CN112263548A - Preparation method of non-fatty acid single-chain anionic surfactant vesicles - Google Patents

Preparation method of non-fatty acid single-chain anionic surfactant vesicles Download PDF

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CN112263548A
CN112263548A CN202011149583.6A CN202011149583A CN112263548A CN 112263548 A CN112263548 A CN 112263548A CN 202011149583 A CN202011149583 A CN 202011149583A CN 112263548 A CN112263548 A CN 112263548A
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fatty acid
sodium
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anionic surfactant
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胥会芳
梁馨
张景亚
陆松
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Henan University of Traditional Chinese Medicine HUTCM
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    • A—HUMAN NECESSITIES
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    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
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    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
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    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds

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Abstract

The invention discloses a preparation method of a vesicle of a non-fatty acid single-chain anionic surfactant, belonging to the technical field of vesicle preparation, wherein the vesicle is formed by self-assembling the non-fatty acid single-chain anionic surfactant in an aqueous solution under the hydrothermal condition of 80-160 ℃; the vesicle is composed of a single-chain surfactant of non-fatty acids, the concentration range of the surfactant is 2-100mmol/L, the particle size is 50-500nm, and the vesicle can be stably placed for more than 1 year at normal temperature; the vesicle of the invention has reasonable coating property, selective permeability and thermal stability, and can be used in the fields of drug carriers, cosmetics, material synthesis, biomembrane simulation and the like.

Description

Preparation method of non-fatty acid single-chain anionic surfactant vesicles
Technical Field
The invention belongs to the technical field of vesicle preparation, and particularly relates to a preparation method of a vesicle of a non-fatty acid single-chain anionic surfactant.
Background
The vesicle is an ordered assembly formed by wrapping a micro-aqueous phase by a closed bilayer of amphiphilic molecules, and due to the unique structure of the vesicle, the vesicle is concerned recently, and has important application value in the fields of biological cell membrane simulation, drug carrier and material synthesis and the like. The preparation method of the double-chain surfactant vesicle is various, for example, phospholipid (natural double-chain surfactant molecule) solution can be processed by ultrasonic treatment or extrusion to prepare the phospholipid vesicle; however, the preparation of single-chain surfactant vesicles is not uncommon at present and generally corresponds to one of the following situations: regulating C8-C18At the pH value of a single-chain saturated fatty acid solution, fatty acid molecules and fatty acid radical anions can form an acid-soap dimer, and then self-assemble to form a fatty acid vesicle; the anion and cation single-chain surfactant compound system can spontaneously form vesicles under the action of static electricity; the concentration, temperature and salinity of the single-chain surfactant with a special structure are changed or illumination, special ions and the like are introduced to induce the spontaneous formation of the vesicles.
For the preparation of the traditional single-chain anionic surfactant vesicles without fatty acids, the traditional preparation method needs to additionally introduce another component into the solution, such as inorganic and organic additives or cationic surfactants with opposite charges are added to form a surfactant compounding system, and no relevant report exists at present about the preparation of the vesicles from the traditional single-chain anionic surfactant solution without fatty acids under a certain external environment.
Disclosure of Invention
In order to solve the problems, the invention provides a preparation method of a non-fatty acid single-chain anionic surfactant vesicle.
A preparation method of non-fatty acid single-chain anionic surfactant vesicles comprises the following steps:
dissolving a non-fatty acid single-chain anionic surfactant in water to prepare a micelle aqueous solution; and carrying out hydrothermal reaction on the micelle aqueous solution at the temperature of 80-160 ℃, and carrying out self-assembly to form a vesicle aqueous solution.
Preferably, the non-fatty acid single-chain surfactant is C8-C14Single-chain alkyl sodium sulfate of chain length, C8-C14Sodium Single-chain alkyl sulfonates of chain length or C8-C14Sodium alkyl benzene sulphonate of chain length.
Preferably, said C8-C14The single-chain sodium alkyl sulfate with the chain length is sodium octyl sulfate, sodium decyl sulfate, sodium lauryl sulfate or sodium myristyl sulfate.
Preferably, said C8-C14The single-chain sodium alkyl sulfonate with the chain length is sodium octyl sulfonate, sodium decyl sulfonate, sodium lauryl sulfonate or sodium myristyl sulfonate.
Preferably, said C8-C14The sodium alkyl benzene sulfonate with chain length is sodium octyl benzene sulfonate, sodium decyl benzene sulfonate, sodium lauryl benzene sulfonate or sodium myristyl benzene sulfonate.
Preferably, the concentration of the aqueous micellar solution is 2 to 100 mmol/L.
Preferably, the hydrothermal reaction time is 2-6 h.
Preferably, the size of the vesicle in the vesicle aqueous solution is 50-500 nm.
Preferably, the pH of the aqueous vesicle solution is 1.5-6.8.
Compared with the prior art, the invention has the following beneficial effects:
(1) the invention provides a preparation method of non-fatty acid single-chain anionic surfactant vesicles for the first time, the preparation method is simple, the vesicles can be formed only by dissolving the surfactant in water and carrying out hydrothermal reaction at 80-160 ℃, the particle size of the vesicles is 50-500nm, the vesicles have certain storage stability, and the vesicles can be stably placed for more than 1 year at normal temperature;
(2) the vesicle can be formed under the condition of extremely low surfactant concentration, the physical and chemical properties of the vesicle are basically consistent with those of the traditional surfactant vesicle, the synthetic method is simple and easy to implement, and the vesicle has necessary size selective permeability and effective load capacity on model drug molecules, and can be used in the fields of biomembrane simulation, drug carriers, bioengineering, daily chemical industry and the like.
Drawings
FIG. 1 is a negative stain Transmission Electron Microscope (TEM) photograph of a sodium lauryl sulfate vesicle solution prepared in example 1;
FIG. 2 is a graph of the particle size distribution of the sodium lauryl sulfate solution before and after hydrothermal treatment in example 1;
FIG. 3 is a comparison of NMR spectra of sodium lauryl sulfate deuterated DMSO solutions without hydrothermal treatment, and after hydrothermal lyophilization in example 1(a) and example 3(b), respectively;
FIG. 4 is a confocal laser microscopy (CLSM) of the sodium lauryl sulfate vesicle solution prepared in example 1, wherein (a), (b) and (c) are labeled with calcein, fluorescein isothiocyanate-labeled bovine serum albumin (FITC-BSA) and Nile Red, respectively.
Detailed Description
In order to make the technical solutions of the present invention better understood and implemented by those skilled in the art, the present invention is further described below with reference to the following specific embodiments and the accompanying drawings, but the embodiments are not meant to limit the present invention.
The experimental methods and the detection methods described in the following examples are all conventional methods unless otherwise specified; the reagents and materials are commercially available, unless otherwise specified.
Example l
A preparation method of non-fatty acid single-chain anionic surfactant vesicles comprises the following steps:
weighing a designed amount of sodium lauryl sulfate (SDS) to prepare a 20mmol/L aqueous solution, uniformly stirring at room temperature, placing the solution in a small reaction kettle lining made of polytetrafluoroethylene, carrying out hydrothermal reaction at 160 ℃ for 2h, and cooling to prepare the vesicle aqueous solution.
The turbidity of the solution after the hydrothermal reaction is increased, which can be attributed to the possibility that SDS molecules are decomposed under the action of high temperature and high pressure to generate alkyl alcohol or alkyl sulfate with lower solubility.
The negative staining TEM photograph of the vesicle sample is shown in FIG. 1, the SDS solution forms vesicles after hydrothermal reaction, the spherical vesicles have clear and visible shapes, the particle size is 50-500nm, and the vesicle has certain storage stability and can be stably placed for more than 1 year at normal temperature.
Dynamic Light Scattering (DLS) analysis showed (FIG. 2) that the SDS original solution before hydrothermal reaction at 160 ℃ was a micellar solution with a diameter of about 4nm, and the hydration kinetic diameter of the vesicles formed after hydrothermal reaction was 50-500nm, slightly larger than the diameter shown in the electron micrograph, probably due to the influence of the hydration layer of the vesicles.
Sampling for pH value measurement, and reducing the pH value of the solution after the hydrothermal treatment at 160 ℃ from 6.84 of the original solution before the hydrothermal treatment to 1.90, wherein the pH value shows that part of SDS molecules are decomposed under the action of high temperature and high pressure to generate alkyl alcohol or alkyl sulfate in a protonated form, and then the SDS molecules and SDS in an anionic form an acid-soap dimer similar to a fatty acid system under the action of a hydrogen bond, so that the single-chain anionic surfactant solution can be regarded as a quasi-binary mixed surfactant system.
The SDS solution before and after the hydrothermal reaction at 160 ℃ was lyophilized to obtain a white powder, which was then dissolved in DMSO-d6 to measure its hydrogen nuclear magnetic resonance spectrum (FIG. 3). It can be seen that the chemical shift (δ value) of the hydrogen atom of the sample after the 160 ℃ hydrothermal treatment (fig. 3(a)) is shifted compared to the chemical shift (δ value) of the SDS sample before the hydrothermal reaction (fig. 3(c)), and a broad peak is observed at δ of 5.65ppm, indicating the appearance of active hydrogen (δ of 5.65ppm), and multiple peaks appear at 1.39, 1.47, 3.36, and 3.99, indicating that the SDS solution undergoes a decomposition reaction after the 160 ℃ hydrothermal treatment to produce an alkyl alcohol or alkyl ester. Further illustrates that the possible mechanism of vesicle formation under high temperature hydrothermal conditions (100 ℃ to T to 160 ℃) is SDS (DS) in anionic form-) With the resulting alkyl alcohol or alkyl ester in protonated form, a "pseudo-gemini surfactant" is formed by hydrogen bonding, followed by self-assembly to form vesicles.
Two hydrophilic fluorescent probes (small-sized calcein and large-sized FITC-BSA) and a hydrophobic fluorescent probe (Nile red) are respectively adopted to examine the size-selective permeability of the vesicle membrane and the loading capacity of model drug molecules (dye molecules) with different hydrophilicity and hydrophobicity. The above hydrothermally prepared vesicle solution was mixed with a dye and observed in fluorescence mode using CLSM (fig. 4). For the calcein-labeled sample solution (fig. 4(a)), a green-fluorescent spherical spot can be seen, indicating that small-sized hydrophilic calcein molecules can permeate through the vesicle membrane, with payload in the inner water core of the vesicle; in contrast, for the FITC-BSA labeled sample solution (FIG. 4(b)), no green fluorescent spot was observed, indicating that the large-sized hydrophilic fluorescent protein cannot permeate the vesicle membrane. For the nile red labeled sample solution (fig. 4(c)), red fluorescent spherical spots were observed, indicating that hydrophobic nile red molecules can be effectively loaded in the hydrophobic region of the vesicle bilayer membrane. These results demonstrate the necessary "size selective" permeability and payload capacity for model drug molecules of the vesicle membranes prepared by the present invention, which are important for their applications in the fields of biofilm simulation, drug carriers, and the like.
Example 2
A preparation method of non-fatty acid single-chain anionic surfactant vesicles is disclosed, wherein the surfactant is SDS and is prepared by the following steps:
weighing SDS in a designed amount, preparing into 50mmol/L aqueous solution, stirring uniformly at room temperature, placing in a small reaction kettle lining made of polytetrafluoroethylene, carrying out hydrothermal reaction for 2h at 120 ℃, and cooling to obtain a vesicle sample, wherein the pH value of the solution is 1.76. TEM and DLS results show particle sizes between 85-500 nm.
Example 3
A preparation method of non-fatty acid single-chain anionic surfactant vesicles is disclosed, wherein the surfactant is SDS and is prepared by the following steps:
weighing SDS in a designed amount, preparing into 100mmol/L aqueous solution, stirring uniformly at room temperature, placing in a small reaction kettle lining made of polytetrafluoroethylene, carrying out hydrothermal reaction for 2h at 80 ℃, and cooling.
After 80 ℃ hydrothermal reaction, the solution appearance has no obvious change, the pH value is 6.65, the solution is basically kept unchanged, and the solution is hydrothermal at 80 DEG CThe NMR spectrum of the SDS sample after the treatment (FIG. 3(b)) was not significantly changed from that of the SDS sample before the hydrothermal treatment (FIG. 3(c)), indicating that alkyl alcohol or ester was not formed under these conditions. These results demonstrate that the vesicle formation pathway at lower hydrothermal temperatures (80 ℃ T100 ℃) is different from that at higher hydrothermal conditions and is attributable to the high energy imparted by hydrothermal conditions-、Na+The ions (counter ions) and water molecules move violently and are rearranged, so that the electrostatic repulsion between polar heads of the surfactant is reduced, and the surfactant molecules accidentally form a pseudo-gemini surfactant under the action of electrostatic force, hydrogen bonds and van der Waals force, and then form a stable vesicle structure. TEM and DLS results show particle sizes between 85-500 nm.
Example 4
A preparation method of non-fatty acid single-chain anionic surfactant vesicles is disclosed, wherein the surfactant is sodium octyl sulfate and is prepared by the following steps:
weighing octyl sodium sulfate with a designed amount, preparing into 100mmol/L aqueous solution, stirring uniformly at room temperature, placing in a small reaction kettle lining made of polytetrafluoroethylene, carrying out hydrothermal reaction at 160 ℃ for 6h, and cooling to obtain a vesicle sample, wherein the pH value of the solution is 1.51. TEM results show particle sizes between 50 and 500 nm.
Example 5
A preparation method of non-fatty acid single-chain anionic surfactant vesicles is disclosed, wherein the surfactant is sodium lauryl sulfate and is prepared by the following steps:
weighing sodium lauryl sulfate with a designed amount, preparing into 20mmol/L aqueous solution, stirring uniformly at room temperature, placing in a small reaction kettle lining made of polytetrafluoroethylene, carrying out hydrothermal reaction for 6h at 140 ℃, and cooling to obtain a vesicle sample, wherein the pH value of the solution is 3.52. TEM and DLS results show particle sizes between 50-500 nm.
Example 6
A preparation method of non-fatty acid single-chain anionic surfactant vesicles is disclosed, wherein the surfactant is sodium dodecyl benzene sulfonate and is prepared by the following steps:
weighing sodium dodecyl benzene sulfonate with the design amount, preparing into 2mmol/L aqueous solution, stirring uniformly at room temperature, placing in a small reaction kettle lining made of polytetrafluoroethylene, carrying out hydrothermal reaction at 80 ℃ for 6 hours, wherein the appearance of the solution is not obviously changed, the pH value is 6.73, and the solution is basically kept unchanged. TEM and DLS results show particle sizes between 50-500 nm.
Comparative example 1
The surfactant is sodium lauryl sulfate and is prepared by the following method:
weighing sodium lauryl sulfate with a designed amount, preparing into 20mmol/L aqueous solution, uniformly stirring at room temperature, placing in a small reaction kettle lining made of polytetrafluoroethylene, carrying out hydrothermal reaction at 200 ℃ for 2h, and carrying out high-temperature hydrothermal reaction on a large amount of sodium lauryl sulfate to generate alkyl alcohol or ester with low solubility, wherein oil drops visible to naked eyes are separated out and a stable vesicle solution cannot be formed.
Comparative example 2
The surfactant adopts SDS and is prepared by the following method:
weighing SDS in a designed amount, preparing into 100mmol/L aqueous solution, stirring uniformly at room temperature, placing in a small reaction kettle lining made of polytetrafluoroethylene, and carrying out hydrothermal reaction for 6h at 60 ℃. The hydrothermal temperature is low, so that the high energy effect is not enough to drive molecules in a solution system to move violently, and the absorbance of the sample solution is not changed obviously after hydrothermal. No vesicular particles were observed with both TEM and DLS results.
Comparative example 3
The surfactant is prepared by adopting sodium alkyl sulfate with an alkyl chain of more than 14 carbons, such as sodium n-octadecyl sulfate, according to the following method:
weighing a designed amount of sodium n-octadecyl sulfate, preparing into a 20mmol/L aqueous solution, uniformly stirring at room temperature, placing in a small reaction kettle lining made of polytetrafluoroethylene, carrying out hydrothermal reaction at 160 ℃ for 2h, and after the hydrothermal reaction, generating a large amount of alkyl alcohol or ester with low solubility from the sodium n-octadecyl sulfate, wherein a large amount of oil drops are separated out and a stable vesicle solution cannot be formed.
In conclusion, the invention provides a preparation method of a non-fatty acid single-chain anionic surfactant vesicle for the first time, the preparation method is simple, the surfactant is only dissolved in water, the vesicle can be formed by hydrothermal reaction at 80-160 ℃, the particle size of the vesicle is 50-500nm, the vesicle has certain storage stability, and the vesicle can be stably placed for more than 1 year at normal temperature; the vesicle can be formed under the condition of extremely low surfactant concentration, the physical and chemical properties of the vesicle are basically consistent with those of the traditional surfactant vesicle, the synthetic method is simple and easy to implement, and the vesicle has necessary size selective permeability and effective load capacity on model drug molecules, and can be used in the fields of biomembrane simulation, drug carriers, bioengineering, daily chemical industry and the like.
It will be apparent to those skilled in the art that various changes and modifications may be made in the present invention without departing from the spirit and scope of the invention. Thus, it is intended that such changes and modifications be included within the scope of the appended claims and their equivalents.

Claims (9)

1. A preparation method of non-fatty acid single-chain anionic surfactant vesicles is characterized by comprising the following steps:
dissolving a non-fatty acid single-chain anionic surfactant in water to prepare a micelle aqueous solution; and carrying out hydrothermal reaction on the micelle aqueous solution at the temperature of 80-160 ℃, and carrying out self-assembly to form a vesicle aqueous solution.
2. The method for producing a non-fatty acid single-chain anionic surfactant vesicle according to claim 1, wherein the non-fatty acid single-chain surfactant is C8-C14Single-chain alkyl sodium sulfate of chain length, C8-C14Sodium Single-chain alkyl sulfonates of chain length or C8-C14Sodium alkyl benzene sulphonate of chain length.
3. The method for preparing non-fatty acid single-chain anionic surfactant vesicles according to claim 2, wherein C is8-C14The single-chain alkyl sodium sulfate with the chain length is octyl sodium sulfate, decyl sodium sulfate, lauryl sodium sulfate orSodium myristyl sulfate.
4. The method for producing a non-fatty acid-based single-chain anionic surfactant vesicle according to claim 2, wherein C is8-C14The single-chain sodium alkyl sulfonate with the chain length is sodium octyl sulfonate, sodium decyl sulfonate, sodium lauryl sulfonate or sodium myristyl sulfonate.
5. The method for preparing non-fatty acid single-chain anionic surfactant vesicles according to claim 2, wherein C is8-C14The sodium alkyl benzene sulfonate with chain length is sodium octyl benzene sulfonate, sodium decyl benzene sulfonate, sodium lauryl benzene sulfonate or sodium myristyl benzene sulfonate.
6. The method for preparing a non-fatty acid single-chain anionic surfactant vesicle according to claim 1, wherein the concentration of the aqueous micelle solution is 2-100 mmol/L.
7. The method for preparing non-fatty acid single-chain anionic surfactant vesicles according to claim 1, wherein the hydrothermal reaction time is 2-6 h.
8. The method for preparing non-fatty acid single-chain anionic surfactant vesicles according to claim 1, wherein the size of the vesicles in the aqueous vesicle solution is 50-500 nm.
9. The method for preparing non-fatty acid single-chain anionic surfactant vesicles according to claim 1, wherein the pH of the aqueous vesicle solution is 1.5 to 6.8.
CN202011149583.6A 2020-10-23 2020-10-23 Preparation method of non-fatty acid single-chain anionic surfactant vesicles Withdrawn CN112263548A (en)

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Application publication date: 20210126