JP5373961B2 - 熱処理およびuv架橋により芳香族ポリイミド膜から調製された高分子膜 - Google Patents
熱処理およびuv架橋により芳香族ポリイミド膜から調製された高分子膜 Download PDFInfo
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- JP5373961B2 JP5373961B2 JP2012502071A JP2012502071A JP5373961B2 JP 5373961 B2 JP5373961 B2 JP 5373961B2 JP 2012502071 A JP2012502071 A JP 2012502071A JP 2012502071 A JP2012502071 A JP 2012502071A JP 5373961 B2 JP5373961 B2 JP 5373961B2
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- 239000002861 polymer material Substances 0.000 description 1
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- 238000012805 post-processing Methods 0.000 description 1
- 238000007781 pre-processing Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- AIISZVRFZVBASR-UHFFFAOYSA-N propan-1-ol;propyl acetate Chemical compound CCCO.CCCOC(C)=O AIISZVRFZVBASR-UHFFFAOYSA-N 0.000 description 1
- SAALQYKUFCIMHR-UHFFFAOYSA-N propan-2-ol;2-propan-2-yloxypropane Chemical compound CC(C)O.CC(C)OC(C)C SAALQYKUFCIMHR-UHFFFAOYSA-N 0.000 description 1
- AAZYNPCMLRQUHI-UHFFFAOYSA-N propan-2-one;2-propan-2-yloxypropane Chemical compound CC(C)=O.CC(C)OC(C)C AAZYNPCMLRQUHI-UHFFFAOYSA-N 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 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
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012492 regenerant Substances 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 1
- 238000010555 transalkylation reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- DCGLONGLPGISNX-UHFFFAOYSA-N trimethyl(prop-1-ynyl)silane Chemical compound CC#C[Si](C)(C)C DCGLONGLPGISNX-UHFFFAOYSA-N 0.000 description 1
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- B01D53/22—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by diffusion
- B01D53/228—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by diffusion characterised by specific membranes
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01D2323/345—UV-treatment
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02C—CAPTURE, STORAGE, SEQUESTRATION OR DISPOSAL OF GREENHOUSE GASES [GHG]
- Y02C20/00—Capture or disposal of greenhouse gases
- Y02C20/20—Capture or disposal of greenhouse gases of methane
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PCT/US2010/025820 WO2010110994A2 (en) | 2009-03-27 | 2010-03-02 | Polymer membranes prepared from aromatic polyimide membranes by thermal treating and uv crosslinking |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2640545A1 (en) * | 2008-05-19 | 2009-11-19 | Industry-University Cooperation Foundation, Hanyang University | Polyimides dope composition, preparation method of hollow fiber using the same and hollow fiber prepared therefrom |
WO2010038810A1 (ja) * | 2008-09-30 | 2010-04-08 | 宇部興産株式会社 | 非対称ガス分離膜、及びガス分離方法 |
US9630141B2 (en) * | 2009-02-20 | 2017-04-25 | Cameron Solutions, Inc. | Membrane filter element with multiple fiber types |
US8132678B2 (en) * | 2009-03-27 | 2012-03-13 | Uop Llc | Polybenzoxazole polymer-based mixed matrix membranes |
US8127937B2 (en) | 2009-03-27 | 2012-03-06 | Uop Llc | High performance cross-linked polybenzoxazole and polybenzothiazole polymer membranes |
US8132677B2 (en) | 2009-03-27 | 2012-03-13 | Uop Llc | Polymer membranes prepared from aromatic polyimide membranes by thermal treating and UV crosslinking |
US8613362B2 (en) * | 2009-03-27 | 2013-12-24 | Uop Llc | Polymer membranes derived from aromatic polyimide membranes |
US8127936B2 (en) * | 2009-03-27 | 2012-03-06 | Uop Llc | High performance cross-linked polybenzoxazole and polybenzothiazole polymer membranes |
US8561812B2 (en) * | 2009-03-27 | 2013-10-22 | Uop Llc | Blend polymer membranes comprising thermally rearranged polymers derived from aromatic polyimides containing ortho-positioned functional groups |
US20100326913A1 (en) * | 2009-06-25 | 2010-12-30 | Uop Llc | Polybenzoxazole membranes prepared from aromatic polyamide membranes |
US8459469B2 (en) * | 2009-06-25 | 2013-06-11 | Uop Llc | Polybenzoxazole membranes prepared from aromatic polyamide membranes |
US7810652B2 (en) * | 2009-09-25 | 2010-10-12 | Uop Llc | Method to improve the selectivity of polybenzoxazole membranes |
US8915379B2 (en) * | 2009-09-25 | 2014-12-23 | Uop Llc | Method to improve the selectivity of polybenzoxazole membranes |
US8931646B2 (en) * | 2009-09-25 | 2015-01-13 | Uop Llc | Polybenzoxazole membranes |
JP2013075264A (ja) * | 2011-09-30 | 2013-04-25 | Fujifilm Corp | ガス分離膜、その製造方法、それを用いたガス分離膜モジュール |
GB201211309D0 (en) * | 2012-06-26 | 2012-08-08 | Fujifilm Mfg Europe Bv | Process for preparing membranes |
KR102014880B1 (ko) * | 2012-12-28 | 2019-08-28 | 삼성디스플레이 주식회사 | 표시 장치 및 이의 제조방법 |
WO2014130844A1 (en) | 2013-02-21 | 2014-08-28 | The Regents Of The University Of California | Universal scalable and cost-effective surface modifications |
US20140255636A1 (en) * | 2013-03-06 | 2014-09-11 | Saudi Basic Industries Corporation | Polymeric Membranes |
EP3069784B1 (en) * | 2013-11-15 | 2020-01-08 | IUCF-HYU (Industry-University Cooperation Foundation Hanyang University) | Flue gas separation membrane comprising thermally rearranged poly(benzoxazole-imide) copolymer having cross-linked structure, and preparation method therefor |
CN105899580B (zh) * | 2013-11-15 | 2019-01-01 | 汉阳大学校产学协力团 | 经交联、热重排的聚(苯并*唑-共-酰亚胺),包含其的气体分离膜以及其制备方法 |
EP3057689A4 (en) | 2013-12-16 | 2016-08-31 | Sabic Global Technologies Bv | POLYMERIC MEMBRANES TREATED BY ULTRAVIOLET AND THERMALLY RADIATION |
JP6203393B2 (ja) * | 2013-12-16 | 2017-09-27 | サビック グローバル テクノロジーズ ビー.ブイ. | 処理済み混合マトリックス高分子膜 |
US9669382B2 (en) | 2013-12-20 | 2017-06-06 | Uop Llc | Methods and apparatuses for isomerizing hydrocarbons |
JP6681663B2 (ja) * | 2014-04-22 | 2020-04-15 | 株式会社日本触媒 | エーテル結合及び/又はチオエーテル結合とフッ素原子とを含むポリイミドを表面に含む細胞培養用基材 |
EP3135752A4 (en) * | 2014-04-22 | 2018-03-14 | Nippon Shokubai Co., Ltd. | Cell culture substrate containing fluorine-containing polymer on surface |
JP6681665B2 (ja) * | 2014-04-22 | 2020-04-15 | 株式会社日本触媒 | 加熱処理によりイミド化された含フッ素ポリイミドを表面に含む細胞培養用基材 |
KR101692133B1 (ko) * | 2015-01-13 | 2017-01-02 | 연세대학교 원주산학협력단 | 폴리이미드 수용액을 이용한 폴리이미드 성형방법 |
US10501579B2 (en) * | 2015-02-20 | 2019-12-10 | Sabic Global Technologies B.V. | Poly(amic acid) synthesis and conversion to high molecular weight polyimide |
WO2016136404A1 (ja) | 2015-02-27 | 2016-09-01 | 富士フイルム株式会社 | ガス分離膜、ガス分離モジュール、ガス分離装置、及びガス分離方法 |
US9920168B2 (en) | 2015-03-17 | 2018-03-20 | Dow Global Technologies Llc | Polymers of intrinsic microporosity |
US10029217B2 (en) | 2015-05-22 | 2018-07-24 | Chevron U.S.A. Inc. | Methods of making crosslinked membranes utilizing an inert gas atmosphere |
WO2016195977A1 (en) | 2015-05-29 | 2016-12-08 | Dow Global Technologies Llc | Isatin copolymers having intrinsic microporosity |
WO2016206008A1 (en) | 2015-06-24 | 2016-12-29 | Dow Global Technologies Llc | Isatin copolymers having intrinsic microporosity |
US10737214B2 (en) | 2015-10-01 | 2020-08-11 | Jgc Corporation | Nonhydrocarbon gas separation device and nonhydrocarbon gas separation method |
WO2017087180A1 (en) * | 2015-11-20 | 2017-05-26 | Uop Llc | High selectivity copolyimide membranes for separations |
CN108291026A (zh) | 2015-11-24 | 2018-07-17 | 陶氏环球技术有限责任公司 | 具有固有微孔性的troger碱聚合物 |
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TWI718592B (zh) * | 2018-08-20 | 2021-02-11 | 財團法人紡織產業綜合研究所 | 聚醯胺醯亞胺的製備方法 |
TWI670295B (zh) | 2018-08-20 | 2019-09-01 | 財團法人紡織產業綜合研究所 | 聚醯胺醯亞胺及其製備方法 |
EP3841151A1 (en) * | 2018-08-23 | 2021-06-30 | Dow Global Technologies LLC | Cross-linked polyimide membranes and carbon molecular sieve hollow fiber membranes made therefrom |
CN111171856A (zh) * | 2018-11-13 | 2020-05-19 | 中国科学院大连化学物理研究所 | 一种碳分子筛膜用于c4-c6正异构烷烃的分离方法 |
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KR102236277B1 (ko) | 2020-03-11 | 2021-04-02 | 한국화학연구원 | H2o 안정성을 가지는 물의 선택적 분리를 위한 고온 고분자 분리막 및 이를 이용한 반응-분리 하이브리드 시스템 |
CN111530298B (zh) * | 2020-05-12 | 2021-11-23 | 福建师范大学 | 一种含酞菁水解离催化基团单片型聚芳醚砜酮双极膜的制备方法 |
CN113217313B (zh) * | 2021-04-22 | 2022-05-17 | 北京航空航天大学杭州创新研究院 | 响应致动器件、制备方法及应用 |
CN114085393B (zh) * | 2021-11-12 | 2023-03-24 | 苏州大学 | 一种热交联聚合物分离膜的制备方法及应用 |
Family Cites Families (54)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL271831A (US08132677-20120313-C00008.png) | 1960-11-29 | |||
US4230463A (en) | 1977-09-13 | 1980-10-28 | Monsanto Company | Multicomponent membranes for gas separations |
US4847350A (en) | 1986-05-27 | 1989-07-11 | The Dow Chemical Company | Preparation of aromatic heterocyclic polymers |
US4717393A (en) | 1986-10-27 | 1988-01-05 | E. I. Du Pont De Nemours And Company | Polyimide gas separation membranes |
US4855048A (en) | 1987-09-22 | 1989-08-08 | Air Products And Chemicals, Inc. | Air dried cellulose acetate membranes |
JPH01159024A (ja) * | 1987-12-16 | 1989-06-22 | Central Glass Co Ltd | 気体分離膜 |
US4877528A (en) | 1988-10-27 | 1989-10-31 | Bend Research, Inc. | Siloxane-grafted membranes |
JPH02164427A (ja) * | 1989-11-13 | 1990-06-25 | Nitto Denko Corp | 複合膜の製造方法 |
EP0525113A4 (en) | 1990-04-20 | 1993-04-21 | The Dow Chemical Company | Porous polybenzoxazole and polybenzothiazole membranes |
JP2984716B2 (ja) * | 1990-08-31 | 1999-11-29 | ダイセル化学工業株式会社 | 芳香族系分離膜 |
US5837032A (en) | 1991-01-30 | 1998-11-17 | The Cynara Company | Gas separations utilizing glassy polymer membranes at sub-ambient temperatures |
JP3116976B2 (ja) * | 1992-05-08 | 2000-12-11 | 宇部興産株式会社 | ポリイミド分離膜 |
JP2684582B2 (ja) * | 1992-08-25 | 1997-12-03 | 宇部興産株式会社 | ポリイミド分離膜 |
US5409524A (en) | 1992-12-01 | 1995-04-25 | The Dow Chemical Company | Membranes having improved selectivity and recovery, and process for making same |
JPH08215550A (ja) * | 1995-02-15 | 1996-08-27 | Unitika Ltd | 複合膜及びその製造方法 |
US5749943A (en) | 1995-02-27 | 1998-05-12 | Petroleum Energy Center | Method of selectively separating unsaturated hydrocarbon |
US5679131A (en) | 1996-03-13 | 1997-10-21 | Photran Corporation | Method for producing titanium oxide from ore concentrates |
JP3473300B2 (ja) * | 1996-12-03 | 2003-12-02 | 宇部興産株式会社 | 芳香族ポリイミド気体分離膜 |
US6248469B1 (en) * | 1997-08-29 | 2001-06-19 | Foster-Miller, Inc. | Composite solid polymer electrolyte membranes |
JP4070292B2 (ja) * | 1998-03-11 | 2008-04-02 | 日東電工株式会社 | フッ素含有ポリイミド樹脂による気体分離膜 |
JP3361770B2 (ja) * | 1999-04-05 | 2003-01-07 | 財団法人石油産業活性化センター | 炭化水素の分離方法 |
US6368382B1 (en) | 2000-07-27 | 2002-04-09 | Uop Llc | Epoxysilicone coated membranes |
US6500233B1 (en) * | 2000-10-26 | 2002-12-31 | Chevron U.S.A. Inc. | Purification of p-xylene using composite mixed matrix membranes |
US6896796B2 (en) | 2001-02-16 | 2005-05-24 | W. R. Grace & Co.-Conn. | Membrane separation for sulfur reduction |
US6626980B2 (en) | 2001-09-21 | 2003-09-30 | L'air Liquide Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude | Mixed matrix membranes incorporating chabazite type molecular sieves |
WO2003064015A2 (en) | 2002-01-25 | 2003-08-07 | Colorado School Of Mines | Polymer blends and methods of separation using the same |
US20070022877A1 (en) | 2002-04-10 | 2007-02-01 | Eva Marand | Ordered mesopore silica mixed matrix membranes, and production methods for making ordered mesopore silica mixed matric membranes |
US6896717B2 (en) * | 2002-07-05 | 2005-05-24 | Membrane Technology And Research, Inc. | Gas separation using coated membranes |
KR100464317B1 (ko) * | 2002-07-06 | 2005-01-03 | 삼성에스디아이 주식회사 | 측쇄사슬에 산기를 갖는 양성자전도성 고분자, 상기 고분자를 이용한 고분자막 및 이를 이용한 연료전지 |
US6663805B1 (en) * | 2002-09-20 | 2003-12-16 | L'air Liquide Societe Anonyme A Directoire Et Conseil De Surveillance Pour L'etude Et L'exploitation Des Procedes Georges Claude | Process for making hollow fiber mixed matrix membranes |
CN1705551A (zh) * | 2002-10-24 | 2005-12-07 | 东洋纺织株式会社 | 耐热性薄膜和复合离子交换膜 |
JP2004231875A (ja) | 2003-01-31 | 2004-08-19 | Toyobo Co Ltd | ポリベンゾオキサゾールフィルムおよびその製造方法 |
US7166146B2 (en) | 2003-12-24 | 2007-01-23 | Chevron U.S.A. Inc. | Mixed matrix membranes with small pore molecular sieves and methods for making and using the membranes |
US20050268782A1 (en) | 2004-03-26 | 2005-12-08 | Kulkarni Sudhir S | Novel polyimide based mixed matrix membranes |
KR100782959B1 (ko) * | 2005-01-25 | 2007-12-11 | 한양대학교 산학협력단 | 다공성 유기 고분자, 이의 제조방법 및 이를 이용한 기체 분리막 |
FR2893623B1 (fr) | 2005-11-22 | 2008-02-01 | Inst Nat Polytech Grenoble | Preparation de films constitues par un polymere reticule ayant des groupes ioniques |
US7485173B1 (en) | 2005-12-15 | 2009-02-03 | Uop Llc | Cross-linkable and cross-linked mixed matrix membranes and methods of making the same |
US20080300336A1 (en) | 2007-06-01 | 2008-12-04 | Chunqing Liu | Uv cross-linked polymer functionalized molecular sieve/polymer mixed matrix membranes |
US20090114089A1 (en) * | 2007-11-02 | 2009-05-07 | Chunqing Liu | Microporous Aluminophosphate Molecular Sieve Membranes for Highly Selective Separations |
US20090277837A1 (en) * | 2008-05-06 | 2009-11-12 | Chunqing Liu | Fluoropolymer Coated Membranes |
US8083834B2 (en) * | 2008-05-07 | 2011-12-27 | Uop Llc | High permeability membrane operated at elevated temperature for upgrading natural gas |
CA2640545A1 (en) * | 2008-05-19 | 2009-11-19 | Industry-University Cooperation Foundation, Hanyang University | Polyimides dope composition, preparation method of hollow fiber using the same and hollow fiber prepared therefrom |
US20100133171A1 (en) | 2009-03-27 | 2010-06-03 | Chunqing Liu | Polybenzoxazole Polymer-Based Mixed Matrix Membranes |
US8132678B2 (en) | 2009-03-27 | 2012-03-13 | Uop Llc | Polybenzoxazole polymer-based mixed matrix membranes |
US8127936B2 (en) | 2009-03-27 | 2012-03-06 | Uop Llc | High performance cross-linked polybenzoxazole and polybenzothiazole polymer membranes |
US8132677B2 (en) | 2009-03-27 | 2012-03-13 | Uop Llc | Polymer membranes prepared from aromatic polyimide membranes by thermal treating and UV crosslinking |
US8561812B2 (en) | 2009-03-27 | 2013-10-22 | Uop Llc | Blend polymer membranes comprising thermally rearranged polymers derived from aromatic polyimides containing ortho-positioned functional groups |
US8613362B2 (en) | 2009-03-27 | 2013-12-24 | Uop Llc | Polymer membranes derived from aromatic polyimide membranes |
US8127937B2 (en) | 2009-03-27 | 2012-03-06 | Uop Llc | High performance cross-linked polybenzoxazole and polybenzothiazole polymer membranes |
US20100326913A1 (en) | 2009-06-25 | 2010-12-30 | Uop Llc | Polybenzoxazole membranes prepared from aromatic polyamide membranes |
US20100133188A1 (en) | 2009-06-25 | 2010-06-03 | Chunqing Liu | Polybenzoxazole Membranes Prepared From Aromatic Polyamide Membranes |
US8459469B2 (en) | 2009-06-25 | 2013-06-11 | Uop Llc | Polybenzoxazole membranes prepared from aromatic polyamide membranes |
US8915379B2 (en) * | 2009-09-25 | 2014-12-23 | Uop Llc | Method to improve the selectivity of polybenzoxazole membranes |
US8931646B2 (en) * | 2009-09-25 | 2015-01-13 | Uop Llc | Polybenzoxazole membranes |
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CN102448591A (zh) | 2012-05-09 |
CA2755919A1 (en) | 2010-09-30 |
US8132677B2 (en) | 2012-03-13 |
WO2010110994A3 (en) | 2011-01-06 |
MY152462A (en) | 2014-10-15 |
US9138692B2 (en) | 2015-09-22 |
AU2010229168A1 (en) | 2011-10-06 |
BRPI1013681A2 (pt) | 2016-04-26 |
WO2010110994A2 (en) | 2010-09-30 |
EP2411131A2 (en) | 2012-02-01 |
JP2012521872A (ja) | 2012-09-20 |
US20120276300A1 (en) | 2012-11-01 |
KR20110130486A (ko) | 2011-12-05 |
US20110278227A1 (en) | 2011-11-17 |
US8241501B2 (en) | 2012-08-14 |
KR101422903B1 (ko) | 2014-07-30 |
AU2010229168B2 (en) | 2014-11-20 |
US20100133192A1 (en) | 2010-06-03 |
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