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Applications of Polymer, Composite, and Coating Materials

Easily prepared and reusable film for fast-response rewritable light printing Yongqi Yang, Jiaqi Li, Xinyao Li, Lin Guan, Zijian Gao, LiJie Duan, Fei Jia, and Guanghui Gao ACS Appl. Mater. Interfaces, Just Accepted Manuscript • Publication Date (Web): 26 Mar 2019 Downloaded from http://pubs.acs.org on March 27, 2019

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Easily prepared and reusable film for fast-response rewritable light printing Yongqi Yang, Jiaqi Li, Xinyao Li, Lin Guan, Zijian Gao, Lijie Duan, Fei Jia*, Guanghui Gao* Polymeric and Soft Materials Laboratory, School of Chemical Engineering, and Advanced Institute of Materials Science, Changchun University of Technology, Changchun, 130012, P. R. China. E-mail: [email protected]; [email protected] KEYWORDS: photochromism, polyoxometalate, gelatin, light printing, rewritable paper.


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ABSTRACT:

Paper, for hand-writing and printing, consumed a lot in the modern life. However, the production of conventional paper could cause many problems, such as deforestation and environmental pollution. Therefore, it is necessary and urgent to explore novel strategies to solve these problems. In this work, a polyoxometalate doped gelatin film with high strength, excellent transparency and fast photochromic properties is designed and prepared. The film can display different colors by using a variety of reagents, exhibiting its potential application as a paper medium. Its rapid photochromic properties allow complex high-resolution images to be displayed by UV light printing. It is found that the mechanical and photochromic properties could be regulated by the introduction of triethylene glycol, and the fading process could be controlled by changing temperature and humidity. Moreover, it is rewritable, self-repairable and recyclable, and can also achieve long-term preservation without fading. It is envisioned that the environmentally friendly film with low cost, easy-to-prepare and recycling advantages, have the potential to be an alternative of conventional paper for hand-writing and printing.


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Introduction Although electronic reading devices have been developed rapidly recently, however, paper still occupies a crucial position in communication and information storage. Disposable paper causes serious problems, such as deforestation and environmental pollution.1 Therefore, new strategies should be explored to solve these problems. Color changing technologies responding to light,2–8 temperature,9–14 water15–21 and force,22–27 have provided new strategies to design papers with rewriteable ability.18,28–31 Photochromism, as a promising technology, could be used to design and fabricate rewritable paper. At present, many photochromic materials were prepared by incorporating organic dyes (typically, spiropyran32–35 or diarylethene36–40) into conventional papers. However, these strategies still face the challenge that the organic dye-based rewritable papers were sensitive to light and the fading progress would happen under the visible light irradiation. Moreover, many of these rewritable materials are paper-based materials3,9,18 and it is still difficult to solve environmental problems. Film materials have similar properties to papers with thin and flexible properties. Therefore, the environmentally friendly films would widely expect to be alternatives of conventional papers. Gelatin, as a common protein derived from biological tissues, has good film-forming ability.41,42 Moreover, gelatin has been produced in large quantities with low cost. Therefore, it is considered to form an ideal material to replace conventional paper. Protein chains derived from gelatin allow to be combined with charged color changing materials to fabricate rewritable materials. Polyoxometalates (POMs) with negative charges, as photochromic materials,43–46 can complex with gelatin due to the electrostatic interaction. It is expected to prepare gelatin-based


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film by adding ammonium molybdate (Mo7) with stable and reversible photochromism, allowing the flexible film to be used as rewritable "paper". In this investigation, gelatin-based photochromic films were prepared by adding Mo7 to gelatin via solution volatilization. Non-toxic triethylene glycol (TEG) was added to adjust the mechanical and photochromic properties of the film. As a result, this low cost and easy-prepared film exhibited high mechanical strength, excellent transparency, fast and reversible photochromic ability, which could be used for hand-writing and printing. Moreover, it was allowed to use the reducing agent as the "ink" for writing and could also be used for highresolution "light printing". It was envisioned that this low cost, environmentally friendly and recyclable photochromic film exhibited promise of new generation of printing and writing carriers. Experimental Section Materials: Gelatin (gel strength ~250 g Bloom), triethylene glycol (TEG, 98%) and ammonium molybdate [(NH4)6Mo7O24·4H2O] (Mo7, 99%) were supplied by Shanghai Aladdin Reagent Co. Ltd. Deionized water (18.2 MΩ·cm resistivity at 25°C) was used in the experiment. Preparation of films: TEG0 was prepared as follows: Gelatin (2.0g) was dissolved in water (20mL) at 50 °C and then the solution was cooled to 35 °C. Then Mo7 was added and stirred to obtain clear solution. The solution was evenly spread on a piece of PVC substrate at room temperature and placed for 48h to evaporate the water to obtain TEG0. From TEG20 to TEG100 were prepared as follows: Gelatin (2.0g) was dissolved in water (20mL) at 50 °C and different amounts of TEG were added and stirred. Then the solution was cooled to 35 °C. Then Mo7 was added and stirred to obtain clear solution. The solution was evenly spread on a piece of PVC


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substrate at room temperature and placed for 48h to evaporate the water to obtain films. The preparation process was shown in Scheme 1 and the contents of each component were shown in Table 1.

Scheme 1. The preparation process of the films. Table 1. Recipes of the films Gelatin(g)

TEG(g)

Mo7(g)

H2O(mL)

TEG0

2.0

0

0.9

20

TEG20

2.0

0.4

0.9

20

TEG40

2.0

0.8

0.9

20

TEG60

2.0

1.2

0.9

20

TEG80

2.0

1.6

0.9

20

TEG100

2.0

2.0

0.9

20


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Mechanical measurement: Tensile measurement was performed on the equipment (Instron 5965) at room temperature with a tensile rate of 2 mm min-1. Each sample was cut into ribbons with length of 30 mm and width of 5 mm. The thickness of the samples was measured before the test. Absorbance measurement: The UV-Vis-NIR spectrum and transmission measurements were measured by a UV-vis-NIR spectroscopy (Cary 5000, Agilent). The scanning wavelength was recorded in the range of 200-1200 nm. The scanning speed was 2000 nm·min-1. Photochromic and fading process: The samples for photochromic experiment were treated by a UV light irradiation source (Intelli-ray 600, maximum light intensity of 150 mw/cm2, Uvitron International). The height of the sample from the light source was set as 20 cm. The fading experiments were conducted in a closed box (5L) with a small amount of water and air or oxygen was filled into. The relative humidity of the gas was 90%RH. Results and discussion Tensile tests had shown mechanical properties of these films. As shown in Figure 1a, TEG0 was strong and brittle. With the addition of TEG, the fracture stress gradually decreased, and the fracture strain increased. In addition, the modulus of the films also decreased with the increase of TEG in Figure 1b. These films also exhibited significant optical transparency (Figure 1c). The films were almost incapable of transmitting UV light, but could efficiently transmit visible and near-infrared light. This was because that gelatin and Mo7 were transparent under visible and near-infrared light. The Mo=O bond in Mo7 exhibits strong absorption in the UV light region due to the presence of a ligand-to-metal charge transfer transition of O→Mo (VI),47 therefore the


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film exhibited strong absorption under UV light. Further, as the TEG content increased, the transmittance also increased from 88.4% to 94.0% at the wavelength of 550nm (Figure 1d).

Figure 1. (a) Stress and strain tests, (b) modulus tests, (c) transparency exhibition and (d) transmittance tests of the films. The photochromic properties of the films were measured by exposing to UV light for different times. The results demonstrated that these films had rapid photochromic ability, and as the TEG content increased, the efficiency of photochromism was obviously increased (Figure 2a and S2). The color went darker with the increase of UV light irradiation time. It could be observed that


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the corresponding maximum absorbance intensity exhibited a series of curves fitting with the irradiation time (Figure S3, S4 and S5). Interestingly, as the TEG content increased, the color of the allochroic films also changed. After 60s of UV irradiation, TGE0 was grayish, TEG20 was gold, TEG40 and TEG60 were brown, and TEG80 and TEG100 were dark green. UV-Vis-NIR spectra showed that all the films showed an absorption peak at 480 nm after irradiation of 60 s. The absorbance increased with the increase of TEG content (Figs 2b and 2c) and the absorbances at 480 nm could be fitted to a logarithmic curve. Since the absorption peak at 480 nm was derived from d-d transition of Mo(V), this phenomenon could be attributed to that the internal structure of the films became loose as the TEG content increased, which was beneficial to the thermal motion of Mo7 molecules, thereby accelerating the photochromic rate. It was noticeable that there were also shown absorption peaks at 730 nm. These absorption peaks were hardly observed on TEG0 and TEG20, but were noticeable on TEG60, TEG80 and TEG100. The absorbance at 730 nm exhibited an excellent “S” curve profile fitting with the TEG content (Figure 2c). The absorption peak at 730 nm was derived from the intervalence charge transfer of Mo(V)→Mo(VI) in Mo7.47 As the solvent content increased, Mo7 was affected by changes in the external molecular environment, leading to remarkable changes at 730 nm. The photochromic principle of Mo7 was an UV-induced reduction reaction, which was capable of fading under the oxidation of oxygen. The films were placed in an air environment for 7 days and the fading process was observed in Figure 2d. As the TEG content increased, the fading rate became fast. This was due to that the addition of TEG could facilitate the entry of oxygen into films, resulting in the fading process. The absorbance at 480 nm showed this trend that the absorbance decrease became apparent with the increase of TEG (Figure 2e). The change of absorbance could be fitted to a straight line with the TEG content.


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Due to the moisture absorption properties of TEG, the films could absorb water vapor in humid environments, which could speed up the fading rate. As shown in Figure 2f, TEG80 consumed the fading process in humid air for 36h, significantly faster than that in dry air. In addition, the humidity oxygen environment could faintly accelerate the fade process compared to the humid air environment. In a humid oxygen environment, the fading process consumed 24h. It could be observed from the UV-Vis-NIR spectra that the absorbance at 480 nm gradually decreased with the increase of time (Figure S6), but the absorbance at 730 nm showed a trend of increase and then decrease in Figure 2g. The color of the films turned to blue firstly and then faded. This supported the assumption that the difference of color for films was related to the water content after photochromism. Simultaneously, it could be seen that the fading process of the films in a humid environment was affected by water and oxygen. The increase of the water content significantly increased the absorbance of the film at 730 nm. Subsequently, oxygen gradually oxidizes Mo(V) to colorless Mo(VI), resulting in a decrease of absorbance and the film eventually became colorless. Further, the effect of temperature on the fading process was also evaluated in Figure 2h. The fading process became fast at high temperature. Especially, the fading process needs 12 h at 40 °C under the humid air condition. When the temperature was further raised to 60 °C, it was only 2 h to complete the fading process. The absorbance at 730 nm also showed a tendency of increase and then decrease from Figure 2i, indicating that the fading process was also affected by water and oxygen, and high temperature could speed up the fading rate significantly. Water was an important factor to affect the color of films after photochromism. Here, the allochroic films were treated by water. It could be seen from Figure 2j that the color of films was changed from their original color to blue after treatment of water. Also, UV-Vis-NIR spectra


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showed that the absorption intensity of all films increased significantly at 730 nm in Figure 2k, and the curve of the absorbance at 730 nm exhibited logarithmic (Figure S7 and S8). This result indicated that the intervalence charge transfer of Mo(V)→Mo(VI) in Mo7 became strong under the existence of water. In addition, the appeared absorption peak at 630 nm attributed to the change of energy levels from d-d transition, which was affected by the surrounding environment of water molecules.

Figure 2. (a) Photos of all films after different UV irradiation times. (b) Corresponding UVVis-NIR spectra after UV irradiation for 60s. (c) Corresponding absorbances of all films at 480nm and 730nm. (d) Photos of the fading process of allochroic films in room environment for 7 days and (e) corresponding residual absorbances at 480nm. (f) Photos of the fading process in


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different gas environment under wet condition (90%RH) and (g) corresponding normalized absorbances at 730nm. (h) Photos of the fading process at different temperature under wet condition (90%RH) and (i) corresponding normalized absorbances at 730nm. (j) Photos of the allochroic films after on treatment with water and (k) corresponding UV-Vis-NIR spectra. These photochromic films could be used for writing like conventional papers. Taking TEG80 as an example in Figure 3a, the film could be written on using different kinds of pens including oil-based and water-based inks. In addition, the film was also compatible with reducing agents as inks. As shown in Figure 3b, letters with different color could be written on the film by using sodium dithionite or dithiothreitol (DTT) aqueous solutions. The letters were green by using sodium dithionite and yellow by employing the DTT aqueous solutions. It was also found that the text could be sensitive to the specific wavelength light under the treatment of an aqueous solution of rare earth compounds in Figure 3c. A EuCl3 aqueous solution was used as "ink" to write on the film and the written texts were invisible under the visible and 254 nm UV light. However, significant red fluorescence was observed when irradiated with 365 nm UV light. These interesting properties could be applied in the field of cryptographic writing and anticounterfeiting. In addition, the film could also be used for writing after photochromism. As shown in Figure 3d, the letters could be written on the allochroic film by using water, while the green film could be written on with colorless letters by using NaClO aqueous solutions as inks. This was because that NaClO could oxidize Mo(V) to Mo(VI), leading to the fading process. Except hand-writing, the film could be utilized for printing like conventional papers. As shown in Figure 3e, clear texts could be printed on the film by using a laser printer and an inkjet printer. In addition, the film also had "light printing" ability. By using masks, it could display texts, images or QR codes clearly after the illumination of UV light in Figure 3f. Subsequently,


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a film with a large size of 200 mm × 160 mm was easily prepared and the text was printed on it by UV light printing in Figure 3g. These letters were highly recognizable and could be easily identified, and the printing quality was similar to that of the conventional printing technology (Figure 3h). The film could also be used to print complex images such as photos in Figure 3i. To confirm the resolution of "UV light printing", a light printing process at micrometer scale was carried out. It was successfully printed circles with a diameter of 50 μm and distances between each circle of 20 μm on the film (Figure 3j). These results demonstrated that the film could be printed with high-resolution not only by conventional coating method technology like papers, but also by UV light printing technology.

Figure 3. (a) Photos of writing on TEG80 films with different ink pens, (b) different reducing reagents (0.1mol L-1 aqueous) and (c) europium chloride aqueous (0.2mol L-1). (d) Photos of the allochroic TEG80 films after on treatment with water and NaClO (0.1mol L-1 aqueous). (e)


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Photos of printing on TEG80 films with laser printer and inkjet printer. (f) Photos of light printing of pattern, letters and QR code. (g) Photo of large size (200*160mm) preparation and light printing of TEG80 film and (h) enlarged photo. (i) Print a complex image by light printing on TEG80 film. (j) Light printing on micrometer scale on TEG80 film. It was found that the film had the ability of self-repairing. As shown in Figure 4a, the film was cut with a knife, placed in different environments for 1 h and then observed through a microscope. At 20 °C, the film could not be self-repaired at the conditions of dry air and humid air. However, the film could be completely recovered to the original state under humid air at 60 °C, showing the self-repairing ability. Further, the film could be easily regenerated after being destroyed. It only needs to dissolve the film in water at 35 °C and then manufacture it via the coating method. The regenerated film still retained the original "light printing" capability and no loss of mechanical properties in Figure 4(b,c), demonstrating excellent regeneration ability. Although conventional papers could also be regenerated, its process was more complicated than that of this film. Moreover, the film could be reused by erasing. As shown in Figure 4d, UV-visNIR spectra had shown that the photochromic properties of this film were repeatable. After photochromic-fading cycles for 5 times, the photochromic property of the film was still stable, allowing that allowed the film could be reused and display different information by multiple "printing-erasing” cycles in Figure 4e. Since the fading process was not conducive to the longterm preservation of printed information, a method was explored and developed. By treating with AgNO3 aqueous solutions, the fading process of the film could be prevented and the information on the film would be preserved for good (Figure 4f). The principle was that Ag(I) could be reduced by Mo(V) in the allochroic film to Ag, thus showed dark brown in the photochromic region.


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Figure 4. (a) Photos of self-repairable ability of TEG80 films under different conditions. (b) Photos of recyclable ability of TEG80 film and (c) corresponding normalized stress before and after regeneration. (d) Normalized absorbances of TEG80 film with 5 times photochromism– fading cycles and (e) corresponding photos. (f) Photos of long-term preservation ability of TEG80 film by treating by AgNO3 (0.1mol L-1). Conclusions In summary, the films with excellent mechanical, optical and photochromic properties were successfully prepared and exhibited great potential in hand-writing and printing. The color of the photochromic films could be adjusted from gray to dark green by using different contents of TEG. The allochroic films could gradually fade in the air environment and the fading process could be significantly accelerated by heating in the wet condition. Moreover, they had the ability to write with reducing reagent aqueous or rare earth metal salts solution as ink, and also could print via micron resolution light. The rewritable, self-repairable, and recyclable performances ensured the films reusable. As a result, the low-cost, high strength, high transparency and rapidly


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photochromic films could be used as rewritable paper and extensively replace the conventional papers. It is expected that this simple design strategy could be used to produce advanced rewritable paper as green printing technology.

Supporting Information. Supporting Information is available free of charge on the ACS Publication website: FT-IR spectra of all films, photos of all films after different UV irradiation times (0-5s), UV-Vis-NIR spectra of the films after different UV irradiation times, Normalized absorbances at 480nm of the fading process in different gas environment and different temperature under wet condition and UV-Vis-NIR spectra of the allochroic films before and after on treatment with water. ACKNOWLEDGMENT This research was supported by grants from National Natural Science Foundation of China (Nos. 51703012 and 51873024), Science and Technology Department of Jilin Province (No. 20180101207JC), and Education Department of Jilin Province (No. JJKH20181027KJ). REFERENCES (1) Hermy, M.; Honnay, O.; Firbank, L.; Grashof-Bokdam, C.; Lawesson, J. E. An Ecological Comparison between Ancient and Other Forest Plant Species of Europe, and the Implications

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