CA2702511A1 - Curable toner compositions and processes - Google Patents

Curable toner compositions and processes Download PDF

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Publication number
CA2702511A1
CA2702511A1 CA2702511A CA2702511A CA2702511A1 CA 2702511 A1 CA2702511 A1 CA 2702511A1 CA 2702511 A CA2702511 A CA 2702511A CA 2702511 A CA2702511 A CA 2702511A CA 2702511 A1 CA2702511 A1 CA 2702511A1
Authority
CA
Canada
Prior art keywords
process according
weight
particles
polyaluminum
toner particles
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
CA2702511A
Other languages
French (fr)
Other versions
CA2702511C (en
Inventor
Guerino G. Sacripante
Nathan Dyck
Daryl W. Vanbesien
Edward G. Zwartz
Cuong Vong
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
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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 CA2702511A1 publication Critical patent/CA2702511A1/en
Application granted granted Critical
Publication of CA2702511C publication Critical patent/CA2702511C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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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
    • G03G9/0802—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
    • G03G9/08755—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
    • G03G9/093—Encapsulated toner particles
    • G03G9/09307—Encapsulated toner particles specified by the shell material
    • G03G9/09314—Macromolecular compounds
    • G03G9/09321—Macromolecular compounds obtained 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
    • G03G9/09314—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
    • G03G9/09335—Non-macromolecular organic compounds
    • 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
    • G03G9/0935—Encapsulated toner particles specified by the core material
    • G03G9/09357—Macromolecular compounds
    • G03G9/09364—Macromolecular compounds obtained 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
    • G03G9/0935—Encapsulated toner particles specified by the core material
    • G03G9/09357—Macromolecular compounds
    • G03G9/09371—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds

Abstract

Processes for producing emulsion aggregation toners are provided. In embodiments, methods of the present disclosure may be utilized to produce toners suitable for low melt applications, including use in flexible packaging applications, where low pile height is desired for low cost and flexibility. In embodiments, the EA toners may be prepared by optimizing the particle size of the emulsion, the choice of and amount of aggregating agent utilized, and the solids content of the emulsion.

Claims (20)

1. A process comprising:

contacting an emulsion comprising at least one amorphous polyester resin in combination with at least one crystalline polyester resin with an optional wax and an optional colorant, the emulsion having a particle size of from about 50 nm to about 200 nm and a solids content of from about 10% to about 50% by weight;

aggregating the particles by contacting the particles with from about 0.1 parts per hundred to about 2 parts per hundred of an aggregating agent selected from the group consisting of aluminum sulfate, polyaluminum chloride, polyaluminum bromide, polyaluminum fluoride, polyaluminum iodide, polyaluminum silicate, polyaluminum sulfosilicate, aluminum chloride, aluminum nitrite, aluminum sulfate, potassium aluminum sulfate, and combinations thereof to form aggregated particles;

contacting the aggregated particles with at least one unsaturated polymeric resin in combination with a photoinitiator to form a shell over the aggregated particles;

coalescing the aggregated particles to form toner particles; and recovering the toner particles.
2. The process according to claim 1, wherein the polymeric resin comprises an amorphous polyester resin.
3 The process according to claim 1, wherein the polymeric resin comprises a crystalline polyester having a number average molecular weight of from about 1,000 to about 50,000, a weight average molecular weight of from about 2,000 to about 100,000, and a molecular weight distribution (Mw/Mn) of from about 2 to about 6.
4. The process according to claim 1, wherein the wherein the polymeric resin comprises an amorphous polyester resin of the formula:

wherein m may be from about 5 to about 1000, in combination with a crystalline polyester resin of the formula:

wherein b is from about 5 to about 2000 and d is from about 5 to about 2000.
5. The process according to claim 1, wherein the photoinitiator is selected from the group consisting of hydroxycyclohexylphenyl ketones, other ketones, benzoins, benzoin alkyl ethers, benzophenones, trimethylbenzoylphenylphosphine oxides, azo compounds, anthraquinones, substituted anthraquinones, other substituted or unsubstituted polynuclear quinines, acetophenones, thioxanthones, ketals, acylphosphines, and mixtures thereof.
6. The process according to claim 1, wherein the photoinitiator is selected from the group consisting of alpha-amino ketone, 4-(2-hydroxyethoxy)phenyl-(2-hydroxy-2-propyl) ketone, 2,4,6-trimethylbenzophenone, 4-methylbenzophenone, 2,4,6-trimethylbenzoyl-diphenyl--phosphine oxide, phenylbis(2,4,6-trimethylvbenzyoyl) phosphine oxide, alkyl substituted or halo substituted anthraquinones, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, 2-isopropyl-9H--thioxanthen-9-one, 2-Hydrox-4'-hydroxyethoxy-2-methylpropiophenone, 1--hydroxycyclohexylphenyl ketone, ethyl-2,4,6-trimethylbenzoylphenylphosphinate, and mixtures thereof.
7. The process according to claim 1, wherein the polymeric resin is present in an amount of from about 65 percent by weight to about 95 percent by weight of the toner particles and the photoinitiator is present in an amount of from about 0.5 percent by weight to about 15 percent by weight of the toner particles.
8. The process according to claim 1, wherein the toner particles possess a Number Average Geometric Standard Deviation or Volume Average Geometric Standard Deviation of from about 1.18 to about 1.30.
9. The process according to claim 1, wherein the toner particles have a gloss of from about 20 ggu to about 100 ggu.
10. The process according to claim 1, wherein the aggregating agent comprises aluminum sulfate.
11. A process comprising:

contacting an emulsion comprising at least one amorphous polyester resin in combination with at least one crystalline polyester resin with an optional wax and an optional colorant, the emulsion having a particle size of from about 50 nm to about 200 nm and a solids content of from about 10% to about 50% by weight;

aggregating the particles by contacting the particles with from about 0.1 parts per hundred to about 2 parts per hundred of an aggregating agent selected from the group consisting of aluminum sulfate, polyaluminum chloride, polyaluminum bromide, polyaluminum fluoride, polyaluminum iodide, polyaluminum silicate, polyaluminum sulfosilicate, aluminum chloride, aluminum nitrite, aluminum sulfate, potassium aluminum sulfate, and combinations thereof to form aggregated particles;

contacting the aggregated particles with at least one unsaturated polymeric resin in combination with a photoinitiator to form a shell over the aggregated particles;

coalescing the aggregated particles to form toner particles;
recovering the toner particles;

applying the toner particles to a substrate; and fusing the toner particles to the substrate by non-contact fusing to form an image on the substrate, wherein the toner has a gloss of from about 20 ggu to about 100 ggu and the image on the substrate has a toner pile height of from about 1 micron to about 6 microns.
12. The process according to claim 11, wherein the polymeric resin comprises an amorphous polyester resin.
13. The process according to claim 11, wherein the polymeric resin comprises a crystalline polyester having a number average molecular weight of from about 1,000 to about 50,000, a weight average molecular weight of from about 2,000 to about 100,000, and a molecular weight distribution (Mw/Mn) of from about 2 to about 6.
14. The process according to claim 11, wherein the wherein the polymeric resin comprises an amorphous polyester resin of the formula:

wherein m may be from about 5 to about 1000, in combination with a crystalline polyester resin of the formula:

wherein b is from about 5 to about 2000 and d is from about 5 to about 2000.
15. The process according to claim 11, wherein the photoinitiator is selected from the group consisting of hydroxycyclohexylphenyl ketones, other ketones, benzoins, benzoin alkyl ethers, benzophenones, trimethylbenzoylphenylphosphine oxides, azo compounds, anthraquinones, substituted anthraquinones, other substituted or unsubstituted polynuclear quinines, acetophenones, thioxanthones, ketals, acylphosphines, and mixtures thereof.
16. The process according to claim 11, wherein the photoinitiator is selected from the group consisting of alpha-amino ketone, 4-(2-hydroxyethoxy)phenyl-(2-hydroxy-2-propyl) ketone, 2,4,6-trimethylbenzophenone, 4-methylbenzophenone, 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide, phenylbis(2,4,6-trimethylvbenzyoyl) phosphine oxide, alkyl substituted or halo substituted anthraquinones, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, 2-isopropyl-9H-thioxanthen-9-one, 2-Hydrox-4'-hydroxyethoxy-2-methylpropiophenone, 1-hydroxycyclohexylphenyl ketone, ethyl-2,4,6-trimethylbenzoylphenylphosphinate, and mixtures thereof.
17. The process according to claim 11, wherein the polymeric resin is present in an amount of from about 65 percent by weight to about 95 percent by weight of the toner particles and the photoinitiator is present in an amount of from about 0.5 percent by weight to about 15 percent by weight of the toner particles.
18. The process according to claim 11, wherein the toner particles possess a Number Average Geometric Standard Deviation or Volume Average Geometric Standard Deviation of from about 1.18 to about 1.30.
19. The process according to claim 11, wherein the aggregating agent comprises aluminum sulfate.
20. The process according to claim 11, wherein the image on the substrate has a toner pile height of from about 2 microns to about 4 microns.
CA2702511A 2009-05-08 2010-04-30 Curable toner compositions and processes Expired - Fee Related CA2702511C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US12/437,582 2009-05-08
US12/437,582 US8192912B2 (en) 2009-05-08 2009-05-08 Curable toner compositions and processes

Publications (2)

Publication Number Publication Date
CA2702511A1 true CA2702511A1 (en) 2010-11-08
CA2702511C CA2702511C (en) 2012-07-10

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Family Applications (1)

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CA2702511A Expired - Fee Related CA2702511C (en) 2009-05-08 2010-04-30 Curable toner compositions and processes

Country Status (4)

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US (1) US8192912B2 (en)
EP (1) EP2249210B1 (en)
JP (1) JP5442528B2 (en)
CA (1) CA2702511C (en)

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Also Published As

Publication number Publication date
JP5442528B2 (en) 2014-03-12
EP2249210B1 (en) 2014-11-05
US8192912B2 (en) 2012-06-05
CA2702511C (en) 2012-07-10
US20100285403A1 (en) 2010-11-11
JP2010262301A (en) 2010-11-18
EP2249210A1 (en) 2010-11-10

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