Synthesis of poly(alkylaniline)s by aqueous chemical oxidative polymerization and their use as stimuli-responsive liquid marble stabilizer

Uda, Makoto; Higashimoto, Shinya; Hirai, Tomoyasu; Nakamura, Yoshinobu; Fujii, Syuji

doi:10.1016/j.polymer.2020.123295

Cited by 9 publications

(12 citation statements)

References 76 publications

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“…The decay time of the locomotion was 1.10 ± 0.25 s ( Figure S9 ), which was also similar to those determined for the LMs previously reported. 30 , 39 , 52 , 73 , 75 , 76 …”

Section: Resultsmentioning

confidence: 99%

Synthesis of Polypyrrole and Its Derivatives as a Liquid Marble Stabilizer via a Solvent-Free Chemical Oxidative Polymerization Protocol

et al. 2022

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Solvent-free chemical oxidative polymerizations of pyrrole and its derivatives, namely N -methylpyrrole and N -ethylpyrrole, were conducted by mechanical mixing of monomer and solid FeCl 3 oxidant under nitrogen atmosphere. Polymerizations occurred at the surface of the oxidant, and optical and scanning electron microscopy studies confirmed production of atypical grains with diameters of a few tens of micrometers. Fourier transform infrared spectroscopy studies indicated the presence of hydroxy and carbonyl groups which were introduced during the polymerization due to overoxidation. The polymer grains were doped with chloride ions, and the chloride ion dopant could be removed by dedoping using an aqueous solution of sodium hydroxide, which was confirmed by elemental microanalysis and X-ray photoelectron spectroscopy studies. Water contact angle measurements confirmed that the larger the alkyl group on the nitrogen of pyrrole ring the higher the hydrophobicity and that the contact angles increased after dedoping in all cases. The grains before and after dedoping exhibited photothermal properties: the near-infrared laser irradiation induced a rapid temperature increase to greater than 430 °C. Furthermore, dedoped poly( N -ethylpyrrole) grains adsorbed to the air–water interface and could work as an effective liquid marble stabilizer. The resulting liquid marble could move on a planar water surface due to near-infrared laser-induced Marangoni flow and could disintegrate by exposure to acid vapor via redoping of the poly( N -ethylpyrrole) grains.

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“…The decay time of the locomotion was 1.10 ± 0.25 s ( Figure S9 ), which was also similar to those determined for the LMs previously reported. 30 , 39 , 52 , 73 , 75 , 76 …”

Section: Resultsmentioning

confidence: 99%

Synthesis of Polypyrrole and Its Derivatives as a Liquid Marble Stabilizer via a Solvent-Free Chemical Oxidative Polymerization Protocol

et al. 2022

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“…Given the similarity of the velocity and decay time in both systems and smaller temperature‐based surface tension gradient, it is possible that another driving force acts on the LM. The dissolution of BEH dopant from the grain by the NIR laser irradiation could work to generate surface tension gradient 40,71 . Actually, the surface tension of the aqueous dispersion of the PPy‐BEH grains synthesized at molar ratio of 3/1 (0.1 wt%) decreased from 67.90 to 59.18 mN/m by heat treatment at 80°C for 1 h. The average force generated by the NIR irradiation, calculated using the Newton's equation of motion, was 4.13 μN.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of dioctyl sulfosuccinate‐doped polypyrrole grains by aqueous chemical oxidative polymerization and their use as light‐responsive liquid marble stabilizer

Osumi

Seike

Oyama

et al. 2021

J of Applied Polymer Sci

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Polypyrrole grains are synthesized by aqueous chemical oxidative polymerization using ferric chloride as an oxidant in the presence of bis(2‐ethylhexyl) sulfosuccinate sodium salt as both a dopant and a hydrophobizing agent. The resulting grain products are characterized in terms of their size, morphology, surface and bulk chemical compositions, hydrophilicity‐hydrophobicity balance, (photo) thermal property, and electrical conductivity. Scanning electron microscopy studies indicate that the grains are aggregates of atypical primary grains with submicrometer size. Elemental microanalysis and thermogravimetric analysis confirm that the polypyrrole is preferably doped with dioctyl sulfosuccinate compared with chloride ion, and dioctyl sulfosuccinate/chloride ion dopant ratio increases with an increase of bis(2‐ethylhexyl) sulfosuccinate sodium salt concentration in the polymerization systems. The grains show near‐infrared light‐to‐heat photothermal property, which is confirmed by thermography. The data obtained through X‐ray photoelectron spectroscopy indicate the presence of dioctyl sulfosuccinate dopants on the surface of the grains, and therefore the dried polypyrrole grains show hydrophobic character. The dried grains can work as a light‐responsive liquid marble (LM) stabilizer. Motions of the LM can be driven by near‐infrared laser irradiation‐induced Marangoni flow on planar air‐water surface. The release of internal liquid can be achieved by controlled disruption of the LM via external stimulus application.

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“…There has been increasing interest in the handling of liquid droplets with possible applications including microfluidics, which enable chemical reactions, medical analysis, separation and extraction of target analytes, water harvesting, and triboelectric generation. − LMs have been reported as one of the fascinating approaches to manipulating liquid droplets, because of their ability to encapsulate liquid materials and to release them on demand in response to an external stimulus. − Recently, we synthesized hydrophobic polyaniline (PANI) grains via an aqueous chemical oxidative polymerization protocol in the presence of hydrophobic dopant and have succeeded in the fabrication of LMs using the dried PANI grains as a stabilizer and water as an internal liquid . Furthermore, we demonstrated that transport of the LM over the planar water surface can be achieved on the basis of light-induced Marangoni flow.…”

Section: Introductionmentioning

confidence: 99%

Locomotion of a Nonaqueous Liquid Marble Induced by Near-Infrared-Light Irradiation

et al. 2021

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Micrometer-sized hydrophobic polyaniline (PANI) grains were synthesized via an aqueous chemical oxidative polymerization protocol in the presence of dopant carrying perfluoroalkyl or alkyl groups. The critical surface tensions of the PANIs synthesized in the presence of heptadecafluorooctanesulfonic acid and sodium dodecyl sulfate dopants were lower than that of PANI synthesized in the absence of dopant, indicating the presence of hydrophobic dopant on the grain surfaces. The PANI grains could adsorb to air–liquid interfaces, and aqueous and nonaqueous liquid marbles (LMs) were successfully fabricated using liquids with surface tensions ranging between 72.8 and 42.9 mN/m. Thermography studies confirmed that the surface temperature of the LMs increased by near-infrared light irradiation thanks to the photothermal property of the PANI, and the maximum temperatures measured for nonaqueous LMs were higher than that measured for aqueous LM. We demonstrated that transport of the LMs on a planar water surface can be achieved via Marangoni flow generated by the near-infrared light-induced temperature gradient. Numerical analyses indicated that the LMs containing liquids with lower specific heat and thermal conductivity and higher density showed longer path length per one light irradiation shot and longer decay time. This is because generated heat could efficiently transfer from the LMs to the water surface and larger inertial force could work on the LMs. The LMs could also move over the solid substrate thanks to their near-spherical shapes. Furthermore, it was also demonstrated that the inner liquids of the LMs could be released on site by an external stimulus.

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Synthesis of poly(alkylaniline)s by aqueous chemical oxidative polymerization and their use as stimuli-responsive liquid marble stabilizer

Cited by 9 publications

References 76 publications

Synthesis of Polypyrrole and Its Derivatives as a Liquid Marble Stabilizer via a Solvent-Free Chemical Oxidative Polymerization Protocol

Synthesis of Polypyrrole and Its Derivatives as a Liquid Marble Stabilizer via a Solvent-Free Chemical Oxidative Polymerization Protocol

Synthesis of dioctyl sulfosuccinate‐doped polypyrrole grains by aqueous chemical oxidative polymerization and their use as light‐responsive liquid marble stabilizer

Locomotion of a Nonaqueous Liquid Marble Induced by Near-Infrared-Light Irradiation

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