DE60308490T2 - Verfahren zum vernetzen von asphaltzusammensetzungen und daraus hergestellte produkte - Google Patents
Verfahren zum vernetzen von asphaltzusammensetzungen und daraus hergestellte produkte Download PDFInfo
- Publication number
- DE60308490T2 DE60308490T2 DE60308490T DE60308490T DE60308490T2 DE 60308490 T2 DE60308490 T2 DE 60308490T2 DE 60308490 T DE60308490 T DE 60308490T DE 60308490 T DE60308490 T DE 60308490T DE 60308490 T2 DE60308490 T2 DE 60308490T2
- Authority
- DE
- Germany
- Prior art keywords
- crosslinking
- polymer
- group
- tert
- asphalt
- 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.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 85
- 239000010426 asphalt Substances 0.000 title claims abstract description 80
- 238000000034 method Methods 0.000 title claims abstract description 55
- 230000006855 networking Effects 0.000 title claims description 4
- 238000004132 cross linking Methods 0.000 claims abstract description 87
- 229920000642 polymer Polymers 0.000 claims abstract description 80
- 239000003999 initiator Substances 0.000 claims abstract description 37
- 230000008569 process Effects 0.000 claims abstract description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 229920001577 copolymer Polymers 0.000 claims description 10
- 239000005062 Polybutadiene Substances 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- 150000007973 cyanuric acids Chemical class 0.000 claims description 6
- 150000001451 organic peroxides Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 229920002857 polybutadiene Polymers 0.000 claims description 4
- CTWUNIKBHNWJSR-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2-methylheptane Chemical compound CC(C)(C)OOC(CC)CCC(C)(C)OOC(C)(C)C CTWUNIKBHNWJSR-UHFFFAOYSA-N 0.000 claims description 3
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 claims description 3
- KRDXTHSSNCTAGY-UHFFFAOYSA-N 2-cyclohexylpyrrolidine Chemical compound C1CCNC1C1CCCCC1 KRDXTHSSNCTAGY-UHFFFAOYSA-N 0.000 claims description 3
- VXPSQDAMFATNNG-UHFFFAOYSA-N 3-[2-(2,5-dioxopyrrol-3-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C=2C(=CC=CC=2)C=2C(NC(=O)C=2)=O)=C1 VXPSQDAMFATNNG-UHFFFAOYSA-N 0.000 claims description 3
- 239000004793 Polystyrene Substances 0.000 claims description 3
- 229920006037 cross link polymer Polymers 0.000 claims description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 3
- 229920002223 polystyrene Polymers 0.000 claims description 3
- -1 (tert-butyl) peroxyisopropyl Chemical group 0.000 claims 2
- YKTNISGZEGZHIS-UHFFFAOYSA-N 2-$l^{1}-oxidanyloxy-2-methylpropane Chemical group CC(C)(C)O[O] YKTNISGZEGZHIS-UHFFFAOYSA-N 0.000 claims 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 2
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 44
- 229910052717 sulfur Inorganic materials 0.000 abstract description 41
- 239000011593 sulfur Substances 0.000 abstract description 41
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 150000002978 peroxides Chemical class 0.000 description 30
- 238000007792 addition Methods 0.000 description 29
- 239000000523 sample Substances 0.000 description 24
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 12
- 239000003431 cross linking reagent Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- 230000006872 improvement Effects 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 238000011084 recovery Methods 0.000 description 8
- IPJGAEWUPXWFPL-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(N2C(C=CC2=O)=O)=C1 IPJGAEWUPXWFPL-UHFFFAOYSA-N 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- 229920003048 styrene butadiene rubber Polymers 0.000 description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 239000002174 Styrene-butadiene Substances 0.000 description 6
- 238000013019 agitation Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 230000035515 penetration Effects 0.000 description 5
- 238000005191 phase separation Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 230000008901 benefit Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000035882 stress Effects 0.000 description 3
- CCNDOQHYOIISTA-UHFFFAOYSA-N 1,2-bis(2-tert-butylperoxypropan-2-yl)benzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1C(C)(C)OOC(C)(C)C CCNDOQHYOIISTA-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229940005561 1,4-benzoquinone Drugs 0.000 description 1
- OXGOEZHUKDEEKS-UHFFFAOYSA-N 3-tert-butylperoxy-1,1,5-trimethylcyclohexane Chemical compound CC1CC(OOC(C)(C)C)CC(C)(C)C1 OXGOEZHUKDEEKS-UHFFFAOYSA-N 0.000 description 1
- CIUYQWLUGFWHCW-UHFFFAOYSA-N C(C)CC(C#CC(C)(OOC(C)(C)C)CC)OOC(C)(C)C Chemical compound C(C)CC(C#CC(C)(OOC(C)(C)C)CC)OOC(C)(C)C CIUYQWLUGFWHCW-UHFFFAOYSA-N 0.000 description 1
- 102100039851 DNA-directed RNA polymerases I and III subunit RPAC1 Human genes 0.000 description 1
- 101710112289 DNA-directed RNA polymerases I and III subunit RPAC1 Proteins 0.000 description 1
- 229920013645 Europrene Polymers 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000010382 chemical cross-linking Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 125000002897 diene group Chemical group 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L95/00—Compositions of bituminous materials, e.g. asphalt, tar, pitch
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L53/02—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Civil Engineering (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Engineering & Computer Science (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Graft Or Block Polymers (AREA)
- Working-Up Tar And Pitch (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/092,629 US6713540B2 (en) | 2002-03-08 | 2002-03-08 | Method for crosslinking asphalt compositions and the product resulting therefrom |
| US92629 | 2002-03-08 | ||
| PCT/EP2003/001394 WO2003076517A1 (en) | 2002-03-08 | 2003-02-11 | Method for crosslinking asphalt compositions and the product resulting therefrom |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60308490D1 DE60308490D1 (de) | 2006-11-02 |
| DE60308490T2 true DE60308490T2 (de) | 2007-06-06 |
Family
ID=27804173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60308490T Expired - Lifetime DE60308490T2 (de) | 2002-03-08 | 2003-02-11 | Verfahren zum vernetzen von asphaltzusammensetzungen und daraus hergestellte produkte |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6713540B2 (enExample) |
| EP (1) | EP1485434B1 (enExample) |
| JP (1) | JP4472993B2 (enExample) |
| KR (1) | KR100950817B1 (enExample) |
| CN (1) | CN100494285C (enExample) |
| AT (1) | ATE340227T1 (enExample) |
| AU (1) | AU2003218986B2 (enExample) |
| CA (1) | CA2477796C (enExample) |
| DE (1) | DE60308490T2 (enExample) |
| DK (1) | DK1485434T3 (enExample) |
| ES (1) | ES2272961T3 (enExample) |
| HR (1) | HRP20040794B1 (enExample) |
| MX (1) | MXPA04008615A (enExample) |
| PL (1) | PL203988B1 (enExample) |
| PT (1) | PT1485434E (enExample) |
| RS (1) | RS51022B (enExample) |
| RU (1) | RU2296143C2 (enExample) |
| WO (1) | WO2003076517A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040152805A1 (en) * | 2003-02-04 | 2004-08-05 | Buras Paul J. | Process for preparing bitumen/rubber compositions |
| JP2006022159A (ja) * | 2004-07-06 | 2006-01-26 | Kao Corp | 改質アスファルト添加剤 |
| KR101357647B1 (ko) | 2005-11-28 | 2014-02-03 | 갈라 인더스트리스 인코포레이티드 | 제어가능한 펠렛제조 공정을 위한 장치 및 방법 |
| US8136562B2 (en) * | 2006-12-29 | 2012-03-20 | Bridgestone Firestone North American Tire, Llc | Tire bead insulation |
| CA2609893C (en) | 2007-11-06 | 2013-09-10 | Husky Oil Operations Limited | Process of polymer modified asphalt preparation |
| CN102002249A (zh) * | 2010-12-15 | 2011-04-06 | 上海交通大学 | 废白土复合改性沥青及其制备方法 |
| CN103270104B (zh) * | 2010-12-21 | 2014-12-10 | 国际壳牌研究有限公司 | 具有降低的硫化氢排放的沥青组合物 |
| FR2984342B1 (fr) * | 2011-12-20 | 2014-01-03 | Total Raffinage Marketing | Procede de production d'une composition bitume/polymere reticulee avec reduction des emissions de h2s |
| US8765847B2 (en) | 2012-11-12 | 2014-07-01 | Exxonmobil Research And Engineering Company | Asphalt compositions with cracking resistance additives |
| US9340931B2 (en) | 2013-09-10 | 2016-05-17 | Fermi Research Alliance, Llc | Method and system for in-situ cross linking of polymers, bitumen and similar materials to increase strength, toughness and durability via irradiation with electron beams from mobile accelerators |
| US9186645B2 (en) | 2013-09-10 | 2015-11-17 | Fermi Research Alliance, Llc | Method and system for in-situ cross linking of polymers, bitumen and similar materials to increase strength, toughness and durability via irradiation with electron beams from mobile accelerators |
| KR101578201B1 (ko) * | 2015-04-02 | 2015-12-16 | 충남대학교산학협력단 | 폐아스콘을 포함하는 투수성 아스팔트 조성물 시공 방법 |
| US20230086227A1 (en) * | 2015-10-03 | 2023-03-23 | Asphalt Sciences Llc | System and method for modifying and enhancing tire rubber bitumen |
| US11224918B2 (en) | 2018-01-19 | 2022-01-18 | Fermi Research Alliance, Llc | SRF e-beam accelerator for metal additive manufacturing |
| US11059941B2 (en) * | 2018-04-12 | 2021-07-13 | Exxonmobil Research And Engineering Company | Methods for preparing materials from polyaromatic heavy feedstocks |
| US11123921B2 (en) | 2018-11-02 | 2021-09-21 | Fermi Research Alliance, Llc | Method and system for in situ cross-linking of materials to produce three-dimensional features via electron beams from mobile accelerators |
| US11639010B2 (en) | 2019-07-08 | 2023-05-02 | Fermi Research Alliance, Llc | Electron beam treatment for invasive pests |
| US11465920B2 (en) | 2019-07-09 | 2022-10-11 | Fermi Research Alliance, Llc | Water purification system |
| CN113667315B (zh) * | 2021-08-20 | 2022-10-14 | 华中科技大学 | 一种聚合物改性沥青及其制备方法 |
| US12371905B2 (en) | 2022-12-31 | 2025-07-29 | Asphalt Sciences Llc | Impact resistant shingle including local polymer concentration asphalt shingle coating |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3963659A (en) * | 1969-08-06 | 1976-06-15 | Chemische Werke Huls Aktiengesellschaft | Production of bitumen compositions containing ethylene-α-olefin rubber |
| US5221703A (en) * | 1992-05-14 | 1993-06-22 | Mcconnaughay Technologies, Inc. | Engineered modified asphalt cement |
| US5256710A (en) * | 1992-07-17 | 1993-10-26 | Asphalt Technology & Consultants, Inc. | Method of producing, using and composition of phenolic-type polymer modified asphalts or bitumens |
| FR2699186B1 (fr) * | 1992-12-14 | 1995-03-10 | Total Raffinage Distribution | Compositions bitume-polymère, leur procédé de préparation et leurs applications. |
| GB9227035D0 (en) * | 1992-12-29 | 1993-02-24 | Univ Toronto Innovation Found | Treatment of rubber |
| GB9306517D0 (en) * | 1993-03-29 | 1993-05-19 | Polyphalt Inc | Stabilized bitumen compositions |
| CN1140589C (zh) * | 1997-04-04 | 2004-03-03 | 波利法尔特有限公司 | 弹性体改性的沥青组合物 |
| FR2762322B1 (fr) * | 1997-04-21 | 1999-05-28 | Elf Antar France | Procede de preparation de compositions bitume/polymere, application des compositions obtenues a la production de liants bitume/polymere pour revetements et solution mere de polymere pour l'obtention desdites compositions |
| US6414056B1 (en) * | 1998-05-08 | 2002-07-02 | Exxonmobil Research And Engineering Company | Asphalt compositions and method for making (LAW617) |
| US6057390A (en) * | 1998-06-03 | 2000-05-02 | Ashland Inc. | Crosslinkable polymer-modified asphalt and its method of preparation |
| CN1167736C (zh) * | 2000-08-17 | 2004-09-22 | 上海交通大学 | 用于道路的改性沥青材料 |
-
2002
- 2002-03-08 US US10/092,629 patent/US6713540B2/en not_active Expired - Lifetime
-
2003
- 2003-02-11 WO PCT/EP2003/001394 patent/WO2003076517A1/en not_active Ceased
- 2003-02-11 ES ES03714741T patent/ES2272961T3/es not_active Expired - Lifetime
- 2003-02-11 JP JP2003574729A patent/JP4472993B2/ja not_active Expired - Lifetime
- 2003-02-11 KR KR1020047012867A patent/KR100950817B1/ko not_active Expired - Lifetime
- 2003-02-11 PT PT03714741T patent/PT1485434E/pt unknown
- 2003-02-11 DE DE60308490T patent/DE60308490T2/de not_active Expired - Lifetime
- 2003-02-11 CA CA2477796A patent/CA2477796C/en not_active Expired - Lifetime
- 2003-02-11 MX MXPA04008615A patent/MXPA04008615A/es active IP Right Grant
- 2003-02-11 RS YUP-751/04A patent/RS51022B/sr unknown
- 2003-02-11 DK DK03714741T patent/DK1485434T3/da active
- 2003-02-11 RU RU2004122923/04A patent/RU2296143C2/ru active
- 2003-02-11 AT AT03714741T patent/ATE340227T1/de active
- 2003-02-11 EP EP03714741A patent/EP1485434B1/en not_active Expired - Lifetime
- 2003-02-11 HR HRP20040794AA patent/HRP20040794B1/xx not_active IP Right Cessation
- 2003-02-11 PL PL371467A patent/PL203988B1/pl unknown
- 2003-02-11 CN CNB038050951A patent/CN100494285C/zh not_active Expired - Lifetime
- 2003-02-11 AU AU2003218986A patent/AU2003218986B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA2477796C (en) | 2011-04-19 |
| EP1485434B1 (en) | 2006-09-20 |
| US6713540B2 (en) | 2004-03-30 |
| PL203988B1 (pl) | 2009-11-30 |
| CN1697857A (zh) | 2005-11-16 |
| RU2004122923A (ru) | 2005-06-27 |
| AU2003218986B2 (en) | 2007-09-06 |
| US20030171460A1 (en) | 2003-09-11 |
| WO2003076517A1 (en) | 2003-09-18 |
| CN100494285C (zh) | 2009-06-03 |
| KR100950817B1 (ko) | 2010-04-02 |
| HRP20040794A2 (en) | 2004-12-31 |
| AU2003218986A1 (en) | 2003-09-22 |
| ATE340227T1 (de) | 2006-10-15 |
| PT1485434E (pt) | 2007-01-31 |
| DK1485434T3 (da) | 2007-01-15 |
| KR20040091061A (ko) | 2004-10-27 |
| ES2272961T3 (es) | 2007-05-01 |
| WO2003076517A8 (en) | 2004-07-22 |
| MXPA04008615A (es) | 2004-12-13 |
| RS51022B (sr) | 2010-10-31 |
| JP4472993B2 (ja) | 2010-06-02 |
| EP1485434A1 (en) | 2004-12-15 |
| HRP20040794B1 (en) | 2012-09-30 |
| CA2477796A1 (en) | 2003-09-18 |
| DE60308490D1 (de) | 2006-11-02 |
| JP2005519181A (ja) | 2005-06-30 |
| RU2296143C2 (ru) | 2007-03-27 |
| RS75104A (sr) | 2007-02-05 |
| PL371467A1 (en) | 2005-06-13 |
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