Mechanically robust and reprocessable imine exchange networks from modular polyester pre-polymers

Snyder, Rachel L.; Lidston, Claire L.; De Hoe, Guilhem X.; Parvulescu, Maria J. S.; Hillmyer, Marc A.; Coates, Geoffrey W.

doi:10.1039/c9py01957j

Mechanically robust and reprocessable imine exchange networks from modular polyester pre-polymers

Journal Article · Thu Feb 27 00:00:00 EST 2020 · Polymer Chemistry

DOI:https://doi.org/10.1039/c9py01957j· OSTI ID:1770322

^[1]; ^[1]; ^[2]; ^[3]; ^[4]; ^[1]

Cornell Univ., Ithaca, NY (United States). Baker Lab.
Univ. of Minnesota, Minneapolis, MN (United States); Argonne National Lab. (ANL), Argonne, IL (United States)
Cornell Univ., Ithaca, NY (United States). Baker Lab.; UES, Inc., Dayton, OH (United States)
Univ. of Minnesota, Minneapolis, MN (United States)

Covalent adaptable networks (CANs) containing reversible cross-links impart recyclability to thermoset materials without sacrificing their desirable properties (e.g. high tensile strength and solvent resistance). In addition to thermal recycling, the sustainability of these materials may be further improved by incorporating bio-sourced monomers or by enabling alternate end-of-life fates, such as biodegradation or recovery of starting materials. The alternating ring-opening copolymerisation of epoxides and cyclic anhydrides permits the modular synthesis of polyester pre-polymers that can then be cross-linked to form dynamic imine-linked networks. In this work, we report the synthesis and characterisation of five imine exchange polyester CANs with varied cross-linking densities and pre-polymer architectures. While the materials exhibit characteristic thermoset properties at service temperatures, differences in pre-polymer architecture produce distinct dynamic mechanical effects at elevated temperatures. The networks may be thermally reprocessed with full recovery of their tensile strengths and cross-linking densities, dissociated to pre-polymer, or hydrolytically degraded.

View Accepted Manuscript (DOE)

Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States)

Sponsoring Organization:: National Science Foundation (NSF); USDOE

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1770322

Journal Information:: Polymer Chemistry, Journal Name: Polymer Chemistry Journal Issue: 33 Vol. 11; ISSN 1759-9954

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

References (91)

Vinylogous Urethane Vitrimers Denissen, Wim; Rivero, Guadalupe; Nicolaÿ, Renaud Advanced Functional Materials, Vol. 25, Issue 16 https://doi.org/10.1002/adfm.201404553	journal	March 2015
Heat- or Water-Driven Malleability in a Highly Recyclable Covalent Network Polymer Taynton, Philip; Yu, Kai; Shoemaker, Richard K. Advanced Materials, Vol. 26, Issue 23 https://doi.org/10.1002/adma.201400317	journal	March 2014
Repairable Woven Carbon Fiber Composites with Full Recyclability Enabled by Malleable Polyimine Networks Taynton, Philip; Ni, Huagang; Zhu, Chengpu Advanced Materials, Vol. 28, Issue 15 https://doi.org/10.1002/adma.201505245	journal	February 2016
Recyclable Crosslinked Polymer Networks via One-Step Controlled Radical Polymerization Jin, Kailong; Li, Lingqiao; Torkelson, John M. Advanced Materials, Vol. 28, Issue 31 https://doi.org/10.1002/adma.201600871	journal	May 2016
A Stiff and Healable Polymer Based on Dynamic-Covalent Boroxine Bonds Lai, Jian-Cheng; Mei, Jin-Feng; Jia, Xiao-Yong Advanced Materials, Vol. 28, Issue 37 https://doi.org/10.1002/adma.201602332	journal	July 2016
Dynamic Covalent Polymer Networks: from Old Chemistry to Modern Day Innovations Zou, Weike; Dong, Jiante; Luo, Yingwu Advanced Materials, Vol. 29, Issue 14 https://doi.org/10.1002/adma.201606100	journal	February 2017
Alternating Copolymerization of Propylene Oxide with Biorenewable Terpene-Based Cyclic Anhydrides: A Sustainable Route to Aliphatic Polyesters with High Glass Transition Temperatures Van Zee, Nathan J.; Coates, Geoffrey W. Angewandte Chemie International Edition, Vol. 54, Issue 9 https://doi.org/10.1002/anie.201410641	journal	January 2015
Control of Imine Exchange Kinetics with Photoswitches to Modulate Self-Healing in Polysiloxane Networks by Light Illumination Kathan, Michael; Kovaříček, Petr; Jurissek, Christoph Angewandte Chemie International Edition, Vol. 55, Issue 44 https://doi.org/10.1002/anie.201605311	journal	July 2016
Dynamic Covalent Bonds in Polymeric Materials Chakma, Progyateg; Konkolewicz, Dominik Angewandte Chemie International Edition, Vol. 58, Issue 29 https://doi.org/10.1002/anie.201813525	journal	July 2019
Ueber die Pyroguajacsäure, Product der trocknen Destillation des Guajacharzes Sobrero, Ascanio Annalen der Chemie und Pharmacie, Vol. 48, Issue 1 https://doi.org/10.1002/jlac.18430480103	journal	January 1843
From Lignin-derived Aromatic Compounds to Novel Biobased Polymers Llevot, Audrey; Grau, Etienne; Carlotti, Stéphane Macromolecular Rapid Communications, Vol. 37, Issue 1 https://doi.org/10.1002/marc.201500474	journal	October 2015
Influence of molecular weight and molecular weight distribution on mechanical properties of polymers Nunes, Ronald W.; Martin, John R.; Johnson, Julian F. Polymer Engineering and Science, Vol. 22, Issue 4 https://doi.org/10.1002/pen.760220402	journal	March 1982
Alternating ring-opening copolymerization of cyclohexene oxide with phthalic anhydride catalyzed by iron(III) salen complexes Mundil, Robert; Hošt’álek, Zdeněk; Šeděnková, Ivana Macromolecular Research, Vol. 23, Issue 2 https://doi.org/10.1007/s13233-015-3022-4	journal	January 2015
Biodegradation of polyesters containing aromatic constituents Müller, Rolf-Joachim; Kleeberg, Ilona; Deckwer, Wolf-Dieter Journal of Biotechnology, Vol. 86, Issue 2 https://doi.org/10.1016/S0168-1656(00)00407-7	journal	March 2001
Viscoelastic response of linear defects trapped in polymer networks Roth, Leandro E.; Agudelo, Diana C.; Ressia, Jorge A. European Polymer Journal, Vol. 64 https://doi.org/10.1016/j.eurpolymj.2014.12.036	journal	March 2015
From landfilling to vitrimer chemistry in rubber life cycle Imbernon, Lucie; Norvez, Sophie European Polymer Journal, Vol. 82 https://doi.org/10.1016/j.eurpolymj.2016.03.016	journal	September 2016
Vanillin-based degradable epoxy vitrimers: Reprocessability and mechanical properties study Yu, Qingqing; Peng, Xionghou; Wang, Yuli European Polymer Journal, Vol. 117 https://doi.org/10.1016/j.eurpolymj.2019.04.053	journal	August 2019
Structure–mechanical property correlations of model siloxane elastomers with controlled network topology Urayama, Kenji; Kawamura, Takanobu; Kohjiya, Shinzo Polymer, Vol. 50, Issue 2 https://doi.org/10.1016/j.polymer.2008.10.027	journal	January 2009
Environmental friendly polymers based on schiff-base reaction with self-healing, remolding and degradable ability Li, Hui; Bai, Jing; Shi, Zixing Polymer, Vol. 85 https://doi.org/10.1016/j.polymer.2016.01.050	journal	February 2016
Polymer engineering based on reversible covalent chemistry: A promising innovative pathway towards new materials and new functionalities Zhang, Ze Ping; Rong, Min Zhi; Zhang, Ming Qiu Progress in Polymer Science, Vol. 80 https://doi.org/10.1016/j.progpolymsci.2018.03.002	journal	May 2018
Ring-Opening Copolymerization of Epoxides and Cyclic Anhydrides with Discrete Metal Complexes: Structure–Property Relationships Longo, Julie M.; Sanford, Maria J.; Coates, Geoffrey W. Chemical Reviews, Vol. 116, Issue 24 https://doi.org/10.1021/acs.chemrev.6b00553	journal	December 2016
Dinuclear Zinc Salen Catalysts for the Ring Opening Copolymerization of Epoxides and Carbon Dioxide or Anhydrides Thevenon, Arnaud; Garden, Jennifer A.; White, Andrew J. P. Inorganic Chemistry, Vol. 54, Issue 24 https://doi.org/10.1021/acs.inorgchem.5b02233	journal	November 2015
Stress Relaxation and Self-Adhesion of Rubbers with Exchangeable Links Imbernon, Lucie; Norvez, Sophie; Leibler, Ludwik Macromolecules, Vol. 49, Issue 6 https://doi.org/10.1021/acs.macromol.5b02751	journal	March 2016
Alternating Copolymerization of Propylene Oxide and Cyclohexene Oxide with Tricyclic Anhydrides: Access to Partially Renewable Aliphatic Polyesters with High Glass Transition Temperatures Sanford, Maria J.; Peña Carrodeguas, Leticia; Van Zee, Nathan J. Macromolecules, Vol. 49, Issue 17 https://doi.org/10.1021/acs.macromol.6b01425	journal	August 2016
Dynamic Covalent Polymer Networks Based on Degenerative Imine Bond Exchange: Tuning the Malleability and Self-Healing Properties by Solvent Chao, Albert; Negulescu, Ioan; Zhang, Donghui Macromolecules, Vol. 49, Issue 17 https://doi.org/10.1021/acs.macromol.6b01443	journal	August 2016
50th Anniversary Perspective : There Is a Great Future in Sustainable Polymers Schneiderman, Deborah K.; Hillmyer, Marc A. Macromolecules, Vol. 50, Issue 10 https://doi.org/10.1021/acs.macromol.7b00293	journal	May 2017
Effect of Sterics and Degree of Cross-Linking on the Mechanical Properties of Dynamic Poly(alkylurea–urethane) Networks Zhang, Longhe; Rowan, Stuart J. Macromolecules, Vol. 50, Issue 13 https://doi.org/10.1021/acs.macromol.7b01016	journal	June 2017
Reprocessable Acid-Degradable Polycarbonate Vitrimers Snyder, Rachel L.; Fortman, David J.; De Hoe, Guilhem X. Macromolecules, Vol. 51, Issue 2 https://doi.org/10.1021/acs.macromol.7b02299	journal	January 2018
Vinylogous Urea Vitrimers and Their Application in Fiber Reinforced Composites Denissen, Wim; De Baere, Ives; Van Paepegem, Wim Macromolecules, Vol. 51, Issue 5 https://doi.org/10.1021/acs.macromol.7b02407	journal	February 2018
Well-Defined and Structurally Diverse Aromatic Alternating Polyesters Synthesized by Simple Phosphazene Catalysis Li, Heng; Luo, Huitong; Zhao, Junpeng Macromolecules, Vol. 51, Issue 6 https://doi.org/10.1021/acs.macromol.8b00159	journal	March 2018
Effects of Cross-Link Density and Distribution on Static and Dynamic Properties of Chemically Cross-Linked Polymers Shen, Jianxiang; Lin, Xiangsong; Liu, Jun Macromolecules, Vol. 52, Issue 1 https://doi.org/10.1021/acs.macromol.8b01389	journal	December 2018
Robust, Fire-Safe, Monomer-Recovery, Highly Malleable Thermosets from Renewable Bioresources Wang, Sheng; Ma, Songqi; Li, Qiong Macromolecules, Vol. 51, Issue 20 https://doi.org/10.1021/acs.macromol.8b01601	journal	October 2018
Recyclable and Malleable Epoxy Thermoset Bearing Aromatic Imine Bonds Zhao, Shou; Abu-Omar, Mahdi M. Macromolecules, Vol. 51, Issue 23 https://doi.org/10.1021/acs.macromol.8b01976	journal	November 2018
Phase Separation and Self-Assembly in Vitrimers: Hierarchical Morphology of Molten and Semicrystalline Polyethylene/Dioxaborolane Maleimide Systems Ricarte, Ralm G.; Tournilhac, François; Leibler, Ludwik Macromolecules, Vol. 52, Issue 2 https://doi.org/10.1021/acs.macromol.8b02144	journal	December 2018
Catalyst-Free Vitrimers from Vinyl Polymers Lessard, Jacob J.; Garcia, Luis F.; Easterling, Charles P. Macromolecules, Vol. 52, Issue 5 https://doi.org/10.1021/acs.macromol.8b02477	journal	February 2019
Thermally Healable and Reprocessable Bis(hindered amino)disulfide-Cross-Linked Polymethacrylate Networks Takahashi, Akira; Goseki, Raita; Ito, Kohzo ACS Macro Letters, Vol. 6, Issue 11 https://doi.org/10.1021/acsmacrolett.7b00762	journal	November 2017
Vitrimeric Silicone Elastomers Enabled by Dynamic Meldrum’s Acid-Derived Cross-Links Ishibashi, Jacob S. A.; Kalow, Julia A. ACS Macro Letters, Vol. 7, Issue 4 https://doi.org/10.1021/acsmacrolett.8b00166	journal	March 2018
Approaches to Sustainable and Continually Recyclable Cross-Linked Polymers Fortman, David J.; Brutman, Jacob P.; De Hoe, Guilhem X. ACS Sustainable Chemistry & Engineering, Vol. 6, Issue 9 https://doi.org/10.1021/acssuschemeng.8b02355	journal	August 2018
Vanillin-Based Polyschiff Vitrimers: Reprocessability and Chemical Recyclability Geng, Hongwei; Wang, Yuli; Yu, Qingqing ACS Sustainable Chemistry & Engineering, Vol. 6, Issue 11 https://doi.org/10.1021/acssuschemeng.8b03925	journal	September 2018
Aliphatic Polyesters: Great Degradable Polymers That Cannot Do Everything ^† Vert, Michel Biomacromolecules, Vol. 6, Issue 2 https://doi.org/10.1021/bm0494702	journal	March 2005
Molecular Size Distribution in Three Dimensional Polymers. I. Gelation ¹ Flory, Paul J. Journal of the American Chemical Society, Vol. 63, Issue 11 https://doi.org/10.1021/ja01856a061	journal	November 1941
Amorphous Linear Aliphatic Polyesters for the Facile Preparation of Tunable Rapidly Degrading Elastomeric Devices and Delivery Vectors Olson, David A.; Gratton, Stephanie E. A.; DeSimone, Joseph M. Journal of the American Chemical Society, Vol. 128, Issue 41 https://doi.org/10.1021/ja063092m	journal	October 2006
A Surprise from 1954: Siloxane Equilibration Is a Simple, Robust, and Obvious Polymer Self-Healing Mechanism Zheng, Peiwen; McCarthy, Thomas J. Journal of the American Chemical Society, Vol. 134, Issue 4 https://doi.org/10.1021/ja2113257	journal	January 2012
Selective Polymerization Catalysis: Controlling the Metal Chain End Group to Prepare Block Copolyesters Zhu, Yunqing; Romain, Charles; Williams, Charlotte K. Journal of the American Chemical Society, Vol. 137, Issue 38 https://doi.org/10.1021/jacs.5b04541	journal	September 2015
Mechanically Activated, Catalyst-Free Polyhydroxyurethane Vitrimers Fortman, David J.; Brutman, Jacob P.; Cramer, Christopher J. Journal of the American Chemical Society, Vol. 137, Issue 44 https://doi.org/10.1021/jacs.5b08084	journal	November 2015
Silyl Ether as a Robust and Thermally Stable Dynamic Covalent Motif for Malleable Polymer Design Nishimura, Yoshio; Chung, Jaeyoon; Muradyan, Hurik Journal of the American Chemical Society, Vol. 139, Issue 42 https://doi.org/10.1021/jacs.7b08826	journal	October 2017
Sustainable Polyester Elastomers from Lactones: Synthesis, Properties, and Enzymatic Hydrolyzability De Hoe, Guilhem X.; Zumstein, Michael T.; Tiegs, Brandon J. Journal of the American Chemical Society, Vol. 140, Issue 3 https://doi.org/10.1021/jacs.7b10173	journal	January 2018
Mechanism-Inspired Design of Bifunctional Catalysts for the Alternating Ring-Opening Copolymerization of Epoxides and Cyclic Anhydrides Abel, Brooks A.; Lidston, Claire A. L.; Coates, Geoffrey W. Journal of the American Chemical Society, Vol. 141, Issue 32 https://doi.org/10.1021/jacs.9b05570	journal	July 2019
Internal Catalysis in Covalent Adaptable Networks: Phthalate Monoester Transesterification As a Versatile Dynamic Cross-Linking Chemistry Delahaye, Maarten; Winne, Johan M.; Du Prez, Filip E. Journal of the American Chemical Society, Vol. 141, Issue 38 https://doi.org/10.1021/jacs.9b07269	journal	August 2019
Adaptable Crosslinks in Polymeric Materials: Resolving the Intersection of Thermoplastics and Thermosets Scheutz, Georg M.; Lessard, Jacob J.; Sims, Michael B. Journal of the American Chemical Society, Vol. 141, Issue 41 https://doi.org/10.1021/jacs.9b07922	journal	September 2019
Block Copolymer Vitrimers Lessard, Jacob J.; Scheutz, Georg M.; Sung, Seung Hyun Journal of the American Chemical Society, Vol. 142, Issue 1 https://doi.org/10.1021/jacs.9b10360	journal	December 2019
Amorphous Unsaturated Aliphatic Polyesters Derived from Dicarboxylic Monomers Synthesized by Diels−Alder Chemistry Brown, Andrew H.; Sheares, Valerie V. Macromolecules, Vol. 40, Issue 14 https://doi.org/10.1021/ma070185v	journal	July 2007
Dynamic Viscoelasticity of Poly(butyl acrylate) Elastomers Containing Dangling Chains with Controlled Lengths Yamazaki, Haruna; Takeda, Masanao; Kohno, Yoshiyuki Macromolecules, Vol. 44, Issue 22 https://doi.org/10.1021/ma201941v	journal	November 2011
Influence of Dangling Chains on Molecular Dynamics of Polyurethanes Yu, Wenwen; Du, Miao; Zhang, Dezhi Macromolecules, Vol. 46, Issue 18 https://doi.org/10.1021/ma401260d	journal	September 2013
Catalytic Control of the Vitrimer Glass Transition Capelot, Mathieu; Unterlass, Miriam M.; Tournilhac, François ACS Macro Letters, Vol. 1, Issue 7 https://doi.org/10.1021/mz300239f	journal	June 2012
Inherently Photohealable and Thermal Shape-Memory Polydisulfide Networks Michal, Brian T.; Jaye, Colin A.; Spencer, Emily J. ACS Macro Letters, Vol. 2, Issue 8 https://doi.org/10.1021/mz400318m	journal	July 2013
Chemical control of the viscoelastic properties of vinylogous urethane vitrimers Denissen, Wim; Droesbeke, Martijn; Nicolaÿ, Renaud Nature Communications, Vol. 8, Issue 1 https://doi.org/10.1038/ncomms14857	journal	March 2017
Unraveling substituent effects on the glass transition temperatures of biorenewable polyesters Yu, Xiaopeng; Jia, Junteng; Xu, Shu Nature Communications, Vol. 9, Issue 1 https://doi.org/10.1038/s41467-018-05269-3	journal	July 2018
Controlling polymer properties through the shape of the molecular-weight distribution Gentekos, Dillon T.; Sifri, Renee J.; Fors, Brett P. Nature Reviews Materials, Vol. 4, Issue 12 https://doi.org/10.1038/s41578-019-0138-8	journal	October 2019
Covalent adaptable networks: smart, reconfigurable and responsive network systems Kloxin, Christopher J.; Bowman, Christopher N. Chem. Soc. Rev., Vol. 42, Issue 17 https://doi.org/10.1039/C3CS60046G	journal	January 2013
Renewable production of phthalic anhydride from biomass-derived furan and maleic anhydride Mahmoud, Eyas; Watson, Donald A.; Lobo, Raul F. Green Chem., Vol. 16, Issue 1 https://doi.org/10.1039/C3GC41655K	journal	January 2014
Vanillin, a promising biobased building-block for monomer synthesis Fache, Maxence; Darroman, Emilie; Besse, Vincent Green Chem., Vol. 16, Issue 4 https://doi.org/10.1039/C3GC42613K	journal	January 2014
Ring-opening copolymerization (ROCOP): synthesis and properties of polyesters and polycarbonates Paul, Shyeni; Zhu, Yunqing; Romain, Charles Chemical Communications, Vol. 51, Issue 30 https://doi.org/10.1039/C4CC10113H	journal	January 2015
Renewable polycarbonates and polyesters from 1,4-cyclohexadiene Winkler, Matthias; Romain, Charles; Meier, Michael A. R. Green Chemistry, Vol. 17, Issue 1 https://doi.org/10.1039/C4GC01353K	journal	January 2015
Mechanisms of imine exchange reactions in organic solvents Ciaccia, Maria; Di Stefano, Stefano Organic & Biomolecular Chemistry, Vol. 13, Issue 3 https://doi.org/10.1039/C4OB02110J	journal	January 2015
Di-magnesium and zinc catalysts for the copolymerization of phthalic anhydride and cyclohexene oxide Saini, Prabhjot K.; Romain, Charles; Zhu, Yunqing Polym. Chem., Vol. 5, Issue 20 https://doi.org/10.1039/C4PY00748D	journal	January 2014
Influence of stoichiometry on the glass transition and bond exchange reactions in epoxy thermoset polymers Yu, Kai; Taynton, Philip; Zhang, Wei RSC Adv., Vol. 4, Issue 89 https://doi.org/10.1039/C4RA06543C	journal	January 2014
Epoxy thermosets from model mixtures of the lignin-to-vanillin process Fache, M.; Boutevin, B.; Caillol, S. Green Chemistry, Vol. 18, Issue 3 https://doi.org/10.1039/C5GC01070E	journal	January 2016
Vitrimers: permanent organic networks with glass-like fluidity Denissen, Wim; Winne, Johan M.; Du Prez, Filip E. Chemical Science, Vol. 7, Issue 1 https://doi.org/10.1039/C5SC02223A	journal	January 2016
Epoxy resin with exchangeable disulfide crosslinks to obtain reprocessable, repairable and recyclable fiber-reinforced thermoset composites Ruiz de Luzuriaga, Alaitz; Martin, Roberto; Markaide, Nerea Materials Horizons, Vol. 3, Issue 3 https://doi.org/10.1039/C6MH00029K	journal	January 2016
Re-healable polyimine thermosets: polymer composition and moisture sensitivity Taynton, Philip; Zhu, Chengpu; Loob, Samuel Polymer Chemistry, Vol. 7, Issue 46 https://doi.org/10.1039/C6PY01395C	journal	January 2016
Multiple welding of long fiber epoxy vitrimer composites Chabert, Erwan; Vial, Jérôme; Cauchois, Jean-Pierre Soft Matter, Vol. 12, Issue 21 https://doi.org/10.1039/C6SM00257A	journal	January 2016
Chemically recyclable polymers: a circular economy approach to sustainability Hong, Miao; Chen, Eugene Y. -X. Green Chemistry, Vol. 19, Issue 16 https://doi.org/10.1039/C7GC01496A	journal	January 2017
Recyclable 3D printing of vitrimer epoxy Shi, Qian; Yu, Kai; Kuang, Xiao Materials Horizons, Vol. 4, Issue 4 https://doi.org/10.1039/C7MH00043J	journal	January 2017
Tuning the physical properties of malleable and recyclable polyimine thermosets: the effect of solvent and monomer concentration Zhu, Chengpu; Xi, Cally; Doro, William RSC Adv., Vol. 7, Issue 76 https://doi.org/10.1039/C7RA10956C	journal	January 2017
Reversible-deactivation anionic alternating ring-opening copolymerization of epoxides and cyclic anhydrides: access to orthogonally functionalizable multiblock aliphatic polyesters Sanford, Maria J.; Van Zee, Nathan J.; Coates, Geoffrey W. Chemical Science, Vol. 9, Issue 1 https://doi.org/10.1039/C7SC03643D	journal	January 2018
Rehealable imide–imine hybrid polymers with full recyclability Lei, Xingfeng; Jin, Yinghua; Sun, Hongliang J. Mater. Chem. A, Vol. 5, Issue 40 https://doi.org/10.1039/C7TA07076D	journal	January 2017
Facile in situ preparation of high-performance epoxy vitrimer from renewable resources and its application in nondestructive recyclable carbon fiber composite Wang, Sheng; Ma, Songqi; Li, Qiong Green Chemistry, Vol. 21, Issue 6 https://doi.org/10.1039/C8GC03477J	journal	January 2019
Tunable, self-healing and corrosion inhibiting dynamic epoxy–polyimine network built by post-crosslinking Mo, Ruibin; Hu, Jin; Huang, Haowei Journal of Materials Chemistry A, Vol. 7, Issue 7 https://doi.org/10.1039/C8TA11546J	journal	January 2019
Dynamic covalent chemistry in polymer networks: a mechanistic perspective Winne, Johan M.; Leibler, Ludwik; Du Prez, Filip E. Polymer Chemistry, Vol. 10, Issue 45 https://doi.org/10.1039/C9PY01260E	journal	January 2019
Tuning the mechanical and dynamic properties of imine bond crosslinked elastomeric vitrimers by manipulating the crosslinking degree Liu, Yingjun; Tang, Zhenghai; Chen, Junlong Polymer Chemistry, Vol. 11, Issue 7 https://doi.org/10.1039/C9PY01826C	journal	January 2020
Tailoring polymer dispersity and shape of molecular weight distributions: methods and applications Whitfield, Richard; Truong, Nghia P.; Messmer, Daniel Chemical Science, Vol. 10, Issue 38 https://doi.org/10.1039/C9SC03546J	journal	January 2019
Tunable “soft and stiff”, self-healing, recyclable, thermadapt shape memory biomass polymers based on multiple hydrogen bonds and dynamic imine bonds Song, Fei; Li, Zhaoshuang; Jia, Puyou Journal of Materials Chemistry A, Vol. 7, Issue 21 https://doi.org/10.1039/C9TA03872H	journal	January 2019
Dynamic imine chemistry Belowich, Matthew E.; Stoddart, J. Fraser Chemical Society Reviews, Vol. 41, Issue 6 https://doi.org/10.1039/c2cs15305j	journal	January 2012
Theory of Molecular Size Distribution and Gel Formation in Branched Polymers II. General Cross Linking Stockmayer, Walter H. The Journal of Chemical Physics, Vol. 12, Issue 4 https://doi.org/10.1063/1.1723922	journal	April 1944
Thermomechanical insight into the reconfiguration of Diels–Alder networks Pratchayanan, Danaya; Yang, Jeh-Chang; Lewis, Christopher L. Journal of Rheology, Vol. 61, Issue 6 https://doi.org/10.1122/1.4997580	journal	November 2017
Melt rheology of poly(lactic acid): Entanglement and chain architecture effects Dorgan, John R.; Williams, Joshua S.; Lewis, David N. Journal of Rheology, Vol. 43, Issue 5 https://doi.org/10.1122/1.551041	journal	September 1999
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
Silica-Like Malleable Materials from Permanent Organic Networks Montarnal, D.; Capelot, M.; Tournilhac, F. Science, Vol. 334, Issue 6058 https://doi.org/10.1126/science.1212648	journal	November 2011
High-performance vitrimers from commodity thermoplastics through dioxaborolane metathesis Röttger, Max; Domenech, Trystan; van der Weegen, Rob Science, Vol. 356, Issue 6333 https://doi.org/10.1126/science.aah5281	journal	April 2017
Copolymerization and terpolymerization of carbon dioxide/propylene oxide/phthalic anhydride using a (salen)Co(III) complex tethering four quaternary ammonium salts Jeon, Jong Yeob; Eo, Seong Chan; Varghese, Jobi Kodiyan Beilstein Journal of Organic Chemistry, Vol. 10 https://doi.org/10.3762/bjoc.10.187	journal	January 2014

Similar Records

Chemically Recyclable Polyester Thermosets from Activated Adipic Acid and Renewable Polyols

Journal Article · Mon Jun 30 00:00:00 EDT 2025 · ChemSusChem · OSTI ID:2588447

Thermally stable and self-healable lignin-based polyester

Journal Article · Fri Jul 19 20:00:00 EDT 2024 · Polymer Testing · OSTI ID:2447259

Synthesis, characterization, and recycling of bio-derivable polyester covalently adaptable networks for industrial composite applications

Journal Article · Mon Dec 04 19:00:00 EST 2023 · Matter (Online) · OSTI ID:2282716

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Mechanically robust and reprocessable imine exchange networks from modular polyester pre-polymers

Citation Formats

References (91)

Similar Records

Related Subjects