CN114854431B - Intelligent Pickering emulsion based on dynamic covalent bonds and preparation method thereof - Google Patents
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Abstract
The invention discloses an intelligent Pickering emulsion based on dynamic covalent bonds and a preparation method thereof, belonging to the field of colloid and interface chemistry. The invention utilizes a surfactant system (H) + AA and FA) and oppositely charged SiO 2 The particles act to form surface active particles with pH as a trigger mechanism, and the Pickering emulsion is synergistically stabilized; bola compounds which are "strongly polar" under alkaline conditions, which compounds do not possess surface activity and cannot synergistically act on SiO 2 The granules stabilize Pickering emulsions; the intelligent conversion of the compound from 'amphiphilicity', 'strong polarity' and the conversion of the emulsion from 'milk formation' to 'non-milk formation' are realized, and the circulation times are six times; meanwhile, the surfactant does not remain in the oil phase, so that the recovery and the reutilization of the surfactant are realized, and the surfactant has important roles in the fields of oil transportation, emulsion polymerization, nano material synthesis, heterogeneous catalysis, oil exploitation, cosmetics, food science and the like.
Description
Technical Field
The invention belongs to the field of colloid and interface chemistry, and particularly relates to an intelligent Pickering emulsion based on a dynamic covalent bond and a preparation method thereof.
Background
In recent years, with the rapid development of nanotechnology, pickering emulsions stabilized by colloidal particles or surface-active particles have attracted widespread attention. The colloid particles can be closely arranged at the oil-water interface, so that the Pickering emulsion has super-strong stability. However, when the emulsion is applied to the fields of oil transportation, emulsion polymerization, nano material synthesis, heterogeneous catalysis and the like, the super-strong stability brings great challenges to demulsification, and a Pickering emulsion with stimulus response performance is generated.
The formation of stimulus-responsive Pickering emulsions often relies on surfactants that are stimulus-responsive. The currently reported modes of stimulation include pH, redox, CO 2 /N 2 The main regulation modes are that the polar groups are converted into nonpolar groups or weak polar groups. However, in emulsion systems, this type of conditioning can cause the surfactant to migrate into the oil phase after deactivation, which not only contaminates the oil phase, but also is detrimental to recovery and reuse of the surfactant. The main regulation mode of the surfactant capable of intelligently switching between the amphiphilicity and the strong polarity is to convert the weak polar group into the polar group, so that the surfactant is too strong in hydrophilicity, and is dissolved in water after losing the surface activity, thereby realizing the recovery and the reutilization of the surfactant. However, the synthesis process of the surfactant is complex, the conversion rate is extremely low (about 15.16%), the use of a plurality of organic solvents is involved, the synthesis process is not green enough, and the application of the surfactant in the fields of petroleum exploitation, cosmetics, food science and the like is greatly limited.
Therefore, it is important to develop an "environmentally friendly" emulsifier process that is "recyclable".
Disclosure of Invention
Technical problem
The general stimulus-responsive surfactant is converted between 'surface active' and 'no surface active' by regulating and controlling the polar groups, but the regulating and controlling mode often ensures that the surfactant is dissolved in the oil phase after being deactivated, thereby not only influencing the quality of the oil phase, but also being unfavorable for the recovery and the reuse of the surfactant. The existing surfactant capable of realizing recovery and reutilization has the problems of complex synthesis process, high synthesis cost, low conversion rate, non-green synthesis process, limited application field and the like. In addition, the emulsion stabilized by the conventional surfactant has the defects of poor stability, excessively high use concentration and the like.
Accordingly, the present invention seeks to provide a smart Pickering emulsion based on dynamic covalent bonds, solving the above problems. The Pickering emulsion is prepared from cationic surfactant H + AA (switchable between "amphiphilic" and "strongly polar") and oppositely charged SiO 2 The particles are synergistic and stable, the synthesis is simple, the synthesis cost is low, the synthesis process is green, the emulsion stability is good, the use concentration is low, and the advantages of recycling and the like are integrated. Wherein, the introduction of dynamic covalent bonds enables the surfactant to be intelligently switched between 'amphiphilicity' and 'strong polarity'. Under acidic conditions, surfactants (H + AA) remain amphiphilic, having surface activity; under alkaline conditions, the surfactant and the other substance form Bola compounds (FA-AA), which exhibit "strong polarity", lose surface activity, and dissolve in water. The whole process can be circulated for a plurality of times, intelligent conversion of 'amphiphilicity' and 'strong polarity' is realized, and the surfactant is always in the aqueous solution, so that the recovery and the reutilization are convenient.
Technical proposal
The invention utilizes a surface active system (H) based on dynamic covalent bonds + AA and FA), which have "amphiphilicity" and which can be combined with oppositely charged SiO 2 The particles act to form surface active particles taking pH as a trigger mechanism, n-decane is selected as an oil phase, and the mixture is homogenized for 2min at the rotating speed of 11000r/min, so that the stable Pickering emulsion can be prepared. Then alternately adding acid and alkali, and converting the structure of surfactant in the solution to form "strong polar" Bola compound FA-AA, which can not be combined with SiO due to its strong hydrophilicity 2 The particles together stabilize the emulsion; the surface-active particles can be switched between "amphiphilic" and "strongly polar", i.e. "surface-active" and "surface-inactive". Adding proper amount of acid into the system, and breaking dynamic covalent bond in FA-AA to generate 'amphiphilicity' cationic surfactant H + AA and FA, thereby achieving a loop. Notably, the FA plays a considerable role during this cycleThe large effect not only imparts stimulus response properties to the surfactant, but is also critical to the system being cycled. Meanwhile, after the emulsion is broken, a fresh oil phase is replaced, and whether the surfactant is dissolved in the oil phase or not is verified, and the surfactant is taken away by the n-decane after the emulsion breaking.
The first object of the invention is to provide an intelligent Pickering emulsion based on dynamic covalent bonds, which is prepared by mixing aqueous phase and hydrophilic SiO 2 Mixing the particles, the surface active system and the oil phase, and homogenizing to obtain the product;
the surface active system is composed of a component H + AA. FA composition:
wherein n=7 to 9, and x is Cl or Br.
In one embodiment of the invention, the molar ratio of the two components is 1:1.
in one embodiment of the invention, a process for preparing a surface-active system is described as follows:
reacting amino alkyl acid AA and FA under alkaline condition at normal temperature to form covalent bond to obtain FA-AA; then FA-AA is subjected to the action of acid HX to obtain a surfactant system; the surface active system can be recovered again under the alkaline action to obtain FA-AA, thereby realizing the reuse of the surface active system.
In one embodiment of the invention, AA in the method is a primary amine-containing compound that forms a dynamic covalent bond with an aldehyde group at ambient temperature and is negatively charged under alkaline conditions.
In one embodiment of the invention, FA in the method is a compound that contains a benzene ring, forms a dynamic covalent bond with a primary amine at normal temperature, and is negatively charged under alkaline conditions.
In one embodiment of the invention, the alkaline pH in the process is from 10 to 13, preferably from 11 to 12.
In one embodiment of the invention, the reaction temperature in the process is ambient temperature.
In one embodiment of the invention, the reaction time in the process is ≡30min to ensure sufficient reaction.
In one embodiment of the invention, the reaction conditions in the process are stirring.
In one embodiment of the invention, fA-AA in the method has a relatively strong hydrophilicity.
In one embodiment of the invention, the acidic pH in the process is in the range of 3 to 5.
In one embodiment of the invention, H in the method + AA is a surfactant.
In one embodiment of the invention, the surfactant system achieves a smart response by:
in one embodiment of the invention, the pH of the base is from 10 to 13, preferably from 11 to 12; the pH value of the acid is 3-5.
In one embodiment of the invention, hydrophilic SiO 2 The mass concentration of the particles relative to the water phase is 0.001-3%.
In one embodiment of the invention, the concentration of the surface-active system, calculated as FA, relative to the aqueous phase is from 0.01 to 10mmol/L.
In one embodiment of the invention, the oil phase comprises any one or more of the following: n-decane, toluene, glyceryl tricaprylate.
The invention further aims to apply the intelligent Pickering emulsion based on the dynamic covalent bond to the fields of oil transportation, emulsion polymerization, nano material synthesis, heterogeneous catalysis, oil exploitation, cosmetics, food science and the like.
Advantageous effects
The invention utilizes a surface active system (H + AA and FA), which have "amphiphilicity" and which can be combined with oppositely charged SiO 2 The particles act to form surface active particles with pH as a trigger mechanism, and the particles cooperate with SiO 2 The granules stabilize Pickering emulsions; bola compounds which are "strongly polar" under alkaline conditions, which compounds do not possess surface activity and cannot synergistically act on SiO 2 The particles stabilize the Pickering emulsion. The intelligent conversion of the compound from 'amphiphilicity' and 'strong polarity' and the conversion of the emulsion from 'milk forming' to 'non-milk forming' are realized, and the conversion can be circulated for six times. Meanwhile, ultraviolet absorbance detection is carried out on the demulsified oil phase, so that the surfactant is proved to be not remained in the oil phase, and the recovery and the reutilization of the surfactant are realized. This feature has important roles in the fields of oil transportation, emulsion polymerization, nanomaterial synthesis, heterogeneous catalysis, oil exploitation, cosmetics, food science, etc.
Drawings
FIG. 1 is an ESI-MS spectrum of a Bola compound FA-AA.
FIG. 2 shows the Bola compound FA-AA 1 H NMR spectrum (60 mm, ph=12.00, d) 2 O)。
FIG. 3 is a diagram of (A) FA-AA, (B) AA and (C) FA 1 Comparison of H NMR spectra (60 mm, ph=12.00, d 2 O)。
FIG. 4 is a comparison of FT-IR spectra of (A) FA-AA, (B) AA and (C) FA (pH=12.00).
FIG. 5 shows surfactant H + AA (AA) 1 HNMR spectra (60 mm, ph=4.00, dmso).
FIG. 6 is a nano SiO 2 Graphs of particle (a) SEM and (b) TEM and (c) Zeta potential as a function of pH.
FIG. 7 is a single nano SiO 2 Photograph of the appearance of a particle (0.1 wt.%) stable n-decane/water (3 mL/3 mL) emulsion relative to the aqueous phase.
FIG. 8 is 0.1wt.% nano SiO 2 Particles and different concentrations of H + AA-stabilized n-decane/water Pickering milkAppearance photographs of (A and B) and (C) micrographs of the liquids. Wherein A is photographed immediately after milk beating, and (B and C) is photographed after the milk is stabilized for 24 hours.
FIG. 9 is 0.1wt.% nano SiO 2 Particles and different concentrations of H + Photographs of the appearance of (a) and (B) micrographs of AA-stabilised n-decane/water Pickering emulsions. Wherein, A and B are both shooting after being stable for one month.
FIG. 10 is a flow chart of the emulsion stimulus response. HCl and NaOH were added for switching: (a) initial solution, (b) n-decane was added and homogenized for 2min, (c) the oil phase was separated off and acidified by addition of HCl, (d) fresh n-decane was added and homogenized for 2min.
FIG. 11 is 0.1wt.% nano SiO 2 Particles with 0.6mM H + Photographs of (a) appearance and (B) micrographs of AA stabilized Pickering emulsions. The on or off cycle is performed by adding HCl and NaOH.
FIG. 12 is a nano SiO 2 Granules and surfactant H + Mechanism diagram of AA stabilized smart Pickering emulsion.
Fig. 13 is a graph of absorbance versus wavelength scan (ph=12.00) for (a) aqueous solutions of different concentrations FA-AA; (b) Absorbance-concentration standard curve (ph=12.00) at 296nm for different concentrations of FA-AA aqueous solutions.
Detailed Description
The emulsion appearance photo is taken by a digital camera or a mobile phone; the emulsion micrograph was taken using a super depth of field three-dimensional microscope from Kidney Co., ltd, with a lower light source, magnification of 250-2500 times, and test temperature of 25 ℃.
Example 1:
the synthetic route for the Bola compound FA-AA is as follows:
equal molar amounts of FA and AA, and 2-fold molar amounts of NaOH were added to a 100mL volumetric flask, and the volume was fixed using ultrapure water. The pH of the solution was then adjusted to 12.00, magnetons were added and stirred for half an hour to ensure the reaction was complete. FinallyAn aqueous solution of FA-AA constructed by dynamic covalent bonds was obtained. ESI-MS of FA-AA, 1 h NMR and FT-IR spectra as shown in FIGS. 1-4.
Similarly, the substitution of 11-aminoundecanoic acid for 10-aminodecanoic acid and 12-aminododecanoic acid, respectively, gives the corresponding Bola compounds 10-FA-AA and 12-FA-AA.
Example 2: preparation of surface-active systems
10mmol of 11-aminoundecanoic acid was added to a 100mL volumetric flask, and the volume was fixed using ultrapure water. The pH of the system was then adjusted to 4.00 using a 2M hydrochloric acid solution, magnetons were added and stirred for half an hour to ensure complete protonation. Finally, surfactant 11-H is obtained + Aqueous AA solution. Of surfactants 1 H NMR is shown in FIG. 5.
Similarly, the corresponding surfactant 10-H can be obtained by replacing 11-aminoundecanoic acid with 10-aminononanoic acid and 12-aminododecanoic acid, respectively + AA and 12-H + AA。
Respectively 10-H + AA、11-H + AA and 12-H + AA is compounded with equimolar FA to obtain a surface active system.
Example 3: nano SiO 2 Surface Activity test of particles
In a 10mL glass bottle, 0.003g of commercial nano SiO was weighed 2 Particles (primary particle diameter of about 20nm, specific surface area S BET About 200.+ -. 20m 2 /g, SEM and TEM see FIG. 6), 3mL of ultrapure water was added and the particles were then uniformly dispersed (0.1 wt.%) using an ultrasonic disperser. Then adding 3mL of n-decane into a glass bottle, and homogenizing and emulsifying for 2min at 11000r/min by using a high shear homogenizer, as shown in FIG. 7, a stable emulsion cannot be obtained, which indicates the commercial nano SiO used 2 The particles are not surface active.
Example 4: preparation of Pickering emulsion
Weighing 0.003g of nano SiO 2 The particles were ultrasonically dispersed in 3mL of a surface active system of different concentrations (calculated as FA, the concentrations relative to the aqueous phase were 0.01mM, 0.03mM, 0.06mM, 0.1mM, 0.3mM, 0.6mM, 1.0mM, 3.0mM, 6.0mM, respectively), 3mL of n-decane was added,after homogenizing and emulsifying for 2min with a high shear homogenizer, a stable O/W type Pickering emulsion was obtained, as shown in FIG. 8. After the emulsion was left for one month, no creaming or breaking of the emulsion occurred, indicating that the obtained Pickering emulsion had very good stability, as shown in FIG. 9.
Example 5: pH stimulus-response Property of Pickering emulsions
To facilitate the experiment, the test was performed according to the procedure of fig. 10.
0.1wt.% nano SiO 2 The particles were studied on the basis of 0.6mM FA-AA. Weighing 0.003g of nano SiO 2 The particles were dispersed sonicated in 0.6mM FA-AA solution (ph=12.00), 7mL n-decane was added and homogenized for 2min with a high shear homogenizer, failing to form a stable Pickering emulsion. The oil phase separated from the upper layer was separated, then 50. Mu.L of 20mM HCl solution was added to the lower aqueous phase, and 3mL of fresh n-decane was added thereto, and after homogenizing for 2 minutes with a high shear homogenizer, a stable O/W type Pickering emulsion was formed, and the emulsion was placed in a incubator at 25℃and allowed to stand for 24 hours to examine its stability. At least 6 cycles can be achieved by alternating NaOH and HCl addition, as shown in fig. 11. The mechanism diagram is shown in fig. 12.
Example 6: emulsifying Properties of different surfactants
Referring to example 3, 0.003g of nano SiO was weighed out 2 The particles are dispersed in 3mL of 0.6mM surfactant system by ultrasonic, 3mL of n-decane is added, and after homogenizing and emulsifying for 2min by a high shear homogenizer, stable O/W Pickering emulsion is obtained.
Replacement of surfactant only for 10-H + AA (n=7) and 12-H + AA (n=9), the other conditions being unchanged, the corresponding Pickering emulsion was obtained. The emulsion thus obtained was left at room temperature, and its stability was measured.
Referring to example 4, pH response performance was tested by adjusting pH. The performance results of the resulting emulsions are shown in Table 1.
TABLE 1 results of emulsifying Properties of different surfactants
Example 7: detection of residual surfactant in oil phase
The detection was performed using an ultraviolet spectrophotometer, and as shown in FIG. 13, the maximum absorption wavelength and absorbance at the maximum absorption wavelength of different concentrations of FA-AA were detected. As can be seen from FIG. 13 (a), fA-AA has two maximum absorption wavelengths, and since the absorption intensity of the E1 band is large, the absorbance is not easily controlled to be within 1, and thus the maximum absorption wavelength (lambda) in the E2 absorption band is selected max =296 nm) was used as the experimental basis. Then, an absorbance-concentration standard curve is drawn from the absorbance of different concentrations FA-AA at this absorption wavelength (fig. 13 (b)). The equation of the fitted curve is y= 1.7333x, variance r 2 ＝0.9995。
The oil phase separated out in each cycle was collected, its ultraviolet absorbance was measured, and its interfacial tension with ultrapure water was measured, and the test results are shown in table 2.
TABLE 2 fresh n-decane and UV absorbance of n-decane isolated after each demulsification
The total absorbance of the separated oil phase was 0.098, which means that 9.4% of the FA was lost for six cycles, which affects H to some extent + The recovery and reuse of AA is probably why it can only be recycled six times, which, of course, is also affected by dilution and accumulation of NaCl.
Claims (9)
1. A method for preparing intelligent Pickering emulsion based on dynamic covalent bonds is characterized in that aqueous phase and hydrophilic SiO 2 Mixing the particles, the surface active system and the oil phase, and homogenizing to obtain the product;
the saidThe surface active system is composed of a component H + AA. FA composition:
wherein n=7 to 9, and x is Cl or Br;
dynamic covalent bonding refers to:
intelligence refers to intelligent switching between amphiphilicity and strong polarity.
2. The method of claim 1, wherein the hydrophilic SiO 2 The mass concentration of the particles relative to the water phase is 0.001-3%.
3. The process according to claim 1, wherein the concentration of the surface-active system, calculated as FA, relative to the aqueous phase is from 0.01 to 10mmol/L.
4. The method of claim 1, wherein the oil phase comprises any one or more of: n-decane, toluene, glyceryl tricaprylate.
5. The method according to claim 1, wherein the molar ratio of the two components in the surface-active system is 1:1.
6. the method according to claim 1, characterized in that the method for preparing the surface-active system is as follows:
reacting amino alkyl acid AA and FA under alkaline condition at normal temperature to form covalent bond to obtain FA-AA; then FA-AA is subjected to the action of acid HX to obtain a surfactant system; the surface active system can be recovered again under the alkaline action to obtain FA-AA for repeated use.
7. An intelligent Pickering emulsion prepared by the method of any one of claims 1-6; wherein the surfactant system achieves intelligent response by:
8. the intelligent Pickering emulsion of claim 7, wherein the pH of the base is 10 to 13; the pH value of the acid is 3-5.
9. Use of the intelligent Pickering emulsion of claim 7 in the fields of oil transportation, emulsion polymerization, nanomaterial synthesis, heterogeneous catalysis, oil exploitation, cosmetics, food science, and the like.
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