CA2585680A1 - Toner compositions and processes - Google Patents

Toner compositions and processes Download PDF

Info

Publication number
CA2585680A1
CA2585680A1 CA002585680A CA2585680A CA2585680A1 CA 2585680 A1 CA2585680 A1 CA 2585680A1 CA 002585680 A CA002585680 A CA 002585680A CA 2585680 A CA2585680 A CA 2585680A CA 2585680 A1 CA2585680 A1 CA 2585680A1
Authority
CA
Canada
Prior art keywords
copoly
poly
adipate
sulfo
toner
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
CA002585680A
Other languages
French (fr)
Other versions
CA2585680C (en
Inventor
Valerie M. Farrugia
Raj D. Patel
Michael S. Hawkins
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 CA2585680A1 publication Critical patent/CA2585680A1/en
Application granted granted Critical
Publication of CA2585680C publication Critical patent/CA2585680C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
    • G03G9/08Developers with toner particles
    • G03G9/097Plasticisers; Charge controlling agents
    • G03G9/09733Organic compounds
    • G03G9/09741Organic compounds cationic
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
    • G03G9/08Developers with toner particles
    • G03G9/097Plasticisers; Charge controlling agents
    • G03G9/09733Organic compounds
    • G03G9/0975Organic compounds anionic
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
    • G03G9/08Developers with toner particles
    • G03G9/097Plasticisers; Charge controlling agents
    • G03G9/09783Organo-metallic compounds

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Developing Agents For Electrophotography (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

A toner composition includes toner particles including a polymeric resin, a colorant, a wax, and an optional coagulant, and a coagulant applied as a surface additive to a surface of the toner particles to alter a triboelectric charge of the toner particles.

Claims (29)

1. A toner composition comprising:
toner particles comprising:
a polymeric resin;
a colorant;
a wax; and an optional second coagulant, and a first coagulant applied as a surface additive to a surface of said toner particles to alter a triboelectric charge of said toner particles.
2. The toner composition of claim 1, wherein the polymeric resin is a polyester resin.
3. The toner composition of claim 1, wherein the polymeric resin is selected from the group consisting of polyethylene-terephthalate, polypropylene-terephthalate, polybutylene-terephthalate, polypentylene-terephthalate, polyhexalene-terephthalate, polyheptadene-terephthalate, polyoctalene-terephthalate, polyethylene-sebacate, polypropylene sebacate, polybutylene-sebacate, polyethylene-adipate, polypropylene-adipate, polybutylene-adipate, polypentylene-adipate, polyhexalene-adipate, polyheptadene-adipate, polyoctalene-adipate, polyethylene-glutarate, polypropylene-glutarate, polybutylene-glutarate, polypentylene-glutarate, polyhexalene-glutarate, polyheptadene-glutarate, polyoctalene-glutarate polyethylene-pimelate, polypropylene-pimelate, polybutylene-pimelate, polypentylene-pimelate, polyhexalene-pimelate, polyheptadene-pimelate, poly(propoxylated bisphenol-fumarate), poly(propoxylated bisphenol-succinate), poly(propoxylated bisphenol-adipate), poly(propoxylated bisphenol-glutarate), sulfonated forms of the preceding resins, and mixtures thereof.
4. The toner composition of claim 1, wherein the polymeric resin is selected from the group consisting of alkali copoly(5-sulfoisophthaloyl)-co-poly(ethylene-adipate), alkali copoly(5-sulfoisophthaloyl)-copoly(propylene-adipate), alkali copoly(5-sulfoisophthaloyl)-copoly(butylene-adipate), alkali copoly(5-sulfo-isophthaloyl)-copoly(pentylene-adipate), alkali copoly(5-sulfo-iosphthaloyl)-copoly(octylene-adipate), alkali copoly(5-sulfo-isophthaloyl)-copoly(ethylene-adipate), alkali copoly(5-sulfo-isophthaloyl)-copoly(propylene-adipate), alkali copoly(5-sulfo-isophthaloyl)-co-poly(butylene-adipate), alkali copoly(5-sulfo-isophthaloyl)-copoly(pentylene-adipate), alkali copoly(5-sulfo-isophthaloyl)-copoly(hexylene-adipate), alkali copoly(5-sulfo-isophthaloyl)-copoly(octylene-adipate), alkali copoly(5-sulfoisophthaloyl)-copoly(ethylene-succinate), alkali copoly(5-sulfoisophthaloyl-copoly(butylene-succinate), alkali copoly(5-sulfoisophthaloyl)-copoly(hexylene-succinate), alkali copoly(5-sulfoisophthaloyl)-copoly(octylene-succinate), alkali copoly(5-sulfo-isophthaloyl)-copoly(ethylene-sebacate), alkali copoly(5-sulfo-isophthaloyl)-copoly(propylene-sebacate), alkali copoly(5-sulfo-isophthaloyl)-copoly(butylene-sebacate), alkali copoly(5-sulfo-isophthaloyl)-copoly(pentylene-sebacate), alkali copoly(5-sulfo-isophthaloyl)-copoly(hexylene-sebacate), alkali copoly(5-sulfo-isophthaloyl)-copoly(octylene-sebacate), alkali copoly(5-sulfo-isophthaloyl)-copoly(ethylene-adipate), alkali copoly(5-sulfo-isophthaloyl)-copoly(propylene-adipate), alkali copoly(5-sulfo-iosphthaloyl)-copoly(butylene-adipate), alkali copoly(5-sulfo-isophthaloyl)-copoly(pentylene-adipate), alkali copoly(5-sulfo-isophthaloyl) copoly(hexylene-adipate), and poly(octylene-adipate).
5. The toner composition of claim 1, wherein the polymeric resin is a sulfonated polyester resin.
6. The toner composition of claim 1, wherein the polymeric resin is selected from the group consisting of styrene acrylates, styrene methacrylates, butadienes, isoprene, acrylonitrile, acrylic acid, methacrylic acid, beta-carboxy ethyl acrylate, polyesters, poly(styrene-butadiene), poly(methyl styrene-butadiene), poly(methyl methacrylate-butadiene), poly(ethyl methacrylate-butadiene), poly(propyl methacrylate-butadiene), poly(butyl methacrylate-butadiene), poly(methyl acrylate-butadiene), poly(ethyl acrylate-butadiene), poly(propyl acrylate-butadiene), poly(butyl acrylate-butadiene), poly(styrene-isoprene), poly(methyl styrene-isoprene), poly(methyl methacrylate-isoprene), poly(ethyl methacrylate-isoprene), poly(propyl methacrylate-isoprene), poly(butyl methacrylate-isoprene), poly(methyl acrylate-isoprene), poly(ethyl acrylate-isoprene), poly(propyl acrylate-isoprene), poly(butyl acrylate-isoprene);
poly(styrene-propyl acrylate), poly(styrene-butyl acrylate), poly(styrene-butadiene-acrylic acid), poly(styrene-butadiene-methacrylic acid), poly(styrene-butyl acrylate-acrylic acid), poly(styrene-butyl acrylate-methacrylic acid), poly(styrene-butyl acrylate-acrylonitrile), poly(styrene-butyl acrylate-acrylonitrile-acrylic acid), and styrene/butyl acrylate/carboxylic acid terpolymers, and mixtures thereof.
7. The toner composition of claim 1, wherein the polymeric resin comprises a crystalline polyester resin, an amorphous polyester resin, or a mixture of a crystalline polyester resin and an amorphous polyester resin.
8. The toner composition of claim 1, wherein the polymeric resin is present in the toner particles, exclusive of any optional external additives, and on a dry weight basis, in an amount of from about 70 to about 95% by weight of the toner particles.
9. The toner composition of claim 1, wherein the toner particles further comprise the second coagulant incorporated into the toner particles as an aggregating agent.
10. The toner composition of claim 9, wherein the second coagulant is the same as the first coagulant.
11. The toner composition of claim 9, wherein the second coagulant is present in the toner particles, exclusive of any optional external additives, and on a dry weight basis, in an amount of from 0 to about 5 % by weight of the toner particles.
12. The toner composition of claim 1, wherein the first coagulant is a metal salt or a metal oxide, the metal having a valance of at least 3.
13. The toner composition of claim 1, wherein the first coagulant is selected from the group consisting of polyaluminum halides, polyaluminum silicates, polyaluminum hydroxides, and polyaluminum phosphate.
14. The toner composition of claim 1, wherein the first coagulant is selected from the group consisting of polyaluminum chloride and polyaluminum sulfosilicate.
15. The toner composition of claim 1, wherein the first coagulant is anchored to the surface of the toner particles.
16. The toner composition of claim 1, wherein the first coagulant is present in the toner composition in an amount of from about 0.001 to about 10 % by weight of the toner particles on a dry weight basis.
17. The toner composition of claim 1, wherein the first coagulant is present in the toner composition in an amount of from about 0.01 to about 5 % by weight of the toner particles on a dry weight basis.
18. The toner composition of claim 1, wherein the wax is an alkylene wax present in an amount of about 5 % to about 15 % by weight based upon the total weight of the composition.
19. The toner composition of claim 18, wherein the wax is a polyethylene wax, a polypropylene wax, or mixtures thereof.
20. The toner composition of claim 1, wherein the colorant comprises a pigment, a dye, or mixtures thereof, in an amount of about 1 % to about 25 %
by weight based upon the total weight of the composition.
21. The toner composition of claim 1, wherein the toner particles have a negative triboelectric charge, but the toner composition has a neutral or positive triboelectric charge.
22. A process for preparing a toner, comprising:
mixing a polymeric resin emulsion, a colorant dispersion, and a wax to form a mixture;
adding an organic or an inorganic acid to said mixture;
optionally adding a second coagulant to said mixture;
heating the mixture, permitting aggregation and coalescence of said polymeric resin, colorant, and wax, to form toner particles, optionally cooling the mixture and isolating the toner particles, and adding a first coagulant as a surface additive to a surface of said toner particles to alter a triboelectric charge of said toner particles.
23. The process of claim 22, wherein the first coagulant does not cause further appreciable aggregation or coalescence of the toner particles.
24. The process of claim 22, wherein the first coagulant and the second coagulant are poly metal halides.
25. The process of claim 22, wherein the first coagulant neutralizes, pacifies, or masks existing negative charges of said toner particles.
26. The process of claim 22, wherein the heating comprises a first heating below about the glass transition temperature of the polymeric resin and a second heating above about the glass transition temperature of the polymeric resin.
27. The toner process of claim 26, wherein the first heating is from about 45°C to about 60°C and the second heating is from about 80°C to about 95°C.
28. A developer comprising:
the toner of claim 1, and a carrier.
29. A method of developing an image, comprising:
applying the toner composition of claim 1 to an image; and fusing the toner composition to a substrate.
CA2585680A 2006-04-26 2007-04-19 Toner compositions and processes Expired - Fee Related CA2585680C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US11/380,302 2006-04-26
US11/380,302 US7553595B2 (en) 2006-04-26 2006-04-26 Toner compositions and processes

Publications (2)

Publication Number Publication Date
CA2585680A1 true CA2585680A1 (en) 2007-10-26
CA2585680C CA2585680C (en) 2011-04-05

Family

ID=38206869

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2585680A Expired - Fee Related CA2585680C (en) 2006-04-26 2007-04-19 Toner compositions and processes

Country Status (6)

Country Link
US (1) US7553595B2 (en)
EP (1) EP1850187B1 (en)
JP (1) JP5085968B2 (en)
BR (1) BRPI0701796A (en)
CA (1) CA2585680C (en)
DE (1) DE602007001998D1 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8211609B2 (en) * 2007-11-14 2012-07-03 Xerox Corporation Toner compositions
US8133649B2 (en) 2008-12-01 2012-03-13 Xerox Corporation Toner compositions
US20110094320A1 (en) * 2009-10-26 2011-04-28 Liang Hong Method for evaluating de-agglomeration/coagulation stability of agglomerates materials
US9316936B2 (en) * 2013-08-28 2016-04-19 Xerox Corporation Colored toners
CN113703296B (en) * 2021-08-28 2023-12-22 湖北鼎龙控股股份有限公司 Toner and preparation method thereof

Family Cites Families (68)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3847604A (en) 1971-06-10 1974-11-12 Xerox Corp Electrostatic imaging process using nodular carriers
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
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
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
US5308734A (en) 1992-12-14 1994-05-03 Xerox Corporation Toner processes
US5346797A (en) 1993-02-25 1994-09-13 Xerox Corporation Toner processes
US5348832A (en) 1993-06-01 1994-09-20 Xerox Corporation Toner compositions
US5370963A (en) 1993-06-25 1994-12-06 Xerox Corporation Toner emulsion aggregation processes
US5405728A (en) 1993-06-25 1995-04-11 Xerox Corporation Toner aggregation processes
US5418108A (en) 1993-06-25 1995-05-23 Xerox Corporation Toner emulsion aggregation process
US5344738A (en) 1993-06-25 1994-09-06 Xerox Corporation Process of making toner compositions
US5403693A (en) 1993-06-25 1995-04-04 Xerox Corporation Toner aggregation and coalescence processes
US5364729A (en) 1993-06-25 1994-11-15 Xerox Corporation Toner aggregation processes
US5366841A (en) 1993-09-30 1994-11-22 Xerox Corporation Toner aggregation processes
EP0716344A1 (en) 1994-12-05 1996-06-12 Konica Corporation Light-sensitive composition and light-sensitive lithographic printing plate using the same
US5501935A (en) 1995-01-17 1996-03-26 Xerox Corporation Toner aggregation processes
US5977210A (en) 1995-01-30 1999-11-02 Xerox Corporation Modified emulsion aggregation processes
US5527658A (en) 1995-03-13 1996-06-18 Xerox Corporation Toner aggregation processes using water insoluble transition metal containing powder
US5496676A (en) 1995-03-27 1996-03-05 Xerox Corporation Toner aggregation processes
US5565296A (en) 1995-07-03 1996-10-15 Xerox Corporation Coated carriers by aggregation processes
US5585215A (en) 1996-06-13 1996-12-17 Xerox Corporation Toner compositions
US5723252A (en) 1996-09-03 1998-03-03 Xerox Corporation Toner processes
US5650255A (en) 1996-09-03 1997-07-22 Xerox Corporation Low shear toner aggregation processes
US5683848A (en) 1996-10-02 1997-11-04 Xerox Corporation Acrylonitrile-modified toner composition and processes
US5650256A (en) 1996-10-02 1997-07-22 Xerox Corporation Toner processes
US5763133A (en) 1997-03-28 1998-06-09 Xerox Corporation Toner compositions and processes
US5827633A (en) 1997-07-31 1998-10-27 Xerox Corporation Toner processes
US5766818A (en) 1997-10-29 1998-06-16 Xerox Corporation Toner processes with hydrolyzable surfactant
US5840462A (en) 1998-01-13 1998-11-24 Xerox Corporation Toner processes
US5853944A (en) 1998-01-13 1998-12-29 Xerox Corporation Toner processes
US5919595A (en) 1998-01-13 1999-07-06 Xerox Corporation Toner process with cationic salts
US5945245A (en) 1998-01-13 1999-08-31 Xerox Corporation Toner processes
US5869215A (en) 1998-01-13 1999-02-09 Xerox Corporation Toner compositions and processes thereof
US5916725A (en) 1998-01-13 1999-06-29 Xerox Corporation Surfactant free toner processes
US5910387A (en) 1998-01-13 1999-06-08 Xerox Corporation Toner compositions with acrylonitrile and processes
US5994020A (en) 1998-04-13 1999-11-30 Xerox Corporation Wax containing colorants
US5863698A (en) 1998-04-13 1999-01-26 Xerox Corporation Toner processes
US6132924A (en) 1998-10-15 2000-10-17 Xerox Corporation Toner coagulant processes
US5922501A (en) 1998-12-10 1999-07-13 Xerox Corporation Toner processes
US6395442B1 (en) 1999-07-30 2002-05-28 Konica Corporation Toner and production method of the same
US6268102B1 (en) 2000-04-17 2001-07-31 Xerox Corporation Toner coagulant processes
US6472117B2 (en) 2000-07-25 2002-10-29 Konica Corporation Toner for developing electrostatic image and image forming method
JP3915383B2 (en) 2000-08-02 2007-05-16 コニカミノルタホールディングス株式会社 Toner, method for producing the same, and image forming method
US6617091B2 (en) 2000-08-03 2003-09-09 Konica Corporation Production method of toner
US6210853B1 (en) 2000-09-07 2001-04-03 Xerox Corporation Toner aggregation processes
US6673501B1 (en) 2000-11-28 2004-01-06 Xerox Corporation Toner compositions comprising polyester resin and polypyrrole
US6416920B1 (en) 2001-03-19 2002-07-09 Xerox Corporation Toner coagulant processes
US6677097B2 (en) 2001-03-21 2004-01-13 Konica Corporation Toner for developing static image and an image forming method
US6495302B1 (en) 2001-06-11 2002-12-17 Xerox Corporation Toner coagulant processes
US6500597B1 (en) 2001-08-06 2002-12-31 Xerox Corporation Toner coagulant processes
US6576389B2 (en) 2001-10-15 2003-06-10 Xerox Corporation Toner coagulant processes
US6541175B1 (en) 2002-02-04 2003-04-01 Xerox Corporation Toner processes
US6638677B2 (en) 2002-03-01 2003-10-28 Xerox Corporation Toner processes
US6673505B2 (en) 2002-03-25 2004-01-06 Xerox Corporation Toner coagulant processes
US6656658B2 (en) 2002-03-25 2003-12-02 Xerox Corporation Magnetite toner processes
US6617092B1 (en) 2002-03-25 2003-09-09 Xerox Corporation Toner processes
US6627373B1 (en) 2002-03-25 2003-09-30 Xerox Corporation Toner processes
US6656657B2 (en) 2002-03-25 2003-12-02 Xerox Corporation Toner processes
US6664017B1 (en) 2002-08-20 2003-12-16 Xerox Corporation Document security processes
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
US7097954B2 (en) 2004-01-28 2006-08-29 Xerox Corporation Toner processes
US7041425B2 (en) * 2004-02-10 2006-05-09 Xerox Corporation Toner processes
JP2005266565A (en) * 2004-03-19 2005-09-29 Fuji Xerox Co Ltd Electrostatic charge image developing toner, toner manufacturing method, and image forming method
JP4446342B2 (en) 2004-07-16 2010-04-07 株式会社リコー Image forming apparatus and toner
US7455943B2 (en) * 2005-10-17 2008-11-25 Xerox Corporation High gloss emulsion aggregation toner incorporating aluminized silica as a coagulating agent

Also Published As

Publication number Publication date
US7553595B2 (en) 2009-06-30
BRPI0701796A (en) 2007-12-11
JP2007293343A (en) 2007-11-08
EP1850187B1 (en) 2009-08-19
US20070254228A1 (en) 2007-11-01
JP5085968B2 (en) 2012-11-28
DE602007001998D1 (en) 2009-10-01
EP1850187A1 (en) 2007-10-31
CA2585680C (en) 2011-04-05

Similar Documents

Publication Publication Date Title
CA2626544A1 (en) Toner processes
CA2639951C (en) Grafting metal oxides onto polymer for toner
US5290654A (en) Microsuspension processes for toner compositions
JP5221932B2 (en) Particle formation method
EP2026134B1 (en) Use of nano-sized clay composites for improving blocking temperature and vinyl offset of a toner
CA2107800C (en) Toner processes
EP2071405B1 (en) Toner Process
CA2585680A1 (en) Toner compositions and processes
CA2707758A1 (en) Purified polyester resins for toner performance improvement
JP5629173B2 (en) Emulsion polymerization aggregation toner composition
CA2638575C (en) Nano-sized composites containing polymer modified clays and method for making toner particles using same
CA2636808A1 (en) Toner compositions
CA2798832C (en) Mixer apparatus and method of making developer
US20120156605A1 (en) Toner compositions and processes
CA2585599A1 (en) Toner compositions
US20200308328A1 (en) Toner Compositions And Processes Including Polymeric Toner Additives
US8431318B2 (en) Toner compositions and processes
CA2622656A1 (en) Core-shell polymer particles
US7829255B2 (en) Polyester-wax based emulsion aggregation toner compositions
US8227159B1 (en) Toner compositions and processes
US11397387B2 (en) Toner compositions and additives
JP2022151672A (en) Toner composition and additive
US20090130588A1 (en) Acid-base property considerations for improved additive attachement on toner
EP4246238A1 (en) Toner comprising reactive charge control agent
KR20230136049A (en) Toner comprising charge control agent

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20210419