2-Ethy-4-methylimidazole terminated polyurethane prepolymer as functional latent curing agents for epoxy resin crosslinking

References

• Kinjo, N.; Ogata, M.; Nishi, K.; Kaneda, A.; Dušek, K. Speciality Polymers/Polymer Physics; Springer: Berlin, 1989.
   Google Scholar
• Hodgkin, J. H.; Simon, G. P.; Varley, R. J. Thermoplastic Toughening of Epoxy Resins: A Critical Review. Polym. Adv. Technol. 1998, 9, 3–10. DOI: 10.1002/(SICI)1099-1581(199801)9:1 < 3::AID-PAT727 > 3.0.CO;2-I.
   Web of Science ®Google Scholar
• Ooi, S. K.; Cook, W. D.; Simon, G. P.; Such, C. H. DSC Studies of the Curing Mechanisms and Kinetics of DGEBA Using Imidazole Curing Agents. Polymer. 2000, 41, 3639–3649. DOI: 10.1016/S0032-3861(99)00600-X.
   Web of Science ®Google Scholar
• Rahmathullah, M. A. M.; Jeyarajasingam, A.; Merritt, B.; VanLandingham, M.; McKnight, S. H.; Palmese, G. R. Room Temperature Ionic Liquids as Thermally Latent Initiators for Polymerization of Epoxy Resins. Macromolecules. 2009, 42, 3219–3221. DOI: 10.1021/ma802669k.
   Web of Science ®Google Scholar
• White, L. A.; Weber, J. W.; Mathias, L. J. Synthesis and Thermal Characterization of a One Component Maleimide-Epoxy Resin. Polym. Bull. 2001, 46, 339–344. DOI: 10.1007/s002890170033.
   Google Scholar
• Mir, I.; Kumar, D. Recent Advances in Isotropic Conductive Adhesives for Electronics Packaging Applications. Int. J. Adhes. Adhes. 2008, 28, 362–371. DOI: 10.1016/j.ijadhadh.2007.10.004.
   Web of Science ®Google Scholar
• Wang, F.; Xiao, J.; Wang, J.-W.; Li, S.-Q. A Novel Imidazole Derivative Curing Agent for Epoxy Resin: synthesis, Characterization, and Cure Kinetic. J. Appl. Polym. Sci. 2008, 107, 223–227. DOI: 10.1002/app.27053.
   Web of Science ®Google Scholar
• Wong, F.-F.; Chen, K.-L.; Lin, C.-M.; Yeh, M.-Y. New Investigation of 1‐Substituted Imidazole Derivatives as Thermal Latent Catalysts for Epoxy‐Phenolic Resins. J. Appl. Polym. Sci. 2007, 104, 3292–3300. DOI: 10.1002/app.26002.
   Web of Science ®Google Scholar
• Lei, D.-F.; Ma, W.-S.; Wang, L.-F.; Zhang, D.-Q. Preparation of 2-Ethyl-4-Methylimidazole Derivatives as Latent Curing Agents and Their Application in Curing Epoxy Resin. J. Appl. Polym. Sci. 2015, 132. DOI: 10.1002/app.42563.
   Web of Science ®Google Scholar
• Brown, J.; Hamerton, I.; Howlin, B. J. Preparation, Characterization, and Thermal Properties of Controllable Metal–Imidazole Complex Curing Agents for Epoxy Resins. J. Appl. Polym. Sci. 2000, 75, 201–217. DOI: 10.1002/(SICI)1097-4628(20000110)75:2 < 201::AID-APP2 > 3.0.CO;2-#.
   Web of Science ®Google Scholar
• Maka, H.; Spychaj, T. Epoxy Resin Crosslinked with Conventional and Deep Eutectic Ionic Liquids. Polimery 2012, 57, 34–40. DOI: 10.14314/polimery.2012.456.
   Web of Science ®Google Scholar
• Soares, B. G.; Livi, S.; Duchet-Rumeau, J.; Gerard, J. F. Preparation of Epoxy/MCDEA Networks Modified with Ionic Liquids. Polymer 2012, 53, 60–66. DOI: 10.1016/j.polymer.2011.11.043.
   Web of Science ®Google Scholar
• Mąka, H.; Spychaj, T.; Adamus, J. Lewis Acid Type Deep Eutectic Solvents as Catalysts for Epoxy Resin Crosslinking. RSC Adv. 2015, 5, 82813–82821. DOI: 10.1039/C5RA12664A.
   Web of Science ®Google Scholar
• Chen, K.-L.; Shen, Y.-H.; Yeh, M.-Y.; Wong, F.-F. Complexes of Imidazole with Poly (Ethylene Glycol) s as the Thermal Latency Catalysts for Epoxy–Phenolic Resins. J. Taiwan. Inst. Chem. E 2012, 43, 306–312. DOI: 10.1016/j.jtice.2011.08.007.
   Web of Science ®Google Scholar
• Xing, S.; Yang, J.; Huang, Y.; Zheng, Q.; Zeng, J. Preparation and Characterization of a Novel Microcapsule-Type Latent Curing Agent for Epoxy Resin. Mater. Design 2015, 85, 661–670. DOI: 10.1016/j.matdes.2015.07.098.
   Web of Science ®Google Scholar
• Lee, J. Y.; Jang, J. Effect of Substituents on the Curing of Liquid Crystalline Epoxy Resin. J. Polym. Sci. A Polym. Chem. 1998, 36, 911–917. DOI: 10.1002/(SICI)1099-0518(19980430)36:6 < 911::AID-POLA6 > 3.0.CO;2-J.
   Web of Science ®Google Scholar
• Calvert, P. Materials Science-Rough Guide to the Nanoworld. Nature 1996, 383, 300–301. DOI: 10.1038/383300a0.
   Web of Science ®Google Scholar
• Qi, D.; Bai, F.; Yang, X.; Huang, W. Synthesis of Core-Shell Polymer Microspheres by Two-Stage Distillation–Precipitation Polymerization. Eur. Polym. J. 2005, 41, 2320–2328. DOI: 10.1016/j.eurpolymj.2005.04.034.
   Web of Science ®Google Scholar
• Choi, J.; Kim, S. G.; Laine, R. M. Organic/Inorganic Hybrid Epoxy Nanocomposites from Aminophenylsilsesquioxanes. Macromolecules 2004, 37, 99–109. DOI: 10.1021/ma030309d.
   Web of Science ®Google Scholar
• Harani, H.; Fellahi, S.; Bakar, M. Toughening of Epoxy Resin Using Synthesized Polyurethane Prepolymer Based on Hydroxyl‐Terminated Polyesters. J. Appl. Polym. Sci. 1998, 70, 2603–2618. DOI: 10.1002/(SICI)1097-4628(19981226)70:13 < 2603::AID-APP6 > 3.0.CO;2-4.
   Web of Science ®Google Scholar
• Lou, C.; Zhang, X.; Wang, Y.; Chen, Z.; H, L. Toughening Epoxy Resin with Blocked Isocyanate Containing Soft Chain. J. Appl. Polym. Sci. 2015, 132. DOI: 10.1002/app.41345.
   Web of Science ®Google Scholar
• Ricciardi, F.; Romanchick, W. A.; Joullié, M. M. 1, 3‐Dialkylimidazolium Salts as Latent Catalysts in the Curing of Epoxy Resins. J. Polym. Sci. B Polym. Lett. Ed. 1983, 21, 633–638. DOI: 10.1002/pol.1983.130210808.
   Google Scholar
• Gnanarajan, T. P.; Iyer, N. P.; Nasar, A. S.; Radhakrishnan, G. Preparation and Properties of Poly (Urethane-Imide) s Derived from Amine-Blocked-Polyurethane Prepolymer and Pyromellitic Dianhydride. Eur. Polym. J 2002, 38, 487–495. DOI: 10.1016/S0014-3057(01)00216-6.
   Web of Science ®Google Scholar
• Eren, B.; Aydın, R.; Eren, E. Synthesis, Characterization, and Performance of a Benzimidazole-Based Membrane in Removal of Phosphate: first Lab-Scale Experimental Results. J. Mater. Sci. 2013, 48, 7456–7465. DOI: 10.1007/s10853-013-7560-x.
   Web of Science ®Google Scholar
• Delebecq, E.; Pascault, J. P.; Boutevin, B.; Ganachaud, F. On the Versatility of Urethane/Urea Bonds: reversibility, Blocked Isocyanate, and Non-Isocyanate Polyurethane. Chem. Rev. 2013, 113, 80–118. DOI: 10.1021/cr300195n.
   PubMed Web of Science ®Google Scholar
• Yin, L.; Liu, Y.; Ke, Z.; Yin, J. Preparation of a Blocked Isocyanate Compound and Its Grafting onto Styrene-b-(Ethylene-co-1-Butene)-b-Styrene Triblock Copolymer. Eur. Polym. J. 2009, 45, 191–198. DOI: 10.1016/j.eurpolymj.2008.10.016.
   Web of Science ®Google Scholar
• Gnanarajan, T. P.; Iyer, N. P.; Nasar, A. S.; Radhakrishnan, G. Synthesis and Dissociation of Amine‐Blocked Diisocyanates and Polyurethane Prepolymers. Polym. Int. 2002, 51, 195–202. DOI: 10.1002/pi.807.
   Web of Science ®Google Scholar
• Cai, H.; Li, P.; Sui, G.; Yu, Y.; Li, G.; Yang, X.; Ryu, S. Curing Kinetics Study of Epoxy Resin/Flexible Amine Toughness Systems by Dynamic and Isothermal DSC. Thermochim. Acta 2008, 473, 101–105. DOI: 10.1016/j.tca.2008.04.012.
   Web of Science ®Google Scholar
• Ricciardi, F.; Romanchick, W. A.; Joullié, M. M. Mechanism of Imidazole Catalysis in the Curing of Epoxy Resins. J. Polym. Sci. Polym. Chem. Ed. 1983, 21, 1475–1490. DOI: 10.1002/pol.1983.170210520.
   Web of Science ®Google Scholar
• Liu, L.; Li, M. Curing Mechanisms and Kinetic Analysis of DGEBA Cured with a Novel Imidazole Derivative Curing Agent Using DSC Techniques. J.Appl. Polym. Sci. 2010, 117, 3220–3227. DOI: 10.1002/app.32196.
   Web of Science ®Google Scholar
• Heise, M. S.; Martin, G. C. Curing Mechanism and Thermal Properties of Epoxy-Imidazole Systems. Macromolecules 1989, 22, 99–104. DOI: 10.1021/ma00191a020.
   Web of Science ®Google Scholar
• Vyazovkin, S.; Burnham, A. K.; Criado, J. M.; Pérez-Maqueda, L. A.; Popescu, C.; Sbirrazzuoli, N. ICTAC Kinetics Committee Recommendations for Performing Kinetic Computations on Thermal Analysis Data. Thermochim Acta 2011, 520, 1–19. DOI: 10.1016/j.tca.2011.03.034.
   Web of Science ®Google Scholar
• Liu, W.-B.; Wang, J.; Qiu, Q.-H.; Zhang, M.-L. Synthesis and Characterisation of an Epoxy Resin Containing Fluorene Moieties and Its Cured Polymer. Pigm. Resin. Technol. 2008, 37, 389–394. DOI: 10.1108/03699420810915085.
   Web of Science ®Google Scholar
• Kahraman, R.; Sunar, M.; Yilbas, B. Influence of Adhesive Thickness and Filler Content on the Mechanical Performance of Aluminum Single-Lap Joints Bonded with Aluminum Powder Filled Epoxy Adhesive. J. Mater. Process. Technol. 2008, 205, 183–189. DOI: 10.1016/j.jmatprotec.2007.11.121.
   Web of Science ®Google Scholar
• Rahmanian, S.; Suraya, A. R.; Shazed, M. A.; Zahari, R.; Zainudin, E. S. Mechanical Characterization of Epoxy Composite with Multiscale Reinforcements: Carbon Nanotubes and Short Carbon Fibers. Mater. Design 2014, 60, 34–40. DOI: 10.1016/j.matdes.2014.03.039.
   Web of Science ®Google Scholar
• Rimdusit, S.; Ishida, H. Development of New Class of Electronic Packaging Materials Based on Ternary Systems of Benzoxazine, Epoxy, and Phenolic Resins. Polymer 2000, 41, 7941–7949. DOI: 10.1016/S0032-3861(00)00164-6.
   Web of Science ®Google Scholar