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Preparation method of fluorine-containing compound for hydrophobic surface treatment agent

A hydrophobic surface and treatment agent technology, which is applied in the field of preparation of fluorine-containing compounds for hydrophobic surface treatment agents, can solve problems such as complex preparation methods, and achieve the effect of being suitable for large-scale production and avoiding oxidation

Inactive Publication Date: 2021-03-23
湖北福力德鞋业有限责任公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the preparation method of the treatment agent reported so far is relatively complicated, including five-step reactions, and the phenolic hydroxyl and amino groups of the starting material-dopa need to be protected separately.

Method used

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  • Preparation method of fluorine-containing compound for hydrophobic surface treatment agent
  • Preparation method of fluorine-containing compound for hydrophobic surface treatment agent

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preparation example Construction

[0031] The invention provides a preparation method of a fluorine-containing compound for a hydrophobic surface treatment agent. Dopa is used as a starting material, and its functional group is protected by a benzyl chloride reagent or a benzyl bromide reagent, and then the carboxyl protection is removed by alcoholysis. Then carry out esterification or amidation reaction with long-chain perfluoroalkanols or alkylamines, and finally deprotect to obtain long-chain perfluoroalkanes based on the dopa structure. The typical reaction route is as follows:

[0032]

[0033] Specific steps are as follows:

[0034] 1) Group protection

[0035] Use benzyl chloride reagents or benzyl bromide reagents to react with dopa in polar organic solvents, and add an acid-binding agent to protect the phenolic hydroxyl and amino groups of dopa molecules, specifically:

[0036] Dopa (3,4-dihydroxyphenylalanine) is completely dissolved in a polar organic solvent, and the polar organic solvent prefer...

Embodiment 1

[0067] 1) Dissolve 1.97g levodopa in 30ml N,N-dimethylformamide, then add 8.5g 4-methoxybenzyl chloride and 9g potassium carbonate (K 2 CO 3 ), under the protection of nitrogen, after stirring and reacting for 12h under the temperature condition of 60°C, 100ml of dichloromethane and 100ml of water were added to the reaction solution for extraction, the organic phase was separated and washed 3 times, and the solvent was evaporated to dryness Afterwards, a light yellow viscous product is obtained;

[0068] 2) Dissolve 5g of the product from the previous step in 50ml of methanol, add 1g of potassium hydroxide and 2ml of water, then reflux for 6 hours, add dilute hydrochloric acid dropwise after the reaction to adjust the pH to about 4.0, evaporate the solvent and add 100ml of water , extracted 3 times with dichloromethane, and evaporated to dryness to obtain a light yellow solid;

[0069] 3) Dissolve 1.36g of the light yellow solid in the previous step in 100ml of dichlorometha...

Embodiment 2

[0077] The difference with embodiment 1 is:

[0078] In step 1), the solvent N,N-dimethylformamide is replaced by dimethyl sulfoxide, and the addition is still 30ml; 4-methoxybenzyl chloride is replaced by 4-methoxybenzyl bromide, and the addition is 11 g; replace potassium carbonate with cesium carbonate (Cs 2 CO 3 ), the addition amount is 18g; the reaction environment is adjusted to react at 0°C for 1h, and then react at 50°C for 2h;

[0079] In step 2), methanol is replaced by ethanol, and the addition is still 50ml; potassium hydroxide is replaced by sodium hydroxide, and the addition is still 1g;

[0080] In step 3), the solvent dichloromethane is replaced by chloroform, and 2-perfluorooctyl ethanol is replaced by 1H, 1H-perfluoro-1-nonanol, and the addition amount is 0.85g; 1-(3-di The catalytic system of methylaminopropyl)-3-ethylcarbodiimide (EDC1) / 1-hydroxybenzotriazole (HOBt) / 4-dimethylaminopyridine (DMAP) was replaced by dicyclohexylcarbodiimide Imine (DCC) / 4-d...

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Abstract

The invention relates to the technical field of chemical synthesis and application, and discloses a preparation method of a fluorine-containing compound for a hydrophobic surface treatment agent, which comprises the following steps: 1) group protection: reacting a benzyl chloride reagent or benzyl bromide reagent with dopa in a polar organic solvent, and adding an acid-binding agent to protect phenolic hydroxyl groups and amino groups of dopa molecules; 2) alcoholysis: dissolving the reaction product in the previous step in an organic solvent, adding water, and carrying out heating reflux under an alkaline condition; 3) esterification or amidation: dissolving the reaction product in the step 2) in an organic solvent, adding a catalyst or a dehydrating agent, and carrying out esterificationreaction with fluoroalkanol or amidation reaction with alkylamine; and 4) protecting group removal: removing the protecting group from the reaction product in the step 3). Compared with the prior art, the method has the advantages that a new preparation route is shorter, respective protection of phenolic hydroxyl groups and amino groups of dopa is avoided, and the long-chain perfluoro-substitutedalkane based on the dopa structure can be prepared through four-step reaction.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis and application, in particular to a method for preparing a fluorine-containing compound for a hydrophobic surface treatment agent. Background technique [0002] Hydrophobic coatings are characterized by easy cleaning and low adhesion, and are widely used in many applications, such as optical lenses, TV screens, cooking utensils, clothing, medical equipment, etc. In particular, the rapid development of superhydrophobic technology in recent years has attracted widespread attention. This is a new type of technology with special surface properties. Preventing current conduction etc. shows great advantages and promises. [0003] At present, the most reported (super) hydrophobic coating preparation methods can be roughly divided into two categories, and the most commonly used method includes two steps of material preparation and surface coating. First, a rough micro / nano structure is formed...

Claims

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Application Information

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IPC IPC(8): C07C227/18C07C229/36C07C231/02C07C237/20C03C17/28
CPCC07C227/18C07C231/02C03C17/28C03C2217/70C03C2218/111C03C2218/322C07C229/36C07C237/20Y02P20/55
Inventor 范伟伟梁嘉健
Owner 湖北福力德鞋业有限责任公司
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