Rosinyl quaternary ammonium salt dimeric surfactant as well as preparation method and application thereof

A technology of rosin-based quaternary ammonium salts and gemini surfaces, which is applied in the preparation of amino compounds, botany equipment and methods, applications, etc., can solve the problems that the research on rosin-based heterogemini surfactants has not been reported, and achieve good surface activity and Bacteriostatic properties, high efficiency, and short-term effects

Active Publication Date: 2014-02-26
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there are also reports about symmetrical rosin-based gemini surfactan...

Method used

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  • Rosinyl quaternary ammonium salt dimeric surfactant as well as preparation method and application thereof
  • Rosinyl quaternary ammonium salt dimeric surfactant as well as preparation method and application thereof
  • Rosinyl quaternary ammonium salt dimeric surfactant as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Synthesis of N,N-dimethylabietinamine:

[0040] With dichloromethane as solvent, SOCl 2 (2.4g, 20mmol) and abietic acid (3.0g, 10mmol) reacted 4h at reflux temperature, removed solvent and excess SOCl 2 Obtain abietic acid chloride. Dissolve the obtained abietic acid chloride in 20mL of tetrahydrofuran, slowly add it dropwise into 40% dimethylamine aqueous solution (4.5g, 40mmol) at 0°C and react for 4h. After the reaction is completed, filter, and the filtrate is acidified and alkalized. 1. After washing with water, distill off the solvent under reduced pressure to obtain N,N-dimethyl dehydroabietamide. Finally, N,N-dimethyl dehydroabietamide was dissolved in tetrahydrofuran solvent, lithium aluminum hydride (0.8g, 20mmol) was added with stirring at 0°C, and the temperature was slowly raised to 70°C and reacted for 6h. After the reaction is completed, continue to dropwise add water equivalent to the quality of lithium aluminum hydride and 15% sodium hydroxide soluti...

Embodiment 2

[0042] Synthesis of bromoalkyl abietyl dimethyl ammonium bromide:

[0043] (1) Synthesis of 3-bromopropyl abietyl dimethyl ammonium bromide (n=3):

[0044] Take N,N-dimethyl abietamine (3.1g, 10mmol) in a reactor filled with absolute ethanol, add 1,3-dibromopropane (2.0g, 10mmol) dropwise under stirring, and react at 50°C for 30h Afterwards, the temperature was raised to 80° C., and the reaction was continued for 8 hours. After the reaction was completed, the solvent was distilled off under reduced pressure, excess dibromopropane was washed off with petroleum ether, and dried to obtain 3-bromopropyl abietyl dimethyl ammonium bromide.

[0045] (2) Synthesis of 4-bromobutyl abietyl dimethyl ammonium bromide (n=4):

[0046] Take N,N-dimethyl abietamine (3.1g, 10mmol) in a reactor filled with absolute ethanol, add 1,4-dibromobutane (7.4g, 35mmol) dropwise under stirring, and react at 50°C After 24h, react at 80°C for another 24h. After the reaction was completed, the solvent w...

Embodiment 3

[0050] Synthesis of rosin-based quaternary ammonium salt heterogemini surfactant:

[0051] (1) Synthesis of conventional heating rosin-based quaternary ammonium salt heterogemini surfactant A:

[0052] Add N,N-dimethyldodecylamine (2.3g, 10.5mmol) and 3-bromopropyl abietyl dimethylammonium bromide ( 4.1g, 10mmol) and 100ml acetone, heated, stirred and refluxed for 36h. After the reaction was completed, the solvent was distilled off under reduced pressure, followed by recrystallization and vacuum drying to obtain the rosin-based quaternary ammonium salt heterogemini surfactant A with a yield of 70%.

[0053] (2) Synthesis of Rosin-based Quaternary Ammonium Heterogemini Surfactant A by Microwave Radiation:

[0054] Add N,N-dimethyldodecylamine (2.3g, 10.5mmol) and 3-bromopropyl abietyl dimethylammonium bromide (4.1g, 10mmol) to a 100ml round bottom single-necked bottle, in 40ml acetone Dissolved in a microwave reactor and placed in a microwave reactor, the microwave reaction ...

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Abstract

The invention discloses a rosinyl quaternary ammonium salt dimeric surfactant as well as a preparation method and application thereof. The molecular structural formula of the rosinyl quaternary ammonium salt dimeric surfactant is as shown in the specification, wherein R is a rosinyl tricyclic phenanthrene structure, and n is equal to 3, 4, 5 or 6. The rosinyl quaternary ammonium salt dimeric surfactant which takes rosin as a raw material satisfies the demand of environment-friendly raw materials for preparation of the surfactant. The surfactant prepared by the invention has good surface activity and antibacterial activity. The CMC (Critical Micelle Concentration) value of the surfactant is (2.28-3.38)*10<-5>mol/L, the gamma cmc value is 24.7-32.3mN/m, and the Krafft point ranges from 12 to 23 DEG C. The time of separating turpentine and water in an aqueous emulsion is 42-53 hours. The initial foaming height is 128-137mm. The foam height in 5 minutes is 121-131mm. The antibacterial activity of the surfactant to escherichia coli is superior to that of the marketed bacteriostatic agent bromogeramine.

Description

technical field [0001] The invention relates to a rosin-based quaternary ammonium salt heterogemini surfactant, a preparation method and application thereof, and belongs to the field of surfactant science and application. Background technique [0002] Gemini surfactants with high surface activity are research hotspots in the field of surfactants in recent years. The commonly studied gemini surfactant is a symmetrical structure formed by connecting two identical surfactant molecules at or close to the hydrophilic group through a linking group, that is, a gemini surfactant with a symmetrical molecular structure. Heterogemini surfactants with asymmetrical molecular structure contain head groups of different chemical structures, alkane main chains of different lengths and varied linking chains, so it is possible to obtain surfactants with better performance. It plays an important role in understanding the mechanism of molecular self-organization and building ordered molecular a...

Claims

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Application Information

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IPC IPC(8): B01F17/18C07C209/12C07C211/31A01N33/12A01P1/00C09K23/18
Inventor 商士斌王娟王丹宋杰沈明贵饶小平齐帆
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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