双子表面活性剂N,N′-双十二烷基对苯二甲胺丙酸的合成及性能研究

doi:10.13218/j.cnki.csdc.2017.08.001

Abstract

Abstract: Gemini surfactant N,N′-bis(dodecyl)-1,4-xylylene diamine propionate acid was synthesized from dodecylamine,methyl acrylate and p-xylylene dichloride as starting materials with trichloromethane as solvent.The chemical structure of the product was characterized by ¹H NMR and ¹³C NMR.Performance of the product at (25±1) ℃ were studied and the results show that when the pH value is separately prepared at 8,10 and 12,the critical micellar concentration (cmc) is 1.6×10^-5,3.3×10^-5 and 2.1×10^-5 mol/L respectively;the surface tension (γ_cmc) is 32.39,33.24 and 36.94 mN/m;the pc₂₀ is 2.56,2.14 and 2.09;the Γ_max is 3.45×10^-6,3.97×10^-6 and 4.34×10^-6 mol/m²;the A_min is 0.48,0.42 and 0.38 nm².When the pH value rises to 12,following the raise of temperature,the values of pc₂₀ and A_min increase but the Γ_max decreases.

Key words: Gemini surfactant, N,N′-bis(dodecyl)-1,4-xylylene diamine propionate acid, surface activity

CLC Number:

TQ423.1

ZHAO Lin-xiu, LI Gang-sen, WANG Ping, SHEN Ya-mei. Synthesis and performance of Gemini surfactant N,N′-bis(dodecyl)-1,4-xylylene diamine propionate acid[J].China Surfactant Detergent & Cosmetics, 2017, 47(8): 421-424.

References

[1] Menger F M,Littau C A.Gemini surfactants:synthesis and properties [J].Journal of the American Chemical Society,1991,113(4):1451-1452.
[2] 王军,栾立辉,杨许召,等.季铵盐双子表面活性剂的合成和表面活性[J].精细化工,2009,26(1):14-17.
[3] Oelschlaeger C,Waton G,Candau S J,et al.Structural,kinetics,and rheological properties of low ionic strength dilute solutions of a dimeric (Gemini) surfactant [J].Langmuir,2002,18(20):7265-7271.
[4] 高欢泉,于文.阴离子双子表面活性剂合成现状及应用前景[J].日用化学品科学,2011,34(3):19-22.
[5] 刘凡,许虎君.非对称阳离子双子表面活性剂的合成和性能研究[J].日用化学工业,2016,46(2):80-83.
[6] 李小芳,陈爱明,姚志钢,等.Gemini表面活性剂——乙二醇双琥珀酸正辛醇双酯磺酸钠的合成与性能研究[J].化学世界,2007,48(7):421-424.
[7] Wu H,Du X,Zhang X,et al.Synthesis and properties of alkylbenzene sulfonate Gemini surfactants with high viscosity in dilute solution without additives [J].Journal of Dispersion Science and Technology,2011,32:596-600.
[8] 何志强.芳香联接基与双子表面活性剂的构效关系研究[D].无锡:江南大学,2014.
[9] Prahl M A.Diaryl oxide sulphonic acids and processes for preparing:US2081876 [P].1937-05-25.
[10] Perkins R P.Alkylated diphenyl oxide:US2170809 [P].1939-08-22.
[11] Prutton C F.Sulfurized derivatives of alkyl diphenyl oxide sulfonic acids and salts:US2555370 [P].1951-06-05.
[12] Grossmann M,Faber R,Uhrig H.Dispersing and wetting agents for use in organic biocides:US3919429 [P].1975-11-11.
[13] Song B L,Zhao J X.Orientation of the azobenzene spacer of carboxylic methyl ester Gemini surfactants in Langmuir monolayer [J].Chinese Journal of Chemistry,2010,28(2):189-192.
[14] Zhu D,Cheng F,Chen Y,et al.Preparation,characterization and properties of anionic Gemini surfactants with long rigid or semi-rigid spacers [J].Colloids and Surfaces A:Physicochemical and Engineering Aspects,2012,397:1-7.
[15] 李刚森,赵林秀,王培义,等.N,N′-对苯二亚甲基-双(十二烷基二甲基氯化铵)/AEO₉复配体系表面活性研究[J].日用化学工业,2016,46(7):392-396.
[16] 王培义,尹浩,张应军,等.酰胺型Gemini表面活性剂的合成与性能[J].精细化工,2009,26(9):863-866.
[17] 王培义,尹浩,张应军,等.酰胺型Gemini表面活性剂的提纯与表征[J].石油化工,2009,38(12):1322-1326.
[18] Li H,Yu C,Chen R,et al.Novel ionic liquid-type Gemini surfactants:synthesis,surface property and antimicrobial activity [J].Colloids and Surfaces A:Physicochemical and Engineering Aspects,2012,395:116-124.
[19] Huang X,Cao M W,Wang J B,et al.Controllable organization of a carboxylic acid type Gemini surfactant at different pH values by adding copper (II) ions [J].The Journal of Physical Chemistry B,2006,110(39):19479-19486.
[20] Rosen M J.Surfactants and interfacial phenomena [M].New Jersey:A John Wiley & Sons,Inc.,2004:60-63.
[21] Li Z X,Dong C C,Thomas R K.Neutron reflectivity studies of the surface excess of Gemini surfactants at the air-water interface [J].Langmuir,1999,15(13):4392-4396.

Synthesis and performance of Gemini surfactant N,N′-bis(dodecyl)-1,4-xylylene diamine propionate acid

PDF (PC)

Like

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Metrics

Comments

Recommended 10

[1]	Zhisheng Zhang, Chanliang Shen, Jianxun Li, Yanqiang Liu, Weiwei Han, Sanbao Dong. Preparation and performance of betaine/AOS/Gemini ternary surfactant foam for gas well deliquification [J]. China Surfactant Detergent & Cosmetics, 2024, 54(3): 239-249.
[2]	Haokang Ai, Yajie Jiang, Yakui Wang, Lu Zhang, Tao Geng. Synthesis and properties of Gemini quaternary ammonium surfactant based on stearate [J]. China Surfactant Detergent & Cosmetics, 2024, 54(1): 16-23.
[3]	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.
[4]	Xing Huanyu, Jia Lihua, Zhao Zhenlong, Yang Rui, Guo Xiangfeng. Synthesis and properties of novel surfactants containing naphthalimide and alkyl segments [J]. China Surfactant Detergent & Cosmetics, 2023, 53(7): 742-747.
[5]	Yongkang Zhang, Mengmeng Liu, Zhiwei Wan, Yaocong Wang, Mimi Tian, Liewei Qiu. Effect of spacer on the performance of Gemini betaine surfactant in clean fracturing fluid [J]. China Surfactant Detergent & Cosmetics, 2023, 53(12): 1398-1404.
[6]	Ting Pan, Junhui Wu, Xiaomei Pei, Zhenggang Cui. Temperature and pH responsive behavior of wormlike micelles formed by novel pseudo-gemini surfactant [J]. China Surfactant Detergent & Cosmetics, 2023, 53(12): 1361-1368.
[7]	Zheng Lanjian,Zang Ying,Lin Tong,Xie Yiwen,Wang Honglei. The production of high yield biosurfactant rhamnolipid and performance research [J]. China Surfactant Detergent & Cosmetics, 2022, 52(9): 937-944.
[8]	Zhao Shufen,Zheng Danmiao,Liu Huaxi,Song Songlin,Chen Zhan,Yang Ningyuan,Wei Xingchuan. Progress in synthesis and application of rosin based gemini surfactants [J]. China Surfactant Detergent & Cosmetics, 2022, 52(8): 892-903.
[9]	Wang Junxia,Liu Jianhua,Lu Xiaomeng,Sun Yongqiang,Hu Zhiyong,Zhu Hailin. Corrosion inhibition effect of a quaternary ammonium surfactant containing thiadiazole on Q235 steel [J]. China Surfactant Detergent & Cosmetics, 2022, 52(8): 797-804.
[10]	Lu Xiaohao,Xu Hujun,Lin Liangliang,Chang Kuan,Gao Haiyan. Synthesis and properties of an amide cationic Gemini surfactant with ester groups [J]. China Surfactant Detergent & Cosmetics, 2021, 51(7): 598-605.
[11]	WANG Jun,ZHANG Chen-long,YANG Xu-zhao,BAI Ya-rong. Research progress of magnetic surfactants [J]. China Surfactant Detergent & Cosmetics, 2021, 51(6): 546-553.
[12]	LI Ying,XU Hu-jun. Study on the synthesis and performance of sodium N-lauroyl methylalaninate [J]. China Surfactant Detergent & Cosmetics, 2021, 51(6): 496-501.
[13]	ZHU Hai-lin,LI Xiao-fen,LU Xiao-meng,HUANG Hao-yu,WANG Zi-xiang,HU Zhi-yong. Study on the synthesis of a sulfonate surfactant and its corrosion inhibition performance for carbon steel [J]. China Surfactant Detergent & Cosmetics, 2021, 51(5): 375-382.
[14]	ZHONG Guo-yuan,ZHANG Li-ming,HU Dong-min,PENG Hua-nan,YANG Yan-chun,ZHENG Jie. Study on preparation and properties of thermal responsive poly （dimethylaminoethyl methacrylate） quaternary ammonium [J]. China Surfactant Detergent & Cosmetics, 2021, 51(5): 428-432.
[15]	FU Duo-jiao,ZHOU Yin,CHEN Han-yu,LIU Hong-qin,XU Bao-cai. Advances in research and application of quaternary ammonium Gemini surfactants and their modified clay [J]. China Surfactant Detergent & Cosmetics, 2021, 51(4): 338-347.