Shape recovery and reprocessable polyurethanes crosslinked with double decker silsesquioxane via Diels-Alder reaction

Zhao, Bingjie; Mei, Honggang; Hang, Guohua; Li, Lei; Zheng, Sixun

doi:10.1016/j.polymer.2021.124042

Cited by 17 publications

(19 citation statements)

References 53 publications

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“…Under this circumstance, the materials can not only possess the excellent thermomechanical properties but also displayed the reprocessing performance via the exchange of the dynamic chemical bonds. For instance, reversible (or dynamic) covalent bonds such as Diels-Alder, [4][5][6][7][8][9][10][11] exchanges of esterification, [12][13][14][15][16][17] boronic ester bonds [18][19][20][21][22] and hindered urea bonds [23][24][25][26] have been introduced into PU thermosets to impart self-healing (or preprocessing) properties to the materials. Disulfide bonds are a type of important dynamic covalent bonds, which can undergo intense exchanges under mild conditions.…”

Section: Introductionmentioning

confidence: 99%

Poly(hydroxyurethane‐co‐thiourethane)s cross‐linked with disulfide bonds: Synthesis via isocyanate‐free approach, thermomechanical and reprocessing properties

Liu

Mei

et al. 2022

Journal of Polymer Science

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Both difunctional five-membered cyclic carbonate (E5CC) and trithiocarbonate (E5CTC) were synthesized via the reactions of diglycidyl ether of bisphenol A (DGEBA) with carbon dioxide (CO 2 ) and carbon disulfide (CS 2 ), respectively. These two monomers were employed to synthesize linear poly(hydroxyurethaneco-mecaptotrithiourethane) [P(HU-co-MTU)] copolymers via the polymerization with an α,ω-diamino-terminated poly(propylene oxide). By controlling the mole ratios of E5CC to E5CTC, the P(HU-co-MTU) copolymers were synthesized with variable contents of thiol groups. It was found that the linear P(HU-co-MTU) copolymers were readily cross-linked with the disulfide bonds which were in situ generated via the radical coupling of the side thiol groups. The cross-linking exerted a profound impact on the thermomechanical properties of the materials. The glass transition temperature (T g 's), Young's moduli and tensile strengths were significantly enhanced with increasing the contents of disulfide bonds. More importantly, the networks significantly displayed the self-healing and reprocessing properties, which are attributable to the dynamic exchanges of disulfide bonds.

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Section: Introductionmentioning

confidence: 99%

Poly(hydroxyurethane‐co‐thiourethane)s cross‐linked with disulfide bonds: Synthesis via isocyanate‐free approach, thermomechanical and reprocessing properties

Liu

Mei

et al. 2022

Journal of Polymer Science

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“…NH 2 -PPO-NH 2 and/or 3,13-dianilino DDSQ] with carbon dioxide (CO 2 ) (see Scheme 1). 3,13-Dianilino DDSQ was synthesized via the Heck reaction of 3,13-divinyl DDSQ with 4-bromoaniline; 3,13-divinyl DDSQ was obtained via the silyl ether reaction of Na 4 O 14 Si 8 (C 6 H 5 ) 8 with vinylmethyldichlorosilane 44 (see Scheme S1). The successful synthesis of 3,13-dianilino DDSQ was demonstrated by means of 1 H NMR spectroscopy (see Figure S1).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…α,ω-Diamino-terminated poly(propylene oxide) (denoted NH 2 -PPO-NH 2 ) was supplied by Huntsman Co., Shanghai, China, under the trade name of Jeffamine D-2000; it had a quoted molecular weight of M n = 2000 Da. 3,13-Dianilino double decker silsesquioxane (3,13-dianilino DDSQ) was synthesized following the method reported previously, 44 as detailed in the Supporting Information. Carbon dioxide (CO 2 ) was supplied by Shanghai Gas Co., China.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…Polyhedral oligomeric silsesquioxanes are a class of important building blocks of organic–inorganic hybrids. − The introduction of POSS into organic polymers can significantly improve the thermomechanical properties and even endow the materials with some functional properties. − In past years, there have been some reports on the synthesis of PUreas via the diamine–CO 2 approach. However, there has been no report on the synthesis of organic–inorganic PUreas via this approach.…”

Section: Introductionmentioning

confidence: 99%

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Organic–Inorganic Polyureas with POSS Cages in the Main Chains via Polycondensation of Diamines with Carbon Dioxide

Zhao

Mei

Wang

et al. 2021

ACS Appl. Polym. Mater.

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Linear organic–inorganic polyureas (PUreas) with polyhedral oligomeric silsesquioxane (POSS) cages in the main chains were synthesized via polycondensation of diamines with carbon dioxide (CO2). First, 3,13-dianilino double decker silsesquioxane (denoted 3,13-dianilino DDSQ) was synthesized. An α,ω-diamino-terminated poly(propylene oxide) as well as the POSS diamine was exploited for polycondensation with CO2; PUrea and PUrea-DDSQ with sufficiently high molecular weights were obtained with various contents of POSS. The morphological investigation shows that the linear PUreas with POSS cages in the main chains were microphase-separated; the POSS cages were aggregated into spherical microdomains with the size of 50–120 nm in diameter. Owing to the introduction of POSS cages, PUrea was transformed from a viscous liquid into elastic solids in the ranges of composition investigated. At room temperature, linear organic–inorganic PUreas behaved as cross-linked elastomers. This behavior is ascribed to the generation of physical cross-linking with POSS microdomains as the cross-linking sites. In addition, the organic–inorganic PUreas displayed self-healing properties via the dynamic exchange of multiple hydrogen bonds. It was found that the self-healing properties were significantly affected by the content of 3,13-dianilino DDSQ.

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“…The as-obtained Na 4 O 14 Si 8 (C 6 H 5 ) 8 was functionalized with the silylation reaction with dichlorosilane bearing a functional group, forming a class of so-called double-decker silsesquioxane (DDSQ) macromers. In the past few years, many difunctional DDSQ macromers carrying a variety of functional groups have been reported. − More recently, Lee and Maleczka et al reported the synthesis of DDSQ macromers with an asymmetrically difunctionalized DDSQ macromer via selective protection with a boronic acid and then an isolation approach. To the best of our knowledge, nonetheless, the R groups ( viz.…”

Section: Introductionmentioning

confidence: 99%

Organic–Inorganic Polyimides with POSS Cages in the Main Chains: An Impact of POSS R Groups on Morphologies and Properties

Wang,

Hang,

et al. 2023

ACS Appl. Polym. Mater.

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Two well-defined POSS diamines were synthesized with phenyl (Ph) and iso-butyl (i-Bu) POSS trisilanols as the starting compounds. This approach involves the protection and deprotection of silanol hydroxyl groups with phenylboronic acid and pinacol, followed by the silylation of silanol hydroxyl groups with mono- and dichlorosilanes. With this route of synthesis, two well-defined divinyl POSS macromers were obtained, as evidenced by 1H, 29Si NMR, and mass spectroscopy. These two divinyl POSS macromers were further functionalized into well-defined POSS diamines via the Heck reaction with p-bromoaniline. The successful synthesis of POSS diamines enabled the synthesis of organic–inorganic polyimides with the POSS cages in the main chains. More importantly, the syntheses of these two POSS diamines allowed the examination of the effect of POSS R groups (i.e., Ph and i-Bu) on the morphologies and thermomechanical and dielectric properties of organic–inorganic polyimides. Notably, the types of POSS R groups exerted a profound impact on the morphologies and properties of the organic–inorganic polyimides.

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Shape recovery and reprocessable polyurethanes crosslinked with double decker silsesquioxane via Diels-Alder reaction

Cited by 17 publications

References 53 publications

Poly(hydroxyurethane‐co‐thiourethane)s cross‐linked with disulfide bonds: Synthesis via isocyanate‐free approach, thermomechanical and reprocessing properties

Poly(hydroxyurethane‐co‐thiourethane)s cross‐linked with disulfide bonds: Synthesis via isocyanate‐free approach, thermomechanical and reprocessing properties

Organic–Inorganic Polyureas with POSS Cages in the Main Chains via Polycondensation of Diamines with Carbon Dioxide

Organic–Inorganic Polyimides with POSS Cages in the Main Chains: An Impact of POSS R Groups on Morphologies and Properties

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