Enhanced properties of well-defined polymer networks prepared by a sequential thiol-Michael - radical thiol-ene (STMRT) strategy

Cespedes, Sergio; Hand, Rachel A.; Chmel, Nikola Paul; Moad, Graeme; Keddie, Daniel J.; Schiller, Tara L.

doi:10.1016/j.eurpolymj.2021.110440

Cited by 6 publications

(4 citation statements)

References 29 publications

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“…PDMS: δ 0.57 (d, 2H, −NH 2 ), 1.80 (d, 2H, −CH 2 −), 1.49 (d, 2H, −CH 2 −), 2.69 (d, 2H, −CH 2 −), 0.12 (d, 3H, −CH 3 ) and DAP: δ 5.90 (d, 2H, −NH 2 ), 4.19 (t, 1H, −CH). The chemical shift at 7.28 ppm was due to the deuterated solvent, CDCl 3 . − In the 1 H NMR spectra of the HPDPU samples, chemical shifts appeared at 0.12, 1.49, 1.80, 2.69, and 4.19 ppm, which are attributed to PDMS and DAP, indicating that these two substances have been successfully grafted into HPDPU. In addition, no chemical shift was observed at 0.57 and 5.90 ppm, which indicates that the −NH 2 groups of PDMS and DAP were consumed, further confirming the successful synthesis of HPDPU.…”

Section: Resultsmentioning

confidence: 94%

Low-Temperature Self-Healing Supramolecular Zinc-Poly(Urea–Urethane) Elastomer

Zhang,

Xiong,

et al. 2024

ACS Appl. Polym. Mater.

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In the exploration of extreme environments such as polar and outer space, the elastomers used in flexible structures on equipment/facilities tend to harden and brittle, losing deformability and even break. This will cause huge maintenance costs and serious safety risks. To solve this problem, we designed a rapidly, cryogenically self-repairing supramolecular zinc-poly(urea–urethane) elastomer with excellent mechanical properties. The elastomer exhibits excellent flexibility and bends over 90° easily after a period of time in liquid nitrogen (−196 °C). At −90 °C, the elastomer exhibits good ductility and can realize self-repair. In the cantilever mode, the loaded end can produce a displacement of ∼9000 μm under 18 N, which is considerably larger than those of hydroxyl-terminated polybutadiene and polydimethylsiloxane (approximately 95 and 75 μm, respectively). In addition, at −40 °C, the elastomer possesses a high elongation at break of ∼1819.1%, the fastest self-repairing ability among the reported elastomers of similar strength. This supramolecular zinc-poly(urea–urethane) elastomer has a broad application prospect at extremely low temperatures.

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Section: Resultsmentioning

confidence: 94%

Low-Temperature Self-Healing Supramolecular Zinc-Poly(Urea–Urethane) Elastomer

Zhang,

Xiong,

et al. 2024

ACS Appl. Polym. Mater.

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“…The catechol conjugation is achieved through the addition of one of the thiol groups to the corresponding oxidized o -quinone, inspired by the alleged role of free thiol groups of cysteine residues in mussel foot proteins [ 43 , 44 , 45 , 46 ]. A second thiol group allows for the simultaneous incorporation of an alkyl chain bearing a terminal vinyl or acrylate group using a thiol-ene click reaction [ 47 , 48 , 49 ]. And finally, the last two available thiols polymerize through the formation of disulfide bridges, in very mild and selective conditions, without protecting the catechol moieties, using iodine [ 50 ].…”

Section: Introductionmentioning

confidence: 99%

Mussel-Inspired Lego Approach for Controlling the Wettability of Surfaces with Colorless Coatings

et al. 2022

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The control of surface wettability with polyphenol coatings has been at the forefront of materials research since the late 1990s, when robust underwater adhesion was linked to the presence of L-DOPA—a catecholic amino acid—in unusually high amounts, in the sequences of several mussel foot proteins. Since then, several successful approaches have been reported, although a common undesired feature of most of them is the presence of a remnant color and/or the intrinsic difficulty in fine-tuning and controlling the hydrophobic character. We report here a new family of functional catechol-based coatings, grounded in the oxidative condensation of readily available pyrocatechol and thiol-capped functional moieties. The presence of at least two additional thiol groups in their structure allows for polymerization through the formation of disulfide bonds. The synthetic flexibility, together with its modular character, allowed us to: (I) develop coatings with applications exemplified by textiles for oil-spill water treatment; (II) develop multifunctional coatings, and (III) fine-tune the WCA for flat and textile surfaces. All of this was achieved with the application of colorless coatings.

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“…The Michael reaction is a versatile synthesis type for linking electron-poor olefins to a wide range of nucleophiles [ 18 ]. Enolates [ 19 , 20 ], nitrogen-containing [ 21 , 22 , 23 , 24 , 25 , 26 ] reagents, and thiols [ 26 , 27 , 28 , 29 , 30 , 31 , 32 ] are typical Michael donors, while alkyl acrylates are mainly used as Michael acceptors [ 33 ]. Adding an enolate anion to the α,β-unsaturated carbonyl compound to form a carbon–carbon bond is a Michael reaction [ 19 , 20 , 34 ].…”

Section: Introductionmentioning

confidence: 99%

“…A type of polymerization for the addition of hydroxyl monomers with electrophilic double or triple bonds is called the oxa-Michael reaction [ 35 , 36 ]. In the case of nitrogen and sulphur-containing donors, the reaction is called aza-Michael [ 21 , 22 , 23 , 24 , 25 , 26 , 37 ] and thio-Michael [ 26 , 27 , 28 , 29 , 30 , 31 , 32 ] addition reactions, respectively. In recent years, aza- and thio-Michael reactions have gained attention for polymerization [ 35 , 38 ].…”

Section: Introductionmentioning

confidence: 99%

Bio-Based Polymer Developments from Tall Oil Fatty Acids by Exploiting Michael Addition

et al. 2022

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In this study, previously developed acetoacetates of two tall-oil-based and two commercial polyols were used to obtain polymers by the Michael reaction. The development of polymer formulations with varying cross-link density was enabled by different bio-based monomers in combination with different acrylates—bisphenol A ethoxylate diacrylate, trimethylolpropane triacrylate, and pentaerythritol tetraacrylate. New polymer materials are based on the same polyols that are suitable for polyurethanes. The new polymers have qualities comparable to polyurethanes and are obtained without the drawbacks that come with polyurethane extractions, such as the use of hazardous isocyanates or reactions under harsh conditions in the case of non-isocyanate polyurethanes. Dynamic mechanical analysis, differential scanning calorimetry, thermal gravimetric analysis, and universal strength testing equipment were used to investigate the physical and thermal characteristics of the created polymers. Polymers with a wide range of thermal and mechanical properties were obtained (glass transition temperature from 21 to 63 °C; tensile modulus (Young’s) from 8 MPa to 2710 MPa and tensile strength from 4 to 52 MPa). The synthesized polymers are thermally stable up to 300 °C. The suggested method may be used to make two-component polymer foams, coatings, resins, and composite matrices.

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Enhanced properties of well-defined polymer networks prepared by a sequential thiol-Michael - radical thiol-ene (STMRT) strategy

Cited by 6 publications

References 29 publications

Low-Temperature Self-Healing Supramolecular Zinc-Poly(Urea–Urethane) Elastomer

Low-Temperature Self-Healing Supramolecular Zinc-Poly(Urea–Urethane) Elastomer

Mussel-Inspired Lego Approach for Controlling the Wettability of Surfaces with Colorless Coatings

Bio-Based Polymer Developments from Tall Oil Fatty Acids by Exploiting Michael Addition

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