JP2006512472A5 - - Google Patents
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- JP2006512472A5 JP2006512472A5 JP2005507914A JP2005507914A JP2006512472A5 JP 2006512472 A5 JP2006512472 A5 JP 2006512472A5 JP 2005507914 A JP2005507914 A JP 2005507914A JP 2005507914 A JP2005507914 A JP 2005507914A JP 2006512472 A5 JP2006512472 A5 JP 2006512472A5
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- JP
- Japan
- Prior art keywords
- nanofilm
- amphiphilic
- polymer component
- composition
- nanofilm composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229920000642 polymer Polymers 0.000 claims description 376
- 239000000203 mixture Substances 0.000 claims description 344
- -1 polyethylene Chemical group 0.000 claims description 101
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 97
- 238000000034 method Methods 0.000 claims description 96
- 239000012071 phase Substances 0.000 claims description 84
- OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 claims description 62
- 230000035699 permeability Effects 0.000 claims description 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
- 239000000178 monomer Substances 0.000 claims description 32
- 238000001914 filtration Methods 0.000 claims description 25
- 239000007788 liquid Substances 0.000 claims description 25
- 239000007795 chemical reaction product Substances 0.000 claims description 21
- 230000003993 interaction Effects 0.000 claims description 20
- 150000001412 amines Chemical class 0.000 claims description 19
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 19
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 17
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- 150000002148 esters Chemical class 0.000 claims description 16
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- 229910052740 iodine Inorganic materials 0.000 claims description 15
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- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 12
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- 239000004698 Polyethylene Chemical group 0.000 claims description 11
- 229920000573 polyethylene Chemical group 0.000 claims description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 10
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- 239000002202 Polyethylene glycol Substances 0.000 claims description 10
- 239000004642 Polyimide Substances 0.000 claims description 10
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- 239000007789 gas Substances 0.000 claims description 10
- 229920006393 polyether sulfone Polymers 0.000 claims description 10
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- 108010039918 Polylysine Proteins 0.000 claims description 8
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- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 8
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- 229920001567 vinyl ester resin Polymers 0.000 claims description 8
- 239000004711 α-olefin Substances 0.000 claims description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- 229920000936 Agarose Polymers 0.000 claims description 7
- 235000021355 Stearic acid Nutrition 0.000 claims description 7
- 150000001993 dienes Chemical class 0.000 claims description 7
- 150000002009 diols Chemical class 0.000 claims description 7
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 7
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 7
- 229920000058 polyacrylate Polymers 0.000 claims description 7
- 230000000379 polymerizing effect Effects 0.000 claims description 7
- 108091033319 polynucleotide Proteins 0.000 claims description 7
- 229920005862 polyol Polymers 0.000 claims description 7
- 150000003077 polyols Chemical class 0.000 claims description 7
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 7
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 7
- 239000011118 polyvinyl acetate Substances 0.000 claims description 7
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 7
- 239000008117 stearic acid Substances 0.000 claims description 7
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 6
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims description 6
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
- 239000004793 Polystyrene Substances 0.000 claims description 6
- 229920001328 Polyvinylidene chloride Polymers 0.000 claims description 6
- 239000001913 cellulose Substances 0.000 claims description 6
- 229920002301 cellulose acetate Polymers 0.000 claims description 6
- 229930016911 cinnamic acid Natural products 0.000 claims description 6
- 235000013985 cinnamic acid Nutrition 0.000 claims description 6
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 claims description 6
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 6
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 6
- 229920001707 polybutylene terephthalate Polymers 0.000 claims description 6
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 6
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 6
- 229920001195 polyisoprene Polymers 0.000 claims description 6
- 102000040430 polynucleotide Human genes 0.000 claims description 6
- 239000002157 polynucleotide Substances 0.000 claims description 6
- 229920002223 polystyrene Polymers 0.000 claims description 6
- 239000005033 polyvinylidene chloride Substances 0.000 claims description 6
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 claims description 5
- 229920000945 Amylopectin Polymers 0.000 claims description 5
- 229920000856 Amylose Polymers 0.000 claims description 5
- 229920002101 Chitin Polymers 0.000 claims description 5
- 229920001661 Chitosan Polymers 0.000 claims description 5
- 229920002307 Dextran Polymers 0.000 claims description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 5
- 229920002527 Glycogen Polymers 0.000 claims description 5
- 229930186217 Glycolipid Natural products 0.000 claims description 5
- 108090000288 Glycoproteins Proteins 0.000 claims description 5
- 102000003886 Glycoproteins Human genes 0.000 claims description 5
- 229920002683 Glycosaminoglycan Polymers 0.000 claims description 5
- MSFSPUZXLOGKHJ-UHFFFAOYSA-N Muraminsaeure Natural products OC(=O)C(C)OC1C(N)C(O)OC(CO)C1O MSFSPUZXLOGKHJ-UHFFFAOYSA-N 0.000 claims description 5
- 108010013639 Peptidoglycan Proteins 0.000 claims description 5
- 239000004697 Polyetherimide Substances 0.000 claims description 5
- 229920000954 Polyglycolide Polymers 0.000 claims description 5
- 108010067787 Proteoglycans Proteins 0.000 claims description 5
- 102000016611 Proteoglycans Human genes 0.000 claims description 5
- 108091034057 RNA (poly(A)) Proteins 0.000 claims description 5
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 5
- 239000004202 carbamide Substances 0.000 claims description 5
- 150000001720 carbohydrates Chemical class 0.000 claims description 5
- 239000008103 glucose Substances 0.000 claims description 5
- 229940096919 glycogen Drugs 0.000 claims description 5
- 229920000554 ionomer Polymers 0.000 claims description 5
- 230000001404 mediated effect Effects 0.000 claims description 5
- 102000039446 nucleic acids Human genes 0.000 claims description 5
- 150000007523 nucleic acids Chemical class 0.000 claims description 5
- 229920000141 poly(maleic anhydride) Polymers 0.000 claims description 5
- 229920002401 polyacrylamide Polymers 0.000 claims description 5
- 229920001601 polyetherimide Polymers 0.000 claims description 5
- 239000004633 polyglycolic acid Substances 0.000 claims description 5
- 239000004626 polylactic acid Substances 0.000 claims description 5
- 229920000136 polysorbate Polymers 0.000 claims description 5
- 229950008882 polysorbate Drugs 0.000 claims description 5
- 108010088751 Albumins Proteins 0.000 claims description 4
- 102000009027 Albumins Human genes 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 150000003949 imides Chemical class 0.000 claims description 4
- 239000004615 ingredient Substances 0.000 claims description 4
- 108020004707 nucleic acids Proteins 0.000 claims description 4
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- 108010058846 Ovalbumin Proteins 0.000 claims description 3
- 238000005266 casting Methods 0.000 claims description 3
- 229940109239 creatinine Drugs 0.000 claims description 3
- 238000003618 dip coating Methods 0.000 claims description 3
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- 239000010954 inorganic particle Substances 0.000 claims description 3
- 229940092253 ovalbumin Drugs 0.000 claims description 3
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- 108010062374 Myoglobin Proteins 0.000 claims description 2
- 102000036675 Myoglobin Human genes 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims description 2
- 239000007863 gel particle Substances 0.000 claims description 2
- 239000001307 helium Substances 0.000 claims description 2
- 229910052734 helium Inorganic materials 0.000 claims description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 2
- 229940027941 immunoglobulin g Drugs 0.000 claims description 2
- 230000003612 virological effect Effects 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 description 148
- 241000894007 species Species 0.000 description 116
- 239000000243 solution Substances 0.000 description 115
- 238000005859 coupling reaction Methods 0.000 description 106
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
- 238000010168 coupling process Methods 0.000 description 101
- 230000008878 coupling Effects 0.000 description 99
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 89
- 239000011148 porous material Substances 0.000 description 89
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 73
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- 125000003118 aryl group Chemical group 0.000 description 32
- RZVGUUMNWCDIBV-UHFFFAOYSA-N diethyl propanediimidate Chemical compound CCOC(=N)CC(=N)OCC RZVGUUMNWCDIBV-UHFFFAOYSA-N 0.000 description 31
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
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- 125000001424 substituent group Chemical group 0.000 description 26
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- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
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- 238000000089 atomic force micrograph Methods 0.000 description 10
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- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 10
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- 125000001931 aliphatic group Chemical group 0.000 description 9
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- 125000004432 carbon atom Chemical group C* 0.000 description 9
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Families Citing this family (56)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US6001067A (en) | 1997-03-04 | 1999-12-14 | Shults; Mark C. | Device and method for determining analyte levels |
| US8527026B2 (en) | 1997-03-04 | 2013-09-03 | Dexcom, Inc. | Device and method for determining analyte levels |
| ATE409215T1 (de) | 1998-05-05 | 2008-10-15 | Massachusetts Inst Technology | Emittierende polymere und vorrichtungen diese polymere enthaltend |
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| US20030032874A1 (en) | 2001-07-27 | 2003-02-13 | Dexcom, Inc. | Sensor head for use with implantable devices |
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| US10022078B2 (en) | 2004-07-13 | 2018-07-17 | Dexcom, Inc. | Analyte sensor |
| AU2003266021A1 (en) * | 2002-09-10 | 2004-04-30 | California Institute Of Technology | High-capacity nanostructured silicon and lithium alloys thereof |
| US20040106741A1 (en) * | 2002-09-17 | 2004-06-03 | Kriesel Joshua W. | Nanofilm compositions with polymeric components |
| JP4708342B2 (ja) | 2003-07-25 | 2011-06-22 | デックスコム・インコーポレーテッド | 埋設可能な装置に用いる酸素増大膜システム |
| US7368564B2 (en) * | 2003-08-06 | 2008-05-06 | Covalent Partners, Llc | Bridged macrocyclic module compositions |
| US7920906B2 (en) | 2005-03-10 | 2011-04-05 | Dexcom, Inc. | System and methods for processing analyte sensor data for sensor calibration |
| US9247900B2 (en) | 2004-07-13 | 2016-02-02 | Dexcom, Inc. | Analyte sensor |
| US7781102B2 (en) * | 2004-04-22 | 2010-08-24 | California Institute Of Technology | High-capacity nanostructured germanium-containing materials and lithium alloys thereof |
| US8277713B2 (en) | 2004-05-03 | 2012-10-02 | Dexcom, Inc. | Implantable analyte sensor |
| DE602005020806D1 (de) * | 2004-06-15 | 2010-06-02 | Dentsply Int Inc | Mensetzungen mit geringer polymerisationsspannung |
| WO2006002086A1 (en) * | 2004-06-15 | 2006-01-05 | Dentsply International Inc. | Low shrinkage and low stress dental compositions |
| US8989833B2 (en) | 2004-07-13 | 2015-03-24 | Dexcom, Inc. | Transcutaneous analyte sensor |
| WO2006034081A2 (en) * | 2004-09-17 | 2006-03-30 | Massachusetts Institute Of Technology | Polymers for analyte detection |
| US20090246887A1 (en) * | 2005-01-07 | 2009-10-01 | Academia Sinica | Diamond Crystallites For Biotechnological Applications |
| US8744546B2 (en) | 2005-05-05 | 2014-06-03 | Dexcom, Inc. | Cellulosic-based resistance domain for an analyte sensor |
| US7671166B2 (en) * | 2005-11-22 | 2010-03-02 | Massachusetts Institute Of Technology | High internal free volume compositions for low-k dielectric and other applications |
| US7863381B2 (en) * | 2006-03-08 | 2011-01-04 | 3M Innovative Properties Company | Polymer composites |
| WO2007120381A2 (en) | 2006-04-14 | 2007-10-25 | Dexcom, Inc. | Analyte sensor |
| US7678838B2 (en) * | 2006-08-04 | 2010-03-16 | University Of Memphis Research Foundation | Nanothin polymer films with selective pores and method of use thereof |
| WO2008042289A2 (en) | 2006-09-29 | 2008-04-10 | Massachusetts Institute Of Technology | Polymer synthetic technique |
| US8802447B2 (en) * | 2006-10-05 | 2014-08-12 | Massachusetts Institute Of Technology | Emissive compositions with internal standard and related techniques |
| US20090215189A1 (en) | 2006-10-27 | 2009-08-27 | Massachusetts Institute Of Technology | Sensor of species including toxins and chemical warfare agents |
| US7829155B1 (en) | 2006-11-22 | 2010-11-09 | The University Of Memphis Research Foundation | Nanothin polymer coatings containing thiol and methods of use thereof |
| US20090247855A1 (en) * | 2008-03-28 | 2009-10-01 | Dexcom, Inc. | Polymer membranes for continuous analyte sensors |
| US11730407B2 (en) | 2008-03-28 | 2023-08-22 | Dexcom, Inc. | Polymer membranes for continuous analyte sensors |
| US8583204B2 (en) | 2008-03-28 | 2013-11-12 | Dexcom, Inc. | Polymer membranes for continuous analyte sensors |
| US8682408B2 (en) | 2008-03-28 | 2014-03-25 | Dexcom, Inc. | Polymer membranes for continuous analyte sensors |
| US8560039B2 (en) | 2008-09-19 | 2013-10-15 | Dexcom, Inc. | Particle-containing membrane and particulate electrode for analyte sensors |
| TWI398353B (zh) * | 2009-03-02 | 2013-06-11 | Ind Tech Res Inst | 奈米纖維材料與脫鹽過濾材料 |
| US8273306B2 (en) * | 2009-07-15 | 2012-09-25 | Kimberly-Clark Worldwide, Inc. | Color-changing materials and multiple component materials having a color-changing composition |
| US8574673B2 (en) * | 2009-07-31 | 2013-11-05 | Nantero Inc. | Anisotropic nanotube fabric layers and films and methods of forming same |
| US8128993B2 (en) * | 2009-07-31 | 2012-03-06 | Nantero Inc. | Anisotropic nanotube fabric layers and films and methods of forming same |
| WO2012050399A2 (ko) * | 2010-10-14 | 2012-04-19 | 주식회사 엘지화학 | 용융 가공용 수지 혼합물 |
| EP2756167B1 (en) * | 2011-09-12 | 2018-01-17 | Saudi Arabian Oil Company | Nanostructured fluid sampling device |
| JP6551641B2 (ja) * | 2014-05-21 | 2019-07-31 | 凸版印刷株式会社 | 構造体および構造体の製造方法 |
| WO2016010061A1 (ja) | 2014-07-15 | 2016-01-21 | 国立研究開発法人科学技術振興機構 | 自己組織化膜形成材料として有用なトリプチセン誘導体、その製造方法、それを用いた膜、当該膜の製造方法、及びそれを用いた電子デバイス |
| KR102562973B1 (ko) * | 2015-12-31 | 2023-08-02 | 엘지디스플레이 주식회사 | 표시장치 |
| KR101808122B1 (ko) | 2016-08-08 | 2017-12-14 | 휴먼켐 주식회사 | 안티블락킹 입자를 포함한 이형필름 제조 방법 및 그 이형필름 |
| CN107413210B (zh) * | 2017-05-17 | 2020-04-17 | 宁波聚仁塑化材料有限公司 | 一种多巴胺和葡萄糖改性交联聚酰亚胺纳滤膜的制备方法 |
| KR102212128B1 (ko) * | 2018-05-10 | 2021-02-17 | 주식회사 엘지화학 | 역삼투막, 이의 제조방법 및 수처리 모듈 |
| CN108854265A (zh) * | 2018-06-26 | 2018-11-23 | 桐乡守敬应用技术研究院有限公司 | 一种复合过滤材料及其制备方法 |
| CN108721702B (zh) * | 2018-06-29 | 2021-06-29 | 江西理工大学 | 一种镁/左旋聚乳酸复合骨支架的制备方法 |
| CN109192922B (zh) * | 2018-08-07 | 2021-06-29 | 格林美(无锡)能源材料有限公司 | 一种具有特殊结构的固态锂离子电池正极及其制备方法 |
| KR102040496B1 (ko) * | 2018-08-14 | 2019-11-05 | 한국화학연구원 | 연속상 나노다공성 구조의 광확산 필름의 제조방법, 그 광확산 필름 및 이를 포함하는 광학장치 |
| CN109942731B (zh) * | 2019-04-08 | 2021-04-27 | 武汉轻工大学 | 一种纳米金/聚甲基丙烯酸甲酯导电材料的制备方法 |
| KR102538214B1 (ko) * | 2020-11-20 | 2023-05-31 | 고려대학교 산학협력단 | 바이러스 포집용 마스크 |
| CN113509848B (zh) * | 2021-04-27 | 2023-03-21 | 北京工业大学 | 一种基于液-液界面制备聚醚嵌段酰胺渗透汽化复合膜的方法 |
| CN113522037A (zh) * | 2021-07-21 | 2021-10-22 | 江苏盈天化学有限公司 | 一种渗透汽化四氢呋喃脱水复合膜的制备方法 |
Family Cites Families (118)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3847949A (en) * | 1970-05-12 | 1974-11-12 | Du Pont | Macrocyclic hetero imine complexing agents |
| FR2155926B1 (https=) * | 1971-10-15 | 1973-11-30 | Cetrane Laboratoire | |
| US4031111A (en) * | 1973-01-08 | 1977-06-21 | E. I. Du Pont De Nemours And Company | Macrocyclic hetero imine complexing agents |
| US4155793A (en) * | 1977-11-21 | 1979-05-22 | General Electric Company | Continuous preparation of ultrathin polymeric membrane laminates |
| CS213944B1 (en) * | 1980-04-24 | 1982-04-09 | Jaromir Petranek | Calcium/ii/-selective polymeric diaphragm |
| US4997676A (en) * | 1982-02-26 | 1991-03-05 | Limitinstant Limited | Immobilized inorganic diffusion barriers and the use thereof in the separation of small molecular species from a solution |
| US4554076A (en) * | 1982-08-18 | 1985-11-19 | Georgia Tech Research Corporation | Method of modifying membrane surface with oriented monolayers of amphiphilic compounds |
| US4661526A (en) * | 1983-02-02 | 1987-04-28 | Memtec Limited | Cross linked porous membranes |
| US4438251A (en) * | 1983-05-16 | 1984-03-20 | Armstrong World Industries, Inc. | Polyurethane polymers comprising macrocyclic crown ethers in the polymer backbone |
| SU1139731A1 (ru) | 1983-10-12 | 1985-02-15 | Ордена Ленина Институт Геохимии И Аналитической Химии Им.В.И.Вернадского | 1 @ ,15 @ -Тетрасульфо-1 @ ,15 @ -тетраокси-2,3,13,14,16,17,27,28-октааза-5,8,11,19,22,25-гексаокса-1,15 ди(2,7)нафта-4,12,18,26 тетра(1,2)фена-циклооктакоза-2,13,16,27-тетраен в качестве реагента дл фотометрического определени бари |
| SU1139730A1 (ru) | 1983-10-12 | 1985-02-15 | Ордена Ленина Институт Геохимии И Аналитической Химии Им.В.И.Вернадского | 1 @ ,12 @ -Тетрасульфо-1 @ ,12 @ -тетраокси-2,3,10,11,13,14,21,22-октааза-5,8,16,19-тетраокса-1,12 ди(2,7)нафта-4,9,15,20-тетра(1,2)фена-циклодокоза-2,10,13,21-тетраен в качестве реагента дл фотометрического определени берилли |
| DE3477183D1 (en) * | 1983-11-05 | 1989-04-20 | Akzo Nv | Organoclay materials |
| US4560599A (en) * | 1984-02-13 | 1985-12-24 | Marquette University | Assembling multilayers of polymerizable surfactant on a surface of a solid material |
| FR2564004B1 (fr) * | 1984-05-10 | 1993-04-09 | Commissariat Energie Atomique | Procede de fabrication d'un film mince comportant au moins une couche monomoleculaire de molecules non amphiphiles |
| US5362476A (en) * | 1984-10-18 | 1994-11-08 | Board Of Regents, The University Of Texas System | Alkyl phosphonate polyazamacrocyclic cheates for MRI |
| SU1266849A1 (ru) | 1985-01-31 | 1986-10-30 | Ордена Ленина Институт Геохимии И Аналитической Химии Им.В.И.Вернадского | Макроциклические бисазорезорцины систем ундека,-тетрадека,гептадекадиена |
| US5059510A (en) * | 1985-02-04 | 1991-10-22 | Hoechst Celanese Corp. | Media for optical information storage comprising an organic macrocyclic chromophore substituted with a film conferring organic substituent |
| US5173365A (en) * | 1985-03-25 | 1992-12-22 | Nanofilm Corporation | Ultra-thin molecular film |
| CA1290490C (en) * | 1985-11-20 | 1991-10-08 | Masakazu Uekita | Amphiphilic high polymer and process for producing the same |
| US5023252A (en) * | 1985-12-04 | 1991-06-11 | Conrex Pharmaceutical Corporation | Transdermal and trans-membrane delivery of drugs |
| US4722856A (en) * | 1986-01-02 | 1988-02-02 | Molecular Electronics Corporation | Method and apparatus for depositing monomolecular layers on a substrate |
| CA1302675C (en) * | 1986-05-20 | 1992-06-09 | Masakazu Uekita | Thin film and device having the same |
| US4948506A (en) * | 1986-07-07 | 1990-08-14 | Bend Research, Inc. | Physicochemically functional ultrathin films by interfacial polymerization |
| US5069945A (en) * | 1986-10-20 | 1991-12-03 | Memtec America Corporation | Ultrapous thin-film membranes |
| US4814082A (en) * | 1986-10-20 | 1989-03-21 | Memtec North America Corporation | Ultrafiltration thin film membranes |
| US4808480A (en) * | 1986-11-25 | 1989-02-28 | Lehigh University | Polymerizable heterocyclic disulfide-based compounds and membranes made therefrom |
| US4828917A (en) * | 1987-05-08 | 1989-05-09 | Basf Aktiengesellschaft | Layer of metallomacrocyclic polymer on substrate |
| US5229465A (en) * | 1990-06-30 | 1993-07-20 | Praxair Technology, Inc. | Oxygen-permeable polymeric membranes |
| US5489425A (en) * | 1987-06-24 | 1996-02-06 | The Dow Chemical Company | Functionalized polyamine chelants |
| US5064956A (en) * | 1987-06-24 | 1991-11-12 | The Dow Chemical Company | Process for preparing mono-n-alkylated polyazamacrocycles |
| DE3724543A1 (de) * | 1987-07-24 | 1989-02-02 | Basf Ag | Verfahren zur herstellung von duennen schichten |
| US5179213A (en) * | 1987-09-04 | 1993-01-12 | Brigham Young University | Macrocyclic ligands bonded to an inorganic support matrix and a process for selectively and quantitatively removing and concentrating ions present at low concentrations from mixtures thereof with other ions |
| SU1532560A1 (ru) | 1988-04-22 | 1989-12-30 | Институт геохимии и аналитической химии им.В.И.Вернадского | Способ получени симметричных макроциклических олигоэфиров |
| EP0449831A4 (en) * | 1988-06-03 | 1992-05-20 | Board Of Regents The University Of Texas System | Compounds and methods based on 1.1.1)propellane |
| US5102798A (en) * | 1988-09-08 | 1992-04-07 | Allage Associates | Surface functionalized Langmuir-Blodgett films for immobilization of active moieties |
| GB8922069D0 (en) * | 1989-09-29 | 1989-11-15 | Alcan Int Ltd | Separation devices incorporating porous anodic films |
| US5798261A (en) * | 1989-10-31 | 1998-08-25 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Distributed pore chemistry in porous organic polymers |
| US5368712A (en) * | 1989-11-02 | 1994-11-29 | Synporin Technologies, Inc. | Biologically mimetic synthetic ion channel transducers |
| DE3938992A1 (de) * | 1989-11-21 | 1991-05-23 | Schering Ag | Kaskadenpolymer-gebundene komplexbildner, deren komplexe und konjugate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
| DE4012750A1 (de) * | 1990-04-21 | 1991-10-24 | Hoechst Ag | Ferroelektrisches fluessigkristalldisplay mit hohem kontrast und hoher helligkeit |
| IL93020A (en) * | 1990-01-09 | 1995-06-29 | Yeda Res & Dev | Biosensors comprising a lipid bilayer doped with ion channels anchored to a recording electrode by bridging molecules |
| US5143784A (en) * | 1990-05-10 | 1992-09-01 | Nec Corporation | Soluble calixarene derivative and films thereof |
| FR2666092B1 (fr) * | 1990-08-23 | 1993-12-03 | Commissariat A Energie Atomique | Membranes organiques bidimensionnelles et leurs procedes de preparation. |
| DE4035378C2 (de) | 1990-11-07 | 2000-11-02 | Oeffentliche Pruefstelle Und T | Textiles Material sowie Verfahren zur Herstellung eines derartigen textilen Materials |
| KR930702967A (ko) | 1991-01-29 | 1993-11-29 | 프랭크 쿵 | 마크로고리 화합물의 항응고 특성 및 그것을 이용한 치료방법 |
| DE4135847A1 (de) * | 1991-10-31 | 1993-05-06 | Bayer Ag, 5090 Leverkusen, De | Asymmetrische, semipermeable membranen aus aromatischen polykondensaten, verfahren zu ihrer herstellung und ihre verwendung |
| EP1067134B1 (en) * | 1991-11-07 | 2004-07-28 | Nanotronics, Inc. | Hybridization of polynucleotides conjugated with chromophores and fluorophores to generate donor-to-donor energy transfer system |
| US5278051A (en) * | 1991-12-12 | 1994-01-11 | New York University | Construction of geometrical objects from polynucleotides |
| US5237067A (en) * | 1992-02-04 | 1993-08-17 | Schumaker Robert R | Optoelectronic tautomeric compositions |
| US5919369A (en) * | 1992-02-06 | 1999-07-06 | Hemocleanse, Inc. | Hemofiltration and plasmafiltration devices and methods |
| US5788862A (en) * | 1992-05-13 | 1998-08-04 | Pall Corporation | Filtration medium |
| US5342934A (en) * | 1992-06-19 | 1994-08-30 | The Trustees Of Columbia University In The City Of New York | Enantioselective receptor for amino acid derivatives, and other compounds |
| JP3624315B2 (ja) * | 1992-07-29 | 2005-03-02 | バクスター、インターナショナル、インコーポレイテッド | 親水性表面を有する生物材料 |
| US5410045A (en) * | 1992-08-04 | 1995-04-25 | Board Of Regents, The University Of Texas System | Rubyrin and related expanded porphyrins |
| DE4226556A1 (de) * | 1992-08-11 | 1994-02-17 | Hoechst Ag | Modifizierter Polyzucker als Orientierungsschicht für Flüssigkristalldisplays |
| US5231161A (en) * | 1992-10-22 | 1993-07-27 | General Electric Company | Method for preparation of macrocyclic poly(alkylene dicarboxylate) oligomers from bis(hydroxyalkyl) dicarboxylates |
| DE4305970A1 (de) * | 1993-02-26 | 1994-09-01 | Hoechst Ag | Cyclische Strukturelemente enthaltende Silan-Koppler als Orientierungsfilme |
| US5368889A (en) * | 1993-04-16 | 1994-11-29 | The Dow Chemical Company | Method of making thin film composite membranes |
| US6001364A (en) * | 1993-05-05 | 1999-12-14 | Gryphon Sciences | Hetero-polyoxime compounds and their preparation by parallel assembly |
| US5357029A (en) * | 1993-06-24 | 1994-10-18 | General Electric Co. | Macrocyclic polyimide oligomers and method for their preparation |
| US5449761A (en) * | 1993-09-28 | 1995-09-12 | Cytogen Corporation | Metal-binding targeted polypeptide constructs |
| GB9321545D0 (en) | 1993-10-19 | 1993-12-08 | Secr Defence | Sensors for neutral molecules |
| AU704878B2 (en) * | 1994-01-05 | 1999-05-06 | Arqule, Inc. | Method of making polymers having specific properties |
| US5561043A (en) * | 1994-01-31 | 1996-10-01 | Trustees Of Boston University | Self-assembling multimeric nucleic acid constructs |
| US5831087A (en) * | 1994-03-02 | 1998-11-03 | Hoechst Celanese Corp. | Macrocyclic imide compounds |
| EP0804249A2 (en) * | 1994-03-15 | 1997-11-05 | Brown University Research Foundation | Polymeric gene delivery system |
| ATE509102T1 (de) * | 1994-07-15 | 2011-05-15 | Univ Iowa Res Found | Immunomodulatorische oligonukleotide |
| GB9420390D0 (en) * | 1994-10-10 | 1994-11-23 | Nycomed Salutar Inc | Liposomal agents |
| US5614099A (en) * | 1994-12-22 | 1997-03-25 | Nitto Denko Corporation | Highly permeable composite reverse osmosis membrane, method of producing the same, and method of using the same |
| US6076318A (en) * | 1995-03-06 | 2000-06-20 | Polyceramics, Inc. | Interlocking puzzle |
| US5560151A (en) * | 1995-03-06 | 1996-10-01 | Polyceramics, Inc. | Building blocks forming hexagonal and pentagonal building units for modular structures |
| GB9504910D0 (en) * | 1995-03-10 | 1995-04-26 | Nycomed Imaging As | Compounds |
| US6340588B1 (en) * | 1995-04-25 | 2002-01-22 | Discovery Partners International, Inc. | Matrices with memories |
| DE19518624C1 (de) * | 1995-05-24 | 1996-11-21 | Akzo Nobel Nv | Synthetische Trennmembran |
| GB9511396D0 (en) | 1995-06-06 | 1995-08-02 | British Nuclear Fuels Plc | Chemical complexes |
| US6210551B1 (en) * | 1995-08-01 | 2001-04-03 | Australian Membrane And Biotechnology Research Institute | Composite membrane sensor |
| US5876830A (en) * | 1995-09-08 | 1999-03-02 | Board Of Regents Of The University Of Colorado | Method of assembly of molecular-sized nets and scaffolding |
| EP0856026A1 (en) * | 1995-10-19 | 1998-08-05 | Receptagen Corporation | Discrete-length polyethylene glycols |
| US5830539A (en) * | 1995-11-17 | 1998-11-03 | The State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of The University Of Oregon | Methods for functionalizing and coating substrates and devices made according to the methods |
| US20010009904A1 (en) * | 1997-12-30 | 2001-07-26 | Jon A. Wolff | Process of delivering a polynucleotide to a cell via the vascular system |
| US6171497B1 (en) * | 1996-01-24 | 2001-01-09 | Nitto Denko Corporation | Highly permeable composite reverse osmosis membrane |
| US5883246A (en) * | 1996-03-07 | 1999-03-16 | Qlt Phototherapeutics, Inc. | Synthesis of polypyrrolic macrocycles from meso-substituted tripyrrane compounds |
| JP3681214B2 (ja) * | 1996-03-21 | 2005-08-10 | 日東電工株式会社 | 高透過性複合逆浸透膜 |
| CA2251072A1 (en) * | 1996-04-05 | 1997-10-16 | Philip A. Gale | Calixpyrroles, calixpyridinopyrroles and calixpyridines |
| US6072044A (en) * | 1996-04-26 | 2000-06-06 | New York University | Nanoconstructions of geometrical objects and lattices from antiparallel nucleic acid double crossover molecules |
| US5695887A (en) * | 1996-05-09 | 1997-12-09 | Bell Communications Research, Inc. | Chelation treatment for reduced self-discharge in Li-ion batteries |
| CA2256900A1 (en) * | 1996-05-29 | 1997-12-04 | Xiao-Ying Meng | Cationic polymer/lipid nucleic acid delivery vehicles |
| US5852127A (en) * | 1996-07-09 | 1998-12-22 | Rensselner Polytechnic Institute | Modification of porous and non-porous materials using self-assembled monolayers |
| DE19636337A1 (de) | 1996-08-30 | 1998-03-05 | Inst Angewandte Chemie Berlin | Polyazacalix[5]arene, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19646537A1 (de) | 1996-10-30 | 1998-05-07 | Inst Angewandte Chemie Berlin | Polyazacalix[6]arene, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US5677399A (en) * | 1996-11-07 | 1997-10-14 | Bridgestone Corporation | Synthesis of macrocyclic polymers with group IIA and IIB metal cyclic organometallic initiators |
| EP0889080A1 (en) * | 1996-12-10 | 1999-01-07 | Daicel Chemical Industries, Ltd. | Porous films, process for producing the same, and laminate films and recording sheets made with the use of the porous films |
| US5936100A (en) * | 1996-12-16 | 1999-08-10 | Studiengesellschaft Kohle Mbh | Synthesis of functionalized macrocycles by ring closing metathesis |
| US5912069A (en) * | 1996-12-19 | 1999-06-15 | Sigma Laboratories Of Arizona | Metal nanolaminate composite |
| DE19711078A1 (de) | 1997-01-05 | 1998-09-24 | Franz Dietrich Oeste | Organische Käfigverbindungen, Verfahren zu ihrer Herstellung und Anwendung |
| US5908692A (en) * | 1997-01-23 | 1999-06-01 | Wisconsin Alumni Research Foundation | Ordered organic monolayers and methods of preparation thereof |
| US6275866B1 (en) * | 1997-03-14 | 2001-08-14 | Mathsoft Engineering & Education, Inc. | Manipulation and coupling of object oriented components |
| US6033773A (en) * | 1997-04-18 | 2000-03-07 | The Regents Of The University Of California | Polar self-assembled thin films for non-linear optical materials |
| US6524613B1 (en) * | 1997-04-30 | 2003-02-25 | Regents Of The University Of Minnesota | Hepatocellular chimeraplasty |
| US5919440A (en) * | 1997-05-05 | 1999-07-06 | Procter & Gamble Company | Personal care compositions containing an odor masking base |
| US5933819C1 (en) * | 1997-05-23 | 2001-11-13 | Scripps Research Inst | Prediction of relative binding motifs of biologically active peptides and peptide mimetics |
| DE69809122T2 (de) * | 1997-05-30 | 2003-04-03 | Canon K.K., Tokio/Tokyo | Vorrichtung zur Herstellung Lagmuir-Blodgett-Filmen |
| DE19808844A1 (de) * | 1998-03-03 | 1999-09-09 | Huels Chemische Werke Ag | Verfahren zur Herstellung von makrocyclischen Estern |
| DE19808843C2 (de) * | 1998-03-03 | 2003-10-02 | Degussa | Verfahren zur Herstellung von makrocyclischen Estern |
| NL1008789C2 (nl) | 1998-04-02 | 1999-10-05 | Stichting Tech Wetenschapp | Anion-complexerende verbinding, werkwijze voor de bereiding ervan, een ionselectief membraan alsmede een sensor voorzien van een dergelijke verbinding of membraan. |
| US6271209B1 (en) * | 1998-04-03 | 2001-08-07 | Valentis, Inc. | Cationic lipid formulation delivering nucleic acid to peritoneal tumors |
| US6048736A (en) * | 1998-04-29 | 2000-04-11 | Kosak; Kenneth M. | Cyclodextrin polymers for carrying and releasing drugs |
| US6056903A (en) * | 1999-02-08 | 2000-05-02 | Osmonics, Inc. | Preparation of polyethersulfone membranes |
| US6380347B1 (en) * | 1999-04-09 | 2002-04-30 | Honeywell International Inc. | Nanoporous polymers comprising macrocycles |
| US6203850B1 (en) * | 1999-05-18 | 2001-03-20 | Neomecs Incorporated | Plasma-annealed porous polymers |
| JP2001151904A (ja) * | 1999-09-17 | 2001-06-05 | Univ Tokyo | J会合体配向分散膜及びその製造方法 |
| US6564288B2 (en) * | 2000-11-30 | 2003-05-13 | Hewlett-Packard Company | Memory controller with temperature sensors |
| US20040034223A1 (en) * | 2002-02-07 | 2004-02-19 | Covalent Partners, Llc. | Amphiphilic molecular modules and constructs based thereon |
| EP1481268A4 (en) * | 2002-02-07 | 2005-06-29 | Covalent Partners Llc | NANOFILM AND MEMBRANE COMPOSITIONS |
| EP1480635A4 (en) * | 2002-02-07 | 2005-06-29 | Covalent Partners Llc | COMPOSITIONS OF MACROCYCLIC MODULES |
| AU2003212293A1 (en) * | 2002-02-28 | 2003-09-09 | Switch Biotech Ag | Use of a fibroblast growth factor-binding protein for the treatment and diagnosis of diabetic wound healing problems |
| US20040106741A1 (en) * | 2002-09-17 | 2004-06-03 | Kriesel Joshua W. | Nanofilm compositions with polymeric components |
| US7368564B2 (en) * | 2003-08-06 | 2008-05-06 | Covalent Partners, Llc | Bridged macrocyclic module compositions |
-
2003
- 2003-04-29 US US10/426,475 patent/US20040106741A1/en not_active Abandoned
- 2003-09-05 WO PCT/US2003/027749 patent/WO2005018013A2/en not_active Ceased
- 2003-09-05 KR KR1020057004632A patent/KR20060056266A/ko not_active Ceased
- 2003-09-05 JP JP2005507914A patent/JP2006512472A/ja active Pending
- 2003-09-05 EP EP03816729A patent/EP1573833A4/en not_active Withdrawn
- 2003-09-05 AU AU2003304453A patent/AU2003304453B2/en not_active Ceased
-
2005
- 2005-08-10 US US11/202,322 patent/US7595368B2/en not_active Expired - Fee Related
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