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 Tg 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.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
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.
Billiet, L.; Hillewaere, X. K. D.; Du Prez, F. E. Highly functionalized, aliphatic polyamides via CuAAC and thiolyne chemistries. Eur. Polym. J.2012, 48, 2085–2096.
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. Macromolecules2019, 52, 167–175.
Liu, Y. L.; Hsieh, C. Y.; Chen, Y. W. Thermally reversible crosslinked polyamides and thermoresponsive gels by means of Diels- Alder reaction. Polymer2006, 47, 2581–2586.
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. Macromolecules2014, 47, 8247–8254.
Williams, J. C.; Meador, M. A. B.; McCorkle, L.; Mueller, C.; Wilmoth, N. Synthesis and properties of step-growth polyamide aerogels crosslinked with triacid chlorides. Chem. Mater.2014, 26, 4163–4171.
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.
Gao, C.; Yan, D. Hyperbranched polymers: From synthesis to applications. Prog. Polym. Sci.2004, 29, 183–275.
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.
Buckwalter, D. J.; Dennis, J. M.; Long, T. E. Amide-containing segmented copolymers. Prog. Polym. Sci.2015, 45, 1–22.
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.
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.
Zhang, C. Q.; Madbouly, S. A.; Kessler, M. R. Biobased polyurethanes prepared from different vegetable oils. ACS Appl. Mater. Interfaces2015, 7, 1226–1233.
Acknowledgments
This work was financially supported by the Beijing Natural Science Foundation (No. 2182056) and the National Natural Science Foundation of China (No. 21244006).
Author information
Authors and Affiliations
Corresponding authors
Electronic Supplementary Information
10118_2019_2332_MOESM1_ESM.pdf
Cross-linked Polyamides Prepared through Direct Bulk Michael Addition and Polycondensation from 1,6-Hexanediamine and Methyl Acrylate
Rights and permissions
About this article
Cite this article
Yang, SQ., Zhao, JN., Zhao, JB. et al. Cross-linked Polyamides Prepared through Direct Bulk Michael Addition and Polycondensation from 1,6-Hexanediamine and Methyl Acrylate. Chin J Polym Sci 38, 143–150 (2020). https://doi.org/10.1007/s10118-019-2332-y
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10118-019-2332-y