In-Out Surface Modification of Halloysite Nanotubes (HNTs) for Excellent Cure of Epoxy: Chemistry and Kinetics Modeling

Nanomaterials - Tập 11 Số 11 - Trang 3078
Shahab Moghari1, Seyed Hassan Jafari1, Mohsen Khodadadi Yazdi2, Maryam Jouyandeh2, Aleksander Hejna3, Payam Zarrintaj4, Mohammad Reza Saeb3
1School of Chemical Engineering, College of Engineering, University of Tehran, Tehran, 11155-4563, Iran
2Center of Excellence in Electrochemistry, School of Chemistry, College of Science, University of Tehran, Tehran 141746-6191, Iran
3Department of Polymer Technology, Gdańsk University of Technology, Narutowicza, 11/12, 80-233 Gdańsk, Poland
4School of Chemical Engineering, Oklahoma State University, 420 Engineering North, Stillwater, OK 74078, USA

Tóm tắt

In-out surface modification of halloysite nanotubes (HNTs) has been successfully performed by taking advantage of 8-hydroxyquinolines in the lumen of HNTs and precisely synthesized aniline oligomers (AO) of different lengths (tri- and pentamer) anchored on the external surface of the HNTs. Several analyses, including FTIR, H-NMR, TGA, UV-visible spectroscopy, and SEM, were used to establish the nature of the HNTs’ surface engineering. Nanoparticles were incorporated into epoxy resin at 0.1 wt.% loading for investigation of the contribution of surface chemistry to epoxy cure behavior and kinetics. Nonisothermal differential scanning calorimetry (DSC) data were fed into home-written MATLAB codes, and isoconversional approaches were used to determine the apparent activation energy (Eα) as a function of the extent of cure reaction (α). Compared to pristine HNTs, AO-HNTs facilitated the densification of an epoxy network. Pentamer AO-HNTs with longer arms promoted an Excellent cure; with an Eα value that was 14% lower in the presence of this additive than for neat epoxy, demonstrating an enhanced cross-linking. The model also predicted a triplet of cure (m, n, and ln A) for autocatalytic reaction order, non-catalytic reaction order, and pre-exponential factor, respectively, by the Arrhenius equation. The enhanced autocatalytic reaction in AO-HNTs/epoxy was reflected in a significant rise in the value of m, from 0.11 to 0.28. Kinetic models reliably predict the cure footprint suggested by DSC measurements.

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Tài liệu tham khảo

Jouyandeh, 2020, Synthesis, characterization, and high potential of 3D metal–organic framework (MOF) nanoparticles for curing with epoxy, J. Alloys Compd., 829, 154547, 10.1016/j.jallcom.2020.154547

Karami, 2019, Cure Index for labeling curing potential of epoxy/LDH nanocomposites: A case study on nitrate anion intercalated Ni-Al-LDH, Prog. Org. Coat., 136, 105228, 10.1016/j.porgcoat.2019.105228

Seidi, F., Jouyandeh, M., Taghizadeh, M., Taghizadeh, A., Vahabi, H., Habibzadeh, S., Formela, K., and Saeb, M.R. (2020). Metal-Organic Framework (MOF)/Epoxy Coatings: A Review. Materials, 13.

Jouyandeh, 2020, Nonisothermal cure kinetics of epoxy/MnxFe3-xO4 nanocomposites, Prog. Org. Coat., 140, 105505, 10.1016/j.porgcoat.2019.105505

Jouyandeh, 2019, Cure kinetics of epoxy/graphene oxide (GO) nanocomposites: Effect of starch functionalization of GO nanosheets, Prog. Org. Coat., 136, 105217, 10.1016/j.porgcoat.2019.105217

Jouyandeh, 2019, Curing epoxy with polyvinylpyrrolidone (PVP) surface-functionalized ZnxFe3-xO4 magnetic nanoparticles, Prog. Org. Coat., 136, 105227, 10.1016/j.porgcoat.2019.105227

Bayat, 2019, Thin films of epoxy adhesives containing recycled polymers and graphene oxide nanoflakes for metal/polymer composite interface, Prog. Org. Coat., 136, 105201, 10.1016/j.porgcoat.2019.06.047

Jouyandeh, 2018, Epoxy coatings physically cured with hydroxyl-contained silica nanospheres and halloysite nanotubes, Prog. Color Colorants Coat., 11, 199

Jouyandeh, 2019, Curing epoxy with electrochemically synthesized NixFe3-xO4 magnetic nanoparticles, Prog. Org. Coat., 136, 105198, 10.1016/j.porgcoat.2019.06.044

Jouyandeh, 2019, Curing epoxy with electrochemically synthesized GdxFe3-xO4 magnetic nanoparticles, Prog. Org. Coat., 136, 105245, 10.1016/j.porgcoat.2019.105245

Jouyandeh, 2019, Properties of nano-Fe3O4 incorporated epoxy coatings from Cure Index perspective, Prog. Org. Coat., 133, 220, 10.1016/j.porgcoat.2019.04.034

Farzad, 2021, Polyhedral oligomeric silsesquioxane/epoxy coatings: A review, Surf. Innov., 9, 3, 10.1680/jsuin.20.00037

Jouyandeh, 2019, Curing epoxy with polyethylene glycol (PEG) surface-functionalized NixFe3-xO4magnetic nanoparticles, Prog. Org. Coat., 136, 105250, 10.1016/j.porgcoat.2019.105250

Jouyandeh, 2019, Curing epoxy with electrochemically synthesized ZnxFe3-xO4 magnetic nanoparticles, Prog. Org. Coat., 136, 105246, 10.1016/j.porgcoat.2019.105246

Tikhani, F., Moghari, S., Jouyandeh, M., Laoutid, F., Vahabi, H., Saeb, M.R., and Dubois, P. (2020). Curing Kinetics and Thermal Stability of Epoxy Composites Containing Newly Obtained Nano-Scale Aluminum Hypophosphite (AlPO2). Polymers, 12.

Karami, 2019, Curing epoxy with Mg-Al LDH nanoplatelets intercalated with carbonate ion, Prog. Org. Coat., 136, 105278, 10.1016/j.porgcoat.2019.105278

Mostafaei, 2014, Epoxy/polyaniline–ZnO nanorods hybrid nanocomposite coatings: Synthesis, characterization and corrosion protection performance of conducting paints, Prog. Org. Coat., 77, 146, 10.1016/j.porgcoat.2013.08.015

Dehghanian, 2015, Corrosion protection of the reinforcing steels in chloride-laden concrete environment through epoxy/polyaniline–camphorsulfonate nanocomposite coating, Corros. Sci., 90, 239, 10.1016/j.corsci.2014.10.015

Mozafari, M., and Chauhan, N.P.S. (2019). Chapter 7—PANI-Based Nanostructures. Fundamentals and Emerging Applications of Polyaniline, Elsevier.

Jia, 2020, Preparation of pH responsive smart nanocontainer via inclusion of inhibitor in graphene/halloysite nanotubes and its application in intelligent anticorrosion protection, Appl. Surf. Sci., 504, 144496, 10.1016/j.apsusc.2019.144496

Zhou, 2020, Epoxy composite coating with excellent anticorrosion and self-healing performances based on multifunctional zeolitic imidazolate framework derived nanocontainers, Chem. Eng. J., 385, 123835, 10.1016/j.cej.2019.123835

Rahsepar, 2017, Synthesis and characterization of inhibitor-loaded silica nanospheres for active corrosion protection of carbon steel substrate, J. Alloys Compd., 709, 519, 10.1016/j.jallcom.2017.03.104

Zahidah, 2017, Halloysite nanotubes as nanocontainer for smart coating application: A review, Prog. Org. Coat., 111, 175, 10.1016/j.porgcoat.2017.05.018

Paran, 2019, Thermal decomposition kinetics of dynamically vulcanized polyamide 6–acrylonitrile butadiene rubber–halloysite nanotube nanocomposites, J. Appl. Polym. Sci., 136, 47483, 10.1002/app.47483

Akbari, V., Jouyandeh, M., Paran, S.M.R., Ganjali, M.R., Abdollahi, H., Vahabi, H., Ahmadi, Z., Formela, K., Esmaeili, A., and Mohaddespour, A. (2020). Effect of Surface Treatment of Halloysite Nanotubes (HNTs) on the Kinetics of Epoxy Resin Cure with Amines. Polymers, 12.

Vahedi, 2014, Instrumented impact properties and fracture behaviour of epoxy/modified halloysite nanocomposites, Polym. Test., 39, 101, 10.1016/j.polymertesting.2014.07.017

Ravichandran, 2019, Enhancement of mechanical properties of epoxy/halloysite nanotube (HNT) nanocomposites, SN Appl. Sci., 1, 296, 10.1007/s42452-019-0323-9

Lvov, 2019, Interfacial Self-Assembly in Halloysite Nanotube Composites, Langmuir, 35, 8646, 10.1021/acs.langmuir.8b04313

Ghodke, 2019, Functionalization, Uptake and Release Studies of Active Molecules Using Halloysite Nanocontainers, J. Inst. Eng. (India) Ser. E, 100, 59, 10.1007/s40034-019-00140-6

Lvov, 2008, Halloysite Clay Nanotubes for Controlled Release of Protective Agents, ACS Nano, 2, 814, 10.1021/nn800259q

Cavallaro, G., Danilushkina, A.A., Evtugyn, V.G., Lazzara, G., Milioto, S., Parisi, F., Rozhina, E.V., and Fakhrullin, R.F. (2017). Halloysite Nanotubes: Controlled Access and Release by Smart Gates. Nanomaterials, 7.

Abdullayev, 2010, Clay nanotubes for corrosion inhibitor encapsulation: Release control with end stoppers, J. Mater. Chem., 20, 6681, 10.1039/c0jm00810a

Suner, 2019, Cryogel composites based on hyaluronic acid and halloysite nanotubes as scaffold for tissue engineering, Int. J. Biol. Macromol., 130, 627, 10.1016/j.ijbiomac.2019.03.025

Lisuzzo, L., Cavallaro, G., Parisi, F., Milioto, S., Fakhrullin, R., and Lazzara, G. (2019). Core/Shell Gel Beads with Embedded Halloysite Nanotubes for Controlled Drug Release. Coatings, 9.

Zahidah, 2017, Benzimidazole-loaded halloysite nanotube as a smart coating application, Int. J. Eng. Technol. Innov., 7, 243

Vijayan, 2016, Halloysite Nanotube as Multifunctional Component in Epoxy Protective Coating, Ind. Eng. Chem. Res., 55, 11186, 10.1021/acs.iecr.6b02736

Hoseinzadeh, 2020, Formulation of a smart nanocomposite coating with pH-responsive loaded halloysite and investigation of its anticorrosion behaviour, Bull. Mater. Sci., 43, 230, 10.1007/s12034-020-02130-6

Luo, 2013, Liquid Crystalline Phase Behavior and Sol–Gel Transition in Aqueous Halloysite Nanotube Dispersions, Langmuir, 29, 12358, 10.1021/la402836d

Akbari, 2019, Surface chemistry of halloysite nanotubes controls the curability of low filled epoxy nanocomposites, Prog. Org. Coat., 135, 555, 10.1016/j.porgcoat.2019.06.009

Jouyandeh, 2019, Bushy-surface hybrid nanoparticles for developing epoxy superadhesives, Appl. Surf. Sci., 479, 1148, 10.1016/j.apsusc.2019.01.283

He, 2015, pH-Responsive nanovalves based on encapsulated halloysite for the controlled release of a corrosion inhibitor in epoxy coating, RSC Adv., 5, 90609, 10.1039/C5RA19296J

Ye, 2020, POSS-tetraaniline modified graphene for active corrosion protection of epoxy-based organic coating, Chem. Eng. J., 383, 123160, 10.1016/j.cej.2019.123160

Wei, 2008, Aniline oligomers—Architecture, function and new opportunities for nanostructured materials, Macromol. Rapid Commun., 29, 280, 10.1002/marc.200700741

Cao, 1986, Spectroscopic and electrical characterization of some aniline oligomers and polyaniline, Synth. Met., 16, 305, 10.1016/0379-6779(86)90167-0

Taka, 2018, Preparation of Aniline Dimer-COOH Modified Magnetite (Fe3O4) Nanoparticles by Ultrasonic Dispersion Method, Int. J. Eng. Technol., 7, 185, 10.14419/ijet.v7i4.30.22108

Tang, 1988, Infrared Spectra of Soluble Polyaniline, Synth. Met., 24, 231, 10.1016/0379-6779(88)90261-5

2004, Synthesis and spectroscopic properties of aniline tetramers. Comparative studies, New J. Chem., 28, 669, 10.1039/B311096F

Jouyandeh, M., Ganjali, M.R., Seidi, F., Xiao, H., and Saeb, M.R. (2020). Nonisothermal Cure Kinetics of Epoxy/Polyvinylpyrrolidone Functionalized Superparamagnetic Nano-Fe3O4 Composites: Effect of Zn and Mn Doping. J. Compos. Sci., 4.

Rossier, J.N.S., Pavic, A., Vojnovic, S., Stringer, T., Bättig, S., Smith, G.S., Nikodinovic-Runic, J., and Zobi, F. (2019). Antiplasmodial Activity and In Vivo Bio-Distribution of Chloroquine Molecules Released with a 4-(4-Ethynylphenyl)-Triazole Moiety from Organometallo-Cobalamins. Molecules, 24.

Jouyandeh, 2020, Highly curable self-healing vitrimer-like cellulose-modified halloysite nanotube/epoxy nanocomposite coatings, Chem. Eng. J., 396, 125196, 10.1016/j.cej.2020.125196

Zhang, 2020, Fabrication and characterization of surface modified HMX@ PANI core-shell composites with enhanced thermal properties and desensitization via in situ polymerization, Appl. Surf. Sci., 515, 146042, 10.1016/j.apsusc.2020.146042

Jana, 2015, Halloysite nanotubes capturing isotope selective atmospheric CO2, Sci. Rep., 5, 8711, 10.1038/srep08711

Filip, 2009, Some aspects of 8-hydroxyquinoline in solvents, Acta Chem. Iasi, 17, 85

Peng, 2017, Facile synthesis and characterization of ZnO nanoparticles grown on halloysite nanotubes for enhanced photocatalytic properties, Sci. Rep., 7, 2250, 10.1038/s41598-017-02501-w

Jouyandeh, 2019, Curing epoxy with polyvinylpyrrolidone (PVP) surface-functionalized MnxFe3-xO4 magnetic nanoparticles, Prog. Org. Coat., 136, 105247, 10.1016/j.porgcoat.2019.105247

Seidi, 2020, Super-crosslinked ionic liquid-intercalated montmorillonite/epoxy nanocomposites: Cure kinetics, viscoelastic behavior and thermal degradation mechanism, Polym. Eng. Sci., 60, 1940, 10.1002/pen.25441

Boonlert-Uthai, T., Samthong, C., and Somwangthanaroj, A. (2019). Synthesis, Thermal Properties and Curing Kinetics of Hyperbranched BPA/PEG Epoxy Resin. Polymers, 11.

Tikhani, 2019, Cure Index demonstrates curing of epoxy composites containing silica nanoparticles of variable morphology and porosity, Prog. Org. Coat., 135, 176, 10.1016/j.porgcoat.2019.05.017

Jeyranpourkhameneh, 2016, The Thermo-Mechanical Properties estimation of Fullerene-Reinforced Resin Epoxy Composites by Molecular Dynamics Simulation- A Comparative Study, Polymer, 88, 9, 10.1016/j.polymer.2016.02.018

Jouyandeh, 2019, Curing epoxy with electrochemically synthesized MnxFe3-xO4 magnetic nanoparticles, Prog. Org. Coat., 136, 105199, 10.1016/j.porgcoat.2019.06.045

Jouyandeh, 2019, Curing epoxy with polyethylene glycol (PEG) surface-functionalized GdxFe3-xO4 magnetic nanoparticles, Prog. Org. Coat., 137, 105283, 10.1016/j.porgcoat.2019.105283

Karami, Z., Paran, S.M.R., Vijayan, P., Ganjali, M.R., Jouyandeh, M., Esmaeili, A., Habibzadeh, S., Stadler, F.J., and Saeb, M.R. (2020). A Comparative Study on Cure Kinetics of Layered Double Hydroxide (LDH)/Epoxy Nanocomposites. J. Compos. Sci., 4.

Jouyandeh, 2019, Nonisothermal cure kinetics of epoxy/ZnxFe3-xO4 nanocomposites, Prog. Org. Coat., 136, 105290, 10.1016/j.porgcoat.2019.105290

Jouyandeh, 2018, Acid-aided epoxy-amine curing reaction as reflected in epoxy/Fe3O4 nanocomposites: Chemistry, mechanism, and fracture behavior, Prog. Org. Coat., 125, 384, 10.1016/j.porgcoat.2018.09.024

Nabil, 2012, Effects of partial replacement of commercial fillers by recycled poly(ethylene terephthalate) powder on the properties of natural rubber composites, J. Vinyl Addit. Technol., 18, 139, 10.1002/vnl.20291

Guo, 2010, Molecular Architecture of Electroactive and Biodegradable Copolymers Composed of Polylactide and Carboxyl-Capped Aniline Trimer, Biomacromolecules, 11, 855, 10.1021/bm9011248

Hu, 2008, A new oxidation state of aniline pentamer observed in water-soluble electroactive oligoaniline-chitosan polymer, J. Polym. Sci. Part A Polym. Chem., 46, 1124, 10.1002/pola.22454

Shchukin, 2008, Active Anticorrosion Coatings with Halloysite Nanocontainers, J. Phys. Chem. C, 112, 958, 10.1021/jp076188r