CN114891517B - Rosin-based CO 2 /N 2 Responsive microemulsion, and preparation method and application thereof - Google Patents
Rosin-based CO 2 /N 2 Responsive microemulsion, and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a rosin-based CO 2 /N 2 The responsive microemulsion comprises the following substances in parts by mass: 1-9 parts of surfactant compound system (ME), 1-15 parts of n-butanol (cosurfactant) and 1-9 parts of oil phase; wherein ME is derived from rosin-based CO 2 /N 2 The responsive surfactant MPANGG, sodium dodecyl sulfate and water are mixed. The microemulsion can be alternately introduced with CO 2 /N 2 The process can be repeated many times with no change in emulsion particle size before and after the response. The invention also discloses a method for preparing silver nano particles by using the microemulsion, which utilizes tertiary amine groups contained in MPANGG in the microemulsion to cause the tertiary amine groups to have oxidation-reduction reaction with silver ions to prepare the silver nano particles, thereby realizing the rapid separation of the nano particles from a system and having simple operation.
Description
Technical Field
The invention belongs to the technical field of green surfactants, and in particular relates to a rosin-based CO 2 /N 2 Responsive microemulsion and preparation method thereofAnd applications.
Background
Nano silver as one of the noble metal nano materials has a wide application in many fields, for example, they can be used for antibacterial materials, antistatic materials, low temperature superconducting materials, biosensor materials, etc. The nano silver composite fiber with permanent antibacterial activity can be prepared by adding nano silver into common synthetic textiles; the antibacterial activity of the spinning fiber taking nano silver as a cladding is good; as a catalytic material, nano silver has catalytic activity.
The microemulsion can be used as a novel reaction medium for synthesizing nano particles. The W/O type microemulsion contains monodisperse nano-scale droplets, and can be used as a micro-reaction tank for synthesizing nano particles. When two or more precursor microemulsions of synthetic nanoparticles are mixed, mass exchange occurs in the droplets as a microreactor, resulting in the final generation of nanoparticles, due to random brownian motion of the nanoscale dispersed phase (droplets) in the microemulsion. Meanwhile, the water droplets are wrapped by the surfactant and the cosurfactant, so that the agglomeration of the prepared nano particles can be effectively prevented. The microemulsion method is a multifunctional preparation technology, can control the size, geometry, morphology, uniformity, surface area and other properties of particles, and has one of the main advantages of being capable of preparing the nano-scale metal-based catalyst with high surface area and high catalytic activity. The microemulsion process also has some disadvantages. For example, the addition of large amounts of surfactants and organic solvents to the system, which are difficult to separate and remove from the final product, is also important for breaking emulsions, since breaking is often an important step in obtaining/separating the product from the (micro) emulsion. For common emulsions, demulsification can be generally achieved by adjusting the temperature and adding an electrolyte; more complex methods are demulsifier addition and centrifugation, pulsed voltage centrifugation, application of non-uniform electric fields, magnetic fluidized bed technology, simultaneous application of electric and magnetic fields, application of strong electric fields and microwaves. Since microemulsions are thermodynamically stable systems, breaking their stability or emulsion breaking is more difficult, and furthermore, if a large amount of surfactant/cosurfactant is contained in the system during subsequent processingThe direct discharge of the active agent, oil phase or additive not only causes environmental pollution but also causes resource waste. Therefore, development of stimulus-responsive microemulsions to achieve cyclic regeneration and reuse of microemulsions is increasingly attracting attention of numerous scientific researchers. Common stimulus-responsive triggers include light, heat, magnetic field, redox agent, pH, etc., which require either consumption of significant amounts of energy or irreversibly alter the composition of the system, affecting cyclic regeneration and reuse of the microemulsion, CO 2 There is a great interest in the use of such a low-cost and easily removable stimulant that is environmentally friendly, nontoxic.
At present, research on stimulus-responsive surfactants for emulsion preparation is mainly limited to common emulsions, and reports on the use of stimulus-responsive surfactants for microemulsion preparation are relatively few. The application of stimulus-responsive microemulsions is a potential way for realizing the cyclic regeneration and the repeated utilization of the microemulsions, stimulus-responsive surfactants are used as stimulus-responsive energy sources prepared by the microemulsions, but the report of the application of the stimulus-responsive surfactants in the preparation of the microemulsions is less, and the stimulus-responsive surfactants reported at present are mainly long-chain alkane, so the invention provides a rosin-based surfactant prepared from natural rosin resources and a CO prepared based on the surfactant 2 /N 2 Responsive microemulsion, and studied for CO 2 /N 2 Use of a responsive microemulsion in the preparation of nanoparticles.
Disclosure of Invention
To overcome the defects in the prior art, the invention aims to provide a rosin-based CO 2 /N 2 A responsive microemulsion, and its preparation method and application are provided.
In order to achieve the above purpose, the invention adopts the following technical scheme:
rosin-based CO 2 /N 2 The responsive microemulsion consists of the following substances in parts by mass:
1-9 parts of surfactant compound system (ME),
1-15 parts of n-butyl alcohol (cosurfactant),
1-9 parts of oil phase;
wherein the surfactant complex system (ME) is composed of rosin-based CO 2 /N 2 The responsive surfactant MPANGG, sodium Dodecyl Sulfate (SDS) and water are mixed according to the mass ratio of (2-10): (1-5): (6-30).
As a preferable technical scheme, the oil phase is an alkane liquid compound such as n-hexane, n-heptane, liquid paraffin and the like; more preferably, the oil phase is n-hexane.
The rosin-based CO 2 /N 2 The structural formula of the responsive surfactant mpangag (hereinafter abbreviated as mpangag) is as follows:
the preparation method of the MPANGG comprises the following steps: firstly, carrying out addition reaction on rosin and maleic anhydride to prepare maleopimaric acid; then, carrying out imidization reaction on the maleopimaric acid and N, N-dimethyl-1, 3-propanediamine to generate MPAN; finally, the MPAN and the glycidol are subjected to esterification reaction in an absolute ethyl alcohol solvent to obtain a target product.
It is another object of the present invention to provide a process for preparing rosin-based CO using the above 2 /N 2 The preparation method of the responsive microemulsion comprises the following steps:
(1) Rosin-based CO 2 /N 2 The responsive surfactant MPANGG and sodium dodecyl sulfate are dissolved in water to prepare a surfactant compound system;
(2) Then mixing the surfactant compound system with n-hexane, and dropwise adding n-butanol under stirring to obtain CO 2 /N 2 Responsive microemulsions. Capillary CO extraction 2 Slowly introducing into the microemulsion from a condensing tube, making the system become turbid, and continuously introducing CO 2 The system has white precipitation, and the microemulsion breaks emulsion; and then N is added 2 In the same way, the emulsion breaking system is introduced into the system, the microemulsion is intermittently subjected to ultrasonic treatment during the process, the emulsion breaking system is changed into clear and transparent microemulsion again, and the process can be repeated for a plurality of times.
A third object of the present invention is to provide a process for producing a rosin-based CO using the above 2 /N 2 The method for preparing Ag nano particles by the responsive microemulsion comprises the following steps:
(1) AgNO is to be carried out 3 Adding aqueous solution to rosin-based CO 2 /N 2 Stirring and mixing the reactive microemulsion to obtain uniform, colorless and transparent microemulsion, and reacting in a dark environment to generate microemulsion containing Ag nano particles; preferably, the temperature of the reaction in the light-shielding environment is room temperature for 3-4 days, preferably 4 days;
(2) CO is introduced into the microemulsion containing Ag nano particles 2 Breaking emulsion to separate out white precipitate, and separating the white precipitate to obtain Ag nanometer particle.
The reaction mechanism of the invention is as follows:
rosin-based CO 2 /N 2 The responsive surfactant MPANGG is nonionic surfactant, and CO is introduced into the microemulsion 2 Then, MPANGG becomes a cationic surfactant MPANGGH by protonation + The method comprises the steps of carrying out a first treatment on the surface of the Cationic MPANGGH + The sodium dodecyl sulfate which can be combined with anionic sodium dodecyl sulfate into salt through electrostatic action loses the surface activity so as to demulsify the microemulsion; and then to MPANGGH + N is introduced into the aqueous solution of (2) 2 The deprotonation is changed into a nonionic surfactant MPANGG, the system is returned to the state of the microemulsion again, and the process can be repeated for a plurality of times; system pair CO 2 /N 2 The response process and schematic diagram are as follows:
the formation of Ag nanoparticles is the tertiary amine group in MPANGG and AgNO 3 The oxidation-reduction reaction occurs by the following reaction mechanism:
compared with the prior art, the invention has the following beneficial effects:
(1) The surfactant MPANGG disclosed by the invention is prepared from natural rosin resources, accords with the concept of green sustainable development, is a microemulsion, and is simple in preparation method and green in raw material and free of pollution; the particle size of the prepared microemulsion is basically unchanged after the prepared microemulsion responds for a plurality of times, and the microemulsion can be recycled for a plurality of times.
(2) The invention utilizes tertiary amine groups in MPANGG to treat CO 2 The responsiveness of the polymer is interacted with sodium dodecyl sulfate to prepare a responsive microemulsion; the stimulus-responsive trigger factor of the microemulsion is CO 2 /N 2 ，CO 2 /N 2 The emulsion is easy to remove from the system, and can not pollute the microemulsion system, so that the microemulsion can be recycled, and the input cost is obviously reduced; and CO 2 /N 2 Environment-friendly, nontoxic, low in price and easy for industrial application.
(3) The tertiary amine group contained in the MPANGG in the microemulsion is utilized to cause the tertiary amine group to have oxidation-reduction reaction with silver ions, so that the silver nano particles are prepared, the rapid separation of the nano particles from the system can be realized, the operation is simple, and the production efficiency is improved.
Drawings
FIG. 1 shows MPANGG 1 H NMR spectrum;
FIG. 2 is CO 2 /N 2 An appearance diagram of a response process of the response type microemulsion;
FIG. 3 is an analytical graph of emulsion particle size after 3 repeated responses of the microemulsion;
FIG. 4 shows AgNO 3 The appearance of the aqueous solution was compared before and after 4 days of standing in the microemulsion.
Detailed Description
The invention will be further illustrated with reference to examples. It will be apparent that the described embodiments are some, but not all, embodiments of the invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
EXAMPLE 1 preparation of MPANGG
100g (0.33 mol, total amount of abietic acid, neoabietic acid and palustric acid is calculated according to 80 percent, 0.265 mol) of pinus massoniana rosin, 35g (0.357 mol) of maleic anhydride, 40g of acetic acid, and reacting for 4 hours at 140 ℃, cooling, adding 100g of glacial acetic acid, cooling, crystallizing, and filtering by suction to obtain the maleopimaric acid.
10g of maleopimaric acid was added to the reactor and dissolved in ethanol, followed by stirring at 85℃for 0.5 h. Dissolving 2.55g of N, N-dimethyl-1, 3-propylene diamine in ethanol solvent, dropwise adding into a reactor, continuously stirring for 5h after the dropwise adding, cooling, precipitating white crystal, filtering, and drying to obtain MPAN
10g of MPAN is added into a reactor and dissolved in ethanol, after stirring for 0.5h at 85 ℃, 2.36g of glycidol is dissolved in solvent ethanol, the mixture is added into the reactor dropwise, after the dripping is finished, triethylamine (the amount of the triethylamine is 1wt% of the total mass of the reactants) is added, stirring is continued for 8h, the solvent is distilled off, and the crude product is purified by a chromatographic column (the volume ratio of methanol to dichloromethane is 2:8) to obtain the product MPANGG.
MPANGG 1 The H NMR spectrum is shown in FIG. 1, from FIG. 1 1 The H NMR spectrum shows that the prepared product is the target product. The structural formula is as follows:
EXAMPLE 2CO 2 /N 2 Preparation of responsive microemulsions
Firstly, 2.345g of MPANGG and 1g of Sodium Dodecyl Sulfate (SDS) are dissolved in 6.06g of water (the amounts of substances strictly controlling the MPANGG and the SDS are the same) to prepare a surfactant compound system (ME); after 0.4g of gME and 0.6g of n-hexane were mixed, 1g of n-butanol was added dropwise under stirring to obtain a clear and transparent microemulsion. The prepared microemulsion is respectively dripped into water and n-hexane, and is O/W type microemulsion if the microemulsion is dispersed in water and not dispersed in n-hexane, W/O type microemulsion if the microemulsion is not dispersed in water and dispersed in n-hexane, and bicontinuous microemulsion if the microemulsion is dispersed in water and n-hexane. Through experiments, the invention is preparedThe result is a W/O type microemulsion. Through experimental verification, when ME: n-butanol: the mass ratio of the n-hexane is (1-9): (1-15): (1-9), and MPANGG in ME: SDS: the mass ratio of water is (2-10): (1-5): (6-30) preparing CO 2 /N 2 A responsive microemulsion; in addition to n-hexane, the same experimental purposes can be achieved by using an alkane liquid compound such as n-heptane or liquid paraffin as the oil phase.
Example 3
In order to make the experimental phenomenon more obvious, the microemulsion is placed in a test tube with a plug scale, a condensing tube is placed above the test tube, and a capillary tube is used for placing CO 2 Slowly introducing into the microemulsion from a condensing tube, making the system become turbid, and continuously introducing CO 2 The system has white precipitation, and the microemulsion breaks emulsion; and then N is added 2 In the same way, the emulsion breaking system is introduced into the system, the microemulsion is intermittently subjected to ultrasonic treatment during the process, the emulsion breaking system is changed into clear and transparent microemulsion again, and the process can be repeated for a plurality of times. With CO being introduced into the microemulsion 2 /N 2 The change in appearance of (2) is shown in figure 2. FIG. 3 is an analytical graph of emulsion particle size after 3 microemulsion responses, and it can be seen from the graph that the emulsion particle size is not substantially changed after several repetitions.
Example 4
After 0.4g of gME and 0.6g of n-hexane were mixed, 1g of n-butanol was added dropwise under stirring to obtain a clear and transparent microemulsion. 0.01g of AgNO with a mass concentration of 2% was added to the microemulsion 3 Mixing the aqueous solution in dark place to obtain uniform colorless transparent microemulsion, standing at room temperature in dark place for 4 days, sampling at intervals to measure ultraviolet visible near infrared, and gradually changing the microemulsion from uniform, colorless transparent to reddish brown with the extension of dark place time, wherein the appearance chart is shown in figure 4, and shows that tertiary amine in the system gently changes AgNO under low temperature condition 3 Reduced into Ag nano particles, and the plasma excitation of electrons on the surfaces of the Ag nano particles can cause the Ag nano particles to absorb ultraviolet and visible light due to the small-size effect, and the absorbance enhancement shows that the silver ions Ag are generated along with the extension of the standing time + Gradually reduced to metalSilver Ag.
Although the present disclosure describes embodiments, not every embodiment is described in terms of a single embodiment, and such description is for clarity only, and one skilled in the art will recognize that the embodiments described in the disclosure as a whole may be combined appropriately to form other embodiments that will be apparent to those skilled in the art. Therefore, the above description is only of the preferred embodiments of the present application and is not intended to limit the scope of the present application; all changes which come within the meaning and range of equivalency of the claims are to be embraced within their scope.
Claims (6)
1. Rosin-based CO 2 /N 2 The responsive microemulsion is characterized in that: the material comprises the following components in parts by mass:
1-9 parts of surfactant compound system,
1-15 parts of n-butyl alcohol,
1-9 parts of oil phase;
wherein the surfactant compound system is composed of rosin-based CO 2 /N 2 The responsive surfactant MPANGG, sodium dodecyl sulfate and water are mixed according to the mass ratio of (2-10): (1-5): (6-30);
the rosin-based CO 2 /N 2 The structural formula of the responsive surfactant mpangag is as follows:
2. rosin-based CO according to claim 1 2 /N 2 The responsive microemulsion is characterized in that: the oil phase comprises at least one of normal hexane, normal heptane and liquid paraffin.
3. Rosin-based CO according to claim 1 2 /N 2 The preparation method of the responsive microemulsion is characterized by comprising the following steps: the method comprises the following steps:
(1) Rosin-based CO 2 /N 2 Dispersing a responsive surfactant MPANGG and sodium dodecyl sulfate in water to prepare a surfactant compound system, which is marked as ME;
(2) Mixing ME with oil phase, adding n-butanol under stirring to obtain CO 2 /N 2 A responsive microemulsion; capillary CO extraction 2 Slowly introducing the emulsion into the microemulsion, and demulsifying the microemulsion; and then N is added 2 In the same way, the emulsion breaking system is introduced into the system, the microemulsion is intermittently subjected to ultrasonic treatment during the process, the emulsion breaking system is changed into clear and transparent microemulsion again, and the process can be repeated for a plurality of times.
4. A preparation method of Ag nano particles is characterized in that: the method comprises the following steps:
(1) AgNO is to be carried out 3 Addition of an aqueous solution to a rosin-based CO according to any one of claims 1 to 3 2 /N 2 Uniformly mixing the reactive microemulsion to obtain colorless and transparent microemulsion, and reacting in a dark environment to generate microemulsion containing Ag nano particles;
(2) CO is introduced into the microemulsion containing Ag nano particles 2 Breaking emulsion to separate out white precipitate, and separating the white precipitate to obtain Ag nanometer particle.
5. The method for producing Ag nanoparticle according to claim 4, wherein: in the step (1), the reaction temperature in the light-shielding environment is room temperature, and the reaction time is 3-4 days.
6. The method according to claim 4, wherein: in step (1), the AgNO 3 The mass concentration of the solute in the aqueous solution is 1-3%.
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