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Bis-quaternary ammonium salt cationic surfactant, preparation and use thereof

A technology of surfactant and double quaternary ammonium salt, which is applied in the application of oilfield fungicides, and the field of preparation of Gemini quaternary ammonium salt cationic surfactant, can solve the problems of drug resistance, high cost, and complicated preparation process.

Inactive Publication Date: 2008-10-08
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although quaternary ammonium salt type cationic surfactant has good bactericidal properties and is widely used, there are following shortcomings in the use and production of this type of surfactant: i. the cost performance of quaternary ammonium salt type cationic surfactant bactericide is relatively high , compared with other types of fungicides, the cost is higher than other types of fungicides when achieving the same degree of sterilization effect; ii. During use, it is found that if a quaternary ammonium salt cationic surfactant is used in the same system for a long time , microorganisms will develop resistance to it; iii. The cost of production equipment is high and the preparation process is complicated
However, microorganisms often develop resistance to a fungicide, resulting in a decrease in the bactericidal rate of the fungicide

Method used

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  • Bis-quaternary ammonium salt cationic surfactant, preparation and use thereof
  • Bis-quaternary ammonium salt cationic surfactant, preparation and use thereof
  • Bis-quaternary ammonium salt cationic surfactant, preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Example 1: N, N, N', N'-tetramethyl-N, N'-didodecyl-1,2-xylylene diammonium dibromide (1,2-BGBn) Synthesis:

[0069] Accurately measure 2.8mL (density=0.76g / mL, 0.01mol) of N,N-dimethyldodecylamine, weigh 1.06g (0.004mol) of o-dibromomethylbenzene, put the above reagent in 100mL In the round bottom flask, add 5mL ethanol in the reflux device, heat to reflux until a light yellow solid is produced, remove the ethanol by rotary evaporation, add 10mL CH 2 Cl 2 Solvent, to dissolve the solidified reactant as much as possible, filter out the insoluble matter, and place the filtrate to precipitate 1.46 g of transparent flaky crystals (52.8% yield), with a melting point of 54-56°C.

[0070] Infrared analysis results: the main infrared absorption peaks are:

[0071] IR (KBr, cm -1 ): 3016(m), 2917(v), 2852(m), 1486(m), 1450(m), 1433(w), 1395(w), 962(m), 935(m), 915(m ), 846(vs), 722(m), 448(w).

[0072] NMR:

[0073] 1 H NMR (CDCl 3, δ / ppm): 7.68 (s, 2H, Ph-H), 7.70 (s,...

Embodiment 2

[0075] Example 2: N, N, N', N'-tetramethyl-N, N'-dodedecyl-1,3-xylylene diammonium dibromide (1,3-BGBn) Synthesis:

[0076] Weigh 1.06g (0.004mol) m-dibromomethylbenzene, add it to a round-bottomed flask filled with 10mL of acetone, and under magnetic stirring, mix 2.8mL (density=0.76g / mL, 0.01mol) N, N - Add dimethyl dodecylamine to it, and stir at room temperature for about 15 minutes to form a white solid. After continuing to stir for half an hour, filter under reduced pressure and dry to obtain 1.83 g of solid (yield 66.3%). The melting point of the compound was 225-227°C as measured by a melting point apparatus.

[0077] Infrared analysis results: the main infrared absorption peaks are:

[0078] IR (KBr, cm -1 ): 3012(w), 2955(m), 2925(s), 2858(m), 1466(m), 1380(w), 1335(w), 1262(w), 927(w), 832(w ), 750(w), 723(m).

[0079] NMR: 1 H NMR (CDCl 3 , δ / ppm): 7.91 (s, 2H, Ph-H), 7.78-7.76 (d, 2H, J=7.6HzPh-H), 7.62 (s, 1H, Ph-H), 4.68 (s, 4H, Ph-CH 2 -N + ), 3.35(s,...

Embodiment 3

[0081] Example 3: N, N, N', N'-tetramethyl-N, N'-dodedecyl-1,4-xylylene diammonium dibromide (abbreviated as 1,4-BGBn )Synthesis:

[0082] Weigh 1.06g (0.004mol) m-dibromomethylbenzene, add it to a round-bottomed flask filled with 10mL of acetone, and under magnetic stirring, mix 2.8mL (density=0.76g / mL, 0.01mol) N, N -Dimethyldodecylamine was added thereto, a white precipitate was produced immediately, and stirring was continued for 30 minutes. It was filtered under reduced pressure and dried to obtain 2.03 g of solid (yield 73.6%). The melting point of the compound was 224-226°C as measured by a melting point apparatus.

[0083] Infrared analysis results: the main infrared absorption peaks are:

[0084] IR (KBr, cm -1 ): 3010(m), 2922(v), 2858(m), 1485(m), 1465(m), 1402(w), 1226(w), 1005(w), 880(w), 825(w ), 720(m), 415(w).

[0085] NMR: 1 H NMR (CDCl 3 , δ / ppm): 7.67 (s, 4H, Ph-H), 4.59 (s, 4H, Ph-CH 2 -N + ), 3.27(s, 4H, N + -CH 2 ), 2.98(s, 12H, N + -CH 3 ), ...

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Abstract

The invention discloses a Gemini quaternary ammonium salt cationic surfactant with sterilization effect. The preparation method of the Gemini quaternary ammonium salt cationic surfactant disclosed by the invention relates to that a dihalide and a fatty amine are reacted in an organic solvent, i.e. a dibromo-matter and an alkyl tertiary amine perform chemical reaction in an ethanol (or acetone or ethyl acetate) solution at the room temperature or at a low temperature and normal pressure condition, so as to synthesize a series of Gemini quaternary ammonium salt cationic surfactants. The method for synthesizing the Gemini quaternary ammonium salt cationic surfactant is simple and convenient, stable in reaction process, easy for operating and controlling with a higher product purity and yield; besides, compared with the novel geramine, the method has better sterilization effect and has important application in the aspect of oil field germicide at the same time.

Description

technical field [0001] The invention belongs to the technical field of preparation of cationic surfactants, and relates to a preparation method and application of a Gemini quaternary ammonium salt cationic surfactant. More specifically, the double halides react with long-chain alkyl tertiary amines in organic solvents to prepare a new method for the preparation of Gemini quaternary ammonium salt cationic surfactants with a bactericidal effect superior to that of bromogeramine and their use in oilfield fungicides aspects of application. Background technique [0002] The compound molecules of cationic surfactants have strong adsorption capacity on the surface of the substance, that is, the molecules can gather to form a thin film on the surface of the substance to which it is attached. and other excellent performance. In particular, quaternary ammonium salt cationic surfactants, in addition to the basic properties of general cationic surfactants such as surface adsorption, a...

Claims

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Application Information

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IPC IPC(8): B01F17/18C09K23/18
Inventor 史学芳
Owner TIANJIN NORMAL UNIVERSITY
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