酯基季铵盐双子表面活性剂的合成研究进展

doi:10.13218/j.cnki.csdc.2015.10.010

摘要/Abstract

摘要： 综述了酯基分别为连接基和疏水基的对称型季铵盐双子(Gemini)表面活性剂以及不对称酯基季铵盐Gemini表面活性剂的合成方法,并对合成产物的性能及应用进行了简单介绍,最后对酯基季铵盐Gemini表面活性剂的发展进行了展望。

关键词: 酯基季铵盐, 双子表面活性剂, 可分解性, 合成

Abstract: Synthesis methods of symmetric and asymmetric Gemini quaternary ammonium salt surfactants with ester group (esterquats) as the spacer and as the hydrophobic group were summarized separately.Meanwhile,performance and applications of the synthesized Gemini esterquats were briefed.Future development of such category of surfactant was prospected.

Key words: esterquats, Gemini surfactant, degradation, synthesis

中图分类号:

TQ423.12

王渊, 刘强, 高文超, 李兴, 魏文珑, 常宏宏. 酯基季铵盐双子表面活性剂的合成研究进展[J]. 日用化学工业, 2015, 45(10): 582-588.

WANG Yuan, LIU Qaing, GAO Wen-chao, LI Xing, WEI Wen-long, CHANG Hong-hong. Progress in research work field for synthesis of Gemini quaternary ammonium salt surfactants with ester group[J]. China Surfactant Detergent & Cosmetics, 2015, 45(10): 582-588.

参考文献

[1] MENGER F M,LITTAU C A.Gemini surfactants:Synthesis and properties[J].Journal of the American Chemical Society,1991,113:1451-1452.
[2] ROSEN M J.Geminis:A new generation of surfactants[J].Chemtech,1993,23(3):30-33.
[3] ZANA R,BENRRAOU M,RUEFF R.Alkanediyl-α,ω-bis(dimethyl-alkylammonium bromide) surfactants.1.Effect of the spacer chain length on the critical micelle concentration and micelle ionization degree[J].Langmuir,1991,7(6):1072-1075.
[4] ROSEN M J,TRACY D J.Gemini surfactants[J].Journal of Surfactants and Detergents,1998,1(4):547-554.
[5] MENGER F M,KEIPER J S.Gemini surfactants[J].Angewandte Chemie International Edition,2000,39:1906-1920.
[6] 赵剑曦. 新一代表面活性剂:Geminis[J].化学进展,1999,11(4):348-356.
[7] 张立,张哲,王红利,等.季铵盐型Gemini表面活性剂的合成研究进展[J].中国洗涤用品工业,2014(6):62-68.
[8] QIU L G,WU Y,WANG Y M,et al.Synergistic effect between cationic Gemini surfactant and chloride ion for the corrosion inhibition of steel in sulphuric acid[J].Corrosion Science,2008,50(2):576-582.
[9] LAURENT C,ELISABETH T G,RICHARD L,et al.Polymerizable semi-?uorinated Gemini surfactants designed for antimicrobial mate-rials[J].Journal of Colloid and Interface Science,2009,332:201-207.
[10] CZECHURA K,SAYARI A.Synthesis of MCM-48 silica using a Gemini surfactant with a rigid spacer[J].Chemistry of Materials,2006,18(17):4147-4150.
[11] WANG X L,ZHANG X H,CAO M W,et al.Gemini surfactant-induced DNA condensation into a beadlike structure[J].Journal of Physical Chemistry B,2009,113(8):2328-2332.
[12] CHOI T S,SHIMIZU Y,SHIRAI H,et al.Disperse dyeing of nylon 6 fiber using Gemini surfactants containing ammonium cations as auxiliaries[J].Dyes and Pigments,2001,48:217-226.
[13] STJERNDAHL M,HOLMBERG K.Hydrolyzable nonionic surfactants:Stability and physicochemical properties of surfactants containing carbonate,ester,and amide bonds[J].Journal of Colloid and Interface Science,2005,291(2):570-576.
[14] ALIREZA T B,KRISTER H.Cleavable surfactants[J].Current Opinion in Colloid and Interface Science Curr,2007,12:81-91.
[15] 赵剑曦. Gemini表面活性剂:联接链在自组织中的作用及意义[J].化学进展,2014,26(8):1339-1351.
[16] 姚志刚,李干佐,董凤兰,等.Gemini表面活性剂合成进展[J].化学进展,2004,16(3):350-363.
[17] 高志农,吕波,魏俊超.含酯基季铵盐Gemini表面活性剂的合成及表面活性[J].武汉大学学报:理学版,2006,52(2):159-162.
[18] ANSARI W H,FATMA N,PANDA M,et al.Solubilization of polycyclic aromatic hydrocarbons by novel biodegradable cationic Gemini surfactant ethane-1,2-diyl bis(N,N-dimethyl-N-hexadecylammoniumacetoxy) dichloride and its binary mixtures with conventional surfactants[J].Soft Matter,2013,9(5):1478-1487.
[19] FATMA N,ANSARI W H,PANDA M,et al.Mixed micellization behavior of Gemini (cationic ester-bonded) surfactants with conventional (cationic,anionic and nonionic) surfactants in aqueous medium[J].Zeitschrift fuer Physikalische Chemie,2013,227(1):133-149.
[20] ZAHID Y,SAYEED U R,MOHAMMAD T,et al.Interaction between DNA and cationic diester-bonded Gemini surfactants[J].Journal of Molecular Liquids,2014,197:322-327.
[21] 赵国玺,朱瑶.表面活性剂作用原理[M].北京:中国轻工业出版社,2003.
[22] WANG Y X,HANY C,HUANG X,et al.Aggregation behavior of a series of anionic sulfonate Gemini surfactants and their corresponding monomeric surfactant[J].Journal of Colloid and Interface Science,2008,319(2):534-541.
[23] WANG Y X,HUANG X,LI Y J,et al.Aggregation properties of zwitterionic surfactants with different ionic headgroups,hydrophobic chain length and inter-charge spacers[J].Colloids and Surfaces A:Physicochemical and Engineering Aspects,2009,333:108-114.
[24] XU D Q,PAN Z W.Phase-transfer catalysis of a new cationic Gemini surfactant with ester groups for nucleophilic substitution reaction[J].Chinese Chemical Letters,2014,25:1169-1173.
[25] 陈五洋,高志农,刘学国,等.二酯基连接链乙基头基季铵盐Gemini表面活性剂的合成及性质[J].武汉大学学报:理学版,2013,59(4):311-316.
[26] AVINASH B,REKHA G S,SET K S,et al.Self-aggregation properties of new ester-based Gemini surfactants and their rheological behavior in the presence of cosurfactant-monolaurin[J].Colloids and Surfaces A:Physicochemical and Engineering Aspects,2014,461:258-266.
[27] 刘佳煊. 双酯基季铵盐表面活性剂的合成及性能研究[J].河南化工,2011,28(12):37-39.
[28] 苗宗成,王义伟,王登武,等.Gemini型可降解阳离子表面活性剂制备与应用[J].针织工业,2014(1):40-42.
[29] 苗宗成,王义伟,王登武,等.新型草酸二酯类Gemini季铵盐表面活性剂的制备[J].化工新型材料,2013,41(8):65-66.
[30] 苗宗成,张永明,霍小平,等.新型双生阳离子季铵盐的合成及其表面活性[J].合成化学,2014,22(2):234-237.
[31] 苗宗成,王义伟,王登武,等.一种双子型双酯类阳离子表面活性剂的生物降解行为研究[J].日用化学工业,2013,43(5):354-357.
[32] 贾丽华,郭祥峰,于宏,等.含酯基双子季铵盐阳离子表面活性剂的合成及性能[J].日用化学工业,2002,32(3):34-35.
[33] TEHRANI-BAGHA A R,OSKARSSON H,HOLMBERG K.Cationic ester-containing Gemini surfactants:Chemical hydrolysis and biode-gradation[J].Journal of Colloid and Interface Science,2007,312:444-452.
[34] 阿不都热合曼·乌斯曼,买尔哈巴·赛都.双酯基阳离子Gemini表面活性剂的合成[J].化学试剂,2008,30(10):761-765.
[35] 王中才,许虎君,包新颜,等.酯基Gemini型季铵盐表面活性剂的合成与性能[J].江南大学学报:自然科学版,2005,4(3):306-309.
[36] TEHRANI-BAGHA A R,HOLMBERG K.Cationic ester-containing Gemini surfactants:Physical-chemical properties[J].Langmuir,2010,26(12):9276-9282.
[37] TEHRANI-BAGHA A R,KÄRNBRATT J,LÖFROTH J E,et al.Cationic ester-containing Gemini surfactants:Determination of aggregation numbers by time-resolved ?uorescence quenching[J].Journal of Colloid and Interface Science,2012,376:126-132.
[38] 娄平均,朱红军,丁徽,等.双酯基Gemini季铵盐织物柔软剂的制备与性能研究[J].印染助剂,2011,28(5):28-29.
[39] 杨英宜,卢峰,马毅.双十四叔胺羟丙基甘氨酸季铵盐的合成及性能[J].汕头大学学报:自然科学版,2006,21(4):43-45.
[40] 魏俊超,高志农,吕波.不对称季铵盐Gemini表面活性剂的合成及性质[J].武汉大学学报:理学版,2006,52(2):163-166.
[41] 唐世华,黄建斌,李子臣.Gemini表面活性剂研究的新进展[J].自然科学进展,2011,11(12):1240-1251.
[42] 赵剑曦. Gemini高效稳泡剂[J].精细与专用化学品,2011,19(6):11-14.
[43] WEYTS A F,DHAWAN P,CHRISTAKOS S,et al.Novel Gemini analogs of 1,25-dihydroxyvitamin D3 with enhanced transcriptional activity[J].Biochemical Pharmacology,2004,67:1327-1336.
[44] 牛华,娄平均,朱红军,等.含酯基Gemini季铵盐柔软剂的合成工艺研究[J].精细化工,2010,27(8):824-832.
[45] 潘忠稳,王磊,夏岚.一种含酯基不对称阳离子Gemini表面活性剂的合成[J].精细化工,2009,26(3):227-229.