酯基三甲氧基有机硅季铵盐的合成及其表面活性

doi:10.13218/j.cnki.csdc.2014.11.136

摘要/Abstract

摘要： 以硬脂酸、N,N-二甲基乙醇胺(DMEA)和γ-氯丙基三甲氧基硅烷为原料合成酯基三甲氧基有机硅季铵盐,采用FTIR,ESI-MS和¹HNMR对中间体及终产物进行了结构表征,结果与目标结构一致。通过正交试验,得到中间体硬脂酸二甲基乙醇胺酯的优化合成工艺条件:反应温度为180 ℃,反应时间为8 h,n(硬脂酸):n(DMEA)=1:1.6,催化剂用量为原料总质量的0.5%。季铵化合成产物的优化工艺条件:在N₂保护下,反应温度为110 ℃,n(硬脂酸二甲基乙醇胺酯):n(γ-氯丙基三甲氧基硅烷)=1:1.4,催化剂用量为原料总质量的0.5%,反应时间为28 h。并通过稳态荧光法测得产物在298 K下的临界胶束浓度为0.009 3 g·L^-1。

关键词: 酯基三甲氧基有机硅季铵盐, 合成, 表面活性, 稳态荧光法

Abstract: An ester group trimethoxy organosilicon quaternary ammonium salt was synthesized with stearic acid,dimethylethanolamine (DMEA) and γ-chloropropyl trimethoxy siloxane as starting materials.Structure of the product was characterized by FTIR,ESI-MS and ¹HNMR,and the characterization results showed that the product is accord with the target.Via orthogonal designed experiments,the optimum reaction conditions for preparing the intermediate stearic acid dimethylethanolamine ester were obtained as:reaction temperature,180 ℃;reaction time,8 h;mole ratio,n(stearic acid):n(DMEA)=1:1.6;dosage of the catalyst,0.5%;and for the quaternarization,reaction temperature,110 ℃ under nitrogen atmosphere;mole ratio,n(stearic acid dimethylethanolamine ester):n(γ-chloropropyl trimethoxy siloxane)=1:1.4;dosage of the catalyst,0.5%;reaction time,28 h.The cmc of the product under 298 K were determined by steady-state fluorescence analysis as 0.009 3 g·L^-1.

Key words: ester group trimethoxy organosilicon quaternary ammonium salt, synthesis, surface activity, steady-state fluorescence analysis

中图分类号:

TQ423

陈瑞兰, 张俊杰, 毛桃嫣, 郑成. 酯基三甲氧基有机硅季铵盐的合成及其表面活性[J]. 日用化学工业, 2014, 44(11): 611-614.

CHEN Rui-lan, ZHANG Jun-jie, MAO Tao-yan, ZHENG Cheng. Synthesis and surface activity of the ester group trimethoxy organosilicon quaternary ammonium salt[J]. China Surfactant Detergent & Cosmetics, 2014, 44(11): 611-614.

参考文献

[1] 李俊英,冯圣玉,李天铎.聚硅氧烷季铵盐抗菌整理剂的合成及应用[J].日用化学工业,2003,33(4):249-251.
[2] 蒋波.γ-氯丙基三甲氧基硅烷季铵化反应规律研究[D].杭州:浙江大学,2005.
[3] SHAO HUI,MENG WEIDONG,QING FENGLING,et al.Synthesis and surface antimicrobial activity of a novel perfluorooctylated quaternary ammonium silane coupling agent [J].Journal of Fluorine Chemistry,2004,125:721-724.
[4] MYONGSEON G,JAEUK K,JONGGYU K.Preparation of water-durable humidity sensor by attachment of polyelectrolyte membrane to electrode substrate by photochemical crosslinking reaction [J].Sensors and Actuators B,2010,147:539-547.
[5] BRUNO M,CHRISTINE L.Production of silyl quaternary ammonium compounds:US,4845256 [P].1989-07-04.
[6] 赵洁,安秋凤,李献起,等.有机硅在抗菌整理剂中的应用[J].化学进展,2014,26(2/3):310-319.
[7] 谢瑜,张昌辉,徐旋.有机硅季铵盐抗菌剂的研究进展[J].中国胶粘剂,2008,17(2):52-55,64.
[8] 冯耀平,黄亚茹,葛赞,等.有机硅表面活性剂研究进展[J].中国洗涤用品工业,2011(1):69-71,76.
[9] 张博,吴桐,赵富华,等.含硅表面活性剂的应用及其绿色化发展[J].化工科技市场,2010(5):29-32.
[10] 河合博.道康宁5700抗微生物处理剂[J].印染,1996(3):38-42.
[11] COLURCIELLO JR,FRANCIS A,BENNETT,et al.Alkaline hard surface cleaning and disinfecting compositions including silicone quarternary ammonium salts:US,6376448B1 [P].2002-04-23.
[12] COLURCIELLO JR,FRANCIS A,BENNETT,et al.Acidic hard surface cleaning and disinfecting compositions which include silicone quarternary ammonium salts:US,6559111B2 [P].2003-05-06.
[13] 黄武欢,郑成,毛桃嫣,等.酯基有机硅季铵盐柔软整理剂的合成与表征[J].精细化工,2012,29(12):1167-1171.
[14] 徐清,蒋波,詹晓力,等.γ-氯丙基三甲氧基硅烷季铵化反应中的溶剂效应研究[J].高校化学工程学报,2007(4):640-644.
[15] 蒋波,詹晓力,陈丰秋.γ-氯丙基三甲氧基硅烷季铵化反应规律探讨[J].化学反应工程与工艺,2006(1):33-36,42.
[16] WU JIE,WANG LIMIN,ZHAO PING,et al.A new type of quaternary ammonium salt containing siloxane group and used as favorable dispersant in the surface treatment of C.I.pigment red 170 [J].Progress in Organic Coatings,2008,63:189-194.
[17] LI JUNYING,ZHANG QINGSI,WANG YAN,et al.Synthesis and properties of organosilicon quaternary salts surfactants [J].J Surfact Deterg,2012,15:339-344.
[18] GONG SHIQIANG,NIU LINA,LISA K K,et al.Quaternary ammonium silane-functionalized,methacrylate resin composition with antimicrobial activities and self-repair potential [J].Acta Biomaterialia,2012,8:3270-3282.
[19] BARBARA S,BRIGITA T.Multifunctional water and oil repellent and antimicrobial properties of finished cotton:influence of sol-gel finishing procedure [J].J Sol-Gel Sci Technol,2012,61:340-354.
[20] SHAILESH P S,PIYUSH N K,DIPAK K R.Acidic ionic liquid immobilized on cellulose:An efficient and recyclable heterogeneous catalyst for the solventfree synthesis of hydroxylated trisubstituted pyridines [J].RSC Advances,2013,3:3184-3188.
[21] 王友国,王佩维,姚晨之,等.织物柔软剂酯基季铵盐生物降解性的研究[J].化工新型材料,2005,33(7):19-21.