脂肪酰胺丙基磷酸酯甜菜碱的合成和性能研究

doi:10.3969/j.issn.1001-1803.2020.07.003

摘要/Abstract

摘要：

以三种脂肪酸酰胺基丙基叔胺和2-羟基-3-氯丙基磷酸酯钠为原料,通过不同的实验方法,合成了三种脂肪酰胺丙基磷酸酯甜菜碱（简称C_n-APA,n=12,14或16）,结果表明加压反应的产率高达95%,相比于常压反应,加压反应能极大地缩短反应时间,提高反应产率,产物结构通过红外图谱和质谱表征。研究了三种产物的表面活性、去污性能、泡沫性能、乳化性能以及抗静电性能。结果表明C₁₂-APA,C₁₄-APA和C₁₆-APA的cmc分别为5.1×10^-4,3.4×10^-4和8.2×10^-5 mol/L,产物拥有良好的发泡稳泡性、乳化性能,对皮脂的去污力良好,且具有优良的抗静电性能。

关键词: 磷酸酯甜菜碱, 表面活性, 去污性能, 泡沫性能, 乳化性能, 抗静电性能

Abstract:

Three fatty amide propyl phosphobetaines （abbreviated as C_n-APA, where n=12, 14 or 16） were synthesized with three fatty acid amidopropyl tertiary amines and sodium 2-hydroxy-3-chloropropyl phosphate by different experimental methods. The results show that the yield of the pressurized reaction is as high as 95%. Compared with the atmospheric pressure reaction, the pressurized reaction can greatly shorten the reaction time and increase the reaction yield. The structure of the products was characterized by infrared spectroscopy and mass spectroscopy. The surface activity, detergency performance, foam properties, emulsifying properties and antistatic performance of the three products were investigated. The results show that the cmc of C₁₂-APA, C₁₄-APA and C₁₆-APA are 5.1×10^-4, 3.4×10^-4 and 8.2×10^-5 mol/L, respectively, and all products possess good foam stability, good emulsifying properties, good detergency to sebum, and excellent antistatic properties.

Key words: phosphobetaine, surface activity, detergency performance, foam property, emulsifying property, antistatic performance

中图分类号:

TQ423

刘佳佳,许虎君. 脂肪酰胺丙基磷酸酯甜菜碱的合成和性能研究[J]. 日用化学工业, 2020, 50(7): 446-451.

LIU Jia-jia,XU Hu-jun. Study on the synthesis and properties of fatty amido propyl phosphobetaine[J]. China Surfactant Detergent & Cosmetics, 2020, 50(7): 446-451.

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参考文献 21

[1]	Shi Leicheng. Synthesis and properties of a novel of amphoteric surfactants sulfobetaines[D]. Daqing: Northeast Petroleum University, 2012.
[2]	Feng Lianxiang, Chen junzhi. The types, synjournal and progress research of betaine amphoteric surfactants[J]. China Surfactant Soap and Detergent, 2005 ( 6) : 39-41.
[3]	Wu Hailong, Huang Jianbang, Luo Xiaoqiu, et al. Synjournal and characterization of cocamidopropyl betaine[J]. China Surfactant Detergent & Cosmetics, 2014,44(1) : 23-25.
[4]	Ding Wei, Li Jinhong, Yu Tao, et al. Surface/Interface performance of new sulfobetaine/polyacrylamide system[J]. Chinese Journal of Applied Chemistry, 2013,30(11) : 1270-1275.
[5]	Lv Huitian, Chen Cunshe. Briefing on phosphoric acid ester salt surfactants[J]. China Surfactant Detergent & Cosmetics, 2005,35(3) : 174-177.
[6]	Wang Changjian, Jiang Huiliang. Synjournal of novel phosphoric acid ester surfactants[J]. Hebei Chemical Industry, 2009 ( 8) : 29-31.
[7]	Li Danping. Synthesis and properties of di-hydrophobic betaine with amide group[D]. Wuxi: Jiangnan University, 2012.
[8]	Feng Yunsheng, Tong Bai, Wang Tiansheng. Synjournal and performance of alkyl phosphate amphoteric surfactants[J]. Printing and Dyeing, 2017 ( 11) : 40-42.
[9]	Jiang Pingping. Research status and development trend of synjournal and application of phosphate surfactants at home and abroad[J]. China Surfactant Detergent & Cosmetics, 1997,35(3) : 32-37.
[10]	He Yunjun, Zhang Zhuyong. Synjournal and properties of novel amphoteric surfactant alkylamidophobetaines[J]. Journal of East China University of Science and Technology, 1998 ( 6) : 741-745.
[11]	Cao Yafeng, Li Yuan. Synjournal and application of alkylamide phosphobetaine[J]. Surfactant Industry, 1999 ( 4) : 21-23.
[12]	Anthony J O’Lenick, Jr Dacula, John Imperante, et al. Glyceryl phosphobetaine compounds: US6620794 [P]. 2003 -09-16.
[13]	Scott Smith, Dean Smith, Chattanoga T N, et al. Dimer amidopropyl dimethyl phospholipids as barrier compounds: US6331293 [P]. 2001 -12-18.
[14]	Yu Mingying, Wang Jing, Cao Guangqun. Silicone-free shampoo is it a false proposition?: Application of silicone oil in cosmetics[J]. China Cosmetics Review, 2019 ( 8) : 89-93.
[15]	Li Mingyong, Chen Zhengguo. Synjournal of sodium 3-chloro-2-hydroxy propanephosphate[J]. Fine Chemical Intermediates, 2011,41(5) : 35-37.
[16]	Bales B L, Benrraou M, Zana R. Krafft temperature and micelle ionization of aqueous solutions of cesium dodecyl sulfate[J]. Journal of Physical Chemistry B, 2002,106(35) : 9033-9035.
[17]	People’s Republic of China Textile Industry Standard. Textile materials-electrostatic properties-determination of static voltage half-life [M]. Beijing: China Standard Press, 1996.
[18]	Cui Zhenggang, Jiang Jianzhong, Pei Xiaomei, et al. Surfactant and interfacial phenomena [M]. Beijing: Chemical Industry Press, 2015: 111-117.
[19]	Jian Guoqing, Hou Qingfeng, Zhu Youyi. Stability of polymer and surfactant mixture enhanced foams in the presence of oil under static and dynamic conditions[J]. Journal of Dispersion Science and Technology, 2015,36(4) : 477-488.
[20]	Dai Qing. Antistatic fabric and its antistatic performance test method[J]. Technology and Frontier, 2008 ( 8) : 44-46.
[21]	State Administration of Quality Supervision, Inspection and Quarantine of the People’s Republic of China; China National Standardization Administration. Textiles- Evaluation of electrostatic properties: Part 1: Static half period: GB/T 12703.1—2008 [S]. Beijing: China Standard Press, 2008.

产物	cmc/（mol·L^-1）	γ_cmc/（mN·m^-1）	pc₂₀	cmc/c₂₀	10¹⁰Γ_max/（mol·cm^-2）	A_min/nm²
C₁₂-APA	5.1×10^-4	40.4	3.80	3.20	4.06	0.41
C₁₄-APA	3.4×10^-4	37.3	4.02	3.62	4.45	0.37
C₁₆-APA	8.2×10^-5	41.4	4.40	2.03	5.80	0.29

产物	碳黑污布去污值	蛋白污布去污值	皮脂污布去污值
C₁₂-APA	0.18	0.18	7.72
C₁₄-APA	0.92	0.93	10.34
C₁₆-APA	1.67	1.64	9.42

产物	泡沫高度/mm		稳泡率/%
产物	0 min	5 min	稳泡率/%
C₁₂-APA	155	152	98.1
C₁₄-APA	179	177	98.9
C₁₆-APA	166	165	99.4

等级	静电半衰期/s
A	≤2.0
B	≤5.0
C	≤15.0