Advertisement

Journal of Materials Science

, Volume 55, Issue 5, pp 2068–2076 | Cite as

Zeolitic imidazolate framework promoters in one-pot epoxy–amine reaction

  • Mi R. Kim
  • Taehee Kim
  • Hyeong S. Rye
  • Wonjoo Lee
  • Hyeon-Gook Kim
  • Moon Il Kim
  • Bongkuk SeoEmail author
  • Choong-Sun LimEmail author
Chemical routes to materials
First Online:
  • 85 Downloads

Abstract

Epoxy composites are widely used in commercial products. For industrial purposes, storage stability is one of their most important characteristics. To enable this feature, alternative promoters that are stable at a low-energy state, where they do not react, are needed. Zeolitic imidazolate frameworks (ZIFs) are organic–inorganic complexes, and they contain imidazolate linkers, which are one of the promoters in the epoxy–amine reaction. In this study, the stability of a one-pot epoxy–amine composite was improved by using ZIFs as promoters. ZIFs were synthesized using the solvothermal method, and their structure were confirmed using X-ray diffraction analysis and field-emission scanning electron microscopy. The activation energy of the ZIFs was measured using the non-isothermal method of differential scanning calorimetry, and it was calculated using the Kissinger equation. Furthermore, the storage stability of the one-pot epoxy–amine system was measured considering the viscosity change with time at constant temperature. The viscoelastic behavior of the cured sample was demonstrated using dynamic mechanical analysis.

This is a preview of subscription content, log in to check access.

Notes

Acknowledgements

This work was financially supported by the Korea Research Institute of Chemical Technology (KRICT), Grant No. SI 1941-20.

Author’s contributions

The manuscript was written through contributions of all authors. All authors have given approval to the final version of the manuscript.

Compliance with ethical standards

Conflict of interest

The authors declare no competing financial interest.

References

  1. 1.
    Rebizant V, Venet AS, Tournilhac F, Reydet EG, Navarro C, Pascault JP, Leibler L (2004) Chemistry and mechanical properties of epoxy-based thermosets reinforced by reactive and nonreactive SBMX block copolymers. Macromolecules 37:8017–8027CrossRefGoogle Scholar
  2. 2.
    Cole KC, Hechler J-J, Noel DA (1991) A new approach to modeling the cure kinetics of epoxy/amine thermosetting resins. 2. Application to a typical system based on bis[4-(diglycidylamino)phenyl]methane and bis(4-aminophenyl) sulfone. Macromolecules 24:3098–3110CrossRefGoogle Scholar
  3. 3.
    Wegmann A (1997) Chemical resistance of waterborne epoxy/amine coatings. Prog Org Coat 32:231–239CrossRefGoogle Scholar
  4. 4.
    Awja F, Gilbert M, Kelly G, Fox B, Pigram PJ (2009) Adhesion of polymers. Prog Polym Sci 34:948–968CrossRefGoogle Scholar
  5. 5.
    Vyazovkin S, Sbirrazzuoli N (1996) Mechanism and kinetics of epoxy–amine cure studied by differential scanning calorimetry. Macromolecules 29:1867–1873CrossRefGoogle Scholar
  6. 6.
    Gao L, Zhang Q, Li H, Yu S, Zhong W, Sui G, Yang X (2017) Effect of epoxy monomer structure on the curing process and thermo-mechanical characteristics of tri-functional epoxy/amine systems: a methodology combining atomistic molecular simulation with experimental analyses. Polym Chem 8:2016–2027CrossRefGoogle Scholar
  7. 7.
    Musto P (2003) Two-dimensional FTIR spectroscopy studies on the thermal-oxidative degradation of epoxy and epoxy–bis(maleimide) networks. Macromolecules 36:3210–3221CrossRefGoogle Scholar
  8. 8.
    Konuray AO, Fernández-Francos X, Ramis X (2017) Analysis of the reaction mechanism of the thiol–epoxy addition initiated by nucleophilic tertiary amines. Polym Chem 8:5934–5947CrossRefGoogle Scholar
  9. 9.
    Yang T, Zhang C, Zhang J, Cheng J (2014) The influence of tertiary amine accelerators on the curing behaviors of epoxy/anhydride systems. Thermochim Acta 577:11–16CrossRefGoogle Scholar
  10. 10.
    Hesabi M, Salimi A, Beheshty MH (2017) Effect of tertiary amine accelerators with different substituents on curing kinetics and reactivity of epoxy/dicyandiamide system. Polym Test 59:344–354CrossRefGoogle Scholar
  11. 11.
    LaLiberte BR, Bornstein J, Sacher RE (1983) Cure behavior of an epoxy resin-dicyandiamide system accelerated by monuron. Ind Eng Chem Prod Res Dev 22:261–262CrossRefGoogle Scholar
  12. 12.
    Park WH, Lee JK, Kwon KJ (1996) Cure behavior of an epoxy-anhydride-imidazole system. Polym J 28:407–411CrossRefGoogle Scholar
  13. 13.
    Heise MS, Martin GC (1989) Curing mechanism and thermal properties of epoxy-imidazole systems. Macromolecules 22:99–104CrossRefGoogle Scholar
  14. 14.
    Rahmathulah MA, Jeyarajasingam MA, Merritt B, VanLandingham M, McKnight SH, Palmese GR (2009) Room temperature ionic liquids as thermally latent initiators for polymerization of epoxy resins. Macromolecules 42:3219–3221CrossRefGoogle Scholar
  15. 15.
    Suzuki K, Matsu-ura N, Horii H, Sugita Y, Sanda F, Endo T (2003) One-pot curing system of epoxy resin imines initiated with water. J Appl Polym Sci 88:878–882CrossRefGoogle Scholar
  16. 16.
    Ham YR, Lee DH, Kim SH, Shin YJ, Yang M, Shin JS (2010) Microencapsulation of imidazole curing agent for epoxy resin. J Ind Eng Chem 16:728–733CrossRefGoogle Scholar
  17. 17.
    Xu J, Liu J, Li Z, Wang X, Wang Z (2019) Synthesis, structure and properties of Pd@MOF-808. J Mater Sci 54:12911–12924.  https://doi.org/10.1007/s10853-019-03786-0 CrossRefGoogle Scholar
  18. 18.
    Kim H, Moon H-S, Sohail M, Yoon Y-N, Shah SFA, Yim K, Moon J-H, Park YC (2019) Synthesis of cyclic carbonate by CO2 fixation to epoxides using interpenetrated MOF-5/n-Bu4NBr. J Mater Sci 54:11796–11803.  https://doi.org/10.1007/s10853-019-03702-6 CrossRefGoogle Scholar
  19. 19.
    Wang S, Ye B, An C, Wang J, Li Q (2019) Synergistic effects between Cu metal-organic framework (Cu-MOF) and carbon nanomaterials for the catalyzation of the thermal decomposition of ammonium perchlorate (AP). J Mater Sci 54:4928–4941.  https://doi.org/10.1007/s10853-018-03219-4 CrossRefGoogle Scholar
  20. 20.
    Yaghi MO, O’Keeffe MN, Ockwig W, Chae HK, Eddaoudi M, Kim J (2003) Reticular synthesis and the design of new materials. Nature 423:705–714CrossRefGoogle Scholar
  21. 21.
    Li H, Eddaoudi M, O’Keeffe M, Yaghi OM (1999) Design and synthesis of an exceptionally stable and highly porous metal-organic framework. Nature 402:276–279CrossRefGoogle Scholar
  22. 22.
    Furukawa H, Cordova KE, O’Keeffe M, Yaghi OM (2013) The chemistry and applications of metal-organic frameworks. Science 341:1230444CrossRefGoogle Scholar
  23. 23.
    Kreno LE, Leong K, Farha OK, Allendorf M, Van Duyne RP, Hupp JT (2012) Metal-organic framework materials as chemical sensors. Chem Rev 112:1105–1125CrossRefGoogle Scholar
  24. 24.
    Lee JY, Farha OK, Roberts J, Scheidt KA, Nguyen ST, Hupp JT (2009) Metal-organic framework materials as catalysts. Chem Soc Rev 38:1450–1459CrossRefGoogle Scholar
  25. 25.
    Horcajada P, Chalati T, Serre C, Gillet B, Sebrie C, Baati T, Eubank JF, Heurtaux D, Clayette P, Kreuz C, Chang JS, Hwang YK, Marsaud V, Bories PN, Cynober L, Gil S, Férey G, Couvreur P, Gref R (2010) Porous metal-organic-framework nanoscale carriers as a potential platform for drug delivery and imaging. Nat Mater 9:172–178CrossRefGoogle Scholar
  26. 26.
    Park KS, Ni Z, Cote AP, Choi JY, Huang R, Uribe-Romo FJ, Chae HK, O’Keeffe M, Yaghi OM (2006) Exceptional chemical and thermal stability of zeolitic imidazolate frameworks. Proc Natl Acad Sci USA 103:10186–10191CrossRefGoogle Scholar
  27. 27.
    Venna SR, Carreon MA (2010) Highly permeable zeolite imidazolate framework-8 membranes for CO2/CH4 separation. J Am Chem Soc 132:76–78CrossRefGoogle Scholar
  28. 28.
    Tran UPN, Le KKA, Phan NTS (2011) Expanding applications of metal-organic frameworks: zeolite imidazolate framework ZIF-8 as an efficient heterogeneous catalyst for the Knoevenagel reaction. ACS Catal 1:120–127CrossRefGoogle Scholar
  29. 29.
    Nguyen LTL, Le KKA, Phan NTS (2012) A zeolite imidazolate framework ZIF-8 catalyst for Friedel-Crafts acylation. Chin J Catal 33:688–696CrossRefGoogle Scholar
  30. 30.
    Miralda MC, Macias EE, Zhu M, Ratnasamy P, Carreon MA (2012) Zeolitic imidazole framework-8 catalysts in the conversion of CO2 to chloropropene carbonate. ACS Catal 2:180–183CrossRefGoogle Scholar
  31. 31.
    Dang TT, Zhu Y, Ngiam JSY, Ghosh SC, Chen A, Seayad AM (2013) Palladium nanoparticles supported on ZIF-8 as an efficient heterogeneous catalyst for aminocarbonylation. ACS Catal 3:1406–1410CrossRefGoogle Scholar
  32. 32.
    He M, Yao J, Liu Q, Zhong Z, Wang H (2013) Toluene-assisted synthesis of RHO-type zeolitic imidazolate frameworks: synthesis and formation mechanism of ZIF-11 and ZIF-12. Dalton Trans 42:16608–16613CrossRefGoogle Scholar
  33. 33.
    Kissinger HE (1957) Reaction kinetics in differential thermal analysis. Anal Chem 29:1702–1706CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Advanced Industrial Chemistry Research CenterKorea Research Institute of Chemical TechnologyUlsanRepublic of Korea
  2. 2.Environmental AdministrationCatholic University of PusanBusanRepublic of Korea

Personalised recommendations

Cite article

Buy options