JP6116642B2 - 親水性改質フッ素化膜(v) - Google Patents
親水性改質フッ素化膜(v) Download PDFInfo
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- JP6116642B2 JP6116642B2 JP2015209921A JP2015209921A JP6116642B2 JP 6116642 B2 JP6116642 B2 JP 6116642B2 JP 2015209921 A JP2015209921 A JP 2015209921A JP 2015209921 A JP2015209921 A JP 2015209921A JP 6116642 B2 JP6116642 B2 JP 6116642B2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09D147/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Coating compositions based on derivatives of such polymers
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- 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
- B01D67/0006—Organic membrane manufacture by chemical reactions
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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Description
[0001]多孔質フルオロポリマー膜、例えば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、及び架橋結合されたポリマー網目構造を含む被覆を含む、親水性複合多孔質膜であって、多孔質フルオロポリマー支持体を、溶媒、架橋剤、光開始剤、及び重合された1,5−シクロオクタジエン繰返し単位からなる主鎖を含み、繰返し単位の少なくとも1つが、主鎖に結合したペンダント親水性基を含み、繰返し単位の少なくとももう1つが、主鎖に結合したペンダントフッ素化疎水性基を含む、テレケリックポリマーを含む被覆組成物で被覆し、得られた被覆をin situ架橋結合させることによって製造される、親水性複合多孔質膜を提供する。
[0009]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、及び架橋結合されたポリマー網目構造を含む被覆を含む、親水性複合多孔質膜であって、多孔質フルオロポリマー支持体を、溶媒、架橋剤、光開始剤、及び重合された1,5−シクロオクタジエン繰返し単位からなる主鎖を含み、前記繰返し単位の少なくとも1つが、主鎖に結合したペンダント親水性基を含み、該繰返し単位の少なくとももう1つが、主鎖に結合したペンダントフッ素化疎水性基を含む、テレケリックポリマーを含む被覆組成物で被覆し、得られた被覆をin situ架橋結合させることによって製造される、親水性複合多孔質膜を提供する。
式中、Rは親水性基である。
式中、x及びmは、独立してn+m+xの0〜35モル%であり、但し、n+m+x=10〜1000、n及びmは、独立して約10〜約1000であり、Rは親水性基である。
式中、Rは、親水性基、例えば、カルボキシアルキル、スルホンアルキル、又はヒドロキシアルキルの各基であり、nは約10〜約1000であり、但し、Pは重合開始可能な基である。
式中、Pは重合開始可能な基であり、x及びmは、独立してn+m+xの0〜35モル%であり、但し、n+m+x=10〜1000、Rは親水性基である。
式中、Pは重合開始可能な基であり、x及びmは、独立してn+m+xの0〜35モル%であり、但し、n+m+x=10〜1000、Rは親水性基である。
[0024](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、
[0025](ii)溶媒、架橋剤、光開始剤、及び上記のテレケリック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、
[0026](iii)(ii)からの被覆フルオロポリマー支持体を乾燥させて、被覆溶液から溶媒の少なくとも一部を取り除くステップと、
[0027](iv)被覆に存在する前記テレケリック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をさらに提供する。
がある。
但し、m+x=n。
但し、m+x=y+1(XIII)。
式中、n+m+x=y+1(VII)。
[0013]材料:以下の材料を購入し、そのまま使用した。
[0016]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。
[0018]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。
[0020]移動相:ジクロロメタン(DCM)
[0021]移動相温度:30℃
[0022]UV波長:245nm
[0023]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
[0024]流量:1mL/分
[0025]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
[0026]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
[0100]本実施例は、本発明の一実施形態のポリシクロオクタジエン(P−COD)の合成方法を説明する。
[0102]本実施例は、本発明の一実施形態の式(X)、ポリ(gly−hb−COD−hb−gly)であるグリシジル末端基を有するテレケリックポリマーを合成する方法を説明する。
[0104]本実施例は、ポリシクロオクタジエン及びそのハイパーブランチブロックコポリマーをフッ素含有試薬で後官能化する方法を説明する。
[0106]本実施例は、PTFE多孔質支持体の、PCOD及びポリ(gly−hb−COD−hb−gly)を被覆する工程、及び架橋結合させる工程を説明する。
Claims (18)
- 多孔質フルオロポリマー支持体、及び架橋結合されたポリマー網目構造を含む被覆を含む、親水性複合多孔質膜であって、多孔質フルオロポリマー支持体を、溶媒、架橋剤、光開始剤、及び重合された1,5−シクロオクタジエン繰返し単位からなる主鎖を含み、前記繰返し単位の少なくとも1つが、主鎖に結合したペンダント親水性基を含み、前記繰返し単位の少なくとももう1つが、主鎖に結合したペンダントフッ素化疎水性基を含む、テレケリックポリマーを含む被覆組成物で被覆し、得られた被覆をin situ架橋結合させることによって製造される、親水性複合多孔質膜。
- テレケリックポリマーが、疎水性末端基及び/又は親水性末端基を含む、請求項1に記載の親水性複合多孔質膜。
- テレケリックポリマーが、繰返し単位B及びCの少なくとも1つ、並びに任意選択で、1つ又は複数の繰返し単位Aを含み、繰返し単位A〜Cは次式のものであり、
- Rが、カルボキシアルキル、スルホンアルキル、及びヒドロキシアルキルの各基から選択される、請求項3に記載の親水性複合多孔質膜。
- 繰返し単位A、B及びCを含む、請求項1〜4のいずれか一項に記載の親水性複合多孔質膜。
- 疎水性末端基を有する、請求項1〜5のいずれか一項に記載の親水性複合多孔質膜。
- テレケリックポリマーが、次式のものであり、
- テレケリックポリマーが、親水性末端基を有する、請求項1〜6のいずれか一項に記載の親水性複合多孔質膜。
- テレケリックポリマーが、以下の式のものを含み、
- Rが、カルボキシアルキル、スルホンアルキル、及びヒドロキシアルキルの各基から選択される、請求項9に記載の親水性複合多孔質膜。
- 架橋剤が、バイチオール又はマルチチオールである、請求項1〜10のいずれか一項に記載の親水性複合多孔質膜。
- テレケリックポリマーが、次式のものであり、
- 光開始剤が、カンファーキノン、ベンゾフェノン、ベンゾフェノン誘導体、アセトフェノン、アセトフェノン誘導体、ホスフィンオキシド及び誘導体、ベンゾインアルキルエーテル、ベンジルケタール、フェニルグリオキサルエステル及びその誘導体、二量体フェニルグリオキサルエステル、ペルエステル、ハロメチルトリアジン、ヘキサアリールビスイミダゾール/共開始剤系、フェロセニウム化合物、チタノセン、並びにその組み合わせから選択される、請求項1〜12のいずれか一項に記載の親水性複合多孔質膜。
- 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1〜13のいずれか一項に記載の親水性複合多孔質膜。
- 被覆の架橋結合が、被覆をUV放射へ曝すことによって形成される、請求項1〜14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、架橋剤、光開始剤、及び次式のテレケリック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、
(iii)(ii)からの被覆多孔質フルオロポリマー支持体を乾燥させて、被覆から溶媒の少なくとも一部を取り除くステップと、
(iv)被覆に存在するテレケリック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。 - 請求項16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、親水性改質フルオロポリマー多孔質膜。
- 請求項1〜15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17に記載の親水性改質フルオロポリマー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。
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9855534B1 (en) * | 2016-12-28 | 2018-01-02 | Pall Corporation | Porous PTFE membranes for metal removal |
WO2019177966A1 (en) | 2018-03-15 | 2019-09-19 | Entegris, Inc. | Fluorinated filter membrane, filters, and methods |
CN111683736A (zh) | 2018-03-22 | 2020-09-18 | 富士胶片株式会社 | 过滤装置、纯化装置、药液的制造方法 |
US11010092B2 (en) | 2018-05-09 | 2021-05-18 | Micron Technology, Inc. | Prefetch signaling in memory system or sub-system |
US10714159B2 (en) | 2018-05-09 | 2020-07-14 | Micron Technology, Inc. | Indication in memory system or sub-system of latency associated with performing an access command |
US10942854B2 (en) | 2018-05-09 | 2021-03-09 | Micron Technology, Inc. | Prefetch management for memory |
US20200171442A1 (en) * | 2018-11-30 | 2020-06-04 | Entegris, Inc. | Hydrophilic filter membrane with pendant hydrophilic groups, and related methods of preparation and use |
US12076705B2 (en) * | 2019-02-08 | 2024-09-03 | The University Of Queensland | Capture of fluorinated carbon compounds |
KR102695013B1 (ko) | 2019-04-24 | 2024-08-13 | 삼성전자주식회사 | 펠리클 조립체의 제조 방법 및 포토마스크 조립체의 제조 방법 |
CN110256724B (zh) * | 2019-06-17 | 2021-04-20 | 西安交通大学 | 一种用于光固化连续面成型3d打印的防粘附薄膜制备方法 |
CN112297475B (zh) * | 2020-11-05 | 2021-08-03 | 中国长江三峡集团有限公司 | 一种增强基于ptfe膜强度的高温高线压力微共晶方法 |
Family Cites Families (60)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1538810A (en) | 1976-08-10 | 1979-01-24 | Sumitomo Electric Industries | Hydrophilic porous fluorocarbon structures and process for their production |
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 |
JPS61161103A (ja) | 1985-01-10 | 1986-07-21 | Terumo Corp | 親水性多孔質膜およびその製法 |
JPS61249503A (ja) | 1985-04-25 | 1986-11-06 | Sumitomo Electric Ind Ltd | 親水性ポリテトラフルオロエチレン濾過膜及びその製造方法 |
US4975507A (en) | 1987-05-27 | 1990-12-04 | Monsanto Company | Cyclopentanedioxocarbonyl vinylene polymers |
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 |
US5219662A (en) | 1991-05-23 | 1993-06-15 | E. I. Du Pont De Nemours And Company | Biocompatible polyurethanes by treatment with polyoxazoline block copolymers |
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 |
CN1077804C (zh) | 1994-07-28 | 2002-01-16 | 米利波尔公司 | 多孔复合膜及其制法 |
JP3809201B2 (ja) | 1995-04-14 | 2006-08-16 | 住友電気工業株式会社 | 親水性四弗化エチレン樹脂多孔質膜及びその製造方法 |
EP0935494A4 (en) | 1996-07-08 | 2000-06-14 | CATIONIC MEMBRANES WITH MODIFIED LOAD | |
WO1998015595A1 (fr) | 1996-10-09 | 1998-04-16 | Nippon Zeon Co., Ltd. | Composition a base d'un polymere de norbornene |
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 |
US6355081B1 (en) | 1999-06-01 | 2002-03-12 | Usf Filtration And Separations Group, Inc. | Oleophobic filter materials for filter venting applications |
GB9916235D0 (en) | 1999-07-09 | 1999-09-15 | Univ Durham | Process for polymerisation of olefins and novel polymerisable olefins |
DE60015600T2 (de) | 1999-08-25 | 2005-11-10 | Zeon Corp. | Geöffnete norbornenringpolymere, deren hydrierungsprodukte sowie verfahren zur herstellung beider produkte |
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 |
DE60212965T2 (de) | 2001-04-27 | 2007-10-25 | Millipore Corp., Billerica | Vernetzte multipolymere beschichtung |
EP1483300A4 (en) | 2002-02-19 | 2009-04-08 | California Inst Of Techn | RINGER EXPLOITATION OF CYCLIC OLEFINES BY OLEFINMETATHESE ACTIONS WITH ACYCLIC SERVICE |
AU2003260009A1 (en) | 2002-09-03 | 2004-03-29 | Whatman Plc | Porous composite membrane and method for making the same |
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 |
CN1926081B (zh) | 2004-02-26 | 2011-06-15 | 特林公司 | 用于烯烃易位和原子或基团转移反应的金属配合物 |
WO2006053071A2 (en) | 2004-11-09 | 2006-05-18 | E.I. Dupont De Nemours And Company | Ring opening polymerization of cyclic amides using n-heterocyclic carbene catalysts |
CN101084057B (zh) | 2004-12-03 | 2013-10-23 | 西门子工业公司 | 膜的后处理方法 |
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 |
KR20080059243A (ko) | 2005-09-22 | 2008-06-26 | 니폰 제온 가부시키가이샤 | 노보넨 화합물 부가 중합체, 그 제조 방법, 상기 중합체로이루어지는 성형품 및 그 용도 |
US7381331B2 (en) | 2005-09-30 | 2008-06-03 | General Electric Company | Hydrophilic membrane and associated method |
TW200736311A (en) | 2006-01-30 | 2007-10-01 | Zeon Corp | Film comprising norbornene compound addition polymer |
JPWO2007105653A1 (ja) | 2006-03-10 | 2009-07-30 | 旭硝子株式会社 | 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 |
MX2009004161A (es) | 2006-10-17 | 2009-05-28 | Firestone Polymers Llc | Elastomeros, proceso para su preparacion, y uso de los mismos. |
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 |
US10092881B2 (en) | 2008-01-25 | 2018-10-09 | Bha Altair, Llc | Permanent hydrophilic porous coatings and methods of making them |
US8215496B2 (en) | 2008-01-28 | 2012-07-10 | Promerus Llc | Polynorbornene pervaporation membrane films, preparation and use thereof |
US8132676B2 (en) | 2008-08-18 | 2012-03-13 | Emd Millipore Corporation | Hydrophilic, high protein binding, low fluorescence, western blotting membrane |
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 |
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 |
US8505743B2 (en) | 2009-04-08 | 2013-08-13 | Michigan Molecular Institute | Surface modification of polyamide reverse osmosis membranes |
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 |
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 |
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 |
JP6219812B2 (ja) | 2011-04-07 | 2017-10-25 | ソルヴェイ・スペシャルティ・ポリマーズ・イタリー・エッセ・ピ・ア | 架橋フッ素化ポリマーを製造する方法 |
US20130004690A1 (en) | 2011-06-29 | 2013-01-03 | Mikhael Michael G | Hydrophilic expanded fluoropolymer composite and method of making same |
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) |
JP2014042878A (ja) | 2012-08-27 | 2014-03-13 | Nitto Denko Corp | 撥油性が付与された通気フィルタ |
MY188144A (en) | 2013-02-27 | 2021-11-23 | Materia Inc | Metal carbene olefin metathesis two catalyst composition |
ITGE20130096A1 (it) | 2013-09-27 | 2015-03-28 | Consiglio Nazionale Ricerche | Membrane ricoperte da microemulsioni bicontinue polimerizzate per il trattamento delle acque. |
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US9630151B2 (en) | 2017-04-25 |
US20160288060A1 (en) | 2016-10-06 |
CN106010062B (zh) | 2019-01-15 |
JP2016194037A (ja) | 2016-11-17 |
KR101780018B1 (ko) | 2017-09-19 |
TWI593725B (zh) | 2017-08-01 |
SG10201508801PA (en) | 2016-10-28 |
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