IP Library Granted Patent US 9,109,124
Granted Patent B2
US 9,109,124 · App. 13/432,549 · Granted Aug 18, 2015

Solid ink compositions comprising semicrystalline oligomer resins

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Quick Facts
Patent No.
US 9,109,124
App. No.
13/432,549
Granted
Aug 18, 2015
Kind
B2
Abstract

A solid ink composition comprising oligomer resins which are suitable for direct-to-paper (DTP) and/or transfix inkjet printing. In embodiments, the oligomer resins are poly/oligoester and poly/oligoesteramide compounds, which are non-wax materials having semi-crystalline properties.

Claims (29)

1. A solid phase change ink comprising:

a semi-crystalline oligomer resin selected from the group consisting of a polyester, an oligoester, a polyesteramide and oligoesteramide;

an optional colorant; and

an ink vehicle, wherein the semi-crystalline oligomer resin is made from a condensation reaction of a dicarboxylic acid or anhydride or diester, a difunctional alkanol monomer, and an optional monofunctional end-capping reactant, and further wherein the oligomer resin is an oligoesteramide and has the following formula

wherein R 1 , R 2 , and R 3 are independent from one another and further wherein R 1 is an alkylene group having from about 1 to about 20 carbons; alkyleneoxy having from about 1 to about 20 carbons; arylene group having from about 6 to about 20 carbons; or arylalkylene group having from about 7 to about 20 carbons; R 2 is an alkylene group having from about 1 to about 20 carbons; alkyleneoxy having from about 1 to about 20 carbons; arylene group having from about 6 to about 20 carbons; or arylalkylene group having from about 7 to about 20 carbons; R 3 is H; alkyl group having from about 1 to about 50 carbons; aryl group having from about 6 to about 50 carbon atoms or alkylaryl group having from about 7 to about 50 carbons; and n is a number of from about 1 to about 10.

2. The solid phase change ink of claim 1 , wherein the ink vehicle has a crystallization temperature that lies within ±15° C. of the crystallization temperature of the oligomer resin.

3. The solid phase change ink of claim 1 , wherein said ink has a melt temperature of 80° C. or higher.

4. The solid phase change ink of claim 3 , wherein said ink has a melt temperature of from about 80 to about 130° C.

5. The solid phase change ink of claim 1 , wherein said ink has a crystallization of from about 50 to about 110° C.

6. The solid phase change ink of claim 5 , wherein said ink has a crystallization of from about 60 to about 100° C.

7. The solid phase change ink of claim 1 , wherein said ink has a viscosity of greater than 1×10 6 cPs over a temperature range of from about 20° C. to about 60° C.

8. The solid phase change ink of claim 1 , wherein the ink vehicle further comprises other crystalline components present in an amount of 1 to 70 wt % of the ink.

9. The solid phase change ink of claim 1 having a phase-transition from liquid (molten) state to solid (crystallized) state at a temperature ranging from about 50° C. to about 110° C.

10. The solid phase change ink of claim 1 having an ink crystallization phase transition from liquid state to solid state that ranges in temperature of from about 5° C. to about 15° C.

11. A solid phase change ink comprising:

a semi-crystalline oligomer resin selected from the group consisting of a polyester, an oligoester, a polyesteramide and oligoesteramide;

a colorant; and

an ink vehicle, wherein the oligomer resin is made by the condensation reactions of a dicarboxylic acid, a difunctional alkanol monomer, and an optional monofunctional end-capping reactant, represented by the following reaction:

wherein X═O, NH, and mixtures thereof, group Z═O or NH in the optional end-capping agent R 3 ZH, and R 1 , R 2 , and R 3 are independent from one another and are unsubstituted and further wherein R 1 is an alkylene group having from about 1 to about 20 carbons; alkyleneoxy having from about 1 to about 20 carbons; arylene group having from about 6 to about 20 carbons; or arylalkylene group having from about 7 to about 20 carbons; R 2 is an alkylene group having from about 1 to about 20 carbons; alkyleneoxy having from about 1 to about 20 carbons; arylene group having from about 6 to about 20 carbons; or arylalkylene group having from about 7 to about 20 carbons; R 3 is H; alkyl group having from about 1 to about 50 carbons; aryl group having from about 6 to about 50 carbon atoms or alkylaryl group having from about 7 to about 50 carbons; and n is a number of from about 1 to about 10;

further wherein the ink vehicle comprises a crystalline compound.

12. The solid phase change ink of claim 11 , wherein a mol percent ratio of the dicarboxylic acid to the difunctional alkanol monomer is from about 2:1 to about 0.5:1.

13. A solid phase change ink comprising:

A semi-crystalline oligoesteramide or oligoester resin;

a colorant; and

an ink vehicle, wherein the oligoesteramide resin has the following formula

wherein R 1 , R 2 , and R 3 are independent from one another and further wherein R 1 is an alkylene group having from about 1 to about 20 carbons; alkyleneoxy having from about 1 to about 20 carbons; arylene group having from about 6 to about 20 carbons; or arylalkylene group having from about 7 to about 20 carbons; R 2 is an alkylene group having from about 1 to about 20 carbons; alkyleneoxy having from about 1 to about 20 carbons; arylene group having from about 6 to about 20 carbons; or arylalkylene group having from about 7 to about 20 carbons; R 3 is H; alkyl group having from about 1 to about 50 carbons; aryl group having from about 6 to about 50 carbon atoms or alkylaryl group having from about 7 to about 50 carbons; and n is a number of from about 1 to about 10, and the oligoester resin has the following formula

wherein R 1 , R 2 , and R 3 are independent from one another and further wherein R 1 is an alkylene group having from about 1 to about 20 carbons; alkyleneoxy having from about 1 to about 20 carbons; arylene group having from about 6 to about 20 carbons; or arylalkylene group having from about 7 to about 20 carbons; R 2 is an alkylene group having from about 1 to about 20 carbons; alkyleneoxy having from about 1 to about 20 carbons; arylene group having from about 6 to about 20 carbons; or arylalkylene group having from about 7 to about 20 carbons; R 3 is H; alkyl group having from about 1 to about 50 carbons; aryl group having from about 6 to about 50 carbon atoms or alkylaryl group having from about 7 to about 50 carbons; and n is a number of from about 1 to about 10;

further wherein the ink vehicle comprises a crystalline compound.

14. The solid phase change ink of claim 13 , wherein the oligoesteramide or oligoester resin is present in an amount of from about 10 to about 90 percent by weight of the total weight of the solid phase change ink.

Assignments (9)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 6, 2025
From: XEROX CORPORATION
To: GENESEE VALLEY INNOVATIONS, LLC
Reel/Frame 073842/0479 →
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 →