Phase change inks containing crystalline trans-cinnamic diesters and polyterpene resins

• US 8,906,150 B2
• Filed: 11/23/2011
• Issued: 12/09/2014
• Est. Priority Date: 04/27/2011
• Status: Expired due to Fees

• Current Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Original Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Inventors: Goredema, Adela, Carlini, Rina, Turek, Caroline M., Zwartz, Edward G.
• Primary Examiner(s): Qian, Yun
• Application Number:
  US13/303,516
• Publication Number:
  US 20130131226A1
• Time in Patent Office: 1,112 Days
• Field of Search: None
• US Class Current: 106/31.13
• CPC Class Codes: C09D 11/102 containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
• CPC Class Codes: C09D 11/34 Hot-melt inks
• CPC Class Codes: C09D 11/38 characterised by non-macromolecular additives other than solvents, pigments or dyes

Abstract

Disclosed is a phase change ink comprising an ink carrier which comprises: (a) a crystalline trans-cinnamic diester; and (b) an amorphous polyterpene resin.

Claims

1. A phase change ink comprising an ink carrier which comprises

(a) a crystalline trans-cinnamic diester selected from the group consisting of trans-cyclohexane-1,4-dimethanol-trans-cinnamate, para-phenyl-1,4-dimethanol-trans-cinnamate, bis(hydroxymethyl)furan-trans-cinnamate, 2,5-dihydroxymethyl-tetrahydrofuran-trans-cinnamate, trans-cinnamic acid-2,3-butanediol diester, and a mixture thereof;

and

(b) an amorphous polyterpene resin.

2. An ink according to claim 1 wherein the trans-cinnamic diester is present in the ink carrier in an amount of from 50 to 95 percent by weight.

3. An ink according to claim 1 wherein the polyterpene resin contains monomers selected from alpha-pinene, beta-pinene, limonene, norbornene, myrcene, phellandrene, carvone, camphene, 2-carene, 3-carene, perillyl alcohol, perillyl aldehyde, perillic acid, alkyl esters of perillyl alcohol, aryl esters of perillyl alcohol, arylalkyl esters of perillyl alcohol, alkylaryl esters of perillyl alcohol, α

-ionone, β

-ionone, γ

-terpinene, β

-citronellene, β

-citronellol, citronellal, citronellic acid, alkyl esters of β

-citronellol, aryl esters of β

-citronellol, arylalkyl esters of β

-citronellol, alkylaryl esters of β

-citronellol, geraniol, geranial, alkyl esters of geraniol, aryl esters of geraniol, arylalkyl esters of geraniol, alkylaryl esters of geraniol, linalool, alkyl esters of linalool, aryl esters of linalool, arylalkyl esters of linalool, alkylaryl esters of linalool, nerolidol, alkyl esters of nerolidol, aryl esters of nerolidol, arylalkyl esters of nerolidol, alkylaryl esters of nerolidol, verbenol, verbenone, alkyl esters of verbenol, aryl esters of verbenol, arylalkyl esters of verbenol, alkylaryl esters of verbenol, and mixtures thereof.

4. An ink according to claim 1 wherein the polyterpene resin is on an α

-pinene/β

-pinene copolymer, a β

-pinene polymer, a limonene polymer, or a mixture thereof.

5. An ink according to claim 1 wherein the polyterpene resin is present in the ink carrier in on amount of from 5 to 50 percent by weight.

6. An ink according to claim 1 further containing a viscosity modifier.

7. An ink according to claim 6 wherein the viscosity modifier is a sorbitol ester, a pentaerythritol ester, or a mixture thereof.

8. An ink according to claim 6 wherein the viscosity modifier is pentaerythritol tetrastearate, pentaerythritol tetrabenzoate, a sorbitan tristearate ester, stearyl stearamide, erucamide, stearone, sucrose tetrastearate, sucrose tetrastearate triacetate, an ester of the formula:

9. An ink according to claim 6 wherein the viscosity modifier is present in the ink in on amount of from 0.5 to 15 percent by weight of the ink.

10. An ink according to claim 1 having a hardness value of at least 70 as measured at 25°

C.

11. An ink according to claim 1 having a peak melting point, as measured by DSC, of from 60 to 120°

C.

12. An ink according to claim 1 wherein the ink carrier has a bio-renewable content of at least 10%.

13. An ink according to claim 1 having a crystallization temperature, as measured by differential scanning calorimetry, of from 65 to 150°

C.

14. An ink according to claim 1 wherein the polyterpene resin contains monomers selected from alpha-pinene, norbornene, myrcene, phellandrene, carvone, camphene, 2-carene, 3-carene, perillyl alcohol, perillyl aldehyde, perillic acid, alkyl esters of perillyl alcohol, aryl esters of perillyl alcohol, arylalkyl esters of perillyl alcohol, alkylaryl esters of perillyl alcohol, α

-ionone, β

-ionone, γ

-terpinene, β

-citronellene, β

-citronellol, citronellal, citronellic acid, alkyl esters of β

-citronellol, aryl esters of β

-citronellol, arylalkyl esters of β

-citronellol, alkylaryl esters of β

-citronellol, geraniol, geranial, alkyl esters of geraniol, aryl esters of geraniol, arylalkyl esters of geraniol, alkylaryl esters of geraniol, linalool, alkyl esters of linalool, aryl esters of linalool, arylalkyl esters of linalool, alkylaryl esters of linalool, nerolidol, alkyl esters of nerolidol, aryl esters of nerolidol, arylalkyl esters of nerolidol, alkylaryl esters of nerolidol, verbenol, verbenone, alkyl esters of verbenol, aryl esters of verbenol, arylalkyl esters of verbenol, alkylaryl esters of verbenol, and mixtures thereof.

15. An ink according to claim 6 wherein the viscosity modifier is a sorbitol ester.

16. An ink according to claim 1 wherein the trans-cinnamic diester is trans-cyclohexane-1,4-dimethanol-trans-cinnamate.

17. An ink according to claim 1 wherein the trans-cinnamic diester is para-phenyl-1,4-dimethanol-trans-cinnamate.

18. An ink according to claim 1 wherein the trans-cinnamic diester is bis(hydroxymethyl)furan-trans-cinnamate.

19. An ink according to claim 1 wherein the trans-cinnamic diester is 2,5-dihydroxymethyl-tetrahydrofuran-trans-cinnamate.

20. A phase change ink comprising:

(1) an ink carrier comprising;

(a) a crystalline trans-cinnamic diester in an amount of from 50 to 95 percent by weight, wherein said trans-cinnamic diester is trans-cinnamic acid-2,3-butanediol diester; and

(b) an amorphous polyterpene resin in an amount of from 5 to 50 percent by weight, said polyterpene resin containing monomers selected from alpha-pinene, beta-pinene, limonene, norbornene, myrcene, phellandrene, carvone, camphene, 2-carene, 3-carene, perillyl alcohol, perillyl aldehyde, perillic acid, alkyl esters of perillyl alcohol, aryl esters of perillyl alcohol, arylalkyl esters of perillyl alcohol, alkylaryl esters of perillyl alcohol, α

-ionone, β

-ionone, γ

-terpinene, β

-citronellene, β

-citronellol, citronellal, citronellic acid, alkyl esters of β

-citronellol, aryl esters of β

-citronellol, arylalkyl esters of β

-citronellol, alkylaryl esters of β

-citronellol, geraniol, geranial, alkyl esters of geraniol, aryl esters of geraniol, arylalkyl esters of geraniol, alkylaryl esters of geraniol, linalool, alkyl esters of linalool, aryl esters of linalool, arylalkyl esters of linalool, alkylaryl esters of linalool, nerolidol, alkyl esters of nerolidol, aryl esters of nerolidol, arylalkyl esters of nerolidol, alkylaryl esters of nerolidol, verbenol, verbenone, alkyl esters of verbenol, aryl esters of verbenol, arylalkyl esters of verbenol, alkylaryl esters of verbenol, and mixtures thereof; and

(2) a colorant.