JP2012133356A - トナー組成物およびプロセス - Google Patents
トナー組成物およびプロセス Download PDFInfo
- Publication number
- JP2012133356A JP2012133356A JP2011270495A JP2011270495A JP2012133356A JP 2012133356 A JP2012133356 A JP 2012133356A JP 2011270495 A JP2011270495 A JP 2011270495A JP 2011270495 A JP2011270495 A JP 2011270495A JP 2012133356 A JP2012133356 A JP 2012133356A
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- Prior art keywords
- resin
- acid
- derived
- toner
- biologically
- 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
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- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 2
- QDCPNGVVOWVKJG-VAWYXSNFSA-N 2-[(e)-dodec-1-enyl]butanedioic acid Chemical compound CCCCCCCCCC\C=C\C(C(O)=O)CC(O)=O QDCPNGVVOWVKJG-VAWYXSNFSA-N 0.000 description 2
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- 239000005720 sucrose Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- HHIMNFJHTNVXBJ-UHFFFAOYSA-L zinc;dinitrite Chemical compound [Zn+2].[O-]N=O.[O-]N=O HHIMNFJHTNVXBJ-UHFFFAOYSA-L 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
- G03G9/087—Binders for toner particles
- G03G9/08742—Binders for toner particles comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- G03G9/08755—Polyesters
-
- 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
- G03G9/0802—Preparation methods
- G03G9/0804—Preparation methods whereby the components are brought together in a liquid dispersing medium
-
- 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
- G03G9/087—Binders for toner particles
- G03G9/08775—Natural macromolecular compounds or derivatives thereof
-
- 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
- G03G9/087—Binders for toner particles
- G03G9/08784—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775
-
- 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
- G03G9/087—Binders for toner particles
- G03G9/08784—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775
- G03G9/08791—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775 characterised by the presence of specified groups or side chains
-
- 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
- G03G9/087—Binders for toner particles
- G03G9/08784—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775
- G03G9/08795—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775 characterised by their chemical properties, e.g. acidity, molecular weight, sensitivity to reactants
-
- 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
- G03G9/087—Binders for toner particles
- G03G9/08784—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775
- G03G9/08797—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775 characterised by their physical properties, e.g. viscosity, solubility, melting temperature, softening temperature, glass transition temperature
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Developing Agents For Electrophotography (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
【解決手段】いくつかの実施形態では、生物由来のアモルファスポリエステル樹脂は、生物由来の多官能の酸で修飾され、これによって、酸で官能基化されたポリエステルが得られ、この物質は、トナーを製造するための乳化凝集プロセスで簡単に乳化させることができる。
【選択図】なし
Description
式中、mは、約5〜約1000であってもよい。
式中、bは、約5〜約2000であり、dは、約5〜約2000である。
Mw=重量平均分子量
Tg(on)=ガラス転移開始温度
AV=酸価
C/O=炭素/酸素比
Claims (10)
- 少なくとも1つの生物由来のアモルファスポリエステル樹脂を、少なくとも1つの生物由来の酸と組み合わせて含む、酸性化した生物由来の樹脂と;
場合により、結晶性樹脂、着色剤、ワックス、およびこれらの組み合わせからなる群から選択される1つ以上の成分とを含み、
前記酸性化した生物由来の樹脂は、樹脂の酸価が約2mg KOH/g〜約200mg KOH/gである、トナー。 - 前記生物由来のアモルファスポリエステル樹脂が、ダイマージオール、D−イソソルビド、ナフタレンジカルボキシレート、ジカルボン酸から誘導される、請求項1に記載のトナー。
- 前記ジカルボン酸が、アゼライン酸、ナフタレンジカルボン酸、ダイマー二酸、テレフタル酸、およびこれらの組み合わせからなる群から選択される、請求項2に記載のトナー。
- 前記生物由来のアモルファスポリエステル樹脂が、脂肪族ダイマージオール、脂肪族ダイマー二酸、D−イソソルビド、L−チロシン、グルタミン酸、およびこれらの組み合わせからなる群から選択される成分を含む、請求項1に記載のトナー。
- 前記少なくとも1つの生物由来のアモルファスポリエステル樹脂は、炭素/酸素比が約2〜約15である、請求項1に記載のトナー。
- 前記生物由来の酸は、クエン酸、無水クエン酸、およびこれらの組み合わせからなる群から選択される多官能の酸を、前記生物由来のアモルファス樹脂の約0.1重量%〜約20重量%の量で含む、請求項1に記載のトナー。
- 前記酸性化した生物由来のアモルファス樹脂は、重量平均分子量が約2,000〜約150,000である、請求項1に記載のトナー。
- 前記酸性化した生物由来の樹脂および任意要素の結晶性樹脂は、約140℃での溶融粘度が約10〜約1,000,000Pa*Sである、請求項1に記載のトナー。
- 少なくとも1つの生物由来のアモルファスポリエステル樹脂と、少なくとも1つの生物由来の酸とを接触させ、樹脂の酸価が約2mg KOH/g〜約200mg KOH/gの酸性化した生物由来の樹脂を作成することと;
前記酸性化した生物由来の樹脂と、少なくとも1つの結晶性樹脂、少なくとも1つの着色剤、少なくとも1つの界面活性剤、任意要素のワックスとを接触させ、小さな粒子を含むエマルションを作成することと;
この小さな粒子を凝集させ、複数の大きな凝集物を作成することと;
この大きな凝集物を融着させてトナー粒子を作成することと;
この粒子を回収することとを含む、トナーを調製するプロセス。 - 前記生物由来のアモルファスポリエステル樹脂を前記生物由来の酸と約150℃〜約170℃の温度で、約30分〜約480分間接触させる、請求項9に記載のプロセス。
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US12/974,310 US8557493B2 (en) | 2010-12-21 | 2010-12-21 | Toner compositions and processes |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014088097A1 (ja) * | 2012-12-07 | 2014-06-12 | 三菱レイヨン株式会社 | トナー用ポリエステル樹脂、その製造方法、およびトナー |
JP2014118573A (ja) * | 2012-12-18 | 2014-06-30 | Xerox Corp | ポリエステルポリマートナー樹脂中のチモール誘導体 |
JP2014118565A (ja) * | 2012-12-18 | 2014-06-30 | Xerox Corp | ポリエステルトナー樹脂中のカルダノール誘導体 |
JP2015004831A (ja) * | 2013-06-21 | 2015-01-08 | コニカミノルタ株式会社 | 静電荷像現像用トナー |
US9290615B2 (en) | 2012-06-13 | 2016-03-22 | Mitsubishi Rayon Co., Ltd. | Toner polyester resin, method for producing same, and toner |
JP2019099699A (ja) * | 2017-12-04 | 2019-06-24 | 日華化学株式会社 | 非結晶性ポリエステル樹脂、トナー用結着樹脂及び静電荷像現像用トナー |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9581926B2 (en) * | 2010-04-13 | 2017-02-28 | Xerox Corporation | Imaging processes |
US9857708B2 (en) * | 2011-04-26 | 2018-01-02 | Xerox Corporation | Toner compositions and processes |
US8697324B2 (en) * | 2011-04-26 | 2014-04-15 | Xerox Corporation | Toner compositions and processes |
JP6194601B2 (ja) * | 2012-09-10 | 2017-09-13 | 株式会社リコー | トナー、現像剤及び画像形成装置 |
US20150111141A1 (en) * | 2013-10-22 | 2015-04-23 | Xerox Corporation | Bio-Based Toner Resin with Increased Fusing Performance |
US11314179B2 (en) * | 2015-05-15 | 2022-04-26 | Mitsubishi Chemical Corporation | Polyester resin, method for producing polyester resin, and toner using said polyester resin |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008533290A (ja) * | 2005-03-18 | 2008-08-21 | バッテル メモリアル インスティテュート | 樹脂、低温配合物、およびそれに由来するコーティング |
US20090246679A1 (en) * | 2008-03-27 | 2009-10-01 | Xerox Corporation | Toner process |
JP2010503736A (ja) * | 2006-09-15 | 2010-02-04 | スティッチング ダッチ ポリマー インスティテュート | ジアンヒドロヘキシトールをベースとしたポリエステルの製造方法 |
JP2010102338A (ja) * | 2008-10-21 | 2010-05-06 | Xerox Corp | トナー組成物およびプロセス |
Family Cites Families (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3590000A (en) | 1967-06-05 | 1971-06-29 | Xerox Corp | Solid developer for latent electrostatic images |
US3847604A (en) | 1971-06-10 | 1974-11-12 | Xerox Corp | Electrostatic imaging process using nodular carriers |
US4298672A (en) | 1978-06-01 | 1981-11-03 | Xerox Corporation | Toners containing alkyl pyridinium compounds and their hydrates |
DE2966986D1 (en) | 1979-07-26 | 1984-06-20 | Baker Chem Co J T | Reagent for the quantitative determination of water, and its use |
US4338390A (en) | 1980-12-04 | 1982-07-06 | Xerox Corporation | Quarternary ammonium sulfate or sulfonate charge control agents for electrophotographic developers compatible with viton fuser |
SU1291921A1 (ru) * | 1985-05-07 | 1987-02-23 | Специальное Конструкторское Бюро Оргтехники Г.Вильнюс | Электрографический про витель дл скрытого электростатического изображени |
US4937166A (en) | 1985-10-30 | 1990-06-26 | Xerox Corporation | Polymer coated carrier particles for electrophotographic developers |
US4935326A (en) | 1985-10-30 | 1990-06-19 | Xerox Corporation | Electrophotographic carrier particles coated with polymer mixture |
US5236629A (en) | 1991-11-15 | 1993-08-17 | Xerox Corporation | Conductive composite particles and processes for the preparation thereof |
US5302486A (en) | 1992-04-17 | 1994-04-12 | Xerox Corporation | Encapsulated toner process utilizing phase separation |
US5290654A (en) | 1992-07-29 | 1994-03-01 | Xerox Corporation | Microsuspension processes for toner compositions |
US5278020A (en) | 1992-08-28 | 1994-01-11 | Xerox Corporation | Toner composition and processes thereof |
US5330874A (en) | 1992-09-30 | 1994-07-19 | Xerox Corporation | Dry carrier coating and processes |
US5308734A (en) | 1992-12-14 | 1994-05-03 | Xerox Corporation | Toner processes |
US5414052A (en) * | 1993-05-21 | 1995-05-09 | Xerox Corporation | Processes for preparing toner |
US5344738A (en) | 1993-06-25 | 1994-09-06 | Xerox Corporation | Process of making toner compositions |
DE19538700A1 (de) | 1995-10-18 | 1997-04-24 | Hoechst Ag | Cholesterische Phasen bildende Polymere, Verfahren zu deren Herstellung sowie Verwendung |
US5853943A (en) | 1998-01-09 | 1998-12-29 | Xerox Corporation | Toner processes |
US6025061A (en) | 1998-04-23 | 2000-02-15 | Hna Holdings, Inc. | Sheets formed from polyesters including isosorbide |
US5959066A (en) | 1998-04-23 | 1999-09-28 | Hna Holdings, Inc. | Polyesters including isosorbide as a comonomer and methods for making same |
US6063464A (en) | 1998-04-23 | 2000-05-16 | Hna Holdings, Inc. | Isosorbide containing polyesters and methods for making same |
US6063827A (en) | 1998-07-22 | 2000-05-16 | Xerox Corporation | Polyester process |
US6214507B1 (en) | 1998-08-11 | 2001-04-10 | Xerox Corporation | Toner compositions |
US6673501B1 (en) | 2000-11-28 | 2004-01-06 | Xerox Corporation | Toner compositions comprising polyester resin and polypyrrole |
US6593049B1 (en) | 2001-03-26 | 2003-07-15 | Xerox Corporation | Toner and developer compositions |
US6924075B2 (en) * | 2002-02-22 | 2005-08-02 | Xeikon International N.V. | Dry toner composition |
US6756176B2 (en) | 2002-09-27 | 2004-06-29 | Xerox Corporation | Toner processes |
US6830860B2 (en) | 2003-01-22 | 2004-12-14 | Xerox Corporation | Toner compositions and processes thereof |
JP4532469B2 (ja) | 2003-02-27 | 2010-08-25 | バテル・メモリアル・インスティテュート | 易脱墨性トナー粒子 |
US7029817B2 (en) | 2004-02-13 | 2006-04-18 | Xerox Corporation | Toner processes |
US7494757B2 (en) | 2005-03-25 | 2009-02-24 | Xerox Corporation | Ultra low melt toners comprised of crystalline resins |
US7329476B2 (en) | 2005-03-31 | 2008-02-12 | Xerox Corporation | Toner compositions and process thereof |
JP4600273B2 (ja) * | 2005-12-26 | 2010-12-15 | 富士ゼロックス株式会社 | 静電荷像現像トナー用結着樹脂、静電荷像現像トナー用結着樹脂分散液及び、静電荷像現像トナー並びにそれらの製造方法 |
US7858285B2 (en) | 2006-11-06 | 2010-12-28 | Xerox Corporation | Emulsion aggregation polyester toners |
US7968266B2 (en) | 2006-11-07 | 2011-06-28 | Xerox Corporation | Toner compositions |
US7547499B2 (en) | 2006-12-22 | 2009-06-16 | Xerox Corporation | Low melt toner |
US7749673B2 (en) | 2007-03-29 | 2010-07-06 | Xerox Corporation | Toner processes |
US7695884B2 (en) | 2007-08-15 | 2010-04-13 | Xerox Corporation | Toner compositions and processes |
US8137884B2 (en) | 2007-12-14 | 2012-03-20 | Xerox Corporation | Toner compositions and processes |
US20090286176A1 (en) * | 2008-05-16 | 2009-11-19 | Konica Minolta Business Technologies, Inc. | Electrophotographic color toner |
US8221948B2 (en) * | 2009-02-06 | 2012-07-17 | Xerox Corporation | Toner compositions and processes |
US8318398B2 (en) * | 2009-02-06 | 2012-11-27 | Xerox Corporation | Toner compositions and processes |
-
2010
- 2010-12-21 US US12/974,310 patent/US8557493B2/en active Active
-
2011
- 2011-12-07 MX MX2011013124A patent/MX2011013124A/es active IP Right Grant
- 2011-12-09 JP JP2011270495A patent/JP5717615B2/ja active Active
- 2011-12-14 CA CA2762641A patent/CA2762641C/en not_active Expired - Fee Related
- 2011-12-20 RU RU2011152040/04A patent/RU2564019C2/ru active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008533290A (ja) * | 2005-03-18 | 2008-08-21 | バッテル メモリアル インスティテュート | 樹脂、低温配合物、およびそれに由来するコーティング |
JP2010503736A (ja) * | 2006-09-15 | 2010-02-04 | スティッチング ダッチ ポリマー インスティテュート | ジアンヒドロヘキシトールをベースとしたポリエステルの製造方法 |
US20090246679A1 (en) * | 2008-03-27 | 2009-10-01 | Xerox Corporation | Toner process |
JP2010102338A (ja) * | 2008-10-21 | 2010-05-06 | Xerox Corp | トナー組成物およびプロセス |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9290615B2 (en) | 2012-06-13 | 2016-03-22 | Mitsubishi Rayon Co., Ltd. | Toner polyester resin, method for producing same, and toner |
WO2014088097A1 (ja) * | 2012-12-07 | 2014-06-12 | 三菱レイヨン株式会社 | トナー用ポリエステル樹脂、その製造方法、およびトナー |
US9434813B2 (en) | 2012-12-07 | 2016-09-06 | Mitsubishi Rayon Co., Ltd. | Polyester resin for toners, method for producing same, and toner |
JPWO2014088097A1 (ja) * | 2012-12-07 | 2017-01-05 | 三菱レイヨン株式会社 | トナー用ポリエステル樹脂、その製造方法、およびトナー |
JP2014118573A (ja) * | 2012-12-18 | 2014-06-30 | Xerox Corp | ポリエステルポリマートナー樹脂中のチモール誘導体 |
JP2014118565A (ja) * | 2012-12-18 | 2014-06-30 | Xerox Corp | ポリエステルトナー樹脂中のカルダノール誘導体 |
JP2015004831A (ja) * | 2013-06-21 | 2015-01-08 | コニカミノルタ株式会社 | 静電荷像現像用トナー |
JP2019099699A (ja) * | 2017-12-04 | 2019-06-24 | 日華化学株式会社 | 非結晶性ポリエステル樹脂、トナー用結着樹脂及び静電荷像現像用トナー |
JP7060948B2 (ja) | 2017-12-04 | 2022-04-27 | 日華化学株式会社 | 非結晶性ポリエステル樹脂、トナー用結着樹脂及び静電荷像現像用トナー |
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RU2564019C2 (ru) | 2015-09-27 |
CA2762641A1 (en) | 2012-06-21 |
US8557493B2 (en) | 2013-10-15 |
US20120156607A1 (en) | 2012-06-21 |
MX2011013124A (es) | 2012-06-20 |
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JP5717615B2 (ja) | 2015-05-13 |
RU2011152040A (ru) | 2013-06-27 |
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