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WO1997036951A1 - Film continu de polyurethane repoussant l'eau et l'huile - Google Patents

Film continu de polyurethane repoussant l'eau et l'huile Download PDF

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Publication number
WO1997036951A1
WO1997036951A1 PCT/US1997/000512 US9700512W WO9736951A1 WO 1997036951 A1 WO1997036951 A1 WO 1997036951A1 US 9700512 W US9700512 W US 9700512W WO 9736951 A1 WO9736951 A1 WO 9736951A1
Authority
WO
WIPO (PCT)
Prior art keywords
water
oil
film
treated
polyurethane film
Prior art date
Application number
PCT/US1997/000512
Other languages
English (en)
Inventor
Ya Xi Shen
Original Assignee
W.L. Gore & Associates, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by W.L. Gore & Associates, Inc. filed Critical W.L. Gore & Associates, Inc.
Priority to AU16982/97A priority Critical patent/AU1698297A/en
Publication of WO1997036951A1 publication Critical patent/WO1997036951A1/fr

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Classifications

    • 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
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04—Homopolymers or copolymers of esters
    • C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • C09D133/16—Homopolymers or copolymers of esters containing halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/0427—Coating with only one layer of a composition containing a polymer binder
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/043—Improving the adhesiveness of the coatings per se, e.g. forming primers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2433/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers

Definitions

  • This invention relates to water and oil repellent, polyurethane continuous films with good water vapor transmission rate (MVTR).
  • Method 1 employs hydrophobic polymeric membranes with microporous structures which allow only molecules in the vapor phase to pass through.
  • a representative of this class of membranes or films is expanded porous polytetrafluoroethylene (ePTFE) which is described in U.S. Patent No. 3,953,566.
  • Method 2 is to make a nonporous continuous hydrophilic polymeric film which is waterproof. The hydrophilicity of these films allows water molecules to pass through. It is obvious that the water vapor transmission mechanism is totally different for these two types of films.
  • water vapor passes through the micropores but liquid water is prevented from passing through because of the hydrophobic nature of the polymer.
  • Method 2 there are no pores in the polymer, but water vapor can pass through because the polymer structure is such that it is amenable to molecular transfer of individual water vapor molecules.
  • Hydrophilic polyurethanes i.e., polyurethanes with hydrophilic soft segments such as polyethylene oxide
  • hydrophilic polymers used to make waterproof, water vapor permeable films, laminates thereof and continuous coatings thereof on textiles.
  • These polymer films are disclosed in U.S. Patent No. 4,273,911 , U.S. Patent No. 3,164,565, U.S. Patent No. 3,901 ,852, U.S. Patent No. 4,367,327, U. S. Patent No. 4,532,316, and U.S. Patent No. 4,686,137.
  • polyurethane films Due to the affinity of polyurethane for many solvents, oils and other organic liquids, polyurethane films have limited applications. They either swell or are dissolved upon contacting with solvents, oils and other liquids including water for hydrophilic polyurethane films. This property precludes their use or become a disadvantage in applications involving contacting with liquids that swell or dissolve the film. It would be advantageous, and it is a purpose of this invention to provide a hydrophilic polyurethane, i.e., one that transports water vapor molecules, but which also has enhanced resistance to oil and water.
  • U.S. Patent No. 3,879,493 discloses a water vapor permeable polymeric composition comprising a homogeneous blend of a hydrophilic thermoplastic polymer with a hydrophobic polymer, mainly polyurethane. This has some enhanced polymer properties but does not have good water and oil repellence, or solvent resistance.
  • U. S. Patent No. 5,447,783 discloses a multicomponent film having three layers.
  • the outer layers comprise a continuous layer of a hydrophobic copolyetherester elastomer.
  • the inner middle layer is a continuous layer of a hydrophilic copolyetherester elastomer.
  • U. S. Patent No. 4,769,273 disclosed a bicomponent film with a hydrophilic copolyester elastomeric layer and a hydrophobic copolyester elastomeric layer. These films are not adequate as water, oil and solvent repellents.
  • Japanese Patent JP 62,103,134 discloses a waterproof, water vapor permeable composite by impregnating a hydrophobic polymer with cellulosic fiber, paper or non-woven fabrics.
  • the hydrophobic polymers can be acrylic emulsions, synthetic rubber latex, polyurethane emulsion or vinylidenechloride latex.
  • this invention is directed to the use of organic polymers containing perfluoroalkyl alkyl pendant side chain or side chains terminated with perfluoroalkyl alkyl groups as coatings on hydrophilic polyurethane substrate films.
  • the organic polymer imparts water and oil repellence, while the hydrophilic polyurethane film remains hydrophilic and provides good moisture vapor transmission rates (MVTR).
  • MVTR moisture vapor transmission rates
  • hydrophilic is meant that the polymer has an affinity for water and will allow water molecules to pass through.
  • pendant is meant that the side chains depend from recurring backbone units of the polymer.
  • the following polymers are examples of the polymers of this class.
  • R H or CH 3
  • R' H or lower alkyl such as methyl, ethyl, butyl
  • m is an integer from 1 to 15
  • n is an integer from 3 to 17.
  • polymers contain urethane and/or urea groups and have pendant perfluoroalkyl groups or perfluoroalkyl group terminated side chains.
  • This class of materials are particularly important because of their urethane nature which offers good adhesion with the polyurethane substrate film surface through strong interface interaction including hydrogen bonding and compatibility.
  • the urethane and/or urea linkages can be either incorporated in main chain backbone or in pendant side chains. In other words, they can either be polyurethanes and/or ureas having pendant side chains terminated with perfluoroalkyl groups or any polymers having pendant side chains containing urethane and/or urea linkages as well as perfluoroalkyl groups as the terminate group.
  • R 2 polyethers such as poly(ethylene oxide), poly(tetramethylene oxide), polyesters such as polycaproluctone, poly(hexamethylene adipate), alkyls such as (CH 2 ) 2- ⁇ 4 and the like.
  • m is an integer from 1 to 15 and n is an integer from 3 to 17.
  • N denotes number of repeating units of the polymer.
  • R 1 R 2 , N, m and n are the same as those in 4.
  • R 3 is a linkage introduced from Poly-Fox Polyols which is a polyether backbone with perfluoroalkyl pendant groups
  • polymers that contain perfluoroalkyl group or perfluoroalkylalkyl can be used as coating materials.
  • Such polymers include perfluorinated polyesters, polyamides, polyimides and vinyl polymers.
  • the hydrophilic polyurethane films used in this invention can be any type of polyurethanes having hydrophilic soft segments which have water vapor transmission properties. Films made from polyurethanes derived from polyethylene glycol diol and any type of diisocyanates and chain extender are particularly preferred. A specific example is the polyurethane made from polyethylene glycol diol, methylenedi-p-phenylene diisocyanate and a chain extender such as butanediol. The films can be made by extrusion or casting and range from 0.5 mil to 5.0 mil in thickness.
  • Coating can be done by spray coating or dip-in coating or the like. Coating thickness is controlled by the method and by solid content (concentration) in the coating solution. Any other conventional coating methods may also be used.
  • the guidelines for solvent selection are (1) the coating material must be able to be dissolved in the solvent, (2) the solvent should not dissolve the polyurethane film (3) the solvent can be removed below the temperature at which the polyurethane film melts and (4) the polyurethane film can be wetted by the solvent for uniform coating. Many common solvents meet these requirements.
  • Coating may be on both sides through dip-in coating method
  • the two side coated film of the invention is totally water and oil repellent and resistant It has oil repellence rating greater than #8 (AATCC standard testing method-
  • Coating can be performed only on one side of the film through either spray or kiss coating methods
  • the one side coated film results in an asymmetric film
  • This type of film has unique properties which offer special applications
  • the asymmet ⁇ c film has one side with extremely low surface free energy and the other side with extremely high surface free energy
  • the low surface free energy side is hydrophobic and oleophobic It is water and oil repellent and resistant has oil rating greater than #8 (AATCC standard testing method-118) and water contact angles ranging from 112° to 118°, depending on coating material and coating thickness
  • the high surface free energy side is hydrophilic and oleophilic, the same as uncoated film It can be wetted by water and oil readily
  • the asymmetric film will have a different water vapor transmission rate depending on which side is placed toward a vapor source In one test, when the low surface free energy side was toward water, an MVTR was obtained slightly lower than the untreated film When the high surface free energy side was toward water, an MVTR was obtained that was
  • the film can be used in places where selective MVTR is required It can be used in lamination with the high surface free energy side having better adhesion to the substrate, while the low surface free energy side is water and oil repellent and resistant
  • the oil rating tests were done with AATCC standard test method 118
  • the water contact angle measurements were performed on Rame-Hart Goniometer Model A100 MVTR values were obtained with Dry Modified Desiccant Method (MDM dry method).
  • MDM dry method the sample is exposed to approximately 90% relative humidity (no water contact) on one side while a desiccant on the opposite side draws vapor through the material.
  • the transmission rate is expressed in grams weight gain of the desiccant per square meter of material exposed to the desiccant per 24 hours (g/m 2 .24hrs).
  • Milease F-95 emulsion a perfluoroalkylalkyl acrylate emulsion (50 ml), from Asahi Glass Co., Japan was mixed with 150 ml of water at room temperature to make a diluted emulsion.
  • Example 2 The same polyurethane film as that used in Example 1 was treated with the same diluted emulsion as that in Example 1 on one side of the film by spraying the emulsion on one side.
  • the treated film was first air dried to dryness and then oven dried at 100°C for 10 minutes.
  • Test results from the treated side Tested with #8 oil, the oil rolled off from the surface, indicating that it has oil rating #8 or above. Water contact angle was 113°.
  • MVTR measured by facing the treated side toward water
  • Test results from the untreated side Tested with #1 oil, the oil was absorbed into the film immediately, indicating that it has an oil rating less than #1. Water was also absorbed into the film immediately.
  • MVTR measured by facing the untreated side toward water is 4,071 (g/m 2 .24hrs).
  • a further diluted emulsion was prepared by adding 350 ml of water into 50 ml of the diluted emulsion from Example 1.
  • the same film as in Example 1 was treated on both sides with such further diluted emulsion.
  • the treated film was first air dried to dryness and then oven dried at 100°C for 10 minutes.
  • Example 2 The same film as that used in Example 1 was treated on one side of the film with the same further diluted emulsion as that in Example 3 by spraying the emulsion on one side.
  • the treated film was first air dried to dryness and then oven dried at 100°C for 10 minutes.
  • Test results from the treated side Tested with #8 oil, the oil rolled off from the surface, indicating that it has an oil rating #8 or above. Water contact angle was 118°. MVTR (measured by facing the treated side toward water) was 3,472 (g/m 2 .24hrs).
  • Test results from the untreated side Tested with #1 oil and also with water, both the oil and water were absorbed into the film immediately, indicating that it is water wettable and has an oil rating less than #1.
  • MVTR measured by facing the untreated side toward water
  • a polyethylene glycol diol and methylenedi-p-phenylene diisocyanate based hydrophilic polyurethane film of 2.0 mil thickness was treated on one side of the film with the same further diluted emulsion as that in Example 3 by spraying the emulsion on one side.
  • the treated film was first air dried to dryness and then oven dried at 100°C for 10 minutes.
  • Test results from the treated side Tested with #8 oil, the oil rolled off from the surface, indicating that it has an oil rating #8 or above. Water contact angle was 117°.
  • MVTR measured by facing the treated side toward water was 4,253 (g/m 2 .24hrs).
  • Test results from the untreated side Tested with #1 oil and also with water, both the oil and water were absorbed into the film immediately, indicating that it is water wettable and has an oil rating less than #1.
  • MVTR measured by facing the untreated side toward water
  • Example 6 Example 6:
  • a solution was prepared by dissolving 1.5 grams of a copolymer containing units of perfluoroalkyl methacrylate in 100 ml of 1,3-trifluoromethyl benzene by warming.
  • the same film as that used in Example 1 was treated with the solution on both sides by spraying.
  • the treated film was first air dried to dryness and then oven dried at 100°C for 10 minutes.
  • Example 1 The same film as that used in Example 1 was treated on one side of the film with the same solution as that in Example 6 by spraying the solution on one side.
  • the treated film was air dried to dryness and then oven dried at 100 c C for 10 minutes.
  • Test results from the treated side Tested with #8 oil, the oil rolled off from the surface, indicating that it has an oil rating #8 or above. Water contact angle was 118°. MVTR (measured by facing the treated side toward water) was 6,885 (g/m 2 .24hrs).
  • Test results from the untreated side Tested with #1 oil and also water, both the oil and water were absorbed into the film immediately, indicating that it is water wettable and has oil rating less than #1.
  • MVTR measured by facing the untreated side toward water was 8,795 (g/m 2 .24hrs).
  • a diluted solution was prepared by adding 50 ml of 1 ,3-trifluoromethyl benzene to 25 ml of the solution from Example 6. The same film as that in
  • Example 1 was treated with the diluted solution on both sides by spraying.
  • the treated film was air dried to dryness and then oven dried at 100°C for 10 minutes.
  • Example 1 The same film as that used in Example 1 was treated with the same diluted solution as that in Example 8 on one side of the film by spraying the solution on one side.
  • the treated film was air dried to dryness and then oven dried at 100°C for 10 minutes.
  • Test results from the treated side Tested with #8 oil, the oil rolled off from the surface, indicating that it has oil rating #8 or above. Water contact angle was 117°. MVTR (measured by facing the treated side toward water) was 8,043 (g/m 2 .24hrs).
  • Test results from the untreated side Tested with #1 oil and also water, both the oil and water were absorbed into the film immediately, indicating that it is water wettable and has an oil rating less than #1.
  • MVTR measured by facing the untreated side toward water was 13,163 (g/m 2 .24hrs).
  • Example 5 The same film as that used in Example 5 was treated on both sides with the same diluted solution as that in Example 8 by spraying.
  • the treated film was first air dried to dryness and then oven dried at 100°C for 10 minutes.
  • Example 5 The same film as that used in Example 5 was treated on one side of the film with the same solution as that in Example 8 by spraying the solution on one side.
  • the treated film was air dried to dryness and then oven dried at 100°C for 10 minutes.
  • Test results from the treated side Tested with #8 oil, the oil rolled off from the surface, indicating that it has an oil rating #8 or above. Water contact angle was 117°. MVTR (measured by facing the treated side toward water) was 5,494 (g/m 2 .24hrs).
  • Test results from the untreated side Tested with #1 oil and also water, both the oil and water were absorbed into the film immediately, indicating that it is water wettable and has an oil rating less than #1.
  • MVTR measured by facing the untreated side toward water was 7,667 (g/m .24hrs).
  • Milease F-95 emulsion a perfluoroalkyl acrylate aqueous emulsion from (20 ml) Asahi Glass Company, Japan was mixed with 80 ml of water at room temperature to make a diluted emulsion.
  • the same film as that used in Example 1 was treated with the emulsion on one side of the film by spraying the emulsion on one side.
  • the treated film was air dried to dryness and then oven dried at 100°C for 10 minutes.
  • Test results from the treated side Tested with #8 oil, the oil rolled off from the surface, indicating that it has an oil rating #8 or above. It was water repellent.
  • MVTR measured by facing the treated side toward water was 2,112 (g/m 2 .24hrs).
  • Test results from the untreated side Tested with #1 oil and also water, both the oil and water were absorbed into the film immediately, indicating that it is water wettable and has an oil rating less than #1.
  • MVTR measured by facing the untreated side toward water was 5,092 (g/m 2 .24hrs).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Laminated Bodies (AREA)
  • Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)

Abstract

L'invention concerne un film de polyuréthane hydrophile présentant au moins une surface recouverte d'un polymère organique comportant des groupes pendants perfluoroalkylalkyles ou perfluoroalkyles en suspension. Le polymère organique confère une caractéristique d'oléophobie et d'hydrophobie au film de polyuréthane. Ces films présentent un degré élevé de transmission de la vapeur d'eau.
PCT/US1997/000512 1996-04-02 1997-01-14 Film continu de polyurethane repoussant l'eau et l'huile WO1997036951A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU16982/97A AU1698297A (en) 1996-04-02 1997-01-14 Water and oil repellent polyurethane film

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US62640996A 1996-04-02 1996-04-02
US08/626,409 1996-04-02

Publications (1)

Publication Number Publication Date
WO1997036951A1 true WO1997036951A1 (fr) 1997-10-09

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PCT/US1997/000512 WO1997036951A1 (fr) 1996-04-02 1997-01-14 Film continu de polyurethane repoussant l'eau et l'huile

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WO (1) WO1997036951A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10120989A1 (de) * 2001-04-25 2002-11-07 Inst Polymerforschung Dresden Hydrophobe permanente Beschichtungen auf Substraten und Verfahren zu ihrer Herstellung
WO2005007722A1 (fr) * 2003-07-11 2005-01-27 Construction Research & Technology Gmbh Resines de polyurethanne modifiees au fluor a un ou deux constituants, leur procede de production et leur utilisation
CN103935096A (zh) * 2014-04-02 2014-07-23 中国科学院合肥物质科学研究院 改性的水性聚氨酯乳胶膜及其制备方法
EP3176237A4 (fr) * 2014-07-30 2018-02-07 Mitsubishi Materials Corporation Agent oléofuge hydrophile et procédé de fabrication associé, et matériau de recouvrement de surface, film de revêtement, composition de résine, milieu de filtre de séparation huile-eau et corps poreux
US10294125B2 (en) 2014-07-30 2019-05-21 Mitsubishi Materials Corporation Filter medium, method for producing filter medium, water treatment module, and water treatment device
US10364360B2 (en) 2014-07-30 2019-07-30 Mitsubishi Materials Corporation Surface coating material, coating film, and hydrophilic oil repellent member
US10399868B2 (en) 2014-07-30 2019-09-03 Mitsubishi Materials Corporation Oil-water separation apparatus and drainage system

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1262526A (en) * 1969-03-21 1972-02-02 Minnesota Mining & Mfg Coating for optical element
EP0331307A2 (fr) * 1988-03-02 1989-09-06 E.I. Du Pont De Nemours And Company Polyétherglycol perfluoroalcoylé et sa préparation
EP0339880A2 (fr) * 1988-04-27 1989-11-02 Minnesota Mining And Manufacturing Company Compositions de perfluoropolyéthers à basse adhésion
JPH0361041A (ja) * 1989-07-29 1991-03-15 Dynic Corp 揆水・揆油性を有するシートおよびその製法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1262526A (en) * 1969-03-21 1972-02-02 Minnesota Mining & Mfg Coating for optical element
EP0331307A2 (fr) * 1988-03-02 1989-09-06 E.I. Du Pont De Nemours And Company Polyétherglycol perfluoroalcoylé et sa préparation
EP0339880A2 (fr) * 1988-04-27 1989-11-02 Minnesota Mining And Manufacturing Company Compositions de perfluoropolyéthers à basse adhésion
JPH0361041A (ja) * 1989-07-29 1991-03-15 Dynic Corp 揆水・揆油性を有するシートおよびその製法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 9117, Derwent World Patents Index; AN 91-121691, XP002030976 *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10120989A1 (de) * 2001-04-25 2002-11-07 Inst Polymerforschung Dresden Hydrophobe permanente Beschichtungen auf Substraten und Verfahren zu ihrer Herstellung
WO2005007722A1 (fr) * 2003-07-11 2005-01-27 Construction Research & Technology Gmbh Resines de polyurethanne modifiees au fluor a un ou deux constituants, leur procede de production et leur utilisation
CN103935096A (zh) * 2014-04-02 2014-07-23 中国科学院合肥物质科学研究院 改性的水性聚氨酯乳胶膜及其制备方法
CN103935096B (zh) * 2014-04-02 2016-08-31 中国科学院合肥物质科学研究院 改性的水性聚氨酯乳胶膜及其制备方法
EP3176237A4 (fr) * 2014-07-30 2018-02-07 Mitsubishi Materials Corporation Agent oléofuge hydrophile et procédé de fabrication associé, et matériau de recouvrement de surface, film de revêtement, composition de résine, milieu de filtre de séparation huile-eau et corps poreux
US10208210B2 (en) 2014-07-30 2019-02-19 Mitsubishi Materials Corporation Hydrophilic oil repellent and production method of same, surface coating material, coating film, resin composition, oil-water separation filter material, and porous body
US10294125B2 (en) 2014-07-30 2019-05-21 Mitsubishi Materials Corporation Filter medium, method for producing filter medium, water treatment module, and water treatment device
US10364360B2 (en) 2014-07-30 2019-07-30 Mitsubishi Materials Corporation Surface coating material, coating film, and hydrophilic oil repellent member
US10399868B2 (en) 2014-07-30 2019-09-03 Mitsubishi Materials Corporation Oil-water separation apparatus and drainage system

Also Published As

Publication number Publication date
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