头基含羟基的季铵盐双子表面活性剂的合成与性能

doi:10.3969/j.issn.1001-1803.2019.03.001

摘要/Abstract

摘要：

以溴代烷、二乙醇胺和1,4-二溴丁烷为原料,通过两步反应合成了一类头基含羟基的季铵盐双子表面活性剂亚丁基-1,4-双（烷基二羟乙基溴化铵）（m-4-m（OH）,m=8,10,12,14）,通过核磁共振氢谱（ ¹H NMR）和质谱（MS）对中间体和目标产物的结构进行表征。通过表面张力仪和电导率仪测定m-4-m（OH）在水溶液中的平衡表面张力（γ_cmc）和临界胶束浓度（cmc）,并测定了其水溶液的乳化性能和泡沫性能。结果表明,烷基链越长,表面活性剂越容易自发形成胶束,14-4-14（OH）的cmc最低,可达0.48 mmol/L,γ_cmc为33.6 mN/m;头基中引入羟基可有效降低表面活性剂的cmc和γ_cmc;随着烷基链的增长,乳化性能越好;起泡性随着烷基链的增长呈先升后降的趋势。

关键词: 双子表面活性剂, 多羟基, 表面活性, 乳化性, 泡沫性

Abstract:

A series of quaternary ammonium Gemini surfactants with hydroxyl in headgroups, butylene-1,4-bis[di（2-hydroxyethyl）alkylammonium]dibromide （abbreviated as m-4-m（OH）, where m=8, 10, 12, 14） were synthesized by two-step reactions with bromoalkane, diethanolamine and 1,4-dibromobutane. The structure of intermediate and final products were characterized by ¹H NMR and mass spectrometry （MS）. The surface tension （γ_cmc） and critical micelle concentration （cmc） of m-4-m（OH） in aqueous solution were determined by the surface tension and conductivity measurements. The emulsifying and foaming properties of m-4-m（OH） in aqueous solution were determined. It is shown that the aggregation of these Gemini surfactants are all spontaneous and the tendency of aggregation is increased with the alkyl chain length. The 14-4-14（OH） shows the lowest cmc （0.48 mmol/L） and γ_cmc （33.6 mN/m） among these Geminis. The cmc and γ_cmc of these surfactants in aqueous solution are significantly decreased due to the introduction of hydroxyethyl in the headgroup. The emulsifying property of m-4-m（OH） is better with the longer alkyl chain. The foaming property undergoes a maximum with increasing alkyl chain length.

Key words: Gemini surfactant, polyhydroxy, surface activity, emulsification, foamability

中图分类号:

TQ423

孙亚,潘华,韩富,周雅文,徐宝财. 头基含羟基的季铵盐双子表面活性剂的合成与性能[J]. 日用化学工业, 2019, 49(3): 135-140.

Ya SUN,Hua PAN,Fu HAN,Ya-wen ZHOU,Bao-cai XU. Synthesis and properties of quaternary ammonium Gemini surfactants with hydroxyl in headgroups[J]. China Surfactant Detergent & Cosmetics, 2019, 49(3): 135-140.

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表面活性剂	γ_cmc/ （mN·m^-1）	cmc^a/ （mmol·L^-1）	cmc^b/ （mmol·L^-1）
8-4-8（OH）	36.8	5.92	2.63
10-4-10（OH）	35.8	0.61	0.55
12-4-12（OH）	34.4	0.50	0.49
14-4-14（OH）	33.6	0.48	0.42
8-4-8（Me） ^[15]	41.6	56.1	-
10-4-10（Me）^[15]	40.2	8.78	-
12-4-12（Me）^[15]	39.9	0.93	-
14-4-14（Me）^[15]	40.5	0.14	-

表面活性剂	cmc/ （mmol·L^-1）	α	β	ΔG_m⁰/ （kJ·mol^-1）
8-4-8（OH）	2.63	0.70	0.30	-22.49
10-4-10（OH）	0.55	0.76	0.24	-26.54
12-4-12（OH）	0.49	0.72	0.28	-28.43
14-4-14（OH）	0.42	0.36	0.64	-41.84