CN102875410A - N, N-dimethyl-N [3-(carbohydrate amide group)] propyl group-N-alkyl ammonium bromide and synthetic method thereof - Google Patents
N, N-dimethyl-N [3-(carbohydrate amide group)] propyl group-N-alkyl ammonium bromide and synthetic method thereof Download PDFInfo
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- 238000010189 synthetic method Methods 0.000 title claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 title claims 3
- 235000000346 sugar Nutrition 0.000 claims abstract description 38
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- 125000003368 amide group Chemical group 0.000 claims abstract description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims abstract description 8
- 125000000600 disaccharide group Chemical group 0.000 claims abstract description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 33
- 239000002904 solvent Substances 0.000 claims description 22
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 claims description 11
- 235000012209 glucono delta-lactone Nutrition 0.000 claims description 11
- 229960003681 gluconolactone Drugs 0.000 claims description 11
- UOQHWNPVNXSDDO-UHFFFAOYSA-N 3-bromoimidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=CC(C#N)=CN2C(Br)=CN=C21 UOQHWNPVNXSDDO-UHFFFAOYSA-N 0.000 claims description 8
- 229940099563 lactobionic acid Drugs 0.000 claims description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 150000008163 sugars Chemical class 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000002772 monosaccharides Chemical group 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 14
- 238000003786 synthesis reaction Methods 0.000 abstract description 14
- 238000000034 method Methods 0.000 abstract description 7
- 239000003054 catalyst Substances 0.000 abstract description 2
- 125000001483 monosaccharide substituent group Chemical group 0.000 abstract 1
- -1 amide quaternary ammonium salt Chemical class 0.000 description 26
- 239000004094 surface-active agent Substances 0.000 description 14
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 13
- 238000003756 stirring Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- 239000000843 powder Substances 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- 229930182470 glycoside Natural products 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- QFCNPWWLXUYFFU-UHFFFAOYSA-N N-[3-(dimethylamino)propyl]-2-hydroxypropanamide Chemical compound CC(O)C(=O)NCCCN(C)C QFCNPWWLXUYFFU-UHFFFAOYSA-N 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 238000001308 synthesis method Methods 0.000 description 5
- 239000013543 active substance Substances 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003093 cationic surfactant Substances 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 238000005956 quaternization reaction Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- 239000008233 hard water Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000003945 chlorohydrins Chemical class 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
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- 238000005553 drilling Methods 0.000 description 1
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- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
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Abstract
一种N,N-二甲基-N[3-(糖酰胺基)]丙基-N-烷基溴化铵的结构通式如下:
其中:R为C8-C14的长链烃基,糖基为单糖基或二糖基。本发明具有合成工艺简单,设备要求低,适合工业化,反应温度低、无需压力和催化剂,糖基上的反应位置确定,反应均衡,不会出现多取代产物,产率高的优点。A kind of N,N-dimethyl-N [3-(sugar amido)] propyl-N-alkylammonium bromide has a general structural formula as follows:
Wherein: R is a C 8 -C 14 long-chain hydrocarbon group, and the sugar group is a monosaccharide group or a disaccharide group. The invention has the advantages of simple synthesis process, low equipment requirements, suitability for industrialization, low reaction temperature, no need for pressure and catalyst, definite reaction position on sugar groups, balanced reaction, no multi-substituted products and high yield.Description
技术领域 technical field
本发明涉及一种糖基酰胺季铵盐表面活性剂及其合成方法,具体地说涉及一种N,N-二甲基-N[3-(糖酰胺基)]丙基-N-烷基溴化铵及其合成方法。 The invention relates to a sugar-based amide quaternary ammonium salt surfactant and a synthesis method thereof, in particular to a N,N-dimethyl-N[3-(sugar amido)]propyl-N-alkyl Ammonium bromide and its synthesis method.
背景技术 Background technique
近年来,随着人们对环境问题的日益重视,制备环境友好型表面活性剂也越来越引起人们关注。用碳水化合物生产表面活性剂不仅原料价格低廉、资源丰富,而且所得产品温和、无毒、性能优良、环境兼容性好,是21世纪人们关注的热点之一。葡萄糖酸内酯和乳糖酸是由可再生资源淀粉制备而来的,具有价格便宜、绿色环保、易于与烷基胺进行胺酯反应等优点,且该反应无需对糖上的羟基进行繁琐、昂贵的保护,反应具有温度低,反应转化率高,无副反应发生等优点,很符合原子经济性反应的特点。因而,以葡萄糖酸内酯和乳糖酸为原料生产的糖基酰胺型表面活性剂,具有良好的发展空间。 In recent years, with people's increasing attention to environmental issues, the preparation of environmentally friendly surfactants has attracted more and more attention. The production of surfactants from carbohydrates is not only cheap in raw materials and rich in resources, but also mild, non-toxic, excellent in performance and good in environmental compatibility. It is one of the hot spots that people pay attention to in the 21st century. Gluconolactone and lactobionic acid are prepared from renewable resource starch, which have the advantages of low price, environmental protection, and easy amine ester reaction with alkylamines, and the reaction does not require cumbersome and expensive reactions on the hydroxyl groups on sugars. The protection of the reaction has the advantages of low temperature, high reaction conversion rate, no side reaction, etc., which is in line with the characteristics of atom-economical reaction. Therefore, the glycosylamide type surfactant produced from gluconolactone and lactobionic acid has a good development space.
糖基季铵盐表面活性剂结合了糖基表面活性剂的温和性与季铵盐型表面活性剂的高效性,使其具有非离子表面活性剂的温和性、低毒性、低刺激性,兼有阳离子表面活性剂的杀菌性、抗静电性和抗硬水性,还有一般阳离子表面活性剂所不具备的能和阴离子表面活性剂良好的配伍性能,是一种多功能型表面活性剂。 The sugar-based quaternary ammonium salt surfactant combines the mildness of the sugar-based surfactant and the high efficiency of the quaternary ammonium salt surfactant, making it have the mildness, low toxicity, and low irritation of the non-ionic surfactant, and also It has the bactericidal, antistatic and anti-hard water properties of cationic surfactants, as well as good compatibility with anionic surfactants that general cationic surfactants do not have. It is a multifunctional surfactant.
糖基季铵盐表面活性剂目前的合成方法主要是用葡萄糖或烷基糖苷为原料,先季铵化再糖苷化或先糖苷化再季铵化的方法来合成。Kenneth B. Moser等人用低级叔胺(三甲胺、三乙胺、三丙胺)与环氧氯丙烷反应生成阳离子化试剂,然后再与烷基糖苷反应生成糖苷基季铵盐。Manfred Weuthen等人开发出先将烷基糖苷与环氧氯丙烷反应,生成氯代糖苷中间体,然后再与叔胺反应生成糖苷基季铵盐。这两种方法的主要不足在于烷基糖苷中各羟基的活性差别不大,反应在什么位置不确定,反应不均衡,常出现多取代;John J. Tsai等人用葡萄糖先与氯代醇反应,得到氯代糖苷,再与高级叔胺进行季铵化反应,得到目标产物。此反应中不仅需要催化剂,而且季铵化反应过程中由于氯代糖苷和高级叔胺的相溶性不好,加之葡萄糖的位阻很大,反应速率很慢。且在目前报道的糖基季铵盐表面活性剂中大多都是以醚键相结合的产物,以酰胺键相结合的糖基季铵盐表面活性剂未见报道。酰胺键类似于蛋白质中的肽键,可以与皮肤具有更好的相容性,可赋予毛、皮肤自然光泽,并使之柔润。 The current synthesis method of sugar-based quaternary ammonium salt surfactant is mainly to use glucose or alkyl glycoside as raw material, first quaternized and then glycosidized or first glycosidized and then quaternized to synthesize. Kenneth B. Moser et al. used lower tertiary amines (trimethylamine, triethylamine, tripropylamine) to react with epichlorohydrin to generate cationization reagents, and then reacted with alkyl glycosides to generate glycoside-based quaternary ammonium salts. Manfred Weuthen and others developed the reaction of alkyl glycosides with epichlorohydrin to generate chloroglycoside intermediates, and then reacted with tertiary amines to generate glycoside-based quaternary ammonium salts. The main disadvantage of these two methods is that the activity of each hydroxyl group in the alkyl glycoside is not very different, the position of the reaction is uncertain, the reaction is unbalanced, and multiple substitutions often occur; John J. Tsai and others use glucose to react with chlorohydrins first. , to obtain chloroglucoside, and then carry out quaternization reaction with higher tertiary amine to obtain the target product. Not only need catalyzer in this reaction, and because the intermiscibility of chloroglucoside and advanced tertiary amine is bad in the quaternization reaction process, the steric hindrance of glucose is very big in addition, and reaction rate is very slow. And most of the sugar-based quaternary ammonium salt surfactants reported at present are products combined with ether bonds, and the sugar-based quaternary ammonium salt surfactants combined with amide bonds have not been reported. The amide bond is similar to the peptide bond in the protein, which can have better compatibility with the skin, and can give the hair and skin a natural luster and make it soft and moist.
用葡萄糖酸内酯或乳糖酸与N,N-二甲基-1,3-丙二胺反应,再与溴代烷发生季铵化反应生成N,N-二甲基-N[3-(糖酰胺基)]丙基-N-烷基溴化铵这类新型表面活性剂的合成方法和产物结构尚未见报道。 Use gluconolactone or lactobionic acid to react with N,N-dimethyl-1,3-propanediamine, and then react with brominated alkyl to generate N,N-dimethyl-N[3-( Sugar amido)] propyl-N-alkylammonium bromide synthesis method and product structure of this new class of surfactants have not been reported yet.
发明内容 Contents of the invention
本发明的目的是提供一种利用葡萄糖酸内酯或乳糖酸先与N,N-二甲基-1,3-丙二胺反应生成N,N-二甲基-N′-糖酰基-1,3-丙二胺中间体,再与溴代烷发生季铵化反应制备的N,N-二甲基-N[3-(糖酰胺基)]丙基-N-烷基溴化铵及其合成方法。 The object of the present invention is to provide a method of utilizing gluconolactone or lactobionic acid to react with N,N-dimethyl-1,3-propanediamine to generate N,N-dimethyl-N'-sugar acyl-1 , 3-propanediamine intermediate, and N,N-dimethyl-N[3-(sugaramido)]propyl-N-alkyl ammonium bromide prepared by quaternization reaction with alkyl bromide and its synthesis method.
本发明提供的N,N-二甲基-N[3-(糖酰胺基)]丙基-N-烷基溴化铵的结构通式如下: The general structural formula of N,N-dimethyl-N [3-(sugar amido)] propyl-N-alkylammonium bromide provided by the invention is as follows:
其中:R为C8-C14的长链烃基,糖基为单糖基或二糖基。 Wherein: R is a C 8 -C 14 long-chain hydrocarbon group, and the sugar group is a monosaccharide group or a disaccharide group.
反应路线如下(以葡萄糖酸内酯为例): The reaction scheme is as follows (taking gluconolactone as an example):
本发明的合成方法: Synthetic method of the present invention:
(1) 按糖和N,N-二甲基-1,3-丙二胺的摩尔配比为1.0:1.0-1.2,最好是1:1,,用甲醇做溶剂,将糖和N,N-二甲基-1,3-丙二胺混合,最好是甲醇回流的情况下反应,于反应温度为45-65 ℃,反应时间为6-10 h;反应完成后,蒸掉溶剂,用乙醚洗涤,得到N,N-二甲基-N′-糖酰基-1,3-丙二胺中间体; (1) According to the molar ratio of sugar and N,N-dimethyl-1,3-propanediamine is 1.0:1.0-1.2, preferably 1:1, using methanol as solvent, sugar and N, N-dimethyl-1,3-propanediamine is mixed, preferably under the condition of methanol reflux, the reaction temperature is 45-65 ℃, and the reaction time is 6-10 h; after the reaction is completed, evaporate the solvent, Wash with ether to obtain N,N-dimethyl-N'-sugaryl-1,3-propanediamine intermediate;
(2)将N,N-二甲基-N′-糖酰基-1,3-丙二胺中间体和溴代烷,用低碳醇作溶剂,反应温度为60-80 ℃,反应时间为15-20 h,其中N,N-二甲基-N′-糖酰基-1,3-丙二胺中间体和溴代烷的摩尔配比为1.0:1.0-1.3,最好为1.0: 1.1,反应完成后,蒸掉溶剂,用乙醚洗涤,得到N,N-二甲基-N[3-(糖酰胺基)]丙基-N-烷基溴化铵。 (2) Mix N,N-dimethyl-N′-sugaryl-1,3-propanediamine intermediate and bromoalkane with lower alcohol as solvent, the reaction temperature is 60-80 ℃, and the reaction time is 15-20 h, wherein the molar ratio of N,N-dimethyl-N′-sugaryl-1,3-propanediamine intermediate and bromoalkane is 1.0:1.0-1.3, preferably 1.0:1.1 , After the reaction was completed, the solvent was distilled off and washed with ether to obtain N,N-dimethyl-N[3-(sugaramido)]propyl-N-alkylammonium bromide.
如上所述的糖为葡萄糖酸内酯和乳糖酸。 Sugars mentioned above are gluconolactone and lactobionic acid.
如上所述的溴代烷为长链C8-C14直链烷基溴代烷。 The brominated alkanes mentioned above are long chain C 8 -C 14 linear alkyl brominated alkanes.
如上所述的低碳醇溶剂为甲醇、无水乙醇或95%乙醇。 The above-mentioned low-carbon alcohol solvent is methanol, absolute ethanol or 95% ethanol.
如上所述的N,N-二甲基-N[3-(糖酰胺基)]丙基-N-烷基溴化铵经改良的佛尔哈特法方法测定,纯度大于98%。用IR和1H NMR进行结构表征确认所分析的N,N-二甲基-N[3-(糖酰胺基)]丙基-N-烷基溴化铵是目标产物。 The N,N-dimethyl-N[3-(sugaramido)]propyl-N-alkylammonium bromide as mentioned above was determined by the improved Volhart method, and the purity was greater than 98%. Structural characterization by IR and 1 H NMR confirmed that the analyzed N,N-dimethyl-N[3-(sugaramido)]propyl-N-alkylammonium bromide was the target product.
本发明所制备的产品为糖基酰胺季铵盐表面活性剂,在结构上不仅具有非离子型的糖基亲水基,而且具有阳离子型季铵盐的特性,还有酰胺键的特性。因此此产品性能温和、低毒、低刺激,兼有阳离子表面活性剂的杀菌性、抗静电性和抗硬水性,还和皮肤有更好的相容性,及其与阴离子表面活性剂的良好配伍性能,是一种多功能型表面活性剂。可广泛应用于纺织、造纸、化妆品、洗涤用品、采矿业和钻井液等行业,具有良好的应用前景。 The product prepared by the present invention is a sugar-based amide quaternary ammonium salt surfactant, which not only has a non-ionic sugar-based hydrophilic group, but also has the characteristics of a cationic quaternary ammonium salt and an amide bond. Therefore, this product has mild performance, low toxicity, and low irritation. It has both the bactericidal, antistatic and hard water resistance of cationic surfactants, and has better compatibility with skin and good compatibility with anionic surfactants. Compatibility, is a multifunctional surfactant. It can be widely used in industries such as textiles, papermaking, cosmetics, washing supplies, mining and drilling fluid, and has a good application prospect.
本发明与现有的糖基季铵盐的技术相比具有如下优点: Compared with the technology of existing glycosyl quaternary ammonium salt, the present invention has the following advantages:
1.本发明合成工艺简单,设备要求低,适合工业化。 1. The synthesis process of the present invention is simple, requires low equipment, and is suitable for industrialization.
2.反应温度低、无需压力和催化剂。 2. Low reaction temperature, no need for pressure and catalyst.
3.糖基上的反应位置确定,反应均衡,不会出现多取代产物,产率高。 3. The reaction position on the sugar group is determined, the reaction is balanced, there will be no multiple substitution products, and the yield is high.
附图说明 Description of drawings
图 1 N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺的红外谱图; Figure 1 The infrared spectrum of N,N-dimethyl-N′-glucosyl-1,3-propanediamine;
图 2 N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺的1HNMR谱图; Figure 2 1 H NMR spectrum of N,N-dimethyl-N′-glucosyl-1,3-propanediamine;
图 3 N,N-二甲基-N[3-(葡萄糖酰胺基)]丙基-N-辛烷基溴化铵的1HNMR谱图; Figure 3 1 HNMR spectrum of N,N-dimethyl-N[3-(glucosamido)]propyl-N-octyl ammonium bromide;
图 4 N,N-二甲基-N[3-(葡萄糖酰胺基)]丙基-N-癸烷基溴化铵的1HNMR谱图; Figure 4 1 HNMR spectrum of N,N-dimethyl-N[3-(glucosamido)]propyl-N-decyl ammonium bromide;
图 5 N,N-二甲基-N[3-(葡萄糖酰胺基)]丙基-N-十二烷基溴化铵的1HNMR谱图; Figure 5 1 HNMR spectrum of N,N-dimethyl-N[3-(glucosamido)]propyl-N-dodecylammonium bromide;
图 6 N,N-二甲基-N[3-(葡萄糖酰胺基)]丙基-N-十四烷基溴化铵的1HNMR谱图; Figure 6 1 HNMR spectrum of N,N-dimethyl-N[3-(glucosamido)]propyl-N-tetradecylammonium bromide;
图 7 N,N-二甲基-N′-乳糖酰基-1,3-丙二胺的1HNMR谱图; Figure 7 1 HNMR spectrum of N,N-dimethyl-N′-lactoyl-1,3-propanediamine;
图 8 N,N-二甲基-N[3-(乳糖酰胺基)]丙基-N-十二烷基溴化铵的1HNMR谱图; Figure 8 1 HNMR spectrum of N,N-dimethyl-N[3-(lactosamido)]propyl-N-dodecylammonium bromide;
图 9 N,N-二甲基-N[3-(乳糖酰胺基)]丙基-N-十四烷基溴化铵的1HNMR谱图。 Figure 9 1 H NMR spectrum of N,N-dimethyl-N[3-(lactosamido)]propyl-N-tetradecylammonium bromide.
具体实施方式 Detailed ways
实施例 1 Example 1
1、N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺的合成 1. Synthesis of N,N-dimethyl-N'-glucosyl-1,3-propanediamine
在装有温度计和球形冷凝管的250 mL三颈圆底烧瓶中,加入12.2 g (120 mmol) N,N-二甲基-1,3-丙二胺,葡萄糖酸内酯21.4 g (120 mmol),甲醇80 mL。在搅拌的条件下,保持温度55 ℃,反应8 h。停止加热,静置冷却。用旋转蒸发仪蒸掉溶剂,对所得产品用乙醚洗涤2次,去除残余的N,N-二甲基-1,3-丙二胺,得到白色粉末固体(N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺)32.2 g,产率95.8 %。
In a 250 mL three-neck round bottom flask equipped with a thermometer and a spherical condenser, add 12.2 g (120 mmol) N,N-dimethyl-1,3-propanediamine, 21.4 g (120 mmol) gluconolactone ),
IR(KBr): 3368 cm-1 (ν(O–H)), 2941-2819 cm-1 (ν(C–H) in –CH2– or -CH3 ), ( 1651 cm-1 (ν(C=O) in amide), 1542 cm-1 (δ(N–H) in amide), 1461 cm-1(ν(C–H) in –CH2– ), 1091-1036 cm-1(ν(O–H)), 718 cm-1(δ(C-C) in >4CH2). IR(KBr): 3368 cm -1 ( ν (O–H)), 2941-2819 cm -1 ( ν (C–H) in –CH 2 – or -CH 3 ), ( 1651 cm -1 ( ν ( C=O) in amide), 1542 cm -1 (δ(N–H) in amide), 1461 cm -1 ( ν (C–H) in –CH 2 – ), 1091-1036 cm -1 ( ν ( O–H)), 718 cm -1 (δ(CC) in >4CH 2 ).
1H-NMR (CDCl3, ppm) δ: 1.618 (m, 2H, CH2 CH 2 CH2), 2.223 (s, 6H, N(CH 3 )2), 2.298 (t, 2H, NHCH2CH2 CH 2 ), 2.765 (t, 2H, NHCH 2 CH2CH2), 3.307-4.274 (6H, protons of sugar ), 7.794 (s, 1H, CONH). 1 H-NMR (CDCl 3 , ppm) δ: 1.618 (m, 2H, CH 2 CH 2 CH 2 ), 2.223 (s, 6H, N( CH 3 ) 2 ), 2.298 (t, 2H, NHCH 2 CH 2 CH 2 ), 2.765 (t, 2H, NH CH 2 CH 2 CH 2 ), 3.307-4.274 (6H, protons of sugar ), 7.794 (s, 1H, CO NH ).
2、N,N-二甲基-N[3-(葡萄糖酰胺基)]丙基-N-辛烷基溴化铵的合成 2. Synthesis of N,N-dimethyl-N[3-(glucosamido)]propyl-N-octyl ammonium bromide
在装有温度计和球形冷凝管的250 mL三颈圆底烧瓶中,加入N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺15 g (53.6 mmol),溴代辛烷10.3 g (53.6 mmol), 无水乙醇80 mL。在搅拌的条件下,保持温度60℃,反应20 h。停止加热,静置冷却。用旋转蒸发仪蒸掉溶剂,产品用乙醚洗涤3次,得到棕色糖浆(N,N-二甲基-N[3-(葡萄糖酰胺基)]丙基-N-辛烷基溴化铵)。最后测得产品中季铵盐活性物含量为98.3%。
In a 250 mL three-necked round-bottomed flask equipped with a thermometer and a spherical condenser, add 15 g (53.6 mmol) of N,N-dimethyl-N′-glucosyl-1,3-propanediamine, octyl bromide Alkanes 10.3 g (53.6 mmol),
1H-NMR (CDCl3, ppm) δ: 0.890 (t, 3H, (CH2)5 CH 3 ), 1.268 (m, 10H, (CH 2 ) 5 CH3), 1.729 (m, 2H, CH 2 (CH2)5CH3), 2.108 (m, 2H, NHCH2 CH 2 CH2), 3.230 (s, 6H, N(CH 3 )2), 3.394 (t, 2H, NCH 2 CH2), 3.570 (t, 2H, NHCH2CH2 CH 2 ), 3.781 (t, 2H, NHCH 2 CH2CH2), 4.137-5.516 (6H, protons of sugar ), 8.089 (s, 1H, CONH). 1 H-NMR (CDCl 3 , ppm) δ: 0.890 (t, 3H, (CH 2 ) 5 CH 3 ), 1.268 (m, 10H, (CH 2 ) 5 CH 3 ), 1.729 (m, 2H, CH 2 (CH 2 ) 5 CH 3 ), 2.108 (m, 2H, NHCH 2 CH 2 CH 2 ), 3.230 (s, 6H, N( CH 3 ) 2 ), 3.394 (t, 2H, N CH 2 CH 2 ), 3.570 (t, 2H, NHCH 2 CH 2 CH 2 ), 3.781 (t, 2H, NH CH 2 CH 2 CH 2 ), 4.137-5.516 (6H, protons of sugar ), 8.089 (s, 1H, CO NH ).
实施例 2 Example 2
N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺的合成 Synthesis of N,N-Dimethyl-N'-glucosyl-1,3-propanediamine
在装有温度计和球形冷凝管的250 mL三颈圆底烧瓶中,加入12.2 g (120 mmol) N,N-二甲基-1,3-丙二胺,葡萄糖酸内酯20.5 g (115 mmol),甲醇80 mL。在搅拌的条件下,保持温度60 ℃,反应7 h。停止加热,静置冷却。用旋转蒸发仪蒸掉溶剂,对所得产品用乙醚洗涤2次,去除残余的N,N-二甲基-1,3-丙二胺,得到白色粉末固体(N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺)30.2g,产率92.4 %。
In a 250 mL three-neck round bottom flask equipped with a thermometer and a spherical condenser, add 12.2 g (120 mmol) N,N-dimethyl-1,3-propanediamine, 20.5 g (115 mmol) gluconolactone ),
N,N-二甲基-N[3-(葡萄糖酰胺基)]丙基-N-癸烷基溴化铵的合成 Synthesis of N,N-Dimethyl-N[3-(glucosamido)]propyl-N-decylammonium bromide
在装有温度计和球形冷凝管的250 mL三颈圆底烧瓶中,加入N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺15 g (53.6 mmol),溴代癸烷13 g (59 mmol), 无水乙醇80 mL。在搅拌的条件下,保持温度80℃,反应18 h。停止加热,静置冷却。用旋转蒸发仪蒸掉溶剂,产品用乙醚洗涤3次,得到白色粉末固体(N,N-二甲基-N[3-(葡萄糖酰胺基)]丙基-N-癸烷基溴化铵)。最后测得产品中季铵盐活性物含量为99%。
In a 250 mL three-neck round bottom flask equipped with a thermometer and a spherical condenser, add 15 g (53.6 mmol) of N,N-dimethyl-N′-glucosyl-1,3-propanediamine, bromodecyl Alkanes 13 g (59 mmol),
1H-NMR (CDCl3, ppm) δ: 0.890 (t, 3H, (CH2)7 CH 3 ), 1.267 (m, 14H, (CH 2 ) 7 CH3), 1.731 (m, 2H, CH 2 (CH2)7CH3), 2.112 (m, 2H, NHCH2 CH 2 CH2), 3.234 (s, 6H, N(CH 3 )2), 3.395 (t, 2H, NCH 2 CH2), 3.591 (t, 2H, NHCH2CH2 CH 2 ), 3.782 (t, 2H, NHCH 2 CH2CH2), 4.146-5.518 (6H, protons of sugar ), 8.091 (s, 1H, CONH). 1 H-NMR (CDCl 3 , ppm) δ: 0.890 (t, 3H, (CH 2 ) 7 CH 3 ), 1.267 (m, 14H, (CH 2 ) 7 CH 3 ), 1.731 (m, 2H, CH 2 (CH 2 ) 7 CH 3 ), 2.112 (m, 2H, NHCH 2 CH 2 CH 2 ), 3.234 (s, 6H, N( CH 3 ) 2 ), 3.395 (t, 2H, N CH 2 CH 2 ), 3.591 (t, 2H, NHCH 2 CH 2 CH 2 ), 3.782 (t, 2H, NH CH 2 CH 2 CH 2 ), 4.146-5.518 (6H, protons of sugar ), 8.091 (s, 1H, CO NH ).
实施例 3 Example 3
N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺的合成 Synthesis of N,N-Dimethyl-N'-glucosyl-1,3-propanediamine
在装有温度计和球形冷凝管的250 mL三颈圆底烧瓶中,加入12.2 g (120 mmol) N,N-二甲基-1,3-丙二胺,葡萄糖酸内酯19.6 g (110 mmol),甲醇80 mL。在搅拌的条件下,保持温度65 ℃,反应6 h。停止加热,静置冷却。用旋转蒸发仪蒸掉溶剂,对所得产品用乙醚洗涤2次,去除残余的N,N-二甲基-1,3-丙二胺,得到白色粉末固体(N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺)30 g,产率94.3 %。
In a 250 mL three-neck round bottom flask equipped with a thermometer and a spherical condenser, add 12.2 g (120 mmol) N,N-dimethyl-1,3-propanediamine, 19.6 g (110 mmol) gluconolactone ),
N,N-二甲基-N[3-(葡萄糖酰胺基)]丙基-N-十二烷基溴化铵的合成 Synthesis of N,N-Dimethyl-N[3-(glucosamido)]propyl-N-dodecylammonium bromide
在装有温度计和球形冷凝管的250 mL三颈圆底烧瓶中,加入N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺15 g (53.6 mmol),溴代十二烷15.9 g (64 mmol), 95%乙醇80 mL。在搅拌的条件下,保持温度70℃,反应17 h。停止加热,静置冷却。用旋转蒸发仪蒸掉溶剂,产品用乙醚洗涤3次,得到白色粉末固体(N,N-二甲基-N[3-(葡萄糖酰胺基)]丙基-N-十二烷基溴化铵)。最后测得产品中季铵盐活性物含量为98.8%。
In a 250 mL three-necked round-bottomed flask equipped with a thermometer and a spherical condenser, add 15 g (53.6 mmol) of N,N-dimethyl-N′-glucosyl-1,3-propanediamine, decabromide Dioxane 15.9 g (64 mmol), 95
1H-NMR(CDCl3, ppm) δ: 0.893(t, 3H, (CH2)9 CH 3 ), 1.268 (m, 18H, (CH 2 ) 9 CH3), 1.733 (m, 2H, CH 2 (CH2)9CH3), 2.088 (m, 2H, NHCH2 CH 2 CH2), 3.237 (s, 6H, N(CH 3 )2), 3.420 (t, 2H, NCH 2 CH2), 3.605 (t, 2H, NHCH2CH2 CH 2 ), 3.787 (t, 2H, NHCH 2 CH2CH2), 4.154-5.598 (6H, protons of sugar ), 8.093 (s, 1H, CONH) 1 H-NMR(CDCl 3 , ppm) δ: 0.893(t, 3H, (CH 2 ) 9 CH 3 ), 1.268 (m, 18H, (CH 2 ) 9 CH 3 ), 1.733 (m, 2H, CH 2 (CH 2 ) 9 CH 3 ), 2.088 (m, 2H, NHCH 2 CH 2 CH 2 ), 3.237 (s, 6H, N( CH 3 ) 2 ), 3.420 (t, 2H, N CH 2 CH 2 ), 3.605 (t, 2H, NHCH 2 CH 2 CH 2 ), 3.787 (t, 2H, NH CH 2 CH 2 CH 2 ), 4.154-5.598 (6H, protons of sugar ), 8.093 (s, 1H, CO NH )
实施例 4 Example 4
N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺的合成 Synthesis of N,N-Dimethyl-N'-glucosyl-1,3-propanediamine
在装有温度计和球形冷凝管的250 mL三颈圆底烧瓶中,加入12.2 g (120 mmol) N,N-二甲基-1,3-丙二胺,葡萄糖酸内酯17.8 g (100 mmol),甲醇80 mL。在搅拌的条件下,保持温度45 ℃,反应10 h。停止加热,静置冷却。用旋转蒸发仪蒸掉溶剂,对所得产品用乙醚洗涤2次,去除残余的N,N-二甲基-1,3-丙二胺,得到白色粉末固体(N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺)27.5 g,产率91.7 %。
In a 250 mL three-neck round bottom flask equipped with a thermometer and a spherical condenser, add 12.2 g (120 mmol) N,N-dimethyl-1,3-propanediamine, 17.8 g (100 mmol) gluconolactone ),
N,N-二甲基-N[3-(葡萄糖酰胺基)]丙基-N-十四烷基溴化铵的合成 Synthesis of N,N-Dimethyl-N[3-(glucosamido)]propyl-N-tetradecylammonium bromide
在装有温度计和球形冷凝管的250 mL三颈圆底烧瓶中,加入N,N-二甲基-N′-葡萄糖酰基-1,3-丙二胺15 g (53.6 mmol),溴代十四烷19.3 g (69.7 mmol), 95%乙醇80 mL。在搅拌的条件下,保持温度77℃,反应15 h。停止加热,静置冷却。用旋转蒸发仪蒸掉溶剂,产品用乙醚洗涤3次,得到白色粉末固体(N,N-二甲基-N[3-(葡萄糖酰胺基)]丙基-N-十四烷基溴化铵)。最后测得产品中季铵盐活性物含量为98.6%。
In a 250 mL three-necked round-bottomed flask equipped with a thermometer and a spherical condenser, add 15 g (53.6 mmol) of N,N-dimethyl-N′-glucosyl-1,3-propanediamine, decabromide Tetraxane 19.3 g (69.7 mmol), 95
1H-NMR(CDCl3, ppm) δ: 0.883(t, 3H, (CH2)11 CH 3 ), 1.268 (m, 22H, (CH 2 ) 11 CH3), 1.726 (m, 2H, CH 2 (CH2)11CH3), 2.088 (m, 2H, NHCH2 CH 2 CH2), 3.235 (s, 6H, N(CH 3 )2), 3.393 (t, 2H, NCH 2 CH2), 3.583 (t, 2H, NHCH2CH2 CH 2 ), 3.786 (t, 2H, NHCH 2 CH2CH2), 4.154-5.537 (6H, protons of sugar ), 8.065 (s, 1H, CONH) 1 H-NMR(CDCl 3 , ppm) δ: 0.883(t, 3H, (CH 2 ) 11 CH 3 ), 1.268 (m, 22H, (CH 2 ) 11 CH 3 ), 1.726 (m, 2H, CH 2 (CH 2 ) 11 CH 3 ), 2.088 (m, 2H, NHCH 2 CH 2 CH 2 ), 3.235 (s, 6H, N( CH 3 ) 2 ), 3.393 (t, 2H, N CH 2 CH 2 ), 3.583 (t, 2H, NHCH 2 CH 2 CH 2 ), 3.786 (t, 2H, NH CH 2 CH 2 CH 2 ), 4.154-5.537 (6H, protons of sugar ), 8.065 (s, 1H, CO NH )
实施例 5 Example 5
N,N-二甲基-N′-乳糖酰基-1,3-丙二胺的合成 Synthesis of N,N-Dimethyl-N'-lactoyl-1,3-propanediamine
在装有温度计和球形冷凝管的250 mL三颈圆底烧瓶中,加入6.1 g (60 mmol) N,N-二甲基-1,3-丙二胺,乳糖酸21.5 g (60 mmol),甲醇80 mL。在搅拌的条件下,保持温度65 ℃,反应8 h。停止加热,静置冷却。用旋转蒸发仪蒸掉溶剂,对所得产品用乙醚洗涤2次,去除残余的N,N-二甲基-1,3-丙二胺,得到浅棕色粉末固体(N,N-二甲基-N′-乳糖酰基-1,3-丙二胺)26 g,产率94.2 %。
In a 250 mL three-neck round bottom flask equipped with a thermometer and a spherical condenser, add 6.1 g (60 mmol) of N,N-dimethyl-1,3-propanediamine, 21.5 g (60 mmol) of lactobionic acid,
IR(KBr): 3384 cm-1 (ν(O–H)), 2938-2828 cm-1 (ν(C–H) in –CH2– or -CH3 ), ( 1653 cm-1 (ν(C=O) in amide), 1541 cm-1 (δ(N–H) in amide), 1457 cm-1(ν(C–H) in –CH2– ), 1078-1048 cm-1(ν(O–H)), 705 cm-1(δ(C-C) in >4CH2) IR(KBr): 3384 cm -1 ( ν (O–H)), 2938-2828 cm -1 ( ν (C–H) in –CH 2 – or -CH 3 ), ( 1653 cm -1 ( ν ( C=O) in amide), 1541 cm -1 (δ(N–H) in amide), 1457 cm -1 ( ν (C–H) in –CH 2 – ), 1078-1048 cm -1 ( ν ( O–H)), 705 cm -1 (δ(CC) in >4CH 2 )
1H-NMR (D2O, ppm) δ: 1.17 (m, 2H, CH2 CH 2 CH2), 1.73 (t, 2H, NHCH2CH2 CH 2 ), 2.27 (s, 6H, N(CH 3 )2), 2.43 (t, 2H, NHCH 2 CH2CH2), 3.27-4.57 (13H, protons of sugar ) 1 H-NMR (D 2 O, ppm) δ: 1.17 (m, 2H, CH 2 CH 2 CH 2 ), 1.73 (t, 2H, NHCH 2 CH 2 CH 2 ), 2.27 (s, 6H, N( CH 3 ) 2 ), 2.43 (t, 2H, NH CH 2 CH 2 CH 2 ), 3.27-4.57 (13H, protons of sugar )
N,N-二甲基-N[3-(乳糖酰胺基)]丙基-N-十二烷基溴化铵的合成 Synthesis of N,N-Dimethyl-N[3-(lactosamido)]propyl-N-dodecylammonium bromide
在装有温度计和球形冷凝管的250 mL三颈圆底烧瓶中,加入N,N-二甲基-N′-乳糖酰基-1,3-丙二胺6.9 g (15 mmol),溴代十二烷4 g (16 mmol), 甲醇80 mL。在搅拌的条件下,保持温度65℃,反应20 h。停止加热,静置冷却。用旋转蒸发仪蒸掉溶剂,产品用乙醚洗涤3次,得到棕黄色固体(N,N-二甲基-N[3-(乳糖酰胺基)]丙基-N-十二烷基溴化铵)。最后测得产品中季铵盐活性物含量为98.3%。
In a 250 mL three-neck round bottom flask equipped with a thermometer and a spherical condenser, add 6.9 g (15 mmol) of N,N-dimethyl-N′-lactoyl-1,3-propanediamine, decabromide Dioxane 4 g (16 mmol),
1H-NMR(D2O, ppm) δ: 0.82(t, 3H, (CH2)9 CH 3 ), 1.23 (m, 18H, (CH 2 ) 9 CH3), 1.69 (m, 2H, CH 2 (CH2)9CH3), 1.98 (m, 2H, NHCH2 CH 2 CH2), 2.78 (t, 2H, NCH 2 CH2), 3.01 (s, 6H, N(CH 3 )2), 3.27 (m, 4H, NHCH 2 CH2 CH 2 ), 3.53-4.52 (13H, protons of sugar ) 1 H-NMR(D 2 O, ppm) δ: 0.82(t, 3H, (CH 2 ) 9 CH 3 ), 1.23 (m, 18H, (CH 2 ) 9 CH 3 ), 1.69 (m, 2H, CH 2 (CH 2 ) 9 CH 3 ), 1.98 (m, 2H, NHCH 2 CH 2 CH 2 ), 2.78 (t, 2H, N CH 2 CH 2 ), 3.01 (s, 6H, N( CH 3 ) 2 ) , 3.27 (m, 4H, NH CH 2 CH 2 CH 2 ), 3.53-4.52 (13H, protons of sugar )
实施例 6 Example 6
N,N-二甲基-N′-乳糖酰基-1,3-丙二胺的合成 Synthesis of N,N-Dimethyl-N'-lactoyl-1,3-propanediamine
在装有温度计和球形冷凝管的250 mL三颈圆底烧瓶中,加入6.1 g (60 mmol) N,N-二甲基-1,3-丙二胺,乳糖酸21.5 g (60 mmol),甲醇80 mL。在搅拌的条件下,保持温度60 ℃,反应8 h。停止加热,静置冷却。用旋转蒸发仪蒸掉溶剂,对所得产品用乙醚洗涤2次,去除残余的N,N-二甲基-1,3-丙二胺,得到浅棕色粉末固体(N,N-二甲基-N′-乳糖酰基-1,3-丙二胺)26 g,产率93.2 %。
In a 250 mL three-neck round bottom flask equipped with a thermometer and a spherical condenser, add 6.1 g (60 mmol) of N,N-dimethyl-1,3-propanediamine, 21.5 g (60 mmol) of lactobionic acid,
N,N-二甲基-N[3-(乳糖酰胺基)]丙基-N-十四烷基溴化铵的合成 Synthesis of N,N-Dimethyl-N[3-(lactosamido)]propyl-N-tetradecylammonium bromide
在装有温度计和球形冷凝管的250 mL三颈圆底烧瓶中,加入N,N-二甲基-N′-乳糖酰基-1,3-丙二胺6.9 g (15 mmol),溴代十四烷4 g (17 mmol), 甲醇80 mL。在搅拌的条件下,保持温度60℃,反应20 h。停止加热,静置冷却。用旋转蒸发仪蒸掉溶剂,产品用乙醚洗涤3次,得到棕黄色固体(N,N-二甲基-N[3-(乳糖酰胺基)]丙基-N-十四烷基溴化铵)。最后测得产品中季铵盐活性物含量为98.4%。
In a 250 mL three-neck round bottom flask equipped with a thermometer and a spherical condenser, add 6.9 g (15 mmol) of N,N-dimethyl-N′-lactoyl-1,3-propanediamine, decabromide Tetraxane 4 g (17 mmol),
1H-NMR(D2O, ppm) δ: 0.81(t, 3H, (CH2)11 CH 3 ), 1.24 (m, 22H, (CH 2 ) 11 CH3), 1.70 (m, 2H, CH 2 (CH2)11CH3), 1.98 (m, 2H, NHCH2 CH 2 CH2), 2.81 (t, 2H, NCH 2 CH2), 3.04 (s, 6H, N(CH 3 )2), 3.30 (m, 4H, NHCH 2 CH 2 CH 2 ), 3.48-4.50 (13H, protons of sugar)。 1 H-NMR(D 2 O, ppm) δ: 0.81(t, 3H, (CH 2 ) 11 CH 3 ), 1.24 (m, 22H, (CH 2 ) 11 CH 3 ), 1.70 (m, 2H, CH 2 (CH 2 ) 11 CH 3 ), 1.98 (m, 2H, NHCH 2 CH 2 CH 2 ), 2.81 (t, 2H, N CH 2 CH 2 ), 3.04 (s, 6H, N( CH 3 ) 2 ) , 3.30 (m, 4H, NH CH 2 CH 2 CH 2 ), 3.48-4.50 (13H, protons of sugar).
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Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104069773A (en) * | 2014-07-15 | 2014-10-01 | 北京工商大学 | Alkyl sugar amide dimeric surfactant and preparation method |
CN104084085A (en) * | 2014-07-15 | 2014-10-08 | 北京工商大学 | Ethyoxyl modified alkyl glucosamide surfactant and preparation method thereof |
CN104084084A (en) * | 2014-07-15 | 2014-10-08 | 北京工商大学 | Surfactant containing alkyl glucosamide and preparation method of surfactant |
CN104610092A (en) * | 2015-02-10 | 2015-05-13 | 齐齐哈尔大学 | Quaternary ammonium salt cationic surfactant and preparation method thereof |
JP2016516021A (en) * | 2013-03-14 | 2016-06-02 | アクゾ ノーベル ケミカルズ インターナショナル ベスローテン フエンノートシャップAkzo Nobel Chemicals International B.V. | Nitrogen-containing surfactants having alkoxylation on the hydroxyl group of the fatty chain |
CN108246042A (en) * | 2018-02-07 | 2018-07-06 | 太原科技大学 | A kind of chemical agglomeration agent for reducing coal-fired superfine particulate matters and preparation method |
CN108452630A (en) * | 2018-02-07 | 2018-08-28 | 太原科技大学 | Reduce chemical agglomeration agent and the preparation method of waste incineration superfine particulate matter |
CN114230481A (en) * | 2021-12-29 | 2022-03-25 | 太原科技大学 | A kind of low toxicity bactericidal glycosyl amide ionic liquid and its preparation method and application |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0559748B1 (en) * | 1990-11-30 | 1994-07-27 | Richardson-Vicks, Inc. | Gel type compositions having improved oil control |
US5753245A (en) * | 1994-08-26 | 1998-05-19 | The Procter & Gamble Company | Personal cleansing compositions |
CN1562960A (en) * | 2004-03-29 | 2005-01-12 | 中国日用化学工业研究院 | Quaternary ammonium salt in ester-amines and synthetic method |
CN1951908A (en) * | 2006-11-10 | 2007-04-25 | 中国日用化学工业研究院 | Preparation process for synthesizing AGA using loop reactor |
CN101972612A (en) * | 2010-11-10 | 2011-02-16 | 郑州轻工业学院 | Sugar-based quaternary ammonium salt gemini surfactant and synthesis method thereof |
CN102492146A (en) * | 2011-12-07 | 2012-06-13 | 北京工商大学 | Method for preparing polysiloxane containing alkyl and glucosamide |
CN102503841A (en) * | 2011-10-08 | 2012-06-20 | 中国日用化学工业研究院 | Ethoxylate ester quaternary ammonium salt and its preparation method |
-
2012
- 2012-09-17 CN CN201210341915.XA patent/CN102875410B/en not_active Expired - Fee Related
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0559748B1 (en) * | 1990-11-30 | 1994-07-27 | Richardson-Vicks, Inc. | Gel type compositions having improved oil control |
US5753245A (en) * | 1994-08-26 | 1998-05-19 | The Procter & Gamble Company | Personal cleansing compositions |
CN1562960A (en) * | 2004-03-29 | 2005-01-12 | 中国日用化学工业研究院 | Quaternary ammonium salt in ester-amines and synthetic method |
CN1951908A (en) * | 2006-11-10 | 2007-04-25 | 中国日用化学工业研究院 | Preparation process for synthesizing AGA using loop reactor |
CN101972612A (en) * | 2010-11-10 | 2011-02-16 | 郑州轻工业学院 | Sugar-based quaternary ammonium salt gemini surfactant and synthesis method thereof |
CN102503841A (en) * | 2011-10-08 | 2012-06-20 | 中国日用化学工业研究院 | Ethoxylate ester quaternary ammonium salt and its preparation method |
CN102492146A (en) * | 2011-12-07 | 2012-06-13 | 北京工商大学 | Method for preparing polysiloxane containing alkyl and glucosamide |
Non-Patent Citations (1)
Title |
---|
姜小明等: "一种非对称双尾阳离子表面活性剂的合成及表面活性", 《精细化工》 * |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016516021A (en) * | 2013-03-14 | 2016-06-02 | アクゾ ノーベル ケミカルズ インターナショナル ベスローテン フエンノートシャップAkzo Nobel Chemicals International B.V. | Nitrogen-containing surfactants having alkoxylation on the hydroxyl group of the fatty chain |
CN104069773A (en) * | 2014-07-15 | 2014-10-01 | 北京工商大学 | Alkyl sugar amide dimeric surfactant and preparation method |
CN104084085A (en) * | 2014-07-15 | 2014-10-08 | 北京工商大学 | Ethyoxyl modified alkyl glucosamide surfactant and preparation method thereof |
CN104084084A (en) * | 2014-07-15 | 2014-10-08 | 北京工商大学 | Surfactant containing alkyl glucosamide and preparation method of surfactant |
CN104610092A (en) * | 2015-02-10 | 2015-05-13 | 齐齐哈尔大学 | Quaternary ammonium salt cationic surfactant and preparation method thereof |
CN108246042A (en) * | 2018-02-07 | 2018-07-06 | 太原科技大学 | A kind of chemical agglomeration agent for reducing coal-fired superfine particulate matters and preparation method |
CN108452630A (en) * | 2018-02-07 | 2018-08-28 | 太原科技大学 | Reduce chemical agglomeration agent and the preparation method of waste incineration superfine particulate matter |
CN108452630B (en) * | 2018-02-07 | 2020-06-02 | 太原科技大学 | Chemical aggregating agent for reducing waste incineration ultrafine particles and preparation method thereof |
CN114230481A (en) * | 2021-12-29 | 2022-03-25 | 太原科技大学 | A kind of low toxicity bactericidal glycosyl amide ionic liquid and its preparation method and application |
CN114230481B (en) * | 2021-12-29 | 2023-09-22 | 太原科技大学 | A low-toxicity bactericidal glycosyl amide ionic liquid and its preparation method and application |
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