Thiol-norbornene reactions to improve natural rubber dispersion in cellulose nanofiber coatings

Fein, Kendra; Bousfield, Douglas W.; Gramlich, William M.

doi:10.1016/j.carbpol.2020.117001

Cited by 27 publications

(10 citation statements)

References 38 publications

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“…Base‐catalyzed aqueous reactions have functionalized CNFs with norbornene groups that have facilitated small molecule [ 16 ] and natural rubber particle secondary modifications. [ 17 ] Through similar reactions, methacrylate groups have been bonded to cellulose derivatives. [ 18,19 ] These completely aqueous modifications can be carried out without the solvent exchanges needed to create CNF macroinitiators, [ 9,20 ] although the efficiency of the functionalization will decrease because of the competing hydrolysis reaction.…”

Section: Methodsmentioning

confidence: 99%

Aqueous Polymer Modification of Cellulose Nanofibrils by Grafting‐Through a Reactive Methacrylate Group

Kelly

Peng

Gardner

et al. 2020

Macromol. Rapid Commun.

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Modifying the surface of cellulose nanofibrils (CNFs) produced by mechanical refinement with a variety of polymer functional groups in an entirely water‐based system is challenging because only surface hydroxyl groups are accessible. To address this limitation, an entirely water‐based, polymer modification scheme is developed. CNFs are functionalized with a reactive methacrylate functional group followed by subsequent grafting‐through polymerization. This modification worked with a variety of water‐soluble and water‐insoluble (meth)acrylates and (meth)acrylamides, grafting up to 45 wt% polymer on to the CNFs. The reaction conditions introducing the methacrylate functional group are adjusted to vary the degree of functionality. Soxhlet extraction of modified samples demonstrates that the reactive methacrylate group is necessary to facilitate polymer grafting. The degree of functionalization of the polymers is studied via quantitative transmission IR spectroscopy and the morphology of the resulting cellulose nanofibrils is studied via a combination of optical, scanning electron, and atomic force microscopy. High levels of polymer modification do not significantly affect the micrometer‐scale fibril morphology.

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Section: Methodsmentioning

confidence: 99%

Aqueous Polymer Modification of Cellulose Nanofibrils by Grafting‐Through a Reactive Methacrylate Group

Kelly

Peng

Gardner

et al. 2020

Macromol. Rapid Commun.

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“…Also, the incorporation of nanocellulose in NR matrix contributes to the enhancement in the biodegradability of the composites 109 . The use of CNF as filler in the NR matrix could also enhanced the grease resistance which makes this material more useful for packaging applications 110 .…”

Section: Cnc Based Rubber Composites For Packaging Applicationmentioning

confidence: 99%

Bioresourced fillers for rubber composite sustainability: current development and future opportunities

Chang

Gupta

Muthuraj³

et al. 2021

Green Chem.

118

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“…[128][129][130][131] Although in industry cross-linked rubber is produced mainly by the vulcanization process, the ability to adjust the structure of cross-links with thiol-X reactions to more specific applications is largely investigated in the literature. [132][133][134][135][136][137] The most commonly employed thiols to photo-cross-link are shown in Figure 9. Schlögl and coworkers employed thiol-ene reactions to photocross-link liquid isoprene rubber to obtain precise structures by 3D printing.…”

Section: Rubber Modifications Via Thiol-x Reactionsmentioning

confidence: 99%

“…Moreover, the thiol-ene reactions are frequently employed to introduce "clickable" functional groups in the polymer backbone. Rubber functionalization through thiol-ene click reactions also include modulation of the polymer hydrophobicity by introduction of polar groups, [142][143][144] introduction of inorganic materials, [63,145] improvement of the dispersion of nanomaterials, [137,146,147] polymer coating, [148] introduction of biomolecules, [149][150][151][152] synthesis of patterned microstructures, [153,154] linking of ionic liquids, [155] and introduction of dynamic hydrogen bonds for self-healing properties. [143,[156][157][158] Some biological applications include preparation of antibacterial materials, [159,160] surface preparation to protein adsorption [161] and synthesis of chiral materials by introduction of chiral amino acids.…”

Section: Rubber Modifications Via Thiol-x Reactionsmentioning

confidence: 99%

Enzymatic and Chemical Approaches for Post‐Polymerization Modifications of Diene Rubbers: Current state and Perspectives

Soares

Steinbüchel

2021

Macromolecular Bioscience

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Diene rubbers are polymeric materials which present elastic properties and have double bonds in the macromolecular backbone after the polymerization process. Post-polymerization modifications of rubbers can be conducted by enzymatic or chemical methods. Enzymes are environmentally friendly catalysts and with the increasing demand for rubber waste management, biodegradation and biomodifications have become hot topics of research. Some rubbers are renewable materials and are a source of organic molecules, and biodegradation can be conducted to obtain either oligomers or monomers. On the other hand, chemical modifications of rubbers by click-chemistry are important strategies for the creation and combination of new materials. In a way to expand the scope of uses to other non-traditional applications, several and effective modifications can be conducted with diene rubbers. Two groups of efficient tools, enzymatic, and chemical modifications in diene rubbers, are summarized in this review. By analyzing stereochemical and reactivity aspects, the authors also point to some applications perspectives for biodegradation products and to rational modifications of diene rubbers by combining both methodologies.

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Thiol-norbornene reactions to improve natural rubber dispersion in cellulose nanofiber coatings

Cited by 27 publications

References 38 publications

Aqueous Polymer Modification of Cellulose Nanofibrils by Grafting‐Through a Reactive Methacrylate Group

Aqueous Polymer Modification of Cellulose Nanofibrils by Grafting‐Through a Reactive Methacrylate Group

Bioresourced fillers for rubber composite sustainability: current development and future opportunities

Enzymatic and Chemical Approaches for Post‐Polymerization Modifications of Diene Rubbers: Current state and Perspectives

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