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Polymerizable nonionic surfactant containing adamantane structure and preparation method thereof

A technology of non-ionic surfactants and active agents, applied in the field of polymerizable non-ionic surfactants and their preparation, to achieve good water solubility and expand the types and scope of effects

Pending Publication Date: 2022-07-15
PETROCHINA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Based on the fact that the adamantane structure has not been involved in the synthesis of hydrophobic association polymers as a hydrophobic monomer in the prior art, it is necessary to explore the application of the adamantane structure in hydrophobic monomers

Method used

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  • Polymerizable nonionic surfactant containing adamantane structure and preparation method thereof
  • Polymerizable nonionic surfactant containing adamantane structure and preparation method thereof
  • Polymerizable nonionic surfactant containing adamantane structure and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0031] The present embodiment provides a preparation method of an adamantane structure-containing polymerizable nonionic surfactant, which is specifically as follows:

[0032] Under ice-water bath conditions, take 3.6 g of polyethylene glycol methacrylate (Mw=360, CAS number: 25736-86-1) and 2 g of 1-adamantanecarbonyl chloride, add them into 50 mL of dichloromethane, and after stirring evenly, A dichloromethane solution containing 1.05 g of triethylamine was slowly added dropwise, and after stirring for 4 h, the precipitate was removed by filtration, washed twice with 20 mL of 1% sodium bicarbonate solution and 1% hydrochloric acid in turn, and then separated. Then the oily liquid obtained is the product methacrylate polyethylene glycol 360 adamantyl methyl ester, which is named as A1. figure 1 It is the infrared contrast spectrum of the raw material polyethylene glycol methacrylate and the product A1. Compared with the raw material, the 1728cm in A1 -1 The peak of ester car...

Embodiment 2

[0034] The present embodiment provides a method for preparing an adamantane structure-containing polymerizable nonionic surfactant, which is specifically as follows:

[0035] Under ice-water bath conditions, take 5 g of polyethylene glycol methacrylate (Mw=500) and 2 g of 1-adamantanecarbonyl chloride, add them to 50 mL of dichloromethane, and after stirring evenly, slowly add triethylamine 1.05 g dropwise. The dichloromethane solution was stirred for 4 hours, and the precipitate was removed by filtration. After washing twice with 20 mL of 1% sodium bicarbonate solution and 1% hydrochloric acid, the liquid was separated. Ester polyethylene glycol 500 adamantyl methyl ester.

Embodiment 3

[0037] The present embodiment provides a method for preparing an adamantane structure-containing polymerizable nonionic surfactant, which is specifically as follows:

[0038] Take 3.6 g of polyethylene glycol methacrylate (Mw=360) and 1.8 g of 1-adamantanecarboxylic acid, add them to 50 mL of tetrahydrofuran, stir evenly, and slowly dropwise add a dichloromethane solution containing 1.5 g of thionyl chloride, After refluxing at 60°C for 4 hours, the solvent was evaporated to dryness, then ethyl acetate was added to dissolve it, washed twice with a mixture of sodium bicarbonate and ice-water, and then the liquid was separated. Acrylate polyethylene glycol 360 adamantyl methyl ester.

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Abstract

The invention provides a polymerizable nonionic surfactant containing an adamantane structure and a preparation method of the polymerizable nonionic surfactant. The synthesis method of the polymerizable nonionic surfactant comprises the following step: carrying out esterification reaction on adamantyl acyl chloride and polyethylene glycol acrylate in an organic solvent under the condition that organic alkali is used as an acid-binding agent, so as to obtain the polymerizable nonionic surfactant. Or adamantane carboxylic acid and polyethylene glycol acrylate are subjected to esterification reaction in an organic solvent by using a catalyst. A polymerizable double-bond structure is contained on a molecular terminal group of a product obtained after reaction, the product can be applied to polymerization reaction to serve as a hydrophobic monomer, and the product has surface activity.

Description

technical field [0001] The invention relates to the technical field of surfactants, in particular to an adamantane structure-containing polymerizable nonionic surfactant and a preparation method. Background technique [0002] Adamantane is a highly symmetrical and very stable compound, and its special cage-like structure has aroused great interest in the chemical community, giving birth to the birth of cage-like compound chemistry. Later, it was found that adamantane derivatives have antiviral activity, and it has received special attention from the pharmaceutical industry. Many documents and patents have reported the application prospects of adamantane derivatives as drugs; the systematic research around adamantane in the chemical industry has formed a system. Separate subject: Adamantane chemistry. Common patents and literature focus on the application of adamantane in drugs and new materials. CN105829284A discloses a method for synthesizing adamantane carboxamide compou...

Claims

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Application Information

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IPC IPC(8): C07C69/753C07C67/14C07C67/08C09K23/44C09K8/584C09K8/72C08F20/28C08F220/56C08F220/28C08F2/10
CPCC07C69/753C07C67/14C07C67/08C09K8/584C09K8/725C08F20/28C08F220/56C08F2/10C07C2603/74C08F220/286
Inventor 敬显武熊颖李伟蒋泽银周厚安龙顺敏付子倚
Owner PETROCHINA CO LTD
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