CA2541183A1 - Toner processes - Google Patents

Toner processes Download PDF

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Publication number
CA2541183A1
CA2541183A1 CA002541183A CA2541183A CA2541183A1 CA 2541183 A1 CA2541183 A1 CA 2541183A1 CA 002541183 A CA002541183 A CA 002541183A CA 2541183 A CA2541183 A CA 2541183A CA 2541183 A1 CA2541183 A1 CA 2541183A1
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CA
Canada
Prior art keywords
poly
toner particles
chloride
sulfonated polyester
bromide
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
CA002541183A
Other languages
French (fr)
Other versions
CA2541183C (en
Inventor
Raj D. Patel
Michael S. Hawkins
Paul J. Gerroir
Richard P.N. Veregin
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Xerox Corp
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Xerox Corp
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Publication date
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Publication of CA2541183A1 publication Critical patent/CA2541183A1/en
Application granted granted Critical
Publication of CA2541183C publication Critical patent/CA2541183C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
    • G03G9/08Developers with toner particles
    • G03G9/087Binders for toner particles
    • G03G9/08702Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • G03G9/08724Polyvinylesters
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
    • G03G9/08Developers with toner particles
    • G03G9/0802Preparation methods
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
    • G03G9/08Developers with toner particles
    • G03G9/0802Preparation methods
    • G03G9/0804Preparation methods whereby the components are brought together in a liquid dispersing medium
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
    • G03G9/08Developers with toner particles
    • G03G9/0802Preparation methods
    • G03G9/0804Preparation methods whereby the components are brought together in a liquid dispersing medium
    • G03G9/0806Preparation methods whereby the components are brought together in a liquid dispersing medium whereby chemical synthesis of at least one of the toner components takes place
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
    • G03G9/08Developers with toner particles
    • G03G9/0819Developers with toner particles characterised by the dimensions of the particles
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
    • G03G9/08Developers with toner particles
    • G03G9/0825Developers with toner particles characterised by their structure; characterised by non-homogenuous distribution of components
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
    • G03G9/08Developers with toner particles
    • G03G9/087Binders for toner particles
    • G03G9/08702Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
    • G03G9/08Developers with toner particles
    • G03G9/087Binders for toner particles
    • G03G9/08702Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • G03G9/08706Polymers of alkenyl-aromatic compounds
    • G03G9/08708Copolymers of styrene
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
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    • G03G9/087Binders for toner particles
    • G03G9/08702Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • G03G9/08706Polymers of alkenyl-aromatic compounds
    • G03G9/08708Copolymers of styrene
    • G03G9/08711Copolymers of styrene with esters of acrylic or methacrylic acid
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
    • G03G9/08Developers with toner particles
    • G03G9/087Binders for toner particles
    • G03G9/08702Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • G03G9/08726Polymers of unsaturated acids or derivatives thereof
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
    • G03G9/08Developers with toner particles
    • G03G9/087Binders for toner particles
    • G03G9/08702Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • G03G9/08726Polymers of unsaturated acids or derivatives thereof
    • G03G9/08728Polymers of esters
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
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    • G03G9/087Binders for toner particles
    • G03G9/08702Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • G03G9/08726Polymers of unsaturated acids or derivatives thereof
    • G03G9/08733Polymers of unsaturated polycarboxylic acids
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
    • G03G9/08Developers with toner particles
    • G03G9/087Binders for toner particles
    • G03G9/08702Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • G03G9/08737Polymers derived from conjugated dienes
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
    • G03G9/08Developers with toner particles
    • G03G9/087Binders for toner particles
    • G03G9/08742Binders for toner particles comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • G03G9/08755Polyesters
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
    • G03G9/08Developers with toner particles
    • G03G9/087Binders for toner particles
    • G03G9/08784Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775
    • G03G9/08791Macromolecular 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
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
    • G03G9/08Developers with toner particles
    • G03G9/093Encapsulated toner particles
    • G03G9/09307Encapsulated toner particles specified by the shell material
    • G03G9/09314Macromolecular compounds
    • G03G9/09321Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
    • G03G9/08Developers with toner particles
    • G03G9/093Encapsulated toner particles
    • G03G9/0935Encapsulated toner particles specified by the core material
    • G03G9/09357Macromolecular compounds
    • G03G9/09364Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
    • G03G9/08Developers with toner particles
    • G03G9/093Encapsulated toner particles
    • G03G9/0935Encapsulated toner particles specified by the core material
    • G03G9/09357Macromolecular compounds
    • G03G9/09371Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03GELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00Developers
    • G03G9/08Developers with toner particles
    • G03G9/093Encapsulated toner particles
    • G03G9/09392Preparation thereof
    • 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

Abstract

A process including mixing a sulfonated polyester resin, a colorant, and a coagulant; heating the resulting sulfonated polyester mixture; adding a polymetal halide and an anionic latex to form coated toner particles; and heating the coated toner particles is disclosed.

Claims (30)

1. A process comprising:
mixing a sulfonated polyester resin, a colorant, and a coagulant;
heating the resulting sulfonated polyester mixture;
adding a polymetal halide and an anionic latex to form coated toner particles;
and heating the coated toner particles.
2. The process of Claim 1, wherein the sulfonated polyester resin is selected from the group consisting of poly(1,2-propylene-sodio 5-sulfoisophthalate), poly(neopentylene-sodio 5-sulfoisophthalate), poly(diethylene-sodio 5-sulfoisophthalate), copoly(1,2-propylene-sodio 5-sulfoisophthalate)-copoly-(1,2-propylene-terephthalate-phthalate), copoly(1,2-propylene-diethylene sodio 5-sulfoisophthalate)-copoly-(1,2-propylene-diethylene-terephthalate-phthal ate), copoly(ethylene-neopentyiene-sodio 5-sulfoisophthalate)-copoly-(ethylene-neopentylene-terephthalate-phthalate), copoly(propoxylated bisphenol A)-copoly-(propoxylated bisphenol A-sodio 5-sulfoisophthalate), crystalline sulfonated polyester resin, and branched sulfonated polyester resin.
3. The process of Claim 1, wherein the colorant is selected from the group consisting of dyes, pigments, and mixtures thereof.
4. The process of Claim 1, wherein the coagulant is selected from the group consisting of aluminum chloride, zinc sulfate, magnesium sulfate, potassium-aluminum sulfate, sodium chloride, sodium bromide, sodium iodide, sodium fluoride, sodium acetate, sodium acetoacetate, lithium chloride, lithium bromide, lithium iodide, lithium fluoride, lithium acetate, lithium acetoacetate, potassium chloride, potassium bromide, potassium iodide, potassium fluoride, acetate, potassium acetoacetate, rubidium bromide, rubidium chloride, rubidium iodide, rubidium fluoride, rubidium acetate, rubidium acetoacetate, cesium bromide, cesium chloride, cesium iodide, cesium fluoride, cesium acetate, cesium acetoacetate, beryllium bromide, beryllium chloride, beryllium iodide, beryllium fluoride, beryllium acetate, beryllium acetoacetate, magnesium bromide, magnesium chloride, magnesium iodide, magnesium fluoride, magnesium acetate, magnesium acetoacetate, calcium bromide, barium bromide, barium chloride, barium iodide, barium fluoride, barium acetate, barium acetoacetate, strontium bromide, strontium chloride, strontium iodide, strontium fluoride, strontium acetate, strontium acetoacetate, zinc bromide, zinc chloride, zinc iodide, zinc fluoride, zinc acetate, zinc acetoacetate, copper bromide, copper chloride, copper iodide, copper fluoride, copper acetate, copper acetoacetate, manganese bromide, manganese chloride, manganese iodide, manganese fluoride, manganese acetate, manganese acetoacetate, chromium bromide, chromium chloride, chromium iodide, chromium fluoride, chromium acetate, chromium acetoacetate, iron bromide, iron chloride, iron iodide, iron fluoride, iron acetate, iron acetoacetate, vanadyl bromide, vanadyl chloride, vanadyl iodide, vanadyl fluoride, vanadyl acetate, and vanadyl acetoacetate.
5. The process of Claim 1, wherein a first portion of the coagulant is added at a temperature of about 20°C to about 35°C.
6. The process of Claim 5, wherein after the first portion of the coagulant is added the temperature is increased to about 50°C and the pH is about 5.5.
7. The process of Claim 6, wherein after the temperature is increased a second portion of the coagulant is added.
8. The process of Claim 7, wherein after the addition of the second portion of the coagulant the sulfonated polyester toner particles have a particle size of about 2 to about 3 microns.
9. The process of Claim 1, further comprising after heating the sulfonated polyester toner particles reducing the pH to about 4.
10. The process of Claim 1, wherein the polymetal halide is selected from the group consisting of polyaluminum chloride and polyaluminum sulfo silicate.
11. The process of Claim 1, wherein the anionic latex comprises a vinyl polymer resin selected from the group consisting of poly(styrene/butadiene), poly(p-methyl styrene/butadiene), poly(m-methyl styrene/butadiene), poly(.alpha.-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(p-methyl styrene/isoprene), poly(m-methyl styrene/isoprene), poly(.alpha. -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(butylacrylate-isoprene), poly(styrene/n-butyl acrylate/acrylic acid), poly(styrene/n-butyl methacrylate/acrylic acid), poly(styrene/n-butyl methacrylate/.beta.-carboxyethyl acrylate), poly(styrene/n-butyl acrylate/ .beta. -carboxyethyl acrylate) poly(styrene/butadiene/methacrylic acid), poly(styrene/n-butyl acrylate/styrene sulfonate sodium salt/acrylic acid), and mixtures thereof.
12. The process of Claim 1, wherein the coated toner particles are negatively charged.
13. The process of Claim 1, wherein the first heating is below the Tg of the sulfonated polyester resin and the second heating is above the Tg of the sulfonated polyester resin.
14. The process of Claim 1, wherein the coated toner particles are heated to a temperature of about 50°C to about 65°C.
15. The process of Claim 1, wherein the heating of the coated toner particles fuses the vinyl polymer resin onto a surface of the toner particles.
16. The process of Claim 1, wherein the colorant is a cyan pigment and wherein the vinyl polymer resin is styrene acrylate carboxylic acid.
17. A process comprising:
mixing a colorant, a sulfonated polyester resin, and a coagulant to form toner particles having a particle size of from about 1 to about 5 microns;
heating the resulting sulfonated polyester toner particles;
adding a polymetal halide and an anionic latex comprising a vinyl polymer resin;
and fusing the vinyl polymer resin to a surface of the toner particles by heating.
18. The process of Claim 17, wherein the coagulant is zinc acetate and the vinyl polymer resin is styrene acrylate carboxylic acid.
19. A process comprising:
mixing a sulfonated polyester toner particle with a coagulant to form a core toner particle; and adding a polymetal halide onto a surface of the core toner particle to form a coated toner particle.
20. The process of Claim 19, wherein the sulfonated polyester toner particle has a particle size of from about 25 to about 100 nm.
21. The process of Claim 19, wherein the core toner particle has a particle size of from about 3 to about 4 microns.
22. A process comprising:
mixing a sulfonated polyester resin, a colorant, and a first portion of a coagulant;
heating the mixture; and adding a second portion of the coagulant to form sulfonated polyester toner particles.
23. The process of Claim 22, wherein an initial temperature of the mixture is about 23°C to about 25°C.
24. The process of Claim 22, wherein an initial pH of the mixture is 5.5.
25. The process of Claim 22, wherein the sulfonated polyester toner particles have a particle size of from about 2 to about 3 microns.
26. A process comprising:
mixing a sulfonated polyester resin, a colorant, a wax and a coagulant;
heating the resulting sulfonated polyester toner particles;
adding a polymetal halide and an anionic latex to form coated toner particles;
and heating the coated toner particles.
27. The process of Claim 26, wherein the polymetal halide is added to the toner particles at a pH of about 5.4.
28. The process of Claim 26, wherein the polymetal halide is present in an amount of from about 0.1 % to about 10% by weight relative to the weight of the sulfonated polyester toner particles.
29. The process of Claim 26, further comprising reducing the pH of the coated toner particles to about 4 after the polymetal halide is added.
30. The process of Claim 26, further comprising reducing the pH of the coated toner particles to less than about 3 after the anionic latex is added.
CA2541183A 2005-03-31 2006-03-24 Toner processes Expired - Fee Related CA2541183C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US11/094,404 2005-03-31
US11/094,404 US7799502B2 (en) 2005-03-31 2005-03-31 Toner processes

Publications (2)

Publication Number Publication Date
CA2541183A1 true CA2541183A1 (en) 2006-09-30
CA2541183C CA2541183C (en) 2010-05-11

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CA2541183A Expired - Fee Related CA2541183C (en) 2005-03-31 2006-03-24 Toner processes

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US (1) US7799502B2 (en)
EP (1) EP1708037B1 (en)
JP (1) JP4908030B2 (en)
CN (1) CN1841216B (en)
BR (1) BRPI0601046A (en)
CA (1) CA2541183C (en)
DE (1) DE602006001677D1 (en)

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JP5639859B2 (en) * 2010-11-19 2014-12-10 花王株式会社 Method for producing toner for electrophotography
JP5861437B2 (en) * 2011-12-15 2016-02-16 三洋電機株式会社 Negative electrode for nonaqueous electrolyte secondary battery and method for producing the same
JP6040859B2 (en) * 2013-05-13 2016-12-07 富士ゼロックス株式会社 Electrostatic image developing toner, electrostatic image developer, toner cartridge, process cartridge, image forming apparatus, and image forming method
US9134635B1 (en) 2014-04-14 2015-09-15 Xerox Corporation Method for continuous aggregation of pre-toner particles

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