CA2519652C - Cellulose matrix encapsulation and method - Google Patents
Cellulose matrix encapsulation and method Download PDFInfo
- Publication number
- CA2519652C CA2519652C CA2519652A CA2519652A CA2519652C CA 2519652 C CA2519652 C CA 2519652C CA 2519652 A CA2519652 A CA 2519652A CA 2519652 A CA2519652 A CA 2519652A CA 2519652 C CA2519652 C CA 2519652C
- Authority
- CA
- Canada
- Prior art keywords
- cellulose
- ionic liquid
- active substance
- regenerated cellulose
- solvent
- 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.)
- Expired - Fee Related
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- 229920002678 cellulose Polymers 0.000 title claims abstract description 183
- 239000001913 cellulose Substances 0.000 title claims abstract description 182
- 238000000034 method Methods 0.000 title claims abstract description 68
- 239000011159 matrix material Substances 0.000 title claims abstract description 40
- 238000005538 encapsulation Methods 0.000 title description 14
- 239000002608 ionic liquid Substances 0.000 claims abstract description 119
- 239000013543 active substance Substances 0.000 claims abstract description 54
- 239000004627 regenerated cellulose Substances 0.000 claims abstract description 39
- 125000001424 substituent group Chemical group 0.000 claims abstract description 13
- 239000007857 degradation product Substances 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 43
- 229910001868 water Inorganic materials 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 31
- 150000001768 cations Chemical class 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 28
- -1 -C1-C6 alkyl imidazolium ion Chemical compound 0.000 claims description 23
- 108090000790 Enzymes Proteins 0.000 claims description 23
- 102000004190 Enzymes Human genes 0.000 claims description 23
- 239000007788 liquid Substances 0.000 claims description 23
- 150000001450 anions Chemical class 0.000 claims description 15
- 238000010438 heat treatment Methods 0.000 claims description 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 12
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 11
- 125000001145 hydrido group Chemical group *[H] 0.000 claims description 11
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
- 230000002209 hydrophobic effect Effects 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000002917 insecticide Substances 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000002577 pseudohalo group Chemical group 0.000 claims description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
- 150000007942 carboxylates Chemical class 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000012071 phase Substances 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 4
- 230000000844 anti-bacterial effect Effects 0.000 claims description 4
- 239000003899 bactericide agent Substances 0.000 claims description 4
- 239000003337 fertilizer Substances 0.000 claims description 4
- 239000000796 flavoring agent Substances 0.000 claims description 4
- 239000000417 fungicide Substances 0.000 claims description 4
- 239000004009 herbicide Substances 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 230000000813 microbial effect Effects 0.000 claims description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 3
- 241000238631 Hexapoda Species 0.000 claims description 3
- 239000003463 adsorbent Substances 0.000 claims description 3
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- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 3
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- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 2
- USXDFAGDIOXNML-UHFFFAOYSA-N Fulminate Chemical compound [O-][N+]#[C-] USXDFAGDIOXNML-UHFFFAOYSA-N 0.000 claims description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000007790 solid phase Substances 0.000 claims 6
- 230000000855 fungicidal effect Effects 0.000 claims 2
- 230000002363 herbicidal effect Effects 0.000 claims 2
- 230000005855 radiation Effects 0.000 claims 1
- 238000009826 distribution Methods 0.000 abstract description 9
- 235000010980 cellulose Nutrition 0.000 description 153
- 239000000243 solution Substances 0.000 description 78
- 239000010408 film Substances 0.000 description 53
- 239000000463 material Substances 0.000 description 47
- 230000008929 regeneration Effects 0.000 description 22
- 238000011069 regeneration method Methods 0.000 description 22
- 229940088598 enzyme Drugs 0.000 description 21
- 239000007787 solid Substances 0.000 description 19
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 18
- 238000004090 dissolution Methods 0.000 description 18
- 230000008569 process Effects 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 13
- 230000001172 regenerating effect Effects 0.000 description 13
- 238000000576 coating method Methods 0.000 description 11
- 239000000975 dye Substances 0.000 description 11
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 10
- 229940098773 bovine serum albumin Drugs 0.000 description 10
- 239000012528 membrane Substances 0.000 description 10
- 239000002245 particle Substances 0.000 description 10
- 239000002585 base Substances 0.000 description 9
- 239000002131 composite material Substances 0.000 description 9
- 238000010348 incorporation Methods 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000012530 fluid Substances 0.000 description 8
- SGZRFMMIONYDQU-UHFFFAOYSA-N n,n-bis(2-methylpropyl)-2-[octyl(phenyl)phosphoryl]acetamide Chemical compound CCCCCCCCP(=O)(CC(=O)N(CC(C)C)CC(C)C)C1=CC=CC=C1 SGZRFMMIONYDQU-UHFFFAOYSA-N 0.000 description 8
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 8
- LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 7
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 7
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 7
- 239000002105 nanoparticle Substances 0.000 description 7
- 229910017604 nitric acid Inorganic materials 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 description 6
- 235000017471 coenzyme Q10 Nutrition 0.000 description 6
- 238000013270 controlled release Methods 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 238000007654 immersion Methods 0.000 description 6
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
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- KSFOVUSSGSKXFI-GAQDCDSVSA-N CC1=C/2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(C=C)=C5C)C(C=C)=C4C)C(C)=C3CCC(O)=O)=C1CCC(O)=O Chemical compound CC1=C/2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(C=C)=C5C)C(C=C)=C4C)C(C)=C3CCC(O)=O)=C1CCC(O)=O KSFOVUSSGSKXFI-GAQDCDSVSA-N 0.000 description 4
- ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 4
- 108010029541 Laccase Proteins 0.000 description 4
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
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- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 4
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- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
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- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2989—Microcapsule with solid core [includes liposome]
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- Chemical & Material Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
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- Zoology (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Genetics & Genomics (AREA)
- Toxicology (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
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- Agronomy & Crop Science (AREA)
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- Agricultural Chemicals And Associated Chemicals (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/394,989 US6808557B2 (en) | 2001-10-03 | 2003-03-21 | Cellulose matrix encapsulation and method |
| US10/394,989 | 2003-03-21 | ||
| PCT/US2004/008411 WO2004084627A2 (en) | 2003-03-21 | 2004-03-19 | Cellulose matrix encapsulation and method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2519652A1 CA2519652A1 (en) | 2004-10-07 |
| CA2519652C true CA2519652C (en) | 2012-07-24 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2519652A Expired - Fee Related CA2519652C (en) | 2003-03-21 | 2004-03-19 | Cellulose matrix encapsulation and method |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6808557B2 (enExample) |
| EP (1) | EP1648692A4 (enExample) |
| JP (2) | JP5213329B2 (enExample) |
| KR (2) | KR101064345B1 (enExample) |
| CN (1) | CN100564019C (enExample) |
| AU (1) | AU2004224375B2 (enExample) |
| BR (1) | BRPI0408606A (enExample) |
| CA (1) | CA2519652C (enExample) |
| EA (1) | EA009256B1 (enExample) |
| MX (1) | MXPA05010057A (enExample) |
| WO (1) | WO2004084627A2 (enExample) |
| ZA (1) | ZA200508446B (enExample) |
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2003
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2004
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- 2004-03-19 EP EP04757863A patent/EP1648692A4/en not_active Withdrawn
- 2004-03-19 BR BRPI0408606-6A patent/BRPI0408606A/pt not_active IP Right Cessation
- 2004-03-19 CA CA2519652A patent/CA2519652C/en not_active Expired - Fee Related
- 2004-03-19 CN CNB2004800135605A patent/CN100564019C/zh not_active Expired - Fee Related
-
2005
- 2005-10-18 ZA ZA200508446A patent/ZA200508446B/en unknown
-
2011
- 2011-02-10 JP JP2011027888A patent/JP2011125864A/ja not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| KR101064345B1 (ko) | 2011-09-14 |
| KR20060002839A (ko) | 2006-01-09 |
| AU2004224375B2 (en) | 2008-07-10 |
| ZA200508446B (en) | 2007-04-25 |
| US20040038031A1 (en) | 2004-02-26 |
| MXPA05010057A (es) | 2005-11-23 |
| EA009256B1 (ru) | 2007-12-28 |
| JP2011125864A (ja) | 2011-06-30 |
| US6808557B2 (en) | 2004-10-26 |
| JP5213329B2 (ja) | 2013-06-19 |
| BRPI0408606A (pt) | 2006-03-07 |
| KR20110042243A (ko) | 2011-04-25 |
| EA200501498A1 (ru) | 2006-06-30 |
| CN1867448A (zh) | 2006-11-22 |
| EP1648692A4 (en) | 2009-06-10 |
| CA2519652A1 (en) | 2004-10-07 |
| JP2006526673A (ja) | 2006-11-24 |
| WO2004084627A3 (en) | 2006-01-05 |
| EP1648692A2 (en) | 2006-04-26 |
| AU2004224375A1 (en) | 2004-10-07 |
| WO2004084627A2 (en) | 2004-10-07 |
| CN100564019C (zh) | 2009-12-02 |
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