JP2016199733A - 親水性改質フッ素化膜(ii) - Google Patents
親水性改質フッ素化膜(ii) Download PDFInfo
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- JP2016199733A JP2016199733A JP2015209925A JP2015209925A JP2016199733A JP 2016199733 A JP2016199733 A JP 2016199733A JP 2015209925 A JP2015209925 A JP 2015209925A JP 2015209925 A JP2015209925 A JP 2015209925A JP 2016199733 A JP2016199733 A JP 2016199733A
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- Prior art keywords
- copolymer
- porous membrane
- hydrophilic
- formula
- porous
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- 239000000047 product Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000002352 surface water Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 229920000785 ultra high molecular weight polyethylene Polymers 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Abstract
Description
[0001]フルオロポリマー膜、例えば多孔質PTFE膜の機械的強度、耐薬品性又は化学的不活性、非付着性、優れた誘電特性、高温での熱的安定性、及び低摩擦係数を含む特性によって、フルオロポリマー膜は様々な用途に対して非常に魅力あるものになる。しかし、ある種の用途に対しては、その本質的な特性に影響することなく、PTFE表面を改質することが便益となるであろう。特定の用途に対する膜の適合性を改善するために、PTFE膜の表面特性及び化学的性質を改質することが試みられてきた。例えば、表面被覆、混合、例えば、膜を波長250〜450nmのUV放射に曝す広帯域紫外線放射又はBBUV、及びプラズマ処理などの高エネルギー表面改質、遊離基、及びオゾンエッチング、原子層蒸着、及び改質PTFE様ポリマーの合成などが試みられた。しかし、大抵の試みは、BBUV及びプラズマなどの高エネルギー処理に集中した。これら表面改質法の正確なメカニズムは報告されていないが、C−C結合の強度はF−F結合よりも約40%低いことが知られているため、結合切断による遊離基形成からもたらされると考えられる。遊離基の大部分が、C−C切断又はポリマー主鎖切断からもたらされている場合、PTFE膜の機械的安定性及び化学的安定性を損なう恐れがある。またプラズマ処理は、膜表面に限られるため、長時間では膜を不安定にさせることも知られている。
[0003]本発明は、多孔質フルオロポリマー支持体、及びコポリマーを含む被覆を含む、親水性複合多孔質膜であって、コポリマーが繰返し単位A及びBを含み、Aは次式のものであり、
Bは次式のものであり、
コポリマーは、ブロックコポリマー又はランダムコポリマーであり、
xは3〜約10であり、
n及びmは、コポリマーに存在する繰返し単位A及びBの数であり、1〜約1000の範囲であり、但し、nとmの合計が10以上であり、
コポリマーは、任意選択で架橋結合されている、親水性複合多孔質膜を提供する。
[0013]一実施形態によれば、本発明は、多孔質フルオロポリマー支持体、及びコポリマーを含む被覆を含む、親水性複合多孔質膜であって、コポリマーが繰返し単位A及びBを含み、Aは次式のものであり、
Bは次式のものであり、
式中、
コポリマーは、ブロックコポリマー又はランダムコポリマーであり、
xは3〜約10であり、
n及びmは、コポリマーに存在する繰返し単位A及びBの数であり、1〜約1000の範囲であり、但し、nとmの合計が10以上であり、
コポリマーは、任意選択で架橋結合されている、親水性複合多孔質膜を提供する。
Bは次式のものであり、
ここで、*は、キレート官能基又はイオン交換官能基の結合点であり、コポリマーは、ブロックコポリマー又はランダムコポリマーであり、xは3〜約10であり、n及びmは、コポリマーに存在する繰返し単位A及びBの数であり、1〜約1000の範囲であり、但し、nとmの合計が10以上であり、
コポリマーは、任意選択で架橋結合されている、親水性複合多孔質膜を提供する。
[0020]上記実施形態のコポリマーの例として、
が挙げられる。
がある。
(i)開環メタセシス重合(ROMP)触媒によって触媒させて、5−(モノメトキシトリエチレングリコール)ノルボルネン(NTEG)を重合して、ホモポリマー、ポリNTEGを得るステップと、
(ii)(i)で得られたホモポリマーの分子鎖末端で、ROMP触媒によって触媒させて、5−(パーフルオロヘキシル)ノルボルネン又は5−(パーフルオロデシル)ノルボルネンを逐次重合するステップとを含む、コポリマー、ポリ(NTEG−b−NPF6)又はポリ(NTEG−b−NPF10)を調製する方法を提供する。
Bは次式のものであるステップと、
コポリマーをメルカプト酢酸、メルカプトエチルスルホン酸塩、又はチオグリセロールと反応させるステップと
を含む、上記のイオン交換官能基又はキレート官能基を有するコポリマーを調製する方法をさらに提供する。
[0044](i)多孔質フルオロポリマー支持体を用意するステップと、
[0045](ii)上記の溶媒及びコポリマーを含む溶液で、多孔質フルオロポリマー支持体を被覆するステップと、
[0046](iii)(ii)からの被覆された支持体を乾燥させて、溶液から溶媒の少なくとも一部を取り除くステップと、任意選択で、
[0047](iv)被覆された膜に存在するコポリマーを架橋結合させるステップと
を含む、多孔質フルオロカーボン支持体を親水性改質する方法をさらに提供する。
[0063]材料:以下の材料を購入し、そのまま使用した。
[0066]本実施例は、ジクロロ[1,3−ビス(2,4,6−トリメチルフェニル)−2−イミダゾリジニリデン](ベンジリデン)ビス(3−ブロモピリジン)ルテニウム(II)(G3)触媒の調製を説明する。
[0068]本実施例は、本発明の一実施形態の、ホモポリマー及びコポリマーの、ゲル浸透クロマトグラフィーによる特性決定を説明する。
[0070]移動相:ジクロロメタン(DCM)
[0071]移動相温度:30℃
[0072]UV波長:245nm
[0073]使用するカラム:3本のPSS SVD Lux分析カラム(スチレン−ジビニルベンゼンコポリマー網目構造)、直径5μm、孔径が1000A、100,000A、及び1,000,000Aであるビーズを固定相として有するカラム、及びガードカラム
[0074]流量:1mL/分
[0075]GPCシステム:UV検出器及びRI検出器を備える、Waters HPLC Alliance e2695システム
[0076]MALSシステム:664.5nmのレーザーを作動させる、8個の検出器を備えるDAWN HELEOS8システム
[0077]本実施例は、本発明の一実施形態のNPF6モノマーを調製する工程を説明する。
[0080]本実施例は、本発明の一実施形態のNPF10モノマーを調製する工程を説明する。
[0083]本実施例は、トリエチレングリコールモノメチルエーテルトシラート(TEG−OTs)を調製する工程を説明する。
[0089]本実施例は、本発明の一実施形態の、コポリマーの合成及び特性を説明する。
1H−NMR(300MHz,CDCl3):δ(ppm) 6.0〜6.35(s,広幅)、5.5〜6.0(s,広幅)、4.5〜5.2(s,広幅)、4.3〜4.5(s,広幅)、3.5〜3.8(m,広幅)、3.0〜3.3(s,広幅、2.0〜2.4(s,広幅)、1.5〜1.7(s,広幅)、1.0〜1.3(s)。
[0095]本実施例は、ポリ(NTEG−b−NPF6)コポリマーをUV架橋結合させる方法、及び本発明の一実施形態の、コポリマーの特性を説明する。
[0098]本実施例は、本発明の一実施形態の、他のコポリマーの合成及び特性を説明する。
[0106]本実施例は、本発明の一実施形態の、フルオロポリマー膜内のコポリマー、ポリ(NTEG−r−NPF6)を架橋結合させる方法を説明する。被覆工程を図4に示す。得られた結果を表4に示す。
[0108]本実施例は、本発明の一実施形態の、他のコポリマーの合成及び特性を説明する。
[0119]本実施例は、本発明の一実施形態のキレート特性及び/又はイオン交換特性をもたらすために、コポリマー、ポリ(NTEG−b−NPF6)を化学的改質する方法を説明する。
ポリ(NTEG−b−NPF6)(0.99g)、チオグリコール酸(MAcOH、0.9g)、及びAIBN(79.8mg)をTHF33mlに溶解させ、窒素下、55℃で26時間反応させた。反応混合物を水中に注ぎ込んだ。得られた沈殿物をTHFに再度溶解させ、再びヘプタンから沈殿させて、暗褐色の固体を得た。
ポリ(NTEG−b−NPF6)(0.99g)、2−メルカプトエタンスルホン酸ナトリウム(MeSNa、1.6g)及びAIBN(79.8mg)をTHF33mlに溶解させ、窒素下、55℃で26時間反応させた。反応混合物を水に注ぎ込んだ。得られた沈殿物を、THFに再度溶解させ、再びヘプタンから沈殿させて、黄色がかった固体を得た。
ポリ(NTEG−b−NPF6)(0.99g)、1−チオグリセロール(1.05g)、及びAIBN(79.8mg)をTHF33mlに溶解させ、窒素下、55℃で26時間反応させた。反応混合物を水に注ぎ込んだ。得られた沈殿物を、THFに再度溶解させ、再びヘプタンから沈殿させて、くすんだ白色の固体を得た。
Claims (17)
- 多孔質フルオロポリマー支持体、及びコポリマーを含む被覆を含む、親水性複合多孔質膜であって、コポリマーが繰返し単位A及びBを含み、Aは次式のものであり、
Bは次式のものであり、
コポリマーは、ブロックコポリマー又はランダムコポリマーであり、
xは3〜約10であり、
n及びmは、コポリマーに存在する繰返し単位A及びBの数であり、1〜約1000の範囲であり、但し、nとmの合計が10以上であり、
コポリマーは、任意選択で架橋結合されている、親水性複合多孔質膜。 - コポリマーが、アリール基及びアルコキシ基から選択される、分子鎖末端基を有する、請求項1に記載の親水性複合多孔質膜。
- コポリマーが、以下の式
の1つである、請求項1又は2に記載の親水性複合多孔質膜。 - 次式のブロックコポリマーである、
請求項3に記載の親水性複合多孔質膜。 - 次式のランダムコポリマーである、
請求項3に記載の親水性複合多孔質膜。 - 多孔質フルオロポリマー支持体、及びコポリマーを含む被覆を含む、親水性複合多孔質膜であって、コポリマーが、繰返し単位A及びB、並びに1つ又は複数の繰返し単位Aに結合した1つ又は複数のキレート官能基又はイオン交換官能基を含み、Aは次式のものであり、
Bは次式のものであり、
ここで、
*は、キレート官能基又はイオン交換官能基の結合点であり、
コポリマーは、ブロックコポリマー又はランダムコポリマーであり、
xは3〜約10であり、
n及びmは、コポリマーに存在する繰返し単位A及びBの数であり、1〜約1000の範囲であり、但し、nとmの合計が10以上であり、
コポリマーは、任意選択で架橋結合されている、親水性複合多孔質膜。 - コポリマーが、アリール基及びアルコキシ基から選択される分子鎖末端基を有する、請求項6に記載の親水性複合多孔質膜。
- キレート官能基又はイオン交換官能基が、カルボキシルアルキルチオ、スルホニルアルキルチオ、及びグリセリルチオの各基、並びにその組み合わせから選択される、請求項6又は7に記載の親水性複合多孔質膜。
- コポリマーが次式のものである、
請求項6〜8のいずれか一項に記載の親水性複合多孔質膜。 - (i)多孔質フルオロポリマー支持体を用意するステップと、
(ii)溶媒及びコポリマーを含む溶液で、多孔質フルオロポリマー支持体を被覆するステップであって、コポリマーは繰返し単位A及びBを有し、Aは次式のものであり、
Bは次式のものであり、
コポリマーは、ブロックコポリマー又はランダムコポリマーであり、
xは3〜約10であり、
n及びmは、コポリマーに存在する繰返し単位A及びBの数であり、1〜約1000の範囲であり、但し、nとmの合計が10以上である、ステップと、
(iii)(ii)からの被覆支持体を乾燥させて、前記コポリマーを含む溶液から溶媒の少なくとも一部を取り除くステップと、任意選択で、
(iv)被覆膜に存在する前記コポリマーを架橋結合させるステップと
を含む、多孔質フルオロポリマー支持体を親水性改質する方法。 - コポリマーが次式のものである、
請求項10に記載の多孔質フルオロポリマー支持体を親水性改質する方法。 - (i)多孔質フルオロポリマー支持体を用意するステップと、
(ii)溶媒及びコポリマーを含む溶液で、多孔質フルオロポリマー支持体を被覆するステップであって、コポリマーは繰返し単位A及びB、並びに1つ又は複数の繰返し単位Aに結合した、1種又は複数の、キレート官能基又はイオン交換官能基を有し、Aは次式のものであり、
Bは次式のものであり、
式中、
*は、キレート官能基又はイオン交換官能基の結合点であり、
コポリマーは、ブロックコポリマー又はランダムコポリマーであり、
xは3〜約10であり
n及びmは、コポリマーに存在する繰返し単位A及びBの数であり、1〜約1000の範囲であり、但し、nとmの合計が10以上である、ステップと、
(iii)(ii)から被覆支持体を乾燥させて、前記コポリマーを含む溶液から、溶媒の少なくとも一部を取り除くステップと、任意選択で、
(iv)被覆膜中に存在する前記コポリマーを架橋結合させるステップと
を含む、多孔質フルオロポリマー支持体を親水性改質する方法。 - コポリマーが次式のものである、
請求項12に記載の多孔質フルオロポリマー支持体を親水性改質する方法。 - 請求項10〜13のいずれか一項に記載の多孔質フルオロポリマー支持体を親水性改質する方法によって製造される、親水性多孔質膜。
- 前記多孔質フルオロポリマー支持体が、PTFE、PVDF、PVF(ポリフッ化ビニル)、PCTFE(ポリクロロトリフルオロエチレン)、FEP(フッ素化エチレンプロピレン)、ETFE(ポリエチレンテトラフルオロエチレン)、ECTFE(ポリ(エチレンクロロトリフルオロエチレン))、PFPE(パーフルオロポリエーテル)、PFSA(パーフルオロスルホン酸)、及びパーフルオロポリオキセタンから選択される、請求項1〜9のいずれか一項に記載の親水性複合多孔質膜、又は請求項14に記載の親水性改質多孔質フルオロポリマー膜。
- 請求項1〜9、14若しくは15のいずれか一項に記載の親水性多孔質膜に流体を通すステップを含む、流体を濾過する方法。
- 平面、平坦なシート、ひだ状、管状、らせん状、又は中空繊維の形状に形成される、請求項1〜9、14若しくは15のいずれか一項に記載の親水性複合多孔質膜。
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20200113262A (ko) | 2018-03-22 | 2020-10-06 | 후지필름 가부시키가이샤 | 여과 장치, 정제 장치, 약액의 제조 방법 |
JP2021519843A (ja) * | 2018-03-27 | 2021-08-12 | ジョージア テック リサーチ コーポレイション | アニオン交換膜並びにその製造方法及び使用方法 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH08283447A (ja) * | 1995-04-14 | 1996-10-29 | Sumitomo Electric Ind Ltd | 親水性四弗化エチレン樹脂多孔質膜及びその製造方法 |
JP2010059427A (ja) * | 2001-04-27 | 2010-03-18 | Millipore Corp | 新規なコート膜およびその他の製品 |
JP2011131208A (ja) * | 2009-11-25 | 2011-07-07 | Fujifilm Corp | 結晶性ポリマー微孔性膜及びその製造方法、並びに濾過用フィルタ |
Family Cites Families (61)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5833886B2 (ja) | 1976-09-14 | 1983-07-22 | 東ソー株式会社 | 陽イオン交換膜並びにその製法 |
US4975507A (en) | 1987-05-27 | 1990-12-04 | Monsanto Company | Cyclopentanedioxocarbonyl vinylene polymers |
DE69017197T2 (de) | 1990-05-18 | 1995-09-14 | Japan Gore Tex Inc | Hydrophile poröse Membrane aus Fluoropolymer. |
US5294493A (en) | 1990-12-07 | 1994-03-15 | E. I. Du Pont De Nemours And Company | Polymeric films for second order nonlinear optics |
US5200470A (en) | 1990-12-19 | 1993-04-06 | Monsanto Company | Norbornene dicarboxy phenylimide polymers |
US5117327A (en) | 1990-12-19 | 1992-05-26 | Monsanto Company | Norbornene dicarboximide polymer dielectric devices |
JP3077113B2 (ja) | 1991-03-15 | 2000-08-14 | ジャパンゴアテックス株式会社 | 白金族または白金族合金をめっきした微細多孔質フッ素樹脂材およびその製造法 |
US5219662A (en) | 1991-05-23 | 1993-06-15 | E. I. Du Pont De Nemours And Company | Biocompatible polyurethanes by treatment with polyoxazoline block copolymers |
JP3149970B2 (ja) | 1991-08-06 | 2001-03-26 | ジャパンゴアテックス株式会社 | 散気材及びそれを用いたガスの散気方法 |
US5266076A (en) | 1992-01-24 | 1993-11-30 | E. I. Du Pont De Nemours And Company | Fluorinated finishes for aramids |
US5418277A (en) | 1994-04-26 | 1995-05-23 | E. I. Du Pont De Nemours And Company | Aqueous ink jet inks containing fluorinated polymers |
US6254978B1 (en) | 1994-11-14 | 2001-07-03 | W. L. Gore & Associates, Inc. | Ultra-thin integral composite membrane |
JP4267073B2 (ja) | 1996-10-09 | 2009-05-27 | 日本ゼオン株式会社 | ノルボルネン系重合体組成物を溶媒に溶解させた溶液 |
EP0922486B1 (en) | 1996-12-02 | 2006-08-23 | Fuji Photo Film Co., Ltd. | Microporous membranes and process for the production thereof |
US6126825A (en) | 1996-12-02 | 2000-10-03 | Fuji Photo Film Co., Ltd. | Microporous membrane and process for the production thereof |
US6080826A (en) | 1997-01-06 | 2000-06-27 | California Institute Of Technology | Template-directed ring-closing metathesis and ring-opening metathesis polymerization of functionalized dienes |
DE69921718T2 (de) | 1998-04-01 | 2005-12-22 | Solvay Solexis, Inc., Wilmington | Verträgliche Mischungen aus Polyvinylidenfluorid und aromatischem Polyimid |
TW558559B (en) | 1998-06-30 | 2003-10-21 | Ind Tech Res Inst | An oxygen atom-containing heterocyclic dione polymer and photosensitive composition comprising the same |
GB2346095B (en) | 1999-01-21 | 2000-12-13 | Membrane Extraction Tech Ltd | Membrane extraction process |
GB9916235D0 (en) | 1999-07-09 | 1999-09-15 | Univ Durham | Process for polymerisation of olefins and novel polymerisable olefins |
WO2001014446A1 (fr) | 1999-08-25 | 2001-03-01 | Zeon Corporation | Polymeres de norbornene par ouverture de cycle, produits de leur hydrogenation et procedes de productions de ces deux types de polymeres |
US6436476B1 (en) | 2000-02-14 | 2002-08-20 | Owens Corning Fiberglas Technology, Inc. | Polyolefin fiber-reinforced composites using a fiber coating composition compatible with romp catalysts |
US7034096B2 (en) | 2002-02-19 | 2006-04-25 | California Institute Of Technology | Ring-expansion of cyclic olefins metathesis reactions with an acyclic diene |
EP1509635A4 (en) | 2002-05-09 | 2009-09-30 | Massachusetts Inst Technology | PREPARATION OF ASYMMETRIC MEMBRANES BY CHEMICAL VAPOR DEPOSITION WITH HOT FILAMENT |
JP2005029527A (ja) | 2003-07-09 | 2005-02-03 | Central Glass Co Ltd | フッ素系環状化合物、フッ素系重合性単量体、フッ素系高分子化合物、並びにそれを用いたレジスト材料及びパターン形成方法 |
US7132565B2 (en) | 2004-02-13 | 2006-11-07 | National Taiwan University Of Science & Technology | Norbornene compounds with cross-linkable groups and their derivatives |
US7514499B2 (en) | 2004-11-09 | 2009-04-07 | E. I. Du Pont De Nemours And Company | Ring opening polymerization of cyclic amides using N-heterocyclic carbene catalysts |
EP1826221A4 (en) | 2004-12-15 | 2008-03-05 | Univ Nihon | PROCESS FOR PREPARING (CO) POLYMERISATE BASED ON NORBORNENE |
GB0428172D0 (en) | 2004-12-23 | 2005-01-26 | Ici Plc | Olefin metathesis polymerisation |
US20060205301A1 (en) | 2005-03-11 | 2006-09-14 | Bha Technologies, Inc. | Composite membrane having hydrophilic properties and method of manufacture |
JPWO2007034653A1 (ja) | 2005-09-22 | 2009-03-19 | 日本ゼオン株式会社 | ノルボルネン化合物付加重合体、その製造方法、該重合体からなる成形品、及びその用途 |
US20070087245A1 (en) | 2005-10-14 | 2007-04-19 | Fuller Timothy J | Multilayer polyelectrolyte membranes for fuel cells |
US7631768B2 (en) | 2005-11-04 | 2009-12-15 | General Electric Company | Membrane and associated method |
TW200736311A (en) | 2006-01-30 | 2007-10-01 | Zeon Corp | Film comprising norbornene compound addition polymer |
WO2007105653A1 (ja) | 2006-03-10 | 2007-09-20 | Asahi Glass Co., Ltd. | 含フッ素エポキシ化合物の開環重合による含フッ素重合体の製造方法 |
TW200804479A (en) | 2006-05-23 | 2008-01-16 | Zeon Corp | Oriented film of addition polymer of norbornene compound alone, process for producing the same and use thereof |
WO2008048536A2 (en) | 2006-10-17 | 2008-04-24 | Firestone Polymers, Llc | Elastomers, process for preparation, and uses thereof |
WO2008068897A1 (ja) | 2006-12-05 | 2008-06-12 | Mitsui Chemicals, Inc. | 環状オレフィン系重合体組成物、その用途、環状オレフィン系重合体 |
EP1942125A1 (en) | 2006-12-20 | 2008-07-09 | 3M Innovative Properties Company | Compositions curable by ring opening metathesis polymerarization at low temperatures and their application in the dental field |
TWI347955B (en) | 2007-07-19 | 2011-09-01 | Univ Nat Taiwan Science Tech | Norbornene monomers with fluorene group and polymer material thereof |
TWI357416B (en) | 2007-08-08 | 2012-02-01 | Univ Nat Taiwan Science Tech | Norbornene monomers with epoxy group and polymer m |
US20090191357A1 (en) * | 2008-01-25 | 2009-07-30 | General Electric Company | Processes for forming permanent hydrophilic porous coatings onto a substrate, and porous membranes thereof |
US8215496B2 (en) | 2008-01-28 | 2012-07-10 | Promerus Llc | Polynorbornene pervaporation membrane films, preparation and use thereof |
US8223472B1 (en) | 2008-11-14 | 2012-07-17 | Sandia Corporation | Norbornylene-based polymer systems for dielectric applications |
US20110266220A1 (en) | 2009-01-07 | 2011-11-03 | Cms Technologies Holdings, Inc. | Separations with highly selective fluoropolymer membranes |
EP2397217A4 (en) * | 2009-02-16 | 2013-07-31 | Sumitomo Elec Fine Polymer Inc | POROUS MULTILAYER FILTER AND MANUFACTURING METHOD THEREFOR |
WO2010101882A1 (en) | 2009-03-02 | 2010-09-10 | Isp Investments Inc. | Thermosetting ring-opening metathesis polymerization materials with thermally degradable linkages |
US8283410B2 (en) | 2009-03-30 | 2012-10-09 | Isp Investments Inc. | Ring-opening metathesis polymerization of norbornene and oxanorbornene moieties and uses thereof |
US8143369B2 (en) | 2009-06-02 | 2012-03-27 | International Business Machines Corporation | Polymers bearing pendant pentafluorophenyl ester groups, and methods of synthesis and functionalization thereof |
US8207351B2 (en) | 2010-04-30 | 2012-06-26 | International Business Machines Corporation | Cyclic carbonyl compounds with pendant carbonate groups, preparations thereof, and polymers therefrom |
US8906999B2 (en) | 2011-02-17 | 2014-12-09 | Ccp Composites Us Llc | Styrene-free unsaturated polyester |
WO2012124745A1 (ja) | 2011-03-14 | 2012-09-20 | 日本ゴア株式会社 | 水処理フィルター用濾材およびその製造方法 |
US20130108845A1 (en) | 2011-10-31 | 2013-05-02 | YitHong Tee | Oleophobic membrane structures including a porous polymeric coating |
CN102423642B (zh) | 2011-12-13 | 2013-12-11 | 北京碧水源科技股份有限公司 | 一种多孔膜表面的永久亲水改性方法与采用所述方法得到的多孔膜 |
US9206271B2 (en) | 2012-03-25 | 2015-12-08 | Wisconsin Alumni Research Foundation | Fully backbone degradable and functionalizable polymers derived from the ring-opening metathesis polymerization (ROMP) |
CN104540798B (zh) * | 2012-08-07 | 2016-12-21 | 住友电木株式会社 | 环烷基降冰片烯单体、衍生自其的聚合物和它们在渗透蒸发中的用途 |
US20140231340A1 (en) | 2013-02-15 | 2014-08-21 | Pall Corporation | Composite including ptfe membrane |
MY191997A (en) | 2013-02-27 | 2022-07-22 | Materia Inc | Metal carbene olefin metathesis two catalyst composition |
JP6075452B2 (ja) | 2013-06-26 | 2017-02-08 | ダイキン工業株式会社 | 組成物、高分子多孔質膜及び親水化剤 |
US9441078B2 (en) * | 2014-05-30 | 2016-09-13 | Pall Corporation | Self-assembling polymers—I |
US9169361B1 (en) | 2014-05-30 | 2015-10-27 | Pall Corporation | Self-assembling polymers—VI |
-
2015
- 2015-03-31 US US14/675,547 patent/US9724650B2/en active Active
- 2015-10-26 JP JP2015209925A patent/JP6060448B2/ja active Active
- 2015-10-27 SG SG10201508869VA patent/SG10201508869VA/en unknown
- 2015-10-29 TW TW104135573A patent/TWI585132B/zh active
- 2015-10-30 CN CN201511035780.4A patent/CN106009020B/zh active Active
- 2015-10-30 KR KR1020150151710A patent/KR101780380B1/ko active IP Right Grant
- 2015-10-30 EP EP15192304.2A patent/EP3075763B1/en active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH08283447A (ja) * | 1995-04-14 | 1996-10-29 | Sumitomo Electric Ind Ltd | 親水性四弗化エチレン樹脂多孔質膜及びその製造方法 |
JP2010059427A (ja) * | 2001-04-27 | 2010-03-18 | Millipore Corp | 新規なコート膜およびその他の製品 |
JP2011131208A (ja) * | 2009-11-25 | 2011-07-07 | Fujifilm Corp | 結晶性ポリマー微孔性膜及びその製造方法、並びに濾過用フィルタ |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20200113262A (ko) | 2018-03-22 | 2020-10-06 | 후지필름 가부시키가이샤 | 여과 장치, 정제 장치, 약액의 제조 방법 |
KR20230022451A (ko) | 2018-03-22 | 2023-02-15 | 후지필름 가부시키가이샤 | 여과 장치, 정제 장치, 약액의 제조 방법 |
US11759749B2 (en) | 2018-03-22 | 2023-09-19 | Fujifilm Corporation | Filtering device, purification device, and method for manufacturing chemical liquid |
JP2021519843A (ja) * | 2018-03-27 | 2021-08-12 | ジョージア テック リサーチ コーポレイション | アニオン交換膜並びにその製造方法及び使用方法 |
US12030981B2 (en) | 2018-03-27 | 2024-07-09 | Georgia Tech Research Corporation | Anion-exchange membranes and methods of making and using the same |
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US20160288059A1 (en) | 2016-10-06 |
US9724650B2 (en) | 2017-08-08 |
EP3075763B1 (en) | 2017-12-13 |
JP6060448B2 (ja) | 2017-01-18 |
KR20160117132A (ko) | 2016-10-10 |
TWI585132B (zh) | 2017-06-01 |
TW201634538A (zh) | 2016-10-01 |
EP3075763A1 (en) | 2016-10-05 |
CN106009020B (zh) | 2019-03-22 |
KR101780380B1 (ko) | 2017-09-21 |
CN106009020A (zh) | 2016-10-12 |
SG10201508869VA (en) | 2016-10-28 |
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