Synthesis of organic bisurea compounds and their roles as crystallization nucleating agents of poly(l-lactic acid)

European Polymer Journal

Volumn 49, Issue 4, 2013, Pages 865-872

  Xu, Yutao ^a   Wu, Linbo ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

Biodegradable polymers; Bisurea compounds; Crystallization; Nucleating agents; Poly(l lactic acid)

Indexed keywords

BIS-UREA COMPOUNDS; CRYSTALLIZATION RATES; HETEROGENEOUS NUCLEATION; ISOTHERMAL MELT CRYSTALLIZATION; NUCLEATING AGENTS; POLARIZED OPTICAL MICROSCOPY; POLY L LACTIC ACID; WIDE-ANGLE X-RAY DIFFRACTION;

BIODEGRADABLE POLYMERS; CRYSTALLIZATION; CRYSTALLIZATION KINETICS; DIFFERENTIAL SCANNING CALORIMETRY; LACTIC ACID; NUCLEATION; OPTICAL MICROSCOPY; POLYPROPYLENES; X RAY DIFFRACTION;

ORGANIC POLYMERS;

EID: 84875217186     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2012.12.015     Document Type: Article

References (49)

1. J. Lunt Large-scale production, properties and commercial applications of polylactic acid polymers Polym Degrad Stab 59 1-3SI 1998 145 152
2. D.W. Grijpma, J.P. Penning, and A.J. Pennings Chain entanglement, mechanical properties and drawability of poly(lactide) Colloid Polym Sci 272 9 1994 1068 1081
3. P. Pan, Z. Liang, A. Cao, and Y. Inoue Layered metal phosphonate reinforced poly(l-lactide) composites with a highly enhanced crystallization rate ACS Appl Mater Interfaces 1 2 2009 402 411
4. H. Xiao, L. Yang, X. Ren, T. Jiang, and J. Yeh Kinetics and crystal structure of poly(lactic acid) crystallized nonisothermally: effect of plasticizer and nucleating agent Polym Compos 31 12 2010 2057 2068
5. A.M. Harris, and E.C. Lee Improving mechanical performance of injection molded PLA by controlling crystallinity J Appl Polym Sci 107 4 2008 2246 2255
6. J.Y. Nam, S.S. Ray, and M. Okamoto Crystallization behavior and morphology of biodegradable polylactide/layered silicate nanocomposite Macromolecules 36 19 2003 7126 7131
7. G.Z. Papageorgiou, D.S. Achilias, S. Nanaki, T. Beslikas, and D. Bikiaris PLA nanocomposites: effect of filler type on non-isothermal crystallization Thermochim Acta 511 1-2 2010 129 139
8. A. Tsimpliaraki, I. Tsivintzelis, S.I. Marras, I. Zuburtikudis, and C. Panayiotou The effect of surface chemistry and nanoclay loading on the microcellular structure of porous poly(d, l lactic acid) nanocomposites J Supercrit Fluids 57 3 2011 278 287
9. V. Krikorian, and D.J. Pochan Unusual crystallization behavior of organoclay reinforced poly(l-lactic acid) nanocomposites Macromolecules 37 17 2004 6480 6491
10. J. Hwang, S. Huang, H. Liu, H. Chu, L. Lin, and C. Chung Crystallization kinetics of poly (l-lactic acid)/montmorillonite nanocomposites under isothermal crystallization condition J Appl Polym Sci 124 3 2012 2216 2226
11. M. Pluta Morphology and properties of polylactide modified by thermal treatment, filling with layered silicates and plasticization Polymer 45 24 2004 8239 8251
12. 2 nanowires J Appl Polym Sci 124 4 2012 2968 2977
13. R. Liao, B. Yang, W. Yu, and C. Zhou Isothermal cold crystallization kinetics of polylactide/nucleating agents J Appl Polym Sci 104 1 2007 310 317
14. S.S. Ray, K. Yamada, M. Okamoto, Y. Fujimoto, A. Ogami, and K. Ueda New polylactide/layered silicate nanocomposites. 5. Designing of materials with desired properties Polymer 44 21 2003 6633 6646
15. B. Li, F. Dong, X. Wang, J. Yang, D. Wang, and Y. Wang Organically modified rectorite toughened poly(lactic acid): nanostructures, crystallization and mechanical properties Eur Polym J 45 11 2009 2996 3003
16. S. Zhou, X. Zheng, X. Yu, J. Wang, J. Weng, and X. Li Hydrogen bonding interaction of poly(d, l-lactide)/hydroxyapatite nanocomposites Chem Mater 19 2 2007 247 253
17. H. Tsuji, H. Takai, N. Fukada, and H. Takikawa Non-isothermal crystallization behavior of poly(l-lactic acid) in the presence of various additives Macromol Mater Eng 291 4 2006 325 335
18. M.J. Sobkowicz, R. Sosa, and J.R. Dorgan Supramolecular bionanocomposites. Part 2. Effects of carbon nanoparticle surface functionality on polylactide crystallization J Appl Polym Sci 121 4 2011 2029 2038
19. J.Y. Nam, M. Okamoto, H. Okamoto, M. Nakano, A. Usuki, and M. Matsuda Morphology and crystallization kinetics in a mixture of low-molecular weight aliphatic amide and polylactide Polymer 47 4 2006 1340 1347
20. N. Kawamoto, A. Sakai, T. Horikoshi, T. Urushihara, and E. Tobita Nucleating agent for poly(l-lactic acid)-an optimization of chemical structure of hydrazide compound for advanced nucleation ability J Appl Polym Sci 103 1 2007 198 203
21. Q. Xing, X. Zhang, X. Dong, G. Liu, and D. Wang Low-molecular weight aliphatic amides as nucleating agents for poly (l-lactic acid): conformation variation induced crystallization enhancement Polymer 53 11 2012 2306 2314
22. P. Song, G. Chen, Z. Wei, Y. Chang, W. Zhang, and J. Liang Rapid crystallization of poly(l-lactic acid) induced by a nanoscaled zinc citrate complex as nucleating agent Polymer 53 19 2012 4300 4309
23. J. Li, D. Chen, B. Gui, M. Gu, and J. Ren Crystallization morphology and crystallization kinetics of poly(lactic acid): effect of N-aminophthalimide as nucleating agent Polym Bull 67 5 2011 775 791
24. H. Nakajima, M. Takahashi, and Y. Kimura Induce crystallization of PLLA in the presence of 1,3,5-benzenetricarboxylamide derivatives as nucleators: preparation of haze-free crystalline PLLA materials Macromol Mater Eng 295 5 2010 460 468
25. H. Bai, W. Zhang, H. Deng, Q. Zhang, and Q. Fu Control of crystal morphology in poly(l-lactide) by adding nucleating agent Macromolecules 44 6 2011 1233 1237
26. L. Wen, Z. Xin, and D. Hu A new route of manipulation of poly(l-lactic acid) crystallization by self-assembly of p-tert-butylcalix[8]arene and toluene J Polym Sci Pol Phys 48 11 2010 1235 1243
27. S. Wang, C. Han, J. Bian, L. Han, X. Wang, and L. Dong Morphology, crystallization and enzymatic hydrolysis of poly(l-lactide) nucleated using layered metal phosphonates Polym Int 60 2 2011 284 295
28. 3)-supported nucleating agent of poly(l-lactide) Polym Eng Sci 52 7 2012 1474 1484
29. Y. Tachibana, T. Maeda, O. Ito, Y. Maeda, and M. Kunioka Biobased myo-inositol as nucleator and stabilizer for poly(lactic acid) Polym Degrad Stab 95 8SI 2010 1321 1329
30. N. Kawamoto, A. Sakai, T. Horikoshi, T. Urushihara, and E. Tobita Physical and mechanical properties of poly(l-lactic acid) nucleated by dibenzoylhydrazide compound J Appl Polym Sci 103 1 2007 244 250
31. Y. Cai, S. Yan, J. Yin, Y. Fan, and X. Chen Crystallization behavior of biodegradable poly(l-lactic acid) filled with a powerful nucleating agent: N,N′-bis(benzoyl) suberic acid dihydrazide J Appl Polym Sci 121 3 2011 1408 1416
32. M. Yamato, Y. Kudo, K. Takahashi, K. Watanabe, and N. Kawamoto Magnetic alignment of poly(l-lactic acid) containing a nucleating agent Chem Lett 40 7 2011 765 767
33. Y. Cai Synthesis, thermal properties and nucleating effect of N,N,N,N′-tetra(benzoyl) ethylene diamine tetraacetic acid dihydrazide as nucleating agent of poly(l-lactic acid) E-J Chem 9 3 2012 1575 1580
34. Pan P, Yang J, Shan G, Bao Y, Weng Z, Inoue Y. Nucleation effects of nucleobases on the crystallization kinetics of poly(l-lactide). Macromol Mater Eng 2012 [Epub online].
35. Z. Qiu, and Z. Li Effect of orotic acid on the crystallization kinetics and morphology of biodegradable poly(l-lactide) as an efficient nucleating agent Ind Eng Chem Res 50 21 2011 12299 12303
36. K.S. Anderson, and M.A. Hillmyer Melt preparation and nucleation efficiency of polylactide stereocomplex crystallites Polymer 47 6 2006 2030 2035
37. J. Narita, M. Katagiri, and H. Tsuji Highly enhanced nucleating effect of melt-recrystallized stereocomplex crystallites on poly(l-lactic acid) crystallization Macromol Mater Eng 296 10 2011 887 893
38. H. Tsuji, S. Yamamoto, and A. Okumura Homo- and hetero-stereocomplexes of substituted poly(lactide)s as promising biodegradable crystallization- accelerating agents of poly(l-lactide) J Appl Polym Sci 122 1 2011 321 333
39. R. Mincheva, J. Raquez, V. Lison, E. Duquesne, O. Talon, and P. Dubois Stereocomplexes from biosourced lactide/butylene succinate-based copolymers and their role as crystallization accelerating agent Macromol Chem Phys 213 6 2012 643 653
40. K.S. Kang, S.I. Lee, T.J. Lee, R. Narayan, and B.Y. Shin Effect of biobased and biodegradable nucleating agent on the isothermal crystallization of poly(lactic acid) Korean J Chem Eng 25 3 2008 599 608
41. J. Cai, M. Liu, L. Wang, K. Yao, S. Li, and H. Xiong Isothermal crystallization kinetics of thermoplastic starch/poly(lactic acid) composites Carbohydr Polym 86 2 2011 941 947
42. T.Y. Ke, and X.Z. Sun Melting behavior and crystallization kinetics of starch and poly(lactic acid) composites J Appl Polym Sci 89 5 2003 1203 1210
43. A. Pei, Q. Zhou, and L.A. Berglund Functionalized cellulose nanocrystals as biobased nucleation agents in poly(l-lactide) (PLLA)-crystallization and mechanical property effects Compos Sci Technol 70 5 2010 815 821
44. Zhang R, Wang Y, Wang K, Zheng G, Li Q, Shen C. Crystallization of poly(lactic acid) accelerated by cyclodextrin complex as nucleating agent. Polym Bull 2012 [Epub online].
45. H. Tsuji, H. Takai, and S.K. Saha Isothermal and non-isothermal crystallization behavior of poly(l-lactic acid): effects of stereocomplex as nucleating agent Polymer 47 11 2006 3826 3837
46. B. Kalb, and A.J. Pennings General crystallization behavior of poly(l-lactic acid) Polymer 21 6 1980 607 612
47. W. Hoogsteen, A.R. Postema, A.J. Pennings, G. Tenbrinke, and P. Zugenmaier Crystal structure, conformation, and morphology of solution-spun poly(l-lactide) fibers Macromolecules 23 2 1990 634 642
48. B. Fillon, B. Lotz, A. Thierry, and J.C. Whierry Self-nucleation and enhanced nucleation of polymers-definition of a convenient calorimetric efficiency scale and evaluation of nucleating additives in isotactic polypropylene (alpha-phase) J Polym Sci Polym Part B: Phys 31 10 1993 1395 1405
49. B. Fillon, J.c. Wittmann, B. Lotz, and A. Thierry Self-nucleation and recrystallization of isotactic polypropylene (alpha-phase) investigated by differential scanning calorimetry J Polym Sci Part B: Polym Phys 31 10 1993 1383 1393