공업화학 (Applied Chemistry for Engineering)

  • 제33권2호
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  • Pages.179-187
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  • 2022
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  • 1225-0112(pISSN)
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  • 2288-4505(eISSN)
한국공업화학회 (The Korean Society of Industrial and Engineering Chemistry)
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보존제로서 1,2-도데실아미노프로판디올의 합성 및 1,2-알칸디올 화합물의 혼합 효과

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

  • 차경온 (충남대학교 응용화학공학과) ;
  • 곽상운 (충남대학교 응용화학공학과) ;
  • 정국인 ((주)비제이바이오켐) ;
  • 김영호 (충남대학교 응용화학공학과)
  • 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)
  • 투고 : 2022.01.12
  • 심사 : 2022.03.07
  • 발행 : 2022.04.10
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초록

본 연구에서는 1,2-알칸디올계 화합물의 보존력과 친수성을 향상할 목적으로 12개의 탄소 사슬 길이와 아민기를 갖는 1,2-도데실아미노프로판디올(1,2-dodecylaminopropanediol, 1,2-DDAP)의 합성을 설계하였다. 1,2-DDAP는 40 ℃의 에탄올(ethanol) 용매에서 도데실아민(dodecyl amine, DDA)과 3-모노클로로-1,2-프로판디올(3-monochloro-1,2-propanediol, 3-MCPD)의 반응에 의해 제조하였으며, 그 수율과 순도는 1:0.8의 DDA:3-MCPD 몰 비와 2 h의 반응 조건에서 각각 약 56%와 98%였다. 1,2-DDAP의 항균 효과는 1,2-옥탄디올(1,2-octanediol, 1,2-ODIOL) 또는 1,2-데칸디올(1,2-decanediol, 1,2-DDIOL)과 비교하여 10~100배 낮은 농도에서 미생물에 대한 최소억제농도와 최소살균농도 값을 나타내었다. 1,2-DDAP의 친수성을 바탕으로 1,2-DDAP로 물에 난용성인 1,2-ODIOL 또는 1,2-DDIOL을 소량 첨가하여 혼합 보존제를 제조하였다. 항균력 시험에서 혼합 보존제는 1,2-DDAP 단독사용 대비 동등 이상의 미생물 억제효과를 나타내었다. 응용을 위해 로션(화장품 제형)에서 보존 효과를 확인한 결과, 1,2-DDAP는 1,2-ODIOL 또는 1,2-DDIOL과 비교하여 0.3~0.6배의 낮은 농도에서 유사한 항균력을 나타내었다. 따라서 1,2-DDAP의 단독 사용 및 1,2-ODIOL 또는 1,2-DDIOL을 소량 혼합하여 사용하는 것이 제품 내 보존제에 대한 좋은 대안으로 사용될 수 있을 것이다.

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.

키워드

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