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Guanidyl long chain gemini quaternary ammonium salt and preparation method thereof

A technology of gemini quaternary ammonium salt and diquaternary ammonium salt, which is applied in chemical instruments and methods, preparation of organic compounds, chemicals for biological control, etc., can solve complex reaction process, few action centers, poor hydrophilicity, etc. problem, to achieve the effect of simple reaction process, high surface activity and low foaming performance

Active Publication Date: 2016-02-03
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The object of the present invention is to provide a kind of gemini quaternary ammonium salt and preparation method thereof, it has improved common quaternary ammonium salt few action centers, the shortcoming of poor hydrophilicity, complex reaction process, expensive raw material

Method used

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  • Guanidyl long chain gemini quaternary ammonium salt and preparation method thereof
  • Guanidyl long chain gemini quaternary ammonium salt and preparation method thereof
  • Guanidyl long chain gemini quaternary ammonium salt and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] see figure 1 , 1) in the there-necked flask that NaCl is housed, drip the concentrated sulfuric acid (mass fraction is 98%) gradually, slightly heat, produce HCl gas, pass the HCl gas that produces into the concentrated sulfuric acid (mass fraction is 98%) and carry out drying , and then slowly poured into the ether solution containing dodecyldimethyl tertiary amine, stirring continuously at 25°C and 350r / min speed to obtain a white precipitate, which is dodecyldimethyl tertiary amine hydrochloride , After 2h, the reaction ended. Wash with ether several times to obtain pure dodecyl dimethyl tertiary amine hydrochloride, dry at 20°C for 6 hours, and set aside.

[0034] 2) Add 7.497g (0.03mol) dodecyldimethyl tertiary amine hydrochloride and 0.3195g (0.0015mol) dodecyldimethyl tertiary amine to a three-necked flask containing 25mL of acetone, at 30°C , stirring at 400r / min for 45min; raise the temperature to 50°C, at 500r / min, add 2.275g (0.03mol) of epichlorohydrin (EC...

Embodiment 2

[0037] 1) with embodiment 1.

[0038] 2) Add 7.497g (0.03mol) dodecyldimethyl tertiary amine hydrochloride and 0.0639g (0.0003mol) dodecyldimethyl tertiary amine to a three-necked flask filled with 30mL acetone, at 30°C, Stir at 400r / min for 45min; raise the temperature to 60°C, at 450r / min, add 2.275g (0.03mol) of epichlorohydrin (ECH) dropwise within 60min, stop the reaction after 4h; distill under reduced pressure to remove Remove excess solvent and reactants, and perform multiple recrystallizations in acetone to obtain 2-hydroxypropyl-3-chloro-dimethyl dodecyl ammonium chloride.

[0039] 3) Add 10.26g (0.03mol) 2-hydroxypropyl-3-chloro-dimethyldodecyl ammonium chloride to a three-necked flask filled with 30mL of ethanol, and stir at 30°C and 400r / min After 10 minutes, the temperature was raised to 60°C, and 3.999 g (0.031 mol) of 1,1,2,3,3-pentamethylguanidine was gradually added dropwise at 450 r / min, and the addition was completed after 30 minutes. Stop the reaction af...

Embodiment 3

[0041] 1) with embodiment 1

[0042] 2) Add 7.497g (0.03mol) dodecyldimethyl tertiary amine hydrochloride and 0.639g (0.003mol) dodecyldimethyl tertiary amine to a three-necked flask containing 20mL of acetone, at 30°C, Stir at 400r / min for 45min; raise the temperature to 60°C, at 450r / min, add 3.2375g (0.035mol) epichlorohydrin (ECH) dropwise within 60min, stop the reaction after 5h; distill under reduced pressure to remove Remove excess solvent and reactants, and perform multiple recrystallizations in acetone to obtain 2-hydroxypropyl-3-chloro-dimethyl dodecyl ammonium chloride.

[0043] 3) Add 10.26g (0.03mol) of 2-hydroxypropyl-3-chloro-dimethyl dodecyl ammonium chloride to a three-necked flask containing 20mL of ethanol solution, and stir fully at 30°C and 400r / min After 10 minutes, the temperature was raised to 70°C, and 4.128 g (0.032 mol) of 1,1,2,3,3-pentamethylguanidine was gradually added dropwise at 450 r / min, and the addition was completed after 30 minutes. After ...

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Abstract

The invention discloses a guanidyl long chain gemini quaternary ammonium salt and a preparation method thereof, wherein long chain gemini quaternary ammonium salts and long chain alkyl tertiary amines are added into a solvent, are added with epichlorohydrin drop by drop in 40-90 DEG C, and obtain intermediate products by reacting after being added drop by drop; and the intermediate products are added into alcohol, are added with long chain guanidine drop by drop in 30-110 DEG C after being uniformly stirred, and react for 4-48h after being added drop by drop to obtain guanidyl long chain gemini quaternary ammonium salts. The guanidyl long chain gemini quaternary ammonium salt and the preparation method thereof adopt open loops of epoxide and bimolecular nucleophilic reactions, wherein H+ and epoxy groups are easy to combine in an open ring reaction of the epoxide, and enable tertiary amines which are used as nucleophilic reagents to be more rapid when attacking carbonium ions. Quaternary ammonium surfactants are in a system in a second reaction, are used as a surface active agent to greatly promote quaternization, and improve reaction speed as a whole. The guanidyl long chain gemini quaternary ammonium salt and the preparation method thereof are simple in reaction process, clear in target products, less in accessory substances and concise in purification process, and further reduces cost.

Description

technical field [0001] The invention relates to a preparation method of a quaternary ammonium salt, in particular to a guanidino long-chain gemini quaternary ammonium salt and a preparation method thereof. Background technique [0002] Quaternary ammonium salts are widely used as cationic surfactants. At present, it can be roughly divided into: alkyl trimethyl ammonium salt type, dialkyl dimethyl ammonium salt type, alkyl dimethyl benzyl ammonium type, pyridinium salt type, alkyl isoquinolinium salt type, chlorine Benzyl ammonium salt type. [0003] Quaternary ammonium compounds play an important role in the field of sterilization and disinfection. However, because its active part has only one charge center, when it is applied, the distance between molecules increases due to charge repulsion, and the performance is obviously weakened. [0004] Chinese patent CN102388910A obtains a quaternary ammonium salt grafted guanidinium salt bactericide by grafting polyguanidine salt...

Claims

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Application Information

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IPC IPC(8): C07C277/08C07C279/12B01F17/18B01F17/00A01P1/00A61P31/04C09K23/00C09K23/18
Inventor 郭睿李欢乐王超程敏刘爱玉李晓芳杨江月甄建斌
Owner SHAANXI UNIV OF SCI & TECH
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