplex Formation of Densely Grafted Brush Polymers ACS Macro Lett. 2014, 3 (1) 26-29 10.1021/mz400568j
51. Dorgan, J. R.; Janzen, J.; Knauss, D. M.; Hait, S. B.; Limoges, B. R.; Hutchinson, M. H. Fundamental solution and single-chain properties of polylactides J. Polym. Sci., Part B: Polym. Phys. 2005, 43 (21) 3100-3111 10.1002/polb.20577
52. Liu, Z. H.; Zhang, X. D.; Zhu, X. G.; Li, R. K. Y.; Qi, Z. N.; Wang, F. S.; Choy, C. L. Effect of morphology on the brittle ductile transition of polymer blends: 2. Analysis on poly(vinyl chloride) nitrile rubber blends Polymer 1998, 39 (21) 5019-5025 10.1016/S0032-3861(98)00090-1
53. Fischer, E. W.; Sterzel, H.; Wegner, G. Investigation of the structure of solution grown crystals of lactide copolymers by means of chemical reactions Kolloid Z. Z. Polym. 1973, 251 (11) 980-990 10.1007/BF01498927
54. Witzke, D. R.; Narayan, R.; Kolstad, J. J. Reversible Kinetics and Thermodynamics of the Homopolymerization of l-Lactide with 2-Ethylhexanoic Acid Tin(II) Salt Macromolecules 1997, 30 (23) 7075-7085 10.1021/ma970631m
55. Crist, B.; Nesarikar, A. R. Coarsening in Polyethylene-Copolymer Blends Macromolecules 1995, 28 (4) 890-896 10.1021/ma00108a014
56. Song, S.-W.; Torkelson, J. M. Coarsening effects on the formation of microporous membranes produced via thermally induced phase separation of polystyrene-cyclohexanol solutions J. Membr. Sci. 1995, 98 (3) 209-222 10.1016/0376-7388(94)00189-6
57. Lopez-Barron, C. R.; Macosko, C. W. A new model for the coarsening of cocontinuous morphologies Soft Matter 2010, 6 (12) 2637-2647 10.1039/b926191e
58. Guner, F. S.; Yagci, Y.; Erciyes, A. T. Polymers from triglyceride oils Prog. Polym. Sci. 2006, 31 (7) 633-670 10.1016/j.progpolymsci.2006.07.001
59. Meng, B.; Deng, J.; Liu, Q.; Wu, Z.; Yang, W. Transparent and ductile poly(lactic acid)/poly(butyl acrylate) (PBA) blends: Structure and properties Eur. Polym. J. 2012, 48 (1) 127-135 10.1016/j.eurpolymj.2011.10.009
60. Dell'Erba, R.; Groeninckx, G.; Maglio, G.; Malinconico, M.; Migliozzi, A. Immiscible polymer blends of semicrystalline biocompatible components: thermal properties and phase morphology analysis of PLLA/PCL blends Polymer 2001, 42 (18) 7831-7840 10.1016/S0032-3861(01)00269-5
61. Margolina, A.; Wu, S. H. Percolation model for brittle-tough transition in nylon rubber blends Polymer 1988, 29 (12) 2170-2173 10.1016/0032-3861(88)90108-5
62. Jansen, B. J. P.; Rastogi, S.; Meijer, H. E. H.; Lemstra, P. J. Rubber-modified glassy amorphous polymers prepared via chemically induced phase separation. 2. Mode of microscopic deformation studied by in-situ small-angle X-ray scattering during tensile deformation Macromolecules 2001, 34 (12) 4007-4018 10.1021/ma001810y
63. Corneillie, S.; Smet, M. PLA architectures: the role of branching Polym. Chem. 2015, 6 (6) 850-867 10.1039/C4PY01572J
64. Dorgan, J. R.; Williams, J. S.; Lewis, D. N. Melt rheology of poly(lactic acid): Entanglement and chain architecture effects J. Rheol. 1999, 43 (5) 1141-1155 10.1122/1.551041
65. Khajeheian, M. B.; Rosling, A. Preparation and characterization of linear and star-shaped poly L-lactide blends J. Appl. Polym. Sci. 2016, 10.1002/app.42231
66. Phuphuak, Y.; Miao, Y.; Zinck, P.; Chirachanchai, S. Balancing crystalline and amorphous domains in PLA through star-structured polylactides with dual plasticizer/nucleating agent functionality Polymer 2013, 54 (26) 7058-7070 10.1016/j.polymer.2013.10.006
67. Ristić, I.; Marinović-Cincović, M.; Cakić, S.; Tanasić, L.; Budinski-Simendić, J. Synthesis and properties of novel star-shaped polyesters based on l-lactide and castor oil Polym. Bull. 2013, 70 (6) 1723-1738 10.1007/s00289-013-0917-0
68. Tsujimoto, T.; Haza, Y.; Yin, Y.; Uyama, H. Synthesis of branched poly(lactic acid) bearing a castor oil core and its plasticization effect on poly(lactic acid) Polym. J. 2011, 43 (4) 425-430 10.1038/pj.2011.3
69. Zou, J.; Chen, X. A.; Shu, Y.; Zhou, H. J.; Huang, F. R. Synthesis, characterization of star-shaped copolymers of L-lactide and epoxidized soybean oil Polym. Bull. 2011, 66 (3) 315-326 10.1007/s00289-010-0280-3