Dual pH/thermal-dependent coloring polymeric dye through Mannich reaction of chitosan: Synthesis and characterization

Chalitangkoon, Jongjit; Monvisade, Pathavuth

doi:10.1016/j.carbpol.2019.115049

Cited by 21 publications

(12 citation statements)

References 40 publications

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“…For guest polymers, CECS‐g‐PHP was successfully synthesized via the Mannich reaction, which was slightly modified from our previous work [ 53 ] – see Figure 1a. To avoid excess crosslinking reaction and to still dissolve in water, the reaction was carried out at the desired mole ratio.…”

Section: Resultsmentioning

confidence: 99%

“…CECS‐g‐PHP synthesis was modified from Chalitangkoon. [ 53 ] In detail, CECS (1 g) solution in 100 mL distilled water was mixed with PHP (1.67 g) solution in 50 mL N,N ‐dimethylformamide (DMF). After adding formaldehyde (0.29 g), the mixture was stirred for 24 h at 60 °C.…”

Section: Methodsmentioning

confidence: 99%

“…Previously, we modified the chitosan structure, with phenolphthalein side chains, via a one‐pot reaction. [ 53 ] It changed color with pH, similar to free phenolphthalein. We expected that phenolphthalein in the derivative could be complexed with β‐cyclodextrin.…”

Section: Introductionmentioning

confidence: 99%

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Stimuli‐Responsive, Self‐Healing, and Injectable Hydrogels with Dual‐Crosslinked Design from Phenolphthalein‐Grafted N‐Carboxyethyl Chitosan

Savetsakulanont

Chalitangkoon

Monvisade

2021

Macro Materials & Eng

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A new biomaterial, a hydrogel, with dual‐crosslinked design, has been created with enhanced mechanical performance. The hydrogels are fabricated based on water‐soluble chitosan, with dual‐crosslinking of imine linkages and host–guest interactions. Phenolphthalein‐grafted N‐carboxyethyl chitosan (CECS‐g‐PHP), as a guest polymer, is synthesized and structurally characterized and complexed with hexamethylenediamine modified β‐cyclodextrin (β‐CD‐HDA), as a host molecule. Oxidized sodium alginate (OSA) is added to form crosslinking networks via imine linkages with the existing amino groups. The hydrogels show significantly shorter gelation times and higher compressive stresses, compared with single‐crosslinked hydrogels. The phenolphthalein units in the hydrogel change color with pH and other added chemicals. Moreover, the hydrogels can be injected and are self‐healing with >80% recovery within 4 h. Thus, these dual‐crosslinked hydrogels, which respond to pH and other stimuli, are promising designs for new multifunctional biomaterials.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Stimuli‐Responsive, Self‐Healing, and Injectable Hydrogels with Dual‐Crosslinked Design from Phenolphthalein‐Grafted N‐Carboxyethyl Chitosan

Savetsakulanont

Chalitangkoon

Monvisade

2021

Macro Materials & Eng

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“…The color changes phenomena can be differentiated based on types of an external stimulus such as thermochromic (color change caused by heat), photochromic (color change caused by light), magnetochromic (color change caused by magnetic field), and halochromic (color change caused by pH). [1][2][3][4] Besides the well-known thermochromic and photochromic, the less favored halochromic might offer a great value for textile, medical, and food packaging. Halochromic is a behavior of visible color changes when response to acid-base of the surrounding medium.…”

Section: Introductionmentioning

confidence: 99%

“…Generally, chromic can be defined as a wide group of materials that lose or change color in response to specific stimulus input resulting from a change in the electron states of molecules. The color changes phenomena can be differentiated based on types of an external stimulus such as thermochromic (color change caused by heat), photochromic (color change caused by light), magnetochromic (color change caused by magnetic field), and halochromic (color change caused by pH) 1–4 …”

Section: Introductionmentioning

confidence: 99%

Halochromic poly (lactic acid) film for acid base sensor

Yam

Rusli

Hamid

et al. 2020

J of Applied Polymer Sci

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A novel strategy to engineer biodegradable halochromic film based on poly (lactic acid) (PLA) for pH sensorial substances was presented. The effect of polyethylene glycol (PEG) compositions and dye amount on the efficiency of halochromic pH film was observed. The interactions between PLA, PEG, and dye was evidence by Fourier transform infrared. UV-VIS results indicated the sensitivity of the halochromic film through color changes. Mechanical performance was investigated by tensile testing to assess the potential of the halochromic film. It was found that the halochromic pH film has a clear color response from yellow to purple at pH 3-11 with a rapid response time within a minute. The results also revealed that varying content of PEG showed a significant effect on response time compared with varying dye compositions. PLA/PEG film and dye formed new interactions where PEG increased the free volume of PLA and made it possible for the PEG and the dye to diffuse and entrap between PLA chain. In term of the film strength, the addition of PEG and dye improved the flexibility of PLA film, which enables great potential in many applications such as medical, textile, and packaging.

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Colorimetric oxygen indicator films based on β‐cyclodextrin grafted chitosan/montmorillonite with redox system for intelligent food packaging

2022

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Oxygen is an important factor in food deterioration; thus, packaging, with an in-built oxygen indicator, has been widely developed. Here, a safer, natural product-based, colorimetric oxygen indicator film based on β-cyclodextrin grafted chitosan/montmorillonite with methylene blue/glucose system was fabricated.Methylene blue in the activated films was reduced to leuco-form (colourless) by glucose and reverted to blue with oxygen exposure. Glucose, as well as the reducing agent for methylene blue, crosslinked the chitosan. In addition, the grafting of β-cyclodextrin onto chitosan and the addition of montmorillonite as well as humidity led to the faster colour changes of the films. The colour recovery of films could delay by covering them with a poly(ethylene terephthalate) (PET) film. The activated films showed good storage stability at low temperature which is suitable for the package of refrigerated food products. The films had the potential to be used as natural-based colorimetric oxygen indicators for food packaging.

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Dual pH/thermal-dependent coloring polymeric dye through Mannich reaction of chitosan: Synthesis and characterization

Cited by 21 publications

References 40 publications

Stimuli‐Responsive, Self‐Healing, and Injectable Hydrogels with Dual‐Crosslinked Design from Phenolphthalein‐Grafted N‐Carboxyethyl Chitosan

Stimuli‐Responsive, Self‐Healing, and Injectable Hydrogels with Dual‐Crosslinked Design from Phenolphthalein‐Grafted N‐Carboxyethyl Chitosan

Halochromic poly (lactic acid) film for acid base sensor

Colorimetric oxygen indicator films based on β‐cyclodextrin grafted chitosan/montmorillonite with redox system for intelligent food packaging

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