scholarly journals Thermally Self-Healing Graphene-Nanoplate/Polyurethane Nanocomposites via Diels–Alder Reaction through a One-Shot Process

Nanomaterials ◽  
2019 ◽  
Vol 9 (3) ◽  
pp. 434 ◽  
Author(s):  
Cho-Rong Oh ◽  
Sang-Hyub Lee ◽  
Jun-Hong Park ◽  
Dai-Soo Lee
Keyword(s):  
Molecular Design ◽  
Alder Reaction ◽  
Chain Extender ◽  
Diels Alder ◽  
Self Healing ◽  
Scanning Calorimetry ◽  
Diels Alder Reaction ◽  
A Chain ◽  
The Fourier Transform

Thermally self-healing graphene-nanoplate/polyurethane (GNP/PU) nanocomposites were prepared via a bulk in-situ Diels–Alder (DA) reaction. Graphene-nanoplate (GNP) was used as a reinforcement and crosslinking platform by a DA reaction with a furfuryl-based chain extender of polyurethane (PU). Results showed that a DA reaction occurred in GNP during the PU forming cure process. This procedure is simple and solvent free because of the absence of any independent surface modification process. Through the calculation of the interfacial tensions, the conditions of the bulk in-situ DA reaction were determined to ensure that GNP and the furfuryl group can react with each other at the interface during the curing process without a solvent. The prepared composites were characterized in terms of thermal, mechanical, and thermally self-healing properties via the DA reaction. In the PU capable of a DA reaction (DPU), characteristic peaks of DA and retro DA reactions were observed in the Fourier transform infrared (FT-IR) spectroscopy and endothermic peaks of retro DA reactions appeared in differential scanning calorimetry (DSC) thermograms. The DPU showed significantly enhanced physical properties and chemical resistance. The thermally self-healing capability was confirmed at 110 °C via the retro DA reactions. It is inferred that thermally self-healable crosslinked GNP/PU nanocomposites via DA reactions could be prepared in a simple bulk process through the molecular design of a chain extender for the in-situ reaction at the interface.

scholarly journals Influence of the Glass Transition Temperature and the Density of Crosslinking Groups on the Reversibility of Diels-Alder Polymer Networks

Polymers ◽  
2021 ◽  
Vol 13 (8) ◽  
pp. 1189
Author(s):  
Merlina Thiessen ◽  
Volker Abetz
Keyword(s):  
Glass Transition ◽  
Transition Temperature ◽  
Glass Transition Temperature ◽  
Radical Polymerization ◽  
Polymer Networks ◽  
Alder Reaction ◽  
Diels Alder ◽  
Self Healing ◽  
Scanning Calorimetry ◽  
Diels Alder Reaction

The interest in self-healing, recyclable, and adaptable polymers is growing. This work addresses the reversibility of crosslink formation based on Diels-Alder reaction in copolymer networks containing furfuryl and maleimide groups, which represent the “diene” and the “dienophile,” respectively. The copolymers are synthesized by atom transfer radical polymerization (ATRP) and free radical polymerization. The diene bearing copolymers are crosslinked either with a small molecule containing two dienophiles or with a dienophile bearing copolymer. The influence of the crosslinking temperature on the Diels-Alder reaction is analyzed. Furthermore, the influence of the glass transition temperature and the influence of the density of crosslinking groups on the thermo-reversibility of crosslinking are investigated by temperature dependent infrared spectroscopy and differential scanning calorimetry. It is shown that the reversibility of crosslinking is strongly influenced by the glass transition temperature of the system.

scholarly journals Diels–Alder-Crosslinked Polymers Derived from Jatropha Oil

Polymers ◽  
2018 ◽  
Vol 10 (10) ◽  
pp. 1177 ◽  
Author(s):  
Muhammad Iqbal ◽  
Remco Knigge ◽  
Hero Heeres ◽  
Antonius Broekhuis ◽  
Francesco Picchioni
Keyword(s):  
Methyl Linoleate ◽  
Alder Reaction ◽  
Diels Alder ◽  
Performic Acid ◽  
Self Healing ◽  
Jatropha Oil ◽  
Fatty Esters ◽  
Diels Alder Reaction ◽  
Solvent Free Reaction

Methyl oleate, methyl linoleate, and jatropha oil were fully epoxidized using in situ-generated performic acid. The epoxidized compounds were further reacted with furfurylamine in a solvent-free reaction to obtain furan-functionalized fatty esters which, then, functioned as oligomers for a network preparation. Thermoreversible crosslinking was obtained through a (retro) Diels–Alder reaction with bismaleimide, resulting in the formation of a brittle network for furan-functionalized methyl linoleate and jatropha oil. The furan-functionalized fatty esters were mixed with alternating (1,4)-polyketone reacted with furfurylamine (PK-Furan) for testing the mechanical and self-healing properties with DMTA and DSC, respectively. Full self-healing properties were found, and faster thermoreversibility kinetics were observed, compared to PK-Furan.

Self-Healing Hydrophobic POSS-functionalized Fluorinated Copolymer via RAFT Polymerization and dynamic Diels-Alder Reaction

2021 ◽  
Author(s):  
Siva Ponnupandian ◽  
Prantik Mondal ◽  
Thomas Becker ◽  
Richard Hoogenboom ◽  
Andrew B Lowe ◽  
...  
Keyword(s):  
Chain Transfer ◽  
Raft Polymerization ◽  
Alder Reaction ◽  
Diels Alder ◽  
Self Healing ◽  
Diels Alder Reaction ◽  
Reversible Addition

This investigation reports the preparation of a tailor-made copolymer of furfuryl methacrylate (FMA) and trifluoroethyl methacrylate (TFEMA) via reversible addition-fragmentation chain transfer (RAFT) polymerization. The furfuryl groups of the copolymer...

Organocatalytic enantioselective Diels–Alder reaction between hydroxymaleimides and in situ generated nitrosoalkenes for direct preparation of chiral hemiketals with 1,2-oxazine skeleton

2021 ◽  
Author(s):  
Min Xiang ◽  
Chen-Yi Li ◽  
Jian Zhang ◽  
Ying Zou ◽  
Wen-Sheng Li ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Direct Preparation

Organocatalytic Enantioselective IEDDA reaction between hydroxymaleimides and in situ generated nitrosoalkenes has been disclosed, a series of chiral hemiketals containing 5,6-dihydro-4H-l,2-oxazines and succinimide frameworks have been prepared.

New Chain Extenders for Self-Healing Polymers

2021 ◽  
Vol 899 ◽  
pp. 628-637
Author(s):  
Daria V. Zakharova ◽  
Zalina A. Lok’yaeva ◽  
Alexander A. Pavlov ◽  
Alexander V. Polezhaev
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Hydroxyl Groups ◽  
Structural Fragment ◽  
Self Healing ◽  
Diels Alder Reaction ◽  
Small Series ◽  
Chain Extenders ◽  
Reversible Covalent ◽  
Thermochemical Parameters

We present here a small series of compounds designed to modify the polymer chain of various polyurethanes in order to introduce a structural fragment with the ability of thermally-triggered reversible covalent interactions. Bismaleimides (2a-2e) were synthesized from commercially available aromatic and aliphatic symmetric diamines (1a-1e) and were further introduced into the Diels-Alder reaction with furfuryl alcohol as dienophiles. The Diels-Alder adducts (3a-3e) were obtained as a mixture of endo- and exo-isomer. The presence of symmetrical hydroxyl groups in the structure of the obtained compounds makes them suitable as chain extenders of low molecular weight diisocyanate prepolymers. The presence of a thermally reversible Diels-Alder reaction adduct in the structure of potential chain-extenders opens a possibility to create unique materials with self-healing properties. All compounds obtained were characterized by 1H, 13C NMR, ESI-HRMS, and IR spectroscopy. The thermochemical parameters of the reverse Diels-Alder reaction were established using DSC analysis.

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