CA2560604A1 - Sulfonated polyester toner - Google Patents

Sulfonated polyester toner Download PDF

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Publication number
CA2560604A1
CA2560604A1 CA002560604A CA2560604A CA2560604A1 CA 2560604 A1 CA2560604 A1 CA 2560604A1 CA 002560604 A CA002560604 A CA 002560604A CA 2560604 A CA2560604 A CA 2560604A CA 2560604 A1 CA2560604 A1 CA 2560604A1
Authority
CA
Canada
Prior art keywords
toner
weight
polyester resin
toner according
sulfonated polyester
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
Application number
CA002560604A
Other languages
French (fr)
Other versions
CA2560604C (en
Inventor
Kimberly D. Nosella
Guerino G. Sacripante
Allan K. Chen
Valerie M. Farrugia
Ke Zhou
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Xerox Corp
Original Assignee
Xerox Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Xerox Corp filed Critical Xerox Corp
Publication of CA2560604A1 publication Critical patent/CA2560604A1/en
Application granted granted Critical
Publication of CA2560604C publication Critical patent/CA2560604C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

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
    • G03G9/08784—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
    • 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
    • G03G9/093—Encapsulated toner particles
    • G03G9/09307—Encapsulated toner particles specified by the shell material
    • G03G9/09314—Macromolecular compounds
    • G03G9/09328—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • G03G9/093—Encapsulated toner particles
    • G03G9/09307—Encapsulated toner particles specified by the shell material
    • G03G9/09342—Inorganic compounds

Abstract

A toner of a sulfonated polyester resin and at least one colorant is made to contain from about 0.01% by weight to about 3% by weight of dry toner in total of lithium, sodium, zinc and calcium. The sulfonated polyester resin may be an alkali metal sulfonated polyester resin, wherein the alkali metal may be sodium and/or lithium. The toner may be formed in an emulsion aggregation process in which an alkali (II) metal salt such as a zinc salt and/or a calcium salt is used as an aggregating agent.

Claims (29)

1. A toner comprised of a sulfonated polyester resin and at least one colorant, wherein the toner contains from about 0.01% by weight to about 3% by weight of dry toner in total of lithium, sodium, zinc and calcium.
2. The toner according to claim 1, wherein the sulfonated polyester resin is an alkali metal sulfonated polyester resin.
3. The toner according to claim 2, wherein the alkali metal is sodium, lithium or a combination thereof.
4. The toner according to claim 1, wherein the sulfonated polyester resin is of the formula wherein R is an alkylene, R' is an arylene, p and n represent the number of repeating segments and X is an alkali metal.
5. The toner according to claim 4, wherein R is an alkylene of from about 2 to about 25 carbon atoms, R' is an arylene of from about 6 to about 36 carbon atoms, and p and n are each from about 10 to about 100,000.
6. The toner according to claim 4, wherein the sulfonated polyester resin is a random copolymer of the formula in which the n and p segments are separated.
7. The toner according to claim 4, wherein R is ethylene, propylene, dipropylene or combination thereof, R' is benzylene, bisphenylene or combination thereof, and X is lithium, sodium or a combination thereof.
8. The toner according to claim 1, wherein the sulfonated polyester resin is linear amorphous, branched amorphous, crystalline or a combination thereof.
9. The toner according to claim 1, wherein the toner contains from about 0% to about 0.1% by weight of the dry toner of calcium, from about 0.1% to about 3%
by weight of the dry toner of zinc, from about 0% to about 1% by weight of the dry toner of sodium and from about 0% to about 1% by weight of the dry toner of lithium.
10. The toner according to claim 1, wherein the toner contains from about 0%
to about 0.1% by weight of the dry toner of calcium, from about 0.1% to about 1.5% by weight of the dry toner of zinc, and from about 0.01% to about 0.5% by weight of the dry toner of sodium and lithium.
11. The toner according to claim 1, wherein the colorant comprises pigment, dye, mixtures of pigment and dye, mixtures of pigments or mixtures of dyes.
12. The toner according to claim 1, wherein the toner further includes a wax.
13. The toner according to claim 1, wherein the toner further has a core-shell structure, both the core and shell including a sulfonated polyester resin, which may be the same or different, therein.
14. The toner according to claim 1, wherein the toner has an average particle size of about 5 to about 15 microns and a geometric size distribution of about 1.10 to about 1.35.
15. A toner comprising an alkali metal sulfonated polyester resin and colorant, wherein the toner contains from about 0% to about 0.1% by weight of dry toner of calcium, from about 0.1% to about 1.5% by weight of the dry toner of zinc, and from about 0.01% to about 0.5% by weight of the dry toner of sodium and lithium.
16. The toner according to claim 15, wherein the alkali metal of the polyester resin is sodium, lithium or a combination thereof.
17. The toner according to claim 15, wherein the sulfonated polyester resin is of the formula wherein R is an alkylene, R' is an arylene, p and n represent the number of repeating segments and X is an alkali metal.
18. The toner according to claim 17, wherein R is an alkylene of from about 2 to about 25 carbon atoms, R' is an arylene of from about 6 to about 36 carbon atoms, and p and n are each from about 10 to about 100,000.
19. The toner according to claim 17, wherein the sulfonated polyester resin is a random copolymer of the formula in which the n and p segments are separated.
20. The toner according to claim 17, wherein R is ethylene, propylene, dipropylene or combination thereof, R' is benzylene, bisphenylene or combination thereof, and X is lithium, sodium or a combination thereof.
21. The toner according to claim 15, wherein the alkali metal sulfonated polyester resin is linear amorphous, branched amorphous, crystalline or a combination thereof.
22. The toner according to claim 15, wherein the colorant comprises pigment, dye, mixtures of pigment and dye, mixtures of pigments or mixtures of dyes.
23. The toner according to claim 15, wherein the toner further includes a wax.
24. The toner according to claim 15, wherein the toner has an average particle size of about 5 to about 15 microns and a geometric size distribution of about 1.10 to about 1.35.
25. A process comprising:
preparing a colloidal solution of an alkali metal sulfonated polyester resin, adding to the colloidal solution a colorant, heating to a temperature of from about 45°C to about 80°C, adding an aqueous solution of an alkali (II) metal salt, and aggregating the mixture to form toner particles, wherein the toner contains from about 0.01% by weight to about 3% by weight of dry toner in total of lithium, sodium, zinc and calcium.
26. The process according to claim 25, wherein the alkali (II) metal salt agent is zinc acetate, calcium chloride or a mixture thereof added in an amount of from about 0.1% to about 5% by weight of the alkali metal sulfonated polyester.
27. The process according to claim 25, wherein after the aggregated toner particles have obtained an average size of from about 3 µm to about 7 µm, the process further comprises adding a colloidal solution of a sulfonated polyester resin followed by the addition of an alkali metal salt to form a shell on the toner particles.
28. An imaging method, comprising forming an image with the toner according to claim 1.
29. An image forming device, wherein the device includes therein the toner according to claim 1 for image formation.
CA2560604A 2005-09-30 2006-09-22 Sulfonated polyester toner Expired - Fee Related CA2560604C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US11/239,168 2005-09-30
US11/239,168 US7425398B2 (en) 2005-09-30 2005-09-30 Sulfonated polyester toner

Publications (2)

Publication Number Publication Date
CA2560604A1 true CA2560604A1 (en) 2007-03-30
CA2560604C CA2560604C (en) 2010-07-20

Family

ID=37547009

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2560604A Expired - Fee Related CA2560604C (en) 2005-09-30 2006-09-22 Sulfonated polyester toner

Country Status (6)

Country Link
US (1) US7425398B2 (en)
EP (1) EP1772778A3 (en)
JP (1) JP4990592B2 (en)
CN (1) CN1940737A (en)
BR (1) BRPI0604005A (en)
CA (1) CA2560604C (en)

Families Citing this family (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4736834B2 (en) * 2006-02-10 2011-07-27 コニカミノルタビジネステクノロジーズ株式会社 Toner for electrostatic image development
US7851116B2 (en) * 2006-10-30 2010-12-14 Xerox Corporation Emulsion aggregation high-gloss toner with calcium addition
US8034527B2 (en) * 2007-08-23 2011-10-11 Xerox Corporation Core-shell polymer nanoparticles and method for making emulsion aggregation particles using same
US20090163449A1 (en) * 2007-12-20 2009-06-25 Eastman Chemical Company Sulfo-polymer powder and sulfo-polymer powder blends with carriers and/or additives
US20090163603A1 (en) * 2007-12-20 2009-06-25 Eastman Chemical Company Sulfo-polymer powder and sulfo-polymer powder blends
JP4560587B2 (en) 2008-02-25 2010-10-13 キヤノン株式会社 toner
US8012254B2 (en) 2008-03-07 2011-09-06 Xerox Corporation Nanosized particles of benzimidazolone pigments
US7938903B2 (en) * 2008-03-07 2011-05-10 Xerox Corporation Nanosized particles of benzimidazolone pigments
US7883574B2 (en) * 2008-03-07 2011-02-08 Xerox Corporation Methods of making nanosized particles of benzimidazolone pigments
US7857901B2 (en) * 2008-03-07 2010-12-28 Xerox Corporation Nonpolar liquid and solid phase change ink compositions comprising nanosized particles of benzimidazolone pigments
US7985290B2 (en) * 2008-03-07 2011-07-26 Xerox Corporation Nonpolar liquid and solid phase change ink compositions comprising nanosized particles of benzimidazolone pigments
US7905954B2 (en) * 2008-03-07 2011-03-15 Xerox Corporation Nanosized particles of benzimidazolone pigments
US8025723B2 (en) 2008-03-07 2011-09-27 Xerox Corporation Nonpolar liquid and solid phase change ink compositions comprising nanosized particles of benzimidazolone pigments
US8530131B2 (en) 2008-08-27 2013-09-10 Xerox Corporation Toner compositions
US8247157B2 (en) * 2008-12-09 2012-08-21 Xerox Corporation Toner process
JP2010244020A (en) * 2009-03-17 2010-10-28 Ricoh Co Ltd Toner
US8076048B2 (en) * 2009-03-17 2011-12-13 Xerox Corporation Toner having polyester resin
US8124307B2 (en) 2009-03-30 2012-02-28 Xerox Corporation Toner having polyester resin
CN102449555B (en) * 2009-05-28 2014-08-13 佳能株式会社 Toner production process and toner
EP2316819B1 (en) 2009-10-19 2017-11-08 Xerox Corporation Self-assembled nanostructures
US8362270B2 (en) 2010-05-11 2013-01-29 Xerox Corporation Self-assembled nanostructures
EP2322512B1 (en) 2009-10-19 2015-10-21 Xerox Corporation Alkylated benzimidazolone compounds and self-assembled nanostructures generated therefrom
US8703988B2 (en) 2010-06-22 2014-04-22 Xerox Corporation Self-assembled nanostructures
US8617781B2 (en) * 2010-01-29 2013-12-31 Dowa Electronics Materials Co., Ltd. Carrier core particles for electrophotographic developer, method for manufacturing the same, carrier for electrophotographic developer and electrophotographic developer
US8431306B2 (en) 2010-03-09 2013-04-30 Xerox Corporation Polyester resin containing toner
US8431318B2 (en) * 2010-04-09 2013-04-30 Xerox Corporation Toner compositions and processes
CN101950133B (en) * 2010-08-31 2012-09-26 珠海思美亚碳粉有限公司 Toner and method for preparing same
US8652720B2 (en) * 2011-05-11 2014-02-18 Xerox Corporation Super low melt toners
JP5830444B2 (en) 2012-07-02 2015-12-09 信越ポリマー株式会社 A conductive polymer composition, a coated article provided with an antistatic film obtained from the composition, and a pattern forming method using the composition.
US8991992B2 (en) 2013-01-22 2015-03-31 Xerox Corporation Inkjet ink containing sub 100 nm latexes
US9243141B1 (en) * 2014-11-03 2016-01-26 Xerox Corporation Coated silver nanoparticle composites comprising a sulfonated polyester matrix and methods of making the same
US9718970B2 (en) * 2015-01-23 2017-08-01 Xerox Corporation Core-shell metal nanoparticle composite
US10007200B2 (en) 2015-05-07 2018-06-26 Xerox Corporation Antimicrobial toner
US10216111B2 (en) * 2015-05-07 2019-02-26 Xerox Corporation Antimicrobial sulfonated polyester resin
EP3296341B1 (en) * 2015-05-15 2019-11-06 Mitsubishi Chemical Corporation Polyester resin, method for producing polyester resin, and toner using said polyester resin
US9908977B2 (en) * 2016-04-13 2018-03-06 Xerox Corporation Styrenic-based polymer coated silver nanoparticle-sulfonated polyester composite powders and methods of making the same
US9863065B2 (en) * 2016-04-13 2018-01-09 Xerox Corporation Polymer coated sulfonated polyester—silver nanoparticle composite filaments and methods of making the same
US10315409B2 (en) 2016-07-20 2019-06-11 Xerox Corporation Method of selective laser sintering
US10649355B2 (en) 2016-07-20 2020-05-12 Xerox Corporation Method of making a polymer composite

Family Cites Families (21)

* Cited by examiner, † Cited by third party
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
US4265990A (en) 1977-05-04 1981-05-05 Xerox Corporation Imaging system with a diamine charge transport material in a polycarbonate resin
US4298672A (en) 1978-06-01 1981-11-03 Xerox Corporation Toners containing alkyl pyridinium compounds and their hydrates
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
US4935326A (en) 1985-10-30 1990-06-19 Xerox Corporation Electrophotographic carrier particles coated with polymer mixture
US4937166A (en) 1985-10-30 1990-06-26 Xerox Corporation Polymer coated carrier particles for electrophotographic developers
US5236629A (en) 1991-11-15 1993-08-17 Xerox Corporation Conductive composite particles and processes for the preparation thereof
US5330874A (en) 1992-09-30 1994-07-19 Xerox Corporation Dry carrier coating and processes
US5593807A (en) 1996-05-10 1997-01-14 Xerox Corporation Toner processes using sodium sulfonated polyester resins
US5919595A (en) 1998-01-13 1999-07-06 Xerox Corporation Toner process with cationic salts
US6214507B1 (en) 1998-08-11 2001-04-10 Xerox Corporation Toner compositions
US6020101A (en) 1999-04-21 2000-02-01 Xerox Corporation Toner composition and process thereof
US6143457A (en) * 1999-10-12 2000-11-07 Xerox Corporation Toner compositions
US6387581B1 (en) * 2000-11-28 2002-05-14 Xerox Corporation Toner compositions comprising polyester resin and poly (3,4-ethylenedioxypyrrole)
US6395445B1 (en) * 2001-03-27 2002-05-28 Xerox Corporation Emulsion aggregation process for forming polyester toners
US6780560B2 (en) 2003-01-29 2004-08-24 Xerox Corporation Toner processes
US6824944B2 (en) 2003-02-20 2004-11-30 Xerox Corporation Toner
US7097954B2 (en) * 2004-01-28 2006-08-29 Xerox Corporation Toner processes
JP2005266317A (en) * 2004-03-18 2005-09-29 Fuji Xerox Co Ltd Electrostatic charge image developing toner, method for manufacturing toner for electrostatic charge image developing toner, electrostatic charge image developer, and image forming method
US7358022B2 (en) * 2005-03-31 2008-04-15 Xerox Corporation Control of particle growth with complexing agents

Also Published As

Publication number Publication date
US7425398B2 (en) 2008-09-16
CN1940737A (en) 2007-04-04
EP1772778A3 (en) 2008-07-23
BRPI0604005A (en) 2007-08-21
EP1772778A2 (en) 2007-04-11
US20070077510A1 (en) 2007-04-05
JP4990592B2 (en) 2012-08-01
JP2007102224A (en) 2007-04-19
CA2560604C (en) 2010-07-20

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Effective date: 20130924