一类以对苯二胺为联接基的双子表面活性剂的合成及性能

doi:10.3969/j.issn.1001-1803.2019.05.003

摘要/Abstract

摘要：

以环氧氯丙烷,对苯二胺和N,N-二甲基烷基胺为原料,分两步合成了一系列具有不同疏水链长的新型双子表面活性剂C₁₂、C₁₆和C₁₈,通过FT-IR和 ¹H NMR对产物结构进行表征,测定了苯二胺型表面活性剂的临界胶束浓度（cmc）和表面张力（γ_cmc）以及Krafft点、乳化、泡沫和抗菌性能。结果表明,在25 ℃时C₁₂、C₁₆和C₁₈的cmc分别为3.29×10 ^-3,2.53×10 ^-4和3.14×10 ^-4 mol/L,γ_cmc分别为28.24,31.95和35.06 mN/m;C₁₂和C₁₆的Krafft点均小于0 ℃,C₁₈的Krafft点为10 ℃;C₁₂的发泡性优于C₁₆和C₁₈;C₁₈的乳化性能强于C₁₂和C₁₆;C₁₂、C₁₆和C₁₈均具有优异的抗微生物活性。

关键词: 双子表面活性剂, 表面活性, 泡沫性, 乳化性, 抗菌性

Abstract:

A series of novel Gemini surfactants C₁₂, C₁₆, and C₁₈with the hydrophobic groups of different lengths were synthesized with epichlorohydrin, N, N-dimethylalkyl amine and p-phenylenediamine as materials in two steps. The products were characterized by FT-IR and ¹H NMR. The critical micelle concentration（cmc）and the corresponding surface tension（γ_cmc）of the phenylenediamine surfactants in aqueous solution were measured at 25 ℃ by surface tensiometer. The Krafft points and the emulsifying, foaming and antimicrobial properties of the aqueous solutions were also determined. The results show that the cmc of C₁₂, C₁₆ and C₁₈ at 25 ℃ are 3.29×10 ^-3, 2.53×10 ^-4 and 3.14×10 ^-4 mol/L, respectively, and the γ_cmc are 28.24, 31.95 and 35.06 mN/m, respectively. The Krafft points of C₁₂ and C₁₆ are both below 0 ℃, and the Krafft point of C₁₈ is 10 ℃. The foaming properties of C₁₂ are better than those of C₁₆ and C₁₈. The emulsifying properties of C₁₈ are better than those of C₁₂ and C₁₆. C₁₂, C₁₆ and C₁₈ have shown excellent antimicrobial activities.

Key words: Gemini surfactant, surface activity, foaming property, emulsifying property, antimicrobial property

中图分类号:

TQ423

王晨,许虎君. 一类以对苯二胺为联接基的双子表面活性剂的合成及性能[J]. 日用化学工业, 2019, 49(5): 293-297.

WANG Chen,XU Hu-jun. Synthesis and properties of a series of Gemini surfactants with p-phenylenediamine as a spacer[J]. China Surfactant Detergent & Cosmetics, 2019, 49(5): 293-297.

图/表 3

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产物	cmc/（mol·L^-1）	γ_cmc/（mN·m^-1）	pc₂₀	10¹⁰Γ_max/（mol·cm^-2）	A_min/nm²
C₁₂	3.29×10^-3	28.24	4.02	1.32	1.25
C₁₆	2.53×10^-4	31.95	4.28	1.44	1.15
C₁₈	3.14×10^-4	35.06	4.12	1.48	1.12

产物	t/min	抑菌率/%
产物	t/min	大肠杆菌	金黄色葡萄球菌	白色念珠菌
C₁₂	2	>99.99	>99.99	>99.99
	5	>99.99	>99.99	>99.99
	10	>99.99	>99.99	>99.99
	20	>99.99	>99.99	>99.99
C₁₆	2	>99.99	>99.99	>99.99
	5	>99.99	>99.99	>99.99
	10	>99.99	>99.99	>99.99
	20	>99.99	>99.99	>99.99
C₁₈	2	0	>99.99	99.89
	5	28.89	>99.99	>99.99
	10	99.78	>99.99	>99.99
	20	>99.99	>99.99	>99.99