JP2007182565A - ポリウレタン膜およびその製造方法 - Google Patents
ポリウレタン膜およびその製造方法 Download PDFInfo
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- 229920006264 polyurethane film Polymers 0.000 title claims abstract description 57
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 28
- 239000002904 solvent Substances 0.000 claims abstract description 54
- 239000004814 polyurethane Substances 0.000 claims abstract description 35
- 229920002635 polyurethane Polymers 0.000 claims abstract description 35
- 239000011148 porous material Substances 0.000 claims abstract description 25
- 230000015271 coagulation Effects 0.000 claims abstract description 18
- 238000005345 coagulation Methods 0.000 claims abstract description 18
- 239000000758 substrate Substances 0.000 claims abstract description 15
- 239000013557 residual solvent Substances 0.000 claims abstract description 7
- 239000002798 polar solvent Substances 0.000 claims abstract description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 39
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 6
- 238000010924 continuous production Methods 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 abstract description 12
- 238000000576 coating method Methods 0.000 abstract description 12
- 230000001112 coagulating effect Effects 0.000 abstract description 2
- 238000007598 dipping method Methods 0.000 abstract 1
- 239000012528 membrane Substances 0.000 description 12
- 239000010408 film Substances 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- -1 polypropylene Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 229920001610 polycaprolactone Polymers 0.000 description 2
- 239000004632 polycaprolactone Substances 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002649 leather substitute Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 230000003075 superhydrophobic effect Effects 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C67/00—Shaping techniques not covered by groups B29C39/00 - B29C65/00, B29C70/00 or B29C73/00
- B29C67/20—Shaping techniques not covered by groups B29C39/00 - B29C65/00, B29C70/00 or B29C73/00 for porous or cellular articles, e.g. of foam plastics, coarse-pored
- B29C67/202—Shaping techniques not covered by groups B29C39/00 - B29C65/00, B29C70/00 or B29C73/00 for porous or cellular articles, e.g. of foam plastics, coarse-pored comprising elimination of a solid or a liquid ingredient
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
- B01D67/0002—Organic membrane manufacture
- B01D67/0009—Organic membrane manufacture by phase separation, sol-gel transition, evaporation or solvent quenching
- B01D67/0016—Coagulation
- B01D67/00165—Composition of the coagulation baths
-
- 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
- B01D71/54—Polyureas; Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
-
- 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
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/06—Polyurethanes from polyesters
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2323/00—Details relating to membrane preparation
- B01D2323/219—Specific solvent system
- B01D2323/22—Specific non-solvents or non-solvent system
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2325/00—Details relating to properties of membranes
- B01D2325/28—Degradation or stability over time
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29K2075/00—Use of PU, i.e. polyureas or polyurethanes or derivatives thereof, as moulding material
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/249921—Web or sheet containing structurally defined element or component
- Y10T428/249953—Composite having voids in a component [e.g., porous, cellular, etc.]
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Manufacturing & Machinery (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Dispersion Chemistry (AREA)
- Mechanical Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Synthetic Leather, Interior Materials Or Flexible Sheet Materials (AREA)
- Laminated Bodies (AREA)
Abstract
【解決手段】複数の細孔が表面から内部に分布しているポリウレタン膜である。また、ポリウレタン溶液を基材に塗布する工程、少なくとも1つの非溶剤を含む凝固浴に前記基材を浸漬して、細孔が表面から内部に分布するポリウレタン膜を凝固させる工程、および非極性または低極性溶剤により前記ポリウレタン膜中の残留溶剤および非溶剤を除去する工程、を備えるポリウレタン膜の製造方法である。
【選択図】図2
Description
メチレンジフェニルジイソシアネート(MDI)および1,2−エタンジオールから得られたポリウレタンと、N,N−ジメチルホルムアミド(DMF)とからなるポリウレタン溶液(CW835、立大化工社製、固形分19重量%)を塗工機でガラス基材上に塗布した。コーティングの厚さは約250〜500μmとした。次いで、その基材を、N,N−ジメチルホルムアミド(DMF)および脱イオン水を含む凝固浴に浸して、ゾル−ゲル型ポリウレタン膜を形成した。なお、DMFと水との重量割合は1:99とした。4時間後、得られたポリウレタン膜をn−ヘキサン中に浸し、残留した溶剤および非溶剤を除去した。最後に、n−ヘキサンを室温下にて真空オーブン中で除去した。そして、スキン層がなく、複数の細孔が表面から内部に分布している対称多孔質ポリウレタン膜を得た。なお、すべての工程は室温(25℃)にて連続で行われた。細孔の直径は5〜30μmであり、水の接触角は122°であった。
実施例1同様にして、ポリウレタン溶液を塗工機でガラス基材上に塗布した。コーティングの厚さは約250〜500μmとした。次いで、その基材を、N,N−ジメチルホルムアミド(DMF)および脱イオン水を含む凝固浴に浸して、ゾル−ゲル型ポリウレタン膜を形成した。なお、DMFと水との重量割合は50:50とした。4時間後、そのポリウレタン膜をn−ヘキサン中に浸し、残留した溶剤および非溶剤を除去した。最後に、n−ヘキサンを室温下にて真空オーブン中で除去した。そして、スキン層がなく、複数の細孔が表面から内部に分布している対称多孔質ポリウレタン膜を得た。なお、すべての工程は室温(25℃)にて連続で行われた。細孔の直径は5〜20μmであり、水の接触角は87°であった。
実施例1同様にして、ポリウレタン溶液を塗工機でガラス基材上に塗布した。コーティングの厚さは約250〜500μmとした。次いで、その基材を、N,N−ジメチルホルムアミド(DMF)および脱イオン水を含む凝固浴に浸して、ゾル−ゲル型ポリウレタン膜を形成した。なお、DMFと水との重量割合は20:80とした。4時間後、そのポリウレタン膜をn−ヘキサン中に浸し、残留した溶剤および非溶剤を除去した。最後に、n−ヘキサンを室温下にて真空オーブン中で除去した。そして、スキン層がなく、複数の細孔が表面から内部に分布している対称多孔質ポリウレタン膜を得た。なお、すべての工程は室温(25℃)にて連続で行われた。細孔の直径は5〜15μmであり、水の接触角は118°であった。
実施例1同様にして、ポリウレタン溶液を塗工機でガラス基材上に塗布した。コーティングの厚さは約250〜500μmとした。次いで、その基材を数時間オーブンにて乾燥させると、如何なる多孔質構造をも持たない、表面接触角が65.96°のポリウレタン膜が得られた。
2 水滴
Claims (13)
- 複数の細孔が表面から内部に分布しているポリウレタン膜。
- 前記ポリウレタンが、一種の溶剤系ポリウレタンである請求項1記載のポリウレタン膜。
- 前記細孔の直径が約0.1〜50μmである請求項1記載のポリウレタン膜。
- ポリウレタン溶液を基材に塗布する工程、
少なくとも1つの非溶剤を含む凝固浴に前記基材を浸漬して、細孔が表面から内部に分布するポリウレタン膜を凝固させる工程、および
非極性または低極性溶剤により前記ポリウレタン膜中の残留溶剤および非溶剤を除去する工程、
を備えるポリウレタン膜の製造方法。 - 前記ポリウレタンが、一種の溶剤系ポリウレタンである請求項4記載のポリウレタン膜の製造方法。
- 少なくとも一つの非溶剤を含む前記凝固浴が、さらに溶剤を含む請求項4記載のポリウレタン膜の製造方法。
- 前記溶剤と非溶剤の重量割合が約1:99〜50:50である請求項6記載のポリウレタン膜の製造方法。
- 前記非溶剤が、水またはグリセロールを含む請求項4記載のポリウレタン膜の製造方法。
- 前記溶剤が、N,N−ジメチルホルムアミドまたはN,N−ジメチルアセトアミドを含む請求項6記載のポリウレタン膜の製造方法。
- 前記非極性または低極性溶剤が、n−ヘキサン、メタノールまたはイソプロパノールを含む請求項4記載のポリウレタン膜の製造方法。
- 前記製造が室温で行われる請求項4記載のポリウレタン膜の製造方法。
- 前記製造が連続プロセスである請求項4記載のポリウレタン膜の製造方法。
- 前記ポリウレタン膜の細孔の直径が、約0.1〜50μmである請求項4記載のポリウレタン膜の製造方法。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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TW94147649A TWI303642B (en) | 2005-12-30 | 2005-12-30 | Polyurethane films and method of fabricating the same |
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JP2007182565A true JP2007182565A (ja) | 2007-07-19 |
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JP2006338255A Pending JP2007182565A (ja) | 2005-12-30 | 2006-12-15 | ポリウレタン膜およびその製造方法 |
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US (1) | US20070154701A1 (ja) |
JP (1) | JP2007182565A (ja) |
TW (1) | TWI303642B (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2014200199A (ja) * | 2013-04-05 | 2014-10-27 | 株式会社ダイセル | 生体親和性多孔体及びその製造方法 |
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KR970020169A (ko) * | 1995-10-28 | 1997-05-28 | 김은영 | 수증기 또는 유기 증기 흡착을 이용한 다공성 분리막의 제조 방법 |
SE9904080D0 (sv) * | 1998-12-03 | 1999-11-11 | Ciba Sc Holding Ag | Fotoinitiatorberedning |
WO2004052641A1 (en) * | 2002-12-10 | 2004-06-24 | Saint Gobain Technical Fabrics | Breathable, waterproofing, tear-resistant fabric |
US20050069692A1 (en) * | 2003-09-25 | 2005-03-31 | Koichi Ito | Method for coating porous polyurethane resin |
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2005
- 2005-12-30 TW TW94147649A patent/TWI303642B/zh active
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- 2006-12-15 JP JP2006338255A patent/JP2007182565A/ja active Pending
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JPS6140336A (ja) * | 1984-07-31 | 1986-02-26 | Mitsubishi Chem Ind Ltd | ポリアミノ酸ウレタン樹脂系多孔質膜の製造法 |
JPH04264144A (ja) * | 1991-02-19 | 1992-09-18 | San Five Kk | 多孔質ポリウレタンシートの製造方法 |
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JP2014200199A (ja) * | 2013-04-05 | 2014-10-27 | 株式会社ダイセル | 生体親和性多孔体及びその製造方法 |
Also Published As
Publication number | Publication date |
---|---|
US20070154701A1 (en) | 2007-07-05 |
TW200724586A (en) | 2007-07-01 |
TWI303642B (en) | 2008-12-01 |
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