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Gemini perfluoroether surfactant and preparation method thereof

A technology of surfactant and perfluoroether, which is applied in the field of gemini-type perfluoroether surfactant and its preparation, can solve the problems of bioaccumulation and high toxicity, achieve low bioaccumulation, simple synthesis process, and easy raw materials The effect

Active Publication Date: 2020-07-24
SANMING HEXAFLUO CHEM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Aiming at the problems of bioaccumulation and high toxicity of existing perfluoroalkyl chain surfactants, the present invention provides a preparation method of gemini-type perfluoroether surfactants

Method used

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Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0051] Another embodiment of the present invention provides a method for preparing the above-mentioned gemini type perfluoroether surfactant, comprising the following steps:

[0052]

[0053] Obtain compounds shown in Structural Formula 2, Structural Formula 3 and Structural Formula 4, mix the compound shown in Structural Formula 2, the compound shown in Structural Formula 3 and the compound shown in Structural Formula 4 in a solvent, heat up to solvent reflux, and remove the solvent after the reaction , to obtain the compound shown in structural formula 1;

[0054]

[0055] Among them, R 1 and R 3 each independently selected from straight or branched perfluoroether chains and perfluoropolyether chains with 2-7 carbon atoms; R 2 A straight-chain or branched hydrocarbon group or ether group selected from 2 to 12 carbon atoms and an aromatic group in the ortho, meta or para position; R 4 and R 5 each independently selected from straight-chain or branched hydrocarbon gr...

Embodiment 1

[0072] This example is used to illustrate the gemini-type perfluoroether surfactant disclosed in the present invention and its preparation method, including the following steps:

[0073] Compound C (2mmol, 1.0eq.), (4mmol, 2.0eq.) and 5mL of acetonitrile / ethanol were added to a 50mL round-bottomed three-neck flask, wherein, compound C was selected from compound 10, and bromide was selected from 1,2- For bis(bromomethyl)benzene, assemble a reflux device, increase the temperature to 70-90° C., reflux the solvent, and react for 8-16 hours. After the reaction was completed, the solvent was removed by rotary evaporation to obtain a solid crude product, which was recrystallized with a yield of 94%. The obtained product was labeled as compound 11.

[0074] Compound 10 was tested by proton nuclear magnetic resonance spectrum, fluorine nuclear magnetic resonance spectrum and infrared absorption spectrum, and the test results obtained are as follows:

[0075] 2-(2-(difluoro(trifluorom...

Embodiment 2

[0083] This example is used to illustrate the gemini-type perfluoroether surfactant disclosed in the present invention and its preparation method, including most of the operating steps in Example 1, the difference being:

[0084] Compound C is selected from compound 10, bromide is selected from 1,3-bis(bromomethyl)benzene;

[0085] The obtained product is labeled as compound 12;

[0086] Compound 12 was tested by proton nuclear magnetic resonance spectrum, fluorine nuclear magnetic resonance spectrum and infrared absorption spectrum, and the test results obtained are as follows:

[0087] N,N'-(1,3-phenylenebis(methylene))bis(1,1,1,3,3,5,5,6,6,8-decafluoro-N,N-dimethyl-9-oxo-8 -(trifluoromethyl)-2,4,7-trioxa-10-azatridecan-13-aminium)bromide(12):

[0088]

[0089] White solid, yield 93%. 1 H NMR (400MHz, CD 3 OD): δ8.04(s,1H),7.83(t,J=8Hz,2H),7.72(t,J=8Hz,1H),4.76(s,4H),3.54–3.40(m,8H), 3.18(s,6H),3.17(s,6H),2.27–2.17(m,4H). 19 F NMR (376MHz, CD 3 OD): δ-55.1–-55.3(m,...

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Abstract

The invention provides a gemini perfluoroether surfactant which comprises a structure shown in the specification, wherein R1 and R3 are each independently selected from a linear or branched perfluoroether chain and a perfluoropolyether chain with the carbon atom number of 2-7 respectively, R2 is selected from linear or branched alkyl or ether groups with the carbon atom number of 2-12 and ortho-position, meta-position or para-position aromatic groups, R4 and R5 are each independently selected from a linear or branched hydrocarbon group or aromatic group having 2-5 carbon atoms, R6 and R7 are each independently selected from O or NR8, R8 is selected from H or a hydrocarbon group having 1-3 carbon atoms, and X is selected from halogen. Meanwhile, the invention also discloses a preparation method of the gemini perfluoroether surfactant. The gemini perfluoroether surfactant provided by the invention has good degradability and low toxicity, and the problems of high biological accumulation and high toxicity of the existing fluorocarbon surfactant can be effectively solved.

Description

technical field [0001] The invention belongs to the technical field of surfactants, and in particular relates to a gemini type perfluoroether surfactant and a preparation method thereof. Background technique [0002] As a new class of special surfactants, fluorocarbon surfactants have become a hot spot in the field of chemical surfactants. Traditional fluorocarbon surfactants refer to the fact that some or all of the hydrogen atoms on the hydrophobic chain are replaced by fluorine atoms. This type of compound At the same time, it has the functions of "water-repellent" and "oil-repellent". Therefore, fluorine-containing surfactants are mainly used in fire-fighting foam fire extinguishing, industry, agriculture, machinery, textiles, medicine and other fields. reputation. [0003] Traditional surfactants consist of a terminal hydrophilic group and a hydrophobic group, while twinned surfactants (Gemini surfactant or Geminis) consist of two or more hydrophilic tail groups, two ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/10C07C231/12B01F17/18B01F17/22B01F17/42C09K23/18C09K23/22C09K23/42
CPCC07C235/10C07C231/12C09K23/00
Inventor 谢伟东郭勇杜芳琼吴成英陈庆云黄美薇王孟英
Owner SANMING HEXAFLUO CHEM CO LTD
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