CN110201603B - Cationic surfactant and preparation method thereof - Google Patents
Cationic surfactant and preparation method thereof Download PDFInfo
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
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Abstract
The invention discloses a novel cationic surfactant and a preparation method thereof, in particular to indole quaternary ammonium of monodisperse pentadecyl three-arm polyglycol ether and a preparation method thereof. Starting from hydroxypentadecanoic acid, under the action of alkali, the pentadecanoic acid three-arm polyethylene glycol is obtained through one addition reaction with three-arm polyethylene glycol p-toluenesulfonate, the pentadecanoic acid three-arm polyethylene glycol and indole quaternary ammonium amine are subjected to addition reaction to obtain quaternary ammonium of pentadecanyl three-arm polyethylene glycol ether, and the quaternary ammonium of the pentadecanyl three-arm polyethylene glycol ether is obtained through acidification. The method can be used for preparing long-chain alkyl ether of monodisperse three-arm polyethylene glycol and indole quaternary ammonium salt thereof. The invention realizes the high-efficiency synthesis of pentadecanoic acid three-arm polyethylene glycol by using single molecular weight three-arm polyethylene glycol p-toluenesulfonic acid ester as a raw material, does not use carboxyl protecting groups in the synthesis, has simple and convenient steps, is suitable for industrial production, and has obvious advantages compared with the PEG aliphatic indole quaternary ammonium salt prepared in the prior art.
Description
Technical Field
The invention belongs to the field of pharmaceutical chemicals, and particularly relates to a preparation method of an indole quaternary ammonium salt of monodisperse pentadecyl three-arm polyglycol ether.
Background
The polar group in the cationic surfactant has positive charge, and an adsorption film with unique performance can be easily formed on the surface of a negatively charged substance: the solid surface has the performances of hydrophobization, softness, antistatic property, sterilization and the like, the performances not only are the application basis of the cationic surfactant in the traditional application field, but also widen the application field, and the cationic surfactant also has wide application in some high and new technologies which are rapidly developed in recent years.
Cationic surfactants were originally developed as bactericides, and it is known that the surface of bacteria has a multilayer structure consisting of protein lecithin and cytoplasm. The sterilization mechanism is of two types: the cationic surfactant has a polar group with positive charge, so that the cationic surfactant can generate a strong adsorption effect with the cell wall of bacteria with negative charge, and molecules of the cationic surfactant penetrate through a cell membrane to enter the interior of cells to finish a semi-permeation effect and interact with proteins in the cells to modify and settle the proteins to play a bactericidal effect; secondly, due to the strong adsorption effect of the cationic surfactant and the cell wall, a layer of closely arranged unique adsorption film can be formed on the interface of the bacterial cell wall and water or air, so as to block the breathing of bacterial organisms or cut off the nutrient source of bacteria, inhibit or kill the biological activity of bacteria and cause the bacteria to die. The bactericidal capacity depends on the permeability of cationic surfactant molecules to cells and the denaturation and sedimentation capacity of proteins, has wide application fields, and is mainly used in the fields of sterilization, disinfection, algae removal, mildew prevention and the like.
Traditional cationic surfactants, such as long-chain alkyl trimethyl ammonium chloride and dialkyl dimethyl ammonium chloride, reduce the foamability of the surfactant system, have poor biodegradability and water solubility, and have limited application range.
Therefore, there is a need to design a new cationic surfactant which can effectively sterilize bacteria and ensure foamability, biodegradability and water solubility of the surfactant.
Disclosure of Invention
The invention aims to provide a novel cationic surfactant aiming at the problems that the traditional cationic surfactant can reduce the foamability of a surfactant system and has poor biodegradability and water solubility.
The specific scheme is as follows: a novel cationic surfactant comprises the following main components in a structure of a formula I:
wherein n is a positive integer of not less than 1 and not more than 48.
Another object of the present invention is to provide a method for preparing the above novel cationic surfactant, comprising the steps of:
taking hydroxypentadecanoic acid as a raw material, and carrying out one-time addition reaction with three-arm polyethylene glycol p-toluenesulfonate under the action of alkali to obtain pentadecanoic acid three-arm polyethylene glycol;
carrying out condensation reaction on the pentadecanoic acid three-arm polyethylene glycol and indole quaternary ammonium amine to obtain quaternary ammonium of pentadecyl three-arm polyethylene glycol ether;
and acidifying the quaternary ammonium of the pentadecyl three-arm polyethylene glycol ether to obtain the indole quaternary ammonium salt of the pentadecyl three-arm polyethylene glycol ether.
Preferably, the base of the addition reaction is an inorganic base.
Preferably, the inorganic base is sodium hydride, sodium hydroxide.
Preferably, the condensation reaction is carried out under the action of an organic base.
Preferably, the organic base is DMAP, DIPEA; the condensing agent of the condensation reaction is HATU and EDCI.
Preferably, the acidification is hydrochloric acid acidification.
Preferably, the addition reaction is: the hydroxypentadecanoic acid and the monodisperse three-arm polyethylene glycol p-toluenesulfonate are subjected to addition reaction in an organic solvent under the action of alkali to obtain the monodisperse pentadecanoic acid three-arm polyethylene glycol.
Preferably, the organic solvent is toluene or DMF.
Preferably, the pentadecanoic acid three-arm polyethylene glycol is represented by formula II:
wherein n is a positive integer greater than or equal to 1 and less than or equal to 48.
Preferably, the process flow of the main components of the novel cationic surfactant is as follows:
compared with the prior art, the invention has the following advantages and effects:
1. the indole quaternary ammonium salt cationic surfactant of pentadecyl three-arm polyglycol ether has the following advantages: has better emulsifying, sterilizing and antistatic performances. Has small irritation, good compounding performance with other surfactants and wide application. Is a green surfactant, and has better biodegradability than the traditional quaternary ammonium salt cationic surfactant.
2. The invention realizes the high-efficiency synthesis of the long-chain alkyl alcohol ether of the glycol with more than two dimers and the indole quaternary ammonium salt thereof by using the single-molecular-weight three-arm polyethylene glycol p-toluene sulfonic acid ester as the raw material, does not use a carboxyl protecting group in the synthesis, has simple and convenient steps, is suitable for industrial production, and has obvious advantages compared with the prior prepared indole quaternary ammonium salt cationic surfactant in industrial practice because the product is the long-chain alkyl ether of the high-purity monodisperse polyethylene glycol and the indole quaternary ammonium salt thereof.
Detailed Description
Example one
Synthesis of indole quaternary ammonium salt of monodisperse pentadecyl three-arm dodecaethylene glycol ether
The synthesis process comprises three steps: (1) synthesis of Tri-armed dodecaethylene glycol p-toluenesulfonate 2) Synthesis of Tri-armed dodecaethylene glycol pentadecanoate; (3) synthesis of indole quaternary ammonium salt of pentadecyl three-arm dodecapolyethylene glycol ether.
(1) Synthesis of three-arm polyethylene glycol p-toluenesulfonate
0oUnder the condition of C, slowly dropwise adding p-toluenesulfonyl chloride (10 mmol) into a dichloromethane (30 ml) solution of three-arm dodecapolyethylene glycol (3 mmol) and triethylamine (3 mmol), and after the dropwise adding is finished, continuously stirring at normal temperature for 12 hours. The reaction was quenched with saturated sodium bicarbonate (100 mL), then separated, the organic phase was concentrated under reduced pressure, and the crude product was directly charged to the next reaction.
(2) Synthesis of pentadecanoic acid tribrachial dodecaethylene glycol
The reaction is carried out according to the following reaction formula: 0oUnder C, sodium hydride (12 mmol) was added to a solution of hydroxypentadecanoic acid (6 mmol) in toluene (150 mL), and after stirring at room temperature for 120 minutes, the reaction mixture was added with three-arm polyethylene glycol p-toluenesulfonate (2 mmol), reacted at room temperature for 24 hours, and quenched with water. Separating the reaction liquid, collecting the water phase, back-extracting the organic phase with a small amount of water, combining the water phases, and concentrating the water phase to obtain the pentadecanoic acid tribrachial dodecaethylene glycol.
(3) Synthesis of indole quaternary ammonium salt of pentadecyl three-arm dodecapolyethylene glycol ether
At normal temperature, 6mmol HATU and 6mol DMAP are added into a toluene (100 mL) solution of pentadecanoic acid tricarballyl acid (2 mmol) and stirred for 2 hours, indole quaternary ammonium amine (10 mmol) is added, after stirring for 2 hours at room temperature, the temperature is raised to 50 ℃, the reaction solution reacts for 12 hours at 50 ℃, after TLC tracing reaction is finished, 28% hydrochloric acid (10 mL) and water (10 mL) are added into the reaction system, and the reaction is continued for 2 hours at room temperature. The organic solvent is evaporated under reduced pressure, the water phase is washed by ethyl acetate for a plurality of times, and the water phase is concentrated to obtain the indole quaternary ammonium salt of pentadecyl three-arm dodecadiglycol ether.
Example two
Synthesis of indole quaternary ammonium salt of monodisperse pentadecyl three-arm twenty-four polyethylene glycol ether
The synthesis process comprises three steps: (1) synthesis of Tri-armed Docosyl Ether on DMF sulfonate 2) Synthesis of Tri-armed Docosyl Ether; (3) synthesis of indole quaternary ammonium salt of pentadecyl three-arm twenty-four polyethylene glycol ether.
(1) Synthesis of tri-arm tetracosanol p-toluenesulfonate
0oUnder C, slowly dropwise adding p-DMF sulfonyl chloride (10 mmol) into dichloromethane (30 ml) solution of three-arm twenty-four polyethylene glycol (3 mmol) and triethylamine (3 mmol), and stirring at normal temperature for 12 hours after dropwise adding. The reaction was quenched with saturated sodium bicarbonate (100 mL), then separated, the organic phase was concentrated under reduced pressure, and the crude product was directly charged to the next reaction.
(2) Synthesis of pentadecanoic acid triglycidyl ether
The reaction is carried out according to the following reaction formula: 0oUnder C, sodium hydride (12 mmol) was added to a solution of hydroxypentadecanoic acid (6 mmol) in DMF (150 mL), and after stirring at room temperature for 120 minutes, the reaction solution was added with tri-arm-eicosatetraolyethylene glycol p-toluenesulfonate (2 mmol), reacted at room temperature for 24 hours, and quenched with water. Separating the reaction liquid, collecting the water phase, back-extracting the organic phase with a small amount of water, combining the water phases, and concentrating the water phase to obtain the pentadecanoic acid triarachidon.
(3) Synthesis of indole quaternary ammonium salt of pentadecyl three-arm twenty-four polyethylene glycol ether
At normal temperature, 6mmol EDCI and 6mol DMAP are added into a solution of pentadecanoic acid tritetradecylpolyethylene glycol (2 mmol) in DMF (100 mL) and stirred for 2 hours, indole quaternary ammonium amine (10 mmol) is added, after stirring for 2 hours at room temperature, the temperature is raised to 50 ℃, the reaction solution reacts for 12 hours at 50 ℃, after TLC tracing reaction is finished, 28% hydrochloric acid (10 mL) and water (10 mL) are added into the reaction system, and the reaction is continued for 2 hours at room temperature. The organic solvent is evaporated under reduced pressure, the water phase is washed by ethyl acetate for a plurality of times, and the water phase is concentrated to obtain the indole quaternary ammonium salt of pentadecyl three-arm twenty-four polyethylene glycol ether.
EXAMPLE III
Synthesis of indole quaternary ammonium salt of monodisperse pentadecyl three-arm forty-eight polyethylene glycol ether
The synthesis process comprises three steps: (1) synthesis of three-armed forty-eight polyethylene glycol on DMF sulfonate 2) synthesis of pentadecanoic acid three-armed forty-eight polyethylene glycol; (3) synthesis of indole quaternary ammonium salt of pentadecyl three-arm forty-eight polyethylene glycol ether.
(1) Synthesis of three-arm forty-eight polyethylene glycol p-toluenesulfonate
0oC, slowly dropwise adding p-toluenesulfonyl chloride (10 mmol) into a dichloromethane (30 ml) solution of three-arm tetraoctadecylpolyethylene glycol (3 mmol) and triethylamine (3 mmol), and stirring at normal temperature for 12 hours after dropwise adding. The reaction was quenched with saturated sodium bicarbonate (100 mL), then separated, the organic phase was concentrated under reduced pressure, and the crude product was directly charged to the next reaction.
(2) Synthesis of pentadecanoic acid triatomic arm tetraoctadecanoethylene glycol
The reaction is carried out according to the following reaction formula: 0oC, adding sodium hydroxide (12 mmol) into a solution of hydroxypentadecanoic acid (6 mmol) in DMF (150 mL), stirring at room temperature for 120 minutes, adding three-arm forty-eight polyethylene glycol p-toluenesulfonate (2 mmol), and reacting at 60%oThe reaction was carried out for 24 hours at C and quenched with water. Separating the reaction liquid, collecting the water phase, back-extracting the organic phase with a small amount of water, combining the water phases, and concentrating the water phase to obtain the pentadecanoic acid triarachialba forty-eight polyethylene glycol.
(3) Synthesis of indole quaternary ammonium salt of pentadecyl three-arm forty-eight polyglycol ether
At normal temperature, 6mmol of EDCI and 6mol of DIPEA are added into a solution of pentadecanoic acid tricarballyl acid (2 mmol) in DMF (100 mL) and stirred for 2 hours, indole quaternary ammonium amine (10 mmol) is added, after stirring for 2 hours at room temperature, the temperature is raised to 50 ℃, the reaction solution reacts at 50 ℃ for 12 hours, after TLC tracing reaction is finished, 28% hydrochloric acid (10 mL) and water (10 mL) are added into the reaction system, and the reaction is continued for 2 hours at room temperature. The organic solvent is evaporated under reduced pressure, the water phase is washed by ethyl acetate for a plurality of times, and the water phase is concentrated to obtain the indole quaternary ammonium salt of pentadecyl three-arm forty-eight polyethylene glycol ether.
Example four
Bacteriostatic property of indole quaternary ammonium salt of pentadecyl three-arm polyglycol ether
1. Bactericidal effect of indole quaternary ammonium salt of pentadecyl three-arm dodecadiglycol ether on staphylococcus aureus
The bactericidal effect of the indole quaternary ammonium salt of pentadecyl three-arm dodecapolyethylene glycol ether, the indole quaternary ammonium salt of pentadecyl three-arm twenty-four polyethylene glycol ether and the indole quaternary ammonium salt of pentadecyl three-arm forty-eight polyethylene glycol ether on staphylococcus aureus is respectively measured, two concentration gradients are set, 15 mu L of surfactant solution with the concentration of 30 mu L of 5mmol/L is respectively added into a filter paper sheet, and the bactericidal effect is shown in a table 1-1:
the specific numerical values of the inhibition zones are shown in the table. As can be seen from the data in Table 1-1, the indole quaternary ammonium salt series surfactants of pentadecyl three-arm polyglycol ether synthesized by the experiment all have certain bactericidal and bacteriostatic effects on Escherichia coli, which can also be seen from the data in Table 1-1. Then, a comparison experiment is carried out on the fact that the concentration gradient of the indole quaternary ammonium salt series surfactant of the pentadecyl three-arm twenty-four polyethylene glycol ether is increased, and the fact that the indole quaternary ammonium salt series surfactant of the pentadecyl three-arm twenty-four polyethylene glycol ether increases the antibacterial activity is found; meanwhile, compared with the same concentration gradient, the indole quaternary ammonium salt of the pentadecyl three-arm forty-eight polyethylene glycol ether has the advantage that the diameter of the inhibition zone is obviously changed and increased. Although the indole quaternary ammonium salt series surfactant of pentadecyl three-arm polyglycol ether can not directly kill staphylococcus aureus, the indole quaternary ammonium salt series surfactant has certain effect of inhibiting the growth and the reproduction of the staphylococcus aureus to a certain extent.
2. Bactericidal effect of indole quaternary ammonium salt of pentadecyl three-arm polyglycol ether on bacillus subtilis
The sterilizing effects of the indole quaternary ammonium salt of pentadecyl three-arm dodecapolyethylene glycol ether, the indole quaternary ammonium salt of pentadecyl three-arm twenty-four polyethylene glycol ether and the indole quaternary ammonium salt of pentadecyl three-arm forty-eight polyethylene glycol ether on bacillus subtilis are respectively measured, two concentration gradients are set, 15 mu L of surfactant solution with the concentration of 30 mu L of 5mmol/L is respectively added into a filter paper sheet, and the sterilizing effects are shown in tables 1-2:
from tables 1-2, it can be seen that the effect is obvious, the inhibition zone is very clear, the comparison of the diameter of the inhibition zone is very obvious compared with the indole quaternary ammonium salt of pentadecyl three-arm forty-eight polyethylene glycol ether, the sterilization effect of the indole quaternary ammonium salt of pentadecyl three-arm twenty-four polyethylene glycol ether on bacillus subtilis is far higher than that of the indole quaternary ammonium salt of pentadecyl three-arm forty-eight polyethylene glycol ether, and tables 1-2 verify the point numerically; from tables 1-2, we can see that the diameter of the inhibition zone of the indole quaternary ammonium salt of the pentadecyl three-arm twenty-four polyethylene glycol ether is not greatly changed in the concentration gradients of 15 μ L and 30 μ L, which shows that the indole quaternary ammonium salt of the pentadecyl three-arm twenty-four polyethylene glycol ether has the greatest effect on the sterilization effect of the bacillus subtilis in the concentration range, and in order to examine the influence of different concentrations of the indole quaternary ammonium salt of the pentadecyl three-arm twenty-four polyethylene glycol ether on the sterilization activity of the bacillus subtilis, the indole quaternary ammonium salt of the pentadecyl three-arm twenty-four polyethylene glycol ether at low concentration is also examined on the sterilization effect of the bacillus subtilis.
As can be seen from tables 1-3, the diameter of the inhibition zone becomes larger with the increase of the concentration of the indole quaternary ammonium salt of the pentadecyl three-arm twenty-four polyethylene glycol ether, the diameter contrast is obvious, when the addition amount of the indole quaternary ammonium salt of the pentadecyl three-arm twenty-four polyethylene glycol ether reaches 20 mu L (10 mmol/L), the diameter of the inhibition zone reaches the maximum, and the change of the diameter of the inhibition zone is not obvious with the increase of the addition amount of the indole quaternary ammonium salt of the pentadecyl three-arm twenty-four polyethylene glycol ether.
EXAMPLE five
Measurement of foam Properties
Taking the compounds of the first embodiment, the second embodiment and the third embodiment, preparing a surfactant, respectively placing the surfactant in test tubes, and marking 1, 2 and 3; placing common surfactant in test tube 4, and placing long-chain alkyl trimethyl ammonium chloride in test tube 5. In which test tubes 4, 5 are the control group. The test tubes 1, 2, 3, 4, 5 were dissolved in 50ml of distilled water, respectively, until ready for use. Carefully remove 25.0mL of the test solution into the cuvette using rinsed pipettes, cover the stopper, press the stopper with the index finger, shake the cuvette 10 times with force, measure the height of the foam with a ruler after the foam is generated and record the results as shown in Table 4.
As can be seen from Table 4, the compounds of examples 1, 2, 3 have foam properties close to those of conventional surfactants, and are much higher than those of conventional cationic surfactants.
Claims (10)
1. A cationic surfactant is characterized in that the main component is a structure shown in a formula I:
wherein n is a positive integer of not less than 1 and not more than 48.
2. A method for preparing the cationic surfactant according to claim 1, comprising the steps of:
taking hydroxypentadecanoic acid as a raw material, and carrying out one-time addition reaction with three-arm polyethylene glycol p-toluenesulfonate under the action of alkali to obtain pentadecanoic acid three-arm polyethylene glycol;
carrying out condensation reaction on the pentadecanoic acid three-arm polyethylene glycol and indole quaternary ammonium amine to obtain a quaternization product of pentadecyl three-arm polyethylene glycol ether;
and acidifying the quaternization product of the pentadecyl three-arm polyethylene glycol ether to obtain the indole quaternary ammonium salt of the pentadecyl three-arm polyethylene glycol ether.
3. The method for producing the cationic surfactant according to claim 2, characterized in that: the base of the addition reaction is an inorganic base.
4. A method for producing the cationic surfactant according to claim 3, characterized in that: the inorganic base is sodium hydride or sodium hydroxide.
5. The method for producing the cationic surfactant according to claim 2, characterized in that: the condensation reaction is carried out under the action of an organic base.
6. The method for producing a cationic surfactant according to claim 5, characterized in that: the organic alkali is DMAP and DIPEA; the condensing agent of the condensation reaction is HATU and EDCI.
7. The method for producing a cationic surfactant according to claim 2, characterized in that: the acidification is hydrochloric acid acidification.
8. The method for producing the cationic surfactant according to claim 2, wherein the addition reaction is: the hydroxypentadecanoic acid and the monodisperse three-arm polyethylene glycol p-toluenesulfonate are subjected to addition reaction in an organic solvent under the action of alkali to obtain the monodisperse pentadecanoic acid three-arm polyethylene glycol.
9. The method for producing a cationic surfactant according to claim 8, characterized in that: the organic solvent is toluene or DMF.
10. The method for producing the cationic surfactant according to any one of claims 2 to 9, characterized in that: the pentadecanoic acid three-arm polyethylene glycol is shown as a formula II:
wherein n is a positive integer greater than or equal to 1 and less than or equal to 48.
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