IP Library Granted Patent US 9,581,923
Granted Patent B2
US 9,581,923 · App. 15/067,898 · Granted Feb 28, 2017

Carboxylic acid or acid salt functionalized polyester polymers

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Quick Facts
Patent No.
US 9,581,923
App. No.
15/067,898
Granted
Feb 28, 2017
Kind
B2
Abstract

The present disclosure describes a polyester that contains plural pendant adjacent carboxylic acid or acid salt side groups for use in making a toner for use in imaging devices.

Claims (23)

1. A toner particle comprising a polyester polymer, the polyester polymer consisting of 25 units, wherein a unit consists of an acid residue and an alcohol residue, wherein two adjacent units each consist of a single pendant carboxylic acid side group or a single pendant carboxylic acid salt side group on the acid residue of each said unit, and the remaining 23 units are non-functionalized and wherein the polyester polymer of 25 units forms a micelle of at least about 60 Å at 330K.

2. The toner particle of claim 1 further comprising an amorphous resin, a crystalline resin or both.

3. The toner particle of claim 2 , wherein the resins are branched or crosslinked.

4. The toner particle of claim 2 , wherein the amorphous resin has a T g of from about 40° C. to about 75° C.

5. The toner particle of claim 2 , wherein the crystalline resin has a number average molecular weight of from about 1,000 to about 60,000.

6. The toner particle of claim 1 , wherein the polyester polymer provides an interfacial tension of at least 35 mJ/m 2 at 330K.

7. The toner particle of claim 1 , wherein the polyester polymer provides an interfacial tension of at least 25 mJ/m 2 at 360K.

8. The toner particle of claim 1 , wherein the polyester polymer forms micelles of at least about 45 Å at 360K.

9. The toner particle of claim 1 , wherein the adjacent units are at a terminus of the polyester polymer.

10. A toner particle comprising a self-assembling micelle, the micelle consisting essentially of a polyester polymer consisting of 25 units, wherein a unit consists of an acid residue and an alcohol residue, wherein two adjacent units each consist of a single pendant carboxylic acid side group or a single pendant carboxylic acid salt side group on the acid residue of each said unit, and the remaining 23 units are non-functionalized, and the micelle is stable at temperatures from about 20° C. to about 90° C.

11. The toner particle of claim 10 , wherein the self-assembling micelle has a solids loading of from about 3 wt % to about 15 wt %.

12. The toner particle of claim 10 , wherein the self-assembling micelle has a diameter of at least about 55 Å at 360K.

13. The toner particle of claim 10 , wherein the self-assembling micelle forms upon cooling from an elevated temperature being from about 1K to about 35K above the polymer T g .

14. A toner composition comprising:

toner particles comprising a polyester polymer, the polyester polymer consisting of 25 units, wherein a unit consists of an acid residue and an alcohol residue, wherein two adjacent units each consist of a single pendant carboxylic acid side group or a single pendant carboxylic acid salt side group on the acid residue of each said unit, and the remaining 23 units are non-functionalized and wherein the polyester polymer of 25 units forms a micelle of at least about 60 Å at 330K;

a colorant; and

one or more toner additives.

15. The toner composition of claim 14 , wherein the one or more toner additives are selected from the group consisting of a wax, a surfactant, a silica, a titania and mixtures thereof.

16. The toner composition of claim 14 , wherein the toner particles further comprise an amorphous resin, a crystalline resin or both.

17. The toner composition of claim 16 , wherein the resins are branched or crosslinked.

18. The toner composition of claim 14 , wherein the polyester polymer provides an interfacial tension of at least 35 mJ/m 2 at 330K or an interfacial tension of at least 25 mJ/m 2 at 360K.

19. The toner composition of claim 14 being an emulsion aggregation toner composition.

20. A developer comprising the toner particle of claim 1 .

Assignments (10)
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 May 1, 2017
From: NATIONAL RESEARCH COUNCIL OF CANADA
To: XEROX CORPORATION
Reel/Frame 042195/0428 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 11, 2016
From: MOFFAT, KAREN A.; FARRUGIA, VALERIE M.; WOSNICK, JORDAN H.; GUSAROV, SERGEY; KOVALENKO, ANDRIY; KOBRYN, ALEXANDER; NIKOLIC, DRAGAN
To: XEROX CORPORATION; NATIONAL RESEARCH COUNCIL OF CANADA
Reel/Frame 037959/0182 →