• Korean Journal of Chemical Engineering
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• 제35권11호
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• pp.2313-2320
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• 2018

Tetramethylene-1,4-bis(N,N-dodecylammonium bromide), cationic gemini surfactant, (12-4-12) was first synthesized with an one-step and shortened procedure and its interfacial and antimicrobial properties were compared with a conventional single-chain cationic surfactant, cetyltrimethylammonium bromide (CTAB). The interfacial and thermodynamic properties of both surfactants reveal that critical micelle concentration (CMC) of this novel synthetic cationic dimeric surfactant is lower than that of cationic monomeric surfactant at almost 15 times of its magnitude, which is due to the increase in hydrophobicity of the surfactant molecules by having dual hydrocarbon chains. In comparison with CTAB, the produced compound 12-4-12 yields much better interfacial and thermodynamic properties. The antimicrobial activities of the synthesized gemini surfactant were tested against eight strains of bacteria, as well as two strains of fungi. The results showed that both 12-4-12 compound and CTAB exhibited higher inhibitory effects on the growth of Gram-positive bacteria and fungi than that of Gram-negative bacteria. The minimum inhibitory concentrations in molar of 12-4-12 against all tested Gram-negative bacteria were lower than those of CTAB, which is hypothetically due to the lower HLB together with smaller CMC values of our gemini surfactant.

• 한국응용과학기술학회지
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• 제30권2호
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• pp.312-319
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• 2013

이 연구는 글리시딜 숙시네이트 양이온 제미니 계면활성제의 합성에 관한 것이다. 제미니 계면활성제는 2-메틸 디소디움 숙시네이트와 에피클로로히드린, N, N-디메틸 도데실 아민을 사용하여 합성하였다. FT-IR과 $^1H$-NMR을 통해 물성을 확인하였다. 표면장력과 cmc 측정, 유화력 및 기포력을 각각 주어진 조건을 이용하여 측정하였다. 제미니 계면활성제의 표면장력은 33~34 dyne/cm이며 cmc 값은 $10^{-4}{\sim}10^{-3}mol/L$ 였다. 제미니 계면활성제의 유화력은 유기용매에서 더 우수하였고 기포력이 안정한 것을 확인하였다.

• 한국응용과학기술학회지
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• 제18권2호
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• pp.95-102
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• 2001

Recently, there has been considerably interested in the development to new functional gemini type anionic surfactant, sodium bis-n-alkyl sulfonatosuccinate, had been synthesized through the addition reaction of sodium bisulfite to bis-n-alkyl maleate, in which water was azeotropically distilled by adding benzene to the reaction system, gave a good yield. All the surface activities including krafft point, surface tension, emulsion power and foaming were measure and cmc was evaluated in dilute solution. This results showed a lower ability in $27{\sim}30dyne/cm$ than single-chain surfactant with $32{\sim}35dyne/cm$ to surface tension. Also its cmc value much smaller in $(6.5{\sim}10){\times}10^{-4}mca{\ell}/{\ell}$ than single-chain surfactant with $(40{\sim}45){\times}10^{-4}mca{\ell}/{\ell}$ concentration. In foaming ability and foam stability of gemini surfactant had especially a good ability in approximately $100{\sim}150ml$, and in emulsing power they exhibited a good emulsing phase and stability, and Krafft points were $0{\sim}10^{\circ}C$.

• 한국토양환경학회지
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• 제5권1호
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• pp.65-73
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• 2000

계면활성제를 사용하여 토양에 존재하는 소수성 유기오염물질을 제거하는 방법이 많이 연구되어져 왔다. 본 연구에서는 계면활성제의 구조적 차이에 따른 오염물질의 용해도 증가 효율을 평가하기 위하여 기존 계면활성제와는 다른 구조를 가진 계면활성제들을 가지고 비교·실험하였다. 그 결과 쌍둥이형 계면활성제(gemini surfactant)인 DADS12가 가장 용해도 증가율이 높게 나타났으며 머리가 두 개인 쌍두형 계면활성제(dianionic surfactant)가 일반 계면활성제인 SDDBS보다 적은 용해도 증가를 나타내었다. 이는 계면활성제의 유기탄소분율이 큰 것일수록 용해도 증가가 크고 계면활성제의 구조적 특성에 따른 마이셀의 형태나 구조에 크게 영향을 받지 않으며, 오염물질과 계면활성제 분자에다 존재하는 벤젠 고리간의 상호 인력 작용이 거의 일어나지 않거나 아주 미미한 것으로 보이며, 이에 따라 나프탈렌과 휘난트렌의 경우 오염물질의 제거 기작이 주로 마이셀 내부에 형성된 소수성 pseudophase로 오염물질이 흡수되는 것으로 추측된다.

• 한국응용과학기술학회지
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• 제28권2호
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• pp.140-145
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• 2011

Cationic gemini-surfactant, namely 1,4-butane-bis(N-alkanoyloxyethyl-N,Ndimethyl)-diammonium bromide was synthesized and their inhibition effect on corrosion of mild steel in 1 M HCl solution was tested by weight loss method. The synthesized product was confirmed by FT-IR and $^1H-NMR$ spectroscopy. Surface tensions were measured by surface tensiometer Sigma 70. Their c.m.c. values evaluated by surface tension method was $4.1{\times}10^{-5}{\sim}5.4{\times}10^{-5}$ mol/L. The Krafft point of the these surfactants were <0~$10.7^{\circ}C$. The emulsifying properties of synthesized cationic gemini surfactants and sodium dodecyl sulfate (SDS), tetradecyl trimethyl ammonium bromide (TTAB) was investigated. Of these, 1,4-butane-bis(N-lauroyloxyethyl-N,N-dimethyl)- diammonium bromide, CGL 14-4-14 has been confirmed as a good emulsifier. The inhibition efficiency increases by increasing cationic gemini surfactant concentration. As a result, these surfactants are expected to be applied as corrosion inhibitors.

• 한국응용과학기술학회지
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• 제31권1호
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• pp.1-6
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• 2014

Gemini type of cationic surfactant, namely ${\alpha},{\omega}$-alkane-bis(N-lauroyloxyethyl-N,N-dimethyl)-diammonium bromide was synthesized and confirmed by FT-IR and $^1H$-NMR spectroscopy. Their inhibition effect on corrosion of mild steel in 1 M HCl solution was tested by weight loss method. Surface tensions were measured by surface tensiometer Sigma 70. Their c.m.c. values evaluated by surface tension method was $4.01{\times}10^{-5}{\sim}4.99{\times}10^{-5}mol/L$. The Krafft point of the these surfactants were < $0^{\circ}C$. The emulsifying properties of synthesized cationic gemini surfactants and sodium dodecyl sulfate (SDS), tetradecyl trimethyl ammonium bromide (TTAB) was investigated. Of these, ${\alpha},{\omega}$-alkane-bis(N-lauroyloxyethyl-N,N-dimethyl)-diammonium bromide has been confirmed as a good emulsifier. The inhibition efficiency increases by increasing cationic gemini surfactant concentration. As a result, these surfactants are expected to be applied as corrosion inhibitors.

• 한국응용과학기술학회지
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• 제27권3호
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• pp.257-265
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• 2010

This study concerned about "Gemini type co-surfactant" which has very interesting properties with new components. They were synthesized by reaction of diethylene glycol monoethyl ether and dicarboxylic acid. The structure could be comfirmed with FT-IR and $^1H$-NMR. Surface active properties such as surface tension, evaluated cmc, cloud point, emulsing power were measured respectively at given conditions. Their surface tensions in the aqueous solution were decreased to 33~35 dyne/cm, which was lower than 39 dyne/cm of SDS, and their cmc values evaluated by surface tension method were $5.0{\times}10^{-1}\sim7.5{\times}10^{-1}$ mol/L. And the emulsifying power was excellent in jojoba oil. All of the synthesized Gemini surfactants possessed good water solubility and their cloud point were $48\sim58^{\circ}C$. As results, Gemini surfactants which were synthesized are expected to be applied as O/W emulsifiers.

• 공업화학
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• 제30권1호
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• pp.17-22
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• 2019

본 연구에서는 소수성 사슬의 길이를 증가시키고 1,4-부탄디올을 스페이서로 사용하여 양이온성 제미니형 계면활성제를 합성하였으며 $^1H-NMR$로 확인하였다. 합성한 계면활성제의 외형은 백색 분말로 나타났으며, Kraffts 점은 $0^{\circ}C$ 이하로 나타났다. 측정된 임계미셀농도(c.m.c)는 표면장력법에 의해 $1.8{\times}10^{-3}{\sim}6.5{\times}10^{-4}mol/L$이었고 표면 장력은 22.5~26.1 dyne/cm이었다. Ross-Miles 방법에 의한 CG 14-6E-14의 초기 거품 높이는 16 cm이었고 5 min 후 높이 14 cm를 나타내어, 가장 좋은 초기 기포력과 기포안정성을 갖는 것을 확인하였다. 또한, 합성한 양이온 제미니 계면활성제와 일반적으로 사용하고 있는 cetyltrimethylammonium bromide (CTAB)의 기포력 및 유화안정성을 비교하였다.

• 공업화학
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• 제31권4호
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• pp.429-437
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• 2020

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.

• Journal of Microbiology and Biotechnology
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• 제21권1호
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• pp.93-99
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• 2011

Amongst a number of potential nonviral vectors, cationic liposomes have been actively researched, with both gemini surfactants and bola amphiphiles reported as being in possession of good structures in terms of cell viability and in vitro transfection. In this study, a cholesterol-based diquaternary ammonium gemini surfactant (Chol-GS) was synthesized and assessed as a novel nonviral gene vector. Chol-GS was synthesized from cholesterol by way of four reaction steps. The optimal efficiency was found to be at a weight ratio of 1:4 of lipid:DOPE (1,2-dioleoyl-L-${\alpha}$- glycero-3-phosphatidylethanolamine), and at a ratio of between 10:1~15:1 of liposome:DNA. The transfection efficiency was compared with commercial liposomes and with Lipofectamine, 1,2-dimyristyloxypropyl-3-dimethylhydroxyethylammonium bromide (DMRIE-C), and N-[1-(2,3-dioleoyloxy)propyl]-N,N,N-trimethylammonium chloride (DOTAP). The results indicate that the efficiency of Chol-GS is greater than that of all the tested commercial liposomes in COS7 and Huh7 cells, and higher than DOTAP and Lipofectamine in A549 cells. Confirmation of these findings was observed through the use of green fluorescent protein expression. Chol-GS exhibited a moderate level of cytotoxicity, at optimum concentrations for efficient transfection, indicating cell viability. Hence, the newly synthesized Chol-GS liposome has the potential of being an excellent nonviral vector for gene delivery.