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Double-branched-chain organosilicon quaternary ammonium salt as well as preparation method and application thereof

A technology of organosilicon quaternary ammonium salt and double branched chain, which is applied in the fields of botanical equipment and methods, applications, organic chemistry, etc., can solve the problems of skin and mucous membrane irritation, high equipment requirements, low output, etc., to reduce High risk and high energy consumption, easy industrial scale-up production, solve the effect of low yield

Pending Publication Date: 2021-08-20
杭州昕洋生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many problems in this kind of synthetic route in the process of actually expanding the production, for example, in the first esterification reaction, toluene or chloroform solvent with high boiling point, high toxicity, and subsequent difficult handling will be used; toluenesulfonic acid or hypophosphorous acid needs to be used as a catalyst, Difficult to purify; the whole reaction requires the help of vacuum equipment, microwave reactors or high-pressure reactors, etc., which is inconvenient to operate and requires high equipment; expensive raw materials and high production costs
The overall preparation process is characterized by high energy consumption, high risk, and low output
[0005] (2) As far as the product is concerned, the organosilicon quaternary ammonium salt compounds reported in the current patent literature all introduce methoxy organosilicon functional groups, and the introduced methoxy organosilicon functional groups cannot effectively improve the antibacterial activity of the core group of the compound. In addition, methoxy silicone functional groups tend to release methanol, which may be irritating to skin and mucous membranes
More importantly, the existing organosilicon quaternary ammonium salts do not have long-term antibacterial effect

Method used

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  • Double-branched-chain organosilicon quaternary ammonium salt as well as preparation method and application thereof
  • Double-branched-chain organosilicon quaternary ammonium salt as well as preparation method and application thereof
  • Double-branched-chain organosilicon quaternary ammonium salt as well as preparation method and application thereof

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preparation example Construction

[0055] Another aspect of the present invention provides a method for preparing a double-branched organosilicon quaternary ammonium salt. In an exemplary embodiment of the preparation method of the double-branched organosilicon quaternary ammonium salt of the present invention, the following steps may be included:

[0056] Step 01, mix N-methyldiethanolamine with the structure of formula I and 3-chloropropyltriethoxysilane with the structure of formula II and place it in a reactor, add the first solvent and catalyst, and heat under an inert atmosphere To the end of the reaction, remove the first solvent, remove the lower layer of liquid after layering, and obtain a colorless transparent liquid-quaternary ammonium salt intermediate with the structure of formula III after washing. The reaction process is as follows:

[0057]

[0058] Step 02, mix the quaternary ammonium salt intermediate with the structure of formula III with the acid chloride, add the second solvent, heat unt...

example 1

[0080] Step 1, N-methyldiethanolamine and 3-chloropropyltriethoxysilane are mixed in a molar ratio of 1:1.2 and then added to the reaction vessel, 30%wt of isopropanol is added as a solvent, and KI is used as a catalyst ( KI and N-methyldiethanolamine molar ratio 0.01:1), in N 2 Under protection, heat to 110°C and reflux for 16 hours. After completion, vaporize to remove the isopropanol solvent. After layering, take the lower layer liquid and wash with a small amount of ethyl acetate to obtain a colorless transparent liquid, which is the quaternary ammonium salt intermediate;

[0081] Step 2, mix the quaternary ammonium salt intermediate obtained in step 1 with 2-ethylhexanoyl chloride at a molar ratio of 1:3, add it to the reaction vessel, add acetonitrile solvent, heat to 100°C for reflux reaction for 12 hours, and then vaporize and remove the acetonitrile Solvent, let it stand to be separated, wash with a small amount of ethyl acetate, and remove the lower layer of transpar...

example 2

[0088] Step 1, N-methyldiethanolamine and 3-chloropropyltriethoxysilane are mixed in a molar ratio of 1:1.5 and added to the reaction vessel, 30wt% isopropanol is added as a solvent, and KI is used as a catalyst (KI and N -Methyldiethanolamine mol ratio 0.01:1) and add reaction system gross mass 0.02%wt BHT antioxidant, in N 2 Under protection, heat to 100°C and reflux for 20 hours. After completion, vaporize to remove the solvent. After layering, take the lower layer liquid and wash with a small amount of ethyl acetate to obtain a colorless transparent liquid, which is the quaternary ammonium salt intermediate;

[0089] Mix the above-mentioned quaternary ammonium salt intermediate with 2,2-dimethylbutyryl chloride in a molar ratio of 1:3 and add it into the reaction vessel, add acetonitrile solvent, heat up to 100°C for reflux reaction for 12 hours, evaporate the solvent after completion, and let it stand for The layers were separated, washed with a small amount of ethyl acet...

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Abstract

The invention provides double-branched-chain organosilicon quaternary ammonium salt as well as a preparation method and application thereof. The preparation method comprises the following steps: mixing N-methyldiethanolamine with 3-chloropropyltriethoxysilane, adding a first solvent and a catalyst, conducting heating in an inert atmosphere until the reaction is finished, removing the first solvent, conducting layering, taking lower-layer liquid, and conducting washing to obtain a quaternary ammonium salt intermediate; and mixing the quaternary ammonium salt intermediate with acyl chloride, adding a second solvent, conducting heating until the reaction is finished, removing the second solvent, conducting layering, taking lower-layer liquid, and conducting washing to obtain the double-branched-chain organosilicon quaternary ammonium salt. The double-branched-chain organosilicon quaternary ammonium salt disclosed by the invention has a continuous and long-acting sterilization effect and a good antibacterial and bacteriostatic effect.

Description

technical field [0001] The invention relates to the field of antibacterial agents and their preparation, more specifically, to a double-branched organosilicon quaternary ammonium salt and its preparation method and application. Background technique [0002] Antibacterial agents are mainly divided into inorganic antibacterial agents and organic antibacterial agents. Inorganic antibacterial agents include metal ion-type inorganic antibacterial agents and oxide photocatalytic inorganic antibacterial agents, which are subject to application restrictions because of their easy discoloration, high cost, and unstable antibacterial performance. Organic antibacterial agents are divided into natural, high molecular and small molecular organic antibacterial agents. Among them, among low-molecular organic antibacterial agents, quaternary ammonium salt organic antibacterial agents have received widespread attention because of their broad-spectrum antibacterial effect, good antibacterial ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/18A01N55/10A01P3/00
CPCC07F7/1804C07F7/1892A01N55/00
Inventor 陶红朱聪张坤孙浩
Owner 杭州昕洋生物科技有限公司
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