IP Library Granted Patent US 9,982,088
Granted Patent B2
US 9,982,088 · App. 15/356,307 · Granted May 29, 2018

Carboxylic acid or acid salt functionalized polyester polymers

Inventors: Karen A. Moffat (Brantford, CA); Dragan Nikolic (Edmonton, CA); Valerie M. Farrugia (Oakville, CA); Jordan H. Wosnick (Toronto, CA); Andriy Kovalenko (Edmonton, CA); Alexander Kobryn (Edmonton, CA); Sergey Gusarov (Edmonton, CA)
Assignees: XEROX CORPORATION; NATIONAL RESEARCH COUNCIL OF CANADA
C08G63/183C08G63/16C08G63/688C08G63/916G03G9/0804G03G9/0819G03G9/0825G03G9/08755G03G9/08797G03G9/09321G03G9/09371
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Quick Facts
Patent No.
US 9,982,088
App. No.
15/356,307
Granted
May 29, 2018
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 (18)

1. A polyester polymer comprising 25 to 150 monomer units, the polyester polymer being prepared from at least one block oligomer of the monomer units, wherein a first monomer unit comprises an acid residue and an alcohol residue, wherein the first monomer unit comprises either a single pendant carboxylic acid side group or a single pendant carboxylic acid salt side group on said acid residue, wherein a second monomer unit comprises an acid residue and an alcohol residue neither of which is functionalized, wherein the at least one block oligomer comprises two adjacent first monomers centrally located in the at least one block oligomer and wherein the polyester polymer comprising the 25 to 150 monomer units forms a micelle of predetermined mass median diameter at 360K.

2. The polyester polymer of claim 1 , wherein the polyester polymer comprises 25 to 100 monomer units.

3. The polyester polymer of claim 2 , wherein the polyester polymer comprises 25 to 50 monomer units.

4. The polyester polymer of claim 2 , wherein the micelle formed at 360K has a predetermined mass median diameter of 30 Å to 100 nm.

5. The polyester polymer of claim 3 , wherein the micelle formed at 360K has a predetermined mass median diameter of 40 Å to 150 nm.

6. The polyester polymer of claim 3 , wherein the micelle formed at 360K has a predetermined mass median diameter of 47 Å to 200 nm.

7. A toner particle comprising the polyester polymer of claim 1 , the polyester polymer comprising 25 to 150 monomer units, wherein a monomer unit comprises an acid residue and an alcohol residue, wherein at least two adjacent monomer units each comprise either a single pendant carboxylic acid side group or a single pendant carboxylic acid salt side group on said acid residue, wherein the remaining monomer units are non-functionalized, and wherein the polyester polymer comprising 25 to 150 monomer units forms a micelle of predetermined mass median diameter at 360K.

8. The toner particle of claim 7 , wherein the polyester polymer comprises 25 to 100 monomer units.

9. The toner particle of claim 8 , wherein the polyester polymer comprises 25 to 50 monomer units.

10. The toner particle of claim 8 , wherein the micelle formed at 360K has a predetermined mass median diameter of 30 Å to 100 nm.

11. The toner particle of claim 9 , wherein the micelle formed at 360K has a predetermined mass median diameter of 40 Å to 150 nm.

12. The toner particle of claim 9 , wherein the micelle formed at 360K has a predetermined mass median diameter of 47 Å to 200 nm.

13. A developer comprising the toner particle of claim 7 .

14. A toner particle comprising a polyester polymer core and a resin shell disposed over the core, the polyester polymer comprising 25 to 150 monomer units, wherein a monomer unit comprises an acid residue and an alcohol residue, wherein at least two adjacent monomer units each comprise either a single pendant carboxylic acid side group or a single pendant carboxylic acid salt side group on said acid residue, wherein the remaining monomer units are non-functionalized, and wherein the polyester polymer comprising 25 to 150 monomer units forms a micelle of predetermined mass median diameter at 360K, wherein the resin shell is formed from a polymer having a weight average molecular weight of about 300,000 to about 350,000.

15. The toner particle of claim 14 , wherein the resin shell is formed from a polymer selected from the group consisting of a fluoropolymer, terpolymers of styrene, methyl methacrylates, silanes, tetrafluoroethylenes, and polymethylmethacrylate (PMMA).

16. The toner particle of claim 14 , wherein the resin shell is formed from a mixture of PMMA and polyvinylidenefluoride in a weight ratio range of from about 30 to about 70 wt % to about 70 to about 30 wt %.

17. The toner particle of claim 14 , wherein the polyester polymer comprises 25 to 100 monomer units.

18. The toner particle of claim 14 , wherein the micelle formed at 360K has a predetermined mass median diameter of 30 Å to 100 nm.

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 Nov 18, 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 040372/0653 →
Continuity (3)
Continuation 15067898 · Mar 11, 2016
Division 13316585 · Dec 12, 2011
Related Publication 20170066872A1 · Mar 9, 2017