Using click chemistry to dial up the modulus of doubly crosslinked microgels through precise control of microgel building block functionalisation

Farley, Rebecca; Halacheva, Silvia; Bramhill, Jane; Saunders, Brian R.

doi:10.1039/c4py01753f

Cited by 6 publications

(4 citation statements)

References 36 publications

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“…[13][14][15][16] For example, the presence of large-size fractures greater than inches resulted in severe lost circulation and water early breakthrough since such technical challenges posed potential threats to field production. [17][18][19] However, large fractures treatments using traditional granular hydrogels proved to be fruitless due to weak interactions. [20][21][22] Severe lost circulation required granular hydrogels with excellent injectivity, mechanical robustness against destructive forces, and self-regenerative functions to seal the fractures.…”

Section: Introductionmentioning

confidence: 99%

High Temperature Self‐Regenerative Granular Hydrogels for Fracture Treatments During Subsurface Energy Recovery

Wang

Jiang

Long

et al. 2023

Macromol. Rapid Commun.

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The uses of granular hydrogels to assemble macroscopic bulk hydrogels display numerous distinct advantages. However, prior assembly of bulk hydrogels is accomplished by interparticle linking strategy, which compromised mechanical property and thermal stability under hostile conditions. To expand their applications as engineering soft materials, self‐regenerative granular hydrogels via a seamless integrating approach to regenerate bulk hydrogels is highly desirable. Herein, covalent regenerative granular hydrogels (CRHs) are prepared at low‐temperature synthetic conditions and re‐construct bulk seamless hydrogels at high‐temperature aqueous environments. The re‐formed bulk hydrogels display rubber‐like viscoelastic behaviors over a wide range of temperatures from 90 to 150 °C, where the covalent re‐crosslinking reactions homogeneously occurr along the periphery and in the matrix of granular hydrogels, accounting for the increased structural integrity at high temperatures. The bulk hydrogel shows increased elasticity and long‐term thermal integrity at 150 °C for more than six months in the confined fractures. Moreover, regenerative granular CRH‐based bulk hydrogels significantly improve mechanical robustness under destructive pressure. Thus, high temperature water induced regenerative granular hydrogels present the paradigm to treat engineering scenarios such as large fractures for hydraulic fracturing, drilling operation, and disproportionate permeability reduction under extremely hostile conditions during subsurface energy recovery.

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Section: Introductionmentioning

confidence: 99%

High Temperature Self‐Regenerative Granular Hydrogels for Fracture Treatments During Subsurface Energy Recovery

Wang

Jiang

Long

et al. 2023

Macromol. Rapid Commun.

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“…[22][23][24][25][26] The highly stable aromatic structure of triazole has the advantages of being tolerable to acidic, basic, and oxidative mediums, 27 mimicking amide groups and acting as hydrogen bond acceptors to improve mechanical strength. 28,29 Although some research toward improving mechanical properties 30,31 using click chemistry has been reported, application of CuAAC in the crosslinking of waterborne polymers has not been reported to date.…”

Section: Introductionmentioning

confidence: 99%

“…Click chemistry, especially copper-catalyzed 1,3-dipolar azide–alkyne cycloaddition (CuAAC), is insensitive to oxygen, water, solvents, and a wide range of functionalities and can be site-specifically performed at room temperature , with high reaction rates and quantitative yields . As one of the most effective chemical reactions, click chemistry has been widely used in the synthesis, modification, and engineering of polymers, to obtain linear or branched polymers, , to conjugate or link small molecules or macromolecules, − and to cross-link click-suitable polymers. − The highly stable aromatic structure of triazole has the advantages of being tolerable to acidic, basic, and oxidative mediums, mimicking amide groups, and acting as hydrogen bond acceptors to improve mechanical strength. , Although some research toward improving mechanical properties , using click chemistry has been reported, application of CuAAC in the cross-linking of waterborne polymers has not been reported to date.…”

Section: Introductionmentioning

confidence: 99%

Click Cross-Linking-Improved Waterborne Polymers for Environment-Friendly Coatings and Adhesives

Peng

Guo³

et al. 2016

ACS Appl. Mater. Interfaces

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Waterborne polymers, including waterborne polyurethanes (WPU), polyester dispersions (PED), and polyacrylate emulsions (PAE), are employed as environmentally friendly water-based coatings and adhesives. An efficient, fast, stable, and safe cross-linking strategy is always desirable to impart waterborne polymers with improved mechanical properties and water/solvent/thermal and abrasion resistance. For the first time, click chemistry was introduced into waterborne polymer systems as a cross-linking strategy. Click cross-linking rendered waterborne polymer films with significantly improved tensile strength, hardness, adhesion strength, and water/solvent resistance compared to traditional waterborne polymer films. For example, click cross-linked WPU (WPU-click) has dramatically improved the mechanical strength (tensile strength increased from 0.43 to 6.47 MPa, and Young's modulus increased from 3 to 40 MPa), hardness (increased from 59 to 73.1 MPa), and water resistance (water absorption percentage dropped from 200% to less than 20%); click cross-linked PED (PED-click) film also possessed more than 3 times higher tensile strength (∼28 MPa) than that of normal PED (∼8 MPa). The adhesion strength of click cross-linked PAE (PAE-click) to polypropylene (PP) was also improved (from 3 to 5.5 MPa). In addition, extra click groups can be preserved after click cross-linking for further functionalization of the waterborne polymeric coatings/adhesives. In this work, we have demonstrated that click modification could serve as a convenient and powerful approach to significantly improve the performance of a variety of traditional coatings and adhesives.

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“…[47][48][49][50][51] However, while being a valuable tool for many coupling reactions, this family of reactions has never been investigated so far in DX microgel formation, except to introduce vinyl functions onto microparticle surfaces as reported recently by Saunders et al In their strategy, copper catalyzed azide-alkyne cycloaddition (CuAAC) was investigated to precisely control the extent of vinyl functionalization of the microgel (MG) particles and therefore dial up the modulus of the resulting DX microgels. 52 Herein, we describe for the first time the use of a metalfree, click coupling reaction to interlink well-defined microparticles. In particular, we are taking advantage of the 1,2,4triazoline-3,5-dione (TAD) based click chemistry, as previously introduced by some of us.…”

Section: Introductionmentioning

confidence: 99%

Click reactive microgels as a strategy towards chemically injectable hydrogels

et al. 2016

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Doubly crosslinked microgels (DX microgels) are hydrogels constructed by covalently interlinked microgel particles, offering two levels of hierarchy within the network, the first one being the microgel and the second being the interlinked microgel network. Herein we describe an efficient approach for DX microgel synthesis via the ultrafast triazolinedione (TAD)-based click reaction. Cyclopentadienyl functional microgels were prepared by a conventional water in oil (W/O) suspension, free-radical copolymerization of poly (ethylene glycol) methyl ether methacrylate (M-n = 500 g mol(-1)) with glycidyl methacrylate and ethylene glycol dimethacrylate as crosslinkers. Microgel post-modification was subsequently achieved by reacting glycidyl functions with sodium cyclopentadienide (NaCp), resulting in Cp-functionalized microgels. Finally, the microgels were mixed with a bis-TAD functional crosslinker, resulting in crosslinking with adequate kinetics (minutes to seconds) to form a doubly crosslinked microgel network. Size distributions of swollen microgels before creation of the second network were followed by optical microscopy and particle size measurements. The efficient functionalization of the microgels with Cp units was demonstrated by a fluorescence labelling study. Dynamic rheology data showed the increase of mechanical properties from the microgels to the doubly crosslinked microgel network formed after addition of the TAD crosslinker. The current study thus highlights the efficiency of catalyst free modular ligation chemistry to synthesize DX microgels with a very fast gelation process from 5 minutes to 15 seconds depending on the crosslinker to Cp ratio, from 0.7 to 1 respectively

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Using click chemistry to dial up the modulus of doubly crosslinked microgels through precise control of microgel building block functionalisation

Cited by 6 publications

References 36 publications

High Temperature Self‐Regenerative Granular Hydrogels for Fracture Treatments During Subsurface Energy Recovery

High Temperature Self‐Regenerative Granular Hydrogels for Fracture Treatments During Subsurface Energy Recovery

Click Cross-Linking-Improved Waterborne Polymers for Environment-Friendly Coatings and Adhesives

Click reactive microgels as a strategy towards chemically injectable hydrogels

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