JP5925409B2 - 熱硬化性樹脂多孔シートの製造方法、熱硬化性樹脂多孔シート、及びそれを用いた複合半透膜 - Google Patents
熱硬化性樹脂多孔シートの製造方法、熱硬化性樹脂多孔シート、及びそれを用いた複合半透膜 Download PDFInfo
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- JP5925409B2 JP5925409B2 JP2009242653A JP2009242653A JP5925409B2 JP 5925409 B2 JP5925409 B2 JP 5925409B2 JP 2009242653 A JP2009242653 A JP 2009242653A JP 2009242653 A JP2009242653 A JP 2009242653A JP 5925409 B2 JP5925409 B2 JP 5925409B2
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- epoxy resin
- porous sheet
- thermosetting resin
- porogen
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- 230000005540 biological transmission Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- MRNZSTMRDWRNNR-UHFFFAOYSA-N bis(hexamethylene)triamine Chemical compound NCCCCCCNCCCCCCN MRNZSTMRDWRNNR-UHFFFAOYSA-N 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- BZFATHSFIGBGOT-UHFFFAOYSA-N butane-1,1,1-tricarbonyl chloride Chemical compound CCCC(C(Cl)=O)(C(Cl)=O)C(Cl)=O BZFATHSFIGBGOT-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
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- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
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- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
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- XWALRFDLDRDCJG-UHFFFAOYSA-N cyclobutane-1,1,2,2-tetracarbonyl chloride Chemical compound ClC(=O)C1(C(Cl)=O)CCC1(C(Cl)=O)C(Cl)=O XWALRFDLDRDCJG-UHFFFAOYSA-N 0.000 description 1
- LXLCHRQXLFIZNP-UHFFFAOYSA-N cyclobutane-1,1-dicarbonyl chloride Chemical compound ClC(=O)C1(C(Cl)=O)CCC1 LXLCHRQXLFIZNP-UHFFFAOYSA-N 0.000 description 1
- PBWUKDMYLKXAIP-UHFFFAOYSA-N cyclohexane-1,1,2-tricarbonyl chloride Chemical compound ClC(=O)C1CCCCC1(C(Cl)=O)C(Cl)=O PBWUKDMYLKXAIP-UHFFFAOYSA-N 0.000 description 1
- MLCGVCXKDYTMRG-UHFFFAOYSA-N cyclohexane-1,1-dicarbonyl chloride Chemical compound ClC(=O)C1(C(Cl)=O)CCCCC1 MLCGVCXKDYTMRG-UHFFFAOYSA-N 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- GEQHKFFSPGPGLN-UHFFFAOYSA-N cyclohexane-1,3-diamine Chemical compound NC1CCCC(N)C1 GEQHKFFSPGPGLN-UHFFFAOYSA-N 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- DCXMNNZFVFSGJX-UHFFFAOYSA-N cyclopentane-1,1,2,2-tetracarbonyl chloride Chemical compound ClC(=O)C1(C(Cl)=O)CCCC1(C(Cl)=O)C(Cl)=O DCXMNNZFVFSGJX-UHFFFAOYSA-N 0.000 description 1
- JREFGECMMPJUHM-UHFFFAOYSA-N cyclopentane-1,1,2-tricarbonyl chloride Chemical compound ClC(=O)C1CCCC1(C(Cl)=O)C(Cl)=O JREFGECMMPJUHM-UHFFFAOYSA-N 0.000 description 1
- YYLFLXVROAGUFH-UHFFFAOYSA-N cyclopentane-1,1-dicarbonyl chloride Chemical compound ClC(=O)C1(C(Cl)=O)CCCC1 YYLFLXVROAGUFH-UHFFFAOYSA-N 0.000 description 1
- CRMQURWQJQPUMY-UHFFFAOYSA-N cyclopropane-1,1,2-tricarbonyl chloride Chemical compound ClC(=O)C1CC1(C(Cl)=O)C(Cl)=O CRMQURWQJQPUMY-UHFFFAOYSA-N 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
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- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
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- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
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- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
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- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- OCIDXARMXNJACB-UHFFFAOYSA-N n'-phenylethane-1,2-diamine Chemical compound NCCNC1=CC=CC=C1 OCIDXARMXNJACB-UHFFFAOYSA-N 0.000 description 1
- ZETYUTMSJWMKNQ-UHFFFAOYSA-N n,n',n'-trimethylhexane-1,6-diamine Chemical compound CNCCCCCCN(C)C ZETYUTMSJWMKNQ-UHFFFAOYSA-N 0.000 description 1
- WUQGUKHJXFDUQF-UHFFFAOYSA-N naphthalene-1,2-dicarbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(C(=O)Cl)=CC=C21 WUQGUKHJXFDUQF-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- LSHSZIMRIAJWRM-UHFFFAOYSA-N oxolane-2,3-dicarbonyl chloride Chemical compound ClC(=O)C1CCOC1C(Cl)=O LSHSZIMRIAJWRM-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- MTAAPVANJNSBGV-UHFFFAOYSA-N pentane-1,1,1-tricarbonyl chloride Chemical compound CCCCC(C(Cl)=O)(C(Cl)=O)C(Cl)=O MTAAPVANJNSBGV-UHFFFAOYSA-N 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
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- GHAIYFTVRRTBNG-UHFFFAOYSA-N piperazin-1-ylmethanamine Chemical compound NCN1CCNCC1 GHAIYFTVRRTBNG-UHFFFAOYSA-N 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
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- 229940113115 polyethylene glycol 200 Drugs 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
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- 229920001155 polypropylene Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
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- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
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- 238000002459 porosimetry Methods 0.000 description 1
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- VLRIRAGKJXODNO-UHFFFAOYSA-N propane-1,1,1-tricarbonyl chloride Chemical compound CCC(C(Cl)=O)(C(Cl)=O)C(Cl)=O VLRIRAGKJXODNO-UHFFFAOYSA-N 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
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- 229940083575 sodium dodecyl sulfate Drugs 0.000 description 1
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- 239000007787 solid Substances 0.000 description 1
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- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
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- 150000005846 sugar alcohols Polymers 0.000 description 1
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- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
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- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
Images
Classifications
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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Description
(エポキシ樹脂多孔シートの空孔率及び平均孔径の測定)
エポキシ樹脂多孔シートの空孔率及び平均孔径は、水銀圧入法により、(株)島津製作所製オートポア9520型装置にて測定した。なお、平均孔径は、初期圧7kPaの条件のメディアン径を採用した。
作製した平膜状の複合半透膜を所定の形状、サイズに切断し、平膜評価用のセルにセットする。約1500mg/LのNaClを含みかつNaOHを用いてpH6.5〜7.5に調整した水溶液を25℃で膜の供給側と透過側に1.5MPaの差圧を与えて膜に接触させる。この操作によって得られた透過水の透過速度および電導度を測定し、透過流束(m3/m2・d)および塩阻止率(%)を算出した。塩阻止率は、NaCl濃度と水溶液電導度の相関(検量線)を事前に作成し、それらを用いて下式により算出した。
塩阻止率(%)={1−(透過液中のNaCl濃度[mg/L])/(供給液中のNaCl濃度[mg/L])}×100
(エポキシ樹脂多孔シートの作製)
ビスフェノールA型エポキシ樹脂(ジャパンエポキシレジン(株)、エピコート828)139重量部、ビスフェノールA型エポキシ樹脂(ジャパンエポキシレジン(株)、エピコート1010)93.2重量部、ビス(4−アミノシクロヘキシル)メタン52重量部、及びポリエチレングリコール200(三洋化成(株))500重量部を容器に入れ、スリーワンモーターを用いて400rpmで15分間撹拌してエポキシ樹脂組成物を得た。
調製したエポキシ樹脂組成物を円筒状モールド(外径35cm、内径10.5cm)内に高さ30cmまで充填して25℃で12時間室温硬化し、さらに130℃で18時間反応硬化させて円筒状樹脂ブロックを作製した。その後、該ブロックを円筒軸を中心に回転させながら切削装置(東芝機械社製)を用いて、その表面を厚さ150μmで連続的にスライスし、長尺状のエポキシ樹脂シート(長さ:150m)を得た。そして、エポキシ樹脂シートを水中に12時間浸漬してポリエチレングリコールを除去してエポキシ樹脂多孔シートを得た。その後、エポキシ樹脂多孔シートを50℃の乾燥機内で約4時間乾燥させた。乾燥後のエポキシ樹脂多孔シートの厚さは145μmであり、空孔率は45%、平均孔径は0.106μmであった。
m−フェニレンジアミン3重量%、トリエチルアミン3重量%、及びカンファースルホン酸6重量%を含有するアミン水溶液を前記エポキシ樹脂多孔シート上に塗布し、その後余分なアミン水溶液をワイピング除去することにより水溶液被覆層を形成した。次に、前記水溶液被覆層の表面にトリメシン酸クロライド0.2重量%を含有するイソオクタン溶液を塗布した。その後、余分な溶液を除去し、さらに120℃の熱風乾燥機中で3分間保持して、エポキシ樹脂多孔シート上にポリアミド系樹脂を含むスキン層を形成して複合半透膜を作製した。作製した複合半透膜を用いて上記透過試験を行った。透過試験の結果、塩阻止率は99.0(%)、透過流束は0.9(m3/m2・d)であった。
60℃で3時間反応硬化させ、その後130℃で15時間反応硬化させて円筒状樹脂ブロックを作製した以外は実施例1と同様の方法でエポキシ樹脂多孔シートを作製した。乾燥後のエポキシ樹脂多孔シートの厚さは148μmであり、空孔率は48%、平均孔径は0.08μmであった。該エポキシ樹脂多孔シートを用いた以外は実施例1と同様の方法で複合半透膜を作製し、上記透過試験を行った。透過試験の結果、塩阻止率及び透過流束は実施例1と同等であった。
60℃で3時間反応硬化させ、その後130℃で13時間反応硬化させ、さらに160℃で2時間反応硬化させて円筒状樹脂ブロックを作製した以外は実施例1と同様の方法でエポキシ樹脂多孔シートを作製した。乾燥後のエポキシ樹脂多孔シートの厚さは141μmであり、空孔率は42%、平均孔径は0.09μmであった。該エポキシ樹脂多孔シートを用いた以外は実施例1と同様の方法で複合半透膜を作製し、上記透過試験を行った。透過試験の結果、塩阻止率及び透過流束は実施例1と同等であった。
(エポキシ樹脂多孔シートの作製)
5Lのステンレス容器の内側に離型剤(ナガセケムテックス製、QZ−13)を薄く塗布し、該ステンレス容器を40〜100℃に設定した乾燥機中で乾燥させた。ビスフェノールA型エポキシ樹脂(ジャパンエポキシレジン(株)社製、商品名「jER827」)1094.6g、ビスフェノールA型エポキシ樹脂(ジャパンエポキシレジン(株)社製、商品名「jER1001」)156.4g、及びビスフェノールA型エポキシ樹脂(ジャパンエポキシレジン(株)社製、商品名「jER1009」)312.8gをポリエチレングリコール(三洋化成(株)製、商品名「PEG200」)3087.2gに溶解させてエポキシ樹脂/ポリエチレングリコール溶液を調製した。そして、調製したエポキシ樹脂/ポリエチレングリコール溶液を前記ステンレス容器内に加えた。その後、4,4’−ジシクロへキシルジアミン(DKSH社製、商品名「PACM−20」)349gを前記ステンレス容器内に加えた。スリーワンモータを用いて、アンカー翼で300rpmにて30分撹拌した。その後、真空盤(AZONE VZ型)を用いて、約0.1MPaにて泡がなくなるまで真空脱泡した。約2時間放置後、再度スリーワンモータを用いて約30分撹拌し、再度真空脱泡した。その後、25℃で24時間放置して硬化させた。次に、80℃に設定した熱風循環乾燥機で24時間二次硬化を行った。ステンレス容器からエポキシ樹脂ブロックを取り出し、切削旋盤装置(東芝機械社製)を用いて100〜150μmの厚みでスライスしてエポキシ樹脂シートを得た。該エポキシ樹脂シートを純水中で水洗してポリエチレングリコールを除去し、その後、70℃で2分間、80℃で1分間、及び90℃で1分間乾燥してエポキシ樹脂多孔シートを作製した。その後、作製したエポキシ樹脂多孔シートをイソプロピルアルコール20wt%の水溶液に10分間浸漬して親水化処理を施した。
親水化処理を施したエポキシ樹脂多孔シートを用いて実施例1と同様の方法で複合半透膜を作製した。作製した複合半透膜を用いて透過試験を行った。透過試験の結果、塩阻止率は99.5(%)、透過流束は0.9(m3/m2・d)であった。また、透過試験後の複合半透膜の断面の走査型電子顕微鏡(SEM)写真(2万倍)を図2に示す。エポキシ樹脂多孔シート上に欠陥なくスキン層が形成されていることがわかる。
ポリエチレングリコール(三洋化成(株)製、商品名「PEG200」)3087.2gの代わりに、ポリプロピレングリコール(日油(株)製、商品名「D−250」)を3355.7g用いた以外は実施例4と同様の方法で親水化処理を施したエポキシ樹脂多孔シートを作製した。親水化処理を施したエポキシ樹脂多孔シートを用いて実施例1と同様の方法で複合半透膜を作製した。作製した複合半透膜を用いて透過試験を行った。透過試験の結果、塩阻止率は99.3(%)、透過流束は0.9(m3/m2・d)であった。また、透過試験後の複合半透膜の断面の走査型電子顕微鏡(SEM)写真(800倍、4000倍)を図3−1及び3−2に示す。エポキシ樹脂多孔シート上に欠陥なくスキン層が形成されていることがわかる。
2:スライサー
3:回転軸
4:エポキシ樹脂シート
Claims (10)
- 熱硬化性樹脂、硬化剤、及びポロゲンを含む熱硬化性樹脂組成物の硬化体からなる円筒状又は円柱状樹脂ブロックを作製する工程、該樹脂ブロックの表面を所定厚みで切削して長尺状の熱硬化性樹脂シートを作製する工程、及び熱硬化性樹脂シート中のポロゲンを除去する工程を含み、
前記熱硬化性樹脂が、エポキシ樹脂であり、
前記エポキシ樹脂は、エポキシ当量が100以上異なる2種以上のエポキシ樹脂を混合して含む熱硬化性樹脂多孔シートの製造方法。 - 円筒状又は円柱状樹脂ブロックの円筒軸又は円柱軸を中心に回転させながら前記切削を行う請求項1記載の熱硬化性樹脂多孔シートの製造方法。
- エポキシ樹脂と硬化剤の組み合わせが、芳香族エポキシ樹脂と脂環族アミン硬化剤の組み合わせ、又は脂環族エポキシ樹脂と芳香族アミン硬化剤の組み合わせである請求項1又は2記載の熱硬化性樹脂多孔シートの製造方法。
- ポロゲンの含有量は、エポキシ樹脂、硬化剤、及びポロゲンの総重量に対して40〜80重量%である請求項1〜3のいずれかに記載の熱硬化性樹脂多孔シートの製造方法。
- ポロゲンの含有量は、エポキシ樹脂、硬化剤、及びポロゲンの総重量に対して60〜70重量%である請求項1〜3のいずれかに記載の熱硬化性樹脂多孔シートの製造方法。
- エポキシ樹脂、硬化剤、及びポロゲンを含むエポキシ樹脂組成物を15〜150℃で硬化させ、さらに50〜160℃でポストキュアを行って硬化体を作製する請求項1〜5のいずれかに記載の熱硬化性樹脂多孔シートの製造方法。
- 熱硬化性樹脂シート中のポロゲンを除去した後に、得られた熱硬化性樹脂多孔シートを乾燥処理する工程を含む請求項1〜6のいずれかに記載の熱硬化性樹脂多孔シートの製造方法。
- ポロゲンが、ポリエチレングリコールである請求項1〜7のいずれかに記載の熱硬化性樹脂多孔シートの製造方法。
- ポロゲンが、分子量500以下のポリプロピレングリコールである請求項1〜7のいずれかに記載の熱硬化性樹脂多孔シートの製造方法。
- 円筒状又は円柱状樹脂ブロックの幅(軸方向の長さ)が、20〜200cmである請求項1〜9のいずれかに記載の熱硬化性樹脂多孔シートの製造方法。
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JP2004338208A (ja) | 2003-05-15 | 2004-12-02 | Nitto Denko Corp | 改質ポリテトラフルオロエチレンの製造方法 |
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JP2008515668A (ja) | 2004-10-06 | 2008-05-15 | ザ リサーチ ファウンデーション オブ ステイト ユニバーシティー オブ ニューヨーク | 高流量かつ低付着の濾過媒体 |
WO2006069307A2 (en) * | 2004-12-22 | 2006-06-29 | Entegris, Inc. | Multilayer porous membrane and process of manufacture |
JP5153142B2 (ja) * | 2005-01-07 | 2013-02-27 | 株式会社エマオス京都 | エポキシ樹脂硬化物多孔体 |
JP2008013672A (ja) * | 2006-07-06 | 2008-01-24 | Kyoto Institute Of Technology | エポキシ樹脂硬化物多孔体と繊維を含んでなる複合材料 |
WO2008118228A2 (en) | 2006-12-05 | 2008-10-02 | Stonybrook Water Purification | Articles comprising a fibrous support |
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2009
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- 2009-10-23 KR KR1020117011526A patent/KR101361873B1/ko not_active IP Right Cessation
- 2009-10-23 WO PCT/JP2009/068235 patent/WO2010047383A1/ja active Application Filing
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US9186633B2 (en) | 2015-11-17 |
CN102197073A (zh) | 2011-09-21 |
US20110192788A1 (en) | 2011-08-11 |
KR20110079735A (ko) | 2011-07-07 |
JP2010121122A (ja) | 2010-06-03 |
CN102197073B (zh) | 2016-01-13 |
KR101361873B1 (ko) | 2014-02-12 |
WO2010047383A1 (ja) | 2010-04-29 |
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