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Degradable cationic Gemini surface active agent

A surfactant, cationic technology, applied in the directions of dissolution, biocide, bactericide, etc., can solve the problems of unfriendly environment, drug resistance, refractory degradation, etc., and achieve the effect of environmental friendliness, easy biodegradation, and good sterilization

Inactive Publication Date: 2011-08-31
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, most of the single-chain quaternary ammonium cationic surfactants in the market are difficult to degrade as fungicides and are not friendly to the environment; and if the same fungicide is used for a long time, microorganisms will develop resistance to it

Method used

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  • Degradable cationic Gemini surface active agent
  • Degradable cationic Gemini surface active agent
  • Degradable cationic Gemini surface active agent

Examples

Experimental program
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preparation example Construction

[0023] The method for the compound shown in the preparation formula I provided by the invention, its synthetic route is as follows:

[0024]

[0025] Specifically include the following steps:

[0026] (1) Put the aliphatic carboxylic acid (compound shown in formula IV) and hydroxyl-containing tertiary amine (compound shown in formula V) in a molar ratio of 1: (1.5~2.0) in the reactor, add catalyst, in reflux state Keep for 8 hours to 15 hours to obtain an intermediate (compound shown in formula VI); and

[0027] (2) The compound shown in formula VI and the corresponding halogenated hydrocarbon are placed in another reactor in a molar ratio of (2 to 3): 1, and ethyl acetate is used as the reaction solvent, and kept in a reflux state for at least 48 hours, The target compound (compound represented by formula I) was obtained.

[0028] The cationic surfactant designed and prepared by the invention has good bactericidal and bacteriostatic properties to Staphylococcus aureus, E...

Embodiment 1

[0032] The synthesis of cationic surfactant shown in formula I-1

[0033]

[0034] (1) Synthesis of long-chain ester group tertiary amine:

[0035] Add 0.01mol dodecanoic acid and 0.02mol hydroxyl-containing tertiary amine (compound shown in formula V, R 1 and R 2 Both CH 3 , m=2), add 1-3‰ p-toluenesulfonic acid and 50ml xylene, reflux reaction for 10h, judge the reaction process with a water trap, stop the reaction when anhydrous is generated, and fractionate to obtain a long-chain ester group tertiary amine;

[0036] (2) Synthesis of target object (compound shown in formula I-1):

[0037] Add 0.02mol and 0.01mol of the long-chain ester-based tertiary amine prepared in the step (1) into the three-necked flask, add 50ml of ethyl acetate as a solvent, and react at room temperature for 48h to obtain the crude product Recrystallized from dichloromethane and ethyl acetate to obtain the target compound (compound represented by formula I-1).

[0038] 1 H NMR (CDCl 3 , 400...

Embodiment 2

[0040] The synthesis of cationic surfactant shown in formula I-2

[0041]

[0042] Add 0.02mol of long-chain ester group tertiary amine and 0.01mol of 1,4-dibromobutene-2 ​​in the three-necked flask, and add 50ml of ethyl acetate as a solvent, react at room temperature for 48h, and recrystallize the crude product. The obtained crude product was recrystallized from dichloromethane and ethyl acetate to obtain the target compound (compound represented by formula I-2).

[0043] 1 H NMR (CDCl 3 , 400MHz): δ6.64(s, J=8.0Hz, 2H), 5.08(d, J=4.8Hz, 4H), 4.58(d, J=2.0Hz, 4H), 4.13(s, 4H), 3.48 (s, 16H), 2.37 (t, J = 7.6Hz, 4H), 1.23 (s, 32H), 0.88 (t, J = 6.8Hz, 6H).

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Abstract

The invention relates to a cationic Gemini surface active agent (which comprises a Gemini type cationic surface active agent). The cationic Gemini surface active agent is a chemical compound as shown in the formula I. The cationic Gemini surface active agent not only is good in sterilization performance, but also can be biodegraded. In the formula I, R1 and R2 are respectively and independently selected from one of C1-C6 catenulate alkyls; R3 is C7-C20 catenulate alkyl or catenulate perfluor alkyl; m is an integral number from 1 to 6; n is 2 or 3; A is C1-C6 catenulate unsaturated alkyl, or a C7-C24 aromatic ring group; and X is halogen.

Description

technical field [0001] The invention relates to a cationic surfactant, in particular to a cationic quaternary ammonium salt surfactant (including a Gemini cationic surfactant) which meets the requirements in the field of cosmetics. Background technique [0002] Cationic surfactants have a strong adsorption capacity on the surface of the substance, and the molecules can form a thin film on the surface of the substance, which has the properties of softness, antistatic, anticorrosion, protein precipitation and sterilization. In particular, quaternary ammonium salt cationic surfactants, in addition to the basic characteristics of other cationic surfactants, have particularly outstanding characteristics of killing bacteria, and are widely used in many fields. Dodecyl dimethyl benzyl bromide quaternary ammonium salt cationic surfactant is a commonly used fungicide. [0003] The bactericidal mechanism of cationic quaternary ammonium salt surfactants is mainly to use positive charg...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01F17/18A01N37/12A01P3/00C09K23/18
Inventor 王利民胡霞云韩超杨阳何铭铭田禾
Owner EAST CHINA UNIV OF SCI & TECH
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