Cross-linked Polyamides Prepared through Direct Bulk Michael Addition and Polycondensation from 1,6-Hexanediamine and Methyl Acrylate

Sheng-Qing Yang; Jin-Nan Zhao; Jing-Bo Zhao; Zhi-Yuan Zhang; Jun-Ying Zhang

doi:10.1007/s10118-019-2332-y

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Cross-linked Polyamides Prepared through Direct Bulk Michael Addition and Polycondensation from 1,6-Hexanediamine and Methyl Acrylate

ARTICLE | Updated：2019-10-12

- Cross-linked Polyamides Prepared through Direct Bulk Michael Addition and Polycondensation from 1,6-Hexanediamine and Methyl Acrylate
- Chinese Journal of Polymer Science Vol. 38, Issue 2, Pages: 143-150(2020)
- Affiliations：
  
  Key Laboratory of Carbon Fiber and Functional Polymers (Beijing University of Chemical Technology), Ministry of Education; College of Materials Science and Engineering, Beijing University of Chemical Technology, Beijing 100029, China
- Author bio：
  
  zhaojb@mail.buct.edu.cn (J.B.Z.)
  zhangjy@mail.buct.edu.cn (J.Y.Z.)
- Funds：
- DOI：10.1007/s10118-019-2332-y
  CLC：
- Received：22 April 2019，
  
  Revised：2019-7-5，
  
  Accepted：19 July 2019，
  
  Online First：12 October 2019，
  
  Published：2020-02
- Accepted：
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Citation: Yang, S. Q.; Zhao, J. N.; Zhao, J. B.; Zhang, Z. Y.; Zhang, J. Y. Cross-linked polyamides prepared through direct bulk Michael addition and polycondensation from 1,6-hexanediamine and methyl acrylate. Chinese J. Polym. Sci. 2020, 38, 143–150

Sheng-Qing Yang, Jin-Nan Zhao, Jing-Bo Zhao, et al. Cross-linked Polyamides Prepared through Direct Bulk Michael Addition and Polycondensation from 1,6-Hexanediamine and Methyl Acrylate[J]. Chinese Journal of Polymer Science, 2020, 38(2): 143-150.
Citation: Yang, S. Q.; Zhao, J. N.; Zhao, J. B.; Zhang, Z. Y.; Zhang, J. Y. Cross-linked polyamides prepared through direct bulk Michael addition and polycondensation from 1,6-hexanediamine and methyl acrylate. Chinese J. Polym. Sci. 2020, 38, 143–150 DOI： 10.1007/s10118-019-2332-y.

Sheng-Qing Yang, Jin-Nan Zhao, Jing-Bo Zhao, et al. Cross-linked Polyamides Prepared through Direct Bulk Michael Addition and Polycondensation from 1,6-Hexanediamine and Methyl Acrylate[J]. Chinese Journal of Polymer Science, 2020, 38(2): 143-150. DOI： 10.1007/s10118-019-2332-y.

摘要

Abstract

Cross-linked polyamides (cPAs) were prepared through direct bulk Michael addition and subsequent polycondensation. Several mixed hexanediamine multi-esters (HDAMEs) were generated through the Michael addition of 1

6-hexanediamine (HDA) and methyl acrylate (MA) at 50 °C with different HDA/MA molar ratios. Melt polycondensation of HDAMEs then proceeded at 150 or 170 °C in flasks to obtain viscous fluids

and curing was continued in tetrafluoroethylene molds to obtain cPA films. The Michael addition was monitored on the basis of FTIR and ESI-MS spectra. The cPA films were characterized by DSC

TGA

dynamic mechanical analysis

and tensile test. These directly prepared cPAs exhibited

of 1–39 °C

tensile strength of up to 45 MPa

and strain at break from 18% to 40%. The cPAs with high tensile strength and good toughness were successfully synthesized through the direct bulk Michael addition from HDA and MA followed with polycondensation.

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references

Jeong, S.; Kwak, G.; Takagi, A.; Fujiki, M.; Lee, D. H.; Park, L. S.; Yoon, K. B . Luminous, fully aliphatic polyamides: multicolor photoluminescence, their pH and solvent dependency . Eur. Polym. J. , 2008 . 44 1149 - 1156 . DOI: 10.1016/j.eurpolymj.2008.01.036 http://doi.org/10.1016/j.eurpolymj.2008.01.036 .

Billiet, L.; Hillewaere, X. K. D.; Du Prez, F. E . Highly functionalized, aliphatic polyamides via CuAAC and thiol-yne chemistries . Eur. Polym. J. , 2012 . 48 2085 - 2096 . DOI: 10.1016/j.eurpolymj.2012.08.013 http://doi.org/10.1016/j.eurpolymj.2012.08.013 .

Desbois, P.; Bruchmann, B.; Scherzer, D.; Wollny, A.; Radtke, A. Process for producing polyamides via anionic polymerization. 2013 , U.S. Pat., 20130079465 A1.

Minematsu, H.; Masuko, T. Preparation of crosslinked polyamides with high viscosity. 1990 , Jpn. Kokai Tokkyo Koho, 02032128 A.

Howland, C. P.; Bailey, K. M.; Workman, D. P.; Moeggenborg, K. J. Crosslinked polyamide binders for ceramics, ceramic precursor, and its manufacture. 1999 , PCT Int. Appl., WO 9928377 A1.

Sathyan, A.; Hayward, R. C.; Emrick, T . Ring-opening polymerization of allyl-functionalized lactams . Macromolecules , 2019 . 52 167 - 175 . DOI: 10.1021/acs.macromol.8b02148 http://doi.org/10.1021/acs.macromol.8b02148 .

Liu, Y. L.; Hsieh, C. Y.; Chen, Y. W . Thermally reversible cross-linked polyamides and thermoresponsive gels by means of Diels-Alder reaction . Polymer , 2006 . 47 2581 - 2586 . DOI: 10.1016/j.polymer.2006.02.057 http://doi.org/10.1016/j.polymer.2006.02.057 .

Trigo-López, M.; Barrio-Manso, J. L.; Serna, F.; García, F. C.; García, J. M . Crosslinked aromatic polyamides: a further step in high-performance materials . Macromol. Chem. Phys. , 2013 . 214 2223 - 2231 . .

Tunc, D.; Le Coz, C.; Alexandre, M.; Desbois, P.; Lecomte, P.; Carlotti, S . Reversible cross-linking of aliphatic polyamides bearing thermo- and photoresponsive cinnamoyl moieties . Macromolecules , 2014 . 47 8247 - 8254 . DOI: 10.1021/ma502083p http://doi.org/10.1021/ma502083p .

Williams, J. C.; Meador, M. A. B.; McCorkle, L.; Mueller, C.; Wilmoth, N . Synthesis and properties of step-growth polyamide aerogels cross-linked with triacid chlorides . Chem. Mater. , 2014 . 26 4163 - 4171 . DOI: 10.1021/cm5012313 http://doi.org/10.1021/cm5012313 .

Tylkowski, B.; Pregowska, M.; Jamowska, E.; Garcia-Valls, R.; Giamberini, M . Preparation of a new lightly cross-linked liquid crystalline polyamide by interfacial polymerization application to the obtainment of microcapsules with photo-triggered release . Eur. Polym. J. , 2009 . 45 1420 - 1432 . .

Wu, T.; Wang, N. X.; Li, J.; Wang, L.; Zhang, W.; Zhang, G. J.; Ji, S. L . Tubular thermal crosslinked-PEBA/ceramic membrane for aromatic/aliphatic pervaporation . J. Membr. Sci. , 2015 . 486 1 - 9 . DOI: 10.1016/j.memsci.2015.03.037 http://doi.org/10.1016/j.memsci.2015.03.037 .

Gao, C.; Yan, D . Hyperbranched polymers: from synthesis to applications . Prog. Polym. Sci. , 2004 . 29 183 - 275 . DOI: 10.1016/j.progpolymsci.2003.12.002 http://doi.org/10.1016/j.progpolymsci.2003.12.002 .

Han, W. S.; Lin, B. P.; Yang, H.; Zhang, X. Q . Synthesis of novel poly(ester amine) dendrimers by Michael addition and acrylate esterification . Des. Monomers Polym. , 2013 . 16 67 - 71 . DOI: 10.1080/15685551.2012.705491 http://doi.org/10.1080/15685551.2012.705491 .

Buckwalter, D. J.; Dennis, J. M.; Long, T. E . Amide-containing segmented copolymers . Prog. Polym. Sci. , 2015 . 45 1 - 22 . DOI: 10.1016/j.progpolymsci.2014.11.003 http://doi.org/10.1016/j.progpolymsci.2014.11.003 .

Jiang, M.; Chen, W.; Fang, P.; Chen, S. L.; Bai, J. X.; Huang, Y. F.; Han, M. W.; Lu, P.; Dong, J . Solvent-free polymerization of citric acid and hexamethylenediamine for novel carboxylated polyamides . J. Polym. Sci., Part A: Polym. Chem. , 2012 . 50 3819 - 3829 . DOI: 10.1002/pola.v50.18 http://doi.org/10.1002/pola.v50.18 .

Jiang, M.; Chen, G. S.; Lu, P.; Dong, J . Preparation of aqueous soluble polyamides from renewable succinic acid and citric acid as a new approach to design bio-inspired polymers . J. Appl. Polym. Sci. , 2014 . 131 39807 .

Yi, C. F.; Zhao, J. B.; Zhang, Z. Y.; Zhang, J. Y . Cross-linked polyamides synthesized through a Michael addition reaction coupled with bulk polycondensation . Ind. Eng. Chem. Res. , 2017 . 56 13743 - 13750 . DOI: 10.1021/acs.iecr.7b03416 http://doi.org/10.1021/acs.iecr.7b03416 .

Zhang, C. Q.; Madbouly, S. A.; Kessler, M. R . Biobased polyurethanes prepared from different vegetable oils . ACS Appl. Mater. Interfaces , 2015 . 7 1226 - 1233 . DOI: 10.1021/am5071333 http://doi.org/10.1021/am5071333 .

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