A kind of silane coupling agent with double stimulation response and its preparation method and application

A dual-stimuli-response, silane coupling agent technology, applied in the field of silane coupling agent preparation, can solve the problems of cumbersome conditions, complex synthesis, single control method, etc., and achieve the effect of improving hydrophobicity and simple modification method

Inactive Publication Date: 2021-03-30
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method is complicated to synthesize, the conditions are cumbersome, polymerization reaction is required, and the control method is single, which can only be realized by changing the relevant anions.

Method used

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  • A kind of silane coupling agent with double stimulation response and its preparation method and application
  • A kind of silane coupling agent with double stimulation response and its preparation method and application
  • A kind of silane coupling agent with double stimulation response and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Under nitrogen protection, add 1g (2.8mmol) 3-hydroxyl, 5-ferrocenehexyloxymethylbenzoate, 1.52g (4.2mmol) hexabromohexyloxyazobenzene, 1.37g to a 150mL three-necked flask (4.2mmol) cesium carbonate, 50mL N, N-dimethylformamide (DMF), warming up to 85 ℃ for reaction, during the reaction, use thin-layer chromatography to determine the reaction process, after 12 hours, the reaction is complete, stop heating, and cool After reaching room temperature, the cesium carbonate was removed by suction filtration, the cesium salt was rinsed with dichloromethane until it was colorless, and the solvent was removed by rotary evaporation under reduced pressure to obtain an orange-yellow crude product. The crude product was dissolved in butanone, placed in a refrigerator to cool and crystallize, and repeated three times to obtain methyl 3-ferrocenehexyloxy-5-azophenylhexyloxybenzoate.

[0045]Under nitrogen protection, add 10mL of anhydrous tetrahydrofuran to a 150mL three-necked flask,...

Embodiment 2

[0055] Under nitrogen protection, add 1g (2.6mmol) 3-hydroxyl, 5-ferrocene octyloxymethyl benzoate, 0.8g (2.6mmol) hexabromooctyloxyazobenzene, 0.54g to a 150mL three-necked flask (3.9mmol) Potassium Carbonate, 50mL N, N-dimethylformamide (DMF), warming up to 85 ° C for reaction, during the reaction, use thin layer chromatography to determine the reaction process, after 12 hours, the reaction is complete, stop heating, and cool After reaching room temperature, potassium carbonate was removed by suction filtration, the potassium salt was rinsed with dichloromethane until it was colorless, and the solvent was removed by rotary evaporation under reduced pressure to obtain an orange-yellow crude product. The crude product was dissolved in methyl ethyl ketone, put into the refrigerator to cool and crystallize, and repeated 3 times to obtain 3-ferrocenyl octyloxy, 5-azobenzyloxybenzoic acid methyl ester.

[0056] Under nitrogen protection, 10 mL of anhydrous tetrahydrofuran was adde...

Embodiment 3

[0062] Under nitrogen protection, in a 150mL three-necked flask, add 1g (2.5mmol) 3-hydroxy-5-ferrocenedecyloxymethyl benzoate, 1.54g (3.75mmol) hexabromodecyloxyazobenzene, 1.22g (3.75mmol) cesium carbonate, 50mL N, N-dimethylformamide (DMF), warming up to 85 ℃ for reaction, during the reaction, use thin layer chromatography to determine the reaction process, after 12 hours, the reaction is complete, stop heating, and cool After reaching room temperature, the cesium carbonate was removed by suction filtration, the cesium salt was rinsed with dichloromethane until it was colorless, and the solvent was removed by rotary evaporation under reduced pressure to obtain an orange-yellow crude product. The crude product was dissolved in butanone, placed in a refrigerator for cooling and crystallization, and repeated 3 times to obtain methyl 3-ferrocenedecyloxy-5-azobendecyloxybenzoate.

[0063] Under nitrogen protection, 10 mL of anhydrous tetrahydrofuran was added to a 150 mL three-n...

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PUM

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Abstract

The invention discloses a silane coupling agent with double stimulation response and a preparation method and application thereof. The preparation method comprises the following steps that 3-hydroxyl,5-dicyclopentadienyl alkoxy methyl benzoate and bromoalkoxy azobenzene generate 3-dicyclopentadienyl alkoxy,5-azobenzene alkoxy methyl benzoate under base catalysis, and then the 3-dicyclopentadienylalkoxy,5-azobenzene alkoxy methyl benzoate is reduced to a 3-dicyclopentadienyl alkoxy,5-azobenzene alkoxy benzyl alcohol end capping agent; under the protection of nitrogen, the 3-dicyclopentadienylalkoxy,5-azobenzene alkoxy benzyl alcohol, propyl isocyanate triethoxysilane and a catalyst organic tin are added into methylbenzene, the temperature is increased to 80-110 DEG C, and a reaction is carried out to obtain the dicyclopentadienyl azobenzene silane coupling agent. The silane coupling agent can be used for modifying the surface of glass, and the modified glass has the characteristic ofbeing able to be oxidized by ultraviolet light for double stimulation response to change the hydrophilicity of the surface.

Description

technical field [0001] The present invention relates to a preparation method of a silane coupling agent with double stimulus response, in particular to a preparation method of a silane coupling agent modified with ferroceneazobenzene; the silane coupling agent can be used for glass surface modification properties, to prepare glass with controllable surface wettability. Background technique [0002] Silane coupling agent is a kind of organosilicon compound with special structure, which has both reactive groups that can be combined with inorganic materials (such as glass, cement, metal, etc.) and reactive groups that can be combined with organic materials, so it can The surface properties of inorganic substances are changed by silane coupling agents. [0003] The wettability of the solid surface is one of the very important surface properties. Controlling the wettability of the surface is very important in many practical applications. The hydrophobic / hydrophilic reversible ma...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/18C03C17/30
CPCC03C17/30C07F7/1892
Inventor 任碧野严小龙杜柱康
Owner SOUTH CHINA UNIV OF TECH
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