Self‐healing polyurethane based on a difuranic monomer from biorenewable source

Platonova, E. O.; Vlasov, Evgeny; Павлов, А. А.; Kireynov, A. V.; Nelyub, V. A.; Polezhaev, Alexander V.

doi:10.1002/app.47869

Cited by 20 publications

(28 citation statements)

References 33 publications

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“…For example, if we consider the formation a two-substituted product with n = 6, it could be formed from the reaction of one-substituted derivative with n = 3 and a PTHF chain with n = 3, and the reaction of one-substituted derivative with n = 2 and a PTHF chain with n = 4, and the reaction of one-substituted derivative with n = 4 and a PTHF chain with n = 2. Thus, the fits of Equation (4) and Equations (7) and (8) to the experimental data are good as demonstrated in Figure 7b. The values of k 1,app and k 2,app were found to be (1.13±0.01)•10 -2 and (1.25±0.02)•10 -2 min -1 , respectively, which are in line with those obtained by fitting to the summed product distributions.…”

Section: The Reaction Between 13-xdi and Polytetrahyrofuran (Pthf)mentioning

confidence: 55%

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Uncatalyzed urethane forming reaction of 1,3-xylylene diisocyanate with aliphatic alcohols of varying chain lengths and polyols

Nagy¹,

Juhász²,

Zsuga³

2020

Express Polym. Lett.

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In this article, we report a detailed study on the kinetics of the reaction of 1,3-xylylene diisocyanate (1,3-XDI) with alcohols of varying alkyl chain lengths and with low molecular weight polyols such as monomethoxylated polyethylene glycol (mPEG) and polytetrahydrofuran (PTHF) in toluene, in the absence of a catalyst. It was found that the pseudo-firstorder rate coefficient increased with the increasing alkyl chain length (k 1,app was found to be 0.0166 and 0.0341 min-1 for 1-propanol and 1-hexanol, respectively) and the reactivities of the 1,3-xylyene diisocyanate towards the alcohols and polyols are between those of the aromatic and alkyl isocyanates. The activation energies were also determined and were found to vary from 25.6 to 38.6 kJ/mol (from 1-propanol to 1-hexanol). According to further kinetic studies, the rate coefficients k 1,app and k 2,app for the reaction of 1,3-XDI with PTHF were determined to be (1.13±0.01)•10-2 and (1.28±0.01)•10-2 min-1 , respectively. It was also found that the rate constants did not depend significantly on the length of the polymer chain. However, significantly lower rate coefficients were obtained for the 1,3-XDI-mPEG reaction (k 1,app = (2.64±0.03)•10-3 min-1 and k 2,app = (2.45±0.03)•10-3 min-1). Besides, the dependence of the pseudo-first-order rate coefficient on the concentration of the alcohols was also studied, and based on these findings a reaction mechanism is proposed.

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Section: The Reaction Between 13-xdi and Polytetrahyrofuran (Pthf)mentioning

confidence: 55%

“…PUs can also be used as functional substances such as high-performance 'smart' materials e.g. with shape-memory [5,6] and/or self-healing properties [7]. The manufacturing of PUs is based on a simple nucleophilic addition reaction taking place between diisocyanates and polyether-or polyester-based polyols [8,9].…”

Section: Introductionmentioning

confidence: 99%

Uncatalyzed urethane forming reaction of 1,3-xylylene diisocyanate with aliphatic alcohols of varying chain lengths and polyols

Nagy¹,

Juhász²,

Zsuga³

2020

Express Polym. Lett.

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“…Difurfurylamine was prepared by a modified literature procedure [31] (Scheme 1). Hydrofuramide (50 g, 0.19 mol) was gradually added to the ice-cold suspension of sodium borohydride (excess) in methanol.…”

Section: Synthesis Of Difurfurylaminementioning

confidence: 99%

“…It is also essential for sustainability to increase the number of carbon atoms derived from renewable sources. Furans, maleimides [31], and polyols [11,[32][33][34] are bioderived and therefore are ideal candidates for this purpose. Our previous work [31] presented linear thermally remendable PUs extended via reversible DAreaction that demonstrated excellent self-healing ability.…”

Section: Introductionmentioning

confidence: 99%

“…Furans, maleimides [31], and polyols [11,[32][33][34] are bioderived and therefore are ideal candidates for this purpose. Our previous work [31] presented linear thermally remendable PUs extended via reversible DAreaction that demonstrated excellent self-healing ability. Several reports showed [35][36][37] that branched PUs have enhanced mechanics and self-healing properties than their linear counterparts.…”

Section: Introductionmentioning

confidence: 99%

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Thermally Remendable Polyurethane Network Cross-Linked via Reversible Diels–Alder Reaction

et al. 2021

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We prepared a series of thermally remendable and recyclable polyurethanes crosslinked via reversible furan-maleimide Diels–Alder reaction based on TDI end-caped branched Voranol 3138 terminated with difurfurylamine and 4,4′-bis(maleimido)diphenylmethane (BMI). We showed that Young modulus strongly depends on BMI content (from 8 to 250 MPa) that allows us to obtain materials of different elasticity as simple as varying BMI content. The ability of DA and retro-DA reactions between furan and maleimide to reversibly bind material components was investigated by NMR spectroscopy, differential scanning calorimetry, and recycle testing. All polymers obtained demonstrated high strengths and could be recovering without significant loss in mechanical properties for at least five reprocessing cycles.

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Polybutadiene derived allophanate as the crosslinker for Diels–Alder type self‐healing polyurethane networks

Liu

Zhang

Yang

et al. 2022

J of Applied Polymer Sci

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Intrinsic self‐healing materials have drawn great interest in recent years. The design of novel building blocks is essential for developing polymer networks with different properties. Allophanate is usually regarded as a side product during the preparation of polyurethanes. During the research of self‐healing polyurethane networks, we have studied the terminal functionalization of hydroxyl‐terminated polybutadiene with furfuryl isocyanate and occasionally obtained the furan‐terminated polybutadiene allophanate. The tetra‐branched molecule is employed as the crosslinker in the construction of a series of Diels–Alder type polyurethane networks. These polyurethane networks exhibit good mechanical performance and excellent self‐healing ability. Damages can be healed via the thermo‐promoted dissociation and recombination cycle, giving good to excellent recovery of tensile strength within three cycles of “damage‐repair” processes.

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Self‐healing polyurethane based on a difuranic monomer from biorenewable source

Cited by 20 publications

References 33 publications

Uncatalyzed urethane forming reaction of 1,3-xylylene diisocyanate with aliphatic alcohols of varying chain lengths and polyols

Uncatalyzed urethane forming reaction of 1,3-xylylene diisocyanate with aliphatic alcohols of varying chain lengths and polyols

Thermally Remendable Polyurethane Network Cross-Linked via Reversible Diels–Alder Reaction

Polybutadiene derived allophanate as the crosslinker for Diels–Alder type self‐healing polyurethane networks

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