A self-healing PDMS elastomer based on acylhydrazone groups and the role of hydrogen bonds

Zhang, Dongdong; Ruan, Yingbo; Zhang, Baoqing; Qiao, Xuguang; Deng, Guohua; Chen, Yongming; Liu, Chenyang

doi:10.1016/j.polymer.2017.05.060

Cited by 104 publications

(51 citation statements)

References 39 publications

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“…It can be observed that N-H peaks were shifted from 3349 to 3353 cm −1 , alkene C-H bonds were shifted from 3067 to 3070 cm −1 , and alkane C-H bonds were shifted from 2936 to 2938 cm −1 . These represent a type of blue shift which was related to the dissociation of the hydrogen bonds [38]. These results clearly proved that, with an increase in temperature, H-bonds in this composite became weaker.…”

Section: Self-healing Property and Mechanism Of Lpsesupporting

confidence: 65%

Synthesis and Characterization of Linear Polyisoprene Supramolecular Elastomers Based on Quadruple Hydrogen Bonding

2020

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Supramolecular elastomers based on quaternary hydrogen bonding of ureido-pyrimidinone (UPy) groups own special properties such as reversibility, self-healing, and good processability, which can be used in many special fields. In this paper, a novel type of linear polyisoprene supramolecular elastomer (LPSE) was prepared via anionic polymerization by deliberately introducing hydroxyl, isocyanate, and UPy groups into the ends. The formation of supramolecular structure showed significant effects on the microphase structures of LPSE, which was characterized by Fourier-transform infrared spectroscopy (FTIR), gel permeation chromatography (GPC), hydrogen nuclear magnetic resonance (1H-NMR), and dynamic mechanical analysis (DMA). Results showed that the introduction of UPy groups played a certain role in the improvement of the thermal stability, toughness, and tensile strength of the elastomer. Moreover, from self-healing tests, the hydrogen bonds of UPy showed dynamic characteristics which were different from covalent sacrificial bonds and exhibited the reassociation phenomenon. This study can not only extend our understanding of the toughening effect of strong hydrogen bonds, but also help us to rationally design new and tough elastomers.

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Section: Self-healing Property and Mechanism Of Lpsesupporting

confidence: 65%

Synthesis and Characterization of Linear Polyisoprene Supramolecular Elastomers Based on Quadruple Hydrogen Bonding

2020

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“…Multiple groups have studied self‐healing materials based on acylhydrazone and oxime bonds . Deng et al.…”

Section: Imine Chemistrymentioning

confidence: 99%

Dynamic Covalent Bonds in Polymeric Materials

2019

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Dynamic covalent bonds (DCBs) have received significant attention over the past decade. These are covalent bonds that are capable of exchanging or switching between several molecules. Particular focus has recently been on utilizing these DCBs in polymeric materials. Introduction of DCBs into a polymer material provides it with powerful properties including self‐healing, shape‐memory properties, increased toughness, and ability to relax stresses as well as to change from one macromolecular architecture to another. This Minireview summarizes commonly used powerful DCBs formed by simple, often “click” reactions, and highlights the powerful materials that can result. Challenges and potential future developments are also discussed.

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“…Moreover, acylhydrazine (−CONHNH 2 ) could be classified as an amino-containing group and attracted our attention because of the existence of active eNH 2 . They were readily prepared from organic acid methyl esters by hydrazinolysis (Khattab et al, 2017;Zhang et al, 2017), so methyl propiolate was selected as terminal alkyne to synthesize acylhydrazinefunctionalized chitosan derivatives. In addition, propargyl alcohol was also used to prepare hydroxyl-modified chitosan derivatives as antioxidant control group.…”

Section: -Deoxy-n-phthaloyl Chitosan Derivatives (6a-6c and 8a-8c)mentioning

confidence: 99%

Synthesis and antioxidant action of chitosan derivatives with amino-containing groups via azide-alkyne click reaction and N-methylation

Tan

Zhang

Zhao

et al. 2018

Carbohydrate Polymers

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Amino functionality has been paid growing attention in chemical modification of polysaccharides due to their potential biomedical applications. Here, the preparation of novel antioxidant materials based on chitosan derivatives bearing amino-containing groups equipped with 1,2,3-triazole and 1,2,3-triazolium by Cuprous-catalyzed azide-alkyne cycloaddition and N-methylation was described for the first time. The structural characteristics of the synthesized derivatives were examined by FTIR, H NMR, and elemental analysis. The antioxidant activities of the chitosan derivatives were assessed in vitro. The results indicated that chitosan derivatives bearing 1,2,3-triazoles displayed superior antioxidant activity over pristine chitosan, especially against superoxide anion radical. Moreover, antioxidant efficiency of chitosan derivatives further enhanced after N-methylation of 1,2,3-triazole moieties with iodomethane, which is comparative to that of ascorbic acid. Notably, of all chitosan derivatives bearing 1,2,3-triazole or 1,2,3-triazolium moieties, acylhydrazine-functionalized and amino-functionalized chitosan showed the stronger antioxidant capacity than hydroxyl-modified chitosan at the test concentration. Besides, the cytotoxicities of them were also evaluated in vitro on HaCaT cells. These results suggested that amino and acylhydrazine-functionalized chitosan derivatives with 1,2,3-triazolium could be used as novel antioxidant biomaterials.

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A self-healing PDMS elastomer based on acylhydrazone groups and the role of hydrogen bonds

Cited by 104 publications

References 39 publications

Synthesis and Characterization of Linear Polyisoprene Supramolecular Elastomers Based on Quadruple Hydrogen Bonding

Synthesis and Characterization of Linear Polyisoprene Supramolecular Elastomers Based on Quadruple Hydrogen Bonding

Dynamic Covalent Bonds in Polymeric Materials

Synthesis and antioxidant action of chitosan derivatives with amino-containing groups via azide-alkyne click reaction and N-methylation

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