IP Library Granted Patent US 8,034,522
Granted Patent B2
US 8,034,522 · App. 11/937,077 · Granted Oct 11, 2011

Polyester toner resin compositions

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Quick Facts
Patent No.
US 8,034,522
App. No.
11/937,077
Granted
Oct 11, 2011
Kind
B2
Abstract

Provided herein are polyester toner resins that may reduce or eliminate the use of Bis A, a common polyester toner resin material that may pose environmental and/or toxicity risks. In addition, the polyester toner resins according to some embodiments of the present invention may have desirable toner resin properties, such as hot offset resistance.

Claims (36)

1. A toner composition comprising

a polyester toner resin formed from the reaction of monomers comprising

40 to 65 weight percent of an aromatic polycarboxylic acid;

0 to 15 weight percent of an unsaturated aliphatic polycarboxylic acid;

6 to 50 weight percent of at least one of an aliphatic diol and a glycidyl ester of an alkanoic acid;

2 to 5 weight percent of a branching agent; and

1 to 5 weight percent of an epoxy comprising a glycidyl methacrylate/styrene copolymer or glycidyl methacrylate/acrylic acid copolymer; and

a charge control agent.

2. The toner composition of claim 1 ,

wherein the aliphatic diol comprises at least one of ethylene glycol and propylene glycol.

3. The toner composition of claim 1 ,

wherein the glycidyl ester of an alkanoic acid is a glycidyl ester of neodecanoic acid.

4. The toner composition of claim 1 ,

wherein the branching agent comprises at least one of trimethylol propane and trimellitic anhydride.

5. The toner composition of claim 1 , wherein the epoxy comprises a glycidyl methacrylate/styrene copolyiner.

6. The toner composition of claim 1 ,

wherein the aromatic polycarboxylic acid is terephthalic acid.

7. The toner composition of claim 1 ,

wherein the unsaturated aliphatic polycarboxylic acid is fumaric acid.

8. The toner composition of claim 1 , further comprising one or more of the additives selected from the group consisting of paraffins, rheology modifying agents, inhibitors, lubricants, colorants, carrier materials and shrink-reducing additives.

9. A toner composition comprising

a polyester toner resin formed from the reaction of monomers comprising

0 to 25 weight percent of alkoxylated bisphenol A;

8 to 40 weight percent of an aliphatic diol;

5 to 30 weight percent of an unsaturated aliphatic polycarboxylic acid;

10 to 50 weight percent of an aromatic polycarboxylic acid;

2 to 5 weight percent of a branching agent; and

1 to 5 weight percent of an epoxy comprising a glycidyl methacrylate/styrene copolymer or a glycidyl methacrylate/acrylic acid copolymer; and

a charge control agent.

10. The toner composition of claim 9 , wherein the aliphatic diol comprises at least one of ethylene glycol and propylene glycol.

11. The toner composition of claim 9 , wherein the epoxy comprises a glycidyl methacrylate/styrene copolymer.

12. The toner composition of claim 9 , wherein the branching agent comprises at least one of an aliphatic triol and trimellitic anhydride.

13. The toner composition of claim 9 , wherein the aliphatic triol is trimethylol propane.

14. The toner composition of claim 9 , wherein the aromatic polycarboxylic acid comprises at least one of terephthalic acid and isophthalic acid.

15. The toner composition of claim 9 , wherein the unsaturated aliphatic polycarboxylic acid is fumaric acid.

16. The toner composition of claim 9 , further comprising one or more of the additives selected from the group consisting of paraffins, rheology modifying agents, inhibitors, lubricants, colorants, carrier materials and shrink-reducing additives.

Assignments (16)
MERGER Recorded Jan 28, 2025
From: REICHHOLD LLC 2
To: POLYNT COMPOSITES USA INC.
Reel/Frame 070029/0209 →
RELEASE OF SECURITY INTEREST Recorded Jul 3, 2022
From: U.S. BANK TRUSTEES LIMITED
To: REICHHOLD LLC 2
Reel/Frame 060394/0118 →
SECURITY INTEREST Recorded Mar 1, 2022
From: REICHHOLD LLC 2
To: BNY MELLON CORPORATE TRUSTEE SERVICES LIMITED, AS SECURITY AGENT
Reel/Frame 059133/0612 →
RELEASE OF SECURITY INTEREST Recorded May 23, 2017
From: REICHHOLD LLC 2
To: CANTOR FITZGERALD SECURITIES, AS COLLATERAL AGENT
Reel/Frame 042480/0046 →
RELEASE OF SECURITY INTEREST Recorded May 23, 2017
From: REICHHOLD, INC.
To: CANTOR FITZGERALD SECURITIES, AS COLLATERAL AGENT
Reel/Frame 042480/0067 →
RELEASE OF SECURITY INTEREST Recorded May 23, 2017
From: REICHHOLD, INC.
To: CANTOR FITZGERALD SECURITIES, AS COLLATERAL AGENT
Reel/Frame 042480/0025 →
RELEASE OF SECURITY INTEREST Recorded May 23, 2017
From: REICHHOLD LLC 2
To: CANTOR FITZGERALD SECURITIES, AS COLLATERAL AGENT
Reel/Frame 042480/0040 →
SECURITY INTEREST Recorded May 17, 2017
From: REICHHOLD LLC 2
To: U.S. BANK TRUSTEES LIMITED
Reel/Frame 042415/0687 →
NOTICE OF SECURITY INTEREST IN PATENTS (FIRST LIEN) Recorded Apr 17, 2015
From: REICHHOLD LLC 2
To: CANTOR FITZGERALD SECURITIES, AS COLLATERAL AGENT
Reel/Frame 035453/0234 →
NOTICE OF SECURITY INTEREST IN PATENTS (SECOND LIEN) Recorded Apr 17, 2015
From: REICHHOLD LLC 2
To: CANTOR FITZGERALD SECURITIES, AS COLLATERAL AGENT
Reel/Frame 035453/0507 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 10, 2015
From: REICHHOLD, INC.
To: REICHHOLD LLC 2
Reel/Frame 035385/0017 →
SECURITY INTEREST Recorded Oct 14, 2014
From: REICHHOLD, INC.
To: CANTOR FITZGERALD SECURITIES, AS COLLATERAL AGENT
Reel/Frame 033977/0776 →
SECURITY INTEREST Recorded Oct 14, 2014
From: REICHHOLD, INC.
To: CANTOR FITZGERALD SECURITIES, AS COLLATERAL AGENT
Reel/Frame 033977/0756 →
RELEASE OF SECURITY INTEREST IN PATENTS AT REEL/FRAME NO. 28154/0643 Recorded Oct 9, 2014
From: BANK OF AMERICA, N.A.
To: REICHHOLD, INC.
Reel/Frame 033949/0261 →
SECURITY AGREEMENT Recorded May 3, 2012
From: REICHHOLD, INC.
To: BANK OF AMERICA, N.A., AS AGENT
Reel/Frame 028154/0643 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 18, 2008
From: LIU, YONGNING; TOMAN, ALAN; DUMAIN, ERIC
To: REICHHOLD, INC.
Reel/Frame 020663/0436 →