Gemini surface active agent using pyrrole ring as hydrophilic head group and preparation method of Gemini surface active agent using pyrrole ring as hydrophilic head group

A surfactant and pyrrole ring technology, applied in the field of surfactant preparation, can solve the problems of complex preparation steps of Gemini surfactant, unsuitable for large-scale production and application, surface activity needs to be improved, etc., and achieve low critical micelle concentration , strong industrial operability, good viscoelastic effect

Inactive Publication Date: 2013-02-27
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, surfactants with excellent properties still need to be developed. The preparation steps of Gemini surfactants are more complicated. The reaction conditions in the preparation process of current Gemini surfactants are not easy to control, which is not suitable for large-scale production and application.
Currently reported Gemini surfactants with the pyrrole ring as the hydrophilic head group (C n -s- n PB), where s=4, n=10~16, Journal of Colloid and InterfaceScience 370(2012) 111–116, but its surface activity needs to be improved

Method used

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  • Gemini surface active agent using pyrrole ring as hydrophilic head group and preparation method of Gemini surface active agent using pyrrole ring as hydrophilic head group
  • Gemini surface active agent using pyrrole ring as hydrophilic head group and preparation method of Gemini surface active agent using pyrrole ring as hydrophilic head group
  • Gemini surface active agent using pyrrole ring as hydrophilic head group and preparation method of Gemini surface active agent using pyrrole ring as hydrophilic head group

Examples

Experimental program
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Embodiment 1

[0030] The preparation (C 8 -3- 8 PB)

[0031] Add 14.2g (0.2 moles) of pyrrolidine to 200ml of methanol, add 24g (0.6 moles) of sodium hydroxide and 84.5g (0.44 moles) of bromooctane in turn, and keep the reaction at 40°C for 6 hours; after the reaction is completed, depressurize Remove methanol and unreacted pyrrolidine, and the obtained light yellow liquid is separated by a chromatographic column filled with 40 times its weight of silica gel, and petroleum ether, dichloromethane, ethyl acetate / dichloromethane / ammonia water are used as eluents in sequence , collect the eluate and concentrate to obtain N-octylpyrrolidine with a yield of 96%. Add 250ml of isopropanol or acetonitrile and 13.3g (0.0665 moles) of 1,3-dibromopropane to the N-octylpyrrolidine obtained above, stir vigorously, and react at 100°C for 12 hours; Isopropanol, the obtained pale yellow solid was recrystallized with a mixed solvent of ethanol / acetone, and the resulting product was vacuum-dried to obtain ...

Embodiment 2

[0040] The preparation (C 12 -3- 12 PB)

[0041]Add 14.2g (0.2 moles) of pyrrolidine to 200ml of ethanol, add 32g (0.8 moles) of sodium hydroxide and 124g (0.5 moles) of dodecane bromide in turn, and keep it at 60°C for 10 hours; after the reaction is completed, depressurize Remove ethanol and unreacted pyrrolidine, and the obtained pale yellow liquid is separated by a chromatographic column filled with 40 times its weight of silica gel, and sequentially use n-hexane, dichloromethane, ethyl acetate / dichloromethane / ammonia water as eluent , collect the eluate and concentrate to obtain N-dodecylpyrrolidine with a yield of 98%. Add 250ml of isopropanol and 15.7g (0.0784 moles) of 1,3-dibromopropane to the N-dodecylpyrrolidine obtained above, stir vigorously, and react at 80°C for 48 hours; after the reaction, remove isopropanol under reduced pressure. propanol, the obtained light yellow solid is recrystallized with the mixed solvent of ethanol / ethyl acetate, and the product ob...

Embodiment 3

[0049] The preparation (C 18 -3- 18 PB)

[0050] Add 14.2g (0.2 mole) of pyrrole ring to 200ml of N,N-dimethylformamide, add 50.4g (0.6 mole) of sodium bicarbonate and 353g (0.8 mole) of octadecane bromide in sequence, and keep the reaction at 80°C 24 hours; after the reaction was completed, N,N-dimethylformamide and unreacted pyrrolidine were removed under reduced pressure, and the obtained light yellow liquid was separated by a chromatographic column equipped with 40 times its weight of silica gel, and then washed with n-hexane, Dichloromethane, ethyl acetate / dichloromethane / ammonia water were used as eluents, and the eluent was collected and concentrated to obtain N-octadecylpyrrolidine with a yield of 95%. Add 250ml of N,N-dimethylformamide and 13.3g (0.0665 moles) of 1,3-dibromopropane to the N-octadecylpyrrolidine obtained above, stir vigorously, and react at 120°C for 72 hours; After the end, N,N-dimethylformamide was removed under reduced pressure, and the wine-red ...

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Abstract

The invention discloses a cation Gemini surface active agent using a pyrrole ring as a hydrophilic head group, and relates to a preparation method of the surface active agent. The preparation method comprises the specific steps of generating N-alkyl pyrrolidine by pyrrolidine and long-chain alkyl under the actions of N2 (nitrogen) protection and catalyst function, and carrying out reaction of the obtained N-alkyl pyrrolidine and dibromo-paraffin so as to obtain the cation Gemini surface active agent using the pyrrole ring as the hydrophilic head group. The Gemini surface active agent has good surface activity and viscoelasticity, the Gemini surface active agent can be singly used or compounded with other surface active agents due to the good property, and further the Gemini surface active agent is widely applied to the industrial practices, such as daily-use chemical industry, sterilizers, pesticide agents, petroleum production, and thick oil viscosity reduction.

Description

technical field [0001] The invention relates to a cationic Gemini surfactant with a pyrrole ring as a hydrophilic head group, and also relates to a preparation method of the Gemini surfactant, which belongs to the technical field of surfactant preparation. Background technique [0002] Surfactant refers to a large class of substances that have fixed hydrophilic and lipophilic groups, can form directional arrangements on the surface of a solution, and can significantly reduce surface tension. According to the traditional structural classification method of surfactants, surfactants can be divided into ionic and nonionic, and ionic includes cationic, anionic and zwitterionic. Due to their structural characteristics, Gemini surfactants have many advantages compared with traditional monadic surfactants, such as lower critical micelle concentration (cmc), lower surface tension and Krafft point, higher Surface activity, richer aggregate structure and better synergistic effect. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01F17/32C07D295/037C07D295/023C09K23/32
Inventor 李学丰蔡波董金凤
Owner WUHAN UNIV
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