Surface modification of chitin and chitosan with poly(3-hexylthiophene) via oxidative polymerization

Hai, Thien An Phung; Sugimoto, Ryuichi

doi:10.1016/j.apsusc.2017.10.197

Cited by 33 publications

(16 citation statements)

References 78 publications

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“…The first temperature corresponds to the evaporation water. The temperature of 287.95°C is related to the evaporation of volatiles due to the degradation of chitosan through its deacetylation and depolymerization (Altınkaya et al., 2018; Hai & Sugimoto, 2018; Zohuriaan & Shokrolahi, 2004).…”

Section: Resultsmentioning

confidence: 99%

Effect of glutaraldehyde/glycerol ratios on the properties of chitosan films

Oliveira

Ugucioni

Borges

2020

J Food Process Preserv

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Chitosan is a biodegradable polymer and could be applied as packaging. To make chitosan more competitive, plasticizers and cross‐linking agents are added in films. The aim of this paper was to obtain and characterize films of chitosan without or with glutaraldehyde (0; 0.99 mg/150 ml) in different concentrations of glycerol (0, 10, 20, and 30%w/w), for improving the properties like tensile resistance and the water vapor permeability. The films were homogeneous, without phase separation, and with a similar chemical structure. The glutaraldehyde makes the chitosan partly hydrophobic, leading to glycerol saturation in samples with glutaraldehyde and 20 or 30% of glycerol. The Principal Component Analysis for the film with glutaraldehyde and 10% of glycerol presented 3.60 g.mm/kPa.day.m2 of water vapor permeability and 36.96 MPa of tensile resistance. The use of plasticizer and cross‐linking in combination is promising to make chitosan film more competitive on the market of packaging. Practical Applications The addition of glutaraldehyde and glycerol was efficient to improve film properties like water vapor permeability and mechanical properties. The chitosan films with glycerol and glutaraldehyde exhibited similar physical and chemical properties to non‐biodegradable polymers from the petrochemical origin and non‐renewable sources. Furthermore, chitosan films with these additives can be applied as packaging, improving the competitiveness of this biopolymer to the market. The technology described in the paper is important for application as secondary or tertiary packaging in the food industry.

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Section: Resultsmentioning

confidence: 99%

Effect of glutaraldehyde/glycerol ratios on the properties of chitosan films

Oliveira

Ugucioni

Borges

2020

J Food Process Preserv

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“…[31][32][33][34][35][36] In our previous reports, the surface modication of cellulose and polysaccharides with conjugated polymers has been successfully accomplished via oxidative polymerization using FeCl 3 . [37][38][39] In this study, copolymers composed of two different conjugated polymers, including 3-hexylthiophene and uorene were applied for the surface modication of chitin and chitosan. It is noticeable that multicolor materials can be manipulated by controlling the monomer composition of 3-hexylthiophene and uorene.…”

mentioning

confidence: 99%

Fluorescence control of chitin and chitosan fabricatedviasurface functionalization using direct oxidative polymerization

Hai

Sugimoto

2018

RSC Adv.

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The copolymer of 3-hexylthiophene (3HT) and fluorene (F) was directly grafted onto chitin and chitosan using FeCl 3 as an oxidant. The properties of the grafted chitin/chitosan were characterized by Fourier transform infrared (FT-IR) spectroscopy, UV-Vis spectroscopy, fluorescence spectroscopy, X-ray diffraction analysis, thermogravimetric analysis (TGA), transmission electron microscopy-energy dispersive X-ray spectroscopy, and quantum yield measurements. The UV-Vis absorption peaks of the chitin/chitosan grafted with 3-hexylthiophene and fluorene copolymer were increasingly blue-shifted upon increasing the fluorene content and the red-shifted emission of the grafted chitin/chitosan were controlled by varying the monomers feed of the 3HT/F units. The hypsochromic and bathochromic shifts of chitin/chitosan were ascribed to the (3HT/F) moieties grafted to their surface. The quantum yield of grafted chitin/chitosan increased upon increasing the fluorene content. The TGA and XRD analysis revealed that the thermal stability and crystallinity of chitin/chitosan decreased upon grafting the copolymer of fluorene and 3-hexylthiophene. This article represents a simple route towards the surface modification of chitin and chitosan using conducting copolymers, providing multicolor chitin and chitosan via a one-step reaction.

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“…This process utilizes either sodium hydroxide or potassium hydroxide. The alkaline condition created drives the hydrolysis of polyesters via the nucleophilic attack by [72,73] Citric acid/CS EDC and NHS cross-linker Improved biomineralization due to the accumulation of carboxyl groups and inorganic ions [135][136][137] Gentamicin/CS Dip coating Enhanced antimicrobial property and biocompatibility [75,76,138] Phosvitin/CS Layer by layer coating Chelating agent, allowed iron binding capabilities to aid in improved antimicrobial property [74,77] HLF-11/CS Polyethylene glycol spacer Exposed the arginine-rich portion for binding of the peptide thereby enhanced the antimicrobial activity [139] Poly(3-hexylthiophene)/CS Oxidative polymerization Increased the thermal stability making it resistant to decomposition and enhances cell adhesion [82] Ferulic acid/CS and Ethyl ferulate/CS Dip coating Improved cell attachment, spreading, and proliferation by reducing the cystallinity [79,80,140] Epoxides/CS Enhanced the interaction with albumin over the plasma proteins thereby supporting cell adhesion [141][142][143] RGD/CS Carbodiimide reaction Improved cell adhesion due to the presence of GRGDS-peptides [92] hydroxide ions of the carbonyl carbon. [102] In CS, the glycosidic bonds are involved in the hydrolysis process, which is catalyzed by the N-acetyl group.…”

Section: Alkaline Hydrolysismentioning

confidence: 99%

“…An enhanced biodegradability and protein adsorption potential were observed in plasma‐treated CS films . Oxidative polymerization is another technique utilized for modification of CS with poly(3‐hexylthiophene), which can decrease wettability of the graft, thus maintaining the structural integrity during implantation . Enzyme‐induced biomineralization on CS scaffolds acted as an alternative model to the traditional method of incubation of CS scaffolds in simulated body fluid .…”

Section: Surface Modification Of Cs Biocomposites In Btementioning

confidence: 99%

Chitosan in Surface Modification for Bone Tissue Engineering Applications

Abinaya

Prasith

Ashwin

et al. 2019

Biotechnology Journal

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Traditional methods of bone defect repair include autografts, allografts, surgical reconstruction, and metal implants that have several disadvantages such as donor site morbidity, rejection, risk of disease transmission, and repetitive surgery. Biomaterial‐based bone reconstructions can, therefore, be an efficient alternative due to the inherent properties of the materials. Chitosan (CS), the deacetylated form of chitin, is a biopolymer having a wide array of applicability in regenerative tissue applications owing to its biocompatible, in vitro degradative and bioresorbable nature. Extensive studies are being carried out using CS to augment the properties of the already existing methods and to also improve the applicability of CS‐based biocomposites in bone tissue repair. In this review, the suitability of CS as a surface modifier has been discussed in detail for the already existing implants, surface modifications of CS‐based natural biocomposites for bone tissue regeneration, and the wide range of techniques that can introduce these modifications. CS, being a natural polymer, possesses advantageous properties including surface modifier that makes it a suitable candidate for bone regeneration, and further research to investigate its osteogenic potential in vivo along with the molecular and signaling mechanisms involved in bone regeneration can aid in expanding its applicability in clinical trials.

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Surface modification of chitin and chitosan with poly(3-hexylthiophene) via oxidative polymerization

Cited by 33 publications

References 78 publications

Effect of glutaraldehyde/glycerol ratios on the properties of chitosan films

Effect of glutaraldehyde/glycerol ratios on the properties of chitosan films

Fluorescence control of chitin and chitosan fabricatedviasurface functionalization using direct oxidative polymerization

Chitosan in Surface Modification for Bone Tissue Engineering Applications

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