IP Library › Granted Patent US 10,725,394
Granted Patent B1
US 10,725,394 · App. 16/369,206 · Granted Jul 28, 2020

Cross-linked polymeric latex prepared with a low surface tension surfactant

Inventors: Richard P. N. Veregin (Mississauga, CA); Shivanthi Easwari Sriskandha (Misissauga, CA); David R. Kurceba (Hamilton, CA); Scott Edward Silver (Guelph, CA); Melanie Lynn Davis (Hamilton, CA); Cuong Vong (Hamilton, CA)
Assignee: Xerox Corporation
G03G9/09775C08K5/41C08K5/42G03G9/0804G03G9/0819G03G9/09392G03G9/09708G03G9/09725G03G9/09733C08K2201/013
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Quick Facts
Patent No.
US 10,725,394
App. No.
16/369,206
Filed
Mar 29, 2019
Granted
Jul 28, 2020
Kind
B1
Examiner
CHEA, THORL
Art Unit
1737
USPC
430/108.22
Abstract

A polymeric composition including a copolymer comprising a first monomer having a high carbon to oxygen ratio of from about 3 to about 8; a second monomer comprising two or more vinyl groups, wherein the second monomer is present in the copolymer in an amount of from greater than about 8 percent by weight to about 40 percent by weight, based on the weight of the copolymer; and optionally, a third monomer comprising an amine, wherein the third monomer is present in an amount of from about 0.1 percent by weight to about 1.5 percent by weight, based on the weight of the copolymer; and a surfactant, wherein the surfactant has a minimum surface tension at critical micelle concentration of less than about 30 mN/m. A toner including the copolymer as a toner surface additive. An emulsion aggregation toner process including the copolymer as a toner surface additive.

Claims (29)

1. A toner comprising:

toner particles comprising at least one resin, in combination with an optional colorant, and an optional wax; and

a copolymer toner surface additive on at least a portion of an external surface of the toner particles, the copolymer toner surface additive comprising:

a first monomer having a high carbon to oxygen ratio of from about 3 to about 8;

a second monomer comprising two or more vinyl groups, wherein the second monomer is present in the copolymer in an amount of from greater than about 8 percent by weight to about 40 percent by weight, based on the weight of the copolymer; and

optionally, a third monomer comprising an amine, wherein the third monomer, if present, is present in an amount of from about 0.1 percent by weight to about 1.5 percent by weight, based on the weight of the copolymer; and

a surfactant, wherein the surfactant has a minimum surface tension at critical micelle concentration of less than about 30 mN/m;

wherein the copolymer toner additive has a volume average particle diameter of from about 20 nanometers to less than 50 nanometers.

2. The toner of claim 1 , wherein the surfactant has a minimum surface tension at critical micelle concentration of from about 15 to about 25 mN/m; or

where the critical micelle concentration cannot be reached, wherein the surfactant has a minimum surface tension of from about 15 to less than about 30 mN/m.

3. The toner of claim 1 , wherein the surfactant is a dodecylbenzene sulfonate.

4. The toner of claim 1 , wherein the surfactant is selected from the group consisting of ((CH 3 ) 3 SiO 2 ) 2 Si—(CH 3 )(CH 2 ) 3 (OCH 2 CH 2 ) n OH wherein n is from about 4 to about 12, oxyethylated alcohols, dimethyldidodecyl-ammonium bromide, perfluorocarboxylic acids and salts thereof, perfluoroalkanesulfonic acid salts, isostearyl sulphate salts, (CH 3 ) 3 CCH 2 CH(CH 3 )CH 2 PO 4 Na, dioctyl ammonium sulfosuccinate, dioctyl triethylamine sulfosuccinate, dioctyl trimethylamine sulfosuccinate, dioctyl tetrapropylammonium sulfosuccinate, and combinations thereof.

5. The toner of claim 1 , wherein the toner is free of titania surface additive; or

wherein the toner contains a titania surface additive in an amount of less than about 1 part per hundred by weight, based upon a total weight of the toner components.

6. The toner of claim 1 , wherein the toner contains at least one hydrophobic silica surface additive; and wherein the toner is free of titania surface additive; or

wherein the toner contains at least one hydrophobic silica surface additive; and wherein the toner contains a titania surface additive in an amount of less than about 1 part per hundred by weight, based upon a total weight of the toner components.

7. The toner of claim 1 , wherein the toner further contains at least one hydrophobic silica surface additive and a sol-gel silica surface additive.

8. The toner of claim 1 , wherein the toner further contains a second copolymer toner surface additive comprising an organic cross-linked surface additive having a volume average particle size (d50) of from about 70 nanometers to about 250 nanometers in diameter.

9. The toner of claim 1 , wherein the copolymer toner surface additive is present in an amount of from about 0.1 part per hundred to about 2 parts per hundred by weight based on 100 parts by weight of base toner particles.

10. The toner of claim 1 , wherein the copolymer toner surface additive has a volume average particle diameter of about 20 nanometers to less than 50 nanometers; and

wherein the copolymer toner surface additive is present in an amount of from about 0.1 part per hundred to about 2 parts per hundred by weight based on 100 parts by weight of base toner particles.

11. A toner process comprising:

contacting at least one resin; an optional wax; an optional colorant; and an optional aggregating agent;

heating to form aggregated toner particles;

optionally, adding a shell resin to the aggregated toner particles, and heating to a further elevated temperature to coalesce the particles;

adding a surface additive, wherein the surface additive comprises: a first monomer having a high carbon to oxygen ratio of from about 3 to about 8; a second monomer comprising two or more vinyl groups, wherein the second monomer is present in the copolymer in an amount of from greater than about 8 percent by weight to about 40 percent by weight, based on the weight of the copolymer; optionally, a third monomer comprising an amine, wherein the third monomer, if present, is present in an amount of from about 0.1 percent by weight to about 1.5 percent by weight, based on the weight of the copolymer; and a surfactant, wherein the surfactant has a minimum surface tension at critical micelle concentration of less than about 30 mN/m;

wherein the copolymer toner surface additive has a volume average particle diameter of from about 20 nanometers to less than 50 nanometers; and

optionally, recovering the toner particles.

12. The toner process of claim 11 , wherein the copolymer surface additive surfactant is a dodecylbenzene sulfonate.

Assignments (9)
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 29, 2019
From: VEREGIN, RICHARD P. N.; SRISKANDHA, SHIVANTHI EASWARI; KURCEBA, DAVID R.; SILVER, SCOTT EDWARD; DAVIS, MELANIE LYNN; VONG, CUONG
To: XEROX CORPORATION
Reel/Frame 048737/0683 →
Cited By (2)
US 12,252,568 US 12,681,400