JP2009535450A5 - - Google Patents
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- Publication number
- JP2009535450A5 JP2009535450A5 JP2009507729A JP2009507729A JP2009535450A5 JP 2009535450 A5 JP2009535450 A5 JP 2009535450A5 JP 2009507729 A JP2009507729 A JP 2009507729A JP 2009507729 A JP2009507729 A JP 2009507729A JP 2009535450 A5 JP2009535450 A5 JP 2009535450A5
- Authority
- JP
- Japan
- Prior art keywords
- mole percent
- component
- dibasic acid
- acid
- diol
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims 48
- 239000002253 acid Substances 0.000 claims 47
- 150000002009 diols Chemical class 0.000 claims 44
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims 22
- 229920000728 polyester Polymers 0.000 claims 22
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 19
- 238000006243 chemical reaction Methods 0.000 claims 16
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims 14
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims 11
- 229920001169 thermoplastic Polymers 0.000 claims 8
- 239000004416 thermosoftening plastic Substances 0.000 claims 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 7
- 238000010438 heat treatment Methods 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 claims 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 2
- 230000003796 beauty Effects 0.000 claims 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims 2
- 125000001142 dicarboxylic acid group Chemical group 0.000 claims 2
- 230000032050 esterification Effects 0.000 claims 2
- 238000005886 esterification reaction Methods 0.000 claims 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N fumaric acid group Chemical group C(\C=C\C(=O)O)(=O)O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims 2
- 238000006116 polymerization reaction Methods 0.000 claims 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims 1
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims 1
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 claims 1
- ZVMAGJJPTALGQB-UHFFFAOYSA-N 2-[3-(carboxymethoxy)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=CC(OCC(O)=O)=C1 ZVMAGJJPTALGQB-UHFFFAOYSA-N 0.000 claims 1
- YZTJKOLMWJNVFH-UHFFFAOYSA-N 2-sulfobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1S(O)(=O)=O YZTJKOLMWJNVFH-UHFFFAOYSA-N 0.000 claims 1
- HSSYVKMJJLDTKZ-UHFFFAOYSA-N 3-phenylphthalic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1C(O)=O HSSYVKMJJLDTKZ-UHFFFAOYSA-N 0.000 claims 1
- WVDRSXGPQWNUBN-UHFFFAOYSA-N 4-(4-carboxyphenoxy)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C=C1 WVDRSXGPQWNUBN-UHFFFAOYSA-N 0.000 claims 1
- VTDMBRAUHKUOON-UHFFFAOYSA-N 4-[(4-carboxyphenyl)methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CC1=CC=C(C(O)=O)C=C1 VTDMBRAUHKUOON-UHFFFAOYSA-N 0.000 claims 1
- SBBQDUFLZGOASY-OWOJBTEDSA-N 4-[(e)-2-(4-carboxyphenyl)ethenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1\C=C\C1=CC=C(C(O)=O)C=C1 SBBQDUFLZGOASY-OWOJBTEDSA-N 0.000 claims 1
- QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 1
- LUSFFPXRDZKBMF-UHFFFAOYSA-N [3-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCC(CO)C1 LUSFFPXRDZKBMF-UHFFFAOYSA-N 0.000 claims 1
- 239000001361 adipic acid Substances 0.000 claims 1
- 235000011037 adipic acid Nutrition 0.000 claims 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims 1
- MGIAHHJRDZCTHG-UHFFFAOYSA-N benzene-1,3-dicarboxylic acid;terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1.OC(=O)C1=CC=CC(C(O)=O)=C1 MGIAHHJRDZCTHG-UHFFFAOYSA-N 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
- OHAFBMGBKBQYSK-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylic acid;methanol Chemical compound OC.OC(=O)C1(C(O)=O)CCCCC1 OHAFBMGBKBQYSK-UHFFFAOYSA-N 0.000 claims 1
- 239000001530 fumaric acid Substances 0.000 claims 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 claims 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 claims 1
- 229920001515 polyalkylene glycol Polymers 0.000 claims 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims 1
- 235000013772 propylene glycol Nutrition 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/414,466 US7211634B1 (en) | 2006-04-28 | 2006-04-28 | Process for the preparation of polyesters containing 1,4-cyclohexanedimethanol |
| US11/414,466 | 2006-04-28 | ||
| PCT/US2007/009484 WO2007127117A2 (en) | 2006-04-28 | 2007-04-18 | Process for the preparation of polyesters containing 1,4-cyclohexanedimethanol |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009535450A JP2009535450A (ja) | 2009-10-01 |
| JP2009535450A5 true JP2009535450A5 (enExample) | 2010-04-22 |
| JP5689599B2 JP5689599B2 (ja) | 2015-03-25 |
Family
ID=37991420
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009507729A Expired - Fee Related JP5689599B2 (ja) | 2006-04-28 | 2007-04-18 | １，４−シクロヘキサンジメタノールを含むポリエステルを製造する方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US7211634B1 (enExample) |
| EP (1) | EP2013260B1 (enExample) |
| JP (1) | JP5689599B2 (enExample) |
| KR (1) | KR101389255B1 (enExample) |
| CN (1) | CN101466760B (enExample) |
| WO (1) | WO2007127117A2 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8586701B2 (en) | 2005-10-28 | 2013-11-19 | Eastman Chemical Company | Process for the preparation of copolyesters based on 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 1,4-cyclohexanedimethanol |
| EP2225084B1 (en) | 2007-11-21 | 2013-05-29 | Eastman Chemical Company | Plastic baby bottles, other blow molded articles, and processes for their manufacture |
| CN103270555B (zh) * | 2010-10-13 | 2016-03-02 | 帝人株式会社 | 电线被覆用树脂组合物及使用其的绝缘电线 |
| US20130029068A1 (en) * | 2011-07-28 | 2013-01-31 | Eastman Chemical Company | Extrusion blow molded articles |
| RU2480486C1 (ru) * | 2011-12-16 | 2013-04-27 | Учреждение Российской академии наук Институт катализа им. Г.К. Борескова Сибирского отделения РАН | Способ получения алифатических и алифатически-ароматических полиэфиров |
| KR20140018468A (ko) * | 2012-07-30 | 2014-02-13 | 삼성정밀화학 주식회사 | 방향족 디카르복실산 화합물의 분할 투입에 의한 생분해성 폴리에스테르 공중합체의 제조방법 |
| CN107922598B (zh) * | 2015-09-04 | 2020-01-21 | Dic株式会社 | 聚酯树脂、聚酯树脂的制造方法、树脂组合物、带树脂的布帛及带树脂的布帛的制造方法 |
| IT201600078950A1 (it) * | 2016-07-27 | 2018-01-27 | Versalis Spa | Metodo di sintesi regioselettiva di poliesteri da dioli asimmetrici. |
| CN116987252A (zh) * | 2018-12-17 | 2023-11-03 | 伊士曼化工公司 | 含有低二乙二醇的来自对苯二甲酸的共聚酯 |
| KR20230008065A (ko) * | 2020-04-15 | 2023-01-13 | 도요보 가부시키가이샤 | 공중합 폴리에스테르 수지, 성형품, 열수축성 필름 및 섬유 |
| TWI803384B (zh) * | 2022-07-08 | 2023-05-21 | 南亞塑膠工業股份有限公司 | 透明pet材料及其製造方法以及pet產品 |
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| BE592181A (enExample) | 1955-12-22 | |||
| US3070575A (en) | 1958-01-27 | 1962-12-25 | Du Pont | Process for the preparation of polyesters from dicarboxylic acids and bis (hydroxy-alkyl) esters |
| BE624580A (enExample) | 1961-11-10 | |||
| AT289391B (de) | 1966-12-30 | 1971-04-26 | Alpine Chemische Ag | Verfahren zur Herstellung von Polyestern und Copolyestern |
| US3487049A (en) | 1967-01-04 | 1969-12-30 | Du Pont | Process for producing polyethylene terephthalate |
| US4020049A (en) | 1967-09-14 | 1977-04-26 | The Goodyear Tire & Rubber Company | Process for preparing polyester resin |
| US3551386A (en) | 1968-06-26 | 1970-12-29 | Monsanto Co | Polyester polymerization process,prepolymer and product |
| US3787370A (en) | 1971-03-19 | 1974-01-22 | Teijin Ltd | Process for the preparation of substan-tially linear polyesters of low free carboxyl group content |
| US3984379A (en) | 1971-12-06 | 1976-10-05 | Teijin Limited | Process for preparation of polyesters |
| JPS49117378A (enExample) | 1973-03-13 | 1974-11-09 | ||
| JPS539278B2 (enExample) * | 1973-06-07 | 1978-04-04 | ||
| US4205157A (en) | 1979-04-02 | 1980-05-27 | The Goodyear Tire & Rubber Company | Method for production of high molecular weight polyester with low catalyst level and low carboxyl content |
| US4238593B1 (en) | 1979-06-12 | 1994-03-22 | Goodyear Tire & Rubber | Method for production of a high molecular weight polyester prepared from a prepolymer polyester having an optional carboxyl content |
| US4442269A (en) | 1982-12-15 | 1984-04-10 | E. I. Du Pont De Nemours & Company | Staged copolymerization of polyesters |
| US4480086A (en) * | 1983-09-09 | 1984-10-30 | Eastman Kodak Company | Radiation-resistant copolyesters |
| US4578453A (en) * | 1984-11-23 | 1986-03-25 | Eastman Kodak Company | High molecular weight polyesters |
| US5039717A (en) | 1985-07-25 | 1991-08-13 | Amoco Corporation | Copolyesters |
| US5239018A (en) | 1989-09-06 | 1993-08-24 | Exxon Chemical Patents Inc. | Liquid polymer and polyol compositions, and process for preparing phenol-functional polymer |
| US5034263A (en) * | 1989-11-27 | 1991-07-23 | Eastman Kodak Company | Film laminate |
| US4983711A (en) | 1989-12-04 | 1991-01-08 | Eastman Kodak Company | Copolyesters and articles extrusion blow-molded therefrom |
| DE4137842A1 (de) * | 1991-11-16 | 1993-05-19 | Zimmer Ag | Verfahren zur kontinuierlichen polykondensation von terephthalsaeure und 1,4-bis-(hydroxymethyl)-cyclohexan |
| DE4137841C2 (de) | 1991-11-16 | 2003-08-28 | Zimmer Ag | Diskontinuierliches Verfahren zur Polykondensation von Terephthalsäure und 1,4-Bis-(hydroxymethyl)-cyclohexan |
| US5385773A (en) | 1993-04-27 | 1995-01-31 | Eastman Chemical Company | Copolyester of cyclohexanenedimethanol and process for producing such polyester |
| US5340907A (en) | 1993-06-28 | 1994-08-23 | Eastman Chemical Company | Copolyester of cyclohexanedimethanol and process for producing such polyester |
| US5616404A (en) * | 1995-10-10 | 1997-04-01 | Eastman Chemical Company | Orientable, heat setable semi-crystalline copolyesters |
| US5608031A (en) * | 1995-11-30 | 1997-03-04 | Eastman Chemical Company | Polyesters modified with 1,4-cyclohexaned imethanol having high clarity prepared utilizing an antimony containing catalyst/stabilizer system |
| TW381104B (en) | 1996-02-20 | 2000-02-01 | Eastman Chem Co | Process for preparing copolyesters of terephthalic acid, ethylene glycol, and 1,4-cyclohexanedimethanol |
| US5656715A (en) * | 1996-06-26 | 1997-08-12 | Eastman Chemical Company | Copolyesters based on 1,4-cyclohexanedimethanol having improved stability |
| US6103859A (en) * | 1997-04-09 | 2000-08-15 | Eastman Chemical Company | Late addition of supplemental ethylene glycol in the preparation of copolyesters |
| JP2001514336A (ja) * | 1997-08-28 | 2001-09-11 | イーストマン ケミカル カンパニー | 改良されたコポリマーバインダー繊維 |
| US5986040A (en) | 1998-09-03 | 1999-11-16 | General Electric Company | Crystalline polyester resins and process for their preparation |
| JP3693831B2 (ja) | 1998-12-18 | 2005-09-14 | 三菱化学株式会社 | ポリシクロヘキサンジメチレンテレフタレートの製造方法 |
| JP3696741B2 (ja) | 1998-12-18 | 2005-09-21 | 三菱化学株式会社 | ポリシクロヘキサンジメチレンテレフタレート |
| IT1304797B1 (it) | 1998-12-23 | 2001-03-29 | Sinco Ricerche Spa | Procedimento per la preparazione di resine poliestere (mg33). |
| US6084055A (en) * | 1999-03-30 | 2000-07-04 | General Electric Company | Method for preparing poly(1,4-cyclohexanedicarboxylates) |
| AU764147B2 (en) | 1999-10-19 | 2003-08-14 | Pet Rebirth Co., Ltd. | Method of polymerizing deionized bis-beta-hydroxyethyl terephthalate |
| KR100366483B1 (ko) | 1999-12-17 | 2003-01-14 | 주식회사 이래화학 | 코폴리에스테르 수지 조성물 및 그 제조방법 |
| TWI235754B (en) | 1999-12-27 | 2005-07-11 | Ind Tech Res Inst | Composition and process for preparing a high molecular weight polyester |
| JP3209336B1 (ja) * | 2000-05-17 | 2001-09-17 | エスケー ケミカルズ カンパニー リミテッド | １，４−シクロヘキサンジメタノールが共重合されたポリエステル樹脂の製造方法 |
| JP4649709B2 (ja) | 2000-07-25 | 2011-03-16 | 東亞合成株式会社 | 共重合ポリエステルの製造方法 |
| JP2004517980A (ja) | 2000-09-21 | 2004-06-17 | ローム アンド ハース カンパニー | 極性モノマーと多価カチオンとに関わる方法および組成物 |
| US6458915B1 (en) * | 2000-10-13 | 2002-10-01 | Eastman Chemical Company | Process for producing poly(1,4-cyclohexylenedimethylene 1,4-cyclohexanedicarboxylate) and the reactor grade polyester therefrom |
| US6455664B1 (en) | 2000-11-20 | 2002-09-24 | General Electric Company | Crystalline polyester resins and process for their preparation |
| US6429278B1 (en) * | 2001-01-22 | 2002-08-06 | Eastman Chemical Company | Process for manufacture of polyesters based on 1,4-cyclohexanedimethanol and isophthalic acid |
| US6740377B2 (en) * | 2001-09-14 | 2004-05-25 | Eastman Chemical Company | Polyester having improved crystallization behavior and extrusion blow molded articles made therefrom |
| ITMI20021293A1 (it) | 2002-06-12 | 2003-12-12 | Gen Electric | Metodo per preparare poli(cicloesan-1,4-dicarbossilato) (i) da acido cicloesan-1,4-bicarbossilico e composizione |
| US6828410B2 (en) | 2002-07-10 | 2004-12-07 | General Electric Company | Method for preparing poly(cyclohexane-1,4-dicarboxylate)s from cyclohexane-1,4-dicarboxylic acid, and composition |
| US6924349B2 (en) * | 2003-06-23 | 2005-08-02 | Sk Chemicals Co., Ltd. | Copolyester resin and articles using the same |
-
2006
- 2006-04-28 US US11/414,466 patent/US7211634B1/en active Active
-
2007
- 2007-02-20 US US11/708,244 patent/US20070255020A1/en not_active Abandoned
- 2007-04-18 JP JP2009507729A patent/JP5689599B2/ja not_active Expired - Fee Related
- 2007-04-18 EP EP07775690.6A patent/EP2013260B1/en not_active Not-in-force
- 2007-04-18 CN CN200780021818XA patent/CN101466760B/zh not_active Expired - Fee Related
- 2007-04-18 WO PCT/US2007/009484 patent/WO2007127117A2/en not_active Ceased
- 2007-04-18 KR KR1020087026292A patent/KR101389255B1/ko not_active Expired - Fee Related
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