Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Ring-Opening Dispersion Polymerization of l-Lactide with Polylactide Stabilizer in Supercritical Carbon Dioxide

Jinjun Deng A B , Shiping Zhan C D , Jingchang Wang C , Zhijun Liu A and Zhiyi Li A
+ Author Affiliations
- Author Affiliations

A Institute of Fluid and Powder Engineering, Dalian University of Technology, Dalian 116622, China.

B College of Chemical Engineering, Daqing Normal University, Daqing 163318, China.

C College of Environment and Chemical Engineering, Dalian University, Dalian 116622, China.

D Corresponding author. Email: zhanshiping@dlu.edu.cn

Australian Journal of Chemistry 70(6) 712-717 https://doi.org/10.1071/CH16357
Submitted: 15 June 2016  Accepted: 19 October 2016   Published: 9 November 2016

Abstract

Non-fluorous triblock copolymers of poly(l-lactide)-block-hydroxypropyl-terminated poly(dimethyl siloxanes)-block-poly(l-lactide) (PLLA-HTPDMS-PLLA) with two different molecular weights in the range of 4800 to 6500 Da, were prepared by changing the ratio of HTPDMS to l-lactide (L-LA), and were used as stabilizers for the ring-opening dispersion polymerization (RODP) of L-LA to prepare poly(l-lactide) (PLLA) in supercritical carbon dioxide (ScCO2). The experimental results showed that the prepared non-fluorous triblock copolymers were very effective as new stabilizers for the RODP and fine powders of PLLA were obtained. The structure of the stabilizers and PLLA were characterized by 1H NMR and FTIR spectroscopy. The morphology of PLLA was investigated by scanning electron microscopy (SEM). The effects of the CO2-philic/lipophilic segment lengths of the stabilizers on the RODP were explored. The effects of the stabilizer concentration on the polymerization yield, molecular weight, and morphology of PLLA were investigated.


References

[1]  P. G. Jessop, W. Leitner, Chemical Synthesis Using Supercritical Fluids 1999 (Wiley-VCH: Weinheim).

[2]  M. Yılmaz, S. Eğri, N. Yıldız, A. Çalımlı, E. Pişkin, J. Polym. Res. 2011, 18, 975.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  J. L. Kendall, D. A. Canelas, J. L. Young, J. M. Desimone, Chem. Rev. 1999, 99, 543.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXks1Klsg%3D%3D&md5=5a4d4f696f7362759de9eed27a1a3c89CAS |

[4]  D. D. Hile, M. V. Pishko, Macromol. Rapid Commun. 1999, 20, 511.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXms1Glt7w%3D&md5=bf6e0a9bf067fff89bd12671e04039b7CAS |

[5]  A. F. Mingotaud, F. Cansell, N. Gilbert, A. Soum, Polym. J. 1999, 31, 406.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXjtFequro%3D&md5=028a410cc6ab7c60f0e89955b6aa23dfCAS |

[6]  F. Stassin, O. Halleux, R. Jerome, Macromolecules 2001, 34, 775.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXksVOqtQ%3D%3D&md5=97023c58af9c1c9e20b35217710242a7CAS |

[7]  A. C. Albertsson, I. K. Varma, Biomacromolecules 2003, 4, 1466.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXotlaltro%3D&md5=842468547eac324d1e6467a935270c3bCAS |

[8]  K. M. Stridsberg, M. Ryner, A. C. Albertsson, Adv. Polym. Sci. 2002, 157, 41.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XhtVOqtb8%3D&md5=86cc91bd0e9e767d3a146dc462cc95c4CAS |

[9]  D. D. Hile, M. V. Pishko, Macromol. Rapid Commun. 1999, 20, 511.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXms1Glt7w%3D&md5=bf6e0a9bf067fff89bd12671e04039b7CAS |

[10]  A. C. Albertsson, I. K. Varma, Adv. Polym. Sci. 2000, 157, 1.
         | Crossref | GoogleScholarGoogle Scholar |

[11]  J. C. Middleton, A. J. Tipton, Biomaterials 2000, 21, 2335.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXmslKmtrc%3D&md5=6b3ce7e040ef97a5520c3dec4f93c8e9CAS |

[12]  J. L. Kendall, D. A. Canelas, J. L. Young, J. M. Desimone, Chem. Rev. 1999, 99, 543.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXks1Klsg%3D%3D&md5=5a4d4f696f7362759de9eed27a1a3c89CAS |

[13]  J. M. DeSimone, E. E. Maury, Y. Z. Menceloglu, J. B. McClain, T. R. Romack, J. R. Combes, Science 1994, 265, 356.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXltV2ktbk%3D&md5=8d493e50610660683a8441be28e1a005CAS |

[14]  Y. L. Hsiao, E. E. Maury, J. M. DeSimone, S. M. Mawson, K. P. Johnston, Macromolecules 1995, 28, 8159.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXovFCgtbc%3D&md5=d586520e239fd27148dbd79c6de93155CAS |

[15]  M. L. O’Neill, M. Z. Yates, K. P. Johnston, C. D. Smith, S. P. Wilkinson, Macromolecules 1998, 31, 2838.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXisVSjsL4%3D&md5=3791b9abe0221401fdf1c79652e4ded2CAS |

[16]  W. Wang, R. M. T. Griffiths, A. Naylor, M. R. Giles, D. J. Irvine, S. M. Howdle, Polymer 2002, 43, 6653.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XotlWisL8%3D&md5=b9792bcb4ddcab7760458f8d59cf292bCAS |

[17]  R. Wang, H. M. Cheung, J. Appl. Polym. Sci. 2004, 93, 545.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXktFCgsrk%3D&md5=aa007b44d25a22c99b244e5a54e13315CAS |

[18]  K. A. Shaffer, T. A. Jones, D. A. Canelas, J. M. DeSimone, S. P. Wilkinson, Macromolecules 1996, 29, 2704.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XhsVGnsLc%3D&md5=b6b32352894b7fc35eaa02ef49095ac3CAS |

[19]  C. Lepilleur, E. J. Beckman, Macromolecules 1997, 30, 745.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXhtFeitrg%3D&md5=526e1f86a2326f74513d792113618726CAS |

[20]  M. R. Giles, R. M. T. Griffiths, Macromolecules 2001, 34, 20.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXosF2jsrw%3D&md5=734742b3b1403bad2617b60ad4fe6802CAS |

[21]  J. M. DeSimone, L. Riddick, Proc. – NOBCChE 1999, 26, 53.
         | 1:CAS:528:DC%2BD3cXosl2qt7k%3D&md5=4cc159f0881ca357b9498f9bf2f53452CAS |

[22]  D. A. Canelas, D. E. Betts, J. M. DeSimone, Macromolecules 1996, 29, 2818.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28Xhs1Cgsb4%3D&md5=badc2c1ea0416d7e43db0729291892feCAS |

[23]  D. A. Canelas, J. M. DeSimone, Macromolecules 1997, 30, 5673.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXls1Gnur8%3D&md5=cff5cdee68fb170c9af1c985bf9d9976CAS |

[24]  D. D. Hile, M. V. Pishko, Macromol. Rapid Commun. 1999, 20, 511.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXms1Glt7w%3D&md5=bf6e0a9bf067fff89bd12671e04039b7CAS |

[25]  D. D. Hile, M. Pishko, J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 562.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXhtVGku78%3D&md5=ad1801f935a053267734ba5728065b5bCAS |

[26]  H. S. Ganapathy, H. S. Hwang, Y. T. Jeong, W. K. Lee, K. T. Lim, Eur. Polym. J. 2007, 43, 119.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtlagtLfK&md5=8d4a6f51e92eea41e062b47b78d68548CAS |

[27]  F. C. Loeker, C. J. Duxbury, R. Kumar, W. Gao, R. A. Gross, S. M. Howdle, Macromolecules 2004, 37, 2450.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXitValtrc%3D&md5=87997594f62c1de8c8244603ddbc4214CAS |

[28]  F. Stassin, R. Jerome, Chem. Commun. 2003, 2, 232.
         | Crossref | GoogleScholarGoogle Scholar |

[29]  F. Stassin, O. Halleux, R. Jerome, Macromolecules 2001, 34, 775.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXksVOqtQ%3D%3D&md5=97023c58af9c1c9e20b35217710242a7CAS |

[30]  K. J. Thurecht, A. Heise, M. deGeus, S. Villarroya, J. Zhou, M. F. Wyatt, S. M. Howdle, Macromolecules 2006, 39, 7967.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtV2gt7bN&md5=c40129e24d38dcd410fb8533061d196cCAS |

[31]  D. Bratton, M. Brown, S. M. Howdle, Macromolecules 2003, 36, 5908.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXlsFWqsrw%3D&md5=c51c6605893175859c4f8773c8c0194bCAS |

[32]  C. A. Moody, J. W. Martin, W. C. Kwan, D. C. G. Muir, S. A. Mabury, Environ. Sci. Technol. 2002, 36, 545.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXptV2nu78%3D&md5=90e3188e31c04846a8f4b0b1c67af25cCAS |

[33]  G. W. Olsen, J. M. Burris, J. H. Mandel, L. R. Zobel, J. Occup. Environ. Med. 1999, 41, 799.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXmsVOlt7g%3D&md5=1396d5c29da1baa4c2200c4df77688d5CAS |

[34]  Y. Yamaguchi, T. Usami, H. Natsume, T. Aoyagi, Y. Nagase, K. Sugibayashi, Chem. Pharm. Bull. 1997, 45, 537.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXitFegsL8%3D&md5=5a99572ba1981c04520483a603156d6fCAS |

[35]  H. S. Ganapathy, H. S. Hwang, Y. T. Jeong, W. K. Lee, K. T. Lim, Eur. Polym. J. 2007, 43, 119.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtlagtLfK&md5=8d4a6f51e92eea41e062b47b78d68548CAS |

[36]  H. S. Hwang, H. Yuvaraj, W. S. Kim, W. Lee, Y. Gal, K. T. Lim, J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 1365.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhvF2mtb8%3D&md5=0b23c416824c46081749d58579cd8efbCAS |