Preparation of Degradable Polymenthide and Its Elastomers from Biobased Menthide <italic style="font-style: italic">via</italic> Organocatalyzed Ring-opening Polymerization and UV Curing

Na Zhao; Xin-Xin Cao; Jin-Feng Shi; Zhi-Bo Li

doi:10.1007/s10118-020-2415-9

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Preparation of Degradable Polymenthide and Its Elastomers from Biobased Menthide via Organocatalyzed Ring-opening Polymerization and UV Curing

ARTICLE | Updated：2020-05-09

- Preparation of Degradable Polymenthide and Its Elastomers from Biobased Menthide via Organocatalyzed Ring-opening Polymerization and UV Curing
- Chinese Journal of Polymer Science Vol. 38, Issue 10, Pages: 1092-1098(2020)
- Affiliations：
  
  Key Laboratory of Biobased Polymer Materials, Shandong Provincial Education Department, College of Polymer Science and Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
- Author bio：
  
  zbli@qust.edu.cn
- Funds：
- DOI：10.1007/s10118-020-2415-9
  CLC：
- Received：12 February 2020，
  
  Revised：2020-2-26，
  
  Accepted：28 February 2020，
  
  Online First：09 May 2020，
  
  Published：16 June 2020
- Accepted：
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Zhao, N.; Cao, X. X.; Shi, J. F.; Li, Z. B. Preparation of degradable polymenthide and its elastomers from biobased menthide , via, organocatalyzed ring-opening polymerization and UV curing. Chinese J. Polym. Sci. 2020, 38, 1092–1098

Na Zhao, Xin-Xin Cao, Jin-Feng Shi, et al. Preparation of Degradable Polymenthide and Its Elastomers from Biobased Menthide via Organocatalyzed Ring-opening Polymerization and UV Curing[J]. Chinese Journal of Polymer Science, 2020, 38(10): 1092-1098. DOI: 10.1007/s10118-020-2415-9.
Zhao, N.; Cao, X. X.; Shi, J. F.; Li, Z. B. Preparation of degradable polymenthide and its elastomers from biobased menthide , via, organocatalyzed ring-opening polymerization and UV curing. Chinese J. Polym. Sci. 2020, 38, 1092–1098 DOI： 10.1007/s10118-020-2415-9.

Na Zhao, Xin-Xin Cao, Jin-Feng Shi, et al. Preparation of Degradable Polymenthide and Its Elastomers from Biobased Menthide via Organocatalyzed Ring-opening Polymerization and UV Curing[J]. Chinese Journal of Polymer Science, 2020, 38(10): 1092-1098. DOI: 10.1007/s10118-020-2415-9. DOI：

摘要

Abstract

Development of degradable polyester elastomers plays an important role in the applications of soft mateirals. Noncrystalline polymenthides (PMs) from menthol derived lactone monomers are excellent soft segments for preparing degradable polyester elastomers. By using cyclic trimeric phosphazene base (CTPB) as an organocatalyst

we successfully synthesized PMs with different molecular weights (8.2 kDa to 100.7 kDa) in high yields

via

ring-opening polymerization (ROP) of menthide. When a CTPB/urea binary catalytic system was adopted

the polymerizations proceeded in a more controlled manner. Using glycerol as initiator

star shaped PMs with well-defined structure were synthesized and subsequently end-capped by acrylate. UV irradiation of the terminal acrylate groups in the star-shaped PMs resulted in formation of chemically cross-linked polyester elastomers without heat or other stimuli. The obtained polyester elastomers exhibit matched modulus (3.8−5.5 MPa)

tensile strength (0.56−0.68 MPa)

and strain at break (280%−320%) with soft body tissues

displaying great potential in biomedical applications.

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references

Zhu, Y.; Romain, C.; Williams, C. K. . Sustainable polymers from renewable resources . Nature , 2016 . 540 354 - 362 . DOI: 10.1038/nature21001 http://doi.org/10.1038/nature21001 .

Schneiderman, D. K.; Hillmyer, M. A. . 50 th Anniversary perspective: there is a great future in sustainable polymers . Macromolecules , 2017 . 50 3733 - 3749 . DOI: 10.1021/acs.macromol.7b00293 http://doi.org/10.1021/acs.macromol.7b00293 .

John, G.; Nagarajan, S.; Vemula, P. K.; Silverman, J. R.; Pillai, C. K. S. . Natural monomers: a mine for functional and sustainable materials—occurrence, chemical modification and polymerization . Prog. Polym. Sci. , 2019 . 92 158 - 209 . DOI: 10.1016/j.progpolymsci.2019.02.008 http://doi.org/10.1016/j.progpolymsci.2019.02.008 .

Chen, X. S.; Chen, G. Q.; Tao, Y. H.; Wang, Y. Z.; Lv, X. B.; Zhang, L. Q.; Zhu, J.; Zhang, J.; Wang, X. H. . Research progress in eco-polymers . Acta Polymerica Sinica (in Chinese) , 2019 . 50 1068 - 1082 . .

Wang, S.; Kesava, S. V.; Gomez, E. D.; Robertson, M. L. . Sustainable thermoplastic elastomers derived from fatty acids . Macromolecules , 2013 . 46 7202 - 7212 . DOI: 10.1021/ma4011846 http://doi.org/10.1021/ma4011846 .

Wang, Z.; Yuan, L.; Trenor, N. M.; Vlaminck, L.; Billiet, S.; Sarkar, A.; Du Prez, F. E.; Stefik, M.; Tang, C. . Sustainable thermoplastic elastomers derived from plant oil and their “click-coupling” via TAD chemistry . Green Chem. , 2015 . 17 3806 - 3818 . DOI: 10.1039/C5GC00822K http://doi.org/10.1039/C5GC00822K .

Wang, Z.; Yuan, L.; Tang, C. . Sustainable elastomers from renewable biomass . Acc. Chem. Res. , 2017 . 50 1762 - 1773 . DOI: 10.1021/acs.accounts.7b00209 http://doi.org/10.1021/acs.accounts.7b00209 .

Serrano, M. C.; Chung, E. J.; Ameer, G. A. . Advances and applications of biodegradable elastomers in regenerative medicine . Adv. Funct. Mater. , 2010 . 20 192 - 208 . DOI: 10.1002/adfm.200901040 http://doi.org/10.1002/adfm.200901040 .

Liu, Q.; Jiang, L.; Shi, R.; Zhang, L. . Synthesis, preparation, in vitro degradation, and application of novel degradable bioelastomers—a review . Prog. Polym. Sci. , 2012 . 37 715 - 765 . DOI: 10.1016/j.progpolymsci.2011.11.001 http://doi.org/10.1016/j.progpolymsci.2011.11.001 .

Ye, H.; Zhang, K.; Kai, D.; Li, Z.; Loh, X. J. . Polyester elastomers for soft tissue engineering . Chem. Soc. Rev. , 2018 . 47 4545 - 4580 . DOI: 10.1039/C8CS00161H http://doi.org/10.1039/C8CS00161H .

Wanamaker, C. L.; O'Leary, L. E.; Lynd, N. A.; Hillmyer, M. A.; Tolman, W. B. . Renewable-resource thermoplastic elastomers based on polylactide and polymenthide . Biomacromolecules , 2007 . 8 3634 - 3640 . DOI: 10.1021/bm700699g http://doi.org/10.1021/bm700699g .

Guerin, W.; Helou, M.; Carpentier, J. F.; Slawinski, M.; Brusson, J. M.; Guillaume, S. M. . Macromolecular engineering via ring-opening polymerization (1): L-lactide/trimethylene carbonate block copolymers as thermoplastic elastomers . Polym. Chem. , 2013 . 4 1095 - 1106 . DOI: 10.1039/C2PY20859H http://doi.org/10.1039/C2PY20859H .

Watts, A.; Kurokawa, N.; Hillmyer, M. A. . Strong, resilient, and sustainable aliphatic polyester thermoplastic elastomers . Biomacromolecules , 2017 . 18 1845 - 1854 . DOI: 10.1021/acs.biomac.7b00283 http://doi.org/10.1021/acs.biomac.7b00283 .

Wanamaker, C. L.; Bluemle, M. J.; Pitet, L. M.; O'Leary, L. E.; Tolman, W. B.; Hillmyer, M. A. . Consequences of polylactide stereochemistry on the properties of polylactide-polymenthide-polylactide thermoplastic elastomers . Biomacromolecules , 2009 . 10 2904 - 2911 . DOI: 10.1021/bm900721p http://doi.org/10.1021/bm900721p .

Shin, J.; Lee, Y.; Tolman, W. B.; Hillmyer, M. A. . Thermoplastic elastomers derived from menthide and tulipalin A . Biomacromolecules , 2012 . 13 3833 - 3840 . DOI: 10.1021/bm3012852 http://doi.org/10.1021/bm3012852 .

Hillmyer, M. A.; Tolman, W. B. . Aliphatic polyester block polymers: renewable, degradable, and sustainable . Acc. Chem. Res. , 2014 . 47 2390 - 2396 . DOI: 10.1021/ar500121d http://doi.org/10.1021/ar500121d .

Dey, J.; Xu, H.; Shen, J.; Thevenot, P.; Gondi, S. R.; Nguyen, K. T.; Sumerlin, B. S.; Tang, L.; Yang, J. . Development of biodegradable crosslinked urethane-doped polyester elastomers . Biomaterials , 2008 . 29 4637 - 4649 . DOI: 10.1016/j.biomaterials.2008.08.020 http://doi.org/10.1016/j.biomaterials.2008.08.020 .

Brutman, J. P.; De, Hoe G. X.; Schneiderman, D. K.; Le, T. N.; Hillmyer, M. A. . Renewable, degradable, and chemically recyclable cross-linked elastomers . Ind. Eng. Chem. Res. , 2016 . 55 11097 - 11106 . DOI: 10.1021/acs.iecr.6b02931 http://doi.org/10.1021/acs.iecr.6b02931 .

De Hoe, G. X.; Zumstein, M. T.; Tiegs, B. J.; Brutman, J. P.; McNeill, K.; Sander, M.; Coates, G. W.; Hillmyer, M. A. . Sustainable polyester elastomers from lactones: synthesis, properties, and enzymatic hydrolyzability . J. Am. Chem. Soc. , 2018 . 140 963 - 973 . DOI: 10.1021/jacs.7b10173 http://doi.org/10.1021/jacs.7b10173 .

Xu, S.; Chang, P.; Zhao, B.; Adeel, M.; Zheng, S. . Formation of poly( ε -caprolactone) networks via supramolecular hydrogen bonding interactions . Chinese J. Polym. Sci. , 2018 . 37 197 - 207 . .

Zhang, D.; Hillmyer, M. A.; Tolman, W. B. . Catalytic polymerization of a cyclic ester derived from a "cool" natural precursor . Biomacromolecules , 2005 . 6 2091 - 2095 . DOI: 10.1021/bm050076t http://doi.org/10.1021/bm050076t .

Shin, J.; Martello, M. T.; Shrestha, M.; Wissinger, J. E.; Tolman, W. B.; Hillmyer, M. A. . Pressure-sensitive adhesives from renewable triblock copolymers . Macromolecules , 2011 . 44 87 - 94 . DOI: 10.1021/ma102216d http://doi.org/10.1021/ma102216d .

Wilson, J. A.; Hopkins, S. A.; Wright, P. M.; Dove, A. P. . Synthesis and postpolymerization modification of one-pot ω -pentadecalactone block-like copolymers . Biomacromolecules , 2015 . 16 3191 - 3200 . DOI: 10.1021/acs.biomac.5b00862 http://doi.org/10.1021/acs.biomac.5b00862 .

Kamber, N. E.; Jeong, W.; Waymouth, R. M.; Pratt, R. C.; Lohmeijer, B. G.; Hedrick, J. L. . Organocatalytic ring-opening polymerization . Chem. Rev. , 2007 . 107 5813 - 40 . DOI: 10.1021/cr068415b http://doi.org/10.1021/cr068415b .

Ottou, W. N.; Sardon, H.; Mecerreyes, D.; Vignolle, J.; Taton, D. . Update and challenges in organo-mediated polymerization reactions . Prog. Polym. Sci. , 2016 . 56 64 - 115 . DOI: 10.1016/j.progpolymsci.2015.12.001 http://doi.org/10.1016/j.progpolymsci.2015.12.001 .

Jiang, Z. L.; Zhao, J. P.; Zhang, G. Z. . Readily prepared and tunable ionic organocatalysts for ring-opening polymerization of lactones . Chinese J. Polym. Sci. , 2019 . 37 1205 - 1214 . DOI: 10.1007/s10118-019-2285-1 http://doi.org/10.1007/s10118-019-2285-1 .

Zhang, C. J.; Zhang, X. H. . Organocatalytic polymerization . Sci. Chin. Chem. , 2019 . 62 1087 - 1089 . DOI: 10.1007/s11426-019-9483-2 http://doi.org/10.1007/s11426-019-9483-2 .

Dove, A. P. . Organic catalysis for ring-opening polymerization . ACS Macro Lett. , 2012 . 1 1409 - 1412 . DOI: 10.1021/mz3005956 http://doi.org/10.1021/mz3005956 .

Yuan, P.; Hong, M. . Ring-opening polymerizations of the “non-strained” γ -butyrolactone andits derivatives: an overview and outlook . Acta Polymerica Sinica (in Chinese) , 2019 . 50 327 - 337 . .

An, Z. S.; Chen, C. L.; He, J. P.; Hong, C. Y.; Li, Z. B.; L,; Z., C.; Liu C.; Lv, X. B.; Qin, A. J.; Qu, C. K.; Tang, B. Z.; Tao, Y. H.; Wan, X. H.; Wang, G. W.; Wang, J.; Zheng, K.; Zou, W. K. . Research and development of polymer synthetic chemistry in China . Acta Polymerica Sinica (in Chinese) , 2019 . 50 1083 - 1132 . .

Li, H.; Zhao, N.; Ren, C.; Liu, S.; Li, Z. . Synthesis of linear and star poly( ε -caprolactone) with controlled and high molecular weights via cyclic trimeric phosphazene base catalyzed ring-opening polymerization . Polym. Chem. , 2017 . 8 7369 - 7374 . DOI: 10.1039/C7PY01673E http://doi.org/10.1039/C7PY01673E .

Liu, S.; Li, H.; Zhao, N.; Li, Z. . Stereoselective ring-opening polymerization of rac -lactide using organocatalytic cyclic trimeric phosphazene base . ACS Macro Lett. , 2018 . 7 624 - 628 . DOI: 10.1021/acsmacrolett.8b00353 http://doi.org/10.1021/acsmacrolett.8b00353 .

Li, Y.; Zhao, N.; Wei, C.; Sun, A.; Liu, S.; Li, Z. . Binary organocatalytic system for ring-opening polymerization of ε -caprolactone and δ -valerolactone: synergetic effects for enhanced selectivity . Eur. Polym. J. , 2019 . 111 11 - 19 . DOI: 10.1016/j.eurpolymj.2018.12.012 http://doi.org/10.1016/j.eurpolymj.2018.12.012 .

Zhao, N.; Ren, C.; Li, H.; Li, Y.; Liu, S.; Li, Z. . Selective ring-opening polymerization of non-strained γ -butyrolactone catalyzed by a cyclic trimeric phosphazene base . Angew. Chem. Int. Ed. , 2017 . 56 12987 - 12990 . DOI: 10.1002/anie.201707122 http://doi.org/10.1002/anie.201707122 .

Shen, Y.; Zhang, J.; Zhao, N.; Liu, F.; Li, Z. . Preparation of biorenewable poly( γ -butyrolactone)- b -poly(L-lactide) diblock copolyesters via one-pot sequential metal-free ring-opening polymerization . Polym. Chem. , 2018 . 9 2936 - 2941 . DOI: 10.1039/C8PY00389K http://doi.org/10.1039/C8PY00389K .

Shen, Y.; Zhang, J.; Zhao, Z.; Zhao, N.; Liu, F.; Li, Z. . Preparation of amphiphilic poly(ethylene glycol)- b -poly( γ -butyrolactone) diblock copolymer via ring opening polymerization catalyzed by a cyclic trimeric phosphazene base or alkali alkoxide . Biomacromolecules , 2019 . 20 141 - 148 . DOI: 10.1021/acs.biomac.8b01239 http://doi.org/10.1021/acs.biomac.8b01239 .

Shen, Y.; Zhao, Z.; Li, Y.; Liu, S.; Liu, F.; Li, Z. . A facile method to prepare high molecular weight bio-renewable poly( γ -butyrolactone) using a strong base/urea binary synergistic catalytic system . Polym. Chem. , 2019 . 10 1231 - 1237 . DOI: 10.1039/C8PY01812J http://doi.org/10.1039/C8PY01812J .

Zhao, N.; Ren, C.; Shen, Y.; Liu, S.; Li, Z. . Facile synthesis of aliphatic ω -pentadecalactone containing diblock copolyesters via sequential rop with L-lactide, ε -caprolactone, and δ -valerolactone catalyzed by cyclic trimeric phosphazene base with inherent tribasic characteristics . Macromolecules , 2019 . 52 1083 - 1091 . DOI: 10.1021/acs.macromol.8b02690 http://doi.org/10.1021/acs.macromol.8b02690 .

Dargaville, B. L.; Vaquette, C.; Peng, H.; Rasoul, F.; Chau, Y. Q.; Cooper-White, J. J.; Campbell, J. H.; Whittaker, A. K. . Cross-linked poly(trimethylene carbonate- co -L-lactide) as a biodegradable, elastomeric scaffold for vascular engineering applications . Biomacromolecules , 2011 . 12 3856 - 3869 . DOI: 10.1021/bm201291e http://doi.org/10.1021/bm201291e .

Zumstein, M. T.; Kohler, H. P.; McNeill, K.; Sander, M. . Enzymatic hydrolysis of polyester thin films: real-time analysis of film mass changes and dissipation dynamics . Environ. Sci. Technol. , 2016 . 50 197 - 206 . DOI: 10.1021/acs.est.5b04103 http://doi.org/10.1021/acs.est.5b04103 .

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Preparation of Degradable Polymenthide and Its Elastomers from Biobased Menthide via Organocatalyzed Ring-opening Polymerization and UV Curing

DOI：10.1007/s10118-020-2415-9

摘要

Abstract

关键词

Keywords

references