WO2010073430A1 - 低含水量のフォトレジスト剥離液用濃縮液の製造方法 - Google Patents
低含水量のフォトレジスト剥離液用濃縮液の製造方法 Download PDFInfo
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- WO2010073430A1 WO2010073430A1 PCT/JP2009/004169 JP2009004169W WO2010073430A1 WO 2010073430 A1 WO2010073430 A1 WO 2010073430A1 JP 2009004169 W JP2009004169 W JP 2009004169W WO 2010073430 A1 WO2010073430 A1 WO 2010073430A1
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- quaternary ammonium
- ammonium hydroxide
- solution
- water
- tmah
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/90—Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/42—Stripping or agents therefor
- G03F7/422—Stripping or agents therefor using liquids only
- G03F7/425—Stripping or agents therefor using liquids only containing mineral alkaline compounds; containing organic basic compounds, e.g. quaternary ammonium compounds; containing heterocyclic basic compounds containing nitrogen
Definitions
- the present invention relates to a method for producing a quaternary ammonium hydroxide concentrate used as a raw material for a photoresist stripping solution, and more particularly to a method for producing a quaternary ammonium hydroxide concentrate having a lower water content than conventional ones.
- a semiconductor element such as an IC or LSI, or a liquid crystal panel element
- an insulating film such as a conductive metal film or a SiO 2 film is formed on a substrate such as a silicon wafer or glass.
- a photoresist is uniformly applied on the conductive metal film or the insulating film, and this is selectively exposed and developed to form a resist pattern.
- the substrate is selectively dry-etched using this resist pattern as a mask to form a fine circuit. Thereafter, unnecessary photoresist film residue and etching residue are removed by washing with a stripping solution.
- a sodium hydroxide aqueous solution or a general organic solvent can be used alone to provide a stripping effect, but the stripping property is not sufficient.
- various photoresist stripping solutions have been proposed in order to improve the stripping properties.
- As a general method for example, there is a method using a solution of quaternary ammonium hydroxide such as tetramethylammonium hydroxide (TMAH).
- TMAH tetramethylammonium hydroxide
- the stripping solution is generally prepared from a solution prepared from a commercially available quaternary ammonium hydroxide-containing crystal or a commercially available aqueous solution of quaternary ammonium hydroxide in dimethyl sulfoxide (DMSO) or 3-methoxy- This is done by diluting to the desired concentration with an organic solvent such as 3-methyl-1-butanol (MMB).
- DMSO dimethyl sulfoxide
- MMB 3-methyl-1-butanol
- the peelability of the stripping solution depends on the water content of the stripping solution, and the lower the water content, the higher the peelability.
- the stripping solution is prepared by diluting a quaternary ammonium hydroxide solution with an organic solvent. Therefore, in order to reduce the water content of the stripping solution, a quaternary ammonium hydroxide solution is used. It needs to be concentrated to a low water content.
- TMAH pentahydrate As a method of concentrating a quaternary ammonium hydroxide solution to reduce the water content, TMAH pentahydrate (TMAH: water weight ratio is 1: 1) is dissolved in methanol and concentrated in a batch system under reduced pressure. And a method of adding a molecular sieve to a DMSO solution containing TMAH pentahydrate and drying (see Patent Documents 1 and 2).
- the former method requires the heating for a long time, and has the disadvantage that TMAH is easily decomposed, and the product obtained after the concentration is solid, so that it is difficult to handle.
- the latter method has a drawback that it uses a molecular sieve and is expensive, and a disadvantage that the operation becomes complicated.
- the present invention was devised in view of the current state of the prior art, and an object thereof is to provide a method capable of easily producing a quaternary ammonium hydroxide concentrate having a low water content.
- the present inventors diligently studied production conditions for obtaining a concentrated solution of quaternary ammonium hydroxide having a low water content.
- the inventors have found that a concentrated solution of quaternary ammonium hydroxide having a low water content can be produced by mixing a quaternary ammonium with a specific water-soluble organic solvent and performing thin film distillation, and the present invention has been completed.
- a method for producing a concentrated solution of quaternary ammonium hydroxide comprising quaternary ammonium hydroxide in the form of hydrous crystals or an aqueous solution, glycol ethers, glycols, and triols.
- a production method comprising preparing a mixed solution by mixing with a water-soluble organic solvent selected from the group consisting of the above, and distilling the distillate by thin-film distillation of the mixed solution under reduced pressure.
- DC drying coefficient
- quaternary ammonium hydroxide in the form of water-containing crystals or aqueous solution is mixed with a specific water-soluble organic solvent and thin film distilled to concentrate quaternary ammonium hydroxide having a low water content.
- the liquid can be easily manufactured. Further, the produced concentrated liquid can achieve a lower water content (higher drying coefficient of 3.5 or more) than the concentrated liquid produced by a conventionally known production method. Therefore, when used as a photoresist stripping solution, an extremely high stripping effect can be expected.
- the production method of the present invention uses thin-film distillation, the quaternary ammonium hydroxide solution can be concentrated by heating in a short time, and the quaternary ammonium hydroxide is not easily decomposed during the concentration operation. . Further, since the liquid obtained by the concentration operation is a liquid, it is easy to handle.
- the production method of the present invention is characterized in that quaternary ammonium hydroxide in the form of hydrous crystals or an aqueous solution is mixed with a specific water-soluble organic solvent and thin-film distilled.
- quaternary ammonium hydroxide tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, trimethylethylammonium hydroxide, dimethyldiethylammonium hydroxide, trimethyl (2-hydroxyethyl) )
- Quaternary ammonium hydroxides such as ammonium hydroxide and triethyl (2-hydroxyethyl) ammonium hydroxide, and bipyrrolidinium hydroxides such as spiro- [1,1 ′]-bipyrrolidinium hydroxide may be used. it can.
- TMAH tetramethylammonium hydroxide
- tetrapropylammonium hydroxide tetrapropylammonium hydroxide
- spiro- [1,1 ']-bipyrrolidinium hydroxide are preferable from the viewpoint of improving the peeling performance, and TMAH is particularly preferable.
- quaternary ammonium hydroxide can be used 1 type or in combination of 2 or more types.
- Quaternary ammonium hydroxide is used in the form of hydrous crystals or an aqueous solution.
- the quaternary ammonium hydroxide is TMAH
- the TMAH hydrous crystal TMAH pentahydrate
- TMAH 25 wt. It is preferable to use an aqueous solution of TMAH in terms of cost.
- quaternary ammonium hydroxide is mixed with a water-soluble organic solvent selected from the group consisting of glycol ethers, glycols, and triols.
- glycol ethers that can be used in the present invention include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol monobutyl ether, triethylene glycol
- Examples include ethylene glycol monomethyl ether, 3-methoxy-3-methyl-1-butanol, dipropylene glycol monomethyl ether, and 2- (2-methoxyethoxy) ethanol.
- glycols include ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, and triethylene glycol.
- triols include glycerin. Among these, 3-methoxy-3-methyl-1-butanol (MMB), diethylene glycol, propylene glycol, glycerin or 2- (2-methoxyethoxy) ethanol is preferable, and the concentrate is diluted to produce a stripping solution.
- MMB 3-methoxy-3-methyl-1-butanol
- MMB 3-methoxy-3-methyl-1-butanol
- MMB 2- (2-methoxyethoxy
- the weight blending ratio of the quaternary ammonium hydroxide and the water-soluble organic solvent is not particularly limited, depending on the target concentration of the quaternary ammonium hydroxide in the stripping solution to be finally produced. However, it is generally about 1: 0.5 to about 1:30.
- alkanolamines When mixing the quaternary ammonium hydroxide and the water-soluble organic solvent, alkanolamines may be further mixed. When alkanolamines are mixed, a mixed solution of quaternary ammonium hydroxide and a water-soluble organic solvent can be made uniform. Moreover, when alkanolamines are mixed, more water-soluble organic solvent can be removed during thin film distillation.
- the alkanolamines used in the present invention include monoethanolamine (MEA), diethanolamine, triethanolamine, ethylaminoethanol, dimethylaminoethanol, diethylaminoethanol, 2- (2-aminoethoxy) ethanol and the like. Of these, monoethanolamine and 2- (2-aminoethoxy) ethanol are preferably used. These may be used alone or in combination of two or more.
- the amount of alkanolamines used is not particularly limited, but is generally up to about 20% by weight based on the total amount of 25% quaternary ammonium hydrox
- quaternary ammonium hydroxide, a water-soluble organic solvent, and, if desired, an alkanolamine are mixed to prepare a mixed solution, and then the obtained mixed solution is decompressed.
- Distillate is distilled off by thin film distillation below. This operation can be easily performed using a commercially available thin-film distillation apparatus.
- the distillation temperature and the degree of vacuum are not particularly limited, and can be, for example, 80 ° C. to 130 ° C. and 0.1 kPa to 5.0 kPa, respectively.
- the distillation residue after distillation obtained by the production method of the present invention is the concentrated solution of quaternary ammonium hydroxide of the present invention.
- This concentrate has a DC (drying coefficient) of 3.5 or more, more preferably 4.0 or more, particularly 5.0 or more, and is a concentrate having a very low water content. Therefore, if this concentrated solution is used, it is possible to prepare a photoresist stripping solution with extremely high stripping properties.
- the DC of this concentrated liquid is not particularly limited in theory, but can be, for example, 50 or less, further 30 or less, particularly 15 or less.
- a short path distillation apparatus (hereinafter referred to as SPD) KDL5 or KD10 manufactured by UIC in Germany was used as the thin film distillation apparatus.
- the TMAH content and MEA content (when MEA was used) in the distillation residue were calculated by neutralization titration.
- the water content was calculated with a Karl Fischer moisture meter.
- the content of the water-soluble organic solvent was calculated by subtracting the TMAH content, MEA content (when MEA was used), and water content from the weight of the distillation residue.
- Example 1 Mixing 12.0 g of 25 wt% TMAH aqueous solution and 60.0 g of propylene glycol as a distillation raw material, using SPD (KDL5) as a thin film distillation apparatus, performing thin film distillation at a distillation temperature of 100 ° C. and a vacuum degree of 1.9 kPa, Distillate was distilled off.
- SPD KDL5
- TMAH propylene glycol 17.0 g
- water 0.4 g
- DC 6.3
- Example 3 20.1 g of 25 wt% TMAH aqueous solution and 60.3 g of 2- (2-methoxyethoxy) ethanol were mixed as a raw material for distillation, and SPD (KDL5) was used as a thin-film distillation apparatus, with a distillation temperature of 100 ° C. and a vacuum degree of 1.9 kPa. The distillate was distilled off.
- SPD KDL5
- Example 4 Mixing 12.0 g of 25 wt% TMAH aqueous solution and 60.0 g of MMB as a raw material for distillation, using SPD (KDL5) as a thin film distillation apparatus, performing thin film distillation at a distillation temperature of 100 ° C. and a vacuum degree of 1.7 kPa, and distilling The product was distilled off.
- SPD KDL5
- TMAH TMAH
- DC 5.1
- Example 5 Thin film distillation was performed at a distillation temperature of 100 ° C. and a vacuum of 1.7 kPa using 7.96 kg of 25 wt% TMAH aqueous solution as a raw material for distillation, 16.0 kg of MMB and 1.2 kg of MEA, and using SPD (KD10) as a thin film distillation apparatus. And the distillate was distilled off.
- TMAH TMAH
- MMB MEA
- water 18. 6% by weight: 71.9% by weight: 6.6% by weight: 2.9% by weight
- DC 6.5
- Example 6 Distillate is obtained by mixing 6.2 g of TMAH pentahydrate and 49.6 g of MMB as raw materials for distillation, thin film distillation at a distillation temperature of 100 ° C. and a vacuum of 1.9 kPa using SPD (KDL5) as a thin film distillation apparatus. Was distilled off.
- SPD KDL5
- the production method of the present invention can easily produce a concentrated solution of quaternary ammonium hydroxide having a low water content, which could not be obtained by a conventionally known production method. It is extremely useful for producing a concentrate for raw materials.
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Abstract
Description
しかし、前者の方法は、長時間の加熱が必要であり、TMAHが分解しやすくなるという欠点や、濃縮後に得られるものが固体であるため、取扱いが困難であるという欠点を有する。また、後者の方法は、モレキュラーシーブを使用するので費用がかかるという欠点や、操作が煩雑になるという欠点を有する。また、濃縮液や剥離液に微粒子が含まれることは望ましくないため、乾燥後にモレキュラーシーブを除去する必要があるという欠点も有する。さらに述べると、これらの方法で得られる濃縮液の含水量は十分低いとは言い難い。従って、従来公知の水酸化第4級アンモニウムの濃縮液の製造方法には、未だ改良の余地がある。
なお、蒸留残分中のTMAH含量及びMEA含量(MEAを使用した場合)は中和滴定によって算出した。水分含量はカールフィッシャー水分計によって算出した。水溶性有機溶媒の含量は、蒸留残分の重量からTMAH含量、MEA含量(MEAを使用した場合)、及び水分含量を差し引くことによって算出した。
蒸留原料として25重量%TMAH水溶液32.0g、DMSO80.0gを混合し、薄膜蒸留装置としてSPD(KDL5)を用いて蒸留温度100℃、減圧度1.1kPaにて薄膜蒸留を行い、留出物を留去した。得られた蒸留残分(水酸化第4級アンモニウム濃縮液)の分析を行ったところ、TMAH3.9g、DMSO21.8g、水2.1g(TMAH:DMSO:水=14.1重量%:78.2重量%:7.7重量%)であった(DC=1.8)。蒸留残分はすぐに結晶を析出した。
蒸留原料として25重量%TMAH水溶液12.0g、プロピレングリコール60.0gを混合し、薄膜蒸留装置としてSPD(KDL5)を用いて、蒸留温度100℃、減圧度1.9kPaにて薄膜蒸留を行い、留出物を留去した。得られた蒸留残分(水酸化第4級アンモニウム濃縮液)の分析を行ったところ、TMAH2.5g、プロピレングリコール17.0g、水0.4g(TMAH:プロピレングリコール:水=12.6重量%:85.4重量%:2.0重量%)であった(DC=6.3)。蒸留残分には結晶は見られなかった。
蒸留原料として25重量%TMAH水溶液21.1g、ジエチレングリコール63.3gを混合し、薄膜蒸留装置としてSPD(KDL5)を用いて、蒸留温度100℃、減圧度1.7kPaにて薄膜蒸留を行い、留出物を留去した。得られた蒸留残分(水酸化第4級アンモニウム濃縮液)の分析を行ったところ、TMAH4.9g、ジエチレングリコール49.4g、水0.6g(TMAH:ジメチレングリコール:水=8.9重量%:90.0重量%:1.1重量%)であった(DC=8.1)。蒸留残分には結晶は見られなかった。
蒸留原料として25重量%TMAH水溶液20.1g、2-(2-メトキシエトキシ)エタノール60.3gを混合し、薄膜蒸留装置としてSPD(KDL5)を用いて、蒸留温度100℃、減圧度1.9kPaにて薄膜蒸留を行い、留出物を留去した。得られた蒸留残分(水酸化第4級アンモニウム濃縮液)の分析を行ったところ、TMAH4.5g、2-(2-メトキシエトキシ)エタノール22.9g、水1.1g(TMAH:2-(2-メトキシエトキシ)エタノール:水=15.8重量%:80.2重量%:4.0重量%)であった(DC=4.0)。蒸留残分には結晶は見られなかった。
蒸留原料として25重量%TMAH水溶液12.0g、MMB60.0gを混合し、薄膜蒸留装置としてSPD(KDL5)を用いて、蒸留温度100℃、減圧度1.7kPaにて薄膜蒸留を行い、留出物を留去した。得られた蒸留残分(水酸化第4級アンモニウム濃縮液)の分析を行ったところ、TMAH2.0g、MMB9.9g、水0.4g(TMAH:MMB:水=16.0重量%:80.8重量%:3.1重量%)であった(DC=5.1)。蒸留残分には結晶は見られなかった。
蒸留原料として25重量%TMAH水溶液7.96kg、MMB16.0kgとMEA1.2kgを混合し、薄膜蒸留装置としてSPD(KD10)を用いて、蒸留温度100℃、減圧度1.7kPaにて薄膜蒸留を行い、留出物を留去した。得られた蒸留残分(水酸化第4級アンモニウム濃縮液)の分析を行ったところ、TMAH1.68kg、MMB6.5kg、MEA0.60kg、水0.26kg(TMAH:MMB:MEA:水=18.6重量%:71.9重量%:6.6重量%:2.9重量%)であった(DC=6.5)。蒸留残分には結晶は見られなかった。
蒸留原料としてTMAH5水和物6.2g、MMB49.6gを混合し、薄膜蒸留装置としてSPD(KDL5)を用いて、蒸留温度100℃、減圧度1.9kPaにて薄膜蒸留を行い、留出物を留去した。得られた蒸留残分(水酸化第4級アンモニウム濃縮液)の分析を行ったところ、TMAH2.4g、MMB11.5g、水0.5g(TMAH:MMB:水=17.0重量%:79.5重量%:3.5重量%)であった(DC=4.9)。蒸留残分には若干結晶が析出していた。
蒸留原料として25重量%TMAH水溶液50.4g、グリセリン50.4gを混合し、薄膜蒸留装置としてSPD(KDL5)を用いて、蒸留温度100℃、減圧度1.6kPaにて薄膜蒸留を行い、留出物を留去した。得られた蒸留残分(水酸化第4級アンモニウム濃縮液)の分析を行ったところ、TMAH10.6g、グリセリン39.7g、水0.8g(TMAH:グリセリン:水=20.7重量%:77.8重量%:1.5重量%)であった(DC=13.8)。蒸留残分には結晶は見られなかった。
Claims (6)
- 水酸化第4級アンモニウムの濃縮液の製造方法であって、含水結晶又は水溶液の形態の水酸化第4級アンモニウムと、グリコールエーテル類、グリコール類、及びトリオール類からなる群から選択される水溶性有機溶剤とを混合して混合液を調製し、その混合液を減圧下に薄膜蒸留して留出物を留去することを特徴とする製造方法。
- 水酸化第4級アンモニウムがテトラメチルアンモニウムヒドロキシドであり、テトラメチルアンモニウムヒドロキシドが水溶液の形態であることを特徴とする請求項1に記載の製造方法。
- 水溶性有機溶剤が、3-メトキシ-3-メチル-1-ブタノール、ジエチレングリコール、プロピレングリコール、グリセリン、又は2-(2-メトキシエトキシ)エタノールであることを特徴とする請求項1又は2に記載の製造方法。
- 水溶性有機溶剤が3-メトキシ-3-メチル-1-ブタノールであることを特徴とする請求項3に記載の製造方法。
- 混合液にアルカノールアミン類をさらに混合することを特徴とする請求項1~4のいずれか一項に記載の製造方法。
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US12/863,841 US8299303B2 (en) | 2008-12-26 | 2009-08-27 | Process for producing a concentrated solution for a photoresist-stripping liquid having low water content |
JP2010517219A JP4673935B2 (ja) | 2008-12-26 | 2009-08-27 | 低含水量のフォトレジスト剥離液用濃縮液の製造方法 |
CN200980101738.4A CN101910109B (zh) | 2008-12-26 | 2009-08-27 | 具有低水含量的光刻胶-去膜液的浓缩溶液的生产方法 |
EP09834248.8A EP2371809A4 (en) | 2008-12-26 | 2009-08-27 | PROCESS FOR PRODUCING CONCENTRATED SOLUTION FOR PHOTOSENSITIVE RESIN STRIPPING AGENT HAVING A LOW WATER CONTENT |
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- 2009-08-27 WO PCT/JP2009/004169 patent/WO2010073430A1/ja active Application Filing
- 2009-08-27 US US12/863,841 patent/US8299303B2/en not_active Expired - Fee Related
- 2009-08-27 CN CN200980101738.4A patent/CN101910109B/zh not_active Expired - Fee Related
- 2009-08-27 EP EP09834248.8A patent/EP2371809A4/en not_active Withdrawn
- 2009-12-23 TW TW098144434A patent/TWI428170B/zh not_active IP Right Cessation
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CN102314101A (zh) * | 2010-07-08 | 2012-01-11 | 东友Fine-Chem股份有限公司 | 用于除去聚酰亚胺的清洗剂组合物 |
KR20200033252A (ko) | 2017-08-02 | 2020-03-27 | 주식회사 쿠라레 | 회수 레지스트 박리제로부터의 디메틸술폭시드의 회수 방법 |
US11028047B2 (en) | 2017-08-02 | 2021-06-08 | Kuraray Co., Ltd. | Method for recovering dimethyl sulfoxide from recovered resist remover |
JP2020075908A (ja) * | 2018-09-28 | 2020-05-21 | 株式会社トクヤマ | 水酸化第4級アンモニウムの有機溶媒溶液の製造方法 |
JP2020145406A (ja) * | 2019-02-28 | 2020-09-10 | 株式会社トクヤマ | 水酸化第4級アンモニウムの有機溶媒溶液の製造方法 |
JP7482621B2 (ja) | 2019-02-28 | 2024-05-14 | 株式会社トクヤマ | 水酸化第4級アンモニウムの有機溶媒溶液の製造方法 |
JP2021116236A (ja) * | 2020-01-22 | 2021-08-10 | 株式会社トクヤマ | 低含水水酸化第4級アンモニウム溶液の製造方法 |
JP7426836B2 (ja) | 2020-01-22 | 2024-02-02 | 株式会社トクヤマ | 低含水水酸化第4級アンモニウム溶液の製造方法 |
Also Published As
Publication number | Publication date |
---|---|
EP2371809A4 (en) | 2015-09-02 |
JPWO2010073430A1 (ja) | 2012-05-31 |
TWI428170B (zh) | 2014-03-01 |
CN101910109A (zh) | 2010-12-08 |
TW201032890A (en) | 2010-09-16 |
CN101910109B (zh) | 2014-08-27 |
JP4673935B2 (ja) | 2011-04-20 |
US8299303B2 (en) | 2012-10-30 |
KR20110016854A (ko) | 2011-02-18 |
US20100298605A1 (en) | 2010-11-25 |
KR101260599B1 (ko) | 2013-05-06 |
EP2371809A1 (en) | 2011-10-05 |
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