WO2016132859A1 - Membrane de parylène perméable à l'eau et son procédé de production, et procédé de séparation de l'eau - Google Patents

Membrane de parylène perméable à l'eau et son procédé de production, et procédé de séparation de l'eau Download PDF

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WO2016132859A1
WO2016132859A1 PCT/JP2016/052615 JP2016052615W WO2016132859A1 WO 2016132859 A1 WO2016132859 A1 WO 2016132859A1 JP 2016052615 W JP2016052615 W JP 2016052615W WO 2016132859 A1 WO2016132859 A1 WO 2016132859A1
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parylene
water
membrane
permeable
film
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PCT/JP2016/052615
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English (en)
Japanese (ja)
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木村　睦
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国立大学法人信州大学
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Priority to JP2017500579A priority Critical patent/JP6381772B2/ja
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
    • B01D69/12—Composite membranes; Ultra-thin membranes
    • B01D69/1213—Laminated layers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
    • B01D71/06—Organic material
    • B01D71/72—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, not provided for in a single one of the groups B01D71/46 - B01D71/70 and B01D71/701 - B01D71/702
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
    • B01D71/06—Organic material
    • B01D71/76—Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74
    • B01D71/82—Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74 characterised by the presence of specified groups, e.g. introduced by chemical after-treatment

Definitions

  • the present invention relates to a parylene permeable membrane and a method for producing the same, and a water separation method using the parylene permeable membrane or a composite membrane thereof.
  • parylene polyparaxylylene
  • Parylene is also used in a method for controlling the pore diameter by vapor deposition on the surface of a porous membrane filter (Patent Document 1).
  • Patent Document 2 In recent years, attempts have been made to use parylene as a gas sensor in order to search for new forms of use of parylene (Patent Document 2).
  • the present invention is an invention contrary to the conventional common sense that a parylene membrane has a property of not allowing liquid to permeate, and a parylene permeable membrane capable of transmitting water, a method for producing the same, and the parylene permeable membrane or a composite thereof. It is an object of the present invention to provide a method for separating water from water in which a substance is dissolved and / or dispersed using a membrane.
  • the present invention provides a parylene permeable membrane characterized by having a polar group.
  • the present invention also provides the above-described parylene permeable membrane, wherein the polar group is a cyano group.
  • the present invention provides the above-mentioned parylene permeable membrane, wherein the parylene permeable membrane has a pore diameter of 0.1 to 10 nm.
  • the present invention also provides the above-described parylene permeable membrane, wherein the parylene permeable membrane has a thickness of 10 nm to 10 ⁇ m.
  • the present invention provides a composite membrane characterized by having the above-described parylene permeable membrane.
  • the present invention provides a water separation method characterized by allowing water in which a substance is dissolved and / or dispersed to pass through the parylene permeable membrane or a composite membrane thereof to separate the water.
  • parylene is vapor-deposited by the CVD method on the surface of a porous support containing a deposition target liquid or polymer that does not evaporate during the thin film formation process by the CVD method and can deposit parylene.
  • the process for producing a parylene water permeable membrane is provided by the method described above. Note that CVD is an abbreviation for chemical vapor deposition, and CVD is one of vapor deposition methods for forming thin films of various substances.
  • the present invention also provides a method for depositing parylene by the CVD method on the surface of a porous film containing a deposition target liquid or polymer that does not evaporate during the thin film formation process by the CVD method and on which parylene can be deposited.
  • the present invention provides a method for producing the above-described composite membrane.
  • the present invention provides the above-mentioned composite characterized in that it is obtained by peeling a parylene water permeable film obtained by vapor-depositing parylene on the surface of the substrate by a CVD method and bonding it to the surface of the porous film.
  • a method for producing a film is provided.
  • the present invention provides a resin sheet having a parylene water permeable film obtained by vapor-depositing parylene on the surface of the resin sheet by a CVD method, and then bonding the resin film to the surface of the porous film.
  • the present invention provides a method for producing the above-mentioned composite membrane, which is obtained by removing a sheet.
  • the present invention provides a method for producing the above composite membrane, wherein the resin sheet is removed from the porous membrane by dissolving it in a liquid.
  • the present invention provides the method for producing a composite membrane described above, wherein the resin sheet is a water-soluble polymer, and the resin sheet bonded to the surface of the porous membrane is removed by dissolving in water or an aqueous solution. It is to provide.
  • a water permeable membrane made of parylene can be provided. That is, since the parylene permeable membrane of the present invention has a characteristic that the conventional parylene membrane does not have such that water can permeate, the parylene membrane can be used for a new use of the permeable membrane. Therefore, it can be used as a parylene film for water treatment. For example, water in which a substance is dissolved and / or dispersed can be permeated through a parylene water permeable membrane or a composite membrane having the water permeable membrane to separate the water.
  • the parylene permeable membrane referred to in the present invention means a parylene membrane having water permeability, and is intended mainly for use in the technical field of water treatment.
  • a cyclophane compound having a polar group is usually used. It is obtained by thermal decomposition by the method. More specifically, when a cyclophane compound having a polar group is thermally decomposed, a radical intermediate is formed, and when this is vapor-deposited on the support, surface polymerization occurs on the support. As a result, the parylene permeable membrane of the present invention is deposited on the support.
  • the thermal decomposition temperature of the cyclophane compound having a polar group is preferably 500 ° C. to 750 ° C., more preferably 550 ° C. to 690 ° C.
  • the support is not limited as long as the parylene permeable membrane can be deposited.
  • a flat glass plate, a stainless steel plate, various resin sheets (the resin sheet is also referred to as a resin film), a nonwoven fabric, a silicon wafer, a porous film, and the like can be given.
  • These supports are preferably subjected to various surface treatments so that the parylene film can be easily deposited.
  • the parylene permeable film deposited on the support can be peeled off depending on the film thickness and used as a single film.
  • a composite membrane obtained by using a porous membrane such as a microfiltration membrane as the porous support and depositing a parylene water permeable membrane on the surface of the porous membrane.
  • a resin sheet having a parylene water permeable membrane obtained by vapor-depositing parylene on the surface of the resin sheet is bonded to the surface of various porous membranes (for example, microfiltration membranes), and then the porous It is also preferable to use a “composite film obtained by removing the resin sheet from the conductive film”.
  • the pores of the porous support for example, the through-holes of the microfiltration membrane are ions whose vapor pressure is substantially zero as shown in the schematic diagram of FIG.
  • the ionic liquid it may be filled with a polymer. If the pores of the porous support are not filled with an ionic liquid or polymer, a uniform thin film cannot be formed on the support. However, if the pores are filled with an ionic liquid or polymer, A uniform thin film can be formed on the surface.
  • the ionic liquid is not limited, for example, N-Methyl-N-butylpyrrolidinium bis (trifluoromethanesulfonyl) imide can be used.
  • the polymer is preferably a water-soluble polymer.
  • the pores of the porous support are filled with an aqueous solution of a water-soluble polymer, but the porous support does not damage the porous support.
  • a parylene permeable film of the present invention deposited on a water-soluble polymer is not damaged.
  • damage may be caused when the porous support is made of an organic material.
  • water-soluble polymer is not limited, for example, polyvinyl alcohol, polyvinyl pyrrolidone and the like can be used.
  • parylene permeable membrane When the parylene permeable membrane is used as a porous composite deposited on a porous support or a porous composite deposited on a porous membrane such as a microfiltration membrane, these pores are filled.
  • the ionic liquid or polymer is removed by a conventional method.
  • the parylene permeable membrane of the present invention is a porous support containing a vapor-deposited liquid (for example, an ionic liquid) or a polymer that does not evaporate during the thin film formation process by the CVD method and can deposit parylene. Is obtained by vapor-depositing parylene on the surface by the CVD method. And if a liquid to be vapor-deposited or a polymer is removed from the porous support, a porous composite having a parylene water permeable membrane and a porous support can be obtained.
  • the porous support is a porous membrane such as a microfiltration membrane, a porous composite membrane comprising a parylene water permeable membrane and a porous membrane can be obtained.
  • a composite membrane that is, a composite membrane having a parylene permeable membrane in which a parylene permeable membrane and an arbitrary membrane are combined is also one embodiment of the present invention.
  • the manufacturing method has an advantage that it is not necessary to use an expensive ionic liquid. Furthermore, there is an advantage that a plurality of cleaning processes necessary for removing the ionic liquid or polymer filled in the pores of the porous support such as the porous support membrane are not necessary.
  • a vapor deposition film peeling agent etc. can be used, for example.
  • a water-soluble polymer sheet for the substrate, dissolve the parylene permeable film deposited on the surface of the sheet in water or an aqueous solution, and peel off the parylene permeable film, which is one of the preferred methods.
  • the water-soluble polymer for example, polyvinyl alcohol, polyvinyl pyrrolidone and the like are preferably used.
  • dissolves in an organic solvent for a resin sheet melt
  • the polymer dissolved in the organic solvent for example, polymethyl methacrylate dissolved in acetone, polystyrene dissolved in toluene, or the like is preferably used.
  • parylene is vapor-deposited on the surface of the resin sheet to obtain a parylene water permeable membrane.
  • a resin sheet having a parylene water permeable membrane is bonded to the surface of an arbitrary porous membrane.
  • the said resin sheet is removed from the said porous film, and the composite film which has a parylene water permeable film on the surface of a porous film is manufactured.
  • This manufacturing method also has an advantage that it is not necessary to use an expensive ionic liquid. Furthermore, there is an advantage that a plurality of cleaning processes necessary for removing the ionic liquid or polymer filled in the pores of the porous support such as the porous support membrane are not necessary.
  • the resin sheet side it is preferable to bond the resin sheet side to the surface of a porous film in the process of bonding the resin sheet which has a parylene water permeable film on the surface to the surface of a porous film. This is because there is no fear that the parylene permeable membrane will be damaged when bonded.
  • the resin sheet can be easily removed by water permeation, and a composite membrane in which the parylene water permeable membrane is in close contact with the surface of the porous membrane can be obtained.
  • the water-soluble polymer for example, polyvinyl alcohol, polyvinyl pyrrolidone and the like are preferably used. It is also possible to use a polymer sheet that dissolves in an organic solvent as the resin sheet, and dissolve and remove it in an organic solvent.
  • the polymer dissolved in the organic solvent for example, polymethyl methacrylate dissolved in acetone, polystyrene dissolved in toluene, or the like is preferably used.
  • water in which a substance is dissolved and / or dispersed is an aqueous solution in which the water-soluble compound is dissolved
  • the water in which the substance is dispersed is a dispersion liquid in which, for example, sludge is dispersed.
  • aqueous solutions or dispersions can separate water when the substance is larger than the pore size of the parylene permeable membrane. That is, water can be separated by removing these substances from water in which various substances are dissolved and / or dispersed depending on the pore size of the parylene permeable membrane.
  • the pore size of the parylene permeable membrane of the present invention is preferably 0.1 to 10 nm.
  • the film thickness of the parylene permeable membrane of the present invention is preferably 10 nm to 10 ⁇ m.
  • the hole diameter and film thickness of the parylene permeable membrane can be adjusted to various hole diameters and film thicknesses by appropriately changing the film forming conditions such as the thermal decomposition temperature.
  • the parylene permeable membrane of the present invention is obtained, for example, by thermally decomposing a cyclophane compound having a polar group.
  • R represents an arbitrary polar group.
  • R is CN
  • COOR 1 R 1 represents CH 3 or CH 2 CH 3
  • CONR 2 R 3 R 2 and R 3 are H, CH 3 or CH 2 CH 3 , respectively.
  • R 2 and R 3 may be the same or different.
  • Particularly preferred is a cyano group in which R is CN.
  • cyclophane compounds those having the following structural formula are particularly preferred.
  • Synthesis example 1 Synthesis of Pseudo-meta-dibromo [2.2] paracyclophane (compound 1) and Pseudo-para-dibromo [2.2] paracyclophane (compound 2) The following operations were carried out in the draft and in the atmosphere.
  • [2.2] Paracyclophane 600 mg (2.88 mmol) is added with ClCl 4 8.2 mL and stirred at 55 ° C.
  • a mixed solution of 0.9 mL (17.5 mmol) bromine and 1.0 mL carbon tetrachloride was slowly added dropwise using a liquefaction funnel, and the mixture was stirred at 55 ° C. for 2 hours.
  • Synthesis example 4 Synthesis of 4-Bromo [2.2] paracyclophane (Compound 6) The following operations were carried out in the draft and in the atmosphere. 1 mL of a mixed solution of Bromine 250 ⁇ L (4.80 mmol) and CCl 4 7.5 mL was added to Iron powder 15 mg (0.27 mmol) with a liquefaction funnel and stirred for 15 minutes. Thereto, 20 mL of CH 2 Cl 2 and 1.0 g (4.8 mmol) of [2.2] paracyclophane were added, and the remaining mixed solution was added little by little with a liquefaction funnel and stirred for 2 hours. Thereafter, saturated aqueous Na 2 SO 3 solution was added, was performed three times was extracted with CH 2 Cl 2. It was dried over MgSO 4 and concentrated in vacuo. Silica gel chromatography was performed using n-hexane, and this was concentrated under reduced pressure to obtain Compound 6 as a white solid.
  • Example 1 A porous support membrane (Isopore, manufactured by Merck Milpore) was immersed in an ionic liquid (N-Methyl-N-butylpyrrolidinium bis (trifluoromethanesulfonyl) imide), and the pores in the porous membrane were filled with the ionic liquid. The filling rate is tracked by weight change, and it is confirmed that each porous support membrane is filled with an equal weight of ionic liquid, and the porous support membrane containing the ionic liquid is placed in the chamber in the parylene coating apparatus. Left at rest.
  • an ionic liquid N-Methyl-N-butylpyrrolidinium bis (trifluoromethanesulfonyl) imide
  • Example 2 A composite membrane of a parylene permeable membrane and a microfiltration membrane was produced in the same manner as in Example 1 except that the thermal decomposition temperature was 650 ° C.
  • Example 3 A composite membrane of a parylene permeable membrane and a microfiltration membrane was produced in the same manner as in Example 1 except that the thermal decomposition temperature was 600 ° C.
  • Example 4 A porous support membrane (Isopore, manufactured by Merck Milpore) was immersed in an ionic liquid (N-Methyl-N-butylpyrrolidinium bis (trifluoromethanesulfonyl) imide), and the pores in the porous membrane were filled with the ionic liquid. The filling rate is tracked by weight change, and it is confirmed that each porous support membrane is filled with an equal weight of ionic liquid, and the porous support membrane containing the ionic liquid is placed in the chamber in the parylene coating apparatus. Left at rest.
  • an ionic liquid N-Methyl-N-butylpyrrolidinium bis (trifluoromethanesulfonyl) imide
  • a parylene permeable membrane As a result, a composite membrane was obtained in which a parylene permeable membrane was deposited on a microfiltration membrane (pore diameter 210 nm, film thickness 20 ⁇ m).
  • Example 5 A porous support membrane (Isopore, manufactured by Merck Milpore) was immersed in an ionic liquid (N-Methyl-N-butylpyrrolidinium bis (trifluoromethanesulfonyl) imide), and the pores in the porous membrane were filled with the ionic liquid. The filling rate is tracked by weight change, and it is confirmed that each porous support membrane is filled with an equal weight of ionic liquid, and the porous support membrane containing the ionic liquid is placed in the chamber in the parylene coating apparatus. Left at rest.
  • an ionic liquid N-Methyl-N-butylpyrrolidinium bis (trifluoromethanesulfonyl) imide
  • a parylene permeable membrane As a result, a composite membrane was obtained in which a parylene permeable membrane was deposited on a microfiltration membrane (pore diameter 210 nm, film thickness 20 ⁇ m).
  • Example 6 A polyvinyl alcohol film (Hi-Rhythm M) manufactured by Nippon Synthetic Chemical Co., Ltd. was placed in a chamber in a parylene coating apparatus. 150 mg of 4-Cyano [2.2] paracyclophane (Compound 7) obtained in Synthesis Example 5 is placed in the vaporization section in a parylene coating apparatus manufactured by Parylene Japan, and sublimated by heating under reduced pressure. The sublimated gas is thermally decomposed into a monomer state when passing through a 650 ° C. pyrolysis furnace. The monomer was introduced into the deposition chamber and polymerized on the surface of the polyvinyl alcohol film placed in the chamber to form a thin film on the surface.
  • Example 7 A polyvinyl alcohol film (Hi-Rhythm M) manufactured by Nippon Synthetic Chemical Co., Ltd. was placed in a chamber in a parylene coating apparatus. 150 mg of 4-Cyano [2.2] paracyclophane (Compound 7) obtained in Synthesis Example 5 is placed in the vaporization section in a parylene coating apparatus manufactured by Parylene Japan, and sublimated by heating under reduced pressure. The sublimated gas is thermally decomposed into a monomer state when passing through a 650 ° C. pyrolysis furnace. The monomer was introduced into the deposition chamber and polymerized on the surface of the polyvinyl alcohol film placed in the chamber to form a thin film on the surface.
  • the parylene permeable membrane of the present invention and the microfiltration membrane efficiently eliminate the dye in the aqueous solution as compared with the composite membrane of the comparative example. I understand that. Moreover, it can be understood that the water flow rate and dye exclusion rate of the composite membrane can be adjusted by the production conditions (thermal decomposition temperature) of the parylene permeable membrane.
  • Example 3 Using the composite membranes of Example 1 with different thicknesses of the parylene permeable membrane existing on the surface of the microfiltration membrane (pore diameter 210 nm, thickness 20 ⁇ m), water from an aqueous solution (concentration: 10 ⁇ M) in which rose bengal was dissolved was used. Separation was performed. The results are shown in “Table 3”. From the results shown in Table 3, it can be understood that an excellent dye exclusion rate is exhibited without depending on the film thickness of the parylene permeable membrane.
  • a water permeable membrane made of parylene can be provided.
  • the present invention is an invention contrary to the common sense that a parylene film does not allow liquid to pass through, and provides a new application of the parylene film.
  • it can be used as a nanofilter in the technical field of water treatment.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Separation Using Semi-Permeable Membranes (AREA)

Abstract

[Problème] Fournir une membrane perméable à l'eau constituée de parylène, un procédé de production de la membrane perméable à l'eau, et un procédé de séparation de l'eau au moyen de la membrane perméable à l'eau ou une membrane composite de celle-ci. [Solution] La présente invention concerne une membrane de parylène perméable à l'eau caractérisée en ce qu'elle comporte des groupes polaires ; caractérisée par un procédé spécifique de production de la membrane de parylène perméable à l'eau ou une membrane composite de celle-ci ; et un procédé de séparation de l'eau, caractérisé en ce que l'eau qui contient une substance dissoute et/ou dispersée dans celle-ci est amenée à traverser la membrane de parylène perméable à l'eau ou une membrane composite de celle-ci, de manière à séparer l'eau.
PCT/JP2016/052615 2015-02-19 2016-01-29 Membrane de parylène perméable à l'eau et son procédé de production, et procédé de séparation de l'eau WO2016132859A1 (fr)

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JP2018131520A (ja) * 2017-02-15 2018-08-23 国立大学法人信州大学 新規パリレン、架橋パリレン透水膜、及びこれらの製造方法
WO2018237212A1 (fr) * 2017-06-22 2018-12-27 The Procter & Gamble Company Films comprenant une couche hydrosoluble et un revêtement organique déposé en phase vapeur
JP2019150779A (ja) * 2018-03-05 2019-09-12 Ｋｉｓｃｏ株式会社 イミダゾール側鎖を有するパリレン膜
JP2019150778A (ja) * 2018-03-05 2019-09-12 Ｋｉｓｃｏ株式会社 アミド側鎖を有するパリレン膜
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WO2020161254A1 (fr) * 2019-02-06 2020-08-13 Fostag Formenbau Ag Article en matière plastique soluble dans l'eau
JP2021530351A (ja) * 2018-07-19 2021-11-11 ダブリュ.エル.ゴア アンド アソシエイツ, インコーポレイティドW.L. Gore & Associates, Incorporated 多孔質ポリパラキシリレン膜又は多孔質ポリパラキシリレン／ポリテトラフルオロエチレン複合膜を含むハイフロー液体ろ過デバイス

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Cited By (15)

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Publication number Priority date Publication date Assignee Title
JP2018131520A (ja) * 2017-02-15 2018-08-23 国立大学法人信州大学 新規パリレン、架橋パリレン透水膜、及びこれらの製造方法
US10604632B2 (en) 2017-04-07 2020-03-31 The Procter & Gamble Company Water-soluble films
US10604631B2 (en) 2017-04-07 2020-03-31 The Procter & Gamble Company Water-soluble films
US11192139B2 (en) 2017-06-22 2021-12-07 The Procter & Gamble Company Films including a water-soluble layer and a vapor-deposited organic coating
US10450119B2 (en) 2017-06-22 2019-10-22 The Procter & Gamble Company Films including a water-soluble layer and a vapor-deposited inorganic coating
WO2018237212A1 (fr) * 2017-06-22 2018-12-27 The Procter & Gamble Company Films comprenant une couche hydrosoluble et un revêtement organique déposé en phase vapeur
US11208246B2 (en) 2017-06-22 2021-12-28 The Procter & Gamble Company Films including a water-soluble layer and a vapor-deposited inorganic coating
US11473190B2 (en) 2017-06-22 2022-10-18 The Procter & Gamble Company Films including a water-soluble layer and a vapor-deposited inorganic coating
US11738367B2 (en) 2017-06-22 2023-08-29 The Procter & Gamble Company Films including a water-soluble layer and a vapor-deposited organic coating
JP2019150778A (ja) * 2018-03-05 2019-09-12 Ｋｉｓｃｏ株式会社 アミド側鎖を有するパリレン膜
JP2019150779A (ja) * 2018-03-05 2019-09-12 Ｋｉｓｃｏ株式会社 イミダゾール側鎖を有するパリレン膜
JP7105436B2 (ja) 2018-03-05 2022-07-25 Ｋｉｓｃｏ株式会社 イミダゾール側鎖を有するパリレン膜
JP2021530351A (ja) * 2018-07-19 2021-11-11 ダブリュ.エル.ゴア アンド アソシエイツ, インコーポレイティドW.L. Gore & Associates, Incorporated 多孔質ポリパラキシリレン膜又は多孔質ポリパラキシリレン／ポリテトラフルオロエチレン複合膜を含むハイフロー液体ろ過デバイス
JP7343567B2 (ja) 2018-07-19 2023-09-12 ダブリュ．エル．ゴア アンド アソシエイツ，インコーポレイティド 多孔質ポリパラキシリレン膜又は多孔質ポリパラキシリレン／ポリテトラフルオロエチレン複合膜を含むハイフロー液体ろ過デバイス
WO2020161254A1 (fr) * 2019-02-06 2020-08-13 Fostag Formenbau Ag Article en matière plastique soluble dans l'eau

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