Synthesis of novel tert-butyl substituted fluorans and an investigation of their thermochromic behavior

Oh, Wooram; Angupillai, Satheshkumar; Muthukumar, P.; So, Hee-Soo; Son, Young-Α

doi:10.1016/j.dyepig.2016.01.036

Cited by 31 publications

(15 citation statements)

References 28 publications

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“…At a low temperature (25 °C), the BCP in the thermochromic colorant reacts with stearic acid to form an ion pair composed of anionic stearic acid and cationic BCP (BCP + ) (Figure ). In these circumstances, the central carbon atom of BCP in the thermochromic colorant is in the form of a sp 2 hybrid orbital , and BCP exists as a quinoid conjugated structure and presents as a dark red colour. The colour depth of the thermochromic colorant decreases as the temperature increases, and the colour changes clearly from red to tangerine at the mp of hexadecanol in the thermochromic colorant (45 °C).…”

Section: Resultsmentioning

confidence: 99%

“…Leuco‐dye thermochromic colorant consists of three components, namely colour former, colour developer and solvent. The colour former is an electron‐donating compound, for instance spirolactone, fluorane or spiropyran . The colour developer is an electron‐accepting compound such as bisphenol A, hydroxycoumarin, an alkyl gallate or phenol.…”

Section: Introductionmentioning

confidence: 99%

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A sultone‐based reversible dark red‐yellow conversion thermochromic colorant with adjustable switching temperature

Wan

Zeng

et al. 2018

Coloration Technology

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A reversible, adjustable thermochromic colorant with bichromatic conversion from dark red (cool state) to yellow (heat state) was prepared using bromocresol purple (BCP) as colour former. The thermochromic behaviour of this colorant was investigated during the heating‐cooling cycle, including the colour depth, colour difference and switching temperature. The mechanism of thermochromic colorant switching between dark red and yellow originated from the transformation of the conjugated structures of BCP, which was confirmed by infrared spectrometry. The switching temperature can be flexibility adjusted between 13–46 °C by mixing solvents according to Schröder's equation, which was demonstrated by differential scanning calorimetry measurement. The thermochromic colorant presented good reversible thermochromic performance with stable changes in colour parameters for 50 heating‐cooling cycles. This sultone‐based reversible dark red‐yellow conversion thermochromic colorant is suitable for application as thermal‐indicating material under various conditions.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A sultone‐based reversible dark red‐yellow conversion thermochromic colorant with adjustable switching temperature

Wan

Zeng

et al. 2018

Coloration Technology

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“…To produce microcapsules with shell/core of 0.5/1, a 33.33 g of TS as core material was added to 160 mL of water at 50 C and emulsified using 2 g of PEG1000 as surfactant. Then, a 16.66 g of methyl methacrylate monomer, a 1.66 g of glycidyl methacrylate (10% of the amount of MMA), a 2.5 g of crosslinker (EGDM), 1 mL of freshly prepared FeSO 4 .7H 2 O solution (prepared by dissolving a 0.3 g of FeSO 4 .7H 2 O in 200 mL of distilled water), and a 0.25 g of ammonium persulphate were added to the emulsion and it was stirred at 2000 rpm for 30 min. Then, a 0.25 g of sodium thiosulfate (Na 2 S 2 O 3 5H 2 O) and 1.00 g of 70% tert-butyl hydroperoxide solution were added, and temperature was increased to 80 C in order to initiate addition polymerization reaction.…”

Section: Microencapsulation Of the Tsmentioning

confidence: 99%

“…Thermochromic materials are intriguing substances, which exhibit reversibly color change depending on change of temperature . Because of their temperature sensing property, thermochromic materials have attracted considerable interest and are tested to determine their potential in many products and application areas like thermal indicators, optical storage devices, other luminescent switches, building coatings and cement, security printing plastic strip thermometers, food packaging, medical thermography, nondestructive testing of engineered articles, electronic circuitry, and pharmaceutical industry . Recently, textile industry has become one of the most interested sectors to thermochromic materials.…”

Section: Introductionmentioning

confidence: 99%

Preparation of poly(methyl methacrylate‐co‐ethylene glycol dimethacrylate‐co‐glycidyl methacrylate) walled thermochromic microcapsules and their application to cotton fabrics

Tözüm

Alkan

Aksoy

2019

J of Applied Polymer Sci

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This study focused on fabrication of the thermochromic microcapsules and their application to the cotton fabric. In this study, thermochromic systems composed of crystal violet lactone, bisphenol A, and 1‐tetradecanol were prepared and microencapsulated by emulsion polymerization method in poly(methyl methacrylate‐co‐ethylene glycol dimethacrylate‐co‐glycidyl methacrylate) wall. The microcapsules were analyzed by Fourier transform infrared spectroscopy, scanning electron microscope, transmission electron microscope, differential scanning calorimetry, and thermogravimetric analysis. Their thermoregulating property was tested by T‐history test. The results revealed that microcapsules with smooth surfaces, core–shell structured, and spherical shape were successfully produced. The latent heat storage capacity of the microcapsules decreased from 202 J g−1 to 167 J g−1 when their shell/core ratio changed from 0.5/1 to 2/1. Microcapsules were adequately had sufficient thermal resistance to the temperatures they will encounter during their application to textile products and their usage. According to the UV–visible spectroscopy analysis and color measurements, the microcapsules exhibited reversible color change from blue to colorless and vice versa. Besides, the microcapsule impregnated fabric was able to absorb latent heat energy of 21.79 J g−1 at around 35 °C and had cooling effect. According to the colorimetric parameters, the fabric was at blue color at room temperature and became colorless when heated to the temperature above the melting point of thermochromic system. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2020, 137, 48815.

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“…Among various thermochromic materials, thermochromic leuco dye is mostly reported as thermal regulation materials based on its color change. It consists of color former, color developer and hydrophobic, nonvolatile organic solvents, which possesses an excellent reversibility . The thermochromic transition takes place around the melting point of the solvents .…”

Section: Introductionmentioning

confidence: 99%

Raspberry‐Shaped Thermochromic Energy Storage Nanocapsule with Tunable Sunlight Absorption Based on Color Change for Temperature Regulation

Wan

Wang

Chen

et al. 2019

Small

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A novel raspberry‐shaped thermochromic energy storage nanocapsule (RTESN) is successfully designed and fabricated with switchable sunlight absorption capacity based on color change for temperature regulation. The RTESN is developed by grafting amino‐modified silica shell thermochromic nanoparticles (amino‐TLD@SiO2) on the surface of epoxy‐functionalized energy storage nanocapsules (paraffin@PSG), with a total particle size about 450 nm. RTESN exhibits a deep color under low temperatures, which can absorb sunlight for heating. During the continuous thermal energy supply, paraffin@PSG is capable of storing thermal energy owing to its large latent heat capacity of 118.7 J g–1, thereby maintaining the slow temperature increase. When the temperature is higher than the phase change temperature of paraffin@PSG, the color of amino‐TLD@SiO2 turns to white with more reflection of sunlight so that it reduces the absorption of thermal energy and prevents the further increase of temperature. The thermal regulation behavior is confirmed by setting up a wooden house with the surface covered with RTESN. Compared with the blank wooden house, the RTESN covered wooden house (RTESN‐H) displays thermal insulation performances during heating and cooling with a maximum temperature difference of 7 °C.

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Synthesis of novel tert-butyl substituted fluorans and an investigation of their thermochromic behavior

Cited by 31 publications

References 28 publications

A sultone‐based reversible dark red‐yellow conversion thermochromic colorant with adjustable switching temperature

A sultone‐based reversible dark red‐yellow conversion thermochromic colorant with adjustable switching temperature

Preparation of poly(methyl methacrylate‐co‐ethylene glycol dimethacrylate‐co‐glycidyl methacrylate) walled thermochromic microcapsules and their application to cotton fabrics

Raspberry‐Shaped Thermochromic Energy Storage Nanocapsule with Tunable Sunlight Absorption Based on Color Change for Temperature Regulation

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