Abstract
Three novel side-chain fluoroalkyl polyether oligomers with different molecular weight were synthesized base on the ring-opening polymerization of 3-perfluoro-n-butyl-1,2-epoxypropane, followed by terminal esterification using acryloyl chloride. The oligomer intermediates were used as functional monomers for emulsion copolymerization with methyl methacrylate, butyl acrylate, and hydroxyethyl methacrylate. The produced latexes were used for hydrophobic and oil-phobic finishing on cotton fabric surface and the treated cotton fabrics were tested by scanning electron microscopy and energy-dispersive spectroscopy, combined with chemical composition analysis by X-ray photoelectron spectroscopy. The result showed that fluorinated copolymers were successfully coated on the cotton fibers’ surface. Water contact angles was used to evaluate the wettability and the results showed that treated cotton fabrics possessed good hydrophobicity with the contact angle of 139.1 ± 1°, and the heat resistance of treated cotton fabrics was identified improved through the thermogravimetric analyses (TGA).
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References
Abidi N, Hequet E (2005) Cotton fabric graft copolymerization using microwave plasma II. Physical properties. J Appl Polym Sci 98:896–902. https://doi.org/10.1002/app.22195
Aminayi P, Abidi N (2013) Imparting super hydro/oleophobic properties to cotton fabric by means of molecular and nanoparticles vapor deposition methods. Appl Surf Sci 287:223–231. https://doi.org/10.1016/j.apsusc.2013.09.132
Aminayi P, Abidi N (2015) Ultra-oleophobic cotton fabric prepared using molecular and nanoparticle vapor deposition methods. Surf Coat Technol 276:636–644. https://doi.org/10.1016/j.surfcoat.2015.06.005
An QF, Wang KF, Jia Y (2011) Film morphology, orientation and performance of dodecyl/carboxyl functional polysiloxane on cotton substrates. Appl Surf Sci 257:4569–4574. https://doi.org/10.1016/j.apsusc.2010.12.032
Ayeni NA, Adeniyi A, Abdullahi NN, Bernard E, Ogunleye AO (2013) Thermogravimetric and kinetic study of methylolmelamine phosphate treated—cotton fabric. Bayero J Pure Appl Sci 5:51–55. https://doi.org/10.4314/bajopas.v5i2.9
Berret JF, Calvet D, Collet A, Viguier M (2003) Fluorocarbon associative polymers. Curr Opin Colloid Interface Sci 8:296–306. https://doi.org/10.1016/S1359-0294(03)00048-7
Bhushan B, Jung YC, Koch K (2009) Micro-, nano-, and hierarchical structures for superhydrophobicity, self-cleaning and low adhesion. Philos Trans R Soc A 367:1631–1672. https://doi.org/10.1098/rsta.2009.0014
Bongiovanni R, Beamson G, Mamo A, Priola A, Recca A, Tonelli C (2000) High resolution XPS investigation of photocured films containing perfluoropolyether acrylates. Polymer 41:409–414. https://doi.org/10.1016/S0032-3861(99)00203-7
Cabrales L, Abidi N (2012) Microwave plasma induced grafting of oleic acid on cotton fabric surfaces. Appl Surf Sci 258:4636–4641. https://doi.org/10.1016/j.apsusc.2011.12.130
Cengiz U, Erbil HY (2014) Superhydrophobic perfluoropolymer surfaces having heterogeneous roughness created by dip-coating from solutions containing a nonsolvent. Appl Surf Sci 292:591–597. https://doi.org/10.1016/j.apsusc.2013.12.013
Cheng DF, Masheder B, Urata C, Hozumi A (2013) Smooth perfluorinated surfaces with different chemical and physical natures: their unusual dynamic dewetting behavior toward polar and nonpolar liquids. Langmuir 29:11322–11329. https://doi.org/10.1021/la402398y
Drelich J, Chibowski E, Desheng Meng D, Terpilowski K (2011) Hydrophilic and superhydrophilic surfaces and materials. Soft Matter 7:9804–9828. https://doi.org/10.1039/c1sm05849e
Ferrero F, Periolatto M (2013) Application of fluorinated compounds to cotton fabrics via sol–gel. Appl Surf Sci 275:201–207. https://doi.org/10.1016/j.apsusc.2013.01.001
Ferrero F, Periolatto M, Udrescu C (2012) Water and oil-repellent coatings of perfluoro-polyacrylate resins on cotton fibers: UV curing in comparison with thermal polymerization. Fiber Polym 13:191–198. https://doi.org/10.1007/s12221-012-0191-z
Hansen NML, Jankova K, Hvilsted S (2007) Fluoropolymer materials and architectures prepared by controlled radical polymerizations. Eur Polym J 43:255–293. https://doi.org/10.1016/j.eurpolymj.2006.11.016
Kaplánek R, Paleta O, Michálek J, Přádný M (2005) Perfluoroalkylated diblock-alkyl methacrylate monomers for biomedical applications: wettability of their copolymers with HEMA and DEGMA. Fluor Chem 126:595–600. https://doi.org/10.1016/j.jfluchem.2005.01.004
Kim YS, Lee JS, Ji Q, McGrath JE (2002) Surface properties of fluorinated oxetane polyol modified polyurethane block copolymers. Polymer 43:7161–7170. https://doi.org/10.1016/S0032-3861(02)00458-5
Kim B, Kim H, Kim J, Cho CS, Lee J (2013) Superhydrophobic polytetrafluoroethylene surface obtained using reactive ion etching and duplication with polydimethylsiloxane mould. Micro Nano Lett 8:691–695. https://doi.org/10.1049/mnl.2013.0266
Lafuma A, Quere D (2003) Superhydrophobic states. Nat Matter 2:457–460. https://doi.org/10.1038/nmat924
Latthe SS, Terashima C, Nakata K, Fujishima A (2014) Superhydrophobic surfaces developed by mimicking hierarchical surface morphology of lotus leaf. Molecules 19:4256–4283. https://doi.org/10.3390/molecules19044256
Lau KKS, Bico J, Teo KBK, Chhowalla M, Amaratunga GAJ, Milne WI, McKinley GH, Gleason KK (2003) Superhydrophobic carbon nanotube forests. Nano Lett 3:1701–1705. https://doi.org/10.1021/nl034704t
Liao RJ, Zuo ZP, Guo C, Yuan Y, Zhuang AY (2014) Fabrication of superhydrophobic surface on aluminum by continuous chemical etching and its anti-icing property. Appl Surf Sci 317:701–709. https://doi.org/10.1016/j.apsusc.2014.08.187
Miao H, Bao FF, Cheng LL, Shi WF (2010) Cotton fabric modification for imparting high water and oil repellency using perfluoroalkyl phosphate acrylate via γ-ray-induced grafting. Radiat Phys Chem 79:786–790. https://doi.org/10.1016/j.radphyschem.2010.01.017
Mohsin M, Carr CM, Rigout M (2013) Novel one bath application of oil and water repellent finish with environment friendly cross-linker for cotton. Fiber Polym 14:724–728. https://doi.org/10.1007/s12221-013-0724-0
Periolatto M, Ferrero F (2014) Cotton and polyester surface modification by methacrylic silane and fluorinated alkoxysilane via sol–gel and UV-curing coupled process. Surf Coat Technol 271:165–173. https://doi.org/10.1016/j.surfcoat.2014.12.048
Periolatto M, Ferrero F, Montarsolo A, Mossotti R (2013) Hydrorepellent finishing of cotton fabrics by chemically modified TEOS based nanosol. Cellulose 20:355–364. https://doi.org/10.1007/s10570-012-9821-2
Ruan M, Li W, Wang B, Deng B, Ma F, Yu Z (2013) Preparation and anti-icing behavior of superhydrophobic surfaces on aluminum alloy substrates. Langmuir 29:8482–8491. https://doi.org/10.1021/la400979d
Sauer B, Mclean RS, Thomas RR (1998) Tapping mode AFM studies of nano-phases on fluorine-containing polyester coatings and octadecyltrichlorosilane monolayers. Langmuir 14:3045–3051. https://doi.org/10.1021/la971334d
Wang Z, Li Q, She Z, Chen F, Li L, Zhang X, Zhang P (2013) Facile and fast fabrication of superhydrophobic surface on magnesium alloy. Appl Surf Sci 271:182–192. https://doi.org/10.1016/j.apsusc.2013.01.158
Xu W, An QF, Hao LF, Zhang D, Zhang D (2012) Synthesis and characterization of s elf-crosslinking fluorinated polyacrylatesoap-free latices with core–shell structure. Appl Surf Sci 268:373–380. https://doi.org/10.1016/j.apsusc.2012.12.104
Xu L, Xu L, Dai WS, Tsuboi TJ, Xie HD (2013) Preparation and characterization of a novel fluoro-silicone acrylate copolymer by semi-continuous emulsion polymerization. J Fluor Chem 153:68–73. https://doi.org/10.1016/j.jfluchem.2013.05.01
Xu W, An QF, Hao LF, Zhang D, Zhang M (2014) Synthesis of self-crosslinking fluorinated polyacrylate soap-free latex and its waterproofing application on cotton fabrics. Fiber Polym 15:457–464. https://doi.org/10.1007/s12221-014-0457-8
Yan YY, Gao D, Barthlott W (2011) Mimicking natural superhydrophobic surfaces and grasping the wetting process: a review on recent progress in preparing superhydrophobic surfaces. Adv Colloid Interface Sci 169:80–105. https://doi.org/10.1016/j.cis.2011.08.005
Yan ZL, Liu WQ, Gao N, Wang HL, Su K (2013) Synthesis and properties of a novel UV-cured fluorinated siloxane graft copolymer for improved surface, dielectric and tribological properties of epoxy acrylate coating. Appl Surf Sci 284:683–691. https://doi.org/10.1016/j.apsusc.2013.07.156
Yang X, Zhu LQ, Chen YC, Bao CQ, Xu JL, Zhou WW (2014) Surface properties and self-cleaning ability of the fluorinated acrylate coatings modified with dodecafluoroheptyl methacrylate through two adding ways. Appl Surf Sci 295:44–49. https://doi.org/10.1016/j.apsusc.2013.12.177
Zhong LT, Zhang SS, Li YJ, Lu GL, Huang XY (2008) Synthesis and characterization of perfluorocyclobutyl aryl ether-based amphiphilic diblock copolymer. Polymer 49:4534–4540. https://doi.org/10.1016/j.polymer.2008.08.033
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We gratefully acknowledge the financial supports by the National Natural Science Foundation of China (no. 51673137) and the Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions.
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Zong, Y., Wang, L., Sun, Y. et al. Preparation of novel side-chain fluoroalkyl polyether oligomers with terminal acrylate for emulsion copolymerization and application on cotton fabric finishing. Chem. Pap. 73, 2563–2574 (2019). https://doi.org/10.1007/s11696-019-00810-0
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DOI: https://doi.org/10.1007/s11696-019-00810-0