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72 lines
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"id": 1,
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"chunk": "# Robust UV-Curable Dual-Cross-Linked Coating with Increased Transparency, Long-Term Antifogging, and Efficient Antibacterial Performances \n\nLina Zhang, Kai Feng,\\* Yizhe Liu, Fangrong Wu, Yubo Liu, Bo Yu, Xiaowei Pei, Lijia Liu, Chunhong Zhang, Yang Wu,\\* and Feng Zhou \n\nCite This: ACS Appl. Polym. Mater. 2024, 6, 6645−6657",
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"category": " Abstract"
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},
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"id": 2,
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"chunk": "# ACCESS \n\nMetrics & More \n\nArticle Recommendations s\\*ı Supporting Information \n\nABSTRACT: Antifogging coatings are urgently needed in daily life. However, current research efforts seldom focus on enhancing the mechanical wear resistance of coatings or investigating their antifogging properties under wet and dry conditions. Herein, a robust dual-cross-linked polymeric antifogging coating was developed through the UV curing of poly[(methacryloxyethyl)dimethylheptylammonium bromide−acrylic acid] (pMDHAB− AA) and poly(ethylene glycol) diacrylate (PEGDA). Taking advantage of the dual-crosslinked structure and the delicate balance of hydrophilic−hydrophobic components in pMDHAB−AA, the coating presented durable antifogging performances, including longtime antifogging in hot vapor and numerous antifogging in an alternation of wetting and drying and robust mechanical wear resistance. In addition, based on the hygroscopic nature of the quaternary ammonium groups, the coating was endowed with oleophobicity underwater, an ultralow friction coefficient, and antibacterial and resistance-to-bacterialadhesion performances. More importantly, the antifogging coating plays a crucial role in enhancing substrate transparency by reducing the diffuse reflection. This prepared material addresses current concerns related to antifogging coatings and holds significant potential for applications in various fields, including optical glass, medical devices, agricultural films, etc. \n\n \n\nKEYWORDS: transparent, dual-cross-linked, multifunctional, antifogging, wear resistant",
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"category": " Abstract"
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"id": 3,
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"chunk": "# INTRODUCTION \n\nTransparent substrates are widely used in both daily life and optical analysis instruments.1,2 However, unforeseen variations in the temperature and humidity lead to the condensation of water droplets on the transparent substrate surfaces and the formation of fog.3−5 The presence of fog droplets significantly degrades the light transmittance, which not only leads to considerable inconveniences in daily life but also poses numerous potential safety concerns.6−10 Besides, in agriculture, the formation of fog on greenhouse films will reduce the transmittance of light, seriously affecting plant photosynthesis and thereby decreasing the crop yields.11−13 In medical applications, such as endoscopic, laparoscopic, and medical goggles, the occurrence of fog can impair the operator’s vision, potentially hindering the normal course of operation. Therefore, the development of novel technologies or materials capable of effectively preventing or reducing fogging has garnered significant attention from a wide scope of researchers.7,14 \n\nCurrently, diverse strategies have been proposed by researchers to address the issue of fogging.3,9,15,16 The first strategy is manipulating both the ambient temperature and the surface temperature of the substrate to reduce the temperature difference, thereby achieving the goal of antifogging.8,17 However, this method has been significantly limited due to its high energy consumption and weak environmental adaptation.18,19 Another widely employed strategy is fabricating an antifogging coating.20−22 However, commonly prepared superhydrophilic or superhydrophobic antifogging coatings suffer from several drawbacks. For example, superhydrophilic materials like surfactants,10,23 hydrophilic polymer brushes,24,25 sol−gel coatings,26,27 etc., fail to maintain long-term antifogging properties and often exhibit poor mechanical properties. For superhydrophobic antifogging coating, tedious processes and intricate nanostructures are typically involved. The mechanical vulnerability of the nanostructured surface inevitably limits its practical application.28−30 Consequently, in recent years, amphiphilic coatings (e.g., polymer coatings with a combination of hydrophilic quaternary ammonium groups and hydrophobic chains) have received wide attention in antifogging applications due to their ability to control the hydrophilic/hydrophobic balance,31−35 while previously reported conventional amphiphilic coatings often neglected longterm antifogging effectiveness and abrasion resistance, which are critical concerns for practical antifogging coating applications. \n\n \n\nHerein, we present a highly transparent multifunctional antifogging coating through a delicate hydrophilic/hydrophobic balance using a UV-assisted cross-linking method. The incorporation of quaternary ammonium groups renders the coating with excellent antibacterial, antistatic, oloephobicity performances underwater and upon thousands of friction cycles in both air and water without any influence of antifogging. The stability and wear resistance of the coating was attributed to the dual-cross-linked structure formed between the pMDHAB−AA−aziridine network and PEGDA network. In addition, the hygroscopicity and stability endowed the coating with a long-term antifogging ability. Importantly, the antifogging coating enhances the transparency of a polyolefin (PO) film by reducing diffuse reflection, thereby improving the photosynthetic efficiency of crops. Hence, there is a significant demand for the application of this novel multifunctional antifogging coating in practical scenarios.",
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"category": " Introduction"
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"id": 4,
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"chunk": "# EXPERIMENTAL SECTION \n\nMaterials. 2-(Dimethylamino)ethyl methacrylate (DMAEMA, $99\\%$ ), $^{2,2^{\\prime}}$ -azobis(2-methylpropionitrile) (AIBN, $98\\%$ ), 1-bromoheptane, pentaerythritol tris[3-(1-aziridinyl)propionate] (APA, $99\\%$ ), poly(ethylene glycol) diacrylate (PEGDA), and UV initiator 2- hydroxy- $\\cdot4^{\\prime}$ -(2-hydroxyethoxy)-2-methylpropiophenone $(98\\%)$ were purchased from Shanghai Macklin Biochemical Co., Ltd. AIBN was recrystallized from ethanol before use. Acrylic acid (AA, $>99\\%$ ) was purchased from Aladdin. Solvents, including dichloromethane, ethyl acetate, toluene, hexane, acetonitrile, and so forth, were obtained from Sinopharm Chemical Reagent Co., Ltd. $o$ -Xylene $(98\\%)$ was purchased from XiYa Chemical Technology (Shandong) Co., Ltd. Except for AIBN, all chemicals were used as received. \n\nSynthesis of the Prepolymer pDMAEMA−AA Copolymer. The copolymer was synthesized through conventional free-radical polymerization using the following procedure. A total of $_{\\textrm{40}\\textrm{g}}$ of DMAEMA and ${4\\mathrm{g}}$ of AA were added to a $250~\\mathrm{mL}$ flask, followed by the addition of $\\boldsymbol{44}\\mathrm{~g~}$ of $o$ -xylene and $0.44\\mathrm{~g~}$ of AIBN (1 wt $\\%$ with respect to the total monomer mass) as the thermal initiator. The polymerization was conducted at $80~^{\\circ}\\mathrm{C}$ in an oil bath with magnetic stirring for $^{12\\mathrm{~h~}}$ . After the reaction was finished, the final copolymer was precipitated by hexane, and then the pure pDMAEMA−AA copolymer was obtained by washing three times with hexane and drying in a vacuum oven for $24\\mathrm{~h~}$ at $60~^{\\circ}\\mathrm{C}$ . \n\nPreparation of Quaternary Ammonium Salt. Quaternary ammonium salt was prepared by quaternization of pDMAEMA−AA copolymer with 1-bromoheptane. A total of $_{4\\textrm{g}}$ of pDMAEMA−AA copolymer and $6.24~\\mathrm{g}$ of 1-bromoheptane were introduced to $30~\\mathrm{mL}$ of acetonitrile. Subsequently, the mixture underwent thorough stirring at $80~^{\\circ}\\mathrm{C}$ for $^{12\\mathrm{~h~}}$ to obtain a faint-yellow solution. Next, the solid residues were collected through vacuum rotary evaporation after the flask was cooled to room temperature. The resulting products were purified and washed with hexane three times to remove the monomer and impurity that remained unreacted. Finally, the product was dried in a vacuum oven at $60~^{\\circ}\\mathrm{C}$ for $^{24}\\mathrm{h},$ and then the pure quaternary ammonium copolymer (pMDHAB−AA) was acquired. \n\nPreparation of the Dual-Cross-Linked pMDHAB−AA/PEGDA Coating and Single-Cross-Linked APA and PEGDA Coatings. Before the dual-cross-linked coating was prepared, the poly(ethylene terephthalate) (PET) film was ultrasonically cleaned with ethanol for $30\\ \\mathrm{min},$ , followed by drying in an oven. First, $1.2\\mathrm{~g~}$ of quaternary ammonium copolymer was dissolved in $\\textbf{8g}$ of deionized water at room temperature with magnetic stirring for $^{12\\mathrm{~h~}}$ . Then $0.236\\mathrm{~g~}$ of APA $\\big(}{}^{1}/}_{3}\\mathrm{mol}$ of the copolymer) was added, and the mixture was stirred for $^{2\\mathrm{h},}$ followed by the addition of $0.024\\ \\mathrm{g}$ of PEGDA (2.0 wt $\\%$ with respect to the copolymer) and $0.0024\\ \\mathrm{g}$ of 2-hydroxy- $\\cdot4^{\\prime}$ -(2- hydroxyethoxy)-2-methylpropiophenone (10 wt $\\%$ relative to PEGDA) with magnetic stirring for $^\\mathrm{~1~h~}$ to obtain a homogeneous solution. Then this solution was drop-coated on a clean PET film that was treated with oxygen plasma for $\\textsf{S m i n}$ to completely clean the surfaces and remove organic pollutants. Finally, the coating underwent UV curing using a lamp emitting light at $365~\\mathrm{nm}$ with a power of $300~\\mathrm{W}$ for $30\\ \\mathrm{min}$ , resulting in the formation of a UVcurable pMDHAB−AA coating. The single PEGDA coating was prepared using the same UV-curing method but without pMDHAB− AA and APA. For the single APA coating, the PEGDA and photoinitiator were not involved, and it was cured at room temperature for $24\\mathrm{~h~}$ . \n\nCharacterization. The surface chemical compositions of the coating were characterized by X-ray photoelectron spectroscopy (XPS; Thermo Escalab 250XI). Fourier transform infrared (FTIR) spectroscopy was measured on a Nicolet IS 10 spectrometer for characterizing the functional groups of the synthesized copolymer in the range of $500{-}4000~\\mathrm{cm^{-1}}$ . $\\mathrm{^{1}H}^{\\cdot}$ NMR spectra were recorded on a Bruker AVANCE III 600 M instrument with deuterated dimethyl sulfoxide (DMSO- $d_{6.}$ ) as the solvent. The thermal stability was collected by thermogravimetric analysis (TGA; Netzsch STA 449 F5/ F3 Jupiter analyzer) from 20 to $800^{\\circ}\\mathrm{C}$ at a heating rate of $10~{^\\circ}\\mathrm{C}/\\operatorname*{min}$ under a $\\Nu_{2}$ atmosphere. The surface topography and thickness of the pDMAEMA−AA coating were observed by atomic force microscopy (AFM; Bruker Dension Icon) and field-emission scanning electron microscopy (SEM; Tescan, CLARA GHM). The coatings for SEM were sputter-coated for $180\\ s$ with gold to ensure the coatings had good conductivity. The elemental distribution on the coating surface was obtained by energy-dispersive spectroscopy (EDS). UV−vis spectrophotometry (UV-2600, GGC003) was tested to confirm the transparency of samples in the range of a visible-light wavelength from 400 to $800\\ \\mathrm{nm}$ . Water contact angles (WCAs) were recorded with 5 $\\mu\\mathrm{L}$ of deionized waterdrops. Microscopic images were collected on a research-level intelligent fully automatic inverted fluorescent metallographic microscope (DMi8A, GGC006). \n\nAntifogging Test. The antifogging properties were conducted based on both hot-vapor and cold-warm conditions, separately. For the hot-vapor antifogging test, samples were placed over hot vapor (upon $5\\ {\\mathrm{cm}}\\ {\\mathrm{high}}$ ) with the coated surface facing down by placing it on a $250~\\mathrm{mL}$ glass beaker that contained hot water ( $\\sim60~^{\\circ}\\mathrm{C},$ $100\\%$ relative humidity), and the glass beaker was placed on a hot plate to maintain the temperature. Then digital photographs of the fogging behavior were taken at different time intervals. For the cold-warm antifogging test, samples were first stored in a freezer at $-20{}^{\\circ}\\mathrm{C}$ for 30 min and then transferred immediately to ambient conditions $(\\sim20$ ${}^{\\circ}{\\bf C},$ $55\\%$ relative humidity), and the transparencies of the samples were recorded after 5 s by a camera. In addition, light transmission data were collected on a UV−vis spectrophotometer in the wavelength region of $400{-}800~\\mathrm{nm}$ to quantitatively characterize the antifogging performances of the samples. \n\nAntibacterial Test. Antibacterial tests were carried out according to a standard antibacterial susceptibility test protocol.36,37 Gramnegative Escherichia coli and Gram-positive Staphylococcus aureus were chosen as representative bacteria to test the antibacterial activity of the copolymer and the dual-cross-linked pMDHAB−AA coating. The minimum inhibitory concentrations (MICs) of the synthesized pMDHAB−AA copolymer were first determined. In this work, 4096 $\\mu\\mathrm{g}$ of the pMDHAB−AA copolymer was first dissolved in $2{\\mathrm{~mL~}}$ of Mueller−Hinton broth (MHB) and then diluted by a continuous 2- fold method to obtain a series of copolymer solutions with different concentrations. Bacteria were also diluted immediately to obtain a concentration of $1\\times10^{6}\\mathrm{CFU/mL}$ of the suspension with a decimal dilution method. A total of $100~\\mu\\mathrm{L}$ of copolymer solution with a certain concentration and $100~\\mu\\mathrm{L}$ of bacterial suspension ( $\\mathit{\\Omega}_{1\\times10^{6}}$ $\\mathrm{CFU/mL}$ ) were added to each well of a 96-well plate. A total of 200 $\\mu\\mathrm{L}$ of MHB was set as the negative control and $100\\mu\\mathrm{L}$ of MHB with \n\n \nFigure 1. (a) Preparation process of the pMDHAB−AA copolymer. (b) FTIR spectrum of the pMDHAB−AA copolymer. (c) $^{1}\\mathrm{H}$ NMR spectrum of the quaternary ammonium polymer pMDHAB−AA. (d) Full XPS spectra of the PET and pMDHAB−AA copolymer. (e) Thermal weight loss of the pDMAEMA−AA and pMDHAB−AA copolymers. \n\n$100\\mu\\mathrm{L}$ of bacterial suspension were used as the positive control. After the 96-well plate was incubated at $37^{\\circ}\\mathrm{C}$ for $24\\mathrm{h}$ with a speed of 100 rpm, the optical density (OD) at $600\\ \\mathrm{nm}$ of the microorganism solutions was recorded by an enzyme standard instrument. Each experiment was measured in triplicate. The bacterial growth inhibition rate was calculated by the following equation: \n\n$$\n=\\frac{\\mathrm{OD}_{\\mathrm{positive\\control}}-\\mathrm{OD}_{\\mathrm{sample}}}{\\mathrm{OD}_{\\mathrm{positive\\control}}-\\mathrm{OD}_{\\mathrm{negative\\control}}}\\times100\n$$ \n\nA zone-of-inhibition test was conducted to determine the antibacterial ability of the dual-cross-linked pMDHAB−AA coating. Briefly, the bacterial suspension was diluted with pure MHB to obtain a concentration of approximately $1\\times10^{6}\\ \\mathrm{CFU/mL}$ . After dilution, the bacterial suspension $(100~\\mu\\mathrm{L})$ was carefully applied to a lysogeny broth (LB) culture plate uniformly, and then the dual-cross-linked pMDHAB−AA coatings with diameter of $\\sim1\\ \\mathrm{cm}$ were placed on the lawns, and the coating layer was in contact with the LB agar. After 24 h of incubation at $37^{\\circ}\\mathrm{C},$ the inhibition zone was recorded by a camera. As a comparison, the blank PET film was observed under the same conditions. Furthermore, the antibacterial ability of the dualcross-linked pMDHAB−AA coating was further evaluated using the spread plate method. The PET films and the coatings $(2\\ \\mathrm{cm}\\times2\\ \\mathrm{cm})$ were placed on a 24-well plate, then $200\\mu\\mathrm{L}$ of bacterial suspension (1 $\\times10^{6}\\mathrm{CFU/mL},$ ) was added, and the resulting solution was incubated in a shaker at $37^{\\circ}\\mathrm{C}$ at a speed of $100~\\mathrm{rpm}$ for $24\\mathrm{~h~}$ . After incubation, $30~\\mu\\mathrm{L}$ of bacterial suspension was plated onto sterile LB agar culture plates, and the plates were incubated at $37~^{\\circ}\\mathrm{C}$ for $24\\mathrm{~h~}$ . After that, growth of the bacteria was recorded by a camera. In addition, the morphology and adhesion of the bacteria were observed by SEM. Briefly, $500\\mu\\mathrm{L}$ of bacterial suspension was dropped onto the PET and dual-cross-linked pMDHAB−AA coating on a 24-well plate, respectively, and then incubated for $^\\textrm{\\scriptsize4h}$ at $37~^{\\circ}\\mathrm{C}$ in a shaker. The samples were washed with phosphate-buffered saline (PBS) gently to remove free-floating bacteria. After that, the bacteria were fixed with a mixture solution that consisted of $5\\mathrm{mL}$ of a $2.5\\%$ glutaraldehyde fixed solution, $20~\\mathrm{mL}$ of deionized water, and $25~\\mathrm{mL}$ of PBS at $4^{\\circ}\\mathrm{C}$ for $^{2\\mathrm{h},}$ followed by rinsing with PBS again. Then the PET and dual-crosslinked pMDHAB−AA coating with bacteria were dehydrated with a graded ethanol series (25, 50, 75, 95, and $100\\%$ ) in $15~\\mathrm{min}$ for each concentration and dried in air. Before imaging, the samples were sprayed with gold by an ion sputter coater (GVC-2000) for $180\\ s$ . \n\n \nFigure 2. (a) Preparation process of the dual-cross-linked antifogging coating. (b) Visible transmittance spectra of the bare PET and dual-crosslinked pMDHAB−AA coating. (c) Surface SEM images, (d) AFM images, and (e) EDS analysis of the dual-cross-linked pMDHAB−AA coating. \n\n \nFigure 3. (a) Variation of the WCA values on the dual-cross-linked pMDHAB−AA coating surface in air for $1000\\ s$ . (b) Schematic diagram of hydrophobic−hydrophilic conversion of the dual-cross-linked pMDHAB−AA coating. (c) Contact angle of organic solvents on the dual-crosslinked pMDHAB−AA coating surface underwater. \n\nFriction Test. The wear resistance of the dual-cross-linked pMDHAB−AA coating was measured by an alcohol rubber abrasion test machine (model 339) in air. As for the method, briefly, polyester cloth was used as the upper friction pair, and the bare PET films covered with the dual-cross-linked pMDHAB−AA coating were subjected to different reciprocating friction cycles under a load of $1\\mathrm{N}$ . Then the WCAs of the coating surface were measured after 0, 2000, 4000, 6000, 8000, 10000, and 12000 friction cycles, separately. To evaluate the performance stability after friction, the antifogging property of the dual-cross-linked pMDHAB−AA coating after 12000 friction cycles was tested. In addition, the wear resistance of the pMDHAB−AA coating was conducted on a conventional ball-on-desk reciprocating friction tester (TRB3 tribometer) in water surroundings, and the poly(dimethylsiloxane) (PDMS) hemisphere with a diameter of $6~\\mathrm{mm}$ was employed as an upper friction pair.38",
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"category": " Materials and methods"
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"id": 5,
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"chunk": "# RESULTS AND DISCUSSION \n\nPreparation and Characterization of the Copolymer of pMDHAB−AA. The chemical reaction equation is shown in Figure 1a, and the preparation process of the pMDHAB− AA copolymer is as follows. Initially, pDMAEMA−AA was synthesized through a thermally triggered free-radical polymerization reaction involving DMAEMA and AA units. Then, the copolymer was quaternized by 1-bromoheptane to alter the hydrophobic/hydrophilic balance. The chemical structure of the pMDHAB−AA copolymer was confirmed by FTIR and $\\mathrm{^{1}H}$ NMR spectra. As shown in Figure 1b, the absorption peak at $1160.7~\\mathrm{{\\dot{cm}}^{-1}}$ corresponded to the $\\mathrm{C-N}$ stretching of the quaternary ammonium group, and the absorption peak at $\\bar{17}25.7\\ \\mathrm{cm}^{-1}$ is attributed to the $\\scriptstyle{\\mathrm{C}}={\\mathrm{O}}$ stretching vibration of the ester group. The peaks at 2933.8 and $2866.0\\ \\mathrm{cm^{-1}}$ signified the $\\mathrm{C-H}$ stretching vibration of the alkyl group. Moreover, the characteristic peaks at 3431.0 and $1637.\\dot{1}\\mathrm{{\\cm}^{\\bar{-}1}}$ resulted from the stretching and bending vibrations of water molecules, respectively. The peaks at 1385.7 and $922.9~\\mathrm{{cm}^{-1}}$ were attributed to the hydroxyl stretching vibration of AA. The chemical structure of the quaternary ammonium polymer was also analyzed and confirmed by the $\\mathrm{^{1}H}$ NMR spectrum (Figure 1c). The chemical shifts at $3.1-3.4~\\mathrm{ppm}$ were assigned to the methyl groups (b and $\\mathbf{b}^{\\prime}$ positions) from aminomethyl $[-\\mathrm{N}(\\mathrm{CH}_{3})_{2}]$ and quaternary ammonium $[-\\mathrm{N^{+}}(\\mathrm{CH}_{3})_{2}-$ $\\mathrm{\\DeltaC_{7}H_{15}B r^{-}]},$ , respectively. The chemical shifts at $3.74\\mathrm{-}4.55$ ppm were attributed to methylene protons (f and $\\mathbf{f^{\\prime}}$ positions) that bonded to the ester groups. Also, the chemical shift at 3.43−3.71 ppm was attributed to methylene protons (e position) that bonded to $-\\mathrm{N}^{+}(\\mathrm{CH}_{3})_{2}\\mathrm{-}\\mathrm{C}_{7}\\mathrm{H}_{15}\\mathrm{Br}^{-}$ . The full XPS spectrum was used to determine the chemical compositions of the PET and pMDHAB−AA copolymer (Figure 1d). Also, the fine spectra of Br and N of the PET and pMDHAB−AA copolymer are shown in Figure S1. As shown in the figure, the Br and N elements were observed at binding energies of 67 and $400~\\mathrm{eV}$ for the pMDHAB−AA copolymer, respectively. It can be seen that the N signal was divided into two peaks at 398 and $402\\ \\mathrm{eV}_{;}$ which can be attributed to the tertiary and protonated amino groups, separately. The results confirmed that the tertiary amino groups in the pMDHAB−AA copolymer were not protonated totally by 1-bromoheptane. Figures 1e and S2 illustrate that the onset decomposition temperature of the pMDHAB−AA copolymer decreased from 302 to $233~^{\\circ}\\mathrm{C}$ compared with that of the pDMAEMA−AA copolymer, which was similar to the thermal degradation profile of the reported quaternized polymers.31,39 The decrease in the thermal stability is attributed to the Hofmann elimination of quaternary ammonium salts, which produces an alkene, a tertiary amine, and a low-molecular-weight compound specific to the counterion.40 Overall, these results affirm the successful preparation of quaternary ammonium. \n\n \nFigure 4. Photographs of the PET film covered with different cross-linked coatings containing bare (a) PET film, (b) PEGDA coating, (c) APA coating, and (d) dual-cross-linked pMDHAB−AA coating over hot water $({\\sim}60~^{\\circ}\\dot{\\mathrm{C}}$ , $100\\%$ relative humidity). Photographs of fog condensation of the PET film covered with the (e) dual-cross-linked pMDHAB−AA coating and (f) PET film, which were first stored at $-20~^{\\circ}\\mathrm{C}$ for $30~\\mathrm{min}$ and then exposed quickly to ambient laboratory conditions ${\\bf\\Pi}^{\\prime}{\\sim}20^{\\circ}{\\bf C},$ $55\\%$ relative humidity). $(\\mathbf{g})$ Optical microscopy images of the antifogging process on the pMDHAB−AA coating and PET film in $10~\\mathrm{min}$ upon hot water ( $\\sim60^{\\circ}\\mathrm{C}$ , $100\\%$ relative humidity). (h) Light transmittance of the PET film and coated PET film in ambient conditions $\\mathrm{\\Omega}^{\\sim20\\mathrm{\\Omega}^{\\circ}C}$ , $60\\%$ relative humidity) after being stored at $-20{}^{\\circ}\\mathrm{C}$ for $30\\mathrm{min}$ . The antifogging test of (i) a window and (j) safety goggles when entering indoors $(25~^{\\circ}\\mathrm{C})$ from cold outdoors $(-15^{\\circ}\\mathrm{C})$ . \n\nPreparation and Characterizations of the Dual-CrossLinked Antifogging Coating. The preparation process of the dual-cross-linked pMDHAB−AA coating is shown in Figure 2a. In the coating system, the pMDHAB−AA copolymer was cross-linked by APA at room temperature to form one cross-linked network, and for a second cross-linked network, the PEGDA molecules were triggered by a photoinitiator to form another cross-linked network. As is wellknown, transparency is essential for an antifogging coating. Therefore, the visible-light transmittance of both the PET film and the dual-cross-linked pMDHAB−AA coating were measured in the wavelength range of $400{-}800\\ \\mathrm{nm}$ (Figure 2b). The transmittance values of the dual-cross-linked pMDHAB−AA coatings on the PET film $(84-90\\%)$ ) were slightly higher than those of the bare PET film $(81-87\\%)$ , indicating that the pMDHAB−AA coatings have an antireflection effect, which can mainly be attributed to the fine nanostructure on the coating surface. This nanostructure can change the propagation path of light and reduce the reflection and scattering of light on the coating surface, thereby increasing the transmittance.41 The surface morphology and thickness of the dual-cross-linked pMDHAB−AA coatings were exhibited by SEM. As shown in Figures 2c and S3, the coating surface was very smooth and had a thickness of $2.5\\mu\\mathrm{m}$ . The surface morphology of the coatings was further observed by AFM. As shown in Figure 2d, the root-mean-square roughness $R_{\\mathfrak{q}}$ value of the coating surface was $0.202\\ \\mathrm{\\nm},$ , whereas the ${\\bar{R}}_{\\mathrm{q}}$ value of the pure PET surface was $1.09\\ \\mathrm{nm}$ (Figure S4). The nanoscale roughness further confirmed that smooth surfaces were formed, which can facilitate optical transparency.42 In addition, an electron energy-dispersive spectrometer was also applied to analyze and confirm the chemical composition of the dual-cross-linked pMDHAB−AA coating surface. Figure 2e reveals that the coating surface mainly contains C, N, O, and Br elements with atomic ratios of $75.68\\%$ , $5.74\\%$ , $12.37\\%$ , and $6.21\\%$ , respectively. The appearance of the Br element illustrates that 1-bromoheptane is successfully introduced to the coating. Finally, the TGA curves of different cross-linked coatings are shown in Figure S5. The difference of the initial decomposition temperature proves that the dual-cross-linked coating (pMDHAB−AA coating) shows good thermal stability. \n\nThe wettability of the coating surface was determined with a contact angle meter, and the change of the WCA on the coating surface with time was recorded within 1000 s. As shown in Figure 3a, the coating surface has a high WCA value of $100^{\\circ}$ initially, and with the extension of time, the WCA on the coating surface decreased gradually and decreased to $43^{\\circ}$ at \n\n1000 s. This phenomenon was attributed to the rapid hydration of ionic chain segments on the coating surface. As shown in Figure 3, in air surroundings, the long alkyl chain segments tend to spread to the coating surface, and therefore the coating surface has a large WCA at first. However, the quaternary ammonium groups hydrated and migrated to the coating surface gradually when the coating was in contact with a water droplet. With the extension of time, the coating became hydrophilic, and the water droplets spread. Due to the final hydrophilic state, the coating surface exhibits excellent superoleophobicity underwater. Various oily liquid droplets, including $o$ -xylene, toluene, and dichloromethane, were selected as the representative solvents to investigate the contact angles on the dual-cross-linked pMDHAB−AA coating underwater. As shown in Figure 3c, the contact angles of these oily liquid droplets can exceed $150^{\\circ}$ on the coating surface underwater. In contrast, for the pure PET film surface underwater, the contact angles are below $90^{\\circ}$ . The results confirm that the coating exhibits excellent superoleophobic characteristics underwater, which can be attributed to the presence of the hydrophilic quaternary ammonium components, which can form a hydration layer on the coating surface to prevent the adhesion of oily liquid droplets. \n\nAntifogging Performance. The antifogging performance of the dual-cross-linked pMDHAB−AA coating was evaluated by both hot-vapor and cold-warm methods. Herein, to confirm the long-term availability of the dual-cross-linked pMDHAB− AA coating, two kinds of single-cross-linked PEGDA and APA coatings also were prepared and verified by the hot-vapor method. Three kinds of coatings, including dual-cross-linked pMDHAB−AA coating, PEGDA coating, APA coating, and pure PET film, were exposed $3\\ \\mathrm{cm}$ above the hot water vapor $(\\sim60^{\\circ}\\mathrm{C},$ $100\\%$ relative humidity), and the surface states were recorded by a digital camera. Unsurprisingly, the pure PET film was covered by small fog droplets quickly, and the words below became blurred (Figure 4a and Movie S1). The transparency of the PEGDA coating was maintained for less than $24\\mathrm{~h~}$ (Figure 4b), and the transparency of the APA coating remained for less than $^{40\\mathrm{~h~}}$ (Figure 4c). However, as shown in Figure 4d and Movie S2, the dual-cross-linked pMDHAB−AA coating maintained high transparency for more than 20 days, and no obvious water droplets or water mist were seen, which can be attributed to the hydrophilic quaternary ammonium and the higher cross-linking density. At the beginning, the tiny fog droplets were absorbed in the pMDHAB−AA coating network. With the prolongation of time, the condensed fog drops formed a uniform water film on the coating surface, which can avoid or reduce light scattering and refraction. The obtain results suggest that the pMDHAB− AA coatings have the longest antifogging time. For the coldwarm method, the pMDHAB−AA coating and pure PET film were first stored at $-20~^{\\circ}\\mathrm{C}$ for $30~\\mathrm{min}$ and then exposed to ambient conditions ( ${\\bf\\Gamma}\\sim20\\mathrm{\\Omega}^{\\circ}{\\bf C},$ $55\\%$ relative humidity). As shown in Figure 4e, the dual-cross-linked pMDHAB−AA coating was transparent and the words below were clearly visible, whereas the pure PET film showed a visible fog layer and the words beneath could barely be read. The antifogging behavior of the coating was also investigated on a microscopic scale. As shown in Figure $^{4}\\mathrm{g},$ within the initial ${\\boldsymbol{\\mathsf{S}}}\\ {\\boldsymbol{\\mathsf{s}}},$ a large number of water droplets with a diameter of approximately 25 $\\mu\\mathrm{m}$ were generated on the bare PET film surface, and the water droplets gradually increased with the extension of time. In contrast, no water droplets could be observed on the pMDHAB−AA coating surface at any instant, which illustrates the remarkable antifogging ability. In addition, in order to quantitatively evaluate the antifogging performance of the pMDHAB−AA coating, the transmittances of both the pMDHAB−AA coating and pure PET film were measured using a visible spectrophotometer within the wavelength range of $400{-}800\\ \\mathrm{nm}$ . As shown in Figure $\\mathrm{4h}_{\\cdot}$ , in the cold-warm method, the transmittance of the PET film sharply decreased to about $36{-}48\\%$ from $84-90\\%$ because of the fog forming on the surface. As for the pMDHAB−AA coating, the transparency was still maintained, which showed the efficiency of suppressing fog formation. \n\n \nFigure 5. (a) Schematic diagram of a greenhouse in a winter environment. (b) Transparency comparison between coated and uncoated PO films. (c) Light transmittance of the blank PO film and the film covered with the dual-cross-linked pMDHAB−AA coating. (d) Antifogging comparison of uncoated and coated PO films with the cold-warm method. (e) Antifogging performance test in a simulated winter environment. (f) Light transmittance of the dual-cross-linked pMDHAB−AA coating after repetitive dry−wet alternating antifog test cycles with the cold-warm method. \n\nConsidering possible practical application situations, the pMDHAB−AA coating was coated on various transparent substrates such as a window and safety goggles without affecting their inherent optical transparency. The antifogging performances of a window and safety goggles that were covered with the pMDHAB−AA coating were checked by the cold-warm method. As shown in Figure 4i, the window model was used to verify the antifogging ability of the dual-crosslinked pMDHAB−AA coating in the case of a large temperature difference between inside and outside surroundings. This shows that the uncoated surface became opaque immediately, while the coated surface maintained visible clearness. In addition, when entering warm rooms $(25~^{\\circ}\\mathrm{C})$ from the cold outdoors $(-15^{\\circ}\\mathrm{C})$ , the pure goggle fogged up quickly, whereas the coated goggle remained highly transparent (Figure 4j). The above results show that the dual-cross-linked pMDHAB−AA coating can still maintain good transparency when the external environment changes, which proves its good practical value. \n\nIt is universally acknowledged that fog on a greenhouse film affects the photosynthesis of crops and reduces vegetable yields; therefore, antifogging coatings are very important for use on agricultural greenhouses. As shown in Figure 5a, a greenhouse simulation experiment was used to further test the feasibility of coating on a greenhouse film. Figure 5b shows that the plant under the greenhouse PO film decorated with a coating is clearer than the blank PO film. The visible-light transmittance of the PO film increased from $81.1\\%$ to $91.0\\%$ after it was decorated with the antifogging coating (Figure 5c), which is more conducive to the transmission of sunlight and the growth of crops. Figure 5d shows the antifogging performance under the cold-warm test. As shown by the result, the plant outline under the blank film cannot be seen, while the plant under the coated film is still clear. The longterm antifogging performance of the coated film was determined under a simulation environment in an ice locker. A $-20~^{\\circ}\\mathrm{C}$ value of an ice locker simulated the outdoor temperature in winter, and the internal temperature of greenhouse was $25\\ ^{\\circ}\\mathrm{C},$ provided by a water bath. As shown in Figure 5e, the uncoated film became opaque immediately, and with increasing time, the condensed small fog drops became bigger and dropped due to its nonwettability. In contrast, the film covered with the dual-cross-linked pMDHAB−AA coating showed high optical transparency and was maintained for more than 20 days, which illustrates the long-term antifogging performance. Besides, the dry−wet alternating antifogging test was conducted with the cold-warm method and hot-vapor method to demonstrate the durability of the coating. Briefly, for the cold-warm method, the PO film covered with the dual-cross-linked pMDHAB−AA coating was first stored in a freezer at $-20{}^{\\circ}\\mathrm{C}$ for $30\\mathrm{min}$ , and then the PO film was taken out of the freezer and exposed to ambient conditions for ${\\boldsymbol{\\mathsf{S}}}{\\boldsymbol{\\mathsf{s}}},$ and the visible-light transmittance of the PO film was measured to judge its antifogging performance. For the hot-vapor method, the coating was exposed on hot water vapor $(60~^{\\circ}\\mathrm{C}_{\\mathrm{\\i}}$ , $100\\%$ relative humidity) for $\\textsf{S}\\operatorname*{min}$ , and the transmittance was collected using the same method. After the coatings were dried in air, the experiment was repeated many times. The light transmittance changes of the coated film with various cycles are summarized in Figures 5f and S6. It is easy to see that, after 10 cycles of the dry−wet alternating antifogging test, the transmittance of the coating has no significant changes, which proved that the stable antifogging property could be maintained on the surface after being repeated many times, clearly illustrating the excellent practical relevance of the coating for the desirable application. Beyond that, as shown in Figure S7, the transparency of the coating has not been affected, and there is no cracking on the surface of the coating after bending 100 times, which means that the prepared coating can be deposited on the flexible and foldable film. \n\n \nFigure 6. Antibacterial property tests of the dual-cross-linked pMDHAB-AA coating. (a) Growth inhibition rates of pMDHAB−AA copolymers in aqueous solutions with a sequence of concentrations against S. aureus and E. coli. (b) Photographs of the zone-of-inhibition test results of the PET and dual-cross-linked pMDHAB−AA coating in a cultured lawn of S. aureus and E. coli. (c) Photographs of bacterial colonies of S. aureus and E. coli after incubation with the PET and dual-cross-linked pMDHAB−AA coating at $37^{\\circ}\\mathrm{C}$ for $24\\mathrm{h}.$ . (d) SEM images of S. aureus and $E$ . coli on the PET and dual-cross-linked pMDHAB−AA coating surfaces. \n\nAntibacterial Performance. In addition to the higher transparency and outstanding antifogging performance of the transparent substrates, the antibacterial property is also highly needed for practical application situations.43,44 Generally speaking, quaternary ammonium salts have been widely used as antibacterial agents because of the antibacterial activity.45,46 In this sense, the antibacterial ability of the dual-cross-linked pMDHAB−AA coating was assessed with E. coli and S. aureus according to the following method.36,37,47 First, the MIC of the pMDHAB−AA copolymer was determined to evaluate the antibacterial ability. $\\mathrm{MIC}_{90}$ is defined as the lowest concentration that exhibited more than $90\\%$ inhibition of the bacterial growth.36 Figure 6a shows that the pMDHAB−AA copolymer had MIC values of $1024~\\mu\\mathrm{g/mL}$ toward both E. coli and S. aureus, which was seriously lower than the concentration required for the coating, manifesting the reasonable antibacterial activity. Then, the antibacterial property of the pMDHAB−AA coating was investigated by a zone-ofinhibition test. As shown in Figure 6b, the surroundings of the pure PET was covered with lots of bacterial colonies, whereas for the PET covered with the pMDHAB−AA coating, obvious inhibition zones were shown, which can be attributed to the migration of the quaternary ammonium components from the film to the surrounding agar. In addition, the spread plate method was used to further confirm the antibacterial performance of the coating. As shown in Figure 6c, a large number of bacteria were covered on an agar plate of the blank PET, whereas no bacteria could be observed on the coating plate, indicating the antibacterial activity of the prepared coating, which was in accordance with the zone-of-inhibition test results. At last, the antibacterial activity by observing the attachment of the bacteria on the coating surfaces was assessed via SEM. As shown in Figure 6d, significant quantities of bacteria adhered to the PET film surfaces, whereas in contrast, no bacterium can be observed on the dual-cross-linked pMDHAB−AA coating surfaces, which means that the cationic hydrated layer of the dual-cross-linked pMDHAB−AA coating also can prevent bacteria cell adhesion. \n\n \nFigure 7. (a) WCAs of the dual-cross-linked pMDHAB−AA coating after different friction cycles. (b) Antifogging performance of the coating after 12000 friction cycles. (c) Friction coefficients on the PET and dual-cross-linked pMDHAB−AA coating surfaces with different friction cycles (2N, $2\\ \\mathrm{Hz},$ against a PDMS ball in aqueous solution). (d) Changes of the friction coefficient on the dual-cross-linked pMDHAB−AA coating surface under different loads ( $2\\ \\mathrm{Hz},$ against a PDMS ball in aqueous solution). \n\nWear-Resistance and Self-Lubrication Performances in Water. In addition to the antifogging performance, the wear-resistance performance of a coating is critical for achieving broad applications. To investigate the wearresistance performance of the dual-cross-linked pMDHAB− AA coating, the friction tests were conducted using an alcohol rubber abrasion test machine (model 339) in air. A polyester cloth was selected as the upper friction pair, and a $^\\textrm{\\scriptsize1N}$ force was applied to the coating in reciprocal friction mode. Figure 7a displays the variations in the initial WCA after different friction cycles. The results indicate a gradual decrease in the \n\nWCA of the coating with an increasing number of friction cycles. However, even after 12000 friction cycles (Figure 7b), the coating maintained an excellent antifogging performance, which affirmed its superior wear resistance. The friction coefficients of the pure PET film and the film covered with the dual-cross-linked pMDHAB−AA coating were determined to reveal the self-lubrication performance in the surrounding water. As shown in Figure 7c, the friction coefficient of the PET film can reach up to 0.8, whereas the coating exhibits an impressively low and stable friction coefficient of 0.005 throughout the entire 25000 cycles. The distinct difference is attributed to the presence of the hydrophilic pMDHAB chains in the coating network, allowing water molecules to be absorbed and form a uniform hydration layer, and due to its dual-cross-linked network, the coating maintains stability throughout the entire friction cycle. Notably, Figure 7d shows the changes of the friction coefficient curves under different loadings. The friction coefficient has not increased and even reduced at high pressure, which declared a good load capacity under the water surroundings.",
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"category": " Results and discussion"
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},
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{
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"id": 6,
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"chunk": "# CONCLUSIONS \n\nIn summary, a highly transparent, antifogging, and antibacterial coating containing pMDHAB−AA and PEGDA dual-crosslinked networks was prepared via a UV-curing process. Based on the delicate hydrophilic/hydrophobic balance and the highly cross-linked structure, the resulting coating demonstrated an excellent long-lasting antifogging property in both hot-vapor and cold-warm conditions for 20 days. In addition, the quaternary ammonium groups of the pMDHAB units rendered the coating with a strong antibacterial property against Gram-positive S. aureus and Gram-negative E. coli. Based on the hygroscopicity of pMDHAB blocks and highly cross-linked structure of the coating network, the coating has oleophobicity underwater, an ultralow friction coefficient in water, and wear resistance. The overall results reported herein imply that the long-term antifogging coating with increased transparency and good antibacterial and abrasion resistance could be potentially applied in the field of medical devices, windows, greenhouse films, and so on.",
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"category": " Conclusions"
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},
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{
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"id": 7,
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"chunk": "# ASSOCIATED CONTENT",
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"category": " References"
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},
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{
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"id": 8,
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"chunk": "# $\\bullet$ Supporting Information \n\nThe Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsapm.4c00912. \n\nXPS spectra of the PET and pMDHAB−AA copolymer, DTG curves of copolymers, cross-sectional SEM images of the coating, AFM image of PET, TGA and DTG curves of different cross-linked coatings, transmittance spectra of the coating, and optical microscopy images of the coating (PDF) \n\nMovie S1 showing a hot-vapor fogging test on the bare PET surface (MP4) \n\nMovie S2 showing a hot-vapor fogging test on the dualcross-linked pMDHAB−AA coating surface (MP4)",
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"category": " Results and discussion"
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},
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{
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"id": 9,
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"chunk": "# AUTHOR INFORMATION",
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"category": " References"
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},
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{
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"id": 10,
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"chunk": "# Corresponding Authors \n\nYang Wu − Shandong Laboratory of Advanced Materials and Green Manufacturing, Yantai Zhongke Research Institute of Advanced Materials and Green Chemical Engineering, Yantai, Shandong 264006, P. R. China; State Key Laboratory of Solid Lubrication, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, Gansu 730000, P. R. China; Qingdao Centre of Resource Chemistry and New Materials, Qingdao, Shandong 266100, P. R. China; $\\circledcirc$ orcid.org/0000-0002-4953-1801; Email: yangwu@licp.cas.cn \nKai Feng − Shandong Laboratory of Advanced Materials and Green Manufacturing, Yantai Zhongke Research Institute of Advanced Materials and Green Chemical Engineering, Yantai, Shandong 264006, P. R. China; Email: kaifeng@ amgm.ac.cn",
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"category": " References"
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},
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{
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"id": 11,
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"chunk": "# Authors \n\nLina Zhang − Shandong Laboratory of Advanced Materials and Green Manufacturing, Yantai Zhongke Research Institute of Advanced Materials and Green Chemical Engineering, Yantai, Shandong 264006, P. R. China; Yantai Research Institute of Harbin Engineering University, Yantai, Shandong 264006, P. R. China Yizhe Liu − Shandong Laboratory of Advanced Materials and Green Manufacturing, Yantai Zhongke Research Institute of Advanced Materials and Green Chemical Engineering, Yantai, Shandong 264006, P. R. China; State Key Laboratory of Solid Lubrication, Lanzhou Institute of \n\nChemical Physics, Chinese Academy of Sciences, Lanzhou, Gansu 730000, P. R. China \nFangrong Wu − Shandong Laboratory of Advanced Materials and Green Manufacturing, Yantai Zhongke Research Institute of Advanced Materials and Green Chemical Engineering, Yantai, Shandong 264006, P. R. China \nYubo Liu − Shandong Laboratory of Advanced Materials and Green Manufacturing, Yantai Zhongke Research Institute of Advanced Materials and Green Chemical Engineering, Yantai, Shandong 264006, P. R. China; State Key Laboratory of Solid Lubrication, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, Gansu 730000, P. R. China \nBo Yu − State Key Laboratory of Solid Lubrication, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, Gansu 730000, P. R. China; $\\circledcirc$ orcid.org/0000- 0002-1635-0027 \nXiaowei Pei − Shandong Laboratory of Advanced Materials and Green Manufacturing, Yantai Zhongke Research Institute of Advanced Materials and Green Chemical Engineering, Yantai, Shandong 264006, P. R. China; State Key Laboratory of Solid Lubrication, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, Gansu 730000, P. R. China \nLijia Liu − Yantai Research Institute of Harbin Engineering University, Yantai, Shandong 264006, P. R. China; $\\circledcirc$ orcid.org/0000-0002-2181-747X \nChunhong Zhang − Yantai Research Institute of Harbin Engineering University, Yantai, Shandong 264006, P. R. China; $\\circledcirc$ orcid.org/0000-0001-6068-8140 \nFeng Zhou − State Key Laboratory of Solid Lubrication, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, Gansu 730000, P. R. China; $\\circledcirc$ orcid.org/0000-0001-7136-9233 \n\nComplete contact information is available at: https://pubs.acs.org/10.1021/acsapm.4c00912",
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"category": " References"
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},
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{
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"id": 12,
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"chunk": "# Notes \n\nThe authors declare no competing financial interest.",
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"category": " References"
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},
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{
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"id": 13,
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"chunk": "# ACKNOWLEDGMENTS \n\nWe gratefully acknowledge support from the Key Research and Development Program in Shandong Province (SYS202203 and 2021CXGCDA02), the Shandong Provincial Natural Science Foundation (ZR2023QE089 and ZR2021ZD27), the National Natural Science Foundation of China−China Academy of Engineering Physics NSAF Joint Fund Project (U2030201), the Key Research and Development Program of Gansu (22YF7GA049), the Gansu Province Basic Research Innovation Group Project (22JR5RA093), and the Science Foundation for Distinguished Young Scholars of Gansu Province (23JRRA651).",
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"category": " References"
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},
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{
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"id": 14,
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"category": " References"
|
||
}
|
||
] |