Superhydrophobization of cotton textiles by difunctional cyclic siloxanes via thiol-ene click reaction

Przybylak, Marcin; Przybylska, Agnieszka; Szymańska, Anna; Maciejewski, Hieronim

doi:10.1007/s10570-023-05204-w

Cited by 3 publications

(4 citation statements)

References 39 publications

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“…The addition of alkyl groups causes disorder to increase in the structures. The fluorine derivative has a higher density than oil by 0.113 g/cm 3 . The derivative with aromatic groups was also characterized by high density, similar to the organosilicon precursor.…”

Section: Synthesis and Analysis Of Derivativesmentioning

confidence: 98%

“…Reactions with olefins containing alkyl groups differing in chain length, i.e., hexene, octene, and octadecene, both for the crystalline and oily Density measurements were carried out for the physicochemical characterization of the compounds obtained via the photoaddition of SSQ-8SH oil form with various olefins, and the data are summarized in Table 2. Measurements were carried out at 25 • C. The non-functionalized SSQ-8SH has a density of 1.299 g/cm 3 . The addition of alkyl groups significantly decreased the density of compounds with increasing chain length (1.198 g/cm 3 ; 1.162 g/cm 3 ; 1.095 g/cm 3 for hexene, octene, and octadecene, respectively).…”

Section: Synthesis and Analysis Of Derivativesmentioning

confidence: 99%

“…Measurements were carried out at 25 • C. The non-functionalized SSQ-8SH has a density of 1.299 g/cm 3 . The addition of alkyl groups significantly decreased the density of compounds with increasing chain length (1.198 g/cm 3 ; 1.162 g/cm 3 ; 1.095 g/cm 3 for hexene, octene, and octadecene, respectively). The higher density of SSQ-8SH oil is due to the greater number of thiol groups (SH) present in the compound, which allows for hydrogen interactions, and greater order in the structure, resulting in greater packing and higher parameters.…”

Section: Synthesis and Analysis Of Derivativesmentioning

confidence: 99%

“…Simple reaction mechanisms of thiol-ene in the presence of AIBN or DMPA are shown in Figure 2. Hydrothiolation is a widely used process due to its fast reaction rate, relatively mild conditions, high conversion, minimal or no by-products, variety of substrates, and high selectivity [2,3]. It has numerous applications, including in protective coatings, peptides [4], preparation of dendrimers [5], modification of materials [6,7], optical materials [8], ionogels [9], or hydrogels [10].…”

Section: Introductionmentioning

confidence: 99%

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Click Addition Reaction of Urethane–Acrylate Resin Using Octa(3-thiopropyl)silsesquioxane Derivatives as Cross-Linking Agents

Pakuła,

Sztorch,

Przekop

et al. 2023

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In this work, new partially substituted derivatives of octa(3-thiopropyl)silsesquioxane (SSQ-8SH) were synthesized. The article compares the thiol-ene reaction using two methods: radical mechanism, thermally initiated (AIBN), and in the presence of a photoinitiator (DMPA). Both the crystalline and the oil forms of SSQ-8SH were functionalized. Olefins with nonpolar alkyl groups (hexene, octene, and octadecene) and vinyltrimethoxysilane, allyl glycidyl ether, allyl 2,2,3,3,4,4,5,5-octafluoropentylether, allyl methacrylate, and styrene were used in the reactions, allowing to obtain seven new derivatives. All compounds were characterized using spectroscopic (1H NMR and 29Si NMR) and spectrometric (MALDI-TOF-MS) methods. The influence of functional groups on the water contact angle value was determined. The functionalization of the compound led to a contact angle value above 95° (SSQ-4SH-4OD). Density measurements and thermogravimetric analysis (TGA) were carried out for all compounds. The highest onset temperature (357.4 °C) and temperature at the maximum mass loss rate (377.3 °C) were observed for SSQ-SH-4OD. The addition of alkyl groups significantly decreased the density of compounds with increasing chain length (1.198 g/cm3; 1.162 g/cm3; 1.095 g/cm3 for hexene, octene, and octadecene, respectively). Silsesquioxanes have potential applications in various materials, such as UV-curable resins, allowing to modify, for example, their surface properties. Modification of a commercial photocurable resin with selected derivatives was carried out to determine the impact on physicochemical properties (TGA, WCA).

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Section: Synthesis and Analysis Of Derivativesmentioning

confidence: 98%

Section: Synthesis and Analysis Of Derivativesmentioning

confidence: 99%