IP Library › Granted Patent US 12,252,568
Granted Patent B2
US 12,252,568 · App. 17/493,966 · Granted Mar 18, 2025

Silicone copolymer surface additive

Inventors: Richard P. N. Veregin (Mississauga, CA); Kimberly D. Nosella (Ancaster, CA); Raysa Rodriguez Diaz (Burlington, CA); Nan-Xing Hu (Oakville, CA); Majid Kamel (Mississauga, CA); Cuong Vong (Hamilton, CA)
Assignee: Xerox Corporation
C08F220/22C08F212/36C08F220/34C08F230/08G03G9/08728
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,252,568
App. No.
17/493,966
Granted
Mar 18, 2025
Kind
B2
Abstract

An organic polymeric particle including an optional first monomer comprising a hydrophobic monomer; a second monomer comprising two or more vinyl groups; an optional third monomer comprising an amine; and a vinyl siloxane polymerizable monomer.

Claims (35)

1. An organic polymeric particle consisting of:

an optional first monomer comprising a hydrophobic monomer;

a second monomer comprising two or more vinyl groups;

an optional third monomer comprising an amine; and

a vinyl siloxane polymerizable monomer, wherein the vinyl siloxane polymerizable monomer is vinyl terminated silicone-polyether.

2. The organic polymeric particle of claim 1 , wherein the first monomer comprising a hydrophobic monomer is present, and wherein the first monomer comprises a non-fluorinated hydrophobic monomer having a high carbon to oxygen ratio of from about 3 to about 8 or a fluorinated monomer.

3. The organic polymeric particle of claim 1 , wherein the first monomer comprising a hydrophobic monomer is present, and wherein the first monomer comprises an acrylate, a methacrylate, or a cyclohexylmethacrylate.

4. The organic polymeric particle of claim 1 , wherein the first monomer comprising a hydrophobic monomer comprises an aliphatic cycloacrylate selected from a member of the group consisting of cyclohexyl methacrylate, cyclopropyl acrylate, cyclobutyl acrylate, cyclopentyl acrylate, cyclohexyl acrylate, cyclopropyl methacrylate, cyclobutyl methacrylate, cyclopentyl methacrylate, isobornyl methacrylate, and combinations thereof.

5. The organic polymeric particle of claim 1 , wherein the first monomer comprising a hydrophobic monomer comprises a fluorinated acrylate.

6. The organic polymeric particle of claim 1 , wherein the first monomer comprises trifluoroethylmethacrylate.

7. The organic polymeric particle of claim 1 , wherein the second monomer is selected from a member of the group consisting of diethyleneglycol diacrylate, triethyleneglycol diacrylate, tetraethyleneglycol diacrylate, polyethyleneglycol diacrylate, 1,6-hexanediol diacrylate, neopentylglycol diacrylate, tripropyleneglycol diacrylate, polypropyleneglycol diacrylate, 2,2′,-bis(4-(acryloxy/diethoxy)phenyl)propane, trimethylolpropane triacrylate, tetramethylolmethane tetraacrylate, ethyleneglycol dimethacrylate, diethyleneglycol dimethacrylate, triethyleneglycol dimethacrylate, tetraethyleneglycol dimethacrylate, polyethyleneglycol dimethacrylate, 1,3-butyleneglycol dimethacrylate, 1,6-hexanediol dimethacrylate, neopentylglycol dimethacrylate, polypropyleneglycol dimethacrylate, 2,2′,-bis(4-(methacryloxy/diethoxy)phenyl)propane, 2,2′,-bis(4-(methacryloxy/polyethoxy)phenyl)propane, trimethylolpropane trimethacrylate, tetramethylolmethane tetramethacrylate, divinyl benzene, divinyl naphthalene, divinyl ether, and combinations thereof.

8. The organic polymeric particle of claim 1 , wherein the second monomer is divinyl benzene.

9. The organic polymeric particle of claim 1 , wherein the optional third monomer is present, and wherein the third monomer is selected from a member of the group consisting of dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate, dipropylaminoethyl methacrylate, diisopropylaminoethyl methacrylate, dibutylaminoethyl methacrylate, and combinations thereof.

10. The organic polymeric particle of claim 1 , wherein the hydrophobic monomer is cyclohexyl methacrylate; and wherein the second monomer is divinyl benzene; and wherein the third monomer is dimethylaminoethyl methacrylate.

11. A toner composition comprising:

at least one resin, an optional colorant, an optional wax, and an organic polymeric particle toner additive on at least a portion of an external surface of the toner particles, the particulate organic polymeric particle toner additive consisting of:

an optional first monomer comprising a hydrophobic monomer;

a second monomer comprising two or more vinyl groups;

an optional third monomer comprising an amine; and

a vinyl siloxane polymerizable monomer, wherein the vinyl siloxane polymerizable monomer is vinyl terminated silicone-polyether.

12. The toner composition of claim 11 , wherein the first monomer of the particulate organic polymeric particle toner additive comprising a hydrophobic monomer is present, and wherein the first monomer comprises a non-fluorinated hydrophobic monomer having a high carbon to oxygen ratio of from about 3 to about 8 or a fluorinated monomer.

13. The toner composition of claim 11 , wherein the first monomer of the particulate organic polymeric particle toner additive comprising a hydrophobic monomer is present, and wherein the first monomer comprises an acrylate, a methacrylate, or a cyclohexylmethacrylate.

14. The toner composition of claim 11 , wherein the first monomer of the particulate organic polymeric particle toner additive comprising a hydrophobic monomer comprises an aliphatic cycloacrylate selected from the group consisting of cyclohexyl methacrylate, cyclopropyl acrylate, cyclobutyl acrylate, cyclopentyl acrylate, cyclohexyl acrylate, cyclopropyl methacrylate, cyclobutyl methacrylate, cyclopentyl methacrylate, isobornyl methacrylate, and combinations thereof.

15. The toner composition of claim 11 , wherein the second monomer of the particulate organic polymeric particle toner additive is divinyl benzene.

16. The toner composition of claim 11 , wherein the optional third monomer of the particulate organic polymeric particle toner additive is present, and wherein the third monomer is selected from a member of the group consisting of dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate, dipropylaminoethyl methacrylate, diisopropylaminoethyl methacrylate, dibutylaminoethyl methacrylate, and combinations thereof.

17. The toner composition of claim 11 , wherein the hydrophobic monomer of the particulate organic polymeric particle toner additive is cyclohexyl methacrylate; and wherein the second monomer of the particulate organic polymeric particle toner additive is divinyl benzene; and wherein the third monomer of the particulate organic polymeric particle toner additive is dimethylaminoethyl methacrylate.

18. A developer comprising:

a toner composition, and a toner carrier;

wherein the toner composition comprises:

toner particles comprising at least one resin, an optional colorant, an optional wax, and an organic polymeric particle toner additive on at least a portion of an external surface of the toner particles, the organic polymeric particle toner additive consisting of:

an optional first monomer comprising a hydrophobic monomer;

a second monomer comprising two or more vinyl groups;

an optional third monomer comprising an amine; and

a vinyl siloxane polymerizable monomer, wherein the vinyl siloxane polymerizable monomer is vinyl terminated silicone-polyether.

19. The toner composition of claim 11 , wherein the vinyl siloxane polymerizable monomer comprises 1% polydimethylsiloxane with vinyl termination.

Assignments (7)
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 →
SECURITY INTEREST Recorded Nov 20, 2023
From: XEROX CORPORATION
To: JEFFERIES FINANCE LLC, AS COLLATERAL AGENT
Reel/Frame 065628/0019 →
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 Oct 5, 2021
From: VEREGIN, RICHARD P. N.; NOSELLA, KIMBERLY D.; DIAZ, RAYSA RODRIGUEZ; HU, NAN-XING; KAMEL, MAJID; VONG, CUONG
To: XEROX CORPORATION
Reel/Frame 057699/0423 →
Continuity (1)
Related Publication 20230159683A1 · May 25, 2023
References Cited (58)
US 3590000A · Palermiti et al. · 1971 [cited by applicant]
US 3847604A · Hagenbach et al. · 1974 [cited by applicant]
US 4298672A · Lu · 1981 [cited by applicant]
US 4338390A · Lu · 1982 [cited by applicant]
US 4533614A · Fukumoto et al. · 1985 [cited by applicant]
US 4845006A · Matsubara et al. · 1989 [cited by applicant]
US 4863824A · Uchida et al. · 1989 [cited by applicant]
US 4863825A · Yoshimoto et al. · 1989 [cited by applicant]
US 4917983A · Uchida et al. · 1990 [cited by applicant]
US 4927728A · Isoda et al. · 1990 [cited by applicant]
US 4931370A · Amaya · 1990 [cited by applicant]
US 4933252A · Nishikawa et al. · 1990 [cited by applicant]
US 4935326A · Creatura et al. · 1990 [cited by applicant]
US 4937166A · Creatura et al. · 1990 [cited by applicant]
US 4957774A · Doi et al. · 1990 [cited by applicant]
US 4973539A · Sacripante et al. · 1990 [cited by applicant]
US 4980448A · Tajiri et al. · 1990 [cited by applicant]
US 4981939A · Matsumura et al. · 1991 [cited by applicant]
US 4988794A · Kubo et al. · 1991 [cited by applicant]
US 5057596A · Kubo et al. · 1991 [cited by applicant]
US 5077170A · Tsujihiro · 1991 [cited by applicant]
US 5143809A · Kaneko et al. · 1992 [cited by applicant]
US 5215849A · Makuta et al. · 1993 [cited by applicant]
US 5227460A · Mahabadi et al. · 1993 [cited by applicant]
US 5236629A · Mahabadi et al. · 1993 [cited by applicant]
US 5290654A · Sacripante et al. · 1994 [cited by applicant]
US 5302486A · Patel et al. · 1994 [cited by applicant]
US 5330874A · Mahabadi et al. · 1994 [cited by applicant]
US 5376494A · Mahabadi et al. · 1994 [cited by applicant]
US 5445910A · Ishikawa · 1995 [cited by examiner]
US 5480756A · Mahabadi et al. · 1996 [cited by applicant]
US 5500324A · Mahabadi et al. · 1996 [cited by applicant]
US 5601960A · Mahabadi et al. · 1997 [cited by applicant]
US 5629121A · Nakayama · 1997 [cited by applicant]
US 5650484A · Hawkins et al. · 1997 [cited by applicant]
US 5750909A · Hawkins et al. · 1998 [cited by applicant]
US 6063827A · Sacripante et al. · 2000 [cited by applicant]
US 6120967A · Hopper et al. · 2000 [cited by applicant]
US 6214507B1 · Sokol et al. · 2001 [cited by applicant]
US 6326119B1 · Hollenbaugh, Jr. et al. · 2001 [cited by applicant]
US 6358657B1 · Silence et al. · 2002 [cited by applicant]
US 6359105B1 · Ianni et al. · 2002 [cited by applicant]
US 6592913B2 · Cook et al. · 2003 [cited by applicant]
US 7329476B2 · Sacripante et al. · 2008 [cited by applicant]
US 7960082B2 · Aziz et al. · 2011 [cited by applicant]
US 8663886B2 · Vanbesien et al. · 2014 [cited by applicant]
US 10358557B1 · Veregin et al. · 2019 [cited by applicant]
US 10725394B1 · Veregin · 2020 [cited by examiner]
US 20060216626A1 · Sacripante et al. · 2006 [cited by applicant]
US 20080107990A1 · Field et al. · 2008 [cited by applicant]
US 20080236446A1 · Zhou et al. · 2008 [cited by applicant]
US 20090047593A1 · Mizutani et al. · 2009 [cited by applicant]
US 20200308328A1 · Veregin et al. · 2020 [cited by applicant]
US 20220128920A1 · Shirakawa · 2022 [cited by examiner]
JP 6433562 · 1989 [cited by examiner]
Translation of JP 64-33562. [cited by examiner]
Richard Philip Nelson Veregin, et al., U.S. Appl. No. 17/086,516, filed Nov. 21, 2020, “Toner Compositions And Additives,” not yet published. [cited by applicant]
Richard Philip Nelson Veregin, et al., U.S. Appl. No. 17/213,295, filed Mar. 26, 2021, “Toner Compositions And Additives,” not yet published. [cited by applicant]