Synthesis of Bio‐Based Silane Coupling Agents by the Modification of Eugenol

Abstract

A simple method for the synthesis of new bio-based silane coupling agents (SCAs) with a terpene aromatic core by the functionalization of cheap, natural eugenol and its sulfur derivatives using the hydrosilylation of the C=C bonds with HSi(OEt) 3 , followed by nucleophilic substitution reactions of OH/SH groups is presented. The obtained alkoxysilanes possess different polymerreactive functionalities (alkenyl, epoxide, thiirane, thiocarbamoyl, thioester, thioether moieties). This new group of biogenic SCAs was fully characterized using 1 H, 13 C, 29 Si NMR, FT-IR, GC-MS, and HRMS or elemental analysis. Examples of their application as additives to tire rubbers and their influence on several factors are also discussed.

Water Sorption, Water Solubility, and Rheological Properties of Resin-Based Dental Composites Incorporating Immobilizable Eugenol-Derivative Monomer

“…It is widely known that Eg has beneficially been implicated in various applications and for several purposes [ 13 , 14 , 15 ]. Since ancient times, it has been used as an antimicrobial and antiseptic agent.…”

“…Furthermore, its pungent odor and volatility are another reason for the undesirability of its usage in dental composites. Eg in combination with zinc oxide (ZnO 2 ) is a common luting and temporary restorative material, but its low strength and high oral solubility prevent its application as permanent restoratives [ 17 , 18 , 19 ], thus its polymerizable derivatives may bring solutions [ 1 , 2 , 3 , 13 ]. In this regard, Almaroof et al [ 1 ] have investigated various properties of dental composites incorporating eugenyl methacrylate (EgMA) for post and core build-up restoration, reporting EgMA concentration-dependent properties with reduced values of DC and curing depth with EgMA increase.…”

Hybrid Bio-Based Silicone Coatings with Anti-adhesive Properties

“…2-methoxy-4-(3-(triethoxysilyl)propyl)phenol was prepared according to the literature procedure [ 41 ]. A Schlenk flask was charged under argon with toluene (40 mL) and triethoxysilane (2.4 g, 0.0146 mol).…”

“…Incorporation of phytochemicals into polymeric materials via covalent bonding permanently links active compounds and prevents their leaching over time. Synthesis of functional silicones by hydrosilylation of eugenol [ 36 , 37 , 38 , 39 , 40 , 41 , 42 ] with various Si-H groups containing organosilicon polymers and oligomers was reported. The resulting materials can be used, for example, as anticorrosion additives to commercial epoxy resins [ 37 ] and hybrid polyurethanes [ 42 ], bio-based silane coupling agents [ 41 ] or LED encapsulants [ 40 ].…”

“…Synthesis of functional silicones by hydrosilylation of eugenol [ 36 , 37 , 38 , 39 , 40 , 41 , 42 ] with various Si-H groups containing organosilicon polymers and oligomers was reported. The resulting materials can be used, for example, as anticorrosion additives to commercial epoxy resins [ 37 ] and hybrid polyurethanes [ 42 ], bio-based silane coupling agents [ 41 ] or LED encapsulants [ 40 ]. Eugenol and linalool were also used for functionalization of polyhedral silsesquioxanes [ 38 , 43 ].…”