Gemini nicotinate quaternary ammonium salt and method for making same

A quaternary ammonium salt and nicotinic acid technology, applied in chemical instruments and methods, organic chemistry, transportation and packaging, etc., can solve the problems of decreased use effect, low bactericidal concentration, high water solubility, etc., and achieves weak foaming, high The effect of surface activity and strong sustained release ability

Inactive Publication Date: 2008-06-25
CHINA WEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These cationic surfactants have the advantages of broad-spectrum antibacterial and antibacterial ability, odorless, large water solubility, and low irritation. For example, 1227 has low bactericidal concentration, good water solubility, and low toxicity and irritation, but the price is high. The bactericidal effect also has a certain influence
In practical application, it is also found that if a surfactant is used for a long time in the same system, the

Method used

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  • Gemini nicotinate quaternary ammonium salt and method for making same
  • Gemini nicotinate quaternary ammonium salt and method for making same
  • Gemini nicotinate quaternary ammonium salt and method for making same

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0032] Example 1

[0033] Preparation of brominated di-N-alkylnicotinic acid ethylene glycol / diethylene glycol / triethylene glycol ester (EQn-m-n)

[0034] Synthesis of EQ16-2-16

[0035] Add niacin and thionyl chloride with a molar ratio of 1:5 into the reaction flask, stir and reflux, and the NaOH solution absorbs the tail gas. After 4 hours of reaction, cooling, spin-drying excess thionyl chloride under reduced pressure, white needle-like crystals were obtained. Dry chloroform is used as the solvent, and triethylene glycol with a molar ratio of 1:2 to niacin is slowly dripped. The NaOH solution absorbs the tail gas and refluxes for 10 hours. After cooling, spin dry the solvent, add proper amount of water to dissolve, use saturated Na 2 CO 3 Adjust the pH of the aqueous solution to weakly alkaline, separate the organic phase, extract the aqueous phase with ethyl acetate 2-3 times, combine the organic phases, spin dry and pass through the column with ethyl acetate. The resulting p...

Example Embodiment

[0043] Example 2

[0044] Structural characterization of brominated di-N-alkylnicotinic acid ethylene glycol / diethylene glycol / triethylene glycol ester (EQn-m-n)

[0045] Structural characterization of EQ16-0-16

[0046]

[0047] Refer to Figure 1. Figure 1 is the hydrogen spectrum of EQ16-0-16. According to the spectrum, the chemical shift and related parameters of EQ16-0-16 are listed in Table 1 below:

[0048] Table 1EQ16-0-16 1 HNMR parameters

[0049] Absorption peak

[0050] It can be seen from Table 1: Groups 1, 2, 3, and 4 are hydrogen on the pyridine ring, 5 are methylene hydrogens directly connected to nitrogen, and 6 are methylene hydrogens directly connected to oxygen on the ester group. 7 , Group 8 is the methylene hydrogen on the long chain alkane, and group 9 is the methyl hydrogen on the end of the long chain alkane. The total number of hydrogen atoms is half of the number of hydrogen atoms in the target product molecule, and it is inferred that the mol...

Example Embodiment

[0066] Example 3

[0067] Study on the surface activity of brominated di-N-alkylnicotinic acid ethylene glycol / diethylene glycol / triethylene glycol ester (EQn-m-n)

[0068] The surface active agent to be measured is formulated into a series of aqueous solutions of a certain concentration with double distilled water, and the surface tension of the aqueous solution of the surface active agent is measured by the ring method at 20°C. The measurement results are shown in Figure 4 and Table 4.

[0069] It can be seen from Figure 4 that with the addition of this series of surfactants, the surface tension of the water drops sharply, the concentration increases, the surface tension drops slowly, and finally stabilizes. The alkyl chain increases and the surface activity increases.

[0070] Table 4 cmc and γ of several surfactants cmc And C 20

[0071] substance

[0072] EQ10-0-10

[0073] Note: C 20 It represents the concentration of surfactant needed to reduce the surf...

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Abstract

The invention relates to a gemini nicotinic acid ester quaternary ammonium salt, namely a bromide bi-N-alkyl nicotinic acid athylene glycol/diethylene glycol/triethylene glycol, the preparation method of which is given as follows: (1) the nicotinic acid and the thionyl chloride are added in a reaction bottle in a molar ratio of the nicotinic acid to the thionyl chloride ranging from 1:3 to 1:6; after the reaction between the nicotinic acid and the thionyl chloride lasts for 2 to 4 hours, the nicotinic acid acyl chloride which is in a white needle-shaped crystal is obtained; (2) the nicotinic acid acyl chloride is dissolved in the dried chloroform and then the alcohol with a molar ratio to the nicotinic acid of 1:2 is dropped slowly in the mixtures of the nicotinic acid acyl chloride; the alcohols can be ethylene glycol, diethylene glycol or teg; the alcohols are dissolved by adding a proper amount of water and the nicotinates which are the products of the alcoholysis are subject to the pumping filtration and drying; (3) the nicotinate and the alkyl bromide are added in the reaction bottle in a molar ratio of the nicotinate to the alkyl bromide ranging from 1:2 to 1:6; the number of the carbon atoms of the alkyl bromide is 8, 10, 12, 14 or 16; the anhydrous acetonitrile is used as the solvent and the mixtures in the reaction bottle are heated and refluxed for 30 to 40 hours; after the mixtures are subject to the washing and pumping filtration, the products, gemini nicotinic acid ester quaternary ammonium salts, are obtained. The gemini nicotinic acid ester quaternary ammonium salt has very high surface activity and very strong bactericidal performances and corrosion inhibition, the preparation method of the invention is simple, convenient and feasible, is easy to be operated, delivers high yield and causes no environmental contaminations.

Description

technical field [0001] The invention relates to a gemininic acid ester quaternary ammonium salt and a preparation method thereof. Background technique [0002] Surfactants have become indispensable chemicals in the national economy and human daily life. It is widely used in the fields of energy mining, metal processing, textile, daily chemical industry, food and pharmaceuticals. In 1935, Domagk discovered that cationic surfactants have bactericidal ability, the representatives of which are quaternary ammonium salt-type surfactants, in addition to pyridinium salts, imidazoline salts, and isoquinoline salts. Gemini quaternary ammonium compounds are characterized by their low toxicity, high efficiency, broad-spectrum antibacterial properties and extensive biological activity (Nagamune H et al.Evaluation of the Cytotoxic Effects of Bis-quaternary Ammonium Antimicrobial Reagents on HumanCells[J].Toxicology in Vitro, 2000, 14: 139-147), has been widely used in medicine, food, co...

Claims

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Application Information

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IPC IPC(8): C07D213/80B01F17/18C09K23/18
Inventor 蒋晓慧刘红星
Owner CHINA WEST NORMAL UNIVERSITY
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