多头季铵盐表面活性剂的合成及性能评价

doi:10.3969/j.issn.2097-2806.2023.08.006

Abstract

Abstract:

Bi-headgroup quaternary ammonium surfactant （BTAE-n） and tetra-headgroup quaternary ammonium surfactant （PTAE-n） were synthesized from alkyl halides with different carbon chain length, benzyl chloride and α, α’-dichloro-p-xylene. The structure of products was characterized by HPLC, FT-IR, ¹H NMR and LC-MS, and the Krafft temperature, emulsifying properties, wetting properties and foam properties of the surfactants were evaluated. The results show that the Krafft temperatures of BTAE-n and PTAE-n are both lower than 0 ℃, indicative of good water solubility and low-temperature solubility. Compared with benzalkonium chloride, BTAE-n and PTAE-n have better foam stability. Their foaming performance decreases with the increase of carbon number of alkyl chain, while the emulsification performance increases. The results of contact angle measurement show that the wetting ability of BTAE-n is better than that of PTAE-n. According to the evaluation results of bacteriostatic and bactericidal properties, BTAE-n and PTAE-n show effective bacteriostatic and bactericidal activities against gram-positive bacteria （Staphylococcus aureus）, gram-negative bacteria （Escherichia coli） and fungi （Candida albicans）, and the effectiveness of tetra-headgroup quaternary ammonium salts is better than that of bi-headgroup quaternary ammonium salts with the same carbon chain. For the surfactants of the same type, the bacteriostatic and bactericidal effects are better with the increase of carbon chain length.

Key words: multi-headgroup quaternary ammonium salt, synthesis, surface activity

CLC Number:

TQ423

Cui Congcong,Zhang Hongli,Xuan Guangshan. Study on preparation and performance of multi-headgroup quaternary ammonium surfactant[J].China Surfactant Detergent & Cosmetics, 2023, 53(8): 899-907.

Figures/Tables 12

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References 18

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化合物	保留时间/min	纯度/%
BTAE-8	2.665	99.104
BTAE-10	2.783	95.653
BTAE-12	2.880	99.581
PTAE-8	3.625	99.452
PTAE-10	3.710	97.676
PTAE-12	3.827	98.731

化合物	σ/cm^-1
化合物	-CH₃伸缩振动	-CH₂伸缩振动	-[CH₂]_n-平面振动	苯环骨架振动
BTAE-8	2 933.00	2 858.18	711.55	1 631.32	1 633.82	1 635.55
BTAE-10	2 926.37	2 854.71	716.82	1 576.21	1 576.21	1 480.47
BTAE-12	2 924.59	2 853.47	710.90	1 479.27	1 458.99	1 394.78
PTAE-8	2 933.73	2 858.82	800.89	1 634.64	1 636.07	1 633.19
PTAE-10	2 928.31	2 855.82	802.48	1 578.34	1 480.87	1 481.27
PTAE-12	2 925.55	2 853.69	789.67	1 483.36	1 395.30	1 394.32

化合物	MIC/（μg/mL）
	革兰氏阴性菌			革兰氏阳性菌		真菌
	大肠杆菌	铜绿假单胞菌	伤寒沙门菌	金黄色葡萄球菌	枯草芽孢杆菌	白色念珠菌	黑曲霉
BTAE-8	512	512	512	512	512	512	512
BTAE-10	512	512	512	256	256	512	512
BTAE-12	256	512	512	256	256	512	512
PTAE-8	256	256	256	128	128	128	128
PTAE-10	128	128	128	64	64	64	64
PTAE-12	64	128	128	32	32	32	32
BAC	256	128	256	128	128	128	128

化合物	杀菌率/%
	革兰氏阴性菌			革兰氏阳性菌		真菌
	大肠杆菌	铜绿假单胞菌	伤寒沙门菌	金黄色葡萄球菌	枯草芽孢杆菌	白色念珠菌	黑曲霉
BTAE-8	52.1	53.4	52.3	56.2	54.3	51.8	50.4
BTAE-10	53.2	50.4	51.9	70.4	71.2	53.2	52.4
BTAE-12	74.3	56.4	55.5	75.4	74.3	52.7	53.4
PTAE-8	75.2	77.2	76.4	80.4	81.3	80.4	82.4
PTAE-10	90.3	92.1	90.9	92.3	90.3	91.5	91.9
PTAE-12	99.9	99.9	99.9	99.9	99.9	99.9	99.9
BAC	87.3	90.4	88.6	93.4	92.3	92.6	94.2

Study on preparation and performance of multi-headgroup quaternary ammonium surfactant

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