Synthesis and Surface Properties of Novel Fluoroalkylated Flip-Flop-Type Silane Coupling Agents

Sawada, Hideo; Ikematsu, Yuka; Kawase, Tokuzō; Hayakawa, Yoshio

doi:10.1021/la951041p

Cited by 42 publications

(41 citation statements)

References 14 publications

(5 reference statements)

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“…The relatively higher feed amounts (0.44-0.88 mmol) of Glu-Si(OEt) 3 in the nanocomposite preparation illustrated in Scheme 1 would enable the smooth surface arrangement of the hydrophilic gluconamide segments to provide the completely superhydrophilic surface through the flip-flop motion between the fluoroalkyl groups and gluconamide segments in the nanocomposites. A similar flip-flop motion between longer fluoroalkyl groups and hydrophilic segments has been already reported to exhibit the hydrophilic characteristic with an oleophobic property on the modified surfaces [24][25][26][27][28]. Therefore, the nanocomposites which were prepared under relatively lower feed amounts (0.03 mmol) of Glu-Si(OEt) 3 , can supply a highly oleophobic/superhydrophobic characteristic (dodecane and water contact angle values: 112 and 180 degrees) on the modified surface, due to the lower content of hydrophilic gluconamide segments in the nanocomposites.…”

Section: Resultssupporting

confidence: 73%

Preparation of Fluoroalkyl End-Capped Vinyltrimethoxysilane Oligomeric Silica Nanocomposites Containing Gluconamide Units Possessing Highly Oleophobic/Superhydrophobic, Highly Oleophobic/Superhydrophilic, and Superoleophilic/Superhydrophobic Characteristics on the Modified Surfaces

et al. 2017

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Fluoroalkyl end-capped vinyltrimethoxysilane oligomer [R F -(CH 2 -CHSi(OMe) 3 ) n -R F (R F -(VM) n -R F )] undergoes the sol-gel reaction in the presence of N-(3-triethoxysilylpropyl)gluconamide [Glu-Si(OEt) 3 ] under alkaline conditions to afford the corresponding fluorinated oligomeric silica nanocomposites containing gluconamide units [R F -(VM-SiO 3/2 ) n -R F /Glu-SiO 3/2 ]. These obtained nanocomposites were applied to the surface modification of glass to provide the unique wettability characteristics such as highly oleophobic/superhydrophobic and highly oleophobic/superhydrophilic on the modified surfaces under a variety of conditions. Such a highly oleophobic/superhydrophobic characteristic was also observed on the modified PET (polyethylene terephthalate) fabric swatch, which was prepared under similar conditions, and this modified PET fabric swatch was applied to the separation membrane for the separation of the mixture of fluorocarbon oil and hydrocarbon oil. The R F -(VM-SiO 3/2 ) n -R F /Glu-SiO 3/2 nanocomposites, which were prepared under lower feed amounts of basic catalyst (ammonia), were found to cause gelation in water. Interestingly, it was demonstrated that these gelling nanocomposites are also applied to the surface modification of the PET fabric swatch to give a highly oleophobic/superhydrophobic characteristic on the surface. On the other hand, the modified glass surfaces treated with the corresponding nanocomposite possessing no gelling ability were found to supply the usual hydrophobic characteristic with a highly oleophobic property. More interestingly, the wettability change on the modified PET fabric swatch from highly oleophobic to superoleophilic was observed, and remained superhydrophobic after immersing the modified PET fabric swatch into water.

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Section: Resultssupporting

confidence: 73%

Preparation of Fluoroalkyl End-Capped Vinyltrimethoxysilane Oligomeric Silica Nanocomposites Containing Gluconamide Units Possessing Highly Oleophobic/Superhydrophobic, Highly Oleophobic/Superhydrophilic, and Superoleophilic/Superhydrophobic Characteristics on the Modified Surfaces

et al. 2017

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“…When oil droplets were placed, the hydrophilic units were pushed flat on the surface allowing fluoroalkyl units (Rf) to assume erectile positions -hence making the surface more oilrepellent. Alterations in the positioning of Rf and hydrophilic units are referred to as the "flip-flop" characteristic of FAAO-incorporated coating materials 13) . The spin coating technique employs a centrifugal force to spread the coating material homogenously over the entire substrate to form a thin and smooth surface.…”

Section: Discussionmentioning

confidence: 99%

“…Further on wettability, it has been reported that the superhydrophobicity and superhydrophilicity of surfaces are key properties for the fabrication of self-cleaning surfaces 10) . In 1990s, Sawada et al introduced a newly categorized chemical compound with a self-cleaning property, constituting the first generation of current "fluoroalkylated acrylic acid oligomer" (FAAO) [11][12][13] . A FAAO is generally synthesized by the polymerization of acrylic acid with difluoroalkanoyl peroxides (Fig.…”

Section: Introductionmentioning

confidence: 99%

Inhibition of Biofilm Formation using Newly Developed Coating Materials with Self-cleaning Properties

et al. 2008

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The purpose of this study was to evaluate the inhibition of biofilm formation on newly developed coating materials with self-cleaning properties. A series of experimental coating materials containing fluoroalkylated acrylic acid oligomer (FAAO) were applied to resin composite substrates. The surfaces of the coating materials were analyzed by X-ray photoelectron spectroscopy (XPS) and contact angle measurement. Biofilm formation on the surface was assessed using Streptococcus mutans biofilms inside an oral simulator in vitro. The results indicated that an increase in the concentration of FAAO in the coating materials enhanced surface hydrophilicity and oil-repellency. Biofilm assays demonstrated that the amount of biofilm retained on the coating materials gradually decreased when the concentration of FAAO increased in the materials. It was concluded that the coating materials incorporated with FAAO possessed self-cleaning properties and displayed signs of inhibiting biofilm formation on their surfaces.

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“…This is due to the higher surface tension of water, which results in the respective Young's contact angles 20 satisfying θ water > θ oil . A few studies 14,[21][22][23][24][25][26] have reported surfaces where θ water < θ oil , which was achieved by using specific interactions between water and the substrate to lower the solid-liquid interfacial tension (γ sl ). However, with two exceptions 14,25 all such surfaces were oleophilic.…”

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confidence: 99%

Hygro-responsive membranes for effective oil–water separation

et al. 2012

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There is a critical need for new energy-efficient solutions to separate oil-water mixtures, especially those stabilized by surfactants. Traditional membrane-based separation technologies are energy-intensive and limited, either by fouling or by the inability of a single membrane to separate all types of oil-water mixtures. Here we report membranes with hygro-responsive surfaces, which are both superhydrophilic and superoleophobic, in air and under water. our membranes can separate, for the first time, a range of different oil-water mixtures in a singleunit operation, with >99.9% separation efficiency, by using the difference in capillary forces acting on the two phases. our separation methodology is solely gravity-driven and consequently is expected to be highly energy-efficient. We anticipate that our separation methodology will have numerous applications, including the clean-up of oil spills, wastewater treatment, fuel purification and the separation of commercially relevant emulsions.

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Synthesis and Surface Properties of Novel Fluoroalkylated Flip-Flop-Type Silane Coupling Agents

Cited by 42 publications

References 14 publications

Preparation of Fluoroalkyl End-Capped Vinyltrimethoxysilane Oligomeric Silica Nanocomposites Containing Gluconamide Units Possessing Highly Oleophobic/Superhydrophobic, Highly Oleophobic/Superhydrophilic, and Superoleophilic/Superhydrophobic Characteristics on the Modified Surfaces

Preparation of Fluoroalkyl End-Capped Vinyltrimethoxysilane Oligomeric Silica Nanocomposites Containing Gluconamide Units Possessing Highly Oleophobic/Superhydrophobic, Highly Oleophobic/Superhydrophilic, and Superoleophilic/Superhydrophobic Characteristics on the Modified Surfaces

Inhibition of Biofilm Formation using Newly Developed Coating Materials with Self-cleaning Properties

Hygro-responsive membranes for effective oil–water separation

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