• Applied Chemistry for Engineering
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• v.33 no.2
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• pp.179-187
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• 2022

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.

• Applied Chemistry for Engineering
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• v.33 no.4
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• pp.394-401
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• 2022

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%.