CN108440347B - Star-shaped sulfonic zwitterionic surfactant and preparation method and application thereof - Google Patents
Star-shaped sulfonic zwitterionic surfactant and preparation method and application thereof Download PDFInfo
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- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/13—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/14—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton
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- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
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- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
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Abstract
The invention belongs to the technical field of dispersant preparation, and discloses a star-shaped sulfonic zwitterionic surfactant, a preparation method and application thereof, wherein quantitative trimethylolpropane-tri (3-aziridinyl propionate) reaction liquid is dropwise added into a reaction bottle filled with a long-chain aliphatic primary amine ethanol solution and an acid catalyst to carry out a first step aziridine ring-opening reaction; then adding a certain amount of 2-chloroethyl sodium sulfonate reaction liquid into the reaction liquid to carry out a second step of sulfonic acid group substitution and quaternization reaction, and obtaining a product which is a multi-charge star-shaped amphoteric dispersant. According to the star amphoteric dispersant prepared by the invention, sulfonate ions are introduced into a molecular chain of the star amphoteric dispersant, so that a combination of dispersant molecules and graphene can be fully dispersed in water, the repulsion between graphene particles is enhanced, and the dispersion effect is improved. Meanwhile, quaternary ammonium salt cations are introduced into the molecular chain of the dispersing agent, so that the hydration capability and the thermal stability of the dispersing agent are improved.
Description
Technical Field
The invention relates to the technical field of preparation of multi-quaternary ammonium salt cationic compounds, in particular to a star-shaped sulfonic acid group zwitterionic surfactant, and a preparation method and application thereof.
Background
Gemini surfactants with amphiphilic groups and amphiphilic groups have attracted more and more attention and research in recent years as a new type of surfactant with excellent performance. The gemini surfactant is prepared by linking two common surfactants at or near a hydrophilic head group through a chemical bonding mode by a linking group, so that the surfactants have many special properties, such as low critical micelle concentration, low solid-liquid interface adsorption, strong salt resistance and high capacity of reducing oil-water interfacial tension, and have very good application prospect in the field of tertiary oil recovery. The molecular structure of the aminosulfonic acid type amphoteric gemini surfactant contains two quaternary ammonium salt cationic groups and two sulfonic acid group anionic groups, so that the aminosulfonic acid type amphoteric gemini surfactant has the functions of emulsification, dispersion, flocculation, wetting, foaming, spreading, permeation, lubrication, antistatic, sterilization and the like.
Graphene has excellent electrical, mechanical, optical and thermal properties, and is widely used in the fields of electronic components, energy storage, catalysis, biosensing, and the like. Graphene sheets have strong van der waals force between layers, aggregation is easy to occur, and the graphene sheets are difficult to dissolve in water and common organic solvents, so that the performance of graphene in practical application is greatly influenced. Therefore, in order to fully exert its excellent properties, the preparation of uniform, highly stable graphene dispersions is an important condition for its research and application in many fields.
In order to improve the dispersibility of graphene in an aqueous solution, one way is to perform chemical modification treatment on graphene so as to improve the dispersibility of graphene, but this way may cause changes in the chemical composition, physical morphology and the like of the graphene material. The other method is to add auxiliary dispersing agents such as surfactants and the like into the dispersing medium to improve the dispersion degree of the graphene to a certain extent, but the effect is not obvious. Therefore, the development of a dispersing agent capable of greatly improving the dispersion performance of graphene in an aqueous solution is a problem to be solved in the mass preparation of graphene.
Disclosure of Invention
In order to prepare the amphoteric surfactant containing a plurality of quaternary ammonium salt cationic groups and a plurality of sulfonic acid group anionic groups, the invention uses the reaction of a high-activity aziridine crosslinking agent and a long-chain active amine group to form a star surfactant carrying active secondary amine, and then introduces a sulfonating reagent for reaction to obtain the star sulfonic acid group amphoteric surfactant and a preparation method and application thereof. The invention aims at providing a star-shaped sulfonic acid group zwitterionic surfactant, and the invention aims at providing a preparation method of the compound.
In order to achieve the purpose, the invention adopts the following technical scheme:
a star-shaped sulfonic acid group zwitterionic surfactant has a structural formula as follows:
wherein R1-is a long aliphatic chain, and the number of carbon atoms in the carbon chain is 12-18.
A preparation method of a star-shaped sulfonic zwitterionic surfactant comprises the following steps:
adding trimethylolpropane-tris (3-aziridinyl propionate) reaction liquid into a long-chain fatty primary amine ethanol solution and an acid catalyst to perform aziridine ring-opening reaction, and reacting at 50-80 ℃ for 6-8 h;
under the alkalescent condition, adding 2-chloroethyl sodium sulfonate aqueous solution into the reactant to carry out sulfonic substitution and quaternization reaction, and reacting for 10-16 h at 70-90 ℃; removing insoluble substances after the reaction is finished, concentrating the reaction solution, purifying and separating the product by using a toluene column chromatography, and drying in vacuum until the weight is constant to obtain the product.
In the aziridine ring opening reaction, trimethylolpropane-tris (3-aziridinylpropionate) and methylamine or ethylamine were in a molar ratio of 1: 3.
In the aziridine ring-opening reaction, the acidic catalyst is a phosphoric acid aqueous solution with the mass fraction of 85 percent, and the dosage of the acidic catalyst is 1 percent of the total mass of the raw materials.
In sulfonic acid group substitution and quaternization reaction, under the alkalescent condition, the pH value is 9-10, and the reaction solution is adjusted to alkalescence by NaOH.
In the sulfonic acid group substitution and quaternization reaction, the amount of the substance of sodium 2-chloroethyl sulfonate was 6 times as much as that of trimethylolpropane-tris (3-aziridinyl propionate).
An application of a star-shaped sulfonic zwitterionic surfactant as a graphene dispersing agent.
The mass ratio of the graphene dispersing agent to the graphene powder is as follows: (3-5): 25.
compared with the prior art, the invention has the following advantages:
in order to prepare the amphoteric surfactant containing a plurality of quaternary ammonium salt cationic groups and a plurality of sulfonic acid group anionic groups, the invention uses a high-activity aziridine crosslinking agent to react with a long-chain active amine group to form a star surfactant carrying active secondary amine, and then introduces a sulfonating reagent to react to obtain the star sulfonic acid group amphoteric surfactant. Provides a simple preparation method for preparing the star sulfonic zwitterionic surfactant.
According to the star amphoteric dispersant prepared by the invention, sulfonate ions are introduced into a molecular chain of the star amphoteric dispersant, so that a combination of dispersant molecules and graphene can be fully dispersed in water, the repulsion between graphene particles is enhanced, and the dispersion effect is improved. Meanwhile, quaternary ammonium salt cations are introduced into the molecular chain of the dispersing agent, so that the hydration capability and the thermal stability of the dispersing agent are improved. The main advantages are:
(1) according to the invention, a large amount of sulfonate ions are introduced to a molecular chain of the dispersing agent, and a hydrophilic sulfonic group can enable a combination of molecules and graphene to be fully dispersed in water.
(2) According to the invention, quaternary ammonium salt cations are introduced into the molecular chain of the dispersant, so that the hydration capability and the thermal stability of the star-shaped amphoteric dispersant are improved.
(3) The molecular structure of the dispersant is a star-shaped structure, and the space blocking effect among graphene particles is increased. Therefore, the amphoteric star dispersant has more efficient dispersion effect and good dispersion stability.
Drawings
FIG. 1 is a chemical structural formula of the present invention;
FIG. 2 is a scheme of the synthesis of the reaction of the present invention.
Detailed Description
As shown in fig. 1 and fig. 2, the present invention adopts the following technical solutions:
an amphoteric star-shaped dispersant for dispersing graphene, which has a structural formula as follows:
wherein R is1-is a long aliphatic chain, and the number of carbon atoms in the carbon chain is 12-18.
The preparation method of the amphoteric star-shaped dispersant for dispersing graphene comprises the following steps:
dropwise adding trimethylolpropane-tris (3-aziridinyl propionate) reaction liquid into a reaction bottle filled with a long-chain fatty primary amine ethanol solution and an acid catalyst to perform a first-step aziridine ring-opening reaction, wherein the molar ratio of the trimethylolpropane-tris (3-aziridinyl propionate) to the long-chain fatty primary amine is 1:3, and reacting at 50-70 ℃ for 6-8 h; and adjusting the reaction liquid to be alkaline (pH is 10) by NaOH, dropwise adding a 2-chloroethyl sodium sulfonate aqueous solution to perform a second step of sulfonic acid group substitution and quaternization reaction, wherein the amount of the 2-chloroethyl sodium sulfonate is 6 times of that of trimethylolpropane-tris (3-aziridinyl propionate), and reacting for 10-16 h at 70-90 ℃. Removing insoluble substances after the reaction is finished, concentrating the reaction solution, purifying and separating the product by using a toluene column chromatography, and drying in vacuum until the weight is constant to obtain the product.
The synthesis equation is as follows:
wherein R is1-is a long aliphatic chain, and the number of carbon atoms in the carbon chain is 12-18.
The technical solution in the embodiments of the present invention will be clearly and completely described below. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
(1) In a mixture of an 80% ethanol solution (34.69g, containing 27.75g, 0.15mol of primary dodecylamine) of a primary dodecylamine and an acidic catalyst (85% H)3PO40.50g), heated to 50 ℃, and then 70 percent by mass of trimethylolpropane-tris (3-aziridinyl propionate) ethanol solution (35.42g, which contains 21.25g of trimethylolpropane-tris (3-aziridinyl propionate) and 0.05mol) is added dropwise for 40 min. After the dropwise addition, the temperature is raised to 70 ℃ for reaction for 6 hours
(2) Adjusting the reaction solution to be alkalescent (pH is 10) by NaOH, dropwise adding 80% by mass of 2-chloroethyl sodium sulfonate aqueous solution (62.46g, 49.97g of 2-chloroethyl sodium sulfonate, 0.30mol) for 60min, and reacting at 70 ℃ for 16 h; removing insoluble substances after the reaction is finished, concentrating the reaction solution, purifying and separating the product by using a toluene column chromatography, and drying in vacuum to constant weight to obtain the product.
The structural formula of the product obtained in example 1 is:
1H NMR(300MHz，DMSO)：3.94(s，6H)，3.80～3.85(m，48H)，3.63～3.68(m，18H)，3.22(s，6H)，2.69(t，6H)，1.71(m，8H)，1.26～1.29(s，54H)，0.83～0.88(m，12H)ppm。
13C NMR(300MHz，DMSO)：173.1，65.9，57.2，54.7～55.0，45，35.7，31.9，29.3～29.6，26.0～26.8，22.7，14.1，7.0ppm。
and (3) testing the dispersion performance:
grinding commercially available graphene (Qingdao Jinpeng graphite Co., Ltd.) into graphene powder, selecting a clean reagent bottle, respectively weighing 5mg of the dispersing agent prepared in example 1 and 25mg of graphene powder, adding 10m L of water, oscillating, mixing uniformly, sealing, putting into an ultrasonic instrument for ultrasonic treatment, performing ultrasonic treatment at 100W for 12h, keeping the water temperature at 40-50 ℃ in the ultrasonic treatment process, performing centrifugal separation after the ultrasonic treatment is finished, performing centrifugal separation at the centrifugal rotation speed of 1000r/min for 30min, and obtaining a supernatant as graphene dispersion liquid for blank test.
The graphene dispersion prepared in example 1 was allowed to stand at 25 ℃ for 10 hours, and the stability was observed. The results showed no sedimentation in the dispersion. Whereas the dispersion of the blank test, the graphene was almost completely settled.
Example 2
(1) In a reaction vessel containing 80% by mass of an ethanol solution of primary octadecylamine (50.53g, containing 40.43g, 0.15mol of primary octadecylamine) and an acidic catalyst (85% H)3PO40.60g), heated to 50 ℃, and then 70 percent by mass of trimethylolpropane-tris (3-aziridinyl propionate) ethanol solution (35.42g, which contains 21.25g of trimethylolpropane-tris (3-aziridinyl propionate) and 0.05mol) is added dropwise for 40 min. After the dropwise addition, the temperature is raised to 50 ℃ for reaction for 8 hours.
(2) Adjusting the reaction solution to be alkalescent (pH is 10) by NaOH, dropwise adding 80% by mass of 2-chloroethyl sodium sulfonate aqueous solution (62.46g, 49.97g of 2-chloroethyl sodium sulfonate, 0.30mol) for 60min, and reacting at 90 ℃ for 10 h; removing insoluble substances after the reaction is finished, concentrating the reaction solution, purifying and separating the product by using a toluene column chromatography, and drying in vacuum to constant weight to obtain the product.
The structural formula of the product obtained in example 2 is:
and (3) testing the dispersion performance:
grinding commercially available graphene (Qingdao Jinpeng graphite Co., Ltd.) into graphene powder, selecting a clean reagent bottle, respectively weighing 5mg of the dispersing agent prepared in example 2 and 25mg of graphene powder, adding 10m L of water, oscillating, mixing uniformly, sealing, putting into an ultrasonic instrument for ultrasonic treatment, performing ultrasonic treatment at 100W for 12h, keeping the water temperature at 40-50 ℃ in the ultrasonic treatment process, performing centrifugal separation after the ultrasonic treatment is finished, performing centrifugal separation at the centrifugal rotation speed of 1000r/min for 30min, and obtaining a supernatant as a graphene dispersion liquid, wherein the concentration of graphene is 0.82mg/m L.
The graphene dispersion prepared in example 2 was allowed to stand at 25 ℃ for 14 hours, and the stability was observed. The results showed no sedimentation in the dispersion.
Example 3
(1) In a solution of 80% by mass of an ethanol solution of a primary tetradecyl amine (40.03g, containing 32.03g of a primary tetradecyl amine, 0.15mol) and an acidic catalyst (85% H)3PO40.50g), heated to 50 ℃, and then 70 percent by mass of trimethylolpropane-tris (3-aziridinyl propionate) ethanol solution (35.42g, which contains 21.25g of trimethylolpropane-tris (3-aziridinyl propionate) and 0.05mol) is added dropwise for 40 min. After the dropwise addition, the temperature is raised to 60 ℃ for reaction for 7 hours.
(2) Adjusting the reaction solution to be alkalescent (pH is 10) by NaOH, dropwise adding 80% by mass of 2-chloroethyl sodium sulfonate aqueous solution (62.46g, 49.97g of 2-chloroethyl sodium sulfonate, 0.30mol) for 60min, and reacting at 80 ℃ for 14 h; removing insoluble substances after the reaction is finished, concentrating the reaction solution, purifying and separating the product by using a toluene column chromatography, and drying in vacuum to constant weight to obtain the product.
The structural formula of the product obtained in example 3 is:
and (3) testing the dispersion performance:
grinding commercially available graphene (Qingdao Jinpeng graphite Co., Ltd.) into graphene powder, selecting a clean reagent bottle, respectively weighing 3mg of the dispersing agent prepared in example 3 and 25mg of graphene powder, adding 10m L of water, oscillating, mixing uniformly, sealing, putting into an ultrasonic instrument for ultrasonic treatment, performing ultrasonic treatment at 100W for 12h, keeping the water temperature at 40-50 ℃ in the ultrasonic treatment process, performing centrifugal separation after the ultrasonic treatment is finished, performing centrifugal separation at the centrifugal rotation speed of 1000r/min for 30min, and obtaining a supernatant as a graphene dispersion liquid, wherein the concentration of graphene is 0.97mg/m L.
The graphene dispersion prepared in example 3 was allowed to stand at 50 ℃ for 10 hours, and the stability was observed. The results showed no sedimentation in the dispersion.
Example 4
(1) In a solution containing 80% by mass of an ethanol solution of primary hexadecylamine (45.29g, containing 36.23g, 0.15mol of primary hexadecylamine) and an acidic catalyst (85% H)3PO40.50g), heated to 50 ℃, and then 70 percent by mass of trimethylolpropane-tris (3-aziridinyl propionate) ethanol solution (35.42g, which contains 21.25g of trimethylolpropane-tris (3-aziridinyl propionate) and 0.05mol) is added dropwise for 40 min. After the dropwise addition, the temperature is raised to 60 ℃ for reaction for 7 hours.
(2) Adjusting the reaction solution to be alkalescent (pH is 10) by NaOH, dropwise adding 80% by mass of 2-chloroethyl sodium sulfonate aqueous solution (62.46g, 49.97g of 2-chloroethyl sodium sulfonate, 0.30mol) for 60min, and reacting at 80 ℃ for 12 h; removing insoluble substances after the reaction is finished, concentrating the reaction solution, purifying and separating the product by using a toluene column chromatography, and drying in vacuum to constant weight to obtain the product.
The structural formula of the product obtained in example 4 is:
and (3) testing the dispersion performance:
grinding commercially available graphene (Qingdao Jinpeng graphite Co., Ltd.) into graphene powder, selecting a clean reagent bottle, respectively weighing 3mg of the dispersing agent prepared in example 4 and 25mg of graphene powder, adding 10m L of water, oscillating, mixing uniformly, sealing, putting into an ultrasonic instrument for ultrasonic treatment, performing ultrasonic treatment at 100W for 12h, keeping the water temperature at 40-50 ℃ in the ultrasonic treatment process, performing centrifugal separation after the ultrasonic treatment is finished, performing centrifugal separation at the centrifugal rotation speed of 1000r/min for 30min, and obtaining a supernatant as a graphene dispersion liquid, wherein the concentration of graphene is 0.97mg/m L.
The graphene dispersion prepared in example 4 was allowed to stand at 25 ℃ for 10 hours, and the stability was observed. The results showed no sedimentation in the dispersion.
The foregoing is a more detailed description of the invention and it is not intended that the invention be limited to the specific embodiments described herein, but that various modifications, alterations, and substitutions may be made by those skilled in the art without departing from the spirit of the invention, which should be construed to fall within the scope of the invention as defined by the appended claims.
Claims (6)
1. A preparation method of a star-shaped sulfonic zwitterionic surfactant is characterized in that the structural formula of the surfactant is as follows:
wherein R1-is a long aliphatic chain, and the number of carbon atoms in the carbon chain is 12-18;
the preparation method comprises the following steps:
adding trimethylolpropane-tris (3-aziridinyl propionate) reaction liquid into a long-chain fatty primary amine ethanol solution and an acid catalyst to perform aziridine ring-opening reaction, and reacting at 50-80 ℃ for 6-8 h;
under the alkalescent condition that the pH value is 9-10, adding 2-chloroethyl sodium sulfonate aqueous solution into the reactant to carry out sulfonic acid group substitution and quaternization reaction, and reacting for 10-16 h at 70-90 ℃; removing insoluble substances after the reaction is finished, concentrating the reaction solution, purifying and separating the product by using a toluene column chromatography, and drying in vacuum until the weight is constant to obtain the product.
2. The method for preparing the star-shaped sulfonic zwitterionic surfactant as claimed in claim 1, wherein the molar ratio of trimethylolpropane-tris (3-aziridinyl propionate) to the long-chain aliphatic primary amine in the aziridine ring opening reaction is 1: 3.
3. The method for preparing the star-shaped sulfonic acid group zwitterionic surfactant as claimed in claim 1, wherein: in the aziridine ring-opening reaction, the acidic catalyst is a phosphoric acid aqueous solution with the mass fraction of 85 percent, and the dosage of the acidic catalyst is 1 percent of the total mass of the raw materials.
4. The method for preparing the star-shaped sulfonic zwitterionic surfactant as claimed in claim 1, wherein in the sulfonic substitution and quaternization reaction, the reaction solution is adjusted to be weakly alkaline by NaOH.
5. The application of the star-shaped sulfonic acid group zwitterionic surfactant prepared by the preparation method in claim 1 as a graphene dispersing agent.
6. The application of the graphene powder as claimed in claim 5, wherein the mass ratio of the graphene dispersing agent to the graphene powder is as follows: (3-5): 25.
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Effective date of registration: 20220609 Address after: Room 029, f2006, 20 / F, block 4-A, Xixian financial port, Fengdong new city energy gold trade zone, Xixian New District, Xi'an, Shaanxi 710000 Patentee after: Shaanxi hechen New Material Technology Co.,Ltd. Address before: No. 1, Weiyang District university garden, Xi'an, Shaanxi Province, Shaanxi Patentee before: SHAANXI University OF SCIENCE & TECHNOLOGY |
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