KR101805862B1 - Mesoporous silica catalyst coated with hydrophobic polymer to efficiently remove carbon monoxide and method for preparing the same - Google Patents

Mesoporous silica catalyst coated with hydrophobic polymer to efficiently remove carbon monoxide and method for preparing the same Download PDF

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KR101805862B1
KR101805862B1 KR1020150179764A KR20150179764A KR101805862B1 KR 101805862 B1 KR101805862 B1 KR 101805862B1 KR 1020150179764 A KR1020150179764 A KR 1020150179764A KR 20150179764 A KR20150179764 A KR 20150179764A KR 101805862 B1 KR101805862 B1 KR 101805862B1
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mesoporous silica
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polymer
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rti
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장정호
성대경
이혜선
장서준
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한국세라믹기술원
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    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B33/00—Silicon; Compounds thereof
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    • C01B33/12—Silica; Hydrates thereof, e.g. lepidoic silicic acid
    • A—HUMAN NECESSITIES
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    • B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
    • B01J20/10—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising silica or silicate
    • B01J20/103—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising silica or silicate comprising silica
    • C—CHEMISTRY; METALLURGY
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    • C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
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    • C09D201/00—Coating compositions based on unspecified macromolecular compounds
    • C09D201/02—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C09D201/10—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing hydrolysable silane groups
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/16—Pore diameter

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Abstract

The present invention relates to a mesoporous silica coated with an entangled polymer for efficient removal of carbon monoxide and a method for producing the mesoporous silica. More specifically, the present invention relates to a mesoporous silica coated with a congenerally vibrating polymer for efficient removal of carbon monoxide having a benzene group, a ferrocene group or a benzene group and a ferrocene group as a trimethoxysilane group and a functional group as an immobilizer. The entangled polymer according to the present invention can be applied not only to the surface treatment of mesoporous silica for the removal of carbon monoxide but also to the control of release of functional materials in various fields such as prevention of adsorption of biomolecules such as proteins in biochips or drug delivery systems .

Description

TECHNICAL FIELD The present invention relates to a mesoporous silica coated with an undercoating polymer for efficiently removing carbon monoxide, and a method for producing the mesoporous silica coated with the mesoporous silica coated on the mesoporous silica, and a method for producing the mesoporous silica coated with the mesoporous silica coated on the mesoporous silica.

The present invention relates to a mesoporous silica coated with an entangled polymer for efficient removal of carbon monoxide and a method for producing the mesoporous silica. More specifically, the present invention relates to a mesoporous silica coated with a congenerally vibrating polymer for efficient removal of carbon monoxide having a benzene group, a ferrocene group or a benzene group and a ferrocene group as a trimethoxysilane group and a functional group as an immobilizer.

In modern society, harmful gases such as carbon monoxide and nitrogen oxide, which are harmful to humans, are generated in various places such as daily living space, market and shopping area, automobile, chemical plant, industrial site, incinerator, large power plant and boiler. Particularly, carbon monoxide is a colorless and odorless toxic substance, which is generated by incomplete combustion in transportation means using fossil fuels, heating facilities, power generation facilities, etc., and is one of the major air pollution sources together with SOx and NOx. According to the analysis of the cause of fire death, more than 50% of the deaths were reported as carbon monoxide (Acta Medicinae Legalis et Socialis, Volume 34, 1984, Pages 110-121 Anderson, RA; Cheng, KN Harland, WA). Conventionally, a catalyst in which a noble metal such as platinum (Pt) or palladium (Pd) is supported on a carrier such as alumina or tin oxide has been used for oxidation reaction with oxygen existing in exhaust gas or the like to remove carbon monoxide. For example, Korean Patent Laid-Open Publication No. 2003-0052388 describes coating an active ingredient of palladium and copper on a honeycomb to remove carbon monoxide at low temperatures through oxidation. In the European patent EP 0408528, CO is completely removed at about 150 ° C. by using a catalyst in which Pt is supported on SnO 2. In the Russian patent RU 1695979, Pd is supported on Al 2 O 3 catalyst at 110 to 160 ° C. . In the "Journal of Catalysis, 87, pp. 152-162, 1984", CO is carried out at 230 to 300 ° C with a catalyst carrying Pt or Pd on Al 2 O 3 or CeO 2 / Al 2 O 3 . In Japanese Laid-Open Patent Publication No. 1-94945, CO is removed at room temperature from a catalyst in which gold (Au) is supported on a metal oxide such as Fe 2 O 3 . In addition, Korean Patent No. 10-0651786 discloses a catalyst containing an active material containing Rh and Pt in an Ag-Co-Mn-Ti oxide support as a carbon monoxide removing material. In addition, there is also known a technique of using a catalyst prepared by supporting manganese (Mn) or copper (Cu) or the like on activated carbon as a filler used in a purifier, and in a plant for discharging carbon monoxide, activated carbon is generally used as a filler .

The conventional catalyst for removing carbon monoxide mentioned above generally exhibits activity at a high temperature of 150 ° C or higher. In particular, recently developed catalysts for oxidizing carbon monoxide in a low-temperature active zone also use expensive noble metals such as gold or platinum as active components, which requires a high production cost and requires a high level of technology in production. In addition, the catalyst prepared by supporting the metal oxide on the activated carbon is advantageous in that the production cost is low, but its activity is inferior to that of the catalyst prepared from the noble metal as a raw material. Therefore, there is an urgent need for a production method of an economical catalyst which exhibits excellent carbon monoxide removing activity even at room temperature.

Accordingly, the present inventors have studied polymer-self-assembled monolayers (pSAMs) using a monomer compound having a surface-reactive group while studying mesoporous silica to have excellent carbon monoxide removal efficiency even at room temperature. Has advantages over rapid formation, increased stability, and smooth surface roughness of SAMs compared to self-assembled monolayers (SAMs) of monomeric compounds. In addition, the present inventors have found that the use of a benzene group or a ferrocene group as a functional group in the above polymer is suitable for controlling the mesylation of mesoporous silica.

The present invention provides a mesoporous silica coated with an entangled polymer containing a fixator and a functional group, and a method for producing the mesoporous silica coated with the entrapped polymer.

As used herein, the term "mesoporous silica" means a mesoporous molecular sieve having uniformly sized mesopores regularly arranged and having porous pores having uniform pores . Typically, the mesoporous silica is a porous material having uniform pores of about 2 to 50 nm, preferably of the order of less than about 10 nm, less than about 17 nm, and up to about 30 nm, depending on the pore size And homogeneous nanoporous silica having a pore size of about 3 nm or less can also be used.

As used herein, the term "anchoring group" means a material that can be immobilized through a covalent bond to the mesoporous silica surface.

As used herein, the term "functional group" refers to a material for controlling the hydrophilic / hydrophobic properties of mesoporous silica surfaces.

According to one embodiment,

Mesoporous silica coated with a water-swellable polymer comprising an immobilizer and a functional group is disclosed.

In the mesoporous silica coated with the water-swellable polymer of the present invention, the mesoporous silica may be SBA-15, SBA-3, MSU-H, MCM-41, KIT-6, MCM- F, but it is not limited thereto.

In the mesoporous silica coated with the entangled polymer of the present invention, the immobilizing agent is preferably selected from the group consisting of 3- (trimethoxysilyl) propyl methacrylate, 3-glycidoxypropyltrimethoxysilane, Di (3-acryloxypropyl) dimethoxysilane, but is not limited thereto.

In the mesoporous silica coated with the entangled polymer of the present invention, the functional group may be a benzene group or a ferrocene group, but is not limited thereto.

In the mesoporous silica coated with the entangled polymer of the present invention, the mesoporous silica may be one having a copper manganese oxide supported thereon.

An exemplary embodiment of the mesoporous silica coated with the inventive entangled polymer is shown in Fig. Referring to FIG. 1, the trimethoxysilane group as an immobilizer of a polymer is fixed via a covalent bond with an OH group on the surface of the mesoporous silica, and a benzene group or a ferrocene group as a functional group of the polymer is a polymer So that the hydrophilic and hydrophobic surface characteristics of the mesoporous silica can be controlled.

According to another embodiment,

(A) preparing mesoporous silica; And

(B) coating the mesoporous silica with the entraining polymer comprising an immobilizer and a functional group. ≪ IMAGE >

In the method for producing mesoporous silica coated with a conductive polymer according to the present invention, the mesoporous silica may be one having a copper manganese oxide supported thereon.

In the method of preparing the mesoporous silica coated with mesoporous silica according to the present invention, the step (B) of coating mesoporous silica (B) with the entangled polymer including the immobilizing agent and the functional group may include:

(b-1) a polymerization initiator, a trimethoxysilane group as a fixing agent, and a benzene group, a ferrocene group, or a benzene group and a ferrocene group as a functional group and dissolving the benzene group, the benzene group and the ferrocene group at a temperature of 65 to 75 ° C for 12 to 36 hours To produce an entangled polymer;

(b-2) reacting the entrained polymer with the mesoporous silica at a temperature of 55 to 65 ° C for 5 hours to 10 hours.

In the process for preparing the mesoporous silica coated mesoporous silica of the present invention, the molar ratio of the immobilizer and the functional group may be 1: 1.

In the method for preparing mesoporous silica coated with the present invention, the polymerization initiator may be selected from the group consisting of Potassium Persulfate (KPS), Ammonium Persulfate (APS), Sodium Persulfate (SPS) But are not limited to, azoisobutylonitrile (AIBN) and benzoyl peroxide (BPO).

In the process for preparing the mesogenic silica-coated mesoporous silica of the present invention, the contact angle of the mesoporous silica coated with the mesoporous polymer may be 90 °.

Fig. 1 shows an example of a mesoporous silica coated with the inventive entangled polymer.
Fig. 2 shows a method of synthesizing the entangled polymer according to Example 1. Fig.
3 shows the results of 1 H NMR spectroscopy (500 MHz) analysis of the entangled polymer according to Example 1.
4 shows the SEM analysis results of the mesoporous silica coated with the entangled polymer according to Example 2. Fig.
FIG. 5 shows FT-IR analysis results of mesoporous silica coated with a conductive polymer according to Example 2. FIG.
Fig. 6 shows SEM analysis results of mesoporous silica coated with a water-swellable polymer according to Example 2. Fig.
FIG. 7 shows the BET analysis results of the mesoporous silica coated with the entangled polymer according to Example 2. FIG.
8 shows a method of synthesizing the nanocatalyst-carrying mesoporous silica according to Example 3. FIG.
9 shows the contact angle of the nanocatalyst-carrying mesoporous silica coated with the entangled polymer according to Example 3. Fig.

Hereinafter, the present invention will be described in more detail by way of examples. It will be apparent to those skilled in the art that these embodiments are merely illustrative of the present invention and that the scope of the present invention is not limited to these embodiments.

<Examples>

Example  1. Preparation of Conjugated Polymer

(TMSMA-r-BMA), poly (TMSMA-r-BMA-r-FMMA) and poly (TMSMA-FMMA) were synthesized to control the hydrophilic and hydrophobic properties of the mesoporous silica surface. (Fig. 2). TMSMA (5 mmol), benzyl monomer (BMA, 5 mmol) and AIBN (9 mg, 0.1 mmol) were placed in a vial and dissolved in 10 ml of THF for Poly 1. The mixture was continuously flushed with dry nitrogen for 20 minutes to remove oxygen and the vial was sealed with a Teflon lid. The polymerization reaction was carried out at 70 DEG C for 24 hours. Poly 2 was synthesized in the same manner as Poly 1 except that TMSMA (5 mmol) was kept the same and the content of BMA (2.5 mmol) and ferrocene monomer (FMMA, 2.5 mmol) was controlled. Finally, Poly 3 was synthesized in the same manner as Poly 1 except that TMSMA (5 mmol) was kept the same and the content of TMSMA (5 mmol) and FMMA (5 mmol) was controlled.

TMSMA (silane) BMA
(benzene) FMMA
ferrocene THF Mw 248.4 176 284.1 Poly 1 5 mmol 5 mmol 10ml Poly 2 5 mmol 2.5 mmol 2.5 mmol 10ml Poly 3 5 mmol 5 mmol 10ml

The characteristics of the poly-1, poly-2 and poly-3 were analyzed by 1 H NMR spectroscopy (500 MHz) (FIG. 3) , and the integration of the peak at δ = 4.90 (m, 2H, CO 2 -CH 2 at benzylMA) was compared with the value of the peak at 3.92 (m, 2H, CO 2 -CH 2 at TMSMA) &Lt; / RTI &gt; was consistent with the corresponding feed rate. Similarly, in the case of poly 2 and poly 3, it was confirmed that the characteristic peaks of the monomers disappeared and the characteristic peaks of the polymers appeared, and thus, the polymers were successfully synthesized.

Example  2. Conjugated Polymer-coated Meso  Preparation of silica

Poly 1, Poly 2 and Poly 3 synthesized in Example 1 were prepared and THF was removed by vacuum drying process. 1500 nm-grade mesoporous silica was prepared, and toluene was added thereto, followed by stirring for 2 hours. Then, the reaction was carried out at 60 DEG C for 6 hours so that the polymer could be immobilized on the mesoporous silica surface. Finally, toluene washing followed by vacuum drying was carried out to complete the final polymer coated mesoporous silica in powder form. The surface of the polymer-coated mesoporous silica was analyzed by SEM, FT-IR, TGA and BET, and the results are shown in FIGS. 4 to 7, respectively.

As can be seen from FIG. 4, SEM analysis using a JEOL JSM 6700F model (surface treatment with Au particles) showed that there was a significant change between the group with the accompanying vigorous polymer coating (MS 1500) It was confirmed that it was not observed.

As can be seen from Figure 6, JASCO V-460 FT- IR results using a spectrometer subjected to FR-IR analysis, accompanied by a characteristic peak of Si-O-Si of the speech polymer coated silica from all groups before and after the 1083 cm - 1 and Si-C were observed at 598 cm -1 . However, CH bond and OH bond, which are characteristic peaks of the polymer, were observed at 2900 cm -1 and 3420 cm -1 , respectively, after the water-soluble polymer coating.

As can be seen from FIG. 6, TGA analysis was carried out for the determination of organic matters on the surface of the mesoporous silica with entangled polymer. As a result, it was confirmed that the mesoporous silica with mesoporous polymer coating contained about 12% moisture. Specifically, in the case of mesoporous silica-coated mesoporous silica particles, a rapid weight loss occurred between 0 and 100 ° C., followed by gradual weight loss to 200 ° C., and a sudden weight loss after 200 ° C. . It was confirmed that the organic polymer was stable on the surface of the mesoporous silica due to the formation of the monolayer magnetic film, polymer SAMs (pSAMs) up to 200 ℃, but was rapidly lost under the severe condition of 200 ℃ or more. As a result of observing the disappearance rate of organic matter, weight loss of 20.1% in poly 1, 17.2% in poly 2 and 12.6% in poly 3 was confirmed. As a result, the amount of the accompanying hydrolyzed polymer on the surface of the mesoporous silica was confirmed.

As can be seen from FIG. 7, the specific surface area and the pore size by nitrogen adsorption using the BET specific surface area analyzer were analyzed. As a result, it was confirmed that the characteristics of mesopores were maintained before and after the water-swellable polymer coating. The specific surface area of the mesoporous silica is about 588 m 2 / g. When the coating is carried out using three different kinds of polymers, the specific surface area of poly 1 is 276 m 2 / g, and the specific surface area of poly 2 is 338 m 2 / g And 418 m 2 / g for poly 3. As a result, it was confirmed that the entangled polymer was impregnated into the pores of mesoporous silica.

Example  3. Through surface treatment optimization Water repellency  Control

The nanocatalyst-carrying mesoporous silica was synthesized according to the procedure of FIG. 8 and coated with a polymer, and then the contact angle of the mesoporous silica surface with the polymer was measured using a Phoenix 300 goniometer (Surface Electro Optics) Respectively. Specifically, polymer-coated mesoporous silica particles were fixed flat on the floor through a taping process for contact angle measurement. Then, water droplets were formed using a needle provided on the contact angle measuring instrument, and the silica particles were dropped on the fixed bottom. Finally, the specificity (hydrophilicity or hydrophobicity) of the surface was evaluated by measuring the contact sensation of droplets generated through dropping.

The wettability characteristics of the model substrate prepared by measuring the contact angle of 5 占 퐇 of water drops were analyzed, and the results are shown in Fig. The dynamic advancing water-contact angle? Adv and the backward-contact angle? Rec were determined by a tilting experiment and the contact angles were measured at three different positions for each sample and expressed as their average values .

As can be seen from Fig. 9, the contact angle of all three mesoporous silica substrates used by the surface modification of the entangled polymer was remarkably increased. Specifically, the contact angle before the entangled polymer modification was remarkably more than 10 times from 11.2 ° ± 0.8 to 94.2 ° ± 1.2 ° ±, 98.5 ° ± 1.8 ° and 103.5 ° ± 2.1 ° after poly 1, poly 2 and poly 3 polymer modification Respectively. In addition, since mesoporous silica surfaces generally have OH groups, they exhibit hydrophilic characteristics. Therefore, when the water is dropped, the surface tension is lowered and water is absorbed through mesopores. However, it was observed that the surface tension was increased due to the hydrophobic change of the surface of the water - soluble polymer modified silica particles. In particular, it was observed that the contact angle increases from poly1 to 3, that is, the surface becomes more hydrophobic as the ferrocene ratio in benzene increases as the surface functional group.

The present invention has been described with reference to the preferred embodiments. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims. Therefore, the disclosed embodiments should be considered in an illustrative rather than a restrictive sense. The scope of the present invention is defined by the appended claims rather than by the foregoing description, and all differences within the scope of equivalents thereof should be construed as being included in the present invention.

Claims (9)

Mesoporous silica coated with a water-swellable polymer comprising an immobilizer and a functional group,
The mesoporous silica coated with the entangled polymer is characterized in that the immobilizer is a trimethoxysilane group and the functional group is a ferrocene group.
The method according to claim 1,
The trimethoxysilane group is exemplified by 3- (trimethoxysilyl) propyl methacrylate, 3-glycidoxypropyltrimethoxysilane, vinylpropyltrimethoxysilane, and di (3-acryloxypropyl) dimethoxysilane &Lt; / RTI &gt; wherein the mesoporous silica is selected from the group consisting of hydrosilylation catalysts.
The method according to claim 1,
Wherein the mesoporous silica is supported on a copper manganese oxide.
(A) preparing mesoporous silica; And
(B) coating the mesoporous silica with an entraining polymer comprising an immobilizing agent and a functional group,
Wherein the immobilizing agent is a trimethoxysilane group, and the functional group is a ferrocene group.
5. The method of claim 4,
Wherein the mesoporous silica is supported on copper manganese oxide. &Lt; RTI ID = 0.0 &gt; 21. &lt; / RTI &gt;
5. The method of claim 4,
The step of coating the mesoporous silica (B) with the entraining polymer comprising an immobilizing agent and a functional group comprises:
(b-1) dissolving a polymerization initiator, a trimethoxysilane group as an immobilizer, and a ferrocene group as a functional group, and reacting the mixture at a temperature of 65 to 75 ° C for 12 to 36 hours to prepare a concomitant vigorous polymer; And
(b-2) reacting the entrained polymer with the mesoporous silica at a temperature of 55 to 65 ° C for 5 hours to 10 hours.
5. The method of claim 4,
Wherein the molar ratio of the immobilizer to the functional group is 1: 1. &Lt; RTI ID = 0.0 &gt; 11. &lt; / RTI &gt;
The method according to claim 6,
The polymerization initiator may be selected from the group consisting of potassium persulfate (KPS), ammonium persulfate (APS), sodium persulfate (SPS), azoisobutylonitrile (AIBN) and benzoyl peroxide Peroxide, BPO). &Lt; Desc / Clms Page number 20 &gt;
5. The method of claim 4,
Wherein the contact angle of the mesoporous silica coated with the entangled polymer is 90 DEG or more. &Lt; RTI ID = 0.0 &gt; 11. &lt; / RTI &gt;
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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001340755A (en) * 2000-03-31 2001-12-11 Toyota Central Res & Dev Lab Inc Porous material for adsorbing and separating gas and method of adsorbing and separating gas using the same

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001340755A (en) * 2000-03-31 2001-12-11 Toyota Central Res & Dev Lab Inc Porous material for adsorbing and separating gas and method of adsorbing and separating gas using the same

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