JP2014534307A - ピリドンをベースとするトリスアゾ酸性染料 - Google Patents
ピリドンをベースとするトリスアゾ酸性染料 Download PDFInfo
- Publication number
- JP2014534307A JP2014534307A JP2014536142A JP2014536142A JP2014534307A JP 2014534307 A JP2014534307 A JP 2014534307A JP 2014536142 A JP2014536142 A JP 2014536142A JP 2014536142 A JP2014536142 A JP 2014536142A JP 2014534307 A JP2014534307 A JP 2014534307A
- Authority
- JP
- Japan
- Prior art keywords
- group
- unsubstituted
- alkyl group
- substituted
- alkyl
- 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.)
- Pending
Links
- 239000000980 acid dye Substances 0.000 title abstract description 7
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 title description 6
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 title 1
- 238000004043 dyeing Methods 0.000 claims abstract description 34
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 17
- -1 and R1 represents H Chemical group 0.000 claims abstract description 15
- 239000004952 Polyamide Substances 0.000 claims abstract description 12
- 229920002647 polyamide Polymers 0.000 claims abstract description 12
- 238000007639 printing Methods 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 210000002268 wool Anatomy 0.000 claims description 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000002657 fibrous material Substances 0.000 claims description 5
- 229920001778 nylon Polymers 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 239000004677 Nylon Substances 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 239000012954 diazonium Substances 0.000 claims description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 56
- 230000002378 acidificating effect Effects 0.000 abstract description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 150000003839 salts Chemical class 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000006193 diazotization reaction Methods 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000976 ink Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 238000010186 staining Methods 0.000 description 4
- 229920002292 Nylon 6 Polymers 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000007641 inkjet printing Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000013912 Ceratonia siliqua Nutrition 0.000 description 2
- 240000008886 Ceratonia siliqua Species 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 229940008309 acetone / ethanol Drugs 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- UNNGUFMVYQJGTD-UHFFFAOYSA-N 2-Ethylbutanal Chemical compound CCC(CC)C=O UNNGUFMVYQJGTD-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 235000019687 Lamb Nutrition 0.000 description 1
- 229920001410 Microfiber Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 241001416177 Vicugna pacos Species 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 210000000085 cashmere Anatomy 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 238000011026 diafiltration Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003658 microfiber Substances 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000000050 mohair Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- LJRGBERXYNQPJI-UHFFFAOYSA-M sodium;3-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=CC(S([O-])(=O)=O)=C1 LJRGBERXYNQPJI-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/378—Trisazo dyes of the type
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11008493.6 | 2011-10-22 | ||
| EP20110008493 EP2584007B1 (en) | 2011-10-22 | 2011-10-22 | Trisazo acid dyes based on pyridones |
| PCT/EP2012/004373 WO2013056839A1 (en) | 2011-10-22 | 2012-10-18 | Trisazo acid dyes based on pyridones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2014534307A true JP2014534307A (ja) | 2014-12-18 |
Family
ID=47071221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014536142A Pending JP2014534307A (ja) | 2011-10-22 | 2012-10-18 | ピリドンをベースとするトリスアゾ酸性染料 |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP2584007B1 (https=) |
| JP (1) | JP2014534307A (https=) |
| KR (1) | KR20140091013A (https=) |
| CN (1) | CN104011144A (https=) |
| BR (1) | BR112014009473A2 (https=) |
| ES (1) | ES2497191T3 (https=) |
| IN (1) | IN2014DN02870A (https=) |
| MX (1) | MX347777B (https=) |
| PT (1) | PT2584007E (https=) |
| TW (1) | TWI547527B (https=) |
| WO (1) | WO2013056839A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015167887A (ja) * | 2014-03-05 | 2015-09-28 | 国立大学法人山梨大学 | Ｃｏ選択メタン化触媒 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5641662B1 (https=) * | 1970-10-23 | 1981-09-29 | ||
| JPH0532906A (ja) * | 1991-08-02 | 1993-02-09 | Ricoh Co Ltd | 新規なトリスアゾ化合物 |
| JP2000026746A (ja) * | 1998-05-07 | 2000-01-25 | Basf Ag | アミノ安息香酸ベ―スのカチオン性アゾ染料 |
| JP2003534259A (ja) * | 2000-05-24 | 2003-11-18 | クラリアント インターナショナル リミティド | 有機物質の使用 |
| WO2010000780A1 (en) * | 2008-07-02 | 2010-01-07 | Clariant International Ltd | Acid dyes |
| EP2258685A1 (en) * | 2009-05-14 | 2010-12-08 | Clariant International Ltd | Bisazo compounds |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4014847A1 (de) | 1990-05-09 | 1991-11-14 | Bayer Ag | Neue diaminodiphenylcycloalkane, ihre herstellung und verwendung |
| WO1999051681A1 (en) | 1998-04-03 | 1999-10-14 | Clariant Finance (Bvi) Limited | Triphendioxazine dyestuffs for dyeing organic substrates |
| JP4988140B2 (ja) | 2000-12-05 | 2012-08-01 | クラリアント ファイナンス （ビーブイアイ） リミティド | 三原色染色法 |
| GB0226710D0 (en) * | 2002-11-15 | 2002-12-24 | Avecia Ltd | Inks |
| KR101117652B1 (ko) * | 2003-10-01 | 2012-03-09 | 니폰 가야꾸 가부시끼가이샤 | 아조 화합물, 이것을 함유하는 염료 수용액, 잉크 및 그의용도 |
| EP2163587A1 (en) * | 2008-09-11 | 2010-03-17 | Clariant International Ltd. | Acid dyes |
-
2011
- 2011-10-22 ES ES11008493.6T patent/ES2497191T3/es active Active
- 2011-10-22 PT PT11008493T patent/PT2584007E/pt unknown
- 2011-10-22 EP EP20110008493 patent/EP2584007B1/en not_active Not-in-force
-
2012
- 2012-10-11 TW TW101137469A patent/TWI547527B/zh active
- 2012-10-18 MX MX2014004824A patent/MX347777B/es active IP Right Grant
- 2012-10-18 JP JP2014536142A patent/JP2014534307A/ja active Pending
- 2012-10-18 KR KR1020147013706A patent/KR20140091013A/ko not_active Ceased
- 2012-10-18 IN IN2870DEN2014 patent/IN2014DN02870A/en unknown
- 2012-10-18 CN CN201280051767.6A patent/CN104011144A/zh active Pending
- 2012-10-18 WO PCT/EP2012/004373 patent/WO2013056839A1/en not_active Ceased
- 2012-10-18 BR BR112014009473A patent/BR112014009473A2/pt not_active Application Discontinuation
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5641662B1 (https=) * | 1970-10-23 | 1981-09-29 | ||
| JPH0532906A (ja) * | 1991-08-02 | 1993-02-09 | Ricoh Co Ltd | 新規なトリスアゾ化合物 |
| JP2000026746A (ja) * | 1998-05-07 | 2000-01-25 | Basf Ag | アミノ安息香酸ベ―スのカチオン性アゾ染料 |
| JP2003534259A (ja) * | 2000-05-24 | 2003-11-18 | クラリアント インターナショナル リミティド | 有機物質の使用 |
| WO2010000780A1 (en) * | 2008-07-02 | 2010-01-07 | Clariant International Ltd | Acid dyes |
| EP2258685A1 (en) * | 2009-05-14 | 2010-12-08 | Clariant International Ltd | Bisazo compounds |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015167887A (ja) * | 2014-03-05 | 2015-09-28 | 国立大学法人山梨大学 | Ｃｏ選択メタン化触媒 |
Also Published As
| Publication number | Publication date |
|---|---|
| MX2014004824A (es) | 2014-05-20 |
| MX347777B (es) | 2017-05-11 |
| ES2497191T3 (es) | 2014-09-22 |
| EP2584007B1 (en) | 2014-06-04 |
| WO2013056839A1 (en) | 2013-04-25 |
| TW201319173A (zh) | 2013-05-16 |
| BR112014009473A2 (pt) | 2017-05-09 |
| KR20140091013A (ko) | 2014-07-18 |
| CN104011144A (zh) | 2014-08-27 |
| TWI547527B (zh) | 2016-09-01 |
| PT2584007E (pt) | 2014-07-25 |
| EP2584007A1 (en) | 2013-04-24 |
| IN2014DN02870A (https=) | 2015-05-15 |
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