JP4372539B2 - 熱可塑性ポリオレフィンエラストマー組成物の架橋方法 - Google Patents
熱可塑性ポリオレフィンエラストマー組成物の架橋方法 Download PDFInfo
- Publication number
- JP4372539B2 JP4372539B2 JP2003506349A JP2003506349A JP4372539B2 JP 4372539 B2 JP4372539 B2 JP 4372539B2 JP 2003506349 A JP2003506349 A JP 2003506349A JP 2003506349 A JP2003506349 A JP 2003506349A JP 4372539 B2 JP4372539 B2 JP 4372539B2
- Authority
- JP
- Japan
- Prior art keywords
- thermoplastic polyolefin
- ethylene
- propylene
- copolymer
- elastomer
- 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 - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title claims abstract description 31
- 238000004132 cross linking Methods 0.000 title claims abstract description 30
- 229920002397 thermoplastic olefin Polymers 0.000 title claims abstract description 27
- 229920000098 polyolefin Polymers 0.000 claims abstract description 23
- 229920001971 elastomer Polymers 0.000 claims abstract description 16
- 239000004594 Masterbatch (MB) Substances 0.000 claims abstract description 15
- 239000000806 elastomer Substances 0.000 claims abstract description 14
- 238000002156 mixing Methods 0.000 claims abstract description 13
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 10
- 239000000654 additive Substances 0.000 claims abstract description 9
- 238000001816 cooling Methods 0.000 claims abstract description 8
- 230000000996 additive effect Effects 0.000 claims abstract description 4
- 238000007711 solidification Methods 0.000 claims abstract description 4
- 230000008023 solidification Effects 0.000 claims abstract description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 21
- 239000005977 Ethylene Substances 0.000 claims description 21
- 229920001577 copolymer Polymers 0.000 claims description 18
- 239000004711 α-olefin Substances 0.000 claims description 13
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 12
- 239000008096 xylene Substances 0.000 claims description 12
- 238000004898 kneading Methods 0.000 claims description 11
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 11
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- 150000001993 dienes Chemical class 0.000 claims description 4
- 229920001384 propylene homopolymer Polymers 0.000 claims description 4
- 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 3
- 229920005604 random copolymer Polymers 0.000 claims description 3
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims description 2
- 229920002589 poly(vinylethylene) polymer Polymers 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 description 12
- 229960002447 thiram Drugs 0.000 description 9
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- 229920001169 thermoplastic Polymers 0.000 description 6
- 239000004416 thermosoftening plastic Substances 0.000 description 6
- 229920000181 Ethylene propylene rubber Polymers 0.000 description 5
- 238000007906 compression Methods 0.000 description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 230000006835 compression Effects 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000005662 Paraffin oil Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 150000001451 organic peroxides Chemical class 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000011954 Ziegler–Natta catalyst Substances 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- VVFNNEKHSFZNKA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhex-3-ene Chemical compound CC(C)(C)OOC(C)(C)C=CC(C)(C)OOC(C)(C)C VVFNNEKHSFZNKA-UHFFFAOYSA-N 0.000 description 1
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- RIVJYLGQARVCBI-UHFFFAOYSA-N 2-tert-butylperoxy-2-methylpropane;cumene Chemical compound CC(C)C1=CC=CC=C1.CC(C)(C)OOC(C)(C)C RIVJYLGQARVCBI-UHFFFAOYSA-N 0.000 description 1
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- -1 dimethyl cyanurate derivatives Chemical class 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012968 metallocene catalyst Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000010094 polymer processing Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005606 polypropylene copolymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229920005653 propylene-ethylene copolymer Polymers 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010058 rubber compounding Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/10—Homopolymers or copolymers of propene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/20—Compounding polymers with additives, e.g. colouring
- C08J3/22—Compounding polymers with additives, e.g. colouring using masterbatch techniques
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/16—Ethene-propene or ethene-propene-diene copolymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2207/00—Properties characterising the ingredient of the composition
- C08L2207/02—Heterophasic composition
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/04—Homopolymers or copolymers of ethene
- C08L23/08—Copolymers of ethene
- C08L23/0807—Copolymers of ethene with unsaturated hydrocarbons only containing four or more carbon atoms
- C08L23/0815—Copolymers of ethene with unsaturated hydrocarbons only containing four or more carbon atoms with aliphatic 1-olefins containing one carbon-to-carbon double bond
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01114459 | 2001-06-15 | ||
| PCT/EP2002/005908 WO2002102880A1 (en) | 2001-06-15 | 2002-05-29 | Process for cross-linking thermoplastic polyolefin elastomer compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004530757A JP2004530757A (ja) | 2004-10-07 |
| JP2004530757A5 JP2004530757A5 (enExample) | 2006-01-05 |
| JP4372539B2 true JP4372539B2 (ja) | 2009-11-25 |
Family
ID=8177726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003506349A Expired - Fee Related JP4372539B2 (ja) | 2001-06-15 | 2002-05-29 | 熱可塑性ポリオレフィンエラストマー組成物の架橋方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US7632894B2 (enExample) |
| EP (1) | EP1401925B1 (enExample) |
| JP (1) | JP4372539B2 (enExample) |
| KR (1) | KR20030022892A (enExample) |
| CN (1) | CN1244614C (enExample) |
| AT (1) | ATE307847T1 (enExample) |
| BR (1) | BR0205531A (enExample) |
| CA (1) | CA2455257A1 (enExample) |
| DE (1) | DE60206915T2 (enExample) |
| RU (1) | RU2003128026A (enExample) |
| WO (1) | WO2002102880A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2338910T5 (es) * | 2006-05-26 | 2014-03-28 | Borealis Technology Oy | Composición de poliolefina con resistencia al emblanquecimiento por tensión mejorada |
| CN101479334B (zh) * | 2006-06-23 | 2012-07-04 | 巴塞尔聚烯烃意大利有限责任公司 | 聚烯烃热塑性硫化产品弹性体 |
| US7625980B2 (en) * | 2006-07-11 | 2009-12-01 | Exxonmobil Chemical Patents Inc. | Method for improving extrusion surface smoothness in thermoplastic vulcanizates |
| CN101842432B (zh) * | 2007-10-22 | 2013-02-06 | 巴塞尔聚烯烃意大利有限责任公司 | 可交联的热塑性烯烃弹性体和从它获得的交联的热固性烯烃弹性体 |
| US8158721B2 (en) * | 2008-06-13 | 2012-04-17 | Exxonmobil Chemical Patents Inc. | Process for preparing dynamically vulcanized alloys |
| DE102008033290A1 (de) * | 2008-07-11 | 2010-01-14 | Takata-Petri Ag | Verfahren zur Compoundierung eines Kunststoffmaterials, Kunststoffmaterial und Kunststofferzeugnis |
| CN102352070A (zh) * | 2011-07-08 | 2012-02-15 | 金发科技股份有限公司 | 一种应用于动态硫化制备热塑性橡胶的交联剂母料及其制备的热塑性橡胶 |
| CN112812331B (zh) * | 2021-01-12 | 2021-11-16 | 华南理工大学 | 多相交联橡胶、制备方法和回收方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51132256A (en) * | 1975-04-30 | 1976-11-17 | Japan Synthetic Rubber Co Ltd | Thermoplastic composition |
| US4088714A (en) * | 1976-08-16 | 1978-05-09 | Exxon Research & Engineering Co. | Cross-linked melt-flowable thermoplastic elastomer blend comprising EPR or EPDM, polyethylene and polypropylene |
| FR2614897B1 (fr) | 1987-05-07 | 1991-12-20 | Charbonnages Ste Chimique | Compositions thermoplastiques, contenant un polymere modifie d'ethylene et un polymere d'une olefine en c3-c12, leur procede de preparation et leur application a l'obtention d'articles industriels |
| IT1230133B (it) | 1989-04-28 | 1991-10-14 | Himont Inc | Composizioni polipropileniche plasto-elastiche |
| IT1243188B (it) | 1990-08-01 | 1994-05-24 | Himont Inc | Composizioni poliolefiniche elastoplastiche |
| US5308700A (en) * | 1990-10-03 | 1994-05-03 | Sumitomo Chemical Company Limited | Thermoplastic elastomer powder for powder molding, powder molding method using the same and molded article thereof |
| IT1272874B (it) | 1995-01-10 | 1997-07-01 | Enichem Spa | Composizione termoplastico elastomerica |
| US5539052A (en) * | 1995-02-03 | 1996-07-23 | Surprenant Cable Corp. | Crosslinked thermoplastic elastomers |
| US5891553A (en) * | 1995-12-21 | 1999-04-06 | Clark-Schwebel, Inc. | Crosslinkable polymeric coatings and films and composite structures incorporating same |
| US6441093B2 (en) * | 2000-02-10 | 2002-08-27 | Sumitomo Chemical Company, Limited | Thermoplastic elastomer composition for calender-molding and sheets prepared therefrom |
-
2002
- 2002-05-29 DE DE60206915T patent/DE60206915T2/de not_active Expired - Fee Related
- 2002-05-29 EP EP02764572A patent/EP1401925B1/en not_active Expired - Lifetime
- 2002-05-29 WO PCT/EP2002/005908 patent/WO2002102880A1/en not_active Ceased
- 2002-05-29 US US10/469,657 patent/US7632894B2/en not_active Expired - Lifetime
- 2002-05-29 CA CA002455257A patent/CA2455257A1/en not_active Abandoned
- 2002-05-29 BR BR0205531-7A patent/BR0205531A/pt not_active IP Right Cessation
- 2002-05-29 KR KR10-2003-7002044A patent/KR20030022892A/ko not_active Withdrawn
- 2002-05-29 CN CNB02811888XA patent/CN1244614C/zh not_active Expired - Fee Related
- 2002-05-29 RU RU2003128026/04A patent/RU2003128026A/ru not_active Application Discontinuation
- 2002-05-29 JP JP2003506349A patent/JP4372539B2/ja not_active Expired - Fee Related
- 2002-05-29 AT AT02764572T patent/ATE307847T1/de not_active IP Right Cessation
-
2009
- 2009-10-27 US US12/589,684 patent/US20100048823A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| BR0205531A (pt) | 2003-07-01 |
| EP1401925B1 (en) | 2005-10-26 |
| JP2004530757A (ja) | 2004-10-07 |
| ATE307847T1 (de) | 2005-11-15 |
| WO2002102880A1 (en) | 2002-12-27 |
| CA2455257A1 (en) | 2002-12-27 |
| US20100048823A1 (en) | 2010-02-25 |
| EP1401925A1 (en) | 2004-03-31 |
| DE60206915T2 (de) | 2006-08-31 |
| DE60206915D1 (de) | 2005-12-01 |
| US20040236032A1 (en) | 2004-11-25 |
| KR20030022892A (ko) | 2003-03-17 |
| CN1244614C (zh) | 2006-03-08 |
| US7632894B2 (en) | 2009-12-15 |
| CN1516715A (zh) | 2004-07-28 |
| RU2003128026A (ru) | 2005-02-27 |
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