烯丙基二甲基烷基溴化铵的合成与性能研究

doi:10.13218/j.cnki.csdc.2015.11.004

摘要/Abstract

摘要： 以烯丙基二甲基胺(ADMA)和1-溴代直链烷为原料,合成了2种不同碳链长度(n=16,18)的烯丙基二甲基烷基溴化铵(C₁₆和C₁₈),得到较佳的合成工艺条件为以丙酮作溶剂,ADMA与溴代烷的摩尔比为1∶1.1~1.2,65 ℃下反应60 h,所得产品的收率分别为68.20%和66.05%。用IR,¹HNMR和元素分析对产品结构进行了表征,并测定了产品的表面活性、水溶性、泡沫性能、乳化性及絮凝性。结果表明,C₁₆和C₁₈的临界胶束浓度分别为5.5×10^-4和1.8×10^-4 mol/L,相应的表面张力分别为33.5和32.4 mN/m,产品具有良好的表面活性;C₁₆和C₁₈的Krafft点分别为8和21 ℃;与十二烷基硫酸钠(SDS)相比,产品的乳化能力较弱;C₁₆的发泡能力以及对高岭土的絮凝能力明显强于C₁₈。

关键词: 季铵盐, 烯丙基二甲基烷基溴化铵, 合成, 性能

Abstract: Two kinds of allyldimethylalkylammonium bromide (C₁₆ and C₁₈) with different carbon chain length (n=16,18) were synthesized by using allyldimethylamine (ADMA) and 1-bromo linear alkanes as starting materials.The better synthetic conditions are as follows:acetone as the solvent;reaction temperature,65 ℃;reaction time,60 h;molar ratio of ADMA to 1-bromo alkane,1∶1.1~1.2.Yield of the product are 68.20% and 66.05% respectively.Their structures were characterized by IR,¹HNMR and elemental analysis.Their performance was measured,such as surface activity,water solubility and foaming,emulsifying and flocculating performance.Results showed that critical micelle concentration of the products (C₁₆ and C₁₈) is 5.5×10^-4 and 1.8×10^-4 mol/L respectively.Their corresponding surface tension is 33.5 and 32.4 mN/m respectively.The products display good surface properties.Krafft point is 8 and 21 ℃ respectively.The products display lower emulsifying power than that of sodium dodecyl sulfonate (SDS).The product C₁₆ displays significantly stronger foaming power and stronger flocculating capacity to kaolin than that of the product C₁₈.

Key words: quaternary ammonium salt, allyldimethylalkylammonium bromide, synthesis, performance

中图分类号:

TQ423.12

陶贤平, 张跃军. 烯丙基二甲基烷基溴化铵的合成与性能研究[J]. 日用化学工业, 2015, 45(11): 616-620.

TAO Xian-ping, ZHANG Yue-jun. Synthesis and performance of allyldimethylalkylammonium bromide[J]. China Surfactant Detergent & Cosmetics, 2015, 45(11): 616-620.

参考文献

[1] WANG G J,ENGBERTS J B F N.Non-cross-linked and cross-linked poly(alkylmethyldiallyl ammonium halides):Synthesis and aggregation behavior[J].Journal of Physical Organic Chemistry,1998(11):305-320.
[2] HOSSEIN M,MAHDI M.Synthesis and applications of cross-linked poly(diallyldimethyl ammonium chloride) and its derivative copolymers as efficient phase transfer catalyst for nucleophilic substitution reactions[J].Chinese Journal of Polymer Science,2011,29(2):165-172.
[3] 陶贤平,张跃军.二烯丙基甲基胺/溴代烷系列季铵盐的合成与表征[J].精细化工,2014,31(10):1291-1296.
[4] 朱涛,李潇潇,曾碧涛.季铵盐类阳离子单体的合成工艺研究进展[J].化学研究与应用,2014,26(10):1527-1532.
[5] SMITH K R,ROUGE B,BORLAND J E,et al.Quaternary ammonium compounds:US,4824867 [P].1989-04-25.
[6] PEIFFER D G.Polymerization of cationic N,N-dimethylalkylamine type monomers:US,4853447 [P].1989-08-01.
[7] PEIFFER D G.Viscoelastic fluids formed through the interaction of polymerizable vesicles and alkyl-containing polymers (C-2381):US,4975482 [P].1990-12-04.
[8] PEIFFER D G.Polymerizable cationic viscoelastic monomer fluids:US,5066753 [P].1991-11-19.
[9] WU MINGHUO,WU RENAN,WANG FANGJUN,et al.“One-pot” process for fabrication of organic-silica hybrid monolithic capillary columns using organic monomer and alkoxysilane[J].Analytical Chemistry,2009,81(9):3529-3536.
[10] 张昌辉,谢瑜,曹娟.一种季铵盐阳离子表面活性剂的合成与性质[J].日用化学工业,2007,37(6):364-366,416.
[11] 张新民,罗平亚,郭拥军.堵漏剂及其制备方法:CN,103396774A[P].2013-11-20.
[12] 王湘英,朱建林.N,N-二甲基-N-丙烯基十六烷基溴化铵的合成及表征[J].材料研究与应用,2008,2(1):47-50.
[13] WANG XIANGYING,ZHU JIANLIN,WANG JINBEN,et al.Micelle formation and aggregate morphology transition from vesicle to rod micelle for allylalkyldimethylammonium bromide cationic surfactant[J].Journal of Dispersion Science and Technology,2008,29:83-88.
[14] 谢瑜,张昌辉,徐旋.聚合季铵盐阳离子表面活性剂的合成与性能研究[J].日用化学品科学,2008,31(2):21-24.
[15] 陶贤平,张跃军,李侠,等.二烯丙基甲基烷基溴化铵的结构与性质的关系[J].应用化学,2015,32(3):342-349.
[16] 金光勇,何志强,方云,等.新型伸展型表面活性剂辛基聚氧丙烯(9)聚氧乙烯(6)硫酸酯钠/磺酸钠的合成及其性能[J].石油化工,2014,43(3):310-315.
[17] 崔正刚. 表面活性剂、胶体与界面化学基础[M].北京:化学工业出版社,2013:327.
[18] 朱海林,胡志勇,王建龙,等. 系列羟基磺基甜菜碱表面活性剂的合成及胶束化行为研究[J].日用化学工业,2012,42(6):405-409.
[19] 陈荣圻. 表面活性剂化学与应用[M].北京:纺织工业出版社,1990:8-79,224-233.