IP Library Granted Patent US 9,187,663
Granted Patent B2
US 9,187,663 · App. 13/848,365 · Granted Nov 17, 2015

Ink composition and method of jetting ink

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Quick Facts
Patent No.
US 9,187,663
App. No.
13/848,365
Granted
Nov 17, 2015
Kind
B2
Abstract

A phase change ink composition is disclosed. The composition comprises a crystalline component including a diamide compound with an aromatic ring core; an amorphous component; and optionally a colorant. Methods of printing the phase change ink composition are also disclosed.

Claims (42)

1. A phase change ink composition, comprising:

a crystalline component comprising a diamide compound with an aromatic ring core;

an amorphous component selected from the group consisting of di-DL-menthyl L-tartrate, di-L-menthyl L-tartrate, di-L-menthyl DL-tartrate, di-DL-menthyl DL-tartrate, or stereoisomers or mixtures thereof; and

optionally a colorant.

2. The composition of claim 1 , wherein the diamide compound is a compound of formula 1:

where R′ and R″ are independently selected from organic amide groups of formulae 2 or 3:

where R, R 1 and R 2 are independently selected from the group consisting of a hydrogen atom or a linear, branched or cyclic, saturated or unsaturated, aliphatic or aromatic C 1 to C 40 substituent group, wherein at least one of R, R 1 and R 2 is not a hydrogen atom.

3. The composition of claim 1 , wherein the diamide compound is a compound of formula 4:

where R 1 and R 2 are independently selected from the group consisting of a hydrogen atom, alkyl group, alkenyl group, aryl group, arylalkyl group or alkylaryl group, the alkyl, alkenyl, aryl, arylalkyl and alkylaryl groups optionally containing one or more hetero atoms, wherein at least one of R 1 and R 2 is not a hydrogen atom.

4. The composition of claim 3 , wherein R 1 and R 2 are independently selected from the group consisting of a hydrogen atom, ethyl, n-propyl, i-butyl or substituted or unsubstituted C 10 to C 25 alkyl groups, where the optional substitutent can be an O, N or S containing functional group.

5. The composition of claim 1 , wherein the diamide compound is a compound of formula 5:

where R 1 and R 2 are independently selected from the group consisting of a hydrogen atom, alkyl group, alkenyl group, aryl group, arylalkyl group or alkylaryl group, the alkyl, alkenyl, aryl, arylalkyl and alkylaryl groups optionally containing one or more hetero atoms, wherein at least one of R 1 and R 2 is not a hydrogen atom.

6. The composition of claim 5 , wherein R 1 and R 2 are independently selected from the group consisting of a hydrogen atom, n-propyl, i-propyl, n-butyl, allyl, or substituted or unsubstituted C 10 to C 25 alkyl groups, where the optional substitutent can be an O, N or S containing functional group.

7. The composition of claim 1 , wherein the diamide compound is a compound of formula 6:

where R is selected from the group consisting of an alkyl group, alkenyl group, aryl group, arylalkyl group or alkylaryl group, the alkyl, alkenyl, aryl, arylalkyl and alkylaryl groups optionally containing one or more hetero atoms.

8. The composition of claim 7 , wherein R is a C 5 -C 7 alkyl group.

9. The composition of claim 1 , wherein the colorant is selected from the group consisting of a dye, a pigment or mixtures thereof.

10. The composition of claim 1 , wherein the crystalline and amorphous components are blended in a crystalline to amorphous component weight ratio ranging from about 60:40 to about 95:5.

11. A method comprising:

providing an ink jet printing device including a phase change ink composition, the phase change ink composition being in solid form and comprising (a) a crystalline component comprising a diamide compound with an aromatic ring core, (b) an amorphous component selected from the group consisting of di-DL-menthyl L-tartrate, di-L-menthyl L-tartrate, di-L-menthyl DL-tartrate, di-DL-menthyl DL-tartrate, or stereoisomers or mixtures thereof and (c) optionally a colorant;

heating the solid phase change ink composition to a temperature above the melting point of the composition to liquefy the ink composition; and

jetting the liquefied ink composition from the ink jet printing device onto a substrate to form an image.

12. The method of claim 11 , wherein each organic amide group of the diamide includes at least one aliphatic or aromatic substituent.

13. The method of claim 11 , wherein the crystalline component comprises a compound of formula 4:

where R 1 and R 2 are independently selected from the group consisting of a hydrogen atom, alkyl group, alkenyl group, aryl group, arylalkyl group or alkylaryl group, the alkyl, alkenyl, aryl, arylalkyl and alkylaryl groups optionally containing one or more hetero atoms, wherein at least one of R 1 and R 2 is not a hydrogen atom.

14. The method of claim 11 , wherein the crystalline component comprises a compound of formula 5:

where R 1 and R 2 are independently selected from the group consisting of a hydrogen atom, alkyl group, alkenyl group, aryl group, arylalkyl group or alkylaryl group, the alkyl, alkenyl, aryl, arylalkyl and alkylaryl groups optionally containing one or more hetero atoms, wherein at least one of R 1 and R 2 is not a hydrogen atom.

15. The method of claim 11 , wherein the crystalline component comprises a compound of formula 6:

where R is selected from the group consisting of an alkyl group, alkenyl group, aryl group, arylalkyl group or alkylaryl group, the alkyl, alkenyl, aryl, arylalkyl and alkylaryl groups optionally containing one or more hetero atoms.

16. The method of claim 11 , wherein the colorant is selected from the group consisting of a dye, a pigment or mixtures thereof.

17. The method of claim 11 , wherein the crystalline and amorphous components are blended in a crystalline to amorphous component weight ratio ranging from about 60:40 to about 95:5.

18. A phase change ink composition, comprising:

a crystalline component comprising a diamide compound with an aromatic ring core;

an amorphous component; and

optionally a colorant,

wherein the crystalline component has a viscosity of less than 10 cps at a temperature of 140° C.; the amorphous component has a viscosity less than 100 cps at a temperature of about 140° C.; and the crystalline component has a viscosity of greater than 1×10 6 cps at room temperature; and the amorphous component has a viscosity of greater than 1×10 5 cps at room temperature.

19. The composition of claim 18 , wherein the diamide compound is a compound of formula 1:

where R′ and R″ are independently selected from organic amide groups of formulae 2 or 3:

where R, R 1 and R 2 are independently selected from the group consisting of a hydrogen atom or a linear, branched or cyclic, saturated or unsaturated, aliphatic or aromatic C 1 to C 40 substituent group, wherein at least one of R, R 1 and R 2 is not a hydrogen atom.

20. The composition of claim 19 , wherein:

R is selected from the group consisting of an alkyl group, alkenyl group, aryl group, arylalkyl group or alkylaryl group, the alkyl, alkenyl, aryl, arylalkyl and alkylaryl groups optionally containing one or more hetero atoms; and

R 1 and R 2 are independently selected from the group consisting of a hydrogen atom, alkyl group, alkenyl group, aryl group, arylalkyl group or alkylaryl group, the alkyl, alkenyl, aryl, arylalkyl and alkylaryl groups optionally containing one or more hetero atoms, wherein at least one of R 1 and R 2 is not a hydrogen atom.

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 →