CA2562956A1 - Emulsion containing epoxy resin - Google Patents

Emulsion containing epoxy resin Download PDF

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Publication number
CA2562956A1
CA2562956A1 CA002562956A CA2562956A CA2562956A1 CA 2562956 A1 CA2562956 A1 CA 2562956A1 CA 002562956 A CA002562956 A CA 002562956A CA 2562956 A CA2562956 A CA 2562956A CA 2562956 A1 CA2562956 A1 CA 2562956A1
Authority
CA
Canada
Prior art keywords
emulsion
epoxy resin
polyester resin
sulfonated polyester
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
CA002562956A
Other languages
French (fr)
Other versions
CA2562956C (en
Inventor
Ke Zhou
Anna-Karin Eriksson
Guerino G. Sacripante
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 CA2562956A1 publication Critical patent/CA2562956A1/en
Application granted granted Critical
Publication of CA2562956C publication Critical patent/CA2562956C/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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
    • C08J3/05—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media from solid polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • 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
    • G03G9/0802—Preparation methods
    • G03G9/0804—Preparation methods whereby the components are brought together in a liquid dispersing medium
    • G03G9/0806—Preparation 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
    • 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
    • G03G9/08753—Epoxyresins
    • 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
    • G03G9/08782—Waxes
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
    • C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds

Abstract

The emulsion herein is of an epoxy resin having a glass transition temperature of at least about 40°C, wherein the average diameter of the epoxy resin particles in the emulsion is 500 nm or less. The emulsion may include an epoxy resin, a sulfonated polyester resin and a nonionic surfactant. The emulsion may be used to produce a toner particle in an emulsion aggregation method.

Claims (26)

1. An emulsion comprised of an epoxy resin, a sulfonated polyester resin and a nonionic surfactant.
2. The emulsion according to claim 1, wherein the epoxy resin and the sulfonated polyester resin are present as a mixture in emulsified particles dispersed in an aqueous phase of the emulsion.
3. The emulsion according to claim 2, wherein the emulsified particles have an average diameter of from about 10 nm to about 500 nm.
4. The emulsion according to claim 1, wherein the epoxy resin is a bisphenol A
based epoxy.
5. The emulsion according to claim 1, wherein the epoxy resin has a glass transition temperature of from about 40°C to about 100°C.
6. The emulsion according to claim 1, wherein the sulfonated polyester resin is an alkali metal sulfonated polyester resin.
7. The emulsion 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.
8. The emulsion according to claim 7, 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.
9. The emulsion according to claim 1, wherein the emulsion comprises from about 1% to about 40% by weight of the emulsion of the sulfonated polyester resin and from about 60% to about 99% by weight of the emulsion of the epoxy resin.
10. The emulsion according to claim 1, wherein the nonionic surfactant comprises a block copolymer of polyethylene oxide and polypropylene oxide.
11. The emulsion according to claim 1, wherein the nonionic surfactant comprises from about 0.5% to about 10% by weight of the emulsion.
12. The emulsion according to claim 1, wherein the emulsion further includes an epoxy curing catalyst.
13. A toner comprising a binder, a colorant and optionally a wax, wherein the binder comprises a mixture of an epoxy resin and a sulfonated polyester resin.
14. The toner according to claim 13, wherein the epoxy resin is a bisphenol A
based epoxy.
15. The toner according to claim 13, wherein the epoxy resin has a glass transition temperature of from about 40°C to about 100°C.
16. The toner according to claim 13, wherein the sulfonated polyester resin is an alkali metal sulfonated polyester resin.
17. The toner according to claim 13, 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 13, wherein the binder comprises from about 1 to about 40% by weight of the sulfonated polyester resin and from about 60% to about 99%
by weight of the epoxy resin.
20. The toner according to claim 13, wherein the colorant comprises pigment, dye, mixtures of pigment and dye, mixtures of pigments or mixtures of dyes.
21. A developer comprising the toner of claim 13 admixed with a carrier.
22. A process of preparing the emulsion according to claim 1, comprising heating a mixture of the epoxy resin, the sulfonated polyester resin and the nonionic surfactant, and metering water into the mixture until phase inversion occurs to form the emulsion.
23. The process according to claim 22, wherein the heating is at a temperature of from about 50°C to about 120°C, and wherein the metering is conducted while maintaining the temperature at from about 50°C to about 120°C.
24. The process according to claim 22, wherein the process further comprises adding a colorant to the emulsion, heating to below a glass transition temperature of at least the epoxy resin, adding an aggregating agent, and aggregating the mixture to form toner particles.
25. The process according to claim 22, wherein the toner particles have a volume average diameter of from about 3 µm to about 12 µm.
26. An image forming device comprising a charging component, an imaging component, a photoconductive component, a developing component, a transfer component, and a fusing component, wherein the development component comprises a developer prepared by mixing a carrier with the toner according to claim 13.
CA2562956A 2005-10-13 2006-10-06 Emulsion containing epoxy resin Expired - Fee Related CA2562956C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US11/248,277 2005-10-13
US11/248,277 US7759432B2 (en) 2005-10-13 2005-10-13 Emulsion containing epoxy resin

Publications (2)

Publication Number Publication Date
CA2562956A1 true CA2562956A1 (en) 2007-04-13
CA2562956C CA2562956C (en) 2010-12-07

Family

ID=37499989

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2562956A Expired - Fee Related CA2562956C (en) 2005-10-13 2006-10-06 Emulsion containing epoxy resin

Country Status (7)

Country Link
US (1) US7759432B2 (en)
EP (1) EP1775639B1 (en)
JP (1) JP2007107004A (en)
CN (1) CN1948391A (en)
BR (1) BRPI0604261A (en)
CA (1) CA2562956C (en)
MX (1) MXPA06011786A (en)

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US7985524B2 (en) * 2004-01-28 2011-07-26 Xerox Corporation Emulsion aggregation process for forming curable powder coating compositions, curable powder coating compositions and method for using the same
US7851549B2 (en) * 2007-12-13 2010-12-14 Xerox Corporation Curable polyester latex made by phase inversion emulsification
JP5347273B2 (en) * 2008-01-21 2013-11-20 富士ゼロックス株式会社 Electrostatic image developing toner and method for producing the same, electrostatic image developer, image forming method, and image forming apparatus
US7989135B2 (en) * 2008-02-15 2011-08-02 Xerox Corporation Solvent-free phase inversion process for producing resin emulsions
US8313884B2 (en) * 2009-06-05 2012-11-20 Xerox Corporation Toner processes utilizing a defoamer as a coalescence aid for continuous and batch emulsion aggregation
US8741534B2 (en) 2009-06-08 2014-06-03 Xerox Corporation Efficient solvent-based phase inversion emulsification process with defoamer
US20110129774A1 (en) * 2009-12-02 2011-06-02 Xerox Corporation Incorporation of an oil component into phase inversion emulsion process
US8057849B2 (en) * 2009-12-04 2011-11-15 Xerox Corporation Ultra low melt metal nanoparticle composition for thick-film applications
US8618192B2 (en) * 2010-02-05 2013-12-31 Xerox Corporation Processes for producing polyester latexes via solvent-free emulsification
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Also Published As

Publication number Publication date
US7759432B2 (en) 2010-07-20
JP2007107004A (en) 2007-04-26
EP1775639A1 (en) 2007-04-18
EP1775639B1 (en) 2011-11-09
MXPA06011786A (en) 2007-04-12
US20070088117A1 (en) 2007-04-19
BRPI0604261A (en) 2007-08-21
CN1948391A (en) 2007-04-18
CA2562956C (en) 2010-12-07

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Effective date: 20131009