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http://dx.doi.org/10.14478/ace.2022.1052

Synthesis of Linear 1,2-Alkylaminopropanediols as Preservatives and Antimicrobial Activity  

Cha, Kyung-On (Department of Chemical Engineering and Applied Chemistry, Chungnam National University)
Kwak, Sang-Woon (Department of Chemical Engineering and Applied Chemistry, Chungnam National University)
Jeong, Kook-In (BJ BIOCHEM, Inc.)
Kim, Young-Ho (Department of Chemical Engineering and Applied Chemistry, Chungnam National University)
Publication Information
Applied Chemistry for Engineering / v.33, no.4, 2022 , pp. 394-401 More about this Journal
Abstract
The synthesis of 1,2-alkylaminopropanediols (1,2-AAPs) was designed to improve the hydrophilicity of linear 1,2-alkanediols having 10, 12, 14, and 16 carbon atoms in the alkyl chain. 1,2-AAPs were synthesized by reacting 3-monochloro-1,2-propanediol (3-MCPD) with linear alkylamines having 10, 12, 14 or 16 carbon atoms in an ethanol solvent at 40℃ for 2 h. The yield and purity of four types of 1,2-AAPs synthesized were found to be in the range of 51-58% and 85-99%, respectively. The amine salts of four types of 1,2-AAPs were prepared from a purified paste or solid compound by adding an acidic solution (HCl) to pH 7, and then their solubilities and antibacterial effects were tested. 1,2-decylaminopropanediol, 1,2-dodecylaminopropanediol, and 1,2-tetradecylaminopropanediol were all dissolved in water at concentrations of 100%, 50%, and 0.1%, respectively, however 1,2-hexadecylaminopropanediol was not. The antibacterial effect was improved as the length of the alkyl chain increased. As a result of confirming the preservative effect of the lotion (cosmetic formulation) applied with 1,2-AAP for application, it showed very strong antibacterial activity at low concentrations ranging from 0.005% to 0.2%.
Keywords
Preservatives; Linear 1,2-Alkanediol; 1,2-Alkylaminopropanediol; Antimicrobial efficacy; Antiseptic ability in cosmetics;
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