JP5704891B2 - かご型シルセスキオキサン(poss)及び親水性コモノマーから作成されたポリマー膜 - Google Patents
かご型シルセスキオキサン(poss)及び親水性コモノマーから作成されたポリマー膜 Download PDFInfo
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- JP5704891B2 JP5704891B2 JP2010247449A JP2010247449A JP5704891B2 JP 5704891 B2 JP5704891 B2 JP 5704891B2 JP 2010247449 A JP2010247449 A JP 2010247449A JP 2010247449 A JP2010247449 A JP 2010247449A JP 5704891 B2 JP5704891 B2 JP 5704891B2
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- membrane
- acrylate
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- compound
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- 150000001875 compounds Chemical class 0.000 claims description 59
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- 238000000034 method Methods 0.000 claims description 23
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 20
- 238000001914 filtration Methods 0.000 claims description 15
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- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 9
- 125000005647 linker group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 8
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
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- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 5
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- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
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- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
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- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
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- 125000001624 naphthyl group Chemical group 0.000 description 2
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- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
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- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical class O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
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Description
は式T8 Rで表示され、TはRSiO3/2を表し、
は式T10 Rで表示され、TはRSiO3/2を表し、
は式T12 Rで表示され、TはRSiO3/2を表し、そして
である。
(1)
及び、
を含むメタクリレート、並びに、
(2)
及び、
を含むアクリレート、のような重合可能基から選択される。
ここで、R1=エチル基及びOR2=構造(V)Cであり、
ここで、R3=イソブチル基及びOR4=構造(V)Aである。
以下の調製実施例において詳しく論じるように、自立型薄膜は、ハイブリッドプラスチック社(HybridPlastics Co.)から市販のPOSS化合物である(メタ)アクリル置換かご型シルセスキオキサン(n=8、10、12の(C7H11O2)n(SiO1.5)nのメタクリルPOSSかご混合物、以下のスキーム1にはn=8のみを示す)と、ミズーリ州セントルイスのシグマ−アルドリッチ社から市販の親水性コモノマーであるポリエチレングリコールモノアクリレート(PEG−M)とを反応させて作成した。この膜は、ニューヨーク州タリタウンのチバ社(BASF)から商品名DAROCUR4265で市販の光開始剤TPOの存在下でのUV硬化プロセスで作成した。
増加すること、並びに、吸水率及び透水率もまたPEG添加物の含量に強く依存することを示す。最大の吸水率及び透水率の値(276%、133 L μm m−2h−1atm−1)は、50%(w/w)PEGを用いて調製した膜で観測された(50%は、可能な成膜処理のために加えることができる最大量であった)。
以下の実施例においてさらに詳細に説明するように、メタクリルPOSS、PEG−M及びPEG添加物の、光開始剤を含んだ重合前混合物を、ポリスルホン(PSF)限外ろ過膜の上面に塗布し、UV−硬化させた。塗布するコーティング層の厚さを制御するために、適当な希釈剤を重合前混合物に加えることができる。
コーティングされた膜のろ過中の絶対透過水流束は、コーティング層の厚さ減らすことにより増加させることができる。50%のPEG添加物を用いて調製したコーティング層(POSS−PEG−M A50N)の厚さは、図4(A)に示すように、乾燥状態で約4μmであった。
実施例1:純粋重合前混合物と40%PEG添加物(POSS−PEG−M A40N)から作成された、チャネル形成された膜
自立型膜:0.29gのメタクリルPOSS(かご混合物8−12、ハイブリッドプラスチック社)、5.71gのポリ(エチレングリコール)メタクリレート(Mw:526、アルドリッチ社)、4gのポリエチレングリコール(Mw:400)及び0.06gの開始剤(チバ社、Darocur4265)を窒素グローブボックス内で混合し一晩撹拌した。
自立型膜:0.24gのメタクリルPOSS(かご混合物8−12、ハイブリッドプラスチック社)、4.76gのポリ(エチレングリコール)メタクリレート(Mw:526、アルドリッチ社)、5gのポリエチレングリコール(Mw:400)及び0.05gの開始剤(チバ社、Darocur4265)を窒素グローブボックス内で混合し一晩撹拌した。膜の調製及び特性解析は実施例1と同じ方法で行った。
重合前混合物の調製:0.24gのメタクリルPOSS(かご混合物8−12、ハイブリッドプラスチック社)、4.76gのポリ(エチレングリコール)メタクリレート(Mw:526、アルドリッチ社)、5gのポリエチレングリコール(Mw:400)及び0.05gの開始剤(チバ社、Darocur4265)を窒素グローブボックス内で混合し、2gのエタノール(EtOH)で希釈し、一晩撹拌した。
POSS−PEG−M A40N及びPOSS−PEG−M A50Nでコーティングされた複合膜の透過流束をモニターするために、市販のクロスフローろ過システムを用いて、油/水エマルジョンのクロスフローろ過を行った。油/水エマルジョンは、植物油/界面活性剤(重量比=9:1)を3Lの脱イオン水と混合して調製した(油の濃度:1500ppm)。クロスフローろ過は25℃で行い、クロスフロー速度は100psiにおいて0.35Gal/minであった。透過流束はコンピュータに接続した直示天秤で記録した。
POSS−PEG−M A50N及びPOSS−PEG−M A50Dでコーティングされた複合膜の透過流束をモニターするために、市販のクロスフローろ過システムを用いて、タンパク質供給溶液のクロスフローろ過を行った。タンパク質供給溶液は5gのウシ血清アルブミン(BSA)を、0.1Mリン酸緩衝剤を含む5Lの脱イオン水(pH7.4)に溶解させて調製した。クロスフローろ過は25℃で行い、クロスフロー速度は30psiにおいて0.8L/minであった。透過流束はコンピュータに接続した直示天秤で記録した。
不可逆タンパク質汚染は、複合膜(POSS−PEG−M A50N及びPOSS−PEG−M A50Dでコーティングされた)の汚染実験の前後の純水透水率を比較することにより決定される。汚染実験の前に、膜の純水透過流速(Pw,0)を、汚染実験を行ったのと同じ圧力及びクロスフロー速度(30psi及び0.8L/min)において決定した。
タンパク質付着実験は、標識を付けたウシ血清アルブミン(BSA)の蛍光分析を用いて行った。POSS−PEG−M A50N及びPOSS−PEG−M A50Dにより調製された複合膜の平坦シートから直径2.5cm(1インチ)のサンプルを切り取った。この円形サンプルを、3.5cm2の有効表面積を有するデッドエンド型セル(米国カリフォルニア州ダブリンのアドバンテックMFS社の#UHP25)の内部に配置し、脱イオン水で数回洗浄した。次にR−NHS標識付きBSA溶液(脱イオン水中0.1mg/mL)をセルに加えた。10分後、タンパク質溶液を傾斜除去し、膜表面を脱イオン水で繰り返し洗浄した。
Claims (17)
- 複合膜であって、
ろ過膜と、該ろ過膜の表面上の層とを含み、
前記層は、少なくとも1つの頂点に結合した親水性部分を有するかご型シルセスキオキサン(POSS)誘導体を含むポリマーを含み、前記層は、0.5〜10kDaの分子量カットオフ(MWCO)を有する孔及びチャネルの少なくとも1つを含み、前記MWCOは、前記膜により90%が阻止される基準ポリエチレングリコールの分子量である、
前記複合膜。 - 前記親水性部分は、ポリ(エチレングリコール)アクリレート、ポリ(エチレングリコール)ジアクリレート、ポリ(エチレングリコール)メタクリレート、アクリル酸、2−ヒドロキシエチルメタクリレート、2−ヒドロキシエチルアクリレート、2−(2−エトキシエトキシ)エチルアクリレート、テトラヒドロフルフリルアクリレート、及びそれらの組合せから成る群から選択された化合物から誘導される、請求項1に記載の複合膜。
- 前記層は50nm〜5μmの乾燥厚を有する、請求項1又は2に記載の複合膜。
- 複合膜を作成する方法であって、
ろ過膜の表面に、かご型シルセスキオキサン(POSS)化合物、親水性コモノマー、及び光開始剤、並びに、溶媒抽出可能な犠牲化合物を含む光重合可能組成物を塗布するステップと、
前記組成物を硬化させて前記ろ過膜の上に親水性層を形成するステップと
前記親水性層に溶媒を塗布して前記溶媒抽出可能な犠牲化合物を抽出し、前記親水性層内に孔及びチャネルの少なくとも1つを作成するステップと
を含む、前記方法。 - 複合膜を作成する方法であって、
ろ過膜の表面に、かご型シルセスキオキサン(POSS)化合物、親水性コモノマー、及び光開始剤を含む光重合可能組成物を塗布するステップと、
前記組成物を硬化させて前記ろ過膜の上に親水性層を形成するステップと
を含み、
前記親水性層は、0.5〜10kDaの分子量カットオフ(MWCO)を有する孔及びチャネルの少なくとも1つを含み、前記MWCOは、前記膜により90%が阻止される基準ポリエチレングリコールの分子量である、
前記方法。 - 前記POSS化合物は、各々が1つ又は複数の重合可能基を有する1つ又は複数のかご型シルセスキオキサン構造を有し、
前記重合可能基は、前記かご型シルセスキオキサン構造のそれぞれのシリコン原子に結合する、
請求項4又は5に記載の方法。 - 前記1つ又は複数の重合可能基は、構造−(L)n−Pを含み、ここでLは連結基であり、nは0又は1であり、Pは重合可能基である、請求項6に記載の方法。
- 前記連結基は独立に、アルキル基、シクロアルキル基、シロキサン、アルキルシリル基、アルキルシロキシル基及びそれの組合せから成る群から選択される、請求項7に記載の方法。
- 前記1つ又は複数の重合可能基は独立に(メタ)アクリレートから選択される、請求項7又は8に記載の方法。
- 前記選択された(メタ)アクリレートは、以下のメタクリレートのうちの少なくとも1つである、請求項9に記載の方法。
- 前記選択された(メタ)アクリレートは、
- 前記重合可能基は、
- 前記コモノマーは、ポリ(エチレングリコール)アクリレート、ポリ(エチレングリコール)ジアクリレート、ポリ(エチレングリコール)メタクリレート、アクリル酸、2−ヒドロキシエチルメタクリレート、2−ヒドロキシエチルアクリレート、2−(2−エトキシエトキシ)エチルアクリレート、又はテトラヒドロフルフリルアクリレートのうちの少なくとも1つである、請求項4〜12のいずれか一項に記載の方法。
- 前記コモノマーはPEG(メタ)アクリレートである、請求項4〜12のいずれか一項に記載の方法。
- 前記溶媒は水を含み、
前記犠牲化合物は、ポリエチレングリコール、ポリアクリル酸、ヒドロキシエチルセルロース、及びそれらの組合せから成る群から選択される、
請求項4に記載の方法。 - 前記親水性層は、0.5〜10kDaの分子量カットオフ(MWCO)を有する孔及びチャネルの少なくとも1つを含み、
前記MWCOは、前記膜により90%が阻止される基準ポリエチレングリコールの分子量である、
請求項4又は15に記載の方法。 - 前記親水性層は、1〜10kDaのMWCOを有する孔及びチャネルの少なくとも1つを含む、請求項16に記載の方法。
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