Designing functionalizable hydrogels through thiol–epoxy coupling chemistry

Cengiz, Nergiz; Rao, Jingyi; Sanyal, Amitav; Khan, Arijit

doi:10.1039/c3cc45859h

Cited by 81 publications

(53 citation statements)

References 26 publications

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“…The epoxy-thiol click reaction is also employed for the synthesis of organic molecules [3], functionalized polymers [4][5][6][7][8][9], polymer networks [10][11][12], and two-component healing agents [13][14][15].…”

Section: Introductionmentioning

confidence: 99%

Kinetics of the epoxy–thiol click reaction initiated by a tertiary amine: Calorimetric study using monofunctional components

et al. 2015

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Section: Introductionmentioning

confidence: 99%

Kinetics of the epoxy–thiol click reaction initiated by a tertiary amine: Calorimetric study using monofunctional components

et al. 2015

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“…These characteristics have allowed for the discovery of innovative solutions in the field of coatings technology [4,5]. Among click reactions, thiol-epoxy systems have broad applications [6][7][8][9][10][11] but they present an important drawback which is the low reactivity of the formulation that requires the addition of a catalyst. However, the disadvantage of a too short pot-life appears on catalysing with amines [12].…”

Section: Introductionmentioning

confidence: 99%

Enhancement in the Glass Transition Temperature in Latent Thiol-Epoxy Click Cured Thermosets

et al. 2015

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Tri and tetrafunctional thiol were used as curing agent for diglycidyl ether of bisphenol A (DGEBA) catalyzed by a commercially available amine precursor, LC-80. Triglycidyl isocianurate (TGIC) was added in different proportions to the mixture to increase rigidity and glass transition temperature (Tg). The cooperative effect of increasing functionality of thiol and the presence of TGIC in the formulation leads to an increased Tg without affecting thermal stability. The kinetics of the curing of mixtures was studied by calorimetry under isothermal and non-isothermal conditions. The latent characteristics of the formulations containing amine precursors were investigated by rheometry and calorimetry. The increase in the functionality of the thiol produces a slight decrease in the storage lifetime of the mixture. The materials obtained with tetrathiol as curing agent showed the highest values of Young's modulus and Tg.

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“…This opens the ring of the oxirane and consequently promotes a rapid hydrogen transfer to the resulting alkoxide, terminating the reaction. The final product, a β‐hydroxy thioether, offers strong adhesion and gives the opportunity for additional surface modification . Further functionalization can be achieved, for example, through esterification of the ß‐hydroxyl groups .…”

Section: Methodsmentioning

confidence: 99%

Superhydrophobic/oleophobic coatings based on a catalyst driven thiol‐epoxy‐acrylate ternary system

Rezaei

Talley

Dickey

et al. 2018

J of Applied Polymer Sci

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Superhydrophobic surfaces have attracted much attention for their exceptional properties such as self‐cleaning, anti‐fouling, and anti‐fogging. This study presents a facile approach for creating superhydrophobic coatings that are also oleophobic by utilizing spray deposition of polymers mixed with silica particles as an easy and effective route to control the surface roughness of the coatings. The polymer precursors formulated here are based on a ternary thiol‐epoxy‐acrylate mixture that reacts in the presence of a strong base without a need for external initiation (such as light). This system employs tetrafunctional thiol monomers as hubs where both the acrylate and the epoxy components can covalently bond. The acrylate component contains a perfluorinated side chain offering low surface energy properties and the difunctional epoxy monomers crosslink the thiol hubs to provide strength. Addition of a strong base catalyst (1,8‐diazabicycloundec‐7‐ene, or DBU) to the coating precursors initiates the polymerization reaction without the need for light. To identify the optimal formulation, Fourier transformed infrared spectroscopy (FTIR) measurements quantified the kinetics of the polymerization, X‐ray photoemission spectroscopy analysis revealed the surface composition, an optical goniometer evaluated the wetting behavior, and scanning electron microscopy and confocal laser the microscopy provided information about the surface topography of the coatings. Based on the results from FTIR, addition of 0.08 mol % of DBU effectively carries out the reaction within 10 min on the substrate while providing long solution shelf life for the spray coating process. The goniometer results showed that water contact angle of >150°, n‐dodecane contact angle of >110° and diiodomethane contact angle of >130° is achievable upon optimization of the coating precursors. This simple route to create superhydrophobic and oleophobic coatings by spraying may be useful for packaging, protective coatings, and other surface modifications. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018, 135, 46710.

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Designing functionalizable hydrogels through thiol–epoxy coupling chemistry

Cited by 81 publications

References 26 publications

Kinetics of the epoxy–thiol click reaction initiated by a tertiary amine: Calorimetric study using monofunctional components

Kinetics of the epoxy–thiol click reaction initiated by a tertiary amine: Calorimetric study using monofunctional components

Enhancement in the Glass Transition Temperature in Latent Thiol-Epoxy Click Cured Thermosets

Superhydrophobic/oleophobic coatings based on a catalyst driven thiol‐epoxy‐acrylate ternary system

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