CN110201603A - Novel Cationic Surfactants and preparation method thereof - Google Patents
Novel Cationic Surfactants and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a kind of Novel Cationic Surfactants and preparation method thereof, specially the indoles quaternary ammonium and preparation method of three arm polyglycol ether of monodisperse pentadecyl.From hydroxypentadecanoic acid, three arm polyethylene glycol of pentadecanoic acid is obtained by an addition reaction with three arm polyethylene glycol p-methyl benzenesulfonic acid esters in the presence of alkali, three arm polyethylene glycol of pentadecanoic acid and indoles quaternary ammonium amines occur addition reaction and obtain the quaternary ammonium of three arm polyglycol ether of pentadecyl, and acidification obtains the indoles quaternary ammonium salt of three arm polyglycol ether of pentadecyl.This method can be used in the preparation of the chain alkyl ether and its indoles quaternary ammonium salt of three arm polyethylene glycol of monodisperse.The present invention realizes efficiently synthesizing for three arm polyethylene glycol of pentadecanoic acid using three arm polyethylene glycol p-methyl benzenesulfonic acid ester of unimodal molecular weight as raw material; without using carboxyl-protecting group in synthesis; step is easy; suitable for industrialized production, obtained product has apparent advantage relative to the PEGylated aliphatic indoles quaternary ammonium salt of existing preparation.
Description
Technical field
The invention belongs to field of medicine and chemical technology, and in particular to a kind of indoles of three arm polyglycol ether of monodisperse pentadecyl
The preparation method of quaternary ammonium salt.
Background technique
Polar group in cationic surfactant has positive charge, can be easy to be formed in electronegative material surface
The adsorbed film of unique energy: performances, these performances such as solid hydrophobic surface, softness, antistatic and sterilization are not only
Application foundation of the cationic surfactant in traditional application field, and its application field has been widened, in recent years quickly
It also obtains and is widely applied in some new and high technologies of development.
Cationic surfactant is initially used as fungicide research and development, it is understood that the surface of bacterium
There is multilayered structure, is made of albumen Lecithin, cytoplasm.There are two types of its sterilization mechanisms: one, cationic surfactant due to
There is positively charged polar group, stronger suction-operated, cation form can occur with the cell wall of negatively charged bacterium
Face active agent molecule enters cell interior through cell membrane, completes semi-permeable effect, interacts with the protein of cell interior,
Bactericidal effect is played into protein-modified sedimentation；Two, since the strong adsorption of cationic surfactant and cell wall acts on,
It can form one layer of arrangement closely unique adsorbed film on the interface of bacteria cell wall and water or air, bacterium is blocked with this
The breathing of organism or the nutriment source for cutting off bacterium inhibit or kill the bioactivity of bacterium and cause bacterium dead
It dies.Sterilizing ability depends on permeability of the cationic surfactant molecule to cell and the denaturation to protein settles energy
Power, application field is extensive, is mainly used for sterilization, disinfection, except the fields such as algae, mould proof.
Traditional cationic surfactant, such as chlorination chain alkyl trimethyl ammonium and the double alkyl dimethyl ammoniums of chlorination, meeting
The spumescence of surfactant system is reduced, biological degradability and water solubility are poor, and application range is restricted.
Therefore, it needs to design a kind of new cationic surfactant, can either effectively sterilize, and can guarantee that surface is living
Spumescence, biological degradability and the water solubility of property agent.
Summary of the invention
It is an object of the invention to the foam of surfactant system can be reduced for traditional cationic surfactant
Property, biological degradability and water-soluble poor provide a kind of new cationic surfactant.
Concrete scheme is as follows: a kind of Novel Cationic Surfactants, and main component is Formulas I structure:
Wherein, n takes the positive integer more than or equal to 1, less than or equal to 48.
Another object of the present invention is to provide a kind of preparation methods of above-mentioned Novel Cationic Surfactants, including
Following steps:
Using hydroxypentadecanoic acid as raw material, in the presence of alkali by once adding with three arm polyethylene glycol p-methyl benzenesulfonic acid esters
Three arm polyethylene glycol of pentadecanoic acid is obtained at reaction；
The three arm polyethylene glycol of pentadecanoic acid is obtained three arm of pentadecyl with the generation condensation reaction of indoles quaternary ammonium amines to gather
The quaternary ammonium of glycol ether；
It is acidified the quaternary ammonium of the three arm polyglycol ether of pentadecyl to obtain the Yin of three arm polyglycol ether of pentadecyl
Diindyl quaternary ammonium salt.
Preferably, the alkali of the addition reaction is inorganic base.
Preferably, the inorganic base is sodium hydride, sodium hydroxide.
Preferably, the condensation reaction carries out under organic base effect.
Preferably, the organic base is DMAP, DIPEA；The condensing agent of the condensation reaction is HATU and EDCI.
Preferably, the acidification is that hydrochloric acid is acidified.
Preferably, the addition reaction are as follows: hydroxypentadecanoic acid in the presence of alkali with three arm polyethylene glycol pair of monodisperse
Tosylate carries out addition reaction in organic solvent and obtains three arm polyethylene glycol of monodisperse pentadecanoic acid.
Preferably, the organic solvent is toluene or DMF.
Preferably, the three arm polyethylene glycol of pentadecanoic acid is as shown in Formula II:
Wherein, n is to be less than or equal to 48 positive integers more than or equal to 1.
Preferably, the process flow of the main component of the Novel Cationic Surfactants is as follows:
The present invention has the following advantages compared with the prior art and effect:
1. the indoles quaternary cationics of three arm polyglycol ether of pentadecyl of the invention have following excellent
Point: there are the performances such as preferably emulsification, sterilization, antistatic.Irritation is small, good with the compound property of other surfaces activating agent, application
Extensively.For green surfactant, biological degradability is better than traditional quaternary cationics.
2. the present invention realizes the above second two of dimerization using three arm polyethylene glycol p-methyl benzenesulfonic acid ester of unimodal molecular weight as raw material
The chain alkyl alcohol ether of alcohol and efficiently synthesizing for its indoles quaternary ammonium salt, without using carboxyl-protecting group in synthesis, step is easy,
Suitable for industrialized production, and product is the chain alkyl ether and its indoles quaternary ammonium salt of the monodispersity polyethylene glycol of high-purity,
There is apparent advantage relative to the indoles quaternary cationic surfactant of existing preparation on industrial practice.
Specific embodiment
Embodiment one
The synthesis of the indoles quaternary ammonium salt of three arm of monodisperse pentadecyl, 12 polyglycol ether
Synthesis process contains three steps: (1) synthesis 2 of three arms, 12 polyethylene glycol p-methyl benzenesulfonic acid ester) pentadecanoic acid three
The synthesis of 12 polyethylene glycol of arm；(3) synthesis of the indoles quaternary ammonium salt of three arm of pentadecyl, 12 polyglycol ether.
The synthesis of (1) three arm polyethylene glycol p-methyl benzenesulfonic acid ester
At 0 DEG C, in methylene chloride (30ml) solution of three arms, 12 polyethylene glycol (3mmol) and triethylamine (3mmol)
Paratoluensulfonyl chloride (10mmol) is slowly added dropwise, room temperature continues stirring 12 hours after completion of dropwise addition.Reaction passes through unsaturated carbonate hydrogen
Sodium (100mL) is quenched, then liquid separation, and after organic phase is concentrated under reduced pressure, crude product direct plunges into react in next step.
(2) synthesis of three arm of pentadecanoic acid, 12 polyethylene glycol
It is reacted by following reaction formula, specifically: at 0 DEG C, to the toluene (150mL) of hydroxypentadecanoic acid (6mmol)
Sodium hydride (12mmol) is added in solution, after being stirred at room temperature 120 minutes, three arm polyethylene glycol p-methyl benzenesulfonic acid esters are added
(2mmol), reaction solution react 24 hours at room temperature, and reaction is quenched with water.By reaction solution liquid separation, water phase is collected, organic phase is used
A small amount of water back extraction, merges water phase, and concentration water phase obtains three arm of pentadecanoic acid, 12 polyethylene glycol.
(3) synthesis of the indoles quaternary ammonium salt of three arm of pentadecyl, 12 polyglycol ether
Under room temperature, first it is added into toluene (100mL) solution of three arm of pentadecanoic acid, 12 polyethylene glycol (2mmol)
The DMAP of the HATU and 6mol of 6mmol are stirred 2 hours, are added indoles quaternary ammonium amines (10mmol), after being stirred at room temperature 2 hours, heating
To 50 degree, reaction solution reacts 12 hours under 50 degree, and TLC is tracked after reaction, and 28% hydrochloric acid is added into reaction system
(10ml) and water (10mL), the reaction was continued 2 hours for room temperature.Organic solvent removes under reduced pressure, and water phase is washed repeatedly with ethyl acetate,
Concentration water phase obtains the indoles quaternary ammonium salt of three arm of pentadecyl, 12 polyglycol ether.
Embodiment two
The synthesis of the indoles quaternary ammonium salt of three arm of monodisperse pentadecyl, 24 polyglycol ether
Synthesis process contains three steps: (1) synthesis 2 of three arms, 24 polyethylene glycol to DMF sulphonic acid ester) pentadecanoic acid three
The synthesis of 24 polyethylene glycol of arm；(3) synthesis of the indoles quaternary ammonium salt of three arm of pentadecyl, 24 polyglycol ether.
The synthesis of 24 polyethylene glycol p-methyl benzenesulfonic acid ester of (1) three arm
At 0 DEG C, to methylene chloride (30ml) solution of three arms, 24 polyethylene glycol (3mmol) and triethylamine (3mmol)
In be slowly added dropwise to DMF sulfonic acid chloride (10mmol), room temperature continues stirring 12 hours after completion of dropwise addition.Reaction passes through unsaturated carbonate hydrogen
Sodium (100mL) is quenched, then liquid separation, and after organic phase is concentrated under reduced pressure, crude product direct plunges into react in next step.
(2) synthesis of three arm of pentadecanoic acid, 24 polyethylene glycol
It is reacted by following reaction formula, specifically: at 0 DEG C, to the DMF (150mL) of hydroxypentadecanoic acid (6mmol)
Sodium hydride (12mmol) is added in solution, after being stirred at room temperature 120 minutes, three arms, 24 polyethylene glycol p-methyl benzenesulfonic acid ester is added
(2mmol), reaction solution react 24 hours at room temperature, and reaction is quenched with water.By reaction solution liquid separation, water phase is collected, organic phase is used
A small amount of water back extraction, merges water phase, and concentration water phase obtains three arm of pentadecanoic acid, 24 polyethylene glycol.
(3) synthesis of the indoles quaternary ammonium salt of three arm of pentadecyl, 24 polyglycol ether
Under room temperature, first it is added into DMF (100mL) solution of three arm of pentadecanoic acid, 24 polyethylene glycol (2mmol)
The DMAP of the EDCI and 6mol of 6mmol are stirred 2 hours, are added indoles quaternary ammonium amines (10mmol), after being stirred at room temperature 2 hours, heating
To 50 degree, reaction solution reacts 12 hours under 50 degree, and TLC is tracked after reaction, and 28% hydrochloric acid is added into reaction system
(10ml) and water (10mL), the reaction was continued 2 hours for room temperature.Organic solvent removes under reduced pressure, and water phase is washed repeatedly with ethyl acetate,
Concentration water phase obtains the indoles quaternary ammonium salt of three arm of pentadecyl, 24 polyglycol ether.
Embodiment three
The synthesis of the indoles quaternary ammonium salt of three arm of monodisperse pentadecyl, 48 polyglycol ether
Synthesis process contains three steps: (1) synthesis 2 of three arms, 48 polyethylene glycol to DMF sulphonic acid ester) pentadecanoic acid three
The synthesis of 48 polyethylene glycol of arm；(3) synthesis of the indoles quaternary ammonium salt of three arm of pentadecyl, 48 polyglycol ether.
The synthesis of 48 polyethylene glycol p-methyl benzenesulfonic acid ester of (1) three arm
At 0 DEG C, to methylene chloride (30ml) solution of three arms, 48 polyethylene glycol (3mmol) and triethylamine (3mmol)
In paratoluensulfonyl chloride (10mmol) is slowly added dropwise, after completion of dropwise addition room temperature continue stirring 12 hours.Reaction passes through unsaturated carbonate
Hydrogen sodium (100mL) is quenched, then liquid separation, and after organic phase is concentrated under reduced pressure, crude product direct plunges into react in next step.
(2) synthesis of three arm of pentadecanoic acid, 48 polyethylene glycol
It is reacted by following reaction formula, specifically: at 0 DEG C, to the DMF (150mL) of hydroxypentadecanoic acid (6mmol)
Sodium hydroxide (12mmol) is added in solution, after being stirred at room temperature 120 minutes, three arms, 48 polyethylene glycol p-methyl benzenesulfonic acid is added
Ester (2mmol), reaction are reacted 24 hours at 60 DEG C, and reaction is quenched with water.By reaction solution liquid separation, water phase is collected, organic phase is used
A small amount of water back extraction, merges water phase, and concentration water phase obtains three arm of pentadecanoic acid, 48 polyethylene glycol.
(3) synthesis of the indoles quaternary ammonium salt of three arm of pentadecyl, 48 polyglycol ether
Under room temperature, first it is added into DMF (100mL) solution of three arm of pentadecanoic acid, 48 polyethylene glycol (2mmol)
The DIPEA of the EDCI and 6mol of 6mmol are stirred 2 hours, are added indoles quaternary ammonium amines (10mmol), after being stirred at room temperature 2 hours, heating
To 50 degree, reaction solution reacts 12 hours under 50 degree, and TLC is tracked after reaction, and 28% hydrochloric acid is added into reaction system
(10ml) and water (10mL), the reaction was continued 2 hours for room temperature.Organic solvent removes under reduced pressure, and water phase is washed repeatedly with ethyl acetate,
Concentration water phase obtains the indoles quaternary ammonium salt of three arm of pentadecyl, 48 polyglycol ether.
Example IV
The bacteriostasis property of the indoles quaternary ammonium salt of three arm polyglycol ether of pentadecyl
1. the indoles quaternary ammonium salt of three arm of pentadecyl, 12 polyglycol ether is to the bactericidal effect of staphylococcus aureus
The indoles quaternary ammonium salt of three arm of pentadecyl, 12 polyglycol ether is determined respectively, and three arm 24 of pentadecyl is poly-
The indoles quaternary ammonium salt of 48 polyglycol ether of indoles quaternary ammonium salt and three arm of pentadecyl of glycol ether is to Staphylococcus aureus
The bactericidal effect of bacterium sets two concentration gradients, and 15 μ L are added in filter paper respectively, and 30 μ L concentration are the surface 5mmol/L
Activator solution, bactericidal effect is as shown in table 1-1:
Fungistatic effect of the table 1-1 to staphylococcus aureus
The specific value of inhibition zone is shown in Table.It can be seen that the synthesized three arm polyethylene glycol of pentadecyl of experiment from table 1-1
The indoles quaternary ammonium salt series of surfactants of ether all has certain bactericidal and bacteriostatic effect to Escherichia coli, and this point is from table 1-1's
Data it is also seen that.Then, to the indoles quaternary ammonium salt series of surfactants of three arm of pentadecyl, 24 polyglycol ether
Increase concentration gradient again and done comparative experiments, finds the indoles quaternary ammonium salt series of tables of three arm of pentadecyl, 24 polyglycol ether
Face activating agent increases bacteriostatic activity；Meanwhile to the indoles quaternary ammonium salt of three arm of pentadecyl, 48 polyglycol ether also with same
The concentration gradient of sample compares, and antibacterial circle diameter significant change increases.For the indoles of three arm polyglycol ether of pentadecyl
Quaternary ammonium salt series of surfactants, although staphylococcus aureus cannot directly be killed, to a certain extent to golden yellow
Staphylococcus plays the role of certain its growth and breeding of inhibition.
2. the indoles quaternary ammonium salt of three arm polyglycol ether of pentadecyl is to the bactericidal effect of bacillus subtilis
The indoles quaternary ammonium salt of three arm of pentadecyl, 12 polyglycol ether is determined respectively, and three arm 24 of pentadecyl is poly-
The indoles quaternary ammonium salt of 48 polyglycol ether of indoles quaternary ammonium salt and three arm of pentadecyl of glycol ether is to bacillus subtilis
Bactericidal effect, set two concentration gradients, be added 15 μ L in filter paper respectively, 30 μ L concentration are that the surface 5mmol/L is living
Property agent solution, bactericidal effect is as shown in table 1-2:
Fungistatic effect of the table 1-2 to bacillus subtilis
From table 1-2, it can be seen that the good results are evident, and inhibition zone is very clear, with the poly- second two of three arm of pentadecyl 48
The indoles quaternary ammonium salt of alcohol ether compares, and the comparison of antibacterial circle diameter size is it is obvious that three arm of pentadecyl, 24 polyethylene glycol
The indoles quaternary ammonium salt of ether is significantly larger than three arm of pentadecyl, 48 polyglycol ether to the bactericidal effect of bacillus subtilis
Indoles quaternary ammonium salt, table 1-2 is from numerically demonstrating this point；From table 1-2 it may be seen that in 15 μ L and 30 μ L concentration gradients
Interior, the antibacterial circle diameter variation of the indoles quaternary ammonium salt of three arm of pentadecyl, 24 polyglycol ether less, illustrates dense at this
Spend in range, the indoles quaternary ammonium salt of three arm of pentadecyl, 24 polyglycol ether to the bactericidal effect of bacillus subtilis
Reach maximum efficiency, in order to investigate the indoles quaternary ammonium salt various concentration of three arm of pentadecyl, 24 polyglycol ether to withered grass bud
The influence of the bactericidal activity of spore bacillus, and investigated the indoles quaternary ammonium of three arm of pentadecyl, 24 polyglycol ether under low concentration
Bactericidal effect of the salt to bacillus subtilis.
The indoles quaternary ammonium salt of three arm of pentadecyl, 24 polyglycol ether of table 1-3 various concentration is to bacillus subtilis
Fungistatic effect
It can be seen that from table 1-3 and increase with the indoles quaternary ammonium salinity of three arm of pentadecyl 24 polyglycol ether,
The diameter of inhibition zone becomes larger, and diameter comparison is obvious, when three arm of pentadecyl, 24 polyglycol ether indoles quaternary ammonium salt plus
When entering amount and reaching 20 μ L (10mmol/L), the diameter of inhibition zone reaches maximum, with three arm of pentadecyl, 24 polyethylene glycol
The variation of the increase antibacterial circle diameter of the indoles quaternary ammonium salt additional amount of ether is unobvious.
Embodiment five
Foaming properties measurement
Example one, embodiment two, three compound configuration surface activating agent of embodiment are respectively placed in test tube and mark 1,
2,3；It takes conventional surfactants to be placed in test tube 4, chlorination chain alkyl trimethyl ammonium is taken to be placed in test tube 5.Wherein test tube 4 are in 5
Contrast groups.Test tube 1,2,3,4,5 is respectively plus the dissolution of 50ml distilled water is stand-by.It is carefully pipetted with the pipette of rinse respectively
25.0mL test solution covers plug in colorimetric cylinder, pins plug with index finger, firmly fluctuates colorimetric cylinder 10 times, generates foam
After measure with a yardstick foam height and record the results are shown in Table 4.
4 brbble test result of table
From table 4, it can be seen that the compound of embodiment 1,2,3 has the foaming properties close with conventional surfactants,
Significantly larger than common cation surfactant.
Claims (10)
1. a kind of Novel Cationic Surfactants, which is characterized in that main component is Formulas I structure:
Wherein, n takes the positive integer more than or equal to 1, less than or equal to 48.
2. a kind of preparation method of Novel Cationic Surfactants as described in claim 1, which is characterized in that including as follows
Step:
Using hydroxypentadecanoic acid as raw material, in the presence of alkali by anti-with a three arm polyethylene glycol p-methyl benzenesulfonic acid additions of ester
It should obtain three arm polyethylene glycol of pentadecanoic acid；
Condensation reaction is occurred into for the three arm polyethylene glycol of pentadecanoic acid and indoles quaternary ammonium amines and obtains the poly- second two of three arm of pentadecyl
The quaternary ammonium of alcohol ether；
It is acidified the quaternary ammonium of the three arm polyglycol ether of pentadecyl to obtain the indoles season of three arm polyglycol ether of pentadecyl
Ammonium salt.
3. the preparation method of Novel Cationic Surfactants as claimed in claim 2, it is characterised in that: the addition reaction
Alkali be inorganic base.
4. the preparation method of Novel Cationic Surfactants as claimed in claim 3, it is characterised in that: the inorganic base is
Sodium hydride, sodium hydroxide.
5. the preparation method of Novel Cationic Surfactants as claimed in claim 2, it is characterised in that: the condensation reaction
It is carried out under organic base effect.
6. the preparation method of Novel Cationic Surfactants according to claim 5, it is characterised in that: the organic base
For DMAP, DIPEA；The condensing agent of the condensation reaction is HATU and EDCI.
7. the preparation method of Novel Cationic Surfactants according to claim 2, it is characterised in that: the acidification is
Hydrochloric acid acidification.
8. the preparation method of Novel Cationic Surfactants according to claim 2, which is characterized in that the addition is anti-
It answers are as follows: hydroxypentadecanoic acid is carried out with three arm polyethylene glycol p-methyl benzenesulfonic acid ester of monodisperse in organic solvent in the presence of alkali
Addition reaction obtains three arm polyethylene glycol of monodisperse pentadecanoic acid.
9. the preparation method of Novel Cationic Surfactants according to claim 8, it is characterised in that: described is organic
Solvent is toluene or DMF.
10. according to the preparation method of the described in any item Novel Cationic Surfactants of claim 2-9, feature
Be: the three arm polyethylene glycol of pentadecanoic acid is as shown in Formula II:
Wherein, n is to be less than or equal to 48 positive integers more than or equal to 1.
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| CN111036136A (en) * | 2019-12-25 | 2020-04-21 | 湖南华腾制药有限公司 | Novel cationic surfactant and preparation method thereof |
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