Lysine-Based Silicone Surfactants

Author:

Camacho Ramirez Abygail1,Melendez-Zamudio Miguel2ORCID,Guerra Contreras Antonio1ORCID,Brook Michael A.2ORCID

Affiliation:

1. Department of Chemistry, Division of Natural and Exact Sciences, University of Guanajuato, Noria Alta S/N, Col. Noria Alta, Guanajuato C.P. 36050, Gto., Mexico

2. Department of Chemistry and Chemical Biology, McMaster University, 1280 Main St. W, Hamilton, ON L8S 4M1, Canada

Abstract

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–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 12–25% natural materials, improving their sustainability compared to those containing synthetic hydrophiles.

Funder

Natural Sciences and Engineering Research Council of Canada

Dirección de Apoyo a la Investigación y al Posgrado

División de Ciencias Naturales y Exactas-Universidad de Guanajuato

JuventudEsGto

CONACYT México

Publisher

MDPI AG

Subject

General Medicine

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