One pot stimuli-responsive linear waterborne polyurethanes via Diels-Alder reaction

Aizpurua, Jon; Martin, Loli; Formoso, Elena; González, Alba; Irusta, L.

doi:10.1016/j.porgcoat.2019.01.008

Cited by 24 publications

(15 citation statements)

References 52 publications

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“…In order to study the reversibility of the DA reaction, different heating cycles were carried out (Scheme 3). [41] Therefore, the cured sample (sample 0) was placed 15 min in an oven at 140°C in order to provoke the retroDA reaction. Subsequently, it was placed 5 h in an oven at 60°C (sample 1).…”

Section: Methodsmentioning

confidence: 99%

Recyclable Epoxy Resin via Simultaneous Dual Permanent/Reversible Crosslinking Based on Diels–Alder Chemistry

Puyadena

Calafel

Román

et al. 2021

Macro Chemistry & Physics

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Taking advantage of the reversible Diels-Alder (DA) reaction, a simple strategy to obtain recyclable epoxy resins is presented. For this purpose, blends of furan-functionalized and nonfunctionalized epoxy resin are prepared. After the addition of diamine and bismaleimide, blends are heated at 150°C for 5 min, where the permanent amine/epoxy reaction has taken place and upon cooling to room temperature the reversible DA reaction has happened, giving rise to a dual permanent/nonpermanent network. Both reactions are confirmed by Fourier-transform infrared (FTIR) and 13 C-crosspolarization, magic-angle spinning (CP/MAS) nuclear magnetic resonance (NMR). Modulated differential scanning calorimetry (MDSC)shows that the epoxy/amine and bismaleimide/amine curing reaction take place, after the DA reaction, simultaneously with the retroDA reaction and before the bismaleimide homopolymerization. Therefore, under the appropriate curing conditions, the Michael's addition and the bismaleimide homopolymerization do not avoid the formation of a hybrid network, as stated in other reports. The reversibility of the DA reaction in three consecutive cycles is confirmed by DSC. Finally, the dual-cured sample is reprocessed three times without significant loss of mechanical properties.

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Section: Methodsmentioning

confidence: 99%

Recyclable Epoxy Resin via Simultaneous Dual Permanent/Reversible Crosslinking Based on Diels–Alder Chemistry

Puyadena

Calafel

Román

et al. 2021

Macro Chemistry & Physics

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“…The second strategy based on introducing the DA adduct into the polymer structure using a modified diol, allows the obtaining of novel one-pot stable stimuli-responsive WPU dispersions. [109] A self-healing polymeric binder for energetic composites was developed by incorporation of reversible DA bonds into polyurethane that was synthesized from NCO-terminated prepolymer with furfuryl amine, and cross-linked with bismaleimide. The tensile test indicated that DA polyurethane had excellent mechanical properties (the original tensile strength of TPU film reached 10.68 MPa), and its healing efficiency was up to 80-95%.…”

Section: Diels-alder Bondsmentioning

confidence: 99%

A Short Review on Self‐Healing Thermoplastic Polyurethanes

Yao

Xiao

Liu

2021

Macro Chemistry & Physics

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of self-healing will happen only by satisfying four factors: location, temporality, mobility, [17] and intermolecular interaction. The surface of the damaged part needs to contact with each other properly and the dynamic interaction requires time to reform. Self-healing TPUs can be used as coatings, [18] adhesives, [19] biomedical materials, [20] wearable electronics, [21] and this self-healing property can extend the service life and reduce waste. Early selfhealing materials were design to employ encapsulated external healing agents. [22] With conceptualization and development, the classification of healing agents comprises three types: microcapsules, [23,24] hollow fibers, [25,26] and microvascular networks. [27] Limited by the supply of healing agents, multiple cycle repairs cannot be achieved; in addition, the microcontainers may be harmful to the regular service of the matrix, which change the inherent properties of the matrix, fail to respond quickly and cause the healing agent to flow out when the matrix is damaged. To overcome these restrictions, research on self-healing polymers has focused on the incorporation of self-healing mechanism directly in the material by introducing dynamic bonds or interactions (covalent or non-covalent) that can break and reform in a perpetual manner upon appropriate stimuli. The dynamic non-covalent interactions like hydrogen bond, [28,29] shape-memory assisted self-healing, [30,31] host-guest interaction, [32,33] and metal-ligand coordination [34,35] primarily influence the self-healing efficiency. The dynamic covalent bonds such as Diels-Alder bonds, [36,37] disulfide bonds, [38,39] diselenide bonds, [40,41] and ditelluride bonds [42] exert a major effect on the mechanical property of self-healing polyurethanes. However, there is a contradiction between self-healing efficiency and mechanical property. It is challenging to obtain a material with both remarkable mechanical strengths and a high self-healing efficiency. Interest in homogeneous self-healing materials has been growing because they do not need to be combined with therapeutic agents, which avoids many thorny issues including complicated pre-embedding processes, compatibility, and controlled and sustained release. For healing agents-assisted self-healing materials, they are usually thermosetting, and an obvious limitation is that they only support one self-healing cycle. [43] Self-healing elastomers can achieve repair through dynamic molecular interactions between the damaged surface. In this article, we only focus on self-healing TPU elastomer mechanism based on dynamic covalent or non-covalent bonds. Self-healing polyurethanes based on external healing agents are outside the scope of this article.Thermoplastic polyurethane (TPU) is a melt-processing polymer with a high elasticity, high tensile strength, low-temperature resistance, wear-resistance, and corrosion resistance ability. TPU can be used in the automotive industry, electronics, medical supplies, coatings, and sports equipment. Introduction of self-healin...

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“…A significant limitation of this approach is the low degrees of polymerization by fmDA reaction (Table 4). Other approaches that may be used for the synthesis of high-molecular-weight linear polymers include the DA polymerization of linear oligomers or pre-polymers end-capped with the furan-or maleimide functional groups [92][93][94][95], or co-polymerization of bifunctional fmDA adducts [96]. Scheme 5.…”

Section: Synthesis Of Dynamic Linear Polymers Using the Fmda "Click" Reactionmentioning

confidence: 99%

Diels–Alder Cycloadditions of Bio-Derived Furans with Maleimides as a Sustainable «Click» Approach towards Molecular, Macromolecular and Hybrid Systems

2021

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This mini-review highlights the recent research trends in designing organic or organic-inorganic hybrid molecular, biomolecular and macromolecular systems employing intermolecular Diels–Alder cycloadditions of biobased, furan-containing substrates and maleimide dienophiles. The furan/maleimide Diels–Alder reaction is a well-known process that may proceed with high efficiency under non-catalytic and solvent-free conditions. Due to the simplicity, 100% atom economy and biobased nature of many furanic substrates, this type of [4+2]-cycloaddition may be recognized as a sustainable “click” approach with high potential for application in many fields, such as fine organic synthesis, bioorganic chemistry, material sciences and smart polymers development.

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One pot stimuli-responsive linear waterborne polyurethanes via Diels-Alder reaction

Cited by 24 publications

References 52 publications

Recyclable Epoxy Resin via Simultaneous Dual Permanent/Reversible Crosslinking Based on Diels–Alder Chemistry

Recyclable Epoxy Resin via Simultaneous Dual Permanent/Reversible Crosslinking Based on Diels–Alder Chemistry

A Short Review on Self‐Healing Thermoplastic Polyurethanes

Diels–Alder Cycloadditions of Bio-Derived Furans with Maleimides as a Sustainable «Click» Approach towards Molecular, Macromolecular and Hybrid Systems

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