Citation: Lei Shi, Ruo-Yu Zhang, Wu-Bin Ying, Han Hu, Yu-Bin Wang, Ya-Qian Guo, Wen-Qin Wang, Zhao-Bin Tang, Jin Zhu. Polyether-polyester and HMDI Based Polyurethanes: Effect of PLLA Content on Structure and Property[J]. Chinese Journal of Polymer Science, ;2019, 37(11): 1152-1161. doi: 10.1007/s10118-019-2283-3 shu

Polyether-polyester and HMDI Based Polyurethanes: Effect of PLLA Content on Structure and Property

Lei Shi ^a,b ,
Ruo-Yu Zhang ^a,, ,
Wu-Bin Ying ^a ,
Han Hu ^a ,
Yu-Bin Wang ^a ,
Ya-Qian Guo ^a ,
Wen-Qin Wang ^b ,
Zhao-Bin Tang ^a,, ,
Jin Zhu ^a,,

a.
Key Laboratory of Bio-based Polymeric Materials Technology and Application of Zhejiang Province, Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201, China
b.
School of Material Science and Chemical Engineering, Ningbo University, Ningbo 315211, China

Corresponding author: Ruo-Yu Zhang, zhangruoy@nimte.ac.cn Zhao-Bin Tang, tangzhb04@nimte.ac.cn Jin Zhu, jzhu@nimte.ac.cn
Received Date: 31 March 2019
Revised Date: 1 January 2019
Available Online: 10 June 2019

Thermoplastic poly(ether-ester-urethane)s were synthesized from poly(L-lactide) diols (PLLA diols), polytetrahydrofuran diol (PTMG diols), 4,4′-dicyclohexylmethane diisocyanate (HMDI), and 1,4-butanediol (BDO) by a two-step reaction, and the morphology and property of the resultant TPU could be adjusted by varying the PLLA contents. The soft segment was composed of PLLA and PTMG diols. By controlling the percentage of PLLA in the soft segment, the glass transition temperature and mechanical properties of the polyurethanes could be regulated. Based on the FTIR spectrum, we found that two kinds of hydrogen bonding existed individually in soft matrix and hard domain. The hydrogen bonding in soft matrix was unstable, which could be destroyed during elongation. With in situ stretching WAXS and SAXS experiments, we found that the PLLA crystal was destroyed and the PLLA domain oriented along the stretch direction. Finally, we proposed a schematic model to illustrate the microstructures of these elastomers before and after stretch.
- Poly(L-lactide) diol,
- Polyurethane,
- Mechanical property,
- Hydrogen bonding
1. [1]
  Sheth, J. P.; Xu, J. N.; Wilkes, G. L. Solid state structure-property behavior of semicrystalline poly (ether-block-amide) PEBAX^® thermoplastic elastomers. Polymer 2003, 44, 743-756. doi: 10.1016/S0032-3861(02)00798-X
2. [2]
  Hepburn, C. Polyurethane elastomers. Springer Science & Business Media, 2012.
3. [3]
  Oertel, G. Polyurethane handbook. Reinf. Plast 1986, 30, 51.
4. [4]
  Harrell, L. L. Segmented Polyurethans. Properties as a function of segment size and distribution. Macromolecules 1969, 2, 607-612. doi: 10.1021/ma60012a008
5. [5]
  Oguro, K.; Kun, N.; Nishimura, H.; Kobayashi, M.; Doi, T. Modified PTMG based thermoplastic polyurethane elastomers. J. Elastom. Plast. 1985, 17, 261-272. doi: 10.1177/009524438501700404
6. [6]
  Fang, H.; Wang, H.; Sun, J.; Wei, H.; Ding, Y. Tailoring elastomeric properties of waterborne polyurethane by incorporation of polymethyl methacrylate with nanostructural heterogeneity. RSC Adv. 2016, 6, 13589-13599. doi: 10.1039/C5RA26664E
7. [7]
  Nozaki, S.; Hirai, T.; Higaki, Y.; Yoshinaga, K.; Kojio, K.; Takahara, A. Effect of chain architecture of polyol with secondary hydroxyl group on aggregation structure and mechanical properties of polyurethane elastomer. Polymer 2017, 116, 423-428. doi: 10.1016/j.polymer.2017.03.031
8. [8]
  Petrović, Z. S.; Ferguson, J. Polyurethane elastomers. Prog. Polym. Sci 1991, 16, 695-836. doi: 10.1016/0079-6700(91)90011-9
9. [9]
  Prisacariu, C.; Scortanu, E.; Coseri, S.; Agapie, B. Effect of soft segment polydispersity on the elasticity of polyurethane elastomers. Ind. Eng. Chem. Res. 2013, 56, 2316-2322.
10. [10]
  Tang, D.; Macosko, C. W.; Hillmyer, M. A. Thermoplastic polyurethane elastomers from bio-based poly (δ-decalactone) diols. Polym. Chem. 2014, 5, 3231-3237. doi: 10.1039/C3PY01120H
11. [11]
  Xiang, D.; Liu, L.; Liang, Y. Effect of hard segment content on structure, dielectric and mechanical properties of hydroxyl-terminated butadiene-acrylonitrile copolymer-based polyurethane elastomers. Polymer 2017, 132, 180-187. doi: 10.1016/j.polymer.2017.11.001
12. [12]
  Lempesis, N.; In, t. V., Pieter J; Rutledge, G. C. Atomistic simulation of the structure and mechanics of a semicrystalline polyether. Macromolecules 2016, 49, 5714-5726. doi: 10.1021/acs.macromol.6b00555
13. [13]
  Szycher, M.; Poirier, V. L.; Dempsey, D. J. Development of an aliphatic biomedical-grade polyurethane elastomer. J. Elastom. Plast. 1983, 15, 81-95. doi: 10.1177/009524438301500205
14. [14]
  Cheng, G.; Liu, X.; Ruixiang, X. U.; Zhang, J.; Fang, S.; Jiang, Z. Effect of polyether soft segments on the properties of hmdi based transparent polyurethane elastomers. Polyurethane Industry 2016, 31, 40-43.
15. [15]
  Solíscorrea, R. E.; Vargascoronado, R.; Aguilarvega, M.; Cauichrodríguez, J. V.; Román, J. S.; Marcos, A. Synthesis of HMDI-based segmented polyurethanes and their use in the manufacture of elastomeric composites for cardiovascular applications. J. Biomat. Sci-Polym. E 2007, 18, 561-578. doi: 10.1163/156856207780852488
16. [16]
  Li, Z.; Tan, B. H.; Lin, T.; He, C. Recent advances in stereocomplexation of enantiomeric PLA-based copolymers and applications. Prog. Polym. Sci. 2016, 62, 22-72. doi: 10.1016/j.progpolymsci.2016.05.003
17. [17]
  Li, Z.; Yuan, D.; Jin, G.; Tan, B. H.; He, C. Facile layer-by-layer self-assembly toward enantiomeric poly (lactide) stereocomplex coated magnetite nanocarrier for highly tunable drug deliveries. ACS Appl. Mater. Interfaces 2016, 8, 1842-1853. doi: 10.1021/acsami.5b09822
18. [18]
  Tan, B. H.; Muiruri, J. K.; Li, Z.; He, C. Recent progress in using stereocomplexation for enhancement of thermal and mechanical property of polylactide. ACS Sustain. Chem. Eng. 2016, 4, 5370-5391. doi: 10.1021/acssuschemeng.6b01713
19. [19]
  Huang, J.; Lisowski, M. S.; Runt, J.; Hall, E. S.; Kean, R. T.; Buehler, N.; Lin, J. S. Crystallization and microstructure of poly (L-lactide-co-meso-lactide) copolymers. Macromolecules 1998, 31, 2593-2599. doi: 10.1021/ma9714629
20. [20]
  Lv, R.; Peng, N.; Jin, T.; Na, B.; Wang, J.; Liu, H. Stereocomplex mesophase and its phase transition in enantiomeric polylactides. Polymer 2017, 116, 324-330. doi: 10.1016/j.polymer.2017.04.004
21. [21]
  Abayasinghe, N. K.; Perera, K. P.; Thomas, C.; Daly, A.; Suresh, S.; Burg, K.; Harrison, G. M.; Jr, S. D. Amido-modified polylactide for potential tissue engineering applications. J. Biomat. Sci. Polym. E 2004, 15, 595-606. doi: 10.1163/156856204323046861
22. [22]
  Panyam, J.; Vinod Labhasetwar, V. Sustained cytoplasmic delivery of drugs with intracellular receptors using biodegradable nanoparticles. Mol. Pharm. 2004, 1, 77-84. doi: 10.1021/mp034002c
23. [23]
  Jain, R. A. The manufacturing techniques of various drug loaded biodegradable poly (lactide-co-glycolide) (PLGA) devices. Biomaterials 2000, 21, 2475-2490. doi: 10.1016/S0142-9612(00)00115-0
24. [24]
  Jung, T.; Kamm, W.; Breitenbach, A.; Kaiserling, E.; Xiao, J. X.; Kissel, T. Biodegradable nanoparticles for oral delivery of peptides: is there a role for polymers to affect mucosal uptake? Eur. J. Pharm. Biopharm. 2000, 50, 147-160. doi: 10.1016/S0939-6411(00)00084-9
25. [25]
  Gu, S. Y.; Yang, M.; Yu, T.; Ren, T. B.; Ren, J. Synthesis and characterization of biodegradable lactic acid-based polymers by chain extension. Polym. Inter. 2008, 57, 982-986. doi: 10.1002/pi.v57:8
26. [26]
  Hoshi, M.; Ieshige, M.; Saitoh, T.; Nakagawa, T. Separation of aqueous phenol through polyurethane membranes by pervaporation. II. Influence of diisocyanate and diol compounds and crosslinker. J. Appl. Polym. Sci. 1999, 71, 439-448. doi: 10.1002/(ISSN)1097-4628
27. [27]
  Hiltunen, K.; Härkönen, M.; Seppälä, J. V.; Väänänen, T. Synthesis and characterization of lactic acid based telechelic prepolymers. Macromolecules 1996, 29, 8677-8682. doi: 10.1021/ma960402k
28. [28]
  Schneider, N. S.; Matton, R. W. Thermal transition behavior of polybutadiene containing polyurethanes. Polym. Eng. Sci. 1979, 19, 1122-1128. doi: 10.1002/(ISSN)1548-2634
29. [29]
  Xu, M.; Macknight, W. J.; Chen, C. H. Y.; Thomas, E. L. Structure and morphology of segmented polyurethanes: 1. Influence of incompatability on hard-segment sequence length. Polymer 1983, 24, 1327-1332. doi: 10.1016/0032-3861(83)90068-X
30. [30]
  Hesketh, T. R.; Vanbogart, J. W. C.; Cooper, S. L. Differential scanning calorimetry analysis of morphological-changes in segmented elastomers. Polym. Eng. Sci. 1980, 20, 190-197. doi: 10.1002/(ISSN)1548-2634
31. [31]
  Tsuji, H.; Ishida, T. Poly (L-lactide). X. Enhanced surface hydrophilicity and chain-scission mechanisms of poly (L-lactide) film in enzymatic, alkaline, and phosphate-buffered solutions. J. Appl. Polym. Sci. 2003, 87, 1628-1633. doi: 10.1002/app.11605
32. [32]
  Lucas, J. C.; Failla, M. D.; Smith, F. L.; Mandelkern, L. The double yield in the tensile deformation of the polyethylenes. Polym. Eng. Sci. 1995, 35, 1117-1123. doi: 10.1002/(ISSN)1548-2634
33. [33]
  Popli, R.; Mandelkern, L. Influence of structural and morphological factors on the mechanical-properties of the polyethylenes. J. Polym. Sci. Part. B: Polym. Phys. 1987, 25, 441-483. doi: 10.1002/polb.1987.090250301
34. [34]
  Lendlein, A.; Kelch, S. Shape-memory polymers. Encyclopedia of Materials Science & Technology 2002, 41, 2034-2057.
35. [35]
  Zhang, L.; Jiang, Y.; Xiong, Z.; Liu, X.; Na, H.; Zhang, R.; Zhu, J. Highly recoverable rosin-based shape memory polyurethanes. J. Mater. Chem. A 2013, 1, 3263-3267. doi: 10.1039/c3ta01655b
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