KR100589448B1 - 지르코늄 화합물 및 이를 사용한 전자사진용 토너 - Google Patents
지르코늄 화합물 및 이를 사용한 전자사진용 토너 Download PDFInfo
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- KR100589448B1 KR100589448B1 KR1019997003900A KR19997003900A KR100589448B1 KR 100589448 B1 KR100589448 B1 KR 100589448B1 KR 1019997003900 A KR1019997003900 A KR 1019997003900A KR 19997003900 A KR19997003900 A KR 19997003900A KR 100589448 B1 KR100589448 B1 KR 100589448B1
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- 229960004889 salicylic acid Drugs 0.000 description 1
- VSZWPYCFIRKVQL-UHFFFAOYSA-N selanylidenegallium;selenium Chemical compound [Se].[Se]=[Ga].[Se]=[Ga] VSZWPYCFIRKVQL-UHFFFAOYSA-N 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N serine Chemical compound OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229920003066 styrene-(meth)acrylic acid ester copolymer Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- UONOETXJSWQNOL-UHFFFAOYSA-N tungsten carbide Chemical compound [W+]#[C-] UONOETXJSWQNOL-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/003—Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Developing Agents For Electrophotography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
탄소() | 수소() | 질소() | 지르코늄 () | |
이론치 | 49.1 | 6.6 | 0.0 | 19.9 |
실측치 | 50.0 | 6.2 | 0.0 | 19.8 |
탄소() | 수소() | 질소() | 지르코늄() | |
이론치 | 66.2 | 7.8 | 0.0 | 8.4 |
실측치 | 66.4 | 7.7 | 0.0 | 8.1 |
탄소() | 수소() | 질소() | Zr () | |
이론치 | 36.3 | 3.3 | 0.0 | 27.8 |
실측치 | 36.9 | 3.1 | 0.0 | 27.4 |
탄소() | 수소() | 질소() | Zr () | |
이론치 | 43.1 | 3.6 | 0.0 | 24.0 |
측정값 | 43.8 | 3.5 | 0.0 | 23.6 |
탄소() | 수소() | 질소() | 아연 () | |
이론치 | 63.9 | 7.5 | 0.0 | 11.6 |
실측치 | 64.2 | 7.6 | 0.0 | 11.4 |
Claims (7)
- 삭제
- 하기의 화학식 (1) 로 표시되고, ZrO(HOC6H4COO)2 , ZrO(3,5-디이소프로필살리실레이트)2, ZrO(3,5-디이소프로필살리실레이트)(OH), 및 Zr(3,5-디이소프로필살리실레이트)4 가 아닌 지르코늄 화합물:[화학식 1][식중, R1 은 4급 탄소, 메틴, 메틸렌이며, N, S, O, P 의 헤테로원자를 함유할 수 있고, Y 는 포화결합 또는 불포화결합으로 연결된 환상구조를 나타내며, R2 및 R3 은 서로 독립적으로 알킬기, 알케닐기, 알콕시기, 치환될 수 있는 아릴기, 아릴옥시기, 아랄킬기 또는 아랄킬옥시기, 할로겐기, 수소, 히드록시기, 치환될 수 있는 아미노기, 카르복실기, 카르보닐기, 니트로기, 니트로소기, 술포닐기, 시아노기를 나타내고, R4 는 수소 또는 알킬기를 나타내며, l 은 0 또는 3 내지 12 의 정수, m 은 1 내지 20 의 정수, n 은 0 또는 1 내지 20 의 정수, o 는 0 또는 1 내지 4 의 정수, p 는 0 또는 1 내지 4 의 정수, q 는 0 또는 1 내지 3 의 정수, r 은 1 내지 20 의 정수, s 는 0 또는 1 내지 20 의 정수이다.].
- 방향족 옥시카르복실산 또는 그의 염 및 지르코늄 또는 옥시지르코늄을 함유한 화합물로부터 수득되는 지르코늄 화합물을 전하제어제로서 함유하는 것을 특징으로 하는 전자사진용 토너.
- 제 3 항에 있어서, 하기 화학식 (1) 로 표시되는 지르코늄 화합물을 전하제어제로서 함유하는 것을 특징으로 하는 전자사진용 토너:[화학식 1][식중, R1 은 4급 탄소, 메틴, 메틸렌이며, N, S, O, P 의 헤테로원자를 함유할 수 있고, Y 는 포화결합 또는 불포화결합으로 연결된 환상구조를 나타내며, R2 및 R3 은 서로 독립적으로 알킬기, 알케닐기, 알콕시기, 치환될 수 있는 아릴기, 아릴옥시기, 아랄킬기 또는 아랄킬옥시기, 할로겐기, 수소, 히드록시기, 치환될 수 있는 아미노기, 카르복실기, 카르보닐기, 니트로기, 니트로소기, 술포닐기, 시아노기를 나타내고, R4 는 수소 또는 알킬기를 나타내며, l 은 0 또는 3 내지 12 의 정수, m 은 1 내지 20 의 정수, n 은 0 또는 1 내지 20 의 정수, o 는 0 또는 1 내지 4 의 정수, p 는 0 또는 1 내지 4 의 정수, q 는 0 또는 1 내지 3 의 정수, r 은 1 내지 20 의 정수, s 는 0 또는 1 내지 20 의 정수이다.].
- 제 5 항에 있어서, 화학식 (1) 의 방향족 옥시카르복실산이 3,5-디-t-부틸살리실산인 지르코늄 화합물을 전하제어제로 사용한 전자사진용 토너.
- 제 5 항에 있어서, 전하제어제의 평균입경이 0.01 ㎛ ∼ 10.0 ㎛ 의 범위인 것을 특징으로 하는 전자사진용 토너.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP24076397 | 1997-09-05 | ||
JP97-240763 | 1997-09-05 | ||
JP97-280241 | 1997-10-14 | ||
JP28024197 | 1997-10-14 | ||
PCT/JP1998/003953 WO1999012941A1 (fr) | 1997-09-05 | 1998-09-03 | Composes zirconium et toner electrophotographique les contenant |
Publications (2)
Publication Number | Publication Date |
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KR20000068887A KR20000068887A (ko) | 2000-11-25 |
KR100589448B1 true KR100589448B1 (ko) | 2006-06-13 |
Family
ID=26534903
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019997003900A KR100589448B1 (ko) | 1997-09-05 | 1998-09-03 | 지르코늄 화합물 및 이를 사용한 전자사진용 토너 |
Country Status (7)
Country | Link |
---|---|
US (2) | US6410198B1 (ko) |
EP (1) | EP0970960B1 (ko) |
JP (2) | JP4436936B2 (ko) |
KR (1) | KR100589448B1 (ko) |
CN (1) | CN1331869C (ko) |
DE (1) | DE69828267T2 (ko) |
WO (1) | WO1999012941A1 (ko) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
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US6410198B1 (en) * | 1997-09-05 | 2002-06-25 | Hodogaya Chemical Co., Ltd. | Zirconium compound and electrophotographic toner employing it |
DE69928159T2 (de) * | 1998-04-10 | 2006-07-20 | Canon K.K. | Zweikomponenten-Entwickler und Bilderzeugungsverfahren |
JP2000181120A (ja) * | 1998-12-11 | 2000-06-30 | Toshiba Corp | 現像剤及び画像形成装置 |
JP2000284540A (ja) * | 1999-03-31 | 2000-10-13 | Canon Inc | イエロートナー |
JP2002082483A (ja) * | 2000-09-08 | 2002-03-22 | Ricoh Co Ltd | 現像装置 |
JP4056738B2 (ja) * | 2000-12-20 | 2008-03-05 | 保土谷化学工業株式会社 | 電荷制御剤の製造方法および電荷制御剤を含有する静電荷像現像用トナー |
EP1239334B1 (en) * | 2001-03-08 | 2011-05-11 | Ricoh Company, Ltd. | Toner composition |
EP1260873B1 (en) * | 2001-05-21 | 2006-12-06 | Ricoh Company, Ltd. | Toner, developer and image forming method using the toner |
EP1383011B1 (en) * | 2002-07-19 | 2005-04-06 | Ricoh Company, Ltd. | Toner comprising zirconium based organometallic charge control agent and image forming method |
JP2006039221A (ja) * | 2004-07-27 | 2006-02-09 | Sharp Corp | 電子写真用トナー |
CN100346235C (zh) * | 2005-08-31 | 2007-10-31 | 湖北鼎龙化学有限公司 | 锆化合物电荷调节剂及含该电荷调节剂的电子照相用碳粉 |
US8003286B2 (en) | 2005-09-08 | 2011-08-23 | Hodogaya Chemical Co., Ltd. | Photoreceptor for electrophotography |
US7501218B2 (en) * | 2006-02-17 | 2009-03-10 | Eastman Kodak Company | Electrostatographic toner containing organometallic dimethyl sulfoxide complex charge control agent |
CN100478791C (zh) * | 2007-03-12 | 2009-04-15 | 湖北鼎龙化学股份有限公司 | 一种电荷调节剂以及碳粉 |
JP5440749B2 (ja) * | 2008-03-17 | 2014-03-12 | 株式会社リコー | 静電荷像現像用トナー |
RU2650631C2 (ru) * | 2014-01-17 | 2018-04-16 | Рикох Компани, Лтд. | Тонер для электрофотографии, способ формирования изображения и технологический картридж |
US10126678B2 (en) * | 2015-10-20 | 2018-11-13 | Ricoh Company, Ltd. | Toner, toner housing unit, image forming apparatus, and image forming method |
CN111808434B (zh) * | 2020-07-20 | 2021-07-02 | 青岛科技大学 | 一种制备色酚as系偶氮染料的方法 |
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US1933520A (en) * | 1931-07-18 | 1933-10-31 | Resinous Prod & Chemical Co | Drier and drying oil composition |
NL290109A (ko) * | 1963-03-12 | 1900-01-01 | ||
CH579579A5 (ko) * | 1972-11-22 | 1976-09-15 | Ciba Geigy Ag | |
CH579580A5 (ko) * | 1972-11-22 | 1976-09-15 | Ciba Geigy Ag | |
JPS60213959A (ja) * | 1984-04-09 | 1985-10-26 | Fuji Xerox Co Ltd | 静電荷現像用トナ− |
US4675422A (en) | 1985-10-23 | 1987-06-23 | Stepan Company | Organometallic compounds |
JPS63217362A (ja) * | 1987-03-05 | 1988-09-09 | Konica Corp | 塩基性有機酸金属錯体を含有する静電潜像現像トナ− |
US4921942A (en) * | 1987-03-09 | 1990-05-01 | Stepan Company | Organometallic compounds |
US5085850A (en) * | 1990-11-09 | 1992-02-04 | Warner-Lambert Company | Anti-plaque compositions comprising a combination of morpholinoamino alcohol and metal salts |
US5223368A (en) * | 1991-09-06 | 1993-06-29 | Xerox Corporation | Toner and developer compositions comprising aluminum charge control agent |
US5300387A (en) * | 1992-06-05 | 1994-04-05 | Xerox Corporation | Toner compositions with negative charge enhancing additives |
JP4004080B2 (ja) * | 1995-08-29 | 2007-11-07 | オリヱント化学工業株式会社 | 芳香族オキシカルボン酸の金属化合物及びその関連技術 |
JP3267515B2 (ja) * | 1995-08-30 | 2002-03-18 | キヤノン株式会社 | 静電荷像現像用トナー |
US6410198B1 (en) * | 1997-09-05 | 2002-06-25 | Hodogaya Chemical Co., Ltd. | Zirconium compound and electrophotographic toner employing it |
EP0957406B1 (en) * | 1997-12-01 | 2003-08-13 | Hodogaya Chemical Co Ltd | Electrophotographic toner |
-
1998
- 1998-09-03 US US09/297,568 patent/US6410198B1/en not_active Expired - Lifetime
- 1998-09-03 CN CNB988012804A patent/CN1331869C/zh not_active Expired - Lifetime
- 1998-09-03 KR KR1019997003900A patent/KR100589448B1/ko not_active IP Right Cessation
- 1998-09-03 DE DE69828267T patent/DE69828267T2/de not_active Expired - Lifetime
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- 1998-09-03 WO PCT/JP1998/003953 patent/WO1999012941A1/ja active IP Right Grant
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Also Published As
Publication number | Publication date |
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EP0970960A4 (en) | 2002-05-02 |
JP2009057375A (ja) | 2009-03-19 |
US6410198B1 (en) | 2002-06-25 |
CN1237182A (zh) | 1999-12-01 |
WO1999012941A1 (fr) | 1999-03-18 |
DE69828267D1 (de) | 2005-01-27 |
US20010010887A1 (en) | 2001-08-02 |
CN1331869C (zh) | 2007-08-15 |
EP0970960A1 (en) | 2000-01-12 |
US6552211B2 (en) | 2003-04-22 |
JP4436936B2 (ja) | 2010-03-24 |
JP4532579B2 (ja) | 2010-08-25 |
DE69828267T2 (de) | 2005-12-08 |
EP0970960B1 (en) | 2004-12-22 |
KR20000068887A (ko) | 2000-11-25 |
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