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Self-healing Polymers Based On Thermally Reversible Diels–Alder Chemistry

Y. Liu, Tsai-Wei Chuo
Published 2013 · Chemistry

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The development of self-healing materials has received much research attention in the last two decades. This review paper gathers recent publications on the self-healing polymeric materials with thermally reversible Diels–Alder (DA) chemistry. The DA reaction is a [4 + 2] cycloaddition involving a diene and a dienophile. The self-healing polymers employing the furan group as a diene and the maleimide group as a dienophile have been widely studied. Multifunctional furan and maleimide compounds construct thermally reversible crosslinked networks showing removability and remendability. Self-healing materials have also been utilized as healing agents for conventional thermosets like epoxy resins. Other diene–dienophile pairs, such as anthracene–maleimide and cyclopentadiene–dicyclopentadiene, have also been utilized for the development of thermally induced self-healing materials. Photo-induced self-healing polymers and some novel applications based on DA reactions have been discussed in this review. Moreover, self-healing polymer systems based on other thermally triggered and assisted reactions are also discussed. The discussed publication has provided promising molecular designs and synthetic strategies for the development of high performance self-healing polymers.
This paper references
10.1002/marc.201200599
3D Photofixation Lithography in Diels-Alder Networks.
Brian J. Adzima (2012)
10.1038/nature09963
Optically healable supramolecular polymers
Mark Burnworth (2011)
10.1002/POLA.21184
Crosslinked epoxy materials exhibiting thermal remendablility and removability from multifunctional maleimide and furan compounds
Y. Liu (2006)
10.1002/MACP.200600445
Thermally Reversible Cross‐Linked Polyamides with High Toughness and Self‐Repairing Ability from Maleimide‐ and Furan‐Functionalized Aromatic Polyamides
Y. Liu (2007)
10.1021/CM202635W
Self-Healing of Polymers via Synchronous Covalent Bond Fission/Radical Recombination
Chan′e Yuan (2011)
10.1002/MACP.201100410
Thermoreversible Networks by Diels–Alder Reaction of Cellulose Furoates With Bismaleimides
Jennifer Ax (2012)
10.1002/POLA.1994.080321312
Thermoreversible reaction of diels—alder polymer composed of difurufuryladipate with bismaleimidodiphenylmethane
N. Kuramoto (1994)
10.1016/J.ACTAMAT.2007.06.019
Quantitative evaluation of fracture, healing and re-healing of a reversibly cross-linked polymer
T. Plaisted (2007)
10.1021/MA2001492
Self-Healing Materials Based on Disulfide Links
J. Canadell (2011)
10.1039/c2cc34701f
Multivalent H-bonds for self-healing hydrogels.
J. Cui (2012)
10.1002/POLA.23094
Synthesis of Self-Healing Supramolecular Rubbers from Fatty Acid Derivatives, Diethylene Triamine, and Urea
Damien Montarnal (2008)
10.1021/MA9710141
Application of the Diels−Alder Reaction to Polymers Bearing Furan Moieties. 2. Diels−Alder and Retro-Diels−Alder Reactions Involving Furan Rings in Some Styrene Copolymers
Cécile Goussé (1998)
10.1002/POLA.1992.080300829
Thermally reversible crosslinking of polystyrene via the furan-maleimide diels-alder reaction
Stephen A. Canary (1992)
10.1016/J.POLYMER.2011.05.024
Self-healing linear polymers based on RAFT polymerization
Li Yao (2011)
10.1016/J.POLYMER.2006.05.036
Synthesis and properties of readily recyclable polymers from bisfuranic terminated poly(ethylene adipate) and multi-maleimide linkers
M. Watanabe (2006)
10.1021/MA8027672
Thermally Self-Healing Polymeric Materials : The Next Step to Recycling Thermoset Polymers?
Youchun Zhang (2009)
10.1021/MA062093W
Dendrimers Based on Thermally Reversible Furan−Maleimide Diels−Alder Adducts
Michael L. Szalai (2007)
10.1021/am900104w
Reversibly cross-linked polymer gels as healing agents for epoxy-amine thermosets.
A. M. Peterson (2009)
10.1002/POLA.22195
A tailor‐made polymethacrylate bearing a reactive diene in reversible diels–alder reaction
A. Kavitha (2007)
10.1021/MA2015134
Self-Healing Polymer Films Based on Thiol-Disulfide Exchange Reactions and Self-Healing Kinetics Measured Using Atomic Force Microscopy
J. Yoon (2012)
10.1021/OL0101281
Thermally responsive dendrons and dendrimers based on reversible furan-maleimide Diels-Alder adducts.
J. McElhanon (2001)
10.1021/MA990638Z
Cross-Linking and Modification of Poly(ethylene terephthalate-co-2,6-anthracenedicarboxylate) by Diels-Alder Reactions with Maleimides
J. R. Jones (1999)
10.1002/MACP.201100442
Current trends in the field of self-healing materials
N. Guimard (2012)
10.1126/SCIENCE.1065879
A Thermally Re-mendable Cross-Linked Polymeric Material
Xiangxu Chen (2002)
10.1039/C0PY00104J
Self-healing and self-mendable polymers
Jay A. Syrett (2010)
10.1021/J100786A013
Relaxation of Disulfide and Tetrasulfide Polymers.
A. Tobolsky (1964)
10.1016/S0032-3861(01)00270-1
A sol–gel reaction of vinyl polymers based on thermally reversible urea linkages
J. Chang (2001)
10.1179/095066010X12646898728408
Self-healing polymers and composites
T. C. Mauldin (2010)
10.1021/am900124c
"Click chemistry" in tailor-made polymethacrylates bearing reactive furfuryl functionality: a new class of self-healing polymeric material.
A. Kavitha (2009)
10.1002/MACP.201100377
Low‐Temperature Cu(I)‐Catalyzed “Click” Reactions for Self‐Healing Polymers
M. Schunack (2012)
10.1002/POL.1979.170170714
Thermally reversible polymer systems by cyclopentadienylation. I. A model for termination by cyclopentadienylation of olefin polymerization
J. P. Kennedy (1979)
10.1002/POLA.23957
Reversible click chemistry at the service of macromolecular materials. 2. Thermoreversible polymers based on the Diels‐Alder reaction of an A‐B furan/maleimide monomer
A. Gandini (2010)
10.1002/MACP.201100407
Diffusion and Reaction Phenomena in Solution‐Based Healing of Polymer Coatings Using the Diels–Alder Reaction
P. A. Pratama (2012)
10.1021/ja200356f
Light-induced hetero-Diels-Alder cycloaddition: a facile and selective photoclick reaction.
S. Arumugam (2011)
10.1021/MA902203R
Smart “All Acrylate” ABA Triblock Copolymer Bearing Reactive Functionality via Atom Transfer Radical Polymerization (ATRP): Demonstration of a “Click Reaction” in Thermoreversible Property
A. Kavitha (2010)
10.1002/ADMA.201003036
Self‐Healing Materials
S. Zwaag (2007)
10.1038/NMAT1934
Self-healing materials with microvascular networks.
K. S. Toohey (2007)
10.1039/C1PY00041A
Diels–Alder “click” reactions: recent applications in polymer and material science
M. Tasdelen (2011)
10.1002/adma.201200196
A self-healing conductive ink.
Susan A. Odom (2012)
10.1039/B711716G
Self-healing materials: a review.
R. P. Wool (2008)
10.1021/MA991899B
Thermally Reversible IPN Organic−Inorganic Polymer Hybrids Utilizing the Diels−Alder Reaction
Y. Imai (2000)
10.3144/EXPRESSPOLYMLETT.2012.14
Investigation on the thermal properties of new thermo-reversible networks based on poly(vinyl furfural) and multifunctional maleimide compounds
C. Gaina (2012)
10.1038/nature06669
Self-healing and thermoreversible rubber from supramolecular assembly
Philippe Cordier (2008)
10.1016/J.POLYMER.2012.03.061
Development of optimized autonomous self-healing systems for epoxy materials based on maleimide chemistry
Stijn Billiet (2012)
10.1021/MA020343C
Diels−Alder Reactions with Novel Polymeric Dienes and Dienophiles: Synthesis of Reversibly Cross-Linked Elastomers
Rana Gheneim (2002)
10.1021/MA902180R
Thermally Reversible Dendronized Step-Polymers Based on Sequential Huisgen 1,3-Dipolar Cycloaddition and Diels-Alder ``Click'' Reactions
Nathan W. Polaske (2010)
10.1021/am101012c
Linear/network poly(ε-caprolactone) blends exhibiting shape memory assisted self-healing (SMASH).
E. D. Rodriguez (2011)
10.1002/PI.792
Copolymerization of a bisanthracene compound with bismaleimides by Diels–Alder cycloaddition
M. Grigoraş (2001)
10.1039/b904502n
Healable polymeric materials: a tutorial review.
S. Burattini (2010)
10.1021/MA800432G
Synthesis and Characterization of a Single-Component Thermally Remendable Polymer Network: Staudinger and Stille Revisited
E. Murphy (2008)
10.1039/b910648k
A self-repairing, supramolecular polymer system: healability as a consequence of donor-acceptor pi-pi stacking interactions.
S. Burattini (2009)
10.1021/MA00212A007
Reversible gelation of polyoxazoline by means of diels-alder reaction
Y. Chujo (1990)
10.1002/MACP.201000108
Diels–Alder Cycloaddition‐Cycloreversion: A Powerful Combo in Materials Design
A. Sanyal (2010)
10.1002/adma.201000361
Reversible Diels-Alder chemistry as a modular polymeric color switch.
Thomas Pauloehrl (2010)
10.1021/CM049394+
Crack Healing in Polymeric Materials via Photochemical [2+2] Cycloaddition
Chan-Moon Chung (2004)
10.1002/POL.1979.170170715
Thermally reversible polymer systems by cyclopentadienylation. II. The synthesis of cyclopentadiene‐containing polymers
J. P. Kennedy (1979)
10.1021/MA0210675
New Thermally Remendable Highly Cross-Linked Polymeric Materials
X. Chen (2003)
10.1002/marc.201000643
Towards the generation of self-healing materials by means of a reversible photo-induced approach.
P. Froimowicz (2011)
10.1039/B9PY00316A
Self-healing polymers prepared via living radical polymerisation
Jay A. Syrett (2010)
10.1126/SCIENCE.1110505
Photoinduced Plasticity in Cross-Linked Polymers
T. F. Scott (2005)
10.1016/J.POLYMER.2006.02.057
Thermally reversible cross-linked polyamides and thermo-responsive gels by means of Diels–Alder reaction
Y. Liu (2006)
10.1002/ADFM.200500724
Exploiting Chemical Switching in a Diels–Alder Polymer for Nanoscale Probe Lithography and Data Storage
B. Gotsmann (2006)
10.1021/MZ200195N
Dynamic Hydrogels with an Environmental Adaptive Self-Healing Ability and Dual Responsive Sol–Gel Transitions
G. Deng (2012)
10.1088/0964-1726/18/8/085001
Self-healing flexible laminates for resealing of puncture damage
Brett A. Beiermann (2009)
10.1016/J.EURPOLYMJ.2004.01.036
Kinetic aspects of the Diels–Alder reaction between poly(styrene-co-furfuryl methacrylate) and bismaleimide
E. Goiti (2004)
10.1126/science.1167391
Self-Repairing Oxetane-Substituted Chitosan Polyurethane Networks
Biswajit Ghosh (2009)
10.1039/B811938D
A thermally remendable epoxy resin
Q. Tian (2009)
10.1002/MARC.200350013
Thermal Breakdown by the Retro Diels–Alder Reaction of Crosslinking in Poly[styrene‐co‐(furfuryl methacrylate)]
E. Goiti (2003)
10.1039/B900859D
A novel self-healing supramolecular polymer system.
S. Burattini (2009)
10.1073/pnas.1201122109
Rapid self-healing hydrogels
A. Phadke (2012)
10.1002/MACP.201100406
Functionalization of Reactive Polymeric Coatings via Diels–Alder Reaction Using Microcontact Printing
T. N. Gevrek (2012)
10.1039/B817586A
Temperature and redox responsive hydrogels from ABA triblock copolymers prepared by RAFT polymerization
A. Vogt (2009)
10.1016/S0014-3057(97)00009-8
The application of the Diels-Alder reaction to polymers bearing furan moieties. 1. Reactions with maleimides
H. Laita (1997)
10.1039/C2JM30578J
Reversibility of solid state radical reactions in thermally remendable polymers with C–ON bonds
F. Wang (2012)
10.1021/MA101893U
Photoinduced Conjugation of Dithioester- and Trithiocarbonate-Functional RAFT Polymers with Alkenes
Till Gruendling (2011)
10.1039/C2PY20028G
Self-healable and recyclable triple-shape PPDO–PTMEG co-network constructed through thermoreversible Diels–Alder reaction
J. Zhang (2012)
10.1016/J.PROGPOLYMSCI.2009.10.006
The world of smart healable materials
E. Murphy (2010)
10.1016/J.COMPSCITECH.2010.08.017
Multiple healing effect of thermally activated self-healing composites based on Diels–Alder reaction
J. S. Park (2010)
10.1002/POLA.22960
High performance thermosets from a curable Diels–Alder polymer possessing benzoxazine groups in the main chain
Ching-I Chou (2008)
10.1021/ja903080c
Versatile one-pot synthesis of supramolecular plastics and self-healing rubbers.
Damien Montarnal (2009)
10.1021/MA00026A001
Thermally reversible polymer linkages. 3. Covalently crosslinked poly(azlactone)
K. Wagener (1991)
10.1021/LA047074Z
Thermally cleavable surfactants based on furan-maleimide Diels-Alder adducts.
J. McElhanon (2005)
10.1016/J.POLYMER.2011.11.007
A thermally-stable self-mending polymer networked by Diels–Alder cycloaddition
Naoko Yoshie (2011)
10.1021/am9009378
Room-temperature healing of a thermosetting polymer using the Diels-Alder reaction.
A. M. Peterson (2010)
10.1002/MACP.200500063
The rapid chain extension of anthracene-functional polyesters by the Diels-Alder reaction with bismaleimides
Robert M. Kriegel (2005)
10.1021/ED101109F
Synthesis of a Self-Healing Polymer Based on Reversible Diels–Alder Reaction: An Advanced Undergraduate Laboratory at the Interface of Organic Chemistry and Materials Science
H. Weizman (2011)
10.1016/J.EURPOLYMJ.2003.09.017
Some properties of networks produced by the Diels–Alder reaction between poly(styrene-co-furfuryl methacrylate) and bismaleimide
E. Goiti (2004)
10.1021/MA0400618
Synthesis of organic-inorganic polymer hybrids controlled by Diels-Alder reaction
K. Adachi (2004)
10.1016/J.POLYMDEGRADSTAB.2010.01.032
Thermo-responsive mending of polymers crosslinked by thermally reversible covalent bond: Polymers from bisfuranic terminated poly(ethylene adipate) and tris-maleimide
N. Yoshie (2010)
10.1002/APP.10753
Removable foams based on an epoxy resin incorporating reversible Diels-Alder adducts
J. McElhanon (2002)



This paper is referenced by
10.1002/cssc.201702435
From Conventional Lewis Acids to Heterogeneous Montmorillonite K10: Eco-Friendly Plant-Based Catalysts Used as Green Lewis Acids.
M. Hechelski (2018)
10.1039/C7PY00215G
Synthesis of a self-healing siloxane-based elastomer cross-linked via a furan-modified polyhedral oligomeric silsesquioxane: investigation of a thermally reversible silicon-based cross-link
Amin Nasresfahani (2017)
10.1002/chem.201706100
Reversible Nanogate System for Mesoporous Silica Nanoparticles Based on Diels-Alder Adducts.
R. Castillo (2018)
10.3390/molecules25010074
Bio-Based Thermo-Reversible Aliphatic Polycarbonate Network
P. Durand (2019)
10.1007/12_2015_341
Characterization of Self-Healing Polymers: From Macroscopic Healing Tests to the Molecular Mechanism
Stefan Bode (2015)
10.1021/ACSSUSCHEMENG.6B02007
Polyesters and Poly(ester-urethane)s from Biobased Difuranic Polyols
Zehuai Mou (2016)
10.1039/d0py00741b
Novel clickable and fluorescent poly(siloxane amine)s for reusable adhesives and reprocessable elastomers
Jie Zhou (2020)
10.1016/j.ccr.2020.213711
Supramolecular self-healing materials via host-guest strategy between cyclodextrin and specific types of guest molecules
Masoumeh Mohamadhoseini (2020)
10.1039/C3RA42278J
Synthesis and characterization of linear self-healing polyurethane based on thermally reversible Diels–Alder reaction
P. Du (2013)
10.3144/EXPRESSPOLYMLETT.2016.51
Characterization and kinetic study of Diels-Alder reaction: Detailed study on N-phenylmaleimide and furan based benzoxazine with potential self-healing application
Z. Stirn (2016)
10.1016/J.POLYMER.2016.12.029
A new reactive polymethacrylate bearing pendant furfuryl groups: Synthesis, thermoreversible reactions, and self-healing
Sungmin Jung (2017)
10.1002/cssc.201800595
Clicking Biobased Polyphenols: A Sustainable Platform for Aromatic Polymeric Materials.
P. Buono (2018)
10.1002/marc.201600777
Multiblock Copolymer-Based Dual Dynamic Disulfide and Supramolecular Crosslinked Self-Healing Networks.
S. Y. An (2017)
10.1016/J.COMPSCITECH.2019.03.021
Reversibly cross-linked fullerene/polyamide composites based on Diels-Alder reaction
Jingjing Chen (2019)
10.1016/j.polymer.2019.121882
Alkaline monomer for mechanical enhanced and self-healing hydrogels based on dynamic borate ester bonds
Fei Ji (2019)
10.1021/ACS.MACROMOL.6B01889
Facile Access to Multistimuli-Responsive Self-Assembled Block Copolymers via a Catechol/Boronic Acid Ligation
Fanny Coumes (2016)
10.1002/marc.201700475
Telechelic Polybutadienes or Polyisoprenes Precursors for Recyclable Elastomeric Networks.
P. Berto (2017)
10.3390/polym11061057
Thermally Healable and Recyclable Graphene-Nanoplate/Epoxy Composites Via an In-Situ Diels-Alder Reaction on the Graphene-Nanoplate Surface
Cho-Rong Oh (2019)
10.1021/MA501386V
“Click”-Inspired Chemistry in Macromolecular Science: Matching Recent Progress and User Expectations
Pieter Espeel (2015)
10.1002/anie.201813525
Dynamic Covalent Bonds in Polymeric Materials.
Progyateg Chakma (2019)
10.1039/C7PY00896A
Thermoreversible cross-linking of ethylene/propylene copolymer rubbers
Wang Ai-hui (2017)
10.20944/preprints201809.0145.v1
Multifunctional Biodegradable Polymers with Room Temperature Self-Healing and Rewritable Shape Memory Properties via Diels-Alder Reaction
Shenyang Cai (2018)
10.1039/C3NJ01245J
Synthesis of linear polyurethane bearing pendant furan and cross-linked healable polyurethane containing Diels–Alder bonds
P. Du (2014)
10.1007/s00289-019-02805-z
Kinetic model of a Diels–Alder reaction in a molten state: thermal and viscoelastic behaviour
A. Ručigaj (2019)
Diels Alder Hydrogels as Intraocular Drug Delivery Systems for Antibodies
S. Kirchhof (2015)
10.3390/polym11050773
Recyclable Self-Healing Polyurethane Cross-Linked by Alkyl Diselenide with Enhanced Mechanical Properties
Yuqing Qian (2019)
10.1039/C6TA06213J
Self-healing polymers and composites for extreme environments
Yunseon Heo (2016)
10.1016/j.eurpolymj.2020.109927
Reworkable adhesives: Healable and fast response at ambient environment based on anthracene-based thiol-ene networks
Lijiao Shen (2020)
10.1039/d0py01296c
Temperature-mediated Molecular Ladder Self-assembly Employing Diels-Alder Cycloaddition
S. C. Leguizamon (2020)
10.1016/B978-1-78242-280-8.00006-6
Reversible cross-linking polymer-based self-healing materials
P. Du (2015)
10.1002/APP.45884
Assessment of random aromatic co‐polyamides containing two different bulky pendant groups
J. M. Pérez-Francisco (2018)
RE-HEALABLE COATING BASED UPON THERMALLY RESPONSIVE LINKAGES
Phil Costanzo (2013)
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