Abstract
Fluoroalkyl end-capped vinyltrimethoxysilane oligomer [RF–(CH2CHSiOMe)3)n–RF; n = 2, 3; RF = CF(CF3)OC3F7: RF–(VM)n–RF] undergoes the sol–gel reactions in the presence of α, ω-dihydroxy-terminated poly(dimethylsiloxane) [HO–(SiMe2O)nH: HPDMS] under non-catalytic conditions to provide the crosslinked RF–(VM)n–RF/HPDMS composite rubber in quantitative isolated yields. Especially, we can isolate the expected composite rubber through the sol–gel reactions, in which the contents of the RF–(VM)n–RF oligomer based on employed oligomer and HPDMS are greater than 0.16%. In contrast, traditional silane coupling agents such as tetraethoxysilane, methyltrimethoxysilane and triethoxy-1H, 1H, 2H, 2H-tridecafluoro-n-octylsilane were unable to afford the expected composite rubber through the sol–gel reactions with HPDMS under similar conditions. The fluoroalkylated silicone composite rubber thus obtained gave no swelling behavior toward water, dimethyl sulfoxide and methanol; however, the composite rubber was found to display the higher swelling characteristic for toluene, hexane and tetrahydrofuran, especially for fluorinated aliphatic solvents. Interestingly, it was demonstrated that the fluoroalkylated silicone composite rubber swollen with hexane can adsorb a variety of aromatic compounds in aqueous methanol solutions. More interestingly, we found that the fluoroalkylated silicone composite rubber can exhibit an excellent adsorption ability toward the fluorinated aromatic compounds such as 2′, 3′, 4′, 5′, 6′-pentafluoroacetophenone, compared to that of the corresponding non-fluorinated one.
Graphic abstract
Similar content being viewed by others
References
Ameduri, B, Sawada, H (eds.), Fluorinated Polymers: Volume 1, “Synthesis, Properties, Processing and Simulation.” RSC, Cambridge (2016)
Ameduri, B, Sawada, H (eds.), Fluorinated Polymers: Volume 2, “Applications.” RSC, Cambridge (2016)
Sawada, H, “Synthesis of Self-assembled Fluoroalkyl End-Capped Oligomeric Aggregates: Applications of These Aggregates to Fluorinated Oligomeric Nanocomposites.” Prog. Polym. Sci., 32 509–533 (2007)
Sawada, H, “Development of Fluorinated Polymeric Functional Materials Using Fluorinated Organic Peroxide as Key Material.” Polym. J., 39 637–650 (2007)
Sawada, H, “Fluorinated Peroxides.” Chem. Rev., 96 1779–1808 (1996)
Sawada, H, “Preparation and Applications of Novel Fluoroalkyl End-capped Oligomeric Nanocomposites.” Polym. Chem., 3 46–65 (2012)
Sawada, H, “Novel Self-assembled Molecular Aggregates Formed by Fluoroalkyl End-Capped Oligomers and Their Application.” J. Fluor. Chem., 121 111–130 (2003)
Sawada, H, Suzuki, T, Takashima, H, Takishita, K, “Preparation and Properties of Fluoroalkyl End-capped Vinyltrimethoxysilane Oligomeric Nanoparticles: A New Approach to Facile Creation of A Completely Superhydrophobic Coating Surface with These Nanoparticles.” Colloid Polym. Sci., 286 1569–1574 (2008)
Katayama, S, Fujii, S, Saito, T, Yamazaki, S, Sawada, H, “Preparation of Fluoroalkyl End-Capped Vinyltrimethoxysilane Oligomeric Silica Nanocomposites Containing Gluconamide Units Possessing Highly Oleophobic/Superhydrophobic, Highly Oleophobic/Superhydrophilic, and Superoleophilic/Superhydrophobic Characteristics on the Modified Surfaces.” Polymers, 9 (1–17) 292 (2017). https://doi.org/10.3390/polym9070292
Wang, YZ, Bi, LY, Zhang, HJ, Zhu, XT, Liu, GY, Qiu, GX, Liu, SS, “Predictive Power in Oil Resistance of Fluororubber and Fluorosilicone Rubbers Based on Three-Dimensional Solubility Parameter Theory.” Polym. Test., 75 380–386 (2019)
Li, B, Chen, S, Zhang, J, “Effects of –CH2CH2CF3 on Properties of RTV Polysiloxane Rubber: Processability, Thermal Stability, and Oil/Solvent Resistance.” J. Appl. Polym. Sci., 39708 1–9 (2014). https://doi.org/10.1002/APP.39708
Xu, C, Wang, Y, Lin, B, Liang, X, Chen, Y, “Thermoplastic Vulcanizate Based on Poly(Vinylidene Fluoride) and Methyl Vinyl Silicone Rubber by Using Fluorosilicone Rubber as Interfacial Compatibilizer.” Mater. Des., 88 170–176 (2015)
Liu, Y, Zhou, C, Feng, S, “Effects of γ-Ray Radiation on the Properties of Fluorosilicone Rubber.” Mater. Lett., 78 110–112 (2012)
Guan, Y, Yang, R, Huang, Y, Yu, C, Li, X, Wei, D, “Multi-walled Carbon Nanotubes Acting as Antioxidant for Fluorosilicone Rubber.” Polym. Degard. Stabil., 156 161–169 (2018)
Xu, T, Liu, H, Song, J, Shang, S, Song, Z, Zou, K, Yang, C, “Synthesis and Characterization of Maleated Rosin-Modified Fluorosilicone Resin and Its Fluorosilicone Rubber.” J. Appl. Polym. Sci., 41888 1–9 (2015). https://doi.org/10.1002/APP.41888
Flitney, B, “Extending the Application of Fluorosilicone Elastomers.” Seal. Technol., 2005 6–11 (2005)
Tang, M, Wang, W, Xu, D, Wang, Z, “Synthesis of Structure-Controlled Polyborosiloxanes and Investigation on Their Viscoelastic Response to Molecular Mass of Polydimethylsiloxane Triggered by Both Chemical and Physical Interactions.” Ind. Eng. Chem. Res., 55 12582–12589 (2016)
Sawada, H, Nakayama, M, “Synthesis of Fluorine-Containing Organosilicon Oligomers.” J. Chem. Soc. Chem. Commun., 10 677–678 (1991)
Suzuki, J, Takegahara, Y, Oikawa, Y, Chiba, M, Yamada, S, Sugiya, M, Sawada, H, “Preparation of Fluoroalkyl End-capped Vinyltrimethoxysilane Oligomeric Silica/poly(tetrafluoroethylene) Nanocomposites Possessing a Superoleophilic/superhydrophobic Characteristic: Application to the Separation of Oil and Water.” J. Sol–Gel Sci. Technol., 81 611–622 (2017)
Li, P, Chen, HZ, Chung, T-S, “The Effects of Substrate Characteristics and Pre-wetting Agents on PAN–PDMS Composite Hollow Fiber Membranes for CO2/N2 and O2/N2 Separation.” J. Membr. Sci., 434 18–25 (2013)
Zhang, L, He, G, Zhao, W, Nie, F, Li, X, Tan, M, “Studies on the Coating Layer in a PTFPMS/PEI Composite Membrane for Gaseous Separation.” J. Membr. Sci., 371 141–147 (2011)
Dai, Y, Ruan, X, Bai, F, Yu, M, Li, H, Zhao, Z, He, G, “High Solvent Resistance PTFPMS/PEI Hollow Fiber Composite Membrane for Gas Separation.” Appl. Surf. Sci., 360 164–173 (2016)
Trinh, LTP, Lee, YJ, Bae, H-J, Lee, H-J, “Pervaporative Separation of Butanol Using a Composite PDMS/PEI Hollow Fiber Membrane.” J. Ind. Eng. Chem., 20 2814–2818 (2014)
Bernardo, P, Drioli, E, Golemme, G, “Membrane Gas Separation: A Review/State of the Art.” Ind. Eng. Chem. Res., 48 4638–4663 (2009)
Martin, A, Margoum, C, Randon, J, “Combination of Sorption Properties of Polydimethylsiloxane and Solid-Phase Extraction Sorbents in a Single Composite Material for the Passive Sampling of Polar and Apolar Pesticides in Water.” J. Sep. Sci., 39 3990–3997 (2016)
Lee, X-P, Kumazawa, T, Kondo, K, Furuta, S, Sato, K, “Solid-Phase Microextraction and Liquid Chromatography/Mass Spectrometry in Drug Analysis.” Legal Med., 1 231–237 (1999)
Chen, Y, Pawliszyn, J, “Time-Weighted Average Passive Sampling with a Solid-Phase Microextraction Device.” Anal. Chem., 75 2004–2010 (2003)
Load, HL, Pawliszyn, J, “Method Optimization for the Analysis of Amphetamines in Urine by Solid-Phase Microextraction.” Anal. Chem., 69 3899–3906 (1997)
Dugay, J, Miege, C, Hennion, M-C, “Effect of the Various Parameters Governing Solid-Phase Microextraction for the Trace-determination of Pesticides in Water.” J. Chromatogr. A, 795 27–42 (1998)
Seethapathy, S, Gorecki, T, “Applications of Polydimethylsiloxane in Analytical Chemistry: A Review.” Anal. Chim. Acta, 750 48–62 (2012)
Barletta, JY, de Lima Gomes, PCF, dos Santos-Neto, AJ, Lancas, FM, “Development of a New Stir Bar Sorptive Extraction Coating and Its Application for the Determination of Six Pesticides in Sugarcane Juice.” J. Sep. Sci., 34 1317–1325 (2011)
Schwarzenbach, RP, Escher, BI, Fenner, K, Hofstetter, TB, Johnson, CA, von Gunten, U, Wehrli, B, “The Challenge of Micropollutants in Aquatic Systems.” Science, 313 1072–1077 (2006)
Alsbaiee, A, Smith, BJ, Xiao, L, Ling, Y, Helbling, DE, Dichtel, WR, “Rapid Removal of Organic Micropollutants from Water by a Porous β-Cyclodextrin Polymer.” Nature, 529 190–194 (2016)
Suzuki, J, Takegahara, Y, Oikawa, Y, Aomi, Y, Sawada, H, “Preparation of Fluoroalkyl End-Capped Oligomer/Cyclodextrin Polymer Composites: Development of Fluorinated Composite Material Having a Higher Adsorption Ability toward Organic Molecules.” J. Encapsul. Ads. Sci., 8 117–138 (2018)
Muller, K, Faeh, C, Diederich, F, “Fluorine in Pharmaceuticals: Looking Beyond Intuition.” Science, 317 1881–1887 (2006)
Funding
This work was partially supported by a Grant-in-Aid for Scientific Research (Grant No. 19K05027) from the Ministry of Education, Science, Sports and Culture, Japan.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare that they have no conflict of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Yamashita, K., Yokouchi, T. & Sawada, H. Facile preparation of fluoroalkyl end-capped vinyltrimethoxysilane oligomer/α, ω-dihydroxy-terminated poly(dimethylsiloxane) composite rubber: application to effective removal of fluorinated aromatic compound from aqueous methanol solution by fluoroalkylated silicone composite rubber. J Coat Technol Res 18, 63–73 (2021). https://doi.org/10.1007/s11998-020-00382-9
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11998-020-00382-9