journal article·2015-04Open access

Hydrophobic Materials Based on Fluorocarbofunctional Spherosilicates

Hieronim Maciejewski, Joanna Karasiewicz, Michal Dutkiewicz, Bogdan Marciniec

Silicon· Volume 7· Issue 2

Abstract

Consecutive hydrosilylation-based syntheses were performed of silsesquioxanes containing mixed groups 1H,1H,2H,2H-perfluorooctyl (PFD) or octafluoropentyloxypropyl (OFP) and trimethoxysilylethyl (TMS) in different stoichiometric ratios. The presence of TMS makes it possible to form covalent bonds with substrates due to the reactivity of this group. All obtained derivatives were applied to hydrophobization of glass plates and by comparison of water contact angles (WCA) on modified surfaces the effect of silsesquioxane structure as well as TMS and fluoroalkyl group contents on hydrophobic properties was determined. Moreover, an additional glass plates surface modification was performed in order to obtain superhydrophobic surfaces. Two silica types of different specific surface (300 and 130 m 2 /g) and particle size (7 and 16 nm) parameters were used in this case for initial surface modification in order to increase its roughness. Irrespectively of particle size of applied silica, a dependence was found between the increase in water contact angle and the number of fluoroalkyl substituents in a molecule.
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Research context

OpenAlex topics: Surface Modification and Superhydrophobicity · Silicone and Siloxane Chemistry · Adhesion, Friction, and Surface Interactions

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (39)

Show source-provided references
1. Jiang L, Feng L (2010) Bioinspired Intelligent Nanostructured Interfacial Materials. Chemical Industry Press, New Jersey10.1142/7380 ↗
2. Liu K, Yao X, Jiang L (2010) Recent development in bio-inspired special wettability. Chem Soc Rev 39:3240–3255. doi: 10.1039/B917112F10.1039/b917112f ↗
3. Arkles B, Pan Y, Kim YM (2009) The role of Polarity in the Structure of Silanes Employed in Surface Modification. In: Mittal KI (ed) Silanes and other Coupling Agents VSP, Leiden, pp 51-6510.1163/ej.9789004165915.i-348.37 ↗
4. Pagliaro M, Ciriminna R (2005) New fluorinated functional materials. J Mater Chem 15:4981–4991. doi: 10.1039/b507583c10.1039/b507583c ↗
5. McKeen LW (2006) Fluorinated Coatings and Finishes Handbook. Wiliam Andrew Publishing, New York
6. Owen MJ (2010) Silicones. In: Clarson SJ, Owen MJ, Smith SD, Van Dyhe ME (eds) Silicones and Silicone Modified Materials ACS Publising, Smith SD
7. Owen MJ, Dvornic PR (eds) (2010) Silicone Surface Science. Springer Dordrecht
8. Choi W, Tuteja A, Chhatre S, Mabry JM, Cohen RE, McKinley GH (2009) Fabrics with Tunable Oleophobicity. Adv Mater 21:2190–2195. doi: 10.1002/adma.20080250210.1002/adma.200802502 ↗
9. Choi W, Tuteja A, Mabry JM, Cohen RE, McKinley GH (2009) A modified CassieBaxter relationship to explain contact angle hysteresis and anisotropy on non-wetting textured surfaces. J Colloid Interf Sci 339:208–216. doi: 10.1016/j.jcis.2009.07.02710.1016/j.jcis.2009.07.027 ↗
10. Iacono ST, Bady SM, Mabry JM, Smith DW (2007) Synthesis, characterization, and properties of chain terminated polyhedral oligomeric silsesquioxane-functionalized perfluorocyclobutyl aryl ether copolymers. Polymer 48:4637–4645. doi: 10.1016/j.polymer.2007.06.02210.1016/j.polymer.2007.06.022 ↗
11. Tuteya A, Mabry JM (2012) The Design of Non-wetting Surfaces with FluoroPOSS. In: Owen MJ, Dvornic PR (eds) Silicone Surface Science. Springer, Dordrecht, pp 179-19310.1007/978-94-007-3876-8_6 ↗
12. Lickiss PD, Rataboul F (2008) Chapter 1 Fully Condensed Polyhedral Oligosilsesquioxanes (POSS): From Synthesis to Application. Adv Organometal Chem 57:1–116. doi: 10.1016/S0065-3055(08)00001-410.1016/S0065-3055(08)00001-4 ↗
13. Liu Y, Zheng S, Nie K (2005) Epoxy nanocomposites with octa(propylglycidyl ether) polyhedral oligomeric silsesquioxane. Polymer 46:12016–12025. doi: 10.1016/j.polymer.2005.09.05610.1016/j.polymer.2005.09.056 ↗
14. Liu Y, Yang X, Zhang W, Zheng S (2006) Star-shaped poly(-caprolactone) with polyhedral oligomeric silsesquioxane core. Polymer 47:6814–6825. doi: 10.1016/j.polymer.2006.07.05010.1016/j.polymer.2006.07.050 ↗
15. Itami Y, Marciniec B, Kubicki M (2004) Functionalization of Octavinylsilsesquioxane by Ruthenium-Catalyzed Silylative Coupling versus Cross-Metathesis. Chem Eur J 10:1239–1248. doi: 10.1002/chem.20030543310.1002/chem.200305433 ↗
16. Waehner J, Marciniec B, Pawluc P (2007) Functionalization of Vinylspherosilicates by Ruthenium-Catalyzed Silylative Coupling Reactions. Eur J Inorg Chem 8:2975–2980. doi: 10.1002/ejic.20070014210.1002/ejic.200700142 ↗
17. Dutkiewicz M, Maciejewski H, Marciniec B (2009) Functionalisation of Polyhedral Oligomeric Silsesquioxanes (POSS) via Nucleophilic Substitution. Synthesis 12:2019–2024. doi: 10.1055/s-0029-1216807
18. Hartmann-Thompson C (ed) (2011) Application of Polyhedral Oligomeric Silsesquioxanes. Springer, Dordrecht10.1007/978-90-481-3787-9 ↗
19. Iacono ST, Vij A, Grabow W, Smith DW, Mabry JM (2007) Facile synthesis of hydrophobic fluoroalkyl functionalized silsesquioxane nanostructures. Chem Commun 47:4992–4994. doi: 10.1039/b712976a10.1039/b712976a ↗
20. Mabry JM, Vij A, Iacono ST, Viers BD (2008) Fluorinated polyhedral oligomeric silsesquioxanes (F-POSS). Angew Chem Int Ed 47:4137–4140. doi: 10.1002/anie.20070535510.1002/anie.200705355 ↗
21. Xu J, Li X, Cho CM, Toh CL, Shen L, May KY, Lu X, He C (2009) Polyhedral oligomeric silsesquioxanes tethered with perfluoroalkylthioether corner groups: Facile synthesis and enhancement of hydrophobicity of their polymer blends. J Mater Chem 19:4740–4745. doi: 10.1039/b900299e10.1039/b900299e ↗
22. Koh K, Sugiyama S, Morinaga T, Ohno K, Tsujii Y, Fukuda T, Yamahiro M, Iijima T, Oikawa H, Watanabe K, Miyashita T (2005) Precision synthesis of a fluorinated polyhedral oligomeric silsesquioxane-terminated polymer and surface characterization of its blend film with poly(methyl methacrylate). Macromolecules 38:1264–1270. doi: 10.1021/ma047636l10.1021/ma047636l ↗
23. Zeng K, Wang L, Zheng S, Qian X (2009) Self-assembly behavior of hepta(3,3,3-trifluoropropyl) polyhedral oligomeric silsesquioxane-capped poly(-caprolactone) in epoxy resin: Nanostructures and surface properties. Polymer 50:685–695. doi: 10.1016/j.polymer.2008.11.02410.1016/j.polymer.2008.11.024 ↗
24. Dodiuk H, Rios PF, Dotan A, Kenig S (2007) Hydrophobic and self-cleaning coatings. Polym Adv Technol 18:746–750. doi: 10.1002/pat.95710.1002/pat.957 ↗
25. Jerman I, Orel B, Surca Vuk A, Kozelj M, Kovac J (2010) A structural and corrosion study of triethoxysilyl and perfluorooctyl functionalized polyhedral silsesquioxane nanocomposite films on AA 2024 alloy. Thin Solid Films 518:2710–2721. doi: 10.1016/j.tsf.2009.10.0210.1016/j.tsf.2009.10.023 ↗
26. Jerman I, Vuk AS, Koelj M, Orel B, Kova J (2008) A structural and corrosion study of triethoxysilyl functionalized POSS coatings on AA 2024 alloy. Langmuir 24:5029–5037. doi: 10.1021/la703726210.1021/la7037262 ↗
27. Marciniec B, Maciejewski H, Dabek I, Karasiewicz J (2009) Process for the preparation of fluorocarbofunctional alkoxysilanes Pol Pat Appl P-388929
28. Dutkiewicz M, Maciejewski H, Marciniec B, Karasiewicz J (2011) New fluorocarbofunctional spherosilicates: Synthesis and characterization. Organometallics 30:2149–2153. doi: 10.1021/om101033710.1021/om1010337 ↗
29. Filho NLD, de Aquino HA, Pires G, Caetano L (2006) Relationship between the dielectric and mechanical properties and the ratio of epoxy resin to hardener of the hybrid thermosetting polymers. J Braz Chem Soc 17:533–541. doi: 10.1590/S0103-5053200600030001610.1590/S0103-50532006000300016 ↗
30. Lazzari D, Cassani MC, Solinas G, Pretto M (2013) Fluoroalkyl allyl ethers: Useful building blocks for the synthesis of environmentally safer fluorinated multiblock molecules. J Fluor Chem 156:34–37. doi: 10.1016/j.jfluchem.2013.08.00310.1016/j.jfluchem.2013.08.003 ↗
31. Marciniec B, Krzyzanowski P (1995) Synthesis, characterization and some reactions of [(diene)Rh(-OSiMe3)]2. J Organomet Chem 493:261–266. doi: 10.1016/0022-328X(95)05352-P10.1016/0022-328X(95)05352-P ↗
32. Marciniec B, Krzyzanowski P, Walczuk-Gusciora E, Duczmal W (1999) Catalytic activity of silyloxy-rhodium(I) complexes in hydrosilylation of alkenes. J Mol Catal 144:263–271. doi: 10.1016/S1381-1169(99)00109-010.1016/S1381-1169(99)00109-0 ↗
33. Maciejewski H, Karasiewicz J, Marciniec B (2012) Effective synthesis of fluorofunctional (Poly)siloxanes. Polimery 57:449–455. doi: 10.14314/polimery.2012.44910.14314/polimery.2012.449 ↗
34. Prevo BG, Hon EW, Velev OD (2007) Assembly and characterization of Collodi-based antireflective coatings on multicrystalline silicon solar cells. J Mater Chem 17:791–799. doi: 10.1039/b612734g10.1039/B612734G ↗
35. Zhang G, Wang D, Gu ZZ, Mohwald H (2005) Fabrication of superhydrophobic surfaces from binary colloidal assembly. Langmuir 21:9143–9148. doi: 10.1021/la051194510.1021/la0511945 ↗
36. Tsai HJ, Lee YL (2007) Facile metod to fabricate raspberry-like particulate films for superhydrophobic surfaces. Langmuir 23:12687–12692. doi: 10.1021/la702521u10.1021/la702521u ↗
37. Zhang L, Li Y, Sun J, Shen J (2008) Layer-by-layer fabrication of broad-band superhydrophobic antireflection coatings In near-infrared region. J Colloid Inter Sci 319:302–308. doi: 10.1016/j.jcis.2007.11.02010.1016/j.jcis.2007.11.020 ↗
38. Xu QF, Wang JN, Sanderson KD (2010) A general approach for superhydrophobic coating with strong adhesion strength. J Mater Chem 20:5961–5966. doi: 10.1039/C0JM00001A10.1039/c0jm00001a ↗
39. Boinovich LB, AM Emelyanenko, Muzafarov AM, Myshkovskii AM, Pashinin AS, Tsivadze AYu, Yarova DI (2008) The development of coatings that give superhydrophobic properies to the surface of silicone rubber. Nanotechnologies in Russia 3:587–592. doi: 10.1134/S199507800809008510.1134/S1995078008090085 ↗