Polysiloxane‐Based Autonomic Self‐Healing Elastomers Obtained Through Dynamic Boronic Ester Bonds Prepared by Thiol‐Ene “Click” Chemistry

Zuo, Yujing; Gou, Zhiming; Zhang, Changqiao; Feng, Shengyu

doi:10.1002/marc.201600303

Cited by 5 publications

(7 citation statements)

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“…Recently, the thiol–ene click reaction has attracted much attention due to its high reaction rates, high conversion, oxygen resistance, and fine control of structures. − All of these features make it an excellent candidate for 3D printing technology. Here, as shown in Figure , the thiol–ene click reaction was used to synthesize silicone elastomer with thiol groups from MPS and double bonds from VPS.…”

Section: Resultsmentioning

confidence: 99%

Superstretchable and Processable Silicone Elastomers by Digital Light Processing 3D Printing

Zhao

et al. 2019

ACS Appl. Mater. Interfaces

106

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A series of photosensitive resins suitable for the production of silicone elastomers through digital light processing 3D printing are reported. Based on thiol− ene click reaction between a branched mercaptan-functionalized polysiloxane and different-molecular-weight vinyl-terminated poly(dimethylsiloxane), silicone elastomers with tunable hardness and mechanical properties are obtained. Printed elastomeric objects show high printing resolution and excellent mechanical properties. The break elongation of the silicone elastomers can get up to 1400%, which is much higher than the reported UV-cured elastomers and is even higher than the most stretchable thermocuring silicone elastomers. The superstretchable silicone elastomers are then applied to fabricate stretchable electronics with carbon nanotubes-doped hydrogel. The printable and processable silicone elastomers have great potential applications in various fields, including soft robotics, flexible actuators, and medical implants.

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Section: Resultsmentioning

confidence: 99%

Superstretchable and Processable Silicone Elastomers by Digital Light Processing 3D Printing

Zhao

et al. 2019

ACS Appl. Mater. Interfaces

106

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“…Figure 3 presents the SHSMs based on covalent interactions such as reversible Diels–Alder interactions [ 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 ], disulfide [ 47 , 48 , 49 ], boronic ester [ 50 ], boroxine [ 51 , 52 ], imine [ 53 , 54 , 55 , 56 , 57 ], hydrazine-based [ 58 ], thiourethane [ 59 ], hindered urea bonds [ 60 ], and metal–ligand interactions [ 19 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 , 73 , 74 , 75 , 76 , 77 , 78 , 79 , 80 ]. Some examples of covalent SHSMs are shown in Table 1 .…”

Section: Self-healing Silicone Materials: Looking Backmentioning

confidence: 99%

“…The boronic ester bonds are also used to create non-autonomous SHSMs, which heal via reversible hydrolysis and esterification in the presence of water. Thus, Zuo Y. et al [ 50 ] introduced boric acid and glycol fragments into PDMS by hydrothiolation, developing SH silicone rubbers with dynamic boron-based cross-links ( Figure 3 ). It was reported [ 50 ] that such materials achieved a η of up to 70% after 30 min under the influence of air moisture.…”

Section: Self-healing Silicone Materials: Looking Backmentioning

confidence: 99%

“…Thus, Zuo Y. et al [ 50 ] introduced boric acid and glycol fragments into PDMS by hydrothiolation, developing SH silicone rubbers with dynamic boron-based cross-links ( Figure 3 ). It was reported [ 50 ] that such materials achieved a η of up to 70% after 30 min under the influence of air moisture. For example, if a small amount of water is added to such SHSMs, the time of SH can be <10 min [ 12 ].…”

Section: Self-healing Silicone Materials: Looking Backmentioning

confidence: 99%

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Self-Healing Silicone Materials: Looking Back and Moving Forward

Deriabin,

Filippova,

Islamova

2023

Biomimetics

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This review is dedicated to self-healing silicone materials, which can partially or entirely restore their original characteristics after mechanical or electrical damage is caused to them, such as formed (micro)cracks, scratches, and cuts. The concept of self-healing materials originated from biomaterials (living tissues) capable of self-healing and regeneration of their functions (plants, human skin and bones, etc.). Silicones are ones of the most promising polymer matrixes to create self-healing materials. Self-healing silicones allow an increase of the service life and durability of materials and devices based on them. In this review, we provide a critical analysis of the current existing types of self-healing silicone materials and their functional properties, which can be used in biomedicine, optoelectronics, nanotechnology, additive manufacturing, soft robotics, skin-inspired electronics, protection of surfaces, etc.

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“…The thiol-ene reaction has been increasingly used in the last years for functionalizing polysiloxanes. [25 -31] It has been used notably for preparing hydrophilic or amphiphilic polysiloxanes, [32][33][34][35][36] surface functionalized PDMS elastomers, [37,38] antibacterial silicones, [39] elastomers for modulating cell adhesion, [40] self-healing polysiloxanes, [41] polysiloxane elastomers with optical properties, [42,43] liquid crystal polysiloxanes, [44] electroactive ferrocene-grafted polysiloxanes, [45,46] polysilox-anes with tunable dielectric properties, [47] or contact lens elastomers. [48] Thiol-ene strategy is also used in the case of polysiloxanes for getting an efficient, orthogonal cross-linking, [18,49 -51] often initiated photochemically and consequently, has been adapted to electrospinning [52] and 3D printing.…”

Section: Introductionmentioning

confidence: 99%

Polysiloxanes Modified by Thiol‐Ene Reaction and Their Interaction with Gold Nanoparticles

Lemonier

Marty

Fitremann

2019

Helvetica Chimica Acta

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A poly(vinylmethyl‐co‐dimethyl)siloxane has been functionalized with phenylethanethiol, N‐methylmercaptoacetamide and heptadecafluoro‐1‐decanethiol by a thermal radical thiol‐ene reaction initiated by azobisisobutyronitrile. The resulting polymers were obtained in good yields with most of the time a complete conversion of the vinyl groups. The reaction also preserved the fragile polysiloxane backbone. The polymer, grafted with about 25 % of mercapto‐acetamide groups is soluble in polar solvents such as dimethylformamide and dimethyl sulfoxide, opening the way for further functionalization with polar molecules such as unprotected carbohydrates. Spherical and branched gold nanoparticles were coated with these polymers. This coating induced a surface resonance plasmon shift resulting from the interaction of the grafted polysiloxanes with the nanoparticle surface. The shift can be explained by the variation of the refractive index of the side groups but may be also related to the self‐organization of polysiloxanes and their interactions with the gold surface depending on their polarity.

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Polysiloxane‐Based Autonomic Self‐Healing Elastomers Obtained Through Dynamic Boronic Ester Bonds Prepared by Thiol‐Ene “Click” Chemistry

Cited by 5 publications

References 0 publications

Superstretchable and Processable Silicone Elastomers by Digital Light Processing 3D Printing

Superstretchable and Processable Silicone Elastomers by Digital Light Processing 3D Printing

Self-Healing Silicone Materials: Looking Back and Moving Forward

Polysiloxanes Modified by Thiol‐Ene Reaction and Their Interaction with Gold Nanoparticles

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