KR20110113455A - Surfactant for Nanoparticle Aqueous Dispersion - Google Patents

Abstract

The present invention relates to a surfactant capable of stably dispersing nanoparticles in an aqueous system. The surfactant according to the present invention can stably disperse various kinds of nanoparticles in water, and maintains physical properties of metals and oxides. It can be widely used in various nanoparticles such as metal and quantum dots.

Description

Surfactants for Water Dispersing Nanoparticles

The present invention relates to a surfactant capable of stably dispersing nanoparticles in an aqueous system.

Nanoparticles have a large surface area to volume due to their size, and have a quantum confinement effect that is completely different from the bulk material (see Alivisatos, AP Science, 271: 933). (1996)). Among various nanoparticles, fluorescent quantum dots and magnetic iron oxide nanoparticles can be used for imaging in living organisms. For this purpose, uniformly sized nanoparticles are required and water-soluble. (Gao, X. et al., S. Nat. Biotechnol, 22: 969-976 (2004); Bruchez, JM et al., AP Science, 281: 2013-2016 (1998); Chan, WCW et al., S. Science, 281: 2016-2018 (1998); and Weissleder, R. et al., L. Nat. Biotechnol, 23: 1418 (1998). The simplest method for this purpose is to make nanoparticles from water, but synthetic methods known to date make it impossible to produce uniform nanoparticles by water-soluble methods. In the case of quantum dots, when synthesized in water, the quantum yield is too low to be applied to actual imaging, and even iron oxide has not been reported to have uniform iron oxide nanoparticles.

Therefore, it is generally necessary to synthesize uniform quantum dots or iron oxide nanoparticles in an organic solvent and transfer them to water.

Recently, homogeneous quantum dots such as CdSe (Cadmium Selenide) and CdTe (Cadmium Telluride) and the synthesis of magnetic nanoparticles such as iron oxide, iron-platinum (FePt), and cobalt have been developed, and various surfactants for receiving them have been reported. It became.

To obtain water-soluble quantum dots, water-soluble polymers, lipids, thiol ligands such as thiol dendrimers and dithiol have been used. In addition, various metal nanoparticles could be sent to the aqueous solution layer using dimethylaminopyridine (4- (dimethyl-amino) pyridine). In the case of iron oxide, Weissleder's team was able to dissolve iron oxide of various sizes in water using dextrane and used it for MRI. In addition, various nanoparticles were also dissolved in water using a polymer using cyclodextran or maleic anhydride as a main chain.

Surfactants that can dissolve iron oxide, quantum dots, and various metals in water have been reported, but quantum yield problems and stability problems remain unresolved.

In the case of quantum dots, when the quantum yield is 50% in an organic solvent, when dissolved in water using a surfactant, only 50 to 60% of the original yield (as a result, a yield of 25 to 30%) has a problem.

In the case of iron oxide, research has been poorly performed compared to the need for solubilization, and in most cases, a method of dissolving in water using phospholipid or dextran was used. Since there is a method using the vesicles (Vesicle), there was a problem that aggregation tends to occur when the concentration is diminished. This phenomenon is particularly severe in magnetic nanoparticles, and it may be because the attraction between the magnetic nanoparticles is more active than other nanoparticles.

Therefore, the present inventors have studied to overcome the problems of the prior art, such as the quantum yield problem and stability problem, and found a novel aqueous dispersion surfactant and using various kinds of nano It was found that the particles can be stably dispersed in water, no aggregation phenomenon occurs, and solvent substitution at room temperature can overcome the quantum yield problem in quantum dots, thereby completing the present invention.

Accordingly, an object of the present invention is to provide a novel nanoparticle aqueous dispersion for solving the quantum yield and stability problems of nanoparticles.

In order to achieve the above technical problem, the present invention provides a surfactant for dispersing the aqueous nanoparticles represented by the following Chemical Formula 1.

In Formula 1 n is 1 to 500; R ₁ is C ₁ to C ₃₀ alkyl; R ₂ is hydrogen or C ₁ to C ₅₀ alkyl; R ₃ is hydrogen or C ₁ to C ₃₀ alkyl.

The surfactant for dispersing the aqueous nanoparticles according to the present invention can stably disperse various kinds of nanoparticles in water and is expected to be widely used for various nanoparticles such as metals, metal oxides and quantum dots by maintaining physical properties. .

By accepting the quantum dots of the present invention into living organisms, macroscopic observation of biological metabolism and diagnosis of various diseases including cancer are possible. . In addition, the overall synthesis process is very economical and mass production is possible, so it is possible to replace the expensive phospholipid that is currently used to obtain water-soluble nanoparticles, so it is expected to generate sales by industrialization.

In addition, MRI using magnetic nanoparticles can be widely applied to more research, and it is expected to create a great economic effect, especially in the MRI contrast medium market.

Figure 1 is a photograph showing the result of the gel filteration (left) and the hydration diameter (right) by light scattering.
Figure 2 is a schematic of the shape when the nanoparticles are moved to water using a surfactant under a dichloromethane (MC) solvent (phase); This figure shows the shape of oleic acid, Oleylamine and TOP / TOPO when they were transferred to water.
FIG. 3 is a graph showing MALDI-TOF data of mPEG (Mn2000), one step intermediate and final product from above.
Figure 4 is a graph showing the ¹ H NMR data of the intermediate step (top) and the final product (bottom).
Figure 5 (a) is Fe ₂ O ₃ nanoparticles dissolved in hexane, (b) is Fe ₂ O ₃ nanoparticles contained in a water solvent using a surfactant (using Mn5000 mPEG) made by the present invention, ( c) is Fe ₂ O ₃ nanoparticles contained in a water solvent using a surfactant (using Mn2000 mPEG) made by the present invention, (d) Fe ₂ in a water solvent using a surfactant (using Mn750 mPEG) O ₃ nanoparticles, (e) using Fe ₂ O ₃ nanoparticles with a surfactant in the form of a di (mPEG) -mono (alkyl) in water, and (f) using Fe ₂ O ₃ nanoparticles in water Shown for use with surfactants in mono (mPEG) -di (alkyl) form.
6 is a photograph showing nanoparticles (left) dissolved in hexane and nanoparticles (right) dissolved in water, respectively. (a) is a photograph of the CdSe / ZnS nanoparticles observed under UV light; The picture inserted at the bottom left is a picture of the nanoparticles under normal light; Inserted at the bottom right is a TEM image of the nanoparticles in water. (b) is a photograph showing InP / ZnS nanoparticles; The graph inserted at the bottom right shows the fluorescence of the nanoparticles in hexane and water. (c) is a photograph of gold nanoparticles; The picture inserted at the top right is a TEM image of the nanoparticles; The graph inserted at the bottom left shows a graph of absorbance of nanoparticles in water (red) and hexane (blue). (d) a photograph of Fe ₂ O ₃ nanoparticles; The picture inserted at the top left is a TEM image of the nanoparticles in water; Inserted at the bottom right is a picture of nanoparticles in water under the magnetic field.
Figure 7 is a photograph experiment to confirm that the nanoparticles used as MRI contrast agent was dispersed in a water solvent using a surfactant and then lost the role as MRI contrast agent.
8 is an absorption spectrum measured after dispersing the gold nanoparticles synthesized in an organic solvent in a water solvent.
9 shows a state in which CdSe / ZnS, InP / ZnS, Au, and Fe ₂ O ₃ nanoparticles are dispersed in hexane from the left side (left). The right picture shows the photo of these nanoparticles dispersed in a water solvent using a surfactant. The lower part of each photograph is a water solvent layer, and the upper part is a hexane solvent layer.

The present invention relates to a novel surfactant for aqueous dispersion of nanoparticles, and more particularly, to provide a surfactant represented by the following formula (1).

[Formula 1]

In Formula 1 n is 1 to 500; R ₁ is C ₁ to C ₃₀ alkyl; R ₂ is hydrogen or C ₁ to C ₅₀ alkyl; R ₃ is hydrogen or C ₁ to C ₃₀ alkyl.

In the present invention, the nanoparticles refer to general nanoparticles, for example, metals such as gold (Au) and palladium (Pd), magnetic oxides such as Fe ₂ O ₃ , Fe ₃ O ₄ , or CdSe, InP / ZnS, and CdSe. / ZnS Refers to the same quantum dot as Core-shell.

Such a surfactant represented by the formula (1) according to the present invention is synthesized using a compound represented by the following formula (2) to 7 and the preparation method is the same as Scheme 1.

Scheme 1

N is 1 to 500 in Formulas 2, 3, 4, 5, 6, 7 and Scheme 1; R ₁ is C ₁ to C ₃₀ alkyl; R ₂ is hydrogen or C ₁ to C ₅₀ alkyl; R ₃ represents hydrogen or alkyl of C ₁ to C ₃₀ ; X represents F, Cl, Br or I.

Surfactant for aqueous dispersion of nanoparticles represented by Formula 1 of the present invention

(a) preparing a compound represented by Chemical Formula 6 by reacting the compound represented by Chemical Formula 2 with the compound represented by Chemical Formula 3 at 10 ° C. to 200 ° C. for 1 to 24 hours under a nitrogen atmosphere.

(b) reacting the compound represented by Chemical Formula 6 obtained in (a) with a compound represented by Chemical Formula 4 at a temperature of 10 ° C. to 200 ° C. for 0.5 to 48 hours under a nitrogen atmosphere to prepare a compound represented by Formula 7 step; And

(c) the compound represented by the formula (7) obtained in (b) is prepared through the step of reacting the compound represented by the formula (5) with a nitrogen atmosphere at 10 ℃ to 200 ℃ for 1 to 48 hours, all the above process is It proceeds using a nucleophilic substitution reaction.

First, in the step (a), in the compound represented by Formula 2, X, F, Cl, Br or I may be used as the halogen group element, and preferably Cl is used.

In the case of the compound represented by Formula 3, R ₁ is C ₁ To substituted with C ₃₀ alkyl, preferably C ₁ It is preferable to use those substituted with alkyl of C to C ₅ . For example, methoxy-PEG or ethoxy-PEG may be used as the compound represented by Formula 3. In addition, the n is preferably used to be about 1 to 500, preferably used to be about 10 to 200.

In the case of step (a), in order to induce a 1: 1 reaction, it is preferable to add an excess of the compound represented by the formula (2), otherwise the compound represented by the formula (3) is more than two times to the compound represented by the formula (2) There is a problem that the substitution does not proceed easily to the next step.

In the case of step (b), in the case of the compound represented by Formula 4, R ₂ is hydrogen or C ₁ It is preferable to use those substituted with C to C ₅₀ alkyl, preferably C ₁ It is preferable to use those substituted with C- ₂₀ to alkyl. For example, hexadecylamine (HDA), octadecylamine (Octadecylamine, ODA) may be used as the compound represented by Formula 4.

In the case of step (c), in the case of the compound represented by Formula 5, R ₃ is hydrogen or C ₁ It is preferable to use those substituted with alkyl of C to ₃₀ , preferably C ₁ It is preferable to use those substituted with alkyl of C to C ₅ . For example, methanol, ethanol, propanol or butanol, etc. may be used as the compound represented by the formula (5).

By going through the step (c), it is possible to replace the halogen element of the compound represented by the formula (7) with the compound represented by the formula (5) to make a non-toxic surfactant for nano-based aqueous dispersion.

The reaction process of step (c) may be repeated several times in order to replace the compound represented by Chemical Formula 5 at a high ratio with the compound represented by Chemical Formula 7. This is because when the alkyl chain of the material represented by the formula (4) is long, the nonpolarity is strong, so that the substitution of the compound represented by the formula (5) does not occur easily.

All the process of the present invention is carried out under nitrogen conditions of 30 ℃ to 60 ℃ This is to prevent this in advance because the water in the air also acts as a nucleophile is more reactive than other materials. In the reaction, an aprotic solvent may be used as the solvent, for example, tetrahydrofuran (THF) may be used.

Surfactant for dispersing the aqueous nanoparticles prepared by the present invention, unlike other aqueous dispersible surfactants, solvent substitution is possible at room temperature. In the case of quantum dots, when the organic solvent is substituted with water, the quantum yield decreases due to high temperature heating. However, in the case of the surfactant according to the present invention, the quantum yield is less changed by the substitution reaction at room temperature.

EMBODIMENT OF THE INVENTION Hereinafter, this invention is demonstrated further more concretely based on the Example of this invention. However, the following examples are only for illustrating the present invention and are not intended to limit the scope of the present invention.

< Example  1> Preparation of Surfactant for Aqueous Dispersion of Nanoparticles

2 g (1 mmol) of mPEG (polyethylene glycol methylether (Mn2000)) and 0.5 ml of POCl ₃ were removed in 250 ml flask and reacted at 40 ° C. for 12 hours. At this time, 5 mmol of POCl ₃ was reacted with mPEG to induce a 1: 1 reaction. In order to remove unreacted POCl ₃ and HCl produced in the reaction, the resultant was vacuum dried at 40 ° C. for 2 hours and then dissolved in 15 ml anhydrous THF.

0.241 g (1 mmol) of HDA (Hexadecyl amine) was dried under vacuum at 120 ° C. for 2 hours to remove moisture, and then dissolved in 3 ml THF and placed in a 250 ml flask where the basic reaction proceeded. Vacuum drying was performed for 2 hours to remove HCl and THF, 5 ml of MeOH was added and reacted at 60 ° C. for 1 hour, followed by three times of removal to induce complete substitution of MeOH. This is because the substitution of MeOH is difficult because the alkyl chain of HDA is non-polar and it is difficult to completely substitute. Finally, 1 ml of Ethylene diamine (EDA) was added to remove HCl, followed by stirring for 30 minutes to form a salt, followed by vacuum drying to remove THF and EDA. The resultant was dissolved in dichloromethane (MC) having less polarity than THF and centrifuged to remove the HCl salt, and only the final product dissolved in the supernatant was taken. ³¹ P NMR, ¹ H NMR, MALDI-TOF, and the like were used to analyze the structure of each reactant.

The reaction scheme of the experiment is shown in Scheme 2 below, the MALDI-TOF results of this example are shown in FIG. 3, and the results of ¹ H NMR are shown in FIG. 4. 3 shows the results of MALDI-TOF of mPEG (Mn2000), the intermediate of the reaction between mPEG and POCl ₃ and the final product from above. It was found that the substitution reaction was successful because the peak of mass was shifted in each step. POCl ₃ was used in excess of mPEG in the first reaction step, resulting in a mono-mPEG substituted intermediate. In the second reaction step, due to the low reactivity of the last chloride (Cl), no di-alkyl substituted intermediates are formed, only mono-alkyl substituted intermediates.

In the case of Figure 4 ¹ H NMR spectrum of the final product was confirmed that the mono-mPEG and mono-alkyl substituted compounds. The ethylene group peak of mPEG was observed at 3.6 ppm and at the terminal -OCH ₃ of mPEG at 3.382 ppm. Three broad peaks of 1.76 ppm, 1.23 ppm and 0.88 ppm showed -CH ₂ NHP-, -CH _2- , and terminal -CH ₃ of HDA, respectively.

In addition, ³¹ P NMR data also confirmed that the reaction was successful.

Scheme 2

< Example  2> mPEG  Performance Comparison of Surfactants for Aqueous Dispersion of Nanoparticles by Molecular Weight

Experiments were performed by controlling the molecular weight of mPEG in order to optimize the performance of the nanoparticle aqueous dispersion. Surfactant was synthesized by changing the molecular weight of mPEG to 750, 2000, 5000, etc., and the performances were compared. In the case of the surfactant using mPEG750, 0.75 g (1 mmol) of mPEG (polyethylene glycol methylether (Mn750)) having been dehydrated in a 250 ml flask was dissolved in 0.5 ml of POCl ₃ and reacted at room temperature for 12 hours. The subsequent synthesis process is the same as the method shown in Example 1 above. The synthesis of surfactant using mPEG2000 was synthesized according to Example 1 above. In the case of the surfactant using mPEG5000, 5 g (1 mmol) of mPEG (polyethylene glycol methylether (Mn5000)) and 0.5 ml of POCl ₃ were removed in a 250 ml flask and dissolved in 20 ml of anhydrous THF, and then reacted at 60 ° C. for 12 hours. The subsequent synthesis process is the same as the method shown in Example 1 above. Same amount of Fe ₂ O ₃ Each surfactant synthesized with the nanoparticles was mixed in 5 equivalents of dichloromethane organic solvent, and the solvent was evaporated at room temperature for 15-20 minutes, and water was added to the remaining mixture and dispersed again. When the surfactants were redispersed in water using the same method described above, the nanoparticles of mPEG 5000 and mPEG 2000 were re-dispersed in water, but not of mPEG 750.

The results of this experiment are shown in (b) Mn 5000, (c) Mn 2000 and (d) Mn 750 of FIG.

The amount of Fe in each sample was measured by ICP (Inductively Coupled Plasma), and the amount measured by ICP was 0.203 mg / ml, 0.148 mg / ml and 0.010 mg / ml, respectively (b), (c) and (d). Appeared. That is, it was confirmed that the amount of Fe ₂ O ₃ dispersed in water increases as the molecular weight of mPEG increases. As a result, it can be seen that a long hydrophilic group is necessary to disperse the nanoparticles in water.

mPEG  Performance Comparison of Surfactants for Aqueous Dispersion of Nanoparticles by Molecular Weight Molecular Weight of mPEG Used The amount of Fe measured by ICP
(mg / ml)  Mn 5000 0.203  Mn 2000 0.148 Mn 750 0.010

< Example  3> Comparison of the performance according to the difference of surfactant structure for aqueous dispersion of nanoparticles

In order to verify the performance according to the surfactant structure, surfactants in the form of di (mPEG) -mono (alkyl) and mono (mPEG) -di (alkyl) rather than the general mono (mPEG) -mono (alkyl) substituted forms The synthesis was carried out and tested. mPEG2000 was used and each surfactant according to the form was synthesized by the experimental method shown in Example 1. Same amount of Fe ₂ O ₃ Each of the different types of surfactants synthesized with the nanoparticles were mixed in an organic solvent of dichloromethane by 5 equivalents. After evaporating all the solvents at room temperature for 15-20 minutes, water was added to the remaining mixture and dispersed again.

The results of the experiment are shown in FIGS. 5 (c), (e) and (f). Measurements (e) and (f) show very poor ability to move nanoparticles into water.

Performance Comparison by Difference in Surfactant Structure for Aqueous Dispersion of Nanoparticles Structure of Surfactant Nanoparticle Aqueous Dispersion Capacity Mono (mPEG) -mono (alkyl): FIG. 5 (c) height Di (mPEG) -mono (alkyl): FIG. 5 (e) lowness Mono (mPEG) -di (alkyl): Fig. 5 (f) lowness

Combining Example 2 and Example 3, it can be seen that the surfactant having the best ability to disperse the nanoparticles in the water system is a mono (mPEG) -mono- (alkyl) substituted surfactant using Mn5000.

< Example  4> Comparison of Surfactant Performance for Aqueous Dispersion According to Intrinsic Stabilizers of Nanoparticles

Surfactant formation of micelles around nanoparticles in water is confirmed by ³¹ P-NMR (phosphate shows the same peak in ESI water and hexane solvents). The cause of this phenomenon is the original stabilizer used to stabilize the nanoparticles in the alkyl portion of the surfactant and in the organic solvent, which is a stabilizer on the surface of the nanoparticles. Aggregation occurs well because of the attraction of oleic acid, oleylamine and trioctylphosphine oxide (TOPO), which stabilizes the surface of nanoparticles and stabilizes them in organic solvents. Therefore, the versatility of the surfactant depends on the structure of the original stabilizer.

In this example, Oleic acid, Oleylamine and TOP / TOPO were selected as three commonly used stabilizers. Generally, palladium, Fe ₂ O ₃ , InP / ZnS nanoparticles use oleic acid, gold nanoparticles use oleylamine, and CdSe / ZnS use TOP / TOPO. These were synthesized with reference to the citations ((a) NR Jana, Y. Chen and X. Peng, Chem. Mater., 2004, 16, 3931; (b) J. Park, K. An, Y. Hwang, J .-G. Park, H.-J. Noh, J.-Y. Kim, J.-H. Park, N.-M. Hwang and T. Hyeon, Nat. Mater., 2004, 3, 891; ( c) FX Redl, CT Black, GC Papaefthymiou, RL Sandstorm, M. Yin, H. Zeng, CB Murray and SP O'Brien, J. Am. Chem. Soc., 2004, 126, 14583). Each nanoparticle was transferred from the organic solvent to water in the same manner as in Example 2. The results of the experiment are shown in FIG. 6. The results in FIG. 6 showed that in each case the migration from hexane solvent to water solvent was successful. Each nanoparticle in the water solvent did not change its physical properties and was well dispersed. In the case of (a) and (b) of FIG. 6, the photoluminescence peak did not change even after moving to a water solvent. The quantum yield in water was 65% based on hexane solvent, and the quantum yield was increased to 70% when mPEG Mn5000 surfactant was used.

Quantum yields were calculated using the absorption spectra and fluorescence spectra of CdSe / ZnS nanoparticles in hexane solvent and dispersed in water. Absorption spectra were measured using a UV-vis spectrophotometer, and fluorescence spectra were measured using a fluorescence spectrophotometer. As a reference organic dye, Rodamine 590 was used, and the quantum yield of the dye was 95% in ethanol solvent. Quantum yield was calculated as follows. (Q = quantum yield, A = area of fluorescence spectrum, I = absorption spectrum of excitation wavelength, n = dielectric constant of solvent a = CdSe / ZnS, b = organic dye)

The inner graph of (c) of FIG. 6 shows the surface plasmon resonance of 530 nm in the water absorption (red graph) and hexane solvent (blue graph) in the optical absorption graph of gold nanoparticles. 6 (d) shows that Fe ₂ O ₃ nanoparticles dispersed in a high concentration of water can be applied to various fields in a ferro-fluid state.

< Example  5> Quantum yield measurement when using surfactant for aqueous dispersion of nanoparticles

Same amount of Fe ₂ O ₃ Each surfactant synthesized with the nanoparticles was mixed in 5 equivalents of dichloromethane organic solvent, and the solvent was evaporated at room temperature for 15-20 minutes, and water was added to the remaining mixture to disperse. Quantum yields were calculated using the absorption spectra and fluorescence spectra of CdSe / ZnS nanoparticles in hexane solvent and dispersed in water. Absorption spectra were measured using a UV-vis spectrophotometer, and fluorescence spectra were measured using a fluorescence spectrophotometer. As a reference organic dye, Rodamine 590 was used, and the quantum yield of the dye was 95% in ethanol solvent. Quantum yield was calculated as follows. (Q = quantum yield, A = area of fluorescence spectrum, I = absorption spectrum of excitation wavelength, n = dielectric constant of solvent a = CdSe / ZnS, b = organic dye (rhodamine (590)) using the surfactant of the present invention The quantum yield was about 70-80% based on the hexane solvent.

In order to disperse nanoparticles in water, mercaptopropionic acid or phospholipid, which is used in the past, is only about 50% based on hexane solvents. In comparison, when the surfactant of the present invention was used, the quantum yield was about 70 to 80% based on the hexane solvent. This is because it is carried out at room temperature without applying heat during the process of dispersing in water using a surfactant.

< Example  6> Nanoparticles of Surfactant for Aqueous Dispersion Imaging  In the field Usability test

Hydration radius was measured by light scattering and gel filtration methods to determine whether the surfactant for aqueous dispersion of nanoparticles according to the present invention can be used in nanobio imaging applications. As a result of the measurement, a hydration radius of 12 nm was shown by gel filtering in FIG. 1, and a hydration radius of 15 nm was shown by light scattering. When used in the field of nano-imaging, the hydration radius is a very important factor, and in the case of Sentinel Lymph Node mapping, nanoparticles spread into blood vessels at less than 5 nm, and Sentinel Lymph at 5 to 10 nm. It passes to the next lymph node without standing on the node, and does not move when it is larger than 300 nm. Injecting into the cell in MRI imaging requires a size of less than 30 nm. Hydration radius is a combination of nanoparticle size and surfactant size in water. It depends on the relative bonding strength and three-dimensional structure rather than the size of each one.

In addition, Figure 7 is a photograph experiment to confirm that the nanoparticles used as MRI contrast agent was dispersed in a water solvent using a surfactant, and then the role of MRI contrast agent is not lost. Figure 7 shows the T ₂ -enhanced image was measured at room temperature to 1.5T used in the actual clinical examination, treatment.

Accordingly, the surfactant for dispersing the aqueous nanoparticles according to the present invention is expected to be used in nanobio imaging applications such as MRI contrast agents.

Claims (5)

Surfactant for dispersing the aqueous nanoparticles represented by the formula (1).
[Formula 1]

In Formula 1 n is 1 to 500; R ₁ is C ₁ to C ₃₀ alkyl; R ₂ is hydrogen or C ₁ to C ₅₀ alkyl; R ₃ is hydrogen or C ₁ to C ₃₀ alkyl.
The nanoparticle aqueous dispersion interface according to claim 1, wherein the nanoparticles are gold (Au), palladium (Pd), Fe ₂ O ₃ , Fe ₃ O ₄ , CdSe, InP / ZnS, or CdSe / ZnS. Active agent.
The compound of claim 1, wherein in Formula 1, n is 10 to 200; R ₁ is C ₁ to C5 alkyl; R ₂ is C ₁ to C 20 alkyl; R 3 is a C ₁ to C 5 alkyl, characterized in that the surfactant for aqueous dispersion of nanoparticles.
(a) reacting the compound represented by the following Chemical Formula 2 with the compound represented by the following Chemical Formula 3 at 10 ° C to 200 ° C for 1 to 24 hours to obtain a compound represented by the following Chemical Formula 6;
(b) reacting the compound represented by the following Chemical Formula 6 obtained in (a) with the compound represented by the following Chemical Formula 4 at 10 ° C. to 200 ° C. for 0.5 to 48 hours to obtain a compound represented by the following Chemical Formula 7; And
(c) a compound represented by the following formula (7) obtained in (b) is represented by the following formula (1) comprising the step of reacting the compound represented by the following formula (5) at 10 ℃ to 200 ℃ for 1 to 48 hours Method for producing a nanoparticles aqueous dispersion for water.
[Formula 1]

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Formula 6]

[Formula 7]

In Formulas 1 to 7, n is 1 to 500; R ₁ is C ₁ to C ₃₀ alkyl; R ₂ is hydrogen or C ₁ to C ₃₀ alkyl; R ₃ represents hydrogen or alkyl of C ₁ to C ₃₀ ; X represents F, Cl, Br or I.
The method of claim 4, wherein the surfactant for dispersing the aqueous nanoparticles represented by Chemical Formula 1 is n is 10 to 200; R ₁ is C ₁ to C ₅ alkyl; R ₂ is C ₁ to C ₂₀ alkyl; R ₃ is a C ₁ to C ₅ alkyl method for producing a surfactant for nanoparticle aqueous dispersion, characterized in that.

Images