Functionalization of chitosan with lignin to produce active materials by waste valorization

Crouvisier-Urion, Kevin; Farias, Fernanda Regina da Silva; Arunatat, Sorawit; Griffin, D. N.; Gerometta, Massimiliano; Rocca-Smith, Jeancarlo R.; Weber, Guy; Sok, Nicolas; Karbowiak, Thomas

doi:10.1039/c9gc01372e

Cited by 42 publications

(16 citation statements)

References 61 publications

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“…Among the available biomass precursors, polysaccharides stand out as the most promising and have already dominated research revolving around the design of new biobased nanocomposites. − Among those of interest, chitosan-based marine fishery waste stands as the sole cationic polysaccharides, its amino groups being the basis of its catalytic activity, metal-chelating ability, and biological efficiency. − Moreover, chitosan is biocompatible, fully degradable, and readily soluble in acidic aqueous media and can be used in several forms, including a colloidal state, in coagulated forms as hydrogels or microspheres. It is also moldable and can be caste on demand at a desirable thickness as nanostructured films. − The excellent film-forming ability of chitosan has opened great opportunities for biobased packaging materials. − Coupled to the possibility of conjugating chemicals through its primary amine, a subtly controlled release of active ingredients from chitosan films has also been recently demonstrated. − The poor mechanical strength of chitosan has also been overcome by addition of a small amount of nanosized fillers, for example, Montmorillonite, graphene oxide, − hydroxyapatite, carbon nanotubes, , and metal oxide nanoparticles, among others. − , Recently, nanofibrils, nanocrystals, and nanowhiskers of cellulose, chitin, lignin, and other biomass-sourced building blocks have also been used for sustaining chitosan films. − …”

Section: Introductionmentioning

confidence: 99%

Phosphorylated Micro- and Nanocellulose-Filled Chitosan Nanocomposites as Fully Sustainable, Biologically Active Bioplastics

Blilid

Kędzierska

Miłowska

et al. 2020

ACS Sustainable Chem. Eng.

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Controlled cellulose fragmentation and its downsizing to micro-and nanocrystals have recently captured tremendous attention to access sustainable nanomaterials. Hitherto, few functionalized cellulose derivatives have been used as fillers, and additional knowledge is needed to establish an accurate structure−performance relationship in the realm of sustainable nanocomposites. Herein, a range of phosphorylated microcellulose (MCC) and nanosized cellulose (CNC) have been prepared and used as reinforcing fillers to build transparent and flexible cellulose-filled chitosan nanostructured films. Regardless of their functionalization, all nanocellulose fillers reach good dispersion in the matrix, while those that are microcellulose aggregate slightly inside of the films. Distinctively, improved thermal stability was seen for chitosan films reinforced with cyclotriphosphazene grafted on cellulose nanocrystals (PN-CNC), where only half weight of the bioplastic was decomposed at 700 °C. Moreover, better mechanical properties were obtained using nanocellulose instead of microcellulose as fillers, with PN-CNC-filled chitosan reaching the highest value of 1.649 MPa in tensile modulus compared to 1.195 MPa for neat chitosan films. Phosphorylated cellulose fillers (P-CNC and P-MCC) also bring interesting antibacterial and intercellular catalase activities, compared to neat chitosan and unmodified cellulose-filled chitosan. In total, this study sheds light on the pivotal role of cellulose phosphorylation in improving the thermal, mechanical, and biological properties of the next generation of rationally designed bioplastics.

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Section: Introductionmentioning

confidence: 99%

Phosphorylated Micro- and Nanocellulose-Filled Chitosan Nanocomposites as Fully Sustainable, Biologically Active Bioplastics

Blilid

Kędzierska

Miłowska

et al. 2020

ACS Sustainable Chem. Eng.

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“…Sinapic acid has the highest radical activity due to di-ortho-methoxyl substitution, ferulic acid has an intermediate activity, and coumaric acid has no antioxidant activity. The results could confirm that the higher concentration of syringyl, the higher the antioxidant activity (Crouvisier-Urion et al 2019). Biopolymer matrix from Poly(lactide) (PLA)-lignin results in a good dispersion.…”

Section: Active Packagingmentioning

confidence: 70%

Lignin as an Active Biomaterial: A Review

Solihat

Sari²,

Falah³

et al. 2021

JSL

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Lignin is the second most naturally abundant biopolymer in the cell wall of lignocellulosic compound (15-35%) after cellulose.Lignin can be generated in massive amounts as by-products in biorefineries and pulp and paper industries through differing processes. Most lignin is utilized as generating energy and has always been treated as waste. Due to the high amount of phenolic compounds in lignin, it is considered as a potential material for various polymers, building blocks, and biomaterials production. Even though lignin can be utilized in the form of isolated lignin directly, the modification of lignin can increase the wide range of lignin applications. Lignin-based copolymers and modified lignin show better miscibility with another polymeric matrix, outstanding to the enhanced performance of such lignin-based polymer composites.This article summarizes the properly updated information of lignin’s potential applications, such as bio-surfactant, active packaging, antimicrobial agent, and supercapacitor.Keywords: active packaging, antimicrobial agent, bio-surfactant, lignin, supercapacitor

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“…The UV–vis absorption spectra of DAL, DAL-12ane, and DAL-11ene are shown in Figure b. The absorption peak of DAL at 218 nm was related to the unsaturated CC or CO bonds, while that at 280 nm corresponded to the phenolic hydroxyl and aromatic moieties of the DAL . The spectra of DAL-12ane and DAL-11ene both showed a small blue shift (213 nm) compared to that of DAL, which indicated that the aggregation extent of aromatic moieties decreased due to the introduction of long flexible chains.…”

Section: Results and Discussionmentioning

confidence: 90%

“…The absorption peak of DAL at 218 nm was related to the unsaturated CC or CO bonds, while that at 280 nm corresponded to the phenolic hydroxyl and aromatic moieties of the DAL. 40 The spectra of DAL-12ane and DAL-11ene both showed a small blue shift (213 nm) compared to that of DAL, which indicated that the aggregation extent of aromatic moieties decreased due to the introduction of long flexible chains. In addition, the peak at 280 nm declined obviously for DAL-12ane and DAL-11ene due to the consumption of phenolic hydroxyl groups by the esterification reaction.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Study on Modified Dealkaline Lignin as Visible Light Macromolecular Photoinitiator for 3D Printing

Zhang

Keck

et al. 2020

ACS Sustainable Chem. Eng.

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Under natural light, lignin can produce a small amount of free radicals, resulting in yellowing of lignin-related products. However, the activity of these free radicals is very low, so that few studies on exploring the application potential of lignin as photoinitiator (PI) in photopolymerization have been reported. In this study, based on dealkaline lignin (DAL), two alkylated DAL (DAL-11ene and DAL-12ane) were synthesized through facile one-step esterification reactions between DAL and undecanoyl chloride or dodecanoyl chloride. The photoinitiation properties of DAL, DAL-11ene, and DAL-12ane were investigated by real-time FTIR spectroscopy and NIR-photorheology using 1,6-hexanediol diacrylate as a monomer. The formation of reactive species was elucidated by laser flash photolysis and electron spin resonance. The results indicated that DAL itself showed a certain photoinitiating ability, especially when it was combined with an amine co-initiator, while both DAL-11ene and DAL-12ane presented much higher photoinitiating efficiencies compared with DAL. Moreover, DAL-11ene containing a polymerizable group could be bonded into the network of final polymer products, which can increase their biosafety. 3D structures of polyacrylates were fabricated successfully using DAL-11ene and DAL-12ane as PIs through digital light processing 3D printing upon 405 nm exposure, indicating their large potentials in photopolymerization.

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Functionalization of chitosan with lignin to produce active materials by waste valorization

Abstract: Active films are produced by a grafting reaction based on the reactivity between chitosan amino groups and lignin hydroxyl groups. This opens a new route for the valorization of lignin, with the possibility of tuning the anti-oxidant activity.

Cited by 42 publications

References 61 publications

Phosphorylated Micro- and Nanocellulose-Filled Chitosan Nanocomposites as Fully Sustainable, Biologically Active Bioplastics

Phosphorylated Micro- and Nanocellulose-Filled Chitosan Nanocomposites as Fully Sustainable, Biologically Active Bioplastics

Lignin as an Active Biomaterial: A Review

Study on Modified Dealkaline Lignin as Visible Light Macromolecular Photoinitiator for 3D Printing

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