IP Library Granted Patent US 9,011,587
Granted Patent B1
US 9,011,587 · App. 14/053,592 · Granted Apr 21, 2015

Phase change inks comprising novel crystalline compounds

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Quick Facts
Patent No.
US 9,011,587
App. No.
14/053,592
Granted
Apr 21, 2015
Kind
B1
Abstract

A phase change ink composition suitable for ink jet printing, including robust printing on coated paper substrates. In embodiments, the phase change ink composition comprises both a crystalline compound and an amorphous compound which are derived from bio-renewable materials. In particular, the present embodiments provide novel crystalline compounds with at least two aromatic moieties for use in the phase change inks.

Claims (34)

1. A phase change ink comprising:

an amorphous component;

a crystalline component being a di-ester compound having the following structure:

wherein R is a saturated or ethylenically unsaturated aliphatic group; and

an optional colorant.

2. The phase change ink of claim 1 , wherein R is an alkyl group with at least 6 carbon atoms and no more than 60 carbon atoms.

3. The phase change ink of claim 1 , wherein the crystalline component has at least 60 percent by weight of bio-renewable content.

4. The phase change ink of claim 1 , wherein the crystalline component has a viscosity of less than 10 cps at a temperature of about 140° C.

5. The phase change ink of claim 1 , wherein the crystalline component has a viscosity of from about 1 to about 10 cps in a jetting range of from about 100 to about 140° C.

6. The phase change ink of claim 1 , wherein the crystalline component has T melt of less than 150° C.

7. The phase change ink of claim 1 , wherein the crystalline component has T crys of greater than 65° C.

8. The phase change ink of claim 1 , wherein the crystalline component has a viscosity of greater than about 10 6 cps at room temperature.

9. The phase change ink of claim 1 , wherein the crystalline component comprises a dialkyl naphthalene dicarboxylate compound.

10. The phase change ink of claim 1 , wherein the ink is capable of crystallizing at a total crystallization time of less than 15 seconds as measured by the standardized TROM procedure.

11. The phase change ink of claim 1 having at least 50% percent by weight of bio-renewable content.

12. The phase change ink of claim 1 , wherein the amorphous component is selected from the group consisting of

and mixtures thereof.

13. The phase change ink of claim 1 , wherein the crystalline component is present in an amount of from about 60 percent to about 95 percent by weight of the total weight of the phase change ink.

14. The phase change ink of claim 1 , wherein the amorphous component is present in an amount of from about 5 percent to about 40 percent by weight of the total weight of the phase change ink.

15. The phase change ink of claim 1 having a ratio of crystalline to amorphous ratio of from about 60:40 to about 95:5.

16. The phase change ink of claim 1 , wherein the optional colorant selected from the group consisting of a pigment, dye or mixtures thereof.

17. The phase change ink of claim 1 further comprising an additive selected from the group consisting of antioxidant, defoamer, slip and leveling agents, clarifier, viscosity modifier, adhesive, plasticizer and mixtures thereof.

18. A phase change ink comprising:

an amorphous component;

a crystalline component being a di-ester compound having the following structure:

wherein R is a saturated or ethylenically unsaturated aliphatic group; and

an optional colorant, wherein the phase change ink of claim 1 having a viscosity of from about 1 to about 22 cps in a jetting range of from about 100 to about 140° C.

19. The phase change ink of claim 18 having a viscosity of greater than about 10 6 cps at room temperature.

20. A phase change ink comprising: an amorphous component comprising an ester of tartaric acid of Formula I or an ester of Abitol E of Formula II shown below:

wherein each R 1 and R 2 can be the same or different, and wherein R 1 and R 2 each independently of the other is an alkyl group, wherein the alkyl can be straight, branched or cyclic, saturated or unsaturated, substituted or unsubstituted, having from about 1 to about 40 carbon atoms and R 3 is an alkylene group, including substituted and unsubstituted alkylene group, an amide of formula III shown below:

wherein R is selected from the group consisting of an alkyl group, an aryl group, an alkylaryl group, an arylalkyl group, and combinations thereof or an aromatic rosin ester selected from the group shown in formula IV below:

a crystalline component being a di-ester compound having the following structure:

wherein R is a saturated or ethylenically unsaturated aliphatic group; and

an optional colorant.

Assignments (11)
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 →
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 Oct 31, 2013
From: GOREDEMA, ADELA; SACRIPANTE, GUERINO G.; KEOSHKERIAN, BARKEV; VANBESIEN, DARYL W.; MORIMITSU, KENTARO; CHOPRA, NAVEEN; IFTIME, GABRIEL
To: XEROX CORPORATION
Reel/Frame 031524/0955 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 14, 2013
From: GOREDEMA, ADELA, MS.; SACRIPANTE, GUERINO G., MR.; KEOSHKERIAN, BARKEV, MR.; VANBESIEN, DARYL W., MR.; MORIMITSU, KENTARO, MR.; CHOPRA, NAVEEN, MS.; IFTIME, GABRIEL, MR.
To: XEROX CORPORATION
Reel/Frame 031402/0314 →