CA2883429A1 - Compositions and methods for double encapsulation of a volatile compound - Google Patents
Compositions and methods for double encapsulation of a volatile compound Download PDFInfo
- Publication number
- CA2883429A1 CA2883429A1 CA2883429A CA2883429A CA2883429A1 CA 2883429 A1 CA2883429 A1 CA 2883429A1 CA 2883429 A CA2883429 A CA 2883429A CA 2883429 A CA2883429 A CA 2883429A CA 2883429 A1 CA2883429 A1 CA 2883429A1
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- Prior art keywords
- composition
- resin
- oil
- particles
- melting point
- 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
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- 239000000203 mixture Substances 0.000 title claims abstract description 161
- 238000000034 method Methods 0.000 title claims abstract description 56
- 239000003039 volatile agent Substances 0.000 title claims abstract description 8
- 238000005538 encapsulation Methods 0.000 title description 8
- 239000002245 particle Substances 0.000 claims abstract description 117
- 229920005989 resin Polymers 0.000 claims abstract description 100
- 239000011347 resin Substances 0.000 claims abstract description 100
- SHDPRTQPPWIEJG-UHFFFAOYSA-N 1-methylcyclopropene Chemical compound CC1=CC1 SHDPRTQPPWIEJG-UHFFFAOYSA-N 0.000 claims abstract description 87
- 239000000463 material Substances 0.000 claims abstract description 27
- 239000011159 matrix material Substances 0.000 claims abstract description 26
- OOXWYYGXTJLWHA-UHFFFAOYSA-N cyclopropene Chemical compound C1C=C1 OOXWYYGXTJLWHA-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000011248 coating agent Substances 0.000 claims abstract description 5
- 238000000576 coating method Methods 0.000 claims abstract description 5
- 239000003921 oil Substances 0.000 claims description 109
- 239000005969 1-Methyl-cyclopropene Substances 0.000 claims description 86
- 238000002844 melting Methods 0.000 claims description 51
- 230000008018 melting Effects 0.000 claims description 51
- 239000001993 wax Substances 0.000 claims description 44
- 241000196324 Embryophyta Species 0.000 claims description 43
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 38
- 239000006185 dispersion Substances 0.000 claims description 33
- 239000008393 encapsulating agent Substances 0.000 claims description 29
- 239000004632 polycaprolactone Substances 0.000 claims description 27
- 229920001610 polycaprolactone Polymers 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 238000002156 mixing Methods 0.000 claims description 16
- 239000000839 emulsion Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
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- 238000007711 solidification Methods 0.000 claims description 14
- 230000008023 solidification Effects 0.000 claims description 14
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- 238000009472 formulation Methods 0.000 claims description 13
- 230000002209 hydrophobic effect Effects 0.000 claims description 13
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 claims description 12
- 229940043377 alpha-cyclodextrin Drugs 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 12
- 235000013869 carnauba wax Nutrition 0.000 claims description 11
- 235000010446 mineral oil Nutrition 0.000 claims description 11
- 239000004094 surface-active agent Substances 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 239000008117 stearic acid Substances 0.000 claims description 8
- 235000021355 Stearic acid Nutrition 0.000 claims description 7
- 239000004204 candelilla wax Substances 0.000 claims description 7
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- 229940073532 candelilla wax Drugs 0.000 claims description 7
- IUJAMGNYPWYUPM-UHFFFAOYSA-N hentriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC IUJAMGNYPWYUPM-UHFFFAOYSA-N 0.000 claims description 7
- 239000002609 medium Substances 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
- 125000001424 substituent group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000003822 epoxy resin Substances 0.000 claims description 6
- 239000005038 ethylene vinyl acetate Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 6
- 150000002513 isocyanates Chemical class 0.000 claims description 6
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- 229920000647 polyepoxide Polymers 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 6
- 229920000570 polyether Polymers 0.000 claims description 6
- 239000001116 FEMA 4028 Substances 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims description 5
- 235000011175 beta-cyclodextrine Nutrition 0.000 claims description 5
- 229960004853 betadex Drugs 0.000 claims description 5
- 239000008157 edible vegetable oil Substances 0.000 claims description 5
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 claims description 5
- 229940080345 gamma-cyclodextrin Drugs 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000004927 clay Substances 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 abstract description 69
- 239000004480 active ingredient Substances 0.000 abstract description 6
- 235000019198 oils Nutrition 0.000 description 85
- -1 polyoxyethylene Polymers 0.000 description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- 239000000523 sample Substances 0.000 description 37
- 239000004215 Carbon black (E152) Substances 0.000 description 22
- 229930195733 hydrocarbon Natural products 0.000 description 22
- 150000002430 hydrocarbons Chemical class 0.000 description 22
- 239000002002 slurry Substances 0.000 description 20
- 150000004665 fatty acids Chemical class 0.000 description 17
- 238000010008 shearing Methods 0.000 description 17
- 239000007789 gas Substances 0.000 description 15
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 13
- 239000005977 Ethylene Substances 0.000 description 13
- 235000014113 dietary fatty acids Nutrition 0.000 description 13
- 239000000194 fatty acid Substances 0.000 description 13
- 229930195729 fatty acid Natural products 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
- 125000001931 aliphatic group Chemical group 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 125000003636 chemical group Chemical group 0.000 description 10
- 125000004122 cyclic group Chemical group 0.000 description 9
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 9
- 238000000227 grinding Methods 0.000 description 9
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000004205 dimethyl polysiloxane Substances 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 238000011068 loading method Methods 0.000 description 8
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- 239000002904 solvent Substances 0.000 description 7
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- 235000004977 Brassica sinapistrum Nutrition 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/26—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests in coated particulate form
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
- A01N25/10—Macromolecular compounds
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Toxicology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Fertilizers (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Epoxy Resins (AREA)
- Cultivation Of Plants (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNPCT/CN2012/081468 | 2012-09-17 | ||
| PCT/CN2012/081468 WO2014040288A1 (en) | 2012-09-17 | 2012-09-17 | Compositions with hot melt resin matrix |
| US201261713924P | 2012-10-15 | 2012-10-15 | |
| US61/713,924 | 2012-10-15 | ||
| PCT/CN2013/071362 WO2014040402A1 (en) | 2012-09-17 | 2013-02-05 | Compositions and methods for double encapsulation of a volatile compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2883429A1 true CA2883429A1 (en) | 2014-03-20 |
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2883429A Abandoned CA2883429A1 (en) | 2012-09-17 | 2013-02-05 | Compositions and methods for double encapsulation of a volatile compound |
| CA2884076A Abandoned CA2884076A1 (en) | 2012-09-17 | 2013-02-05 | Suspension of particles comprising cyclopropene complexes dispersed in a resin matrix |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2884076A Abandoned CA2884076A1 (en) | 2012-09-17 | 2013-02-05 | Suspension of particles comprising cyclopropene complexes dispersed in a resin matrix |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US20140080710A1 (forum.php) |
| EP (2) | EP2895543A4 (forum.php) |
| JP (2) | JP2015531780A (forum.php) |
| KR (2) | KR20150058330A (forum.php) |
| AU (2) | AU2013314956B2 (forum.php) |
| BR (2) | BR112015005287A2 (forum.php) |
| CA (2) | CA2883429A1 (forum.php) |
| CL (2) | CL2015000651A1 (forum.php) |
| CR (2) | CR20150138A (forum.php) |
| IL (2) | IL237288A0 (forum.php) |
| IN (2) | IN2015DN01612A (forum.php) |
| MX (2) | MX2015003421A (forum.php) |
| PH (2) | PH12015500572A1 (forum.php) |
| RU (2) | RU2015114260A (forum.php) |
| SG (2) | SG11201501759YA (forum.php) |
| WO (2) | WO2014040402A1 (forum.php) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105246330A (zh) * | 2013-02-08 | 2016-01-13 | 阿格洛法士公司 | 用于挥发性化合物的干燥熔融涂布法和制剂 |
| TW201446144A (zh) * | 2013-03-14 | 2014-12-16 | Agrofresh Inc | 經外塗粉末粒子 |
| US9394216B2 (en) | 2014-11-10 | 2016-07-19 | Mirtech, Inc. | Complexes of 1-methylcyclopropene with metal coordination polymer networks |
| KR20180003600A (ko) * | 2015-05-06 | 2018-01-09 | 애그로프레쉬 인크. | 캡슐화된 휘발성 화합물의 안정적인 에멀전 제제 |
| SG11201806420RA (en) | 2016-02-19 | 2018-08-30 | Hazel Technologies Inc | Compositions for controlled release of active ingredients and methods of making same |
| KR20250011239A (ko) * | 2018-04-27 | 2025-01-21 | 프레쉬 인셋 에스.에이. | 1-메틸사이클로프로펜 및 알파-사이클로덱스트린의 복합체를 포함하는 조성물 및 물품 |
| KR102133837B1 (ko) * | 2018-06-20 | 2020-07-14 | 코스맥스바이오 주식회사 | 슬러리 연질캡슐 제제용 현탁화제 및 이를 포함하는 슬러리 연질캡슐 |
| CN109350060B (zh) * | 2018-10-17 | 2023-12-05 | 四川大学华西医院 | 一种核磁共振踝关节线圈装置 |
| RU2717300C1 (ru) * | 2019-04-02 | 2020-03-19 | Мария Ивановна Иванова | Способ получения модифицированного порошкового препарата для обработки растений |
| US11306046B2 (en) * | 2019-11-16 | 2022-04-19 | Nazir Mir | Generators for 1-methylcyclopropene release from carrier complex |
| AU2021217212A1 (en) | 2020-02-03 | 2022-09-01 | Fresh Inset S.A. | Stable 1-methylcyclopropene compositions and uses thereof |
| US20210331990A1 (en) | 2020-04-27 | 2021-10-28 | Cellresin Technologies, Llc | Compositions and Methods for Differential Release of 1-Methylcyclopropene |
| WO2023288294A1 (en) | 2021-07-16 | 2023-01-19 | Novozymes A/S | Compositions and methods for improving the rainfastness of proteins on plant surfaces |
| WO2023225459A2 (en) | 2022-05-14 | 2023-11-23 | Novozymes A/S | Compositions and methods for preventing, treating, supressing and/or eliminating phytopathogenic infestations and infections |
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| US5238714A (en) * | 1990-10-02 | 1993-08-24 | Board Of Regents, The University Of Texas System | Efficient microcapsule preparation and method of use |
| IL145476A (en) * | 2000-09-29 | 2006-07-05 | Rohm & Haas | Cyclopropene release systems that require less water |
| CA2565427A1 (en) * | 2005-11-08 | 2007-05-08 | Rohm And Haas Company | Compositions with cyclopropenes and non-hydrocarbon oils |
| PL2109641T3 (pl) * | 2007-01-17 | 2017-09-29 | Agrofresh Inc. | Dostarczanie środków blokujących i/lub pobudzających etylen |
| JP5128392B2 (ja) * | 2007-08-03 | 2013-01-23 | ローム アンド ハース カンパニー | 油配合物 |
| EP2385761B1 (en) * | 2009-01-09 | 2018-04-18 | Syngenta Participations AG | Stabilized agrochemical composition |
| EP2542054B9 (en) * | 2010-03-01 | 2016-09-14 | AgroFresh Inc. | Oil formulations comprising 1-methyl cylcopropene |
| WO2011156388A1 (en) * | 2010-06-07 | 2011-12-15 | Syngenta Participations Ag | Cyclopropene compositions |
| CA2743758C (en) * | 2010-07-02 | 2013-01-08 | Rohm And Haas Company | Coated powder particles |
| CA2770949C (en) * | 2011-04-05 | 2013-06-18 | Rohm And Haas Company | Controlled release compositions |
| CN102217671B (zh) * | 2011-04-27 | 2013-07-03 | 武汉双奇科技发展有限公司 | 1-甲基环丙烯缓释剂及其制备方法 |
| MX2015003422A (es) * | 2012-09-17 | 2015-10-22 | Rohm & Haas | Composiciones con matriz de resina fundida en caliente. |
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2013
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2015
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- 2015-02-25 IL IL237412A patent/IL237412A0/en unknown
- 2015-03-16 PH PH12015500572A patent/PH12015500572A1/en unknown
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