Facile generation of highly durable thiol-functionalized polyhedral oligomeric silsesquioxane based superhydrophobic melamine foam

Abstract

In this study, a durable superhydrophobic/superoleophilic melamine foam was fabricated by a facile and rapid one-step thiol-ene click chemistry and Michael addition reaction, which demonstrated excellent robustness in oil/water separation. First, 1H, 1H, 2H-perfluoro-1-hexene reacted with thiol-functionalized polyhedral oligomeric silsesquioxane via the thiol-ene click chemistry to obtain a fluorinated thiol-functionalized polyhedral oligomeric silsesquioxane solution. Subsequently, the melamine foam was immersed to the solution system to form nanoaggregates on the melamine foam surface by the Michael addition reaction in the presence of ultraviolet light. The micro/nano rough structure and low surface energy of the nanoaggregates layer endowed the pristine melamine foam with superhydrophobicity; the water contact angle was greater than 150°. More importantly, the as-prepared melamine foam could withstand harsh conditions, such as a corrosive solution environment, strong ultraviolet light, mechanical compression, high and low temperature exposure, and ultrasonic washing. Driven by gravity, the as-prepared melamine foam could efficiently separate the oil/water mixtures and maintain 98% separation efficiency at high and low temperatures. In addition, it maintained the desirable absorption capability in different oil/organic solvents even after 15 absorption cycles. Accordingly, this facile, low-cost, and robust one-step method provides important support for the superhydrophobic oil/water separation field.

Graphical abstract

Keywords

superhydrophobic melamine foam / thiol-functionalized polyhedral oligomeric silsesquioxane / durable / oil/water separation

References

[1] Li X, Wang M, Wang C, Cheng C, Wang X. Facile immobilization of Ag nanocluster on nanofibrous membrane for oil/water separation. ACS Applied Materials & Interfaces, 2014, 6(17): 15272–15282

[2] Zhou Y, Wu W, Qiu K. Recovery of materials from waste printed circuit boards by vacuum pyrolysis and vacuum centrifugal separation. Waste Management, 2010, 30(11): 2299–2304

[3] Wang B, Liang W, Guo Z, Liu W. Biomimetic super-lyophobic and super-lyophilic materials applied for oil/water separation: a new strategy beyond nature. Chemical Society Reviews, 2015, 44(1): 336–361

[4] Li Z T, Lin B, Jiang L W, Lin E C, Chen J, Zhang S J, Tang Y W, He F A, Li D H. Effective preparation of magnetic superhydrophobic Fe₃O₄/PU sponge for oil-water separation. Applied Surface Science, 2018, 427: 56–64

[5] Cheng Q Y, Guan C S, Wang M, Li Y D, Zeng J B. Cellulose nanocrystal coated cotton fabric with superhydrophobicity for efficient oil/water separation. Carbohydrate Polymers, 2018, 199: 390–396

[6] Ge B, Zhang Z, Zhu X, Men X, Zhou X, Xue Q. A graphene coated cotton for oil/water separation. Composites Science and Technology, 2014, 102: 100–105

[7] Li J, Long Y, Xu C, Tian H, Wu Y, Zha F. Continuous, high-flux and efficient oil/water separation assisted by an integrated system with opposite wettability. Applied Surface Science, 2018, 433: 374–380

[8] Cao C, Cheng J. Fabrication of superhydrophobic copper stearate@Fe₃O₄ coating on stainless steel meshes by dip-coating for oil/water separation. Surface and Coatings Technology, 2018, 349: 296–302

[9] Cheng Q Y, Zhao X L, Weng Y X, Li Y D, Zeng J B. Fully sustainable, nanoparticle-free, fluorine-free, and robust superhydrophobic cotton fabric fabricated via an eco-friendly method for efficient oil/water separation. ACS Sustainable Chemistry & Engineering, 2019, 7(18): 15696–15705

[10] Zhu T, Li S, Huang J, Mihailiasa M, Lai Y. Rational design of multi-layered superhydrophobic coating on cotton fabrics for UV shielding, self-cleaning and oil-water separation. Materials & Design, 2017, 134: 342–351

[11] Fang Y, Liu C, Li M, Miao X, Pei Y, Yan Y, Xiao W, Wu L. Facile generation of durable superhydrophobic fabrics toward oil/water separation via thiol-ene click chemistry. Industrial & Engineering Chemistry Research, 2020, 59(13): 6130–6140

[12] Lu Y, Yuan W. Superhydrophobic three-dimensional porous ethyl cellulose absorbent with micro/nano-scale hierarchical structures for highly efficient removal of oily contaminants from water. Carbohydrate Polymers, 2018, 191: 86–94

[13] Liu C, Fang Y, Miao X, Pei Y, Yan Y, Xiao W, Wu L. Facile fabrication of superhydrophobic polyurethane sponge towards oil-water separation with exceptional flame-retardant performance. Separation and Purification Technology, 2019, 229: 115801

[14] Korhonen J T, Kettunen M, Ras R H, Ikkala O. Hydrophobic nanocellulose aerogels as floating, sustainable, reusable, and recyclable oil absorbents. ACS Applied Materials & Interfaces, 2011, 3(6): 1813–1816

[15] Wang H, Wang E, Liu Z, Gao D, Yuan R, Sun L, Zhu Y. A novel carbon nanotubes reinforced superhydrophobic and superoleophilic polyurethane sponge for selective oil-water separation through a chemical fabrication. Journal of Materials Chemistry. A, Materials for Energy and Sustainability, 2015, 3(1): 266–273

[16] Feng L, Zhang Z, Mai Z, Ma Y, Liu B, Jiang L, Zhu D. A super-hydrophobic and super-oleophilic coating mesh film for the separation of oil and water. Angewandte Chemie International Edition, 2004, 43(15): 2012–2014

[17] Wang P, Chen M, Han H, Fan X, Liu Q, Wang J. Transparent and abrasion-resistant superhydrophobic coating with robust self-cleaning function in either air or oil. Journal of Materials Chemistry. A, Materials for Energy and Sustainability, 2016, 4(20): 7869–7874

[18] Jin Y, Jiang P, Ke Q, Cheng F, Zhu Y, Zhang Y. Superhydrophobic and superoleophilic polydimethylsiloxane-coated cotton for oil-water separation process: an evidence of the relationship between its loading capacity and oil absorption ability. Journal of Hazardous Materials, 2015, 300: 175–181

[19] Du R, Zhao Q C, Li P, Ren H Y, Gao X, Zhang J. Ultrathermostable, magnetic-driven, and superhydrophobic quartz fibers for water remediation. ACS Applied Materials & Interfaces, 2016, 8(1): 1025–1032

[20] Duan C, Zhu T, Guo J, Wang Z, Liu X, Wang H, Xu X, Jin Y, Zhao N, Xu J. Smart enrichment and facile separation of oil from emulsions and mixtures by superhydrophobic/superoleophilic particles. ACS Applied Materials & Interfaces, 2015, 7(19): 10475–10481

[21] Ge B, Zhu X, Li Y, Men X, Li P, Zhang Z. Versatile fabrication of magnetic superhydrophobic foams and application for oil-water separation. Colloids and Surfaces. A, Physicochemical and Engineering Aspects, 2015, 482: 687–692

[22] Panda A, Varshney P, Mohapatra S S, Kumar A. Development of liquid repellent coating on cotton fabric by simple binary silanization with excellent self-cleaning and oil-water separation properties. Carbohydrate Polymers, 2018, 181: 1052–1060

[23] Xiong S, Zhong Z, Wang Y. Direct silanization of polyurethane foams for efficient selective absorption of oil from water. AIChE Journal. American Institute of Chemical Engineers, 2017, 63(6): 2232–2240

[24] Yuan J, Liu X, Akbulut O, Hu J, Suib S L, Kong J, Stellacci F. Superwetting nanowire membranes for selective absorption. Nature Nanotechnology, 2008, 3(6): 332–336

[25] Yan T, Chen X, Zhang T, Yu J, Jiang X, Hu W, Jiao F. A magnetic pH-induced textile fabric with switchable wettability for intelligent oil/water separation. Chemical Engineering Journal, 2018, 347: 52–63

[26] Ge J, Ye Y, Yao H, Zhu X, Wang X, Wu L, Wang J, Ding H, Yong N, He L, Yu S H. Pumping through porous hydrophobic/oleophilic materials: an alternative technology for oil spill remediation. Angewandte Chemie International Edition, 2014, 53(14): 3612–3616

[27] Seeharaj P, Pasupong P, Detsri E, Damrongsak P. Superhydrophobilization of SiO₂ surface with two alkylsilanes for an application in oil/water separation. Journal of Materials Science, 2018, 53(7): 4828–4839

[28] Liu F, Sun F, Pan Q. Highly compressible and stretchable superhydrophobic coating inspired by bio-adhesion of marine mussels. Journal of Materials Chemistry. A, Materials for Energy and Sustainability, 2014, 2(29): 11365–11371

[29] Liu Y, Ma J, Wu T, Wang X, Huang G, Liu Y, Qiu H, Li Y, Wang W, Gao J. Cost-effective reduced graphene oxide-coated polyurethane sponge as a highly efficient and reusable oil-absorbent. ACS Applied Materials & Interfaces, 2013, 5(20): 10018–10026

[30] Liu S, Xu Q, Latthe S S, Gurav A B, Xing R. Superhydrophobic/superoleophilic magnetic polyurethane sponge for oil/water separation. RSC Advances, 2015, 5(84): 68293–68298

[31] Gan Y, Jiang X, Yin J. Self-wrinkling patterned surface of photocuring coating induced by the fluorinated poss containing thiol groups (F-POSS-SH) as the reactive nanoadditive. Macromolecules, 2012, 45(18): 7520–7526

[32] Xu Q F, Wang J N, Sanderson K D. Organic-inorganic composite nanocoatings with superhydrophobicity, good transparency, and thermal stability. ACS Nano, 2010, 4(4): 2201–2209

[33] Xue C H, Fan Q Q, Guo X J, An Q F, Jia S T. Fabrication of superhydrophobic cotton fabrics by grafting of POSS-based polymers on fibers. Applied Surface Science, 2019, 465: 241–248

[34] Lyu Z, An Q, Qin P, Li W, Wang X. Preparation and characterization of POSS-containing poly(perfluoropolyether)methacrylate hybrid copolymer and its superhydrophobic coating performance. RSC Advances, 2019, 9(9): 4765–4770

[35] Hou K, Zeng Y, Zhou C, Chen J, Wen X, Xu S, Cheng J, Pi P. Facile generation of robust poss-based superhydrophobic fabrics via thiol-ene click chemistry. Chemical Engineering Journal, 2018, 332: 150–159

[36] Chen J, You H, Xu L, Li T, Jiang X, Li C M. Facile synthesis of a two-tier hierarchical structured superhydrophobic-superoleophilic melamine sponge for rapid and efficient oil/water separation. Journal of Colloid and Interface Science, 2017, 506: 659–668

[37] Zhang R, Jing X, Chu Y, Wang L, Kang W, Wei D, Li H, Xiong S. Nitrogen/oxygen co-doped monolithic carbon electrodes derived from melamine foam for high-performance supercapacitors. Journal of Materials Chemistry. A, Materials for Energy and Sustainability, 2018, 6(36): 17730–17739

[38] Luo G, Wen L, Yang K, Li X, Xu S, Pi P, Wen X. Robust and durable fluorinated 8-maposs-based superamphiphobic fabrics with buoyancy boost and drag reduction. Chemical Engineering Journal, 2020, 383: 123125

[39] Chen X, Weibel J A, Garimella S V. Continuous oil-water separation using polydimethylsiloxane-functionalized melamine sponge. Industrial & Engineering Chemistry Research, 2016, 55(12): 3596–3602

[40] Liu Y, Ma L, Wang W, Kota A K, Hu H. An experimental study on soft PDMS materials for aircraft icing mitigation. Applied Surface Science, 2018, 447: 599–609

[41] Peng L, Yuan S, Yan G, Yu P, Luo Y. Hydrophobic sponge for spilled oil absorption. Journal of Applied Polymer Science, 2014, 131(20): 40886

[42] Li J, Tenjimbayashi M, Zacharia N S, Shiratori S. One-step dipping fabrication of Fe₃O₄/PVDF-HFP composite 3D porous sponge for magnetically controllable oil-water separation. ACS Sustainable Chemistry & Engineering, 2018, 6(8): 10706–10713

[43] Wei Q, Oribayo O, Feng X, Rempel G L, Pan Q. Synthesis of polyurethane foams loaded with TiO₂ nanoparticles and their modification for enhanced performance in oil spill cleanup. Industrial & Engineering Chemistry Research, 2018, 57(27): 8918–8926

[44] Xu Z, Miyazaki K, Hori T. Dopamine-induced superhydrophobic melamine foam for oil/water separation. Advanced Materials Interfaces, 2015, 2(15): 1500255

[45] Wu L, Zhang J, Li B, Fan L, Li L, Wang A. Facile preparation of super durable superhydrophobic materials. Journal of Colloid and Interface Science, 2014, 432: 31–42

[46] Mahadik S A, Pedraza F D, Relekar B P, Parale V G, Lohar G M, Thorat S S. Synthesis and characterization of superhydrophobic-superoleophilic surface. Journal of Sol-Gel Science and Technology, 2016, 78(3): 475–481

[47] Xia F, Feng L, Wang S, Sun T, Song W, Jiang W, Jiang L. Dual-responsive surfaces that switch between superhydrophilicity and superhydrophobicity. Advanced Materials, 2006, 18(4): 432–436

Acknowledgements

This work was supported by the National Key Research and Development Program (Grant No. 2017YFB0307700), the Department of Scientific and Technology of Zhejiang Province (Grant No. LGG19E030007), and the Project for the Innovation of High Level Returned Overseas Scholars (or team) in Hangzhou. We also thank the financial support from Department of Scientific and Technology of Yunnan Province (Grant No. 202002AB080002).

Electronic Supplementary Material

Supplementary material is available in the online version of this article at https://dx.doi.org/10.1007/s11705-021-2124-0 and is accessible for authorized users.

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