PT109110B - SYNTHESIS PROCESS OF MESOPOROSUS SILICA NANOPARTICLES WITH DIAMETERS UNDER 100 NANOMETERS AND PRECISE CONTROL OF PARTICLE SIZE - Google Patents

Abstract

THE PRESENT INVENTION DESCRIBES THE SYNTHESIS PROCESS OF HYBRID MESOPOROSE SILICA NANOPARTICLES WITH DIAMETERS LESS THAN 100 NM AND PRECISE CONTROL OF PARTICLE SIZE. IN THE NANOPARTICLES SYNTHESIS PROCESS THE SOL-GEL METHOD IS USED, IN AQUEOUS MEDIUM, IN WHICH A STRUCTURE DIRECTING AGENT (IONIC TENSIONACTIVE), SOL-GEL PRECURSORS (METALLIC ALCOXIDES), A BASE, A CONSTITUTIONAL COMPOUND, IS USED BY MONO AND/OR MULTIVALENT CATIONS AND ANIONS, AND ORGANIC MOLECULES THAT HAVE AT LEAST ONE ALCOXISSILAN GROUP. THE DIAMETER CONTROL OF SILICA MESOPOROSUS NANOPARTICLES, AS WELL AS THE PORE DIMENSIONS AND SHAPE, IS DONE THROUGH THE PH VARIATION OR THE IONIC STRENGTH OF THE REACTIONAL MIXTURE. THE MESOPOROSUS SILICA NANOPARTICLES DESCRIBED IN THIS INVENTION MAY BE USED FOR IMAGING APPLICATIONS, AS TRANSPORT AND/OR CONTROLLED RELEASE SYSTEMS, AS SUPPORTS FOR CATALYST, OR IN ADSORPTION.

Description

Description

Synthesis process for mesoporous silica nanoparticles with diameters less than 100 nanometers and precise particle size control

field of invention

Technical field in which the invention is inserted

The present invention relates to the process of synthesizing mesoporous silica nanoparticles with diameters less than 100 nm and precise particle size control, incorporating organic molecules into the silica network. These nanoparticles can be used for application in imaging, as transport and/or controlled release systems, as supports for catalysts, or in adsorption.

State of the art

Mesoporous silica nanoparticles are promising structures due to their structural properties, such as high surface area and pore volume, adjustable pore sizes at the nanoscale, colloidal stability, and the possibility of selective functionalization of the pore and/or internal surface. its outer surface. ¹ Due to their unique characteristics, these particles can be used in several areas, such as bioimaging, ² ' ³ catalysis, ⁴ ' ⁵ adsorption, ⁶ transport and/or release of ^117-16 molecules and biomedicine. ^15-18

Since the discovery of MCM-41 (Mobil Crystalline Materials) type materials in 1992 by Mobil company scientists, ¹⁹ there has been enormous interest in controlling and modifying the characteristics of mesoporous silica materials, both in particle size and in diameter and morphology of your pores. ²⁰

To date, there has been a great deal of effort regarding the development of procedures for the synthesis of mesoporous silica particles. ²⁰ The sol-gel process, based on the Stöber method, ²¹ is the most used in the preparation of this type of particles, in which a structure-directing agent is used. The structure-directing agent molecules must form cylindrical micelles in concentrations above their critical micelle concentration, micelles that later self-assemble into aggregates.

The silicate species, after hydrolysis of silicon alkoxide precursors (such as tetraethoxysilane or tetramethoxysilane), condense on the surface of the micelles, forming the silica network. The structure-directing agents can be ionic surfactants (such as hexadecyltrimethylammonium bromide or chloride), which at the end of the reaction are removed leaving the pores of the particles free. This process is sensitive to different factors such as pH, temperature, concentration of reagents, reaction time and structure-directing agent. ^22-25

Generally, mesoporous silica nanoparticles obtained using the sol-gel method have diameters greater than 100 nm, which are too large, for example, for some in vivo applications. ²⁶ Due to the complexity of the physiological environment, the structure, composition and morphology of mesoporous silica nanoparticles must be adjusted and optimized in order to meet the strict criteria for in vivo applications. These criteria include particle size, pore structure, aggregation status, surface type and degradation rate, in vivo circulation time and penetration into biological tissues. ¹⁷

Another important point to be taken into account is the toxicity of mesoporous silica nanoparticles, both in vitro and in vivo. Haynes et al. ²¹ studied the influence of the size of mesoporous silica nanoparticles, pore structure and stability on hemolytic activities. These authors demonstrated that mesoporous particles show a reduction in hemolytic activity when compared to non-porous particles. On the other hand, they showed that hemolytic activity decreases with decreasing diameter of mesoporous silica nanoparticles.

Control of particle size and pore shape and size is also of prime importance in catalysis and adsorption applications. In heterogeneous catalysis, the confinement of space given by the pore diameter at the nanometer scale, both in zeolites and in mesoporous silicas, allows to selectively promote certain catalytic reactions.

Additionally, increasing the pore size by a few nanometers allows for better diffusion of reagents, which is usually low in heterogeneous catalysis with microporous solids.

increase in pore diameter leads to an increase in pore volume and a decrease in area per unit mass, which in the case of physical adsorption applications is an advantage, as it increases the specific adsorption of materials.

In the literature there are examples of methods for the synthesis of mesoporous silica nanoparticles with particle size control, with diameters between 20 and 200300 nm. ⁴ ' ²⁴ ' ²⁵ ' ² O ² 9 However, in all of these methods the examples for diameters below 100 nm are sparse, with 2 to 3 diameters described per procedure.

Additionally, these methods are laborious, with variations that are difficult to reproduce, with low control over the morphology of the particles, being in some cases necessary to vary more than one reaction parameter to adjust the diameter. The variation of the particle diameter was achieved by changing the proportions of the reactants or structural changes of the structure directing agent, ²⁸ changing the pH, ⁴ ' ²⁵ adding agents to delay the hydrolysis of the precursors of silicon alkoxide ²⁹ or even the variation of the agitation speed of the reaction mixture. ⁴

An important aspect in the synthesis of mesoporous silica particles, mainly with regard to its application for transport and/or release of molecules, catalysis and adsorption, is the pore diameter. The pore diameter can be controlled by choice of structure directing agent, for example, by varying the length of the alkyl chains of derivatives of quaternary nitrogen bases (ionic surfactants), or of the hydrophobic blocks of block copolymers.

It is also possible to vary the pore diameter using micelle swelling agents, such as N,N-dimethylhexadecylamine or 1,3,5-trimethylbenzene, which expand the pore diameter to values above 20 nm. ²⁸ ' ²⁹

In accordance with the above, there is a need to develop a process for the synthesis of mesoporous silica nanoparticles with diameters less than 100 nm in which it is possible to carry out a precise control of the particle size. This process must be easy to carry out, allow to modulate the diameter of nanoparticles below 100 nm with high precision and by variation of a single experimental parameter, must use low base concentrations, and must allow obtaining silica nanoparticles without the addition of organic solvents during the synthesis.

Invention Summary

The present invention refers to the process of synthesis of mesoporous silica nanoparticles, with diameters below 100 nm and precise control of the particle size, incorporating organic molecules in the silica network.

For the synthesis process, the solgel method is used, using a structure-directing agent of the N ⁺ (R ¹ ) 3 (R ² ) X~ type (Figure 1) and a hydroxide base of metallic cations of the first or second group from the periodic table of the type M(OH) _n as a catalyst in an aqueous medium. In this way it is possible to control the diameter of the mesoporous silica nanoparticles by changing the pH of the reaction mixture. An ionic compound consisting of cations and mono- and/or polyvalent anions is also used. In this case, the diameter of the mesoporous silica nanoparticles is controlled by varying the ionic strength, which depends on the amount and type of ionic compound used. Organic molecules containing alkoxysilanes groups in the structure, such as perylenediimide derivatives, are also added in order to be incorporated in the silica network.

This type of nanoparticles can be used for application in imaging, as a transport and/or controlled release system, as a support for catalysts, or in adsorption.

Description of figures

The following is a detailed description of the invention with reference to the attached drawings, in which:

Figure 1 shows the general formula for the structure-directing agent, where R ¹ represents CH3 and/or CH2CH3, R ² represents C _n H(2n+i), with n = 12, 14, 16 or 18; X represents the bromide, chloride, hydroxyl, p-toluene sulphonate or hydrogen sulphate group.

Figure 2 shows images obtained by transmission electron microscopy (TEM) of the mesoporous silica nanoparticles obtained through the process described in the present invention, using increasing concentrations (AG) of the sodium hydroxide solution, between 0.1 mol.Ir ¹ and 2 mol.Ir ¹ . Scale bars represent 100 nm.

Figure 3 shows the distribution of diameters (D) of mesoporous silica nanoparticles obtained for increasing concentrations of the sodium hydroxide solution used, between 0.1 mol.Io ¹ and 2 mol.Io ¹ (AG represent the same concentrations used in Figure 2).

Figure 4 represents the mean diameters (D) obtained by TEM as a function of the concentration of sodium hydroxide used, for exclusively inorganic nanoparticles (circles, example 1) and for hybrid nanoparticles (squares, example 2).

Figure 5 shows images obtained by TEM of mesoporous silica nanoparticles obtained through the process described in the present invention with addition of ionic compound, using different concentrations of the sodium chloride solution, between 0.1 mol.In ¹ and 3 mol .In ¹ (AI) . Scale bars represent 100 nm.

Figure 6 shows the distribution of diameters (D) of the mesoporous silica nanoparticles obtained as a function of the ionic strength (I) of the medium (A-I represent the same concentrations used in Figure 5).

Figure 7 represents the mean diameters (D) of the mesoporous silica nanoparticles obtained by TEM as a function of the ionic strength (I) of the medium, for the sodium chloride solutions used in Figure 5).

Figure 8 shows images obtained by TEM of the hybrid nanoparticles, using different concentrations of the sodium hydroxide solution, between 0.1 mol.Ir ¹ and 2.0 mol.Ir ¹ (AF). Scale bars represent 100 nm.

Detailed description of the invention

The present invention refers to the process of synthesis of mesoporous silica nanoparticles, with diameters less than 100 nm and precise control of the particle size, with incorporation of organic molecules in the silica network. These nanoparticles can be used not only for transport and/or release of molecules, but also for imaging applications, as supports for catalysts, or in adsorption.

Surprisingly, it has been found that the process of the present invention provides a method that allows precise control of the particle size below 100 nm, which is easy to carry out, using low concentrations of base and varying a single experimental parameter. The synthesis process of mesoporous silica nanoparticles does not require the use of organic solvents.

Mesoporous silica nanoparticles are prepared using the sol-gel method, ²⁵ which consists of using a silica precursor, such as silicon alkoxides, in an aqueous basic medium, together with the addition of a structure-directing agent, an ionic compound and organic molecules.

Silicon alkoxide can consist of a silicon atom covalently bonded to at least two methoxide, ethoxide, propoxide or butoxide groups.

The base can be a hydroxide of metallic cations from the first or second group of the periodic table, of the type M(OH) _n .

The structure-directing agent can be a cationic surfactant of the N ⁺ (R ¹ ) 3 (R ² ) X - type (Figure 1), consisting of a quaternary nitrogen with four alkyl and/or aromatic substituents and an anion. The quaternary nitrogen substituents must be three methyl and/or ethyl groups and a fourth group which can be dodecyl, tetradecyl, hexadecyl or octradecyl. The anion can be bromide, chloride, hydroxyl, ptoluene sulphonate or hydrogen sulphate.

ionic compound consists of cations and mono- and/or polyvalent anions, such as, for example, sodium chloride or sodium hydrogen phosphate.

Organic molecules contain in their structure alkoxysilanes groups, these groups consisting of a silicon atom covalently bonded to at least one methoxide, ethoxide, propoxide or butoxide group, such as for example derivatives of perylenediimide with ethoxysilane groups.

Silica nanoparticles form through hydrolysis and condensation reactions. In a first phase, the structure-directing agent molecules organize into cylindrical micelles (incorporating the organic molecule inside), and for concentrations above the CMC (critical micellar concentration) form a supramolecular aggregate. After hydrolysis of the silicon alkoxides, they condense around the micellar aggregates. The subsequent removal of the structure-directing agent gives rise to mesoporous silica nanoparticles with free pores.

The following paragraphs describe in more detail the steps of the process of preparing the hybrid mesoporous silica nanoparticles.

In the present invention, the mesoporous silica nanoparticles are formed in an aqueous medium using structure-directing agents of the N ⁺ (R ¹ )3(R ² )X type (Figure 1), such as hexadecyltrimethylammonium bromide or chloride.

The organic molecules to be incorporated contain alkoxysilane groups in their structure, which groups consist of a silicon atom covalently bonded to at least one methoxide, ethoxide, propoxide or butoxide group, such as perylenediimide derivatives with ethoxysilane groups. These groups can form covalent bonds with the silica network, being covalently incorporated during particle synthesis.

structuring agent is dissolved together with the molecule to be incorporated in an organic solvent, for example tetrahydrofuran, which is then evaporated

To the above mixture, a basic solution of a hydroxide of metallic cations of the first or second group of the periodic table of the type M(OH) _{n is added} , such as sodium hydroxide, with concentrations that can vary between 0.1 mol. In ¹ and 2 mol.In ¹ , and also sol-gel precursors, which may be silicon alkoxides, such as, for example, tetraethoxysilane or tetramethoxysilane.

A saline solution of ionic compounds consisting of cations and mono- and/or polyvalent anions, such as sodium chloride or sodium hydrogen phosphate, is also added to the reaction mixture, with concentrations ranging from 0.1 mol.In ¹ and the 3 mol.In ¹ .

The mixture is kept under stirring for the time necessary for the reaction to take place, and at a controlled temperature between 10°C and 90°C, preferably between 25°C and 85°C. After the synthesis and washing of the nanoparticles, the surfactant is removed from the interior of the pores, for example, by adding an acidic alcoholic solution or by pyrolysis.

The diameters obtained for the mesoporous silica nanoparticles obtained through the process referred to in the present invention can vary between 15 and 100 nm, which are directly related to the concentration of base added to the reaction mixture, or to the increase in ionic strength, determined by the amount of salt added. When the amount of added salt is increased, the ionic strength increases, therefore there is a decrease in the electrostatic repulsion between the micelles and an increase in the number of micelles per aggregate, leading to the formation of larger nanoparticles.

Examples

The following examples describe the synthesis process for mesoporous silica nanoparticles with diameters less than 100 nm and precise particle size control, with addition of salt and organic molecules with alkoxysilane groups in their structure. The mesoporous silica nanoparticles are prepared by the sol-gel method, with the relative amounts of the components of the reaction mixture given as a percentage by mass of the total amount of reactants.

Example 1

Initially, a basic aqueous solution of sodium hydroxide was prepared, with a concentration between the

0.1 mol.Ir ¹ and the 2 mol.Io ¹ . In a plastic bottle 98.22% deionized water and 0.21% hexadecyltrimethylammonium bromide were added. The mixture was kept at a temperature between 65°C and 85°C, with stirring until all the surfactant was dissolved. To this mixture was added 0.72% of the sodium hydroxide solution, followed by the addition of 0.86% of the sol-gel precursor, tetraethoxysilane. The reaction mixture was kept at a temperature between 65°C and 85°C, preferably at 80°C, for 4 hours under stirring. At the end of the reaction, the dispersion was centrifuged and redispersed in water the number of times necessary to clean the obtained nanoparticles. After this process, the nanoparticles were dried at a temperature between 35°C and 65°C, preferably at 50°C. The nanoparticles obtained were characterized by transmission electron microscopy (TEM), and some examples are shown in Figure 2. The diameters of the nanoparticles obtained by TEM (Figure 3) are directly proportional to the concentration of the sodium hydroxide solution used (Figure 4).

Example 2

Initially, a basic aqueous solution of potassium hydroxide was prepared, with a concentration of between 0.1 mol.Ic ¹ and 2 mol.Ic ¹ . In a plastic bottle 98.22% deionized water and 0.21% hexadecyltrimethylammonium bromide were added. The mixture was kept at a temperature between 65°C and 85°C, with stirring until all the surfactant was dissolved. To this mixture was added 0.72% of the potassium hydroxide solution, followed by the addition of 0.86% of the sol-gel precursor, tetraethoxysilane. The reaction mixture was kept at a temperature between 65°C and 85°C, preferably at 80°C, for 4 hours under stirring. At the end of the reaction, the dispersion was centrifuged and redispersed in water the number of times necessary to clean the obtained nanoparticles. After this process, the nanoparticles were dried at a temperature between 35°C and 65°C, preferably at 50°C. The nanoparticles obtained had identical diameters to the particles in example 1, directly proportional to the concentration of the basic solution used.

Example 3

Initially, a basic aqueous solution of sodium hydroxide was prepared, with a concentration between 0.1 mol.L ^-1 and 2 mol.L ^-1 , and an aqueous saline solution of sodium chloride, with a concentration between 0 , 1 mol.L ^-1 and the 3 mol.L ^-1 . In a plastic bottle 98.22% deionized water and 0.21% hexadecyltrimethylammonium bromide were added. The mixture was kept at a temperature between 65°C and 85°C, preferably at 80°C, with stirring, until all the surfactant was dissolved. To this mixture was added 0.36% of the sodium hydroxide solution and 0.36% of the saline solution, after which 0.86% of the sol-gel precursor, the tetraethoxysilane, was added. The rest of the procedure was the same as described in example 1.

The nanoparticles obtained were characterized by TEM, and some examples are shown in Figure 5. The diameters of the nanoparticles obtained by TEM (Figure 6) are proportional to the value of the ionic strength of the medium (Figure 7).

Example 4

Initially, a basic aqueous solution of sodium hydroxide was prepared, with a concentration between 0.1 mol.L ^-1 and 2 mol.L ^-1 , and an aqueous saline solution of sodium bihydrogen phosphate, with a concentration between 0 , 1 mol.Im ¹ and the 3 mol.Io ¹ . The rest of the procedure was the same as described in example 3. The nanoparticles obtained had diameters that increase with the value of the ionic strength of the medium as in example 3.

Example 5

For the preparation of hybrid nanoparticles, 0.21% of hexadecyltrimethylammonium bromide was mixed with 0.0015% of the organic molecule to be incorporated, which contains in its structure at least one trialkoxysilane group, in this example the N,N'di(3- (triethoxysilyl)propyl)-perylene-3,4:9.10tetracarboxydiimide, which were dissolved in tetrahydrofuran. Then, tetrahydrofuran was evaporated and to the mixture 98.22% of deionized water was added. The rest of the procedure is described in example 1.

The nanoparticles obtained were characterized by TEM, with some examples shown in Figure 8. The diameters of the nanoparticles obtained by TEM are directly proportional to the concentration of the sodium hydroxide solution used and similar to those obtained in example 1 (Figure 4).

Example 6

Initially 0.21% of hexadecyltrimethylammonium bromide was mixed with 0.0015% of the organic molecule to be incorporated which contains in its structure at least one trialkoxysilane group, in this example N,N'-di(3(triethoxysilyl)propyl)- perylene-3,4:9.10tetracarboxydiimide, which were dissolved in tetrahydrofuran. Then the tetrahydrofuran was evaporated, the resulting solid was transferred to a plastic bottle and 98.22% deionized water was added. The mixture was kept at a temperature between 25°C and 85°C, preferably at 80°C, with stirring, until all the surfactant was dissolved. To this mixture was added 0.36% of a sodium hydroxide solution with a concentration between 0.1 mol.Ir ¹ and 2 mol.Ir ¹ , and 0.36% of a saline solution with a concentration between the 0.1 mol.Im ¹ and the 3 mol.Im ¹ , after which 0.86% of the sol-gel precursor, tetraethoxysilane, was added. The rest of the procedure was the same as described in example 1.

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Claims (9)

Claims 1. Synthesis process of hybrid mesoporous silica nanoparticles, carried out in an aqueous medium, by mixing a structure-directing agent, a sol-gel precursor and a base, characterized by: a) The structure-directing agent is an ionic surfactant, with a percentage by weight in the reaction mixture of 0.21% b) The sol-gel precursor is a silicon alkoxide derivative, with a weight percentage in the reaction mixture of 0.86%; c) The base is constituted by hydroxyl ions and a metallic cation, added from an aqueous solution, with a percentage by weight in the reaction mixture of 0.72%; d) The solvent is water, with a percentage by weight of the reaction mixture of 98.22%; e) The synthesis is carried out at a temperature comprised between 10°C and 90°C; f) The molar concentration of the aqueous base solution added to the reaction mixture in a percentage by weight of 0.72% is between 0.1 mol.In ¹ and 2 mol.In ¹ , with the determination of the diameter value of the silica nanoparticles hybrid mesoporous, between 15 and 100 nm. 2. Process for the synthesis of hybrid mesoporous silica nanoparticles, according to claim 1, characterized in that the structure directing agent is a cationic surfactant, consisting of a quaternary nitrogen with four alkyl and/or aromatic substituents and an anion. 3. Synthesis process of hybrid mesoporous silica nanoparticles, according to claims 1 and 2, characterized in that the quaternary nitrogen substituents of the structure directing agent are three methyl and/or ethyl groups and a fourth group that can be dodecyl, tetradecyl, hexadecyl or octradecyl. 4. Synthesis process of hybrid mesoporous silica nanoparticles, according to the preceding claims, characterized in that the structure-directing agent anion is bromide, chloride, hydroxyl, p-toluene sulphonate or hydrogen sulphate. 5. Process for the synthesis of hybrid mesoporous silica nanoparticles, according to claim 1, characterized in that the silicon alkoxide is constituted by a silicon atom covalently bonded to at least two methoxide, ethoxide, propoxide or butoxide groups. 6. Process for the synthesis of hybrid mesoporous silica nanoparticles, according to claim 1, characterized in that the base is constituted by hydroxyl ions and cations from the first or second group of the periodic table. 7. Process for the synthesis of hybrid mesoporous silica nanoparticles, according to the preceding claims, characterized in that the value of the diameter of the hybrid mesoporous silica nanoparticles is determined by the ionic strength, adjusted using an aqueous solution of an ionic compound, with molar concentration between 0.1 mol.lv ¹ and 3 mol.Ir ¹ , added to the reaction mixture in a percentage by weight of 0.36%, together with an aqueous solution of base with a molar concentration of 0.1 mol.L ^-1 , added to the reaction mixture in a percentage by weight of 0.36%. Process for the synthesis of hybrid mesoporous silica nanoparticles, according to claim 7, characterized in that the ionic compound is constituted by cations and monovalent and/or polyvalent anions. 9. Process for the synthesis of hybrid mesoporous silica nanoparticles, according to the preceding claims, characterized in that it comprises organic molecules which in their structure contain at least one alkoxysilane group, a group consisting of a silicon atom covalently bonded to at least one group methoxide, ethoxide, propoxide or butoxide, and by having a percentage by weight in the reaction mixture of 0.0015%.