CN115477597A - 一种表面活性剂的制备方法及其应用 - Google Patents
一种表面活性剂的制备方法及其应用 Download PDFInfo
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- 239000002904 solvent Substances 0.000 claims description 30
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- 238000012258 culturing Methods 0.000 description 2
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- JDTUPLBMGDDPJS-UHFFFAOYSA-N 2-methoxy-2-phenylethanol Chemical compound COC(CO)C1=CC=CC=C1 JDTUPLBMGDDPJS-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/13—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/14—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
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- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
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Abstract
本发明涉及表面活性剂技术领域,且公开了一种表面活性剂的制备方法及其应用,以3‑十五烷基苯酚和1,2‑溴乙烷反应合成的3‑十五烷基苯氧乙基溴作为前驱体,依次与二甲胺、3‑氯‑2‑羟基丙磺酸钠发生取代和季铵化反应,再与烷基二酰氯发生酯化交联反应,得到含有双(十五烷基苯氧基烷基磺酸季铵盐)结构的表面活性剂,具有独特的亲水性双磺酸季铵盐基团和疏水性的烷基长链基团,起泡和乳化效果好,润湿性能优良,并且含有季铵盐基团具有优异的抗菌性能,在抗菌消毒洗衣液等洗涤剂中有着广阔的应用前景。
Description
技术领域
本发明涉及表面活性剂技术领域,具体为一种表面活性剂及制备方法。
背景技术
表面活性剂具有固定的亲水亲油基团,可以使目标溶液表面张力显著下降,主要有离子型表面活性剂、非离子型表面活性剂、两性表面活性剂、复配表面活性剂等,可以起到润湿、起泡、消泡、去垢、洗涤等作用,在洗衣粉等洗涤剂、化妆品、抗静电剂等方面有着广泛的应用。
开发新型表面活性剂和洗涤用品具有重要的意义,如文献《十二烷基二甲基苄基氯化铵在抗抑菌洗衣液中的应用》,报道了十二烷基二甲基苄基氯化铵应用于洗衣液配方制备抗抑菌洗衣液,去污效果好,具有较长时效的抗抑菌能力,对人体皮肤无明显刺激作用。腰果酚及其衍生物表面活性剂具有优良的润湿、乳化、去污等性能,广泛应用在洗衣液等洗涤用品中,如专利CN108531308A《一种含有腰果酚聚氧乙烯醚的洗涤剂及其制备方法与应用》,公开了含有腰果酚聚氧乙烯醚的洗涤剂,易溶于水、浊点高、临界胶束浓度低、去污效果好的优点。
发明内容
(一)解决的技术问题
针对现有技术的不足,本发明提供了一种表面活性剂及制备方法,应用于洗涤剂领域中。
(二)技术方案
一种表面活性剂,结构为式(Ⅰ):
优选的,所述表面活性剂制备方法为:
(1)将3-十五烷基苯氧乙基溴溶解到异丙醇溶剂中,然后滴加二甲胺的水溶液,在N2保护下滴加催化剂的水溶液,并在50-80 ℃中搅拌反应6-18 h,反应后旋转除去溶剂,去离子水洗涤后,粗产物进行柱色谱分离,以体积比石油醚:乙酸乙酯=(10-20):1作为洗脱剂,分离得到3-十五烷基苯氧基-N,N-二甲基乙胺,结构式为式(Ⅱ):
(2)将3-十五烷基苯氧基-N,N-二甲基乙胺溶解到异丙醇溶剂中,然后滴加3-氯-2-羟基丙磺酸钠的水溶液,在60-80 ℃中搅拌反应10-20 h,反应后旋转除去溶剂,依次用饱和氯化钠溶液、甲醇和石油醚洗涤,得到3-十五烷基苯氧基羟基磺酸季铵盐,结构式为式(Ⅲ):
(3)将3-十五烷基苯氧基羟基磺酸季铵盐加入到二氯甲烷中,搅拌均匀后在冰浴下加入烷基二酰氯和三乙胺,搅拌均匀后在25-40 ℃中搅拌反应12-36 h,反应后旋转除去溶剂,依次用饱和氯化钠溶液、甲醇和石油醚洗涤,得到含有双(十五烷基苯氧基烷基磺酸季铵盐)结构的表面活性剂。
优选的,所述(1)3-十五烷基苯氧乙基溴、二甲胺的摩尔比为1:1.8-3。
优选的,所述(1)中催化剂的水溶液的浓度为15-25%。
优选的,所述催化剂为氢氧化钾或氢氧化钠。
优选的,所述(2)中3-十五烷基苯氧基-N,N-二甲基乙胺、3-氯-2-羟基丙磺酸钠的摩尔比为1:1.2-1.6。
优选的,所述(3)中3-十五烷基苯氧基羟基磺酸季铵盐、烷基二酰氯和三乙胺的摩尔比例为1:2.5-3.5:2-3.2。
(三)有益的技术效果
与现有技术相比,本发明具备以下有益技术效果:
该一种表面活性剂,以3-十五烷基苯酚和1,2-溴乙烷反应合成的3-十五烷基苯氧乙基溴作为前驱体,依次与二甲胺、3-氯-2-羟基丙磺酸钠发生取代和季铵化反应,合成了3-十五烷基苯氧基羟基磺酸季铵盐中间体,然后再与烷基二酰氯发生酯化交联反应,得到含有双(十五烷基苯氧基烷基磺酸季铵盐)结构的表面活性剂,具有独特的亲水性双磺酸季铵盐基团和疏水性的烷基长链基团,为合成新型磺酸季铵盐型表面活性剂提供了新的方法和策略。含有双(十五烷基苯氧基烷基磺酸季铵盐)结构的表面活性剂的起泡和乳化效果好,润湿性能优良,并且含有季铵盐基团具有优异的抗菌性能,在抗菌消毒洗衣液等洗涤剂中有着广阔的应用前景。
附图说明
图1是3-十五烷基苯氧基-N,N-二甲基乙胺的制备反应式。
图2是3-十五烷基苯氧基羟基磺酸季铵盐的制备反应式。
图3是含有双(十五烷基苯氧基烷基磺酸季铵盐)结构的表面活性剂的制备反应式。
图4是表面活性剂表面张力测试。
图5是表面活性剂起泡性能测试。
具体实施方式
3-十五烷基苯氧乙基溴的制备方法参考文献《Synthesis of Fullerene-Cardanol Derivatives》,SYNLETT, 2004, No.5, pp 0799-08020。
实施例1
(1)将4.1 g的3-十五烷基苯氧乙基溴溶解到10 mL的异丙醇溶剂中,然后滴加3mL含有0.8 g的二甲胺的水溶液,在N2保护下滴加3 mL的15%的氢氧化钠催化剂的水溶液,并在80 ℃中搅拌反应6 h,反应后旋转除去溶剂,去离子水洗涤后,粗产物进行柱色谱分离,以体积比石油醚:乙酸乙酯=10:1作为洗脱剂,分离得到3-十五烷基苯氧基-N,N-二甲基乙胺,结构式为;分子式为C25H45NO;1H NMR (300MHz,CDCl3):δ7.40-7.32(m, 1H),6.77-6.43(m, 3H),4.25-4.10(t,2H),2.93(s,6H),2.86-2.62(m, 4H),1.62-1.52(t,2H),1.33-1.26(m, 24H),0.90-0.83(m, 3H)。
(2)将3.7 g的3-十五烷基苯氧基-N,N-二甲基乙胺溶解到20 mL的异丙醇溶剂中,然后滴加4 mL的含有2.4 g的3-氯-2-羟基丙磺酸钠的水溶液,在70 ℃中搅拌反应10 h,反应后旋转除去溶剂,依次用饱和氯化钠溶液、甲醇和石油醚洗涤,得到3-十五烷基苯氧基羟基磺酸季铵盐,结构式为;分子式为C28H51NO5S;1H NMR(300MHz,CDCl3):δ7.41-7.35(m, 1H),6.78-6.51(m, 3H),4.35-4.20(t,2H),3.85-3.70(m, 3H),3.67-3.40(m, 5H),3.32(s,6H),2.76-2.60(t,2H),1.60-1.23(m, 26H),0.91-0.85(m, 3H)。
(3)将2.5 g的3-十五烷基苯氧基羟基磺酸季铵盐加入到15 mL的二氯甲烷中,搅拌均匀后在冰浴下加入3.1 g的丙二酰氯和1 g的三乙胺,搅拌均匀后在40 ℃中搅拌反应24 h,反应后旋转除去溶剂,依次用饱和氯化钠溶液、甲醇和石油醚洗涤,得到含有双(十五烷基苯氧基烷基磺酸季铵盐)结构的表面活性剂;结构式为,分子式为C59H102N2O12S2;1H NMR (300MHz,CDCl3):δ7.51-7.35(m, 4H),6.88-6.50(m, 4H),4.65-4.50(m, 2H),4.39-4.27(m, 4H),3.80-3.68(m, 2H), 3.66-3.43(m, 6H),3.36(s, 12H),3.32-3.20(m, 2H),2.79-2.58(m,4H),1.62-1.20(m, 56H),0.93-0.82(m, 6H)。
实施例2
(1)将4.1 g的3-十五烷基苯氧乙基溴溶解到15 mL的异丙醇溶剂中,然后滴加3mL含有0.8 g的二甲胺的水溶液,在N2保护下滴加3 mL的25%的氢氧化钠催化剂的水溶液,并在50 ℃中搅拌反应12 h,反应后旋转除去溶剂,去离子水洗涤后,粗产物进行柱色谱分离,以体积比石油醚:乙酸乙酯=20:1作为洗脱剂,分离得到3-十五烷基苯氧基-N,N-二甲基乙胺。
(2)将3.7 g的3-十五烷基苯氧基-N,N-二甲基乙胺溶解到15 mL的异丙醇溶剂中,然后滴加4 mL的含有3 g的3-氯-2-羟基丙磺酸钠的水溶液,在80 ℃中搅拌反应10 h,反应后旋转除去溶剂,依次用饱和氯化钠溶液、甲醇和石油醚洗涤,得到3-十五烷基苯氧基羟基磺酸季铵盐。
(3)将2.5 g的3-十五烷基苯氧基羟基磺酸季铵盐加入到15 mL的二氯甲烷中,搅拌均匀后在冰浴下加入1.9 g的丁二酰氯和1.2 g的三乙胺,搅拌均匀后在25 ℃中搅拌反应36 h,反应后旋转除去溶剂,依次用饱和氯化钠溶液、甲醇和石油醚洗涤,得到含有双(十五烷基苯氧基烷基磺酸季铵盐)结构的表面活性剂;结构式为,分子式为C60H104N2O12S2。1H NMR(300MHz,CDCl3):δ7.50-7.34(m, 4H),6.92-6.51(m, 4H),4.68-4.50(m, 2H),4.36-4.22(m, 4H),3.87-3.70(m, 3H), 3.66-3.40(m, 5H),3.32(s, 12H),2.99-2.59(m, 8H),1.67-1.22(m, 56H),0.93-0.80(m, 6H)。
实施例3
(1)将4.1 g的3-十五烷基苯氧乙基溴溶解到20 mL的异丙醇溶剂中,然后滴加3mL含有1.3 g的二甲胺的水溶液,在N2保护下滴加3 mL的25%的氢氧化钠催化剂的水溶液,并在80 ℃中搅拌反应18 h,反应后旋转除去溶剂,去离子水洗涤后,粗产物进行柱色谱分离,以体积比石油醚:乙酸乙酯=15:1作为洗脱剂,分离得到3-十五烷基苯氧基-N,N-二甲基乙胺。
(2)将3.7 g的3-十五烷基苯氧基-N,N-二甲基乙胺溶解到20 mL的异丙醇溶剂中,然后滴加4 mL的含有3 g的3-氯-2-羟基丙磺酸钠的水溶液,在80 ℃中搅拌反应12 h,反应后旋转除去溶剂,依次用饱和氯化钠溶液、甲醇和石油醚洗涤,得到3-十五烷基苯氧基羟基磺酸季铵盐。
(3)将2.5 g的3-十五烷基苯氧基羟基磺酸季铵盐加入到10 mL的二氯甲烷中,搅拌均匀后在冰浴下加入2.5 g的己二酰氯和1.6 g的三乙胺,搅拌均匀后在30 ℃中搅拌反应24 h,反应后旋转除去溶剂,依次用饱和氯化钠溶液、甲醇和石油醚洗涤,得到含有双(十五烷基苯氧基烷基磺酸季铵盐)结构的表面活性剂;结构式为,分子式为C62H108N2O12S2。1H NMR (300MHz,CDCl3):δ7.40-7.30(m, 4H),6.92-6.53(m, 4H),4.62-4.49 (m, 2H),4.39-4.26(m, 4H),3.87-3.72(m, 4H), 3.70-3.50(m, 8H),3.32(s, 12H),2.92-2.50(m, 8H),1.67-1.22(m,56H),0.93-0.82(m, 6H)。
实施例4
(1)将4.1 g的3-十五烷基苯氧乙基溴溶解到20 mL的异丙醇溶剂中,然后滴加3mL含有1.1 g的二甲胺的水溶液,在N2保护下滴加3 mL的15%的氢氧化钾催化剂的水溶液,并在50 ℃中搅拌反应12 h,反应后旋转除去溶剂,去离子水洗涤后,粗产物进行柱色谱分离,以体积比石油醚:乙酸乙酯=10:1作为洗脱剂,分离得到3-十五烷基苯氧基-N,N-二甲基乙胺。
(2)将3.7 g的3-十五烷基苯氧基-N,N-二甲基乙胺溶解到20 mL的异丙醇溶剂中,然后滴加4 mL的含有2.4 g的3-氯-2-羟基丙磺酸钠的水溶液,在80 ℃中搅拌反应12 h,反应后旋转除去溶剂,依次用饱和氯化钠溶液、甲醇和石油醚洗涤,得到3-十五烷基苯氧基羟基磺酸季铵盐。
(3)将2.5 g的3-十五烷基苯氧基羟基磺酸季铵盐加入到10 mL的二氯甲烷中,搅拌均匀后在冰浴下加入2.4 g的辛二酰氯和1 g的三乙胺,搅拌均匀后在25 ℃中搅拌反应36 h,反应后旋转除去溶剂,依次用饱和氯化钠溶液、甲醇和石油醚洗涤,得到含有双(十五烷基苯氧基烷基磺酸季铵盐)结构的表面活性剂;结构式为,分子式为C64H112N2O12S2。1H NMR(300MHz,CDCl3):δ7.42-7.30(m, 4H),6.91-6.48(m, 4H),4.71-4.54 (m, 2H),4.36-4.26(m, 4H),3.80-3.51(m, 12H),3.28(s, 12H),2.90-2.72(m, 4H),2.69-2.54(m, 4H),1.60-1.24(m, 60H),0.90-0.81(m, 6H)。
分别将实施例1-4制备的表面活性剂加入到蒸馏水中,搅拌均匀后配置成质量分数为2%的溶液,然后滴加0.5 mL的1×106 CFU/mL的大肠杆菌菌悬液,控制作用时间,然后再将其移取0.5 mL加入到PBS缓冲溶液中进行梯度稀释,将稀释后菌悬液通过倾注法接种在琼脂培养基中,以不加表面活性剂的菌悬液作为空白对照,在恒温培养箱中37 ℃下培养48 h,培养后进行菌落计数并计算抑菌率。抑菌率=(空白对照菌落数-实验组菌落数)/空白对照菌落数×100%。
通过态表面张力仪,使用最大泡压法测定表面活性剂的表面张力,参考GB/T22237-2008标准。
将表面活性剂加入到蒸馏水中,配置成0.5 g/L的溶液,在25下测试发泡性能,参考GB/T 13173-2008标准。
Claims (8)
2.一种如权利要求1所述的表面活性剂的制备方法,其特征在于:所述制备方法为:
(1)将3-十五烷基苯氧乙基溴溶解到异丙醇溶剂中,然后滴加二甲胺的水溶液,在N2保护下滴加催化剂的水溶液,并在50-80 ℃中搅拌反应6-18 h,反应后旋转除去溶剂,去离子水洗涤后,粗产物进行柱色谱分离,以体积比石油醚:乙酸乙酯=(10-20):1作为洗脱剂,分离得到3-十五烷基苯氧基-N,N-二甲基乙胺,结构式为式(Ⅱ):
(2)将3-十五烷基苯氧基-N,N-二甲基乙胺溶解到异丙醇溶剂中,然后滴加3-氯-2-羟基丙磺酸钠的水溶液,在60-80 ℃中搅拌反应10-20 h,反应后旋转除去溶剂,依次用饱和氯化钠溶液、甲醇和石油醚洗涤,得到3-十五烷基苯氧基羟基磺酸季铵盐,结构式为式(Ⅲ):
(3)将3-十五烷基苯氧基羟基磺酸季铵盐加入到二氯甲烷中,搅拌均匀后在冰浴下加入烷基二酰氯和三乙胺,搅拌均匀后在25-40 ℃中搅拌反应12-36 h,反应后旋转除去溶剂,依次用饱和氯化钠溶液、甲醇和石油醚洗涤,得到含有双(十五烷基苯氧基烷基磺酸季铵盐)结构的表面活性剂。
3.根据权利要求2所述的表面活性剂的制备方法,其特征在于:所述(1)3-十五烷基苯氧乙基溴、二甲胺的摩尔比为1:1.8-3。
4.根据权利要求2所述的表面活性剂的制备方法,其特征在于:所述(1)中催化剂的水溶液的浓度为15-25%。
5.根据权利要求2或4所述的表面活性剂的制备方法,其特征在于:所述催化剂为氢氧化钾或氢氧化钠。
6.根据权利要求2所述的表面活性剂的制备方法,其特征在于:所述(2)中3-十五烷基苯氧基-N,N-二甲基乙胺、3-氯-2-羟基丙磺酸钠的摩尔比为1:1.2-1.6。
7.根据权利要求2所述的表面活性剂的制备方法,其特征在于:所述(3)中3-十五烷基苯氧基羟基磺酸季铵盐、烷基二酰氯和三乙胺的摩尔比例为1:2.5-3.5:2-3.2。
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