Abstract
To further verify the forming mechanism of multi-core structure during the direct melt copolycondensation of lactic acid (LA) with the compounds containing multifunctional groups, the biodegradable material poly(lactic acid-co-glycerol) [P(LA-co-GL)] was synthesized as designed using L-lactic acid (L-LA) and glycerol (GL) as the starting materials. For the molar feed ratio n(LA)/n(GL) of 60/1, the optimal synthetic conditions were discussed. Using 0.3 wt% stannous oxide (SnO) as the catalyst, after the prepolymerization was carried out at 140 °C for 8 h, the melt copolymerization for 8 h at 160 °C gave the polymer with the biggest intrinsic viscosity ([η]) 0.76 dL•g−1. The copolymers P(LA-co-GL)s at different molar feed ratios were characterized by Fourier transform infrared spectroscopy (FT-IR), proton nuclear magnetic resonance (1H-NMR), gel permeation chromatography (GPC), differential scanning calorimetry (DSC) and X-ray diffraction (XRD). Increasing the molar feed ratio n(LA)/n(GL), the weight-average molecular weight (Mw) didn’t increase all the time, but a peak of Mw was formed, which indeed validated the above special phenomenon during the direct melt copolycondensation of LA with the monomers containing multifunctional groups. However, the forming mechanism of multi-core copolymer was different when multihydroxyl alcohol (e.g. GL) was used as the monomer containing multifunctional groups. Because the multi-core structure was linked by the ether bonds with less reversibility in the reaction, the biggest Mw of copolymers was relatively lower. For GL with three terminal hydroxyls as the core, only when n(LA)/n(GL) was more than 100/1, the star-shaped polylactic acid (SPLA) containing one core could be obtained.
Similar content being viewed by others
References
Rasal RM, Janorkar AV, Hirt DE (2010) Prog Polym Sci 35:338
Maharana T, Mohanty B, Negi YS (2009) Prog Polym Sci 34:99
Konishi S, Yokoi T, Ochiai B, Endo T (2010) Polym Bull 64:435
Sedlarik V, Kucharczyk P, Kasparkova V, Drbohlav J, Salakova A, Saha P (2010) J Appl Polym Sci 116:1597
Gao QW, Lan P, Shao HL, Hu XC (2002) Polym J 34:786
Qian ZY, Li S, Zhang HL, Liu XB (2003) Colloid Polym Sci 281:869
Zhou SB, Deng XM, Li XH (2004) J Appl Polym Sci 91:1848
Moon SI, Deguchi K, Miyamoto M, Kimura Y (2004) Polym Int 53:254
Slivniak R, Langer R, Domb AJ (2005) Macromol 38:5634
Lee CM, Kim HS, Yoon JS (2005) J Appl Polym Sci 95:1116
Matsudo K, Mihara T, Koide N (2005) Polym Prep Jpn 54:1266
Abe H, Tetsuka H, Doi Y (2005) Polym Prep Jpn 54:5243
Deng LD, Li AG, Yao CM, Sun DX, Dong AJ (2005) J Appl Polym Sci 98:2116
Gong QX, Wang LQ, Tu KH (2006) Carbohydr Polym 64:501
Wang ZY, Zhao YM, Wang F, Wang J (2006) J Appl Polym Sci 99:244
Kim HS, Hwang MO, Kim MN, Yoon JS (2006) J Appl Polym Sci 100:466
Du J, Fang YY, Zheng YB (2007) Polymer 48:5541
Duan JF, Du J, Zheng YB (2007) J Appl Polym Sci 103:2654
Duan JF, Du J, Zheng YB (2007) J Appl Polym Sci 103:3585
Sokolsky-Papkov M, Domb AJ (2008) Polym Adv Technol 19:671
Cohen-Arazi N, Katzhendler J, Kolitz M, Domb AJ (2008) Macromol 41:7259
Tsuji H, Matsuoka H, Itsuno S (2008) J Appl Polym Sci 110:3954
Sun ZJ, Wu L, Lu XL, Meng ZX, Zheng YF, Dong DL (2008) Appl Surf Sci 255:350
Sun ZJ, Wu L, Huang W, Zhang XL, Lu XL, Zheng YF, Yang BF, Dong DL (2009) Mat Sci Eng C 29:178
Li WD, Zeng JB, Li YD, Wang XL, Wang YZ (2009) J Polym Sci Part A Polym Chem 47:5898
Zhai YL, Deng LD, Xing JF, Liu Y, Zhang Q, Dong AJ (2009) J Biomat Sci Polym Ed 20:923
Zhang Y, Wang XL, Wang YZ, Qu MH (2009) J Macromol Sci Part A Pure Appl Chem 46:631
Ding J, Chen SC, Wang XL, Wang YZ (2009) Ind Eng Chem Res 48:788
Inkinen S, Stolt M, Södergård A (2010) Biomacromol 11:1196
Akesson D, Skrifvars M, Seppala J, Turunen M, Martinelli A, Matic A (2010) J Appl Polym Sci 115:480
Namkajorn M, Petchsuk A, Opaprakasit M, Opaprakasit P (2010) Express Polym Lett 4:415
Michinobu T, Bito M, Tanimura M, Katayama Y, Masai E, Nakamura M, Otsuka Y, Ohara S, Shigehara K (2010) J Macromol Sci Part A Pure Appl Chem 47:564
Miao PK, Wu DM, Zhao CE, Xu GL, Zeng K, Wang YP, Fu Q, Yang G (2010) E-polym No. 006
Ye RR, Wang ZY, Yang K, Luo SH (2010) Des Monomers Polym 13:415
Wang ZY, Zhao HJ, Wang QF, Ye RR, David EF (2010) J Appl Polym Sci 117:1405
Wang ZY, Luo YF, Ye RR, Song XM (2011) J Polym Res (doi: 10.1007/s10965-010-9442-0)
Xu YP, Li JH, Chen MQ, Ren JJ, Ni ZB, Liu XY (2010) Acta Polym Sin: 300
Arvanitoyannis L, Nakayama A, Kawasaki N, Yamamoto N (1995) Polymer 36:2947
Han DK, Hubbell JA (1996) Macromol 29:5233
Han DK, Hubbell JA (1997) Macromol 30:6077
Han DK, Park KD, Hubbell JA, Kim YH (1998) J Biomater Sci Polym Ed 9:667
Ju YM, Ahn KD, Kim JM, Hubbell JA, Han DK (2003) Polym Bull 50:107
Lee SH, Kim SH, Han YK, Kim YH (2001) J Polym Sci Part A Polym Chem 39:973
Tsuji H, Miyase T, Tezuka Y, Saha SK (2005) Biomacromol 6:244
Grijpma DW, Melchels FPW, Hou Q, Feijen J (2006) Mater Res Innovat 10:321
Zhang WA, Zheng SX (2007) Polym Bull 58:767
Gou PF, Zhu WP, Shen ZQ (2008) J Polym Sci Part A Polym Chem 46:2108
Zhao YM, Wang ZY, Yang F (2005) J Appl Polym Sci 97:195
Moon SI, Lee CW, Miyamoto M, Kimura Y (2000) J Polym Sci Part A Polym Chem 38:1673
Moon SI, Lee CW, Taniguchi I, Miyamoto M, Kimura Y (2001) Polymer 42:5059
Moon SI, Kimura Y (2003) Polym Int 52:299
Sayed FN, Grover V, Dubey KA, Sudarsan V, Tyagi AK (2011) J Colloid Interf Sci 353:445
Ma YD, Huang LQ, Song CX, Zeng XW, Liu G, Mei L (2010) Polymer 51:5952
Park SY, Han BR, Na KM, Han DK, Kim SC (2003) Macromol 36:4115
Ray WC, Grinstaff MW (2003) Macromol 36:3557
Yang F, Song FL, Pan YF, Wang ZY, Yang YQ, Zhao YM, Liang SZ, Zhang YM (2010) J Microencapsul 27:133
Wang N, Wu XS, Lujan-Upton H, Donahue E, Siddiqui A (1997) J Biomater Sci Polym Ed 8:905
Wang N, Wu XS (1998) J Biomater Sci Polym Ed 9:75
Kim ES, Kim BC, Kim SH (2004) J Polym Sci Part B Polym Phys 42:939
Ye RR, Wang ZY, Yang K, Li JX (2009) Chem 72:637
Luo YF, Wang ZY, Song XM, Mao ZZ, Zhao HJ (2008) Chin J Synth Chem 16:166
Acknowledgements
We are grateful to the financial support by Guangdong Provincial Natural Science Foundation of China (No. 5300082) and National Natural Science Foundation of China (No. 20772035).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Luo, SH., Wang, ZY., Mao, CX. et al. Synthesis of biodegradable material poly(lactic acid-co-glycerol) via direct melt polycondensation and its reaction mechanism. J Polym Res 18, 2093–2102 (2011). https://doi.org/10.1007/s10965-011-9619-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10965-011-9619-1