Microwave synthesis and properties of dioctadecyldihydroxyethyl ammonium bromide

doi:10.11949/j.issn.0438-1157.20190005

Abstract

Abstract:

Dioctadecyldihydroxyethyl ammonium bromide (DODAB) was prepared by microwave synthesis of octadecyldiethanolamine and bromooctadecane. The optimum synthetic conditions were determined as follows: the concentration of reactant was 2.17 mol·L^-1, the reaction time was 158.61 min, and the microwave power was 626.06 W. Under these conditions, the predicted conversion was 93.71%. The product was characterized by IR and ¹H NMR. The surface activity of the product is determined as follows: CMC=0.501 g·L^-1, surface tension is 30.27 mN·m^-1, which is better than cationic surfactant D1821. The results show that the softening effect of DODAB is similar to that of D1821. With the increase of treatment times, the softening effect of DODAB treatment is slightly weaker than that of D1821, but its hand feel is more natural and comfortable. At the same time, DODAB is better than D1821 in maintaining fabric whiteness and yellowing resistance.

Key words: microwave, synthesis, surfactants, dioctadecyldihydroxyethyl ammonium bromide, optimization, softener

摘要：

以十八烷基二乙醇胺和溴代十八烷通过微波合成技术制备了双十八烷基二羟基溴化铵季铵盐（DODAB）。确定最佳合成工艺条件为：反应物浓度为2.17 mol·L^-1、反应时间为158.61 min、微波功率为626.06 W，在此条件下转化率的预测值为93.71%。产品由IR和¹H NMR进行表征。测定产品的表面活性为：CMC=0.501 g·L^-1，表面张力为30.27 mN·m^-1，优于阳离子表面活性剂D1821。测定产品应用于织物的柔软性能，结果显示：DODAB的柔软效果与D1821相当，随着处理的次数增多，DODAB处理后的柔软效果虽比D1821稍微弱一些，但其手感上会更为自然，更为舒适。同时，DODAB较D1821有着更好的维持织物白度性能的效果，具有较好的抗黄变能力。

关键词: 微波, 合成, 表面活性剂, 双十八烷基二羟乙基溴化铵, 优化, 柔软剂

CLC Number:

TQ 423.12

Yanrao CHEN, Taoyan MAO, Cheng ZHENG. Microwave synthesis and properties of dioctadecyldihydroxyethyl ammonium bromide[J]. CIESC Journal, 2019, 70(S1): 226-234.

陈燕饶, 毛桃嫣, 郑成. 双十八烷基二羟乙基溴化铵的微波合成及性能[J]. 化工学报, 2019, 70(S1): 226-234.

Figures/Tables 15

References 30

1	张文斌, 王全杰, 魏星星, 等. 季铵盐表面活性剂的合成与应用研究进展[J].皮革与化工, 2015, 32 (3) : 16-21.
	ZhangW B, WangQ J, WeiX X, et al. Progress in the synthesis and application of quaternary ammonium salt surfactants[J]. Leather and Chemical Industry, 2015, 32(3): 16-21.
2	武文涛, 张永民, 刘雪锋. 叔胺基CO₂开关表面活性剂的合成及性能研究[J].日用化学工业, 2016, (5): 251-256.
	WuW T, ZhangY M, LiuX F. Synthesis and properties of tertiary amine based CO₂ switching surfactants[J]. Daily Chemical Industry, 2016, (5): 251-256.
3	王渊. 酯基型和羟基型Gemini双季铵盐表面活性剂的合成及性能研究[D]. 太原: 太原理工大学, 2016.
	WangY. Synthesis and properties of Gemini quaternary ammonium salt surfactants with ester group or hydroxyl [D]. Taiyuan: Taiyuan University of Technology, 2016.
4	程文静, 郑成, 毛桃嫣, 等. 十八烷基甲基二羟乙基溴化铵的微波合成及性能[J].化工学报, 2011, 62(2): 566-573.
	ChengW J, ZhengC, MaoT Y, et al. Microwave synthesis and properties of octadecyl methyl dihydroxyethyl ammonium bromide[J].CIESC Journal, 2011, 62(2): 566-573.
5	周勇强, 程文静, 陈嘉胜, 等. 十八烷基甲基二羟乙基溴化铵的应用性能研究[J].应用化工, 2010, (10): 1466-1470.
	ZhouY Q, ChengW J, ChenJ S, et al. Study on application properties of octadecyl methyl dihydroxyethyl ammonium bromide[J]. Applied Chemical Industry, 2010, (10): 1466-1470.
6	王环环. DTAB及其羟乙基取代表面活性剂的聚集性质研究[D]. 上海: 华东理工大学, 2012.
	WangH H. The study on aggregation behaviors of DTAB and the corresponding hydroxyethyl substituent surfactants in aqueous solutions[D].Shanghai: East China University of Science and Technology, 2012.
7	MohammadA K, MaliheA M, AbdolhamidH M, et al. A new simple method for determining the critical micelle concentration of surfactants using surface plasmon resonance of silver nanoparticles[J] .Journal of Analytical Science and Technology , 2015, (1): 451-452.
8	秦苗, 王红艳, 王聪, 等. 羟乙基对表面活性剂在非极性溶剂中聚集行为的影响[J].宿州学院学报, 2018, 33(8): 110-114.
	QinM, WangH Y, WangC, et al. Effect of hydroxyethyl on the aggregation behavior of surfactants in non-polar solvents[J]. Journal of Suzhou University, 2018, 33(8): 110-114.
9	秦苗, 王红艳, 罗牧晨, 等. DTAB在非极性溶剂中的聚集行为[J].山东农业工程学院学报, 2018, 35(1): 36-40.
	QinM, WangH Y, LuoM C, et al. Aggregation behavior of DTAB in non-polar solvents[J]. Journal of Shandong Agricultural Engineering University, 2018, 35(1): 36-40.
10	王瑞涛, 李运玲, 李秋小. 十二烷基二羟乙基叔胺衍生物的合成与性能研究[J].印染助剂, 2014, 31(7): 12-15.
	WangR T, LiY L, LiQ X. Synthesis and properties of dodecyl dihydroxyethyl tertiary amine derivatives[J].Textile Auxiliaries, 2014, 31(7): 12-15.
11	LiY L, LiQ X, ZhiL F, et al. Synthesis, characterization and surface-activity of hydroxyethyl group-containing quaternary ammonium surfactants[J]. J. Surfact. Deterg., 2011, 14: 529-533.
12	JordanD, TanE, D. SynthesisHegh, characterization and conductivity of quaternary nitrogen surfactants modified by the addition of ahydroxymethyl substructure on the head group[J].J. Surfact. Deterg., 2012, 15: 587-592.
13	HuangX, HanY C, WangY X, et al. Aggregation properties of cationic Gemini surfactants with dihydroxyethylamino head groups in aqueous solution[J].Colloids Surf. A, 2008, 325: 26-32.
14	侯璐, 胡志勇, 姜欣欣, 等. 含羟基-磺酸基不对称表面活性剂的合成及表面活性[J].日用化学工业, 2014, 44(3): 121-125.
	HouL, HuZ Y, JiangX X, et al. Synthesis and surface activity of asymmetric surfactants containing hydroxy-sulfonic acid groups[J].Daily Chemical Industry, 2014, 44(3): 121-125.
15	XuQ, WangL Y, XingF L. Synthesis and properties of dissymmetric Gemini surfactants [J]. Journal of Surfactants and Detergents, 2011, 14(1): 85-90.
16	周飞. 绿色织物柔软剂的合成及其生物降解性[J].西安石油大学学报(自然科学版) , 2011, 26 (1): 61-64.
	ZhouF. Synthesis and biodegradability of green fabric softener[J]. Journal of Xi’an Shiyou University (Natural Science Edition), 2011, 26 (1): 61-64.
17	刘国华, 王振艳, 朱莹, 等. 双酯基季铵盐生物降解性影响因素研究[J].河南师范大学学报(自然科学版), 2013, 41(5): 131-134.
	LiuG H, WangZ Y, ZhuY, et al. Study on factors affecting biodegradability of diester quaternary ammonium salt[J].Journal of Henan Normal University (Natural Science), 2013, 41(5): 131-134.
18	罗志刚, 杨卓鸿, 卢其明, 等. 膨润土织物柔软剂的研制[J].上海纺织科技, 2014, 42(2): 21-24.
	LuoZ G, YangZ H, LuQ M, et al. Development of bentonite fabric softener[J]. Shanghai Textile Science & Technology, 2014, 42(2): 21-24.
19	侯林. 微波加快化学反应中非热效应研究的新进展[J].科技资讯, 2016, (9): 153-154.
	HouL. New progress in microwave accelerating non-thermal effects in chemical reactions[J]. Science & Technology Information, 2016, (9): 153-154.
20	钱志强, 张慧芳, 王世栋, 等. 微波技术在吸附分离中的应用研究进展[J].化工新型材料, 2018, 46(2): 272-274.
	QianZ Q, ZhangH F, WangS D, et al. Advances in the application of microwave technology in adsorption separation[J]. New Chemical Materials, 2018, 46(2): 272-274.
21	黄卡玛, 杨晓庆. 微波加快化学反应中非热效应研究的新进展[J].自然科学进展, 2006, 16(3): 273-279.
	HuangK M, YangX Q. New progress in microwave accelerating non-thermal effects in chemical reactions[J]. Natural Science Progress, 2006, 16(3): 273-279.
22	AdamD. Microwave chemistry: out of the kitchen[J]. Nature, 2003, 421(6923): 571-572.
23	郑成, 毛桃嫣, 卫云路, 等. 沸腾状态下十二烷基甲基二羟乙基溴化铵微波合成的动力学研究[J]. 精细化工, 2009, 26(2): 131-135.
	ZhengC, MaoT Y, WeiY L, et al. Kinetic study on microwave synthesis of dodecylmethyl dihydroxyethyl ammonium bromide in boiling state[J]. Fine Chemicals, 2009, 26(2): 131-135.
24	郑成, 张新强, 卫云路, 等. 甲基二羟乙基苄基氯化铵的微波合成, 结构和性能表征[J]. 化工学报, 2009, 60(1): 244-253.
	ZhengC, ZhangX Q, WeiY L, et al. Microwave synthesis, structure and characterization of methyl dihydroxyethylbenzyl ammonium chloride[J].CIESC Journal, 2009, 60(1): 244-253.
25	黎敏珊. 芥酸酰胺丙基羟基磺酸甜菜碱的微波合成及其性能应用研究[D]. 广州: 广州大学, 2016.
	LiM S. Microwave synthesis of eructopropylpropyl hydroxysulfonic acid betaine and its application study[D]. Guangzhou: Guangzhou University, 2016.
26	郑革. 微波催化合成三乙醇胺双硬脂酸酯季铵盐[J]. 印染助剂, 2013, 30(3): 20-22.
	ZhengG. Study on microwave catalysis in preparation of quaternized triethanolamine double stearic acid ester[J]. Textile Auxiliaries, 2013, 30(3): 20-22.
27	黄志. 氢化松香基季铵盐表面活性剂的微波合成及其阳离子中性施胶剂制备与应用[D]. 南宁: 广西大学, 2012.
	HuangZ. Microwave synthesis of hydrogenated rosin based quaternary ammonium salt surfactant and preparation and application of its cationic neutral sizing agent[D]. Nanning: Guangxi University, 2012.
28	毛桃嫣. 新型的表面活性剂十二烷基甲基二羟乙基溴化铵的合成与性能研究[D]. 广州: 广州大学, 2010.
	MaoT Y. Synthesis and properties of a novel surfactant dodecyl methyl dihydroxyethyl ammonium bromide[D]. Guangzhou: Guangzhou University, 2010.
29	李玉珍, 肖怀秋, 姜明姣, 等. 响应面优化微波固相合成花生肽亚铁金属配位螯合工艺[J]. 中国油脂, 2017, (9): 38-43.
	LiY Z, XiaoH Q, JiangM J, et al. Response surface optimization microwave solid phase synthesis peanut peptide ferrous metal coordination chelation process[J].China Oils and Fats, 2017, (9): 38-43.
30	郑成, 黄武欢, 毛桃嫣, 等. 酯基有机硅季铵盐合成工艺的响应面优化及表面性能[J].日用化学工业, 2015, 45(8): 429-433.
	ZhengC, HuangW H, MaoT Y, et al. Response surface optimization and surface properties of ester-based silicone quaternary ammonium salt synthesis process[J]. Daily Chemical Industry, 2015, 45(8): 429-433.

溶剂	转化率/%	产物颜色
正丁醇	12.4	淡黄色
正戊醇	30.77	浅黄色
正己醇	74.8	黄色

溶剂	转化率/%	产物颜色
正丁醇	12.4	淡黄色
正戊醇	30.77	浅黄色
正己醇	74.8	黄色

水平	因素
水平	反应物浓度（A）/(mol·L^-1)	微波功率（B）/W	反应时间（C）/min
-1	2	500	120
0	2.2	600	150
1	2.4	700	180

水平	因素
水平	反应物浓度（A）/(mol·L^-1)	微波功率（B）/W	反应时间（C）/min
-1	2	500	120
0	2.2	600	150
1	2.4	700	180

No.	Reactant concentration（A）/ （mol·L^-1）	Power（B）/W	Time（C）/min	Conversion rate（response 1）/%
1	2.20	180.00	600.00	92.12
2	2.40	120.00	500.00	82.52
3	2.20	150.00	600.00	92.89
4	2.20	150.00	600.00	93.25
5	2.20	150.00	500.00	90.0
6	2.00	180.00	700.00	89.87
7	2.00	150.00	600.00	91.89
8	2.20	150.00	600.00	93.24
9	2.00	120.00	500.00	83.33
10	2.00	120.00	700.00	87.18
11	2.40	150.00	600.00	90.84
12	2.40	120.00	700.00	86.5
13	2.20	150.00	600.00	93.68
14	2.40	180.00	500.00	86.37
15	2.20	150.00	600.00	93.75
16	2.00	180.00	500.00	87.56
17	2.20	120.00	600.00	88.77
18	2.20	150.00	600.00	93.4
19	2.40	180.00	700.00	88.57
20	2.20	150.00	700.00	91.4