KR101867135B1 - Method of fabricating sponge having superhydrophobic and superoleophilic - Google Patents
Method of fabricating sponge having superhydrophobic and superoleophilic Download PDFInfo
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- KR101867135B1 KR101867135B1 KR1020150071504A KR20150071504A KR101867135B1 KR 101867135 B1 KR101867135 B1 KR 101867135B1 KR 1020150071504 A KR1020150071504 A KR 1020150071504A KR 20150071504 A KR20150071504 A KR 20150071504A KR 101867135 B1 KR101867135 B1 KR 101867135B1
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- superhydrophobic
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05C—APPARATUS FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05C3/00—Apparatus in which the work is brought into contact with a bulk quantity of liquid or other fluent material
- B05C3/02—Apparatus in which the work is brought into contact with a bulk quantity of liquid or other fluent material the work being immersed in the liquid or other fluent material
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Abstract
A method for producing a sponge having a superhydrophobic and chopped oil phase is provided. Specifically, a fluorinated alkylsilane compound, an acid catalyst, and an organic solvent may be mixed to form a fluorine-substituted polysiloxane, and the polysiloxane may be coated on the sponge. Accordingly, the present invention can provide the surface of the sponge with a superhydrophobic and / or superhydrophobic lubricant by preparing a fluorine-substituted polysiloxane solution and dip coating the sponge in the solution, thereby realizing a simplification of the manufacturing process and a reduction in the manufacturing cost . In addition, the sponge produced by the present invention can selectively absorb only oil from a mixture of oil and water, and thus can be utilized for processes requiring marine oil spillage or separation of oil and water.
Description
BACKGROUND OF THE
In recent years, there has been a growing awareness of such oil spills due to the frequent occurrence of marine pollution problems caused by ship oil spills at sea. This is because, as the oil spills on the sea, marine predators living in coastal livelihoods of seaweeds and coral are lost, coastal fish species are killed, and marine predators belonging to the food chain consuming marine life mixed with oil are seriously damaged, Is threatened. In addition, oil spills can cause damage to fisheries and seaweed aquaculture in polluted areas, and serious damage to the local economy due to loss of travel income due to decrease in travelers.
Generally, a method of removing oil from the sea is to collect the oil by using an oil boom, collect the oil by using the oil refiner, and use a thin oil layer as the oil absorbing material Method, a chemical method of spraying oil treatment agent or oiling agent, or a biological method of dissolving oil by microbial decomposition action. The oil absorbing materials used in the above-mentioned physical methods include activated carbon, zeolite or fiber. However, these oil absorbing materials are not suitable for nonselectivity, low absorbency and difficulty in reusing. And there is an increasing demand for the development of oil absorbing materials.
In order to solve the above-mentioned problems, research is being conducted on an oil absorbing material having a superhydrophobic surface capable of separating not only water repellency but also oil and water. In order to produce an oil absorbing material having such a superhydrophobic surface, it is important to control the energy and roughness of the surface coating layer so that the oil absorbing material has low surface energy. Accordingly, a method of coating a polymer material having a low surface energy by modifying a nanostructure on the surface of a porous material by using silica nanoparticles, copper nanoparticles, or carbon nanotubes has been attempted. However, the production of such a porous material has a disadvantage that a high manufacturing cost and a complicated manufacturing process are required.
It is an object of the present invention to provide a method of manufacturing a sponge having an oil-repellent and superficial oil-repellent surface, which can easily remove oil while reducing the manufacturing cost by simplifying the manufacturing process.
According to an aspect of the present invention, there is provided a method of preparing a fluorine-substituted polysiloxane, comprising: mixing a fluorinated alkylsilane compound, an acid catalyst, and an organic solvent to form a fluorine-substituted polysiloxane; and coating the sponge with the fluorine- The present invention provides a method for producing a sponge having a superhydrophobic and superficial oil repellency.
The fluorinated alkylsilane compound may be a silane compound represented by the following general formula (1).
[Chemical Formula 1]
CF 3 (CF 2 ) m (CH 2) n SiX 3
M is an integer of 5 to 11, n is an integer of 2 to 5, and X is an alkoxy group or a halogen group.
In one embodiment of the present invention, the fluorinated alkylsilane-based compound is heptadecafluoro-1,1,2,2-tetrahydrodecyl trimethoxysilane (HFTHTMS ).
The acid catalyst may be at least one selected from the group consisting of phosphonic acid, hydrochloric acid, acetic acid, hydrogen fluoride, nitric acid, sulfuric acid chlorosulfonic acid and iodic acid.
The organic solvent may be methanol, ethanol, isopropyl alcohol (IPA), ethylene glycol, or butanol.
The step of coating the fluorine-substituted polysiloxane with the sponge may be performed by dip coating.
The present invention can provide the surface of the sponge with a superhydrophobic and accelerated oil repellent by the production of the fluorine-substituted polysiloxane solution and the dip coating of the sponge in the solution, thereby simplifying the manufacturing process and reducing the manufacturing cost.
In addition, the sponge produced by the present invention can selectively absorb only oil from a mixture of oil and water, and thus can be utilized for processes requiring marine oil spillage or separation of oil and water.
However, the effects of the present invention are not limited to those mentioned above, and other effects not mentioned can be clearly understood by those skilled in the art from the following description.
1 is a flow chart for explaining a method of manufacturing a sponge having a superhydrophobic and chopped oil phase according to an embodiment of the present invention.
2 (a) to 2 (b) are images showing the result of immersing the sponge produced in Comparative Example 1 and Example 1 in water, respectively.
3 (a) to 3 (d) are FE-SEM images of the sponge of Comparative Example 1 and Example 1. Fig.
4 (a) to 4 (b) are graphs showing the X-ray photoelectron spectroscopy (XPS) and high resolution X-ray photoelectron spectroscopy (high resolution XPS) measurement results of the sponge of Example 1.
5 (a) to 5 (b) are graphs showing the results of energy dispersive X-ray spectroscopy (EDS) measurement of the sponges of Comparative Examples 1 and 1, respectively.
6 is an image showing a process of separating and absorbing soybean oil from water using the sponge of Example 1. Fig.
7 is a graph showing the oil adsorption capacity of the sponge of Example 1 according to repeated use in soybean oil and three kinds of organic solvents.
8 is an image showing a selective oil removal process using the sponge of Example 1. FIG.
Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings.
While the invention is susceptible to various modifications and alternative forms, specific embodiments thereof are shown by way of example in the drawings and will herein be described in detail. Rather, the intention is not to limit the invention to the particular forms disclosed, but rather, the invention includes all modifications, equivalents and substitutions that are consistent with the spirit of the invention as defined by the claims.
In the drawings, the thicknesses of the layers and regions may be exaggerated or reduced for clarity. Like reference numerals throughout the specification denote like elements.
As used throughout this specification, the term "alkyl group" may mean a substituted or unsubstituted hydrocarbon group having 1 to 30 carbon atoms, such as methyl, ethyl, propyl, isopropyl, isobutyl, pentyl, , Octyl, nonyl, decyl, undecyl, tridecyl, pentadecyl or heptadecyl.
Throughout this specification, "alkoxy" means an alkoxy group having 1 to 30 carbon atoms in which an alkyl group and an oxygen atom are bonded, and includes, for example, methoxy, ethoxy, propoxy, butoxy, pentoxy , Hexoxy, heptoxy, octoxy, nonoxy, decoxy or isomers thereof.
Throughout this specification, a "halogen group" may include fluorine (F), chlorine (Cl), bromine (Cr), or iodine (I).
The present invention can provide a method for producing a sponge having a superhydrophobic and superficial oil repellency. Specifically, the method for producing a sponge having a superhydrophobic and superhydrophilic oil phase comprises the steps of: forming a fluorosubstituted polysiloxane by mixing a fluorinated alkylsilane compound, an acid catalyst and an organic solvent; and applying the fluorosilver polysiloxane to the sponge .
1 is a flow chart for explaining a method of manufacturing a sponge having a superhydrophobic and chopped oil phase according to an embodiment of the present invention.
Referring to FIG. 1, a fluorine-substituted polysiloxane can be formed by mixing a fluorinated alkylsilane compound, an acid catalyst, and an organic solvent (S100).
The fluorinated alkylsilane-based compound may be a fluorine-substituted alkylsilane-based compound as a main material for forming a polysiloxane having fluorine (F) described later. In one embodiment of the present invention, the fluorinated alkylsilane compound may be added in an amount of about 10% by weight to about 20% by weight based on the total amount of the mixed solution, but the present invention is not limited thereto.
Specifically, the fluorinated alkylsilane compound may be a silane compound represented by the following general formula (1).
[Chemical Formula 1]
CF 3 (CF 2 ) m (CH 2) n SiX 3
In Formula 1, m is an integer of 5 to 11, n is an integer of 2 to 5, and X is an alkoxy group or a halogen group. For example, X may be a methoxy, ethoxy or chloride group, but is not limited thereto. Specifically, the fluorinated alkylsilane compound may be, for example, CF 3 (CF 2 ) 11 CH 2 CH 2 Si (OCH 3 ) 3 , CF 3 (CF 2 ) 9 CH 2 CH 2 Si (OCH 3 ) 3, CF 3 (CF 2) 7 CH 2 CH2Si (OCH 3) 3, CF 3 (CF 2) 11 CH 2 CH 2
Further, an acid catalyst can be prepared as a material for forming the fluorine-substituted polysiloxane. The acid catalyst may be added to suppress the hydrolysis and condensation reaction rate control and side reaction occurrence of the fluorinated alkylsilane compound in the polysiloxane formation reaction. Specifically, the acid catalyst may be at least one selected from the group consisting of phosphonic acid, hydrochloric acid, acetic acid, nitric acid, sulfonic acid, sulfuric acid and iodic acid. The alkylphosphonic acid may be one or more selected from the group consisting of methyl phosphonic acid, ethyl phosphonic acid, propyl phosphonic acid, butyl phosphonic acid and octyl phosphonic acid. But is not limited thereto.
In addition, an organic solvent may be prepared as a material for forming the fluorine-substituted polysiloxane. Specifically, the organic solvent may be an alcohol. Specifically, the organic solvent may be methanol, ethanol, isopropyl alcohol (IPA), ethylene glycol, or butanol.
When the fluorinated alkylsilane compound, the acid catalyst and the organic solvent are mixed and stirred, the reaction product X of the fluorinated alkylsilane compound is hydrolyzed to form a hydroxyl group (OH), and the hydroxyl group and other hydroxyl groups in the compound are dehydrated and condensed And siloxane bonds composed of Si-O can be formed. That is, the polysiloxane in which fluorine is substituted due to the siloxane bond of the fluorinated alkylsilane compound can be formed.
When the fluorinated alkylsilane compound, the acid catalyst and the organic solvent are mixed, the fluorinated alkylsilane compound is gradually added to the mixed solution containing the organic solvent and the acid catalyst so that the hydrolysis and condensation reaction do not proceed too fast And stirring the mixed solution at room temperature for 24 hours to 30 hours at the time of stirring.
Then, the fluorine-substituted polysiloxane may be coated on the sponge (S200).
The sponge may be formed of a three-dimensional porous foam structure having a large surface area therein, or may be made of a polymer compound. The sponge may be any conventional sponge. In an embodiment of the present invention, the sponge may be a sponge made of polyurethane material. Generally, a polyurethane sponge refers to a product obtained by foaming polyol and isocyanate as main materials and adding functional additives such as a foaming agent and a catalyst, It is widely used in the field.
Specifically, the step of coating the fluorine-substituted polysiloxane with the sponge may be performed by dip coating. That is, after immersing the sponge in a reaction tank containing the fluorine-substituted polysiloxane for a predetermined period of time, the sponge is taken out and dried to coat the polysiloxane on the sponge. The drying step may be performed at room temperature or at a temperature of 15 to 30 DEG C for about 24 to 30 hours. As described above, as the fluorine-substituted polysiloxane is coated on the sponge, the surface of the sponge may be imparted with superhydrophobic and superficial oil repellency. Specifically, this can be explained through the following examples and drawings.
Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the scope of the present invention is not limited to the following examples.
[Example]
≪ Example 1: Preparation of a sponge having a superhydrophobic and chopped oil phase >
Heptadecafluoro-1,1,2,2-tetrahydrodecyl trimethoxysilane (HFTHTMS) purchased from Gelest (USA), Sigma-Aldrich (USA) 95% propylphosphonic acid and 95% ethanol purchased from Duksan Chemical Korea were prepared. The above HFTHTMS (0.24 g, 0.42 mmol) was added to a solution of the above propylphosphoric acid (37 mg, 0.3 mmol) in 30 mL of ethanol and stirred at room temperature for 24 hours to prepare a fluorine-substituted polysiloxane. The polyurethane sponge purchased from the shop was immersed in the polysiloxane solution for 24 hours at room temperature, taken out and dried for 24 hours.
≪ Comparative Example 1: Sponge without surface treatment >
A polyurethane sponge was prepared without a separate surface treatment process.
2 (a) to 2 (b) are images showing the result of immersing the sponge produced in Comparative Example 1 and Example 1 in water, respectively.
The general sponge shown in FIG. 2 (a) has a hydrophilic surface, so that water can be easily absorbed into the porous structure of the sponge. On the other hand, referring to FIG. 2 (b), it can be confirmed that the sponge of Example 1 does not change in size or volume even after being immersed in water, so that water is not absorbed. Thus, it can be seen that the sponge of Example 1 prepared in the present invention has a superhydrophobic surface.
3 (a) to 3 (d) are FE-SEM images of the sponge of Comparative Example 1 and Example 1. Fig. Specifically, this is an optical image of water droplets disposed on each sponge. The optical image was measured using hitashi S3400, which is an FE-SEM (field emission scanning electron microscope) apparatus.
3 (a) and 3 (c) are FE-SEM images of the sponge of Comparative Example 1, wherein the water contact angle of the sponge with respect to water is 129 °, Referring to the FE-SEM image of the sponge of Example 1 in (d), it can be seen that the contact angle of the sponge of Example 1 with respect to water is 154 °. Generally, when the contact angle with water exceeds 150 °, it can be regarded as having super-hydrophobicity. As described above, the contact angle of the sponge of Example 1 with respect to water was changed as the surface was coated with the polysiloxane substituted with fluorine. However, when comparing the sponge of Example 1 and the sponge of Comparative Example 1, the morphology ) It can be seen that the change has not changed to an appreciable degree. That is, the sponge produced in Example 1 of the present invention can have a superhydrophobic surface while retaining the porous structure and the shape thereof, as in the sponge of Comparative Example 1, which is not surface-treated. This is an improvement of the conventional method of coating a material capable of lowering the surface energy after forming a nanostructure that controls the roughness on the surface of the sponge, and the present invention provides a dip coating process without a separate nanostructure forming process It is possible to impart super hydrophobicity to the surface of the sponge while maintaining the original shape and structure of the sponge through a simple process.
4 (a) to 4 (b) are graphs showing the X-ray photoelectron spectroscopy (XPS) and high resolution X-ray photoelectron spectroscopy (high resolution XPS) measurement results of the sponge of Example 1.
4 (a) to 4 (b), it can be seen that the surface of the sponge produced in Example 1 of the present invention is composed of C, O, Si and F. FIG. Specifically, the highest peak observed at 688.2 eV is consistent with the CF group of the fluorine-substituted polysiloxane. Further, CF, CC and CO groups were found at 288 eV, 285 eV and 285.9 eV, respectively, of the high-resolution C 1s spectrum, and the -CF 2 - , CF 2 -CF 2 and fluorine-substituted carbonate moieties were found to be 292.9 eV and 290.5 eV And 291.5 eV, respectively. This confirms that the fluorine-substituted polysiloxane was easily coated on the surface of the sponge prepared in Example 1 of the present invention.
5 (a) to 5 (b) are graphs showing the results of energy dispersive X-ray spectroscopy (EDS) measurement of the sponges of Comparative Examples 1 and 1, respectively.
5 (a) to 5 (b), unlike Comparative Example 1, it can be confirmed that the fluorine content of the sponge of Example 1 is 14.4%. This indicates that fluorine can lower the surface energy as an important factor for imparting super-hydrophobicity, so that the sponge of Example 1 has a super-hydrophobic surface.
6 is an image showing a process of separating and absorbing soybean oil from water using the sponge of Example 1. Fig.
Referring to FIG. 6, first, 0.5 ml of soybean oil is dyed with Oil red O reagent, and then the dyed soybean oil is floated on the surface of water. Thereafter, the soybean oil can be completely absorbed by using the sponge produced in Example 1. This is because the sponge produced in the present invention has high selectivity for oil, so that it can be seen that only oil is absorbed from the mixture of oil and water. That is, it can be seen that the sponge produced in the present invention has lipophilic property capable of selectively absorbing oil and hydrophobic property having repellency of water.
7 is a chart showing the oil absorption capacity of the sponge of Example 1 according to repeated use in soybean oil and three kinds of organic solvents. As the three types of organic solvents, cyclohexane, octane and toluene were used. In order to measure the oil adsorption capacity due to repeated use of the sponge, first, the sponge of Example 1 was immersed in the soybean oil and the organic solvent for about 10 minutes to measure the saturated absorption capacity, and then the sponge was squeezed, The absorbed solvent was removed. Then, after washing for 1 minute with acetone, squeezing, and drying at room temperature, the absorption capacity of the sponge was measured.
Referring to FIG. 7, it is confirmed that the absorption capacity of the sponge is 15 times or more the weight of the sponge. That is, it can be seen that the sponge having the superhydrophobic and superhydrophobic oil prepared in Example 1 efficiently absorbs not only soybean oil but also other organic solvents such as cyclohexane, octane and toluene. As a result of repeating the above-described absorption capacity measurement method, it was found that while the absorption capacity of the sponge in the soybean oil did not change much while the cycle was performed seven times, the absorption capacity of the sponge in the three organic solvents Is slightly reduced when the cycle is performed twice.
8 is an image showing a selective oil removal process using the sponge of Example 1. FIG.
As shown in FIG. 8, octane was stained with red, water was stained with blue, and the stained solutions were successively poured into the sponge of Example 1. As a result, red stained octane passed through the sponge while the blue Can be confirmed to be accumulated on the sponge. That is, the octane was absorbed by the superficial oil of the sponge, but it is resilient to water because of the super hydrophobicity of the sponge.
As described above, the method of manufacturing a sponge of the present invention can efficiently impart a super hydrophobic property to a sponge by a simple process of dip coating in which a fluorine-substituted polysiloxane solution is prepared and the sponge is immersed in the solution. Thus, the sponge manufactured by the method of the present invention can selectively remove oil from a mixture of oil and water and remove the oil through the compression of the absorbed sponge, so that the oil spill accident and separation of oil and water And can be utilized positively in the required process.
It should be noted that the embodiments of the present invention disclosed in the present specification and drawings are only illustrative of specific examples for the purpose of understanding and are not intended to limit the scope of the present invention. It will be apparent to those skilled in the art that other modifications based on the technical idea of the present invention are possible in addition to the embodiments disclosed herein.
Claims (6)
Dip coating a sponge on the fluorine-substituted polysiloxane,
Characterized in that the acid catalyst is a propylphosphonic acid
A method for producing a sponge having a superhydrophobic and superhydrophobic oil phase without forming a nanostructure on the surface.
Wherein the fluorinated alkylsilane compound is a silane compound represented by the following general formula (1): < EMI ID = 1.0 >
[Chemical Formula 1]
CF 3 (CF 2 ) m (CH 2) n SiX 3
In Formula 1,
M is an integer of 5 to 11,
N is an integer of 2 to 5,
X is an alkoxy group or a halogen group.
Wherein the fluorinated alkylsilane-based compound is heptadecafluoro-1,1,2,2-tetrahydrodecyl trimethoxysilane (HFTHTMS). A method for producing a sponge having a superhydrophobic and superficial oil phase without structure formation.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20230053900A (en) * | 2021-10-15 | 2023-04-24 | 주식회사 드림바이오스 | Manufacturing method for superhydrophobic oil/water seperation material and Sampling method for NAPL in soil using the same |
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| KR101959121B1 (en) * | 2017-04-28 | 2019-03-15 | 단국대학교 산학협력단 | Coating composition for surface treatment of Magnesium, a method for producing the same and a coating method using the same |
| KR102177314B1 (en) * | 2018-09-28 | 2020-11-10 | 한밭대학교 산학협력단 | Superhydrophobic - superoleophilic nickel foams and method for making same |
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| KR102653462B1 (en) * | 2021-11-03 | 2024-03-29 | 한남대학교 산학협력단 | A a method for manufacturing oil absorbent using polyurethane sponge |
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| KR100492396B1 (en) * | 1997-03-11 | 2005-05-31 | 닛본 이따 가라스 가부시끼가이샤 | A substrate having a treatment surface and surface treating method for a substrate |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20230053900A (en) * | 2021-10-15 | 2023-04-24 | 주식회사 드림바이오스 | Manufacturing method for superhydrophobic oil/water seperation material and Sampling method for NAPL in soil using the same |
| KR102646829B1 (en) | 2021-10-15 | 2024-03-12 | 주식회사 드림바이오스 | Manufacturing method for superhydrophobic oil/water seperation material and Sampling method for NAPL in soil using the same |
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| E902 | Notification of reason for refusal | ||
| AMND | Amendment | ||
| E601 | Decision to refuse application | ||
| AMND | Amendment | ||
| E902 | Notification of reason for refusal | ||
| AMND | Amendment | ||
| X701 | Decision to grant (after re-examination) | ||
| GRNT | Written decision to grant |