IP Library Granted Patent US 9,804,513
Granted Patent B2
US 9,804,513 · App. 14/327,695 · Granted Oct 31, 2017

Toner compositions

Inventors: Daryl Vanbesien (Burlington, CA); Yixin Gong (Mississauga, CA); Karen A Moffat (Brantford, CA); Richard P N Veregin (Mississauga, CA); Cuong Vong (Hamilton, CA); Jordan H Wosnick (Toronto, CA); Suxia Yang (Mississauga, CA)
Assignee: Xerox Corporation
G03G9/0804G03G9/0806G03G9/0819G03G9/0827G03G9/08704G03G9/08708G03G9/08711G03G9/08726G03G9/08728G03G9/091G03G9/09392
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Quick Facts
Patent No.
US 9,804,513
App. No.
14/327,695
Granted
Oct 31, 2017
Kind
B2
Abstract

The present disclosure provides processes for producing toners by emulsion aggregation where the resulting toner particles have high pigment loadings and desired circularity. The methods include adding a metal, in embodiments a metal salt, at the beginning of coalescence, which surprisingly speeds the coalescence process and produces toner particles having a desired size and circularity for use in electrophotographic imaging systems.

Claims (34)

1. A process comprising:

a) contacting a resin comprising at least two monomers selected from acrylate monomers, styrene monomers and combinations thereof with a colorant, a surfactant and an optional wax to form an emulsion;

b) contacting said emulsion with a coagulant;

c) adding a transition metal salt, wherein said transition metal is copper, zinc, cobalt, nickel, molybdenum, manganese, chromium, vanadium, titanium or alloys thereof, to the emulsion of step b) comprising said coagulant;

d) coalescing the emulsion of step c) comprising said transition metal powder or said transition metal salt over a period of time from about 0.5 hours to about 3.5 hours to form toner; and

e) recovering said toner.

2. The process according to claim 1 , wherein said resin further comprises poly(styrene-alkyl acrylate), poly (styrene-alkyl acrylate-acrylic acid), poly(styrene-alkyl methacrylate-acrylic acid), poly(alkyl methacrylate-alkyl acrylate), poly(alkyl methacrylate-aryl acrylate), poly(aryl methacrylate-alkyl acrylate), poly(alkyl methacrylate-acrylic acid), poly(styrene-alkyl acrylate-acrylonitrile-acrylic acid), poly(alkyl acrylate-acrylonitrile-acrylic acid), poly(styrene-butadiene), poly(methylstyrene-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(methylstyrene-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-butadiene-acrylonitrile-acrylic 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), poly(styrene-butadiene), poly(styrene-isoprene), poly(styrene-butyl methacrylate), poly(styrene-butyl acrylate-acrylic acid), poly(styrene-butyl methacrylate-acrylic acid), poly(butyl methacrylate-butyl acrylate), poly(butyl methacrylate-acrylic acid), poly(acrylonitrile-butyl acrylate-acrylic acid) or a combination thereof.

3. The process according to claim 1 , further comprising adding in step a), a stabilizer of formula (I):

wherein R1 is hydrogen or a methyl group, R2 and R3 are independently selected from alkylene groups containing from about 1 to about 12 carbon atoms or a phenylene group, and n is from about 0 to about 20.

4. The process according to claim 3 , wherein said stabilizer comprises β carboxyethyl acrylate, poly(2-carboxyethyl)acrylate, 2-carboxyethyl methacrylate or a combination thereof.

5. The process according to claim 1 , wherein said colorant comprises a dye, a pigment, a combination of dyes, a combination of pigments or a combination of a dye and a pigment.

6. The process of claim 1 , wherein said colorant is present in an amount from about 8 percent to about 40 percent by weight of said toner.

7. The process according to claim 1 , wherein said toner comprises a wax.

8. The process of claim 7 , wherein said wax comprises polytetrafluoroethylene wax, polyethylene wax, polypropylene wax, carnauba wax, candelilla wax, beeswax, montan wax, ozokerite, ceresin, paraffin wax, microcrystalline wax, a Fischer-Tropsch wax, or a combination thereof.

9. The process of claim 7 , wherein said wax is present in an amount from about 0.1 percent to about 30 percent by weight of said toner.

10. The process according to claim 1 , wherein said coagulant comprises a polymetal salt.

11. The process of claim 1 , wherein said coagulant comprises a polyaluminum halide, a polyaluminum silicate, a water soluble metal salt, or a combination thereof.

12. The process of claim 1 , further comprising following step b) and before step c), adding to said emulsion of step b), a shell resin.

13. A process comprising:

a) contacting a resin comprising at least two monomers comprising an acrylate monomer, a styrene monomer or a combination thereof with, a colorant, a surfactant and an optional wax to form an emulsion;

b) contacting said emulsion with a coagulant;

c) adding a transition metal salt wherein said transition metal salt comprises copper II nitrate or iron nitrate to the emulsion of step b) comprising a coagulant;

d) coalescing the emulsion of step c) comprising said transition metal salt of step c) over a period of time from about 0.5 hours to about 3.5 hours to form toner; and

e) recovering said toner.

14. A process comprising:

a) contacting a resin comprising at least two monomers comprising an acrylate monomer, a styrene monomer or a combination thereof with, a colorant, a surfactant and an optional wax to form an emulsion;

b) contacting said emulsion with a coagulant;

c) adding a transition metal salt selected from the group consisting of nitrates, sulfates, halides, acetates, phosphates, oxides, hydroxides, carbonates and combinations thereof, comprising a metal selected from the group consisting of copper, iron and combinations thereof to the emulsion of step b) comprising a coagulant;

d) coalescing the emulsion of step c) comprising said transition metal salt of step c) over a period of time from about 0.5 hours to about 3.5 hours to form toner; and

e) recovering said toner;

further comprising adding in step a), a stabilizer of formula (I):

wherein R1 is hydrogen or a methyl group, R2 and R3 are independently selected from alkylene groups containing from about 1 to about 12 carbon atoms or a phenylene group, and n is from about 0 to about 20.

15. The process according to claim 14 , wherein said colorant is present in an amount from about 8 percent to about 40 percent by weight of said toner.

16. The process according to claim 14 , further comprising following step b) and prior to step c), adding to said emulsion of step b), a shell resin.

Assignments (9)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 6, 2025
From: XEROX CORPORATION
To: GENESEE VALLEY INNOVATIONS, LLC
Reel/Frame 073842/0479 →
SECOND LIEN NOTES PATENT SECURITY AGREEMENT Recorded Jul 2, 2025
From: XEROX CORPORATION
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 071785/0550 →
FIRST LIEN NOTES PATENT SECURITY AGREEMENT Recorded Apr 11, 2025
From: XEROX CORPORATION
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 070824/0001 →
SECURITY INTEREST Recorded Feb 13, 2024
From: XEROX CORPORATION
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 066741/0001 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS RECORDED AT RF 064760/0389 Recorded Feb 13, 2024
From: CITIBANK, N.A., AS COLLATERAL AGENT
To: XEROX CORPORATION
Reel/Frame 068261/0001 →
SECURITY INTEREST Recorded Nov 20, 2023
From: XEROX CORPORATION
To: JEFFERIES FINANCE LLC, AS COLLATERAL AGENT
Reel/Frame 065628/0019 →
SECURITY INTEREST Recorded Jun 22, 2023
From: XEROX CORPORATION
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 064760/0389 →
RELEASE OF SECURITY INTEREST IN PATENTS AT R/F 062740/0214 Recorded May 18, 2023
From: CITIBANK, N.A., AS AGENT
To: XEROX CORPORATION
Reel/Frame 063694/0122 →
SECURITY INTEREST Recorded Nov 10, 2022
From: XEROX CORPORATION
To: CITIBANK, N.A., AS AGENT
Reel/Frame 062740/0214 →
Continuity (2)
Continuation 12248939 · Oct 10, 2008
Related Publication 20170031254A1 · Feb 2, 2017