Photosensitive mixed surfactant as well as preparation method and application thereof

A surfactant and hybrid technology, which is applied in the field of photosensitive mixed surfactant and its preparation, can solve the problems of perfluorocarbon groups that have not been reported, and achieve the effect of significant surface activity and large surface tension difference

Pending Publication Date: 2022-04-12
蒲城驭腾新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Some existing studies have reported the modulation of linear micelles formation or destruction conditions that directly act as photosensitizers, and these are mostly based on cetyltrimethylammonium bromide and azobenzene-containing amphiphile mixtures [H. Sakai, Y .Orihara, H. Kodashima, A. Matsumura, T. Ohkubo, K. Tsuchiya, M. Abe, J. Am. Chem. Soc. 127 (2005) 13454–13455] or cinnamic acid derivatives [A.M.Ketner, R. Kumar, T.S.Davies, P.W.Elder, S.R.Raghavan, J.Am.Chem.Soc.129(2007) 1553–1559], but there are few reports on the formation of linear micelles using stilbene derivatives as photosensitive materials, micelles The introduction of perfluoroalkyl groups in the group has not been reported, so it is of great significance to explore the synthesis of new photosensitive materials

Method used

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  • Photosensitive mixed surfactant as well as preparation method and application thereof
  • Photosensitive mixed surfactant as well as preparation method and application thereof
  • Photosensitive mixed surfactant as well as preparation method and application thereof

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preparation example Construction

[0048] The present invention further discloses the preparation method of the above-mentioned stilbene-based mixed surfactant, which specifically includes the following steps:

[0049](1) In terms of moles, put 50-100 parts of 1,4-diiodobenzene, 50-100 parts of perfluoroalkyl iodide, 150-300 parts of copper powder, and 900-1800 parts of dehydrated dimethyl Under dry N2 atmosphere, reflux at 120°C for 24h. After the reaction, the Cu powder was filtered off, and the precipitated solid was washed with ether and water successively.

[0050] (2) In terms of moles, put 50-100 parts of 4-(perfluoroalkyl) iodobenzene, 75-150 parts of 4-(vinyl)phenyl acetate, 500- 1000 parts of N-methyl-2-pyrrolidone as a solvent, 60-120 parts of potassium carbonate as an acid-binding agent, 25-50 parts of palladium acetate and 25-50 parts of 4-dimethylaminobutyric acid hydrochloride as a catalyst, 130 ℃ reaction 20h. The crude product was purified with chloroform, and the resulting chloroform soluti...

Embodiment 1

[0054] A 250ml three-necked flask is equipped with a thermometer, a reflux condenser, and a stirring magnet, and 29mmol of 1,4-diiodobenzene, 29mmol of perfluorooctyl iodide, 90mmol of copper powder, and 50ml of dehydrated dimethyl sulfoxide are placed in a dry N2 atmosphere , 120 ° C reflux reaction for 24h. After the reaction, the Cu powder was filtered off, and the precipitated solid was washed with ether and water successively.

[0055] A 250ml three-necked flask is equipped with a thermometer, a reflux condenser, and a stirring magnet, and 25mmol of 4-(perfluoroalkyl) iodobenzene obtained in the step reaction of (1), 37.5mmol of 4-(vinyl)phenyl acetate, and 50ml of N-methyl - 2-pyrrolidone as solvent, 30mmol potassium carbonate as acid-binding agent, 12mmol palladium acetate and 12mmol 4-dimethylaminobutyric acid hydrochloride as catalyst, react at 130°C for 20h. The crude product was purified with chloroform, and the resulting chloroform solution was washed successively...

Embodiment 2

[0059] A 250ml three-necked flask is equipped with a thermometer, a reflux condenser, and a stirring magnet, and 29mmol of 1,4-diiodobenzene, 29mmol of perfluorooctyl iodide, 150mmol of copper powder, and 100ml of dehydrated dimethyl sulfoxide are placed in a dry N2 atmosphere , 120 ° C reflux reaction for 24h. After the reaction, the Cu powder was filtered off, and the precipitated solid was washed with ether and water successively.

[0060] A 250ml three-necked flask is equipped with a thermometer, a reflux condenser, a stirring magnet, and 25mmol of 4-(perfluoroalkyl) iodobenzene obtained in the step reaction of (1), 50mmol of 4-(vinyl)phenyl acetate, 50ml of N-methyl- 2-Pyrrolidone was used as a solvent, 35mmol potassium carbonate was used as an acid-binding agent, 12mmol palladium acetate and 12mmol 4-dimethylaminobutyric acid hydrochloride were used as catalysts, and the reaction was carried out at 130°C for 20h. The crude product was purified with chloroform, and the r...

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Abstract

The invention relates to a photosensitive mixed surfactant and a preparation method and application thereof, in particular to a photosensitive mixed surfactant based on a stilbene cation mixed surfactant represented as CFm StilCHn, CFm represents a perfluorohydrocarbon chain segment with the carbon atom number of m (m = 4, 6, 8), Stil represents diphenylethylene, CHn represents an alkane chain with the carbon atom number of n (n = 1, 4, 8), and the surface and micellization properties of the surfactants are researched. In the most meaningful property, due to the existence of a fluorocarbon chain, the stilbene-based mixed surfactant shows remarkable surface activity on the surface tension of a water / air interface. In addition, ultraviolet irradiation enables the surface tension of an air / water interface to be obviously increased, and compared with a traditional stilbene-based surfactant, the mixed surfactant cis / trans-isomer has larger surface tension difference.

Description

technical field [0001] The invention belongs to the technical field of surfactants, in particular to a photosensitive mixed surfactant, its preparation method and application. Background technique [0002] In photochemical reactions, photochromism is the reversible photoswitching of two forms when a substance is exposed to heat or light, and these two forms have different absorption spectra. Photoisomerization not only changes the absorption spectrum of the substance, but also affects the physical and chemical properties of the substance, such as refractive index, redox site and geometric structure. These properties have been applied in many fields such as liquid crystals, photochemical recording, molecular switching devices, micellar catalysis, photoelectric foams and gels. Recently, researchers have applied photochromism to biological systems and polymer preparation. [0003] Stilbenoid, a photochromic material, switches between two isomers depending on the wavelength of...

Claims

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Application Information

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IPC IPC(8): C07C217/20C07C213/02C09K23/42
Inventor 陈力群蔡志红李小强苗玉
Owner 蒲城驭腾新材料科技有限公司
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