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http://dx.doi.org/10.14478/ace.2022.1005

Synthesis of 1,2-Dodecylaminopropanediol and Its Mixing Effect with 1,2-Alkanediols as Preservatives  

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.2, 2022 , pp. 179-187 More about this Journal
Abstract
In this study, the synthesis of 1,2-dodecylaminopropanediol (1,2-DDAP) having a 12 carbon chain length and an amine group was designed to improve the preservation and hydrophilicity of 1,2-alkanediol-based compounds. 1,2-DDAP was prepared by reacting dodecylamine (DDA) with 3-monochloro-1,2-propanediol (3-MCPD) in an ethanol solvent at 40 ℃, and its yield and purity were about 56% and 98%, respectively, under a reaction condition of 2 h and a DDA:3-MCPD molar ratio of 1:0.8. The antimicrobial effect of 1,2-DDAP showed the values of the minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) against microorganisms at concentrations of 10 to 100 times lower than those of 1,2-octanediol(1,2-ODIOL) or 1,2-decanediol (1,2-DDIOL). Based on the hydrophilic properties of 1,2-DDAP, mixed preservatives were prepared by adding small amounts of 1,2-ODIOL or 1,2-DDIOL, which are poorly soluble in water, with 1,2-DDAP. Mixed preservatives exhibited an effect of inhibiting microorganisms equal to or greater than that of 1,2-DDAP alone in antimicrobial activity tests. As a result of confirming the preservation effect in lotion (cosmetic formulation) for application, 1,2-DDAP showed similar antimicrobial activity at concentrations of 0.3 to 0.6 times lower than that of 1,2-ODIOL or 1,2-DDIOL. Therefore, it is considered that the use of 1,2-DDAP alone and the mixed use with small amounts of 1,2-ODIOL or 1,2-DDIOL can be a good alternative to preservatives in the product.
Keywords
Preservatives; 1,2-Alkanediol; 1,2-Dodecylaminopropanediol; Anti-microbial efficacy; Antiseptic ability in cosmetics;
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