Diels–Alder Augmented Epoxies with Plasmonic Nanoparticle Fillers for Efficient Photothermal Depolymerization

Mojtabai, Kavon D.; Lindholm, Samantha J.; McReynolds, Brandon T.; Penners, Nicole; McCoy, John D.; Chowdhury, Sanchari; Lee, Youngmin

doi:10.1021/acsapm.2c00025

Title: Diels–Alder Augmented Epoxies with Plasmonic Nanoparticle Fillers for Efficient Photothermal Depolymerization

Journal Article · Thu Mar 17 00:00:00 EDT 2022 · ACS Applied Polymer Materials

DOI:https://doi.org/10.1021/acsapm.2c00025· OSTI ID:1855396

Mojtabai, Kavon D. ^[1]; Lindholm, Samantha J. ^[1]; McReynolds, Brandon T. ^[1]; Penners, Nicole ^[1];

^[1];

^[1]

New Mexico Tech, Socorro, NM (United States)

Thermally reversible epoxies through the Diels–Alder (DA) reaction have been used for applications such as recycling, self-healing, and 3D printing. Depolymerization by bulk heating, however, would be a slow and inefficient process due to its low thermal conductivity. In this paper, photothermal conversion using refractory plasmonic titanium nitride (TiN) nanoparticles was employed for efficient and rapid depolymerization of reversible epoxies. TiN nanoparticles have superior thermal stability, broader light absorption, and higher light-to-heat conversion efficiency. They are also less expensive than more common plasmonic gold nanoparticles. Photothermal behavior of TiN nanoparticle-filled reversible epoxies was investigated as a function of concentration of TiN nanoparticles and as a function of the intensity of a light source. TiN nanoparticles could induce sufficient heat for depolymerization with a trace content, 0.01% by weight, under a broad-spectrum white light of intensity 1760 mW/cm² instead of a strong light source such as a laser. The reversible epoxies were prepared by a reaction between furan precursors and a bismaleimide compound. Crosslinking density was controlled by altering the architecture of furan precursors and the feed ratio between the furan precursor and the bismaleimide compound. These changes in chemical structure and degree of crosslinking permit the control of the thermomechanical properties of the reversible epoxy from soft elastomers to hard elastomers. Here, the reversible epoxies display a flow region at around 110 °C. Depolymerization through the retro-DA was confirmed by Fourier transform infrared spectroscopy as a function of duration at a high temperature. Light-induced removability and recyclability were demonstrated by adhesion tests using the reversible epoxy/nanoparticle composites.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: New Mexico Institute of Mining and Technology, Socorro, NM (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0022261

OSTI ID:: 1855396

Journal Information:: ACS Applied Polymer Materials, Vol. 4, Issue 4; ISSN 2637-6105

Publisher:: ACS PublicationsCopyright Statement

Country of Publication:: United States

Language:: English

References (59)

Diels-Alder polymerization of difurans with bismaleimides Goussé, Cécile; Gandini, Alessandro Polymer International, Vol. 48, Issue 8 https://doi.org/10.1002/(SICI)1097-0126(199908)48:8<723::AID-PI200>3.0.CO;2-#	journal	August 1999
An Experimental and Theoretical Study of Stereoselectivity of Furan−Maleic Anhydride and Furan−Maleimide Diels−Alder Reactions Rulíšek, Lubomír; Šebek, Pavel; Havlas, Zdeněk The Journal of Organic Chemistry, Vol. 70, Issue 16 https://doi.org/10.1021/jo050759z	journal	July 2005
Recycling technologies for thermoset composite materials—current status Pickering, S. J. Composites Part A: Applied Science and Manufacturing, Vol. 37, Issue 8 https://doi.org/10.1016/j.compositesa.2005.05.030	journal	August 2006
Epoxy-amine based thermoresponsive networks designed by Diels-Alder reactions: Epoxy-amine based thermoresponsive networks Marref, Mohamed; Mignard, Nathalie; Jegat, Corinne Polymer International, Vol. 62, Issue 1 https://doi.org/10.1002/pi.4287	journal	June 2012
Stereoisomeric effects in thermo-remendable polymer networks based on Diels-Alder crosslink reactions Canadell, Judit; Fischer, Hartmut; De With, Gijsbertus Journal of Polymer Science Part A: Polymer Chemistry, Vol. 48, Issue 15 https://doi.org/10.1002/pola.24134	journal	June 2010
Crosslinked epoxy materials exhibiting thermal remendablility and removability from multifunctional maleimide and furan compounds Liu, Ying-Ling; Hsieh, Chia-Yun Journal of Polymer Science Part A: Polymer Chemistry, Vol. 44, Issue 2 https://doi.org/10.1002/pola.21184	journal	January 2005
Photothermal Conversion Triggered Precisely Targeted Healing of Epoxy Resin Based on Thermoreversible Diels–Alder Network and Amino-Functionalized Carbon Nanotubes Li, Qiu-Tong; Jiang, Miao-Jie; Wu, Gang ACS Applied Materials & Interfaces, Vol. 9, Issue 24 https://doi.org/10.1021/acsami.7b01954	journal	June 2017
An Efficient Method of Recycling of CFRP Waste Using Peracetic Acid Das, Mohan; Chacko, Rinu; Varughese, Susy ACS Sustainable Chemistry & Engineering, Vol. 6, Issue 2 https://doi.org/10.1021/acssuschemeng.7b01456	journal	January 2018
Thermophysical characterization of a reversible dynamic polymer network based on kinetics and equilibrium of an amorphous furan-maleimide Diels-Alder cycloaddition Diaz, M. M.; Van Assche, G.; Maurer, F. H. J. Polymer, Vol. 120 https://doi.org/10.1016/j.polymer.2017.05.058	journal	June 2017
One-component Diels–Alder based polyurethanes: a unique way to self-heal Willocq, B.; Khelifa, F.; Brancart, J. RSC Adv., Vol. 7, Issue 76 https://doi.org/10.1039/C7RA09898G	journal	January 2017
PMMA thermoreversible networks by Diels–Alder reaction Okhay, Nidhal; Jegat, Corinne; Mignard, Nathalie Reactive and Functional Polymers, Vol. 73, Issue 5 https://doi.org/10.1016/j.reactfunctpolym.2013.02.006	journal	May 2013
Ambient temperature induced Diels–Alder crosslinked networks based on controlled methacrylate copolymers for enhanced thermoreversibility and self-healability Jung, Sungmin; Kim, So Young; Kim, Jin Chul RSC Advances, Vol. 7, Issue 42 https://doi.org/10.1039/C7RA04222A	journal	January 2017
Thermoplastic Healing in Epoxy Networks: Exploring Performance and Mechanism of Alternative Healing Agents: Thermoplastic Healing in Epoxy Networks Varley, Russell J.; Craze, David A.; Mouritz, Adrian P. Macromolecular Materials and Engineering, Vol. 298, Issue 11 https://doi.org/10.1002/mame.201200394	journal	April 2013
Conductive nitrides: Growth principles, optical and electronic properties, and their perspectives in photonics and plasmonics Patsalas, P.; Kalfagiannis, N.; Kassavetis, S. Materials Science and Engineering: R: Reports, Vol. 123 https://doi.org/10.1016/j.mser.2017.11.001	journal	January 2018
Dynamic Polyamide Networks via Amide–Imide Exchange Chen, Yinjun; Zhang, Huiyi; Majumdar, Soumabrata Macromolecules, Vol. 54, Issue 20 https://doi.org/10.1021/acs.macromol.1c01389	journal	October 2021
Alternative Plasmonic Materials: Beyond Gold and Silver Naik, Gururaj V.; Shalaev, Vladimir M.; Boltasseva, Alexandra Advanced Materials, Vol. 25, Issue 24 https://doi.org/10.1002/adma.201205076	journal	May 2013
Thermo‐adjusted self‐healing epoxy resins based on Diels–Alder dynamic chemical reaction Zhang, Yunpeng; Ye, Jiaofeng; Qu, Dongan Polymer Engineering & Science, Vol. 61, Issue 9 https://doi.org/10.1002/pen.25753	journal	July 2021
The influence of stereochemistry on the reactivity of the Diels–Alder cycloaddition and the implications for reversible network polymerization Cuvellier, Audrey; Verhelle, Robrecht; Brancart, Joost Polymer Chemistry, Vol. 10, Issue 4 https://doi.org/10.1039/C8PY01216D	journal	January 2019
Titanium nitride nanoparticles for the efficient photocatalysis of bicarbonate into formate Beierle, Alyssa; Gieri, Paul; Pan, Hanqing Solar Energy Materials and Solar Cells, Vol. 200 https://doi.org/10.1016/j.solmat.2019.109967	journal	September 2019
Chemical recycling of waste plastics for new materials production Rahimi, AliReza; García, Jeannette M. Nature Reviews Chemistry, Vol. 1, Issue 6 https://doi.org/10.1038/s41570-017-0046	journal	June 2017
Interparticle Coupling Effect on the Surface Plasmon Resonance of Gold Nanoparticles: From Theory to Applications Ghosh, Sujit Kumar; Pal, Tarasankar Chemical Reviews, Vol. 107, Issue 11 https://doi.org/10.1021/cr0680282	journal	November 2007
Reversible click chemistry at the service of macromolecular materials. Part 4: Diels–Alder non-linear polycondensations involving polyfunctional furan and maleimide monomers Gandini, Alessandro; Silvestre, Armando; Coelho, Dora Polym. Chem., Vol. 4, Issue 5 https://doi.org/10.1039/C2PY20805A	journal	January 2013
Thermally Remendable Polyurethane Network Cross-Linked via Reversible Diels–Alder Reaction Platonova, Elena; Chechenov, Islam; Pavlov, Alexander Polymers, Vol. 13, Issue 12 https://doi.org/10.3390/polym13121935	journal	June 2021
Thermally Reversible IPN Organic−Inorganic Polymer Hybrids Utilizing the Diels−Alder Reaction Imai, Yusuke; Itoh, Hideaki; Naka, Kensuke Macromolecules, Vol. 33, Issue 12 https://doi.org/10.1021/ma991899b	journal	June 2000
Properties of Reversible Diels-Alder Furan/Maleimide Polymer Networks as Function of Crosslink Density Toncelli, Claudio; De Reus, Dennis C.; Picchioni, Francesco Macromolecular Chemistry and Physics, Vol. 213, Issue 2 https://doi.org/10.1002/macp.201100405	journal	January 2012
A new approach to the synthesis of monomers and polymers incorporating furan/maleimide Diels-Alder adducts Banella, Maria Barbara; Gioia, Claudio; Vannini, Micaela VIII INTERNATIONAL CONFERENCE ON “TIMES OF POLYMERS AND COMPOSITES”: From Aerospace to Nanotechnology, AIP Conference Proceedings https://doi.org/10.1063/1.4949584	conference	January 2016
A Thermally Re-mendable Cross-Linked Polymeric Material Chen, Xiangxu; Dam, Matheus A.; Ono, Kanji Science, Vol. 295, Issue 5560, p. 1698-1702 https://doi.org/10.1126/science.1065879	journal	March 2002
An approach to chemical recycling of epoxy resin cured with amine using nitric acid Dang, Weirong; Kubouchi, Masatoshi; Yamamoto, Shurou Polymer, Vol. 43, Issue 10 https://doi.org/10.1016/S0032-3861(02)00100-3	journal	May 2002
Design and ageing of adhesives for structural adhesive bonding – A review Pethrick, Richard A. Proceedings of the Institution of Mechanical Engineers, Part L: Journal of Materials: Design and Applications, Vol. 229, Issue 5 https://doi.org/10.1177/1464420714522981	journal	February 2014
Simultaneous Recovery of Matrix and Fiber in Carbon Reinforced Composites through a Diels–Alder Solvolysis Process Fortunato, Giovanni; Anghileri, Luca; Griffini, Gianmarco Polymers, Vol. 11, Issue 6 https://doi.org/10.3390/polym11061007	journal	June 2019
Ultrafast relaxation dynamics in bimetallic plasmonic catalysts Sim, Sangwan; Beierle, Alyssa; Mantos, Philip Nanoscale, Vol. 12, Issue 18 https://doi.org/10.1039/D0NR00831A	journal	January 2020
Catalytic Hydrothermal Depolymerization Technology and Kinetics of DGEBA/EDA Epoxy Resin Zhang, Jian Qiu; Deng, Wu Yan; Zu, Jian Hua Advanced Materials Research, Vol. 201-203 https://doi.org/10.4028/www.scientific.net/AMR.201-203.2814	journal	February 2011
New Thermally Remendable Highly Cross-Linked Polymeric Materials Chen, Xiangxu; Wudl, Fred; Mal, Ajit K. Macromolecules, Vol. 36, Issue 6 https://doi.org/10.1021/ma0210675	journal	March 2003
Thermoreversible Reactions on Inorganic Nanoparticle Surfaces: Diels–Alder Reactions on Sterically Crowded Surfaces Engel, Tom; Kickelbick, Guido Chemistry of Materials, Vol. 25, Issue 2 https://doi.org/10.1021/cm303049k	journal	January 2013
Study of the Diels–Alder and retro-Diels–Alder reaction between furan derivatives and maleimide for the creation of new materials Froidevaux, V.; Borne, M.; Laborbe, E. RSC Advances, Vol. 5, Issue 47 https://doi.org/10.1039/C5RA01185J	journal	January 2015
Self‐healing semi‐IPN materials from epoxy resin by solvent‐free furan–maleimide Diels–Alder polymerization Zolghadr, Mohsen; Shakeri, Alireza; Zohuriaan‐Mehr, Mohammad Jalal Journal of Applied Polymer Science, Vol. 136, Issue 40 https://doi.org/10.1002/app.48015	journal	May 2019
A Dual-Cure, Solid-State Photoresist Combining a Thermoreversible Diels–Alder Network and a Chain Growth Acrylate Network Berg, Gayla J.; Gong, Tao; Fenoli, Christopher R. Macromolecules, Vol. 47, Issue 10 https://doi.org/10.1021/ma500244r	journal	May 2014
Rapid self-healing and recycling of multiple-responsive mechanically enhanced epoxy resin/graphene nanocomposites Cai, Chenting; Zhang, Yue; Zou, Xueting RSC Adv., Vol. 7, Issue 73 https://doi.org/10.1039/C7RA09258J	journal	January 2017
In situ curing of liquid epoxy via gold-nanoparticle mediated photothermal heating Dong, Ju; Firestone, Gabriel E.; Bochinski, J. R. Nanotechnology, Vol. 28, Issue 6 https://doi.org/10.1088/1361-6528/aa521b	journal	January 2017
Synthesis and properties of UV-curable acrylate functionalized tung oil based resins via Diels–Alder reaction Huang, Yugang; Ye, Guodong; Yang, Jianwen Progress in Organic Coatings, Vol. 78 https://doi.org/10.1016/j.porgcoat.2014.10.011	journal	January 2015
High-performance, multi-functional and well-dispersed graphene/epoxy nanocomposites via internal antiplasticization and π-πF interactions Ma, Tian; Ma, Jiahao; Yang, Chao Composites Science and Technology, Vol. 215 https://doi.org/10.1016/j.compscitech.2021.109008	journal	October 2021
New Design of Composite Structures Used in Automotive Engineering Gheorghe, Vasile; Scutaru, Maria Luminita; Ungureanu, Virgil Barbu Symmetry, Vol. 13, Issue 3 https://doi.org/10.3390/sym13030383	journal	February 2021
Diels-Alder-based thermo-reversibly crosslinked polymers: Interplay of crosslinking density, network mobility, kinetics and stereoisomerism Orozco, Felipe; Li, Jing; Ezekiel, Unwana European Polymer Journal, Vol. 135 https://doi.org/10.1016/j.eurpolymj.2020.109882	journal	July 2020
Effect of the polymer matrix on the thermal behaviour of a furan-maleimide type adduct in the molten state Jegat, Corinne; Mignard, Nathalie Polymer Bulletin, Vol. 60, Issue 6 https://doi.org/10.1007/s00289-008-0913-y	journal	February 2008
Comparative environmental and human health evaluations of thermolysis and solvolysis recycling technologies of carbon fiber reinforced polymer waste Khalil, Y. F. Waste Management, Vol. 76 https://doi.org/10.1016/j.wasman.2018.03.026	journal	June 2018
Polyether-maleimide-based crosslinked self-healing polyurethane with Diels-Alder bonds Zhong, Yiting; Wang, Xinling; Zheng, Zhen Journal of Applied Polymer Science, Vol. 132, Issue 19 https://doi.org/10.1002/app.41944	journal	January 2015
Hindering the decrease in wear resistance of UV-exposed epoxy powder coatings by adding nano-SiO2 through ball milling Fernández-Álvarez, M.; Velasco, F.; Torres-Carrasco, M. Wear, Vol. 480-481 https://doi.org/10.1016/j.wear.2021.203935	journal	September 2021
Note: Thermally removable epoxy adhesives incorporating thermally reversible diels-alder adducts Aubert, James H. The Journal of Adhesion, Vol. 79, Issue 6 https://doi.org/10.1080/00218460309540	journal	June 2003
Kinetic study of Diels–Alder reaction involving in maleimide–furan compounds and linear polyurethane Liu, Xuanxuan; Du, Pengfei; Liu, Li Polymer Bulletin, Vol. 70, Issue 8 https://doi.org/10.1007/s00289-013-0954-8	journal	March 2013
Diels-Alder-Chitosan based dissociative covalent adaptable networks Chapelle, Camille; Quienne, Baptiste; Bonneaud, Céline Carbohydrate Polymers, Vol. 253 https://doi.org/10.1016/j.carbpol.2020.117222	journal	February 2021
Biosourced Acetal and Diels–Alder Adduct Concurrent Polyurethane Covalent Adaptable Network Li, Qiong; Ma, Songqi; Li, Pengyun Macromolecules, Vol. 54, Issue 4 https://doi.org/10.1021/acs.macromol.0c02699	journal	February 2021
Epoxy Polymer Solder Pastes for Micro-Electronic Packaging Applications Sharma, Ashutosh; Jung, Do Hyun; Cheon, Ju Seon Journal of Welding and Joining, Vol. 37, Issue 2 https://doi.org/10.5781/JWJ.2019.37.2.2	journal	April 2019
A novel shape memory-assisted and thermo-induced self-healing boron nitride/epoxy composites based on Diels–Alder reaction Cao, Ying; Zhang, Jiatian; Zhang, Dandan Journal of Materials Science, Vol. 55, Issue 25 https://doi.org/10.1007/s10853-020-04842-w	journal	May 2020
Application of toughened epoxy-adhesives for strengthening of fatigue-damaged steel structures Kasper, Yann; Albiez, Matthias; Ummenhofer, Thomas Construction and Building Materials, Vol. 275 https://doi.org/10.1016/j.conbuildmat.2020.121579	journal	March 2021
Plasmonic Materials Murray, W. A.; Barnes, W. L. Advanced Materials, Vol. 19, Issue 22 https://doi.org/10.1002/adma.200700678	journal	November 2007
Rapid removal of resin from a unidirectional carbon fiber reinforced plastic laminate by a high-voltage electrical treatment Oshima, Kazumasa; Matsuda, Shinya; Hosaka, Masaki Separation and Purification Technology, Vol. 231 https://doi.org/10.1016/j.seppur.2019.115885	journal	January 2020
Diels-Alder Reversible Thermoset 3D Printing: Isotropic Thermoset Polymers via Fused Filament Fabrication Yang, Kejia; Grant, Jesse C.; Lamey, Patrice Advanced Functional Materials, Vol. 27, Issue 24 https://doi.org/10.1002/adfm.201700318	journal	April 2017
Biobased furan-based epoxy/TiO2 nanocomposites for the preparation of coatings with improved chemical resistance Marotta, Angela; Faggio, Noemi; Ambrogi, Veronica Chemical Engineering Journal, Vol. 406 https://doi.org/10.1016/j.cej.2020.127107	journal	February 2021
The furan/maleimide Diels–Alder reaction: A versatile click–unclick tool in macromolecular synthesis Gandini, Alessandro Progress in Polymer Science, Vol. 38, Issue 1 https://doi.org/10.1016/j.progpolymsci.2012.04.002	journal	January 2013

Similar Records

Understanding the Effect of Side Reactions on the Recyclability of Furan–Maleimide Resins Based on Thermoreversible Diels–Alder Network

Journal Article · Thu Feb 23 00:00:00 EST 2023 · Polymers · OSTI ID:1855396

McReynolds, Brandon T.; Mojtabai, Kavon D.; Penners, Nicole; +5 more

Polyethylene Incorporating Diels–Alder Comonomers: A “Trojan Horse” Strategy for Chemically Recyclable Polyolefins

Journal Article · Thu Jun 15 00:00:00 EDT 2023 · Angewandte Chemie · OSTI ID:1855396

Parke, Sarah M.; Lopez, Jaqueline C.; Cui, Shilin; +2 more

Polyethylene Incorporating Diels–Alder Comonomers: A “Trojan Horse” Strategy for Chemically Recyclable Polyolefins

Journal Article · Thu Jun 15 00:00:00 EDT 2023 · Angewandte Chemie (International Edition) · OSTI ID:1855396

Parke, Sarah M.; Lopez, Jaqueline C.; Cui, Shilin; +2 more

Related Subjects

77 NANOSCIENCE AND NANOTECHNOLOGY
36 MATERIALS SCIENCE
plasmonic nanoparticles
photothermal conversion
Diels−Alder reaction
dynamic covalent bonds
epoxy
depolymerization
organic polymers
nanoparticles
light

Title: Diels–Alder Augmented Epoxies with Plasmonic Nanoparticle Fillers for Efficient Photothermal Depolymerization

Citation Formats

References (59)

Similar Records

Related Subjects