이소소르비드 기반의 양이온 제미니 계면활성제 합성 및 물성

조정은; 정노희; Jung-Eun Cho; Noh-Hee Jeong

Applied Chemistry for Engineering, Vol.31, No.4, 429-437, August, 2020

DOI10.14478/ace.2020.1051 Export Citation

이소소르비드 기반의 양이온 제미니 계면활성제 합성 및 물성

Syntheses and Properties of Isosorbide-based Cationic Gemini Surfactants

조정은, 정노희^†

충북대학교 공과대학 공업화학과

Jung-Eun Cho, and Noh-Hee Jeong^†

Department of Engineering Chemistry, Chungbuk National University, Cheongju 28644, Korea

E-mail:

초록

본 연구에서는 이소소르비드를 이용하여 양이온 제미니 계면활성제의 알킬기가 C10∼C16개로 변화시키면서 합성하였다. 합성한 양이온 제미니 계면활성제에 대한 c.m.c는 5.13 × 10-4∼1.62 × 10-4 mol/L의 범위에서 표면장력은 31.86∼39.24 dyne/cm로 측정되었으며, 알킬기의 길이가 길어질수록 표면장력이 상승하였다. 또한, 흡착량는 감소하여 계면에 흡착된 계면활성제의 분자 당 차지하는 면적이 커지게 되면서 공기-물 계면에 기포력이 감소하였다. 벤젠에서의 유화력은 8 h이 지난 후 60 ± 5% 이상의 유화력이 유지되었으며, 대두유에서의 유화력이 50 ± 5% 이상 감소하는 경향을 보였다. 소수성이 강한 벤젠에서 우수하며, 유상과 수상의 프리에멀젼 제조 시, 유화 안정성이 일정한 시간 이상 유지되는 것을 확인할 수 있었다. 항균력은 Escherichia coli (E.coli)과 Staphylococcus aureus에서의 clean zone의 크기가 증가하여 합성한 양이온 제미니 계면활성제의 소수성 사슬의 길이에 의존하였다.

In this study, a cationic gemini surfactant was synthesized using isosorbide, in order to modify the alkyl chain length in the range of C10∼C16. The c.m.c and surface tension of the synthesized cationic gemini surfactant were measured to be in the ranges of 5.13 × 10-4~1.62 × 10-4 mol/L and 31.86~37.41 dyne/cm, respectively. The surface tension increased with increasing the length of the alkyl group. In addition, as the area per molecule occupied by the surfactant adsorbed on the interface increased with the reduced extent of adsorption, the bubble generation at the air.water interface decreased. The emulsifying capacity in benzene was maintained above 60 ± 5% after 8 h while that in soybean oil tended to decrease above 50 ± 5%. The performance was superior in benzene, a highly hydrophobic substance, and the emulsion stability was shown to be consistent beyond 1 h during the preparation of pre-emulsion in oil and water. The antimicrobial activity was dependent on the length of the hydrophobic chain of the synthesized cationic gemini surfactant due to the increased size of the clean zone in Escherichia coli (E.coli) and Staphylococcus aureus.

Keywords:Isosorbide;Cationic gemini surfactant;Critical micelle concentration;Antimicrobial activity

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[1] Lavergne A, Zhu Y, Pizzino A, Molinier V, Aubry JM, J. Colloid Interface Sci., 360(2), 645 (2011)

[2] Huynh K, Ibrahim H, Kolodziej E, Toffano M, Vo-Thanh G, New J. Chem., 35, 2622 (2011)

[3] Vujosevic ZT, Cekovic Z, Heterocycl. Comm., 7, 43 (2001)

[4] Fenouillot F, Rousseau A, Colomines G, Saint-Loup R, Pascault J, Prog. Polym. Sci, 35, 578 (2010)

[5] Gogolewski S, Gorna K, Zaczynska E, Czarny A, J. Biomed. Mater. Res. A, 85A, 456 (2008)

[6] Fiorentino G, Ripa M, Biofuel Bioprod. Biorefin., 11, 195 (2017)

[7] Cukalovic A, Stevens CV, Biofuel Bioprod. Biorefin., 2, 505 (2008)

[8] Pasquali RC, Sacco N, Bregni C, Lat. Am. J. Pharm., 28, 313 (2009)

[9] Devi TSR, Gayathri S, Int. J. Pharm. Sci. Rev. Res., 2, 106 (2010)

[10] Cho JE, Sim DS, Kim YW, Lim JC, Jeong NH, Kang HC, J. Surfact. Deterg., 21, 817 (2018)

[11] Patel U, Parekh P, Sastry N, Aswal V, Bahadur P, J. Mol. Liq., 225, 888 (2017)

[12] Phan C, Yusa S, Honda T, Sharker K, Hyde A, Nguyen C, ACS Omega, 3, 10907 (2018)

[13] KS M ISO696, Surface active agents measurement of foaming power modified Ross-miles method (2008).

[14] Xu D, Zhang J, Cao Y, Wang J, Xiao J, LWT - Food Sci. Technol., 66, 590 (2016)

[15] Jo WJ, Lee DH, Park EJ, Lee JS, J. Korean Soc. Cloth. Ind., 13, 425 (2011)

[16] Kim JY, Lee JA, Kim KN, Yoo WJ, Lee WJ, Park SY, J. Korean Soc. Food Sci. Nutr., 36, 663 (2007)