WO2013008734A1 - 有機el素子用水分吸着剤及びその製造方法 - Google Patents
有機el素子用水分吸着剤及びその製造方法 Download PDFInfo
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- WO2013008734A1 WO2013008734A1 PCT/JP2012/067292 JP2012067292W WO2013008734A1 WO 2013008734 A1 WO2013008734 A1 WO 2013008734A1 JP 2012067292 W JP2012067292 W JP 2012067292W WO 2013008734 A1 WO2013008734 A1 WO 2013008734A1
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- WIPO (PCT)
- Prior art keywords
- organic
- calcium oxide
- moisture
- display element
- organic electroluminescence
- Prior art date
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- 238000005401 electroluminescence Methods 0.000 title abstract 4
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims abstract description 70
- 239000000292 calcium oxide Substances 0.000 claims abstract description 50
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims abstract description 30
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- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 4
- 239000000920 calcium hydroxide Substances 0.000 description 4
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- 230000000052 comparative effect Effects 0.000 description 3
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
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- 239000002250 absorbent Substances 0.000 description 2
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- 229910052786 argon Inorganic materials 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
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- IATRAKWUXMZMIY-UHFFFAOYSA-N strontium oxide Chemical compound [O-2].[Sr+2] IATRAKWUXMZMIY-UHFFFAOYSA-N 0.000 description 2
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- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- MUJRNJDKBBSXSE-UHFFFAOYSA-N calcium;butan-1-olate Chemical compound [Ca+2].CCCC[O-].CCCC[O-] MUJRNJDKBBSXSE-UHFFFAOYSA-N 0.000 description 1
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- OEPJXTZQPRTGCX-UHFFFAOYSA-N calcium;propan-1-olate Chemical compound [Ca+2].CCC[O-].CCC[O-] OEPJXTZQPRTGCX-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
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- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
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- YWXYYJSYQOXTPL-SLPGGIOYSA-N isosorbide mononitrate Chemical compound [O-][N+](=O)O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 YWXYYJSYQOXTPL-SLPGGIOYSA-N 0.000 description 1
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- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2253/00—Adsorbents used in seperation treatment of gases and vapours
- B01D2253/25—Coated, impregnated or composite adsorbents
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2253/00—Adsorbents used in seperation treatment of gases and vapours
- B01D2253/30—Physical properties of adsorbents
- B01D2253/302—Dimensions
- B01D2253/304—Linear dimensions, e.g. particle shape, diameter
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2253/00—Adsorbents used in seperation treatment of gases and vapours
- B01D2253/30—Physical properties of adsorbents
- B01D2253/302—Dimensions
- B01D2253/306—Surface area, e.g. BET-specific surface
Definitions
- the present invention relates to a moisture adsorbent for organic EL elements and a method for producing the same.
- Organic light-emitting materials used in organic EL elements have a problem that they deteriorate due to moisture and shorten their lifetime.
- the organic light-emitting materials absorb moisture remaining in the element during manufacturing of the organic EL element and moisture entering from the outside.
- a hygroscopic material moisture getter
- the moisture getter is required to rapidly adsorb moisture after sealing, barium oxide, strontium oxide, or calcium oxide with an increased moisture adsorption rate is used.
- rate can be obtained by baking calcium hydroxide on pressure reduction conditions, for example as disclosed by patent document 1.
- calcium oxide is strongly alkaline, it can be used only for some resins such as fluororesin, which may break the polymer bond when used in organic polymer materials such as resins. There is.
- calcium oxide is hydrophilic, there is a problem that it is difficult to fill an organic polymer material such as a hydrophobic resin.
- a method for modifying the particle surface is known as a method for solving these problems.
- the surface of calcium oxide is coated with a surface treatment agent such as a fatty acid, it can be modified to be hydrophobic, but the problem is that the moisture absorption rate decreases and the original activity is lost. .
- the present invention has been made in view of the above problems, and an object thereof is to provide a moisture adsorbent for organic EL elements that has hydrophobicity and does not decrease the moisture absorption rate, and a method for producing the same.
- the present invention relates to a moisture adsorbent for organic EL devices, characterized in that the main component is calcium oxide particles having an alkoxide layer on the surface.
- the present inventors have found that calcium oxide particles can be obtained by atomizing calcium oxide in the presence of alcohol to increase the activity by atomization and having an alkoxide layer on the surface, leading to the present invention. It was. That is, the present invention relates to a method for producing a moisture adsorbent for an organic EL device, which comprises dry pulverizing calcium oxide in the presence of alcohol and then performing a drying treatment.
- the water adsorbent for organic EL devices according to the present invention is characterized by containing calcium oxide particles having an alkoxide layer as a main component.
- the alkoxide layer is present on the surface of the calcium oxide particles, and examples thereof include layers of calcium methoxide, calcium ethoxide, calcium propoxide, calcium butoxide and the like.
- BET specific surface area of the organic EL element water absorbent according to the present invention is preferably 10 ⁇ 100m 2 / g, more preferably 15 ⁇ 100m 2 / g, more preferably 15 ⁇ 60m 2 / g.
- the average particle size is preferably 0.2 to 10 ⁇ m, more preferably 0.5 to 3 ⁇ m.
- the bulk density is preferably 0.5 to 1.5 g / cm 3 and more preferably 0.7 to 1.2 g / cm 3 .
- the alkoxide is hydrolyzed, decomposed into water and alcohol, and the alkoxide is generated by the reaction between the alcohol and calcium oxide.
- the reaction represented by the following formula (1) occurs from right to left through the alkoxide layer, and the alkoxide is generated again from alcohol and calcium oxide by the left to right reaction represented by the following formula (1).
- moisture content reacts with the calcium oxide inside particle
- the moisture adsorbent for organic EL elements according to the present invention can be produced by dry-grinding calcium oxide in the presence of alcohol and then performing a drying treatment.
- the BET specific surface area of calcium oxide used as a raw material is not particularly limited, but is preferably 0.1 to 60 m 2 / g, 5 to 30 m 2 / g is more preferable.
- the average particle diameter of calcium oxide is not particularly limited, but is preferably 1 ⁇ m to 5 mm.
- the alcohol used is preferably an alcohol having 1 to 6 carbon atoms, and is easily obtained and easy to handle. Alcohol is particularly preferred. Specific preferred alcohols include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol and the like. You may use these individually or in mixture of 2 or more types.
- the amount used is preferably 1 to 20% by mass relative to calcium oxide, and 5 to 15% by mass. % Is more preferable.
- the dry pulverization method is not particularly limited, but a pulverizer such as a media mill, a rotating ball mill, a vibration ball mill, a planetary ball mill, a rocking mill, or a paint shaker is used. can do.
- a pulverizer such as a media mill, a rotating ball mill, a vibration ball mill, a planetary ball mill, a rocking mill, or a paint shaker is used. can do.
- a pulverizer using a metal, resin, or ceramic medium as a medium such as a media mill or a rocking mill is preferable.
- the material of the medium is preferably made of nylon or zirconia with little wear because of its low contamination.
- the size of the media can be appropriately selected according to the particle size of the material to be crushed.
- the pulverization is preferably performed in an inert gas atmosphere.
- the inert gas include helium and argon, but it is particularly preferable that the inert gas is performed in a nitrogen gas atmosphere from an economical viewpoint.
- the pulverization process may be performed in a single stage, but the pulverization may be performed in multiple stages by changing the media diameter and the pulverization apparatus.
- the drying treatment is performed by heat drying, and examples of the drying device include a shelf dryer, a rotary dryer, and a vibration dryer.
- Calcium oxide particles having an alkoxide layer are dried with nitrogen gas in the dryer to prevent decomposition of the alkoxide layer or formation of calcium hydroxide or calcium carbonate by reaction with water vapor or carbon dioxide in the atmosphere. It is preferable to carry out while introducing an inert gas such as argon gas.
- the temperature of the heat drying treatment is preferably 80 to 180 ° C., more preferably 120 to 170 ° C. below the decomposition temperature of the alkoxide layer.
- the moisture adsorbent for organic EL elements has excellent effects such as high bulk density and easy filling of the resin, low oil absorption and high filling of the resin.
- the oil absorption is an index for evaluating the filling property of the powder into the resin, and this method can be used for the evaluation of the filling property (magazine “Industrial Materials” vol. 39, No. 1, p 116-117 (1991). ).
- the moisture adsorbent for organic EL elements according to the present invention can be used by being dispersed in a synthetic resin and molded into a sheet, pellet, plate, or film. These molded products can be advantageously used as a desiccant for electronic devices such as organic EL displays.
- synthetic resin polyolefin resin, polyacrylic resin, polyacrylonitrile resin, polyamide resin, polyester resin, epoxy resin, polycarbonate resin, and fluorine resin can be used.
- the moisture adsorbent for organic EL elements according to the present invention can be used by being housed in a moisture-permeable bag or container used for a normal moisture absorbent.
- moisture-content adsorption agent for organic EL elements which concerns on this invention may be used independently, and may be used together with another hygroscopic material (for example, a silica gel or molecular sieve).
- Oil absorption-Section 2 Measurement was carried out in accordance with the oil method.
- the oil absorption amount (mL / 100 g) was determined from the amount of dripping at the end point at which the sample prepared by dripping the oil into the boiled sesame and kneading the oil into the boiled sesame was able to be wound in a spiral shape.
- Ethanol was used as a dispersion solvent for the sample, and dispersion treatment was performed for 3 minutes with an ultrasonic homogenizer (MODEL US-150T, manufactured by Memoto Seiki Seisakusho).
- the average particle size of the dispersed sample was measured using a laser diffraction particle size distribution analyzer (MICROTRAC HRA9320-X100, manufactured by Nikkiso Co., Ltd.).
- the BET specific surface area was measured by the BET single point method using Monosorb (manufactured by Quantachrome).
- the FT-IR was measured by assembling a Fourier transform infrared spectrophotometer (FT / IR-6100, manufactured by JASCO Corporation) with a single reflection measurement device (ATR PRO470-H).
- the measured wavenumber range is 4000-400 cm ⁇ 1 .
- Example 1 A high specific surface area calcium oxide granular product (BET) obtained by calcining a granulated product of 120 g of zirconia beads (made by Nikkato Co., Ltd.) having a diameter of 4.0 mm and calcium hydroxide fine powder at 600 ° C. in a 100 mL sealed container (made of polypropylene) 6 g of a specific surface area of 16.5 m 2 / g and a particle size of 2-3 mm) and 0.45 g of ethanol were added and sealed. The above operation was performed in a glove box filled with nitrogen so that the sealed container was filled with nitrogen.
- BET calcium oxide granular product
- the sealed container taken out from the glove box was pulverized at 700 rpm for 4 hours with a rocking mill (Seiwa Giken Co., Ltd.). After the treatment, zirconia beads and CaO powder were separated using a sieve having an opening of 500 ⁇ m in a nitrogen-filled glove box. The separated and collected CaO powder was dried in a nitrogen atmosphere at 150 ° C. for 18 hours with a shelf dryer to obtain a CaO powder whose particle surface was covered with alkoxide. The presence of an alkoxide layer on the surface of the obtained CaO powder was confirmed by FT-IR. Table 1 shows the physical properties of the obtained CaO powder.
- Example 2 Instead of high specific surface area calcium oxide granular products, high purity calcium oxide powder (ultra high purity calcia (CSQ), BET specific surface area 2.3 m 2 / g, average particle size 16.5 ⁇ m, manufactured by Ube Materials Co., Ltd.) Manufactured in the same manner as in Example 1 except that it was used. The presence of an alkoxide layer on the surface of the obtained CaO powder was confirmed by FT-IR. Table 1 shows the physical properties of the obtained CaO powder.
- CSQ ultra high purity calcia
- BET specific surface area 2.3 m 2 / g average particle size 16.5 ⁇ m, manufactured by Ube Materials Co., Ltd.
- Example 3 Prepared by the same method as Example 2 except that 2-propanol was used instead of ethanol. The presence of an alkoxide layer on the surface of the obtained CaO powder was confirmed by FT-IR. Table 1 shows the physical properties of the obtained CaO powder.
- Example 4 Prepared by the same method as Example 2 except that 1-butanol was used instead of ethanol. The presence of an alkoxide layer on the surface of the obtained CaO powder was confirmed by FT-IR. Table 1 shows the physical properties of the obtained CaO powder.
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Abstract
Description
水分ゲッターは、封止後に水分を急速に吸着することが要求されるため、酸化バリウムや酸化ストロンチウム、もしくは水分吸着速度を速めた酸化カルシウムが使用されている。そして、水分吸着速度を速めた酸化カルシウムは、例えば特許文献1に開示されているように、水酸化カルシウムを減圧条件下にて焼成することにより得ることが出来る。
従来、これらの問題点を解決する方法としては、粒子表面を改質する方法が知られている。しかし、本用途に関しては、酸化カルシウムの表面を脂肪酸などの表面処理剤でコーティングすると、疎水性に改質することは出来るが、吸湿速度が低下し本来の活性を失ってしまうことが問題となる。
なお、粉砕処理は、一段で行っても良いが、メディア径や粉砕装置を換えて多段で粉砕を行っても良い。
予め乾燥したシャーレの重量を測定し[A(g)]とした。測定対象となる粉末約0.6gをシャーレに仕込み、重量を正確に秤量し[B(g)]とした。粉体を仕込んだシャーレを24℃、相対湿度55%に保った恒温恒湿槽に入れ120分後の重量を計測し[C(g)]として、下記式(2)によって重量増加率を算出した。
JIS K5101-13-2:2004 顔料試験方法-第13部:吸油量-第2節:煮あまに油法に従って測定を行った。所定量の粉末試料に煮あまに油を滴下し煮あまに油と練り合わせた試料がらせん形に巻くことができる状態になった終点の滴下量より吸油量(mL/100g)を求めた。
試料の分散溶媒としてエタノールを使用し、超音波ホモジナイザー(MODEL US-150T、(株)目本精機製作所製)で3分間分散処理を行った。分散させた試料をレーザー回折式粒度分布測定装置(MICROTRAC HRA9320-X100、日機装(株)製)を用いて平均粒子径の測定をした。
BET比表面積の測定は、Monosorb(Quantachrome製)を用いてBET一点法により測定した。
試料の有機溶媒への分散性評価は、n-ヘキサンを用いて行った。ガラス瓶にn-ヘキサン5mlをとり、試料を約0.1g加え、一分間振盪後、静置し30秒後の溶液の様子を観察した。ヘキサン中に分散して濁っていれば、有機溶媒と試料の分散性が良好(○)であると評価し、ヘキサン中では凝集してヘキサンが透明のまま試料が沈殿していれば有機溶媒と試料の分散性は悪い(×)と評価した。
窒素充填したグローブボックス内で容積4.4cm3の石英容器(底面10mm×10mm、高さ44mm)に試料を静かに詰め、山盛り充填した。粉の表面をすり切って試料重量を正確に秤量し[D(g)]として、下記式(3)によりかさ密度を算出した。
FT-IRの測定は、フーリエ変換赤外分光光度計(FT/IR-6100、日本分光(株)製)に1回反射測定装置(ATR PRO470-H)を組み付け測定を行った。測定した波数の範囲は4000-400cm-1である。
100mL密閉容器(ポリプロピレン製)に直径φ4.0mmのジルコニア製ビーズ((株)ニッカトー製)を120gと水酸化カルシウム微粉末の造粒品を600℃で焼成した高比表面積酸化カルシウム粒状品(BET比表面積16.5m2/g、粒度2-3mm)6gとエタノール0.45gを加え密封した。以上の操作は、窒素を充填したグローブボックス内で行い、本密閉容器が窒素で充填されるようにした。グローブボックスから取り出した本密閉容器をロッキングミル((株)セイワ技研)で4時間700rpmで粉砕処理した。処理後、窒素充填したグローブボックス内で目開き500μmの篩を用いてジルコニア製ビーズとCaO粉末を分離した。分離・回収したCaO粉末を棚式乾燥機にて窒素雰囲気中で150℃、18時間乾燥処理を行い、粒子表面をアルコキシドで覆ったCaO粉末を得た。得られたCaO粉末の表面にアルコキシド層が存在することをFT-IRにより確認した。得られたCaO粉末の物性は、表1に示す。
高比表面積酸化カルシウム粒状品の代わりに高純度酸化カルシウム粉末(超高純度カルシア(CSQ)、BET比表面積2.3m2/g、平均粒子径16.5μm、宇部マテリアルズ(株)製)を使用したことを除いては、実施例1と同じ方法によって製造した。得られたCaO粉末の表面にアルコキシド層が存在することをFT-IRにより確認した。得られたCaO粉末の物性は、表1に示す。
エタノールの代わりに2-プロパノールを使用したことを除いては、実施例2と同じ方法によって製造した。得られたCaO粉末の表面にアルコキシド層が存在することをFT-IRにより確認した。得られたCaO粉末の物性は、表1に示す。
エタノールの代わりに1-ブタノールを使用したことを除いては、実施例2と同じ方法によって製造した。得られたCaO粉末の表面にアルコキシド層が存在することをFT-IRにより確認した。得られたCaO粉末の物性は、表1に示す。
高純度酸化カルシウム粉末(超高純度カルシア(CSQ)、BET比表面積2.3m2/g、平均粒子径16.5μm、宇部マテリアルズ(株)製)を使用した。本CaO粉末の物性は、表1に示す。
シグマ・アルドリッチ製酸化カルシウム(nanopowder particle size<160nm(BET))を使用した。本CaO粉末の物性は、表1に示す。
ステアリン酸0.065gをジエチルエーテル40mLで溶解した。この溶液にシグマ・アルドリッチ製酸化カルシウム(nanopowder particle size<160nm(BET))を1.3g添加し10分間混合した。混合溶液を30℃にて12時間真空乾燥し溶媒を除去した。回収した乾燥粉を窒素充填したグローブボックス内でメノウ乳鉢を用いて解砕処理を行い脂肪酸で表面処理をしたCaO粉末を得た。得られたCaO粉末の物性は、表1に示す。
Claims (2)
- 表面にアルコキシド層を有する酸化カルシウム粒子を主成分とすることを特徴とする有機EL素子用水分吸着剤。
- 酸化カルシウムをアルコール存在下にて乾式粉砕を行った後、乾燥処理を行うことを特徴とする有機EL素子用水分吸着剤の製造方法。
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US14/131,241 US9115033B2 (en) | 2011-07-14 | 2012-07-06 | Moisture absorbent for organic electroluminescence element and production method for same |
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JPH06200245A (ja) * | 1992-12-28 | 1994-07-19 | Toyo Alum Kk | 誘電体被覆物およびその製造方法 |
JP2004335136A (ja) * | 2003-04-30 | 2004-11-25 | Canon Inc | 有機発光素子 |
JP2005216636A (ja) * | 2004-01-28 | 2005-08-11 | Kyocera Corp | 封止用カバーおよびエレクトロルミネッセンス装置 |
JP2005302688A (ja) * | 2004-04-06 | 2005-10-27 | Samsung Sdi Co Ltd | 有機電界発光素子及びその製造方法 |
JP2008249559A (ja) * | 2007-03-30 | 2008-10-16 | Mitsubishi Heavy Ind Ltd | 凝集系構造体の製造方法および凝集系構造体の製造装置 |
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US9115033B2 (en) | 2015-08-25 |
US20140166927A1 (en) | 2014-06-19 |
KR101925282B1 (ko) | 2018-12-06 |
CN103797896B (zh) | 2016-04-13 |
JP5252327B2 (ja) | 2013-07-31 |
KR20140048260A (ko) | 2014-04-23 |
TW201311561A (zh) | 2013-03-16 |
CN103797896A (zh) | 2014-05-14 |
TWI525045B (zh) | 2016-03-11 |
JP2013020900A (ja) | 2013-01-31 |
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