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

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

doi:10.1007/s10118-019-2283-3

Your Location：

Home >

Browse articles >

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

ARTICLE | Updated：2021-02-18

- Polyether-polyester and HMDI Based Polyurethanes: Effect of PLLA Content on Structure and Property
- Chinese Journal of Polymer Science Vol. 37, Issue 11, Pages: 1152-1161(2019)
- Affiliations：
  
  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
- Author bio：
  
  zhangruoy@nimte.ac.cn (R.Y.Z.)
  tangzhb04@nimte.ac.cn (Z.B.T.)
  jzhu@nimte.ac.cn (J.Z.)
- Funds：
- DOI：10.1007/s10118-019-2283-3
  CLC：
- Received：31 March 2019，
  
  Revised：2019-1-1，
  
  Accepted：25 April 2019，
  
  Online First：10 June 2019，
  
  Published：2019-11
- Accepted：
Scan QR Code
Shi, L.; Zhang, R. Y.; Ying, W. B.; Hu, H.; Wang, Y. B.; Guo, Y. Q.; Wang, W. Q.; Tang, Z. B.; Zhu, J. Polyether-polyester and HMDI Based polyurethanes: Effect of PLLA content on structure and property. Chinese J. Polym. Sci. 2019, 37, 1152–1161.

Lei Shi, Ruo-Yu Zhang, Wu-Bin Ying, et al. 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.
Shi, L.; Zhang, R. Y.; Ying, W. B.; Hu, H.; Wang, Y. B.; Guo, Y. Q.; Wang, W. Q.; Tang, Z. B.; Zhu, J. Polyether-polyester and HMDI Based polyurethanes: Effect of PLLA content on structure and property. Chinese J. Polym. Sci. 2019, 37, 1152–1161. DOI： 10.1007/s10118-019-2283-3.

Lei Shi, Ruo-Yu Zhang, Wu-Bin Ying, et al. 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.

摘要

Abstract

Thermoplastic poly(ether-ester-urethane)s were synthesized from poly(L-lactide) diols (PLLA diols)

polytetrahydrofuran diol (PTMG diols)

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.

关键词

Keywords

references

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 http://doi.org/10.1016/S0032-3861(02)00798-X .

Hepburn, C. Polyurethane elastomers . Springer Science & amp; Business Media, 2012 .

Oertel, G. Polyurethane handbook . Reinf. Plast 1986 , 30 , 51.

Harrell, L. L . Segmented Polyurethans. Properties as a function of segment size and distribution . Macromolecules , 1969 . 2 607 - 612 . DOI: 10.1021/ma60012a008 http://doi.org/10.1021/ma60012a008 .

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 http://doi.org/10.1177/009524438501700404 .

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 http://doi.org/10.1039/C5RA26664E .

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 http://doi.org/10.1016/j.polymer.2017.03.031 .

Petrović, Z. S.; Ferguson, J . Polyurethane elastomers . Prog. Polym. Sci. , 1991 . 16 695 - 836 . DOI: 10.1016/0079-6700(91)90011-9 http://doi.org/10.1016/0079-6700(91)90011-9 .

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 . .

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 http://doi.org/10.1039/C3PY01120H .

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 http://doi.org/10.1016/j.polymer.2017.11.001 .

Lempesis, N.; in’t Veld, P. 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 http://doi.org/10.1021/acs.macromol.6b00555 .

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 http://doi.org/10.1177/009524438301500205 .

Cheng, G.; Liu, X.; Xu, R. X.; Zhang, J.; Fang, S.; Jiang, Z . Effect of polyether soft segments on the properties of hmdi based transparent polyurethane elastomers . Polyurethane Industry (in Chinese) , 2016 . 31 40 - 43 . .

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 http://doi.org/10.1163/156856207780852488 .

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 http://doi.org/10.1016/j.progpolymsci.2016.05.003 .

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 http://doi.org/10.1021/acsami.5b09822 .

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 http://doi.org/10.1021/acssuschemeng.6b01713 .

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 http://doi.org/10.1021/ma9714629 .

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 http://doi.org/10.1016/j.polymer.2017.04.004 .

Abayasinghe, N. K.; Perera, K. P.; Thomas, C.; Daly, A.; Suresh, S.; Burg, K.; Harrison, G. M.; Smith, D. W . Amido-modified polylactide for potential tissue engineering applications . J. Biomat. Sci. Polym. E , 2004 . 15 595 - 606 . DOI: 10.1163/156856204323046861 http://doi.org/10.1163/156856204323046861 .

Panyam, J.; Labhasetwar, V . Sustained cytoplasmic delivery of drugs with intracellular receptors using biodegradable nanoparticles . Mol. Pharm. , 2004 . 1 77 - 84 . DOI: 10.1021/mp034002c http://doi.org/10.1021/mp034002c .

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 http://doi.org/10.1016/S0142-9612(00)00115-0 .

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 http://doi.org/10.1016/S0939-6411(00)00084-9 .

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. Int. , 2008 . 57 982 - 986 . DOI: 10.1002/pi.v57:8 http://doi.org/10.1002/pi.v57:8 .

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 http://doi.org/10.1002/(ISSN)1097-4628 .

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 http://doi.org/10.1021/ma960402k .

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 http://doi.org/10.1002/(ISSN)1548-2634 .

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 http://doi.org/10.1016/0032-3861(83)90068-X .

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 http://doi.org/10.1002/(ISSN)1548-2634 .

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 http://doi.org/10.1002/app.11605 .

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 http://doi.org/10.1002/(ISSN)1548-2634 .

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 http://doi.org/10.1002/polb.1987.090250301 .

Lendlein, A.; Kelch, S . Shape-memory polymers . Encyclopedia of Materials Science & Technology , 2002 . 41 2034 - 2057 . .

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 http://doi.org/10.1039/c3ta01655b .

Views

Downloads

CSCD

Alert me when the article has been cited

Submit

Tools

Publicity Resources

Squaramide-directed Cooperative One-dimensional Assembly in Telechelic Polydimethylsiloxane for Hierarchical Network Formation

Two-way Shape Memory Effect of Polycaprolactone-based Polyurethane via Synergistic Role of Hydrogen Bonding and Crystallization Tuned by Malic Acid

Regulation of Microphase Separation in Bio-based Thermoplastic Polyurethanes Driven by Hard Segment Content

Processing-integrated Machine Learning Models for Predicting and Optimizing Mechanical Properties of Polyimides

Soft-segment-engineered Self-healing Polyurethane for High-performance Electrorheological Elastomers and Capacitive Sensors

Related Author

Yu-Hong Zhang

Jian-Fei Ma

Hao-Bo Wei

Jie Wang

Feng Wang

Xue-Qing Li

Shuai Lu

Jun-Jie Tan

Related Institution

Department of Polymer Science and Engineering, University of Science and Technology of China

School of Chemistry and Pharmaceutical Engineering, Jilin University of Chemical Technology

School of Chemistry and Chemical Engineering, Wuhan University of Science and Technology

School of Textile Science and Engineering, State Key Laboratory of New Textile Materials and Advanced Processing Technology, Wuhan Textile University

Hubei Key Laboratory of Pollutant Analysis & Reuse Technology, Hubei Normal University

⁰