Dynamic Semi IPNs with Duple Dynamic Linkers: Self-Healing, Reprocessing, Welding, and Shape Memory Behaviors

Thermoset polymers show favorable material properties, while bringing about environmental pollution due to non-reprocessing and unrecyclable. Diels–Alder (DA) chemistry or reversible exchange boronic ester bonds have been employed to fabricate recycled polymers with covalent adaptable networks (CANs). Herein, a novel type of CANs with multiple dynamic linkers (DA chemistry and boronic ester bonds) was firstly constructed based on a linear copolymer of styrene and furfuryl methacrylate and boronic ester crosslinker. Thermoplastic polyurethane is introduced into the CANs to give a semi Interpenetrating Polymer Networks (semi IPNs) to enhance the properties of the CANs. We describe the synthesis and dynamic properties of semi IPNs. Because of the DA reaction and transesterification of boronic ester bonds, the topologies of semi IPNs can be altered, contributing to the reprocessing, self-healing, welding, and shape memory behaviors of the produced polymer. Through a microinjection technique, the cut samples of the semi IPNs can be reshaped and mechanical properties of the recycled samples can be well-restored after being remolded at 190 °C for 5 min.

[1]  M. Hakkarainen,et al.  Photocurable, Thermally Reprocessable, and Chemically Recyclable Vanillin-Based Imine Thermosets , 2020 .

[2]  Yaodong Liu,et al.  Dynamic self-stiffening in polyacrylonitrile/thermoplastic polyurethane composites , 2020 .

[3]  Hongfu Zhou,et al.  Thermoplastic polyurethane (TPU) modifier to develop bimodal cell structure in polypropylene/TPU microcellular foam in presence of supercritical CO2 , 2020, Journal of Vinyl and Additive Technology.

[4]  H. Akat,et al.  Investigations on thermal and radiation shielding properties of the poly(hydroxyethyl methacrylate-co-styrene)/tungsten(VI) oxide composites , 2020 .

[5]  William R. Dichtel,et al.  Reprocessable Cross-Linked Polymer Networks: Are Associative Exchange Mechanisms Desirable? , 2020, ACS central science.

[6]  Zachary A. Digby,et al.  Controlling polymer architecture to design dynamic network materials with multiple dynamic linkers , 2020, Molecular Systems Design & Engineering.

[7]  Jie Liu,et al.  Study on the rheological properties of regenerated cellulose/thermoplastic polyurethane blend spinning solutions , 2020 .

[8]  B. P. Tripathi,et al.  Polyethylenimine‐Based Shape Memory Polyurethane with Low Transition Temperature and Excellent Memory Performance , 2020, Macromolecular Materials and Engineering.

[9]  M. Sigalov,et al.  E→Z photoinduced isomerization and hydrogen bonding in the peri-acetamido substituted (1H-pyrrol-2-ylmethylene)benzocycloalkanones , 2020 .

[10]  Zhe Ma,et al.  Highly elastic, strong, and reprocessable cross-linked polyolefin elastomers enabled by boronic ester bonds , 2020 .

[11]  L. Irusta,et al.  Recyclable, remendable and healing polyurethane/acrylic coatings from UV curable waterborne dispersions containing Diels-Alder moieties , 2020 .

[12]  R. Sun,et al.  Alkaline monomer for mechanical enhanced and self-healing hydrogels based on dynamic borate ester bonds , 2019 .

[13]  L. Leibler,et al.  Dynamic covalent chemistry in polymer networks: a mechanistic perspective , 2019, Polymer Chemistry.

[14]  Xinle Huang,et al.  Weldable, malleable and programmable epoxy vitrimers with high mechanical properties and water insensitivity , 2019, Chemical Engineering Journal.

[15]  Jianguo Mi,et al.  Microcellular morphology evolution of polystyrene/thermoplastic polyurethane blends in the presence of supercritical CO2 , 2019, Cellular Polymers.

[16]  B. Guo,et al.  Mechanically Robust, Self-Healable, and Reprocessable Elastomers Enabled by Dynamic Dual Cross-Links , 2019, Macromolecules.

[17]  Qiang Zheng,et al.  A Tough and Stiff Hydrogel with Tunable Water Content and Mechanical Properties Based on the Synergistic Effect of Hydrogen Bonding and Hydrophobic Interaction , 2018, Macromolecules.

[18]  B. Guo,et al.  Covalently Cross-Linked Elastomers with Self-Healing and Malleable Abilities Enabled by Boronic Ester Bonds. , 2018, ACS applied materials & interfaces.

[19]  Z. Guan,et al.  Recyclable, Strong, and Highly Malleable Thermosets Based on Boroxine Networks. , 2018, Journal of the American Chemical Society.

[20]  Tuan Liu,et al.  Eugenol-Derived Biobased Epoxy: Shape Memory, Repairing, and Recyclability , 2017 .

[21]  Jaeyoon Chung,et al.  Silyl Ether as a Robust and Thermally Stable Dynamic Covalent Motif for Malleable Polymer Design. , 2017, Journal of the American Chemical Society.

[22]  E. Alsberg,et al.  Highly Elastic and Tough Interpenetrating Polymer Network-Structured Hybrid Hydrogels for Cyclic Mechanical Loading-Enhanced Tissue Engineering , 2017 .

[23]  T. Ube,et al.  Interpenetrating polymer networks of liquid-crystalline azobenzene polymers and poly(dimethylsiloxane) as photomobile materials. , 2017, Soft matter.

[24]  Sabu Thomas,et al.  Transport behaviour of aromatic solvents through styrene butadiene rubber/poly [methyl methacrylate] (SBR/PMMMA) interpenetrating polymer network (IPN) membranes , 2017 .

[25]  Wen‐Hua Sun,et al.  (Co-)polymerization of methylacrylate with NBE/1-hexene by (8-arylimino-5,6,7-trihydroquinolyl)(methyl)palladium chlorides: an approaching mechanism and the polymeric microstructures , 2017 .

[26]  Borui Zhang,et al.  Effect of Polymer Network Architecture, Enhancing Soft Materials Using Orthogonal Dynamic Bonds in an Interpenetrating Network. , 2017, ACS macro letters.

[27]  Ludwik Leibler,et al.  High-performance vitrimers from commodity thermoplastics through dioxaborolane metathesis , 2017, Science.

[28]  Tao Xie,et al.  Dynamic Covalent Polymer Networks: from Old Chemistry to Modern Day Innovations , 2017, Advanced materials.

[29]  Dujing Wang,et al.  Correlation between stress relaxation dynamics and thermochemistry for covalent adaptive networks polymers , 2017 .

[30]  Maarten M. J. Smulders,et al.  Dynamic covalent polymers , 2016, Journal of polymer science. Part A, Polymer chemistry.

[31]  Liqun Zhang,et al.  Bioinspired Engineering of Sacrificial Metal–Ligand Bonds into Elastomers with Supramechanical Performance and Adaptive Recovery , 2016 .

[32]  Tao Xie,et al.  Shape memory polymer network with thermally distinct elasticity and plasticity , 2016, Science Advances.

[33]  Zhibin Guan,et al.  Malleable and Self-Healing Covalent Polymer Networks through Tunable Dynamic Boronic Ester Bonds. , 2015, Journal of the American Chemical Society.

[34]  Damien Montarnal,et al.  Reprocessing and Recycling of Highly Cross-Linked Ion-Conducting Networks through Transalkylation Exchanges of C-N Bonds. , 2015, Journal of the American Chemical Society.

[35]  M. Hillmyer,et al.  Polylactide Vitrimers. , 2014, ACS macro letters.

[36]  H. Grande,et al.  The processability of a poly(urea-urethane) elastomer reversibly crosslinked with aromatic disulfide bridges , 2014 .

[37]  Costantino Creton,et al.  Toughening Elastomers with Sacrificial Bonds and Watching Them Break , 2014, Science.

[38]  Qiang Wu,et al.  Bio‐Inspired High‐Performance and Recyclable Cross‐Linked Polymers , 2013, Advanced materials.

[39]  C. Bowman,et al.  Covalent adaptable networks: smart, reconfigurable and responsive network systems. , 2013, Chemical Society reviews.

[40]  Yaling Zhang,et al.  Facilely prepared inexpensive and biocompatible self-healing hydrogel: a new injectable cell therapy carrier , 2012 .

[41]  C. Bowman,et al.  A Simple Relationship Relating Linear Viscoelastic Properties and Chemical Structure in a Model Diels–Alder Polymer Network , 2012 .

[42]  Ludwik Leibler,et al.  Catalytic Control of the Vitrimer Glass Transition. , 2012, ACS macro letters.

[43]  Ludwik Leibler,et al.  Metal-catalyzed transesterification for healing and assembling of thermosets. , 2012, Journal of the American Chemical Society.

[44]  T. J. McCarthy,et al.  A surprise from 1954: siloxane equilibration is a simple, robust, and obvious polymer self-healing mechanism. , 2012, Journal of the American Chemical Society.

[45]  Ludwik Leibler,et al.  Silica-Like Malleable Materials from Permanent Organic Networks , 2011, Science.

[46]  Yong‐Chan Chung,et al.  Grafting of shape memory polyurethane with poly(ethyleneimine) and the effect on electrolytic attraction in aqueous solution and shape recovery properties , 2011, Macromolecular Research.

[47]  J. Berg,et al.  A review of the feasibility of lightening structural polymeric composites with voids without compromising mechanical properties. , 2010, Advances in colloid and interface science.

[48]  Patricia Krawczak,et al.  Thermosetting (bio)materials derived from renewable resources: A critical review , 2010 .

[49]  Brian J. Adzima,et al.  Covalent Adaptable Networks (CANs): A Unique Paradigm in Crosslinked Polymers. , 2010, Macromolecules.

[50]  R. Grubbs,et al.  Ruthenium-based heterocyclic carbene-coordinated olefin metathesis catalysts. , 2010, Chemical reviews.

[51]  M. Maspoch,et al.  Study of the interface behaviour between MABS/TPU bi-layer structures obtained through over moulding , 2009 .

[52]  Yan-Min Shen,et al.  Thermosensitive hydrogels synthesized by fast Diels–Alder reaction in water , 2009 .

[53]  J. Lee,et al.  Mechanical and three-body abrasive wear behaviour of PMMA/TPU blends , 2008 .

[54]  A. Kavitha,et al.  Atom-Transfer Radical Copolymerization of Furfuryl Methacrylate (FMA) and Methyl Methacrylate (MMA): A Thermally-Amendable Copolymer , 2007 .

[55]  W. Brostow,et al.  Nanoscale confinement effects on the relaxation dynamics in networks of diglycidyl ether of bisphenol-A and low-molecular-weight poly(ethylene oxide). , 2007, The journal of physical chemistry. B.

[56]  A. Simmons,et al.  The effect of sterilisation on a poly(dimethylsiloxane)/poly(hexamethylene oxide) mixed macrodiol-based polyurethane elastomer. , 2006, Biomaterials.

[57]  Fuquan Guo,et al.  Novel Shape‐Memory Polymer Based on Hydrogen Bonding , 2006 .

[58]  H. A. Stefani,et al.  An Easy Synthesis of Enaminones in Water as Solvent. , 2001 .

[59]  B. Baysal,et al.  Interpenetrating hydrogel networks based on polyacrylamide and poly(itaconic acid): synthesis and characterization , 1999 .