CA2614117A1 - Ionic liquid reconstituted cellulose composites as solid support matrices - Google Patents
Ionic liquid reconstituted cellulose composites as solid support matrices Download PDFInfo
- Publication number
- CA2614117A1 CA2614117A1 CA002614117A CA2614117A CA2614117A1 CA 2614117 A1 CA2614117 A1 CA 2614117A1 CA 002614117 A CA002614117 A CA 002614117A CA 2614117 A CA2614117 A CA 2614117A CA 2614117 A1 CA2614117 A1 CA 2614117A1
- Authority
- CA
- Canada
- Prior art keywords
- active substance
- linker
- cellulose
- composite
- ionic liquid
- 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.)
- Abandoned
Links
- 239000002131 composite material Substances 0.000 title claims abstract description 115
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 101
- 229920002678 cellulose Polymers 0.000 title claims description 187
- 239000001913 cellulose Substances 0.000 title claims description 186
- 239000007787 solid Substances 0.000 title description 17
- 239000013543 active substance Substances 0.000 claims abstract description 330
- 238000000034 method Methods 0.000 claims abstract description 145
- 239000004627 regenerated cellulose Substances 0.000 claims abstract description 78
- 125000000524 functional group Chemical group 0.000 claims description 95
- 230000000269 nucleophilic effect Effects 0.000 claims description 84
- 239000000203 mixture Substances 0.000 claims description 78
- -1 linters Polymers 0.000 claims description 74
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 68
- 150000001412 amines Chemical class 0.000 claims description 57
- 239000011159 matrix material Substances 0.000 claims description 51
- 125000001424 substituent group Chemical group 0.000 claims description 46
- 102000004190 Enzymes Human genes 0.000 claims description 43
- 108090000790 Enzymes Proteins 0.000 claims description 43
- 102000004169 proteins and genes Human genes 0.000 claims description 40
- 108090000623 proteins and genes Proteins 0.000 claims description 40
- 229910001868 water Inorganic materials 0.000 claims description 35
- 239000002904 solvent Substances 0.000 claims description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 27
- 102000039446 nucleic acids Human genes 0.000 claims description 27
- 108020004707 nucleic acids Proteins 0.000 claims description 27
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- 150000001768 cations Chemical class 0.000 claims description 25
- 150000007942 carboxylates Chemical class 0.000 claims description 22
- 239000007788 liquid Substances 0.000 claims description 17
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
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- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 6
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- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 5
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
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- 125000005647 linker group Chemical group 0.000 description 173
- 235000010980 cellulose Nutrition 0.000 description 168
- 239000000463 material Substances 0.000 description 72
- 125000000217 alkyl group Chemical group 0.000 description 55
- 239000000243 solution Substances 0.000 description 43
- 229940088598 enzyme Drugs 0.000 description 39
- 125000003118 aryl group Chemical group 0.000 description 36
- 235000018102 proteins Nutrition 0.000 description 36
- 239000000126 substance Substances 0.000 description 36
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- 238000011069 regeneration method Methods 0.000 description 33
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- 235000001014 amino acid Nutrition 0.000 description 21
- 150000001299 aldehydes Chemical class 0.000 description 20
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- 125000003729 nucleotide group Chemical group 0.000 description 20
- 125000003342 alkenyl group Chemical group 0.000 description 19
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- 125000000304 alkynyl group Chemical group 0.000 description 18
- 125000000753 cycloalkyl group Chemical group 0.000 description 18
- 150000003573 thiols Chemical class 0.000 description 18
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- 108010029541 Laccase Proteins 0.000 description 16
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- 238000010168 coupling process Methods 0.000 description 16
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 125000000392 cycloalkenyl group Chemical group 0.000 description 15
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 15
- 229920002873 Polyethylenimine Polymers 0.000 description 14
- 239000002585 base Substances 0.000 description 14
- 125000004366 heterocycloalkenyl group Chemical group 0.000 description 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 14
- 125000003545 alkoxy group Chemical group 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 13
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- 239000012634 fragment Substances 0.000 description 12
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- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 150000004820 halides Chemical class 0.000 description 11
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- 239000000047 product Substances 0.000 description 11
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- 229910052799 carbon Inorganic materials 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
- 230000000840 anti-viral effect Effects 0.000 description 9
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
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Classifications
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
- C08L1/02—Cellulose; Modified cellulose
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/02—Polyamines
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L89/00—Compositions of proteins; Compositions of derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D189/00—Coating compositions based on proteins; Coating compositions based on derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/14—Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/14—Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
- C08L2666/20—Macromolecular compounds having nitrogen in the main chain according to C08L75/00 - C08L79/00; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/26—Natural polymers, natural resins or derivatives thereof according to C08L1/00 - C08L5/00, C08L89/00, C08L93/00, C08L97/00 or C08L99/00
Landscapes
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
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- Medicinal Preparation (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
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| US69490205P | 2005-06-29 | 2005-06-29 | |
| US60/694,902 | 2005-06-29 | ||
| PCT/US2006/024863 WO2007005388A2 (en) | 2005-06-29 | 2006-06-27 | Ionic liquid reconstituted cellulose composites as solid support matrices |
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| CA2614117A1 true CA2614117A1 (en) | 2007-01-11 |
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| EP (1) | EP1907470B1 (enExample) |
| JP (1) | JP2009500016A (enExample) |
| KR (1) | KR20080036184A (enExample) |
| CN (1) | CN101258196B (enExample) |
| AU (1) | AU2006266151B2 (enExample) |
| BR (1) | BRPI0612612A2 (enExample) |
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| MX (1) | MX2008000068A (enExample) |
| NO (1) | NO20080505L (enExample) |
| NZ (1) | NZ565286A (enExample) |
| WO (1) | WO2007005388A2 (enExample) |
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| US7888412B2 (en) * | 2004-03-26 | 2011-02-15 | Board Of Trustees Of The University Of Alabama | Polymer dissolution and blend formation in ionic liquids |
| DE102005017733A1 (de) * | 2005-04-15 | 2006-10-19 | Basf Ag | Löslichkeit von Cellulose in ionischen Flüssigkeiten unter Zugabe von Aminbase |
| US8883193B2 (en) | 2005-06-29 | 2014-11-11 | The University Of Alabama | Cellulosic biocomposites as molecular scaffolds for nano-architectures |
| US7833643B2 (en) * | 2005-09-26 | 2010-11-16 | Arizona Board Of Regents For And On Behalf Of Arizona State University | Neutral protic-salt electrolytes and protic-salt imbibed polymer membranes for high temperature fuel cell applications |
| GB0623473D0 (en) | 2006-11-24 | 2007-01-03 | Bristol Myers Squibb Co | Dissolution and processing of cellulose |
| US8182557B2 (en) | 2007-02-06 | 2012-05-22 | North Carolina State University | Use of lignocellulosics solvated in ionic liquids for production of biofuels |
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- 2006-06-27 ZA ZA200800731A patent/ZA200800731B/xx unknown
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| EP1907470B1 (en) | 2013-04-10 |
| EP1907470A2 (en) | 2008-04-09 |
| WO2007005388A2 (en) | 2007-01-11 |
| MX2008000068A (es) | 2008-04-17 |
| EA200800160A1 (ru) | 2008-06-30 |
| CN101258196A (zh) | 2008-09-03 |
| US20070006774A1 (en) | 2007-01-11 |
| JP2009500016A (ja) | 2009-01-08 |
| BRPI0612612A2 (pt) | 2009-01-27 |
| WO2007005388A3 (en) | 2007-03-29 |
| KR20080036184A (ko) | 2008-04-25 |
| AU2006266151A1 (en) | 2007-01-11 |
| ZA200800731B (en) | 2009-08-26 |
| AU2006266151B2 (en) | 2011-09-22 |
| NO20080505L (no) | 2008-03-27 |
| CN101258196B (zh) | 2011-12-21 |
| EP1907470A4 (en) | 2011-08-10 |
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