IP Library Granted Patent US 9,594,319
Granted Patent B2
US 9,594,319 · App. 12/553,306 · Granted Mar 14, 2017

Curable toner compositions and processes

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Quick Facts
Patent No.
US 9,594,319
App. No.
12/553,306
Granted
Mar 14, 2017
Kind
B2
Abstract

An emulsion aggregation toner composition includes toner particles including: an unsaturated polymeric resin, such as amorphous resins, crystalline resins, and combinations thereof; an optional colorant; an optional wax; an optional coagulant; and a photoinitiator. By optimizing the particle size of the emulsion, the aggregant concentration utilized in the emulsion aggregation process, and the solids content of the emulsion, toners may be produced capable of generating images with non-contact fusing that have high gloss.

Claims (44)

1. A process comprising:

contacting an emulsion comprising at least one polyester resin comprising particles of a size of from about 80 nanometers to about 120 nanometers with an optional colorant, and an optional wax;

aggregating the particles by contacting the particles with from about 0.01 to about 0.35 parts per hundred of an aggregating agent to form aggregated particles;

contacting the aggregated particles with at least one unsaturated polyester 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 of a size of from about 3 microns to about 4 microns,

wherein the emulsion comprising at least one polyester resin has a solids content of from about 15 to about 50% solids in water; and

wherein the at least one polyester resin comprises an amorphous polyester resin of the formula:

wherein m is 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.

2. The process according to claim 1 , wherein the aggregating agent is selected from the group consisting of aluminum sulfate, polyaluminum chloride, polyaluminum bromide, polyaluminum fluoride, polyaluminum iodide, polyaluminum silicate, polyaluminum sulfosilicate aluminum chloride, aluminum nitrite, potassium aluminum sulfate, calcium acetate, calcium chloride, calcium nitrite, calcium oxylate, calcium sulfate, magnesium acetate, magnesium nitrate, magnesium sulfate, zinc acetate, zinc nitrate, zinc sulfate, zinc chloride, zinc bromide, magnesium bromide, copper chloride, copper sulfate, and combinations thereof.

3. The process according to claim 1 , wherein the at least one polyester 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 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.

5. 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.

6. A process comprising:

contacting an emulsion comprising at least one polyester resin comprising particles of a size of from about 80 nanometers to about 120 nanometers with an optional colorant, and an optional wax;

aggregating the particles by contacting the particles with from about 0.01 to about 0.35 parts per hundred of an aggregating agent to form aggregated particles;

contacting the aggregated particles with at least one unsaturated polyester 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 of a size of from about 3 microns to about 4 microns,

wherein the at least one polyester 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, and

wherein the at least one polyester resin comprises an amorphous polyester resin of the formula:

wherein m is 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.

7. 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 1.05 to about 1.55.

8. A process comprising:

contacting an emulsion comprising at least one polyester resin comprising particles of a size of from about 80 nanometers to about 120 nanometers with an optional colorant; and an optional wax;

aggregating the particles by contacting the particles with from about 0.01 to about 0.35 parts per hundred of an aggregating agent to form aggregated particles;

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

coalescing the aggregated particles to form toner particles; and

recovering the toner particles of a size of from about 3 microns to about 4 microns,

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 possesses a gloss of from about 20 ggu to about 100 ggu; and

wherein the at least one polyester resin comprises an amorphous polyester resin of the formula:

wherein m is 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.

9. The process according to claim 8 , wherein the emulsion comprising at least one unsaturated polyester resin has a solids content of from about 15 to about 50% solids in water.

10. The process according to claim 8 , wherein the at least one polyester resin comprises an amorphous polyester resin.

11. The process according to claim 8 , wherein the at least one polyester 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.

12. The process according to claim 8 , wherein the aggregating agent is selected from the group consisting of aluminum sulfate, polyaluminum chloride, polyaluminum bromide, polyaluminum fluoride, polyaluminum iodide, polyaluminum silicate, polyaluminum sulfosilicate aluminum chloride, aluminum nitrite, potassium aluminum sulfate, and combinations thereof, and 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.

13. The process according to claim 8 , wherein the at least one polyester 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.

14. The process according to claim 8 , wherein the non-contact fusing occurs by exposing the toner particles to infrared light at a wavelength of from about 750 nm to about 2500 nm for a period of time of from about 30 milliseconds to about 3 seconds.

15. The process according to claim 8 , wherein the toner particles possess a Number Average Geometric Standard Deviation or Volume Average Geometric Standard Deviation of from about 1.05 to about 1.55.

Assignments (10)
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 →
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 Feb 13, 2024
From: XEROX CORPORATION
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 066741/0001 →
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 3, 2009
From: ZWARTZ, EDWARD GRAHAM; SACRIPANTE, GUERINO G.
To: XEROX CORPORATION
Reel/Frame 023189/0101 →