Trimeric quaternary ammonium salt surfactant constructed by dynamic imine bonds, preparation method and application thereof

A compound, selected technology, applied in the fields of botanical equipment and methods, preparation of organic compounds, preparation of imino compounds, etc., can solve problems such as unreported

Active Publication Date: 2020-09-15
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There have been some reports on single-chain and Gemini surfactants constructed by dynamic

Method used

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  • Trimeric quaternary ammonium salt surfactant constructed by dynamic imine bonds, preparation method and application thereof
  • Trimeric quaternary ammonium salt surfactant constructed by dynamic imine bonds, preparation method and application thereof
  • Trimeric quaternary ammonium salt surfactant constructed by dynamic imine bonds, preparation method and application thereof

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preparation example Construction

[0103] The preparation method of the present invention will be further described in detail below in conjunction with specific examples. It should be understood that the following embodiments are only illustrative and explaining the present invention, and should not be construed as limiting the protection scope of the present invention. All technologies implemented based on the foregoing contents of the present invention are covered by the scope of the present invention.

[0104] The experimental methods used in the following examples are conventional methods unless otherwise specified; the reagents and materials used in the following examples, unless otherwise specified, can be obtained from commercial sources.

preparation example 1

[0105] Preparation Example 1. Preparation of raw material 4-(3-bromopropyl)-benzaldehyde

[0106]

[0107] Dissolve 20g (100mmol) of 1-bromo-3-phenylpropane in 120mL of dichloromethane, cool to 0-5°C in an ice bath, and add 28.45g (150mmol) of TiCl 4 As a catalyst, keep the temperature at 0-2°C, and then slowly add the carbonylation reagent 1,1-dichloromethyl ether 10.44 (90mmol) to the mixed system dropwise. After the dropwise addition, continue to stir and react for 5 minutes, and slowly raise the temperature to 35°C Continue to stir for 15 min. After the reaction, the reaction mixture is slowly poured into a flask filled with ice water, and then transferred to a separatory funnel, extracted twice with dichloromethane to obtain the organic phase, and then saturated NaHCO 3 The organic phase was washed with aqueous solution, and the solvent was evaporated to obtain a crude product, which was then subjected to column chromatography (ethyl acetate / petroleum ether volume ratio 1:7 as...

preparation example 2

[0112] Preparation Example 2. Quaternary ammonium salt compound TDA-(PhC=O) 3 Preparation

[0113]

[0114] Dissolve 2.76g (12mmol) of tris-(2-dimethylaminoethyl)amine in a 1:5 mixed solvent of 120ml ethanol and acetone, protect the reaction mixture with nitrogen, stir and heat to reflux temperature, then add 10.896g The raw material 4-(3-bromopropyl)-benzaldehyde (48 mmol) was added dropwise to the above mixture, and the reaction was continued for 48 hours after the addition was completed, until the reactants reached a higher conversion rate (the conversion rate of the reaction was monitored by mass spectrometry). After the reaction, the reaction mixture was cooled to room temperature, and acetone was added to wash the reaction mixture. After washing, the mixture is filtered to obtain a filter residue, and the filter residue is washed 3 times with the above-mentioned washing reagent. After filtration, the organic solvent is evaporated to dryness, and a yellow-brown solid crude p...

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Abstract

The invention discloses a trimeric cationic quaternary ammonium salt surfactant constructed by dynamic imine bonds, a preparation method and application thereof. The preparation method is simple in preparation process, mild in reaction condition, short in reaction period, simple in post-treatment and easy for industrial production. The trimeric cationic quaternary ammonium salt compound disclosedby the invention can be dissociated under the action of acid or CO2, can be used as a surfactant, has good surface activity and aggregation behavior, and can be applied to washing, emulsification, phase transfer catalysts, micelle catalysis, substance extraction, substance separation and promotion of spreading of water drops on a super-hydrophobic surface, and in an example, the aqueous solution of the trimeric quaternary ammonium salt compound can also form liquid-liquid phase separation and is applied to embedding, slow release, storage and enrichment of substances.

Description

Technical field [0001] The invention relates to the technical field of novel compounds containing quaternary ammonium salts, in particular to a tripolycationic quaternary ammonium salt surfactant constructed by dynamic imine bonds, and a preparation method and application thereof. Background technique [0002] Trimeric surfactants have a lower critical aggregation concentration, higher surface activity, higher aggregate charge density and richer aggregation behavior than traditional single-chain surfactants and Gemini surfactants, so they have more abundant Application potential. However, the traditional covalent bond type trimerized surfactants are generally difficult to synthesize and expensive, which limits the application of trimerized surfactants. On the one hand, the existing thinking is to optimize the synthesis route of trimeric surfactants, but it still faces many obstacles; on the other hand, it is to construct trimeric surfactants through non-covalent bond constructio...

Claims

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Application Information

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IPC IPC(8): C07C251/24C07C249/02B01F17/18C07C223/06C07C221/00A01N25/30C09B67/02C09K23/18
CPCC07C251/24C07C249/02C07C223/06A01N25/30C09B67/0008C09B67/0097C09K23/00
Inventor 王毅琳刘斌范雅珣李浩飞赵微微罗思琪王华
Owner INST OF CHEM CHINESE ACAD OF SCI
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