CN103923352B - 羧基化离子液体方法制备的区域选择性取代的纤维素酯以及由此制备的产物 - Google Patents
羧基化离子液体方法制备的区域选择性取代的纤维素酯以及由此制备的产物 Download PDFInfo
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- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
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- C08B1/003—Preparation of cellulose solutions, i.e. dopes, with different possible solvents, e.g. ionic liquids
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- C—CHEMISTRY; METALLURGY
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- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
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- C—CHEMISTRY; METALLURGY
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- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B3/00—Preparation of cellulose esters of organic acids
- C08B3/16—Preparation of mixed organic cellulose esters, e.g. cellulose aceto-formate or cellulose aceto-propionate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B3/00—Preparation of cellulose esters of organic acids
- C08B3/22—Post-esterification treatments, including purification
- C08B3/26—Isolation of the cellulose ester
- C08B3/28—Isolation of the cellulose ester by precipitation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
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- G—PHYSICS
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- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
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- G02B5/30—Polarising elements
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- C08J2301/08—Cellulose derivatives
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| CN102441433B (zh) * | 2011-09-13 | 2014-07-30 | 昆明理工大学 | 一种离子液催化剂及其催化生物质废弃物液化气化的方法 |
| US20130178614A1 (en) | 2011-10-25 | 2013-07-11 | Virginia Tech Intellectual Properties, Inc. | Regioselectively substituted cellulose esters and efficient methods of preparing them |
| US20140048221A1 (en) | 2012-08-20 | 2014-02-20 | Celanese International Corporation | Methods for extracting hemicellulose from a cellulosic material |
| US9939554B2 (en) * | 2013-01-24 | 2018-04-10 | Akron Polymer Systems, Inc. | Wide-view optical film having reversed wavelength dispersion |
| CN103588883A (zh) * | 2013-11-22 | 2014-02-19 | 南开大学 | 一种基于离子液体的改性纤维素膜材料的制作方法 |
| US9309360B2 (en) | 2013-12-17 | 2016-04-12 | Eastman Chemical Company | Cellulose ester based quarter wave plates having normal wavelength dispersion |
| US9309362B2 (en) | 2013-12-17 | 2016-04-12 | Eastman Chemical Company | Optical films containing optical retardation-enhancing additive |
| US20160044955A1 (en) | 2014-08-13 | 2016-02-18 | R.J. Reynolds Tobacco Company | Smokeless tobacco products |
| WO2016068053A1 (ja) * | 2014-10-27 | 2016-05-06 | 国立大学法人金沢大学 | 多糖類誘導体及びリグニン誘導体の製造方法 |
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| JP6582485B2 (ja) * | 2015-03-27 | 2019-10-02 | セイコーエプソン株式会社 | 組成物、造形物の製造方法および造形物 |
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| CN105175760B (zh) * | 2015-07-16 | 2018-12-04 | 广西科开成林科技有限公司 | 一种醋酸丁酸纤维素膜的制备方法 |
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| US10293584B2 (en) | 2016-03-11 | 2019-05-21 | Solutia Inc. | Cellulose ester multilayer interlayers |
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| US10195826B2 (en) | 2016-03-11 | 2019-02-05 | Solutia Inc. | Cellulose ester multilayer interlayers |
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| WO2023175787A1 (ja) * | 2022-03-16 | 2023-09-21 | 国立大学法人金沢大学 | イオン液体の回収方法 |
| WO2023175788A1 (ja) * | 2022-03-16 | 2023-09-21 | 国立大学法人金沢大学 | イオン液体の回収方法 |
| JP2025104846A (ja) * | 2023-12-28 | 2025-07-10 | 広栄化学株式会社 | エステル化多糖類の製造方法 |
| JP2025133236A (ja) * | 2024-03-01 | 2025-09-11 | 国立大学法人神戸大学 | イオン液体中の着色成分の除去 |
| JP2025133235A (ja) * | 2024-03-01 | 2025-09-11 | 国立大学法人神戸大学 | イオン液体中のセルロース由来不純物の除去 |
Family Cites Families (186)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2563506A (en) | 1951-08-07 | Quaternary ammonium salts of | ||
| US2083A (en) * | 1841-05-06 | And cleaning out docks | ||
| US787994A (en) * | 1901-05-08 | 1905-04-25 | Walter P Sawyer | Harness-saddle. |
| US1996754A (en) | 1928-09-26 | 1935-04-09 | Celanese Corp | Improving the color of cellulose derivatives |
| US1943176A (en) | 1930-09-27 | 1934-01-09 | Chem Ind Basel | Cellulose solution |
| US1924238A (en) | 1930-09-27 | 1933-08-29 | Chem Ind Basel | Cellulose solution and cellulose derivative and process of making same |
| GB581046A (en) | 1943-07-27 | 1946-09-30 | British Celanese | Improvements in bleaching organic acid esters of cellulose |
| GB572017A (en) | 1943-10-04 | 1945-09-19 | Henry Dreyfus | Improvements relating to coating and impregnating compositions |
| GB611665A (en) | 1945-05-03 | 1948-11-02 | British Celanese | Improvements in the production of cellulose esters |
| US2651629A (en) | 1949-07-01 | 1953-09-08 | Celanese Corp | Cellulose esters |
| GB736964A (en) | 1951-05-17 | 1955-09-14 | Hercules Powder Co Ltd | Improvements in or relating to the treatment of cellulose esters |
| US3042408A (en) | 1957-07-05 | 1962-07-03 | Kenneth G Johnson | Game |
| US3042508A (en) | 1959-05-28 | 1962-07-03 | Stanley Works | Non-loading metal-backed abrader and method for its production |
| US3038708A (en) | 1959-11-02 | 1962-06-12 | Willard H Rice | Humidifier |
| GB1139616A (en) | 1967-04-17 | 1969-01-08 | Teijin Ltd | Process for producing bleached and purified cellulose acetate |
| DE2262829C3 (de) | 1972-12-22 | 1980-05-14 | Haarmann & Reimer Gmbh, 3450 Holzminden | Rauchbare Produkte |
| CA1071464A (en) | 1975-02-13 | 1980-02-12 | Carlton K. Bergsbaken | Dried soft curd cheese |
| US4028132A (en) | 1975-11-25 | 1977-06-07 | International Playtex, Inc. | Cellulose solutions and products prepared therefrom |
| US4189761A (en) | 1977-08-12 | 1980-02-19 | Sprague Electric Company | Non-aqueous electrolytic capacitor electrolyte |
| US4278790A (en) | 1978-07-31 | 1981-07-14 | Hopkins Agricultural Chemical Co. | Novel cellulose solutions |
| JPS56162617A (en) | 1980-05-20 | 1981-12-14 | Fuji Photo Film Co Ltd | Preparation of film |
| US4557951A (en) | 1983-11-22 | 1985-12-10 | A. E. Staley Manufacturing Company | Cellulosic organic solvent soluble products |
| JPS60144332A (ja) | 1983-12-26 | 1985-07-30 | Tachikawa Kenkyusho | 有機溶媒にセルロ−スを溶解する方法 |
| US4501888A (en) | 1984-01-24 | 1985-02-26 | A. E. Staley Manufacturing Company | Process for producing esters of carbohydrate materials |
| EP0330106A1 (de) | 1988-02-25 | 1989-08-30 | Akzo Nobel N.V. | Modifizierte Cellulose für biocompatible Dialysemembranen II und Verfahren zu deren Herstellung |
| DE4000092C2 (de) * | 1990-01-03 | 1994-01-13 | Mauricio Kling | Rotorlagerungsanordnung für eine Windkraftmaschine |
| DE4142761A1 (de) | 1991-12-23 | 1993-06-24 | Wolff Walsrode Ag | Verfahren zur herstellung von methyl-hydroxyalkyl-celluloseethern |
| JP3419412B2 (ja) | 1993-05-21 | 2003-06-23 | 三菱瓦斯化学株式会社 | 第四級アンモニウム有機カルボン酸塩の製造方法 |
| US5750677A (en) | 1994-12-30 | 1998-05-12 | Eastman Chemical Company | Direct process for the production of cellulose esters |
| US5876567A (en) | 1995-04-28 | 1999-03-02 | Yamamoto; Soichiro | Solvent recycling system |
| US5610233A (en) | 1995-08-03 | 1997-03-11 | Eastman Chemical Company | Aqueous coating compositions containing cellulose esters |
| US5977347A (en) | 1996-07-30 | 1999-11-02 | Daicel Chemical Industries, Ltd. | Cellulose acetate propionate |
| GB9719551D0 (en) | 1997-09-16 | 1997-11-19 | British Nuclear Fuels Plc | Treatment of molten salt reprocessing wastes |
| EP0911656B1 (en) * | 1997-10-20 | 2005-01-26 | Fuji Photo Film Co., Ltd. | Optical compensatory sheet and liquid crystal display |
| US7122660B1 (en) | 1998-03-17 | 2006-10-17 | Daicel Chemical Industries, Ltd. | Cellulose acetate and dope containing the same |
| ATE276043T1 (de) | 1999-05-26 | 2004-10-15 | Biotage Ab | Herstellung und verwendung von ionischen flüssigkeiten in mikrowellen-assistierten chemischen umwandlungen |
| GB0008707D0 (en) | 2000-04-07 | 2000-05-31 | Bp Chem Int Ltd | Imidazole carbenes |
| US6500215B1 (en) | 2000-07-11 | 2002-12-31 | Sybron Chemicals, Inc. | Utility of selected amine oxides in textile technology |
| JP2002179701A (ja) | 2000-12-15 | 2002-06-26 | Fuji Photo Film Co Ltd | セルロースアシレート |
| DE60112229T2 (de) | 2000-12-15 | 2006-01-12 | Fuji Photo Film Co., Ltd., Minami-Ashigara | Celluloseester einer aromatischen Carbonsäure |
| KR20030070607A (ko) | 2001-01-17 | 2003-08-30 | 후지 샤신 필름 가부시기가이샤 | 셀룰로스 아실레이트 및 이의 용액 |
| EP1285931B1 (en) | 2001-03-14 | 2013-05-15 | Daicel Chemical Industries, Ltd. | Method for adjusting the degree of substitution with acetyl group of cellulose acetate |
| JP2002265501A (ja) | 2001-03-14 | 2002-09-18 | Fuji Photo Film Co Ltd | セルロースアシレート溶液およびセルロースアシレートフイルムの製造方法 |
| JP2002275132A (ja) | 2001-03-21 | 2002-09-25 | Japan Carlit Co Ltd:The | 高純度四級アンモニウム無機酸塩の製造方法 |
| USH2083H1 (en) | 2001-03-27 | 2003-10-07 | Eastman Chemical Company | Cellulose acetate film for use in liquid crystal displays |
| US20030036493A1 (en) | 2001-05-01 | 2003-02-20 | The Procter & Gamble Company | Stable liquid or gel bleaching composition containing diacyl peroxide particles |
| EP1266740B1 (en) | 2001-06-15 | 2007-10-31 | FUJIFILM Corporation | Method of producing of cellulose ester film |
| DE10145747A1 (de) | 2001-09-17 | 2003-04-03 | Solvent Innovation Gmbh | Ionische Flüssigkeiten |
| US6824599B2 (en) | 2001-10-03 | 2004-11-30 | The University Of Alabama | Dissolution and processing of cellulose using ionic liquids |
| US6808557B2 (en) | 2001-10-03 | 2004-10-26 | The University Of Alabama | Cellulose matrix encapsulation and method |
| US6872766B2 (en) | 2001-10-03 | 2005-03-29 | Eastman Kodak Company | Ultraviolet light filter element |
| FR2831171B1 (fr) | 2001-10-24 | 2007-02-02 | Rhodia Chimie Sa | Procede de preparation d'acide poly-ou copoly-glucuronique |
| US6827773B2 (en) | 2001-10-31 | 2004-12-07 | North Carolina State University | Cellulose solvent compositions and methods of making and employing same |
| US6991718B2 (en) | 2001-11-21 | 2006-01-31 | Sachem, Inc. | Electrochemical process for producing ionic liquids |
| AR038161A1 (es) | 2002-01-24 | 2004-12-29 | Basf Ag | Procedimiento para separar acidos de mezclas de reaccion quimicas con la ayuda de liquidos ionicos |
| WO2003086605A2 (en) | 2002-04-05 | 2003-10-23 | University Of South Alabama | Functionalized ionic liquids, and methods of use thereof |
| US7324180B2 (en) | 2002-09-06 | 2008-01-29 | Dai Nippon Printing Co., Ltd. | Laminated retardation optical element, process of producing the same, and liquid crystal display |
| JP2004175785A (ja) | 2002-10-04 | 2004-06-24 | Keio Gijuku | グリコシル化法と、それに用いるための溶媒及び触媒 |
| CN1261496C (zh) | 2002-10-22 | 2006-06-28 | 中国科学院化学研究所 | 一种纤维素溶液及其制备方法 |
| JP4280486B2 (ja) | 2002-11-25 | 2009-06-17 | 富士フイルム株式会社 | 溶液製膜方法 |
| CN100424259C (zh) | 2002-12-12 | 2008-10-08 | 中国科学院化学研究所 | 一种含不饱和双键的室温离子液体及制备方法和应用 |
| US7585905B2 (en) | 2003-03-14 | 2009-09-08 | Eastman Chemical Company | Low molecular weight cellulose mixed esters and their use as low viscosity binders and modifiers in coating compositions |
| CN100470334C (zh) | 2003-03-28 | 2009-03-18 | 富士胶片株式会社 | 液晶显示装置 |
| DE10333239A1 (de) | 2003-07-21 | 2005-03-10 | Basf Ag | Verfahren zur Herstellung von gereinigten 1,3- substituierten Imidazoliumsalzen |
| AU2003904323A0 (en) | 2003-08-13 | 2003-08-28 | Viridian Chemical Pty Ltd | Solvents based on salts of aryl acids |
| FI115835B (fi) | 2003-08-15 | 2005-07-29 | Kemira Oyj | Liuotusmenetelmä |
| FI116142B (fi) | 2003-09-11 | 2005-09-30 | Kemira Oyj | Esteröintimenetelmä |
| JP4186063B2 (ja) | 2003-09-19 | 2008-11-26 | 富士フイルム株式会社 | セルロース組成物、セルロースフィルム、およびセルロースフィルム用の改質剤 |
| EP2532684A3 (en) | 2003-11-28 | 2013-03-20 | Eastman Chemical Company | Cellulose interpolymers and method of oxidation |
| FI116140B (fi) | 2003-12-03 | 2005-09-30 | Kemira Oyj | Eetteröintimenetelmä |
| FI116141B (fi) | 2004-01-05 | 2005-09-30 | Kemira Oyj | Depolymerointimenetelmä |
| DE102004003958A1 (de) | 2004-01-26 | 2005-08-11 | Basf Ag | Herstellungsmethode für ionische Flüssigkeiten |
| DE102004010662A1 (de) | 2004-03-04 | 2005-09-22 | Basf Ag | Verfahren zur Herstellung von Verbindungen mit quaternären sp2-hybridisierten Stickstoffatomen |
| WO2005093476A1 (en) | 2004-03-25 | 2005-10-06 | Fuji Photo Film Co., Ltd. | Transparent film and optical compensatory film, polarizing plate and liquid-crystal display device employing it |
| US7888412B2 (en) | 2004-03-26 | 2011-02-15 | Board Of Trustees Of The University Of Alabama | Polymer dissolution and blend formation in ionic liquids |
| JP4681245B2 (ja) | 2004-03-31 | 2011-05-11 | ダイセル化学工業株式会社 | セルロースエステル及びそのフィルム |
| JP2005307055A (ja) | 2004-04-22 | 2005-11-04 | Fuji Photo Film Co Ltd | セルロースアシレートの製造方法、セルロースアシレートフイルム、それを用いた光学機能性シート、偏光板、液晶表示装置 |
| US20060004192A1 (en) | 2004-07-02 | 2006-01-05 | Fuji Photo Film Co., Ltd. | Method of preparing a cellulose acylate, cellulose acylate film, polarizing plate, and liquid crystal display device |
| WO2006013869A1 (en) | 2004-08-04 | 2006-02-09 | Fujifilm Corporation | Thermoplastic film and method of producing the same |
| CN101039913A (zh) | 2004-08-24 | 2007-09-19 | 巴斯福股份公司 | 制备高纯度季铵化合物的方法 |
| JP2008510741A (ja) | 2004-08-24 | 2008-04-10 | ビーエーエスエフ ソシエタス・ヨーロピア | イオン液体を製造するための出発化合物としてのイミダゾリウム−メチルスルファイト |
| DE102004043631A1 (de) | 2004-09-07 | 2006-03-09 | Basf Ag | Verfahren zur Herstellung heterocyclischer quartärer Ammonium- Verbindungen und/oder Guanidinium- Verbindungen hoher Reinheit |
| DE102004043632A1 (de) | 2004-09-07 | 2006-03-09 | Basf Ag | Verfahren zur Herstellung heterocyclischer quartärer Ammonium- und/oder Guanidinium-Verbindungen |
| US20060062749A1 (en) | 2004-09-16 | 2006-03-23 | Shelton Michael C | personal care products incorporating cellulosic fatty acid esters |
| JP4108077B2 (ja) | 2004-09-22 | 2008-06-25 | ダイセル化学工業株式会社 | セルロースエステル及びその製造方法 |
| GB0422447D0 (en) | 2004-10-08 | 2004-11-10 | Univ Cambridge Tech | Use of ionic liquids |
| US7737102B2 (en) | 2004-11-01 | 2010-06-15 | The Procter & Gamble Company | Ionic liquids derived from functionalized anionic surfactants |
| JP4951750B2 (ja) | 2004-11-10 | 2012-06-13 | 国立大学法人東京農工大学 | 難溶性多糖類の溶解剤および該溶解剤と多糖類を含有してなる組成物 |
| JP2006137977A (ja) * | 2004-11-11 | 2006-06-01 | Hitachi Metals Ltd | 連続溶融金属めっき用ロール |
| JP4786909B2 (ja) | 2005-02-01 | 2011-10-05 | ダイセル化学工業株式会社 | セルロース混酸エステル及びその製造方法 |
| JP4594131B2 (ja) | 2005-02-24 | 2010-12-08 | 富士フイルム株式会社 | セルロースアシレートフィルム、位相差板、偏光板、液晶表示装置およびセルロースアシレートフィルムの製造方法 |
| JP5160040B2 (ja) | 2005-02-28 | 2013-03-13 | 千葉製粉株式会社 | 糖脂肪酸エステルの製造方法 |
| JP2006251439A (ja) | 2005-03-11 | 2006-09-21 | Nitto Denko Corp | 液晶パネル、液晶テレビおよび液晶表示装置 |
| US7438832B2 (en) | 2005-03-29 | 2008-10-21 | Eastman Kodak Company | Ionic liquid and electronically conductive polymer mixtures |
| JP4499594B2 (ja) | 2005-03-29 | 2010-07-07 | 第一工業製薬株式会社 | 超高純度イオン性液体 |
| US7550520B2 (en) | 2005-05-31 | 2009-06-23 | The University Of Alabama | Method of preparing high orientation nanoparticle-containing sheets or films using ionic liquids, and the sheets or films produced thereby |
| JP4646030B2 (ja) | 2005-03-31 | 2011-03-09 | 株式会社 日立ディスプレイズ | 液晶表示装置 |
| DE102005017733A1 (de) | 2005-04-15 | 2006-10-19 | Basf Ag | Löslichkeit von Cellulose in ionischen Flüssigkeiten unter Zugabe von Aminbase |
| DE102005017715A1 (de) | 2005-04-15 | 2006-10-19 | Basf Ag | Lösungen von Cellulose in ionischen Flüssigkeiten |
| US7763715B2 (en) | 2005-04-22 | 2010-07-27 | The Procter & Gamble Company | Extracting biopolymers from a biomass using ionic liquids |
| EP1911792A4 (en) | 2005-05-24 | 2009-09-23 | Fujifilm Corp | CELLULOSE ACRYLATE FILM, AND POLARIZING PLATE, OPTICAL COMPENSATING FILM, AND LIQUID CRYSTAL DISPLAY USING THE SAME |
| JP2006328298A (ja) | 2005-05-30 | 2006-12-07 | Konica Minolta Opto Inc | 光学フィルム、偏光板及び液晶表示装置 |
| AU2006266151B2 (en) | 2005-06-29 | 2011-09-22 | The University Of Alabama | Ionic liquid reconstituted cellulose composites as solid support matrices |
| KR100843594B1 (ko) | 2005-09-07 | 2008-07-03 | 주식회사 엘지화학 | 액상 산화 반응을 이용한 알데히드 화합물로부터의유기산의 제조 방법 |
| WO2007029508A1 (ja) | 2005-09-02 | 2007-03-15 | Konica Minolta Medical & Graphic, Inc. | 近赤外線吸収材料及びその製造方法 |
| BRPI0616976A2 (pt) | 2005-10-07 | 2009-11-24 | Univ Alabama | composições lìquidas iÈnicas multi-funcionais para superar polimorfismos e conferir propriedades a ingredientes ativos farmacêuticos, biológicos, nutricionais e energéticos |
| JP2007138141A (ja) | 2005-10-21 | 2007-06-07 | Fujifilm Corp | セルロースアシレートの製造方法、セルロースアシレートフィルム、並びに、該フィルムを用いた偏光板、位相差フィルム、光学フィルムおよび液晶表示装置 |
| WO2007049485A1 (ja) | 2005-10-25 | 2007-05-03 | Nisshinbo Industries, Inc. | セルロース溶液の製造方法、セルロース溶液および再生セルロースの製造方法 |
| CN100537603C (zh) | 2005-11-01 | 2009-09-09 | 中国科学院过程工程研究所 | 利用植物纤维素生产醋酸纤维素酯的方法 |
| DE102005055815A1 (de) | 2005-11-21 | 2007-05-24 | Basf Ag | Verfahren zur Herstellung von ionischen Flüssigkeiten |
| CN1978433A (zh) | 2005-12-09 | 2007-06-13 | 中国科学院兰州化学物理研究所 | 咪唑基双功能化的室温离子液体及其制备方法 |
| EP1966284B1 (de) | 2005-12-23 | 2013-04-17 | Basf Se | Lösungssystem auf der basis geschmolzener ionischer flüssigkeiten, dessen herstellung sowie verwendung zur herstellung regenerierter kohlenhydrate |
| CN100355960C (zh) | 2005-12-26 | 2007-12-19 | 东华大学 | 一种离子液体为溶剂的纤维素纤维制备中溶剂的回收方法 |
| JP4774303B2 (ja) | 2006-01-26 | 2011-09-14 | 富士フイルム株式会社 | セルロースアシレートフィルム、光学補償シート、偏光板、及び液晶表示装置 |
| DE102006011075A1 (de) | 2006-03-08 | 2007-09-13 | Basf Ag | Verfahren zum Abbau von Cellulose in Lösung |
| DE102006011077A1 (de) | 2006-03-08 | 2007-09-13 | Basf Ag | Verfahren zum Abbau von Cellulose mit Nucleophilen |
| KR20080110608A (ko) | 2006-03-08 | 2008-12-18 | 바스프 에스이 | 셀룰로오스의 분해 방법 |
| JP5072393B2 (ja) | 2006-03-20 | 2012-11-14 | 富士フイルム株式会社 | セルロースアシレートフィルムおよびその製造方法、並びに、それを用いた位相差フィルム、偏光板および液晶表示装置 |
| US20070225191A1 (en) | 2006-03-27 | 2007-09-27 | The Procter & Gamble Company | Methods for modifying bioplymers in ionic liquids |
| US7714124B2 (en) | 2006-03-27 | 2010-05-11 | The Procter & Gamble Company | Methods for modifying cellulosic polymers in ionic liquids |
| JP5278720B2 (ja) | 2006-03-27 | 2013-09-04 | Nltテクノロジー株式会社 | 液晶パネル、液晶表示装置及び端末装置 |
| JP4887072B2 (ja) | 2006-05-02 | 2012-02-29 | 富士フイルム株式会社 | セルロース体フィルム、光学補償シート、偏光板、液晶表示装置 |
| EP1860201A1 (en) | 2006-05-25 | 2007-11-28 | BP p.l.c. | Conversion method |
| EP1911829A1 (en) | 2006-10-10 | 2008-04-16 | The Queen's University of Belfast | Process for deacidifying crude oil |
| JP2007332292A (ja) | 2006-06-15 | 2007-12-27 | Fujifilm Corp | セルロース体、セルロース体フィルム、光学補償シート、偏光板、液晶表示装置 |
| DE102006028165A1 (de) | 2006-06-16 | 2007-12-20 | Basf Ag | Verfahren zur Acylierung von Cellulose |
| US7976914B2 (en) | 2006-06-16 | 2011-07-12 | Fujifilm Corporaton | Resin film, production method thereof, polarizing plate and liquid crystal display device |
| US20090281303A1 (en) | 2006-06-23 | 2009-11-12 | Basf Se | Process for silylating cellulose |
| JP5112652B2 (ja) * | 2006-06-28 | 2013-01-09 | 富士フイルム株式会社 | セルロースアシレート組成物の製造方法およびセルロースアシレートフィルム |
| US20090182138A1 (en) * | 2006-06-30 | 2009-07-16 | Basf Se | Method for acylating cellulose with a specific average degree of polymerization |
| EP2041183A1 (de) | 2006-07-07 | 2009-04-01 | Basf Se | Verfahren zur darstellung von celluloseacetalen |
| US7939681B2 (en) | 2006-08-07 | 2011-05-10 | Battelle Memorial Institute | Methods for conversion of carbohydrates in ionic liquids to value-added chemicals |
| CN101522985B (zh) | 2006-10-13 | 2013-01-16 | 巴斯夫欧洲公司 | 增溶聚合物的离子液体 |
| GB0623473D0 (en) | 2006-11-24 | 2007-01-03 | Bristol Myers Squibb Co | Dissolution and processing of cellulose |
| JP2008156623A (ja) | 2006-11-30 | 2008-07-10 | Sanyo Chem Ind Ltd | アルキルエーテル化セルロースの製造方法 |
| JP2009063983A (ja) | 2006-12-21 | 2009-03-26 | Fujifilm Corp | 光学フィルム、及びそれを有する偏光板 |
| BRPI0806908A2 (pt) | 2007-01-23 | 2014-04-29 | Basf Se | Processos para a prepração de um produto de glicose a partir de um material lignocelulósico, e para a preparação de um produto de metabolismo microbiano, produto de glicose, e, produto de lignina |
| US20080188636A1 (en) | 2007-02-06 | 2008-08-07 | North Carolina State University | Polymer derivatives and composites from the dissolution of lignocellulosics in ionic liquids |
| CN100572432C (zh) | 2007-02-08 | 2009-12-23 | 中国纺织科学研究院 | 一种纤维素溶液及其制备方法 |
| US9834516B2 (en) | 2007-02-14 | 2017-12-05 | Eastman Chemical Company | Regioselectively substituted cellulose esters produced in a carboxylated ionic liquid process and products produced therefrom |
| US8153782B2 (en) | 2007-02-14 | 2012-04-10 | Eastman Chemical Company | Reformation of ionic liquids |
| JP2010111707A (ja) | 2007-02-22 | 2010-05-20 | Nisshinbo Holdings Inc | ポリマー処理剤およびドープ |
| US7674608B2 (en) | 2007-02-23 | 2010-03-09 | The University Of Toledo | Saccharifying cellulose |
| JP2008248217A (ja) | 2007-03-08 | 2008-10-16 | Kri Inc | 熱可塑性多糖ゲルおよびその製造方法ならびに多糖成形材料の製造方法 |
| JP5563313B2 (ja) | 2007-03-14 | 2014-07-30 | ザ・ユニバーシティ・オブ・トレド | バイオマス前処理 |
| JP2010132558A (ja) | 2007-03-16 | 2010-06-17 | Nisshinbo Holdings Inc | 多糖類の処理剤 |
| JP5021537B2 (ja) | 2007-03-28 | 2012-09-12 | 三洋化成工業株式会社 | セルロースエーテルの製造方法 |
| US20080241536A1 (en) | 2007-03-29 | 2008-10-02 | Weyerhaeuser Co. | Method for processing cellulose in ionic liquids and fibers therefrom |
| WO2008119770A1 (de) | 2007-03-30 | 2008-10-09 | Basf Se | Verfahren zur modifizierung der struktur eines cellulosematerials durch behandeln mit einer ionischen flüssigkeit |
| CN101289817B (zh) | 2007-04-20 | 2010-07-28 | 中国科学院大连化学物理研究所 | 一种在离子液体中高效水解纤维素的方法 |
| JP5339452B2 (ja) | 2007-04-24 | 2013-11-13 | 国立大学法人東京農工大学 | イオン液体およびこのイオン液体からなるポリマー処理剤 |
| US8071813B2 (en) | 2007-05-03 | 2011-12-06 | Lawrence Livermore National Security, Llc | Methods of using ionic liquids having a fluoride anion as solvents |
| US20090096962A1 (en) | 2007-05-14 | 2009-04-16 | Eastman Chemical Company | Cellulose Esters with High Hyrdoxyl Content and Their Use in Liquid Crystal Displays |
| JP5296334B2 (ja) | 2007-06-08 | 2013-09-25 | サンダイヤポリマー株式会社 | 吸水性ポリマーの製造方法及び吸収性樹脂粒子 |
| KR101436170B1 (ko) | 2007-06-26 | 2014-09-01 | 후지필름 가부시키가이샤 | 셀룰로오스아실레이트 조성물, 셀룰로오스아실레이트 필름,및 그 용도 |
| CN101085838B (zh) | 2007-07-03 | 2011-03-30 | 中国科学院化学研究所 | 一种连续制备纤维素/离子液体溶液的方法 |
| DE102007035322B4 (de) | 2007-07-25 | 2011-11-17 | Friedrich-Schiller-Universität Jena | Verfahren zur Herstellung wasserlöslicher, niedrig substituierter Cellulosesulfate |
| TW200912484A (en) | 2007-07-30 | 2009-03-16 | Fujifilm Corp | Retardation film, polarizing plate, and liquid-crystal display device comprising it |
| TWI448497B (zh) | 2007-08-24 | 2014-08-11 | Eastman Chem Co | 具有低雙折射之纖維素酯組合物及由其製得之膜 |
| US8349921B2 (en) | 2007-08-24 | 2013-01-08 | Eastman Chemical Company | Mixed cellulose ester films having +C plate and −A plate optical properties |
| DE102007041416A1 (de) | 2007-08-31 | 2009-03-05 | Basf Se | Destillation ionischer Flüssigkeiten |
| EP2033974A1 (en) | 2007-09-06 | 2009-03-11 | The Queens University of Belfast | Conversion method |
| JP2009091542A (ja) | 2007-09-21 | 2009-04-30 | Daicel Chem Ind Ltd | セルロース混合アシレートの製造方法、及び新規なセルロース混合アシレート |
| US20090084509A1 (en) | 2007-09-28 | 2009-04-02 | Weyerhaeuser Company | Dissolution of Cellulose in Mixed Solvent Systems |
| CN104635291A (zh) | 2007-10-11 | 2015-05-20 | 瑞尔D股份有限公司 | 弯曲光学滤光器 |
| JP5291431B2 (ja) | 2007-10-29 | 2013-09-18 | 富士フイルム株式会社 | セルロースアシレートフィルム、反射防止フィルム、偏光板及び画像表示装置 |
| EP2062922A1 (de) | 2007-11-14 | 2009-05-27 | Basf Se | Verfahren zur Herstellung von regenerierten Biopolymeren und die danach erhältlichen regenerierten Erzeugnisse |
| CN101918368B (zh) | 2007-12-14 | 2013-04-24 | 巴斯夫欧洲公司 | 改善离子液体的水解稳定性的方法 |
| EP2072530A1 (de) | 2007-12-21 | 2009-06-24 | Dow Wolff Cellulosics GmbH | Verfahren zur Herstellung aminogruppenhaltiger Cellulosederivate in ionischer Flüssigkeit |
| JP4740938B2 (ja) | 2007-12-27 | 2011-08-03 | ダイセル化学工業株式会社 | 6位高アセチル化セルロースジアセテート及びその製造方法 |
| CN101234197B (zh) | 2008-01-29 | 2010-05-12 | 中国人民解放军第三军医大学 | 一种重组减毒鼠伤寒沙门氏菌载体疫苗及制备方法 |
| US8999211B2 (en) | 2008-02-11 | 2015-04-07 | Basf Se | Method for producing porous structures from synthetic polymers |
| US8354525B2 (en) | 2008-02-13 | 2013-01-15 | Eastman Chemical Company | Regioselectively substituted cellulose esters produced in a halogenated ionic liquid process and products produced therefrom |
| US20090203900A1 (en) | 2008-02-13 | 2009-08-13 | Eastman Chemical Comapany | Production of cellulose esters in the presence of a cosolvent |
| US8158777B2 (en) | 2008-02-13 | 2012-04-17 | Eastman Chemical Company | Cellulose esters and their production in halogenated ionic liquids |
| US8188267B2 (en) | 2008-02-13 | 2012-05-29 | Eastman Chemical Company | Treatment of cellulose esters |
| EP2098539B1 (en) | 2008-03-03 | 2017-05-10 | SE Tylose GmbH & Co.KG | Homogeneous synthesis of cellulose ethers in ionic liquids |
| WO2009116512A1 (ja) | 2008-03-19 | 2009-09-24 | 住友化学株式会社 | カルボニル化合物の製造方法 |
| CN101285213A (zh) | 2008-05-22 | 2008-10-15 | 高小山 | 一种精制棉纤维的制备方法 |
| CN101284913A (zh) | 2008-05-22 | 2008-10-15 | 高小山 | 以离子液体为溶剂的纤维素膜的制备方法 |
| JP5222064B2 (ja) | 2008-09-02 | 2013-06-26 | 富士フイルム株式会社 | セルロースアシレート積層フィルム、その製造方法、偏光板および液晶表示装置 |
| US8067488B2 (en) | 2009-04-15 | 2011-11-29 | Eastman Chemical Company | Cellulose solutions comprising tetraalkylammonium alkylphosphate and products produced therefrom |
| US8254417B2 (en) * | 2010-06-14 | 2012-08-28 | Ipg Photonics Corporation | Fiber laser system with controllably alignable optical components thereof |
| US20120003403A1 (en) | 2010-07-02 | 2012-01-05 | Eastman Chemical Company | Multilayer cellulose ester film having reversed optical dispersion |
| JP5811651B2 (ja) | 2010-09-14 | 2015-11-11 | 株式会社リコー | 画像形成装置、画像形成装置の制御方法及びプログラム |
| US9096691B2 (en) | 2011-04-13 | 2015-08-04 | Eastman Chemical Company | Cellulose ester optical films |
-
2009
- 2009-08-12 US US12/539,800 patent/US9834516B2/en active Active
- 2009-08-13 CN CN201410147527.7A patent/CN103923352B/zh active Active
- 2009-08-13 CN CN201210459351XA patent/CN102977216A/zh active Pending
- 2009-08-13 KR KR1020117005787A patent/KR20110043757A/ko not_active Abandoned
- 2009-08-13 WO PCT/US2009/004637 patent/WO2010019244A1/en not_active Ceased
- 2009-08-13 EP EP09789131A patent/EP2313439A1/en not_active Withdrawn
- 2009-08-13 EP EP17172680.5A patent/EP3239179B1/en active Active
- 2009-08-13 CN CN200980131585.8A patent/CN102124031B/zh not_active Expired - Fee Related
- 2009-08-13 JP JP2011522997A patent/JP2011530643A/ja active Pending
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2011
- 2011-12-29 US US13/339,814 patent/US20120101269A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP2011530643A (ja) | 2011-12-22 |
| US9834516B2 (en) | 2017-12-05 |
| KR20110043757A (ko) | 2011-04-27 |
| US20100029927A1 (en) | 2010-02-04 |
| CN102124031B (zh) | 2014-05-14 |
| EP3239179A1 (en) | 2017-11-01 |
| CN102977216A (zh) | 2013-03-20 |
| CN102124031A (zh) | 2011-07-13 |
| EP3239179B1 (en) | 2023-02-22 |
| WO2010019244A1 (en) | 2010-02-18 |
| CN103923352A (zh) | 2014-07-16 |
| US20120101269A1 (en) | 2012-04-26 |
| EP2313439A1 (en) | 2011-04-27 |
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