JPS6169073A - 静電荷像現像用トナ− - Google Patents
静電荷像現像用トナ−Info
- Publication number
- JPS6169073A JPS6169073A JP59191117A JP19111784A JPS6169073A JP S6169073 A JPS6169073 A JP S6169073A JP 59191117 A JP59191117 A JP 59191117A JP 19111784 A JP19111784 A JP 19111784A JP S6169073 A JPS6169073 A JP S6169073A
- Authority
- JP
- Japan
- Prior art keywords
- toner
- parts
- resin
- oxycarboxylic acid
- zinc complex
- 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000011701 zinc Substances 0.000 claims abstract description 15
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 15
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 11
- 229920005989 resin Polymers 0.000 claims abstract description 10
- 239000011347 resin Substances 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 150000002500 ions Chemical class 0.000 abstract description 8
- 239000000203 mixture Substances 0.000 abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 8
- 238000002156 mixing Methods 0.000 abstract description 6
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003513 alkali Substances 0.000 abstract description 3
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000010979 pH adjustment Methods 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000843 powder Substances 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 230000006866 deterioration Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000000975 dye Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- DFYKHEXCUQCPEB-UHFFFAOYSA-N butyl 2-methylprop-2-enoate;styrene Chemical compound C=CC1=CC=CC=C1.CCCCOC(=O)C(C)=C DFYKHEXCUQCPEB-UHFFFAOYSA-N 0.000 description 3
- 229920006026 co-polymeric resin Polymers 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ZWQBZEFLFSFEOS-UHFFFAOYSA-N 3,5-ditert-butyl-2-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=C(O)C(C(C)(C)C)=C1 ZWQBZEFLFSFEOS-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 239000000025 natural resin Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 2
- 229960001763 zinc sulfate Drugs 0.000 description 2
- 229910000368 zinc sulfate Inorganic materials 0.000 description 2
- GUYIZQZWDFCUTA-UHFFFAOYSA-N (pentadecachlorophthalocyaninato(2-))-copper Chemical compound [Cu+2].N1=C([N-]2)C3=C(Cl)C(Cl)=C(Cl)C(Cl)=C3C2=NC(C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C22)=NC2=NC(C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C22)=NC2=NC2=C(C(Cl)=C(C(Cl)=C3)Cl)C3=C1[N-]2 GUYIZQZWDFCUTA-UHFFFAOYSA-N 0.000 description 1
- OSNILPMOSNGHLC-UHFFFAOYSA-N 1-[4-methoxy-3-(piperidin-1-ylmethyl)phenyl]ethanone Chemical compound COC1=CC=C(C(C)=O)C=C1CN1CCCCC1 OSNILPMOSNGHLC-UHFFFAOYSA-N 0.000 description 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- XBQCHPYJCIOWIX-UHFFFAOYSA-N 4-tert-butyl-3-hydroxynaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C(C(C)(C)C)=C(O)C(C(O)=O)=CC2=C1 XBQCHPYJCIOWIX-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 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
- 239000006229 carbon black Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- VVOLVFOSOPJKED-UHFFFAOYSA-N copper phthalocyanine Chemical compound [Cu].N=1C2=NC(C3=CC=CC=C33)=NC3=NC(C3=CC=CC=C33)=NC3=NC(C3=CC=CC=C33)=NC3=NC=1C1=CC=CC=C12 VVOLVFOSOPJKED-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000696 magnetic material Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003870 salicylic acids Chemical class 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229920005792 styrene-acrylic resin Polymers 0.000 description 1
- 230000009747 swallowing Effects 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/097—Plasticisers; Charge controlling agents
- G03G9/09783—Organo-metallic compounds
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Developing Agents For Electrophotography (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59191117A JPS6169073A (ja) | 1984-09-12 | 1984-09-12 | 静電荷像現像用トナ− |
| US06/775,485 US4656112A (en) | 1984-09-12 | 1985-09-12 | Toner for developing electrostatic latent images |
| EP19860100043 EP0227874B1 (en) | 1984-09-12 | 1986-01-03 | Toner for developing electrostatic latent images |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59191117A JPS6169073A (ja) | 1984-09-12 | 1984-09-12 | 静電荷像現像用トナ− |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6169073A true JPS6169073A (ja) | 1986-04-09 |
| JPH0260183B2 JPH0260183B2 (enrdf_load_stackoverflow) | 1990-12-14 |
Family
ID=16269146
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59191117A Granted JPS6169073A (ja) | 1984-09-12 | 1984-09-12 | 静電荷像現像用トナ− |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP0227874B1 (enrdf_load_stackoverflow) |
| JP (1) | JPS6169073A (enrdf_load_stackoverflow) |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63118756A (ja) * | 1986-11-07 | 1988-05-23 | Mitsubishi Kasei Corp | 静電荷像現像用トナ− |
| JPH03185457A (ja) * | 1989-12-15 | 1991-08-13 | Konica Corp | カラートナー |
| US5153090A (en) * | 1990-06-28 | 1992-10-06 | Commtech International Management Corporation | Charge directors for use in electrophotographic compositions and processes |
| US6218065B1 (en) | 1997-12-05 | 2001-04-17 | Canon Kabushiki Kaisha | Toner having negative triboelectric chargeability and developing method |
| US6232027B1 (en) | 1998-05-26 | 2001-05-15 | Canon Kabushiki Kaisha | Toner having negative triboelectric chargeability and image forming method |
| US6514654B1 (en) | 1998-04-10 | 2003-02-04 | Canon Kabushiki Kaisha | Two-component developer and image forming method |
| US6964835B2 (en) | 2002-07-19 | 2005-11-15 | Ricoh Company, Ltd. | Toner and image forming method using the toner |
| WO2007111346A1 (ja) | 2006-03-29 | 2007-10-04 | Hodogaya Chemical Co., Ltd. | 混合環状フェノール硫化物、それを用いた電荷制御剤及びトナー |
| WO2007119797A1 (ja) | 2006-04-13 | 2007-10-25 | Hodogaya Chemical Co., Ltd. | 酸化型混合環状フェノール硫化物、それを用いた電荷制御剤及びトナー |
| WO2011105334A1 (ja) | 2010-02-26 | 2011-09-01 | 保土谷化学工業株式会社 | 電荷制御剤およびそれを用いたトナー |
| US8088540B2 (en) | 2006-01-23 | 2012-01-03 | Hodogaya Chemical Co., Ltd. | Photoreceptor for electrophotography |
| JPWO2010035561A1 (ja) * | 2008-09-29 | 2012-02-23 | 日本碍子株式会社 | ガス吸着材料、その前駆体及びガス吸着材料の製造方法 |
| WO2012035996A1 (ja) | 2010-09-14 | 2012-03-22 | 保土谷化学工業株式会社 | 電荷制御剤及びそれを用いたトナー |
| WO2012036171A1 (ja) | 2010-09-15 | 2012-03-22 | 保土谷化学工業株式会社 | 電荷制御剤及びそれを用いたトナー |
| WO2012102137A1 (ja) | 2011-01-27 | 2012-08-02 | 保土谷化学工業株式会社 | 電荷制御剤及びそれを用いたトナー |
| US8790855B2 (en) | 2010-09-13 | 2014-07-29 | Hodogaya Chemical Co., Ltd | Charge control agent and toner using same |
| US9152069B2 (en) | 2011-02-28 | 2015-10-06 | Ricoh Company, Ltd. | Toner, and full-color image forming method and full-color image forming apparatus using the toner |
| JPWO2015046214A1 (ja) * | 2013-09-24 | 2017-03-09 | 保土谷化学工業株式会社 | 電荷制御剤及びそれを用いたトナー |
| US10474050B2 (en) | 2015-09-17 | 2019-11-12 | Hodogaya Chemical Co., Ltd. | Toner and charge control agent using pyrazolone derivative or salt of derivative |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4762763A (en) * | 1985-12-19 | 1988-08-09 | Ricoh Co., Ltd. | Toner for developing electrostatic latent image |
| US4985328A (en) * | 1988-09-22 | 1991-01-15 | Hitachi Chemical Co., Ltd. | Dry toner, dry developer and process for forming electrophotographic images |
| JP2609356B2 (ja) * | 1990-11-28 | 1997-05-14 | 三田工業株式会社 | 負帯電性電子写真用トナー |
| JP2609357B2 (ja) * | 1990-11-28 | 1997-05-14 | 三田工業株式会社 | 負帯電用電子写真用トナー |
| JP2609359B2 (ja) * | 1990-11-28 | 1997-05-14 | 三田工業株式会社 | 負帯電用電子写真用トナー |
| AU8897391A (en) * | 1990-12-12 | 1992-06-18 | Mitsubishi Kasei Corporation | Electrostatic image-developing toner |
| GB9306456D0 (en) * | 1993-03-29 | 1993-05-19 | Zeneca Ltd | Composition and use |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5779964A (en) * | 1980-11-06 | 1982-05-19 | Canon Inc | Developing method |
| JPS5979256A (ja) * | 1982-10-29 | 1984-05-08 | Ricoh Co Ltd | 静電潜像現像用トナ− |
| JPS5988745A (ja) * | 1982-11-15 | 1984-05-22 | Hodogaya Chem Co Ltd | 電子写真用トナ− |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53127726A (en) * | 1977-04-13 | 1978-11-08 | Canon Inc | Electrostatic image developing toner |
| JPS5841508B2 (ja) * | 1980-12-22 | 1983-09-12 | オリヱント化学工業株式会社 | 静電荷像現像用トナ− |
| JPS5929255A (ja) * | 1982-08-12 | 1984-02-16 | Canon Inc | 静電荷現像用トナ− |
-
1984
- 1984-09-12 JP JP59191117A patent/JPS6169073A/ja active Granted
-
1986
- 1986-01-03 EP EP19860100043 patent/EP0227874B1/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5779964A (en) * | 1980-11-06 | 1982-05-19 | Canon Inc | Developing method |
| JPS5979256A (ja) * | 1982-10-29 | 1984-05-08 | Ricoh Co Ltd | 静電潜像現像用トナ− |
| JPS5988745A (ja) * | 1982-11-15 | 1984-05-22 | Hodogaya Chem Co Ltd | 電子写真用トナ− |
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63118756A (ja) * | 1986-11-07 | 1988-05-23 | Mitsubishi Kasei Corp | 静電荷像現像用トナ− |
| JPH03185457A (ja) * | 1989-12-15 | 1991-08-13 | Konica Corp | カラートナー |
| US5153090A (en) * | 1990-06-28 | 1992-10-06 | Commtech International Management Corporation | Charge directors for use in electrophotographic compositions and processes |
| US6218065B1 (en) | 1997-12-05 | 2001-04-17 | Canon Kabushiki Kaisha | Toner having negative triboelectric chargeability and developing method |
| US6514654B1 (en) | 1998-04-10 | 2003-02-04 | Canon Kabushiki Kaisha | Two-component developer and image forming method |
| US6232027B1 (en) | 1998-05-26 | 2001-05-15 | Canon Kabushiki Kaisha | Toner having negative triboelectric chargeability and image forming method |
| US6964835B2 (en) | 2002-07-19 | 2005-11-15 | Ricoh Company, Ltd. | Toner and image forming method using the toner |
| US8088540B2 (en) | 2006-01-23 | 2012-01-03 | Hodogaya Chemical Co., Ltd. | Photoreceptor for electrophotography |
| WO2007111346A1 (ja) | 2006-03-29 | 2007-10-04 | Hodogaya Chemical Co., Ltd. | 混合環状フェノール硫化物、それを用いた電荷制御剤及びトナー |
| WO2007119797A1 (ja) | 2006-04-13 | 2007-10-25 | Hodogaya Chemical Co., Ltd. | 酸化型混合環状フェノール硫化物、それを用いた電荷制御剤及びトナー |
| JPWO2010035561A1 (ja) * | 2008-09-29 | 2012-02-23 | 日本碍子株式会社 | ガス吸着材料、その前駆体及びガス吸着材料の製造方法 |
| WO2011105334A1 (ja) | 2010-02-26 | 2011-09-01 | 保土谷化学工業株式会社 | 電荷制御剤およびそれを用いたトナー |
| US8790855B2 (en) | 2010-09-13 | 2014-07-29 | Hodogaya Chemical Co., Ltd | Charge control agent and toner using same |
| US8900785B2 (en) | 2010-09-14 | 2014-12-02 | Hodogaya Chemical Co., Ltd. | Charge control agent and toner using the same |
| WO2012035996A1 (ja) | 2010-09-14 | 2012-03-22 | 保土谷化学工業株式会社 | 電荷制御剤及びそれを用いたトナー |
| WO2012036171A1 (ja) | 2010-09-15 | 2012-03-22 | 保土谷化学工業株式会社 | 電荷制御剤及びそれを用いたトナー |
| WO2012102137A1 (ja) | 2011-01-27 | 2012-08-02 | 保土谷化学工業株式会社 | 電荷制御剤及びそれを用いたトナー |
| KR20140005986A (ko) | 2011-01-27 | 2014-01-15 | 호도가야 가가쿠 고교 가부시키가이샤 | 전하 제어제 및 그것을 이용한 토너 |
| US9152069B2 (en) | 2011-02-28 | 2015-10-06 | Ricoh Company, Ltd. | Toner, and full-color image forming method and full-color image forming apparatus using the toner |
| JPWO2015046214A1 (ja) * | 2013-09-24 | 2017-03-09 | 保土谷化学工業株式会社 | 電荷制御剤及びそれを用いたトナー |
| US9835965B2 (en) | 2013-09-24 | 2017-12-05 | Hodogaya Chemical Co., Ltd. | Charge control agent and toner using same |
| US10474050B2 (en) | 2015-09-17 | 2019-11-12 | Hodogaya Chemical Co., Ltd. | Toner and charge control agent using pyrazolone derivative or salt of derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0260183B2 (enrdf_load_stackoverflow) | 1990-12-14 |
| EP0227874B1 (en) | 1990-09-26 |
| EP0227874A1 (en) | 1987-07-08 |
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