A General Aqueous Silanization Protocol to Introduce Vinyl, Mercapto or Azido Functionalities onto Cellulose Fibers and Nanocelluloses

Beaumont, Marco; Bacher, Markus; Opietnik, Martina; Gindl‐Altmutter, Wolfgang; Potthast, Antje; Rosenau, Thomas

doi:10.3390/molecules23061427

Cited by 57 publications

(80 citation statements)

References 50 publications

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“…Moreover, azide group containing cellulose derivative could be crosslinked with propargyl modified cyclodextrin to obtain biocompatible gels . The surface of cellulose fibers was modified as well, for example, by copolymerization of alkyne‐containing monomers, by silane chemistry, or by tosylation of the paper surface followed by nucleophilic displacement with azide ions . The functionalities attached can possess photomicrobicidal properties or increase the strength of pulp fibers .…”

Section: Introductionmentioning

confidence: 99%

All Sugar Based Cellulose Derivatives Synthesized by Azide–Alkyne Click Chemistry

Koschella

Chien

Iwata

et al. 2019

Macro Chemistry & Physics

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chemically by, for example, glycosylation reactions. [3,4] Cellulose can be converted to the corresponding orthoesters by reaction with acetobromoglucose in presence of triethylamine. [5] However, the methods described so far require the use of hazardous reagents. The copper-catalyzed azide-alkyne cycloaddition was found to be advantageous for the preparation of numerous cellulose derivatives. [6,7] This reaction proceeds under mild conditions and even in aqueous media. In addition to a proof of principle, for example, [8,9] this type of click reaction has been utilized for the synthesis of highlyengineered cellulose derivatives. Dendron-like moieties could be attached to cellulose, [10] where either the azide [11] or the alkyne moiety was attached to the complementarily modified polymer backbone. [12] Moreover, azide group containing cellulose derivative could be crosslinked with propargyl modified cyclodextrin to obtain biocompatible gels. [13] The surface of cellulose fibers was modified as well, for example, by copoly merization of alkyne-containing monomers, [14] by silane chemistry, [15,16] or by tosylation of the paper surface followed by nucleophilic displacement with azide ions. [17] The functionalities attached can possess photomicrobicidal properties [18-20] or increase the strength of pulp fibers. [21] Maltose derivatives bearing N-and O-linked propargyl moieties attached to cellulose by azide-alkyne click chemistry increase the water solubility of the polymer. [22,23] This approach of click chemistry enabled the preparation of cellulose block copolymers by using cellulose derivatives bearing alkyne-or azide groups at position 1 of the reducing end of the oligosaccharide chain. [24] The reactive groups can be introduced regioselectively by, for example, 3-O-azidopropoxypoly(ethylene glycol)-2,6-di-O-thexyldimethylsilyl cellulose [25] or 3-O-propargyl cellulose. [26] In the context of plastic waste including the micro-plastic problems, biobased and biodegradable polymers are highly desirable. In this respect, solubility is an interesting parameter to enhance the biocompability of polymers. Moreover, functional polymers synthesized completely based on renewable resource (polymeric and monomeric carbohydrates) are important in order to save fossil resources. In the present paper the synthesis and structural characterization of cellulose derivatives bearing sugar moieties is reported that impart solubility to the polymer by taking advantages of the click chemistry approach. Cellulose is functionalized with different monosaccharides by the azide-alkyne click chemistry approach. Either azide or alkyne moieties are attached to the cellulose backbone and allowed to react with sugar moieties bearing the opposite clickable groups. Between 16% and 100% of the reactive sites at the polymer can be functionalized with sugar molecules and a clear correlation between steric demand and DS Sugar is observed. The polymers remain soluble in aprotic dipolar media like dimethyl sulfoxide. Products with a sufficient hydroph...

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Section: Introductionmentioning

confidence: 99%

All Sugar Based Cellulose Derivatives Synthesized by Azide–Alkyne Click Chemistry

Koschella

Chien

Iwata

et al. 2019

Macro Chemistry & Physics

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“…Thus, in this type of modification the condensation reaction occurs between silanol groups (Si-OH) as well as between the silanol and the BC hydroxyls (10) . The condensation step can also be induced by employing strong or weak bases such as NaOH (7) and NH 4 OH (9) .…”

Section: Resultsmentioning

confidence: 99%

“…Traditionally, surface modification protocols to impart hydrophobic properties (6) onto nanocellulose do not respect the green-chemistry principles. Besides being time-consuming, most of them use to employ previous solvent-exchange steps with hazardous aprotic organic solvents such as dimethyl sulfoxide and N,N-dimethylformamide in addition to heat curing process after the chemical treatment (7) .…”

Section: Introductionmentioning

confidence: 99%

Surface-Modified Bacterial Cellulose with Mercaptosilane as a Multifunctional Platform

Amaral

Claro

Monteiro

et al. 2020

IJAMB

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Cellulose synthesized by bacteria has unique properties such as high water retention capacity, biocompatibility, biodegradability and flexibility. Nevertheless, modification of this biomaterial is required in order to obtain multifunctional materials, which may be applied in several high-value added products, as catalytic and cell culture platforms. The surface of bacterial cellulose (BC) can be modified by several approaches, namely: (i) physical treatment by plasma, (ii) adsorption of molecules onto BC surface, and (iii) chemical modification. In this sense, the aim of this study was to modify the BC surface by silanization reaction at room temperature using a mixture of ethanol and water, using two different protocols. Thus, BC membranes synthesized by Komagataeibacter xylinus were modified by adding the thiol (SH) functional group with (3-mercaptopropyl)trimethoxysilane under mild conditions. The produced materials were analyzed by elemental analysis, ATR-FTIR, TGA and SEM, and the successful modification was proven by elemental analysis and SEM.

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“…Recently, an aqueous silanization protocol was established to introduce multiple functional groups onto (nano)cellulose in aqueous media using catalytic amounts of HCl and NaOH. 290 , 291 This approach is a highly versatile method to introduce functional alkoxysilanes with azido, thiol, and other groups and lead to polysaccharides that can be postfunctionalized via click chemistry. 290 , 291 …”

Section: Chemical Modificationmentioning

confidence: 99%

Hydrogel-Forming Algae Polysaccharides: From Seaweed to Biomedical Applications

et al. 2021

Self Cite

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With the increasing growth of the algae industry and the development of algae biorefinery, there is a growing need for high-value applications of algae-extracted biopolymers. The utilization of such biopolymers in the biomedical field can be considered as one of the most attractive applications but is challenging to implement. Historically, polysaccharides extracted from seaweed have been used for a long time in biomedical research, for example, agarose gels for electrophoresis and bacterial culture. To overcome the current challenges in polysaccharides and help further the development of high-added-value applications, an overview of the entire polysaccharide journey from seaweed to biomedical applications is needed. This encompasses algae culture, extraction, chemistry, characterization, processing, and an understanding of the interactions of soft matter with living organisms. In this review, we present algae polysaccharides that intrinsically form hydrogels: alginate, carrageenan, ulvan, starch, agarose, porphyran, and (nano)cellulose and classify these by their gelation mechanisms. The focus of this review further lays on the culture and extraction strategies to obtain pure polysaccharides, their structure-properties relationships, the current advances in chemical backbone modifications, and how these modifications can be used to tune the polysaccharide properties. The available techniques to characterize each organization scale of a polysaccharide hydrogel are presented, and the impact on their interactions with biological systems is discussed. Finally, a perspective of the anticipated development of the whole field and how the further utilization of hydrogel-forming polysaccharides extracted from algae can revolutionize the current algae industry are suggested.

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A General Aqueous Silanization Protocol to Introduce Vinyl, Mercapto or Azido Functionalities onto Cellulose Fibers and Nanocelluloses

Cited by 57 publications

References 50 publications

All Sugar Based Cellulose Derivatives Synthesized by Azide–Alkyne Click Chemistry

All Sugar Based Cellulose Derivatives Synthesized by Azide–Alkyne Click Chemistry

Surface-Modified Bacterial Cellulose with Mercaptosilane as a Multifunctional Platform

Hydrogel-Forming Algae Polysaccharides: From Seaweed to Biomedical Applications

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