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WO2008054560A3 - Certain polyester compositions which comprise tetramethylcyclobutanediol, cyclohexanedimethanol and high trans-cyclohexanedicarboxylic acid - Google Patents

Certain polyester compositions which comprise tetramethylcyclobutanediol, cyclohexanedimethanol and high trans-cyclohexanedicarboxylic acid Download PDF

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Publication number
WO2008054560A3
WO2008054560A3 PCT/US2007/015713 US2007015713W WO2008054560A3 WO 2008054560 A3 WO2008054560 A3 WO 2008054560A3 US 2007015713 W US2007015713 W US 2007015713W WO 2008054560 A3 WO2008054560 A3 WO 2008054560A3
Authority
WO
WIPO (PCT)
Prior art keywords
mole
cyclohexanedicarboxylic acid
acid residues
residues
cyclohexanedimethanol
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.)
Ceased
Application number
PCT/US2007/015713
Other languages
French (fr)
Other versions
WO2008054560A2 (en
Inventor
Leslie Shane Moody
Emmett Dudley Crawford
Jeremy Richards Lizotte
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eastman Chemical Co
Original Assignee
Eastman Chemical Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from US11/588,883 external-priority patent/US20070105993A1/en
Priority claimed from US11/588,458 external-priority patent/US20070100122A1/en
Priority claimed from US11/588,906 external-priority patent/US8193302B2/en
Priority claimed from PCT/US2006/042292 external-priority patent/WO2007053549A1/en
Priority claimed from PCT/US2006/042069 external-priority patent/WO2007053460A1/en
Priority claimed from US11/588,524 external-priority patent/US20100096589A1/en
Priority claimed from US11/588,527 external-priority patent/US20100087574A1/en
Priority claimed from US11/588,554 external-priority patent/US20070100125A1/en
Priority claimed from US11/588,907 external-priority patent/US20070106054A1/en
Priority claimed from US11/635,434 external-priority patent/US7737246B2/en
Priority claimed from US11/635,433 external-priority patent/US20070142511A1/en
Priority claimed from US11/706,476 external-priority patent/US20070232778A1/en
Priority claimed from US11/706,791 external-priority patent/US20070232779A1/en
Priority claimed from PCT/US2007/007632 external-priority patent/WO2007126855A1/en
Priority claimed from PCT/US2007/010590 external-priority patent/WO2007139655A1/en
Priority claimed from US11/773,275 external-priority patent/US8586701B2/en
Application filed by Eastman Chemical Co filed Critical Eastman Chemical Co
Publication of WO2008054560A2 publication Critical patent/WO2008054560A2/en
Publication of WO2008054560A3 publication Critical patent/WO2008054560A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/199—Acids or hydroxy compounds containing cycloaliphatic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/181—Acids containing aromatic rings
    • C08G63/183—Terephthalic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/78—Preparation processes
    • C08G63/82—Preparation processes characterised by the catalyst used
    • C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)

Abstract

Described as one aspect of the invention are polyester compositions comprising at least one polyester which comprises: (A) a dicarboxylic acid component comprising: i) 70 to 100 mole % of cyclohexanedicarboxylic acid residues or an ester thereof comprising: (a) 70 to 98 mole % trans-cyclohexanedicarboxylic acid residues or an ester thereof; and (b) 2 to 30 mole % cis-cyclohexanedicarboxylic acid residues or an ester thereof; ii) 0 to 30 mole % of aliphatic dicarboxylic acid residues, other than cyclohexanedicarboxylic acid residues, having up to 16 carbon atoms or esters thereof, other than cyclohexanedicarboxylic acid residues,; and iii) 0 to 10 mole % of aromatic dicarboxylic acid residues having up to 20 carbon atoms; and (B) a glycol component comprising: i) 1 to 99 mole % of 2, 2, 4, 4-tetramethyl-1, 3-cyclobutanediol residues; and ii) 1 to 99 mole % of 1, 4-cyclohexanedimethanol residues, 1, 3-cyclohexariedimethanol residues, 1, 2-cyclohexanedimethanol residues or esters thereof or mixtures thereof, wherein the total mole % of said dicarboxylic acid component is equal to 100 mole %; the total mole % of said glycol component is equal to 100 mole %; wherein the inherent viscosity of said polyester is from 0.35 to 1.2 dL/g as determined in 60/40 (wt/wt) phenol/ tetrachloroethane at a concentration of 0.5 g/100 ml at 25°C; and wherein said polyester has a Tg of from 60 to 155°C. The polyesters may be manufactured into articles.
PCT/US2007/015713 2006-10-27 2007-07-10 Certain polyester compositions which comprise tetramethylcyclobutanediol, cyclohexanedimethanol and high trans-cyclohexanedicarboxylic acid Ceased WO2008054560A2 (en)

Applications Claiming Priority (46)

Application Number Priority Date Filing Date Title
PCT/US2006/042292 WO2007053549A1 (en) 2005-10-28 2006-10-27 Polyester compositions containing cyclobutanediol having a certain combination of inherent viscosity and moderate glass transition temperature and articles made therefrom
PCT/US2006/042069 WO2007053460A1 (en) 2005-10-28 2006-10-27 Polyester compositions which comprise cyclobutanediol and at least one phosphorus compound
US11/588,524 US20100096589A1 (en) 2005-10-28 2006-10-27 Polyester compositions containing low amounts of cyclobutanediol and articles made therefrom
US11/588,527 US20100087574A1 (en) 2005-10-28 2006-10-27 Polyester compositions containing cyclobutanediol having a certain combination of inherent viscosity and moderate glass transition temperature and articles made therefrom
USPCT/US06/42292 2006-10-27
US11/588,906 2006-10-27
US11/588,524 2006-10-27
US11/588,527 2006-10-27
US11/588,907 2006-10-27
US11/588,554 US20070100125A1 (en) 2005-10-28 2006-10-27 Polyester compositions comprising minimal amounts of cyclobutanediol
US11/588,458 2006-10-27
US11/588,883 2006-10-27
USPCT/US06/41917 2006-10-27
US11/588,554 2006-10-27
USPCT/US06/42291 2006-10-27
US11/588,907 US20070106054A1 (en) 2005-10-28 2006-10-27 Polyester compositions containing cyclobutanediol having a certain combination of inherent viscosity and high glass transition temperature and articles made therefrom
US11/588,906 US8193302B2 (en) 2005-10-28 2006-10-27 Polyester compositions which comprise cyclobutanediol and certain phosphate thermal stabilizers, and/or reaction products thereof
PCT/US2006/042293 WO2007053550A1 (en) 2005-10-28 2006-10-27 Polyester compositions containing cyclobutanediol having high glass transition temperature and articles made therefrom
PCT/US2006/041917 WO2007053434A1 (en) 2005-10-28 2006-10-27 Polyester compositions which comprise cyclobutanediol and certain thermal stabilizers, and/or reaction products thereof
USPCT/US06/42293 2006-10-27
US11/588,883 US20070105993A1 (en) 2005-10-28 2006-10-27 Polyester compositions which comprise cyclobutanediol and at least one phosphorus compound
USPCT/US06/42069 2006-10-27
PCT/US2006/042291 WO2007053548A2 (en) 2005-10-28 2006-10-27 Polyester compositions comprising minimal amounts of cyclobutanediol
US11/588,458 US20070100122A1 (en) 2005-10-28 2006-10-27 Polyester compositions containing cyclobutanediol and articles made therefrom
US11/635,434 US7737246B2 (en) 2005-12-15 2006-12-07 Polyester compositions which comprise cyclobutanediol, cyclohexanedimethanol, and ethylene glycol and manufacturing processes therefor
US11/635,433 US20070142511A1 (en) 2005-12-15 2006-12-07 Polyester compositions which comprise cyclobutanediol ethylene glycol, titanium, and phosphorus with improved color and manufacturing processes therefor
US11/635,433 2006-12-07
US11/635,434 2006-12-07
US11/706,476 2007-02-14
US11/706,791 2007-02-14
US11/706,476 US20070232778A1 (en) 2006-03-28 2007-02-14 Certain polyester compositions which comprise cyclobutanediol, cyclohexanedimethanol, and high trans-cyclohexanedicarboxylic acid
US11/706,791 US20070232779A1 (en) 2006-03-28 2007-02-14 Certain polyester compositions which comprise cyclohexanedimethanol, moderate cyclobutanediol, cyclohexanedimethanol, and high trans cyclohexanedicarboxylic acid
USPCT/US07/07632 2007-03-27
USPCT/US07/07532 2007-03-27
PCT/US2007/007632 WO2007126855A1 (en) 2006-03-28 2007-03-27 Polyester compositions which comprise cyclobutanediol and certain thermal stabilizers, and/or reaction products thereof
PCT/US2007/007532 WO2007123631A1 (en) 2006-03-28 2007-03-27 Polyester compositions which comprise cyclobutanediol and at least one phosphorus compound
PCT/US2007/010590 WO2007139655A1 (en) 2006-05-23 2007-05-02 Polyester compositions which comprise cyclobutanediol and certain thermal stabilizers, and/or reaction products thereof
USPCT/US07/10551 2007-05-02
PCT/US2007/010551 WO2007139653A1 (en) 2006-05-23 2007-05-02 Lcd films or sheets comprising films comprising polyester compositions formed from 2,2,4,4,-tetramethyl-1,3-cyclobutanediol and 1,4-cyclohexanedimethanol
USPCT/US07/10590 2007-05-02
PCT/US2007/011150 WO2007139663A1 (en) 2006-05-23 2007-05-09 Polyester compositions which comprise cyclobutanediol and certain thermal stabilizers, and/or reaction products thereof
USPCT/US07/11150 2007-05-09
US91731607P 2007-05-10 2007-05-10
US60/917,316 2007-05-10
US11/773,275 2007-07-03
US11/773,275 US8586701B2 (en) 2005-10-28 2007-07-03 Process for the preparation of copolyesters based on 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 1,4-cyclohexanedimethanol

Publications (2)

Publication Number Publication Date
WO2008054560A2 WO2008054560A2 (en) 2008-05-08
WO2008054560A3 true WO2008054560A3 (en) 2008-07-24

Family

ID=47831243

Family Applications (4)

Application Number Title Priority Date Filing Date
PCT/US2007/015702 Ceased WO2008054559A1 (en) 2006-10-27 2007-07-10 Certain polyester compositions which comprise tetramethylcyclobutanediol, cyclohexanedimethanol and high trans- cyclohexanedicarboxylic acid
PCT/US2007/015713 Ceased WO2008054560A2 (en) 2006-10-27 2007-07-10 Certain polyester compositions which comprise tetramethylcyclobutanediol, cyclohexanedimethanol and high trans-cyclohexanedicarboxylic acid
PCT/US2007/015701 Ceased WO2008051320A1 (en) 2006-10-27 2007-07-10 Polyester compositions which comprise tetramethylcyclobutanediol, cyclohexanedimethanol and ethylene glycol, and manufacturing processes therefor
PCT/US2007/015704 Ceased WO2008051321A1 (en) 2006-10-27 2007-07-10 Polyester compositions which comprise cyclobutanediol, ethylene glycol, titanium, and phosphorus with improved color and manufacturing processes therefor

Family Applications Before (1)

Application Number Title Priority Date Filing Date
PCT/US2007/015702 Ceased WO2008054559A1 (en) 2006-10-27 2007-07-10 Certain polyester compositions which comprise tetramethylcyclobutanediol, cyclohexanedimethanol and high trans- cyclohexanedicarboxylic acid

Family Applications After (2)

Application Number Title Priority Date Filing Date
PCT/US2007/015701 Ceased WO2008051320A1 (en) 2006-10-27 2007-07-10 Polyester compositions which comprise tetramethylcyclobutanediol, cyclohexanedimethanol and ethylene glycol, and manufacturing processes therefor
PCT/US2007/015704 Ceased WO2008051321A1 (en) 2006-10-27 2007-07-10 Polyester compositions which comprise cyclobutanediol, ethylene glycol, titanium, and phosphorus with improved color and manufacturing processes therefor

Country Status (8)

Country Link
EP (2) EP2074174A1 (en)
JP (2) JP2010507717A (en)
KR (2) KR20090079212A (en)
BR (2) BRPI0717755A2 (en)
CA (2) CA2666571A1 (en)
MX (2) MX2009003369A (en)
TW (2) TW200819497A (en)
WO (4) WO2008054559A1 (en)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8168721B2 (en) * 2009-02-06 2012-05-01 Eastman Chemical Company Coating compositions containing tetramethyl cyclobutanediol
US8163850B2 (en) * 2009-02-06 2012-04-24 Eastman Chemical Company Thermosetting polyester coating compositions containing tetramethyl cyclobutanediol
US9029460B2 (en) * 2009-02-06 2015-05-12 Stacey James Marsh Coating compositions containing acrylic and aliphatic polyester blends
US7915374B2 (en) * 2009-04-27 2011-03-29 Eastman Chemical Company Copolyesters having improved thermal stability and methods for making them
US9156941B2 (en) * 2010-12-20 2015-10-13 Eastman Chemical Company Color in titanium catalyzed polyesters
US20120184668A1 (en) * 2011-01-17 2012-07-19 Eastman Chemical Company Clear Ternary Blends of Polycarbonate with an Aliphatic Polyester and an Aromatic-Aliphatic Polyester
US8580872B2 (en) * 2011-07-21 2013-11-12 Eastman Chemical Company Sulfopolyester polymer compositions with improved water dispersibility
JP5806326B2 (en) * 2011-11-01 2015-11-10 ミドリ安全株式会社 Resin composition and molded body
US8623483B1 (en) * 2012-10-23 2014-01-07 Eastman Chemical Company Copolyesters containing neopentyl glycol and 2,2,4,4-tetraalkyl 1,3-cyclobutanediol
JP6489012B2 (en) * 2014-02-24 2019-03-27 東レ株式会社 Polyester film
WO2015129500A1 (en) * 2014-02-27 2015-09-03 東レ株式会社 Laminate film
JP6323872B2 (en) * 2014-07-31 2018-05-16 花王株式会社 Toner for electrophotography
JP6323871B2 (en) * 2014-07-31 2018-05-16 花王株式会社 Toner for electrophotography
JP2015028177A (en) * 2014-09-22 2015-02-12 イーストマン ケミカル カンパニー Improved method for producing polyester
CN109563252B (en) 2016-08-18 2022-04-26 伊士曼化工公司 Polyester composition comprising tetramethylcyclobutanediol and ethylene glycol using improved catalyst system
EP3500615B1 (en) 2016-08-18 2025-08-06 Eastman Chemical Company Oriented films and shrink films comprising polyesters which comprise tetramethyl cyclobutanediol and ethylene glycol
EP3878888A1 (en) 2016-08-18 2021-09-15 Eastman Chemical Company Polyester compositions which comprise tetramethyl cyclobutanediol and ethylene glycol, with improved catalyst system
KR102589382B1 (en) * 2018-08-08 2023-10-12 에스케이케미칼 주식회사 Polyester resin and preparation method of the same
CN118893887A (en) * 2019-08-02 2024-11-05 伊士曼化工公司 Multilayer sheet
CN114729113B (en) * 2019-10-08 2025-03-18 伊士曼化工公司 Catalyst systems for crystallizable reactor-grade resins
KR102498421B1 (en) * 2020-08-19 2023-02-10 효성티앤씨 주식회사 Polyester molded article and method for preparing the same
US11788317B2 (en) * 2020-09-28 2023-10-17 Kathryn Corcoran Cell phone canopy
CN116529284A (en) * 2020-10-08 2023-08-01 伊士曼化工公司 Shrinkable polyester film
JP7647301B2 (en) * 2021-04-28 2025-03-18 三菱ケミカル株式会社 Resin composition for cards or passports, film for cards or passports, cards, and passports
JP7647302B2 (en) * 2021-04-28 2025-03-18 三菱ケミカル株式会社 Resin composition for cards or passports, film for cards or passports, cards, and passports
JP7700515B2 (en) * 2021-05-28 2025-07-01 三菱ケミカル株式会社 Resin composition for cards or passports, film for cards or passports, cards, and passports
KR20250141152A (en) * 2023-02-09 2025-09-26 이스트만 케미칼 (차이나) 컴퍼니 리미티드 Molded polyester articles with improved aesthetic and chemical resistance
WO2025136741A1 (en) * 2023-12-18 2025-06-26 Eastman Chemical Company Films for use in dental appliances

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US4525504A (en) * 1983-10-24 1985-06-25 Eastman Kodak Company Stabilized polyester compositions suitable for outdoor applications
US5498668A (en) * 1994-10-31 1996-03-12 Eastman Chemical Company Blends of certain polyesters with acrylics

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US6495656B1 (en) * 1990-11-30 2002-12-17 Eastman Chemical Company Copolyesters and fibrous materials formed therefrom
US6037424A (en) * 1996-12-28 2000-03-14 Eastman Chemical Company Clear blends of polycarbonates and polyesters
US6043322A (en) * 1996-12-28 2000-03-28 Eastman Chemical Company Clear polycarbonate and polyester blends
US5989663A (en) * 1996-12-30 1999-11-23 Eastman Chemical Company Blow-molding polyesters from terephthalic acid, 2, 2, 4, 4-tetramethyl-1,3-cyclobutanediol, and ethylene glycol
US6120889A (en) * 1999-06-03 2000-09-19 Eastman Chemical Company Low melt viscosity amorphous copolyesters with enhanced glass transition temperatures
EP1644436A2 (en) * 2003-07-11 2006-04-12 Eastman Chemical Company Addition of uv absorbers to pet process for maximum yield
US20050010017A1 (en) * 2003-07-11 2005-01-13 Blakely Dale Milton Addition of UV inhibitors to pet process for maximum yield
US20060094858A1 (en) * 2004-10-28 2006-05-04 Turner Sam R Novel copolyester compositions with improved impact strength at low temperatures
WO2007053549A1 (en) * 2005-10-28 2007-05-10 Eastman Chemical Company Polyester compositions containing cyclobutanediol having a certain combination of inherent viscosity and moderate glass transition temperature and articles made therefrom
WO2007053434A1 (en) * 2005-10-28 2007-05-10 Eastman Chemical Company Polyester compositions which comprise cyclobutanediol and certain thermal stabilizers, and/or reaction products thereof

Patent Citations (2)

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Publication number Priority date Publication date Assignee Title
US4525504A (en) * 1983-10-24 1985-06-25 Eastman Kodak Company Stabilized polyester compositions suitable for outdoor applications
US5498668A (en) * 1994-10-31 1996-03-12 Eastman Chemical Company Blends of certain polyesters with acrylics

Also Published As

Publication number Publication date
WO2008054560A2 (en) 2008-05-08
TW200819497A (en) 2008-05-01
WO2008051320A1 (en) 2008-05-02
MX2009003369A (en) 2009-04-14
WO2008051321A8 (en) 2008-07-10
TW200819496A (en) 2008-05-01
JP2010507716A (en) 2010-03-11
CA2666585A1 (en) 2008-05-02
EP2074158A1 (en) 2009-07-01
CA2666571A1 (en) 2008-05-02
WO2008051321A1 (en) 2008-05-02
KR20090079211A (en) 2009-07-21
BRPI0717761A2 (en) 2013-03-12
MX2009003375A (en) 2009-04-14
KR20090079212A (en) 2009-07-21
BRPI0717755A2 (en) 2013-03-12
JP2010507717A (en) 2010-03-11
EP2074174A1 (en) 2009-07-01
WO2008054559A1 (en) 2008-05-08

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