IP Library Granted Patent US 8,431,318
Granted Patent B2
US 8,431,318 · App. 12/757,321 · Granted Apr 30, 2013

Toner compositions and processes

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Quick Facts
Patent No.
US 8,431,318
App. No.
12/757,321
Granted
Apr 30, 2013
Kind
B2
Abstract

The present disclosure provides processes for producing polyester 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 compound, at the beginning of coalescence, which speeds the coalescence process and produces toner particles having a desired size and circularity for use in electrophotographic imaging systems.

Claims (51)

1. A process comprising:

contacting at least one polyester resin with at least one colorant, at least one surfactant, and an optional wax to form an emulsion possessing small particles;

optionally contacting the emulsion with an aggregating agent comprising a first metal compound;

aggregating the small particles;

halting aggregation;

adding a second metal compound comprising a metal selected from the group consisting of copper, iron, and alloys thereof to the aggregated small particles;

coalescing the aggregated particles in the presence of said second metal compound to form toner particles; and

recovering the toner particles, wherein the toner particles possess a volume average diameter of from about 3 microns to about 10 microns.

2. A process according to claim 1 , wherein the at least one polyester resin comprises at least one amorphous polyester resin, optionally in combination with at least one crystalline polyester resin.

3. The process according to claim 2 , wherein the at least one amorphous resin is of the formula:

wherein m is from about 5 to about 1000.

4. The process according to claim 2 , wherein the at least one crystalline resin is of the formula:

wherein b is from about 5 to about 2000 and d is from about 5 to about 2000.

5. A process according to claim 1 , wherein the second metal compound is selected from the group consisting of nitrates, sulfates, halides, acetates, phosphates, oxides, hydroxides, carbonates, and combinations thereof.

6. A process according to claim 1 , wherein the second metal compound is selected from the group consisting of copper II nitrate and iron nitrate.

7. A process according to claim 1 , wherein coalescing the aggregated small particles to form toner particles occurs for a period of from about 0.5 hours to about 5 hours and produces toner particles having a circularity of from about 0.95 to about 0.998.

8. A process according to claim 2 , wherein the at least one amorphous resin comprises at least one low molecular weight amorphous resin in combination with at least one high molecular weight amorphous resin.

9. A process according to claim 1 , wherein the at least one colorant comprises dyes, pigments, combinations of dyes, combinations of pigments, and combinations of dyes and pigments, present in an amount of from about 4 percent to about 40 percent by weight of the toner, and wherein the optional wax is selected from the group consisting of polyolefins, carnauba wax, rice wax, candelilla wax, sumacs wax, jojoba oil, beeswax, montan wax, ozokerite, ceresin, paraffin wax, microcrystalline wax, Fischer-Tropsch wax, stearyl stearate, behenyl behenate, butyl stearate, propyl oleate, glyceride monostearate, glyceride distearate, pentaerythritol tetra behenate, diethyleneglycol monostearate, dipropyleneglycol distearate, diglyceryl distearate, triglyceryl tetrastearate, sorbitan monostearate, cholesteryl stearate, and combinations thereof, present in an amount from about 0.1 percent to about 30 percent by weight of the toner.

10. A process according to claim 1 , further comprising:

applying the toner particles to a substrate; and

fusing the toner particles to the substrate, wherein an image formed with the toner has a toner pile height from about 0.5 microns to about 7 microns.

11. A process comprising:

contacting at least one amorphous resin with at least one crystalline resin, at least one colorant, at least one surfactant, and an optional wax to form an emulsion possessing small particles;

optionally contacting the emulsion with an aggregating agent comprising a first metal compound;

aggregating the small particles;

halting aggregation;

adding to the aggregated small particles, a second metal compound selected from the group consisting of nitrates, sulfates, halides, acetates, phosphates, oxides, hydroxides, carbonates, and combinations thereof, possessing a metal selected from the group consisting of copper, iron, and alloys thereof;

coalescing the aggregated particles in the presence of said second metal compound to form toner particles; and

recovering the toner particles, wherein the toner particles possess a volume average diameter of from about 3 microns to about 10 microns.

12. The process according to claim 11 , wherein the at least one amorphous resin is of the formula:

wherein m is from about 5 to about 1000, and the crystalline resin is of the formula:

wherein b is from about 5 to about 2000 and d is from about 5 to about 2000.

13. A process according to claim 11 , wherein the second metal compound is selected from the group consisting of copper II nitrate and iron nitrate.

14. A process according to claim 11 , wherein coalescing the aggregated small particles to form toner particles occurs for a period of from about 0.5 hours to about 5 hours and produces toner particles having a circularity of from about 0.95 to about 0.998.

15. A process according to claim 11 , wherein the at least one amorphous resin comprises at least one low molecular weight amorphous resin in combination with at least one high molecular weight amorphous resin.

16. A process according to claim 11 , wherein the at least one colorant comprises dyes, pigments, combinations of dyes, combinations of pigments, and combinations of dyes and pigments, present in an amount of from about 5 percent to about 15 percent by weight of the toner, and wherein the optional wax is selected from the group consisting of polyolefins, carnauba wax, rice wax, candelilla wax, sumacs wax, jojoba oil, beeswax, montan wax, ozokerite, ceresin, paraffin wax, microcrystalline wax, Fischer-Tropsch wax, stearyl stearate, behenyl behenate, butyl stearate, propyl oleate, glyceride monostearate, glyceride distearate, pentaerythritol tetra behenate, diethyleneglycol monostearate, dipropyleneglycol distearate, diglyceryl distearate, triglyceryl tetrastearate, sorbitan monostearate, cholesteryl stearate, and combinations thereof, present in an amount from about 0.1 percent to about 30 percent by weight of the toner.

17. A process according to claim 11 , further comprising:

applying the toner particles to a substrate; and

fusing the toner particles to the substrate, wherein an image formed with the toner has a toner pile height from about 0.5 microns to about 7 microns.

18. A process comprising:

contacting at least one amorphous resin with at least one crystalline resin, at least one colorant, at least one surfactant, and an optional wax to form an emulsion possessing small particles;

contacting the emulsion with an aggregating agent comprising a first metal compound;

aggregating the small particles;

halting aggregation;

adding to the aggregated small particles a second metal compound selected from the group consisting of nitrates, sulfates, halides, acetates, phosphates, oxides, hydroxides, carbonates, and combinations thereof, possessing a metal selected from the group consisting of copper, iron, and alloys thereof;

coalescing the aggregated particles in the presence of said second metal compound for a period of time of from about 0.5 hours to about 5 hours to form toner particles; and

recovering the toner particles, wherein the colorant comprises dyes, pigments, combinations of dyes, combinations of pigments, and combinations of dyes and pigments, present in an amount of from about 4 percent to about 40 percent by weight of the toner, and wherein the toner particles possess a volume average diameter of from about 3 microns to about 10 microns, and a circularity of from about 0.95 to about 0.998.

19. A process according to claim 18 , wherein the second metal compound comprises copper II nitrate.

20. A process according to claim 18 , further comprising:

applying the toner particles to a substrate; and

fusing the toner particles to the substrate, wherein an image formed with the toner has a toner pile height from about 0.5 microns to about 7 microns.

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 →