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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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  • Reference
1 J. J. Choi, W. G. Cho, and M. J. Rang, Synergistic surface activities and phase behavior in mixtures of a diglyceryl cationic surfactant and a conventional anionic surfactant, Korean Chem. Eng. Res., 46, 799-805 (2008).
2 M. G. Soni, I. G. Carabin, and G. A. Burdock, Safety assessment of esters of p-hydroxybenzoic acid (parabens), Food Chem. Toxicol., 43, 985-1015 (2005).   DOI
3 B. Dreno, T. Zuberbier, C. Gelmetti, G. Gontijo, and M. Marinovich, Safety review of phenoxyethanol when used as a preservative in cosmetics, J. Eur. Acad. Dermatol. Venereol., 33, 15-24 (2019).
4 A. Kunicka-Styczynska, M. Sikora, and D. Kalemba, Antimicrobial activity of lavender, tea tree and lemon oils in cosmetic preservative systems, J. Appl. Microbiol., 107, 1903-1911 (2009).   DOI
5 H. Mekata, The viewpoint of formulation design for preservative-free and paraben-free cosmetics, J. Soc. Cosmet. Chem. Jpn., 51, 2-11 (2017).   DOI
6 P. D. Darbre and P. W. Harvey, Paraben esters: review of recent studies of endocrine toxicity, absorption, esterase and human exposure, and discussion of potential human health risks, J. Appl. Toxicol., 28, 561-578 (2008).   DOI
7 E. Lee, S. An, S. A. Cho, Y. Yun, J. Han, Y. K. Hwang, and T. R. Lee, The influence of alkane chain length on the skin irritation potential of 1, 2-alkanediols, Int. J. Cosmet. Sci., 33, 421-425 (2011).   DOI
8 K. S. Warner, S. K. Li, and W. I. Higuchi, Influences of alkyl group chain length and polar head group on chemical skin permeation enhancement, J. Pharm. Sci., 90, 1143-1153 (2001).   DOI
9 W. Siegert, Comparison of microbial challenge testing methods for cosmetics, Househ. Pers. Care Today, 8, 32-39 (2013).
10 M. Okukawa, T. Watanabe, M. Miura, H. Konno, S. Yano, and Y. Nonomura, Antibacterial activity of 1,2-alkanediol against Staphylococcus aureus and Staphylococcus epidermidis, J. Oleo. Sci., 68, 759-763 (2019).   DOI
11 J. K. Poudrier, Final Report on the Safety Assessment of Phenoxyethanol, J. Am. Coll. Toxicol., 9, 259-277 (1990).   DOI
12 J. Geier, H. Lessmann, A. Schnuch, and W. Uter, Recent increase in allergic reactions to methylchloroisothiazolinone/methylisothiazolinone: Is methylisothiazolinone the culprit?, Contact Derm., 67, 334-341 (2012).   DOI
13 B. Croshaw, Preservatives for cosmetics and toiletries, J. Soc. Cosmet. Chem., 28, 3-16 (1977).
14 F. A. Andersen, Final amended report on the safety assessment of methyl paraben. ethylparaben, propylparaben, isopropylparaben, butylparaben, isobutylparaben, and benzylparaben as used in cosmetic products, Int. J. Toxicol., 27, 1-82 (2008).
15 I. K. Yoo, J. I. Kim, and Y. K. Kang, Conformational preferences and antimicrobial activities of alkanediols, Comput. Theor. Chem., 1064, 15-24 (2015).   DOI
16 M. S. Ryu, Effect of Antiseptics for Prevention of Microbial Contamination in Cosmetics, Master Dissertation, Sungkyunkwan University, Seoul, Korea (1990).
17 S. J. Hiom, Preservation of medicines and cosmetics. In: A. P. Fraise, P. A. Lambert, and J. Y. Maillard (eds.). Russell, Hugo and Ayliffe's, Principles and Practice of Disinfection, Preservation & Sterilization, 4th ed., 484-486, Wiley-Blackwell, Oxford, UK (2004).
18 T. A. Gaonkar, I. Geraldo, M. Shintre, and S. M. Modak, In vivo efficacy of an alcohol-based surgical hand disinfectant containing a synergistic combination of ethylhexylglycerin and preservatives. J. Hosp. Infect., 63, 412-427 (2006).   DOI
19 M. Sigg and R. Daniels, Investigations on alkanediols as alternative preservatives in a nonionic hydrophilic cream, Pharmaceutics, 12, 1117 (2020).   DOI
20 S. B. Levy, A. M. Dulichan, and M. Helman, Safety of a preservative system containing 1,2-hexanediol and caprylyl glycol, Cutan. Ocul. Toxicol., 28, 23-24 (2009).   DOI
21 F. Schambil and M. J. Schwuger, Interfacial and colloidal properties. In: J. Falbe (ed.). Surfactants in Consumer Products, 170-177, Springer, Berlin, Germany (1987).
22 P. Ziosi, S. Manfredini, A. Vandini, S. Vertuani, and M. Fraternali, Caprylyl glycol/phenethyl alcohol blend for alternative preservation of cosmetics, Cosmet. Toilet., 128, 538-549 (2013).
23 J. I. Kim, Study on the Challenge Test and Safety Assessments of 1,2-Alkanediols in Cosmetics, PhD Dissertation, Hannam University, Daejeon, Korea (2016).
24 K. O. Cha, S. W. Kwak, K. I. Jeong, and Y. H. Kim, Synthesis of 1,2-dodecylaminopropanediol and its mixing effect with 1,2-alkanediols as preservatives, Appl. Chem. Eng., 33, 179-187 (2022).