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Cationic type gemini fluorinated surfactant based on perfluorinated nonene and perfluorinated hexene and preparation method of cationic type gemini fluorinated surfactant

A technology of fluorosurfactant and perfluorononene, which is applied in the field of cationic gemini surfactant and its preparation, can solve the problems of insufficient surface activity of surfactants, achieve improved decontamination and washing ability, high bactericidal effect, Low toxicity and low effect

Active Publication Date: 2013-02-06
江苏超至和新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to overcome the defect of insufficient surface activity of existing hexafluoropropylene oligomer derivatives surfactants, the present invention has prepared a fluoropropylene trimer) and perfluorohexene (hexafluoropropylene dimer) gemini fluorosurfactant, the general formula is

Method used

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  • Cationic type gemini fluorinated surfactant based on perfluorinated nonene and perfluorinated hexene and preparation method of cationic type gemini fluorinated surfactant
  • Cationic type gemini fluorinated surfactant based on perfluorinated nonene and perfluorinated hexene and preparation method of cationic type gemini fluorinated surfactant
  • Cationic type gemini fluorinated surfactant based on perfluorinated nonene and perfluorinated hexene and preparation method of cationic type gemini fluorinated surfactant

Examples

Experimental program
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Effect test

Embodiment 1

[0018] One, the preparation of perfluorononenyloxybenzoic acid intermediate

[0019] Add 90g (0.2mol) of perfluorononene, 27.6g (0.2mol) of p-hydroxybenzoic acid and 200mL of N,N-dimethylformamide into a four-necked flask, and dropwise add 40.4g (0.4 mol), after 40 minutes of dripping, the reaction was continued for 8 hours after dripping, the reaction solution was poured into dilute hydrochloric acid to precipitate a white solid, filtered, washed with water, and dried to obtain 110.5 g of a white solid, with a yield of 97.3%.

[0020] 2. Preparation of dimethylaminoethanol perfluorononenyloxybenzoate

[0021] Stir and mix 28.4 g (0.05 mol) of perfluorononenyloxybenzoic acid and 84.5 g (0.71 mol) of thionyl chloride, slowly raise the temperature to 45°C, keep the temperature for 5 hours, and absorb the tail gas with lye at the same time. After the reaction was completed, excess thionyl chloride was recovered by distillation under reduced pressure to obtain a light yellow ...

Embodiment 2

[0025] One, the preparation of perfluorononenyloxybenzoic acid intermediate

[0026] With embodiment 1.

[0027] 2. Preparation of N-(3-dimethylaminopropyl) perfluorononenyloxybenzamide

[0028] 28.4g (0.05mol) of perfluorononenyloxybenzoic acid and 84.5g (0.71mol) of thionyl chloride were stirred and mixed, and the temperature was slowly raised to 45°C, and the reaction was kept for 5 hours, while the tail gas was absorbed with lye. After the reaction was completed, excess thionyl chloride was recovered by distillation under reduced pressure to obtain a light yellow liquid. Add 50 mL of acetonitrile and 10.2 g (0.1 mol) of 3-dimethylaminopropylamine, and reflux for 5 h. Cool to room temperature, dilute with water, adjust the pH to above 10, let stand to separate the layers, extract the aqueous layer with acetonitrile, combine the organic phases, wash with water, dry, and precipitate to obtain a light yellow residue with a yield of 91.3%.

[0029] 3. Preparation of ...

Embodiment 3

[0032] One, the preparation of perfluorohexenyloxybenzoic acid intermediate

[0033] Add 60g (0.2mol) of perfluorohexene, 27.6g (0.2mol) of p-hydroxybenzoic acid and 200mL of N,N-dimethylformamide into a four-necked flask, and drop 40.4g (0.4 mol), after 40 minutes of dripping, the reaction was continued for 8 hours after dripping, the reaction solution was poured into dilute hydrochloric acid to precipitate a white solid, filtered, washed with water, and dried to obtain 79.8 g of a white solid, with a yield of 95.4%.

[0034] 2. Preparation of 3-dimethylaminopropanol perfluorohexenyloxybenzoate

[0035]20.9g (0.05mol) of perfluorohexenyloxybenzoic acid and 84.5g (0.71mol) of thionyl chloride were stirred and mixed, the temperature was slowly raised to 45°C, and the reaction was kept for 5 hours while the tail gas was absorbed with lye. After the reaction was completed, excess thionyl chloride was recovered by distillation under reduced pressure to obtain a light yellow l...

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Abstract

The invention discloses a cationic type gemini fluorinated surfactant based on perfluorinated nonene and perfluorinated hexene and a preparation method of the cationic type gemini fluorinated surfactant. The preparation method comprises the following steps of: with the perfluorinated nonene or perfluorinated hexene as a raw material, condensing the perfluorinated nonene or perfluorinated hexene with p-hydroxybenzoic acid, and carrying out chlorination on a matter obtained after condensation and thionyl chloride to prepare perfluorinated alkene oxyl benzoyl chloride; condensing the perfluorinated alkene oxyl benzoyl chloride without separation with 2-dimethylamino ethanol, 3-dimethylamino propanol, 2-dimethylamino ethylamine and 3-dimethylamino propylamine to obtain perfluorinated alkene oxyl benzoate or perfluorinated alkene oxyl benzamide with tertiary amine at an alkanol part or amine part; and finally, condensing the perfluorinated alkene oxyl benzoate or perfluorinated alkene oxyl benzamide with 1,2-dihaloethane, 1,3-dihalopropane, 1,4-dichlorobutane, 1,5-dichloropentane or 3-oxa-1,5-dichloropentane to prepare a quaternary ammonium gemini fluorinated surfactant. The synthesized compound is high in surface activity and is low in critical micelle concentration, has the characteristics of simpleness in synthesization, low cost and the like and has good application prospect.

Description

technical field [0001] The invention relates to a class of fluorine surfactants, in particular to a class of cationic gemini surfactants containing perfluorononenyloxy or perfluorohexenyloxy groups and a preparation method thereof. Background technique [0002] Surfactant is an important fine chemical product, which has multiple functions such as wetting, emulsifying, foaming, defoaming, and dispersing, and is known as industrial monosodium glutamate. Surfactants are generally classified into anionic, cationic, amphoteric and nonionic. [0003] Fluorosurfactants are a special class of surfactants, which have typical three-high amphiphobic (high thermal stability, high chemical stability, high surface activity, both oil-repellent and water-repellent) characteristics, so they are widely used in fire protection, oil extraction, etc. aspects play an extremely important role. The most widely used fluorosurfactants are perfluorooctanoic acid (PFOA) and perfluorooctane sulfonic a...

Claims

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Application Information

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IPC IPC(8): B01F17/18B01F17/22B01F17/42C07C213/08C07C219/14C07C231/12C07C235/50C09K23/18C09K23/22C09K23/42
Inventor 郑土才赵颖俊吕延文吾国强
Owner 江苏超至和新材料有限公司
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