Diels–Alder‐based crosslinked self‐healing polyurethane/urea from polymeric methylene diphenyl diisocyanate

Du, Pengfei; Wu, Meiyin; Liu, Xuanxuan; Zheng, Zhen; Wang, Xinling; Joncheray, Thomas J.; Zhang, Yuefan

doi:10.1002/app.40234

Cited by 76 publications

(53 citation statements)

References 44 publications

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“…This effect was also observed by Kavitha and Singha [16][17][18][19]. Additional, other studies revealed that more polar environments of the maleimide/furan unit resulted in a slightly decreased rDA temperature [25][26][27][28]. Toncelli et al pointed out that at relatively low maleimide/furan ratio the RDA transitions become broader and shifts asymmetrically towards lower temperatures, while the crosslinking density drops significantly.…”

Section: A N U S C R I P Tmentioning

confidence: 49%

Tuning the self-healing behavior of one-component intrinsic polymers

Kötteritzsch

Hager

Schubert

2015

Polymer

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Section: A N U S C R I P Tmentioning

confidence: 49%

Tuning the self-healing behavior of one-component intrinsic polymers

Kötteritzsch

Hager

Schubert

2015

Polymer

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“…During the development of self-healing material much attention is often given to the understanding the mechanistic perspective of a given reaction as much as possible. Such studies are frequently accompanied by kinetic investigations of the reaction [11][12][13][14][15][16]. Benzoxazines, because of their unique characteristics, are recently gaining much attention in polymer synthesis and design.…”

Section: Introductionmentioning

confidence: 99%

Characterization and kinetic study of Diels-Alder reaction: Detailed study on N-phenylmaleimide and furan based benzoxazine with potential self-healing application

Štirn¹,

Ručigaj²,

Krajnc³

2016

Express Polym. Lett.

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Abstract. The Diels-Alder reaction between N-phenylmaleimide and benzoxazine bearing furan group was investigated for the purpose of successful appliance of self-healing in benzoxazine polymer networks. The reaction as a function of temperature/time was performed in molten state and in a solution, where also the kinetic study was performed. The Diels-Alder reaction leads to a mixture of two diastereomers: endo presented at lower cyclo-reversion temperature and exo at higher. Therefore, the conversion rates and exo/endo ratio were studied in detail for both systems. For instance, in molten state the Diels-Alder reaction was triggered by the temperature of the melting point at 60°C with exo/endo ratio preferable to the endo adduct. The study of the kinetics in a solution revealed that the Diels-Alder reaction followed typical bimolecular reversible second-order reaction. The activation energies were close to the previous literature data; 48.4 and 51.9 kJ·mol -1 for Diels-Alder reaction, and 91.0 and 102.3 kJ·mol -1 for retro-Diels-Alder reaction, in acetonitrile and chloroform, respectively. The reaction equilibrium in a solution is much more affected by the retro-Diels-Alder reaction than in a molten state. This study shows detailed investigation of DA reaction and provides beneficial knowledge for further use in self-healing polymer networks.

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“…Comparing the two series of networks, Ursache et al -eXPRESS Polymer Letters Vol.11, No.6 (2017) there can be noticed that the use of TF-2 instead of TF-1 in the synthesis of networks leads to a higher rDA temperature of networks which varies in the range of 138.90 and 141.64°C. The obtained values of the T rDA for the crosslinked networks were higher than the ones of similar networks from other studies [38,39]. The thermally reversible character of the compounds can be evidenced with DSC by applying multiple heating-cooling cycles to the sample.…”

Section: Dscmentioning

confidence: 60%

Polyurethanes based on thermoreversible networks designed by Diels-Alder reaction

Ursache¹,

Găină²,

Gaina³

2017

Express Polym. Lett.

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Polyurethanes appeared as a Bayer's response to the successful development of high molecular weight polyamides by E.I. Dupont, given the competition between the two companies. The need for PUs steadily increased ever since then, because of its high abrasion, chemical resistance, flexibility, and good mechanical property [1]. Nowadays they are considered one of the most versatile polymeric materials class since they can be used in many forms and in a large number of applications including elastomers [2][3][4][5], flexible and rigid foams [6][7][8], biomedical applications [9][10][11], adhesives and coatings [12][13][14], polymers for electronics [15], etc. The reaction between diisocyanates or multiisocyanates and di-or polyols generates polyurethanes with different molecular structures varying from linear to crosslinked ones depending on the structure, functionality and stoichiometry of the reactants. These thermosetting polymers cannot be reprocessed or reused if, according to the desired applications, chemical crosslinkers are used [16]. For de-crosslinking of polyurethane networks, dynamic covalent chemistry is used, especially by means of the DA and retro-DA (rDA) reactions [17]. Due to its reversibility the DA reaction also represents a choice to create self-healing properties for polymer networks [18]. Concerning polyurethane, the DA reaction was employed in thermally remendable linear polymers [19][20][21][22] and thermally reversible networks [23][24][25][26][27]. The latter were designed in three different ways: i) by polymerization reaction of monomers containing maleimide-furan cycloadduct [26,28], ii) by crosslinking of linear polyurethane containing furan or maleimide pendant groups [27,29,30] and iii) by cycloaddition DA reaction between polyurethane containing furan end groups and multimaleimide monomers [19,[23][24][25][31][32][33]. Abstract. Urethane bismaleimides (BMIs) were used in order to obtain crosslinked structures by their reaction with an aromatic trifuran compound. The Diels-Alder (DA) reaction between the maleimide and furan moieties was investigated using proton nuclear magnetic resonance ( 1 H-NMR) spectroscopy for a model compound (CTF), due to the fact that the networks are insoluble in usual NMR solvents. The structure of the networks was confirmed by infrared spectroscopy. Thermal properties were investigated (by means of differential scanning calorimetry (DSC) and thermogravimetrical analyses (TGA)) and compared with the ones of similar compounds, previously obtained from the same BMIs and a different trifuran compound (which contains tertiary nitrogen in its structure). Mechanical and rheological properties were also investigated. The influence of the nature of the polyol from the BMIs structure and/or the influence of using a trifurylic compound with or without tertiary nitrogen on the properties of the crosslinked networks were also discussed.

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Diels–Alder‐based crosslinked self‐healing polyurethane/urea from polymeric methylene diphenyl diisocyanate

Cited by 76 publications

References 44 publications

Tuning the self-healing behavior of one-component intrinsic polymers

Tuning the self-healing behavior of one-component intrinsic polymers

Characterization and kinetic study of Diels-Alder reaction: Detailed study on N-phenylmaleimide and furan based benzoxazine with potential self-healing application

Polyurethanes based on thermoreversible networks designed by Diels-Alder reaction

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