Lysine-Based Silicone Surfactants
2023
Abygail Camacho Ramirez | Miguel Melendez-Zamudio | Antonio Guerra Contreras | Michael A. Brook
Highly efficient silicone surfactants are typically based on polyether hydrophiles. As part of a program to increase the natural content of silicones, we describe the synthesis of silicone surfactants with amino acid hydrophiles (cysteine, arginine, and lysine). The compounds were prepared using a radial thiol&ndash:ene reaction with vinylsilicones for cysteine derivatives and a catalyst-free aza-Michael reaction with arginine and lysine. Short chain surfactants with silicone monomer:hydrophile ratios of 5:1 or less (e.g., telechelic silicones of lysine-linker-(Me2OSi)n-linker-lysine n = 10) were ineffective at stabilizing emulsions of silicone oil (D4): water. However, excellent surfactants were realized as the chain length (n) increased to 25 or 50, stabilizing water-in-oil emulsions with high water content (80% or 90%). The surfactants, especially the longer chain compounds, were stable against pH except <:4 or >:9 and survived freeze/thaw cycles. These surfactants contain 12&ndash:25% natural materials, improving their sustainability compared to those containing synthetic hydrophiles.
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