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Thiol-ene chemistry as an effective tool for hydrophobization of cotton fabrics

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Abstract

In this paper, several methods of hydrophobization of cotton fabrics using the thio-ene click reaction were compared. Durable, superhydrophobic textiles were obtained in an easy way. Various variants of functionalized silsesquioxanes were used for the hydrophobization of fabrics. The synthesis of bifunctional silsesquioxanes (RSiMe2O)4(ViSiMe2O)4Si8O12 and (RSiMe2O)4(R’SiMe2O)4Si8O12 were performed via hydrothiolation of silsesquioxane derivative (ViSiMe2O)8Si8O12. Alkoxysilyl, alkyl and fluoroalkyl moieties were introduced as functional groups. Samples were prepared using four methods, differing in the modification method and the number of stages. During the research, fabrics were modified via (a) the dip-coating process, (b) carrying out thiol-ene click reactions directly on the surface of the fabric and (c) using both of these methods. The hydrophobicity of the fabric was evaluated by measuring the Water contact angle (WCA). The obtained samples were also examined using infrared analysis (FT-IR), Scanning electron microscope (SEM), and Elemental analysis (SEM–EDS). All analyses were performed before and after the washing process in order to verify the stability of the performed modifications.

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modified by silsesquioxanes in Method 1 and Method 2 (Fig. 2.)

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modified by 3-mercaptopropyltrimethoxysilane (M) via dip-coating process, then by POSS with vinyl groups (thiol-ene click reaction) (1) and finally by fluoro-funcionalized thiol (F) or octanethiol (C) (thiol-ene click reaction) and values of samples modified by POSS with 4 vinyl groups and substituted by 4 alkoksysilyl group (2c) va dip coating and subsequently modified by fluoro-funcionalized thiol (F) or octanethiol (C) via thiol-ene click reaction

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Data availability

Data available on request due to privacy restrictions. The data presented in this study are available on request from the corresponding author. The data are not publicly available due to the lack of availability of a suitable repository.

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Acknowledgments

The authors acknowledge financial support from the National Science Centre (Poland), project OPUS UMO-2018/29/B/ST8/00913, entitled “Synthesis and characterization of materials with defined surface properties”.

Funding

This work was supported by funds from the National Science Centre (Poland), project OPUS 2018/29/B/ST8/00913, entitled “Synthesis and characterization of materials with defined surface properties”.

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Contributions

Performed cotton fabrics modifications and wrote the manuscript—MP; synthesized and characterized the obtained compounds –thiol-ene click reaction, participated in writing the manuscript—AS; participated in the conceptualization, provided guidance during the planning of experiments and reviewed the manuscript—HM; Washing process, thiol-ene click reaction –AP

Corresponding author

Correspondence to Marcin Przybylak.

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The authors declare no conflict of interest. The funders had no role in the design of the study; in the collection, analyses, or interpretation of data; in the writing of the manuscript, nor in the decision to publish the results.

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This article does not contain any studies with human participants or animals performed by any of the authors.

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Szymańska, A., Przybylak, M., Maciejewski, H. et al. Thiol-ene chemistry as an effective tool for hydrophobization of cotton fabrics. Cellulose 29, 1231–1247 (2022). https://doi.org/10.1007/s10570-021-04357-w

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  • DOI: https://doi.org/10.1007/s10570-021-04357-w

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