JP2009209361A5 - - Google Patents
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- Publication number
- JP2009209361A5 JP2009209361A5 JP2009024686A JP2009024686A JP2009209361A5 JP 2009209361 A5 JP2009209361 A5 JP 2009209361A5 JP 2009024686 A JP2009024686 A JP 2009024686A JP 2009024686 A JP2009024686 A JP 2009024686A JP 2009209361 A5 JP2009209361 A5 JP 2009209361A5
- Authority
- JP
- Japan
- Prior art keywords
- solvent
- cellulose
- ionic liquid
- cellulose ether
- weight
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims 12
- 229920003086 cellulose ether Polymers 0.000 claims 10
- 239000002904 solvent Substances 0.000 claims 9
- 239000002608 ionic liquid Substances 0.000 claims 8
- -1 tetrafluoroborate Chemical compound 0.000 claims 5
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims 3
- 229920002678 cellulose Polymers 0.000 claims 3
- 239000001913 cellulose Substances 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 150000001450 anions Chemical class 0.000 claims 2
- 150000007942 carboxylates Chemical class 0.000 claims 2
- 150000001768 cations Chemical class 0.000 claims 2
- 239000006184 cosolvent Substances 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- OFTSSFREMCBZMF-UHFFFAOYSA-M 1-ethyl-2,3-dimethylimidazol-3-ium;acetate Chemical compound CC([O-])=O.CC[N+]=1C=CN(C)C=1C OFTSSFREMCBZMF-UHFFFAOYSA-M 0.000 claims 1
- XIYUIMLQTKODPS-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;acetate Chemical compound CC([O-])=O.CC[N+]=1C=CN(C)C=1 XIYUIMLQTKODPS-UHFFFAOYSA-M 0.000 claims 1
- CWSZBVAUYPTXTG-UHFFFAOYSA-N 5-[6-[[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxymethyl]-3,4-dihydroxy-5-[4-hydroxy-3-(2-hydroxyethoxy)-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxyoxan-2-yl]oxy-6-(hydroxymethyl)-2-methyloxane-3,4-diol Chemical group O1C(CO)C(OC)C(O)C(O)C1OCC1C(OC2C(C(O)C(OC)C(CO)O2)OCCO)C(O)C(O)C(OC2C(OC(C)C(O)C2O)CO)O1 CWSZBVAUYPTXTG-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 1
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 claims 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-L Oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 150000008052 alkyl sulfonates Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims 1
- QWJNFFYFEKXZBF-UHFFFAOYSA-N cyanocyanamide Chemical compound N#CNC#N QWJNFFYFEKXZBF-UHFFFAOYSA-N 0.000 claims 1
- 238000006266 etherification reaction Methods 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 229920000151 polyglycol Polymers 0.000 claims 1
- 239000010695 polyglycol Substances 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 125000002577 pseudohalo group Chemical group 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- RVKZDIDATLDTNR-UHFFFAOYSA-N sulfanylideneeuropium Chemical compound [Eu]=S RVKZDIDATLDTNR-UHFFFAOYSA-N 0.000 claims 1
- 229940066528 trichloroacetate Drugs 0.000 claims 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08003876.3 | 2008-03-03 | ||
| EP08003876.3A EP2098539B1 (en) | 2008-03-03 | 2008-03-03 | Homogeneous synthesis of cellulose ethers in ionic liquids |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009209361A JP2009209361A (ja) | 2009-09-17 |
| JP2009209361A5 true JP2009209361A5 (https=) | 2012-03-08 |
| JP5744379B2 JP5744379B2 (ja) | 2015-07-08 |
Family
ID=39511011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009024686A Expired - Fee Related JP5744379B2 (ja) | 2008-03-03 | 2009-02-05 | イオン性液体におけるセルロースエーテルの均質合成 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8541571B2 (https=) |
| EP (1) | EP2098539B1 (https=) |
| JP (1) | JP5744379B2 (https=) |
| KR (1) | KR101611611B1 (https=) |
| MX (1) | MX2009002345A (https=) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7919631B2 (en) * | 2007-02-14 | 2011-04-05 | Eastman Chemical Company | Production of ionic liquids |
| 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 |
| US10174129B2 (en) | 2007-02-14 | 2019-01-08 | Eastman Chemical Company | Regioselectively substituted cellulose esters produced in a carboxylated ionic liquid process and products produced therefrom |
| US9777074B2 (en) | 2008-02-13 | 2017-10-03 | Eastman Chemical Company | Regioselectively substituted cellulose esters produced in a halogenated ionic liquid process and products produced therefrom |
| US8188267B2 (en) | 2008-02-13 | 2012-05-29 | Eastman Chemical Company | Treatment of cellulose esters |
| US8158777B2 (en) | 2008-02-13 | 2012-04-17 | Eastman Chemical Company | Cellulose esters and their production in halogenated ionic liquids |
| 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 |
| US8524887B2 (en) | 2009-04-15 | 2013-09-03 | Eastman Chemical Company | Regioselectively substituted cellulose esters produced in a tetraalkylammonium alkylphosphate ionic liquid process and products produced therefrom |
| US8980050B2 (en) | 2012-08-20 | 2015-03-17 | Celanese International Corporation | Methods for removing hemicellulose |
| US9394375B2 (en) * | 2011-03-25 | 2016-07-19 | Board Of Trustees Of The University Of Alabama | Compositions containing recyclable ionic liquids for use in biomass processing |
| US9096691B2 (en) | 2011-04-13 | 2015-08-04 | Eastman Chemical Company | Cellulose ester optical films |
| US9683309B2 (en) * | 2012-07-24 | 2017-06-20 | Board Of Trustees Of The University Of Alabama | Process for electrospinning chitin fibers from chitinous biomass solution |
| US8986501B2 (en) | 2012-08-20 | 2015-03-24 | Celanese International Corporation | Methods for removing hemicellulose |
| DE102012024727A1 (de) * | 2012-12-18 | 2014-06-18 | Friedrich-Schiller-Universität Jena | Cellulose- und Celluloseether-Lösungen und deren Verwendung |
| WO2014125438A1 (en) | 2013-02-14 | 2014-08-21 | The Board Of Trustees Of The University Of Alabama | Coagulation of biopolymers from ionic liquid solutions using co2 |
| CN103172754A (zh) * | 2013-04-07 | 2013-06-26 | 中国科学院过程工程研究所 | 一种利用离子液体制备羧甲基纤维素的方法 |
| CN103831021B (zh) * | 2014-01-28 | 2016-02-24 | 中国科学院化学研究所 | 以n-甲基吗啉氧化物为溶剂制备再生纤维素纳滤膜的方法 |
| US10100131B2 (en) | 2014-08-27 | 2018-10-16 | The Board Of Trustees Of The University Of Alabama | Chemical pulping of chitinous biomass for chitin |
| US10982381B2 (en) | 2014-10-06 | 2021-04-20 | Natural Fiber Welding, Inc. | Methods, processes, and apparatuses for producing welded substrates |
| US10011931B2 (en) | 2014-10-06 | 2018-07-03 | Natural Fiber Welding, Inc. | Methods, processes, and apparatuses for producing dyed and welded substrates |
| EP3214097B1 (en) * | 2014-10-27 | 2018-12-12 | National University Corporation Kanazawa University | Method for producing polysaccharide derivative and lignin derivative |
| EP3348579A4 (en) * | 2015-09-07 | 2019-05-01 | Kao Corporation | MODIFIED CELLULOSE FIBER |
| CN107949577B (zh) * | 2015-09-07 | 2021-04-06 | 花王株式会社 | 改性纤维素纤维 |
| US20190010253A1 (en) * | 2015-09-07 | 2019-01-10 | Kao Corporation | Modified cellulose fibers |
| MX2018010421A (es) | 2016-03-25 | 2019-05-20 | Natural Fiber Welding Inc | Metodos, procesos y aparatos para producir sustratos soldados. |
| CN109196149B (zh) | 2016-05-03 | 2021-10-15 | 天然纤维焊接股份有限公司 | 用于生产染色的焊接基质的方法、工艺和设备 |
| US20190177756A1 (en) | 2016-08-18 | 2019-06-13 | The Board Of Trustees Of The Leland Stanford Junior University | Production and use of phosphoethanolamine cellulose and derivatives |
| US20190263938A1 (en) * | 2016-09-29 | 2019-08-29 | Sumitomo Seika Chemicals Co., Ltd. | Method for producing water-soluble hydroxyethyl cellulose |
| EP3542784B1 (en) * | 2016-11-18 | 2024-03-06 | Panasonic Intellectual Property Management Co., Ltd. | Film to be adhered to living body and method for manufacturing same |
| US10927191B2 (en) | 2017-01-06 | 2021-02-23 | The Board Of Trustees Of The University Of Alabama | Coagulation of chitin from ionic liquid solutions using kosmotropic salts |
| JP6779158B2 (ja) * | 2017-03-07 | 2020-11-04 | 花王株式会社 | 改質セルロース繊維の製造方法 |
| US20210130499A1 (en) * | 2017-03-07 | 2021-05-06 | Kao Corporation | Method for producing modified cellulose fiber |
| US10941258B2 (en) | 2017-03-24 | 2021-03-09 | The Board Of Trustees Of The University Of Alabama | Metal particle-chitin composite materials and methods of making thereof |
| CN107200787B (zh) * | 2017-05-23 | 2019-08-13 | 四川大学 | 一种咪唑鎓海藻酸盐离子液体及其合成方法 |
| TWI829660B (zh) | 2017-11-11 | 2024-01-21 | 美商天然纖維焊接股份有限公司 | 紗與熔接紗 |
| JP7336870B2 (ja) * | 2019-04-18 | 2023-09-01 | 花王株式会社 | 樹脂組成物 |
| EP3741887A1 (de) * | 2019-05-21 | 2020-11-25 | Aurotec GmbH | Verfahren und vorrichtung zum regenerieren eines lösungsmittels von zellulose aus einem spinnverfahren |
| CN114292340B (zh) * | 2022-01-18 | 2023-03-03 | 万华化学集团股份有限公司 | 一种制备聚季铵盐-10的方法 |
| CN114524881A (zh) * | 2022-03-28 | 2022-05-24 | 华北水利水电大学 | 一种利用秸秆制备纤维素基减水剂的方法 |
| CN114716573A (zh) * | 2022-05-13 | 2022-07-08 | 南京林业大学 | 一种羟丙基纤维素的均相合成方法 |
| CN115386011B (zh) * | 2022-08-23 | 2023-11-07 | 中国科学院宁波材料技术与工程研究所 | 一种氰乙基纤维素的制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US3447939A (en) | 1966-09-02 | 1969-06-03 | Eastman Kodak Co | Compounds dissolved in cyclic amine oxides |
| US4196282A (en) | 1977-11-25 | 1980-04-01 | Akzona Incorporated | Process for making a shapeable cellulose and shaped cellulose products |
| DD207380A1 (de) | 1982-11-02 | 1984-02-29 | Adw Inst Polymerenchemie | Verfahren zur herstellung hochquellender carboxymethylcellulose |
| JPH0660201B2 (ja) * | 1984-02-22 | 1994-08-10 | ダイセル化学工業株式会社 | 水溶性セルロース誘導体の製法 |
| DE19730090A1 (de) | 1997-07-14 | 1999-01-21 | Wolff Walsrode Ag | Neuartige Celluloseether und Verfahren zu deren Herstellung |
| DE50209901D1 (de) | 2001-09-14 | 2007-05-24 | Wolff Cellulosics Gmbh & Co Kg | Verfahren und Vorrichtung zur industriellen Herstellung von Methylhydroxyalkylcellulose |
| US6824599B2 (en) | 2001-10-03 | 2004-11-30 | The University Of Alabama | Dissolution and processing of cellulose using ionic liquids |
| FI116140B (fi) | 2003-12-03 | 2005-09-30 | Kemira Oyj | Eetteröintimenetelmä |
| KR20060086069A (ko) | 2005-01-26 | 2006-07-31 | 주식회사 코오롱 | 셀룰로오스 에테르 유도체의 제조방법 |
| 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 |
-
2008
- 2008-03-03 EP EP08003876.3A patent/EP2098539B1/en not_active Not-in-force
-
2009
- 2009-02-05 JP JP2009024686A patent/JP5744379B2/ja not_active Expired - Fee Related
- 2009-02-25 US US12/392,222 patent/US8541571B2/en not_active Expired - Fee Related
- 2009-03-02 MX MX2009002345A patent/MX2009002345A/es active IP Right Grant
- 2009-03-02 KR KR1020090017431A patent/KR101611611B1/ko not_active Expired - Fee Related
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