Pyridine bis-quaternary ammonium salt surfactant and preparation method and application thereof

A surfactant and biquaternary ammonium salt technology, applied in the directions of botanical equipment and methods, applications, chemical instruments and methods, can solve the problems of small scale, complex synthesis process, etc., and achieve simple preparation, easy availability of raw materials, Excellent antibacterial effect

Pending Publication Date: 2018-12-28
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, many cationic gemini surfactants containing heterocycles such as imidazole, pyridine, thiazole, quinoline, tetrahydropyrrole and hexahydropyridine have been reported, but most of the synthesis processes are relatively complicated and are still on a small scale. Therefore, The development of gemini surfactants with novel structures and their performance research has always been a hot spot in this research field

Method used

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  • Pyridine bis-quaternary ammonium salt surfactant and preparation method and application thereof
  • Pyridine bis-quaternary ammonium salt surfactant and preparation method and application thereof
  • Pyridine bis-quaternary ammonium salt surfactant and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: N bromide, the preparation of N'-bis (1-n-octyl-3-pyridyl) malonamide diquaternary ammonium salt (surfactant a)

[0024]

[0025] (1) Preparation of N, N'-bis(3-pyridyl)malonamide: in a reaction flask, add 3-aminopyridine (7.05g, 75mmol), diethyl malonate (4.00g, 25mmol) and 10mL N, N-dimethylformamide, install a water separator, start stirring, and heat the reaction. During the reaction process, the low-boiling ethanol generated by the reaction was separated with a water separator, and finally the reaction temperature was reached to 140°C for 7 hours, cooled, filtered, washed with ethyl acetate, and dried to obtain 4.16g N, N'-bis( 3-pyridyl)malonamide, yield 65%, melting point: 215-218°C. 1 H NMR (600MHz, DMSO-d 6 ,ppm)δ:10.43(s,2H),8.75(d,J=2.3Hz,2H),8.29(m,2H),8.06(m,2H),7.37(m,2H),3.56(s,2H ).

[0026] (2) In the reaction flask, add N,N'-bis(3-pyridyl)malonamide (2.05g, 8mmol) and n-octane bromide (15.45g, 80mmol), heat to 110°C for 7 hours , ...

Embodiment 2

[0027] Embodiment 2: N bromide, the preparation of N'-two (1-n-decyl-3-pyridyl) malonamide diquaternary ammonium salt (surfactant b)

[0028]

[0029] (1) Preparation of N, N'-bis(3-pyridyl) malonamide: in a reaction flask, add 3-aminopyridine (9.41g, 100mmol), diethyl malonate (4.00g, 25mmol) and 10mL N, N-dimethylformamide, install a water separator, start stirring, and heat the reaction. During the reaction process, the ethanol with a low boiling point generated by the reaction was separated with a water separator, and finally the reaction temperature reached 150°C for 6 hours, cooled, filtered, washed with ethyl acetate, and dried to obtain 4.29g N, N'-bis(3 -pyridyl)malonamide, yield 67%, melting point: 215-218°C. 1 H NMR (600MHz, DMSO-d 6 ,ppm)δ:10.43(s,2H),8.75(d,J=2.3Hz,2H),8.29(m,2H),8.06(m,2H),7.37(m,2H),3.56(s,2H ).

[0030] (2) In the reaction flask, add N,N'-bis(3-pyridyl)malonamide (2.05g, 8mmol) and brominated n-decane (17.69g, 80mmol), heat to 120°C for ...

Embodiment 3

[0031] Embodiment 3: N bromide, the preparation of N'-bis (1-n-dodecyl-3-pyridyl) malonamide diquaternary ammonium salt (surfactant c)

[0032]

[0033] (1) Preparation of N, N'-bis(3-pyridyl) malonamide: in a reaction flask, add 3-aminopyridine (9.41g, 100mmol), diethyl malonate (4.00g, 25mmol) and 11.25mLN, N-dimethylformamide, install a water trap, start stirring, and heat to react. During the reaction process, the low-boiling ethanol generated by the reaction was separated with a water separator, and finally the reaction temperature was reached at 140°C for 7 hours, cooled, filtered, washed with ethyl acetate, and dried to obtain 4.06g N, N'-bis( 3-pyridyl)malonamide, yield 63.5%, melting point: 215-218°C. 1 H NMR (600MHz, DMSO-d 6 ,ppm)δ:10.43(s,2H),8.75(d,J=2.3Hz,2H),8.29(m,2H),8.06(m,2H),7.37(m,2H),3.56(s,2H ).

[0034](2) In the reaction flask, add N,N'-bis(3-pyridyl)malonamide (2.05g, 8mmol) and n-dodecane bromide (15.95g, 64mmol), and heat to 120°C to react 6 ...

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Abstract

The invention discloses a pyridine bis-quaternary ammonium salt surfactant and a preparation method and an application thereof. The preparation method of the pyridine bis-quaternary ammonium salt surfactant includes utilizing 3-aminopyridine as a starting raw material to react with diethyl malonate to obtain N,N'-di(3-pyridyl) malonamide and then reacting with brominated alkane under a solvent-free condition to obtain the pyridine bis-quaternary ammonium salt surfactant. The pyridine bis-quaternary ammonium salt surfactant not only has good surface activity with the critical micelle concentration as low as 1.69*10^5 mol L-1, but also has excellent antibacterial property with the minimum semi-inhibitory concentration of escherichia coli as 2.699-6.538Mug / mL, and the antibacterial effect isbetter than that of ampicillin.

Description

technical field [0001] The invention relates to a pyridine type diquaternary ammonium salt surfactant, a preparation method and application thereof, and belongs to the technical field of surfactants. Background technique [0002] Surfactants are known as "industrial monosodium glutamate". They are widely used in the national market due to their functions of washing, wetting or anti-sticking, emulsifying or breaking, foaming or defoaming, solubilizing, dispersing, antiseptic, and antistatic. all areas of economic development. With the rapid development of science and technology and economy, traditional surfactants can no longer meet the needs of people's production and life, and the requirements for the surfactant industry are getting higher and higher. Due to its low critical micelle concentration, good water solubility, good foaming and emulsifying properties, gemini surfactants have attracted the attention of researchers in related fields. In particular, cationic gemini ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/75A01N43/40B01F17/18A01P1/00C09K23/18
CPCA01N43/40C07D213/75C09K23/00
Inventor 郝俊生秦涛张永斌于海英
Owner SHANXI UNIV
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