JP5058827B2 - 高分子微多孔体の製造方法ならびに高分子微多孔体および分離膜 - Google Patents
高分子微多孔体の製造方法ならびに高分子微多孔体および分離膜 Download PDFInfo
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
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- 125000005265 dialkylamine group Chemical group 0.000 claims description 3
- 229920005597 polymer membrane Polymers 0.000 claims description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
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- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 238000000034 method Methods 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
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- 239000000203 mixture Substances 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000000235 small-angle X-ray scattering Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
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- GRFNSWBVXHLTCI-UHFFFAOYSA-N 1-ethenyl-4-[(2-methylpropan-2-yl)oxy]benzene Chemical compound CC(C)(C)OC1=CC=C(C=C)C=C1 GRFNSWBVXHLTCI-UHFFFAOYSA-N 0.000 description 1
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
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- 125000004432 carbon atom Chemical group C* 0.000 description 1
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- 238000000502 dialysis Methods 0.000 description 1
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- 238000010550 living polymerization reaction Methods 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 238000005949 ozonolysis reaction Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
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- 230000000717 retained effect Effects 0.000 description 1
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- 238000001797 two-dimensional small-angle X-ray scattering Methods 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
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- 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
- B01D71/80—Block polymers
-
- 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
- B01D67/0023—Organic membrane manufacture by inducing porosity into non porous precursor membranes
- B01D67/003—Organic membrane manufacture by inducing porosity into non porous precursor membranes by selective elimination of components, e.g. by leaching
- B01D67/0031—Organic membrane manufacture by inducing porosity into non porous precursor membranes by selective elimination of components, e.g. by leaching by elimination of at least one of the blocks of a block copolymer
-
- 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
- B01D71/28—Polymers of vinyl aromatic compounds
-
- 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
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/0061—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof characterized by the use of several polymeric components
-
- 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
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/26—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a solid phase from a macromolecular composition or article, e.g. leaching out
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2325/00—Details relating to properties of membranes
- B01D2325/14—Membrane materials having negatively charged functional groups
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2325/00—Details relating to properties of membranes
- B01D2325/16—Membrane materials having positively charged functional groups
-
- 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
- B01D71/24—Rubbers
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- 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
- C08J2201/00—Foams characterised by the foaming process
- C08J2201/04—Foams characterised by the foaming process characterised by the elimination of a liquid or solid component, e.g. precipitation, leaching out, evaporation
- C08J2201/046—Elimination of a polymeric phase
- C08J2201/0462—Elimination of a polymeric phase using organic solvents
-
- 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
- C08J2353/00—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
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- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Description
本実施例では、ブロックコポリマー(I)として、ポリイソプレン−ポリスチレン−ポリ2-ビニルピリジン(ISP−s)の三成分トリブロックコポリマーを用いた。以下にその合成方法を示す。
本実施例では、ポリマー(II)として、ポリ4-ヒドロキシスチレン(H−s)を用いた。以下にその合成方法を、図2に具体的な合成スキームを示す。
次に、上記のようにして形成したISP−sおよびH−sのそれぞれをTHFに溶解させて、濃度5重量%のISP−s溶液およびH−s溶液を作製した。次に、ISP−sが84重量%ならびにH−sが16重量%となるように両溶液を混合した後に、混合溶液を容器に流し込み、自然乾燥によりTHFを揮発、除去し、さらに真空下における乾燥(一日間)および熱処理(180℃、24時間)を経て、薄膜状の高分子体を形成した。なお、両溶液の混合比率、ならびに、ISP−sにおける各セグメントの体積分率および密度から算出したISP−sの各セグメントおよびH−sの体積比は、およそI(イソプレン):S(スチレン):P(2-ビニルピリジン)+H(4-ヒドロキシスチレン)=1:2:0.75であり、体積分率としては、I:S:P:H=0.255:0.553:0.052:0.140であった。
上記のように形成した高分子体および高分子微多孔体における相分離構造の確認および観察を、透過型電子顕微鏡(TEM)および小角X線散乱(SAXS)により実施した。TEM観察では、測定サンプルとして、I領域、S領域およびP/H領域間のコントラストが得られるように、オスミウム酸染色およびヨウ素染色を行った非常に薄い切片を、それぞれ準備した。また、SAXS測定は、線源にCuKα線を用い、カメラ長を980mm、測定時間を10時間として行った。
Claims (14)
- 互いに異なるモノマーユニットを有する3種以上のセグメントからなり、1つ以上の前記セグメントが、イオン結合および/または水素結合を形成しうる第1の官能基を備えるモノマーユニットからなり、前記セグメント間の非相容性に基づく相分離により、各々の前記セグメントからなる領域が互いに独立して連続する共連続構造が形成されるブロックコポリマー(I)と、
第1の官能基との間でイオン結合および/または水素結合を形成する第2の官能基をポリマー鎖の末端以外に有するポリマー(II)と、を、
熱溶融により混合した後に温度を低下させる、または、溶媒中において混合した後に溶媒を除去する、ことにより、
コポリマー(I)における前記1つ以上のセグメントとポリマー(II)とを、第1および第2の官能基の間に生じるイオン結合および/または水素結合により多点で会合させるとともに、前記相分離により、ポリマー(II)およびポリマー(II)と会合した前記セグメントからなる領域を含む前記共連続構造を有する高分子体を形成し、
該領域から、第1および第2の官能基の間のイオン結合および/または水素結合を弱めてポリマー(II)を除去することにより、該領域に対応した形状を有する連続した細孔を前記高分子体に形成する、高分子微多孔体の製造方法。 - コポリマー(I)が、互いに異なるモノマーユニットを有する3種のセグメントからなるブロックコポリマーである請求項1に記載の高分子微多孔体の製造方法。
- 1つの前記セグメントのみが第1の官能基を備える請求項1または2に記載の高分子微多孔体の製造方法。
- ポリマー(II)が、第2の官能基を有するモノマーユニットからなるホモポリマーである請求項1に記載の高分子微多孔体の製造方法。
- 第1および第2の官能基の組み合わせが、両官能基の間に水素結合が生じる組み合わせである請求項1に記載の高分子微多孔体の製造方法。
- 第1および第2の官能基の組み合わせが、窒素を含む官能基と、酸素を含む官能基との組み合わせである請求項1に記載の高分子微多孔体の製造方法。
- 第1および第2の官能基の組み合わせが、アザフェニル基、ジアルキルアミン基、シアノ基およびモルフォリン基から選ばれる少なくとも1種と、ヒドロキシフェニル基、スルホン酸基およびカルボキシル基から選ばれる少なくとも1種である請求項1に記載の高分子微多孔体の製造方法。
- 第1および第2の官能基の組み合わせが、アザフェニル基とヒドロキシフェニル基である請求項1に記載の高分子微多孔体の製造方法。
- コポリマー(I)が、(ポリイソプレン−ポリスチレン−ポリ2-ビニルピリジン)トリブロックコポリマーである請求項1に記載の高分子微多孔体の製造方法。
- ポリマー(II)が、ポリ(4-ヒドロキシスチレン)である請求項1に記載の高分子微多孔体の製造方法。
- 酸またはアルカリにより、第1および第2の官能基間のイオン結合および/または水素結合を弱める請求項1に記載の高分子微多孔体の製造方法。
- 前記酸またはアルカリが、有機酸または有機塩基である請求項11に記載の高分子微多孔体の製造方法。
- 請求項1〜12のいずれかに記載の高分子微多孔体の製造方法によって得た高分子微多孔体。
- 膜の双方の主面をつなぐ連続した細孔を有する高分子膜を備える分離膜であって、
前記高分子膜が、請求項13に記載の高分子微多孔体からなる分離膜。
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US (2) | US8338534B2 (ja) |
EP (1) | EP2108674A4 (ja) |
JP (1) | JP5058827B2 (ja) |
CN (1) | CN101583657B (ja) |
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JP5546719B2 (ja) * | 2007-03-28 | 2014-07-09 | 日東電工株式会社 | ミクロ相分離構造を有する高分子体の製造方法ならびにミクロ相分離構造を有する高分子体 |
WO2010114097A1 (ja) * | 2009-04-01 | 2010-10-07 | オーミケンシ株式会社 | スポンジの製造方法 |
WO2011036778A1 (ja) | 2009-09-25 | 2011-03-31 | 株式会社 東芝 | パターン形成方法 |
CN103781537B (zh) | 2011-08-22 | 2016-04-06 | 陶氏环球技术有限责任公司 | 由包含自组装嵌段共聚物的聚合物掺合物形成的复合膜 |
WO2013126238A1 (en) | 2012-02-21 | 2013-08-29 | Dow Global Technologies Llc | Composite membrane |
WO2013176267A1 (ja) * | 2012-05-25 | 2013-11-28 | 独立行政法人産業技術総合研究所 | 機能性樹脂及びその製造方法 |
EP2695669B1 (de) * | 2012-08-09 | 2016-10-12 | Helmholtz-Zentrum Geesthacht Zentrum für Material- und Küstenforschung GmbH | Membran mit isoporöser trennaktiver Schicht und Verfahren zur Herstellung einer Membran |
JP6330230B2 (ja) * | 2013-03-11 | 2018-05-30 | ユニヴァーシティー オブ ノートル ダム デュ ラック | マルチブロックコポリマー及び使用方法 |
JP2015073980A (ja) | 2013-10-11 | 2015-04-20 | 富士フイルム株式会社 | ガス分離膜およびガス分離膜モジュール |
WO2015056650A1 (ja) * | 2013-10-17 | 2015-04-23 | リンテック株式会社 | 断熱フィルム及びその製造方法 |
KR102596197B1 (ko) * | 2016-11-17 | 2023-11-02 | 테라포어 테크놀로지스, 인코포레이티드 | 고 분자량 친수성 첨가제를 포함하는 이소포러스 자기-조립 블록 공중합체 필름 및 이의 제조방법 |
CN106943895B (zh) * | 2017-04-07 | 2019-07-05 | 华东师范大学 | 一种丙酮刺激响应的柔性仿生双层高分子薄膜及制备方法和应用 |
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US4975469A (en) * | 1989-03-20 | 1990-12-04 | Amoco Corporation | Oriented porous polypropylene films |
JPH02279741A (ja) * | 1989-04-19 | 1990-11-15 | Mitsubishi Kasei Corp | 微多孔質膜の製造方法 |
JP2845571B2 (ja) * | 1990-05-17 | 1999-01-13 | ダイセル化学工業株式会社 | 極微多孔膜および極微多孔膜用組成物並びに極微多孔膜の製造方法 |
JP3245683B2 (ja) * | 1992-04-13 | 2002-01-15 | 科学技術振興事業団 | 三次元共連続ミクロ相分離構造を持つ多成分多相系高分子材料の製造方法 |
US5700902A (en) * | 1995-07-27 | 1997-12-23 | Circe Biomedical, Inc. | Block copolymers |
EP1007998A1 (en) * | 1997-02-11 | 2000-06-14 | Massachusetts Institute Of Technology | Polymeric photonic band gap materials |
JPH10330528A (ja) * | 1997-05-29 | 1998-12-15 | Res Dev Corp Of Japan | 金属・有機ポリマー複合体 |
JP3321392B2 (ja) | 1997-08-29 | 2002-09-03 | 科学技術振興事業団 | 二重構造連続多孔体とその製造方法 |
DE19829397A1 (de) * | 1998-07-01 | 2000-01-05 | Basf Ag | Verwendung mikrophasenseparierter Polymermischungen für die Herstellung von permeablen Membranen |
JP3940546B2 (ja) * | 1999-06-07 | 2007-07-04 | 株式会社東芝 | パターン形成方法およびパターン形成材料 |
JP3673179B2 (ja) * | 2001-02-16 | 2005-07-20 | 株式会社東芝 | パターン形成方法 |
DE20107778U1 (de) | 2001-05-08 | 2001-10-11 | B. Braun Melsungen Ag, 34212 Melsungen | Punktionskanüle |
DE102006045282C5 (de) * | 2006-09-22 | 2012-11-22 | Helmholtz-Zentrum Geesthacht Zentrum für Material-und Küstenforschung GmbH | Isoporöse Membran und Verfahren zu ihrer Herstellung |
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JP2008189910A (ja) | 2008-08-21 |
US20100036009A1 (en) | 2010-02-11 |
EP2108674A1 (en) | 2009-10-14 |
US8338534B2 (en) | 2012-12-25 |
US20120252912A1 (en) | 2012-10-04 |
CN101583657B (zh) | 2012-04-25 |
WO2008084778A1 (ja) | 2008-07-17 |
EP2108674A4 (en) | 2011-04-20 |
CN101583657A (zh) | 2009-11-18 |
US8357754B2 (en) | 2013-01-22 |
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